#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209018.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209018
loop_
_publ_author_name
'Anilkumar, G. N.'
'Kokila, M. K.'
Puttaraja
'Karki, S. S.'
'Kulkarni, M. V.'
_publ_section_title
;
 6-(4-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide
;
_journal_coeditor_code           TK2024
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2014
_journal_page_last               o2016
_journal_paper_doi               10.1107/S1600536806013687
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H7 Cl N4 O2 S2'
_chemical_formula_moiety         'C10 H7 Cl N4 O2 S2'
_chemical_formula_sum            'C10 H7 Cl N4 O2 S2'
_chemical_formula_weight         314.77
_chemical_name_systematic
;
6-(4-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 103.408(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.469(2)
_cell_length_b                   18.640(5)
_cell_length_c                   9.156(3)
_cell_measurement_reflns_used    240
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.3
_cell_volume                     1240.0(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al.,
1993)
;
_computing_publication_material
'PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9149
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0565P)²+0.6933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.102
_reflns_number_gt                2103
_reflns_number_total             2298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2024.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1239.9(6)
_cod_original_sg_symbol_Hall     '-P 2 ybc'
_cod_original_sg_symbol_H-M      ' P 21/c'
_cod_database_code               2209018
_cod_database_fobs_code          2209018
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'
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_occupancy
Cl Cl1 0.85700(11) -0.08408(4) 0.03688(9) 0.0678(2) Uani d 1
N N1 0.4281(3) 0.14128(10) 0.4272(2) 0.0413(4) Uani d 1
N N2 -0.2963(3) 0.24856(13) 0.5196(3) 0.0429(5) Uani d 1
N N3 0.0164(3) 0.12208(10) 0.5387(2) 0.0395(4) Uani d 1
N N4 0.1662(2) 0.10736(10) 0.4817(2) 0.0364(4) Uani d 1
O O1 -0.0490(2) 0.29611(10) 0.7213(2) 0.0549(5) Uani d 1
O O2 -0.2081(3) 0.18312(10) 0.75363(19) 0.0532(5) Uani d 1
S S1 0.23694(9) 0.23278(3) 0.58574(8) 0.0476(2) Uani d 1
S S2 -0.13608(8) 0.23118(3) 0.66104(6) 0.03948(18) Uani d 1
C C1 0.2961(3) 0.15949(12) 0.4916(3) 0.0395(5) Uani d 1
C C2 0.0385(3) 0.18558(12) 0.5944(2) 0.0381(5) Uani d 1
C C5 0.2179(3) 0.05106(13) 0.4040(3) 0.0390(5) Uani d 1
C C6 0.3791(3) 0.07267(12) 0.3710(2) 0.0364(5) Uani d 1
C C7 0.4949(3) 0.03417(12) 0.2880(2) 0.0376(5) Uani d 1
C C8 0.4553(4) -0.03592(13) 0.2405(3) 0.0456(6) Uani d 1
C C9 0.5657(4) -0.07181(14) 0.1631(3) 0.0516(6) Uani d 1
C C10 0.7166(3) -0.03831(14) 0.1329(3) 0.0455(6) Uani d 1
C C11 0.7581(4) 0.03148(15) 0.1770(3) 0.0492(6) Uani d 1
C C12 0.6467(4) 0.06722(14) 0.2544(3) 0.0465(6) Uani d 1
H H2A -0.268(4) 0.2769(16) 0.467(3) 0.051(9) Uiso d 1
H H2B -0.363(4) 0.2139(16) 0.489(3) 0.046(8) Uiso d 1
H H5 0.151(4) 0.0111(15) 0.384(3) 0.048(7) Uiso d 1
H H8 0.352(4) -0.0579(15) 0.260(3) 0.053(8) Uiso d 1
H H9 0.538(4) -0.1130(17) 0.128(3) 0.060(9) Uiso d 1
H H11 0.863(4) 0.0528(15) 0.155(3) 0.059(8) Uiso d 1
H H12 0.673(4) 0.1154(15) 0.282(3) 0.052(7) Uiso d 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C6 104.11(19) ?
S2 N2 H2A 113(2) ?
S2 N2 H2B 113.8(19) ?
H2A N2 H2B 123(3) ?
C2 N3 N4 107.19(18) ?
N3 N4 C1 117.72(18) ?
N3 N4 C5 134.80(19) ?
C1 N4 C5 107.35(19) ?
C1 S1 C2 86.69(11) ?
O2 S2 O1 120.43(11) ?
O2 S2 N2 107.36(13) ?
O1 S2 N2 109.55(13) ?
O2 S2 C2 108.19(11) ?
O1 S2 C2 103.54(11) ?
N2 S2 C2 107.04(11) ?
N1 C1 N4 112.7(2) ?
N1 C1 S1 137.63(18) yes
N4 C1 S1 109.69(16) ?
N3 C2 S1 118.66(17) ?
N3 C2 S2 122.68(17) ?
S1 C2 S2 118.27(13) ?
C6 C5 N4 104.9(2) ?
C6 C5 H5 132.7(17) ?
N4 C5 H5 122.4(17) ?
C5 C6 N1 111.0(2) ?
C5 C6 C7 128.7(2) yes
N1 C6 C7 120.3(2) ?
C12 C7 C8 118.3(2) ?
C12 C7 C6 120.6(2) ?
C8 C7 C6 121.0(2) ?
C9 C8 C7 120.6(2) ?
C9 C8 H8 120.5(17) ?
C7 C8 H8 118.9(17) ?
C10 C9 C8 120.0(3) ?
C10 C9 H9 119(2) ?
C8 C9 H9 121(2) ?
C9 C10 C11 120.7(2) ?
C9 C10 Cl1 119.9(2) ?
C11 C10 Cl1 119.4(2) ?
C10 C11 C12 119.0(2) ?
C10 C11 H11 118.4(18) ?
C12 C11 H11 122.6(18) ?
C7 C12 C11 121.3(2) ?
C7 C12 H12 119.8(17) ?
C11 C12 H12 118.9(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C10 1.740(2) ?
N1 C1 1.306(3) ?
N1 C6 1.395(3) ?
N2 S2 1.580(2) yes
N2 H2A 0.77(3) ?
N2 H2B 0.82(3) ?
N3 C2 1.285(3) ?
N3 N4 1.367(3) ?
N4 C1 1.362(3) ?
N4 C5 1.373(3) ?
O1 S2 1.4232(19) yes
O2 S2 1.4221(18) yes
S1 C1 1.726(2) yes
S1 C2 1.741(2) yes
S2 C2 1.778(2) yes
C5 C6 1.368(3) ?
C5 H5 0.89(3) ?
C6 C7 1.465(3) yes
C7 C12 1.386(3) ?
C7 C8 1.387(3) ?
C8 C9 1.379(4) ?
C8 H8 0.93(3) ?
C9 C10 1.371(4) ?
C9 H9 0.84(3) ?
C10 C11 1.376(4) ?
C11 C12 1.383(4) ?
C11 H11 0.94(3) ?
C12 H12 0.94(3) ?
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
N2 H2A O2 4_565 0.78(3) 2.23(3) 2.955(3) 155(3) yes
N2 H2B N1 1_455 0.82(3) 2.04(3) 2.853(3) 167(3) yes
C8 H8 O2 3_556 0.93(3) 2.56(3) 3.315(3) 139(2) yes
C12 H12 N1 . 0.94(3) 2.54(3) 2.876(4) 101(2) yes
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
_geom_torsion_publ_flag
C2 N3 N4 C1 -1.4(3) ?
C2 N3 N4 C5 -176.5(2) ?
C6 N1 C1 N4 0.4(3) ?
C6 N1 C1 S1 -178.6(2) ?
N3 N4 C1 N1 -176.70(18) ?
C5 N4 C1 N1 -0.3(3) ?
N3 N4 C1 S1 2.6(2) ?
C5 N4 C1 S1 178.94(15) ?
C2 S1 C1 N1 176.9(3) ?
C2 S1 C1 N4 -2.14(17) ?
N4 N3 C2 S1 -0.4(2) ?
N4 N3 C2 S2 172.33(15) ?
C1 S1 C2 N3 1.6(2) ?
C1 S1 C2 S2 -171.51(15) ?
O2 S2 C2 N3 47.2(2) yes
O1 S2 C2 N3 176.04(19) ?
N2 S2 C2 N3 -68.3(2) yes
O2 S2 C2 S1 -140.05(14) ?
O1 S2 C2 S1 -11.18(17) ?
N2 S2 C2 S1 104.53(16) ?
N3 N4 C5 C6 175.6(2) ?
C1 N4 C5 C6 0.1(2) ?
N4 C5 C6 N1 0.1(2) ?
N4 C5 C6 C7 -179.3(2) ?
C1 N1 C6 C5 -0.3(2) ?
C1 N1 C6 C7 179.19(19) ?
C5 C6 C7 C12 174.5(2) yes
N1 C6 C7 C12 -4.8(3) ?
C5 C6 C7 C8 -5.2(4) yes
N1 C6 C7 C8 175.4(2) ?
C12 C7 C8 C9 0.6(4) ?
C6 C7 C8 C9 -179.6(2) ?
C7 C8 C9 C10 0.2(4) ?
C8 C9 C10 C11 -1.0(4) ?
C8 C9 C10 Cl1 179.3(2) ?
C9 C10 C11 C12 0.9(4) ?
Cl1 C10 C11 C12 -179.4(2) ?
C8 C7 C12 C11 -0.7(4) ?
C6 C7 C12 C11 179.6(2) ?
C10 C11 C12 C7 0.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3390363
