data_00
#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic      2021-10-30
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted     ?
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code      AW5064
_journal_coeditor_notes
; ?
;
_journal_paper_category      FA
_journal_techeditor_code      ?
_iucr_compatibility_tag          ACTA95
_journal_techeditor_notes  
;
;
_journal_coden_ASTM               ?
_journal_name_full                ?
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

#==============================================================================

 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H16 N O3 P' 
_chemical_formula_weight          325.29

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    9.8195(4)
_cell_length_b                    9.8992(4)
_cell_length_c                    16.2764(7)
_cell_angle_alpha                 90
_cell_angle_beta                  94.985(2)
_cell_angle_gamma                 90
_cell_volume                      1576.17(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9870
_cell_measurement_theta_min       2.34
_cell_measurement_theta_max       30.06
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.371          
_exptl_crystal_F_000              680
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.340
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.150
_exptl_absorpt_coefficient_mu     0.189
_shelx_estimated_absorpt_T_min    0.939
_shelx_estimated_absorpt_T_max    0.972
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7033 
_exptl_absorpt_correction_T_max   0.7460
_exptl_absorpt_process_details    'SADABS 2014/5'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker D8 Venture PHOTON 100 CMOS type'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             36542
_diffrn_reflns_av_unetI/netI      0.0424
_diffrn_reflns_av_R_equivalents   0.0665
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.336
_diffrn_reflns_theta_max          29.574
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4429
_reflns_number_gt                 3507
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics     'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material   'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+0.9836P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4429
_refine_ls_number_parameters      211
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0649
_refine_ls_R_factor_gt            0.0436
_refine_ls_wR_factor_ref          0.1002
_refine_ls_wR_factor_gt           0.0920
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
P1 P 0.05889(4) 0.18853(4) 0.43683(2) 0.00939(10) Uani 1 1 d . . . . .
O1 O -0.04223(10) 0.31204(10) 0.44570(6) 0.0125(2) Uani 1 1 d . . . . .
O2 O 0.16064(10) 0.26913(10) 0.38484(6) 0.0128(2) Uani 1 1 d . . . . .
O3 O -0.00572(10) 0.06778(10) 0.39826(6) 0.0127(2) Uani 1 1 d . . . . .
N1 N 0.13674(13) 0.14996(13) 0.52600(8) 0.0120(2) Uani 1 1 d . . . . .
H1N H 0.1106(18) 0.0742(18) 0.5446(11) 0.014 Uiso 1 1 d . U . . .
C1 C -0.16213(14) 0.28487(14) 0.48551(9) 0.0124(3) Uani 1 1 d . . . . .
C2 C -0.16974(16) 0.33394(15) 0.56439(9) 0.0159(3) Uani 1 1 d . . . . .
H2 H -0.095202 0.381634 0.591925 0.019 Uiso 1 1 calc R U . . .
C3 C -0.28888(17) 0.31193(16) 0.60254(10) 0.0196(3) Uani 1 1 d . . . . .
H3 H -0.296171 0.344991 0.656775 0.023 Uiso 1 1 calc R U . . .
C4 C -0.39742(16) 0.24204(17) 0.56207(10) 0.0189(3) Uani 1 1 d . . . . .
H4 H -0.478682 0.227504 0.588522 0.023 Uiso 1 1 calc R U . . .
C5 C -0.38696(15) 0.19331(16) 0.48271(10) 0.0177(3) Uani 1 1 d . . . . .
H5 H -0.461207 0.145325 0.455075 0.021 Uiso 1 1 calc R U . . .
C6 C -0.26858(15) 0.21444(15) 0.44370(9) 0.0153(3) Uani 1 1 d . . . . .
H6 H -0.260746 0.181337 0.389524 0.018 Uiso 1 1 calc R U . . .
C7 C 0.27063(14) 0.21355(14) 0.34665(8) 0.0112(3) Uani 1 1 d . . . . .
C8 C 0.29072(15) 0.07618(15) 0.33770(9) 0.0155(3) Uani 1 1 d . . . . .
H8 H 0.230616 0.012754 0.359321 0.019 Uiso 1 1 calc R U . . .
C9 C 0.40150(16) 0.03293(16) 0.29609(10) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.417066 -0.061003 0.289467 0.021 Uiso 1 1 calc R U . . .
C10 C 0.48905(16) 0.12573(16) 0.26433(9) 0.0169(3) Uani 1 1 d . . . . .
H10 H 0.564163 0.095546 0.236146 0.020 Uiso 1 1 calc R U . . .
C11 C 0.46603(16) 0.26316(17) 0.27407(10) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.525441 0.326903 0.252110 0.022 Uiso 1 1 calc R U . . .
C12 C 0.35709(15) 0.30795(15) 0.31555(9) 0.0150(3) Uani 1 1 d . . . . .
H12 H 0.341870 0.401858 0.322567 0.018 Uiso 1 1 calc R U . . .
C13 C 0.21430(14) 0.23050(14) 0.58468(9) 0.0110(3) Uani 1 1 d . . . . .
C14 C 0.24462(16) 0.36575(15) 0.57096(9) 0.0154(3) Uani 1 1 d . . . . .
H14 H 0.211591 0.408585 0.520920 0.018 Uiso 1 1 calc R U . . .
C15 C 0.32388(16) 0.43764(16) 0.63134(10) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.345498 0.529519 0.621748 0.021 Uiso 1 1 calc R U . . .
C16 C 0.37155(16) 0.37737(16) 0.70499(9) 0.0162(3) Uani 1 1 d . . . . .
H16 H 0.425211 0.427413 0.745749 0.019 Uiso 1 1 calc R U . . .
C17 C 0.33995(15) 0.24242(15) 0.71870(9) 0.0138(3) Uani 1 1 d . . . . .
H17 H 0.371734 0.200394 0.769236 0.017 Uiso 1 1 calc R U . . .
C18 C 0.26230(14) 0.16912(14) 0.65892(9) 0.0119(3) Uani 1 1 d . . . . .
H18 H 0.241731 0.076982 0.668488 0.014 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
P1 O3 1.4685(10) . ?
P1 O2 1.5804(10) . ?
P1 O1 1.5895(10) . ?
P1 N1 1.6260(13) . ?
O1 C1 1.4181(17) . ?
O2 C7 1.4045(17) . ?
N1 C13 1.4148(18) . ?
N1 H1N 0.856(18) . ?
C1 C2 1.381(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.384(2) . ?
C7 C12 1.387(2) . ?
C8 C9 1.398(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 P1 O2 116.86(6) . . ?
O3 P1 O1 114.51(6) . . ?
O2 P1 O1 95.12(5) . . ?
O3 P1 N1 110.04(6) . . ?
O2 P1 N1 109.05(6) . . ?
O1 P1 N1 110.40(6) . . ?
C1 O1 P1 116.46(9) . . ?
C7 O2 P1 125.84(9) . . ?
C13 N1 P1 130.84(10) . . ?
C13 N1 H1N 114.5(12) . . ?
P1 N1 H1N 112.9(12) . . ?
C2 C1 C6 122.31(14) . . ?
C2 C1 O1 118.19(13) . . ?
C6 C1 O1 119.47(13) . . ?
C1 C2 C3 118.45(14) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.54(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.86(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.33(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 118.51(14) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C12 121.75(14) . . ?
C8 C7 O2 123.63(13) . . ?
C12 C7 O2 114.59(13) . . ?
C7 C8 C9 118.44(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 120.73(14) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.53(14) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.56(14) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.99(14) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C14 C13 C18 119.71(13) . . ?
C14 C13 N1 122.90(13) . . ?
C18 C13 N1 117.39(13) . . ?
C13 C14 C15 119.42(14) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 121.10(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.26(14) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.35(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.17(13) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O3 P1 O1 C1 53.11(11) . . . . ?
O2 P1 O1 C1 175.76(10) . . . . ?
N1 P1 O1 C1 -71.72(11) . . . . ?
O3 P1 O2 C7 -51.28(13) . . . . ?
O1 P1 O2 C7 -172.10(11) . . . . ?
N1 P1 O2 C7 74.25(12) . . . . ?
O3 P1 N1 C13 178.86(12) . . . . ?
O2 P1 N1 C13 49.46(15) . . . . ?
O1 P1 N1 C13 -53.79(15) . . . . ?
P1 O1 C1 C2 106.89(13) . . . . ?
P1 O1 C1 C6 -75.11(15) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
O1 C1 C2 C3 177.67(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
O1 C1 C6 C5 -177.65(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
P1 O2 C7 C8 11.5(2) . . . . ?
P1 O2 C7 C12 -170.52(10) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
O2 C7 C8 C9 177.88(13) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C8 C7 C12 C11 0.3(2) . . . . ?
O2 C7 C12 C11 -177.72(13) . . . . ?
P1 N1 C13 C14 -4.3(2) . . . . ?
P1 N1 C13 C18 176.23(11) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
N1 C13 C14 C15 -178.82(14) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
N1 C13 C18 C17 179.46(13) . . . . ?
 
_refine_diff_density_max    0.362
_refine_diff_density_min   -0.418
_refine_diff_density_rms    0.066



data_2Br
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 Br N O3 P'
_chemical_formula_sum              'C18 H15 Br N O3 P'
_chemical_formula_weight           404.19
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.4356(2)
_cell_length_b                     9.2086(2)
_cell_length_c                     11.2129(2)
_cell_angle_alpha                  79.7190(10)
_cell_angle_beta                   86.2930(10)
_cell_angle_gamma                  73.6770(10)
_cell_volume                       822.39(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      7959
_cell_measurement_temperature      100.15
_cell_measurement_theta_max        30.23
_cell_measurement_theta_min        2.52
_shelx_estimated_absorpt_T_max     0.745
_shelx_estimated_absorpt_T_min     0.523
_exptl_absorpt_coefficient_mu      2.613
_exptl_absorpt_correction_T_max    0.745
_exptl_absorpt_correction_T_min    0.523
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     SADABS-2014/2
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.632
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               408
_exptl_crystal_size_max            0.285
_exptl_crystal_size_mid            0.187
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0253
_diffrn_reflns_av_unetI/netI       0.0278
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              16599
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.699
_diffrn_reflns_theta_min           1.846
_diffrn_ambient_temperature        100.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3852
_reflns_number_total               4229
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.403
_refine_diff_density_min           -0.369
_refine_diff_density_rms           0.065
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       217
_refine_ls_number_reflns           4229
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0292
_refine_ls_R_factor_gt             0.0252
_refine_ls_restrained_S_all        1.053
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0269P)²+0.3561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0581
_refine_ls_wR_factor_ref           0.0593
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br -0.14169(2) 0.81141(2) 0.24884(2) 0.01940(6) Uani 1 1 d . . . . .
 P1 P 0.25748(5) 0.83650(4) 0.48600(3) 0.01011(8) Uani 1 1 d . . . . .
 O1 O 0.36571(13) 0.71687(12) 0.58931(10) 0.0135(2) Uani 1 1 d . . . . .
 O2 O 0.39749(13) 0.80527(12) 0.38443(10) 0.0129(2) Uani 1 1 d . . . . .
 O3 O 0.19924(14) 0.99483(12) 0.50845(10) 0.0142(2) Uani 1 1 d . . . . .
 N1 N 0.10576(16) 0.77428(14) 0.45344(12) 0.0114(3) Uani 1 1 d . . . . .
 H1 H 0.005286 0.832989 0.463291 0.014 Uiso 1 1 d R U . . .
 C1 C 0.31604(19) 0.67630(17) 0.70892(14) 0.0127(3) Uani 1 1 d . . . . .
 C2 C 0.1871(2) 0.76956(18) 0.76606(15) 0.0157(3) Uani 1 1 d . . . . .
 H2 H 0.124090 0.865163 0.723817 0.019 Uiso 1 1 calc R U . . .
 C3 C 0.1517(2) 0.7200(2) 0.88706(15) 0.0201(4) Uani 1 1 d . . . . .
 H3 H 0.063270 0.782185 0.927783 0.024 Uiso 1 1 calc R U . . .
 C4 C 0.2444(2) 0.5806(2) 0.94864(16) 0.0227(4) Uani 1 1 d . . . . .
 H4 H 0.219843 0.547778 1.031240 0.027 Uiso 1 1 calc R U . . .
 C5 C 0.3728(2) 0.4895(2) 0.88930(15) 0.0207(4) Uani 1 1 d . . . . .
 H5 H 0.436445 0.394187 0.931529 0.025 Uiso 1 1 calc R U . . .
 C6 C 0.4093(2) 0.53631(18) 0.76863(15) 0.0165(3) Uani 1 1 d . . . . .
 H6 H 0.496856 0.473439 0.727623 0.020 Uiso 1 1 calc R U . . .
 C7 C 0.11846(19) 0.63514(17) 0.41079(14) 0.0112(3) Uani 1 1 d . . . . .
 C8 C 0.01830(19) 0.63100(17) 0.31795(14) 0.0125(3) Uani 1 1 d . . . . .
 C9 C 0.0264(2) 0.49627(18) 0.27632(15) 0.0150(3) Uani 1 1 d . . . . .
 H9 H -0.043828 0.496699 0.213295 0.018 Uiso 1 1 calc R U . . .
 C10 C 0.1377(2) 0.36091(18) 0.32715(15) 0.0161(3) Uani 1 1 d . . . . .
 H10 H 0.144066 0.267819 0.299304 0.019 Uiso 1 1 calc R U . . .
 C11 C 0.2396(2) 0.36204(18) 0.41889(15) 0.0160(3) Uani 1 1 d . . . . .
 H11 H 0.316382 0.269425 0.453639 0.019 Uiso 1 1 calc R U . . .
 C12 C 0.23015(19) 0.49748(17) 0.46033(14) 0.0139(3) Uani 1 1 d . . . . .
 H12 H 0.300721 0.496528 0.523315 0.017 Uiso 1 1 calc R U . . .
 C13 C 0.37484(19) 0.90917(17) 0.27397(14) 0.0122(3) Uani 1 1 d . . . . .
 C14 C 0.4468(2) 1.02906(18) 0.25957(14) 0.0143(3) Uani 1 1 d . . . . .
 H14 H 0.509470 1.041320 0.322628 0.017 Uiso 1 1 calc R U . . .
 C15 C 0.4252(2) 1.13124(18) 0.15052(15) 0.0169(3) Uani 1 1 d . . . . .
 H15 H 0.473587 1.214355 0.138547 0.020 Uiso 1 1 calc R U . . .
 C16 C 0.3332(2) 1.11223(19) 0.05918(15) 0.0185(3) Uani 1 1 d . . . . .
 H16 H 0.316969 1.183460 -0.014513 0.022 Uiso 1 1 calc R U . . .
 C17 C 0.2648(2) 0.9895(2) 0.07521(15) 0.0190(3) Uani 1 1 d . . . . .
 H17 H 0.203368 0.976110 0.011911 0.023 Uiso 1 1 calc R U . . .
 C18 C 0.2857(2) 0.88600(19) 0.18347(15) 0.0164(3) Uani 1 1 d . . . . .
 H18 H 0.239740 0.801333 0.194903 0.020 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C8 1.8966(15) . ?
 P1 O1 1.5827(11) . ?
 P1 O2 1.5895(11) . ?
 P1 O3 1.4638(11) . ?
 P1 N1 1.6270(13) . ?
 O1 C1 1.3966(18) . ?
 O2 C13 1.4109(18) . ?
 N1 H1 0.8800 . ?
 N1 C7 1.4201(19) . ?
 C1 C2 1.383(2) . ?
 C1 C6 1.385(2) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.393(2) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.388(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.384(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.387(2) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.395(2) . ?
 C7 C12 1.396(2) . ?
 C8 C9 1.384(2) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.385(2) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.386(2) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.387(2) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.383(2) . ?
 C13 C18 1.381(2) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.391(2) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.388(2) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.386(2) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.391(2) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O2 94.06(6) . . ?
 O1 P1 N1 109.86(6) . . ?
 O2 P1 N1 108.40(6) . . ?
 O3 P1 O1 115.76(6) . . ?
 O3 P1 O2 115.90(6) . . ?
 O3 P1 N1 111.52(7) . . ?
 C1 O1 P1 126.78(10) . . ?
 C13 O2 P1 117.38(9) . . ?
 P1 N1 H1 116.6 . . ?
 C7 N1 P1 126.82(11) . . ?
 C7 N1 H1 116.6 . . ?
 C2 C1 O1 123.23(14) . . ?
 C2 C1 C6 121.80(15) . . ?
 C6 C1 O1 114.94(14) . . ?
 C1 C2 H2 120.8 . . ?
 C1 C2 C3 118.42(15) . . ?
 C3 C2 H2 120.8 . . ?
 C2 C3 H3 119.7 . . ?
 C4 C3 C2 120.64(16) . . ?
 C4 C3 H3 119.7 . . ?
 C3 C4 H4 120.1 . . ?
 C5 C4 C3 119.75(16) . . ?
 C5 C4 H4 120.1 . . ?
 C4 C5 H5 119.7 . . ?
 C4 C5 C6 120.52(16) . . ?
 C6 C5 H5 119.7 . . ?
 C1 C6 C5 118.87(16) . . ?
 C1 C6 H6 120.6 . . ?
 C5 C6 H6 120.6 . . ?
 C8 C7 N1 120.98(13) . . ?
 C8 C7 C12 117.44(14) . . ?
 C12 C7 N1 121.58(14) . . ?
 C7 C8 Br1 120.27(11) . . ?
 C9 C8 Br1 117.66(12) . . ?
 C9 C8 C7 122.02(14) . . ?
 C8 C9 H9 120.2 . . ?
 C8 C9 C10 119.55(15) . . ?
 C10 C9 H9 120.2 . . ?
 C9 C10 H10 120.2 . . ?
 C9 C10 C11 119.60(15) . . ?
 C11 C10 H10 120.2 . . ?
 C10 C11 H11 119.8 . . ?
 C10 C11 C12 120.45(15) . . ?
 C12 C11 H11 119.8 . . ?
 C7 C12 H12 119.5 . . ?
 C11 C12 C7 120.93(15) . . ?
 C11 C12 H12 119.5 . . ?
 C14 C13 O2 118.32(14) . . ?
 C18 C13 O2 119.26(13) . . ?
 C18 C13 C14 122.40(14) . . ?
 C13 C14 H14 120.8 . . ?
 C13 C14 C15 118.40(15) . . ?
 C15 C14 H14 120.8 . . ?
 C14 C15 H15 119.9 . . ?
 C16 C15 C14 120.25(15) . . ?
 C16 C15 H15 119.9 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 C15 120.16(15) . . ?
 C17 C16 H16 119.9 . . ?
 C16 C17 H17 119.8 . . ?
 C16 C17 C18 120.34(16) . . ?
 C18 C17 H17 119.8 . . ?
 C13 C18 C17 118.43(15) . . ?
 C13 C18 H18 120.8 . . ?
 C17 C18 H18 120.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C8 C9 C10 -177.85(12) . . . . ?
 P1 O1 C1 C2 -23.0(2) . . . . ?
 P1 O1 C1 C6 158.99(11) . . . . ?
 P1 O2 C13 C14 94.93(15) . . . . ?
 P1 O2 C13 C18 -86.59(16) . . . . ?
 P1 N1 C7 C8 -137.50(13) . . . . ?
 P1 N1 C7 C12 43.0(2) . . . . ?
 O1 P1 O2 C13 -167.62(11) . . . . ?
 O1 P1 N1 C7 -59.46(14) . . . . ?
 O1 C1 C2 C3 -177.79(14) . . . . ?
 O1 C1 C6 C5 177.53(14) . . . . ?
 O2 P1 O1 C1 -176.68(12) . . . . ?
 O2 P1 N1 C7 42.05(14) . . . . ?
 O2 C13 C14 C15 179.73(14) . . . . ?
 O2 C13 C18 C17 -179.95(14) . . . . ?
 O3 P1 O1 C1 61.95(14) . . . . ?
 O3 P1 O2 C13 -46.36(13) . . . . ?
 O3 P1 N1 C7 170.81(12) . . . . ?
 N1 P1 O1 C1 -65.46(13) . . . . ?
 N1 P1 O2 C13 79.89(12) . . . . ?
 N1 C7 C8 Br1 -1.5(2) . . . . ?
 N1 C7 C8 C9 -178.86(14) . . . . ?
 N1 C7 C12 C11 179.09(14) . . . . ?
 C1 C2 C3 C4 0.3(2) . . . . ?
 C2 C1 C6 C5 -0.5(2) . . . . ?
 C2 C3 C4 C5 -0.3(3) . . . . ?
 C3 C4 C5 C6 -0.1(3) . . . . ?
 C4 C5 C6 C1 0.6(3) . . . . ?
 C6 C1 C2 C3 0.1(2) . . . . ?
 C7 C8 C9 C10 -0.4(2) . . . . ?
 C8 C7 C12 C11 -0.4(2) . . . . ?
 C8 C9 C10 C11 -0.1(2) . . . . ?
 C9 C10 C11 C12 0.3(2) . . . . ?
 C10 C11 C12 C7 0.0(2) . . . . ?
 C12 C7 C8 Br1 178.05(11) . . . . ?
 C12 C7 C8 C9 0.7(2) . . . . ?
 C13 C14 C15 C16 0.1(2) . . . . ?
 C14 C13 C18 C17 -1.5(2) . . . . ?
 C14 C15 C16 C17 -1.2(3) . . . . ?
 C15 C16 C17 C18 1.0(3) . . . . ?
 C16 C17 C18 C13 0.4(3) . . . . ?
 C18 C13 C14 C15 1.3(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_2Cl
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 Cl N O3 P'
_chemical_formula_sum              'C18 H15 Cl N O3 P'
_chemical_formula_weight           359.73
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.4547(2)
_cell_length_b                     9.2155(2)
_cell_length_c                     11.0953(2)
_cell_angle_alpha                  79.7420(10)
_cell_angle_beta                   86.9390(10)
_cell_angle_gamma                  72.7840(10)
_cell_volume                       812.55(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9949
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.15
_cell_measurement_theta_min        2.74
_shelx_estimated_absorpt_T_max     0.974
_shelx_estimated_absorpt_T_min     0.889
_exptl_absorpt_coefficient_mu      0.350
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6176
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS-2014/2'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.470
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               372
_exptl_crystal_size_max            0.343
_exptl_crystal_size_mid            0.082
_exptl_crystal_size_min            0.076
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0140
_diffrn_reflns_av_unetI/netI       0.0112
_diffrn_reflns_Laue_measured_fraction_full  0.983
_diffrn_reflns_Laue_measured_fraction_max  0.980
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              23195
_diffrn_reflns_point_group_measured_fraction_full  0.983
_diffrn_reflns_point_group_measured_fraction_max  0.980
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.179
_diffrn_reflns_theta_min           2.348
_diffrn_ambient_temperature        99.95
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.983
_diffrn_measured_fraction_theta_max  0.980
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4535
_reflns_number_total               4715
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.419
_refine_diff_density_min           -0.329
_refine_diff_density_rms           0.050
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           4715
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0299
_refine_ls_R_factor_gt             0.0289
_refine_ls_restrained_S_all        1.056
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0418P)²+0.3613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0794
_refine_ls_wR_factor_ref           0.0803
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Cl1 Cl -0.13402(3) 0.81084(3) 0.75411(2) 0.02425(7) Uani 1 1 d . . . . .
 P1 P 0.25840(3) 0.83625(3) 0.98539(2) 0.01161(6) Uani 1 1 d . . . . .
 O1 O 0.39553(9) 0.80311(8) 0.88209(6) 0.01533(14) Uani 1 1 d . . . . .
 O2 O 0.36968(8) 0.71440(8) 1.08951(6) 0.01514(14) Uani 1 1 d . . . . .
 O3 O 0.20153(9) 0.99531(8) 1.00835(7) 0.01633(14) Uani 1 1 d . . . . .
 N1 N 0.10466(10) 0.77685(9) 0.95396(8) 0.01349(15) Uani 1 1 d . . . . .
 C1 C 0.37132(12) 0.90840(11) 0.77114(9) 0.01446(17) Uani 1 1 d . . . . .
 C2 C 0.27896(13) 0.88860(12) 0.67928(9) 0.01883(19) Uani 1 1 d . . . . .
 H2 H 0.232651 0.807333 0.690355 0.023 Uiso 1 1 calc R U . . .
 C3 C 0.25710(14) 0.99331(13) 0.56993(10) 0.0213(2) Uani 1 1 d . . . . .
 H3 H 0.195238 0.982261 0.507150 0.026 Uiso 1 1 calc R U . . .
 C4 C 0.32698(14) 1.11402(13) 0.55397(10) 0.0210(2) Uani 1 1 d . . . . .
 H4 H 0.310589 1.184374 0.481126 0.025 Uiso 1 1 calc R U . . .
 C5 C 0.42136(14) 1.12972(12) 0.64679(10) 0.01980(19) Uani 1 1 d . . . . .
 H5 H 0.469255 1.209939 0.635418 0.024 Uiso 1 1 calc R U . . .
 C6 C 0.44475(12) 1.02626(12) 0.75668(9) 0.01695(18) Uani 1 1 d . . . . .
 H6 H 0.508246 1.036018 0.819006 0.020 Uiso 1 1 calc R U . . .
 C7 C 0.11568(11) 0.63898(11) 0.90985(8) 0.01297(16) Uani 1 1 d . . . . .
 C8 C 0.01138(12) 0.63992(11) 0.81587(9) 0.01549(17) Uani 1 1 d . . . . .
 C9 C 0.01728(13) 0.50665(12) 0.77191(10) 0.01856(19) Uani 1 1 d . . . . .
 H9 H -0.053711 0.510114 0.709567 0.022 Uiso 1 1 calc R U . . .
 C10 C 0.12988(13) 0.36806(12) 0.82159(10) 0.01948(19) Uani 1 1 d . . . . .
 H10 H 0.134728 0.278124 0.792650 0.023 Uiso 1 1 calc R U . . .
 C11 C 0.23514(12) 0.36426(12) 0.91457(10) 0.01896(19) Uani 1 1 d . . . . .
 H11 H 0.310798 0.271511 0.947791 0.023 Uiso 1 1 calc R U . . .
 C12 C 0.22822(12) 0.49813(11) 0.95836(9) 0.01614(17) Uani 1 1 d . . . . .
 H12 H 0.299401 0.494024 1.020775 0.019 Uiso 1 1 calc R U . . .
 C13 C 0.32105(12) 0.67266(11) 1.20950(9) 0.01443(17) Uani 1 1 d . . . . .
 C14 C 0.41536(13) 0.52993(12) 1.26893(9) 0.01825(18) Uani 1 1 d . . . . .
 H14 H 0.500978 0.468201 1.228184 0.022 Uiso 1 1 calc R U . . .
 C15 C 0.37968(14) 0.48095(13) 1.39018(10) 0.0227(2) Uani 1 1 d . . . . .
 H15 H 0.442602 0.386078 1.431412 0.027 Uiso 1 1 calc R U . . .
 C16 C 0.25052(15) 0.57275(15) 1.45039(10) 0.0247(2) Uani 1 1 d . . . . .
 H16 H 0.226645 0.539200 1.531513 0.030 Uiso 1 1 calc R U . . .
 C17 C 0.15751(14) 0.71439(14) 1.38914(10) 0.0228(2) Uani 1 1 d . . . . .
 H17 H 0.070890 0.775410 1.429579 0.027 Uiso 1 1 calc R U . . .
 C18 C 0.19202(13) 0.76684(12) 1.26748(9) 0.01802(18) Uani 1 1 d . . . . .
 H18 H 0.130135 0.862304 1.226500 0.022 Uiso 1 1 calc R U . . .
 H1 H 0.008(2) 0.842(2) 0.9583(15) 0.030(4) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Cl1 C8 1.7381(10) . ?
 P1 O1 1.5888(7) . ?
 P1 O2 1.5841(7) . ?
 P1 O3 1.4654(7) . ?
 P1 N1 1.6274(8) . ?
 O1 C1 1.4081(11) . ?
 O2 C13 1.3937(11) . ?
 N1 C7 1.4174(12) . ?
 N1 H1 0.859(18) . ?
 C1 C2 1.3848(14) . ?
 C1 C6 1.3846(13) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.3923(14) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.3877(15) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.3883(15) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.3911(14) . ?
 C6 H6 0.9300 . ?
 C7 C8 1.3984(13) . ?
 C7 C12 1.3981(13) . ?
 C8 C9 1.3867(14) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.3881(15) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.3872(15) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.3890(13) . ?
 C12 H12 0.9300 . ?
 C13 C14 1.3882(14) . ?
 C13 C18 1.3858(14) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.3877(14) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.3896(17) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.3847(17) . ?
 C17 H17 0.9300 . ?
 C17 C18 1.3964(15) . ?
 C18 H18 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 N1 108.53(4) . . ?
 O2 P1 O1 94.11(4) . . ?
 O2 P1 N1 109.78(4) . . ?
 O3 P1 O1 115.94(4) . . ?
 O3 P1 O2 115.58(4) . . ?
 O3 P1 N1 111.58(4) . . ?
 C1 O1 P1 117.53(6) . . ?
 C13 O2 P1 126.36(6) . . ?
 P1 N1 H1 114.8(12) . . ?
 C7 N1 P1 126.67(7) . . ?
 C7 N1 H1 118.2(12) . . ?
 C2 C1 O1 119.18(9) . . ?
 C6 C1 O1 118.56(9) . . ?
 C6 C1 C2 122.25(9) . . ?
 C1 C2 H2 120.8 . . ?
 C1 C2 C3 118.39(9) . . ?
 C3 C2 H2 120.8 . . ?
 C2 C3 H3 119.8 . . ?
 C4 C3 C2 120.47(10) . . ?
 C4 C3 H3 119.8 . . ?
 C3 C4 H4 120.0 . . ?
 C3 C4 C5 119.97(10) . . ?
 C5 C4 H4 120.0 . . ?
 C4 C5 H5 119.8 . . ?
 C4 C5 C6 120.43(10) . . ?
 C6 C5 H5 119.8 . . ?
 C1 C6 C5 118.47(9) . . ?
 C1 C6 H6 120.8 . . ?
 C5 C6 H6 120.8 . . ?
 C8 C7 N1 120.37(8) . . ?
 C12 C7 N1 121.99(8) . . ?
 C12 C7 C8 117.63(9) . . ?
 C7 C8 Cl1 119.72(7) . . ?
 C9 C8 Cl1 118.45(8) . . ?
 C9 C8 C7 121.81(9) . . ?
 C8 C9 H9 120.2 . . ?
 C8 C9 C10 119.55(9) . . ?
 C10 C9 H9 120.2 . . ?
 C9 C10 H10 120.1 . . ?
 C11 C10 C9 119.73(9) . . ?
 C11 C10 H10 120.1 . . ?
 C10 C11 H11 119.8 . . ?
 C10 C11 C12 120.40(10) . . ?
 C12 C11 H11 119.8 . . ?
 C7 C12 H12 119.6 . . ?
 C11 C12 C7 120.88(9) . . ?
 C11 C12 H12 119.6 . . ?
 C14 C13 O2 114.77(9) . . ?
 C18 C13 O2 123.28(9) . . ?
 C18 C13 C14 121.93(9) . . ?
 C13 C14 H14 120.6 . . ?
 C15 C14 C13 118.86(10) . . ?
 C15 C14 H14 120.6 . . ?
 C14 C15 H15 119.8 . . ?
 C14 C15 C16 120.42(10) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 120.1 . . ?
 C17 C16 C15 119.74(10) . . ?
 C17 C16 H16 120.1 . . ?
 C16 C17 H17 119.6 . . ?
 C16 C17 C18 120.90(10) . . ?
 C18 C17 H17 119.6 . . ?
 C13 C18 C17 118.14(10) . . ?
 C13 C18 H18 120.9 . . ?
 C17 C18 H18 120.9 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Cl1 C8 C9 C10 -178.62(8) . . . . ?
 P1 O1 C1 C2 -86.91(10) . . . . ?
 P1 O1 C1 C6 94.74(9) . . . . ?
 P1 O2 C13 C14 158.04(7) . . . . ?
 P1 O2 C13 C18 -23.76(13) . . . . ?
 P1 N1 C7 C8 -136.77(8) . . . . ?
 P1 N1 C7 C12 43.88(13) . . . . ?
 O1 P1 O2 C13 -175.15(8) . . . . ?
 O1 P1 N1 C7 41.12(9) . . . . ?
 O1 C1 C2 C3 -179.64(9) . . . . ?
 O1 C1 C6 C5 179.69(9) . . . . ?
 O2 P1 O1 C1 -166.80(7) . . . . ?
 O2 P1 N1 C7 -60.46(9) . . . . ?
 O2 C13 C14 C15 177.81(9) . . . . ?
 O2 C13 C18 C17 -178.25(9) . . . . ?
 O3 P1 O1 C1 -45.72(8) . . . . ?
 O3 P1 O2 C13 63.48(9) . . . . ?
 O3 P1 N1 C7 170.08(8) . . . . ?
 N1 P1 O1 C1 80.75(7) . . . . ?
 N1 P1 O2 C13 -63.77(8) . . . . ?
 N1 C7 C8 Cl1 -0.70(13) . . . . ?
 N1 C7 C8 C9 -179.01(9) . . . . ?
 N1 C7 C12 C11 179.17(9) . . . . ?
 C1 C2 C3 C4 0.18(16) . . . . ?
 C2 C1 C6 C5 1.40(15) . . . . ?
 C2 C3 C4 C5 0.90(17) . . . . ?
 C3 C4 C5 C6 -0.85(17) . . . . ?
 C4 C5 C6 C1 -0.27(16) . . . . ?
 C6 C1 C2 C3 -1.35(15) . . . . ?
 C7 C8 C9 C10 -0.29(15) . . . . ?
 C8 C7 C12 C11 -0.20(14) . . . . ?
 C8 C9 C10 C11 0.02(15) . . . . ?
 C9 C10 C11 C12 0.15(16) . . . . ?
 C10 C11 C12 C7 -0.06(15) . . . . ?
 C12 C7 C8 Cl1 178.68(7) . . . . ?
 C12 C7 C8 C9 0.37(14) . . . . ?
 C13 C14 C15 C16 0.69(16) . . . . ?
 C14 C13 C18 C17 -0.17(15) . . . . ?
 C14 C15 C16 C17 -0.37(17) . . . . ?
 C15 C16 C17 C18 -0.24(17) . . . . ?
 C16 C17 C18 C13 0.50(16) . . . . ?
 C18 C13 C14 C15 -0.42(15) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_2I
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 I N O3 P'
_chemical_formula_sum              'C18 H15 I N O3 P'
_chemical_formula_weight           451.18
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.4777(6)
_cell_length_b                     9.2823(6)
_cell_length_c                     11.4187(8)
_cell_angle_alpha                  79.545(3)
_cell_angle_beta                   85.778(3)
_cell_angle_gamma                  75.120(3)
_cell_volume                       853.67(10)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9913
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.21
_cell_measurement_theta_min        2.49
_shelx_estimated_absorpt_T_max     0.902
_shelx_estimated_absorpt_T_min     0.514
_exptl_absorpt_coefficient_mu      1.985
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.5922
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/5
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.755
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               444
_exptl_crystal_size_max            0.387
_exptl_crystal_size_mid            0.183
_exptl_crystal_size_min            0.053
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0389
_diffrn_reflns_av_unetI/netI       0.0359
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         9
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              16798
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           29.130
_diffrn_reflns_theta_min           2.303
_diffrn_ambient_temperature        100
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4291
_reflns_number_total               4563
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.793
_refine_diff_density_min           -0.929
_refine_diff_density_rms           0.120
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           4563
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0259
_refine_ls_R_factor_gt             0.0238
_refine_ls_restrained_S_all        1.092
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0219P)²+0.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0567
_refine_ls_wR_factor_ref           0.0575
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 I1 I 0.35182(2) 0.30884(2) 0.24224(2) 0.01921(5) Uani 1 1 d . . . . .
 P1 P 0.75377(5) 0.33879(5) 0.48884(4) 0.01108(9) Uani 1 1 d . . . . .
 O1 O 0.89676(15) 0.31046(14) 0.39085(12) 0.0141(3) Uani 1 1 d . . . . .
 O2 O 0.85700(15) 0.22385(15) 0.59228(12) 0.0149(3) Uani 1 1 d . . . . .
 O3 O 0.69374(15) 0.49525(14) 0.50937(13) 0.0153(3) Uani 1 1 d . . . . .
 N1 N 0.60723(18) 0.27111(17) 0.45450(15) 0.0122(3) Uani 1 1 d . . . . .
 C1 C 0.8784(2) 0.4104(2) 0.28119(17) 0.0140(4) Uani 1 1 d . . . . .
 C2 C 0.9469(2) 0.5330(2) 0.26659(18) 0.0154(4) Uani 1 1 d . . . . .
 H2 H 1.004414 0.549615 0.329192 0.018 Uiso 1 1 calc R U . . .
 C3 C 0.9297(2) 0.6312(2) 0.15817(19) 0.0184(4) Uani 1 1 d . . . . .
 H3 H 0.976590 0.715494 0.146066 0.022 Uiso 1 1 calc R U . . .
 C4 C 0.8444(3) 0.6067(2) 0.0676(2) 0.0227(4) Uani 1 1 d . . . . .
 H4 H 0.831087 0.675444 -0.005603 0.027 Uiso 1 1 calc R U . . .
 C5 C 0.7783(3) 0.4817(2) 0.0839(2) 0.0234(4) Uani 1 1 d . . . . .
 H5 H 0.720959 0.464591 0.021439 0.028 Uiso 1 1 calc R U . . .
 C6 C 0.7960(2) 0.3817(2) 0.19152(19) 0.0193(4) Uani 1 1 d . . . . .
 H6 H 0.752315 0.295415 0.203073 0.023 Uiso 1 1 calc R U . . .
 C7 C 0.6234(2) 0.13165(19) 0.41372(17) 0.0116(3) Uani 1 1 d . . . . .
 C8 C 0.5284(2) 0.1214(2) 0.32217(17) 0.0130(3) Uani 1 1 d . . . . .
 C9 C 0.5410(2) -0.0148(2) 0.28378(18) 0.0151(4) Uani 1 1 d . . . . .
 H9 H 0.474369 -0.019371 0.221874 0.018 Uiso 1 1 calc R U . . .
 C10 C 0.6517(2) -0.1445(2) 0.33641(19) 0.0170(4) Uani 1 1 d . . . . .
 H10 H 0.660679 -0.238324 0.311022 0.020 Uiso 1 1 calc R U . . .
 C11 C 0.7486(2) -0.1362(2) 0.42589(19) 0.0167(4) Uani 1 1 d . . . . .
 H11 H 0.825437 -0.224485 0.461194 0.020 Uiso 1 1 calc R U . . .
 C12 C 0.7346(2) 0.0003(2) 0.46471(18) 0.0150(4) Uani 1 1 d . . . . .
 H12 H 0.801578 0.004226 0.526641 0.018 Uiso 1 1 calc R U . . .
 C13 C 0.8045(2) 0.1842(2) 0.70978(18) 0.0149(4) Uani 1 1 d . . . . .
 C14 C 0.8965(2) 0.0489(2) 0.77073(19) 0.0196(4) Uani 1 1 d . . . . .
 H14 H 0.984284 -0.012154 0.731510 0.023 Uiso 1 1 calc R U . . .
 C15 C 0.8580(3) 0.0043(2) 0.8898(2) 0.0260(5) Uani 1 1 d . . . . .
 H15 H 0.920416 -0.087711 0.932621 0.031 Uiso 1 1 calc R U . . .
 C16 C 0.7288(3) 0.0934(3) 0.9468(2) 0.0287(5) Uani 1 1 d . . . . .
 H16 H 0.703114 0.062877 1.028428 0.034 Uiso 1 1 calc R U . . .
 C17 C 0.6377(3) 0.2269(3) 0.8836(2) 0.0244(4) Uani 1 1 d . . . . .
 H17 H 0.548675 0.287288 0.922389 0.029 Uiso 1 1 calc R U . . .
 C18 C 0.6745(2) 0.2740(2) 0.76430(19) 0.0187(4) Uani 1 1 d . . . . .
 H18 H 0.611835 0.365648 0.721284 0.022 Uiso 1 1 calc R U . . .
 H1 H 0.520(3) 0.327(3) 0.456(2) 0.025(7) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 I1 C8 2.0944(18) . ?
 P1 O1 1.5919(13) . ?
 P1 O2 1.5858(14) . ?
 P1 O3 1.4661(13) . ?
 P1 N1 1.6290(16) . ?
 O1 C1 1.409(2) . ?
 O2 C13 1.397(2) . ?
 N1 C7 1.425(2) . ?
 N1 H1 0.79(3) . ?
 C1 C2 1.384(3) . ?
 C1 C6 1.381(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.391(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.386(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.391(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.391(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.396(3) . ?
 C7 C12 1.395(2) . ?
 C8 C9 1.389(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.390(3) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.382(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.392(3) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.389(3) . ?
 C13 C18 1.382(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.388(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.390(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.385(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.392(3) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 N1 107.97(8) . . ?
 O2 P1 O1 94.04(7) . . ?
 O2 P1 N1 109.75(8) . . ?
 O3 P1 O1 115.86(8) . . ?
 O3 P1 O2 115.90(8) . . ?
 O3 P1 N1 111.88(8) . . ?
 C1 O1 P1 117.64(11) . . ?
 C13 O2 P1 127.10(11) . . ?
 P1 N1 H1 114.4(19) . . ?
 C7 N1 P1 127.11(12) . . ?
 C7 N1 H1 118.2(19) . . ?
 C2 C1 O1 118.44(17) . . ?
 C6 C1 O1 119.27(16) . . ?
 C6 C1 C2 122.28(18) . . ?
 C1 C2 H2 120.8 . . ?
 C1 C2 C3 118.47(19) . . ?
 C3 C2 H2 120.8 . . ?
 C2 C3 H3 119.8 . . ?
 C4 C3 C2 120.38(18) . . ?
 C4 C3 H3 119.8 . . ?
 C3 C4 H4 120.0 . . ?
 C3 C4 C5 120.1(2) . . ?
 C5 C4 H4 120.0 . . ?
 C4 C5 H5 119.9 . . ?
 C6 C5 C4 120.1(2) . . ?
 C6 C5 H5 119.9 . . ?
 C1 C6 C5 118.62(18) . . ?
 C1 C6 H6 120.7 . . ?
 C5 C6 H6 120.7 . . ?
 C8 C7 N1 121.32(15) . . ?
 C12 C7 N1 120.85(17) . . ?
 C12 C7 C8 117.83(16) . . ?
 C7 C8 I1 121.47(13) . . ?
 C9 C8 I1 116.87(14) . . ?
 C9 C8 C7 121.60(16) . . ?
 C8 C9 H9 120.2 . . ?
 C8 C9 C10 119.63(18) . . ?
 C10 C9 H9 120.2 . . ?
 C9 C10 H10 120.2 . . ?
 C11 C10 C9 119.63(17) . . ?
 C11 C10 H10 120.2 . . ?
 C10 C11 H11 119.7 . . ?
 C10 C11 C12 120.53(17) . . ?
 C12 C11 H11 119.7 . . ?
 C7 C12 H12 119.6 . . ?
 C11 C12 C7 120.77(19) . . ?
 C11 C12 H12 119.6 . . ?
 C14 C13 O2 115.02(17) . . ?
 C18 C13 O2 123.32(17) . . ?
 C18 C13 C14 121.63(19) . . ?
 C13 C14 H14 120.5 . . ?
 C15 C14 C13 118.98(19) . . ?
 C15 C14 H14 120.5 . . ?
 C14 C15 H15 119.8 . . ?
 C14 C15 C16 120.4(2) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 120.2 . . ?
 C17 C16 C15 119.5(2) . . ?
 C17 C16 H16 120.2 . . ?
 C16 C17 H17 119.5 . . ?
 C16 C17 C18 121.0(2) . . ?
 C18 C17 H17 119.5 . . ?
 C13 C18 C17 118.49(19) . . ?
 C13 C18 H18 120.8 . . ?
 C17 C18 H18 120.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 I1 C8 C9 C10 -177.66(13) . . . . ?
 P1 O1 C1 C2 94.47(17) . . . . ?
 P1 O1 C1 C6 -86.74(19) . . . . ?
 P1 O2 C13 C14 159.92(14) . . . . ?
 P1 O2 C13 C18 -22.2(3) . . . . ?
 P1 N1 C7 C8 -138.56(16) . . . . ?
 P1 N1 C7 C12 41.8(2) . . . . ?
 O1 P1 O2 C13 -177.49(15) . . . . ?
 O1 P1 N1 C7 42.43(18) . . . . ?
 O1 C1 C2 C3 179.65(16) . . . . ?
 O1 C1 C6 C5 179.73(17) . . . . ?
 O2 P1 O1 C1 -168.29(13) . . . . ?
 O2 P1 N1 C7 -58.82(18) . . . . ?
 O2 C13 C14 C15 176.87(17) . . . . ?
 O2 C13 C18 C17 -176.92(17) . . . . ?
 O3 P1 O1 C1 -46.90(16) . . . . ?
 O3 P1 O2 C13 61.16(16) . . . . ?
 O3 P1 N1 C7 171.07(15) . . . . ?
 N1 P1 O1 C1 79.44(14) . . . . ?
 N1 P1 O2 C13 -66.76(16) . . . . ?
 N1 C7 C8 I1 -1.7(2) . . . . ?
 N1 C7 C8 C9 -178.58(17) . . . . ?
 N1 C7 C12 C11 179.10(17) . . . . ?
 C1 C2 C3 C4 0.6(3) . . . . ?
 C2 C1 C6 C5 -1.5(3) . . . . ?
 C2 C3 C4 C5 -1.3(3) . . . . ?
 C3 C4 C5 C6 0.7(3) . . . . ?
 C4 C5 C6 C1 0.7(3) . . . . ?
 C6 C1 C2 C3 0.9(3) . . . . ?
 C7 C8 C9 C10 -0.6(3) . . . . ?
 C8 C7 C12 C11 -0.6(3) . . . . ?
 C8 C9 C10 C11 -0.4(3) . . . . ?
 C9 C10 C11 C12 0.9(3) . . . . ?
 C10 C11 C12 C7 -0.4(3) . . . . ?
 C12 C7 C8 I1 178.00(13) . . . . ?
 C12 C7 C8 C9 1.1(3) . . . . ?
 C13 C14 C15 C16 0.4(3) . . . . ?
 C14 C13 C18 C17 0.8(3) . . . . ?
 C14 C15 C16 C17 0.4(3) . . . . ?
 C15 C16 C17 C18 -0.6(3) . . . . ?
 C16 C17 C18 C13 0.0(3) . . . . ?
 C18 C13 C14 C15 -1.0(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_3Br
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 Br N O3 P'
_chemical_formula_sum              'C18 H15 Br N O3 P'
_chemical_formula_weight           404.19
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     10.06390(10)
_cell_length_b                     10.23060(10)
_cell_length_c                     10.5227(2)
_cell_angle_alpha                  107.9070(10)
_cell_angle_beta                   95.1590(10)
_cell_angle_gamma                  118.0100(10)
_cell_volume                       874.05(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4357
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.12
_cell_measurement_theta_min        2.39
_shelx_estimated_absorpt_T_max     0.667
_shelx_estimated_absorpt_T_min     0.410
_exptl_absorpt_coefficient_mu      2.458
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6834
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/2
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.536
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               408
_exptl_crystal_size_max            0.442
_exptl_crystal_size_mid            0.282
_exptl_crystal_size_min            0.179
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0274
_diffrn_reflns_av_unetI/netI       0.0348
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -14
_diffrn_reflns_number              11517
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.698
_diffrn_reflns_theta_min           2.118
_diffrn_ambient_temperature        100
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3938
_reflns_number_total               4499
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.476
_refine_diff_density_min           -0.375
_refine_diff_density_rms           0.073
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           4499
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0356
_refine_ls_R_factor_gt             0.0287
_refine_ls_restrained_S_all        1.040
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0246P)²+0.5692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0624
_refine_ls_wR_factor_ref           0.0656
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C2(H2), C3(H3), C4(H4), C16(H16), C15(H15),
 C14(H14), C8(H8), C5(H5), C6(H6), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br 0.36775(2) 0.27440(2) 0.29064(2) 0.01957(6) Uani 1 1 d . . . . .
 P1 P 1.03184(5) 0.91186(5) 0.29050(5) 0.01065(10) Uani 1 1 d . . . . .
 O1 O 0.96490(15) 0.95082(15) 0.17457(13) 0.0142(3) Uani 1 1 d . . . . .
 O2 O 1.10196(15) 0.82278(15) 0.19575(13) 0.0127(3) Uani 1 1 d . . . . .
 O3 O 1.14302(14) 1.05231(15) 0.41817(13) 0.0135(3) Uani 1 1 d . . . . .
 N1 N 0.88782(18) 0.78002(18) 0.32705(17) 0.0131(3) Uani 1 1 d . . . . .
 C10 C 0.4950(2) 0.3241(2) 0.0669(2) 0.0183(4) Uani 1 1 d . . . . .
 H10 H 0.406621 0.220285 0.010049 0.022 Uiso 1 1 calc R U . . .
 C11 C 0.6075(2) 0.4113(2) 0.0110(2) 0.0187(4) Uani 1 1 d . . . . .
 H11 H 0.595484 0.366315 -0.085913 0.022 Uiso 1 1 calc R U . . .
 C12 C 0.7377(2) 0.5629(2) 0.09304(19) 0.0159(4) Uani 1 1 d . . . . .
 H12 H 0.813158 0.620985 0.052526 0.019 Uiso 1 1 calc R U . . .
 C7 C 0.7563(2) 0.6288(2) 0.23543(18) 0.0122(3) Uani 1 1 d . . . . .
 C1 C 0.8939(2) 1.0428(2) 0.19806(19) 0.0129(3) Uani 1 1 d . . . . .
 C2 C 0.8494(2) 1.0836(2) 0.3176(2) 0.0189(4) Uani 1 1 d . . . . .
 H2 H 0.867119 1.051270 0.389720 0.023 Uiso 1 1 calc R U . . .
 C3 C 0.7779(3) 1.1733(3) 0.3298(2) 0.0233(4) Uani 1 1 d . . . . .
 H3 H 0.747575 1.203601 0.411581 0.028 Uiso 1 1 calc R U . . .
 C4 C 0.7507(3) 1.2185(3) 0.2241(2) 0.0238(4) Uani 1 1 d . . . . .
 H4 H 0.701784 1.279591 0.233222 0.029 Uiso 1 1 calc R U . . .
 C16 C 1.3482(2) 0.6506(2) 0.3576(2) 0.0204(4) Uani 1 1 d . . . . .
 H16 H 1.404411 0.611560 0.394890 0.025 Uiso 1 1 calc R U . . .
 C15 C 1.4272(2) 0.8065(2) 0.3628(2) 0.0205(4) Uani 1 1 d . . . . .
 H15 H 1.537464 0.873156 0.402678 0.025 Uiso 1 1 calc R U . . .
 C14 C 1.3458(2) 0.8658(2) 0.31012(19) 0.0174(4) Uani 1 1 d . . . . .
 H14 H 1.399098 0.972344 0.313203 0.021 Uiso 1 1 calc R U . . .
 C13 C 1.1850(2) 0.7652(2) 0.25305(18) 0.0133(3) Uani 1 1 d . . . . .
 C9 C 0.5155(2) 0.3933(2) 0.2088(2) 0.0145(4) Uani 1 1 d . . . . .
 C8 C 0.6439(2) 0.5436(2) 0.29398(19) 0.0140(4) Uani 1 1 d . . . . .
 H8 H 0.655350 0.588016 0.390787 0.017 Uiso 1 1 calc R U . . .
 C5 C 0.7950(2) 1.1746(3) 0.1049(2) 0.0217(4) Uani 1 1 d . . . . .
 H5 H 0.775382 1.204786 0.031834 0.026 Uiso 1 1 calc R U . . .
 C6 C 0.8678(2) 1.0867(2) 0.09145(19) 0.0164(4) Uani 1 1 d . . . . .
 H6 H 0.899068 1.057211 0.010055 0.020 Uiso 1 1 calc R U . . .
 C18 C 1.1047(2) 0.6093(2) 0.2453(2) 0.0203(4) Uani 1 1 d . . . . .
 H18 H 0.994513 0.542270 0.204706 0.024 Uiso 1 1 calc R U . . .
 C17 C 1.1881(3) 0.5521(3) 0.2982(2) 0.0233(4) Uani 1 1 d . . . . .
 H17 H 1.134801 0.444865 0.293433 0.028 Uiso 1 1 calc R U . . .
 H1 H 0.881(3) 0.816(3) 0.403(3) 0.023(6) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C9 1.8994(18) . ?
 P1 O1 1.5825(13) . ?
 P1 O2 1.5793(13) . ?
 P1 O3 1.4676(13) . ?
 P1 N1 1.6282(16) . ?
 O1 C1 1.406(2) . ?
 O2 C13 1.414(2) . ?
 N1 C7 1.416(2) . ?
 N1 H1 0.80(2) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.385(3) . ?
 C10 C9 1.390(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.390(3) . ?
 C12 H12 0.9500 . ?
 C12 C7 1.394(3) . ?
 C7 C8 1.396(2) . ?
 C1 C2 1.383(3) . ?
 C1 C6 1.377(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.393(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.380(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.384(3) . ?
 C16 H16 0.9500 . ?
 C16 C15 1.387(3) . ?
 C16 C17 1.382(3) . ?
 C15 H15 0.9500 . ?
 C15 C14 1.393(3) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.385(3) . ?
 C13 C18 1.379(3) . ?
 C9 C8 1.384(2) . ?
 C8 H8 0.9500 . ?
 C5 H5 0.9500 . ?
 C5 C6 1.387(3) . ?
 C6 H6 0.9500 . ?
 C18 H18 0.9500 . ?
 C18 C17 1.391(3) . ?
 C17 H17 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 N1 109.84(8) . . ?
 O2 P1 O1 95.64(7) . . ?
 O2 P1 N1 108.37(8) . . ?
 O3 P1 O1 115.40(7) . . ?
 O3 P1 O2 116.24(7) . . ?
 O3 P1 N1 110.39(8) . . ?
 C1 O1 P1 124.04(11) . . ?
 C13 O2 P1 119.61(11) . . ?
 P1 N1 H1 113.6(18) . . ?
 C7 N1 P1 128.84(13) . . ?
 C7 N1 H1 115.8(18) . . ?
 C11 C10 H10 121.1 . . ?
 C11 C10 C9 117.83(17) . . ?
 C9 C10 H10 121.1 . . ?
 C10 C11 H11 119.2 . . ?
 C10 C11 C12 121.66(18) . . ?
 C12 C11 H11 119.2 . . ?
 C11 C12 H12 120.3 . . ?
 C11 C12 C7 119.35(18) . . ?
 C7 C12 H12 120.3 . . ?
 C12 C7 N1 122.95(16) . . ?
 C12 C7 C8 120.01(17) . . ?
 C8 C7 N1 117.03(16) . . ?
 C2 C1 O1 122.93(17) . . ?
 C6 C1 O1 115.18(16) . . ?
 C6 C1 C2 121.87(17) . . ?
 C1 C2 H2 120.8 . . ?
 C1 C2 C3 118.39(18) . . ?
 C3 C2 H2 120.8 . . ?
 C2 C3 H3 119.7 . . ?
 C4 C3 C2 120.66(19) . . ?
 C4 C3 H3 119.7 . . ?
 C3 C4 H4 120.1 . . ?
 C3 C4 C5 119.74(19) . . ?
 C5 C4 H4 120.1 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 H16 119.9 . . ?
 C17 C16 C15 120.16(19) . . ?
 C16 C15 H15 119.8 . . ?
 C16 C15 C14 120.44(19) . . ?
 C14 C15 H15 119.8 . . ?
 C15 C14 H14 120.9 . . ?
 C13 C14 C15 118.16(18) . . ?
 C13 C14 H14 120.9 . . ?
 C14 C13 O2 118.59(16) . . ?
 C18 C13 O2 119.09(16) . . ?
 C18 C13 C14 122.27(18) . . ?
 C10 C9 Br1 119.11(14) . . ?
 C8 C9 Br1 118.64(14) . . ?
 C8 C9 C10 122.18(17) . . ?
 C7 C8 H8 120.5 . . ?
 C9 C8 C7 118.97(17) . . ?
 C9 C8 H8 120.5 . . ?
 C4 C5 H5 119.8 . . ?
 C4 C5 C6 120.46(19) . . ?
 C6 C5 H5 119.8 . . ?
 C1 C6 C5 118.87(18) . . ?
 C1 C6 H6 120.6 . . ?
 C5 C6 H6 120.6 . . ?
 C13 C18 H18 120.7 . . ?
 C13 C18 C17 118.69(18) . . ?
 C17 C18 H18 120.7 . . ?
 C16 C17 C18 120.26(19) . . ?
 C16 C17 H17 119.9 . . ?
 C18 C17 H17 119.9 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C9 C8 C7 177.35(13) . . . . ?
 P1 O1 C1 C2 -12.3(2) . . . . ?
 P1 O1 C1 C6 169.28(13) . . . . ?
 P1 O2 C13 C14 -91.04(18) . . . . ?
 P1 O2 C13 C18 91.54(18) . . . . ?
 P1 N1 C7 C12 5.4(3) . . . . ?
 P1 N1 C7 C8 -175.83(14) . . . . ?
 O1 P1 O2 C13 177.60(13) . . . . ?
 O1 P1 N1 C7 51.57(18) . . . . ?
 O1 C1 C2 C3 -179.11(18) . . . . ?
 O1 C1 C6 C5 178.59(17) . . . . ?
 O2 P1 O1 C1 -175.51(13) . . . . ?
 O2 P1 N1 C7 -51.72(18) . . . . ?
 O2 C13 C18 C17 178.07(17) . . . . ?
 O3 P1 O1 C1 -52.92(16) . . . . ?
 O3 P1 O2 C13 55.65(15) . . . . ?
 O3 P1 N1 C7 179.93(15) . . . . ?
 N1 P1 O1 C1 72.64(15) . . . . ?
 N1 P1 O2 C13 -69.31(14) . . . . ?
 N1 C7 C8 C9 -178.35(16) . . . . ?
 C10 C11 C12 C7 0.4(3) . . . . ?
 C10 C9 C8 C7 0.3(3) . . . . ?
 C11 C10 C9 Br1 -177.72(14) . . . . ?
 C11 C10 C9 C8 -0.7(3) . . . . ?
 C11 C12 C7 N1 177.93(17) . . . . ?
 C11 C12 C7 C8 -0.8(3) . . . . ?
 C12 C7 C8 C9 0.5(3) . . . . ?
 C1 C2 C3 C4 0.7(3) . . . . ?
 C2 C1 C6 C5 0.1(3) . . . . ?
 C2 C3 C4 C5 -0.1(3) . . . . ?
 C3 C4 C5 C6 -0.6(3) . . . . ?
 C4 C5 C6 C1 0.6(3) . . . . ?
 C16 C15 C14 C13 0.1(3) . . . . ?
 C15 C16 C17 C18 -1.0(3) . . . . ?
 C15 C14 C13 O2 -178.26(16) . . . . ?
 C15 C14 C13 C18 -0.9(3) . . . . ?
 C14 C13 C18 C17 0.7(3) . . . . ?
 C13 C18 C17 C16 0.3(3) . . . . ?
 C9 C10 C11 C12 0.3(3) . . . . ?
 C6 C1 C2 C3 -0.8(3) . . . . ?
 C17 C16 C15 C14 0.8(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_3Cl
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 Cl N O3 P'
_chemical_formula_sum              'C18 H15 Cl N O3 P'
_chemical_formula_weight           359.73
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     9.6702(9)
_cell_length_b                     18.1551(17)
_cell_length_c                     10.1914(10)
_cell_angle_alpha                  90
_cell_angle_beta                   110.184(6)
_cell_angle_gamma                  90
_cell_volume                       1679.4(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      4845
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        27.10
_cell_measurement_theta_min        2.24
_shelx_estimated_absorpt_T_max     0.984
_shelx_estimated_absorpt_T_min     0.896
_exptl_absorpt_coefficient_mu      0.339
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.5978
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0886 after correction.
The Ratio of minimum to maximum transmission is 0.8013.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.423
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               744
_exptl_crystal_size_max            0.332
_exptl_crystal_size_mid            0.091
_exptl_crystal_size_min            0.047
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1100
_diffrn_reflns_av_unetI/netI       0.0588
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         22
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              26387
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           25.680
_diffrn_reflns_theta_min           2.244
_diffrn_ambient_temperature        100.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2472
_reflns_number_total               3184
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SIR2014 (Burla et al., 2014)'
_refine_diff_density_max           0.580
_refine_diff_density_min           -0.665
_refine_diff_density_rms           0.098
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           3184
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0748
_refine_ls_R_factor_gt             0.0588
_refine_ls_restrained_S_all        1.045
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1006P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1491
_refine_ls_wR_factor_ref           0.1593
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.53018(8) 0.02521(4) 0.29604(7) 0.0177(2) Uani 1 1 d . . . . .
 Cl1 Cl 0.13092(8) -0.08945(4) -0.21446(7) 0.0274(2) Uani 1 1 d . . . . .
 O1 O 0.4978(2) 0.07968(10) 0.16861(19) 0.0204(5) Uani 1 1 d . . . . .
 O2 O 0.6062(2) -0.03555(10) 0.23255(19) 0.0200(5) Uani 1 1 d . . . . .
 O3 O 0.6212(2) 0.05258(11) 0.43456(19) 0.0209(5) Uani 1 1 d . . . . .
 N1 N 0.3733(3) -0.00560(14) 0.2982(3) 0.0209(6) Uani 1 1 d . . . . .
 C1 C 0.4111(3) 0.14432(15) 0.1482(3) 0.0186(6) Uani 1 1 d . . . . .
 C2 C 0.3578(3) 0.16844(16) 0.0122(3) 0.0226(7) Uani 1 1 d . . . . .
 H2 H 0.377711 0.141924 -0.059650 0.027 Uiso 1 1 calc R U . . .
 C3 C 0.2738(3) 0.23258(16) -0.0181(3) 0.0254(7) Uani 1 1 d . . . . .
 H3 H 0.235168 0.249806 -0.111799 0.031 Uiso 1 1 calc R U . . .
 C4 C 0.2464(3) 0.27116(17) 0.0861(3) 0.0266(7) Uani 1 1 d . . . . .
 H4 H 0.189772 0.315144 0.065048 0.032 Uiso 1 1 calc R U . . .
 C5 C 0.3023(3) 0.24529(16) 0.2230(3) 0.0274(7) Uani 1 1 d . . . . .
 H5 H 0.283138 0.271831 0.295240 0.033 Uiso 1 1 calc R U . . .
 C6 C 0.3855(3) 0.18135(16) 0.2553(3) 0.0230(7) Uani 1 1 d . . . . .
 H6 H 0.423637 0.163628 0.348680 0.028 Uiso 1 1 calc R U . . .
 C7 C 0.2542(3) -0.03780(15) 0.1902(3) 0.0190(6) Uani 1 1 d . . . . .
 C8 C 0.2565(3) -0.04772(15) 0.0554(3) 0.0210(7) Uani 1 1 d . . . . .
 H8 H 0.339937 -0.033955 0.032055 0.025 Uiso 1 1 calc R U . . .
 C9 C 0.1326(3) -0.07840(16) -0.0440(3) 0.0213(7) Uani 1 1 d . . . . .
 C10 C 0.0107(3) -0.10032(15) -0.0133(3) 0.0226(7) Uani 1 1 d . . . . .
 H10 H -0.072307 -0.121305 -0.083234 0.027 Uiso 1 1 calc R U . . .
 C11 C 0.0125(3) -0.09092(16) 0.1223(3) 0.0232(7) Uani 1 1 d . . . . .
 H11 H -0.070064 -0.105987 0.145779 0.028 Uiso 1 1 calc R U . . .
 C12 C 0.1327(3) -0.06000(16) 0.2234(3) 0.0221(7) Uani 1 1 d . . . . .
 H12 H 0.132418 -0.053854 0.315914 0.027 Uiso 1 1 calc R U . . .
 C13 C 0.6717(3) -0.09740(15) 0.3160(3) 0.0207(7) Uani 1 1 d . . . . .
 C14 C 0.5821(4) -0.15642(16) 0.3199(3) 0.0263(7) Uani 1 1 d . . . . .
 H14 H 0.478259 -0.153883 0.274792 0.032 Uiso 1 1 calc R U . . .
 C15 C 0.6485(4) -0.21927(19) 0.3917(4) 0.0369(9) Uani 1 1 d . . . . .
 H15 H 0.589869 -0.260386 0.396885 0.044 Uiso 1 1 calc R U . . .
 C16 C 0.7991(4) -0.2222(2) 0.4554(4) 0.0411(9) Uani 1 1 d . . . . .
 H16 H 0.843862 -0.265913 0.502261 0.049 Uiso 1 1 calc R U . . .
 C17 C 0.8857(4) -0.1625(2) 0.4519(3) 0.0377(9) Uani 1 1 d . . . . .
 H17 H 0.989463 -0.164785 0.497321 0.045 Uiso 1 1 calc R U . . .
 C18 C 0.8205(3) -0.09859(18) 0.3814(3) 0.0273(7) Uani 1 1 d . . . . .
 H18 H 0.878681 -0.056789 0.379111 0.033 Uiso 1 1 calc R U . . .
 H1 H 0.369(3) -0.0107(18) 0.368(3) 0.016(9) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O1 1.575(2) . ?
 P1 O2 1.582(2) . ?
 P1 O3 1.469(2) . ?
 P1 N1 1.624(3) . ?
 Cl1 C9 1.744(3) . ?
 O1 C1 1.415(3) . ?
 O2 C13 1.419(3) . ?
 N1 C7 1.416(4) . ?
 N1 H1 0.73(3) . ?
 C1 C2 1.374(4) . ?
 C1 C6 1.375(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.392(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.373(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.392(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.386(4) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.394(4) . ?
 C7 C12 1.390(4) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.390(4) . ?
 C9 C10 1.378(4) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.386(4) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.379(4) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.388(4) . ?
 C13 C18 1.361(4) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.388(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.375(5) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.378(5) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.395(5) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O2 95.09(10) . . ?
 O1 P1 N1 107.85(12) . . ?
 O2 P1 N1 109.47(12) . . ?
 O3 P1 O1 117.56(11) . . ?
 O3 P1 O2 114.84(11) . . ?
 O3 P1 N1 110.86(13) . . ?
 C1 O1 P1 125.49(18) . . ?
 C13 O2 P1 118.75(17) . . ?
 P1 N1 H1 115(2) . . ?
 C7 N1 P1 130.1(2) . . ?
 C7 N1 H1 114(3) . . ?
 C2 C1 O1 114.2(2) . . ?
 C2 C1 C6 122.5(3) . . ?
 C6 C1 O1 123.3(2) . . ?
 C1 C2 H2 120.7 . . ?
 C1 C2 C3 118.6(3) . . ?
 C3 C2 H2 120.7 . . ?
 C2 C3 H3 119.7 . . ?
 C4 C3 C2 120.6(3) . . ?
 C4 C3 H3 119.7 . . ?
 C3 C4 H4 120.3 . . ?
 C3 C4 C5 119.4(3) . . ?
 C5 C4 H4 120.3 . . ?
 C4 C5 H5 119.5 . . ?
 C6 C5 C4 120.9(3) . . ?
 C6 C5 H5 119.5 . . ?
 C1 C6 C5 118.0(3) . . ?
 C1 C6 H6 121.0 . . ?
 C5 C6 H6 121.0 . . ?
 C8 C7 N1 122.3(3) . . ?
 C12 C7 N1 117.4(3) . . ?
 C12 C7 C8 120.3(3) . . ?
 C7 C8 H8 121.1 . . ?
 C9 C8 C7 117.8(3) . . ?
 C9 C8 H8 121.1 . . ?
 C8 C9 Cl1 118.7(2) . . ?
 C10 C9 Cl1 118.6(2) . . ?
 C10 C9 C8 122.7(3) . . ?
 C9 C10 H10 120.9 . . ?
 C9 C10 C11 118.2(3) . . ?
 C11 C10 H10 120.9 . . ?
 C10 C11 H11 119.6 . . ?
 C12 C11 C10 120.9(3) . . ?
 C12 C11 H11 119.6 . . ?
 C7 C12 H12 120.0 . . ?
 C11 C12 C7 120.1(3) . . ?
 C11 C12 H12 120.0 . . ?
 C14 C13 O2 118.3(3) . . ?
 C18 C13 O2 119.0(3) . . ?
 C18 C13 C14 122.6(3) . . ?
 C13 C14 H14 121.0 . . ?
 C13 C14 C15 118.0(3) . . ?
 C15 C14 H14 121.0 . . ?
 C14 C15 H15 119.9 . . ?
 C16 C15 C14 120.2(3) . . ?
 C16 C15 H15 119.9 . . ?
 C15 C16 H16 119.6 . . ?
 C15 C16 C17 120.7(3) . . ?
 C17 C16 H16 119.6 . . ?
 C16 C17 H17 120.1 . . ?
 C16 C17 C18 119.8(3) . . ?
 C18 C17 H17 120.1 . . ?
 C13 C18 C17 118.6(3) . . ?
 C13 C18 H18 120.7 . . ?
 C17 C18 H18 120.7 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 P1 O1 C1 C2 -158.9(2) . . . . ?
 P1 O1 C1 C6 22.9(4) . . . . ?
 P1 O2 C13 C14 83.7(3) . . . . ?
 P1 O2 C13 C18 -100.5(3) . . . . ?
 P1 N1 C7 C8 -0.4(4) . . . . ?
 P1 N1 C7 C12 179.3(2) . . . . ?
 Cl1 C9 C10 C11 -179.6(2) . . . . ?
 O1 P1 O2 C13 174.1(2) . . . . ?
 O1 P1 N1 C7 51.2(3) . . . . ?
 O1 C1 C2 C3 -178.6(2) . . . . ?
 O1 C1 C6 C5 178.1(3) . . . . ?
 O2 P1 O1 C1 171.3(2) . . . . ?
 O2 P1 N1 C7 -51.1(3) . . . . ?
 O2 C13 C14 C15 174.5(3) . . . . ?
 O2 C13 C18 C17 -173.8(3) . . . . ?
 O3 P1 O1 C1 -67.2(2) . . . . ?
 O3 P1 O2 C13 50.5(2) . . . . ?
 O3 P1 N1 C7 -178.8(2) . . . . ?
 N1 P1 O1 C1 59.0(2) . . . . ?
 N1 P1 O2 C13 -74.9(2) . . . . ?
 N1 C7 C8 C9 -178.6(3) . . . . ?
 N1 C7 C12 C11 179.2(3) . . . . ?
 C1 C2 C3 C4 0.6(4) . . . . ?
 C2 C1 C6 C5 0.1(4) . . . . ?
 C2 C3 C4 C5 -0.6(5) . . . . ?
 C3 C4 C5 C6 0.2(5) . . . . ?
 C4 C5 C6 C1 0.0(4) . . . . ?
 C6 C1 C2 C3 -0.4(4) . . . . ?
 C7 C8 C9 Cl1 178.6(2) . . . . ?
 C7 C8 C9 C10 -1.3(4) . . . . ?
 C8 C7 C12 C11 -1.0(4) . . . . ?
 C8 C9 C10 C11 0.2(4) . . . . ?
 C9 C10 C11 C12 0.4(4) . . . . ?
 C10 C11 C12 C7 0.0(4) . . . . ?
 C12 C7 C8 C9 1.7(4) . . . . ?
 C13 C14 C15 C16 -0.6(5) . . . . ?
 C14 C13 C18 C17 1.8(5) . . . . ?
 C14 C15 C16 C17 1.6(5) . . . . ?
 C15 C16 C17 C18 -0.9(5) . . . . ?
 C16 C17 C18 C13 -0.8(5) . . . . ?
 C18 C13 C14 C15 -1.2(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_3F
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 F N O3 P' 
_chemical_formula_weight          343.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            29
_space_group_name_H-M_alt         'P c a 21'
_space_group_name_Hall            'P 2c -2ac'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y, z+1/2'
 'x+1/2, -y, z'
 
_cell_length_a                    35.0174(17)
_cell_length_b                    7.3265(3)
_cell_length_c                    12.9270(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3316.5(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     2073
_cell_measurement_theta_min       2.81
_cell_measurement_theta_max       26.10
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.375          
_exptl_crystal_F_000              1424
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.402
_exptl_crystal_size_mid           0.060
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     0.192
_shelx_estimated_absorpt_T_min    0.927
_shelx_estimated_absorpt_T_max    0.989
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.5271
_exptl_absorpt_correction_T_max   0.7460
_exptl_absorpt_process_details    'SADABS-2014/5'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             24220
_diffrn_reflns_av_unetI/netI      0.1171
_diffrn_reflns_av_R_equivalents   0.0950
_diffrn_reflns_limit_h_min        -39
_diffrn_reflns_limit_h_max        48
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          1.958
_diffrn_reflns_theta_max          29.572
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.972
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              9033
_reflns_number_gt                 5559
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.870
_reflns_Friedel_fraction_max      0.944
_reflns_Friedel_fraction_full     0.976
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'olex2.solve 1.3 (Bourhis et al., 2015)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material   'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.30(13)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          9033
_refine_ls_number_parameters      439
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1147
_refine_ls_R_factor_gt            0.0638
_refine_ls_wR_factor_ref          0.1569
_refine_ls_wR_factor_gt           0.1316
_refine_ls_goodness_of_fit_ref    0.972
_refine_ls_restrained_S_all       0.972
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
P1 P 0.11573(4) 0.00988(18) 0.41401(10) 0.0232(3) Uani 1 1 d . . . . .
F1 F 0.09800(12) 0.7220(4) 0.6810(3) 0.0498(10) Uani 1 1 d . . . . .
O1 O 0.07556(9) -0.0766(5) 0.4371(3) 0.0259(8) Uani 1 1 d . . . . .
O2 O 0.13839(9) -0.1168(5) 0.4908(3) 0.0247(8) Uani 1 1 d . . . . .
O3 O 0.12842(11) 0.0069(5) 0.3065(3) 0.0301(9) Uani 1 1 d . . . . .
N1 N 0.11651(12) 0.2178(6) 0.4581(3) 0.0242(9) Uani 1 1 d . . . . .
H1N H 0.1213(16) 0.291(8) 0.412(4) 0.029 Uiso 1 1 d . U . . .
C1 C 0.04068(13) 0.0019(7) 0.4073(4) 0.0261(10) Uani 1 1 d . . . . .
C2 C 0.01012(16) -0.0328(8) 0.4712(5) 0.0349(14) Uani 1 1 d . . . . .
H2 H 0.013498 -0.102553 0.532467 0.042 Uiso 1 1 calc R U . . .
C3 C -0.02545(17) 0.0342(8) 0.4458(5) 0.0419(15) Uani 1 1 d . . . . .
H3 H -0.046670 0.011252 0.489741 0.050 Uiso 1 1 calc R U . . .
C4 C -0.03016(19) 0.1348(8) 0.3564(6) 0.0457(17) Uani 1 1 d . . . . .
H4 H -0.054748 0.179506 0.338460 0.055 Uiso 1 1 calc R U . . .
C5 C 0.00073(17) 0.1708(8) 0.2928(5) 0.0412(15) Uani 1 1 d . . . . .
H5 H -0.002433 0.242288 0.232093 0.049 Uiso 1 1 calc R U . . .
C6 C 0.03647(17) 0.1013(8) 0.3187(5) 0.0366(13) Uani 1 1 d . . . . .
H6 H 0.057802 0.122893 0.274986 0.044 Uiso 1 1 calc R U . . .
C7 C 0.10668(14) 0.2857(7) 0.5565(4) 0.0223(11) Uani 1 1 d . . . . .
C8 C 0.10770(15) 0.4719(7) 0.5722(4) 0.0265(12) Uani 1 1 d . . . . .
H8 H 0.114972 0.552094 0.517872 0.032 Uiso 1 1 calc R U . . .
C9 C 0.09801(17) 0.5387(7) 0.6675(4) 0.0297(12) Uani 1 1 d . . . . .
C10 C 0.08739(16) 0.4319(8) 0.7500(4) 0.0314(12) Uani 1 1 d . . . . .
H10 H 0.081093 0.483419 0.815274 0.038 Uiso 1 1 calc R U . . .
C11 C 0.08635(15) 0.2449(7) 0.7330(4) 0.0267(11) Uani 1 1 d . . . . .
H11 H 0.079052 0.165999 0.787853 0.032 Uiso 1 1 calc R U . . .
C12 C 0.09577(14) 0.1705(7) 0.6373(4) 0.0243(11) Uani 1 1 d . . . . .
H12 H 0.094784 0.042215 0.626948 0.029 Uiso 1 1 calc R U . . .
C13 C 0.17875(14) -0.1050(7) 0.4949(4) 0.0261(11) Uani 1 1 d . . . . .
C14 C 0.19525(16) 0.0016(8) 0.5691(5) 0.0347(13) Uani 1 1 d . . . . .
H14 H 0.180022 0.071374 0.615266 0.042 Uiso 1 1 calc R U . . .
C15 C 0.23472(17) 0.0055(8) 0.5753(5) 0.0397(15) Uani 1 1 d . . . . .
H15 H 0.246710 0.077566 0.627082 0.048 Uiso 1 1 calc R U . . .
C16 C 0.25680(16) -0.0937(8) 0.5076(5) 0.0372(14) Uani 1 1 d . . . . .
H16 H 0.283861 -0.087392 0.511340 0.045 Uiso 1 1 calc R U . . .
C17 C 0.23945(16) -0.2023(8) 0.4341(5) 0.0376(13) Uani 1 1 d . . . . .
H17 H 0.254633 -0.272117 0.387757 0.045 Uiso 1 1 calc R U . . .
C18 C 0.19988(14) -0.2099(7) 0.4275(4) 0.0319(12) Uani 1 1 d . . . . .
H18 H 0.187702 -0.285575 0.377785 0.038 Uiso 1 1 calc R U . . .
P2 P 0.13896(4) 0.50428(18) 0.20986(11) 0.0238(3) Uani 1 1 d . . . . .
F2 F 0.13832(10) 1.2208(4) -0.0593(3) 0.0399(8) Uani 1 1 d . . . . .
O4 O 0.17216(10) 0.3845(5) 0.1640(3) 0.0267(8) Uani 1 1 d . . . . .
O5 O 0.10643(10) 0.4034(5) 0.1482(3) 0.0284(8) Uani 1 1 d . . . . .
O6 O 0.13545(10) 0.5028(5) 0.3226(3) 0.0269(8) Uani 1 1 d . . . . .
N2 N 0.14256(12) 0.7135(6) 0.1696(3) 0.0249(10) Uani 1 1 d . . . . .
H2N H 0.1395(16) 0.782(8) 0.215(4) 0.030 Uiso 1 1 d . U . . .
C19 C 0.06960(14) 0.4771(7) 0.1341(4) 0.0259(11) Uani 1 1 d . . . . .
C20 C 0.05263(15) 0.5894(7) 0.2063(5) 0.0329(12) Uani 1 1 d . . . . .
H20 H 0.065632 0.622334 0.268063 0.040 Uiso 1 1 calc R U . . .
C21 C 0.01618(16) 0.6529(8) 0.1865(5) 0.0371(14) Uani 1 1 d . . . . .
H21 H 0.004076 0.731384 0.234893 0.044 Uiso 1 1 calc R U . . .
C22 C -0.00272(16) 0.6041(8) 0.0979(5) 0.0387(14) Uani 1 1 d . . . . .
H22 H -0.027760 0.648876 0.085293 0.046 Uiso 1 1 calc R U . . .
C23 C 0.01461(17) 0.4896(8) 0.0265(5) 0.0375(14) Uani 1 1 d . . . . .
H23 H 0.001305 0.453947 -0.034269 0.045 Uiso 1 1 calc R U . . .
C24 C 0.05147(16) 0.4273(8) 0.0442(4) 0.0336(13) Uani 1 1 d . . . . .
H24 H 0.063934 0.351537 -0.005003 0.040 Uiso 1 1 calc R U . . .
C25 C 0.14347(14) 0.7820(7) 0.0675(4) 0.0229(11) Uani 1 1 d . . . . .
C26 C 0.13937(14) 0.9706(7) 0.0540(4) 0.0225(11) Uani 1 1 d . . . . .
H26 H 0.135017 1.049421 0.111108 0.027 Uiso 1 1 calc R U . . .
C27 C 0.14188(15) 1.0375(8) -0.0453(4) 0.0280(12) Uani 1 1 d . . . . .
C28 C 0.14851(16) 0.9315(8) -0.1312(4) 0.0299(12) Uani 1 1 d . . . . .
H28 H 0.150702 0.983905 -0.198191 0.036 Uiso 1 1 calc R U . . .
C29 C 0.15186(15) 0.7460(8) -0.1160(4) 0.0303(12) Uani 1 1 d . . . . .
H29 H 0.155876 0.668732 -0.173970 0.036 Uiso 1 1 calc R U . . .
C30 C 0.14951(14) 0.6690(7) -0.0180(4) 0.0260(11) Uani 1 1 d . . . . .
H30 H 0.151972 0.540838 -0.009223 0.031 Uiso 1 1 calc R U . . .
C31 C 0.20977(14) 0.3913(7) 0.2025(4) 0.0267(11) Uani 1 1 d . . . . .
C32 C 0.23707(17) 0.4841(8) 0.1462(5) 0.0386(15) Uani 1 1 d . . . . .
H32 H 0.230031 0.550420 0.085994 0.046 Uiso 1 1 calc R U . . .
C33 C 0.27456(18) 0.4799(9) 0.1780(6) 0.0458(17) Uani 1 1 d . . . . .
H33 H 0.293517 0.543410 0.139704 0.055 Uiso 1 1 calc R U . . .
C34 C 0.28456(18) 0.3839(9) 0.2651(5) 0.0436(15) Uani 1 1 d . . . . .
H34 H 0.310494 0.379776 0.286561 0.052 Uiso 1 1 calc R U . . .
C35 C 0.25711(18) 0.2939(9) 0.3211(5) 0.0440(15) Uani 1 1 d . . . . .
H35 H 0.264296 0.228867 0.381658 0.053 Uiso 1 1 calc R U . . .
C36 C 0.21905(16) 0.2962(8) 0.2911(4) 0.0362(13) Uani 1 1 d . . . . .
H36 H 0.200063 0.234361 0.330216 0.043 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
P1 O3 1.459(4) . ?
P1 O1 1.571(3) . ?
P1 O2 1.574(4) . ?
P1 N1 1.627(4) . ?
F1 C9 1.354(6) . ?
O1 C1 1.404(6) . ?
O2 C13 1.417(6) . ?
N1 C7 1.409(6) . ?
N1 H1N 0.81(5) . ?
C1 C6 1.366(8) . ?
C1 C2 1.375(7) . ?
C2 C3 1.378(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.379(7) . ?
C7 C12 1.396(7) . ?
C8 C9 1.369(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(7) . ?
C10 C11 1.388(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.365(8) . ?
C13 C18 1.377(7) . ?
C14 C15 1.385(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
P2 O6 1.463(4) . ?
P2 O4 1.573(4) . ?
P2 O5 1.575(4) . ?
P2 N2 1.624(5) . ?
F2 C27 1.361(6) . ?
O4 C31 1.408(6) . ?
O5 C19 1.410(6) . ?
N2 C25 1.412(6) . ?
N2 H2N 0.78(6) . ?
C19 C24 1.374(7) . ?
C19 C20 1.379(7) . ?
C20 C21 1.382(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(8) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.397(7) . ?
C25 C26 1.400(7) . ?
C26 C27 1.377(8) . ?
C26 H26 0.9500 . ?
C27 C28 1.374(7) . ?
C28 C29 1.379(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.380(7) . ?
C31 C32 1.381(8) . ?
C32 C33 1.376(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.372(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(8) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 P1 O1 116.6(2) . . ?
O3 P1 O2 116.0(2) . . ?
O1 P1 O2 95.38(19) . . ?
O3 P1 N1 110.0(2) . . ?
O1 P1 N1 109.1(2) . . ?
O2 P1 N1 108.8(2) . . ?
C1 O1 P1 124.2(3) . . ?
C13 O2 P1 119.4(3) . . ?
C7 N1 P1 130.0(4) . . ?
C7 N1 H1N 118(4) . . ?
P1 N1 H1N 111(4) . . ?
C6 C1 C2 121.2(5) . . ?
C6 C1 O1 122.8(5) . . ?
C2 C1 O1 115.9(5) . . ?
C1 C2 C3 119.6(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 119.8(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.6(6) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C12 119.7(5) . . ?
C8 C7 N1 118.4(5) . . ?
C12 C7 N1 121.9(5) . . ?
C9 C8 C7 118.6(5) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
F1 C9 C8 118.1(5) . . ?
F1 C9 C10 117.6(5) . . ?
C8 C9 C10 124.2(5) . . ?
C9 C10 C11 116.5(5) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
C10 C11 C12 121.4(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 119.5(5) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C14 C13 C18 122.4(5) . . ?
C14 C13 O2 118.9(5) . . ?
C18 C13 O2 118.6(4) . . ?
C13 C14 C15 118.4(5) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.7(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.3(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 118.4(5) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
O6 P2 O4 115.7(2) . . ?
O6 P2 O5 116.1(2) . . ?
O4 P2 O5 94.7(2) . . ?
O6 P2 N2 109.4(2) . . ?
O4 P2 N2 110.4(2) . . ?
O5 P2 N2 109.7(2) . . ?
C31 O4 P2 122.6(3) . . ?
C19 O5 P2 123.2(3) . . ?
C25 N2 P2 129.5(4) . . ?
C25 N2 H2N 118(4) . . ?
P2 N2 H2N 111(4) . . ?
C24 C19 C20 122.1(5) . . ?
C24 C19 O5 115.5(4) . . ?
C20 C19 O5 122.4(5) . . ?
C19 C20 C21 118.2(5) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C22 C21 C20 120.9(5) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.1(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 119.8(6) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 118.8(5) . . ?
C19 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C30 C25 C26 120.1(5) . . ?
C30 C25 N2 122.2(5) . . ?
C26 C25 N2 117.7(4) . . ?
C27 C26 C25 117.5(5) . . ?
C27 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?
F2 C27 C28 117.7(5) . . ?
F2 C27 C26 118.0(5) . . ?
C28 C27 C26 124.3(5) . . ?
C27 C28 C29 117.1(5) . . ?
C27 C28 H28 121.5 . . ?
C29 C28 H28 121.5 . . ?
C28 C29 C30 121.7(5) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C25 119.3(5) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C36 C31 C32 121.5(5) . . ?
C36 C31 O4 119.7(5) . . ?
C32 C31 O4 118.6(5) . . ?
C33 C32 C31 119.5(6) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C34 C33 C32 120.0(6) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 120.0(6) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 121.3(6) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 117.7(5) . . ?
C31 C36 H36 121.2 . . ?
C35 C36 H36 121.2 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O3 P1 O1 C1 -71.0(4) . . . . ?
O2 P1 O1 C1 166.3(4) . . . . ?
N1 P1 O1 C1 54.3(4) . . . . ?
O3 P1 O2 C13 51.9(4) . . . . ?
O1 P1 O2 C13 175.0(3) . . . . ?
N1 P1 O2 C13 -72.7(4) . . . . ?
O3 P1 N1 C7 179.8(4) . . . . ?
O1 P1 N1 C7 50.8(5) . . . . ?
O2 P1 N1 C7 -52.0(5) . . . . ?
P1 O1 C1 C6 33.1(7) . . . . ?
P1 O1 C1 C2 -149.3(4) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
O1 C1 C2 C3 -177.9(5) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C2 C3 C4 C5 -0.9(9) . . . . ?
C3 C4 C5 C6 1.4(9) . . . . ?
C2 C1 C6 C5 0.7(8) . . . . ?
O1 C1 C6 C5 178.2(5) . . . . ?
C4 C5 C6 C1 -1.3(9) . . . . ?
P1 N1 C7 C8 -176.0(4) . . . . ?
P1 N1 C7 C12 3.4(7) . . . . ?
C12 C7 C8 C9 0.2(8) . . . . ?
N1 C7 C8 C9 179.7(5) . . . . ?
C7 C8 C9 F1 -178.0(5) . . . . ?
C7 C8 C9 C10 0.4(9) . . . . ?
F1 C9 C10 C11 177.8(5) . . . . ?
C8 C9 C10 C11 -0.6(9) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 C7 0.3(7) . . . . ?
C8 C7 C12 C11 -0.6(7) . . . . ?
N1 C7 C12 C11 -180.0(4) . . . . ?
P1 O2 C13 C14 96.2(5) . . . . ?
P1 O2 C13 C18 -87.5(5) . . . . ?
C18 C13 C14 C15 0.9(9) . . . . ?
O2 C13 C14 C15 177.1(5) . . . . ?
C13 C14 C15 C16 0.9(9) . . . . ?
C14 C15 C16 C17 -1.7(9) . . . . ?
C15 C16 C17 C18 0.8(9) . . . . ?
C14 C13 C18 C17 -1.8(8) . . . . ?
O2 C13 C18 C17 -177.9(5) . . . . ?
C16 C17 C18 C13 0.9(8) . . . . ?
O6 P2 O4 C31 -48.2(4) . . . . ?
O5 P2 O4 C31 -170.2(4) . . . . ?
N2 P2 O4 C31 76.8(4) . . . . ?
O6 P2 O5 C19 75.6(4) . . . . ?
O4 P2 O5 C19 -162.7(4) . . . . ?
N2 P2 O5 C19 -49.0(4) . . . . ?
O6 P2 N2 C25 -174.5(4) . . . . ?
O4 P2 N2 C25 57.1(5) . . . . ?
O5 P2 N2 C25 -46.0(5) . . . . ?
P2 O5 C19 C24 149.6(4) . . . . ?
P2 O5 C19 C20 -31.3(7) . . . . ?
C24 C19 C20 C21 0.0(8) . . . . ?
O5 C19 C20 C21 -179.0(5) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C20 C21 C22 C23 0.0(9) . . . . ?
C21 C22 C23 C24 -1.2(9) . . . . ?
C20 C19 C24 C23 -1.2(8) . . . . ?
O5 C19 C24 C23 177.9(5) . . . . ?
C22 C23 C24 C19 1.8(9) . . . . ?
P2 N2 C25 C30 -14.1(7) . . . . ?
P2 N2 C25 C26 167.9(4) . . . . ?
C30 C25 C26 C27 -0.6(7) . . . . ?
N2 C25 C26 C27 177.4(5) . . . . ?
C25 C26 C27 F2 -179.3(4) . . . . ?
C25 C26 C27 C28 -0.7(8) . . . . ?
F2 C27 C28 C29 -179.7(5) . . . . ?
C26 C27 C28 C29 1.7(8) . . . . ?
C27 C28 C29 C30 -1.4(8) . . . . ?
C28 C29 C30 C25 0.2(8) . . . . ?
C26 C25 C30 C29 0.8(7) . . . . ?
N2 C25 C30 C29 -177.0(5) . . . . ?
P2 O4 C31 C36 80.3(6) . . . . ?
P2 O4 C31 C32 -103.9(5) . . . . ?
C36 C31 C32 C33 1.0(9) . . . . ?
O4 C31 C32 C33 -174.7(5) . . . . ?
C31 C32 C33 C34 0.0(10) . . . . ?
C32 C33 C34 C35 -0.8(10) . . . . ?
C33 C34 C35 C36 0.6(10) . . . . ?
C32 C31 C36 C35 -1.1(8) . . . . ?
O4 C31 C36 C35 174.5(5) . . . . ?
C34 C35 C36 C31 0.4(9) . . . . ?
 
_refine_diff_density_max    0.498
_refine_diff_density_min   -0.530
_refine_diff_density_rms    0.079



data_3I
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 I N O3 P'
_chemical_formula_sum              'C18 H15 I N O3 P'
_chemical_formula_weight           451.18
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     10.0600(2)
_cell_length_b                     10.4577(2)
_cell_length_c                     10.6104(2)
_cell_angle_alpha                  109.0980(10)
_cell_angle_beta                   95.7340(10)
_cell_angle_gamma                  116.9670(10)
_cell_volume                       898.35(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4653
_cell_measurement_temperature      100
_cell_measurement_theta_max        28.04
_cell_measurement_theta_min        2.35
_shelx_estimated_absorpt_T_max     0.840
_shelx_estimated_absorpt_T_min     0.558
_exptl_absorpt_coefficient_mu      1.886
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6492
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/5
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.668
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               444
_exptl_crystal_size_max            0.35
_exptl_crystal_size_mid            0.125
_exptl_crystal_size_min            0.096
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0285
_diffrn_reflns_av_unetI/netI       0.0525
_diffrn_reflns_Laue_measured_fraction_full  0.969
_diffrn_reflns_Laue_measured_fraction_max  0.941
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              11038
_diffrn_reflns_point_group_measured_fraction_full  0.969
_diffrn_reflns_point_group_measured_fraction_max  0.941
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.282
_diffrn_reflns_theta_min           2.126
_diffrn_ambient_temperature        100
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.969
_diffrn_measured_fraction_theta_max  0.941
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3639
_reflns_number_total               4192
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.672
_refine_diff_density_min           -0.896
_refine_diff_density_rms           0.135
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       220
_refine_ls_number_reflns           4192
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0440
_refine_ls_R_factor_gt             0.0358
_refine_ls_restrained_S_all        1.064
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0141P)²+0.9249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0550
_refine_ls_wR_factor_ref           0.0575
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 I1 I 0.36293(2) 0.26885(2) 0.29159(2) 0.01635(7) Uani 1 1 d . . . . .
 P1 P 1.02586(8) 0.90785(9) 0.28786(8) 0.01144(17) Uani 1 1 d . . . . .
 O1 O 1.0962(2) 0.8191(2) 0.1927(2) 0.0124(4) Uani 1 1 d . . . . .
 O2 O 0.9550(2) 0.9415(2) 0.1711(2) 0.0131(5) Uani 1 1 d . . . . .
 O3 O 1.1373(2) 1.0480(2) 0.4158(2) 0.0135(5) Uani 1 1 d . . . . .
 N1 N 0.8857(3) 0.7807(3) 0.3238(3) 0.0124(6) Uani 1 1 d . . . . .
 H1 H 0.881(3) 0.815(4) 0.399(3) 0.015 Uiso 1 1 d . U . . .
 C1 C 1.1818(3) 0.7645(3) 0.2509(3) 0.0137(7) Uani 1 1 d . . . . .
 C2 C 1.1033(4) 0.6117(4) 0.2405(3) 0.0203(7) Uani 1 1 d . . . . .
 H2 H 0.993658 0.545534 0.198265 0.024 Uiso 1 1 calc R U . . .
 C3 C 1.1878(4) 0.5574(4) 0.2929(4) 0.0243(8) Uani 1 1 d . . . . .
 H3 H 1.136056 0.452648 0.286524 0.029 Uiso 1 1 calc R U . . .
 C4 C 1.3475(4) 0.6546(4) 0.3548(3) 0.0190(7) Uani 1 1 d . . . . .
 H4 H 1.404848 0.617328 0.392179 0.023 Uiso 1 1 calc R U . . .
 C5 C 1.4232(4) 0.8061(4) 0.3621(3) 0.0201(7) Uani 1 1 d . . . . .
 H5 H 1.532933 0.872364 0.403670 0.024 Uiso 1 1 calc R U . . .
 C6 C 1.3402(3) 0.8621(4) 0.3091(3) 0.0180(7) Uani 1 1 d . . . . .
 H6 H 1.391953 0.965756 0.313096 0.022 Uiso 1 1 calc R U . . .
 C7 C 0.7565(3) 0.6302(3) 0.2319(3) 0.0114(6) Uani 1 1 d . . . . .
 C8 C 0.6470(3) 0.5464(3) 0.2887(3) 0.0120(6) Uani 1 1 d . . . . .
 H8 H 0.658593 0.591193 0.385658 0.014 Uiso 1 1 calc R U . . .
 C9 C 0.5214(3) 0.3971(3) 0.2022(3) 0.0135(7) Uani 1 1 d . . . . .
 C10 C 0.5013(3) 0.3280(3) 0.0609(3) 0.0158(7) Uani 1 1 d . . . . .
 H10 H 0.415189 0.225000 0.003145 0.019 Uiso 1 1 calc R U . . .
 C11 C 0.6103(3) 0.4132(3) 0.0059(3) 0.0165(7) Uani 1 1 d . . . . .
 H11 H 0.598103 0.367683 -0.091131 0.020 Uiso 1 1 calc R U . . .
 C12 C 0.7366(3) 0.5631(3) 0.0891(3) 0.0156(7) Uani 1 1 d . . . . .
 H12 H 0.809313 0.620082 0.049098 0.019 Uiso 1 1 calc R U . . .
 C13 C 0.8878(3) 1.0368(3) 0.1966(3) 0.0131(7) Uani 1 1 d . . . . .
 C14 C 0.8403(4) 1.0755(4) 0.3139(3) 0.0198(7) Uani 1 1 d . . . . .
 H14 H 0.852878 1.039602 0.383235 0.024 Uiso 1 1 calc R U . . .
 C15 C 0.7731(4) 1.1687(4) 0.3281(4) 0.0258(8) Uani 1 1 d . . . . .
 H15 H 0.740118 1.197381 0.408237 0.031 Uiso 1 1 calc R U . . .
 C16 C 0.7543(4) 1.2195(4) 0.2263(4) 0.0247(8) Uani 1 1 d . . . . .
 H16 H 0.708524 1.282807 0.236495 0.030 Uiso 1 1 calc R U . . .
 C17 C 0.8022(4) 1.1779(4) 0.1097(4) 0.0224(8) Uani 1 1 d . . . . .
 H17 H 0.788418 1.212265 0.039477 0.027 Uiso 1 1 calc R U . . .
 C18 C 0.8701(3) 1.0869(3) 0.0943(3) 0.0147(7) Uani 1 1 d . . . . .
 H18 H 0.903981 1.059211 0.014562 0.018 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 I1 C9 2.106(3) . ?
 P1 O1 1.5838(19) . ?
 P1 O2 1.582(2) . ?
 P1 O3 1.467(2) . ?
 P1 N1 1.625(2) . ?
 O1 C1 1.421(3) . ?
 O2 C13 1.412(3) . ?
 N1 H1 0.78(3) . ?
 N1 C7 1.416(4) . ?
 C1 C2 1.383(4) . ?
 C1 C6 1.371(4) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.379(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.384(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.382(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.385(4) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.396(4) . ?
 C7 C12 1.394(4) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.385(4) . ?
 C9 C10 1.381(4) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.386(4) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.384(4) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.381(4) . ?
 C13 C18 1.380(4) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.397(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.382(4) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.382(4) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.382(4) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 N1 108.31(12) . . ?
 O2 P1 O1 95.44(11) . . ?
 O2 P1 N1 109.77(12) . . ?
 O3 P1 O1 116.13(11) . . ?
 O3 P1 O2 115.46(11) . . ?
 O3 P1 N1 110.70(12) . . ?
 C1 O1 P1 119.34(18) . . ?
 C13 O2 P1 123.55(18) . . ?
 P1 N1 H1 114(2) . . ?
 C7 N1 P1 129.0(2) . . ?
 C7 N1 H1 116(2) . . ?
 C2 C1 O1 118.8(3) . . ?
 C6 C1 O1 118.9(3) . . ?
 C6 C1 C2 122.2(3) . . ?
 C1 C2 H2 120.7 . . ?
 C3 C2 C1 118.5(3) . . ?
 C3 C2 H2 120.7 . . ?
 C2 C3 H3 119.8 . . ?
 C2 C3 C4 120.4(3) . . ?
 C4 C3 H3 119.8 . . ?
 C3 C4 H4 120.1 . . ?
 C5 C4 C3 119.8(3) . . ?
 C5 C4 H4 120.1 . . ?
 C4 C5 H5 119.8 . . ?
 C4 C5 C6 120.5(3) . . ?
 C6 C5 H5 119.8 . . ?
 C1 C6 C5 118.5(3) . . ?
 C1 C6 H6 120.7 . . ?
 C5 C6 H6 120.7 . . ?
 C8 C7 N1 117.8(3) . . ?
 C12 C7 N1 122.6(3) . . ?
 C12 C7 C8 119.5(3) . . ?
 C7 C8 H8 120.4 . . ?
 C9 C8 C7 119.3(3) . . ?
 C9 C8 H8 120.4 . . ?
 C8 C9 I1 118.6(2) . . ?
 C10 C9 I1 119.4(2) . . ?
 C10 C9 C8 121.9(3) . . ?
 C9 C10 H10 120.9 . . ?
 C9 C10 C11 118.2(3) . . ?
 C11 C10 H10 120.9 . . ?
 C10 C11 H11 119.3 . . ?
 C12 C11 C10 121.5(3) . . ?
 C12 C11 H11 119.3 . . ?
 C7 C12 H12 120.2 . . ?
 C11 C12 C7 119.7(3) . . ?
 C11 C12 H12 120.2 . . ?
 C14 C13 O2 122.9(3) . . ?
 C18 C13 O2 115.2(2) . . ?
 C18 C13 C14 121.9(3) . . ?
 C13 C14 H14 120.8 . . ?
 C13 C14 C15 118.3(3) . . ?
 C15 C14 H14 120.8 . . ?
 C14 C15 H15 119.8 . . ?
 C16 C15 C14 120.4(3) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 120.1 . . ?
 C15 C16 C17 119.9(3) . . ?
 C17 C16 H16 120.1 . . ?
 C16 C17 H17 119.7 . . ?
 C18 C17 C16 120.5(3) . . ?
 C18 C17 H17 119.7 . . ?
 C13 C18 C17 118.9(3) . . ?
 C13 C18 H18 120.5 . . ?
 C17 C18 H18 120.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 I1 C9 C10 C11 -177.9(2) . . . . ?
 P1 O1 C1 C2 92.3(3) . . . . ?
 P1 O1 C1 C6 -91.0(3) . . . . ?
 P1 O2 C13 C14 -17.6(4) . . . . ?
 P1 O2 C13 C18 163.6(2) . . . . ?
 P1 N1 C7 C8 -176.8(2) . . . . ?
 P1 N1 C7 C12 4.1(4) . . . . ?
 O1 P1 O2 C13 -172.7(2) . . . . ?
 O1 P1 N1 C7 -50.7(3) . . . . ?
 O1 C1 C2 C3 177.8(3) . . . . ?
 O1 C1 C6 C5 -178.2(3) . . . . ?
 O2 P1 O1 C1 178.10(19) . . . . ?
 O2 P1 N1 C7 52.4(3) . . . . ?
 O2 C13 C14 C15 -179.1(3) . . . . ?
 O2 C13 C18 C17 178.6(3) . . . . ?
 O3 P1 O1 C1 56.3(2) . . . . ?
 O3 P1 O2 C13 -50.3(2) . . . . ?
 O3 P1 N1 C7 -179.0(2) . . . . ?
 N1 P1 O1 C1 -69.0(2) . . . . ?
 N1 P1 O2 C13 75.6(2) . . . . ?
 N1 C7 C8 C9 -178.4(3) . . . . ?
 N1 C7 C12 C11 177.8(3) . . . . ?
 C1 C2 C3 C4 0.2(5) . . . . ?
 C2 C1 C6 C5 -1.6(5) . . . . ?
 C2 C3 C4 C5 -1.1(5) . . . . ?
 C3 C4 C5 C6 0.7(5) . . . . ?
 C4 C5 C6 C1 0.6(5) . . . . ?
 C6 C1 C2 C3 1.1(5) . . . . ?
 C7 C8 C9 I1 177.4(2) . . . . ?
 C7 C8 C9 C10 0.3(4) . . . . ?
 C8 C7 C12 C11 -1.2(4) . . . . ?
 C8 C9 C10 C11 -0.8(4) . . . . ?
 C9 C10 C11 C12 0.2(4) . . . . ?
 C10 C11 C12 C7 0.8(4) . . . . ?
 C12 C7 C8 C9 0.7(4) . . . . ?
 C13 C14 C15 C16 0.4(5) . . . . ?
 C14 C13 C18 C17 -0.2(4) . . . . ?
 C14 C15 C16 C17 0.0(5) . . . . ?
 C15 C16 C17 C18 -0.5(5) . . . . ?
 C16 C17 C18 C13 0.6(5) . . . . ?
 C18 C13 C14 C15 -0.3(5) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_4Br
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 Br N O3 P'
_chemical_formula_sum              'C18 H15 Br N O3 P'
_chemical_formula_weight           404.19
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br' 'Br' -0.2901 2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     24.8534(5)
_cell_length_b                     7.26950(10)
_cell_length_c                     19.7913(4)
_cell_angle_alpha                  90
_cell_angle_beta                   103.3460(10)
_cell_angle_gamma                  90
_cell_volume                       3479.16(11)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      4501
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        27.70
_cell_measurement_theta_min        2.38
_shelx_estimated_absorpt_T_max     0.642
_shelx_estimated_absorpt_T_min     0.603
_exptl_absorpt_coefficient_mu      2.470
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.5420
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/2
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.543
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1632
_exptl_crystal_size_max            0.228
_exptl_crystal_size_mid            0.214
_exptl_crystal_size_min            0.197
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0379
_diffrn_reflns_av_unetI/netI       0.0537
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.977
_diffrn_reflns_limit_h_max         31
_diffrn_reflns_limit_h_min         -34
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              15103
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.977
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.110
_diffrn_reflns_theta_min           2.115
_diffrn_ambient_temperature        100.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.977
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3868
_reflns_number_total               5008
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.759
_refine_diff_density_min           -0.505
_refine_diff_density_rms           0.089
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       217
_refine_ls_number_reflns           5008
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0569
_refine_ls_R_factor_gt             0.0388
_refine_ls_restrained_S_all        1.026
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0367P)²+2.2644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0817
_refine_ls_wR_factor_ref           0.0874
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 Br1 Br -0.00789(2) 0.61444(3) 0.37251(2) 0.02530(8) Uani 1 1 d . . . . .
 P1 P 0.19314(2) 0.01762(7) 0.26800(3) 0.01414(12) Uani 1 1 d . . . . .
 O1 O 0.19385(6) -0.09723(19) 0.33608(7) 0.0171(3) Uani 1 1 d . . . . .
 O2 O 0.13731(6) -0.07085(19) 0.22550(7) 0.0168(3) Uani 1 1 d . . . . .
 O3 O 0.24133(6) -0.0003(2) 0.23803(7) 0.0187(3) Uani 1 1 d . . . . .
 N1 N 0.18167(7) 0.2331(2) 0.28157(8) 0.0156(4) Uani 1 1 d . . . . .
 H1 H 0.201652 0.300032 0.272801 0.019 Uiso 1 1 d R U . . .
 C1 C 0.23441(9) -0.0664(3) 0.39764(11) 0.0169(4) Uani 1 1 d . . . . .
 C2 C 0.21673(10) -0.0094(3) 0.45490(12) 0.0271(5) Uani 1 1 d . . . . .
 H2 H 0.178603 0.013446 0.451819 0.033 Uiso 1 1 calc R U . . .
 C3 C 0.25497(11) 0.0145(4) 0.51722(12) 0.0318(6) Uani 1 1 d . . . . .
 H3 H 0.243084 0.053792 0.557185 0.038 Uiso 1 1 calc R U . . .
 C4 C 0.31014(10) -0.0184(3) 0.52149(12) 0.0279(5) Uani 1 1 d . . . . .
 H4 H 0.336318 -0.001284 0.564307 0.034 Uiso 1 1 calc R U . . .
 C5 C 0.32751(11) -0.0764(3) 0.46355(12) 0.0284(5) Uani 1 1 d . . . . .
 H5 H 0.365692 -0.098173 0.466637 0.034 Uiso 1 1 calc R U . . .
 C6 C 0.28951(10) -0.1033(3) 0.40075(12) 0.0243(5) Uani 1 1 d . . . . .
 H6 H 0.301104 -0.145877 0.360994 0.029 Uiso 1 1 calc R U . . .
 C7 C 0.13608(8) 0.3145(3) 0.30127(10) 0.0144(4) Uani 1 1 d . . . . .
 C8 C 0.12915(9) 0.5043(3) 0.29312(10) 0.0175(4) Uani 1 1 d . . . . .
 H8 H 0.154266 0.573425 0.273634 0.021 Uiso 1 1 calc R U . . .
 C9 C 0.08607(9) 0.5927(3) 0.31313(11) 0.0196(5) Uani 1 1 d . . . . .
 H9 H 0.081435 0.721789 0.307075 0.024 Uiso 1 1 calc R U . . .
 C10 C 0.04984(8) 0.4923(3) 0.34194(10) 0.0168(4) Uani 1 1 d . . . . .
 C11 C 0.05530(9) 0.3031(3) 0.34908(11) 0.0200(5) Uani 1 1 d . . . . .
 H11 H 0.029566 0.234552 0.367748 0.024 Uiso 1 1 calc R U . . .
 C12 C 0.09835(9) 0.2141(3) 0.32894(11) 0.0185(4) Uani 1 1 d . . . . .
 H12 H 0.102209 0.084482 0.333974 0.022 Uiso 1 1 calc R U . . .
 C13 C 0.11755(9) -0.0356(3) 0.15383(10) 0.0173(4) Uani 1 1 d . . . . .
 C14 C 0.12890(9) -0.1616(3) 0.10744(11) 0.0208(5) Uani 1 1 d . . . . .
 H14 H 0.151656 -0.265273 0.122999 0.025 Uiso 1 1 calc R U . . .
 C15 C 0.10629(10) -0.1339(3) 0.03702(12) 0.0244(5) Uani 1 1 d . . . . .
 H15 H 0.113687 -0.219419 0.004015 0.029 Uiso 1 1 calc R U . . .
 C16 C 0.07329(9) 0.0166(3) 0.01485(11) 0.0235(5) Uani 1 1 d . . . . .
 H16 H 0.057856 0.034275 -0.033285 0.028 Uiso 1 1 calc R U . . .
 C17 C 0.06265(9) 0.1415(3) 0.06249(12) 0.0228(5) Uani 1 1 d . . . . .
 H17 H 0.040098 0.245695 0.046917 0.027 Uiso 1 1 calc R U . . .
 C18 C 0.08464(9) 0.1165(3) 0.13327(11) 0.0200(5) Uani 1 1 d . . . . .
 H18 H 0.077212 0.201676 0.166386 0.024 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Br1 C10 1.901(2) . ?
 P1 O1 1.5817(15) . ?
 P1 O2 1.5837(15) . ?
 P1 O3 1.4597(15) . ?
 P1 N1 1.6257(18) . ?
 O1 C1 1.408(3) . ?
 O2 C13 1.413(2) . ?
 N1 H1 0.7436 . ?
 N1 C7 1.410(2) . ?
 C1 C2 1.371(3) . ?
 C1 C6 1.383(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.383(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.375(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.381(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.390(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.395(3) . ?
 C7 C12 1.396(3) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.382(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.381(3) . ?
 C10 C11 1.386(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.385(3) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.371(3) . ?
 C13 C18 1.380(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.392(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.377(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.378(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.393(3) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O2 94.26(8) . . ?
 O1 P1 N1 109.63(8) . . ?
 O2 P1 N1 108.27(8) . . ?
 O3 P1 O1 116.75(8) . . ?
 O3 P1 O2 116.63(8) . . ?
 O3 P1 N1 110.18(9) . . ?
 C1 O1 P1 121.18(13) . . ?
 C13 O2 P1 121.22(13) . . ?
 P1 N1 H1 116.1 . . ?
 C7 N1 P1 129.23(14) . . ?
 C7 N1 H1 114.4 . . ?
 C2 C1 O1 117.5(2) . . ?
 C2 C1 C6 121.7(2) . . ?
 C6 C1 O1 120.76(19) . . ?
 C1 C2 H2 120.3 . . ?
 C1 C2 C3 119.3(2) . . ?
 C3 C2 H2 120.3 . . ?
 C2 C3 H3 119.9 . . ?
 C4 C3 C2 120.2(2) . . ?
 C4 C3 H3 119.9 . . ?
 C3 C4 H4 120.0 . . ?
 C3 C4 C5 120.0(2) . . ?
 C5 C4 H4 120.0 . . ?
 C4 C5 H5 119.8 . . ?
 C4 C5 C6 120.5(2) . . ?
 C6 C5 H5 119.8 . . ?
 C1 C6 C5 118.3(2) . . ?
 C1 C6 H6 120.9 . . ?
 C5 C6 H6 120.9 . . ?
 C8 C7 N1 117.93(17) . . ?
 C8 C7 C12 119.08(18) . . ?
 C12 C7 N1 122.99(19) . . ?
 C7 C8 H8 119.7 . . ?
 C9 C8 C7 120.65(19) . . ?
 C9 C8 H8 119.7 . . ?
 C8 C9 H9 120.2 . . ?
 C10 C9 C8 119.6(2) . . ?
 C10 C9 H9 120.2 . . ?
 C9 C10 Br1 119.78(16) . . ?
 C9 C10 C11 120.60(19) . . ?
 C11 C10 Br1 119.63(15) . . ?
 C10 C11 H11 120.1 . . ?
 C12 C11 C10 119.85(19) . . ?
 C12 C11 H11 120.1 . . ?
 C7 C12 H12 119.9 . . ?
 C11 C12 C7 120.1(2) . . ?
 C11 C12 H12 119.9 . . ?
 C14 C13 O2 118.25(19) . . ?
 C14 C13 C18 122.5(2) . . ?
 C18 C13 O2 119.09(18) . . ?
 C13 C14 H14 120.8 . . ?
 C13 C14 C15 118.4(2) . . ?
 C15 C14 H14 120.8 . . ?
 C14 C15 H15 119.8 . . ?
 C16 C15 C14 120.5(2) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 120.0 . . ?
 C15 C16 C17 120.0(2) . . ?
 C17 C16 H16 120.0 . . ?
 C16 C17 H17 119.7 . . ?
 C16 C17 C18 120.6(2) . . ?
 C18 C17 H17 119.7 . . ?
 C13 C18 C17 118.0(2) . . ?
 C13 C18 H18 121.0 . . ?
 C17 C18 H18 121.0 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 Br1 C10 C11 C12 -177.94(16) . . . . ?
 P1 O1 C1 C2 118.60(19) . . . . ?
 P1 O1 C1 C6 -65.2(2) . . . . ?
 P1 O2 C13 C14 96.9(2) . . . . ?
 P1 O2 C13 C18 -87.4(2) . . . . ?
 P1 N1 C7 C8 -164.45(15) . . . . ?
 P1 N1 C7 C12 16.2(3) . . . . ?
 O1 P1 O2 C13 -172.34(15) . . . . ?
 O1 P1 N1 C7 -59.09(19) . . . . ?
 O1 C1 C2 C3 177.1(2) . . . . ?
 O1 C1 C6 C5 -177.7(2) . . . . ?
 O2 P1 O1 C1 -175.19(15) . . . . ?
 O2 P1 N1 C7 42.49(19) . . . . ?
 O2 C13 C14 C15 175.60(19) . . . . ?
 O2 C13 C18 C17 -175.77(18) . . . . ?
 O3 P1 O1 C1 62.07(17) . . . . ?
 O3 P1 O2 C13 -49.51(18) . . . . ?
 O3 P1 N1 C7 171.11(17) . . . . ?
 N1 P1 O1 C1 -64.07(17) . . . . ?
 N1 P1 O2 C13 75.37(16) . . . . ?
 N1 C7 C8 C9 -178.34(19) . . . . ?
 N1 C7 C12 C11 178.18(19) . . . . ?
 C1 C2 C3 C4 0.1(4) . . . . ?
 C2 C1 C6 C5 -1.7(3) . . . . ?
 C2 C3 C4 C5 -0.3(4) . . . . ?
 C3 C4 C5 C6 -0.5(4) . . . . ?
 C4 C5 C6 C1 1.5(4) . . . . ?
 C6 C1 C2 C3 1.0(4) . . . . ?
 C7 C8 C9 C10 0.5(3) . . . . ?
 C8 C7 C12 C11 -1.1(3) . . . . ?
 C8 C9 C10 Br1 177.80(16) . . . . ?
 C8 C9 C10 C11 -1.9(3) . . . . ?
 C9 C10 C11 C12 1.8(3) . . . . ?
 C10 C11 C12 C7 -0.2(3) . . . . ?
 C12 C7 C8 C9 1.0(3) . . . . ?
 C13 C14 C15 C16 -0.1(3) . . . . ?
 C14 C13 C18 C17 -0.3(3) . . . . ?
 C14 C15 C16 C17 0.3(3) . . . . ?
 C15 C16 C17 C18 -0.5(3) . . . . ?
 C16 C17 C18 C13 0.5(3) . . . . ?
 C18 C13 C14 C15 0.1(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_4Cl
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 Cl N O3 P' 
_chemical_formula_weight          359.73

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.3815(2)
_cell_length_b                    9.3201(2)
_cell_length_c                    17.8130(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90.7250(10)
_cell_angle_gamma                 90
_cell_volume                      1723.39(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     5772
_cell_measurement_theta_min       2.47
_cell_measurement_theta_max       29.60
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.386          
_exptl_crystal_F_000              744
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.398
_exptl_crystal_size_mid           0.094
_exptl_crystal_size_min           0.077
_exptl_absorpt_coefficient_mu     0.330
_shelx_estimated_absorpt_T_min    0.880
_shelx_estimated_absorpt_T_max    0.975
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6894
_exptl_absorpt_correction_T_max   0.7460
_exptl_absorpt_process_details    
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0492 before and 0.0373 after correction.
The Ratio of minimum to maximum transmission is 0.9241.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             19630
_diffrn_reflns_av_unetI/netI      0.0430
_diffrn_reflns_av_R_equivalents   0.0344
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          1.962
_diffrn_reflns_theta_max          30.084
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.978
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.978
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.978
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              4947
_reflns_number_gt                 3926
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'BRUKER APEX2'
_computing_cell_refinement        'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction         'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 1.3 (Dolomanov et al., 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+0.5293P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4947
_refine_ls_number_parameters      221
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0635
_refine_ls_R_factor_gt            0.0475
_refine_ls_wR_factor_ref          0.1163
_refine_ls_wR_factor_gt           0.1095
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
P1 P 0.68144(4) 0.55884(4) 0.56257(2) 0.01609(11) Uani 1 1 d . . . . .
Cl1 Cl 0.97004(4) -0.12570(5) 0.59391(3) 0.02751(12) Uani 1 1 d . . . . .
O1 O 0.74035(11) 0.57807(12) 0.64425(6) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.81052(10) 0.59234(12) 0.51961(6) 0.0179(2) Uani 1 1 d . . . . .
O3 O 0.57284(11) 0.65280(12) 0.54273(6) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.64460(13) 0.39075(15) 0.55080(8) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.72435(15) 0.26979(17) 0.56188(8) 0.0149(3) Uani 1 1 d . . . . .
C14 C 0.88964(16) 0.46568(18) 0.41341(10) 0.0209(4) Uani 1 1 d . . . . .
H14 H 0.934402 0.402778 0.446612 0.025 Uiso 1 1 calc R U . . .
C13 C 0.81314(15) 0.57407(17) 0.44100(9) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.67794(16) 0.13503(18) 0.54050(9) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.594097 0.126796 0.518945 0.023 Uiso 1 1 calc R U . . .
C1 C 0.67426(16) 0.53285(18) 0.70867(9) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.92276(16) 0.15810(18) 0.60303(9) 0.0201(3) Uani 1 1 d . . . . .
H11 H 1.006797 0.165407 0.624415 0.024 Uiso 1 1 calc R U . . .
C10 C 0.87470(16) 0.02637(17) 0.58153(9) 0.0184(3) Uani 1 1 d . . . . .
C18 C 0.74620(17) 0.66708(19) 0.39437(10) 0.0247(4) Uani 1 1 d . . . . .
H18 H 0.694418 0.741350 0.414565 0.030 Uiso 1 1 calc R U . . .
C12 C 0.84769(15) 0.28004(17) 0.59328(9) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.880541 0.371020 0.608088 0.023 Uiso 1 1 calc R U . . .
C9 C 0.75273(17) 0.01322(18) 0.55034(9) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.720553 -0.078218 0.535833 0.025 Uiso 1 1 calc R U . . .
C2 C 0.54817(17) 0.5731(2) 0.72079(10) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.501743 0.627852 0.684489 0.031 Uiso 1 1 calc R U . . .
C6 C 0.74416(19) 0.4546(2) 0.76074(10) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.831248 0.429498 0.751571 0.035 Uiso 1 1 calc R U . . .
C15 C 0.89996(17) 0.4503(2) 0.33625(10) 0.0264(4) Uani 1 1 d . . . . .
H15 H 0.952579 0.376617 0.316171 0.032 Uiso 1 1 calc R U . . .
C16 C 0.83347(19) 0.5424(2) 0.28842(11) 0.0300(4) Uani 1 1 d . . . . .
H16 H 0.840854 0.531877 0.235604 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7565(2) 0.6494(2) 0.31747(11) 0.0321(4) Uani 1 1 d . . . . .
H17 H 0.710216 0.711233 0.284418 0.039 Uiso 1 1 calc R U . . .
C3 C 0.49119(18) 0.5316(2) 0.78728(11) 0.0320(4) Uani 1 1 d . . . . .
H3 H 0.404817 0.559031 0.796919 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5583(2) 0.4509(2) 0.83974(11) 0.0326(4) Uani 1 1 d . . . . .
H4 H 0.517689 0.421374 0.884651 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6853(2) 0.4133(2) 0.82656(11) 0.0365(5) Uani 1 1 d . . . . .
H5 H 0.732059 0.358912 0.862867 0.044 Uiso 1 1 calc R U . . .
H1 H 0.577(2) 0.377(2) 0.5270(11) 0.022(5) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
P1 O3 1.4673(12) . ?
P1 O1 1.5813(11) . ?
P1 O2 1.5826(12) . ?
P1 N1 1.6256(14) . ?
Cl1 C10 1.7412(17) . ?
O1 C1 1.409(2) . ?
O2 C13 1.4111(19) . ?
N1 C7 1.411(2) . ?
N1 H1 0.83(2) . ?
C7 C12 1.394(2) . ?
C7 C8 1.396(2) . ?
C14 C13 1.379(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C13 C18 1.382(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C1 C6 1.379(2) . ?
C1 C2 1.381(2) . ?
C11 C10 1.378(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C10 C9 1.382(2) . ?
C18 C17 1.385(3) . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C6 C5 1.384(3) . ?
C6 H6 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 P1 O1 116.17(7) . . ?
O3 P1 O2 114.74(7) . . ?
O1 P1 O2 95.89(6) . . ?
O3 P1 N1 111.43(7) . . ?
O1 P1 N1 108.39(7) . . ?
O2 P1 N1 109.09(7) . . ?
C1 O1 P1 121.93(10) . . ?
C13 O2 P1 118.89(9) . . ?
C7 N1 P1 127.97(11) . . ?
C7 N1 H1 116.3(13) . . ?
P1 N1 H1 114.3(13) . . ?
C12 C7 C8 118.89(15) . . ?
C12 C7 N1 122.39(14) . . ?
C8 C7 N1 118.72(14) . . ?
C13 C14 C15 118.74(15) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C13 C18 122.19(16) . . ?
C14 C13 O2 117.41(14) . . ?
C18 C13 O2 120.32(15) . . ?
C9 C8 C7 120.78(15) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C6 C1 C2 122.02(17) . . ?
C6 C1 O1 116.65(15) . . ?
C2 C1 O1 121.21(15) . . ?
C10 C11 C12 119.62(15) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C10 C9 121.17(15) . . ?
C11 C10 Cl1 119.13(13) . . ?
C9 C10 Cl1 119.69(13) . . ?
C13 C18 C17 118.38(17) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C11 C12 C7 120.37(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C10 C9 C8 119.18(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C1 C2 C3 118.25(17) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C1 C6 C5 118.88(18) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C16 C15 C14 120.02(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.13(18) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.53(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C4 C3 C2 120.86(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.73(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.24(18) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O3 P1 O1 C1 71.70(14) . . . . ?
O2 P1 O1 C1 -167.00(12) . . . . ?
N1 P1 O1 C1 -54.62(13) . . . . ?
O3 P1 O2 C13 -64.31(13) . . . . ?
O1 P1 O2 C13 173.30(11) . . . . ?
N1 P1 O2 C13 61.50(12) . . . . ?
O3 P1 N1 C7 178.10(13) . . . . ?
O1 P1 N1 C7 -52.87(16) . . . . ?
O2 P1 N1 C7 50.40(15) . . . . ?
P1 N1 C7 C12 7.0(2) . . . . ?
P1 N1 C7 C8 -172.93(13) . . . . ?
C15 C14 C13 C18 0.3(3) . . . . ?
C15 C14 C13 O2 -176.38(14) . . . . ?
P1 O2 C13 C14 -112.72(14) . . . . ?
P1 O2 C13 C18 70.54(18) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
N1 C7 C8 C9 -179.95(15) . . . . ?
P1 O1 C1 C6 132.84(14) . . . . ?
P1 O1 C1 C2 -51.1(2) . . . . ?
C12 C11 C10 C9 0.0(2) . . . . ?
C12 C11 C10 Cl1 179.87(13) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
O2 C13 C18 C17 176.93(15) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
N1 C7 C12 C11 -179.93(15) . . . . ?
C11 C10 C9 C8 0.1(2) . . . . ?
Cl1 C10 C9 C8 -179.76(12) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
O1 C1 C2 C3 -176.44(16) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
O1 C1 C6 C5 177.09(17) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C13 C18 C17 C16 -0.9(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
 
_refine_diff_density_max    0.503
_refine_diff_density_min   -0.379
_refine_diff_density_rms    0.067



data_4F
# start Validation Reply Form
_vrf_PLAT155_4F
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: This is performed in order to coherently depict the 
isostructural relation between 4F and other related crystal 
structures discussed in the manuscript.
;
# end Validation Reply Form
_audit_creation_date               2022-01-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 F N O3 P'
_chemical_formula_sum              'C18 H15 F N O3 P'
_chemical_formula_weight           343.28
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     10.1285(7)
_cell_length_b                     9.1480(7)
_cell_length_c                     17.8798(14)
_cell_angle_alpha                  86.225(3)
_cell_angle_beta                   90.171(3)
_cell_angle_gamma                  91.354(3)
_cell_volume                       1652.6(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9947
_cell_measurement_temperature      100
_cell_measurement_theta_max        30.06
_cell_measurement_theta_min        2.44
_shelx_estimated_absorpt_T_max     0.987
_shelx_estimated_absorpt_T_min     0.942
_exptl_absorpt_coefficient_mu      0.192
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.5969
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/2
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.380
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               712
_exptl_crystal_size_max            0.316
_exptl_crystal_size_mid            0.254
_exptl_crystal_size_min            0.068
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    ?
_diffrn_reflns_av_unetI/netI       0.0839
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.983
_diffrn_reflns_limit_h_max         14
_diffrn_reflns_limit_h_min         -14
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              9620
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.983
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.186
_diffrn_reflns_theta_min           2.232
_diffrn_ambient_temperature        100
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.983
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  6078
_reflns_number_total               9620
_reflns_special_details
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      ?
_refine_diff_density_max           0.776
_refine_diff_density_min           -0.686
_refine_diff_density_rms           0.099
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       442
_refine_ls_number_reflns           9620
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1305
_refine_ls_R_factor_gt             0.0761
_refine_ls_restrained_S_all        1.025
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1157P)²+1.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1902
_refine_ls_wR_factor_ref           0.2262
_refine_special_details
;
 Refined as a 2-component twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.862(3)
 0.138(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C24(H24), C32(H32), C2(H2A), C17(H17), C36(H36), C23(H23), C33(H33),
  C14(H14), C6(H6), C35(H35), C26(H26), C15(H15), C8(H8), C20(H20), C30(H30),
 C29(H29), C3(H3), C12(H12), C5(H5), C9(H9), C28(H28), C27(H27), C22(H22),
 C4(H4), C10(H10), C11(H11), C21(H21)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P2 P 0.69864(7) 1.05048(8) 0.54953(4) 0.02457(19) Uani 1 1 d . . . . .
 P1 P 0.69511(7) 0.45152(7) 0.05533(4) 0.02266(18) Uani 1 1 d . . . . .
 F1 F 0.9289(2) 1.1347(2) 0.08679(12) 0.0433(5) Uani 1 1 d . . . . .
 F2 F 0.9400(2) 0.3743(2) 0.57970(12) 0.0445(5) Uani 1 1 d . . . . .
 O4 O 0.82886(19) 1.0784(2) 0.50176(12) 0.0268(4) Uani 1 1 d . . . . .
 O1 O 0.82725(19) 0.4274(2) 0.01138(11) 0.0254(4) Uani 1 1 d . . . . .
 O3 O 0.58649(19) 0.3492(2) 0.03905(12) 0.0268(4) Uani 1 1 d . . . . .
 O5 O 0.76597(19) 1.0697(2) 0.62820(12) 0.0277(5) Uani 1 1 d . . . . .
 O2 O 0.75788(19) 0.4323(2) 0.13606(12) 0.0269(4) Uani 1 1 d . . . . .
 O6 O 0.5905(2) 1.1500(2) 0.52999(13) 0.0308(5) Uani 1 1 d . . . . .
 N2 N 0.6516(2) 0.8797(3) 0.54570(15) 0.0266(5) Uani 1 1 d . . . . .
 N1 N 0.6520(2) 0.6207(3) 0.04067(15) 0.0257(5) Uani 1 1 d . . . . .
 C18 C 0.6638(3) 0.8834(3) 0.04306(16) 0.0250(6) Uani 1 1 d . . . . .
 H18 H 0.573403 0.885286 0.028864 0.030 Uiso 1 1 calc R U . . .
 C1 C 0.8271(3) 0.4407(3) -0.06719(17) 0.0251(6) Uani 1 1 d . . . . .
 C24 C 0.8972(3) 0.9336(3) 0.40303(17) 0.0273(6) Uani 1 1 d . . . . .
 H24 H 0.940131 0.870268 0.439110 0.033 Uiso 1 1 calc R U . . .
 C32 C 0.6739(3) 0.6214(3) 0.53320(17) 0.0277(6) Uani 1 1 d . . . . .
 H32 H 0.587133 0.618988 0.512933 0.033 Uiso 1 1 calc R U . . .
 C13 C 0.7263(3) 0.7498(3) 0.05242(15) 0.0217(5) Uani 1 1 d . . . . .
 C31 C 0.7282(3) 0.7534(3) 0.55473(16) 0.0226(6) Uani 1 1 d . . . . .
 C19 C 0.8278(3) 1.0517(3) 0.42543(17) 0.0263(6) Uani 1 1 d . . . . .
 C25 C 0.7014(3) 1.0327(3) 0.69613(18) 0.0297(7) Uani 1 1 d . . . . .
 C2 C 0.8942(3) 0.5591(3) -0.10250(19) 0.0314(7) Uani 1 1 d . . . . .
 H2A H 0.933886 0.632611 -0.074102 0.038 Uiso 1 1 calc R U . . .
 C7 C 0.6895(3) 0.4678(3) 0.20080(17) 0.0278(6) Uani 1 1 d . . . . .
 C16 C 0.8619(3) 1.0077(3) 0.07452(17) 0.0288(6) Uani 1 1 d . . . . .
 C17 C 0.7310(3) 1.0141(3) 0.05405(17) 0.0297(6) Uani 1 1 d . . . . .
 H17 H 0.688025 1.105233 0.047649 0.036 Uiso 1 1 calc R U . . .
 C36 C 0.8559(3) 0.7553(3) 0.58528(17) 0.0261(6) Uani 1 1 d . . . . .
 H36 H 0.893514 0.844142 0.601263 0.031 Uiso 1 1 calc R U . . .
 C23 C 0.9034(3) 0.9088(4) 0.32815(19) 0.0358(7) Uani 1 1 d . . . . .
 H23 H 0.951653 0.828590 0.312348 0.043 Uiso 1 1 calc R U . . .
 C33 C 0.7448(3) 0.4929(3) 0.54093(18) 0.0323(7) Uani 1 1 d . . . . .
 H33 H 0.707722 0.402999 0.526050 0.039 Uiso 1 1 calc R U . . .
 C14 C 0.8589(3) 0.7473(3) 0.07333(19) 0.0294(7) Uani 1 1 d . . . . .
 H14 H 0.902710 0.656725 0.080479 0.035 Uiso 1 1 calc R U . . .
 C34 C 0.8698(3) 0.4995(3) 0.57063(18) 0.0309(7) Uani 1 1 d . . . . .
 C6 C 0.7660(3) 0.3337(4) -0.10731(19) 0.0375(8) Uani 1 1 d . . . . .
 H6 H 0.719278 0.253541 -0.082312 0.045 Uiso 1 1 calc R U . . .
 C35 C 0.9274(3) 0.6274(3) 0.59217(18) 0.0306(7) Uani 1 1 d . . . . .
 H35 H 1.014835 0.628473 0.611504 0.037 Uiso 1 1 calc R U . . .
 C26 C 0.5743(3) 1.0770(4) 0.7096(2) 0.0416(9) Uani 1 1 d . . . . .
 H26 H 0.525706 1.130119 0.671708 0.050 Uiso 1 1 calc R U . . .
 C15 C 0.9269(3) 0.8790(3) 0.08367(18) 0.0310(7) Uani 1 1 d . . . . .
 H15 H 1.017724 0.878890 0.096997 0.037 Uiso 1 1 calc R U . . .
 C8 C 0.5617(3) 0.4174(4) 0.2148(2) 0.0405(8) Uani 1 1 d . . . . .
 H8 H 0.515489 0.361386 0.179823 0.049 Uiso 1 1 calc R U . . .
 C20 C 0.7639(4) 1.1455(4) 0.3738(2) 0.0402(8) Uani 1 1 d . . . . .
 H20 H 0.716739 1.226521 0.389554 0.048 Uiso 1 1 calc R U . . .
 C30 C 0.7734(4) 0.9546(4) 0.7510(2) 0.0422(8) Uani 1 1 d . . . . .
 H30 H 0.860337 0.924638 0.740906 0.051 Uiso 1 1 calc R U . . .
 C29 C 0.7169(4) 0.9212(4) 0.8201(2) 0.0494(10) Uani 1 1 d . . . . .
 H29 H 0.765613 0.868903 0.858244 0.059 Uiso 1 1 calc R U . . .
 C3 C 0.9024(4) 0.5687(4) -0.1793(2) 0.0409(8) Uani 1 1 d . . . . .
 H3 H 0.949602 0.648421 -0.204309 0.049 Uiso 1 1 calc R U . . .
 C12 C 0.7583(4) 0.5482(4) 0.2509(2) 0.0456(9) Uani 1 1 d . . . . .
 H12 H 0.845885 0.582346 0.240132 0.055 Uiso 1 1 calc R U . . .
 C5 C 0.7745(4) 0.3462(5) -0.1841(2) 0.0497(10) Uani 1 1 d . . . . .
 H5 H 0.733406 0.273811 -0.212580 0.060 Uiso 1 1 calc R U . . .
 C9 C 0.5030(4) 0.4504(5) 0.2809(2) 0.0492(9) Uani 1 1 d . . . . .
 H9 H 0.415284 0.416510 0.291512 0.059 Uiso 1 1 calc R U . . .
 C28 C 0.5893(4) 0.9635(5) 0.8345(2) 0.0490(9) Uani 1 1 d . . . . .
 H28 H 0.550017 0.938584 0.881901 0.059 Uiso 1 1 calc R U . . .
 C27 C 0.5197(4) 1.0419(5) 0.7796(2) 0.0523(11) Uani 1 1 d . . . . .
 H27 H 0.432994 1.072363 0.789920 0.063 Uiso 1 1 calc R U . . .
 C22 C 0.8401(4) 0.9998(5) 0.2760(2) 0.0475(9) Uani 1 1 d . . . . .
 H22 H 0.843874 0.981721 0.224311 0.057 Uiso 1 1 calc R U . . .
 C4 C 0.8423(4) 0.4630(5) -0.2203(2) 0.0522(10) Uani 1 1 d . . . . .
 H4 H 0.847591 0.470615 -0.273468 0.063 Uiso 1 1 calc R U . . .
 C10 C 0.5695(4) 0.5319(5) 0.3317(2) 0.0508(10) Uani 1 1 d . . . . .
 H10 H 0.527381 0.555777 0.376561 0.061 Uiso 1 1 calc R U . . .
 C11 C 0.6983(5) 0.5785(5) 0.3169(2) 0.0557(11) Uani 1 1 d . . . . .
 H11 H 0.745642 0.631838 0.352576 0.067 Uiso 1 1 calc R U . . .
 C21 C 0.7707(4) 1.1181(5) 0.2988(2) 0.0550(11) Uani 1 1 d . . . . .
 H21 H 0.727461 1.180802 0.262595 0.066 Uiso 1 1 calc R U . . .
 H1 H 0.582(4) 0.627(4) 0.0195(19) 0.031(9) Uiso 1 1 d . . . . .
 H2 H 0.579(4) 0.874(4) 0.526(2) 0.048(12) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P2 O4 1.580(2) . ?
 P2 O5 1.580(2) . ?
 P2 O6 1.467(2) . ?
 P2 N2 1.628(2) . ?
 P1 O1 1.581(2) . ?
 P1 O3 1.4684(19) . ?
 P1 O2 1.576(2) . ?
 P1 N1 1.623(2) . ?
 F1 C16 1.362(3) . ?
 F2 C34 1.363(3) . ?
 O4 C19 1.402(4) . ?
 O1 C1 1.402(4) . ?
 O5 C25 1.399(4) . ?
 O2 C7 1.410(4) . ?
 N2 C31 1.407(4) . ?
 N2 H2 0.82(4) . ?
 N1 C13 1.413(3) . ?
 N1 H1 0.80(4) . ?
 C18 H18 0.9500 . ?
 C18 C13 1.390(4) . ?
 C18 C17 1.386(4) . ?
 C1 C2 1.382(4) . ?
 C1 C6 1.385(4) . ?
 C24 H24 0.9500 . ?
 C24 C19 1.384(4) . ?
 C24 C23 1.375(4) . ?
 C32 H32 0.9500 . ?
 C32 C31 1.392(4) . ?
 C32 C33 1.390(4) . ?
 C13 C14 1.394(4) . ?
 C31 C36 1.403(4) . ?
 C19 C20 1.387(4) . ?
 C25 C26 1.386(4) . ?
 C25 C30 1.390(5) . ?
 C2 H2A 0.9500 . ?
 C2 C3 1.373(5) . ?
 C7 C8 1.382(4) . ?
 C7 C12 1.374(4) . ?
 C16 C17 1.375(4) . ?
 C16 C15 1.363(4) . ?
 C17 H17 0.9500 . ?
 C36 H36 0.9500 . ?
 C36 C35 1.389(4) . ?
 C23 H23 0.9500 . ?
 C23 C22 1.376(5) . ?
 C33 H33 0.9500 . ?
 C33 C34 1.373(5) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.396(4) . ?
 C34 C35 1.372(4) . ?
 C6 H6 0.9500 . ?
 C6 C5 1.372(5) . ?
 C35 H35 0.9500 . ?
 C26 H26 0.9500 . ?
 C26 C27 1.384(5) . ?
 C15 H15 0.9500 . ?
 C8 H8 0.9500 . ?
 C8 C9 1.378(5) . ?
 C20 H20 0.9500 . ?
 C20 C21 1.381(5) . ?
 C30 H30 0.9500 . ?
 C30 C29 1.376(5) . ?
 C29 H29 0.9500 . ?
 C29 C28 1.387(6) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.380(6) . ?
 C12 H12 0.9500 . ?
 C12 C11 1.377(5) . ?
 C5 H5 0.9500 . ?
 C5 C4 1.382(6) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.377(6) . ?
 C28 H28 0.9500 . ?
 C28 C27 1.379(6) . ?
 C27 H27 0.9500 . ?
 C22 H22 0.9500 . ?
 C22 C21 1.388(6) . ?
 C4 H4 0.9500 . ?
 C10 H10 0.9500 . ?
 C10 C11 1.383(6) . ?
 C11 H11 0.9500 . ?
 C21 H21 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O4 P2 N2 108.85(12) . . ?
 O5 P2 O4 95.90(11) . . ?
 O5 P2 N2 108.41(13) . . ?
 O6 P2 O4 115.38(13) . . ?
 O6 P2 O5 115.64(12) . . ?
 O6 P2 N2 111.49(12) . . ?
 O1 P1 N1 109.31(12) . . ?
 O3 P1 O1 114.47(11) . . ?
 O3 P1 O2 116.32(12) . . ?
 O3 P1 N1 111.56(12) . . ?
 O2 P1 O1 95.80(11) . . ?
 O2 P1 N1 108.23(12) . . ?
 C19 O4 P2 119.55(17) . . ?
 C1 O1 P1 119.47(17) . . ?
 C25 O5 P2 122.70(18) . . ?
 C7 O2 P1 122.18(18) . . ?
 P2 N2 H2 110(3) . . ?
 C31 N2 P2 128.6(2) . . ?
 C31 N2 H2 119(3) . . ?
 P1 N1 H1 112(3) . . ?
 C13 N1 P1 128.6(2) . . ?
 C13 N1 H1 119(3) . . ?
 C13 C18 H18 119.4 . . ?
 C17 C18 H18 119.4 . . ?
 C17 C18 C13 121.2(3) . . ?
 C2 C1 O1 118.1(3) . . ?
 C2 C1 C6 121.7(3) . . ?
 C6 C1 O1 120.1(3) . . ?
 C19 C24 H24 120.3 . . ?
 C23 C24 H24 120.3 . . ?
 C23 C24 C19 119.4(3) . . ?
 C31 C32 H32 119.5 . . ?
 C33 C32 H32 119.5 . . ?
 C33 C32 C31 121.0(3) . . ?
 C18 C13 N1 118.4(2) . . ?
 C18 C13 C14 119.3(3) . . ?
 C14 C13 N1 122.3(2) . . ?
 C32 C31 N2 118.4(2) . . ?
 C32 C31 C36 119.0(3) . . ?
 C36 C31 N2 122.6(2) . . ?
 C24 C19 O4 118.0(3) . . ?
 C24 C19 C20 121.3(3) . . ?
 C20 C19 O4 120.6(3) . . ?
 C26 C25 O5 121.9(3) . . ?
 C26 C25 C30 121.4(3) . . ?
 C30 C25 O5 116.6(3) . . ?
 C1 C2 H2A 120.6 . . ?
 C3 C2 C1 118.9(3) . . ?
 C3 C2 H2A 120.6 . . ?
 C8 C7 O2 121.4(3) . . ?
 C12 C7 O2 116.8(3) . . ?
 C12 C7 C8 121.7(3) . . ?
 F1 C16 C17 118.8(3) . . ?
 F1 C16 C15 118.7(3) . . ?
 C15 C16 C17 122.6(3) . . ?
 C18 C17 H17 121.0 . . ?
 C16 C17 C18 118.0(3) . . ?
 C16 C17 H17 121.0 . . ?
 C31 C36 H36 120.0 . . ?
 C35 C36 C31 120.0(3) . . ?
 C35 C36 H36 120.0 . . ?
 C24 C23 H23 119.9 . . ?
 C24 C23 C22 120.3(3) . . ?
 C22 C23 H23 119.9 . . ?
 C32 C33 H33 120.9 . . ?
 C34 C33 C32 118.3(3) . . ?
 C34 C33 H33 120.9 . . ?
 C13 C14 H14 120.3 . . ?
 C13 C14 C15 119.4(3) . . ?
 C15 C14 H14 120.3 . . ?
 F2 C34 C33 119.1(3) . . ?
 F2 C34 C35 118.3(3) . . ?
 C35 C34 C33 122.7(3) . . ?
 C1 C6 H6 120.8 . . ?
 C5 C6 C1 118.4(3) . . ?
 C5 C6 H6 120.8 . . ?
 C36 C35 H35 120.5 . . ?
 C34 C35 C36 119.0(3) . . ?
 C34 C35 H35 120.5 . . ?
 C25 C26 H26 120.8 . . ?
 C27 C26 C25 118.4(4) . . ?
 C27 C26 H26 120.8 . . ?
 C16 C15 C14 119.5(3) . . ?
 C16 C15 H15 120.2 . . ?
 C14 C15 H15 120.2 . . ?
 C7 C8 H8 120.8 . . ?
 C9 C8 C7 118.3(3) . . ?
 C9 C8 H8 120.8 . . ?
 C19 C20 H20 120.8 . . ?
 C21 C20 C19 118.3(3) . . ?
 C21 C20 H20 120.8 . . ?
 C25 C30 H30 120.4 . . ?
 C29 C30 C25 119.1(3) . . ?
 C29 C30 H30 120.4 . . ?
 C30 C29 H29 119.8 . . ?
 C30 C29 C28 120.3(4) . . ?
 C28 C29 H29 119.8 . . ?
 C2 C3 H3 119.9 . . ?
 C2 C3 C4 120.3(3) . . ?
 C4 C3 H3 119.9 . . ?
 C7 C12 H12 120.5 . . ?
 C7 C12 C11 119.0(3) . . ?
 C11 C12 H12 120.5 . . ?
 C6 C5 H5 119.6 . . ?
 C6 C5 C4 120.7(3) . . ?
 C4 C5 H5 119.6 . . ?
 C8 C9 H9 119.5 . . ?
 C10 C9 C8 121.1(3) . . ?
 C10 C9 H9 119.5 . . ?
 C29 C28 H28 120.1 . . ?
 C27 C28 C29 119.8(4) . . ?
 C27 C28 H28 120.1 . . ?
 C26 C27 H27 119.5 . . ?
 C28 C27 C26 121.0(3) . . ?
 C28 C27 H27 119.5 . . ?
 C23 C22 H22 120.0 . . ?
 C23 C22 C21 120.0(3) . . ?
 C21 C22 H22 120.0 . . ?
 C3 C4 C5 120.0(3) . . ?
 C3 C4 H4 120.0 . . ?
 C5 C4 H4 120.0 . . ?
 C9 C10 H10 120.3 . . ?
 C9 C10 C11 119.4(4) . . ?
 C11 C10 H10 120.3 . . ?
 C12 C11 C10 120.5(4) . . ?
 C12 C11 H11 119.8 . . ?
 C10 C11 H11 119.8 . . ?
 C20 C21 C22 120.7(3) . . ?
 C20 C21 H21 119.7 . . ?
 C22 C21 H21 119.7 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 P2 O4 C19 C24 -110.0(3) . . . . ?
 P2 O4 C19 C20 73.0(3) . . . . ?
 P2 O5 C25 C26 -47.8(4) . . . . ?
 P2 O5 C25 C30 135.0(3) . . . . ?
 P2 N2 C31 C32 -166.2(2) . . . . ?
 P2 N2 C31 C36 14.6(4) . . . . ?
 P1 O1 C1 C2 110.4(3) . . . . ?
 P1 O1 C1 C6 -72.4(3) . . . . ?
 P1 O2 C7 C8 49.4(4) . . . . ?
 P1 O2 C7 C12 -133.8(3) . . . . ?
 P1 N1 C13 C18 -173.5(2) . . . . ?
 P1 N1 C13 C14 6.1(4) . . . . ?
 F1 C16 C17 C18 -178.9(3) . . . . ?
 F1 C16 C15 C14 178.3(3) . . . . ?
 F2 C34 C35 C36 -178.2(3) . . . . ?
 O4 P2 O5 C25 -168.9(2) . . . . ?
 O4 P2 N2 C31 46.2(3) . . . . ?
 O4 C19 C20 C21 177.2(3) . . . . ?
 O1 P1 O2 C7 168.7(2) . . . . ?
 O1 P1 N1 C13 -55.0(3) . . . . ?
 O1 C1 C2 C3 175.7(3) . . . . ?
 O1 C1 C6 C5 -176.3(3) . . . . ?
 O3 P1 O1 C1 60.7(2) . . . . ?
 O3 P1 O2 C7 -70.3(2) . . . . ?
 O3 P1 N1 C13 177.4(2) . . . . ?
 O5 P2 O4 C19 170.3(2) . . . . ?
 O5 P2 N2 C31 -57.0(3) . . . . ?
 O5 C25 C26 C27 -176.9(3) . . . . ?
 O5 C25 C30 C29 177.0(3) . . . . ?
 O2 P1 O1 C1 -176.89(19) . . . . ?
 O2 P1 N1 C13 48.2(3) . . . . ?
 O2 C7 C8 C9 177.0(3) . . . . ?
 O2 C7 C12 C11 -176.4(3) . . . . ?
 O6 P2 O4 C19 -67.6(2) . . . . ?
 O6 P2 O5 C25 69.2(2) . . . . ?
 O6 P2 N2 C31 174.6(3) . . . . ?
 N2 P2 O4 C19 58.6(2) . . . . ?
 N2 P2 O5 C25 -56.8(2) . . . . ?
 N2 C31 C36 C35 -179.4(3) . . . . ?
 N1 P1 O1 C1 -65.3(2) . . . . ?
 N1 P1 O2 C7 56.2(2) . . . . ?
 N1 C13 C14 C15 179.7(3) . . . . ?
 C18 C13 C14 C15 -0.7(5) . . . . ?
 C1 C2 C3 C4 1.2(5) . . . . ?
 C1 C6 C5 C4 -0.1(6) . . . . ?
 C24 C19 C20 C21 0.2(5) . . . . ?
 C24 C23 C22 C21 0.7(6) . . . . ?
 C32 C31 C36 C35 1.4(4) . . . . ?
 C32 C33 C34 F2 179.0(3) . . . . ?
 C32 C33 C34 C35 -0.6(5) . . . . ?
 C13 C18 C17 C16 0.1(4) . . . . ?
 C13 C14 C15 C16 1.2(5) . . . . ?
 C31 C32 C33 C34 0.2(5) . . . . ?
 C31 C36 C35 C34 -1.8(5) . . . . ?
 C19 C24 C23 C22 -0.6(5) . . . . ?
 C19 C20 C21 C22 -0.2(6) . . . . ?
 C25 C26 C27 C28 -0.7(6) . . . . ?
 C25 C30 C29 C28 0.8(6) . . . . ?
 C2 C1 C6 C5 0.8(5) . . . . ?
 C2 C3 C4 C5 -0.6(6) . . . . ?
 C7 C8 C9 C10 0.1(6) . . . . ?
 C7 C12 C11 C10 -1.6(6) . . . . ?
 C17 C18 C13 N1 179.7(3) . . . . ?
 C17 C18 C13 C14 0.1(4) . . . . ?
 C17 C16 C15 C14 -1.1(5) . . . . ?
 C23 C24 C19 O4 -176.8(3) . . . . ?
 C23 C24 C19 C20 0.2(4) . . . . ?
 C23 C22 C21 C20 -0.2(7) . . . . ?
 C33 C32 C31 N2 -179.9(3) . . . . ?
 C33 C32 C31 C36 -0.6(5) . . . . ?
 C33 C34 C35 C36 1.4(5) . . . . ?
 C6 C1 C2 C3 -1.4(5) . . . . ?
 C6 C5 C4 C3 0.0(7) . . . . ?
 C26 C25 C30 C29 -0.2(5) . . . . ?
 C15 C16 C17 C18 0.5(5) . . . . ?
 C8 C7 C12 C11 0.3(6) . . . . ?
 C8 C9 C10 C11 -1.4(7) . . . . ?
 C30 C25 C26 C27 0.2(5) . . . . ?
 C30 C29 C28 C27 -1.3(6) . . . . ?
 C29 C28 C27 C26 1.2(6) . . . . ?
 C12 C7 C8 C9 0.4(5) . . . . ?
 C9 C10 C11 C12 2.1(7) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.862(3)
 2 0.138(3)


data_4I
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H15 I N O3 P'
_chemical_formula_sum              'C18 H15 I N O3 P'
_chemical_formula_weight           451.18
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     25.2005(5)
_cell_length_b                     7.3428(2)
_cell_length_c                     19.8275(4)
_cell_angle_alpha                  90
_cell_angle_beta                   103.0830(10)
_cell_angle_gamma                  90
_cell_volume                       3573.69(14)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      8444
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        30.13
_cell_measurement_theta_min        2.90
_shelx_estimated_absorpt_T_max     0.758
_shelx_estimated_absorpt_T_min     0.468
_exptl_absorpt_coefficient_mu      1.897
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6523
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/2
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.677
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               1776
_exptl_crystal_size_max            0.472
_exptl_crystal_size_mid            0.165
_exptl_crystal_size_min            0.155
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0221
_diffrn_reflns_av_unetI/netI       0.0219
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         35
_diffrn_reflns_limit_h_min         -24
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -27
_diffrn_reflns_number              18234
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.991
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.141
_diffrn_reflns_theta_min           1.659
_diffrn_ambient_temperature        100
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  4838
_reflns_number_total               5238
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           1.375
_refine_diff_density_min           -0.685
_refine_diff_density_rms           0.080
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           5238
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0291
_refine_ls_R_factor_gt             0.0258
_refine_ls_restrained_S_all        1.063
_refine_ls_shift/su_max            0.004
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0241P)²+6.8304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0582
_refine_ls_wR_factor_ref           0.0595
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 I1 I 1.00937(2) 0.61390(2) 0.12487(2) 0.02255(5) Uani 1 1 d . . . . .
 P1 P 0.80568(2) 0.00273(6) 0.23160(2) 0.01316(9) Uani 1 1 d . . . . .
 O1 O 0.80484(6) -0.10972(17) 0.16330(7) 0.0172(3) Uani 1 1 d . . . . .
 O2 O 0.86073(5) -0.08474(17) 0.27359(7) 0.0164(2) Uani 1 1 d . . . . .
 O3 O 0.75805(5) -0.01587(18) 0.26200(7) 0.0176(3) Uani 1 1 d . . . . .
 N1 N 0.81668(6) 0.2175(2) 0.21830(8) 0.0151(3) Uani 1 1 d . . . . .
 C1 C 0.76438(8) -0.0763(2) 0.10274(10) 0.0172(3) Uani 1 1 d . . . . .
 C2 C 0.71033(9) -0.1180(3) 0.10012(11) 0.0235(4) Uani 1 1 d . . . . .
 H2 H 0.699472 -0.165993 0.139417 0.028 Uiso 1 1 calc R U . . .
 C3 C 0.67237(9) -0.0876(3) 0.03822(12) 0.0283(5) Uani 1 1 d . . . . .
 H3 H 0.634931 -0.112192 0.035491 0.034 Uiso 1 1 calc R U . . .
 C4 C 0.68861(10) -0.0219(3) -0.01933(11) 0.0285(5) Uani 1 1 d . . . . .
 H4 H 0.662390 -0.002406 -0.061366 0.034 Uiso 1 1 calc R U . . .
 C5 C 0.74259(10) 0.0153(3) -0.01579(11) 0.0309(5) Uani 1 1 d . . . . .
 H5 H 0.753629 0.059740 -0.055489 0.037 Uiso 1 1 calc R U . . .
 C6 C 0.78121(9) -0.0119(3) 0.04582(11) 0.0263(4) Uani 1 1 d . . . . .
 H6 H 0.818585 0.013640 0.048502 0.032 Uiso 1 1 calc R U . . .
 C7 C 0.86109(7) 0.2994(2) 0.19806(9) 0.0137(3) Uani 1 1 d . . . . .
 C8 C 0.89939(8) 0.2002(2) 0.17200(10) 0.0178(4) Uani 1 1 d . . . . .
 H8 H 0.896205 0.071596 0.167773 0.021 Uiso 1 1 calc R U . . .
 C9 C 0.94220(8) 0.2895(3) 0.15222(10) 0.0181(4) Uani 1 1 d . . . . .
 H9 H 0.968290 0.221874 0.134705 0.022 Uiso 1 1 calc R U . . .
 C10 C 0.94666(7) 0.4776(2) 0.15815(9) 0.0154(3) Uani 1 1 d . . . . .
 C11 C 0.90919(8) 0.5770(3) 0.18477(10) 0.0178(3) Uani 1 1 d . . . . .
 H11 H 0.912566 0.705520 0.189219 0.021 Uiso 1 1 calc R U . . .
 C12 C 0.86688(7) 0.4875(2) 0.20478(9) 0.0156(3) Uani 1 1 d . . . . .
 H12 H 0.841446 0.555500 0.223358 0.019 Uiso 1 1 calc R U . . .
 C13 C 0.88008(7) -0.0487(3) 0.34466(10) 0.0160(3) Uani 1 1 d . . . . .
 C14 C 0.91434(8) 0.0984(3) 0.36491(10) 0.0197(4) Uani 1 1 d . . . . .
 H14 H 0.922499 0.180331 0.331568 0.024 Uiso 1 1 calc R U . . .
 C15 C 0.93656(8) 0.1236(3) 0.43522(11) 0.0230(4) Uani 1 1 d . . . . .
 H15 H 0.960095 0.223869 0.450259 0.028 Uiso 1 1 calc R U . . .
 C16 C 0.92445(9) 0.0026(3) 0.48346(11) 0.0235(4) Uani 1 1 d . . . . .
 H16 H 0.939895 0.020126 0.531362 0.028 Uiso 1 1 calc R U . . .
 C17 C 0.89009(9) -0.1428(3) 0.46212(11) 0.0233(4) Uani 1 1 d . . . . .
 H17 H 0.881952 -0.224866 0.495412 0.028 Uiso 1 1 calc R U . . .
 C18 C 0.86721(8) -0.1700(3) 0.39183(11) 0.0209(4) Uani 1 1 d . . . . .
 H18 H 0.843378 -0.269560 0.376801 0.025 Uiso 1 1 calc R U . . .
 H1 H 0.7947(12) 0.285(4) 0.2249(14) 0.036(8) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 I1 C10 2.0992(17) . ?
 P1 O1 1.5820(14) . ?
 P1 O2 1.5834(14) . ?
 P1 O3 1.4663(14) . ?
 P1 N1 1.6326(16) . ?
 O1 C1 1.410(2) . ?
 O2 C13 1.408(2) . ?
 N1 C7 1.407(2) . ?
 N1 H1 0.78(3) . ?
 C1 C2 1.386(3) . ?
 C1 C6 1.376(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.393(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.383(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.373(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.393(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.398(2) . ?
 C7 C12 1.393(2) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.392(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.388(3) . ?
 C10 C11 1.389(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.385(3) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.385(3) . ?
 C13 C18 1.382(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.392(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.389(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.380(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.397(3) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O2 94.51(7) . . ?
 O1 P1 N1 109.62(8) . . ?
 O2 P1 N1 108.42(8) . . ?
 O3 P1 O1 116.73(8) . . ?
 O3 P1 O2 116.57(8) . . ?
 O3 P1 N1 109.94(8) . . ?
 C1 O1 P1 120.33(11) . . ?
 C13 O2 P1 120.91(11) . . ?
 P1 N1 H1 116(2) . . ?
 C7 N1 P1 129.36(13) . . ?
 C7 N1 H1 115(2) . . ?
 C2 C1 O1 120.59(17) . . ?
 C6 C1 O1 117.42(18) . . ?
 C6 C1 C2 121.88(19) . . ?
 C1 C2 H2 121.0 . . ?
 C1 C2 C3 118.09(19) . . ?
 C3 C2 H2 121.0 . . ?
 C2 C3 H3 119.7 . . ?
 C4 C3 C2 120.7(2) . . ?
 C4 C3 H3 119.7 . . ?
 C3 C4 H4 119.9 . . ?
 C5 C4 C3 120.1(2) . . ?
 C5 C4 H4 119.9 . . ?
 C4 C5 H5 119.9 . . ?
 C4 C5 C6 120.2(2) . . ?
 C6 C5 H5 119.9 . . ?
 C1 C6 C5 119.0(2) . . ?
 C1 C6 H6 120.5 . . ?
 C5 C6 H6 120.5 . . ?
 C8 C7 N1 122.91(16) . . ?
 C12 C7 N1 118.02(15) . . ?
 C12 C7 C8 119.07(16) . . ?
 C7 C8 H8 119.9 . . ?
 C9 C8 C7 120.18(16) . . ?
 C9 C8 H8 119.9 . . ?
 C8 C9 H9 120.1 . . ?
 C10 C9 C8 119.82(17) . . ?
 C10 C9 H9 120.1 . . ?
 C9 C10 I1 120.00(13) . . ?
 C9 C10 C11 120.40(16) . . ?
 C11 C10 I1 119.59(13) . . ?
 C10 C11 H11 120.2 . . ?
 C12 C11 C10 119.58(16) . . ?
 C12 C11 H11 120.2 . . ?
 C7 C12 H12 119.5 . . ?
 C11 C12 C7 120.93(17) . . ?
 C11 C12 H12 119.5 . . ?
 C14 C13 O2 119.26(17) . . ?
 C18 C13 O2 118.36(17) . . ?
 C18 C13 C14 122.22(18) . . ?
 C13 C14 H14 120.8 . . ?
 C13 C14 C15 118.50(18) . . ?
 C15 C14 H14 120.8 . . ?
 C14 C15 H15 119.9 . . ?
 C16 C15 C14 120.23(19) . . ?
 C16 C15 H15 119.9 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 C15 120.28(19) . . ?
 C17 C16 H16 119.9 . . ?
 C16 C17 H17 119.8 . . ?
 C16 C17 C18 120.38(19) . . ?
 C18 C17 H17 119.8 . . ?
 C13 C18 C17 118.40(19) . . ?
 C13 C18 H18 120.8 . . ?
 C17 C18 H18 120.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 I1 C10 C11 C12 178.07(14) . . . . ?
 P1 O1 C1 C2 -67.3(2) . . . . ?
 P1 O1 C1 C6 116.61(17) . . . . ?
 P1 O2 C13 C14 -89.96(19) . . . . ?
 P1 O2 C13 C18 94.67(18) . . . . ?
 P1 N1 C7 C8 13.6(3) . . . . ?
 P1 N1 C7 C12 -166.16(15) . . . . ?
 O1 P1 O2 C13 -172.92(14) . . . . ?
 O1 P1 N1 C7 -58.86(18) . . . . ?
 O1 C1 C2 C3 -177.94(18) . . . . ?
 O1 C1 C6 C5 177.29(19) . . . . ?
 O2 P1 O1 C1 -175.21(13) . . . . ?
 O2 P1 N1 C7 43.07(19) . . . . ?
 O2 C13 C14 C15 -174.94(17) . . . . ?
 O2 C13 C18 C17 174.74(17) . . . . ?
 O3 P1 O1 C1 61.97(15) . . . . ?
 O3 P1 O2 C13 -49.98(16) . . . . ?
 O3 P1 N1 C7 171.56(16) . . . . ?
 N1 P1 O1 C1 -63.82(15) . . . . ?
 N1 P1 O2 C13 74.67(15) . . . . ?
 N1 C7 C8 C9 179.39(18) . . . . ?
 N1 C7 C12 C11 -178.96(17) . . . . ?
 C1 C2 C3 C4 1.6(3) . . . . ?
 C2 C1 C6 C5 1.2(3) . . . . ?
 C2 C3 C4 C5 -0.4(3) . . . . ?
 C3 C4 C5 C6 -0.4(4) . . . . ?
 C4 C5 C6 C1 0.0(3) . . . . ?
 C6 C1 C2 C3 -2.0(3) . . . . ?
 C7 C8 C9 C10 -0.3(3) . . . . ?
 C8 C7 C12 C11 1.3(3) . . . . ?
 C8 C9 C10 I1 -177.66(14) . . . . ?
 C8 C9 C10 C11 1.1(3) . . . . ?
 C9 C10 C11 C12 -0.7(3) . . . . ?
 C10 C11 C12 C7 -0.5(3) . . . . ?
 C12 C7 C8 C9 -0.9(3) . . . . ?
 C13 C14 C15 C16 0.2(3) . . . . ?
 C14 C13 C18 C17 -0.5(3) . . . . ?
 C14 C15 C16 C17 -0.3(3) . . . . ?
 C15 C16 C17 C18 0.1(3) . . . . ?
 C16 C17 C18 C13 0.3(3) . . . . ?
 C18 C13 C14 C15 0.2(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_24F
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H14 F2 N O3 P'
_chemical_formula_sum              'C18 H14 F2 N O3 P'
_chemical_formula_weight           361.27
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     10.1665(6)
_cell_length_b                     9.3374(5)
_cell_length_c                     17.5495(10)
_cell_angle_alpha                  90
_cell_angle_beta                   94.912(2)
_cell_angle_gamma                  90
_cell_volume                       1659.83(16)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      8409
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        29.81
_cell_measurement_theta_min        2.33
_shelx_estimated_absorpt_T_max     0.996
_shelx_estimated_absorpt_T_min     0.896
_exptl_absorpt_coefficient_mu      0.204
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6571
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/5
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.446
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               744
_exptl_crystal_size_max            0.55
_exptl_crystal_size_mid            0.103
_exptl_crystal_size_min            0.018
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0936
_diffrn_reflns_av_unetI/netI       0.0531
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         22
_diffrn_reflns_limit_l_min         -21
_diffrn_reflns_number              32876
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.100
_diffrn_reflns_theta_min           2.330
_diffrn_ambient_temperature        99.95
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2703
_reflns_number_total               3652
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.282
_refine_diff_density_min           -0.414
_refine_diff_density_rms           0.066
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       226
_refine_ls_number_reflns           3652
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0786
_refine_ls_R_factor_gt             0.0490
_refine_ls_restrained_S_all        1.031
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0299P)²+1.6612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0881
_refine_ls_wR_factor_ref           0.0981
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.20142(5) 0.52469(6) 0.56332(3) 0.01209(14) Uani 1 1 d . . . . .
 F1 F 0.02276(11) 0.11326(13) 0.55061(7) 0.0193(3) Uani 1 1 d . . . . .
 F2 F 0.41396(12) -0.15317(13) 0.59683(8) 0.0226(3) Uani 1 1 d . . . . .
 O1 O 0.32857(14) 0.56017(15) 0.52076(8) 0.0147(3) Uani 1 1 d . . . . .
 O2 O 0.27572(14) 0.51997(15) 0.64623(8) 0.0151(3) Uani 1 1 d . . . . .
 O3 O 0.09297(14) 0.62757(15) 0.55031(8) 0.0157(3) Uani 1 1 d . . . . .
 N1 N 0.15280(17) 0.36224(18) 0.54189(10) 0.0140(4) Uani 1 1 d . . . . .
 H1 H 0.073094 0.353203 0.518567 0.017 Uiso 1 1 calc R U . . .
 C1 C 0.3163(2) 0.5832(2) 0.44079(12) 0.0149(5) Uani 1 1 d . . . . .
 C2 C 0.2525(2) 0.7036(2) 0.41087(13) 0.0195(5) Uani 1 1 d . . . . .
 H2 H 0.212115 0.769146 0.443096 0.023 Uiso 1 1 calc R U . . .
 C3 C 0.2487(2) 0.7269(3) 0.33269(13) 0.0255(6) Uani 1 1 d . . . . .
 H3 H 0.204864 0.808854 0.310864 0.031 Uiso 1 1 calc R U . . .
 C4 C 0.3085(2) 0.6312(3) 0.28626(14) 0.0294(6) Uani 1 1 d . . . . .
 H4 H 0.306684 0.648395 0.232827 0.035 Uiso 1 1 calc R U . . .
 C5 C 0.3709(2) 0.5103(3) 0.31759(14) 0.0278(6) Uani 1 1 d . . . . .
 H5 H 0.410712 0.444030 0.285471 0.033 Uiso 1 1 calc R U . . .
 C6 C 0.3756(2) 0.4857(2) 0.39570(13) 0.0208(5) Uani 1 1 d . . . . .
 H6 H 0.418655 0.403364 0.417674 0.025 Uiso 1 1 calc R U . . .
 C7 C 0.2247(2) 0.2342(2) 0.55669(11) 0.0125(4) Uani 1 1 d . . . . .
 C8 C 0.1563(2) 0.1061(2) 0.56025(12) 0.0135(4) Uani 1 1 d . . . . .
 C9 C 0.2159(2) -0.0246(2) 0.57278(12) 0.0148(4) Uani 1 1 d . . . . .
 H9 H 0.166087 -0.110593 0.573732 0.018 Uiso 1 1 calc R U . . .
 C10 C 0.3519(2) -0.0249(2) 0.58394(12) 0.0156(5) Uani 1 1 d . . . . .
 C11 C 0.4258(2) 0.0974(2) 0.58288(13) 0.0190(5) Uani 1 1 d . . . . .
 H11 H 0.519260 0.093508 0.591566 0.023 Uiso 1 1 calc R U . . .
 C12 C 0.3617(2) 0.2272(2) 0.56885(13) 0.0178(5) Uani 1 1 d . . . . .
 H12 H 0.412113 0.312640 0.567542 0.021 Uiso 1 1 calc R U . . .
 C13 C 0.2176(2) 0.4657(2) 0.71040(12) 0.0155(5) Uani 1 1 d . . . . .
 C14 C 0.3042(2) 0.4112(2) 0.76783(13) 0.0206(5) Uani 1 1 d . . . . .
 H14 H 0.396131 0.406934 0.761888 0.025 Uiso 1 1 calc R U . . .
 C15 C 0.2550(2) 0.3626(3) 0.83440(14) 0.0252(6) Uani 1 1 d . . . . .
 H15 H 0.313833 0.325913 0.874707 0.030 Uiso 1 1 calc R U . . .
 C16 C 0.1212(3) 0.3671(3) 0.84259(14) 0.0300(6) Uani 1 1 d . . . . .
 H16 H 0.087601 0.332554 0.888004 0.036 Uiso 1 1 calc R U . . .
 C17 C 0.0367(3) 0.4224(3) 0.78402(14) 0.0368(7) Uani 1 1 d . . . . .
 H17 H -0.055344 0.425624 0.789572 0.044 Uiso 1 1 calc R U . . .
 C18 C 0.0840(2) 0.4733(3) 0.71715(13) 0.0271(6) Uani 1 1 d . . . . .
 H18 H 0.025730 0.512201 0.677249 0.032 Uiso 1 1 calc R U . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O1 1.5824(15) . ?
 P1 O2 1.5816(15) . ?
 P1 O3 1.4655(15) . ?
 P1 N1 1.6294(18) . ?
 F1 C8 1.355(2) . ?
 F2 C10 1.364(2) . ?
 O1 C1 1.415(2) . ?
 O2 C13 1.410(2) . ?
 N1 H1 0.8800 . ?
 N1 C7 1.414(3) . ?
 C1 C2 1.380(3) . ?
 C1 C6 1.378(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.386(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.384(4) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.386(4) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.387(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.388(3) . ?
 C7 C12 1.392(3) . ?
 C8 C9 1.372(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.380(3) . ?
 C10 C11 1.367(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.388(3) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.378(3) . ?
 C13 C18 1.375(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.386(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.381(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.382(4) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.389(3) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 N1 109.27(8) . . ?
 O2 P1 O1 95.45(8) . . ?
 O2 P1 N1 107.34(9) . . ?
 O3 P1 O1 115.05(8) . . ?
 O3 P1 O2 117.08(8) . . ?
 O3 P1 N1 111.40(9) . . ?
 C1 O1 P1 119.60(12) . . ?
 C13 O2 P1 123.03(13) . . ?
 P1 N1 H1 116.5 . . ?
 C7 N1 P1 127.06(15) . . ?
 C7 N1 H1 116.5 . . ?
 C2 C1 O1 119.98(19) . . ?
 C6 C1 O1 117.63(19) . . ?
 C6 C1 C2 122.3(2) . . ?
 C1 C2 H2 120.8 . . ?
 C1 C2 C3 118.5(2) . . ?
 C3 C2 H2 120.8 . . ?
 C2 C3 H3 119.8 . . ?
 C4 C3 C2 120.3(2) . . ?
 C4 C3 H3 119.8 . . ?
 C3 C4 H4 119.9 . . ?
 C3 C4 C5 120.1(2) . . ?
 C5 C4 H4 119.9 . . ?
 C4 C5 H5 119.9 . . ?
 C4 C5 C6 120.2(2) . . ?
 C6 C5 H5 119.9 . . ?
 C1 C6 C5 118.6(2) . . ?
 C1 C6 H6 120.7 . . ?
 C5 C6 H6 120.7 . . ?
 C8 C7 N1 118.90(18) . . ?
 C8 C7 C12 116.82(19) . . ?
 C12 C7 N1 124.28(18) . . ?
 F1 C8 C7 116.93(18) . . ?
 F1 C8 C9 119.19(18) . . ?
 C9 C8 C7 123.88(19) . . ?
 C8 C9 H9 121.7 . . ?
 C8 C9 C10 116.59(19) . . ?
 C10 C9 H9 121.7 . . ?
 F2 C10 C9 117.95(19) . . ?
 F2 C10 C11 119.23(19) . . ?
 C11 C10 C9 122.8(2) . . ?
 C10 C11 H11 120.6 . . ?
 C10 C11 C12 118.7(2) . . ?
 C12 C11 H11 120.6 . . ?
 C7 C12 H12 119.4 . . ?
 C11 C12 C7 121.1(2) . . ?
 C11 C12 H12 119.4 . . ?
 C14 C13 O2 115.58(19) . . ?
 C18 C13 O2 122.3(2) . . ?
 C18 C13 C14 122.0(2) . . ?
 C13 C14 H14 120.5 . . ?
 C13 C14 C15 118.9(2) . . ?
 C15 C14 H14 120.5 . . ?
 C14 C15 H15 119.8 . . ?
 C16 C15 C14 120.5(2) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 120.4 . . ?
 C15 C16 C17 119.3(2) . . ?
 C17 C16 H16 120.4 . . ?
 C16 C17 H17 119.4 . . ?
 C16 C17 C18 121.2(2) . . ?
 C18 C17 H17 119.4 . . ?
 C13 C18 C17 118.1(2) . . ?
 C13 C18 H18 121.0 . . ?
 C17 C18 H18 121.0 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 P1 O1 C1 C2 68.7(2) . . . . ?
 P1 O1 C1 C6 -114.42(18) . . . . ?
 P1 O2 C13 C14 152.84(16) . . . . ?
 P1 O2 C13 C18 -30.4(3) . . . . ?
 P1 N1 C7 C8 157.20(16) . . . . ?
 P1 N1 C7 C12 -22.2(3) . . . . ?
 F1 C8 C9 C10 -178.55(18) . . . . ?
 F2 C10 C11 C12 179.29(19) . . . . ?
 O1 P1 O2 C13 -167.75(15) . . . . ?
 O1 P1 N1 C7 60.94(19) . . . . ?
 O1 C1 C2 C3 176.46(19) . . . . ?
 O1 C1 C6 C5 -176.56(19) . . . . ?
 O2 P1 O1 C1 -177.22(14) . . . . ?
 O2 P1 N1 C7 -41.44(19) . . . . ?
 O2 C13 C14 C15 176.74(19) . . . . ?
 O2 C13 C18 C17 -177.3(2) . . . . ?
 O3 P1 O1 C1 -53.89(17) . . . . ?
 O3 P1 O2 C13 70.48(17) . . . . ?
 O3 P1 N1 C7 -170.83(16) . . . . ?
 N1 P1 O1 C1 72.27(16) . . . . ?
 N1 P1 O2 C13 -55.60(17) . . . . ?
 N1 C7 C8 F1 -1.3(3) . . . . ?
 N1 C7 C8 C9 178.72(19) . . . . ?
 N1 C7 C12 C11 -179.8(2) . . . . ?
 C1 C2 C3 C4 -0.3(3) . . . . ?
 C2 C1 C6 C5 0.2(3) . . . . ?
 C2 C3 C4 C5 0.9(4) . . . . ?
 C3 C4 C5 C6 -1.0(4) . . . . ?
 C4 C5 C6 C1 0.4(3) . . . . ?
 C6 C1 C2 C3 -0.2(3) . . . . ?
 C7 C8 C9 C10 1.4(3) . . . . ?
 C8 C7 C12 C11 0.8(3) . . . . ?
 C8 C9 C10 F2 179.75(18) . . . . ?
 C8 C9 C10 C11 0.0(3) . . . . ?
 C9 C10 C11 C12 -1.0(3) . . . . ?
 C10 C11 C12 C7 0.5(3) . . . . ?
 C12 C7 C8 F1 178.15(18) . . . . ?
 C12 C7 C8 C9 -1.8(3) . . . . ?
 C13 C14 C15 C16 0.8(4) . . . . ?
 C14 C13 C18 C17 -0.7(4) . . . . ?
 C14 C15 C16 C17 -0.8(4) . . . . ?
 C15 C16 C17 C18 0.1(4) . . . . ?
 C16 C17 C18 C13 0.7(4) . . . . ?
 C18 C13 C14 C15 0.0(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

data_25F
_audit_creation_date               2021-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H14 F2 N O3 P'
_chemical_formula_sum              'C18 H14 F2 N O3 P'
_chemical_formula_weight           361.27
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     9.2189(6)
_cell_length_b                     10.0245(7)
_cell_length_c                     10.0445(7)
_cell_angle_alpha                  68.276(3)
_cell_angle_beta                   84.831(3)
_cell_angle_gamma                  69.889(3)
_cell_volume                       809.02(10)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      6562
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        29.37
_cell_measurement_theta_min        2.35
_shelx_estimated_absorpt_T_max     0.996
_shelx_estimated_absorpt_T_min     0.929
_exptl_absorpt_coefficient_mu      0.209
_exptl_absorpt_correction_T_max    0.7460
_exptl_absorpt_correction_T_min    0.6775
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     SADABS-2014/5
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.483
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               372
_exptl_crystal_size_max            0.36
_exptl_crystal_size_mid            0.048
_exptl_crystal_size_min            0.018
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0939
_diffrn_reflns_av_unetI/netI       0.0626
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         13
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              22878
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.282
_diffrn_reflns_theta_min           2.322
_diffrn_ambient_temperature        100.25
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2972
_reflns_number_total               4012
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.333
_refine_diff_density_min           -0.543
_refine_diff_density_rms           0.069
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       230
_refine_ls_number_reflns           4012
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0767
_refine_ls_R_factor_gt             0.0461
_refine_ls_restrained_S_all        1.056
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0304P)²+0.5222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0901
_refine_ls_wR_factor_ref           0.1003
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P1 P 0.05565(6) 0.18760(5) 0.02516(5) 0.01272(12) Uani 1 1 d . . . . .
 F1 F -0.08886(14) 0.23889(14) -0.38945(12) 0.0239(3) Uani 1 1 d . . . . .
 F2 F -0.21078(14) 0.77583(13) -0.31823(13) 0.0256(3) Uani 1 1 d . . . . .
 O1 O 0.17258(15) 0.27812(15) -0.00478(14) 0.0156(3) Uani 1 1 d . . . . .
 O2 O -0.06092(15) 0.28456(14) 0.10800(14) 0.0152(3) Uani 1 1 d . . . . .
 O3 O 0.11482(15) 0.02359(15) 0.10545(14) 0.0172(3) Uani 1 1 d . . . . .
 N1 N -0.02350(19) 0.22597(19) -0.12917(17) 0.0155(3) Uani 1 1 d . . . . .
 C1 C 0.2972(2) 0.2645(2) -0.09561(19) 0.0145(4) Uani 1 1 d . . . . .
 C2 C 0.3519(2) 0.3855(2) -0.1419(2) 0.0173(4) Uani 1 1 d . . . . .
 H2 H 0.303849 0.471283 -0.114480 0.021 Uiso 1 1 calc R U . . .
 C3 C 0.4777(2) 0.3806(2) -0.2289(2) 0.0215(4) Uani 1 1 d . . . . .
 H3 H 0.515880 0.463640 -0.261962 0.026 Uiso 1 1 calc R U . . .
 C4 C 0.5478(2) 0.2550(2) -0.2676(2) 0.0225(5) Uani 1 1 d . . . . .
 H4 H 0.633974 0.251582 -0.327294 0.027 Uiso 1 1 calc R U . . .
 C5 C 0.4918(2) 0.1345(2) -0.2192(2) 0.0217(4) Uani 1 1 d . . . . .
 H5 H 0.540694 0.048125 -0.245493 0.026 Uiso 1 1 calc R U . . .
 C6 C 0.3655(2) 0.1375(2) -0.1329(2) 0.0181(4) Uani 1 1 d . . . . .
 H6 H 0.326848 0.054771 -0.100249 0.022 Uiso 1 1 calc R U . . .
 C7 C -0.0875(2) 0.3692(2) -0.2384(2) 0.0146(4) Uani 1 1 d . . . . .
 C8 C -0.1231(2) 0.3745(2) -0.3722(2) 0.0174(4) Uani 1 1 d . . . . .
 C9 C -0.1878(2) 0.5076(3) -0.4850(2) 0.0226(5) Uani 1 1 d . . . . .
 H9 H -0.211927 0.505342 -0.573992 0.027 Uiso 1 1 calc R U . . .
 C10 C -0.2178(2) 0.6456(2) -0.4682(2) 0.0229(5) Uani 1 1 d . . . . .
 H10 H -0.262092 0.739731 -0.544645 0.027 Uiso 1 1 calc R U . . .
 C11 C -0.1811(2) 0.6409(2) -0.3370(2) 0.0183(4) Uani 1 1 d . . . . .
 C12 C -0.1174(2) 0.5081(2) -0.2213(2) 0.0165(4) Uani 1 1 d . . . . .
 H12 H -0.094642 0.511183 -0.132341 0.020 Uiso 1 1 calc R U . . .
 C13 C -0.1737(2) 0.2289(2) 0.1909(2) 0.0138(4) Uani 1 1 d . . . . .
 C14 C -0.1473(2) 0.1623(2) 0.3378(2) 0.0180(4) Uani 1 1 d . . . . .
 H14 H -0.052062 0.146304 0.380647 0.022 Uiso 1 1 calc R U . . .
 C15 C -0.2637(2) 0.1194(2) 0.4212(2) 0.0208(4) Uani 1 1 d . . . . .
 H15 H -0.248018 0.072731 0.522496 0.025 Uiso 1 1 calc R U . . .
 C16 C -0.4026(2) 0.1442(2) 0.3575(2) 0.0222(5) Uani 1 1 d . . . . .
 H16 H -0.482129 0.115646 0.415449 0.027 Uiso 1 1 calc R U . . .
 C17 C -0.4258(2) 0.2103(2) 0.2099(2) 0.0220(5) Uani 1 1 d . . . . .
 H17 H -0.520910 0.226223 0.166872 0.026 Uiso 1 1 calc R U . . .
 C18 C -0.3108(2) 0.2533(2) 0.1247(2) 0.0194(4) Uani 1 1 d . . . . .
 H18 H -0.325618 0.298562 0.023288 0.023 Uiso 1 1 calc R U . . .
 H1 H -0.041(3) 0.154(3) -0.138(3) 0.041(8) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 P1 O1 1.5773(13) . ?
 P1 O2 1.5846(14) . ?
 P1 O3 1.4602(14) . ?
 P1 N1 1.6287(16) . ?
 F1 C8 1.359(2) . ?
 F2 C11 1.366(2) . ?
 O1 C1 1.403(2) . ?
 O2 C13 1.409(2) . ?
 N1 C7 1.407(2) . ?
 N1 H1 0.82(3) . ?
 C1 C2 1.380(3) . ?
 C1 C6 1.384(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.386(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.382(3) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.383(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.386(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.390(3) . ?
 C7 C12 1.396(3) . ?
 C8 C9 1.370(3) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.386(3) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.370(3) . ?
 C11 C12 1.381(3) . ?
 C12 H12 0.9500 . ?
 C13 C14 1.380(3) . ?
 C13 C18 1.384(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.388(3) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.386(3) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.384(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.386(3) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 P1 O2 95.06(7) . . ?
 O1 P1 N1 106.99(8) . . ?
 O2 P1 N1 109.50(8) . . ?
 O3 P1 O1 117.63(8) . . ?
 O3 P1 O2 114.97(8) . . ?
 O3 P1 N1 111.38(8) . . ?
 C1 O1 P1 125.54(12) . . ?
 C13 O2 P1 119.39(11) . . ?
 P1 N1 H1 114.9(18) . . ?
 C7 N1 P1 128.27(14) . . ?
 C7 N1 H1 116.0(18) . . ?
 C2 C1 O1 114.97(17) . . ?
 C2 C1 C6 121.73(18) . . ?
 C6 C1 O1 123.25(17) . . ?
 C1 C2 H2 120.4 . . ?
 C1 C2 C3 119.23(19) . . ?
 C3 C2 H2 120.4 . . ?
 C2 C3 H3 120.0 . . ?
 C4 C3 C2 120.09(18) . . ?
 C4 C3 H3 120.0 . . ?
 C3 C4 H4 120.2 . . ?
 C3 C4 C5 119.70(19) . . ?
 C5 C4 H4 120.2 . . ?
 C4 C5 H5 119.4 . . ?
 C4 C5 C6 121.16(19) . . ?
 C6 C5 H5 119.4 . . ?
 C1 C6 C5 118.08(18) . . ?
 C1 C6 H6 121.0 . . ?
 C5 C6 H6 121.0 . . ?
 C8 C7 N1 118.73(17) . . ?
 C8 C7 C12 117.28(17) . . ?
 C12 C7 N1 123.99(17) . . ?
 F1 C8 C7 116.94(17) . . ?
 F1 C8 C9 119.64(17) . . ?
 C9 C8 C7 123.41(19) . . ?
 C8 C9 H9 120.3 . . ?
 C8 C9 C10 119.37(19) . . ?
 C10 C9 H9 120.3 . . ?
 C9 C10 H10 121.3 . . ?
 C11 C10 C9 117.41(19) . . ?
 C11 C10 H10 121.3 . . ?
 F2 C11 C10 118.20(17) . . ?
 F2 C11 C12 117.60(17) . . ?
 C10 C11 C12 124.20(19) . . ?
 C7 C12 H12 120.8 . . ?
 C11 C12 C7 118.31(18) . . ?
 C11 C12 H12 120.8 . . ?
 C14 C13 O2 117.90(16) . . ?
 C14 C13 C18 122.47(18) . . ?
 C18 C13 O2 119.43(17) . . ?
 C13 C14 H14 120.9 . . ?
 C13 C14 C15 118.25(18) . . ?
 C15 C14 H14 120.9 . . ?
 C14 C15 H15 119.8 . . ?
 C16 C15 C14 120.36(19) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 C15 120.27(19) . . ?
 C17 C16 H16 119.9 . . ?
 C16 C17 H17 119.9 . . ?
 C16 C17 C18 120.24(19) . . ?
 C18 C17 H17 119.9 . . ?
 C13 C18 C17 118.41(19) . . ?
 C13 C18 H18 120.8 . . ?
 C17 C18 H18 120.8 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 P1 O1 C1 C2 159.85(13) . . . . ?
 P1 O1 C1 C6 -22.4(2) . . . . ?
 P1 O2 C13 C14 101.79(17) . . . . ?
 P1 O2 C13 C18 -83.35(19) . . . . ?
 P1 N1 C7 C8 168.17(14) . . . . ?
 P1 N1 C7 C12 -11.6(3) . . . . ?
 F1 C8 C9 C10 -177.88(17) . . . . ?
 F2 C11 C12 C7 179.54(16) . . . . ?
 O1 P1 O2 C13 -164.86(13) . . . . ?
 O1 P1 N1 C7 -47.42(18) . . . . ?
 O1 C1 C2 C3 178.23(16) . . . . ?
 O1 C1 C6 C5 -177.62(17) . . . . ?
 O2 P1 O1 C1 -170.05(14) . . . . ?
 O2 P1 N1 C7 54.48(18) . . . . ?
 O2 C13 C14 C15 174.41(16) . . . . ?
 O2 C13 C18 C17 -174.04(17) . . . . ?
 O3 P1 O1 C1 68.30(16) . . . . ?
 O3 P1 O2 C13 -41.16(15) . . . . ?
 O3 P1 N1 C7 -177.24(16) . . . . ?
 N1 P1 O1 C1 -57.87(16) . . . . ?
 N1 P1 O2 C13 85.11(14) . . . . ?
 N1 C7 C8 F1 -1.9(2) . . . . ?
 N1 C7 C8 C9 178.97(18) . . . . ?
 N1 C7 C12 C11 -179.75(17) . . . . ?
 C1 C2 C3 C4 -0.4(3) . . . . ?
 C2 C1 C6 C5 -0.1(3) . . . . ?
 C2 C3 C4 C5 0.0(3) . . . . ?
 C3 C4 C5 C6 0.4(3) . . . . ?
 C4 C5 C6 C1 -0.4(3) . . . . ?
 C6 C1 C2 C3 0.5(3) . . . . ?
 C7 C8 C9 C10 1.2(3) . . . . ?
 C8 C7 C12 C11 0.4(3) . . . . ?
 C8 C9 C10 C11 -0.3(3) . . . . ?
 C9 C10 C11 F2 -179.60(17) . . . . ?
 C9 C10 C11 C12 -0.4(3) . . . . ?
 C10 C11 C12 C7 0.3(3) . . . . ?
 C12 C7 C8 F1 177.86(16) . . . . ?
 C12 C7 C8 C9 -1.2(3) . . . . ?
 C13 C14 C15 C16 -0.4(3) . . . . ?
 C14 C13 C18 C17 0.6(3) . . . . ?
 C14 C15 C16 C17 0.8(3) . . . . ?
 C15 C16 C17 C18 -0.5(3) . . . . ?
 C16 C17 C18 C13 -0.2(3) . . . . ?
 C18 C13 C14 C15 -0.3(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

