#------------------------------------------------------------------------------
#$Date: 2019-07-16 11:11:52 +0300 (Tue, 16 Jul 2019) $
#$Revision: 217076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233159.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_7233159
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         'C10 H2 I2 O2 S2'
_chemical_formula_sum            'C10 H2 I2 O2 S2'
_chemical_formula_weight         472.04
_chemical_name_common
;
2,7-Diiodo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione
;
_chemical_name_systematic
;
2,7-Diiodo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione
;
_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_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                 92.054(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.766(5)
_cell_length_b                   6.323(2)
_cell_length_c                   17.766(7)
_cell_measurement_reflns_used    7836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9273
_cell_measurement_theta_min      2.2942
_cell_volume                     1433.1(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12838
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    4.662
_exptl_absorpt_correction_T_max  0.6528
_exptl_absorpt_correction_T_min  0.3352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         4.221
_refine_diff_density_min         -2.522
_refine_diff_density_rms         0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0938
_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)+(0.0281P)²+132.5564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2127
_reflns_number_gt                2509
_reflns_number_total             2806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000016.cif
_cod_data_source_block           PCOD1000016
_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_cell_volume        1433.2(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7233159
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
I1 I 0.58004(10) 1.43764(19) -0.22518(8) 0.0328(4) Uani 1 1 d . . .
I2 I 0.89070(9) 0.18413(17) 0.05481(6) 0.0216(3) Uani 1 1 d . . .
S1 S 0.6882(4) 1.0454(7) -0.1254(2) 0.0226(9) Uani 1 1 d . . .
S2 S 0.8011(4) 0.6177(6) -0.0289(2) 0.0204(9) Uani 1 1 d . . .
O1 O 0.8497(10) 0.741(2) -0.3501(6) 0.027(3) Uani 1 1 d . . .
O2 O 0.9593(10) 0.4332(18) -0.2730(6) 0.024(3) Uani 1 1 d . . .
C1 C 0.6753(13) 1.168(2) -0.2099(9) 0.0179(11) Uani 1 1 d . . .
C2 C 0.7337(13) 1.072(2) -0.2705(9) 0.0179(11) Uani 1 1 d . . .
H2 H 0.7365 1.1188 -0.3201 0.022 Uiso 1 1 calc R . .
C3 C 0.7853(13) 0.893(2) -0.2380(9) 0.0179(11) Uani 1 1 d . . .
C4 C 0.7734(13) 0.857(2) -0.1611(9) 0.0179(11) Uani 1 1 d . . .
C5 C 0.8469(13) 0.739(2) -0.2829(9) 0.0179(11) Uani 1 1 d . . .
C6 C 0.9022(13) 0.554(2) -0.2365(9) 0.0179(11) Uani 1 1 d . . .
C7 C 0.8799(13) 0.529(2) -0.1578(9) 0.0179(11) Uani 1 1 d . . .
C8 C 0.8183(13) 0.679(2) -0.1206(9) 0.0179(11) Uani 1 1 d . . .
C9 C 0.9111(13) 0.370(2) -0.1073(9) 0.0179(11) Uani 1 1 d . . .
H9 H 0.9533 0.2580 -0.1217 0.022 Uiso 1 1 calc R . .
C10 C 0.8761(13) 0.387(2) -0.0352(9) 0.0179(11) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0362(7) 0.0172(6) 0.0447(8) -0.0014(5) -0.0038(5) 0.0044(5)
I2 0.0384(7) 0.0133(5) 0.0134(5) 0.0032(4) 0.0049(4) 0.0020(5)
S1 0.033(2) 0.0147(19) 0.020(2) 0.0000(16) 0.0031(17) 0.0026(17)
S2 0.039(2) 0.0117(18) 0.0108(17) 0.0000(14) 0.0055(16) 0.0034(16)
O1 0.039(7) 0.026(7) 0.017(6) -0.001(5) 0.001(5) -0.003(6)
O2 0.045(7) 0.014(6) 0.014(6) -0.006(5) 0.002(5) 0.006(5)
C1 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C2 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C3 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C4 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C5 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C6 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C7 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C8 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C9 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
C10 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2)
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'
I I -0.4742 1.8119 '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 91.9(8) . .
C8 S2 C10 92.2(8) . .
C2 C1 S1 115.3(12) . .
C2 C1 I1 123.2(11) . .
S1 C1 I1 121.5(9) . .
C3 C2 C1 105.7(13) . .
C3 C2 H2 127.1 . .
C1 C2 H2 127.1 . .
C4 C3 C2 117.6(15) . .
C4 C3 C5 119.3(14) . .
C2 C3 C5 123.0(14) . .
C3 C4 C8 124.0(15) . .
C3 C4 S1 109.4(12) . .
C8 C4 S1 126.4(12) . .
O1 C5 C3 123.9(15) . .
O1 C5 C6 120.0(14) . .
C3 C5 C6 115.8(13) . .
O2 C6 C7 125.0(15) . .
O2 C6 C5 116.0(13) . .
C7 C6 C5 119.0(14) . .
C9 C7 C8 109.5(14) . .
C9 C7 C6 129.6(15) . .
C8 C7 C6 120.9(14) . .
C7 C8 C4 120.6(14) . .
C7 C8 S2 113.0(12) . .
C4 C8 S2 126.3(12) . .
C10 C9 C7 116.4(15) . .
C10 C9 H9 121.8 . .
C7 C9 H9 121.8 . .
C9 C10 S2 108.8(12) . .
C9 C10 I2 130.6(12) . .
S2 C10 I2 120.4(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.105(16) .
I2 C10 2.054(16) .
S1 C1 1.693(16) .
S1 C4 1.748(17) .
S2 C8 1.697(16) .
S2 C10 1.750(16) .
O1 C5 1.196(19) .
O2 C6 1.25(2) .
C1 C2 1.46(2) .
C2 C3 1.42(2) .
C2 H2 0.9300 .
C3 C4 1.40(2) .
C3 C5 1.50(2) .
C4 C8 1.44(2) .
C5 C6 1.58(2) .
C6 C7 1.44(2) .
C7 C9 1.40(2) .
C7 C8 1.41(2) .
C9 C10 1.38(2) .
C9 H9 0.9300 .
