#------------------------------------------------------------------------------
#$Date: 2019-07-16 11:10:55 +0300 (Tue, 16 Jul 2019) $
#$Revision: 217070 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233153.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_7233153
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         'C20 H14 N2 O4 S4'
_chemical_formula_sum            'C20 H14 N2 O4 S4'
_chemical_formula_weight         474.57
_chemical_name_common
;
2,7-Bis-(thiophen-2-yl)
-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane)
;
_chemical_name_systematic
;
2,7-Bis-(thiophen-2-yl)
-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane)
;
_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                 94.645(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4786(8)
_cell_length_b                   21.309(2)
_cell_length_c                   12.5339(13)
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.10
_cell_measurement_theta_min      2.51
_cell_volume                     1990.9(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  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23402
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+1.7089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2759
_reflns_number_total             3497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000010.cif
_cod_data_source_block           PCOD1000010
_cod_depositor_comments
;
The following automatic conversions were performed:

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     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7233153
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
S1 S 0.84884(10) 0.60841(3) 0.13194(5) 0.03497(19) Uani 1 1 d . . .
S2 S 0.75851(10) 0.46697(3) -0.02269(5) 0.03553(19) Uani 1 1 d . . .
S3 S 0.56377(12) 0.27734(4) -0.09402(7) 0.0479(2) Uani 1 1 d . . .
S4 S 0.88997(15) 0.72560(4) 0.41856(7) 0.0634(3) Uani 1 1 d . . .
O1 O 0.8650(2) 0.43953(9) 0.35502(15) 0.0351(4) Uani 1 1 d . . .
O2 O 0.6404(3) 0.48952(9) 0.43324(14) 0.0377(5) Uani 1 1 d . . .
O3 O 0.5346(3) 0.38136(8) 0.30733(15) 0.0371(5) Uani 1 1 d . . .
O4 O 0.4057(2) 0.47444(8) 0.25470(15) 0.0335(4) Uani 1 1 d . . .
N1 N 0.8092(3) 0.59117(10) 0.33259(17) 0.0311(5) Uani 1 1 d . . .
N2 N 0.5856(3) 0.38516(10) 0.08133(18) 0.0326(5) Uani 1 1 d . . .
C1 C 0.8576(3) 0.63340(12) 0.2648(2) 0.0305(6) Uani 1 1 d . . .
C2 C 0.7630(3) 0.53676(12) 0.2801(2) 0.0269(6) Uani 1 1 d . . .
C3 C 0.7767(3) 0.53650(12) 0.1722(2) 0.0283(6) Uani 1 1 d . . .
C4 C 0.7247(3) 0.48179(12) 0.1084(2) 0.0294(6) Uani 1 1 d . . .
C5 C 0.6330(3) 0.43339(12) 0.1499(2) 0.0288(6) Uani 1 1 d . . .
C6 C 0.5695(3) 0.43993(12) 0.2614(2) 0.0287(6) Uani 1 1 d . . .
C7 C 0.7087(3) 0.47722(12) 0.3354(2) 0.0284(6) Uani 1 1 d . . .
C8 C 0.8572(5) 0.41233(16) 0.4590(2) 0.0515(8) Uani 1 1 d . . .
H8A H 0.9780 0.4104 0.4975 0.062 Uiso 1 1 calc R . .
H8B H 0.8061 0.3695 0.4538 0.062 Uiso 1 1 calc R . .
C9 C 0.7383(6) 0.4554(2) 0.5137(3) 0.0733(12) Uani 1 1 d . . .
H9A H 0.6564 0.4313 0.5564 0.088 Uiso 1 1 calc R . .
H9B H 0.8104 0.4841 0.5622 0.088 Uiso 1 1 calc R . .
C10 C 0.3518(4) 0.38150(17) 0.3346(3) 0.0559(9) Uani 1 1 d . . .
H10A H 0.3434 0.3944 0.4100 0.067 Uiso 1 1 calc R . .
H10B H 0.2958 0.3397 0.3232 0.067 Uiso 1 1 calc R . .
C11 C 0.2664(4) 0.42908(15) 0.2585(3) 0.0506(8) Uani 1 1 d . . .
H11A H 0.2344 0.4105 0.1871 0.061 Uiso 1 1 calc R . .
H11B H 0.1578 0.4475 0.2861 0.061 Uiso 1 1 calc R . .
C12 C 0.6421(4) 0.39608(12) -0.0129(2) 0.0315(6) Uani 1 1 d . . .
C13 C 0.6185(4) 0.35544(12) -0.1061(2) 0.0334(6) Uani 1 1 d . . .
C14 C 0.6289(4) 0.37127(13) -0.2109(2) 0.0381(7) Uani 1 1 d . . .
H14A H 0.6578 0.4122 -0.2341 0.046 Uiso 1 1 calc R . .
C15 C 0.5925(4) 0.32051(14) -0.2806(2) 0.0440(7) Uani 1 1 d . . .
H15A H 0.5934 0.3236 -0.3562 0.053 Uiso 1 1 calc R . .
C16 C 0.5563(4) 0.26712(14) -0.2299(2) 0.0459(8) Uani 1 1 d . . .
H16 H 0.5297 0.2283 -0.2651 0.055 Uiso 1 1 calc R . .
C17 C 0.9142(3) 0.69694(12) 0.2928(2) 0.0323(6) Uani 1 1 d . . .
C19 C 1.0327(4) 0.79707(15) 0.2874(3) 0.0506(8) Uani 1 1 d . . .
H19A H 1.0878 0.8327 0.2583 0.061 Uiso 1 1 calc R . .
C18 C 0.9906(4) 0.74139(12) 0.2269(3) 0.0391(7) Uani 1 1 d . . .
H18 H 1.0110 0.7353 0.1538 0.047 Uiso 1 1 calc R . .
C20 C 0.9878(5) 0.79463(16) 0.3883(3) 0.0583(9) Uani 1 1 d . . .
H20 H 1.0084 0.8280 0.4380 0.070 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'
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'
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
C3 S1 C1 88.86(12) . .
C4 S2 C12 88.79(13) . .
C16 S3 C13 91.40(14) . .
C20 S4 C17 91.34(16) . .
C7 O1 C8 107.0(2) . .
C7 O2 C9 109.2(2) . .
C6 O3 C10 107.9(2) . .
C11 O4 C6 106.0(2) . .
C1 N1 C2 110.1(2) . .
C12 N2 C5 110.4(2) . .
N1 C1 C17 125.1(2) . .
N1 C1 S1 114.77(19) . .
C17 C1 S1 120.1(2) . .
N1 C2 C3 116.5(2) . .
N1 C2 C7 123.8(2) . .
C3 C2 C7 119.6(2) . .
C2 C3 C4 120.8(2) . .
C2 C3 S1 109.81(19) . .
C4 C3 S1 129.3(2) . .
C5 C4 C3 121.2(2) . .
C5 C4 S2 110.15(19) . .
C3 C4 S2 128.6(2) . .
C4 C5 N2 116.1(2) . .
C4 C5 C6 119.1(2) . .
N2 C5 C6 124.3(2) . .
O3 C6 O4 107.16(19) . .
O3 C6 C5 112.2(2) . .
O4 C6 C5 108.9(2) . .
O3 C6 C7 110.2(2) . .
O4 C6 C7 107.6(2) . .
C5 C6 C7 110.6(2) . .
O2 C7 O1 108.0(2) . .
O2 C7 C2 112.1(2) . .
O1 C7 C2 107.7(2) . .
O2 C7 C6 110.2(2) . .
O1 C7 C6 108.4(2) . .
C2 C7 C6 110.2(2) . .
O1 C8 C9 103.9(2) . .
O1 C8 H8A 111.0 . .
C9 C8 H8A 111.0 . .
O1 C8 H8B 111.0 . .
C9 C8 H8B 111.0 . .
H8A C8 H8B 109.0 . .
O2 C9 C8 106.6(3) . .
O2 C9 H9A 110.4 . .
C8 C9 H9A 110.4 . .
O2 C9 H9B 110.4 . .
C8 C9 H9B 110.4 . .
H9A C9 H9B 108.6 . .
O3 C10 C11 102.4(2) . .
O3 C10 H10A 111.3 . .
C11 C10 H10A 111.3 . .
O3 C10 H10B 111.3 . .
C11 C10 H10B 111.3 . .
H10A C10 H10B 109.2 . .
O4 C11 C10 101.8(2) . .
O4 C11 H11A 111.4 . .
C10 C11 H11A 111.4 . .
O4 C11 H11B 111.4 . .
C10 C11 H11B 111.4 . .
H11A C11 H11B 109.3 . .
N2 C12 C13 126.4(2) . .
N2 C12 S2 114.55(19) . .
C13 C12 S2 119.1(2) . .
C14 C13 C12 127.9(3) . .
C14 C13 S3 110.8(2) . .
C12 C13 S3 121.3(2) . .
C13 C14 C15 112.7(3) . .
C13 C14 H14A 123.6 . .
C15 C14 H14A 123.6 . .
C16 C15 C14 113.2(3) . .
C16 C15 H15A 123.4 . .
C14 C15 H15A 123.4 . .
C15 C16 S3 111.8(2) . .
C15 C16 H16 124.1 . .
S3 C16 H16 124.1 . .
C18 C17 C1 127.6(3) . .
C18 C17 S4 112.2(2) . .
C1 C17 S4 120.2(2) . .
C20 C19 C18 114.1(3) . .
C20 C19 H19A 123.0 . .
C18 C19 H19A 123.0 . .
C17 C18 C19 109.3(3) . .
C17 C18 H18 125.4 . .
C19 C18 H18 125.4 . .
C19 C20 S4 113.0(3) . .
C19 C20 H20 123.5 . .
S4 C20 H20 123.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.714(3) .
S1 C1 1.745(3) .
S2 C4 1.711(3) .
S2 C12 1.753(3) .
S3 C16 1.713(3) .
S3 C13 1.723(3) .
S4 C20 1.700(4) .
S4 C17 1.714(3) .
O1 C7 1.423(3) .
O1 C8 1.432(3) .
O2 C7 1.391(3) .
O2 C9 1.401(4) .
O3 C6 1.408(3) .
O3 C10 1.436(4) .
O4 C11 1.425(3) .
O4 C6 1.425(3) .
N1 C1 1.309(3) .
N1 C2 1.364(3) .
N2 C12 1.307(3) .
N2 C5 1.368(3) .
C1 C17 1.453(4) .
C2 C3 1.364(3) .
C2 C7 1.517(4) .
C3 C4 1.449(4) .
C4 C5 1.365(4) .
C5 C6 1.518(4) .
C6 C7 1.556(4) .
C8 C9 1.484(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.499(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.453(4) .
C13 C14 1.364(4) .
C14 C15 1.404(4) .
C14 H14A 0.9500 .
C15 C16 1.342(4) .
C15 H15A 0.9500 .
C16 H16 0.9500 .
C17 C18 1.408(4) .
C19 C20 1.336(5) .
C19 C18 1.429(4) .
C19 H19A 0.9500 .
C18 H18 0.9500 .
C20 H20 0.9500 .
