##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'APEX4 v2021.10-0'
_journal_date_recd_electronic     2023-10-12
_journal_date_accepted     2023-10-14
_journal_name_full     'IUCrData'
_journal_year     2023
_journal_volume     8
_journal_issue     10
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431462300901X
_journal_coeditor_code     HB4454
_publ_contact_author_name     'Abdulsalam Alsubari'
_publ_contact_author_address
;
Laboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21 September
University,
Yemen
;
_publ_contact_author_email     'alsubaripharmaco@21umas.edu.ye'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
2-[4-(2-Chlorobenzyl)-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl]-N-(4-\
fluorophenyl)acetamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Assila, Hamza' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy, Mohammed V University in Rabat,
Morocco
;
    'Ameziane El Hassani, Issam' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy, Mohammed V University in Rabat,
Morocco
;
    'El Moutaouakil Ala Allah, Abderrazzak' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy, Mohammed V University in Rabat,
Morocco
;
    'Alsubari, Abdulsalam' .
;
Laboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy,
21 September University,
Yemen
;
    'Mague, Joel T' .
;
Department of Chemistry, Tulane University, New Orleans, LA 70118,
USA
;
    'Ramli, Youssef' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy, Mohammed V University in Rabat,
Morocco
Mohammed VI Center for Research and Innovation (CM6), Rabat 10000, Morocco
;
    'Ansar, MHammed' .
;
Laboratory of Medicinal Chemistry, Drug Sciences Research Center,
Faculty of Medicine and Pharmacy, Mohammed V University in Rabat,
Morocco
;
_publ_section_synopsis
;
An intramolecular C---H...O hydrogen bond helps to determine the conformation
of the title molecule in which the 2-chlorobenzyl group is rotationally
disordered.
;
data_I
_audit_creation_method     'SHELXL-2019/1'
_chemical_name_systematic
;\
2-[4-(2-Chlorobenzyl)-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl]-\
N-(4-fluorophenyl)acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H17 Cl F N3 O2'
_chemical_formula_sum     'C20 H17 Cl F N3 O2'
_chemical_formula_iupac     'C20 H17 Cl F N3 O2'
_chemical_formula_weight     385.82
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.0602(13)
_cell_length_b     6.7704(9)
_cell_length_c     14.524(2)
_cell_angle_alpha     90
_cell_angle_beta     110.168(2)
_cell_angle_gamma     90
_cell_volume     928.6(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3275
_cell_measurement_theta_min     3.0181
_cell_measurement_theta_max     23.6233
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.194
_exptl_crystal_size_mid     0.143
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.380
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.236
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min     0.80
_exptl_absorpt_correction_T_max     0.98
_exptl_special_details
;
The diffraction data were collected in three sets of 363 frames
(0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40
sec/frame was used.
;
_diffrn_ambient_temperature     150(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_source_power     1.50
_diffrn_source_voltage     50
_diffrn_source_current     30.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_device     'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     7.3910
_diffrn_reflns_number     6266
_diffrn_reflns_av_R_equivalents     0.0390
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_theta_min     3.018
_diffrn_reflns_theta_max     23.880
_diffrn_reflns_theta_full     23.880
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å) and were
included as riding contributions with isotropic displacement parameters
1.2 - 1.5 times those of the attached atoms. That attached to nitrogen was
located in a difference map and refined with a DFIX 0.91 0.01 instruction.
The o-chlorobenzyl group is rotationally disoordered over two sites
177.2(5)° apart in a 0.656(2)/0.344(2) ratio. The two components were
refined as rigid hexagons with additional restraints to make their
geometries comparable. One reflection affected by the beam stop was omitted
from the final refinement.
;
_reflns_number_total     2856
_reflns_number_gt     2376
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0610
_refine_ls_R_factor_gt     0.0483
_refine_ls_wR_factor_gt     0.1210
_refine_ls_wR_factor_ref     0.1308
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.032
_refine_ls_number_reflns     2856
_refine_ls_number_parameters     240
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0712P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.266
_refine_diff_density_min     -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 904 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     -0.01(7)
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'
    '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'
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.7132(2) 0.6802(4) 0.94862(15) 0.0618(6) Uani d 0.656(2) A 1
    Cl Cl1A 0.3896(4) 0.3635(7) 0.6576(3) 0.0618(6) Uani d 0.344(2) A 2
    F F1 0.9061(5) 0.0075(7) 0.0379(3) 0.1107(17) Uani d 1 . .
    O O1 0.9168(3) 0.3291(5) 0.6332(3) 0.0492(9) Uani d 1 . .
    O O2 0.7561(3) 0.3559(5) 0.4072(2) 0.0485(9) Uani d 1 . .
    N N1 0.8281(4) 0.6205(5) 0.5611(3) 0.0390(9) Uani d 1 . .
    N N2 0.7474(4) 0.7866(6) 0.5485(3) 0.0400(9) Uani d 1 . .
    N N3 0.9225(4) 0.4816(6) 0.3484(3) 0.0391(9) Uani d 1 . .
    H H3 0.983416 0.579248 0.357540 0.047 Uiso calc 1 . .
    C C7 0.5560(15) 0.6816(12) 0.7246(10) 0.046(3) Uani d 0.656(2) A 1
    H H7A 0.463053 0.714697 0.674956 0.055 Uiso calc 0.656(2) A 1
    H H7B 0.585469 0.795035 0.770111 0.055 Uiso calc 0.656(2) A 1
    C C1 0.5373(5) 0.5015(6) 0.7825(3) 0.041(2) Uani d 0.656(2) A 1
    C C2 0.6067(5) 0.4920(7) 0.8834(3) 0.0432(13) Uani d 0.656(2) A 1
    C C3 0.5904(6) 0.3270(8) 0.9354(3) 0.052(2) Uani d 0.656(2) A 1
    H H3A 0.637871 0.320515 1.004371 0.063 Uiso calc 0.656(2) A 1
    C C4 0.5046(6) 0.1717(7) 0.8867(4) 0.059(2) Uani d 0.656(2) A 1
    H H4 0.493389 0.058937 0.922286 0.071 Uiso calc 0.656(2) A 1
    C C5 0.4351(5) 0.1812(7) 0.7858(4) 0.056(2) Uani d 0.656(2) A 1
    H H5 0.376434 0.075013 0.752518 0.067 Uiso calc 0.656(2) A 1
    C C6 0.4514(5) 0.3461(8) 0.7338(3) 0.0432(13) Uani d 0.656(2) A 1
    H H6 0.403960 0.352669 0.664833 0.052 Uiso calc 0.656(2) A 1
    C C7A 0.583(4) 0.712(2) 0.741(2) 0.046(3) Uani d 0.344(2) A 2
    H H7C 0.484915 0.750414 0.700522 0.055 Uiso calc 0.344(2) A 2
    H H7D 0.628844 0.828556 0.780181 0.055 Uiso calc 0.344(2) A 2
    C C1A 0.5776(10) 0.5441(14) 0.8094(7) 0.041(2) Uani d 0.344(2) A 2
    C C2A 0.6600(10) 0.5581(14) 0.9082(7) 0.0432(13) Uani d 0.344(2) A 2
    H H2A 0.718157 0.670747 0.931670 0.052 Uiso calc 0.344(2) A 2
    C C3A 0.6572(11) 0.4075(16) 0.9725(6) 0.052(2) Uani d 0.344(2) A 2
    H H3B 0.713505 0.417063 1.039937 0.063 Uiso calc 0.344(2) A 2
    C C4A 0.5721(13) 0.2427(14) 0.9381(8) 0.059(2) Uani d 0.344(2) A 2
    H H4A 0.570209 0.139715 0.982019 0.071 Uiso calc 0.344(2) A 2
    C C5A 0.4897(12) 0.2286(14) 0.8393(9) 0.056(2) Uani d 0.344(2) A 2
    H H5A 0.431564 0.116050 0.815834 0.067 Uiso calc 0.344(2) A 2
    C C6A 0.4925(10) 0.3793(18) 0.7750(6) 0.0432(13) Uani d 0.344(2) A 2
    C C8 0.6632(4) 0.6569(7) 0.6726(3) 0.0385(11) Uani d 1 . .
    C C9 0.7456(5) 0.4970(7) 0.6832(4) 0.0393(10) Uani d 1 . .
    H H9 0.743747 0.398076 0.729138 0.047 Uiso calc 1 . .
    C C10 0.8370(4) 0.4717(7) 0.6265(3) 0.0374(10) Uani d 1 . .
    C C11 0.6674(4) 0.8051(7) 0.6030(3) 0.0381(11) Uani d 1 . .
    C C12 0.5826(5) 0.9905(8) 0.5867(4) 0.0513(13) Uani d 1 . .
    H H12A 0.606286 1.063382 0.648541 0.077 Uiso calc 1 . .
    H H12B 0.481472 0.957689 0.562809 0.077 Uiso calc 1 . .
    H H12C 0.604076 1.072240 0.537915 0.077 Uiso calc 1 . .
    C C13 0.9116(5) 0.6132(7) 0.4974(4) 0.0429(12) Uani d 1 . .
    H H13A 1.009880 0.574945 0.536509 0.052 Uiso calc 1 . .
    H H13B 0.914605 0.746647 0.470293 0.052 Uiso calc 1 . .
    C C14 0.8535(5) 0.4690(7) 0.4135(3) 0.0393(11) Uani d 1 . .
    C C15 0.9084(4) 0.3573(7) 0.2676(3) 0.0410(11) Uani d 1 . .
    C C16 0.8316(5) 0.1846(8) 0.2489(3) 0.0450(11) Uani d 1 . .
    H H16 0.778599 0.147835 0.289062 0.054 Uiso calc 1 . .
    C C17 0.8311(6) 0.0641(9) 0.1718(4) 0.0572(14) Uani d 1 . .
    H H17 0.779684 -0.056479 0.159180 0.069 Uiso calc 1 . .
    C C18 0.9065(6) 0.1228(10) 0.1143(4) 0.0662(17) Uani d 1 . .
    C C19 0.9804(7) 0.2951(11) 0.1287(4) 0.0687(17) Uani d 1 . .
    H H19 1.029488 0.333303 0.086165 0.082 Uiso calc 1 . .
    C C20 0.9824(5) 0.4130(9) 0.2065(4) 0.0526(14) Uani d 1 . .
    H H20 1.034536 0.532974 0.218520 0.063 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C2 . 1.723(4) ?
    Cl1A C6A . 1.666(9) ?
    F1 C18 . 1.355(7) ?
    O1 C10 . 1.237(5) ?
    O2 C14 . 1.222(5) ?
    N1 N2 . 1.362(5) ?
    N1 C10 . 1.366(6) ?
    N1 C13 . 1.450(6) ?
    N2 C11 . 1.314(6) ?
    N3 C14 . 1.356(5) ?
    N3 C15 . 1.410(6) ?
    N3 H3 . 0.8800 ?
    C7 C8 . 1.525(6) ?
    C7 C1 . 1.529(6) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C1 C2 . 1.3900 ?
    C1 C6 . 1.3900 ?
    C2 C3 . 1.3900 ?
    C3 C4 . 1.3900 ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.3900 ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3900 ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7A C8 . 1.524(7) ?
    C7A C1A . 1.529(6) ?
    C7A H7C . 0.9900 ?
    C7A H7D . 0.9900 ?
    C1A C2A . 1.3900 ?
    C1A C6A . 1.3900 ?
    C2A C3A . 1.3900 ?
    C2A H2A . 0.9500 ?
    C3A C4A . 1.3900 ?
    C3A H3B . 0.9500 ?
    C4A C5A . 1.3900 ?
    C4A H4A . 0.9500 ?
    C5A C6A . 1.3900 ?
    C5A H5A . 0.9500 ?
    C8 C9 . 1.340(6) ?
    C8 C11 . 1.435(7) ?
    C9 C10 . 1.441(6) ?
    C9 H9 . 0.9500 ?
    C11 C12 . 1.490(6) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.512(7) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C15 C16 . 1.376(7) ?
    C15 C20 . 1.393(6) ?
    C16 C17 . 1.384(7) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.367(8) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.360(9) ?
    C19 C20 . 1.378(8) ?
    C19 H19 . 0.9500 ?
    C20 H20 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 N1 C10 . . 126.5(4) ?
    N2 N1 C13 . . 113.1(4) ?
    C10 N1 C13 . . 120.3(4) ?
    C11 N2 N1 . . 117.3(4) ?
    C14 N3 C15 . . 127.9(4) ?
    C14 N3 H3 . . 116.0 ?
    C15 N3 H3 . . 116.0 ?
    C8 C7 C1 . . 115.3(4) ?
    C8 C7 H7A . . 108.4 ?
    C1 C7 H7A . . 108.4 ?
    C8 C7 H7B . . 108.4 ?
    C1 C7 H7B . . 108.4 ?
    H7A C7 H7B . . 107.5 ?
    C2 C1 C6 . . 120.0 ?
    C2 C1 C7 . . 120.3(7) ?
    C6 C1 C7 . . 119.7(7) ?
    C1 C2 C3 . . 120.0 ?
    C1 C2 Cl1 . . 122.4(3) ?
    C3 C2 Cl1 . . 117.6(3) ?
    C4 C3 C2 . . 120.0 ?
    C4 C3 H3A . . 120.0 ?
    C2 C3 H3A . . 120.0 ?
    C3 C4 C5 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C6 C5 C4 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C5 C6 C1 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C1 C6 H6 . . 120.0 ?
    C8 C7A C1A . . 112.7(6) ?
    C8 C7A H7C . . 109.1 ?
    C1A C7A H7C . . 109.1 ?
    C8 C7A H7D . . 109.1 ?
    C1A C7A H7D . . 109.1 ?
    H7C C7A H7D . . 107.8 ?
    C2A C1A C6A . . 120.0 ?
    C2A C1A C7A . . 118.8(17) ?
    C6A C1A C7A . . 121.2(17) ?
    C1A C2A C3A . . 120.0 ?
    C1A C2A H2A . . 120.0 ?
    C3A C2A H2A . . 120.0 ?
    C4A C3A C2A . . 120.0 ?
    C4A C3A H3B . . 120.0 ?
    C2A C3A H3B . . 120.0 ?
    C5A C4A C3A . . 120.0 ?
    C5A C4A H4A . . 120.0 ?
    C3A C4A H4A . . 120.0 ?
    C4A C5A C6A . . 120.0 ?
    C4A C5A H5A . . 120.0 ?
    C6A C5A H5A . . 120.0 ?
    C5A C6A C1A . . 120.0 ?
    C5A C6A Cl1A . . 119.4(7) ?
    C1A C6A Cl1A . . 120.5(8) ?
    C9 C8 C11 . . 118.6(4) ?
    C9 C8 C7A . . 124.8(6) ?
    C11 C8 C7A . . 115.8(5) ?
    C9 C8 C7 . . 123.1(5) ?
    C11 C8 C7 . . 118.0(4) ?
    C8 C9 C10 . . 121.4(4) ?
    C8 C9 H9 . . 119.3 ?
    C10 C9 H9 . . 119.3 ?
    O1 C10 N1 . . 121.0(4) ?
    O1 C10 C9 . . 124.9(4) ?
    N1 C10 C9 . . 114.1(4) ?
    N2 C11 C8 . . 122.0(4) ?
    N2 C11 C12 . . 114.9(4) ?
    C8 C11 C12 . . 123.1(4) ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N1 C13 C14 . . 112.8(4) ?
    N1 C13 H13A . . 109.0 ?
    C14 C13 H13A . . 109.0 ?
    N1 C13 H13B . . 109.0 ?
    C14 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    O2 C14 N3 . . 125.2(4) ?
    O2 C14 C13 . . 122.9(4) ?
    N3 C14 C13 . . 111.9(4) ?
    C16 C15 C20 . . 119.4(4) ?
    C16 C15 N3 . . 124.1(4) ?
    C20 C15 N3 . . 116.5(4) ?
    C15 C16 C17 . . 120.4(5) ?
    C15 C16 H16 . . 119.8 ?
    C17 C16 H16 . . 119.8 ?
    C18 C17 C16 . . 118.4(5) ?
    C18 C17 H17 . . 120.8 ?
    C16 C17 H17 . . 120.8 ?
    F1 C18 C19 . . 117.9(5) ?
    F1 C18 C17 . . 119.1(5) ?
    C19 C18 C17 . . 123.0(5) ?
    C18 C19 C20 . . 118.4(5) ?
    C18 C19 H19 . . 120.8 ?
    C20 C19 H19 . . 120.8 ?
    C19 C20 C15 . . 120.4(5) ?
    C19 C20 H20 . . 119.8 ?
    C15 C20 H20 . . 119.8 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 N1 N2 C11 . . . . -1.5(6) ?
    C13 N1 N2 C11 . . . . 179.6(4) ?
    C8 C7 C1 C2 . . . . 98.6(11) ?
    C8 C7 C1 C6 . . . . -80.7(11) ?
    C6 C1 C2 C3 . . . . 0.0 ?
    C7 C1 C2 C3 . . . . -179.3(3) ?
    C6 C1 C2 Cl1 . . . . -179.3(4) ?
    C7 C1 C2 Cl1 . . . . 1.4(4) ?
    C1 C2 C3 C4 . . . . 0.0 ?
    Cl1 C2 C3 C4 . . . . 179.3(4) ?
    C2 C3 C4 C5 . . . . 0.0 ?
    C3 C4 C5 C6 . . . . 0.0 ?
    C4 C5 C6 C1 . . . . 0.0 ?
    C2 C1 C6 C5 . . . . 0.0 ?
    C7 C1 C6 C5 . . . . 179.3(3) ?
    C8 C7A C1A C2A . . . . 107(2) ?
    C8 C7A C1A C6A . . . . -73(2) ?
    C6A C1A C2A C3A . . . . 0.0 ?
    C7A C1A C2A C3A . . . . 179.9(4) ?
    C1A C2A C3A C4A . . . . 0.0 ?
    C2A C3A C4A C5A . . . . 0.0 ?
    C3A C4A C5A C6A . . . . 0.0 ?
    C4A C5A C6A C1A . . . . 0.0 ?
    C4A C5A C6A Cl1A . . . . -178.2(7) ?
    C2A C1A C6A C5A . . . . 0.0 ?
    C7A C1A C6A C5A . . . . -179.9(4) ?
    C2A C1A C6A Cl1A . . . . 178.2(7) ?
    C7A C1A C6A Cl1A . . . . -1.8(8) ?
    C1A C7A C8 C9 . . . . -13(3) ?
    C1A C7A C8 C11 . . . . 177.5(16) ?
    C1 C7 C8 C9 . . . . -5.9(15) ?
    C1 C7 C8 C11 . . . . 168.9(8) ?
    C11 C8 C9 C10 . . . . -0.1(7) ?
    C7A C8 C9 C10 . . . . -169.2(19) ?
    C7 C8 C9 C10 . . . . 174.7(9) ?
    N2 N1 C10 O1 . . . . -178.3(4) ?
    C13 N1 C10 O1 . . . . 0.6(6) ?
    N2 N1 C10 C9 . . . . 2.5(6) ?
    C13 N1 C10 C9 . . . . -178.7(4) ?
    C8 C9 C10 O1 . . . . 179.2(5) ?
    C8 C9 C10 N1 . . . . -1.6(6) ?
    N1 N2 C11 C8 . . . . -0.5(6) ?
    N1 N2 C11 C12 . . . . 179.5(4) ?
    C9 C8 C11 N2 . . . . 1.2(7) ?
    C7A C8 C11 N2 . . . . 171.4(18) ?
    C7 C8 C11 N2 . . . . -173.8(8) ?
    C9 C8 C11 C12 . . . . -178.7(4) ?
    C7A C8 C11 C12 . . . . -8.6(18) ?
    C7 C8 C11 C12 . . . . 6.2(10) ?
    N2 N1 C13 C14 . . . . -105.4(4) ?
    C10 N1 C13 C14 . . . . 75.6(5) ?
    C15 N3 C14 O2 . . . . -7.4(7) ?
    C15 N3 C14 C13 . . . . 172.5(4) ?
    N1 C13 C14 O2 . . . . -7.6(7) ?
    N1 C13 C14 N3 . . . . 172.5(4) ?
    C14 N3 C15 C16 . . . . -8.1(7) ?
    C14 N3 C15 C20 . . . . 174.3(4) ?
    C20 C15 C16 C17 . . . . 1.9(7) ?
    N3 C15 C16 C17 . . . . -175.5(5) ?
    C15 C16 C17 C18 . . . . -1.1(8) ?
    C16 C17 C18 F1 . . . . -179.4(5) ?
    C16 C17 C18 C19 . . . . -0.8(9) ?
    F1 C18 C19 C20 . . . . -179.6(6) ?
    C17 C18 C19 C20 . . . . 1.8(10) ?
    C18 C19 C20 C15 . . . . -1.0(9) ?
    C16 C15 C20 C19 . . . . -0.9(8) ?
    N3 C15 C20 C19 . . . . 176.8(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N3 H3 O1 2_756 0.88 1.95 2.815(5) 168.1 yes
    C7 H7A O2 2_656 0.99 2.32 3.282(15) 164 y
    C16 H16 O2 . 0.95 2.29 2.900(6) 121 yes
    C19 H19 F1 2_755 0.95 2.42 3.336(7) 162 yes
_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.
;
_shelx_estimated_absorpt_T_min     0.956
_shelx_estimated_absorpt_T_max     0.981
