#------------------------------------------------------------------------------
#$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238993.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2238993
loop_
_publ_author_name
'Bunev, Alexander S.'
'Rudakova, Yana I.'
'Statsyuk, Vladimir E.'
'Ostapenko, Gennady I.'
'Khrustalev, Victor N.'
_publ_section_title
;
 2-Bromo-4-phenyl-1,3-thiazole
;
_journal_coeditor_code           CV5440
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o139
_journal_paper_doi               10.1107/S160053681400066X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H6 Br N S'
_chemical_formula_moiety         'C9 H6 Br N S'
_chemical_formula_sum            'C9 H6 Br N S'
_chemical_formula_weight         240.12
_chemical_name_systematic
;
2-Bromo-4-phenyl-1,3-thiazole
;
_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                 90.8120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8934(3)
_cell_length_b                   10.6591(6)
_cell_length_c                   13.8697(7)
_cell_measurement_reflns_used    3185
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.41
_cell_volume                     871.18(8)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2001)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2005)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2001)'
_computing_molecular_graphics    '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material  '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_structure_refinement  '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXTL</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w 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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12144
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    4.894
_exptl_absorpt_correction_T_max  0.591
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.514
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0286
_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/[\s^2^(Fo^2^)+(0.0323P)^2^+0.1245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                2258
_reflns_number_total             2780
_reflns_threshold_expression     I>2\s(I)
_iucr_refine_instructions_details
;
TITL I in P2(1)/n
CELL 0.71073   5.8934  10.6591  13.8697  90.000  90.812  90.000
ZERR    4.00   0.0003   0.0006   0.0007   0.000   0.001   0.000
LATT  1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N S BR
UNIT 36 24 4 4 4
TEMP -153.0
SIZE 0.12 0.12 0.15
L.S. 12
BOND $H
ACTA
CONF
WGHT    0.032300    0.124500
FVAR       0.18389
BR1   5    0.218244    0.900200    0.576233    11.00000    0.02065    0.02080 =
         0.02561   -0.00725   -0.00253   -0.00021
S1    4   -0.240235    0.758664    0.559842    11.00000    0.01813    0.02096 =
         0.02024   -0.00361    0.00358    0.00233
C2    1    0.032172    0.776587    0.520488    11.00000    0.01557    0.01575 =
         0.01814   -0.00129   -0.00123    0.00056
N3    3    0.095952    0.703298    0.451500    11.00000    0.01668    0.01599 =
         0.01549   -0.00064   -0.00049   -0.00081
C4    1   -0.082493    0.624748    0.424433    11.00000    0.01616    0.01294 =
         0.01416    0.00154   -0.00076    0.00095
C5    1   -0.276754    0.642785    0.475486    11.00000    0.01728    0.01730 =
         0.01896   -0.00115    0.00086    0.00016
AFIX  43
H5    2   -0.413543    0.597155    0.465488    11.00000   -1.20000
AFIX   0
C6    1   -0.050027    0.534850    0.344630    11.00000    0.01866    0.01370 =
         0.01293    0.00151   -0.00129    0.00204
C7    1   -0.215523    0.445274    0.321674    11.00000    0.01937    0.01816 =
         0.01756    0.00100    0.00022   -0.00132
AFIX  43
H7    2   -0.350789    0.441874    0.358032    11.00000   -1.20000
AFIX   0
C8    1   -0.184930    0.361275    0.246522    11.00000    0.02635    0.01800 =
         0.01976   -0.00035   -0.00542   -0.00186
AFIX  43
H8    2   -0.298810    0.300904    0.231769    11.00000   -1.20000
AFIX   0
C9    1    0.013376    0.365476    0.192538    11.00000    0.03065    0.01798 =
         0.01528   -0.00260   -0.00188    0.00451
AFIX  43
H9    2    0.035365    0.308044    0.141133    11.00000   -1.20000
AFIX   0
C10   1    0.177791    0.454441    0.214836    11.00000    0.02245    0.02245 =
         0.01750    0.00057    0.00280    0.00412
AFIX  43
H10   2    0.312998    0.457582    0.178424    11.00000   -1.20000
AFIX   0
C11   1    0.147072    0.539002    0.289784    11.00000    0.01844    0.01650 =
         0.01723   -0.00039    0.00191   -0.00135
AFIX  43
H11   2    0.260501    0.599905    0.303820    11.00000   -1.20000
HKLF 4
REM I in P2(1)/n
REM R1 = 0.0286 for   2258 Fo > 4sig(Fo)  and  0.0412 for all   2780 data
REM    109 parameters refined using      0 restraints
END
WGHT      0.0325      0.0996
REM Highest difference peak  0.401,  deepest hole -0.514,  1-sigma level  0.097
Q1    1   0.3547  0.9005  0.5821  11.00000  0.05    0.40
Q2    1  -0.2686  0.7036  0.5069  11.00000  0.05    0.38
Q3    1   0.1589  0.4964  0.2524  11.00000  0.05    0.38
Q4    1  -0.1035  0.7612  0.5538  11.00000  0.05    0.37
Q5    1  -0.0898  0.5790  0.3736  11.00000  0.05    0.36
Q6    1   0.2340  0.8459  0.6193  11.00000  0.05    0.36
Q7    1  -0.0744  0.3626  0.2205  11.00000  0.05    0.36
Q8    1   0.0624  0.5182  0.3260  11.00000  0.05    0.34
Q9    1  -0.1050  0.4727  0.3368  11.00000  0.05    0.33
Q10   1   0.1970  0.4785  0.1805  11.00000  0.05    0.33
Q11   1   0.2158  0.9449  0.5056  11.00000  0.05    0.33
Q12   1  -0.1761  0.4004  0.2894  11.00000  0.05    0.33
Q13   1   0.0043  0.6811  0.4283  11.00000  0.05    0.31
Q14   1   0.0598  0.4426  0.2005  11.00000  0.05    0.30
Q15   1  -0.1671  0.6176  0.5995  11.00000  0.05    0.29
Q16   1   0.0288  0.3936  0.0943  11.00000  0.05    0.29
Q17   1  -0.0982  0.8991  0.4652  11.00000  0.05    0.28
Q18   1   0.0072  0.7548  0.4811  11.00000  0.05    0.28
Q19   1  -0.1595  0.2776  0.3373  11.00000  0.05    0.28
Q20   1  -0.0774  0.1714  0.2803  11.00000  0.05    0.28
;
_cod_data_source_file            cv5440sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238993
_cod_database_fobs_code          2238993
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_symmetry_multiplicity
Br Br1 0.21824(3) 0.90020(2) 0.576233(15) 0.02238(7) Uani d . 1 1
S S1 -0.24024(8) 0.75866(5) 0.55984(4) 0.01975(11) Uani d . 1 1
C C2 0.0322(3) 0.77659(19) 0.52049(14) 0.0165(4) Uani d . 1 1
N N3 0.0960(3) 0.70330(16) 0.45150(11) 0.0161(3) Uani d . 1 1
C C4 -0.0825(3) 0.62475(17) 0.42443(14) 0.0144(4) Uani d . 1 1
C C5 -0.2768(3) 0.64278(19) 0.47549(14) 0.0178(4) Uani d . 1 1
H H5 -0.4135 0.5972 0.4655 0.021 Uiso calc R 1 1
C C6 -0.0500(3) 0.53485(18) 0.34463(14) 0.0151(4) Uani d . 1 1
C C7 -0.2155(3) 0.4453(2) 0.32167(14) 0.0184(4) Uani d . 1 1
H H7 -0.3508 0.4419 0.3580 0.022 Uiso calc R 1 1
C C8 -0.1849(4) 0.3613(2) 0.24652(14) 0.0214(4) Uani d . 1 1
H H8 -0.2988 0.3009 0.2318 0.026 Uiso calc R 1 1
C C9 0.0134(4) 0.3655(2) 0.19254(15) 0.0213(4) Uani d . 1 1
H H9 0.0354 0.3080 0.1411 0.026 Uiso calc R 1 1
C C10 0.1778(4) 0.4544(2) 0.21484(15) 0.0208(4) Uani d . 1 1
H H10 0.3130 0.4576 0.1784 0.025 Uiso calc R 1 1
C C11 0.1471(3) 0.53900(19) 0.28978(14) 0.0174(4) Uani d . 1 1
H H11 0.2605 0.5999 0.3038 0.021 Uiso calc R 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 0.02065(11) 0.02080(11) 0.02561(12) -0.00021(8) -0.00253(8) -0.00725(8)
S1 0.0181(2) 0.0210(3) 0.0202(2) 0.00233(19) 0.00358(19) -0.00361(19)
C2 0.0156(9) 0.0158(9) 0.0181(9) 0.0006(7) -0.0012(7) -0.0013(7)
N3 0.0167(8) 0.0160(8) 0.0155(8) -0.0008(6) -0.0005(6) -0.0006(6)
C4 0.0162(9) 0.0129(9) 0.0142(8) 0.0009(7) -0.0008(7) 0.0015(7)
C5 0.0173(9) 0.0173(9) 0.0190(10) 0.0002(7) 0.0009(7) -0.0011(8)
C6 0.0187(9) 0.0137(9) 0.0129(8) 0.0020(7) -0.0013(7) 0.0015(7)
C7 0.0194(9) 0.0182(9) 0.0176(9) -0.0013(8) 0.0002(7) 0.0010(8)
C8 0.0264(10) 0.0180(10) 0.0198(10) -0.0019(8) -0.0054(8) -0.0004(8)
C9 0.0307(11) 0.0180(10) 0.0153(9) 0.0045(8) -0.0019(8) -0.0026(7)
C10 0.0224(10) 0.0225(10) 0.0175(9) 0.0041(8) 0.0028(8) 0.0006(8)
C11 0.0184(9) 0.0165(9) 0.0172(9) -0.0013(7) 0.0019(7) -0.0004(7)
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
C5 S1 C2 88.40(10)
N3 C2 S1 116.81(15)
N3 C2 Br1 123.68(15)
S1 C2 Br1 119.49(11)
C2 N3 C4 109.64(17)
C5 C4 N3 114.24(17)
C5 C4 C6 126.63(18)
N3 C4 C6 119.11(17)
C4 C5 S1 110.91(15)
C4 C5 H5 124.5
S1 C5 H5 124.5
C11 C6 C7 118.68(18)
C11 C6 C4 120.27(17)
C7 C6 C4 121.05(17)
C8 C7 C6 120.92(19)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 120.0(2)
C7 C8 H8 120.0
C9 C8 H8 120.0
C10 C9 C8 119.28(19)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 120.80(19)
C9 C10 H10 119.6
C11 C10 H10 119.6
C10 C11 C6 120.30(19)
C10 C11 H11 119.9
C6 C11 H11 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.874(2)
S1 C5 1.713(2)
S1 C2 1.714(2)
C2 N3 1.295(2)
N3 C4 1.392(2)
C4 C5 1.368(3)
C4 C6 1.478(3)
C5 H5 0.9500
C6 C11 1.398(3)
C6 C7 1.398(3)
C7 C8 1.388(3)
C7 H7 0.9500
C8 C9 1.398(3)
C8 H8 0.9500
C9 C10 1.388(3)
C9 H9 0.9500
C10 C11 1.390(3)
C10 H10 0.9500
C11 H11 0.9500
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
C5 S1 C2 N3 -0.65(17)
C5 S1 C2 Br1 178.28(13)
S1 C2 N3 C4 0.5(2)
Br1 C2 N3 C4 -178.35(13)
C2 N3 C4 C5 -0.1(2)
C2 N3 C4 C6 178.41(17)
N3 C4 C5 S1 -0.4(2)
C6 C4 C5 S1 -178.74(16)
C2 S1 C5 C4 0.56(16)
C5 C4 C6 C11 170.74(19)
N3 C4 C6 C11 -7.5(3)
C5 C4 C6 C7 -8.5(3)
N3 C4 C6 C7 173.20(18)
C11 C6 C7 C8 0.5(3)
C4 C6 C7 C8 179.78(19)
C6 C7 C8 C9 0.0(3)
C7 C8 C9 C10 -0.2(3)
C8 C9 C10 C11 -0.1(3)
C9 C10 C11 C6 0.6(3)
C7 C6 C11 C10 -0.8(3)
C4 C6 C11 C10 179.93(18)