##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_general
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-11-10
_journal_date_accepted     2011-11-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     12
_journal_page_first     o3330
_journal_page_last     o3331
_journal_paper_category     QO
_journal_coeditor_code     HG5137
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
Edward.Tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;\
[3-({(E)-2-[(4-Fluorophenyl)carbamothioyl]hydrazinylidene}methyl)-4-\
hydroxybenzyl]methyltriphenylphosphonium chloride
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sinniah, Saravana Kumar ' .
;
Institute of Biological Sciences, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tan, Kong Wai'
;
Additional correspondence author, e-mail: tkongwai@yahoo.com.
;
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Sim, Kae Shin' .
;
Institute of Biological Sciences, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
and Chemistry Department,
Faculty of Science,
King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
[3-({(E)-2-[(4-Fluorophenyl)carbamothioyl]hydrazinylidene}methyl)-4-
hydroxybenzyl]methyltriphenylphosphonium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C33 H28 F N3 O P S, Cl'
_chemical_formula_sum     'C33 H28 Cl F N3 O P S'
_chemical_formula_iupac     'C33 H28 F N3 O P S +, Cl -'
_chemical_formula_weight     600.06
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     17.5495(6)
_cell_length_b     9.4617(3)
_cell_length_c     19.0569(6)
_cell_angle_alpha     90.00
_cell_angle_beta     107.298(4)
_cell_angle_gamma     90.00
_cell_volume     3021.24(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3679
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     29.21
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.319
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     0.286
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.9191
_exptl_absorpt_correction_T_max     0.9450
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                     'Agilent SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     12024
_diffrn_reflns_av_R_equivalents     0.0402
_diffrn_reflns_av_sigmaI/netI     0.0710
_diffrn_reflns_theta_min     2.43
_diffrn_reflns_theta_max     26.50
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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 >
2σ(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.
;
_reflns_number_total     6178
_reflns_number_gt     4374
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0876
_refine_ls_R_factor_gt     0.0544
_refine_ls_wR_factor_gt     0.1252
_refine_ls_wR_factor_ref     0.1537
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     6178
_refine_ls_number_parameters     382
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0639P)²+2.4147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.623
_refine_diff_density_min     -0.375
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                        'X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.91349(4) 0.62474(8) 0.85886(4) 0.02368(19) Uani d . 1 1 . .
    P P1 0.83503(5) 1.15927(8) 0.50731(4) 0.0200(2) Uani d . 1 1 . .
    S S1 0.48397(5) 0.43111(9) 0.38203(4) 0.0283(2) Uani d . 1 1 . .
    F F1 0.58227(13) 0.3645(3) 0.08217(11) 0.0512(6) Uani d . 1 1 . .
    O O1 0.78340(13) 0.6681(2) 0.71688(12) 0.0280(5) Uani d D 1 1 . .
    N N1 0.67395(15) 0.6310(3) 0.49955(14) 0.0253(6) Uani d . 1 1 . .
    N N2 0.60362(15) 0.5553(3) 0.47947(14) 0.0262(6) Uani d D 1 1 . .
    N N3 0.61878(16) 0.5438(3) 0.36568(14) 0.0276(6) Uani d D 1 1 . .
    C C1 0.74010(17) 1.1072(3) 0.44749(15) 0.0212(6) Uani d . 1 1 . .
    C C2 0.66882(19) 1.1318(4) 0.46326(18) 0.0316(8) Uani d . 1 1 . .
    H H2A 0.6687 1.1812 0.5066 0.038 Uiso calc R 1 1 . .
    C C3 0.5978(2) 1.0833(4) 0.41479(19) 0.0386(9) Uani d . 1 1 . .
    H H3A 0.5487 1.0983 0.4253 0.046 Uiso calc R 1 1 . .
    C C4 0.5985(2) 1.0125(4) 0.35068(19) 0.0368(8) Uani d . 1 1 . .
    H H4 0.5501 0.9769 0.3185 0.044 Uiso calc R 1 1 . .
    C C5 0.66894(19) 0.9939(3) 0.33374(18) 0.0301(7) Uani d . 1 1 . .
    H H5 0.6688 0.9491 0.2891 0.036 Uiso calc R 1 1 . .
    C C6 0.73978(19) 1.0410(3) 0.38218(17) 0.0266(7) Uani d . 1 1 . .
    H H6 0.7885 1.0280 0.3708 0.032 Uiso calc R 1 1 . .
    C C7 0.87455(18) 1.2911(3) 0.46083(16) 0.0245(7) Uani d . 1 1 . .
    C C8 0.8314(2) 1.4157(4) 0.4393(3) 0.0535(12) Uani d . 1 1 . .
    H H8 0.7814 1.4273 0.4482 0.064 Uiso calc R 1 1 . .
    C C9 0.8606(2) 1.5209(4) 0.4055(3) 0.0553(12) Uani d . 1 1 . .
    H H9 0.8313 1.6061 0.3919 0.066 Uiso calc R 1 1 . .
    C C10 0.9327(2) 1.5034(4) 0.39112(18) 0.0351(8) Uani d . 1 1 . .
    H H10 0.9522 1.5757 0.3664 0.042 Uiso calc R 1 1 . .
    C C11 0.9762(2) 1.3819(4) 0.4124(2) 0.0373(9) Uani d . 1 1 . .
    H H11 1.0258 1.3699 0.4025 0.045 Uiso calc R 1 1 . .
    C C12 0.9474(2) 1.2765(3) 0.4485(2) 0.0352(8) Uani d . 1 1 . .
    H H12 0.9782 1.1937 0.4649 0.042 Uiso calc R 1 1 . .
    C C13 0.82929(18) 1.2290(3) 0.59315(17) 0.0247(7) Uani d . 1 1 . .
    C C14 0.8756(2) 1.3467(4) 0.62295(19) 0.0340(8) Uani d . 1 1 . .
    H H14 0.9023 1.3982 0.5945 0.041 Uiso calc R 1 1 . .
    C C15 0.8824(2) 1.3879(4) 0.6947(2) 0.0420(9) Uani d . 1 1 . .
    H H15 0.9143 1.4672 0.7153 0.050 Uiso calc R 1 1 . .
    C C16 0.8437(2) 1.3158(4) 0.7353(2) 0.0427(9) Uani d . 1 1 . .
    H H16 0.8484 1.3460 0.7839 0.051 Uiso calc R 1 1 . .
    C C17 0.7978(2) 1.1993(4) 0.70702(19) 0.0372(9) Uani d . 1 1 . .
    H H17 0.7711 1.1495 0.7362 0.045 Uiso calc R 1 1 . .
    C C18 0.7904(2) 1.1543(4) 0.63557(18) 0.0311(8) Uani d . 1 1 . .
    H H18 0.7591 1.0736 0.6159 0.037 Uiso calc R 1 1 . .
    C C19 0.89916(17) 1.0055(3) 0.52567(15) 0.0187(6) Uani d . 1 1 . .
    H H19A 0.8972 0.9582 0.4788 0.022 Uiso calc R 1 1 . .
    H H19B 0.9549 1.0350 0.5499 0.022 Uiso calc R 1 1 . .
    C C20 0.87243(17) 0.9036(3) 0.57481(15) 0.0202(6) Uani d . 1 1 . .
    C C21 0.91367(18) 0.8996(3) 0.64994(16) 0.0229(7) Uani d . 1 1 . .
    H H21 0.9612 0.9532 0.6684 0.027 Uiso calc R 1 1 . .
    C C22 0.88599(18) 0.8185(3) 0.69762(16) 0.0241(7) Uani d . 1 1 . .
    H H22 0.9151 0.8154 0.7483 0.029 Uiso calc R 1 1 . .
    C C23 0.81585(18) 0.7415(3) 0.67172(16) 0.0213(6) Uani d . 1 1 . .
    C C24 0.77585(17) 0.7385(3) 0.59589(16) 0.0207(6) Uani d . 1 1 . .
    C C25 0.80530(17) 0.8198(3) 0.54838(16) 0.0205(6) Uani d . 1 1 . .
    H H25 0.7788 0.8175 0.4971 0.025 Uiso calc R 1 1 . .
    C C26 0.70392(18) 0.6542(3) 0.56854(17) 0.0242(7) Uani d . 1 1 . .
    H H26 0.6788 0.6159 0.6021 0.029 Uiso calc R 1 1 . .
    C C27 0.57265(18) 0.5127(3) 0.40903(16) 0.0244(7) Uani d . 1 1 . .
    C C28 0.60814(18) 0.4968(4) 0.29226(16) 0.0272(7) Uani d . 1 1 . .
    C C29 0.6181(2) 0.5918(4) 0.24096(19) 0.0366(8) Uani d . 1 1 . .
    H H29 0.6300 0.6879 0.2542 0.044 Uiso calc R 1 1 . .
    C C30 0.6108(2) 0.5470(4) 0.1695(2) 0.0392(9) Uani d . 1 1 . .
    H H30 0.6181 0.6110 0.1337 0.047 Uiso calc R 1 1 . .
    C C31 0.59293(19) 0.4090(4) 0.15287(18) 0.0344(8) Uani d . 1 1 . .
    C C32 0.5849(2) 0.3102(4) 0.20287(19) 0.0355(8) Uani d . 1 1 . .
    H H32 0.5738 0.2140 0.1894 0.043 Uiso calc R 1 1 . .
    C C33 0.59363(19) 0.3568(3) 0.27397(17) 0.0292(7) Uani d . 1 1 . .
    H H33 0.5895 0.2911 0.3104 0.035 Uiso calc R 1 1 . .
    H H1 0.8166(17) 0.658(4) 0.7584(10) 0.044(11) Uiso d D 1 1 . .
    H H2 0.576(2) 0.541(4) 0.5103(18) 0.055(12) Uiso d D 1 1 . .
    H H3 0.6576(14) 0.604(3) 0.3836(17) 0.033(10) Uiso d D 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
    P1 C1 . 1.786(3) ?
    P1 C7 . 1.785(3) ?
    P1 C13 . 1.794(3) ?
    P1 C19 . 1.808(3) ?
    S1 C27 . 1.675(3) ?
    F1 C31 . 1.370(4) ?
    O1 C23 . 1.356(3) ?
    O1 H1 . 0.837(10) ?
    N1 C26 . 1.281(4) ?
    N1 N2 . 1.379(3) ?
    N2 C27 . 1.351(4) ?
    N2 H2 . 0.881(10) ?
    N3 C27 . 1.350(4) ?
    N3 C28 . 1.427(4) ?
    N3 H3 . 0.874(10) ?
    C1 C2 . 1.390(4) ?
    C1 C6 . 1.392(4) ?
    C2 C3 . 1.391(5) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.397(5) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.379(5) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.383(4) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C12 . 1.373(4) ?
    C7 C8 . 1.394(5) ?
    C8 C9 . 1.365(5) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.383(5) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.373(5) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.390(4) ?
    C11 H11 . 0.9500 ?
    C12 H12 . 0.9500 ?
    C13 C18 . 1.396(4) ?
    C13 C14 . 1.395(4) ?
    C14 C15 . 1.392(5) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.355(5) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.378(5) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.395(4) ?
    C17 H17 . 0.9500 ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.513(4) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 C25 . 1.385(4) ?
    C20 C21 . 1.400(4) ?
    C21 C22 . 1.383(4) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.388(4) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.407(4) ?
    C24 C25 . 1.399(4) ?
    C24 C26 . 1.453(4) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    C28 C33 . 1.374(5) ?
    C28 C29 . 1.377(4) ?
    C29 C30 . 1.394(5) ?
    C29 H29 . 0.9500 ?
    C30 C31 . 1.358(5) ?
    C30 H30 . 0.9500 ?
    C31 C32 . 1.372(5) ?
    C32 C33 . 1.389(4) ?
    C32 H32 . 0.9500 ?
    C33 H33 . 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
    C1 P1 C7 . . 107.60(14) ?
    C1 P1 C13 . . 112.88(14) ?
    C7 P1 C13 . . 109.30(15) ?
    C1 P1 C19 . . 108.09(14) ?
    C7 P1 C19 . . 110.30(14) ?
    C13 P1 C19 . . 108.65(14) ?
    C23 O1 H1 . . 111(3) ?
    C26 N1 N2 . . 115.7(2) ?
    C27 N2 N1 . . 119.5(2) ?
    C27 N2 H2 . . 119(3) ?
    N1 N2 H2 . . 122(3) ?
    C27 N3 C28 . . 127.2(3) ?
    C27 N3 H3 . . 116(2) ?
    C28 N3 H3 . . 116(2) ?
    C2 C1 C6 . . 120.3(3) ?
    C2 C1 P1 . . 123.0(2) ?
    C6 C1 P1 . . 116.7(2) ?
    C3 C2 C1 . . 119.2(3) ?
    C3 C2 H2A . . 120.4 ?
    C1 C2 H2A . . 120.4 ?
    C2 C3 C4 . . 120.0(3) ?
    C2 C3 H3A . . 120.0 ?
    C4 C3 H3A . . 120.0 ?
    C5 C4 C3 . . 120.5(3) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 119.5(3) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C5 C6 C1 . . 120.4(3) ?
    C5 C6 H6 . . 119.8 ?
    C1 C6 H6 . . 119.8 ?
    C12 C7 C8 . . 119.1(3) ?
    C12 C7 P1 . . 122.2(2) ?
    C8 C7 P1 . . 118.6(2) ?
    C9 C8 C7 . . 120.6(3) ?
    C9 C8 H8 . . 119.7 ?
    C7 C8 H8 . . 119.7 ?
    C8 C9 C10 . . 120.0(4) ?
    C8 C9 H9 . . 120.0 ?
    C10 C9 H9 . . 120.0 ?
    C11 C10 C9 . . 120.2(3) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C10 C11 C12 . . 119.6(3) ?
    C10 C11 H11 . . 120.2 ?
    C12 C11 H11 . . 120.2 ?
    C7 C12 C11 . . 120.4(3) ?
    C7 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C18 C13 C14 . . 119.6(3) ?
    C18 C13 P1 . . 120.8(2) ?
    C14 C13 P1 . . 118.7(2) ?
    C15 C14 C13 . . 119.5(3) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C16 C15 C14 . . 120.6(3) ?
    C16 C15 H15 . . 119.7 ?
    C14 C15 H15 . . 119.7 ?
    C15 C16 C17 . . 120.9(3) ?
    C15 C16 H16 . . 119.6 ?
    C17 C16 H16 . . 119.6 ?
    C16 C17 C18 . . 120.0(3) ?
    C16 C17 H17 . . 120.0 ?
    C18 C17 H17 . . 120.0 ?
    C13 C18 C17 . . 119.4(3) ?
    C13 C18 H18 . . 120.3 ?
    C17 C18 H18 . . 120.3 ?
    C20 C19 P1 . . 110.05(19) ?
    C20 C19 H19A . . 109.7 ?
    P1 C19 H19A . . 109.7 ?
    C20 C19 H19B . . 109.7 ?
    P1 C19 H19B . . 109.7 ?
    H19A C19 H19B . . 108.2 ?
    C25 C20 C21 . . 118.8(3) ?
    C25 C20 C19 . . 121.8(3) ?
    C21 C20 C19 . . 119.3(3) ?
    C22 C21 C20 . . 120.7(3) ?
    C22 C21 H21 . . 119.6 ?
    C20 C21 H21 . . 119.6 ?
    C21 C22 C23 . . 120.3(3) ?
    C21 C22 H22 . . 119.8 ?
    C23 C22 H22 . . 119.8 ?
    O1 C23 C22 . . 122.6(3) ?
    O1 C23 C24 . . 117.8(3) ?
    C22 C23 C24 . . 119.6(3) ?
    C25 C24 C23 . . 119.1(3) ?
    C25 C24 C26 . . 121.2(3) ?
    C23 C24 C26 . . 119.6(3) ?
    C20 C25 C24 . . 121.2(3) ?
    C20 C25 H25 . . 119.4 ?
    C24 C25 H25 . . 119.4 ?
    N1 C26 C24 . . 120.7(3) ?
    N1 C26 H26 . . 119.7 ?
    C24 C26 H26 . . 119.7 ?
    N3 C27 N2 . . 113.9(3) ?
    N3 C27 S1 . . 125.7(2) ?
    N2 C27 S1 . . 120.3(2) ?
    C33 C28 C29 . . 120.2(3) ?
    C33 C28 N3 . . 120.7(3) ?
    C29 C28 N3 . . 119.0(3) ?
    C28 C29 C30 . . 120.0(3) ?
    C28 C29 H29 . . 120.0 ?
    C30 C29 H29 . . 120.0 ?
    C31 C30 C29 . . 117.9(3) ?
    C31 C30 H30 . . 121.0 ?
    C29 C30 H30 . . 121.0 ?
    C30 C31 F1 . . 118.7(3) ?
    C30 C31 C32 . . 123.8(3) ?
    F1 C31 C32 . . 117.5(3) ?
    C31 C32 C33 . . 117.2(3) ?
    C31 C32 H32 . . 121.4 ?
    C33 C32 H32 . . 121.4 ?
    C28 C33 C32 . . 120.8(3) ?
    C28 C33 H33 . . 119.6 ?
    C32 C33 H33 . . 119.6 ?
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
    C26 N1 N2 C27 . . . . -172.7(3) ?
    C7 P1 C1 C2 . . . . -114.6(3) ?
    C13 P1 C1 C2 . . . . 6.1(3) ?
    C19 P1 C1 C2 . . . . 126.3(3) ?
    C7 P1 C1 C6 . . . . 64.5(3) ?
    C13 P1 C1 C6 . . . . -174.8(2) ?
    C19 P1 C1 C6 . . . . -54.6(3) ?
    C6 C1 C2 C3 . . . . 3.2(5) ?
    P1 C1 C2 C3 . . . . -177.8(3) ?
    C1 C2 C3 C4 . . . . -0.9(5) ?
    C2 C3 C4 C5 . . . . -2.0(6) ?
    C3 C4 C5 C6 . . . . 2.6(5) ?
    C4 C5 C6 C1 . . . . -0.3(5) ?
    C2 C1 C6 C5 . . . . -2.6(5) ?
    P1 C1 C6 C5 . . . . 178.2(2) ?
    C1 P1 C7 C12 . . . . -123.2(3) ?
    C13 P1 C7 C12 . . . . 113.9(3) ?
    C19 P1 C7 C12 . . . . -5.5(3) ?
    C1 P1 C7 C8 . . . . 59.7(3) ?
    C13 P1 C7 C8 . . . . -63.2(3) ?
    C19 P1 C7 C8 . . . . 177.4(3) ?
    C12 C7 C8 C9 . . . . 0.9(6) ?
    P1 C7 C8 C9 . . . . 178.1(4) ?
    C7 C8 C9 C10 . . . . 1.2(7) ?
    C8 C9 C10 C11 . . . . -1.6(7) ?
    C9 C10 C11 C12 . . . . -0.1(6) ?
    C8 C7 C12 C11 . . . . -2.6(6) ?
    P1 C7 C12 C11 . . . . -179.7(3) ?
    C10 C11 C12 C7 . . . . 2.2(6) ?
    C1 P1 C13 C18 . . . . 51.5(3) ?
    C7 P1 C13 C18 . . . . 171.2(3) ?
    C19 P1 C13 C18 . . . . -68.4(3) ?
    C1 P1 C13 C14 . . . . -139.3(3) ?
    C7 P1 C13 C14 . . . . -19.6(3) ?
    C19 P1 C13 C14 . . . . 100.8(3) ?
    C18 C13 C14 C15 . . . . 0.0(5) ?
    P1 C13 C14 C15 . . . . -169.3(3) ?
    C13 C14 C15 C16 . . . . -0.8(5) ?
    C14 C15 C16 C17 . . . . 0.8(6) ?
    C15 C16 C17 C18 . . . . -0.2(6) ?
    C14 C13 C18 C17 . . . . 0.6(5) ?
    P1 C13 C18 C17 . . . . 169.7(3) ?
    C16 C17 C18 C13 . . . . -0.5(5) ?
    C1 P1 C19 C20 . . . . -71.1(2) ?
    C7 P1 C19 C20 . . . . 171.5(2) ?
    C13 P1 C19 C20 . . . . 51.7(2) ?
    P1 C19 C20 C25 . . . . 75.2(3) ?
    P1 C19 C20 C21 . . . . -100.9(3) ?
    C25 C20 C21 C22 . . . . -2.9(4) ?
    C19 C20 C21 C22 . . . . 173.3(3) ?
    C20 C21 C22 C23 . . . . -1.1(5) ?
    C21 C22 C23 O1 . . . . -175.4(3) ?
    C21 C22 C23 C24 . . . . 4.4(4) ?
    O1 C23 C24 C25 . . . . 176.3(3) ?
    C22 C23 C24 C25 . . . . -3.5(4) ?
    O1 C23 C24 C26 . . . . -2.2(4) ?
    C22 C23 C24 C26 . . . . 178.0(3) ?
    C21 C20 C25 C24 . . . . 3.8(4) ?
    C19 C20 C25 C24 . . . . -172.4(3) ?
    C23 C24 C25 C20 . . . . -0.6(4) ?
    C26 C24 C25 C20 . . . . 177.9(3) ?
    N2 N1 C26 C24 . . . . -177.1(3) ?
    C25 C24 C26 N1 . . . . 13.1(4) ?
    C23 C24 C26 N1 . . . . -168.4(3) ?
    C28 N3 C27 N2 . . . . 170.9(3) ?
    C28 N3 C27 S1 . . . . -9.9(5) ?
    N1 N2 C27 N3 . . . . 3.7(4) ?
    N1 N2 C27 S1 . . . . -175.5(2) ?
    C27 N3 C28 C33 . . . . -47.5(5) ?
    C27 N3 C28 C29 . . . . 137.0(3) ?
    C33 C28 C29 C30 . . . . 2.2(5) ?
    N3 C28 C29 C30 . . . . 177.7(3) ?
    C28 C29 C30 C31 . . . . 0.7(5) ?
    C29 C30 C31 F1 . . . . 177.3(3) ?
    C29 C30 C31 C32 . . . . -2.8(6) ?
    C30 C31 C32 C33 . . . . 1.8(5) ?
    F1 C31 C32 C33 . . . . -178.3(3) ?
    C29 C28 C33 C32 . . . . -3.2(5) ?
    N3 C28 C33 C32 . . . . -178.6(3) ?
    C31 C32 C33 C28 . . . . 1.2(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
    N3 H3 N1 . 0.874(10) 2.16(3) 2.580(4) 109(3)
    O1 H1 Cl1 . 0.837(10) 2.173(11) 3.005(2) 173(4)
    N2 H2 S1 3_666 0.881(10) 2.579(16) 3.429(3) 162(3)
    C6 H6 Cl1 4_575 0.95 2.69 3.572(3) 154
    C19 H19a Cl1 4_575 0.99 2.51 3.488(3) 168
    C19 H19b Cl1 2_756 0.99 2.59 3.553(3) 165
