#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/15/4111516.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_4111516
loop_
_publ_author_name
'Kazuo Takimiya'
'Yoshihito Kunugi'
'Yuta Toyoshima'
'Tetsuo Otsubo'
_publ_contact_author_address
;
Department of Applied Chemistry, 
Graduate School of Engineering, 
Hiroshima University, Kagamiyama,
739-8527 Japan
;
_publ_contact_author_email       ' ktakimi@hiroshima-u.ac.jp '
_publ_contact_author_fax         ' +81-82-424-7734 '
_publ_contact_author_name        ' Kazuo Takimiya'
_publ_contact_author_phone       ' 81-82-424-5494 '
_publ_section_title
;
 2,6-Diarylnaphtho[1,8-bc:5,4-b'c']dithiophenes as New High-Performance
 Semiconductors for Organic Field-Effect Transistors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3605
_journal_page_last               3612
_journal_paper_doi               10.1021/ja043429p
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C24 H14 S2 '
_chemical_formula_sum            'C24 H14 S2'
_chemical_formula_weight         366.49
_chemical_melting_point          537(1)
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3528(1)
_cell_length_b                   8.1884(1)
_cell_length_c                   28.6857(5)
_cell_measurement_reflns_used    20899
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.1
_cell_volume                     1727.10(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9862
_diffrn_measured_fraction_theta_max 0.9862
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            12688
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.82
_refine_diff_density_min         -0.70
_refine_ls_extinction_coef       0.0308
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.487
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1651
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          -0.0440
_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         0.1821
_reflns_number_gt                1651
_reflns_number_total             1955
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            ja043429psi20041030_013238_2.cif
_cod_data_source_block           DPh-NDT_4
_cod_original_cell_volume        1727.10(5)
_cod_original_formula_sum        'C24 H14 S2 '
_cod_database_code               4111516
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-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_calc_flag
S(1) S 0.57916(8) -0.35917(7) 0.46291(2) 0.0432(3) Uani 1.00 d
C(1) C 0.5242(3) -0.2214(3) 0.41876(7) 0.0400(5) Uani 1.00 d
C(2) C 0.4918(3) -0.0658(2) 0.43679(7) 0.0370(5) Uani 1.00 d
C(3) C 0.5125(3) -0.0682(2) 0.48625(7) 0.0360(5) Uani 1.00 d
C(4) C 0.5588(3) -0.2172(3) 0.50628(7) 0.0375(5) Uani 1.00 d
C(5) C 0.5775(3) -0.2259(3) 0.55574(8) 0.0410(5) Uani 1.00 d
C(6) C 0.5538(3) -0.0900(3) 0.58336(8) 0.0398(5) Uani 1.00 d
C(7) C 0.5098(3) -0.2835(3) 0.37088(7) 0.0424(5) Uani 1.00 d
C(8) C 0.6089(4) -0.4216(4) 0.35724(9) 0.0565(7) Uani 1.00 d
C(9) C 0.5895(4) -0.4866(4) 0.3128(1) 0.0678(8) Uani 1.00 d
C(10) C 0.4729(5) -0.4154(4) 0.2814(1) 0.0713(8) Uani 1.00 d
C(11) C 0.3740(5) -0.2794(4) 0.29430(9) 0.0624(7) Uani 1.00 d
C(12) C 0.3911(4) -0.2145(3) 0.33877(8) 0.0508(6) Uani 1.00 d
H(1) H 0.594(4) -0.338(4) 0.572(1) 0.0759 Uiso 1.00 calc
H(2) H 0.571(4) -0.089(4) 0.614(1) 0.0759 Uiso 1.00 calc
H(3) H 0.694(4) -0.478(4) 0.378(1) 0.0759 Uiso 1.00 calc
H(4) H 0.650(5) -0.594(4) 0.308(1) 0.0759 Uiso 1.00 calc
H(5) H 0.458(5) -0.458(4) 0.249(1) 0.0759 Uiso 1.00 calc
H(6) H 0.287(5) -0.231(4) 0.2734(10) 0.0759 Uiso 1.00 calc
H(7) H 0.328(5) -0.134(4) 0.343(1) 0.0759 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
S S 0.125 0.123
;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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) S(1) C(4) 93.9(1) . . yes
S(1) C(1) C(2) 111.2(1) . . yes
S(1) C(1) C(7) 118.2(2) . . yes
C(2) C(1) C(7) 130.6(2) . . yes
C(1) C(2) C(3) 109.7(2) . . yes
C(1) C(2) C(6) 134.4(2) . 5_656 yes
C(3) C(2) C(6) 115.9(2) . 5_656 yes
C(2) C(3) C(3) 122.9(2) . 5_656 yes
C(2) C(3) C(4) 116.7(2) . . yes
C(3) C(3) C(4) 120.4(2) 5_656 . yes
S(1) C(4) C(3) 108.5(1) . . yes
S(1) C(4) C(5) 133.0(2) . . yes
C(3) C(4) C(5) 118.5(2) . . yes
C(4) C(5) C(6) 121.3(2) . . yes
C(2) C(6) C(5) 120.9(2) 5_656 . yes
C(1) C(7) C(8) 120.2(2) . . yes
C(1) C(7) C(12) 121.6(2) . . yes
C(8) C(7) C(12) 118.0(2) . . yes
C(7) C(8) C(9) 120.9(3) . . yes
C(8) C(9) C(10) 120.2(3) . . yes
C(9) C(10) C(11) 119.7(3) . . yes
C(10) C(11) C(12) 120.5(3) . . yes
C(7) C(12) C(11) 120.7(2) . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(1) 1.744(2) . yes
S(1) C(4) 1.709(2) . yes
C(1) C(2) 1.395(3) . yes
C(1) C(7) 1.469(3) . yes
C(2) C(3) 1.427(3) . yes
C(2) C(6) 1.440(3) 5_656 yes
C(3) C(3) 1.380(4) 5_656 yes
C(3) C(4) 1.391(3) . yes
C(4) C(5) 1.427(3) . yes
C(5) C(6) 1.377(3) . yes
C(7) C(8) 1.401(4) . yes
C(7) C(12) 1.389(3) . yes
C(8) C(9) 1.388(4) . yes
C(9) C(10) 1.374(4) . yes
C(10) C(11) 1.380(5) . yes
C(11) C(12) 1.388(4) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
S(1) S(1) 3.347(1) 5_646
S(1) C(3) 3.521(2) 6_645
S(1) C(3) 3.554(2) 2_546
C(1) C(5) 3.392(3) 2_446
C(2) C(5) 3.498(3) 2_446
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S(1) C(1) C(2) C(3) -0.5(2) . . . yes
S(1) C(1) C(2) C(6) 178.6(2) . . 5_656 yes
S(1) C(1) C(7) C(8) -27.2(3) . . . yes
S(1) C(1) C(7) C(12) 148.9(2) . . . yes
S(1) C(4) C(3) C(2) 0.4(2) . . . yes
S(1) C(4) C(3) C(3) -180.0(2) . . 5_656 yes
S(1) C(4) C(5) C(6) 179.9(2) . . . yes
C(1) S(1) C(4) C(3) -0.5(2) . . . yes
C(1) S(1) C(4) C(5) 178.5(2) . . . yes
C(1) C(2) C(3) C(3) -179.6(2) . . 5_656 yes
C(1) C(2) C(3) C(4) 0.1(3) . . . yes
C(1) C(2) C(6) C(5) -179.8(2) . 5_656 5_656 yes
C(1) C(7) C(8) C(9) 176.7(2) . . . yes
C(1) C(7) C(12) C(11) -177.3(2) . . . yes
C(2) C(1) S(1) C(4) 0.6(2) . . . yes
C(2) C(1) C(7) C(8) 156.5(2) . . . yes
C(2) C(1) C(7) C(12) -27.3(4) . . . yes
C(2) C(3) C(3) C(2) 180.0 . 5_656 5_656 yes
C(2) C(3) C(3) C(4) -0.4(4) . 5_656 5_656 yes
C(2) C(3) C(4) C(5) -178.8(2) . . . yes
C(2) C(6) C(5) C(4) -0.3(3) 5_656 5_656 5_656 yes
C(3) C(2) C(1) C(7) 176.0(2) . . . yes
C(3) C(2) C(6) C(5) -0.8(3) . 5_656 5_656 yes
C(3) C(3) C(2) C(6) -1.2(3) 5_656 5_656 . yes
C(3) C(3) C(4) C(5) -0.8(3) 5_656 5_656 5_656 yes
C(3) C(4) C(5) C(6) -1.2(3) . . . yes
C(4) S(1) C(1) C(7) -176.4(2) . . . yes
C(4) C(3) C(2) C(6) -179.2(2) . . 5_656 yes
C(4) C(3) C(3) C(4) -180.0 . 5_656 5_656 yes
C(6) C(2) C(1) C(7) 4.9(4) 5_656 5_656 5_656 yes
C(7) C(8) C(9) C(10) 0.4(5) . . . yes
C(7) C(12) C(11) C(10) 1.0(4) . . . yes
C(8) C(7) C(12) C(11) -1.0(4) . . . yes
C(8) C(9) C(10) C(11) -0.5(5) . . . yes
C(9) C(8) C(7) C(12) 0.4(4) . . . yes
C(9) C(10) C(11) C(12) -0.2(5) . . . yes
C(9) C(10) C(11) C(12) -0.2(5) . . . yes
