#------------------------------------------------------------------------------
#$Date: 2019-09-19 11:50:47 +0300 (Thu, 19 Sep 2019) $
#$Revision: 218535 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233952.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_7233952
loop_
_publ_author_name
'Takefumi Odajima'
'Minoru Ashizawa'
'Yuichi Konosu'
'Hidetoshi Matsumoto'
'Takehiko Mori'
_publ_section_title
;
 The impact of molecular planarity on electronic devices in
 thienoisoindigo-based organic semiconductors
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10455
_journal_page_last               10467
_journal_paper_doi               10.1039/C4TC02170C
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C44 H46 N2 O2 S4'
_chemical_formula_sum            'C44 H46 N2 O2 S4'
_chemical_formula_weight         763.10
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                110.3188(14)
_cell_angle_beta                 92.1751(15)
_cell_angle_gamma                106.1216(14)
_cell_formula_units_Z            1
_cell_length_a                   5.21365(13)
_cell_length_b                   12.5465(3)
_cell_length_c                   16.7656(4)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.92
_cell_volume                     976.95(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11510
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.540
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             404.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.890
_refine_diff_density_min         -0.700
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.539
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3510
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.1344
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.4030
_reflns_number_gt                2522
_reflns_number_total             3510
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_original_cell_volume        976.95(5)
_cod_database_code               7233952
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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 1.1828(3) 0.17381(13) 0.96209(10) 0.0447(6) Uani 1.0 2 d . . .
S2 S 0.5528(5) 0.1307(2) 0.76404(15) 0.0810(9) Uani 1.0 2 d . . .
O1 O 1.3837(9) -0.2302(4) 0.9067(3) 0.0556(13) Uani 1.0 2 d . . .
N1 N 1.0892(11) -0.1603(5) 0.8461(4) 0.0453(14) Uani 1.0 2 d . . .
C1 C 0.4822(14) 0.2626(6) 0.7873(5) 0.0513(17) Uani 1.0 2 d . . .
C2 C 0.2929(17) 0.2795(8) 0.7366(6) 0.069(3) Uani 1.0 2 d . . .
C3 C 0.2450(18) 0.3880(9) 0.7616(7) 0.087(3) Uani 1.0 2 d . . .
C4 C 0.4013(19) 0.4833(8) 0.8405(7) 0.078(3) Uani 1.0 2 d . . .
C5 C 0.5876(18) 0.4656(7) 0.8899(6) 0.076(3) Uani 1.0 2 d . . .
C6 C 0.6290(14) 0.3529(6) 0.8643(5) 0.0531(18) Uani 1.0 2 d . . .
C7 C 0.8233(11) 0.3274(5) 0.9194(4) 0.0361(13) Uiso 1.0 2 d . . .
C8 C 0.7766(14) 0.1928(6) 0.8580(5) 0.0484(17) Uani 1.0 2 d . . .
C9 C 0.9232(14) 0.1150(6) 0.8780(4) 0.0460(16) Uani 1.0 2 d . . .
C10 C 0.8682(13) -0.0072(5) 0.8315(4) 0.0465(16) Uani 1.0 2 d . . .
C11 C 1.0482(13) -0.0490(5) 0.8663(4) 0.0403(15) Uani 1.0 2 d . . .
C12 C 1.2288(12) 0.0357(6) 0.9375(4) 0.0387(14) Uani 1.0 2 d . . .
C13 C 1.3969(13) -0.0198(6) 0.9669(4) 0.0437(16) Uani 1.0 2 d . . .
C14 C 1.2983(14) -0.1497(6) 0.9049(4) 0.0461(17) Uani 1.0 2 d . . .
C15 C 0.9192(14) -0.2737(6) 0.7845(4) 0.0509(17) Uani 1.0 2 d . . .
C16 C 1.000(3) -0.3021(11) 0.6996(8) 0.130(5) Uiso 1.0 2 d . . .
C17 C 1.062(2) -0.2269(9) 0.6561(7) 0.100(3) Uiso 1.0 2 d . . .
C18 C 1.126(3) -0.2365(11) 0.5721(6) 0.111(4) Uani 1.0 2 d . . .
C19 C 1.204(3) -0.1620(14) 0.5365(10) 0.167(6) Uiso 1.0 2 d . . .
C20 C 1.300(3) -0.1733(14) 0.4541(7) 0.152(6) Uani 1.0 2 d . . .
C21 C 0.849(3) -0.4658(14) 0.6350(8) 0.149(6) Uani 1.0 2 d . . .
C22 C 0.608(3) -0.4521(14) 0.6243(7) 0.144(6) Uani 1.0 2 d . . .
H2 H 0.1987 0.2177 0.6858 0.0830 Uiso 1.0 2 calc R . .
H3 H 0.1159 0.4002 0.7289 0.1040 Uiso 1.0 2 calc R . .
H4 H 0.3736 0.5577 0.8576 0.0937 Uiso 1.0 2 calc R . .
H5 H 0.6863 0.5274 0.9400 0.0907 Uiso 1.0 2 calc R . .
H7 H 0.9334 0.3749 0.9718 0.0433 Uiso 1.0 2 calc R . .
H10 H 0.7329 -0.0534 0.7847 0.0558 Uiso 1.0 2 calc R . .
H15A H 0.7344 -0.2720 0.7802 0.0611 Uiso 1.0 2 calc R . .
H15B H 0.9243 -0.3364 0.8052 0.0611 Uiso 1.0 2 calc R . .
H16 H 1.1833 -0.3018 0.7152 0.1560 Uiso 1.0 2 calc R . .
H17A H 1.2134 -0.1615 0.6939 0.1195 Uiso 1.0 2 calc R . .
H17B H 0.9114 -0.1948 0.6603 0.1195 Uiso 1.0 2 calc R . .
H18A H 1.2609 -0.2775 0.5645 0.1328 Uiso 1.0 2 calc R . .
H18B H 0.9645 -0.2944 0.5339 0.1328 Uiso 1.0 2 calc R . .
H19A H 1.3473 -0.0974 0.5786 0.2004 Uiso 1.0 2 calc R . .
H19B H 1.0547 -0.1302 0.5351 0.2004 Uiso 1.0 2 calc R . .
H20A H 1.1826 -0.2440 0.4096 0.1830 Uiso 1.0 2 calc R . .
H20B H 1.4798 -0.1789 0.4573 0.1830 Uiso 1.0 2 calc R . .
H20C H 1.3009 -0.1045 0.4411 0.1830 Uiso 1.0 2 calc R . .
H21A H 0.9216 -0.4924 0.5817 0.1793 Uiso 1.0 2 calc R . .
H21B H 0.8556 -0.5158 0.6675 0.1793 Uiso 1.0 2 calc R . .
H22A H 0.6169 -0.3997 0.5935 0.1728 Uiso 1.0 2 calc R . .
H22B H 0.5561 -0.4182 0.6795 0.1728 Uiso 1.0 2 calc R . .
H22C H 0.4783 -0.5285 0.5922 0.1728 Uiso 1.0 2 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 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C9 S1 C12 90.6(3) yes . . .
C1 S2 C8 89.8(4) yes . . .
C11 N1 C14 108.9(5) yes . . .
C11 N1 C15 127.0(6) yes . . .
C14 N1 C15 123.3(6) yes . . .
S2 C1 C2 123.9(5) yes . . .
S2 C1 C6 113.9(7) yes . . .
C2 C1 C6 122.2(8) yes . . .
C1 C2 C3 119.7(7) yes . . .
C2 C3 C4 118.5(10) yes . . .
C3 C4 C5 121.2(9) yes . . .
C4 C5 C6 119.4(7) yes . . .
C1 C6 C5 118.9(8) yes . . .
C1 C6 C7 119.9(7) yes . . .
C5 C6 C7 121.2(6) yes . . .
C6 C7 C8 96.5(5) yes . . .
S2 C8 C7 119.9(6) yes . . .
S2 C8 C9 117.4(4) yes . . .
C7 C8 C9 122.7(6) yes . . .
S1 C9 C8 121.0(4) yes . . .
S1 C9 C10 114.1(6) yes . . .
C8 C9 C10 124.9(6) yes . . .
C9 C10 C11 109.2(6) yes . . .
N1 C11 C10 134.3(5) yes . . .
N1 C11 C12 110.5(6) yes . . .
C10 C11 C12 115.2(6) yes . . .
S1 C12 C11 110.8(6) yes . . .
S1 C12 C13 140.1(4) yes . . .
C11 C12 C13 109.1(6) yes . . .
C12 C13 C13 134.1(6) yes . . 2_857
C12 C13 C14 104.4(5) yes . . .
C13 C13 C14 121.5(7) yes 2_857 . .
O1 C14 N1 126.1(5) yes . . .
O1 C14 C13 126.8(6) yes . . .
N1 C14 C13 107.1(6) yes . . .
N1 C15 C16 113.1(7) yes . . .
C15 C16 C17 126.1(11) yes . . .
C15 C16 C21 110.1(10) yes . . .
C17 C16 C21 117.8(10) yes . . .
C16 C17 C18 136.0(11) yes . . .
C17 C18 C19 133.9(12) yes . . .
C18 C19 C20 132.0(15) yes . . .
C16 C21 C22 90.7(12) yes . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C9 1.715(7) yes . .
S1 C12 1.724(7) yes . .
S2 C1 1.711(9) yes . .
S2 C8 1.719(7) yes . .
O1 C14 1.220(10) yes . .
N1 C11 1.398(9) yes . .
N1 C14 1.388(10) yes . .
N1 C15 1.445(7) yes . .
C1 C2 1.385(13) yes . .
C1 C6 1.401(8) yes . .
C2 C3 1.375(15) yes . .
C3 C4 1.457(12) yes . .
C4 C5 1.366(16) yes . .
C5 C6 1.410(12) yes . .
C6 C7 1.515(11) yes . .
C7 C8 1.586(8) yes . .
C8 C9 1.508(12) yes . .
C9 C10 1.396(9) yes . .
C10 C11 1.393(11) yes . .
C11 C12 1.386(7) yes . .
C12 C13 1.428(11) yes . .
C13 C13 1.365(9) yes . 2_857
C13 C14 1.523(8) yes . .
C15 C16 1.451(15) yes . .
C16 C17 1.36(2) yes . .
C16 C21 1.871(18) yes . .
C17 C18 1.431(15) yes . .
C18 C19 1.26(3) yes . .
C19 C20 1.46(2) yes . .
C21 C22 1.33(3) yes . .
