##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section B. It 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 may be obtained from        #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_bIICPA200K
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-10-11
_journal_date_accepted     2011-02-04
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     163
_journal_page_last     176
_journal_paper_category     FA
_journal_coeditor_code     GP5041
_chemical_name_systematic
;
 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide
;
_chemical_name_common     'chlorpropamide, βII-form'
_chemical_formula_moiety     'C10 H13 Cl N2 O3 S'
_chemical_formula_sum     'C10 H13 Cl N2 O3 S'
_chemical_formula_weight     276.73
_chemical_melting_point     'phase transition'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 2/c'
_symmetry_space_group_name_Hall     '-P 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
_cell_length_a     14.5882(5)
_cell_length_b     9.2584(2)
_cell_length_c     19.1532(6)
_cell_angle_alpha     90.00
_cell_angle_beta     93.260(3)
_cell_angle_gamma     90.00
_cell_volume     2582.71(13)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     13850
_cell_measurement_theta_min     2.7783
_cell_measurement_theta_max     29.2335
_cell_measurement_temperature     200(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.423
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1152
_exptl_absorpt_coefficient_mu     0.455
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_exptl_absorpt_correction_T_min     0.8993
_exptl_absorpt_correction_T_max     0.9645
_exptl_special_details
;
The data were processed using CrysAlis RED (Oxford Diffraction, 2008).
This program has determined the orientation matrices of the twin
components, determined the overlapping degree, merged equivalents.
There were 8202 isolated (Rint = 0.051) and 53248 overlapped
reflections (Rint = 0.111) of component 1. Twin component ratio 0.73:0.27.
;
_diffrn_ambient_temperature     200(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction KM4 CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.3457
_diffrn_reflns_number     53248
_diffrn_reflns_av_R_equivalents     0.111
_diffrn_reflns_av_sigmaI/netI     0.2135
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     25.35
_diffrn_reflns_theta_full     25.35
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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.
;
_reflns_number_total     7720
_reflns_number_gt     2794
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1224
_refine_ls_R_factor_gt     0.0553
_refine_ls_wR_factor_gt     0.1373
_refine_ls_wR_factor_ref     0.1467
_refine_ls_goodness_of_fit_ref     0.750
_refine_ls_restrained_S_all     0.750
_refine_ls_number_reflns     7720
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0498P)²+0.0000P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.399
_refine_diff_density_min     -0.304
_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'
    '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 CCD (Oxford Diffraction,2008a)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction,2008b)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction,2008b)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (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_disorder_assembly
    _atom_site_disorder_group
    Cl Cl11 0.16683(11) 0.51394(16) 0.08137(7) 0.0822(5) Uani d . 1 . .
    S S11 0.10693(8) 0.68692(13) 0.39003(6) 0.0501(3) Uani d . 1 . .
    O O11 0.0449(2) 0.8069(3) 0.39041(17) 0.0619(9) Uani d . 1 . .
    O O12 0.0868(2) 0.5584(3) 0.42699(16) 0.0599(9) Uani d . 1 . .
    O O13 0.2854(2) 0.5437(3) 0.41974(18) 0.0617(10) Uani d . 1 . .
    N N11 0.2031(2) 0.7548(4) 0.42096(19) 0.0426(10) Uani d . 1 . .
    H H11N 0.2039 0.8447 0.4359 0.051 Uiso calc R 1 . .
    N N12 0.3607(3) 0.7540(4) 0.4347(2) 0.0485(10) Uani d . 1 . .
    H H12N 0.3551 0.8485 0.4363 0.058 Uiso calc R 1 . .
    C C11 0.1514(3) 0.5624(6) 0.1668(2) 0.0613(14) Uani d . 1 . .
    C C12 0.1423(3) 0.7065(6) 0.1842(3) 0.0676(15) Uani d . 1 . .
    H H12 0.1458 0.7791 0.1494 0.081 Uiso calc R 1 . .
    C C13 0.1281(3) 0.7440(5) 0.2523(3) 0.0566(14) Uani d . 1 . .
    H H13 0.1202 0.8427 0.2641 0.068 Uiso calc R 1 . .
    C C14 0.1253(3) 0.6391(4) 0.3036(2) 0.0444(12) Uani d . 1 . .
    C C15 0.1353(3) 0.4973(5) 0.2844(2) 0.0541(13) Uani d . 1 . .
    H H15 0.1336 0.4243 0.3192 0.065 Uiso calc R 1 . .
    C C16 0.1476(3) 0.4575(5) 0.2163(3) 0.0620(14) Uani d . 1 . .
    H H16 0.1535 0.3586 0.2041 0.074 Uiso calc R 1 . .
    C C17 0.2859(3) 0.6754(5) 0.4248(2) 0.0471(12) Uani d . 1 . .
    C C18 0.4529(3) 0.6912(6) 0.4433(3) 0.0619(14) Uani d . 1 . .
    H H18A 0.4488 0.5946 0.4650 0.074 Uiso calc R 1 . .
    H H18B 0.4915 0.7528 0.4754 0.074 Uiso calc R 1 . .
    C C19 0.4978(3) 0.6773(6) 0.3752(3) 0.0706(16) Uani d . 1 . .
    H H19A 0.5031 0.7740 0.3538 0.085 Uiso calc R 1 . .
    H H19B 0.4590 0.6167 0.3428 0.085 Uiso calc R 1 . .
    C C20 0.5937(4) 0.6094(6) 0.3851(4) 0.111(3) Uani d . 1 . .
    H H20A 0.6334 0.6721 0.4149 0.167 Uiso calc R 1 . .
    H H20B 0.6200 0.5980 0.3395 0.167 Uiso calc R 1 . .
    H H20C 0.5889 0.5145 0.4074 0.167 Uiso calc R 1 . .
    Cl Cl21 0.29708(11) 0.00088(16) 0.07013(7) 0.0840(5) Uani d . 1 . .
    S S21 0.40918(8) 0.18721(13) 0.37561(7) 0.0515(3) Uani d . 1 . .
    O O21 0.4698(2) 0.3092(3) 0.37311(18) 0.0654(10) Uani d . 1 . .
    O O22 0.4384(2) 0.0617(3) 0.41412(16) 0.0596(9) Uani d . 1 . .
    O O23 0.2360(2) 0.0437(3) 0.40534(16) 0.0513(8) Uani d . 1 . .
    N N21 0.3183(3) 0.2551(4) 0.40755(19) 0.0490(11) Uani d . 1 . .
    H H21N 0.3191 0.3468 0.4196 0.059 Uiso calc R 1 . .
    N N22 0.1671(3) 0.2502(4) 0.43610(19) 0.0462(10) Uani d . 1 . .
    H H22N 0.1732 0.3440 0.4420 0.055 Uiso calc R 1 . .
    C C21 0.3274(3) 0.0540(6) 0.1543(2) 0.0541(13) Uani d . 1 . .
    C C22 0.3401(4) 0.1972(6) 0.1706(3) 0.0737(16) Uani d . 1 . .
    H H22 0.3325 0.2683 0.1350 0.088 Uiso calc R 1 . .
    C C23 0.3636(3) 0.2381(5) 0.2377(3) 0.0620(15) Uani d . 1 . .
    H H23 0.3715 0.3376 0.2487 0.074 Uiso calc R 1 . .
    C C24 0.3761(3) 0.1348(5) 0.2900(2) 0.0507(12) Uani d . 1 . .
    C C25 0.3645(3) -0.0089(5) 0.2732(2) 0.0564(13) Uani d . 1 . .
    H H25 0.3738 -0.0806 0.3084 0.068 Uiso calc R 1 . .
    C C26 0.3397(3) -0.0489(5) 0.2062(3) 0.0634(14) Uani d . 1 . .
    H H26 0.3308 -0.1481 0.1952 0.076 Uiso calc R 1 . .
    C C27 0.2387(3) 0.1749(5) 0.4169(2) 0.0434(11) Uani d . 1 . .
    C C28 0.0792(3) 0.1840(5) 0.4479(3) 0.0602(14) Uani d . 1 . .
    H H28A 0.0491 0.2376 0.4850 0.072 Uiso calc R 1 . .
    H H28B 0.0890 0.0833 0.4640 0.072 Uiso calc R 1 . .
    C C29 0.0167(3) 0.1846(6) 0.3806(4) 0.102(3) Uani d . 1 . .
    H H29A 0.0079 0.2852 0.3640 0.122 Uiso calc R 1 . .
    H H29B 0.0465 0.1296 0.3437 0.122 Uiso calc R 1 . .
    C C30 -0.0709(4) 0.1216(6) 0.3924(4) 0.135(3) Uani d . 1 . .
    H H30A -0.0621 0.0230 0.4102 0.202 Uiso calc R 1 . .
    H H30B -0.1085 0.1191 0.3483 0.202 Uiso calc R 1 . .
    H H30C -0.1020 0.1795 0.4267 0.202 Uiso calc R 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
    Cl11 C11 . 1.723(5) ?
    S11 O12 . 1.424(3) ?
    S11 O11 . 1.433(3) ?
    S11 N11 . 1.619(4) ?
    S11 C14 . 1.748(5) ?
    O13 C17 . 1.223(5) ?
    N11 C17 . 1.412(5) ?
    N11 H11N . 0.8800 ?
    N12 C17 . 1.316(5) ?
    N12 C18 . 1.466(5) ?
    N12 H12N . 0.8800 ?
    C11 C16 . 1.361(6) ?
    C11 C12 . 1.384(7) ?
    C12 C13 . 1.375(7) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.385(6) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.374(6) ?
    C15 C16 . 1.377(6) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C18 C19 . 1.498(7) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.535(6) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    Cl21 C21 . 1.719(5) ?
    S21 O22 . 1.428(3) ?
    S21 O21 . 1.437(3) ?
    S21 N21 . 1.618(4) ?
    S21 C24 . 1.752(5) ?
    O23 C27 . 1.235(5) ?
    N21 C27 . 1.399(5) ?
    N21 H21N . 0.8800 ?
    N22 C27 . 1.324(5) ?
    N22 C28 . 1.450(5) ?
    N22 H22N . 0.8800 ?
    C21 C22 . 1.372(7) ?
    C21 C26 . 1.381(6) ?
    C22 C23 . 1.365(6) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.389(6) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.377(6) ?
    C25 C26 . 1.364(6) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    C28 C29 . 1.536(7) ?
    C28 H28A . 0.9900 ?
    C28 H28B . 0.9900 ?
    C29 C30 . 1.436(7) ?
    C29 H29A . 0.9900 ?
    C29 H29B . 0.9900 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
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
    O12 S11 O11 . . 119.8(2) ?
    O12 S11 N11 . . 110.0(2) ?
    O11 S11 N11 . . 103.38(19) ?
    O12 S11 C14 . . 107.83(19) ?
    O11 S11 C14 . . 109.4(2) ?
    N11 S11 C14 . . 105.6(2) ?
    C17 N11 S11 . . 122.5(3) ?
    C17 N11 H11N . . 118.7 ?
    S11 N11 H11N . . 118.7 ?
    C17 N12 C18 . . 123.0(4) ?
    C17 N12 H12N . . 118.5 ?
    C18 N12 H12N . . 118.5 ?
    C16 C11 C12 . . 120.8(5) ?
    C16 C11 Cl11 . . 119.2(4) ?
    C12 C11 Cl11 . . 120.0(4) ?
    C13 C12 C11 . . 119.6(4) ?
    C13 C12 H12 . . 120.2 ?
    C11 C12 H12 . . 120.2 ?
    C12 C13 C14 . . 120.5(4) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C15 C14 C13 . . 118.1(4) ?
    C15 C14 S11 . . 121.3(3) ?
    C13 C14 S11 . . 120.5(3) ?
    C14 C15 C16 . . 122.1(4) ?
    C14 C15 H15 . . 119.0 ?
    C16 C15 H15 . . 119.0 ?
    C11 C16 C15 . . 118.8(5) ?
    C11 C16 H16 . . 120.6 ?
    C15 C16 H16 . . 120.6 ?
    O13 C17 N12 . . 124.3(5) ?
    O13 C17 N11 . . 120.9(4) ?
    N12 C17 N11 . . 114.8(4) ?
    N12 C18 C19 . . 112.4(4) ?
    N12 C18 H18A . . 109.1 ?
    C19 C18 H18A . . 109.1 ?
    N12 C18 H18B . . 109.1 ?
    C19 C18 H18B . . 109.1 ?
    H18A C18 H18B . . 107.9 ?
    C18 C19 C20 . . 111.6(5) ?
    C18 C19 H19A . . 109.3 ?
    C20 C19 H19A . . 109.3 ?
    C18 C19 H19B . . 109.3 ?
    C20 C19 H19B . . 109.3 ?
    H19A C19 H19B . . 108.0 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O22 S21 O21 . . 119.38(19) ?
    O22 S21 N21 . . 110.3(2) ?
    O21 S21 N21 . . 103.1(2) ?
    O22 S21 C24 . . 108.5(2) ?
    O21 S21 C24 . . 108.9(2) ?
    N21 S21 C24 . . 105.9(2) ?
    C27 N21 S21 . . 123.1(3) ?
    C27 N21 H21N . . 118.4 ?
    S21 N21 H21N . . 118.4 ?
    C27 N22 C28 . . 122.6(4) ?
    C27 N22 H22N . . 118.7 ?
    C28 N22 H22N . . 118.7 ?
    C22 C21 C26 . . 119.5(5) ?
    C22 C21 Cl21 . . 120.9(4) ?
    C26 C21 Cl21 . . 119.6(4) ?
    C23 C22 C21 . . 120.4(5) ?
    C23 C22 H22 . . 119.8 ?
    C21 C22 H22 . . 119.8 ?
    C22 C23 C24 . . 120.2(4) ?
    C22 C23 H23 . . 119.9 ?
    C24 C23 H23 . . 119.9 ?
    C25 C24 C23 . . 119.2(5) ?
    C25 C24 S21 . . 120.6(4) ?
    C23 C24 S21 . . 120.1(4) ?
    C26 C25 C24 . . 120.2(5) ?
    C26 C25 H25 . . 119.9 ?
    C24 C25 H25 . . 119.9 ?
    C25 C26 C21 . . 120.5(5) ?
    C25 C26 H26 . . 119.8 ?
    C21 C26 H26 . . 119.8 ?
    O23 C27 N22 . . 123.4(4) ?
    O23 C27 N21 . . 121.1(4) ?
    N22 C27 N21 . . 115.5(4) ?
    N22 C28 C29 . . 110.9(4) ?
    N22 C28 H28A . . 109.5 ?
    C29 C28 H28A . . 109.5 ?
    N22 C28 H28B . . 109.5 ?
    C29 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 108.1 ?
    C30 C29 C28 . . 111.0(5) ?
    C30 C29 H29A . . 109.4 ?
    C28 C29 H29A . . 109.4 ?
    C30 C29 H29B . . 109.4 ?
    C28 C29 H29B . . 109.4 ?
    H29A C29 H29B . . 108.0 ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O12 S11 N11 C17 . . . . 55.8(4) ?
    O11 S11 N11 C17 . . . . -175.1(4) ?
    C14 S11 N11 C17 . . . . -60.3(4) ?
    C16 C11 C12 C13 . . . . -0.9(8) ?
    Cl11 C11 C12 C13 . . . . 178.7(4) ?
    C11 C12 C13 C14 . . . . 1.7(8) ?
    C12 C13 C14 C15 . . . . -1.2(7) ?
    C12 C13 C14 S11 . . . . -179.8(4) ?
    O12 S11 C14 C15 . . . . -11.5(4) ?
    O11 S11 C14 C15 . . . . -143.3(4) ?
    N11 S11 C14 C15 . . . . 106.0(4) ?
    O12 S11 C14 C13 . . . . 167.0(4) ?
    O11 S11 C14 C13 . . . . 35.2(4) ?
    N11 S11 C14 C13 . . . . -75.4(4) ?
    C13 C14 C15 C16 . . . . -0.1(7) ?
    S11 C14 C15 C16 . . . . 178.5(4) ?
    C12 C11 C16 C15 . . . . -0.4(8) ?
    Cl11 C11 C16 C15 . . . . 180.0(4) ?
    C14 C15 C16 C11 . . . . 0.9(8) ?
    C18 N12 C17 O13 . . . . -2.2(8) ?
    C18 N12 C17 N11 . . . . 177.2(4) ?
    S11 N11 C17 O13 . . . . -16.5(7) ?
    S11 N11 C17 N12 . . . . 164.1(3) ?
    C17 N12 C18 C19 . . . . 91.5(6) ?
    N12 C18 C19 C20 . . . . -179.2(4) ?
    O22 S21 N21 C27 . . . . -54.0(4) ?
    O21 S21 N21 C27 . . . . 177.5(4) ?
    C24 S21 N21 C27 . . . . 63.2(4) ?
    C26 C21 C22 C23 . . . . -0.7(8) ?
    Cl21 C21 C22 C23 . . . . 179.6(4) ?
    C21 C22 C23 C24 . . . . 0.8(8) ?
    C22 C23 C24 C25 . . . . 0.1(8) ?
    C22 C23 C24 S21 . . . . 178.3(4) ?
    O22 S21 C24 C25 . . . . 12.1(5) ?
    O21 S21 C24 C25 . . . . 143.5(4) ?
    N21 S21 C24 C25 . . . . -106.3(4) ?
    O22 S21 C24 C23 . . . . -166.1(4) ?
    O21 S21 C24 C23 . . . . -34.7(5) ?
    N21 S21 C24 C23 . . . . 75.5(4) ?
    C23 C24 C25 C26 . . . . -1.0(8) ?
    S21 C24 C25 C26 . . . . -179.3(4) ?
    C24 C25 C26 C21 . . . . 1.1(8) ?
    C22 C21 C26 C25 . . . . -0.2(8) ?
    Cl21 C21 C26 C25 . . . . 179.5(4) ?
    C28 N22 C27 O23 . . . . 2.3(7) ?
    C28 N22 C27 N21 . . . . 179.8(4) ?
    S21 N21 C27 O23 . . . . 5.0(6) ?
    S21 N21 C27 N22 . . . . -172.6(3) ?
    C27 N22 C28 C29 . . . . -91.2(6) ?
    N22 C28 C29 C30 . . . . -179.0(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
    N11 H11N O23 1_565 0.88 2.00 2.737(4) 140.8
    N12 H12N O22 1_565 0.88 2.37 3.100(5) 140.7
    N12 H12N O23 1_565 0.88 2.55 3.271(5) 139.5
    N21 H21N O13 . 0.88 1.89 2.728(4) 158.9
    N22 H22N O12 . 0.88 2.36 3.086(5) 140.0
    N22 H22N O13 . 0.88 2.52 3.244(5) 139.8
data_bIIICPA100K
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide
;
_chemical_name_common     'chlorpropamide, βIII-form'
_chemical_formula_moiety     'C10 H13 Cl N2 O3 S'
_chemical_formula_sum     'C10 H13 Cl N2 O3 S'
_chemical_formula_weight     276.73
_chemical_melting_point     'phase transition'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 2/n'
_symmetry_space_group_name_Hall     '-P 2yac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y, z-1/2'
_cell_length_a     28.4475(12)
_cell_length_b     9.2322(3)
_cell_length_c     19.2298(7)
_cell_angle_alpha     90.00
_cell_angle_beta     95.562(4)
_cell_angle_gamma     90.00
_cell_volume     5026.6(3)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     9693
_cell_measurement_theta_min     3.0710
_cell_measurement_theta_max     29.3054
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.463
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2304
_exptl_absorpt_coefficient_mu     0.468
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_exptl_absorpt_correction_T_min     0.9458
_exptl_absorpt_correction_T_max     0.9725
_exptl_special_details
;
The data were processed using CrysAlis RED (Oxford Diffraction, 2008).
This program has determined the orientation matrices of the twin
components, determined the overlapping degree, merged equivalents.
There were 9590 isolated (Rint = 0.065) and 42040 overlapped
reflections (Rint = 0.087) of component 1. Twin component ratio 0.56:0.44.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction KM4 CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.3457
_diffrn_reflns_number     42040
_diffrn_reflns_av_R_equivalents     0.087
_diffrn_reflns_av_sigmaI/netI     0.1754
_diffrn_reflns_theta_min     3.09
_diffrn_reflns_theta_max     25.68
_diffrn_reflns_theta_full     25.68
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -33
_diffrn_reflns_limit_h_max     34
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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.
;
_reflns_number_total     14436
_reflns_number_gt     6814
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1238
_refine_ls_R_factor_gt     0.0533
_refine_ls_wR_factor_gt     0.1238
_refine_ls_wR_factor_ref     0.1388
_refine_ls_goodness_of_fit_ref     0.809
_refine_ls_restrained_S_all     0.809
_refine_ls_number_reflns     14436
_refine_ls_number_parameters     618
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0519P)²+0.0000P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.370
_refine_diff_density_min     -0.450
_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'
    '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 CCD (Oxford Diffraction,2008a)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction,2008b)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction,2008b)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL-97 (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_disorder_assembly
    _atom_site_disorder_group
    S S11 0.21089(5) 0.71308(13) 0.37489(8) 0.0205(3) Uani d . 1 . .
    Cl Cl11 0.13654(5) 0.52901(15) 0.07238(8) 0.0360(4) Uani d . 1 . .
    O O11 0.24094(12) 0.8357(3) 0.3716(2) 0.0278(9) Uani d . 1 . .
    O O12 0.22796(12) 0.5854(3) 0.4118(2) 0.0233(9) Uani d . 1 . .
    O O13 0.12415(11) 0.5664(3) 0.40638(19) 0.0197(9) Uani d . 1 . .
    N N11 0.16538(14) 0.7787(4) 0.4097(2) 0.0191(10) Uani d . 1 . .
    H H11N 0.1662 0.8698 0.4231 0.023 Uiso calc R 1 . .
    N N12 0.08929(15) 0.7716(4) 0.4398(2) 0.0203(10) Uani d . 1 . .
    H H12N 0.0928 0.8653 0.4468 0.024 Uiso calc R 1 . .
    C C11 0.15720(19) 0.5804(5) 0.1573(3) 0.0222(13) Uani d . 1 . .
    C C12 0.1624(2) 0.7259(5) 0.1722(3) 0.0321(15) Uani d . 1 . .
    H H12 0.1547 0.7970 0.1372 0.039 Uiso calc R 1 . .
    C C13 0.17886(19) 0.7655(6) 0.2390(3) 0.0259(14) Uani d . 1 . .
    H H13 0.1830 0.8652 0.2502 0.031 Uiso calc R 1 . .
    C C14 0.18954(18) 0.6611(5) 0.2905(3) 0.0219(13) Uani d . 1 . .
    C C15 0.18325(18) 0.5164(5) 0.2737(3) 0.0207(13) Uani d . 1 . .
    H H15 0.1900 0.4444 0.3086 0.025 Uiso calc R 1 . .
    C C16 0.1671(2) 0.4761(5) 0.2060(3) 0.0255(13) Uani d . 1 . .
    H H16 0.1631 0.3767 0.1940 0.031 Uiso calc R 1 . .
    C C17 0.12480(18) 0.6968(5) 0.4193(3) 0.0165(12) Uani d . 1 . .
    C C18 0.04397(19) 0.7037(5) 0.4516(3) 0.0263(14) Uani d . 1 . .
    H H18A 0.0282 0.7626 0.4855 0.032 Uiso calc R 1 . .
    H H18B 0.0500 0.6064 0.4722 0.032 Uiso calc R 1 . .
    C C19 0.01092(19) 0.6890(5) 0.3837(3) 0.0292(15) Uani d . 1 . .
    H H19A 0.0046 0.7861 0.3632 0.035 Uiso calc R 1 . .
    H H19B 0.0266 0.6302 0.3497 0.035 Uiso calc R 1 . .
    C C20 -0.03458(18) 0.6193(6) 0.3969(3) 0.0314(14) Uani d . 1 . .
    H H20A -0.0288 0.5185 0.4113 0.047 Uiso calc R 1 . .
    H H20B -0.0563 0.6218 0.3541 0.047 Uiso calc R 1 . .
    H H20C -0.0486 0.6717 0.4341 0.047 Uiso calc R 1 . .
    S S21 0.05747(5) 0.20420(13) 0.39707(7) 0.0193(3) Uani d . 1 . .
    Cl Cl21 0.07533(5) 0.03885(14) 0.08621(7) 0.0272(3) Uani d . 1 . .
    O O21 0.02457(12) 0.3210(3) 0.39749(19) 0.0235(9) Uani d . 1 . .
    O O22 0.04981(13) 0.0740(3) 0.43476(18) 0.0232(9) Uani d . 1 . .
    O O23 0.15094(13) 0.0702(3) 0.4252(2) 0.0275(10) Uani d . 1 . .
    N N21 0.10740(14) 0.2770(4) 0.4269(2) 0.0187(10) Uani d . 1 . .
    H H21N 0.1075 0.3669 0.4422 0.022 Uiso calc R 1 . .
    N N22 0.18848(15) 0.2866(4) 0.4349(2) 0.0219(11) Uani d . 1 . .
    H H22N 0.1849 0.3813 0.4344 0.026 Uiso calc R 1 . .
    C C21 0.07206(17) 0.0859(6) 0.1726(3) 0.0213(13) Uani d . 1 . .
    C C22 0.07025(19) 0.2306(5) 0.1914(3) 0.0275(14) Uani d . 1 . .
    H H22 0.0714 0.3042 0.1571 0.033 Uiso calc R 1 . .
    C C23 0.06678(19) 0.2662(5) 0.2593(3) 0.0257(14) Uani d . 1 . .
    H H23 0.0659 0.3652 0.2726 0.031 Uiso calc R 1 . .
    C C24 0.06450(18) 0.1570(5) 0.3101(3) 0.0190(12) Uani d . 1 . .
    C C25 0.06601(19) 0.0134(5) 0.2904(3) 0.0251(14) Uani d . 1 . .
    H H25 0.0641 -0.0609 0.3242 0.030 Uiso calc R 1 . .
    C C26 0.07030(19) -0.0222(5) 0.2218(3) 0.0239(13) Uani d . 1 . .
    H H26 0.0720 -0.1209 0.2084 0.029 Uiso calc R 1 . .
    C C27 0.14990(19) 0.2019(5) 0.4291(3) 0.0182(12) Uani d . 1 . .
    C C28 0.23616(19) 0.2271(5) 0.4420(3) 0.0275(14) Uani d . 1 . .
    H H28A 0.2364 0.1367 0.4698 0.033 Uiso calc R 1 . .
    H H28B 0.2577 0.2969 0.4680 0.033 Uiso calc R 1 . .
    C C29 0.2547(2) 0.1944(5) 0.3719(3) 0.0289(14) Uani d . 1 . .
    H H29A 0.2551 0.2849 0.3444 0.035 Uiso calc R 1 . .
    H H29B 0.2330 0.1255 0.3455 0.035 Uiso calc R 1 . .
    C C30 0.30442(19) 0.1297(5) 0.3811(3) 0.0338(16) Uani d . 1 . .
    H H30A 0.3264 0.2006 0.4040 0.051 Uiso calc R 1 . .
    H H30B 0.3144 0.1048 0.3352 0.051 Uiso calc R 1 . .
    H H30C 0.3043 0.0421 0.4099 0.051 Uiso calc R 1 . .
    S S31 0.55663(5) 0.15921(12) 0.40022(7) 0.0174(3) Uani d . 1 . .
    Cl Cl31 0.57454(5) 0.00535(14) 0.08763(7) 0.0278(3) Uani d . 1 . .
    O O31 0.52418(12) 0.2755(3) 0.40220(19) 0.0228(9) Uani d . 1 . .
    O O32 0.54986(12) 0.0270(3) 0.43614(18) 0.0195(8) Uani d . 1 . .
    O O33 0.64992(13) 0.0231(3) 0.4279(2) 0.0294(10) Uani d . 1 . .
    N N31 0.60691(14) 0.2305(4) 0.4314(2) 0.0161(10) Uani d . 1 . .
    H H31N 0.6070 0.3193 0.4479 0.019 Uiso calc R 1 . .
    N N32 0.68793(15) 0.2388(4) 0.4386(2) 0.0228(11) Uani d . 1 . .
    H H32N 0.6842 0.3334 0.4394 0.027 Uiso calc R 1 . .
    C C31 0.57098(18) 0.0495(5) 0.1742(3) 0.0200(12) Uani d . 1 . .
    C C32 0.56652(19) 0.1927(5) 0.1936(3) 0.0261(14) Uani d . 1 . .
    H H32 0.5663 0.2673 0.1595 0.031 Uiso calc R 1 . .
    C C33 0.5624(2) 0.2267(5) 0.2626(3) 0.0248(13) Uani d . 1 . .
    H H33 0.5593 0.3250 0.2761 0.030 Uiso calc R 1 . .
    C C34 0.56294(17) 0.1169(5) 0.3128(3) 0.0167(12) Uani d . 1 . .
    C C35 0.56814(18) -0.0276(5) 0.2926(3) 0.0220(13) Uani d . 1 . .
    H H35 0.5691 -0.1029 0.3264 0.026 Uiso calc R 1 . .
    C C36 0.57180(19) -0.0596(5) 0.2233(3) 0.0230(13) Uani d . 1 . .
    H H36 0.5749 -0.1575 0.2093 0.028 Uiso calc R 1 . .
    C C37 0.6501(2) 0.1558(5) 0.4328(3) 0.0195(13) Uani d . 1 . .
    C C38 0.73638(19) 0.1797(6) 0.4439(3) 0.0267(14) Uani d . 1 . .
    H H38A 0.7374 0.0895 0.4718 0.032 Uiso calc R 1 . .
    H H38B 0.7582 0.2502 0.4687 0.032 Uiso calc R 1 . .
    C C39 0.75302(19) 0.1477(5) 0.3733(3) 0.0279(14) Uani d . 1 . .
    H H39A 0.7534 0.2385 0.3460 0.034 Uiso calc R 1 . .
    H H39B 0.7307 0.0800 0.3475 0.034 Uiso calc R 1 . .
    C C40 0.80181(19) 0.0818(6) 0.3804(3) 0.0339(15) Uani d . 1 . .
    H H40A 0.8238 0.1476 0.4069 0.051 Uiso calc R 1 . .
    H H40B 0.8122 0.0660 0.3338 0.051 Uiso calc R 1 . .
    H H40C 0.8011 -0.0110 0.4050 0.051 Uiso calc R 1 . .
    S S41 0.70684(5) 0.66682(13) 0.37669(8) 0.0204(3) Uani d . 1 . .
    Cl Cl41 0.64736(5) 0.47530(14) 0.07030(7) 0.0308(3) Uani d . 1 . .
    O O41 0.73630(12) 0.7908(3) 0.3747(2) 0.0250(9) Uani d . 1 . .
    O O42 0.72302(12) 0.5403(3) 0.41542(18) 0.0227(9) Uani d . 1 . .
    O O43 0.62015(12) 0.5163(3) 0.40394(19) 0.0200(8) Uani d . 1 . .
    N N41 0.65923(15) 0.7324(4) 0.4084(2) 0.0209(11) Uani d . 1 . .
    H H41N 0.6587 0.8249 0.4194 0.025 Uiso calc R 1 . .
    N N42 0.58415(14) 0.7202(4) 0.4404(2) 0.0171(10) Uani d . 1 . .
    H H42N 0.5868 0.8147 0.4457 0.021 Uiso calc R 1 . .
    C C41 0.66228(18) 0.5311(5) 0.1555(3) 0.0239(13) Uani d . 1 . .
    C C42 0.66840(19) 0.6751(5) 0.1707(3) 0.0246(14) Uani d . 1 . .
    H H42 0.6636 0.7458 0.1348 0.030 Uiso calc R 1 . .
    C C43 0.68154(18) 0.7163(6) 0.2385(3) 0.0257(14) Uani d . 1 . .
    H H43 0.6857 0.8160 0.2497 0.031 Uiso calc R 1 . .
    C C44 0.68874(18) 0.6126(5) 0.2907(3) 0.0197(13) Uani d . 1 . .
    C C45 0.68143(19) 0.4673(5) 0.2756(3) 0.0241(13) Uani d . 1 . .
    H H45 0.6853 0.3967 0.3116 0.029 Uiso calc R 1 . .
    C C46 0.66819(19) 0.4259(6) 0.2062(3) 0.0251(13) Uani d . 1 . .
    H H46 0.6634 0.3267 0.1945 0.030 Uiso calc R 1 . .
    C C47 0.62023(19) 0.6481(5) 0.4184(3) 0.0182(13) Uani d . 1 . .
    C C48 0.53991(18) 0.6507(5) 0.4565(3) 0.0270(14) Uani d . 1 . .
    H H48A 0.5319 0.6847 0.5027 0.032 Uiso calc R 1 . .
    H H48B 0.5448 0.5446 0.4595 0.032 Uiso calc R 1 . .
    C C49 0.49769(19) 0.6831(6) 0.4011(3) 0.0270(14) Uani d . 1 . .
    H H49A 0.4683 0.6447 0.4179 0.032 Uiso calc R 1 . .
    H H49B 0.4941 0.7893 0.3958 0.032 Uiso calc R 1 . .
    C C50 0.5041(2) 0.6170(6) 0.3305(3) 0.0420(17) Uani d . 1 . .
    H H50A 0.5357 0.6402 0.3175 0.063 Uiso calc R 1 . .
    H H50B 0.4803 0.6565 0.2953 0.063 Uiso calc R 1 . .
    H H50C 0.5005 0.5116 0.3330 0.063 Uiso calc R 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
    S11 O11 . 1.424(3) ?
    S11 O12 . 1.436(4) ?
    S11 N11 . 1.630(4) ?
    S11 C14 . 1.743(6) ?
    Cl11 C11 . 1.746(5) ?
    O13 C17 . 1.229(5) ?
    N11 C17 . 1.407(6) ?
    N11 H11N . 0.8800 ?
    N12 C17 . 1.315(6) ?
    N12 C18 . 1.470(6) ?
    N12 H12N . 0.8800 ?
    C11 C16 . 1.355(7) ?
    C11 C12 . 1.379(7) ?
    C12 C13 . 1.373(8) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.395(7) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.382(7) ?
    C15 C16 . 1.389(8) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C18 C19 . 1.538(7) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.489(7) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    S21 O21 . 1.428(3) ?
    S21 O22 . 1.431(3) ?
    S21 N21 . 1.625(4) ?
    S21 C24 . 1.759(5) ?
    Cl21 C21 . 1.728(5) ?
    O23 C27 . 1.219(5) ?
    N21 C27 . 1.391(6) ?
    N21 H21N . 0.8800 ?
    N22 C27 . 1.343(6) ?
    N22 C28 . 1.458(6) ?
    N22 H22N . 0.8800 ?
    C21 C26 . 1.380(7) ?
    C21 C22 . 1.386(7) ?
    C22 C23 . 1.359(8) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.410(7) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.381(6) ?
    C25 C26 . 1.376(7) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    C28 C29 . 1.524(8) ?
    C28 H28A . 0.9900 ?
    C28 H28B . 0.9900 ?
    C29 C30 . 1.531(7) ?
    C29 H29A . 0.9900 ?
    C29 H29B . 0.9900 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
    S31 O31 . 1.419(3) ?
    S31 O32 . 1.425(3) ?
    S31 N31 . 1.634(4) ?
    S31 C34 . 1.753(5) ?
    Cl31 C31 . 1.727(5) ?
    O33 C37 . 1.229(5) ?
    N31 C37 . 1.406(6) ?
    N31 H31N . 0.8800 ?
    N32 C37 . 1.317(6) ?
    N32 C38 . 1.477(6) ?
    N32 H32N . 0.8800 ?
    C31 C36 . 1.379(7) ?
    C31 C32 . 1.382(7) ?
    C32 C33 . 1.380(8) ?
    C32 H32 . 0.9500 ?
    C33 C34 . 1.399(7) ?
    C33 H33 . 0.9500 ?
    C34 C35 . 1.401(7) ?
    C35 C36 . 1.378(7) ?
    C35 H35 . 0.9500 ?
    C36 H36 . 0.9500 ?
    C38 C39 . 1.509(8) ?
    C38 H38A . 0.9900 ?
    C38 H38B . 0.9900 ?
    C39 C40 . 1.509(7) ?
    C39 H39A . 0.9900 ?
    C39 H39B . 0.9900 ?
    C40 H40A . 0.9800 ?
    C40 H40B . 0.9800 ?
    C40 H40C . 0.9800 ?
    S41 O41 . 1.421(3) ?
    S41 O42 . 1.437(4) ?
    S41 N41 . 1.653(4) ?
    S41 C44 . 1.756(6) ?
    Cl41 C41 . 1.730(6) ?
    O43 C47 . 1.248(5) ?
    N41 C47 . 1.384(6) ?
    N41 H41N . 0.8800 ?
    N42 C47 . 1.327(6) ?
    N42 C48 . 1.472(6) ?
    N42 H42N . 0.8800 ?
    C41 C42 . 1.370(7) ?
    C41 C46 . 1.375(7) ?
    C42 C43 . 1.375(8) ?
    C42 H42 . 0.9500 ?
    C43 C44 . 1.388(8) ?
    C43 H43 . 0.9500 ?
    C44 C45 . 1.384(7) ?
    C45 C46 . 1.403(7) ?
    C45 H45 . 0.9500 ?
    C46 H46 . 0.9500 ?
    C48 C49 . 1.555(7) ?
    C48 H48A . 0.9900 ?
    C48 H48B . 0.9900 ?
    C49 C50 . 1.515(8) ?
    C49 H49A . 0.9900 ?
    C49 H49B . 0.9900 ?
    C50 H50A . 0.9800 ?
    C50 H50B . 0.9800 ?
    C50 H50C . 0.9800 ?
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
    O11 S11 O12 . . 119.9(2) ?
    O11 S11 N11 . . 103.1(2) ?
    O12 S11 N11 . . 110.2(2) ?
    O11 S11 C14 . . 109.5(2) ?
    O12 S11 C14 . . 107.7(2) ?
    N11 S11 C14 . . 105.4(2) ?
    C17 N11 S11 . . 123.3(3) ?
    C17 N11 H11N . . 118.3 ?
    S11 N11 H11N . . 118.3 ?
    C17 N12 C18 . . 122.2(4) ?
    C17 N12 H12N . . 118.9 ?
    C18 N12 H12N . . 118.9 ?
    C16 C11 C12 . . 122.5(5) ?
    C16 C11 Cl11 . . 118.8(4) ?
    C12 C11 Cl11 . . 118.7(4) ?
    C13 C12 C11 . . 118.3(5) ?
    C13 C12 H12 . . 120.8 ?
    C11 C12 H12 . . 120.8 ?
    C12 C13 C14 . . 120.8(5) ?
    C12 C13 H13 . . 119.6 ?
    C14 C13 H13 . . 119.6 ?
    C15 C14 C13 . . 119.2(5) ?
    C15 C14 S11 . . 120.6(4) ?
    C13 C14 S11 . . 120.2(4) ?
    C14 C15 C16 . . 120.1(5) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C11 C16 C15 . . 119.1(5) ?
    C11 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    O13 C17 N12 . . 125.3(5) ?
    O13 C17 N11 . . 119.7(5) ?
    N12 C17 N11 . . 115.0(4) ?
    N12 C18 C19 . . 112.4(4) ?
    N12 C18 H18A . . 109.1 ?
    C19 C18 H18A . . 109.1 ?
    N12 C18 H18B . . 109.1 ?
    C19 C18 H18B . . 109.1 ?
    H18A C18 H18B . . 107.9 ?
    C20 C19 C18 . . 111.3(5) ?
    C20 C19 H19A . . 109.4 ?
    C18 C19 H19A . . 109.4 ?
    C20 C19 H19B . . 109.4 ?
    C18 C19 H19B . . 109.4 ?
    H19A C19 H19B . . 108.0 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O21 S21 O22 . . 120.0(2) ?
    O21 S21 N21 . . 103.7(2) ?
    O22 S21 N21 . . 109.8(2) ?
    O21 S21 C24 . . 109.1(2) ?
    O22 S21 C24 . . 108.1(2) ?
    N21 S21 C24 . . 105.2(2) ?
    C27 N21 S21 . . 122.2(3) ?
    C27 N21 H21N . . 118.9 ?
    S21 N21 H21N . . 118.9 ?
    C27 N22 C28 . . 122.3(4) ?
    C27 N22 H22N . . 118.9 ?
    C28 N22 H22N . . 118.9 ?
    C26 C21 C22 . . 120.9(5) ?
    C26 C21 Cl21 . . 119.1(4) ?
    C22 C21 Cl21 . . 120.0(4) ?
    C23 C22 C21 . . 119.5(5) ?
    C23 C22 H22 . . 120.3 ?
    C21 C22 H22 . . 120.3 ?
    C22 C23 C24 . . 120.3(5) ?
    C22 C23 H23 . . 119.8 ?
    C24 C23 H23 . . 119.8 ?
    C25 C24 C23 . . 119.5(5) ?
    C25 C24 S21 . . 120.5(4) ?
    C23 C24 S21 . . 120.0(4) ?
    C26 C25 C24 . . 120.0(5) ?
    C26 C25 H25 . . 120.0 ?
    C24 C25 H25 . . 120.0 ?
    C25 C26 C21 . . 119.8(5) ?
    C25 C26 H26 . . 120.1 ?
    C21 C26 H26 . . 120.1 ?
    O23 C27 N22 . . 124.1(5) ?
    O23 C27 N21 . . 121.4(5) ?
    N22 C27 N21 . . 114.4(4) ?
    N22 C28 C29 . . 112.9(4) ?
    N22 C28 H28A . . 109.0 ?
    C29 C28 H28A . . 109.0 ?
    N22 C28 H28B . . 109.0 ?
    C29 C28 H28B . . 109.0 ?
    H28A C28 H28B . . 107.8 ?
    C28 C29 C30 . . 111.7(5) ?
    C28 C29 H29A . . 109.3 ?
    C30 C29 H29A . . 109.3 ?
    C28 C29 H29B . . 109.3 ?
    C30 C29 H29B . . 109.3 ?
    H29A C29 H29B . . 107.9 ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    O31 S31 O32 . . 121.1(2) ?
    O31 S31 N31 . . 103.6(2) ?
    O32 S31 N31 . . 108.8(2) ?
    O31 S31 C34 . . 108.8(2) ?
    O32 S31 C34 . . 107.8(2) ?
    N31 S31 C34 . . 105.9(2) ?
    C37 N31 S31 . . 122.8(3) ?
    C37 N31 H31N . . 118.6 ?
    S31 N31 H31N . . 118.6 ?
    C37 N32 C38 . . 122.7(4) ?
    C37 N32 H32N . . 118.6 ?
    C38 N32 H32N . . 118.6 ?
    C36 C31 C32 . . 120.7(5) ?
    C36 C31 Cl31 . . 119.3(4) ?
    C32 C31 Cl31 . . 120.0(4) ?
    C33 C32 C31 . . 119.7(5) ?
    C33 C32 H32 . . 120.2 ?
    C31 C32 H32 . . 120.2 ?
    C32 C33 C34 . . 120.1(5) ?
    C32 C33 H33 . . 119.9 ?
    C34 C33 H33 . . 119.9 ?
    C33 C34 C35 . . 119.6(5) ?
    C33 C34 S31 . . 120.3(4) ?
    C35 C34 S31 . . 120.1(4) ?
    C36 C35 C34 . . 119.5(5) ?
    C36 C35 H35 . . 120.3 ?
    C34 C35 H35 . . 120.3 ?
    C35 C36 C31 . . 120.5(5) ?
    C35 C36 H36 . . 119.8 ?
    C31 C36 H36 . . 119.8 ?
    O33 C37 N32 . . 125.7(5) ?
    O33 C37 N31 . . 119.3(5) ?
    N32 C37 N31 . . 115.0(4) ?
    N32 C38 C39 . . 112.5(4) ?
    N32 C38 H38A . . 109.1 ?
    C39 C38 H38A . . 109.1 ?
    N32 C38 H38B . . 109.1 ?
    C39 C38 H38B . . 109.1 ?
    H38A C38 H38B . . 107.8 ?
    C38 C39 C40 . . 111.3(5) ?
    C38 C39 H39A . . 109.4 ?
    C40 C39 H39A . . 109.4 ?
    C38 C39 H39B . . 109.4 ?
    C40 C39 H39B . . 109.4 ?
    H39A C39 H39B . . 108.0 ?
    C39 C40 H40A . . 109.5 ?
    C39 C40 H40B . . 109.5 ?
    H40A C40 H40B . . 109.5 ?
    C39 C40 H40C . . 109.5 ?
    H40A C40 H40C . . 109.5 ?
    H40B C40 H40C . . 109.5 ?
    O41 S41 O42 . . 120.6(2) ?
    O41 S41 N41 . . 102.8(2) ?
    O42 S41 N41 . . 109.9(2) ?
    O41 S41 C44 . . 108.9(2) ?
    O42 S41 C44 . . 107.8(2) ?
    N41 S41 C44 . . 106.0(2) ?
    C47 N41 S41 . . 122.8(3) ?
    C47 N41 H41N . . 118.6 ?
    S41 N41 H41N . . 118.6 ?
    C47 N42 C48 . . 123.5(4) ?
    C47 N42 H42N . . 118.3 ?
    C48 N42 H42N . . 118.3 ?
    C42 C41 C46 . . 121.9(5) ?
    C42 C41 Cl41 . . 120.4(4) ?
    C46 C41 Cl41 . . 117.6(4) ?
    C41 C42 C43 . . 119.3(5) ?
    C41 C42 H42 . . 120.4 ?
    C43 C42 H42 . . 120.4 ?
    C42 C43 C44 . . 120.2(5) ?
    C42 C43 H43 . . 119.9 ?
    C44 C43 H43 . . 119.9 ?
    C45 C44 C43 . . 120.5(5) ?
    C45 C44 S41 . . 119.9(4) ?
    C43 C44 S41 . . 119.6(4) ?
    C44 C45 C46 . . 119.0(5) ?
    C44 C45 H45 . . 120.5 ?
    C46 C45 H45 . . 120.5 ?
    C41 C46 C45 . . 119.0(5) ?
    C41 C46 H46 . . 120.5 ?
    C45 C46 H46 . . 120.5 ?
    O43 C47 N42 . . 125.2(5) ?
    O43 C47 N41 . . 120.1(5) ?
    N42 C47 N41 . . 114.6(4) ?
    N42 C48 C49 . . 113.0(4) ?
    N42 C48 H48A . . 109.0 ?
    C49 C48 H48A . . 109.0 ?
    N42 C48 H48B . . 109.0 ?
    C49 C48 H48B . . 109.0 ?
    H48A C48 H48B . . 107.8 ?
    C50 C49 C48 . . 112.6(4) ?
    C50 C49 H49A . . 109.1 ?
    C48 C49 H49A . . 109.1 ?
    C50 C49 H49B . . 109.1 ?
    C48 C49 H49B . . 109.1 ?
    H49A C49 H49B . . 107.8 ?
    C49 C50 H50A . . 109.5 ?
    C49 C50 H50B . . 109.5 ?
    H50A C50 H50B . . 109.5 ?
    C49 C50 H50C . . 109.5 ?
    H50A C50 H50C . . 109.5 ?
    H50B C50 H50C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O11 S11 N11 C17 . . . . 176.1(4) ?
    O12 S11 N11 C17 . . . . -54.7(5) ?
    C14 S11 N11 C17 . . . . 61.3(5) ?
    C16 C11 C12 C13 . . . . 0.9(9) ?
    Cl11 C11 C12 C13 . . . . -179.7(4) ?
    C11 C12 C13 C14 . . . . -0.8(8) ?
    C12 C13 C14 C15 . . . . -0.1(8) ?
    C12 C13 C14 S11 . . . . 179.5(4) ?
    O11 S11 C14 C15 . . . . 143.6(4) ?
    O12 S11 C14 C15 . . . . 11.6(5) ?
    N11 S11 C14 C15 . . . . -106.1(4) ?
    O11 S11 C14 C13 . . . . -36.0(5) ?
    O12 S11 C14 C13 . . . . -168.0(4) ?
    N11 S11 C14 C13 . . . . 74.3(5) ?
    C13 C14 C15 C16 . . . . 0.9(8) ?
    S11 C14 C15 C16 . . . . -178.7(4) ?
    C12 C11 C16 C15 . . . . -0.2(9) ?
    Cl11 C11 C16 C15 . . . . -179.6(4) ?
    C14 C15 C16 C11 . . . . -0.7(8) ?
    C18 N12 C17 O13 . . . . 1.6(8) ?
    C18 N12 C17 N11 . . . . 179.2(4) ?
    S11 N11 C17 O13 . . . . 5.9(7) ?
    S11 N11 C17 N12 . . . . -171.8(4) ?
    C17 N12 C18 C19 . . . . -84.2(6) ?
    N12 C18 C19 C20 . . . . 179.7(4) ?
    O21 S21 N21 C27 . . . . -174.2(4) ?
    O22 S21 N21 C27 . . . . 56.4(5) ?
    C24 S21 N21 C27 . . . . -59.7(4) ?
    C26 C21 C22 C23 . . . . 0.1(8) ?
    Cl21 C21 C22 C23 . . . . 178.8(4) ?
    C21 C22 C23 C24 . . . . -0.7(9) ?
    C22 C23 C24 C25 . . . . 0.3(8) ?
    C22 C23 C24 S21 . . . . -177.3(4) ?
    O21 S21 C24 C25 . . . . -137.3(4) ?
    O22 S21 C24 C25 . . . . -5.3(5) ?
    N21 S21 C24 C25 . . . . 112.0(5) ?
    O21 S21 C24 C23 . . . . 40.2(5) ?
    O22 S21 C24 C23 . . . . 172.2(4) ?
    N21 S21 C24 C23 . . . . -70.5(5) ?
    C23 C24 C25 C26 . . . . 0.8(8) ?
    S21 C24 C25 C26 . . . . 178.3(4) ?
    C24 C25 C26 C21 . . . . -1.4(9) ?
    C22 C21 C26 C25 . . . . 0.9(8) ?
    Cl21 C21 C26 C25 . . . . -177.7(4) ?
    C28 N22 C27 O23 . . . . -4.5(8) ?
    C28 N22 C27 N21 . . . . 176.4(5) ?
    S21 N21 C27 O23 . . . . -18.1(7) ?
    S21 N21 C27 N22 . . . . 161.1(4) ?
    C27 N22 C28 C29 . . . . 86.6(6) ?
    N22 C28 C29 C30 . . . . -179.0(4) ?
    O31 S31 N31 C37 . . . . -174.0(4) ?
    O32 S31 N31 C37 . . . . 56.0(5) ?
    C34 S31 N31 C37 . . . . -59.6(4) ?
    C36 C31 C32 C33 . . . . -0.5(8) ?
    Cl31 C31 C32 C33 . . . . 178.3(4) ?
    C31 C32 C33 C34 . . . . 0.1(9) ?
    C32 C33 C34 C35 . . . . 0.7(8) ?
    C32 C33 C34 S31 . . . . -178.8(4) ?
    O31 S31 C34 C33 . . . . 36.7(5) ?
    O32 S31 C34 C33 . . . . 169.6(4) ?
    N31 S31 C34 C33 . . . . -74.1(5) ?
    O31 S31 C34 C35 . . . . -142.8(4) ?
    O32 S31 C34 C35 . . . . -9.9(5) ?
    N31 S31 C34 C35 . . . . 106.4(4) ?
    C33 C34 C35 C36 . . . . -1.2(8) ?
    S31 C34 C35 C36 . . . . 178.3(4) ?
    C34 C35 C36 C31 . . . . 0.8(8) ?
    C32 C31 C36 C35 . . . . 0.0(8) ?
    Cl31 C31 C36 C35 . . . . -178.8(4) ?
    C38 N32 C37 O33 . . . . -3.5(9) ?
    C38 N32 C37 N31 . . . . 177.5(5) ?
    S31 N31 C37 O33 . . . . -19.2(7) ?
    S31 N31 C37 N32 . . . . 159.9(4) ?
    C37 N32 C38 C39 . . . . 84.7(6) ?
    N32 C38 C39 C40 . . . . -177.7(4) ?
    O41 S41 N41 C47 . . . . 179.0(4) ?
    O42 S41 N41 C47 . . . . -51.5(5) ?
    C44 S41 N41 C47 . . . . 64.8(5) ?
    C46 C41 C42 C43 . . . . 1.0(8) ?
    Cl41 C41 C42 C43 . . . . -178.2(4) ?
    C41 C42 C43 C44 . . . . 0.3(8) ?
    C42 C43 C44 C45 . . . . -1.9(8) ?
    C42 C43 C44 S41 . . . . 178.5(4) ?
    O41 S41 C44 C45 . . . . 147.3(4) ?
    O42 S41 C44 C45 . . . . 14.9(5) ?
    N41 S41 C44 C45 . . . . -102.7(4) ?
    O41 S41 C44 C43 . . . . -33.2(5) ?
    O42 S41 C44 C43 . . . . -165.6(4) ?
    N41 S41 C44 C43 . . . . 76.8(4) ?
    C43 C44 C45 C46 . . . . 2.1(8) ?
    S41 C44 C45 C46 . . . . -178.3(4) ?
    C42 C41 C46 C45 . . . . -0.8(9) ?
    Cl41 C41 C46 C45 . . . . 178.5(4) ?
    C44 C45 C46 C41 . . . . -0.8(8) ?
    C48 N42 C47 O43 . . . . 5.3(8) ?
    C48 N42 C47 N41 . . . . -177.9(5) ?
    S41 N41 C47 O43 . . . . 0.7(7) ?
    S41 N41 C47 N42 . . . . -176.3(4) ?
    C47 N42 C48 C49 . . . . -107.6(5) ?
    N42 C48 C49 C50 . . . . 66.3(6) ?
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
    N11 H11N O23 1_565 0.88 1.90 2.744(5) 159.5
    N12 H12N O22 1_565 0.88 2.28 3.008(5) 139.8
    N12 H12N O23 1_565 0.88 2.57 3.295(5) 139.7
    N21 H21N O13 . 0.88 2.04 2.750(5) 137.2
    N22 H22N O12 . 0.88 2.31 3.027(5) 138.4
    N22 H22N O13 . 0.88 2.45 3.183(5) 140.7
    N31 H31N O43 . 0.88 2.06 2.725(5) 132.0
    N32 H32N O42 . 0.88 2.28 3.005(5) 140.1
    N32 H32N O43 . 0.88 2.53 3.237(5) 138.0
    N41 H41N O33 1_565 0.88 1.86 2.726(5) 169.6
    N42 H42N O32 1_565 0.88 2.22 2.994(5) 146.0
    N42 H42N O33 1_565 0.88 2.68 3.386(5) 138.5
