##############################################################################
#                                                                            #
# 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     2014-01-03
_journal_date_accepted     2014-01-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     o212
_journal_page_last     o213
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814001342
_journal_coeditor_code     RK2420
_publ_contact_author_name     'K. Sethusankar'
_publ_contact_author_address
;
   Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai - 600 004
   India.
;
_publ_contact_author_email     'ksethusankar@yahoo.co.in'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;\
2-(4,5-Dichloro-2-nitrophenyl)-4-methoxy-3-methyl-\
9-phenylsulfonyl-9<i>H</i>-carbazole
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Narayanan'
;  Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai 600 004
   India
;
    'K. Sethusankar'
;  Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai 600 004
   India
;
    'Velu Saravanan'
;  Department of Organic Chemistry
   University of Madras
   Maraimalai campus
   Chennai 600 025
   India
;
    'Arasambattu K. Mohanakrishnan'
;  Department of Organic Chemistry
   University of Madras
   Maraimalai campus
   Chennai 600 025
   India
;
data_I
_audit_creation_method     'SHELXL97'
_database_code_depnum_ccdc_archive     'CCDC 952293'
_chemical_name_systematic
;\
2-(4,5-Dichloro-2-nitrophenyl)-4-methoxy-3-methyl-\
9-phenylsulfonyl-9<i>H</i>-carbazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H18 Cl2 N2 O5 S'
_chemical_formula_sum     'C26 H18 Cl2 N2 O5 S'
_chemical_formula_iupac     'C26 H18 Cl2 N2 O5 S'
_chemical_formula_weight     541.39
_chemical_melting_point_gt     493
_chemical_melting_point_lt     495
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     18.6364(7)
_cell_length_b     12.1665(4)
_cell_length_c     21.1272(7)
_cell_angle_alpha     90.00
_cell_angle_beta     91.461(2)
_cell_angle_gamma     90.00
_cell_volume     4788.8(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4058
_cell_measurement_theta_min     2.00
_cell_measurement_theta_max     27.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.502
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2224
_exptl_absorpt_coefficient_mu     0.401
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.905
_exptl_absorpt_correction_T_max     0.923
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     '\w- and \f-scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     23543
_diffrn_reflns_av_R_equivalents     0.0307
_diffrn_reflns_av_sigmaI/netI     0.0258
_diffrn_reflns_theta_min     2.21
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     ?
_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     5218
_reflns_number_gt     4056
_reflns_threshold_expression     >2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0525
_refine_ls_R_factor_gt     0.0378
_refine_ls_wR_factor_gt     0.0997
_refine_ls_wR_factor_ref     0.1120
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     5218
_refine_ls_number_parameters     327
_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^)+(0.0583P)^2^+2.8891P] 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     0.352
_refine_diff_density_min     -0.386
_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     '<i>APEX2</i>    (Bruker,    2008)'
_computing_cell_refinement     '<i>SAINT</i>    (Bruker,    2008)'
_computing_data_reduction     '<i>SAINT</i>    (Bruker,    2008)'
_computing_structure_solution     '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_refinement     '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_molecular_graphics
;
<i>ORTEP-3 for Windows</i> (Farrugia, 2012) and <i>Mercury</i>
(Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
              '<i>SHELXL97</i> (Sheldrick, 2008) and <i>PLATON</i> (Spek, 2009)'
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
    C C1 0.30233(10) 0.60315(14) 0.46304(8) 0.0376(4) Uani d . 1 1 . .
    C C2 0.31928(12) 0.59976(18) 0.39942(9) 0.0508(5) Uani d . 1 1 . .
    H H2 0.2838 0.6021 0.3677 0.061 Uiso calc R 1 1 . .
    C C3 0.39066(13) 0.59284(19) 0.38525(10) 0.0573(6) Uani d . 1 1 . .
    H H3 0.4035 0.5891 0.3430 0.069 Uiso calc R 1 1 . .
    C C4 0.44365(12) 0.59128(18) 0.43162(11) 0.0539(5) Uani d . 1 1 . .
    H H4 0.4915 0.5875 0.4202 0.065 Uiso calc R 1 1 . .
    C C5 0.42723(10) 0.59515(16) 0.49463(9) 0.0434(4) Uani d . 1 1 . .
    H H5 0.4633 0.5941 0.5259 0.052 Uiso calc R 1 1 . .
    C C6 0.35545(9) 0.60060(13) 0.51051(8) 0.0338(4) Uani d . 1 1 . .
    C C7 0.32037(9) 0.60416(13) 0.57063(8) 0.0321(3) Uani d . 1 1 . .
    C C8 0.34576(9) 0.60187(14) 0.63289(8) 0.0347(4) Uani d . 1 1 . .
    C C9 0.29861(9) 0.60208(14) 0.68281(8) 0.0360(4) Uani d . 1 1 . .
    C C10 0.22473(9) 0.60638(14) 0.66796(8) 0.0353(4) Uani d . 1 1 . .
    C C11 0.19794(9) 0.61140(15) 0.60641(9) 0.0375(4) Uani d . 1 1 . .
    H H11 0.1489 0.6162 0.5978 0.045 Uiso calc R 1 1 . .
    C C12 0.24651(9) 0.60903(13) 0.55824(8) 0.0333(4) Uani d . 1 1 . .
    C C13 0.17149(9) 0.61156(15) 0.71942(8) 0.0367(4) Uani d . 1 1 . .
    C C14 0.15400(10) 0.71305(15) 0.74444(8) 0.0398(4) Uani d . 1 1 . .
    H H14 0.1787 0.7750 0.7313 0.048 Uiso calc R 1 1 . .
    C C15 0.10101(10) 0.72501(15) 0.78834(8) 0.0393(4) Uani d . 1 1 . .
    C C16 0.06477(9) 0.63314(16) 0.81004(8) 0.0384(4) Uani d . 1 1 . .
    C C17 0.07991(9) 0.53179(16) 0.78529(9) 0.0408(4) Uani d . 1 1 . .
    H H17 0.0550 0.4699 0.7983 0.049 Uiso calc R 1 1 . .
    C C18 0.13256(10) 0.52280(15) 0.74091(9) 0.0388(4) Uani d . 1 1 . .
    C C19 0.15457(11) 0.42952(17) 0.46831(10) 0.0504(5) Uani d . 1 1 . .
    C C20 0.19244(13) 0.36252(19) 0.42797(13) 0.0632(6) Uani d . 1 1 . .
    H H20 0.2196 0.3928 0.3960 0.076 Uiso calc R 1 1 . .
    C C21 0.18912(18) 0.2500(2) 0.43609(19) 0.0933(11) Uani d . 1 1 . .
    H H21 0.2144 0.2038 0.4095 0.112 Uiso calc R 1 1 . .
    C C22 0.1490(2) 0.2064(3) 0.4828(2) 0.1137(15) Uani d . 1 1 . .
    H H22 0.1465 0.1305 0.4876 0.136 Uiso calc R 1 1 . .
    C C23 0.1125(2) 0.2727(3) 0.5224(2) 0.1109(13) Uani d . 1 1 . .
    H H23 0.0859 0.2421 0.5546 0.133 Uiso calc R 1 1 . .
    C C24 0.11478(17) 0.3856(2) 0.51522(14) 0.0790(8) Uani d . 1 1 . .
    H H24 0.0894 0.4310 0.5421 0.095 Uiso calc R 1 1 . .
    C C25 0.32572(11) 0.59430(18) 0.75030(9) 0.0488(5) Uani d . 1 1 . .
    H H25A 0.3757 0.5753 0.7510 0.073 Uiso calc R 1 1 . .
    H H25B 0.2992 0.5388 0.7720 0.073 Uiso calc R 1 1 . .
    H H25C 0.3195 0.6638 0.7709 0.073 Uiso calc R 1 1 . .
    C C26 0.45504(12) 0.6937(2) 0.65493(13) 0.0670(7) Uani d . 1 1 . .
    H H26A 0.4489 0.7400 0.6184 0.101 Uiso calc R 1 1 . .
    H H26B 0.5052 0.6799 0.6626 0.101 Uiso calc R 1 1 . .
    H H26C 0.4355 0.7295 0.6911 0.101 Uiso calc R 1 1 . .
    N N1 0.23420(8) 0.61223(12) 0.49177(7) 0.0379(3) Uani d . 1 1 . .
    N N2 0.14522(10) 0.41316(14) 0.71521(9) 0.0547(4) Uani d . 1 1 . .
    O O1 0.10190(8) 0.62053(13) 0.49305(8) 0.0582(4) Uani d . 1 1 . .
    O O2 0.16291(9) 0.59563(13) 0.39235(7) 0.0590(4) Uani d . 1 1 . .
    O O3 0.20623(10) 0.38349(14) 0.70792(11) 0.0838(6) Uani d . 1 1 . .
    O O4 0.09295(11) 0.35658(15) 0.70249(11) 0.0870(6) Uani d . 1 1 . .
    O O5 0.41857(6) 0.59176(11) 0.64406(6) 0.0428(3) Uani d . 1 1 . .
    S S1 0.15720(3) 0.57206(4) 0.45772(2) 0.04322(14) Uani d . 1 1 . .
    Cl Cl1 0.08048(3) 0.85490(4) 0.81386(3) 0.05761(16) Uani d . 1 1 . .
    Cl Cl2 0.00173(3) 0.64492(5) 0.86734(2) 0.05700(16) Uani d . 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
    C1 0.0450(10) 0.0334(9) 0.0349(9) -0.0025(7) 0.0085(8) 0.0000(7)
    C2 0.0599(13) 0.0586(13) 0.0339(10) -0.0034(10) 0.0054(9) 0.0013(8)
    C3 0.0698(15) 0.0659(14) 0.0371(11) 0.0007(11) 0.0208(10) 0.0041(10)
    C4 0.0507(12) 0.0614(13) 0.0508(12) 0.0030(9) 0.0243(10) 0.0079(10)
    C5 0.0392(10) 0.0472(11) 0.0446(11) 0.0025(8) 0.0130(8) 0.0073(8)
    C6 0.0398(9) 0.0281(8) 0.0340(9) -0.0001(6) 0.0093(7) 0.0018(6)
    C7 0.0335(9) 0.0285(8) 0.0345(9) -0.0007(6) 0.0069(7) -0.0003(6)
    C8 0.0323(9) 0.0323(9) 0.0396(9) 0.0011(6) 0.0048(7) 0.0018(7)
    C9 0.0375(9) 0.0367(9) 0.0341(9) 0.0014(7) 0.0053(7) 0.0002(7)
    C10 0.0358(9) 0.0333(9) 0.0371(9) 0.0002(7) 0.0092(7) -0.0008(7)
    C11 0.0308(9) 0.0411(10) 0.0408(10) 0.0002(7) 0.0048(7) -0.0038(7)
    C12 0.0365(9) 0.0314(8) 0.0321(9) -0.0005(6) 0.0031(7) -0.0017(6)
    C13 0.0347(9) 0.0424(10) 0.0333(9) 0.0027(7) 0.0056(7) 0.0011(7)
    C14 0.0409(10) 0.0411(10) 0.0378(10) -0.0016(7) 0.0112(8) 0.0000(7)
    C15 0.0386(9) 0.0455(10) 0.0341(9) 0.0034(7) 0.0059(7) -0.0029(7)
    C16 0.0278(8) 0.0575(12) 0.0301(9) 0.0015(7) 0.0035(7) 0.0003(8)
    C17 0.0334(9) 0.0480(11) 0.0411(10) -0.0046(7) 0.0014(8) 0.0074(8)
    C18 0.0361(9) 0.0413(10) 0.0391(10) 0.0024(7) 0.0045(7) 0.0024(7)
    C19 0.0496(12) 0.0459(11) 0.0549(12) -0.0075(8) -0.0154(10) -0.0018(9)
    C20 0.0598(14) 0.0521(14) 0.0764(16) 0.0053(10) -0.0227(12) -0.0114(11)
    C21 0.090(2) 0.0527(17) 0.134(3) 0.0128(14) -0.053(2) -0.0278(17)
    C22 0.132(3) 0.0504(19) 0.155(4) -0.021(2) -0.068(3) 0.013(2)
    C23 0.131(3) 0.083(3) 0.117(3) -0.054(2) -0.020(3) 0.034(2)
    C24 0.091(2) 0.0693(17) 0.0765(18) -0.0285(14) -0.0045(15) 0.0078(13)
    C25 0.0492(12) 0.0635(13) 0.0340(10) 0.0033(9) 0.0043(9) 0.0026(9)
    C26 0.0422(12) 0.0717(16) 0.0870(18) -0.0142(10) -0.0034(12) 0.0007(13)
    N1 0.0368(8) 0.0445(8) 0.0325(8) -0.0025(6) 0.0025(6) -0.0024(6)
    N2 0.0576(11) 0.0413(10) 0.0659(12) -0.0001(8) 0.0158(9) 0.0014(8)
    O1 0.0407(8) 0.0681(10) 0.0655(10) 0.0108(7) -0.0047(7) -0.0103(7)
    O2 0.0667(10) 0.0666(10) 0.0429(8) -0.0010(7) -0.0159(7) 0.0057(7)
    O3 0.0677(12) 0.0498(10) 0.1355(18) 0.0124(8) 0.0353(12) -0.0033(10)
    O4 0.0775(13) 0.0578(11) 0.1262(17) -0.0173(9) 0.0093(12) -0.0258(10)
    O5 0.0310(6) 0.0498(8) 0.0477(8) 0.0013(5) 0.0021(6) 0.0047(6)
    S1 0.0422(3) 0.0440(3) 0.0430(3) 0.00159(18) -0.0079(2) -0.00157(19)
    Cl1 0.0647(4) 0.0520(3) 0.0571(3) 0.0080(2) 0.0205(3) -0.0108(2)
    Cl2 0.0392(3) 0.0869(4) 0.0457(3) -0.0042(2) 0.0174(2) -0.0040(2)
_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
    C1 C6 . 1.391(3) ?
    C1 C2 . 1.389(3) ?
    C1 N1 . 1.426(2) ?
    C2 C3 . 1.373(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.373(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.374(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.389(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.444(2) ?
    C7 C8 . 1.387(2) ?
    C7 C12 . 1.396(2) ?
    C8 O5 . 1.377(2) ?
    C8 C9 . 1.390(2) ?
    C9 C10 . 1.405(2) ?
    C9 C25 . 1.503(3) ?
    C10 C11 . 1.382(3) ?
    C10 C13 . 1.492(2) ?
    C11 C12 . 1.379(2) ?
    C11 H11 . 0.9300 ?
    C12 N1 . 1.418(2) ?
    C13 C18 . 1.384(3) ?
    C13 C14 . 1.385(3) ?
    C14 C15 . 1.380(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.390(3) ?
    C15 Cl1 . 1.7161(19) ?
    C16 C17 . 1.372(3) ?
    C16 Cl2 . 1.7144(18) ?
    C17 C18 . 1.379(3) ?
    C17 H17 . 0.9300 ?
    C18 N2 . 1.462(2) ?
    C19 C24 . 1.362(4) ?
    C19 C20 . 1.385(3) ?
    C19 S1 . 1.749(2) ?
    C20 C21 . 1.382(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.361(6) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.358(6) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.382(4) ?
    C23 H23 . 0.9300 ?
    C24 H24 . 0.9300 ?
    C25 H25A . 0.9600 ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
    C26 O5 . 1.430(3) ?
    C26 H26A . 0.9600 ?
    C26 H26B . 0.9600 ?
    C26 H26C . 0.9600 ?
    N1 S1 . 1.6623(15) ?
    N2 O3 . 1.207(2) ?
    N2 O4 . 1.217(2) ?
    O1 S1 . 1.4163(16) ?
    O2 S1 . 1.4173(16) ?
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
    C6 C1 C2 . . 121.43(18) ?
    C6 C1 N1 . . 108.66(15) ?
    C2 C1 N1 . . 129.89(18) ?
    C3 C2 C1 . . 117.3(2) ?
    C3 C2 H2 . . 121.4 ?
    C1 C2 H2 . . 121.4 ?
    C2 C3 C4 . . 121.9(2) ?
    C2 C3 H3 . . 119.1 ?
    C4 C3 H3 . . 119.1 ?
    C3 C4 C5 . . 121.1(2) ?
    C3 C4 H4 . . 119.4 ?
    C5 C4 H4 . . 119.4 ?
    C4 C5 C6 . . 118.37(19) ?
    C4 C5 H5 . . 120.8 ?
    C6 C5 H5 . . 120.8 ?
    C5 C6 C1 . . 119.93(17) ?
    C5 C6 C7 . . 132.40(17) ?
    C1 C6 C7 . . 107.67(15) ?
    C8 C7 C12 . . 119.32(15) ?
    C8 C7 C6 . . 133.05(16) ?
    C12 C7 C6 . . 107.63(15) ?
    O5 C8 C7 . . 118.38(15) ?
    O5 C8 C9 . . 120.63(16) ?
    C7 C8 C9 . . 120.84(16) ?
    C8 C9 C10 . . 117.74(16) ?
    C8 C9 C25 . . 121.05(16) ?
    C10 C9 C25 . . 121.18(16) ?
    C11 C10 C9 . . 122.69(16) ?
    C11 C10 C13 . . 116.92(15) ?
    C9 C10 C13 . . 120.32(16) ?
    C12 C11 C10 . . 117.71(16) ?
    C12 C11 H11 . . 121.1 ?
    C10 C11 H11 . . 121.1 ?
    C11 C12 C7 . . 121.67(16) ?
    C11 C12 N1 . . 129.61(16) ?
    C7 C12 N1 . . 108.72(15) ?
    C18 C13 C14 . . 116.10(16) ?
    C18 C13 C10 . . 124.76(16) ?
    C14 C13 C10 . . 118.88(16) ?
    C15 C14 C13 . . 122.00(17) ?
    C15 C14 H14 . . 119.0 ?
    C13 C14 H14 . . 119.0 ?
    C14 C15 C16 . . 119.94(17) ?
    C14 C15 Cl1 . . 118.53(14) ?
    C16 C15 Cl1 . . 121.52(14) ?
    C17 C16 C15 . . 119.40(17) ?
    C17 C16 Cl2 . . 119.72(15) ?
    C15 C16 Cl2 . . 120.88(15) ?
    C16 C17 C18 . . 119.17(17) ?
    C16 C17 H17 . . 120.4 ?
    C18 C17 H17 . . 120.4 ?
    C17 C18 C13 . . 123.32(17) ?
    C17 C18 N2 . . 116.71(17) ?
    C13 C18 N2 . . 119.95(17) ?
    C24 C19 C20 . . 120.8(2) ?
    C24 C19 S1 . . 120.0(2) ?
    C20 C19 S1 . . 119.23(19) ?
    C21 C20 C19 . . 118.8(3) ?
    C21 C20 H20 . . 120.6 ?
    C19 C20 H20 . . 120.6 ?
    C22 C21 C20 . . 120.2(3) ?
    C22 C21 H21 . . 119.9 ?
    C20 C21 H21 . . 119.9 ?
    C21 C22 C23 . . 120.6(3) ?
    C21 C22 H22 . . 119.7 ?
    C23 C22 H22 . . 119.7 ?
    C22 C23 C24 . . 120.4(4) ?
    C22 C23 H23 . . 119.8 ?
    C24 C23 H23 . . 119.8 ?
    C19 C24 C23 . . 119.3(3) ?
    C19 C24 H24 . . 120.4 ?
    C23 C24 H24 . . 120.4 ?
    C9 C25 H25A . . 109.5 ?
    C9 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C9 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    O5 C26 H26A . . 109.5 ?
    O5 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    O5 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C12 N1 C1 . . 107.23(14) ?
    C12 N1 S1 . . 122.47(12) ?
    C1 N1 S1 . . 124.15(12) ?
    O3 N2 O4 . . 123.7(2) ?
    O3 N2 C18 . . 118.82(18) ?
    O4 N2 C18 . . 117.53(19) ?
    C8 O5 C26 . . 114.36(15) ?
    O2 S1 O1 . . 120.21(10) ?
    O2 S1 N1 . . 106.07(9) ?
    O1 S1 N1 . . 106.33(8) ?
    O2 S1 C19 . . 109.16(10) ?
    O1 S1 C19 . . 108.80(11) ?
    N1 S1 C19 . . 105.23(9) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.5(3) ?
    N1 C1 C2 C3 . . . . 178.70(19) ?
    C1 C2 C3 C4 . . . . -1.2(3) ?
    C2 C3 C4 C5 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . 0.1(3) ?
    C4 C5 C6 C1 . . . . -0.6(3) ?
    C4 C5 C6 C7 . . . . 179.07(19) ?
    C2 C1 C6 C5 . . . . 0.3(3) ?
    N1 C1 C6 C5 . . . . -178.16(15) ?
    C2 C1 C6 C7 . . . . -179.44(17) ?
    N1 C1 C6 C7 . . . . 2.06(18) ?
    C5 C6 C7 C8 . . . . -1.0(3) ?
    C1 C6 C7 C8 . . . . 178.70(18) ?
    C5 C6 C7 C12 . . . . -179.87(18) ?
    C1 C6 C7 C12 . . . . -0.12(18) ?
    C12 C7 C8 O5 . . . . 176.94(14) ?
    C6 C7 C8 O5 . . . . -1.8(3) ?
    C12 C7 C8 C9 . . . . 1.3(2) ?
    C6 C7 C8 C9 . . . . -177.38(17) ?
    O5 C8 C9 C10 . . . . -176.46(15) ?
    C7 C8 C9 C10 . . . . -0.9(2) ?
    O5 C8 C9 C25 . . . . 1.6(3) ?
    C7 C8 C9 C25 . . . . 177.13(17) ?
    C8 C9 C10 C11 . . . . -0.6(3) ?
    C25 C9 C10 C11 . . . . -178.71(17) ?
    C8 C9 C10 C13 . . . . -177.44(16) ?
    C25 C9 C10 C13 . . . . 4.5(3) ?
    C9 C10 C11 C12 . . . . 1.8(3) ?
    C13 C10 C11 C12 . . . . 178.68(16) ?
    C10 C11 C12 C7 . . . . -1.4(3) ?
    C10 C11 C12 N1 . . . . 179.54(16) ?
    C8 C7 C12 C11 . . . . -0.1(2) ?
    C6 C7 C12 C11 . . . . 178.87(16) ?
    C8 C7 C12 N1 . . . . 179.12(14) ?
    C6 C7 C12 N1 . . . . -1.87(18) ?
    C11 C10 C13 C18 . . . . 82.6(2) ?
    C9 C10 C13 C18 . . . . -100.5(2) ?
    C11 C10 C13 C14 . . . . -91.3(2) ?
    C9 C10 C13 C14 . . . . 85.6(2) ?
    C18 C13 C14 C15 . . . . 0.1(3) ?
    C10 C13 C14 C15 . . . . 174.57(16) ?
    C13 C14 C15 C16 . . . . 1.8(3) ?
    C13 C14 C15 Cl1 . . . . -177.08(14) ?
    C14 C15 C16 C17 . . . . -3.0(3) ?
    Cl1 C15 C16 C17 . . . . 175.87(14) ?
    C14 C15 C16 Cl2 . . . . 176.85(14) ?
    Cl1 C15 C16 Cl2 . . . . -4.3(2) ?
    C15 C16 C17 C18 . . . . 2.2(3) ?
    Cl2 C16 C17 C18 . . . . -177.65(13) ?
    C16 C17 C18 C13 . . . . -0.2(3) ?
    C16 C17 C18 N2 . . . . -178.70(17) ?
    C14 C13 C18 C17 . . . . -1.0(3) ?
    C10 C13 C18 C17 . . . . -175.02(17) ?
    C14 C13 C18 N2 . . . . 177.48(17) ?
    C10 C13 C18 N2 . . . . 3.4(3) ?
    C24 C19 C20 C21 . . . . 0.1(3) ?
    S1 C19 C20 C21 . . . . -178.99(18) ?
    C19 C20 C21 C22 . . . . 0.3(4) ?
    C20 C21 C22 C23 . . . . -0.8(5) ?
    C21 C22 C23 C24 . . . . 1.0(5) ?
    C20 C19 C24 C23 . . . . 0.1(4) ?
    S1 C19 C24 C23 . . . . 179.2(2) ?
    C22 C23 C24 C19 . . . . -0.7(5) ?
    C11 C12 N1 C1 . . . . -177.70(17) ?
    C7 C12 N1 C1 . . . . 3.11(18) ?
    C11 C12 N1 S1 . . . . -24.3(3) ?
    C7 C12 N1 S1 . . . . 156.49(12) ?
    C6 C1 N1 C12 . . . . -3.19(18) ?
    C2 C1 N1 C12 . . . . 178.47(19) ?
    C6 C1 N1 S1 . . . . -156.01(13) ?
    C2 C1 N1 S1 . . . . 25.7(3) ?
    C17 C18 N2 O3 . . . . -138.2(2) ?
    C13 C18 N2 O3 . . . . 43.3(3) ?
    C17 C18 N2 O4 . . . . 41.6(3) ?
    C13 C18 N2 O4 . . . . -136.9(2) ?
    C7 C8 O5 C26 . . . . 96.3(2) ?
    C9 C8 O5 C26 . . . . -88.1(2) ?
    C12 N1 S1 O2 . . . . 175.29(14) ?
    C1 N1 S1 O2 . . . . -35.85(17) ?
    C12 N1 S1 O1 . . . . 46.24(16) ?
    C1 N1 S1 O1 . . . . -164.90(15) ?
    C12 N1 S1 C19 . . . . -69.08(16) ?
    C1 N1 S1 C19 . . . . 79.77(16) ?
    C24 C19 S1 O2 . . . . -146.25(19) ?
    C20 C19 S1 O2 . . . . 32.82(19) ?
    C24 C19 S1 O1 . . . . -13.3(2) ?
    C20 C19 S1 O1 . . . . 165.73(16) ?
    C24 C19 S1 N1 . . . . 100.3(2) ?
    C20 C19 S1 N1 . . . . -80.66(17) ?
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
    C2 H2 O2 . 0.93 2.33 2.915(3) 121
    C11 H11 O1 . 0.93 2.36 2.955(2) 122
_iucr_refine_instructions_details
;
TITL 25 in C2/c
CELL  0.71073  18.6364  12.1665  21.1272   90.000   91.461   90.000
ZERR     8.00   0.0007   0.0004   0.0007    0.000    0.002    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    O    S    CL
UNIT  208  144  16   40   8    16
MERG   2
FMAP   2
PLAN   20
OMIT -2 54
OMIT 1 1 0
OMIT 2 0 0
BOND $H
ACTA
CONF
L.S.   12
WGHT    0.058300    2.889100
FVAR       0.13613
C1    1    0.302330    0.603145    0.463041    11.00000    0.04504    0.03337 =
         0.03485   -0.00001    0.00851   -0.00249
C2    1    0.319281    0.599765    0.399417    11.00000    0.05990    0.05862 =
         0.03394    0.00129    0.00544   -0.00337
AFIX  43
H2    2    0.283757    0.602092    0.367722    11.00000   -1.20000
AFIX   0
C3    1    0.390657    0.592844    0.385245    11.00000    0.06977    0.06592 =
         0.03712    0.00414    0.02082    0.00072
AFIX  43
H3    2    0.403469    0.589110    0.343043    11.00000   -1.20000
AFIX   0
C4    1    0.443652    0.591281    0.431622    11.00000    0.05072    0.06142 =
         0.05083    0.00789    0.02427    0.00299
AFIX  43
H4    2    0.491452    0.587543    0.420194    11.00000   -1.20000
AFIX   0
C5    1    0.427232    0.595148    0.494628    11.00000    0.03916    0.04719 =
         0.04455    0.00727    0.01304    0.00251
AFIX  43
H5    2    0.463296    0.594137    0.525869    11.00000   -1.20000
AFIX   0
C6    1    0.355452    0.600604    0.510509    11.00000    0.03977    0.02811 =
         0.03403    0.00183    0.00928   -0.00010
C7    1    0.320373    0.604162    0.570625    11.00000    0.03351    0.02847 =
         0.03450   -0.00026    0.00691   -0.00073
C8    1    0.345763    0.601869    0.632892    11.00000    0.03230    0.03230 =
         0.03965    0.00181    0.00479    0.00114
C9    1    0.298609    0.602083    0.682813    11.00000    0.03752    0.03669 =
         0.03410    0.00021    0.00527    0.00139
C10   1    0.224731    0.606378    0.667958    11.00000    0.03577    0.03334 =
         0.03709   -0.00082    0.00920    0.00023
C11   1    0.197942    0.611397    0.606407    11.00000    0.03075    0.04113 =
         0.04080   -0.00382    0.00475    0.00022
AFIX  43
H11   2    0.148860    0.616202    0.597770    11.00000   -1.20000
AFIX   0
C12   1    0.246512    0.609035    0.558237    11.00000    0.03648    0.03139 =
         0.03208   -0.00165    0.00307   -0.00049
C13   1    0.171485    0.611558    0.719421    11.00000    0.03465    0.04240 =
         0.03326    0.00109    0.00560    0.00269
C14   1    0.154004    0.713055    0.744445    11.00000    0.04086    0.04111 =
         0.03782    0.00003    0.01115   -0.00159
AFIX  43
H14   2    0.178743    0.775006    0.731253    11.00000   -1.20000
AFIX   0
C15   1    0.101012    0.725013    0.788338    11.00000    0.03857    0.04551 =
         0.03408   -0.00295    0.00594    0.00341
C16   1    0.064773    0.633135    0.810040    11.00000    0.02784    0.05754 =
         0.03008    0.00030    0.00354    0.00153
C17   1    0.079905    0.531786    0.785285    11.00000    0.03336    0.04803 =
         0.04113    0.00744    0.00140   -0.00462
AFIX  43
H17   2    0.054959    0.469897    0.798271    11.00000   -1.20000
AFIX   0
C18   1    0.132557    0.522800    0.740912    11.00000    0.03613    0.04133 =
         0.03913    0.00239    0.00446    0.00239
C19   1    0.154571    0.429522    0.468312    11.00000    0.04964    0.04590 =
         0.05487   -0.00177   -0.01535   -0.00753
C20   1    0.192439    0.362520    0.427975    11.00000    0.05979    0.05213 =
         0.07642   -0.01143   -0.02271    0.00533
AFIX  43
H20   2    0.219600    0.392757    0.396015    11.00000   -1.20000
AFIX   0
C21   1    0.189120    0.249968    0.436090    11.00000    0.08996    0.05271 =
         0.13426   -0.02776   -0.05321    0.01283
AFIX  43
H21   2    0.214391    0.203833    0.409543    11.00000   -1.20000
AFIX   0
C22   1    0.149000    0.206411    0.482793    11.00000    0.13235    0.05035 =
         0.15463    0.01277   -0.06834   -0.02109
AFIX  43
H22   2    0.146535    0.130535    0.487608    11.00000   -1.20000
AFIX   0
C23   1    0.112530    0.272734    0.522431    11.00000    0.13130    0.08293 =
         0.11744    0.03418   -0.01978   -0.05360
AFIX  43
H23   2    0.085891    0.242069    0.554604    11.00000   -1.20000
AFIX   0
C24   1    0.114783    0.385571    0.515222    11.00000    0.09072    0.06933 =
         0.07654    0.00782   -0.00453   -0.02855
AFIX  43
H24   2    0.089417    0.430988    0.542098    11.00000   -1.20000
AFIX   0
C25   1    0.325721    0.594299    0.750299    11.00000    0.04915    0.06350 =
         0.03404    0.00257    0.00433    0.00332
AFIX 137
H25A  2    0.375725    0.575257    0.751042    11.00000   -1.50000
H25B  2    0.299230    0.538824    0.772030    11.00000   -1.50000
H25C  2    0.319519    0.663845    0.770916    11.00000   -1.50000
AFIX   0
C26   1    0.455038    0.693658    0.654930    11.00000    0.04218    0.07169 =
         0.08696    0.00075   -0.00342   -0.01422
AFIX 137
H26A  2    0.448904    0.739954    0.618396    11.00000   -1.50000
H26B  2    0.505235    0.679914    0.662593    11.00000   -1.50000
H26C  2    0.435467    0.729532    0.691097    11.00000   -1.50000
AFIX   0
N1    3    0.234196    0.612233    0.491774    11.00000    0.03681    0.04447 =
         0.03253   -0.00241    0.00255   -0.00246
N2    3    0.145223    0.413157    0.715210    11.00000    0.05755    0.04131 =
         0.06588    0.00143    0.01580   -0.00011
O1    4    0.101900    0.620530    0.493049    11.00000    0.04066    0.06814 =
         0.06552   -0.01027   -0.00468    0.01075
O2    4    0.162914    0.595630    0.392346    11.00000    0.06669    0.06663 =
         0.04289    0.00572   -0.01591   -0.00104
O3    4    0.206232    0.383490    0.707923    11.00000    0.06766    0.04982 =
         0.13553   -0.00330    0.03525    0.01242
O4    4    0.092946    0.356578    0.702490    11.00000    0.07751    0.05776 =
         0.12621   -0.02579    0.00926   -0.01727
O5    4    0.418565    0.591762    0.644065    11.00000    0.03101    0.04977 =
         0.04773    0.00470    0.00209    0.00125
S1    5    0.157196    0.572062    0.457720    11.00000    0.04219    0.04400 =
         0.04302   -0.00157   -0.00785    0.00159
CL1   6    0.080475    0.854902    0.813861    11.00000    0.06471    0.05199 =
         0.05711   -0.01079    0.02052    0.00801
CL2   6    0.001729    0.644916    0.867341    11.00000    0.03917    0.08693 =
         0.04572   -0.00399    0.01735   -0.00422
HKLF 4
REM  25 in C2/c
REM R1 =  0.0378 for   4056 Fo > 4sig(Fo)  and  0.0525 for all   5218 data
REM    327 parameters refined using      0 restraints
END
;