#------------------------------------------------------------------------------
#$Date: 2019-07-16 11:12:09 +0300 (Tue, 16 Jul 2019) $
#$Revision: 217078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233161.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_7233161
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 F2 O4 S2'
_chemical_formula_sum            'C14 H10 F2 O4 S2'
_chemical_formula_weight         344.34
_chemical_name_common
;
2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(ethyleneoxolane)
;
_chemical_name_systematic
;
2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(ethyleneoxolane)
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.888(6)
_cell_angle_beta                 103.524(6)
_cell_angle_gamma                99.264(4)
_cell_formula_units_Z            2
_cell_length_a                   6.907(3)
_cell_length_b                   10.238(3)
_cell_length_c                   10.674(4)
_cell_measurement_reflns_used    4232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.14
_cell_measurement_theta_min      2.53
_cell_volume                     703.8(5)
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9161
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0342P)²+0.2311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                2436
_reflns_number_total             2769
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000018.cif
_cod_data_source_block           PCOD1000018
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.29621(6) 0.07450(4) -0.07321(4) 0.04132(12) Uani 1 1 d . . .
S2 S 0.27621(7) -0.05432(4) 0.20983(5) 0.04476(13) Uani 1 1 d . . .
F1 F 0.26250(19) 0.20359(13) -0.26671(10) 0.0634(3) Uani 1 1 d . . .
F2 F 0.2662(2) -0.09854(13) 0.44418(13) 0.0788(4) Uani 1 1 d . . .
O1 O -0.12233(15) 0.29274(12) 0.12109(11) 0.0430(3) Uani 1 1 d . . .
O2 O 0.08932(18) 0.37740(12) 0.39123(11) 0.0465(3) Uani 1 1 d . . .
O3 O 0.39502(16) 0.40623(11) 0.34376(10) 0.0390(3) Uani 1 1 d . . .
O4 O 0.11441(17) 0.48603(11) 0.15658(11) 0.0410(3) Uani 1 1 d . . .
C1 C 0.2413(3) 0.20687(18) -0.14345(15) 0.0428(4) Uani 1 1 d . . .
C5 C 0.0894(2) 0.34636(15) 0.15757(15) 0.0320(3) Uani 1 1 d . . .
C8 C 0.2390(2) 0.10297(15) 0.18531(14) 0.0323(3) Uani 1 1 d . . .
C7 C 0.2119(2) 0.18332(15) 0.29487(14) 0.0341(3) Uani 1 1 d . . .
C4 C 0.2300(2) 0.15038(15) 0.06545(14) 0.0312(3) Uani 1 1 d . . .
C3 C 0.1685(2) 0.26840(15) 0.05230(14) 0.0309(3) Uani 1 1 d . . .
C6 C 0.1933(2) 0.32885(15) 0.29805(14) 0.0340(3) Uani 1 1 d . . .
C2 C 0.1748(2) 0.30234(16) -0.07000(15) 0.0371(3) Uani 1 1 d . . .
H13A H 0.1384 0.3790 -0.0953 0.045 Uiso 1 1 calc R . .
C11 C 0.3233(3) 0.55871(16) 0.20300(18) 0.0454(4) Uani 1 1 d . . .
H14A H 0.3309 0.6537 0.2010 0.055 Uiso 1 1 calc R . .
H14B H 0.4003 0.5209 0.1453 0.055 Uiso 1 1 calc R . .
C12 C 0.4130(3) 0.54800(16) 0.34115(17) 0.0466(4) Uani 1 1 d . . .
H15A H 0.5554 0.5944 0.3714 0.056 Uiso 1 1 calc R . .
H15B H 0.3418 0.5910 0.4001 0.056 Uiso 1 1 calc R . .
C9 C 0.2185(3) 0.11904(18) 0.40245(16) 0.0467(4) Uani 1 1 d . . .
H16A H 0.2020 0.1583 0.4842 0.056 Uiso 1 1 calc R . .
C13 C -0.2205(3) 0.3467(2) 0.2187(2) 0.0549(5) Uani 1 1 d . . .
H17A H -0.3649 0.3050 0.1899 0.066 Uiso 1 1 calc R . .
H17B H -0.2060 0.4442 0.2281 0.066 Uiso 1 1 calc R . .
C14 C -0.1265(3) 0.3186(2) 0.3489(2) 0.0567(5) Uani 1 1 d . . .
H18A H -0.1907 0.3568 0.4146 0.068 Uiso 1 1 calc R . .
H18B H -0.1483 0.2210 0.3407 0.068 Uiso 1 1 calc R . .
C10 C 0.2520(3) -0.00682(19) 0.36833(18) 0.0514(4) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 '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
C1 S1 C4 89.11(8) . .
C10 S2 C8 89.09(8) . .
C5 O1 C13 113.04(13) . .
C6 O2 C14 112.91(12) . .
C6 O3 C12 114.18(12) . .
C5 O4 C11 113.38(11) . .
C2 C1 F1 126.38(16) . .
C2 C1 S1 115.59(12) . .
F1 C1 S1 118.00(13) . .
O1 C5 O4 106.47(11) . .
O1 C5 C3 105.60(12) . .
O4 C5 C3 111.67(12) . .
O1 C5 C6 111.13(12) . .
O4 C5 C6 110.48(12) . .
C3 C5 C6 111.30(12) . .
C7 C8 C4 120.79(14) . .
C7 C8 S2 112.20(11) . .
C4 C8 S2 126.99(11) . .
C8 C7 C9 113.39(14) . .
C8 C7 C6 120.69(13) . .
C9 C7 C6 125.77(14) . .
C3 C4 C8 120.99(13) . .
C3 C4 S1 111.91(11) . .
C8 C4 S1 127.09(11) . .
C4 C3 C2 113.69(13) . .
C4 C3 C5 120.84(13) . .
C2 C3 C5 125.35(13) . .
O3 C6 O2 106.80(12) . .
O3 C6 C7 105.27(12) . .
O2 C6 C7 111.97(12) . .
O3 C6 C5 110.19(12) . .
O2 C6 C5 110.82(12) . .
C7 C6 C5 111.54(12) . .
C1 C2 C3 109.69(14) . .
C1 C2 H13A 125.2 . .
C3 C2 H13A 125.2 . .
O4 C11 C12 109.85(14) . .
O4 C11 H14A 109.7 . .
C12 C11 H14A 109.7 . .
O4 C11 H14B 109.7 . .
C12 C11 H14B 109.7 . .
H14A C11 H14B 108.2 . .
O3 C12 C11 109.24(13) . .
O3 C12 H15A 109.8 . .
C11 C12 H15A 109.8 . .
O3 C12 H15B 109.8 . .
C11 C12 H15B 109.8 . .
H15A C12 H15B 108.3 . .
C10 C9 C7 109.89(16) . .
C10 C9 H16A 125.1 . .
C7 C9 H16A 125.1 . .
O1 C13 C14 109.87(14) . .
O1 C13 H17A 109.7 . .
C14 C13 H17A 109.7 . .
O1 C13 H17B 109.7 . .
C14 C13 H17B 109.7 . .
H17A C13 H17B 108.2 . .
O2 C14 C13 110.18(15) . .
O2 C14 H18A 109.6 . .
C13 C14 H18A 109.6 . .
O2 C14 H18B 109.6 . .
C13 C14 H18B 109.6 . .
H18A C14 H18B 108.1 . .
C9 C10 F2 126.90(18) . .
C9 C10 S2 115.43(13) . .
F2 C10 S2 117.67(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7202(18) .
S1 C4 1.7320(15) .
S2 C10 1.725(2) .
S2 C8 1.7288(15) .
F1 C1 1.3524(19) .
F2 C10 1.352(2) .
O1 C5 1.4094(18) .
O1 C13 1.444(2) .
O2 C6 1.4190(18) .
O2 C14 1.443(2) .
O3 C6 1.4101(18) .
O3 C12 1.443(2) .
O4 C5 1.4148(18) .
O4 C11 1.436(2) .
C1 C2 1.343(2) .
C5 C3 1.512(2) .
C5 C6 1.560(2) .
C8 C7 1.367(2) .
C8 C4 1.443(2) .
C7 C9 1.423(2) .
C7 C6 1.511(2) .
C4 C3 1.364(2) .
C3 C2 1.421(2) .
C2 H13A 0.9300 .
C11 C12 1.492(2) .
C11 H14A 0.9700 .
C11 H14B 0.9700 .
C12 H15A 0.9700 .
C12 H15B 0.9700 .
C9 C10 1.343(3) .
C9 H16A 0.9300 .
C13 C14 1.492(3) .
C13 H17A 0.9700 .
C13 H17B 0.9700 .
C14 H18A 0.9700 .
C14 H18B 0.9700 .
