#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/96/2219608.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_2219608
loop_
_publ_author_name
'Yin, Li-He'
'Wan, Rong'
'Wang, Yao'
'Han, Feng'
'Wang, Jin-Tang'
_publ_section_title
;
 5-(2-Bromophenyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           HK2522
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1884
_journal_paper_doi               10.1107/S1600536808027827
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H6 Br N3 S'
_chemical_formula_moiety         'C8 H6 Br N3 S'
_chemical_formula_sum            'C8 H6 Br N3 S'
_chemical_formula_weight         256.13
_chemical_melting_point_gt       486
_chemical_melting_point_lt       487
_chemical_name_systematic
;
5-(2-Bromophenyl)-1,3,4-thiadiazol-2-amine
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.869(3)
_cell_length_b                   8.0250(16)
_cell_length_c                   7.9480(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     940.4(3)
_computing_cell_refinement       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ 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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1832
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.545
_exptl_absorpt_correction_T_max  0.6592
_exptl_absorpt_correction_T_min  0.3425
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.567
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0598
_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)+(0.0838P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                972
_reflns_number_total             1694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2522.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219608
_cod_database_fobs_code          2219608
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
Br Br 0.88329(5) 1.09232(10) 1.09121(14) 0.0845(5) Uani d . 1
S S 0.65602(11) 1.1146(2) 1.0932(2) 0.0458(5) Uani d . 1
N N1 0.6259(3) 0.9573(7) 0.8134(6) 0.0424(13) Uani d . 1
N N2 0.5587(3) 1.0773(6) 0.8048(6) 0.0430(13) Uani d . 1
N N3 0.5081(3) 1.2909(6) 0.9666(6) 0.0480(14) Uani d . 1
H H3A 0.4635 1.3143 0.8901 0.058 Uiso calc R 1
H H3B 0.5158 1.3467 1.0597 0.058 Uiso calc R 1
C C1 0.7308(5) 0.6693(8) 0.9656(9) 0.0512(18) Uani d . 1
H H1 0.6722 0.6431 0.9176 0.061 Uiso calc R 1
C C2 0.7921(5) 0.5423(8) 1.0064(10) 0.0591(19) Uani d . 1
H H2 0.7750 0.4319 0.9866 0.071 Uiso calc R 1
C C3 0.8787(5) 0.5816(10) 1.0769(10) 0.068(2) Uani d . 1
H H3 0.9204 0.4968 1.1067 0.081 Uiso calc R 1
C C4 0.9041(4) 0.7438(10) 1.1036(9) 0.059(2) Uani d . 1
H H4 0.9630 0.7698 1.1506 0.071 Uiso calc R 1
C C5 0.8416(4) 0.8692(8) 1.0602(9) 0.0493(17) Uani d . 1
C C6 0.7542(4) 0.8348(7) 0.9941(8) 0.0378(14) Uani d . 1
C C7 0.6811(4) 0.9618(8) 0.9507(7) 0.0363(14) Uani d . 1
C C8 0.5647(4) 1.1688(7) 0.9412(7) 0.0332(14) Uani d . 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
Br 0.0417(5) 0.0576(5) 0.1483(10) -0.0105(4) -0.0096(5) -0.0066(6)
S 0.0396(9) 0.0538(10) 0.0394(9) 0.0102(8) -0.0131(7) -0.0097(8)
N1 0.042(3) 0.046(3) 0.037(3) 0.000(3) -0.001(3) -0.003(3)
N2 0.045(3) 0.043(3) 0.037(3) 0.008(3) -0.008(2) -0.005(3)
N3 0.049(3) 0.056(4) 0.036(3) 0.015(3) -0.008(2) -0.007(3)
C1 0.046(4) 0.049(4) 0.057(5) -0.003(3) 0.005(3) 0.001(4)
C2 0.057(4) 0.035(4) 0.086(5) 0.004(3) 0.013(4) 0.004(4)
C3 0.050(4) 0.068(6) 0.083(6) 0.021(4) 0.005(4) 0.012(5)
C4 0.037(4) 0.064(5) 0.073(5) 0.009(4) -0.003(4) 0.009(4)
C5 0.031(3) 0.049(4) 0.065(4) -0.004(3) -0.004(3) 0.006(3)
C6 0.038(3) 0.040(3) 0.036(3) -0.002(3) 0.006(3) -0.004(3)
C7 0.029(3) 0.042(3) 0.037(3) -0.006(3) 0.001(3) 0.001(3)
C8 0.029(3) 0.035(3) 0.034(4) 0.000(3) -0.003(3) 0.004(3)
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'
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
C2 C1 C6 121.8(7)
C2 C1 H1 119.1
C6 C1 H1 119.1
C3 C2 C1 118.9(7)
C3 C2 H2 120.5
C1 C2 H2 120.5
C4 C3 C2 120.6(7)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.4(6)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 121.6(6)
C6 C5 Br 121.2(5)
C4 C5 Br 117.1(5)
C5 C6 C1 117.6(6)
C5 C6 C7 125.3(6)
C1 C6 C7 117.1(6)
N1 C7 C6 123.0(6)
N1 C7 S 114.0(5)
C6 C7 S 122.6(4)
N2 C8 N3 124.6(5)
N2 C8 S 113.4(4)
N3 C8 S 122.0(5)
C7 N1 N2 113.7(5)
C8 N2 N1 112.4(5)
C8 N3 H3A 120.0
C8 N3 H3B 120.0
H3A N3 H3B 120.0
C7 S C8 86.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C5 1.901(7)
N1 N2 1.383(7)
N3 H3A 0.8600
N3 H3B 0.8600
C1 C2 1.377(9)
C1 C6 1.384(8)
C1 H1 0.9300
C2 C3 1.373(10)
C2 H2 0.9300
C3 C4 1.365(11)
C3 H3 0.9300
C4 C5 1.383(9)
C4 H4 0.9300
C5 C6 1.365(8)
C6 C7 1.498(8)
C7 N1 1.278(7)
C7 S 1.742(6)
C8 N2 1.302(7)
C8 N3 1.325(7)
C8 S 1.752(6)
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
N3 H3A N1 2_656 0.86 2.27 3.092(7) 160.3 yes
N3 H3A N2 2_656 0.86 2.61 3.221(7) 128.5 yes
N3 H3B N2 4_586 0.86 2.06 2.896(7) 163.2 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
C6 C1 C2 C3 -0.2(11)
C1 C2 C3 C4 -1.0(12)
C2 C3 C4 C5 0.5(12)
C3 C4 C5 C6 1.3(11)
C3 C4 C5 Br -177.2(6)
C4 C5 C6 C1 -2.5(11)
Br C5 C6 C1 176.0(5)
C4 C5 C6 C7 177.2(6)
Br C5 C6 C7 -4.4(9)
C2 C1 C6 C5 1.9(11)
C2 C1 C6 C7 -177.8(6)
C5 C6 C7 N1 136.1(7)
C1 C6 C7 N1 -44.3(9)
C5 C6 C7 S -51.2(8)
C1 C6 C7 S 128.4(6)
C6 C7 N1 N2 174.6(5)
S C7 N1 N2 1.3(7)
N3 C8 N2 N1 -179.0(6)
S C8 N2 N1 0.6(6)
C7 N1 N2 C8 -1.2(7)
N1 C7 S C8 -0.8(5)
C6 C7 S C8 -174.1(5)
N2 C8 S C7 0.1(5)
N3 C8 S C7 179.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 481937
