#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/88/2228829.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_2228829
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Hemamalini, Madhukar'
'Prasad, D. Jagadeesh'
'Nagaraja, G. K.'
'Anitha, V. V.'
_publ_section_title
;
 6-(4-Chlorophenyl)-2-isobutylimidazo[2,1-b][1,3,4]thiadiazole
;
_journal_coeditor_code           NG5089
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o207
_journal_paper_doi               10.1107/S1600536810052621
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H14 Cl N3 S'
_chemical_formula_moiety         'C14 H14 Cl N3 S'
_chemical_formula_sum            'C14 H14 Cl N3 S'
_chemical_formula_weight         291.79
_chemical_name_systematic
;
6-(4-Chlorophenyl)-2-isobutylimidazo[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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.75520(10)
_cell_length_b                   26.4052(5)
_cell_length_c                   9.7662(2)
_cell_measurement_reflns_used    5357
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.26
_cell_volume                     1454.92(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12320
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.8973
_exptl_absorpt_correction_T_min  0.8347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.4615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                2646
_reflns_number_total             3353
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5089.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228829
_cod_database_fobs_code          2228829
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.79047(16) -0.15309(3) 0.31411(7) 0.0936(3) Uani d . 1 . .
S S1 0.87829(9) 0.11339(2) 0.99277(7) 0.0661(2) Uani d . 1 . .
N N1 0.8370(3) 0.03334(6) 0.79472(18) 0.0536(4) Uani d . 1 . .
N N2 1.1813(3) 0.05331(6) 0.93125(17) 0.0517(4) Uani d . 1 . .
N N3 1.3144(3) 0.08204(7) 1.03504(19) 0.0609(5) Uani d . 1 . .
C C1 0.7404(4) -0.04026(8) 0.5763(2) 0.0544(5) Uani d . 1 . .
H H1A 0.6230 -0.0182 0.5931 0.065 Uiso calc R 1 . .
C C2 0.6859(4) -0.07545(8) 0.4702(2) 0.0610(5) Uani d . 1 . .
H H2A 0.5347 -0.0767 0.4147 0.073 Uiso calc R 1 . .
C C3 0.8587(4) -0.10854(8) 0.4479(2) 0.0617(5) Uani d . 1 . .
C C4 1.0837(4) -0.10677(9) 0.5281(3) 0.0686(6) Uani d . 1 . .
H H4A 1.1991 -0.1294 0.5116 0.082 Uiso calc R 1 . .
C C5 1.1370(4) -0.07123(8) 0.6331(2) 0.0613(5) Uani d . 1 . .
H H5A 1.2889 -0.0701 0.6877 0.074 Uiso calc R 1 . .
C C6 0.9657(3) -0.03694(7) 0.65853(19) 0.0471(4) Uani d . 1 . .
C C7 1.0177(3) 0.00199(7) 0.76767(19) 0.0468(4) Uani d . 1 . .
C C8 0.9462(3) 0.06335(7) 0.8937(2) 0.0507(4) Uani d . 1 . .
C C9 1.1782(4) 0.11490(8) 1.0758(2) 0.0578(5) Uani d . 1 . .
C C10 1.2301(3) 0.01388(8) 0.8507(2) 0.0544(5) Uani d . 1 . .
H H10A 1.3760 -0.0015 0.8522 0.065 Uiso calc R 1 . .
C C11 1.2613(5) 0.15173(9) 1.1910(2) 0.0731(6) Uani d . 1 . .
H H11A 1.4291 0.1461 1.2261 0.088 Uiso calc R 1 . .
H H11B 1.1795 0.1445 1.2666 0.088 Uiso calc R 1 . .
C C12 1.2254(5) 0.20690(10) 1.1527(3) 0.0813(7) Uani d . 1 . .
H H12A 1.0588 0.2118 1.1082 0.098 Uiso calc R 1 . .
C C13 1.2777(9) 0.23946(14) 1.2842(4) 0.1384(16) Uani d . 1 . .
H H13A 1.1748 0.2297 1.3459 0.208 Uiso calc R 1 . .
H H13B 1.2516 0.2745 1.2591 0.208 Uiso calc R 1 . .
H H13C 1.4397 0.2347 1.3303 0.208 Uiso calc R 1 . .
C C14 1.3764(8) 0.22228(13) 1.0505(4) 0.1297(15) Uani d . 1 . .
H H14A 1.3400 0.2011 0.9691 0.195 Uiso calc R 1 . .
H H14B 1.5407 0.2185 1.0930 0.195 Uiso calc R 1 . .
H H14C 1.3448 0.2570 1.0240 0.195 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C9 . . 88.02(10) ?
C8 N1 C7 . . 103.40(15) ?
C8 N2 C10 . . 107.48(16) ?
C8 N2 N3 . . 118.26(17) ?
C10 N2 N3 . . 134.26(16) ?
C9 N3 N2 . . 108.46(16) ?
C2 C1 C6 . . 121.66(19) ?
C2 C1 H1A . . 119.2 ?
C6 C1 H1A . . 119.2 ?
C3 C2 C1 . . 118.9(2) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 121.2(2) ?
C2 C3 Cl1 . . 118.99(18) ?
C4 C3 Cl1 . . 119.80(18) ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C1 C6 C5 . . 117.93(19) ?
C1 C6 C7 . . 119.84(17) ?
C5 C6 C7 . . 122.23(17) ?
C10 C7 N1 . . 111.42(17) ?
C10 C7 C6 . . 128.53(17) ?
N1 C7 C6 . . 120.03(15) ?
N1 C8 N2 . . 112.88(17) ?
N1 C8 S1 . . 138.34(15) ?
N2 C8 S1 . . 108.78(14) ?
N3 C9 C11 . . 123.3(2) ?
N3 C9 S1 . . 116.48(16) ?
C11 C9 S1 . . 120.14(18) ?
C7 C10 N2 . . 104.82(16) ?
C7 C10 H10A . . 127.6 ?
N2 C10 H10A . . 127.6 ?
C9 C11 C12 . . 115.8(2) ?
C9 C11 H11A . . 108.3 ?
C12 C11 H11A . . 108.3 ?
C9 C11 H11B . . 108.3 ?
C12 C11 H11B . . 108.3 ?
H11A C11 H11B . . 107.4 ?
C14 C12 C11 . . 110.9(3) ?
C14 C12 C13 . . 111.3(3) ?
C11 C12 C13 . . 110.0(3) ?
C14 C12 H12A . . 108.2 ?
C11 C12 H12A . . 108.2 ?
C13 C12 H12A . . 108.2 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
Cl1 C3 . 1.744(2) ?
S1 C8 . 1.727(2) ?
S1 C9 . 1.757(2) ?
N1 C8 . 1.311(3) ?
N1 C7 . 1.395(2) ?
N2 C8 . 1.356(2) ?
N2 C10 . 1.367(3) ?
N2 N3 . 1.372(2) ?
N3 C9 . 1.284(3) ?
C1 C2 . 1.381(3) ?
C1 C6 . 1.387(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.373(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.376(3) ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.397(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.468(3) ?
C7 C10 . 1.363(3) ?
C9 C11 . 1.492(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.508(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C14 . 1.503(4) ?
C12 C13 . 1.525(4) ?
C12 H12A . 0.9800 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
C11 H11B Cg3 3_757 0.97 2.70 3.544(2) 145 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N2 N3 C9 . . . . -0.8(2) ?
C10 N2 N3 C9 . . . . 179.7(2) ?
C6 C1 C2 C3 . . . . 1.3(3) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 Cl1 . . . . 179.91(16) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
Cl1 C3 C4 C5 . . . . 179.57(17) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
C2 C1 C6 C5 . . . . -1.4(3) ?
C2 C1 C6 C7 . . . . 178.29(18) ?
C4 C5 C6 C1 . . . . 0.9(3) ?
C4 C5 C6 C7 . . . . -178.82(19) ?
C8 N1 C7 C10 . . . . 0.0(2) ?
C8 N1 C7 C6 . . . . -178.69(16) ?
C1 C6 C7 C10 . . . . -174.21(19) ?
C5 C6 C7 C10 . . . . 5.5(3) ?
C1 C6 C7 N1 . . . . 4.2(3) ?
C5 C6 C7 N1 . . . . -176.07(17) ?
C7 N1 C8 N2 . . . . -0.1(2) ?
C7 N1 C8 S1 . . . . 179.56(18) ?
C10 N2 C8 N1 . . . . 0.2(2) ?
N3 N2 C8 N1 . . . . -179.44(16) ?
C10 N2 C8 S1 . . . . -179.60(13) ?
N3 N2 C8 S1 . . . . 0.8(2) ?
C9 S1 C8 N1 . . . . 179.9(2) ?
C9 S1 C8 N2 . . . . -0.42(14) ?
N2 N3 C9 C11 . . . . 178.09(18) ?
N2 N3 C9 S1 . . . . 0.4(2) ?
C8 S1 C9 N3 . . . . -0.01(17) ?
C8 S1 C9 C11 . . . . -177.76(18) ?
N1 C7 C10 N2 . . . . 0.1(2) ?
C6 C7 C10 N2 . . . . 178.64(17) ?
C8 N2 C10 C7 . . . . -0.1(2) ?
N3 N2 C10 C7 . . . . 179.36(19) ?
N3 C9 C11 C12 . . . . 122.0(3) ?
S1 C9 C11 C12 . . . . -60.4(3) ?
C9 C11 C12 C14 . . . . -66.3(3) ?
C9 C11 C12 C13 . . . . 170.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5857702
