#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/26/2232686.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_2232686
loop_
_publ_author_name
'Dobrowolski, Michał A.'
'Struga, Marta'
'Szulczyk, Daniel'
_publ_section_title
;
 6-Bromo-2-methylsulfanyl-1,3-benzothiazole
;
_journal_coeditor_code           GK2424
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3446
_journal_page_last               o3447
_journal_paper_doi               10.1107/S160053681105015X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H6 Br N S2'
_chemical_formula_moiety         'C8 H6 Br N S2'
_chemical_formula_sum            'C8 H6 Br N S2'
_chemical_formula_weight         260.18
_chemical_melting_point_gt       371
_chemical_melting_point_lt       374
_chemical_name_systematic
;
6-Bromo-2-methylsulfanyl-1,3-benzothiazole
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.353(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7843(4)
_cell_length_b                   3.9514(2)
_cell_length_c                   11.6076(5)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.88
_cell_volume                     446.01(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method       'phi and omega 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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3437
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.013
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details 'Flack (1983), 315 Friedel pairs'
_refine_ls_abs_structure_Flack   0.005(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1227
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0165
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0143P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0329
_refine_ls_wR_factor_ref         0.0332
_reflns_number_gt                1125
_reflns_number_total             1227
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2424.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2232686
_cod_database_fobs_code          2232686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C C1 0.7671(3) 0.6254(7) 0.9919(3) 0.0141(7) Uani d . 1 1
C C2 0.8559(3) 0.5366(12) 0.9147(2) 0.0123(6) Uani d . 1 1
C C3 0.8181(3) 0.6157(7) 0.7984(3) 0.0121(7) Uani d . 1 1
C C4 0.6939(3) 0.7815(8) 0.7626(3) 0.0121(7) Uani d . 1 1
C C5 0.6060(3) 0.8712(7) 0.8439(3) 0.0137(7) Uani d . 1 1
C C6 0.6430(3) 0.7938(8) 0.9590(3) 0.0135(7) Uani d . 1 1
C C7 0.7722(3) 0.7402(8) 0.5934(3) 0.0127(7) Uani d . 1 1
C C8 0.6257(3) 0.9551(10) 0.3940(3) 0.0192(8) Uani d . 1 1
N N1 0.6702(3) 0.8486(6) 0.6440(2) 0.0131(6) Uani d . 1 1
S S1 0.90775(7) 0.5420(3) 0.68048(6) 0.01509(19) Uani d . 1 1
S S2 0.79094(8) 0.7776(2) 0.44632(7) 0.01761(19) Uani d . 1 1
Br Br1 0.81246(3) 0.50973(9) 1.15124(2) 0.01701(9) Uani d . 1 1
H H2 0.9403 0.4254 0.9390 0.015 Uiso calc R 1 1
H H5 0.5218 0.9841 0.8205 0.016 Uiso calc R 1 1
H H6 0.5845 0.8546 1.0158 0.016 Uiso calc R 1 1
H H8A 0.6084 1.1556 0.4399 0.029 Uiso calc R 1 1
H H8B 0.5537 0.7867 0.4011 0.029 Uiso calc R 1 1
H H8C 0.6254 1.0196 0.3124 0.029 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 0.0033 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
C3 S1 C7 87.90(14)
C7 N1 C4 109.5(3)
C1 C2 C3 117.3(3)
C1 C2 H2 121.3
C3 C2 H2 121.3
C2 C1 C6 122.7(3)
C2 C1 Br1 118.6(2)
C6 C1 Br1 118.7(2)
C5 C6 C1 119.8(3)
C5 C6 H6 120.1
C1 C6 H6 120.1
C2 C3 C4 121.3(3)
C2 C3 S1 128.6(2)
C4 C3 S1 110.0(2)
C5 C4 N1 124.9(3)
C5 C4 C3 119.9(3)
N1 C4 C3 115.2(3)
C6 C5 C4 119.0(3)
C6 C5 H5 120.5
C4 C5 H5 120.5
N1 C7 S2 126.2(2)
N1 C7 S1 117.4(2)
S2 C7 S1 116.46(18)
C7 S2 C8 100.09(15)
S2 C8 H8A 109.5
S2 C8 H8B 109.5
H8A C8 H8B 109.5
S2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.730(3)
S1 C7 1.760(3)
N1 C7 1.286(4)
N1 C4 1.396(4)
C2 C1 1.362(4)
C2 C3 1.395(4)
C2 H2 0.9500
C1 C6 1.400(4)
C1 Br1 1.909(3)
C6 C5 1.379(4)
C6 H6 0.9500
C3 C4 1.402(4)
C4 C5 1.391(4)
C5 H5 0.9500
C7 S2 1.744(3)
S2 C8 1.805(3)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C3 C2 C1 C6 -0.9(5)
C3 C2 C1 Br1 178.1(3)
C2 C1 C6 C5 1.0(5)
Br1 C1 C6 C5 -178.1(2)
C1 C2 C3 C4 0.3(5)
C1 C2 C3 S1 179.3(3)
C7 S1 C3 C2 -178.8(4)
C7 S1 C3 C4 0.2(2)
C7 N1 C4 C5 178.5(3)
C7 N1 C4 C3 -0.4(4)
C2 C3 C4 C5 0.2(5)
S1 C3 C4 C5 -178.9(2)
C2 C3 C4 N1 179.2(3)
S1 C3 C4 N1 0.1(3)
C1 C6 C5 C4 -0.4(4)
N1 C4 C5 C6 -179.0(3)
C3 C4 C5 C6 -0.1(4)
C4 N1 C7 S2 -178.1(2)
C4 N1 C7 S1 0.6(3)
C3 S1 C7 N1 -0.5(3)
C3 S1 C7 S2 178.36(19)
N1 C7 S2 C8 -6.0(3)
S1 C7 S2 C8 175.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16434209
