#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:05:25 +0300 (Fri, 05 May 2023) $
#$Revision: 283412 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062363.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_7062363
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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-07T18:10:47-00:00
_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                 99.564(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8922(6)
_cell_length_b                   10.1295(7)
_cell_length_c                   14.0460(10)
_cell_measurement_reflns_used    3451
_cell_measurement_temperature    294.10(10)
_cell_measurement_theta_max      76.022
_cell_measurement_theta_min      5.401
_cell_volume                     1107.29(14)
_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      294.10(10)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.971
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4877
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        74
_diffrn_reflns_theta_max         76.168
_diffrn_reflns_theta_min         5.41
_exptl_absorpt_coefficient_mu    12.707
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.44962
_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    2.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.686
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0452
_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)+(0.0751P)²+1.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.121
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0
_reflns_number_gt                2043
_reflns_number_total             2246
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00029j2.cif
_cod_data_source_block           ky113_auto
_cod_depositor_comments
'Adding full bibliography for 7062361--7062363.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062363
_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'
'x-1/2, -y-1/2, z-1/2'
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 0.5870(5) 0.7025(4) 0.6749(3) 0.0344(8) Uani 1 1 d . . . . .
H1 H 0.543655 0.720846 0.731179 0.041 Uiso 1 1 calc R U . . .
C2 C 0.7350(5) 0.6425(4) 0.6719(3) 0.0300(7) Uani 1 1 d . . . . .
C3 C 0.7946(4) 0.6269(3) 0.5774(3) 0.0241(6) Uani 1 1 d . . . . .
H3 H 0.801934 0.533228 0.561201 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6637(4) 0.6987(4) 0.5003(2) 0.0250(7) Uani 1 1 d . . . . .
H4 H 0.624884 0.638615 0.446341 0.03 Uiso 1 1 calc R U . . .
C5 C 0.7593(4) 0.8160(4) 0.4646(2) 0.0274(7) Uani 1 1 d . . . . .
H5 H 0.696397 0.86179 0.408135 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8410(5) 0.9048(4) 0.5447(3) 0.0285(7) Uani 1 1 d . . . . .
H6 H 0.812892 0.993002 0.55183 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9593(4) 0.8383(4) 0.6039(2) 0.0252(7) Uani 1 1 d . . . . .
C8 C 0.9695(4) 0.6974(4) 0.5747(2) 0.0243(7) Uani 1 1 d . . . . .
H8 H 1.071688 0.649545 0.605957 0.029 Uiso 1 1 calc R U . . .
O1 O 0.4447(4) 0.8805(3) 0.5503(2) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.3474(4) 0.6501(4) 0.5295(3) 0.0512(9) Uani 1 1 d . . . . .
O3 O 0.9218(5) 0.6113(4) 0.3862(2) 0.0482(8) Uani 1 1 d . . . . .
S1 S 0.48440(10) 0.74239(9) 0.55865(7) 0.0273(2) Uani 1 1 d . . . . .
S2 S 0.96141(12) 0.73278(10) 0.44417(6) 0.0308(2) Uani 1 1 d . . . . .
Br1 Br 0.87123(6) 0.57186(6) 0.78275(3) 0.0488(2) Uani 1 1 d . . . . .
Br2 Br 1.10763(6) 0.90428(5) 0.71235(3) 0.04582(19) 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'
O O 0.0492 0.0322 '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'
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 110.5(3) . . ?
C2 C1 H1 124.7 . . ?
S1 C1 H1 124.7 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 Br1 122.3(3) . . ?
C3 C2 Br1 118.4(3) . . ?
C2 C3 C4 107.6(3) . . ?
C2 C3 C8 112.7(3) . . ?
C4 C3 C8 104.9(3) . . ?
C2 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
C8 C3 H3 110.5 . . ?
C5 C4 C3 106.5(3) . . ?
C5 C4 S1 115.1(2) . . ?
C3 C4 S1 106.2(2) . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
S1 C4 H4 109.6 . . ?
C6 C5 C4 113.1(3) . . ?
C6 C5 S2 96.6(2) . . ?
C4 C5 S2 100.4(2) . . ?
C6 C5 H5 114.8 . . ?
C4 C5 H5 114.8 . . ?
S2 C5 H5 114.8 . . ?
C7 C6 C5 109.6(3) . . ?
C7 C6 H6 125.2 . . ?
C5 C6 H6 125.2 . . ?
C6 C7 C8 112.2(3) . . ?
C6 C7 Br2 127.3(3) . . ?
C8 C7 Br2 120.5(2) . . ?
C7 C8 C3 110.0(3) . . ?
C7 C8 S2 95.3(2) . . ?
C3 C8 S2 103.1(2) . . ?
C7 C8 H8 115.4 . . ?
C3 C8 H8 115.4 . . ?
S2 C8 H8 115.4 . . ?
O1 S1 O2 117.9(2) . . ?
O1 S1 C1 111.3(2) . . ?
O2 S1 C1 109.0(2) . . ?
O1 S1 C4 112.28(18) . . ?
O2 S1 C4 108.73(19) . . ?
C1 S1 C4 95.27(18) . . ?
O3 S2 C8 110.60(19) . . ?
O3 S2 C5 110.61(19) . . ?
C8 S2 C5 79.96(15) . . ?
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 1.324(6) . ?
C1 S1 1.746(4) . ?
C1 H1 0.93 . ?
C2 C3 1.488(5) . ?
C2 Br1 1.880(4) . ?
C3 C4 1.549(5) . ?
C3 C8 1.561(4) . ?
C3 H3 0.98 . ?
C4 C5 1.535(5) . ?
C4 S1 1.804(4) . ?
C4 H4 0.98 . ?
C5 C6 1.500(5) . ?
C5 S2 1.868(4) . ?
C5 H5 0.98 . ?
C6 C7 1.326(5) . ?
C6 H6 0.93 . ?
C7 C8 1.491(5) . ?
C7 Br2 1.882(3) . ?
C8 S2 1.859(3) . ?
C8 H8 0.98 . ?
O1 S1 1.434(3) . ?
O2 S1 1.436(3) . ?
O3 S2 1.480(4) . ?
