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#$Revision: 280458 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106501.cif $
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#
# 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.
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data_8106501
loop_
_publ_author_name
'Mabkhot, Yahia N.'
'Al-aizari, Faiz A.'
'Al-Showiman, Salim'
'Barakat, Assem'
'Ghabbour, Hazem A.'
'Frey, Wolfgang'
_publ_section_title
;
 Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b]
 thiophene-2,5-diyl)bis(2-bromoethanone), C10H6Br2O4S2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              255
_journal_page_last               256
_journal_paper_doi               10.1515/ncrs-2016-0228
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C10 H6 Br2 O4 S2'
_chemical_formula_sum            'C10 H6 Br2 O4 S2'
_chemical_formula_weight         414.09
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.309(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1199(6)
_cell_length_b                   10.4430(8)
_cell_length_c                   15.4252(13)
_cell_measurement_reflns_used    2522
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.36
_cell_volume                     1300.08(18)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12691
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.557
_exptl_absorpt_correction_T_max  0.4162
_exptl_absorpt_correction_T_min  0.1864
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.631
_refine_diff_density_min         -1.425
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0317P)²+15.0475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                2522
_reflns_number_total             3273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0228_suppl.cif
_cod_data_source_block           bak21a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.94456(9) 0.95528(7) 0.10595(4) 0.02469(18) Uani 0.95 1 d PD A 1
Br1A Br 0.9198(15) 1.0202(9) 0.0961(6) 0.021(3) Uani 0.05 1 d PDU A 2
S1 S 0.88045(19) 0.79677(15) 0.44438(9) 0.0219(3) Uani 1 1 d . . .
Br2 Br 0.57022(8) 1.00955(7) 0.89881(4) 0.02441(18) Uani 0.96 1 d PD B 1
Br2A Br 0.549(2) 1.0675(11) 0.8725(8) 0.040(4) Uani 0.04 1 d PDU B 2
S2 S 0.7507(2) 0.84642(15) 0.62512(10) 0.0233(3) Uani 1 1 d . . .
O1 O 0.9897(6) 0.8105(5) 0.2765(3) 0.0304(11) Uani 1 1 d . . .
C1 C 0.8554(7) 0.9326(7) 0.3739(4) 0.0240(13) Uani 1 1 d . . .
C2 C 0.7876(7) 1.0344(6) 0.4100(4) 0.0226(12) Uani 1 1 d . . .
O2 O 0.5262(6) 1.1388(5) 0.7257(3) 0.0308(10) Uani 1 1 d . . .
C3 C 0.7521(6) 1.0039(5) 0.4975(3) 0.0148(10) Uani 1 1 d . . .
C4 C 0.7948(8) 0.8843(6) 0.5220(4) 0.0236(12) Uani 1 1 d . . .
C5 C 0.6824(7) 1.0770(6) 0.5641(4) 0.0228(12) Uani 1 1 d . . .
C6 C 0.6705(7) 1.0041(6) 0.6357(4) 0.0228(12) Uani 1 1 d . . .
O7 O 0.7505(5) 1.1521(4) 0.3695(3) 0.0239(9) Uani 1 1 d . . .
H7 H 0.7101 1.1398 0.3177 0.036 Uiso 1 1 calc R . .
O8 O 0.6287(6) 1.2047(4) 0.5566(3) 0.0262(10) Uani 1 1 d . . .
H8 H 0.6216 1.2349 0.6065 0.039 Uiso 1 1 calc R . .
C9 C 0.9145(7) 0.9092(7) 0.2875(4) 0.0247(13) Uani 1 1 d . A .
C10 C 0.8699(8) 1.0047(7) 0.2152(4) 0.0262(13) Uani 1 1 d D . .
H10A H 0.9191 1.0887 0.2329 0.031 Uiso 1 1 calc R A 1
H10B H 0.7480 1.0153 0.2069 0.031 Uiso 1 1 calc R A 1
C11 C 0.6048(7) 1.0416(6) 0.7175(4) 0.0220(12) Uani 1 1 d . B .
C12 C 0.6412(8) 0.9479(7) 0.7922(4) 0.0287(14) Uani 1 1 d D . .
H12A H 0.7619 0.9312 0.8011 0.034 Uiso 1 1 calc R B 1
H12B H 0.5847 0.8658 0.7764 0.034 Uiso 1 1 calc R B 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 S1 C1 88.5(3) . .
C4 S2 C6 89.3(3) . .
C2 C1 C9 133.5(6) . .
C2 C1 S1 113.6(4) . .
C9 C1 S1 112.9(5) . .
C1 C2 O7 126.0(6) . .
C1 C2 C3 110.2(5) . .
O7 C2 C3 123.8(5) . .
C4 C3 C5 113.7(5) . .
C4 C3 C2 113.4(5) . .
C5 C3 C2 132.9(5) . .
C3 C4 S1 114.3(5) . .
C3 C4 S2 113.8(5) . .
S1 C4 S2 131.9(4) . .
C6 C5 O8 123.5(5) . .
C6 C5 C3 110.6(5) . .
O8 C5 C3 125.9(5) . .
C5 C6 C11 127.9(6) . .
C5 C6 S2 112.6(5) . .
C11 C6 S2 119.5(5) . .
C2 O7 H7 109.5 . .
C5 O8 H8 109.5 . .
O1 C9 C1 118.6(6) . .
O1 C9 C10 122.6(5) . .
C1 C9 C10 118.7(6) . .
C9 C10 Br1 113.4(5) . .
C9 C10 Br1A 134.4(5) . .
Br1 C10 Br1A 21.5(3) . .
C9 C10 H10A 108.9 . .
Br1 C10 H10A 108.9 . .
Br1A C10 H10A 93.9 . .
C9 C10 H10B 108.9 . .
Br1 C10 H10B 108.9 . .
Br1A C10 H10B 100.3 . .
H10A C10 H10B 107.7 . .
O2 C11 C6 123.7(6) . .
O2 C11 C12 121.4(5) . .
C6 C11 C12 114.9(6) . .
C11 C12 Br2 112.6(5) . .
C11 C12 Br2A 90.7(5) . .
Br2 C12 Br2A 21.9(3) . .
C11 C12 H12A 109.1 . .
Br2 C12 H12A 109.1 . .
Br2A C12 H12A 117.6 . .
C11 C12 H12B 109.1 . .
Br2 C12 H12B 109.1 . .
Br2A C12 H12B 120.5 . .
H12A C12 H12B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C10 1.922(5) .
Br1A C10 1.930(7) .
S1 C4 1.713(6) .
S1 C1 1.785(7) .
Br2 C12 1.914(6) .
Br2A C12 1.963(8) .
S2 C4 1.714(6) .
S2 C6 1.785(7) .
O1 C9 1.220(8) .
C1 C2 1.346(9) .
C1 C9 1.485(8) .
C2 O7 1.397(7) .
C2 C3 1.446(8) .
O2 C11 1.214(8) .
C3 C4 1.340(8) .
C3 C5 1.444(8) .
C5 C6 1.354(9) .
C5 O8 1.404(8) .
C6 C11 1.475(8) .
O7 H7 0.8400 .
O8 H8 0.8400 .
C9 C10 1.510(9) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.515(9) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 S1 C1 C2 0.4(5) . . . .
C4 S1 C1 C9 -179.7(4) . . . .
C9 C1 C2 O7 1.6(11) . . . .
S1 C1 C2 O7 -178.5(5) . . . .
C9 C1 C2 C3 179.7(6) . . . .
S1 C1 C2 C3 -0.5(6) . . . .
C1 C2 C3 C4 0.4(7) . . . .
O7 C2 C3 C4 178.5(5) . . . .
C1 C2 C3 C5 179.2(6) . . . .
O7 C2 C3 C5 -2.7(10) . . . .
C5 C3 C4 S1 -179.1(4) . . . .
C2 C3 C4 S1 -0.1(7) . . . .
C5 C3 C4 S2 1.8(7) . . . .
C2 C3 C4 S2 -179.2(4) . . . .
C1 S1 C4 C3 -0.2(5) . . . .
C1 S1 C4 S2 178.7(5) . . . .
C6 S2 C4 C3 -0.5(5) . . . .
C6 S2 C4 S1 -179.4(5) . . . .
C4 C3 C5 C6 -2.5(7) . . . .
C2 C3 C5 C6 178.7(6) . . . .
C4 C3 C5 O8 179.3(6) . . . .
C2 C3 C5 O8 0.5(10) . . . .
O8 C5 C6 C11 -1.2(10) . . . .
C3 C5 C6 C11 -179.3(5) . . . .
O8 C5 C6 S2 -179.7(5) . . . .
C3 C5 C6 S2 2.1(6) . . . .
C4 S2 C6 C5 -1.0(5) . . . .
C4 S2 C6 C11 -179.7(5) . . . .
C2 C1 C9 O1 171.3(6) . . . .
S1 C1 C9 O1 -8.6(7) . . . .
C2 C1 C9 C10 -12.5(10) . . . .
S1 C1 C9 C10 167.7(4) . . . .
O1 C9 C10 Br1 -0.4(8) . . . .
C1 C9 C10 Br1 -176.5(4) . . . .
O1 C9 C10 Br1A -5.9(11) . . . .
C1 C9 C10 Br1A 178.0(7) . . . .
C5 C6 C11 O2 12.9(10) . . . .
S2 C6 C11 O2 -168.6(5) . . . .
C5 C6 C11 C12 -167.6(6) . . . .
S2 C6 C11 C12 10.8(7) . . . .
O2 C11 C12 Br2 -5.9(8) . . . .
C6 C11 C12 Br2 174.7(4) . . . .
O2 C11 C12 Br2A -7.5(9) . . . .
C6 C11 C12 Br2A 173.1(8) . . . .
