#------------------------------------------------------------------------------
#$Date: 2019-07-16 11:12:39 +0300 (Tue, 16 Jul 2019) $
#$Revision: 217082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233165.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_7233165
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         'C32 H46 Br2 N2 S4 Si2'
_chemical_formula_sum            'C32 H46 Br2 N2 S4 Si2'
_chemical_formula_weight         802.95
_chemical_name_common
;
4,4'-Dibromo-2,2'-bis(4-hexyl-5-(trimethylsilyl)thiophen-2-yl)-5,5'-bithiazole
;
_chemical_name_systematic
;
4,4'-Dibromo-2,2'-bis(4-hexyl-5-(trimethylsilyl)thiophen-2-yl)-5,5'-bithiazole
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 108.2470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   37.478(2)
_cell_length_b                   7.0932(4)
_cell_length_c                   14.7217(8)
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1853
_cell_measurement_theta_min      2.2888
_cell_volume                     3716.8(4)
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20666
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.6353
_exptl_absorpt_correction_T_min  0.3685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0356
_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)+(0.0564P)²+6.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3050
_reflns_number_total             3652
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000022.cif
_cod_data_source_block           PCOD1000022
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

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     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7233165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.244186(9) -0.20620(4) 0.20444(2) 0.02445(12) Uani 1 1 d . . .
Si1 Si 0.38076(3) 0.78142(14) 0.20900(7) 0.0343(2) Uani 1 1 d . . .
S1 S 0.27976(2) -0.00291(11) -0.03420(5) 0.02246(18) Uani 1 1 d . . .
S2 S 0.32776(2) 0.43924(12) 0.17428(6) 0.0278(2) Uani 1 1 d . . .
N1 N 0.27914(7) 0.0792(4) 0.13562(18) 0.0227(6) Uani 1 1 d . . .
C1 C 0.25858(8) -0.1631(4) 0.0226(2) 0.0201(6) Uani 1 1 d . . .
C2 C 0.26183(9) -0.0899(4) 0.1114(2) 0.0214(6) Uani 1 1 d . . .
C3 C 0.29010(9) 0.1421(4) 0.0648(2) 0.0226(6) Uani 1 1 d . . .
C4 C 0.31135(9) 0.3155(4) 0.0690(2) 0.0242(7) Uani 1 1 d . . .
C5 C 0.32267(9) 0.3980(4) -0.0013(2) 0.0254(7) Uani 1 1 d . . .
H5 H 0.3162 0.3508 -0.0647 0.030 Uiso 1 1 calc R . .
C6 C 0.34516(9) 0.5615(5) 0.0299(2) 0.0267(7) Uani 1 1 d . . .
C7 C 0.35096(9) 0.6013(5) 0.1252(2) 0.0281(7) Uani 1 1 d . . .
C8 C 0.36220(10) 0.6700(5) -0.0344(3) 0.0308(7) Uani 1 1 d . . .
H8A H 0.3592 0.8068 -0.0253 0.037 Uiso 1 1 calc R . .
H8B H 0.3484 0.6393 -0.1019 0.037 Uiso 1 1 calc R . .
C9 C 0.40385(10) 0.6256(6) -0.0144(3) 0.0381(9) Uani 1 1 d . . .
H9A H 0.4065 0.4923 -0.0311 0.046 Uiso 1 1 calc R . .
H9B H 0.4170 0.6411 0.0549 0.046 Uiso 1 1 calc R . .
C10 C 0.42255(11) 0.7518(6) -0.0705(3) 0.0436(10) Uani 1 1 d . . .
H10A H 0.4095 0.7343 -0.1398 0.052 Uiso 1 1 calc R . .
H10B H 0.4193 0.8851 -0.0548 0.052 Uiso 1 1 calc R . .
C11 C 0.46414(11) 0.7134(6) -0.0506(3) 0.0455(10) Uani 1 1 d . . .
H11A H 0.4775 0.7413 0.0175 0.055 Uiso 1 1 calc R . .
H11B H 0.4677 0.5778 -0.0612 0.055 Uiso 1 1 calc R . .
C12 C 0.48162(12) 0.8280(7) -0.1122(4) 0.0562(12) Uani 1 1 d . . .
H12A H 0.4796 0.9635 -0.0984 0.067 Uiso 1 1 calc R . .
H12B H 0.4672 0.8065 -0.1803 0.067 Uiso 1 1 calc R . .
C13 C 0.52265(13) 0.7805(8) -0.0966(4) 0.0722(16) Uani 1 1 d . . .
H13A H 0.5374 0.8097 -0.0304 0.108 Uiso 1 1 calc R . .
H13B H 0.5320 0.8552 -0.1404 0.108 Uiso 1 1 calc R . .
H13C H 0.5250 0.6460 -0.1089 0.108 Uiso 1 1 calc R . .
C14 C 0.42848(12) 0.6671(6) 0.2692(3) 0.0525(11) Uani 1 1 d . . .
H14A H 0.4437 0.7504 0.3197 0.079 Uiso 1 1 calc R . .
H14B H 0.4414 0.6460 0.2216 0.079 Uiso 1 1 calc R . .
H14C H 0.4248 0.5461 0.2973 0.079 Uiso 1 1 calc R . .
C15 C 0.38922(11) 0.9960(5) 0.1472(3) 0.0410(9) Uani 1 1 d . . .
H15A H 0.3651 1.0499 0.1091 0.061 Uiso 1 1 calc R . .
H15B H 0.4040 0.9632 0.1052 0.061 Uiso 1 1 calc R . .
H15C H 0.4030 1.0885 0.1947 0.061 Uiso 1 1 calc R . .
C16 C 0.35863(13) 0.8351(6) 0.3008(3) 0.0501(11) Uani 1 1 d . . .
H16A H 0.3754 0.9150 0.3502 0.075 Uiso 1 1 calc R . .
H16B H 0.3537 0.7175 0.3297 0.075 Uiso 1 1 calc R . .
H16C H 0.3349 0.9016 0.2714 0.075 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'
N N 0.0061 0.0033 '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'
Si Si 0.0817 0.0704 '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
C16 Si1 C15 112.2(2) . .
C16 Si1 C7 108.16(17) . .
C15 Si1 C7 113.23(17) . .
C16 Si1 C14 108.7(2) . .
C15 Si1 C14 107.33(19) . .
C7 Si1 C14 107.05(18) . .
C3 S1 C1 89.95(14) . .
C4 S2 C7 92.73(15) . .
C3 N1 C2 109.6(3) . .
C2 C1 C1 130.5(3) . 7_545
C2 C1 S1 107.0(2) . .
C1 C1 S1 122.5(3) 7_545 .
N1 C2 C1 118.4(3) . .
N1 C2 Br1 116.3(2) . .
C1 C2 Br1 125.3(2) . .
N1 C3 C4 123.8(3) . .
N1 C3 S1 115.1(2) . .
C4 C3 S1 121.0(2) . .
C5 C4 C3 128.7(3) . .
C5 C4 S2 110.8(2) . .
C3 C4 S2 120.4(2) . .
C4 C5 C6 113.5(3) . .
C4 C5 H5 123.3 . .
C6 C5 H5 123.3 . .
C7 C6 C5 112.5(3) . .
C7 C6 C8 124.8(3) . .
C5 C6 C8 122.6(3) . .
C6 C7 S2 110.4(2) . .
C6 C7 Si1 132.7(3) . .
S2 C7 Si1 116.75(18) . .
C6 C8 C9 112.4(3) . .
C6 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
C6 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.9 . .
C8 C9 C10 112.8(3) . .
C8 C9 H9A 109.0 . .
C10 C9 H9A 109.0 . .
C8 C9 H9B 109.0 . .
C10 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
C11 C10 C9 114.0(3) . .
C11 C10 H10A 108.8 . .
C9 C10 H10A 108.8 . .
C11 C10 H10B 108.8 . .
C9 C10 H10B 108.8 . .
H10A C10 H10B 107.6 . .
C12 C11 C10 113.5(4) . .
C12 C11 H11A 108.9 . .
C10 C11 H11A 108.9 . .
C12 C11 H11B 108.9 . .
C10 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C11 C12 C13 113.5(4) . .
C11 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
C11 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
Si1 C14 H14A 109.5 . .
Si1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
Si1 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
Si1 C15 H15A 109.5 . .
Si1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
Si1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Si1 C16 H16A 109.5 . .
Si1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
Si1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.887(3) .
Si1 C16 1.833(4) .
Si1 C15 1.850(4) .
Si1 C7 1.881(3) .
Si1 C14 1.910(4) .
S1 C3 1.726(3) .
S1 C1 1.742(3) .
S2 C4 1.718(3) .
S2 C7 1.730(3) .
N1 C3 1.312(4) .
N1 C2 1.357(4) .
C1 C2 1.377(4) .
C1 C1 1.451(6) 7_545
C3 C4 1.456(4) .
C4 C5 1.367(4) .
C5 C6 1.422(4) .
C5 H5 0.9500 .
C6 C7 1.381(4) .
C6 C8 1.508(4) .
C8 C9 1.528(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.530(5) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.518(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.512(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.520(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
