#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:05:25 +0300 (Fri, 05 May 2023) $
#$Revision: 283412 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/23/7062362.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_7062362
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 H4 Br4 O2 S2'
_chemical_formula_sum            'C8 H4 Br4 O2 S2'
_chemical_formula_weight         515.87
_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             2022-09-06T10:01:35-00:00
_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                 97.648(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4291(6)
_cell_length_b                   19.1658(7)
_cell_length_c                   11.4923(7)
_cell_measurement_reflns_used    5203
_cell_measurement_temperature    200.0(7)
_cell_measurement_theta_max      71.491
_cell_measurement_theta_min      4.475
_cell_volume                     2495.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.66a  (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.66a  (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.66a  (Rigaku OD, 2022)'
_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      200.0(7)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.094
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14452
_diffrn_reflns_point_group_measured_fraction_full 0.98
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        68
_diffrn_reflns_theta_max         78.446
_diffrn_reflns_theta_min         4.516
_exptl_absorpt_coefficient_mu    18.748
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.68195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.42.66a (Rigaku Oxford Diffraction, 2022)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.747
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.018
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.228
_refine_ls_extinction_coef       0.00074(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1259P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.2105
_reflns_Friedel_coverage         0
_reflns_number_gt                3211
_reflns_number_total             4919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00029j2.cif
_cod_data_source_block           ky137_200k
_cod_depositor_comments
'Adding full bibliography for 7062361--7062363.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062362
_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 0.1433(10) 0.4866(5) 0.4110(12) 0.050(3) Uani 1 1 d . . . . .
H1 H 0.152898 0.49315 0.491917 0.06 Uiso 1 1 calc R U . . .
C2 C 0.2161(10) 0.5131(5) 0.3430(11) 0.045(3) Uani 1 1 d . . . . .
C3 C 0.1907(9) 0.5022(5) 0.2133(11) 0.042(2) Uani 1 1 d . . . . .
C4 C 0.0798(11) 0.4552(5) 0.1924(10) 0.047(3) Uani 1 1 d . . . . .
H4 H 0.017997 0.478995 0.139579 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1182(11) 0.3874(6) 0.1320(10) 0.048(3) Uani 1 1 d . . . . .
H5 H 0.053332 0.356358 0.101028 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2211(10) 0.3518(5) 0.2044(10) 0.044(2) Uani 1 1 d . . . . .
C7 C 0.3151(10) 0.3961(5) 0.2165(11) 0.045(3) Uani 1 1 d . . . . .
C8 C 0.2874(10) 0.4636(6) 0.1565(10) 0.049(3) Uani 1 1 d . . . . .
H8 H 0.356149 0.492018 0.144849 0.058 Uiso 1 1 calc R U . . .
C9 C 0.0982(10) 0.2950(6) 0.7788(11) 0.051(3) Uani 1 1 d . . . . .
H9 H 0.052125 0.305788 0.837214 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1929(11) 0.2544(6) 0.7971(11) 0.048(3) Uani 1 1 d . . . . .
C11 C 0.2647(10) 0.2436(5) 0.7020(11) 0.044(2) Uani 1 1 d . . . . .
C12 C 0.2089(10) 0.2890(5) 0.5966(9) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.194896 0.260976 0.524773 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3003(11) 0.3457(5) 0.5851(11) 0.050(3) Uani 1 1 d . . . . .
H13 H 0.281503 0.37643 0.517023 0.06 Uiso 1 1 calc R U . . .
C14 C 0.3458(10) 0.3830(5) 0.6992(10) 0.044(2) Uani 1 1 d . . . . .
C15 C 0.4016(9) 0.3375(6) 0.7765(11) 0.048(3) Uani 1 1 d . . . . .
C16 C 0.3933(9) 0.2647(5) 0.7291(10) 0.040(2) Uani 1 1 d . . . . .
H16 H 0.444631 0.230556 0.774164 0.049 Uiso 1 1 calc R U . . .
O1 O 0.0513(8) 0.3629(4) 0.3642(8) 0.056(2) Uani 1 1 d . . . . .
O2 O 0.1405(9) 0.4746(6) -0.0567(9) 0.074(3) Uani 1 1 d . . . . .
O3 O 0.0777(8) 0.4030(4) 0.6360(9) 0.064(2) Uani 1 1 d . . . . .
O4 O 0.4196(7) 0.2325(4) 0.4978(7) 0.0513(19) Uani 1 1 d . . . . .
S1 S 0.0253(2) 0.43743(14) 0.3351(3) 0.0487(7) Uani 1 1 d . . . . .
S2 S 0.2064(3) 0.42371(18) 0.0188(3) 0.0598(8) Uani 1 1 d . . . . .
S3 S 0.0675(3) 0.32691(15) 0.6334(3) 0.0506(7) Uani 1 1 d . . . . .
S4 S 0.4379(2) 0.28960(13) 0.5820(3) 0.0449(6) Uani 1 1 d . . . . .
Br1 Br 0.35517(13) 0.56244(7) 0.39856(14) 0.0654(4) Uani 1 1 d . . . . .
Br2 Br 0.16161(12) 0.59462(6) 0.13897(13) 0.0566(4) Uani 1 1 d . . . . .
Br3 Br 0.46320(11) 0.37450(6) 0.29706(13) 0.0576(4) Uani 1 1 d . . . . .
Br4 Br 0.22242(11) 0.25986(6) 0.25126(11) 0.0505(4) Uani 1 1 d . . . . .
Br5 Br 0.24151(14) 0.21118(8) 0.94304(13) 0.0668(4) Uani 1 1 d . . . . .
Br6 Br 0.25727(11) 0.14270(6) 0.65719(12) 0.0515(4) Uani 1 1 d . . . . .
Br7 Br 0.48793(13) 0.35853(7) 0.92137(12) 0.0613(4) Uani 1 1 d . . . . .
Br8 Br 0.33787(13) 0.47814(6) 0.71688(14) 0.0612(4) 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 114.3(10) . . ?
C2 C1 H1 122.8 . . ?
S1 C1 H1 122.8 . . ?
C1 C2 C3 119.0(10) . . ?
C1 C2 Br1 124.2(10) . . ?
C3 C2 Br1 116.8(8) . . ?
C2 C3 C8 115.6(9) . . ?
C2 C3 C4 106.4(9) . . ?
C8 C3 C4 105.8(9) . . ?
C2 C3 Br2 107.8(7) . . ?
C8 C3 Br2 109.6(7) . . ?
C4 C3 Br2 111.6(7) . . ?
C3 C4 C5 106.3(10) . . ?
C3 C4 S1 109.5(7) . . ?
C5 C4 S1 112.6(7) . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
S1 C4 H4 109.5 . . ?
C6 C5 C4 112.1(9) . . ?
C6 C5 S2 95.6(8) . . ?
C4 C5 S2 102.0(7) . . ?
C6 C5 H5 115 . . ?
C4 C5 H5 115 . . ?
S2 C5 H5 115 . . ?
C7 C6 C5 108.7(10) . . ?
C7 C6 Br4 126.2(9) . . ?
C5 C6 Br4 124.7(8) . . ?
C6 C7 C8 112.4(10) . . ?
C6 C7 Br3 124.3(8) . . ?
C8 C7 Br3 123.3(8) . . ?
C7 C8 C3 110.0(9) . . ?
C7 C8 S2 95.0(7) . . ?
C3 C8 S2 104.5(8) . . ?
C7 C8 H8 115.1 . . ?
C3 C8 H8 115.1 . . ?
S2 C8 H8 115.1 . . ?
C10 C9 S3 114.0(10) . . ?
C10 C9 H9 123 . . ?
S3 C9 H9 123 . . ?
C9 C10 C11 119.3(11) . . ?
C9 C10 Br5 122.4(10) . . ?
C11 C10 Br5 118.2(8) . . ?
C10 C11 C16 115.7(10) . . ?
C10 C11 C12 106.8(9) . . ?
C16 C11 C12 107.3(9) . . ?
C10 C11 Br6 108.6(7) . . ?
C16 C11 Br6 108.5(7) . . ?
C12 C11 Br6 109.9(8) . . ?
C13 C12 C11 104.5(9) . . ?
C13 C12 S3 111.4(7) . . ?
C11 C12 S3 108.5(7) . . ?
C13 C12 H12 110.7 . . ?
C11 C12 H12 110.7 . . ?
S3 C12 H12 110.7 . . ?
C14 C13 C12 114.7(10) . . ?
C14 C13 S4 95.3(7) . . ?
C12 C13 S4 100.1(7) . . ?
C14 C13 H13 114.7 . . ?
C12 C13 H13 114.7 . . ?
S4 C13 H13 114.7 . . ?
C15 C14 C13 110.0(10) . . ?
C15 C14 Br8 126.7(9) . . ?
C13 C14 Br8 123.0(8) . . ?
C14 C15 C16 111.3(10) . . ?
C14 C15 Br7 126.7(9) . . ?
C16 C15 Br7 121.8(8) . . ?
C15 C16 C11 109.7(9) . . ?
C15 C16 S4 94.5(7) . . ?
C11 C16 S4 104.6(7) . . ?
C15 C16 H16 115.2 . . ?
C11 C16 H16 115.2 . . ?
S4 C16 H16 115.2 . . ?
O1 S1 C1 106.5(5) . . ?
O1 S1 C4 107.1(5) . . ?
C1 S1 C4 90.8(6) . . ?
O2 S2 C5 112.3(6) . . ?
O2 S2 C8 112.8(6) . . ?
C5 S2 C8 79.5(5) . . ?
O3 S3 C9 108.6(6) . . ?
O3 S3 C12 108.9(5) . . ?
C9 S3 C12 90.6(5) . . ?
O4 S4 C16 111.9(5) . . ?
O4 S4 C13 112.9(5) . . ?
C16 S4 C13 78.7(5) . . ?
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 1.316(16) . ?
C1 S1 1.777(12) . ?
C1 H1 0.93 . ?
C2 C3 1.495(17) . ?
C2 Br1 1.886(11) . ?
C3 C8 1.545(15) . ?
C3 C4 1.547(15) . ?
C3 Br2 1.974(10) . ?
C4 C5 1.564(15) . ?
C4 S1 1.862(12) . ?
C4 H4 0.98 . ?
C5 C6 1.509(15) . ?
C5 S2 1.882(12) . ?
C5 H5 0.98 . ?
C6 C7 1.362(15) . ?
C6 Br4 1.842(11) . ?
C7 C8 1.480(15) . ?
C7 Br3 1.865(11) . ?
C8 S2 1.885(13) . ?
C8 H8 0.98 . ?
C9 C10 1.327(16) . ?
C9 S3 1.770(14) . ?
C9 H9 0.93 . ?
C10 C11 1.466(18) . ?
C10 Br5 1.887(12) . ?
C11 C16 1.516(15) . ?
C11 C12 1.556(15) . ?
C11 Br6 2.001(10) . ?
C12 C13 1.525(15) . ?
C12 S3 1.871(11) . ?
C12 H12 0.98 . ?
C13 C14 1.524(17) . ?
C13 S4 1.909(12) . ?
C13 H13 0.98 . ?
C14 C15 1.344(16) . ?
C14 Br8 1.838(10) . ?
C15 C16 1.495(15) . ?
C15 Br7 1.863(12) . ?
C16 S4 1.891(12) . ?
C16 H16 0.98 . ?
O1 S1 1.489(8) . ?
O2 S2 1.449(9) . ?
O3 S3 1.462(9) . ?
O4 S4 1.457(8) . ?
