#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:05:25 +0300 (Fri, 05 May 2023) $
#$Revision: 283412 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062361.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_7062361
loop_
_publ_author_name
'Youssef, Khaled'
'Allain, Magali'
'Cauchy, Thomas'
'Gohier, Frédéric'
_publ_section_title
;
 Dimerization reactions with oxidized brominated thiophenes
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7375
_journal_page_last               7380
_journal_paper_doi               10.1039/D3NJ00029J
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C8 H6 Br2 O3 S2'
_chemical_formula_sum            'C8 H6 Br2 O3 S2'
_chemical_formula_weight         374.07
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-07T15:44:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-12-21 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.0891(6)
_cell_length_b                   9.7366(2)
_cell_length_c                   9.1903(2)
_cell_measurement_reflns_used    3869
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      75.92
_cell_measurement_theta_min      3.497
_cell_volume                     2245.03(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6496
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         76.203
_diffrn_reflns_theta_min         3.523
_exptl_absorpt_coefficient_mu    12.534
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.35601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.213
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.45
_refine_diff_density_rms         0.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0398P)²+1.3450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0
_reflns_number_gt                2063
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00029j2.cif
_cod_data_source_block           ky111_autored
_cod_depositor_comments
'Adding full bibliography for 7062361--7062363.cif.'
_cod_database_code               7062361
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.69325(13) 0.8185(3) 0.3732(3) 0.0351(6) Uani 1 1 d . . . . .
C2 C 0.68536(13) 0.7847(3) 0.5108(3) 0.0367(6) Uani 1 1 d . . . . .
H2 H 0.706426 0.820166 0.585079 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64082(11) 0.6866(3) 0.5411(3) 0.0288(5) Uani 1 1 d . . . . .
H3 H 0.654293 0.604341 0.590336 0.035 Uiso 1 1 calc R U . . .
C4 C 0.61330(11) 0.6474(3) 0.3962(3) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.614359 0.54758 0.382945 0.033 Uiso 1 1 calc R U . . .
C5 C 0.55539(12) 0.6958(3) 0.4069(3) 0.0318(6) Uani 1 1 d . . . . .
H5 H 0.531856 0.661156 0.330051 0.038 Uiso 1 1 calc R U . . .
C6 C 0.55139(13) 0.8474(3) 0.4345(3) 0.0374(6) Uani 1 1 d . . . . .
H6 H 0.535167 0.909988 0.372223 0.045 Uiso 1 1 calc R U . . .
C7 C 0.57433(14) 0.8798(3) 0.5607(3) 0.0397(7) Uani 1 1 d . . . . .
H7 H 0.576753 0.967992 0.598987 0.048 Uiso 1 1 calc R U . . .
C8 C 0.59543(13) 0.7536(3) 0.6311(3) 0.0333(6) Uani 1 1 d . . . . .
S1 S 0.65044(3) 0.73045(7) 0.25224(7) 0.03034(16) Uani 1 1 d . . . . .
S2 S 0.53772(3) 0.63910(8) 0.59354(7) 0.03509(17) Uani 1 1 d . . . . .
Br1 Br 0.74278(2) 0.94026(4) 0.29493(4) 0.04995(13) Uani 1 1 d . . . . .
Br2 Br 0.61193(2) 0.76898(4) 0.83457(3) 0.05050(14) Uani 1 1 d . . . . .
O1 O 0.68111(11) 0.6317(3) 0.1713(2) 0.0434(5) Uani 1 1 d . . . . .
O2 O 0.61816(11) 0.8244(2) 0.1714(2) 0.0426(5) Uani 1 1 d . . . . .
O3 O 0.55323(11) 0.4940(3) 0.6173(3) 0.0460(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 112.9(2) . . ?
C2 C1 Br1 128.9(3) . . ?
S1 C1 Br1 118.13(16) . . ?
C1 C2 C3 116.7(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C2 C3 C4 109.3(2) . . ?
C2 C3 C8 112.3(2) . . ?
C4 C3 C8 103.6(2) . . ?
C2 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
C8 C3 H3 110.5 . . ?
C5 C4 C3 107.0(2) . . ?
C5 C4 S1 113.49(19) . . ?
C3 C4 S1 106.81(18) . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
S1 C4 H4 109.8 . . ?
C6 C5 C4 112.1(3) . . ?
C6 C5 S2 96.89(18) . . ?
C4 C5 S2 101.23(17) . . ?
C6 C5 H5 114.8 . . ?
C4 C5 H5 114.8 . . ?
S2 C5 H5 114.8 . . ?
C7 C6 C5 110.6(3) . . ?
C7 C6 H6 124.7 . . ?
C5 C6 H6 124.7 . . ?
C6 C7 C8 109.7(3) . . ?
C6 C7 H7 125.2 . . ?
C8 C7 H7 125.2 . . ?
C7 C8 C3 112.2(2) . . ?
C7 C8 S2 97.9(2) . . ?
C3 C8 S2 102.75(18) . . ?
C7 C8 Br2 115.8(2) . . ?
C3 C8 Br2 113.2(2) . . ?
S2 C8 Br2 113.28(15) . . ?
O2 S1 O1 117.49(14) . . ?
O2 S1 C1 111.16(15) . . ?
O1 S1 C1 108.91(16) . . ?
O2 S1 C4 111.98(14) . . ?
O1 S1 C4 110.79(14) . . ?
C1 S1 C4 94.01(13) . . ?
O3 S2 C5 110.91(14) . . ?
O3 S2 C8 109.86(15) . . ?
C5 S2 C8 78.89(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.321(4) . ?
C1 S1 1.768(3) . ?
C1 Br1 1.862(3) . ?
C2 C3 1.496(4) . ?
C2 H2 0.93 . ?
C3 C4 1.548(3) . ?
C3 C8 1.551(4) . ?
C3 H3 0.98 . ?
C4 C5 1.531(4) . ?
C4 S1 1.809(3) . ?
C4 H4 0.98 . ?
C5 C6 1.501(4) . ?
C5 S2 1.856(3) . ?
C5 H5 0.98 . ?
C6 C7 1.333(5) . ?
C6 H6 0.93 . ?
C7 C8 1.486(5) . ?
C7 H7 0.93 . ?
C8 S2 1.859(3) . ?
C8 Br2 1.921(3) . ?
S1 O2 1.430(2) . ?
S1 O1 1.438(2) . ?
S2 O3 1.482(3) . ?
