#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/71/2237168.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_2237168
loop_
_publ_author_name
'Praveen, A.S.'
'Jasinski, Jerry P.'
'Krauss, Shannon T.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 6-(3-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole
;
_journal_coeditor_code           IM2414
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o66
_journal_paper_doi               10.1107/S1600536812049793
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H6 Cl N3 S'
_chemical_formula_moiety         'C10 H6 Cl N3 S'
_chemical_formula_sum            'C10 H6 Cl N3 S'
_chemical_formula_weight         235.70
_chemical_name_systematic
;
6-(3-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.269(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.43804(19)
_cell_length_b                   12.4222(4)
_cell_length_c                   14.1684(4)
_cell_measurement_reflns_used    2788
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.3481
_cell_measurement_theta_min      3.1673
_cell_volume                     941.78(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et
al.,
2006)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5495
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         4.77
_exptl_absorpt_coefficient_mu    5.366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0362
_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)+(0.0559P)²+0.2711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1650
_reflns_number_total             1846
_reflns_threshold_expression     I>2sigma(I))
_cod_data_source_file            im2414.cif
_cod_data_source_block           I
_cod_original_cell_volume        941.77(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2237168
_cod_database_fobs_code          2237168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.35900(10) 0.10200(4) 0.67741(4) 0.02949(18) Uani d . 1 1
S S1 0.39725(10) 0.62878(4) 0.24567(3) 0.02652(18) Uani d . 1 1
N N1 0.0469(3) 0.61595(14) 0.34925(13) 0.0253(4) Uani d . 1 1
N N2 0.2006(3) 0.52794(13) 0.36757(12) 0.0199(4) Uani d . 1 1
N N3 0.5314(3) 0.43233(13) 0.34504(12) 0.0222(4) Uani d . 1 1
C C1 0.1320(4) 0.67447(17) 0.28675(15) 0.0261(4) Uani d . 1 1
H H1 0.0545 0.7386 0.2645 0.031 Uiso calc R 1 1
C C2 0.3979(4) 0.51895(15) 0.32099(13) 0.0208(4) Uani d . 1 1
C C3 0.2043(4) 0.44025(16) 0.42652(14) 0.0217(4) Uani d . 1 1
H H3 0.0929 0.4235 0.4671 0.026 Uiso calc R 1 1
C C4 0.4101(4) 0.38271(15) 0.41207(13) 0.0190(4) Uani d . 1 1
C C5 0.5067(3) 0.28278(15) 0.46084(13) 0.0192(4) Uani d . 1 1
C C6 0.3963(3) 0.24196(15) 0.53512(14) 0.0205(4) Uani d . 1 1
H H6 0.2605 0.2769 0.5531 0.025 Uiso calc R 1 1
C C7 0.4911(4) 0.14891(16) 0.58176(13) 0.0213(4) Uani d . 1 1
C C8 0.6921(4) 0.09440(16) 0.55644(16) 0.0258(4) Uani d . 1 1
H H8 0.7526 0.0317 0.5881 0.031 Uiso calc R 1 1
C C9 0.8008(4) 0.13562(16) 0.48276(15) 0.0254(4) Uani d . 1 1
H H9 0.9360 0.1001 0.4650 0.030 Uiso calc R 1 1
C C10 0.7107(4) 0.22930(15) 0.43499(14) 0.0219(4) Uani d . 1 1
H H10 0.7861 0.2563 0.3860 0.026 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 S1 C1 87.81(9)
C1 N1 N2 107.27(17)
C2 N2 C3 107.63(16)
C2 N2 N1 118.68(16)
C3 N2 N1 133.69(17)
C2 N3 C4 103.49(15)
N1 C1 S1 117.63(16)
N1 C1 H1 121.2
S1 C1 H1 121.2
N3 C2 N2 112.95(17)
N3 C2 S1 138.46(15)
N2 C2 S1 108.59(14)
N2 C3 C4 104.29(16)
N2 C3 H3 127.9
C4 C3 H3 127.9
C3 C4 N3 111.64(16)
C3 C4 C5 126.96(18)
N3 C4 C5 121.37(17)
C6 C5 C10 119.54(18)
C6 C5 C4 119.66(17)
C10 C5 C4 120.79(18)
C7 C6 C5 119.29(17)
C7 C6 H6 120.4
C5 C6 H6 120.4
C6 C7 C8 121.87(18)
C6 C7 Cl1 118.69(15)
C8 C7 Cl1 119.41(16)
C9 C8 C7 118.44(19)
C9 C8 H8 120.8
C7 C8 H8 120.8
C8 C9 C10 121.00(19)
C8 C9 H9 119.5
C10 C9 H9 119.5
C9 C10 C5 119.86(18)
C9 C10 H10 120.1
C5 C10 H10 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.7432(19)
S1 C2 1.7318(19)
S1 C1 1.744(2)
N1 C1 1.293(3)
N1 N2 1.373(2)
N2 C2 1.361(3)
N2 C3 1.371(2)
N3 C2 1.309(2)
N3 C4 1.393(2)
C1 H1 0.9300
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.471(3)
C5 C6 1.397(3)
C5 C10 1.397(3)
C6 C7 1.385(3)
C6 H6 0.9300
C7 C8 1.386(3)
C8 C9 1.386(3)
C8 H8 0.9300
C9 C10 1.391(3)
C9 H9 0.9300
C10 H10 0.9300
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
C1 N1 N2 C2 0.2(2)
C1 N1 N2 C3 179.7(2)
N2 N1 C1 S1 0.3(2)
C2 S1 C1 N1 -0.45(17)
C4 N3 C2 N2 -0.1(2)
C4 N3 C2 S1 179.75(18)
C3 N2 C2 N3 -0.2(2)
N1 N2 C2 N3 179.44(17)
C3 N2 C2 S1 179.87(13)
N1 N2 C2 S1 -0.5(2)
C1 S1 C2 N3 -179.4(2)
C1 S1 C2 N2 0.47(14)
C2 N2 C3 C4 0.5(2)
N1 N2 C3 C4 -179.12(19)
N2 C3 C4 N3 -0.6(2)
N2 C3 C4 C5 177.43(17)
C2 N3 C4 C3 0.4(2)
C2 N3 C4 C5 -177.68(17)
C3 C4 C5 C6 -4.9(3)
N3 C4 C5 C6 172.90(17)
C3 C4 C5 C10 176.33(19)
N3 C4 C5 C10 -5.9(3)
C10 C5 C6 C7 -0.1(3)
C4 C5 C6 C7 -178.88(17)
C5 C6 C7 C8 -0.4(3)
C5 C6 C7 Cl1 177.50(14)
C6 C7 C8 C9 0.5(3)
Cl1 C7 C8 C9 -177.37(15)
C7 C8 C9 C10 -0.1(3)
C8 C9 C10 C5 -0.4(3)
C6 C5 C10 C9 0.5(3)
C4 C5 C10 C9 179.27(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658278
2 PubChem 107646812
