#------------------------------------------------------------------------------
#$Date: 2019-07-16 11:12:17 +0300 (Tue, 16 Jul 2019) $
#$Revision: 217079 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233162.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_7233162
loop_
_publ_author_name
'Yulia A. Getmanenko'
'Marina Fonari'
'Chad Risko'
'Bhupinder Sandhu'
'Elena Galan'
'Lingyun Zhu'
'Paul Tongwa'
'Do Kyung Hwang'
'Sanjeev Singh'
'He Wang'
'Shree Prakash Tiwari'
'Yueh-Lin Loo'
'Jean-Luc Bredas'
'Bernard Kippelen'
'Tatiana Timofeeva'
'Seth R. Marder'
_publ_section_title
;
 Benzo[1,2-b:6,5-b']dithiophene(dithiazole)-4,5-dione derivatives:
 synthesis, electronic properties, crystal packing and charge transport
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1467
_journal_page_last               1481
_journal_paper_doi               10.1039/C2TC00805J
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C14 H10 Br2 O4 S2'
_chemical_formula_sum            'C14 H10 Br2 O4 S2'
_chemical_formula_weight         466.16
_chemical_name_common
;
2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(1,3-dioxolane)
;
_chemical_name_systematic
;
2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(1,3-dioxolane)
;
_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_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.009(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.021(4)
_cell_length_b                   7.945(2)
_cell_length_c                   14.062(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1560.5(7)
_computing_cell_refinement       'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINTPlus, v. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8859
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    5.476
_exptl_absorpt_correction_T_max  0.383
_exptl_absorpt_correction_T_min  0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0294P)²+0.6086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0545
_reflns_number_gt                2430
_reflns_number_total             2751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000019.cif
_cod_data_source_block           PCOD1000019
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7233162
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.645607(16) 0.61895(3) 0.179494(19) 0.04223(9) Uani 1 1 d . . .
Br2 Br 1.18863(2) 0.06009(4) -0.06545(2) 0.05405(10) Uani 1 1 d . . .
S1 S 0.80557(4) 0.41925(8) 0.09137(4) 0.03609(14) Uani 1 1 d . . .
S2 S 1.00795(4) 0.24115(7) -0.00575(4) 0.03666(14) Uani 1 1 d . . .
O1 O 1.08418(11) 0.6573(2) 0.23310(12) 0.0380(4) Uani 1 1 d . . .
O2 O 1.02719(12) 0.5683(2) 0.37152(11) 0.0421(4) Uani 1 1 d . . .
O3 O 1.19002(10) 0.3940(2) 0.29943(11) 0.0362(4) Uani 1 1 d . . .
O4 O 1.05891(10) 0.23419(19) 0.32555(11) 0.0343(4) Uani 1 1 d . . .
C1 C 0.77326(16) 0.5459(3) 0.18225(17) 0.0340(5) Uani 1 1 d . . .
C2 C 0.84753(16) 0.5821(3) 0.24758(17) 0.0320(5) Uani 1 1 d . . .
H2 H 0.8424 0.6487 0.3013 0.038 Uiso 1 1 calc R . .
C3 C 0.93380(15) 0.5060(3) 0.22387(15) 0.0278(5) Uani 1 1 d . . .
C4 C 0.92235(15) 0.4144(3) 0.14122(15) 0.0291(5) Uani 1 1 d . . .
C5 C 1.03382(15) 0.5251(3) 0.27472(15) 0.0298(5) Uani 1 1 d . . .
C6 C 1.09365(15) 0.3621(3) 0.26568(15) 0.0287(5) Uani 1 1 d . . .
C7 C 1.08513(15) 0.2994(3) 0.16379(15) 0.0289(5) Uani 1 1 d . . .
C8 C 1.00169(15) 0.3238(3) 0.10650(15) 0.0296(5) Uani 1 1 d . . .
C9 C 1.15490(16) 0.2091(3) 0.11745(17) 0.0341(5) Uani 1 1 d . . .
H9 H 1.2150 0.1796 0.1459 0.041 Uiso 1 1 calc R . .
C10 C 1.12267(17) 0.1713(3) 0.02632(17) 0.0363(5) Uani 1 1 d . . .
C11 C 1.0705(2) 0.8041(3) 0.2880(2) 0.0606(8) Uani 1 1 d . . .
H11B H 1.0119 0.8619 0.2655 0.073 Uiso 1 1 calc R . .
H11A H 1.1240 0.8811 0.2862 0.073 Uiso 1 1 calc R . .
C12 C 1.0645(2) 0.7345(4) 0.3860(2) 0.0645(9) Uani 1 1 d . . .
H12B H 1.1274 0.7314 0.4209 0.077 Uiso 1 1 calc R . .
H12A H 1.0223 0.8023 0.4214 0.077 Uiso 1 1 calc R . .
C13 C 1.12714(17) 0.2219(3) 0.40791(17) 0.0413(6) Uani 1 1 d . . .
H13B H 1.1287 0.1092 0.4345 0.050 Uiso 1 1 calc R . .
H13A H 1.1129 0.3017 0.4569 0.050 Uiso 1 1 calc R . .
C14 C 1.21922(17) 0.2642(3) 0.36714(18) 0.0433(6) Uani 1 1 d . . .
H14B H 1.2665 0.3055 0.4160 0.052 Uiso 1 1 calc R . .
H14A H 1.2450 0.1676 0.3360 0.052 Uiso 1 1 calc R . .
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
C1 S1 C4 90.77(11) . .
C8 S2 C10 90.23(11) . .
C5 O1 C11 106.72(19) . .
C5 O2 C12 107.9(2) . .
C6 O3 C14 107.59(16) . .
C6 O4 C13 106.55(16) . .
C2 C1 S1 113.01(17) . .
C2 C1 Br1 128.41(18) . .
S1 C1 Br1 118.57(13) . .
C1 C2 C3 111.7(2) . .
C1 C2 H2 124.1 . .
C3 C2 H2 124.1 . .
C4 C3 C2 112.77(19) . .
C4 C3 C5 119.07(19) . .
C2 C3 C5 128.02(19) . .
C3 C4 C8 121.00(19) . .
C3 C4 S1 111.72(16) . .
C8 C4 S1 127.24(17) . .
O2 C5 O1 107.08(17) . .
O2 C5 C3 109.89(17) . .
O1 C5 C3 110.50(17) . .
O2 C5 C6 111.23(17) . .
O1 C5 C6 106.94(17) . .
C3 C5 C6 111.08(17) . .
O3 C6 O4 107.07(16) . .
O3 C6 C7 111.77(18) . .
O4 C6 C7 108.67(17) . .
O3 C6 C5 109.27(17) . .
O4 C6 C5 109.25(17) . .
C7 C6 C5 110.72(17) . .
C8 C7 C9 112.8(2) . .
C8 C7 C6 120.10(19) . .
C9 C7 C6 127.0(2) . .
C7 C8 C4 120.9(2) . .
C7 C8 S2 112.03(16) . .
C4 C8 S2 127.09(17) . .
C10 C9 C7 111.1(2) . .
C10 C9 H9 124.4 . .
C7 C9 H9 124.4 . .
C9 C10 S2 113.75(17) . .
C9 C10 Br2 127.74(19) . .
S2 C10 Br2 118.49(14) . .
O1 C11 C12 102.6(2) . .
O1 C11 H11B 111.2 . .
C12 C11 H11B 111.2 . .
O1 C11 H11A 111.2 . .
C12 C11 H11A 111.2 . .
H11B C11 H11A 109.2 . .
O2 C12 C11 105.0(2) . .
O2 C12 H12B 110.7 . .
C11 C12 H12B 110.7 . .
O2 C12 H12A 110.7 . .
C11 C12 H12A 110.7 . .
H12B C12 H12A 108.8 . .
O4 C13 C14 102.22(18) . .
O4 C13 H13B 111.3 . .
C14 C13 H13B 111.3 . .
O4 C13 H13A 111.3 . .
C14 C13 H13A 111.3 . .
H13B C13 H13A 109.2 . .
O3 C14 C13 102.08(18) . .
O3 C14 H14B 111.4 . .
C13 C14 H14B 111.4 . .
O3 C14 H14A 111.4 . .
C13 C14 H14A 111.4 . .
H14B C14 H14A 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.879(2) .
Br2 C10 1.874(2) .
S1 C1 1.718(2) .
S1 C4 1.724(2) .
S2 C8 1.719(2) .
S2 C10 1.724(2) .
O1 C5 1.420(3) .
O1 C11 1.420(3) .
O2 C5 1.415(3) .
O2 C12 1.428(3) .
O3 C6 1.415(2) .
O3 C14 1.438(3) .
O4 C6 1.432(3) .
O4 C13 1.440(3) .
C1 C2 1.358(3) .
C2 C3 1.418(3) .
C2 H2 0.9300 .
C3 C4 1.369(3) .
C3 C5 1.525(3) .
C4 C8 1.445(3) .
C5 C6 1.554(3) .
C6 C7 1.512(3) .
C7 C8 1.375(3) .
C7 C9 1.417(3) .
C9 C10 1.355(3) .
C9 H9 0.9300 .
C11 C12 1.494(5) .
C11 H11B 0.9700 .
C11 H11A 0.9700 .
C12 H12B 0.9700 .
C12 H12A 0.9700 .
C13 C14 1.496(4) .
C13 H13B 0.9700 .
C13 H13A 0.9700 .
C14 H14B 0.9700 .
C14 H14A 0.9700 .
