#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/50/2215075.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_2215075
loop_
_publ_author_name
'Jian-Ping Liu'
'Yu-Bin Zheng'
_publ_section_title
;
 5-Bromothiophene-2-sulfonic acid
;
_journal_coeditor_code           CV2285
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3697
_journal_page_last               o3697
_journal_paper_doi               10.1107/S1600536807037208
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C4 H3 Br O3 S2'
_chemical_formula_moiety         'C4 H3 Br O3 S2'
_chemical_formula_sum            'C4 H3 Br O3 S2'
_chemical_formula_weight         243.09
_chemical_name_systematic
;
5-Bromothiophene-2-sulfonic acid
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7633(16)
_cell_length_b                   14.4540(17)
_cell_length_c                   7.7020(9)
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.81
_cell_volume                     1532.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7333
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.853
_exptl_absorpt_correction_T_max  0.5002
_exptl_absorpt_correction_T_min  0.2410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.283
_refine_diff_density_min         -1.215
_refine_ls_extinction_coef       0.0100(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0502
_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)+(0.0718P)²+4.907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                1191
_reflns_number_total             1347
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2285.cif
_cod_data_source_block           I
_cod_database_code               2215075
_cod_database_fobs_code          2215075
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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 Br1 1.17226(5) 0.61516(5) 1.03375(11) 0.0594(4) Uani d . 1
S S1 1.06565(9) 0.80207(10) 0.9827(2) 0.0412(4) Uani d . 1
S S2 0.88696(9) 0.91154(8) 0.88437(17) 0.0346(4) Uani d . 1
O O1 0.8001(3) 0.8886(3) 0.7904(6) 0.0457(10) Uani d . 1
O O2 0.9573(3) 0.9723(2) 0.8092(5) 0.0395(9) Uani d . 1
O O3 0.8528(3) 0.9585(3) 1.0626(5) 0.0459(10) Uani d . 1
H H3 0.8073 0.9291 1.1034 0.069 Uiso calc R 1
C C1 1.0605(4) 0.6842(4) 0.9861(7) 0.0366(12) Uani d . 1
C C2 0.9721(4) 0.6498(4) 0.9457(7) 0.0405(12) Uani d . 1
H H2 0.9574 0.5870 0.9417 0.049 Uiso calc R 1
C C3 0.9050(4) 0.7209(4) 0.9103(7) 0.0377(11) Uani d . 1
H H3A 0.8404 0.7105 0.8809 0.045 Uiso calc R 1
C C4 0.9452(3) 0.8064(3) 0.9237(6) 0.0296(10) 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
Br1 0.0396(5) 0.0554(5) 0.0834(6) 0.0193(3) -0.0019(3) 0.0086(3)
S1 0.0220(7) 0.0379(8) 0.0637(9) -0.0003(5) -0.0064(5) 0.0044(6)
S2 0.0294(7) 0.0336(7) 0.0408(7) -0.0015(5) -0.0021(5) 0.0069(5)
O1 0.0268(19) 0.051(2) 0.059(3) -0.0032(16) -0.0157(18) 0.0120(19)
O2 0.0332(19) 0.0395(19) 0.046(2) -0.0060(15) 0.0035(16) 0.0103(16)
O3 0.038(2) 0.048(2) 0.052(2) 0.0015(18) 0.0066(18) -0.0026(19)
C1 0.034(3) 0.035(3) 0.040(3) 0.009(2) 0.001(2) 0.001(2)
C2 0.042(3) 0.032(3) 0.048(3) 0.001(2) -0.001(2) -0.002(2)
C3 0.029(3) 0.037(3) 0.047(3) -0.004(2) -0.005(2) -0.001(2)
C4 0.021(2) 0.033(3) 0.035(3) -0.0014(18) -0.0023(18) 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'
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
C1 S1 C4 90.0(3)
O2 S2 O1 120.1(2)
O2 S2 O3 106.6(2)
O1 S2 O3 106.6(2)
O2 S2 C4 107.1(2)
O1 S2 C4 105.6(2)
O3 S2 C4 110.8(2)
S2 O3 H3 109.5
C2 C1 S1 113.7(4)
C2 C1 Br1 126.1(4)
S1 C1 Br1 120.1(3)
C1 C2 C3 111.5(5)
C1 C2 H2 124.3
C3 C2 H2 124.3
C4 C3 C2 112.5(5)
C4 C3 H3A 123.8
C2 C3 H3A 123.8
C3 C4 S1 112.3(4)
C3 C4 S2 126.3(4)
S1 C4 S2 121.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.870(5)
S1 C1 1.705(5)
S1 C4 1.720(5)
S2 O2 1.429(4)
S2 O1 1.437(4)
S2 O3 1.602(4)
S2 C4 1.745(5)
O3 H3 0.8200
C1 C2 1.351(8)
C2 C3 1.409(7)
C2 H2 0.9300
C3 C4 1.358(7)
C3 H3A 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
O3 H3 O1 8_756 0.82 2.14 2.920(5) 158
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
C4 S1 C1 C2 -0.3(4)
C4 S1 C1 Br1 177.3(3)
S1 C1 C2 C3 0.0(6)
Br1 C1 C2 C3 -177.5(4)
C1 C2 C3 C4 0.5(7)
C2 C3 C4 S1 -0.8(6)
C2 C3 C4 S2 178.2(4)
C1 S1 C4 C3 0.6(4)
C1 S1 C4 S2 -178.4(3)
O2 S2 C4 C3 -144.9(5)
O1 S2 C4 C3 -15.8(5)
O3 S2 C4 C3 99.3(5)
O2 S2 C4 S1 34.0(4)
O1 S2 C4 S1 163.1(3)
O3 S2 C4 S1 -81.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8258656
