##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 990803'
_chemical_name_systematic
;\
N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-\
4-yl)benzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H11 Cl N4 O2 S'
_chemical_formula_sum     'C13 H11 Cl N4 O2 S'
_chemical_formula_iupac     'C13 H11 Cl N4 O2 S'
_chemical_formula_weight     322.77
_chemical_melting_point     376
_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     13.1045(4)
_cell_length_b     14.7259(5)
_cell_length_c     14.6953(6)
_cell_angle_alpha     90.00
_cell_angle_beta     95.127(3)
_cell_angle_gamma     90.00
_cell_volume     2824.49(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4972
_cell_measurement_theta_min     2.77
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.518
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     0.428
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.7700
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
IR cm⁻¹ (KBr) 3435, 1388; Anal. Calcd for C₁₃H₁₁ClN₄O₂S C, 45.82; H,
2.96; N, 16.44%; Found, C, 45.18; H, 2.92; N, 15.84%.
;
_diffrn_ambient_temperature     293(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 SMART CCD'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16038
_diffrn_reflns_av_R_equivalents     0.0308
_diffrn_reflns_av_sigmaI/netI     0.0291
_diffrn_reflns_theta_min     2.77
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4972
_reflns_number_gt     3759
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0481
_refine_ls_R_factor_gt     0.0339
_refine_ls_wR_factor_gt     0.0939
_refine_ls_wR_factor_ref     0.0976
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     4972
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.303
_refine_diff_density_min     -0.306
_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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'SHELXL97 (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 Cl1A 0.20678(5) 0.52370(5) 0.40718(5) 0.06025(19) Uani d . 1 1 . .
    Cl Cl1B 0.93941(5) 0.41848(4) 0.38570(5) 0.05977(19) Uani d . 1 1 . .
    S S2A 0.28936(4) 0.22270(3) 0.58582(4) 0.03821(16) Uani d . 1 1 . .
    S S2B 0.70463(4) 0.13503(3) 0.40663(4) 0.03622(15) Uani d . 1 1 . .
    O O3A 0.26710(11) 0.21724(10) 0.48964(11) 0.0500(4) Uani d . 1 1 . .
    O O3B 0.70151(13) 0.19837(10) 0.47946(11) 0.0522(4) Uani d . 1 1 . .
    O O4A 0.32556(11) 0.14347(9) 0.63449(13) 0.0562(5) Uani d . 1 1 . .
    O O4B 0.63810(11) 0.05785(9) 0.40271(11) 0.0461(4) Uani d . 1 1 . .
    N N5A 0.51992(13) 0.58429(10) 0.64248(12) 0.0357(4) Uani d . 1 1 . .
    N N5B 0.62508(13) 0.45541(11) 0.14780(12) 0.0369(4) Uani d . 1 1 . .
    N N6A 0.30372(12) 0.41345(11) 0.52175(12) 0.0371(4) Uani d . 1 1 . .
    N N6B 0.79517(13) 0.30202(11) 0.33564(12) 0.0376(4) Uani d . 1 1 . .
    N N7A 0.37871(13) 0.29776(10) 0.61344(13) 0.0439(5) Uani d . 1 1 . .
    H H7A 0.4314 0.2801 0.6480 0.053 Uiso calc R 1 1 . .
    N N7B 0.67403(13) 0.18711(11) 0.30975(12) 0.0394(4) Uani d . 1 1 . .
    H H7B 0.6335 0.1599 0.2693 0.047 Uiso calc R 1 1 . .
    N N8A 0.52770(13) 0.43954(10) 0.69189(12) 0.0360(4) Uani d . 1 1 . .
    N N8B 0.56595(12) 0.31475(11) 0.16965(12) 0.0364(4) Uani d . 1 1 . .
    C C9A 0.17905(15) 0.26081(13) 0.63400(15) 0.0354(5) Uani d . 1 1 . .
    C C9B 0.83185(15) 0.09728(13) 0.40267(14) 0.0354(5) Uani d . 1 1 . .
    C C10A 0.1679(2) 0.23876(17) 0.72382(18) 0.0609(7) Uani d . 1 1 . .
    H H10A 0.2202 0.2094 0.7593 0.073 Uiso calc R 1 1 . .
    C C10B 0.91108(18) 0.14379(15) 0.44983(16) 0.0482(6) Uani d . 1 1 . .
    H H10B 0.8982 0.1949 0.4842 0.058 Uiso calc R 1 1 . .
    C C11A 0.0783(3) 0.2610(2) 0.7596(2) 0.0800(9) Uani d . 1 1 . .
    H H11A 0.0695 0.2463 0.8200 0.096 Uiso calc R 1 1 . .
    C C11B 1.01033(19) 0.11297(18) 0.44508(19) 0.0594(7) Uani d . 1 1 . .
    H H11B 1.0645 0.1433 0.4771 0.071 Uiso calc R 1 1 . .
    C C12A 0.0013(2) 0.30470(19) 0.7073(2) 0.0755(9) Uani d . 1 1 . .
    H H12A -0.0596 0.3187 0.7321 0.091 Uiso calc R 1 1 . .
    C C12B 1.0294(2) 0.03867(19) 0.39389(19) 0.0615(7) Uani d . 1 1 . .
    H H12B 1.0964 0.0189 0.3909 0.074 Uiso calc R 1 1 . .
    C C13A 0.01382(19) 0.32755(18) 0.6197(2) 0.0641(7) Uani d . 1 1 . .
    H H13A -0.0383 0.3579 0.5849 0.077 Uiso calc R 1 1 . .
    C C13B 0.9501(2) -0.00710(18) 0.34674(18) 0.0577(7) Uani d . 1 1 . .
    H H13B 0.9635 -0.0576 0.3117 0.069 Uiso calc R 1 1 . .
    C C14A 0.10334(16) 0.30612(15) 0.58193(17) 0.0458(6) Uani d . 1 1 . .
    H H14A 0.1122 0.3222 0.5219 0.055 Uiso calc R 1 1 . .
    C C14B 0.85071(18) 0.02174(14) 0.35123(16) 0.0458(6) Uani d . 1 1 . .
    H H14B 0.7968 -0.0094 0.3198 0.055 Uiso calc R 1 1 . .
    C C15A 0.37606(14) 0.38857(12) 0.58513(14) 0.0318(4) Uani d . 1 1 . .
    C C15B 0.71004(15) 0.27352(12) 0.28880(13) 0.0321(5) Uani d . 1 1 . .
    C C16A 0.30231(16) 0.50038(14) 0.49461(15) 0.0378(5) Uani d . 1 1 . .
    C C16B 0.82753(15) 0.38663(14) 0.32074(14) 0.0376(5) Uani d . 1 1 . .
    C C17A 0.36691(15) 0.56812(13) 0.52574(14) 0.0356(5) Uani d . 1 1 . .
    H H17A 0.3617 0.6274 0.5041 0.043 Uiso calc R 1 1 . .
    C C17B 0.78186(16) 0.44845(13) 0.26077(14) 0.0367(5) Uani d . 1 1 . .
    H H17B 0.8070 0.5069 0.2538 0.044 Uiso calc R 1 1 . .
    C C18A 0.44159(15) 0.54000(12) 0.59313(13) 0.0298(4) Uani d . 1 1 . .
    C C18B 0.69432(14) 0.41563(13) 0.21132(13) 0.0317(4) Uani d . 1 1 . .
    C C19A 0.44741(14) 0.45033(12) 0.62405(13) 0.0290(4) Uani d . 1 1 . .
    C C19B 0.65665(14) 0.32852(12) 0.22385(13) 0.0309(4) Uani d . 1 1 . .
    C C20A 0.56688(17) 0.52153(13) 0.69992(15) 0.0386(5) Uani d . 1 1 . .
    H H20A 0.6223 0.5356 0.7415 0.046 Uiso calc R 1 1 . .
    C C20B 0.55180(16) 0.39220(14) 0.12623(15) 0.0401(5) Uani d . 1 1 . .
    H H20B 0.4959 0.4029 0.0840 0.048 Uiso calc R 1 1 . .
    C C21A 0.54967(18) 0.67998(13) 0.63396(16) 0.0468(6) Uani d . 1 1 . .
    H H21A 0.5035 0.7092 0.5887 0.070 Uiso calc R 1 1 . .
    H H21B 0.6182 0.6833 0.6159 0.070 Uiso calc R 1 1 . .
    H H21C 0.5467 0.7099 0.6917 0.070 Uiso calc R 1 1 . .
    C C21B 0.62941(19) 0.54775(14) 0.11289(18) 0.0530(6) Uani d . 1 1 . .
    H H21D 0.6901 0.5772 0.1399 0.080 Uiso calc R 1 1 . .
    H H21E 0.5700 0.5808 0.1280 0.080 Uiso calc R 1 1 . .
    H H21F 0.6310 0.5461 0.0477 0.080 Uiso calc R 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1A C16A . 1.746(2) ?
    Cl1B C16B . 1.741(2) ?
    S2A O3A . 1.4198(17) ?
    S2A O4A . 1.4273(15) ?
    S2A N7A . 1.6347(17) ?
    S2A C9A . 1.757(2) ?
    S2B O3B . 1.4230(16) ?
    S2B O4B . 1.4305(14) ?
    S2B N7B . 1.6352(17) ?
    S2B C9B . 1.763(2) ?
    N5A C20A . 1.361(3) ?
    N5A C18A . 1.368(2) ?
    N5A C21A . 1.470(2) ?
    N5B C20B . 1.354(3) ?
    N5B C18B . 1.374(2) ?
    N5B C21B . 1.456(2) ?
    N6A C15A . 1.320(2) ?
    N6A C16A . 1.341(3) ?
    N6B C15B . 1.326(3) ?
    N6B C16B . 1.340(2) ?
    N7A C15A . 1.400(2) ?
    N7A H7A . 0.8600 ?
    N7B C15B . 1.401(2) ?
    N7B H7B . 0.8600 ?
    N8A C20A . 1.313(2) ?
    N8A C19A . 1.392(3) ?
    N8B C20B . 1.312(2) ?
    N8B C19B . 1.385(2) ?
    C9A C14A . 1.371(3) ?
    C9A C10A . 1.380(3) ?
    C9B C10B . 1.378(3) ?
    C9B C14B . 1.380(3) ?
    C10A C11A . 1.369(4) ?
    C10A H10A . 0.9300 ?
    C10B C11B . 1.385(3) ?
    C10B H10B . 0.9300 ?
    C11A C12A . 1.373(4) ?
    C11A H11A . 0.9300 ?
    C11B C12B . 1.363(4) ?
    C11B H11B . 0.9300 ?
    C12A C13A . 1.354(4) ?
    C12A H12A . 0.9300 ?
    C12B C13B . 1.373(4) ?
    C12B H12B . 0.9300 ?
    C13A C14A . 1.379(3) ?
    C13A H13A . 0.9300 ?
    C13B C14B . 1.377(3) ?
    C13B H13B . 0.9300 ?
    C14A H14A . 0.9300 ?
    C14B H14B . 0.9300 ?
    C15A C19A . 1.390(3) ?
    C15B C19B . 1.392(3) ?
    C16A C17A . 1.361(3) ?
    C16B C17B . 1.367(3) ?
    C17A C18A . 1.392(3) ?
    C17A H17A . 0.9300 ?
    C17B C18B . 1.389(3) ?
    C17B H17B . 0.9300 ?
    C18A C19A . 1.396(3) ?
    C18B C19B . 1.393(3) ?
    C20A H20A . 0.9300 ?
    C20B H20B . 0.9300 ?
    C21A H21A . 0.9600 ?
    C21A H21B . 0.9600 ?
    C21A H21C . 0.9600 ?
    C21B H21D . 0.9600 ?
    C21B H21E . 0.9600 ?
    C21B H21F . 0.9600 ?
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
    O3A S2A O4A . . 118.82(10) ?
    O3A S2A N7A . . 111.37(10) ?
    O4A S2A N7A . . 103.28(9) ?
    O3A S2A C9A . . 108.41(10) ?
    O4A S2A C9A . . 107.92(10) ?
    N7A S2A C9A . . 106.31(9) ?
    O3B S2B O4B . . 119.51(9) ?
    O3B S2B N7B . . 109.03(9) ?
    O4B S2B N7B . . 103.68(9) ?
    O3B S2B C9B . . 108.80(10) ?
    O4B S2B C9B . . 108.84(9) ?
    N7B S2B C9B . . 106.16(9) ?
    C20A N5A C18A . . 106.34(15) ?
    C20A N5A C21A . . 126.50(18) ?
    C18A N5A C21A . . 127.14(18) ?
    C20B N5B C18B . . 106.11(15) ?
    C20B N5B C21B . . 127.47(19) ?
    C18B N5B C21B . . 126.40(18) ?
    C15A N6A C16A . . 117.71(17) ?
    C15B N6B C16B . . 118.25(18) ?
    C15A N7A S2A . . 125.03(15) ?
    C15A N7A H7A . . 117.5 ?
    S2A N7A H7A . . 117.5 ?
    C15B N7B S2B . . 123.79(15) ?
    C15B N7B H7B . . 118.1 ?
    S2B N7B H7B . . 118.1 ?
    C20A N8A C19A . . 102.94(16) ?
    C20B N8B C19B . . 103.25(16) ?
    C14A C9A C10A . . 121.0(2) ?
    C14A C9A S2A . . 120.72(17) ?
    C10A C9A S2A . . 118.14(18) ?
    C10B C9B C14B . . 120.8(2) ?
    C10B C9B S2B . . 119.93(17) ?
    C14B C9B S2B . . 119.24(16) ?
    C11A C10A C9A . . 118.7(3) ?
    C11A C10A H10A . . 120.7 ?
    C9A C10A H10A . . 120.7 ?
    C9B C10B C11B . . 118.7(2) ?
    C9B C10B H10B . . 120.6 ?
    C11B C10B H10B . . 120.6 ?
    C10A C11A C12A . . 120.6(3) ?
    C10A C11A H11A . . 119.7 ?
    C12A C11A H11A . . 119.7 ?
    C12B C11B C10B . . 120.6(2) ?
    C12B C11B H11B . . 119.7 ?
    C10B C11B H11B . . 119.7 ?
    C13A C12A C11A . . 120.2(2) ?
    C13A C12A H12A . . 119.9 ?
    C11A C12A H12A . . 119.9 ?
    C11B C12B C13B . . 120.3(2) ?
    C11B C12B H12B . . 119.8 ?
    C13B C12B H12B . . 119.8 ?
    C12A C13A C14A . . 120.4(3) ?
    C12A C13A H13A . . 119.8 ?
    C14A C13A H13A . . 119.8 ?
    C12B C13B C14B . . 120.0(2) ?
    C12B C13B H13B . . 120.0 ?
    C14B C13B H13B . . 120.0 ?
    C9A C14A C13A . . 119.1(2) ?
    C9A C14A H14A . . 120.5 ?
    C13A C14A H14A . . 120.5 ?
    C9B C14B C13B . . 119.4(2) ?
    C9B C14B H14B . . 120.3 ?
    C13B C14B H14B . . 120.3 ?
    N6A C15A C19A . . 121.52(17) ?
    N6A C15A N7A . . 118.16(17) ?
    C19A C15A N7A . . 120.32(18) ?
    N6B C15B C19B . . 121.33(17) ?
    N6B C15B N7B . . 117.25(17) ?
    C19B C15B N7B . . 121.38(18) ?
    N6A C16A C17A . . 127.47(19) ?
    N6A C16A Cl1A . . 113.37(16) ?
    C17A C16A Cl1A . . 119.14(16) ?
    N6B C16B C17B . . 126.69(19) ?
    N6B C16B Cl1B . . 115.09(16) ?
    C17B C16B Cl1B . . 118.22(15) ?
    C16A C17A C18A . . 113.45(18) ?
    C16A C17A H17A . . 123.3 ?
    C18A C17A H17A . . 123.3 ?
    C16B C17B C18B . . 113.53(18) ?
    C16B C17B H17B . . 123.2 ?
    C18B C17B H17B . . 123.2 ?
    N5A C18A C17A . . 133.00(17) ?
    N5A C18A C19A . . 105.18(17) ?
    C17A C18A C19A . . 121.82(18) ?
    N5B C18B C17B . . 132.22(17) ?
    N5B C18B C19B . . 105.20(17) ?
    C17B C18B C19B . . 122.51(18) ?
    N8A C19A C15A . . 131.09(17) ?
    N8A C19A C18A . . 110.89(17) ?
    C15A C19A C18A . . 118.02(18) ?
    N8B C19B C18B . . 110.79(17) ?
    N8B C19B C15B . . 131.45(17) ?
    C18B C19B C15B . . 117.66(18) ?
    N8A C20A N5A . . 114.65(19) ?
    N8A C20A H20A . . 122.7 ?
    N5A C20A H20A . . 122.7 ?
    N8B C20B N5B . . 114.65(18) ?
    N8B C20B H20B . . 122.7 ?
    N5B C20B H20B . . 122.7 ?
    N5A C21A H21A . . 109.5 ?
    N5A C21A H21B . . 109.5 ?
    H21A C21A H21B . . 109.5 ?
    N5A C21A H21C . . 109.5 ?
    H21A C21A H21C . . 109.5 ?
    H21B C21A H21C . . 109.5 ?
    N5B C21B H21D . . 109.5 ?
    N5B C21B H21E . . 109.5 ?
    H21D C21B H21E . . 109.5 ?
    N5B C21B H21F . . 109.5 ?
    H21D C21B H21F . . 109.5 ?
    H21E C21B H21F . . 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
    O3A S2A N7A C15A . . . . 54.0(2) ?
    O4A S2A N7A C15A . . . . -177.38(17) ?
    C9A S2A N7A C15A . . . . -63.9(2) ?
    O3B S2B N7B C15B . . . . 42.58(18) ?
    O4B S2B N7B C15B . . . . 170.92(16) ?
    C9B S2B N7B C15B . . . . -74.47(18) ?
    O3A S2A C9A C14A . . . . -20.6(2) ?
    O4A S2A C9A C14A . . . . -150.49(17) ?
    N7A S2A C9A C14A . . . . 99.25(18) ?
    O3A S2A C9A C10A . . . . 155.31(17) ?
    O4A S2A C9A C10A . . . . 25.4(2) ?
    N7A S2A C9A C10A . . . . -84.85(19) ?
    O3B S2B C9B C10B . . . . -14.6(2) ?
    O4B S2B C9B C10B . . . . -146.40(17) ?
    N7B S2B C9B C10B . . . . 102.56(18) ?
    O3B S2B C9B C14B . . . . 166.09(16) ?
    O4B S2B C9B C14B . . . . 34.3(2) ?
    N7B S2B C9B C14B . . . . -76.70(18) ?
    C14A C9A C10A C11A . . . . 1.7(4) ?
    S2A C9A C10A C11A . . . . -174.2(2) ?
    C14B C9B C10B C11B . . . . -0.4(3) ?
    S2B C9B C10B C11B . . . . -179.61(18) ?
    C9A C10A C11A C12A . . . . -0.3(4) ?
    C9B C10B C11B C12B . . . . 0.7(4) ?
    C10A C11A C12A C13A . . . . -0.9(5) ?
    C10B C11B C12B C13B . . . . -0.5(4) ?
    C11A C12A C13A C14A . . . . 0.8(4) ?
    C11B C12B C13B C14B . . . . -0.2(4) ?
    C10A C9A C14A C13A . . . . -1.7(3) ?
    S2A C9A C14A C13A . . . . 174.03(18) ?
    C12A C13A C14A C9A . . . . 0.5(4) ?
    C10B C9B C14B C13B . . . . -0.3(3) ?
    S2B C9B C14B C13B . . . . 178.94(18) ?
    C12B C13B C14B C9B . . . . 0.6(4) ?
    C16A N6A C15A C19A . . . . 1.2(3) ?
    C16A N6A C15A N7A . . . . -179.50(18) ?
    S2A N7A C15A N6A . . . . -9.7(3) ?
    S2A N7A C15A C19A . . . . 169.53(15) ?
    C16B N6B C15B C19B . . . . 1.8(3) ?
    C16B N6B C15B N7B . . . . -175.93(17) ?
    S2B N7B C15B N6B . . . . 21.4(2) ?
    S2B N7B C15B C19B . . . . -156.28(15) ?
    C15A N6A C16A C17A . . . . -0.9(3) ?
    C15A N6A C16A Cl1A . . . . 177.34(15) ?
    C15B N6B C16B C17B . . . . -0.4(3) ?
    C15B N6B C16B Cl1B . . . . 179.63(15) ?
    N6A C16A C17A C18A . . . . 0.2(3) ?
    Cl1A C16A C17A C18A . . . . -177.92(14) ?
    N6B C16B C17B C18B . . . . -1.1(3) ?
    Cl1B C16B C17B C18B . . . . 178.91(15) ?
    C20A N5A C18A C17A . . . . 179.0(2) ?
    C21A N5A C18A C17A . . . . -2.4(3) ?
    C20A N5A C18A C19A . . . . -0.8(2) ?
    C21A N5A C18A C19A . . . . 177.74(17) ?
    C16A C17A C18A N5A . . . . -179.73(19) ?
    C16A C17A C18A C19A . . . . 0.1(3) ?
    C20B N5B C18B C17B . . . . -176.7(2) ?
    C21B N5B C18B C17B . . . . 2.1(3) ?
    C20B N5B C18B C19B . . . . 0.0(2) ?
    C21B N5B C18B C19B . . . . 178.77(19) ?
    C16B C17B C18B N5B . . . . 177.4(2) ?
    C16B C17B C18B C19B . . . . 1.2(3) ?
    C20A N8A C19A C15A . . . . -179.5(2) ?
    C20A N8A C19A C18A . . . . 0.2(2) ?
    N6A C15A C19A N8A . . . . 178.71(19) ?
    N7A C15A C19A N8A . . . . -0.5(3) ?
    N6A C15A C19A C18A . . . . -1.0(3) ?
    N7A C15A C19A C18A . . . . 179.78(17) ?
    N5A C18A C19A N8A . . . . 0.4(2) ?
    C17A C18A C19A N8A . . . . -179.47(17) ?
    N5A C18A C19A C15A . . . . -179.87(16) ?
    C17A C18A C19A C15A . . . . 0.3(3) ?
    C20B N8B C19B C18B . . . . 0.4(2) ?
    C20B N8B C19B C15B . . . . 176.6(2) ?
    N5B C18B C19B N8B . . . . -0.3(2) ?
    C17B C18B C19B N8B . . . . 176.86(18) ?
    N5B C18B C19B C15B . . . . -177.09(17) ?
    C17B C18B C19B C15B . . . . 0.0(3) ?
    N6B C15B C19B N8B . . . . -177.66(19) ?
    N7B C15B C19B N8B . . . . 0.0(3) ?
    N6B C15B C19B C18B . . . . -1.6(3) ?
    N7B C15B C19B C18B . . . . 176.01(17) ?
    C19A N8A C20A N5A . . . . -0.8(2) ?
    C18A N5A C20A N8A . . . . 1.1(2) ?
    C21A N5A C20A N8A . . . . -177.51(18) ?
    C19B N8B C20B N5B . . . . -0.4(2) ?
    C18B N5B C20B N8B . . . . 0.2(2) ?
    C21B N5B C20B N8B . . . . -178.51(19) ?
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
    N7A H7A N8B 4_566 0.86 2.25 3.014(2) 148 yes
    N7B H7B N8A 4_565 0.86 2.25 3.092(2) 165 yes
    C13A H13A Cl1A 3_566 0.93 2.82 3.620(3) 144 yes
    C20A H20A O4A 2_656 0.93 2.47 3.243(3) 141 yes
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2014-03-09
_journal_date_accepted     2014-03-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      4
_journal_page_first     o445
_journal_page_last     o445
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814005388
_journal_coeditor_code     HB7208
_publ_contact_author_name     'H.C.Devarajegowda'
_publ_contact_author_address
;
Department of Physics
Yuvaraja's College (Constituent College)
University of Mysore Mysore
Karnataka
India
;
_publ_contact_author_email     'devarajegowda@yahoo.com'
_publ_contact_author_fax     '+91 0821 2419292'
_publ_contact_author_phone     '+91 0821 2518101'
_publ_section_title
;\
N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)\
benzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Venkatesh B. Devaru'
;
P. G. Department of Physics
LVD College, Raichur 584 103
Karnataka, India
;
    'K. S. Katagi'
;
Department of Chemistry
Karnatak Science College
Karnatak University, Dharwad
Karnataka 580 001, India
;
    'O. Kotresh'
;
Department of Chemistry
Karnatak Science College
Karnatak University, Dharwad
Karnataka 580 001, India
;
    'H. K. Arunkashi'
;
Department of Physics
Moodlakatte Institute of Technology
Kundapura 576 217, Karnataka, India
;
    'H. C. Devarajegowda'
;
Department of Physics
Yuvaraja's College (Constituent College)
University of Mysore, Mysore 570 005
Karnataka, India
;
