#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/28/2232854.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_2232854
loop_
_publ_author_name
'Kargar, Hadi'
'Kia, Reza'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 5-[(E)-(5-Bromo-2-hydroxybenzylidene)amino]-1,3,4-thiadiazole-2(3H)-thione
;
_journal_coeditor_code           LH5379
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3436
_journal_paper_doi               10.1107/S1600536811049920
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H6 Br N3 O S2'
_chemical_formula_moiety         'C9 H6 Br N3 O S2'
_chemical_formula_sum            'C9 H6 Br N3 O S2'
_chemical_formula_weight         316.20
_chemical_name_systematic
5-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-1,3,4-thiadiazole-2(3H)-thione
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.660(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.3690(13)
_cell_length_b                   4.0016(3)
_cell_length_c                   16.2877(13)
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.31
_cell_measurement_theta_min      2.50
_cell_volume                     1104.82(15)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      291(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2734
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.078
_exptl_absorpt_correction_T_max  0.9229
_exptl_absorpt_correction_T_min  0.6626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.709
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+3.7473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1760
_reflns_number_total             10313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5379.cif
_cod_data_source_block           I
_cod_original_cell_volume        1104.82(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232854
_cod_database_fobs_code          2232854
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.65016(4) 0.82937(19) -0.22477(5) 0.0438(2) Uani d . 1 1
S S1 0.92727(8) 0.4125(4) 0.25824(11) 0.0306(4) Uani d . 1 1
S S2 1.06396(9) 0.3421(4) 0.43539(10) 0.0329(4) Uani d . 1 1
O O1 0.6140(2) 0.1515(13) 0.0870(3) 0.0439(12) Uani d . 1 1
H H1 0.6563 0.1408 0.1296 0.066 Uiso calc R 1 1
N N1 0.7683(3) 0.2398(13) 0.1762(3) 0.0314(12) Uani d . 1 1
N N2 0.8404(3) 0.0884(14) 0.3226(4) 0.0355(13) Uani d . 1 1
N N3 0.9159(3) 0.1150(13) 0.3865(3) 0.0347(13) Uani d . 1 1
H H3 0.9211 -0.0002 0.4408 0.042 Uiso d R 1 1
C C1 0.6244(3) 0.3022(18) 0.0192(4) 0.0340(15) Uani d . 1 1
C C2 0.6990(3) 0.4180(15) 0.0246(4) 0.0286(13) Uani d . 1 1
C C3 0.7065(3) 0.5752(15) -0.0484(4) 0.0315(14) Uani d . 1 1
H H3A 0.7556 0.6477 -0.0453 0.038 Uiso calc R 1 1
C C4 0.6402(3) 0.6216(15) -0.1255(4) 0.0313(14) Uani d . 1 1
C C5 0.5670(4) 0.5144(17) -0.1308(4) 0.0365(15) Uani d . 1 1
H H5A 0.5229 0.5488 -0.1829 0.044 Uiso calc R 1 1
C C6 0.5587(3) 0.3570(17) -0.0598(4) 0.0367(15) Uani d . 1 1
H H6A 0.5091 0.2864 -0.0642 0.044 Uiso calc R 1 1
C C7 0.7688(3) 0.3839(16) 0.1055(4) 0.0339(15) Uani d . 1 1
H H7A 0.8162 0.4697 0.1066 0.041 Uiso calc R 1 1
C C8 0.8377(3) 0.2352(15) 0.2507(4) 0.0260(13) Uani d . 1 1
C C9 0.9707(3) 0.2737(14) 0.3678(4) 0.0261(13) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0511(4) 0.0493(4) 0.0304(4) 0.0088(3) 0.0152(3) 0.0084(3)
S1 0.0242(7) 0.0387(9) 0.0263(8) -0.0014(6) 0.0067(6) 0.0065(7)
S2 0.0252(7) 0.0429(9) 0.0264(9) -0.0014(7) 0.0055(6) -0.0007(7)
O1 0.030(2) 0.065(3) 0.033(3) -0.009(2) 0.008(2) 0.008(3)
N1 0.026(3) 0.039(3) 0.026(3) 0.002(2) 0.006(2) 0.001(2)
N2 0.024(2) 0.051(3) 0.029(3) -0.006(2) 0.006(2) 0.003(3)
N3 0.033(3) 0.047(3) 0.024(3) -0.005(2) 0.010(2) 0.006(3)
C1 0.029(3) 0.053(4) 0.024(3) -0.008(3) 0.014(3) -0.004(3)
C2 0.027(3) 0.031(3) 0.026(3) 0.001(2) 0.008(3) 0.001(3)
C3 0.024(3) 0.041(4) 0.028(3) 0.002(3) 0.008(3) 0.000(3)
C4 0.033(3) 0.032(3) 0.026(3) 0.001(3) 0.007(3) 0.003(3)
C5 0.033(3) 0.044(4) 0.025(3) 0.003(3) 0.003(3) -0.002(3)
C6 0.024(3) 0.045(4) 0.037(4) -0.003(3) 0.008(3) 0.001(3)
C7 0.023(3) 0.042(4) 0.034(4) 0.002(3) 0.007(3) -0.001(3)
C8 0.021(3) 0.033(3) 0.023(3) 0.003(2) 0.007(2) 0.003(2)
C9 0.032(3) 0.026(3) 0.021(3) 0.002(2) 0.010(3) -0.003(2)
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'
Br Br -0.2901 2.4595 '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
C9 S1 C8 89.4(3)
C1 O1 H1 109.5
C7 N1 C8 117.9(5)
C8 N2 N3 108.9(5)
C9 N3 N2 119.8(5)
C9 N3 H3 128.5
N2 N3 H3 111.7
O1 C1 C6 118.9(5)
O1 C1 C2 122.7(6)
C6 C1 C2 118.4(6)
C3 C2 C1 120.3(6)
C3 C2 C7 118.2(5)
C1 C2 C7 121.5(6)
C4 C3 C2 119.4(5)
C4 C3 H3A 120.3
C2 C3 H3A 120.3
C5 C4 C3 120.8(6)
C5 C4 Br1 119.7(5)
C3 C4 Br1 119.6(5)
C6 C5 C4 120.6(6)
C6 C5 H5A 119.7
C4 C5 H5A 119.7
C5 C6 C1 120.6(6)
C5 C6 H6A 119.7
C1 C6 H6A 119.7
N1 C7 C2 123.0(6)
N1 C7 H7A 118.5
C2 C7 H7A 118.5
N2 C8 N1 120.1(5)
N2 C8 S1 114.4(4)
N1 C8 S1 125.5(5)
N3 C9 S2 127.4(5)
N3 C9 S1 107.5(4)
S2 C9 S1 125.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.889(6)
S1 C9 1.741(6)
S1 C8 1.752(6)
S2 C9 1.663(6)
O1 C1 1.334(7)
O1 H1 0.8200
N1 C7 1.292(8)
N1 C8 1.381(7)
N2 C8 1.293(8)
N2 N3 1.381(7)
N3 C9 1.322(8)
N3 H3 0.9690
C1 C6 1.402(8)
C1 C2 1.417(8)
C2 C3 1.399(8)
C2 C7 1.448(8)
C3 C4 1.384(8)
C3 H3A 0.9300
C4 C5 1.382(9)
C5 C6 1.377(9)
C5 H5A 0.9300
C6 H6A 0.9300
C7 H7A 0.9300
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
O1 H1 N1 . 0.82 1.94 2.664(7) 147 y
N3 H3 S2 3_756 0.97 2.36 3.327(5) 173 y
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
C8 N2 N3 C9 0.2(8)
O1 C1 C2 C3 -179.9(6)
C6 C1 C2 C3 -1.7(10)
O1 C1 C2 C7 -1.1(10)
C6 C1 C2 C7 177.1(6)
C1 C2 C3 C4 1.1(9)
C7 C2 C3 C4 -177.7(6)
C2 C3 C4 C5 -0.1(9)
C2 C3 C4 Br1 -179.3(5)
C3 C4 C5 C6 -0.4(10)
Br1 C4 C5 C6 178.8(5)
C4 C5 C6 C1 -0.1(10)
O1 C1 C6 C5 179.4(6)
C2 C1 C6 C5 1.2(10)
C8 N1 C7 C2 -177.1(5)
C3 C2 C7 N1 -179.2(6)
C1 C2 C7 N1 1.9(10)
N3 N2 C8 N1 179.3(5)
N3 N2 C8 S1 -0.1(7)
C7 N1 C8 N2 -178.7(6)
C7 N1 C8 S1 0.6(8)
C9 S1 C8 N2 0.0(5)
C9 S1 C8 N1 -179.3(5)
N2 N3 C9 S2 178.3(5)
N2 N3 C9 S1 -0.2(7)
C8 S1 C9 N3 0.1(5)
C8 S1 C9 S2 -178.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21423156
