#------------------------------------------------------------------------------
#$Date: 2019-12-25 23:19:49 +0200 (Wed, 25 Dec 2019) $
#$Revision: 246008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311598.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_2311598
loop_
_publ_author_name
'Rigin, Sergei'
'Fonari, Marina'
_publ_section_title
;
 Crystal structure of
 4,4'-bis-(4-bromo-phen-yl)-1,1',3,3'-tetra-thia-fulvalene.
;
_journal_coeditor_code           EB2019
_journal_issue                   'Pt 8'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1195
_journal_page_last               1198
_journal_paper_doi               10.1107/S2056989019009952
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H10 Br2 S4'
_chemical_formula_moiety         'C18 H10 Br2 S4'
_chemical_formula_sum            'C18 H10 Br2 S4'
_chemical_formula_weight         514.32
_chemical_name_systematic
;
4,4'-Bis(4-bromophenyl)-1,1',3,3'-tetrathiafulvalene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           39
_space_group_name_Hall           'A 2 -2b'
_space_group_name_H-M_alt        'A e m 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5981(6)
_cell_length_b                   37.411(3)
_cell_length_c                   6.1991(5)
_cell_measurement_reflns_used    9390
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.375
_cell_measurement_theta_min      2.178
_cell_volume                     1762.1(2)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            34235
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.089
_exptl_absorpt_coefficient_mu    5.071
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.287
_refine_ls_abs_structure_details
;
Flack x determined using 663 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.014(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1580
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0171
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0126P)²+2.1911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0404
_refine_ls_wR_factor_ref         0.0407
_reflns_number_gt                1530
_reflns_number_total             1580
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eb2019sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'A 2 -2c'
_cod_original_sg_symbol_H-M      'A b m 2'
_cod_database_code               2311598
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.631
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y+1/2, z'
'-x, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1, z+1/2'
'-x, y+1, 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_occupancy
Br Br1 0.79020(5) 0.53149(2) 0.04905(9) 0.02338(12) Uani d 1
S S1 0.84814(9) 0.70527(2) 0.54322(17) 0.01212(17) Uani d 1
S S2 0.64506(12) 0.70791(2) 0.95068(14) 0.01322(19) Uani d 1
C C1 0.7514(4) 0.73205(10) 0.7447(6) 0.0120(7) Uani d 1
C C2 0.6459(5) 0.66817(10) 0.8081(6) 0.0122(8) Uani d 1
H H2 0.583254 0.648059 0.861560 0.015 Uiso calc 1
C C3 0.7350(5) 0.66579(9) 0.6225(6) 0.0117(8) Uani d 1
C C4 0.7515(4) 0.63362(9) 0.4874(6) 0.0125(8) Uani d 1
C C5 0.6886(4) 0.60030(9) 0.5600(9) 0.0159(7) Uani d 1
H H5 0.637106 0.598599 0.699223 0.019 Uiso calc 1
C C6 0.7004(5) 0.56997(10) 0.4326(7) 0.0182(8) Uani d 1
H H6 0.658485 0.547656 0.484660 0.022 Uiso calc 1
C C7 0.7737(5) 0.57250(10) 0.2289(7) 0.0148(8) Uani d 1
C C8 0.8384(4) 0.60494(10) 0.1519(6) 0.0133(7) Uani d 1
H H8 0.890749 0.606365 0.012995 0.016 Uiso calc 1
C C9 0.8253(4) 0.63529(10) 0.2817(6) 0.0129(8) Uani d 1
H H9 0.867405 0.657541 0.228922 0.015 Uiso calc 1
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C1 S1 C3 . 94.28(17)
C2 S2 C1 . 93.94(18)
S2 C1 S1 . 114.5(2)
C1 C1 S1 3_565 124.66(13)
C1 C1 S2 3_565 120.87(12)
S2 C2 H2 . 120.1
C3 C2 S2 . 119.9(3)
C3 C2 H2 . 120.1
C2 C3 S1 . 115.3(3)
C2 C3 C4 . 125.9(3)
C4 C3 S1 . 118.7(2)
C5 C4 C3 . 120.9(3)
C9 C4 C3 . 121.2(3)
C9 C4 C5 . 117.9(4)
C4 C5 H5 . 119.3
C6 C5 C4 . 121.4(4)
C6 C5 H5 . 119.3
C5 C6 H6 . 120.3
C7 C6 C5 . 119.4(4)
C7 C6 H6 . 120.3
C6 C7 Br1 . 120.5(3)
C6 C7 C8 . 120.9(4)
C8 C7 Br1 . 118.6(3)
C7 C8 H8 . 120.5
C7 C8 C9 . 119.1(3)
C9 C8 H8 . 120.5
C4 C9 C8 . 121.3(3)
C4 C9 H9 . 119.3
C8 C9 H9 . 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C7 . 1.901(4)
S1 C1 . 1.762(4)
S1 C3 . 1.778(4)
S2 C1 . 1.760(4)
S2 C2 . 1.729(4)
C1 C1 3_565 1.343(7)
C2 H2 . 0.9500
C2 C3 . 1.338(5)
C3 C4 . 1.472(5)
C4 C5 . 1.409(5)
C4 C9 . 1.394(5)
C5 H5 . 0.9500
C5 C6 . 1.385(6)
C6 H6 . 0.9500
C6 C7 . 1.384(6)
C7 C8 . 1.394(5)
C8 H8 . 0.9500
C8 C9 . 1.396(6)
C9 H9 . 0.9500
