#------------------------------------------------------------------------------
#$Date: 2019-12-26 21:59:38 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246130 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311837.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_2311837
loop_
_publ_author_name
'Praveen, Aletti S.'
'Yathirajan, Hemmige S.'
'Kaur, Manpreet'
'Narayana, Badiadka'
'Hosten, Eric C.'
'Betz, Richard'
'Glidewell, Christopher'
_publ_section_title
;
 Different patterns of supramolecular assembly in constitutionally similar
 6-arylimidazo[2,1-b][1,3,4]thiadiazoles.
;
_journal_coeditor_code           SK3560
_journal_issue                   'Pt 9'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              920
_journal_page_last               926
_journal_paper_doi               10.1107/S2053229614018762
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H8 Cl N3 S'
_chemical_formula_moiety         'C11 H8 Cl N3 S'
_chemical_formula_sum            'C11 H8 Cl N3 S'
_chemical_formula_weight         249.71
_chemical_name_systematic
;
6-(2-Chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5567(3)
_cell_length_b                   11.4589(5)
_cell_length_c                   24.9006(11)
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.315
_cell_measurement_theta_min      3.153
_cell_volume                     2156.18(16)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL2014 (Sheldrick, 2014 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15450
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         3.153
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.466
_exptl_crystal_size_min          0.268
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+1.0733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                2356
_reflns_number_total             2666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3560sup1.cif
_cod_data_source_block           II
_cod_database_code               2311837
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.873
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
S S1 0.80106(5) 0.65665(3) 0.45158(2) 0.03626(12) Uani d 1
C C2 0.85112(17) 0.51521(13) 0.42998(6) 0.0287(3) Uani d 1
N N3 0.81433(16) 0.43078(11) 0.46262(5) 0.0312(3) Uani d 1
N N4 0.74098(15) 0.47874(10) 0.50798(4) 0.0262(2) Uani d 1
C C5 0.67939(19) 0.43257(12) 0.55510(5) 0.0287(3) Uani d 1
H H5 0.6739 0.3527 0.5652 0.034 Uiso calc 1
C C6 0.62709(16) 0.52820(11) 0.58465(5) 0.0243(3) Uani d 1
N N7 0.65651(16) 0.63161(10) 0.55642(5) 0.0289(2) Uani d 1
C C7A 0.72392(17) 0.59658(12) 0.51079(5) 0.0266(3) Uani d 1
C C21 0.93002(19) 0.49516(15) 0.37581(6) 0.0369(3) Uani d 1
H H21A 0.8435 0.5158 0.3481 0.055 Uiso calc 1
H H21B 0.9626 0.4128 0.3721 0.055 Uiso calc 1
H H21C 1.0358 0.5438 0.3717 0.055 Uiso calc 1
C C61 0.54653(16) 0.53729(11) 0.63833(5) 0.0252(3) Uani d 1
C C62 0.52735(19) 0.44666(12) 0.67546(5) 0.0297(3) Uani d 1
Cl Cl62 0.61184(7) 0.30845(4) 0.66226(2) 0.05021(14) Uani d 1
C C63 0.4444(2) 0.46260(14) 0.72479(6) 0.0352(3) Uani d 1
H H63 0.4322 0.3987 0.7488 0.042 Uiso calc 1
C C64 0.3800(2) 0.57038(15) 0.73882(6) 0.0370(3) Uani d 1
H H64 0.3229 0.5815 0.7724 0.044 Uiso calc 1
C C65 0.3993(2) 0.66291(15) 0.70344(6) 0.0359(3) Uani d 1
H H65 0.3564 0.7380 0.7130 0.043 Uiso calc 1
C C66 0.48064(19) 0.64626(13) 0.65427(5) 0.0304(3) Uani d 1
H H66 0.4922 0.7107 0.6305 0.036 Uiso calc 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'
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'
S S 0.1246 0.1234 '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
C7A S1 C2 88.06(7)
N3 C2 C21 122.58(13)
N3 C2 S1 116.96(11)
C21 C2 S1 120.45(11)
C2 N3 N4 107.71(12)
C7A N4 C5 107.93(11)
C7A N4 N3 118.59(11)
C5 N4 N3 133.46(12)
N4 C5 C6 104.36(12)
N4 C5 H5 127.8
C6 C5 H5 127.8
C5 C6 N7 111.13(12)
C5 C6 C61 131.28(12)
N7 C6 C61 117.58(11)
C7A N7 C6 103.83(11)
N7 C7A N4 112.74(12)
N7 C7A S1 138.59(11)
N4 C7A S1 108.67(10)
C2 C21 H21A 109.5
C2 C21 H21B 109.5
H21A C21 H21B 109.5
C2 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C62 C61 C66 115.96(12)
C62 C61 C6 126.20(12)
C66 C61 C6 117.84(12)
C63 C62 C61 122.21(13)
C63 C62 Cl62 116.87(11)
C61 C62 Cl62 120.90(11)
C64 C63 C62 120.16(14)
C64 C63 H63 119.9
C62 C63 H63 119.9
C63 C64 C65 119.30(14)
C63 C64 H64 120.3
C65 C64 H64 120.3
C66 C65 C64 120.24(15)
C66 C65 H65 119.9
C64 C65 H65 119.9
C65 C66 C61 122.10(14)
C65 C66 H66 119.0
C61 C66 H66 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7A 1.7283(14)
S1 C2 1.7491(15)
C2 N3 1.2937(19)
C2 C21 1.4927(19)
N3 N4 1.3731(16)
N4 C7A 1.3583(17)
N4 C5 1.3686(17)
C5 C6 1.3777(19)
C5 H5 0.9500
C6 N7 1.3957(17)
C6 C61 1.4725(18)
N7 C7A 1.3082(17)
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C61 C62 1.3980(19)
C61 C66 1.4016(19)
C62 C63 1.391(2)
C62 Cl62 1.7389(15)
C63 C64 1.372(2)
C63 H63 0.9500
C64 C65 1.386(2)
C64 H64 0.9500
C65 C66 1.383(2)
C65 H65 0.9500
C66 H66 0.9500
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
C64 H64 Cg1 26_557 0.95 2.690 3.6297(16) 135 no
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
C7A S1 C2 N3 0.40(11)
C7A S1 C2 C21 179.46(12)
C21 C2 N3 N4 -178.84(12)
S1 C2 N3 N4 0.20(15)
C2 N3 N4 C7A -0.96(16)
C2 N3 N4 C5 -179.32(14)
C7A N4 C5 C6 -0.05(14)
N3 N4 C5 C6 178.44(13)
N4 C5 C6 N7 -0.25(15)
N4 C5 C6 C61 178.70(13)
C5 C6 N7 C7A 0.45(15)
C61 C6 N7 C7A -178.66(11)
C6 N7 C7A N4 -0.49(15)
C6 N7 C7A S1 -179.99(13)
C5 N4 C7A N7 0.36(16)
N3 N4 C7A N7 -178.40(11)
C5 N4 C7A S1 -179.99(9)
N3 N4 C7A S1 1.25(15)
C2 S1 C7A N7 178.65(16)
C2 S1 C7A N4 -0.86(10)
C5 C6 C61 C62 9.8(2)
N7 C6 C61 C62 -171.26(13)
C5 C6 C61 C66 -169.56(14)
N7 C6 C61 C66 9.33(17)
C66 C61 C62 C63 1.4(2)
C6 C61 C62 C63 -178.00(13)
C66 C61 C62 Cl62 -177.10(10)
C6 C61 C62 Cl62 3.49(19)
C61 C62 C63 C64 -0.9(2)
Cl62 C62 C63 C64 177.67(12)
C62 C63 C64 C65 -0.2(2)
C63 C64 C65 C66 0.7(2)
C64 C65 C66 C61 -0.2(2)
C62 C61 C66 C65 -0.9(2)
C6 C61 C66 C65 178.58(13)
