##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2012-03-09
_journal_date_accepted     2012-04-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      5
_journal_page_first     o1359
_journal_page_last     o1359
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681201481X
_journal_coeditor_code     RK2344
_publ_contact_author
;
    Siddiqui, Hamid latif
    Institute of Chemistry
    University of the Punjab
    Lahore
    Pakistan
;
_publ_contact_author_email     drhamidlatif@hotmail.com
_publ_contact_author_fax     ' 0092+42-923 1269 '
_publ_contact_author_phone     ' 0092-42-923 0463 '
_publ_section_title
;\
[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2<i>H</i>-1,2-benzothiazin-3-yl]\
(phenyl)methanone
;
loop_
    _publ_author_name
    _publ_author_address
    'Sattar, Nazia'
;
Institute of Chemistry
University of the Punjab
Lahore 54590
Pakistan
;
    'Siddiqui, Hamid Latif'
;
Institute of Chemistry
University of the Punjab
Lahore 54590
Pakistan
;
    'Ahmad, Matloob'
;
Chemistry Department
Govt. College University
Faisalabad
Pakistan
;
    'Akram, Muhammad'
;
Department of Chemistry
Universiti Teknologi Malaysia
81310 UTM Skudai
Johor
Darul Ta'zim
Malaysia
;
    'Parvez, Masood'
;
Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
data_I
_chemical_name_systematic
;
[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2<i>H</i>-1,2-benzothiazin-
3-yl](phenyl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H15 Cl2 N O4 S'
_chemical_formula_sum     'C22 H15 Cl2 N O4 S'
_chemical_formula_iupac     'C22 H15 Cl2 N O4 S'
_chemical_formula_weight     460.32
_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     12.8172(5)
_cell_length_b     9.9215(4)
_cell_length_c     16.7155(5)
_cell_angle_alpha     90.000(2)
_cell_angle_beta     110.511(2)
_cell_angle_gamma     90.000(2)
_cell_volume     1990.89(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8696
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.536
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     944
_exptl_absorpt_coefficient_mu     0.462
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SORTAV</i>; Blessing, 1997)'
_exptl_absorpt_correction_T_min     0.9133
_exptl_absorpt_correction_T_max     0.9297
_exptl_special_details     ?
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     '\w and \f scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16108
_diffrn_reflns_av_R_equivalents     0.0554
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_theta_min     2.69
_diffrn_reflns_theta_max     27.59
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of <i>F</i>^2^ against ALL reflections. The weighted
 <i>R</i>-factor <i>wR</i> and goodness of fit <i>S</i> are based on
 <i>F</i>^2^, conventional <i>R</i>-factors <i>R</i> are based on <i>F</i>,
 with <i>F</i> set to zero for negative <i>F</i>^2^. The threshold expression
 of <i>F</i>^2^ > \s(<i>F</i>^2^) is used only for calculating
 <i>R</i>-factors(gt) <i>etc</i>. and is not relevant to the choice of
 reflections for refinement. <i>R</i>-factors based on <i>F</i>^2^ are
 statistically about twice as large as those based on <i>F</i>, and
 <i>R</i>-factors based on ALL data will be even larger.
;
_reflns_number_total     4592
_reflns_number_gt     3598
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0792
_refine_ls_R_factor_gt     0.0567
_refine_ls_wR_factor_gt     0.1066
_refine_ls_wR_factor_ref     0.1180
_refine_ls_goodness_of_fit_ref     1.110
_refine_ls_restrained_S_all     1.110
_refine_ls_number_reflns     4592
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+2.3517P] where P=(Fo^2^+2Fc^2^)/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     0.328
_refine_diff_density_min     -0.439
_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'
    '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     '<i>COLLECT</i> (Hooft, 1998)'
_computing_cell_refinement     '<i>DENZO</i> (Otwinowski & Minor, 1997)'
_computing_data_reduction     '<i>SCALEPACK</i> (Otwinowski & Minor, 1997)'
_computing_structure_solution     '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_refinement     '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_molecular_graphics     '<i>ORTEP-3</i> (Farrugia, 1997)'
_computing_publication_material     '<i>SHELXL97</i> (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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.52481(7) -0.04749(10) 0.39033(6) 0.0658(3) Uani d . 1 1 . .
    Cl Cl2 0.50174(9) 0.57915(12) 0.37257(7) 0.0804(3) Uani d . 1 1 . .
    S S1 0.87675(5) 0.25684(7) 0.53887(4) 0.03478(16) Uani d . 1 1 . .
    O O1 0.98780(15) 0.2067(2) 0.56375(12) 0.0457(5) Uani d . 1 1 . .
    O O2 0.84712(17) 0.3467(2) 0.59407(11) 0.0465(5) Uani d . 1 1 . .
    O O3 0.79566(17) 0.0186(2) 0.31269(11) 0.0418(5) Uani d . 1 1 . .
    H H3O 0.7866 -0.0624 0.3235 0.050 Uiso calc R 1 1 . .
    O O4 0.77251(15) -0.18006(19) 0.40080(11) 0.0408(5) Uani d . 1 1 . .
    N N1 0.79342(17) 0.1262(2) 0.52149(12) 0.0331(5) Uani d . 1 1 . .
    C C1 0.8421(2) 0.3280(3) 0.43643(16) 0.0339(6) Uani d . 1 1 . .
    C C2 0.8521(2) 0.4653(3) 0.42629(18) 0.0406(6) Uani d . 1 1 . .
    H H2 0.8739 0.5236 0.4744 0.049 Uiso calc R 1 1 . .
    C C3 0.8297(2) 0.5165(3) 0.34482(19) 0.0465(7) Uani d . 1 1 . .
    H H3 0.8365 0.6104 0.3369 0.056 Uiso calc R 1 1 . .
    C C4 0.7977(3) 0.4316(3) 0.27565(18) 0.0483(7) Uani d . 1 1 . .
    H H4 0.7830 0.4676 0.2201 0.058 Uiso calc R 1 1 . .
    C C5 0.7866(2) 0.2949(3) 0.28534(17) 0.0421(7) Uani d . 1 1 . .
    H H5 0.7638 0.2378 0.2366 0.050 Uiso calc R 1 1 . .
    C C6 0.8089(2) 0.2404(3) 0.36662(15) 0.0318(5) Uani d . 1 1 . .
    C C7 0.7989(2) 0.0952(3) 0.37903(15) 0.0326(6) Uani d . 1 1 . .
    C C8 0.7978(2) 0.0396(3) 0.45361(14) 0.0307(5) Uani d . 1 1 . .
    C C9 0.7971(2) -0.1051(3) 0.46462(16) 0.0334(6) Uani d . 1 1 . .
    C C10 0.8276(2) -0.1656(3) 0.55114(16) 0.0357(6) Uani d . 1 1 . .
    C C11 0.9160(2) -0.1140(3) 0.61913(17) 0.0403(6) Uani d . 1 1 . .
    H H11 0.9531 -0.0345 0.6119 0.048 Uiso calc R 1 1 . .
    C C12 0.9498(2) -0.1792(3) 0.69745(18) 0.0463(7) Uani d . 1 1 . .
    H H12 1.0107 -0.1448 0.7438 0.056 Uiso calc R 1 1 . .
    C C13 0.8954(3) -0.2934(3) 0.70810(19) 0.0498(8) Uani d . 1 1 . .
    H H13 0.9190 -0.3376 0.7619 0.060 Uiso calc R 1 1 . .
    C C14 0.8066(3) -0.3445(3) 0.6410(2) 0.0505(8) Uani d . 1 1 . .
    H H14 0.7685 -0.4226 0.6491 0.061 Uiso calc R 1 1 . .
    C C15 0.7735(3) -0.2815(3) 0.56220(19) 0.0448(7) Uani d . 1 1 . .
    H H15 0.7137 -0.3175 0.5157 0.054 Uiso calc R 1 1 . .
    C C16 0.6823(2) 0.1408(3) 0.53043(16) 0.0376(6) Uani d . 1 1 . .
    H H16A 0.6906 0.1968 0.5813 0.045 Uiso calc R 1 1 . .
    H H16B 0.6560 0.0507 0.5403 0.045 Uiso calc R 1 1 . .
    C C17 0.5954(2) 0.2036(3) 0.45391(16) 0.0396(6) Uani d . 1 1 . .
    C C18 0.5232(2) 0.1274(4) 0.38632(19) 0.0502(8) Uani d . 1 1 . .
    C C19 0.4486(3) 0.1900(5) 0.3150(2) 0.0661(11) Uani d . 1 1 . .
    H H19 0.4009 0.1372 0.2695 0.079 Uiso calc R 1 1 . .
    C C20 0.4435(3) 0.3273(5) 0.3101(2) 0.0685(11) Uani d . 1 1 . .
    H H20 0.3933 0.3699 0.2606 0.082 Uiso calc R 1 1 . .
    C C21 0.5114(3) 0.4044(4) 0.37701(19) 0.0564(9) Uani d . 1 1 . .
    C C22 0.5870(2) 0.3432(3) 0.44836(17) 0.0437(7) Uani d . 1 1 . .
    H H22 0.6336 0.3972 0.4938 0.052 Uiso calc R 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0454(4) 0.0807(7) 0.0762(6) -0.0194(4) 0.0274(4) -0.0311(5)
    Cl2 0.0780(7) 0.0882(8) 0.0780(6) 0.0331(6) 0.0310(5) 0.0324(6)
    S1 0.0355(3) 0.0382(4) 0.0259(3) -0.0025(3) 0.0048(2) -0.0050(3)
    O1 0.0316(10) 0.0547(13) 0.0402(10) -0.0033(9) -0.0006(8) -0.0019(9)
    O2 0.0582(13) 0.0452(12) 0.0332(10) -0.0025(10) 0.0124(9) -0.0114(9)
    O3 0.0569(12) 0.0388(11) 0.0303(9) -0.0066(10) 0.0160(9) -0.0086(8)
    O4 0.0440(11) 0.0395(11) 0.0358(10) -0.0041(9) 0.0102(8) -0.0087(8)
    N1 0.0342(11) 0.0379(12) 0.0265(10) -0.0022(10) 0.0100(9) -0.0041(9)
    C1 0.0311(13) 0.0375(15) 0.0310(13) -0.0010(11) 0.0082(10) -0.0024(11)
    C2 0.0414(15) 0.0378(15) 0.0399(15) -0.0015(12) 0.0108(12) -0.0062(12)
    C3 0.0529(18) 0.0349(16) 0.0515(17) 0.0000(13) 0.0178(14) 0.0047(13)
    C4 0.0578(19) 0.0464(18) 0.0389(15) -0.0002(15) 0.0146(14) 0.0081(13)
    C5 0.0469(16) 0.0474(17) 0.0304(13) -0.0005(13) 0.0117(12) -0.0024(12)
    C6 0.0305(12) 0.0366(14) 0.0276(11) -0.0021(11) 0.0092(10) -0.0020(11)
    C7 0.0281(12) 0.0398(15) 0.0290(12) -0.0016(11) 0.0088(10) -0.0074(11)
    C8 0.0276(12) 0.0380(14) 0.0246(11) -0.0008(11) 0.0066(9) -0.0035(10)
    C9 0.0274(12) 0.0388(15) 0.0337(13) -0.0021(11) 0.0103(10) -0.0028(11)
    C10 0.0379(14) 0.0354(14) 0.0349(13) 0.0042(12) 0.0140(11) 0.0028(11)
    C11 0.0391(15) 0.0417(16) 0.0387(14) 0.0041(12) 0.0119(12) 0.0034(12)
    C12 0.0454(16) 0.0536(19) 0.0365(15) 0.0096(14) 0.0102(13) 0.0026(13)
    C13 0.062(2) 0.0496(19) 0.0413(16) 0.0147(16) 0.0226(15) 0.0116(14)
    C14 0.067(2) 0.0375(17) 0.0579(19) 0.0017(15) 0.0351(17) 0.0071(14)
    C15 0.0504(17) 0.0423(17) 0.0449(16) -0.0002(13) 0.0206(14) -0.0016(13)
    C16 0.0365(14) 0.0490(17) 0.0306(13) -0.0006(12) 0.0156(11) -0.0037(12)
    C17 0.0292(13) 0.0628(19) 0.0296(13) 0.0001(13) 0.0138(11) -0.0029(12)
    C18 0.0313(14) 0.079(2) 0.0444(16) -0.0037(15) 0.0190(13) -0.0138(16)
    C19 0.0351(17) 0.119(4) 0.0399(18) -0.002(2) 0.0073(14) -0.013(2)
    C20 0.0389(18) 0.124(4) 0.0366(17) 0.018(2) 0.0057(14) 0.015(2)
    C21 0.0395(16) 0.088(3) 0.0434(17) 0.0170(17) 0.0171(14) 0.0127(17)
    C22 0.0343(14) 0.065(2) 0.0340(14) 0.0068(14) 0.0142(12) 0.0029(13)
_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
    Cl1 C18 . 1.736(4) ?
    Cl2 C21 . 1.738(4) ?
    S1 O1 . 1.425(2) ?
    S1 O2 . 1.4268(19) ?
    S1 N1 . 1.640(2) ?
    S1 C1 . 1.759(3) ?
    O3 C7 . 1.333(3) ?
    O3 H3O . 0.8400 ?
    O4 C9 . 1.247(3) ?
    N1 C8 . 1.440(3) ?
    N1 C16 . 1.491(3) ?
    C1 C2 . 1.384(4) ?
    C1 C6 . 1.397(3) ?
    C2 C3 . 1.386(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.372(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.379(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.396(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.467(4) ?
    C7 C8 . 1.368(3) ?
    C8 C9 . 1.448(4) ?
    C9 C10 . 1.486(3) ?
    C10 C15 . 1.389(4) ?
    C10 C11 . 1.391(4) ?
    C11 C12 . 1.386(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.375(4) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.384(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.384(4) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.506(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C22 . 1.389(4) ?
    C17 C18 . 1.404(4) ?
    C18 C19 . 1.387(5) ?
    C19 C20 . 1.365(6) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.383(5) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.386(4) ?
    C22 H22 . 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
    O1 S1 O2 . . 119.62(12) ?
    O1 S1 N1 . . 107.33(12) ?
    O2 S1 N1 . . 107.70(12) ?
    O1 S1 C1 . . 108.03(12) ?
    O2 S1 C1 . . 110.19(12) ?
    N1 S1 C1 . . 102.62(11) ?
    C7 O3 H3O . . 109.5 ?
    C8 N1 C16 . . 116.06(19) ?
    C8 N1 S1 . . 114.13(16) ?
    C16 N1 S1 . . 119.42(18) ?
    C2 C1 C6 . . 121.6(2) ?
    C2 C1 S1 . . 120.8(2) ?
    C6 C1 S1 . . 117.5(2) ?
    C1 C2 C3 . . 119.0(3) ?
    C1 C2 H2 . . 120.5 ?
    C3 C2 H2 . . 120.5 ?
    C4 C3 C2 . . 120.1(3) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 121.2(3) ?
    C3 C4 H4 . . 119.4 ?
    C5 C4 H4 . . 119.4 ?
    C4 C5 C6 . . 120.1(3) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C5 C6 C1 . . 118.1(2) ?
    C5 C6 C7 . . 121.3(2) ?
    C1 C6 C7 . . 120.6(2) ?
    O3 C7 C8 . . 121.4(2) ?
    O3 C7 C6 . . 114.9(2) ?
    C8 C7 C6 . . 123.7(2) ?
    C7 C8 N1 . . 119.5(2) ?
    C7 C8 C9 . . 121.2(2) ?
    N1 C8 C9 . . 119.2(2) ?
    O4 C9 C8 . . 119.6(2) ?
    O4 C9 C10 . . 119.6(2) ?
    C8 C9 C10 . . 120.8(2) ?
    C15 C10 C11 . . 119.9(3) ?
    C15 C10 C9 . . 119.4(2) ?
    C11 C10 C9 . . 120.5(2) ?
    C12 C11 C10 . . 119.7(3) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C13 C12 C11 . . 120.1(3) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 120.5(3) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C13 C14 C15 . . 119.8(3) ?
    C13 C14 H14 . . 120.1 ?
    C15 C14 H14 . . 120.1 ?
    C14 C15 C10 . . 120.0(3) ?
    C14 C15 H15 . . 120.0 ?
    C10 C15 H15 . . 120.0 ?
    N1 C16 C17 . . 113.8(2) ?
    N1 C16 H16A . . 108.8 ?
    C17 C16 H16A . . 108.8 ?
    N1 C16 H16B . . 108.8 ?
    C17 C16 H16B . . 108.8 ?
    H16A C16 H16B . . 107.7 ?
    C22 C17 C18 . . 118.0(3) ?
    C22 C17 C16 . . 119.1(3) ?
    C18 C17 C16 . . 122.9(3) ?
    C19 C18 C17 . . 120.7(3) ?
    C19 C18 Cl1 . . 118.4(3) ?
    C17 C18 Cl1 . . 120.8(3) ?
    C20 C19 C18 . . 120.3(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 119.9(3) ?
    C19 C20 H20 . . 120.0 ?
    C21 C20 H20 . . 120.0 ?
    C20 C21 C22 . . 120.4(4) ?
    C20 C21 Cl2 . . 120.1(3) ?
    C22 C21 Cl2 . . 119.4(3) ?
    C21 C22 C17 . . 120.5(3) ?
    C21 C22 H22 . . 119.7 ?
    C17 C22 H22 . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 S1 N1 C8 . . . . -61.89(19) ?
    O2 S1 N1 C8 . . . . 168.09(17) ?
    C1 S1 N1 C8 . . . . 51.8(2) ?
    O1 S1 N1 C16 . . . . 154.46(18) ?
    O2 S1 N1 C16 . . . . 24.5(2) ?
    C1 S1 N1 C16 . . . . -91.83(19) ?
    O1 S1 C1 C2 . . . . -96.7(2) ?
    O2 S1 C1 C2 . . . . 35.6(3) ?
    N1 S1 C1 C2 . . . . 150.1(2) ?
    O1 S1 C1 C6 . . . . 80.8(2) ?
    O2 S1 C1 C6 . . . . -146.9(2) ?
    N1 S1 C1 C6 . . . . -32.4(2) ?
    C6 C1 C2 C3 . . . . -0.8(4) ?
    S1 C1 C2 C3 . . . . 176.6(2) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    C2 C3 C4 C5 . . . . 0.3(5) ?
    C3 C4 C5 C6 . . . . -0.5(5) ?
    C4 C5 C6 C1 . . . . 0.0(4) ?
    C4 C5 C6 C7 . . . . -179.3(3) ?
    C2 C1 C6 C5 . . . . 0.7(4) ?
    S1 C1 C6 C5 . . . . -176.8(2) ?
    C2 C1 C6 C7 . . . . -180.0(2) ?
    S1 C1 C6 C7 . . . . 2.5(3) ?
    C5 C6 C7 O3 . . . . 16.2(4) ?
    C1 C6 C7 O3 . . . . -163.1(2) ?
    C5 C6 C7 C8 . . . . -166.5(2) ?
    C1 C6 C7 C8 . . . . 14.2(4) ?
    O3 C7 C8 N1 . . . . -175.6(2) ?
    C6 C7 C8 N1 . . . . 7.3(4) ?
    O3 C7 C8 C9 . . . . 2.3(4) ?
    C6 C7 C8 C9 . . . . -174.8(2) ?
    C16 N1 C8 C7 . . . . 101.2(3) ?
    S1 N1 C8 C7 . . . . -43.8(3) ?
    C16 N1 C8 C9 . . . . -76.8(3) ?
    S1 N1 C8 C9 . . . . 138.3(2) ?
    C7 C8 C9 O4 . . . . -16.1(4) ?
    N1 C8 C9 O4 . . . . 161.9(2) ?
    C7 C8 C9 C10 . . . . 162.6(2) ?
    N1 C8 C9 C10 . . . . -19.5(3) ?
    O4 C9 C10 C15 . . . . -36.4(4) ?
    C8 C9 C10 C15 . . . . 144.9(3) ?
    O4 C9 C10 C11 . . . . 138.0(3) ?
    C8 C9 C10 C11 . . . . -40.7(4) ?
    C15 C10 C11 C12 . . . . 0.3(4) ?
    C9 C10 C11 C12 . . . . -174.1(3) ?
    C10 C11 C12 C13 . . . . -0.7(4) ?
    C11 C12 C13 C14 . . . . 0.0(4) ?
    C12 C13 C14 C15 . . . . 1.1(5) ?
    C13 C14 C15 C10 . . . . -1.5(4) ?
    C11 C10 C15 C14 . . . . 0.8(4) ?
    C9 C10 C15 C14 . . . . 175.3(3) ?
    C8 N1 C16 C17 . . . . -62.6(3) ?
    S1 N1 C16 C17 . . . . 80.4(3) ?
    N1 C16 C17 C22 . . . . -86.3(3) ?
    N1 C16 C17 C18 . . . . 92.3(3) ?
    C22 C17 C18 C19 . . . . 2.1(4) ?
    C16 C17 C18 C19 . . . . -176.5(3) ?
    C22 C17 C18 Cl1 . . . . -177.5(2) ?
    C16 C17 C18 Cl1 . . . . 3.9(4) ?
    C17 C18 C19 C20 . . . . -0.7(5) ?
    Cl1 C18 C19 C20 . . . . 178.9(3) ?
    C18 C19 C20 C21 . . . . -1.2(5) ?
    C19 C20 C21 C22 . . . . 1.8(5) ?
    C19 C20 C21 Cl2 . . . . -177.8(3) ?
    C20 C21 C22 C17 . . . . -0.4(4) ?
    Cl2 C21 C22 C17 . . . . 179.2(2) ?
    C18 C17 C22 C21 . . . . -1.5(4) ?
    C16 C17 C22 C21 . . . . 177.1(2) ?
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
    C3 H3 O4 1_565 0.95 2.60 3.310(4) 132.0 y
    O3 H3O O4 . 0.84 1.80 2.539(3) 146.3 y
    C11 H11 N1 . 0.95 2.62 3.003(3) 104.7 y
    C16 H16A O2 . 0.99 2.45 2.862(3) 104.7 y
    C16 H16B Cl1 . 0.99 2.67 3.120(3) 108.2 y