#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/11/4001143.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_4001143
loop_
_publ_author_name
'Ashizawa, Minoru'
'Yamada, Koichi'
'Fukaya, Atsuko'
'Kato, Reizo'
'Hara, Kouji'
'Takeya, Jun'
_publ_section_title
;
 Effect of Molecular Packing on Field-Effect Performance of Single
 Crystals of Thienyl-Substituted Pyrenes
;
_journal_issue                   15
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4883
_journal_paper_doi               10.1021/cm703499q
_journal_volume                  20
_journal_year                    2008
_chemical_formula_moiety         'C32 H18 S4 '
_chemical_formula_sum            'C32 H18 S4'
_chemical_formula_weight         530.73
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      13
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.158(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   14.192(14)
_cell_length_b                   6.135(5)
_cell_length_c                   15.912(17)
_cell_measurement_reflns_used    983
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1244(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.210
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9825
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             548.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.58
_refine_diff_density_min         -1.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     167
_refine_ls_number_reflns         593
_refine_ls_R_factor_gt           0.1144
_refine_ls_shift/su_max          0.0007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    18146400.0000    24111100.0000    6024960.0000
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2415
_reflns_number_gt                582
_reflns_number_total             2833
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cm703499q-file001.cif
_cod_data_source_block           '__1b'
_cod_original_cell_volume        1243(2)
_cod_original_formula_sum        'C32 H18 S4 '
_cod_database_code               4001143
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2-Z
3 -X,-Y,-Z
4 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S(1) S 0.8268(5) 0.3687(14) 0.3866(5) 0.092(2) Uani 0.91 1 d P
S(2) S 0.4257(4) 0.0360(12) 0.1649(3) 0.082(2) Uani 1.00 1 d .
C(1) C 0.5887(14) 0.289(3) 0.3445(12) 0.049(6) Uani 1.00 1 d .
C(2) C 0.6433(12) 0.453(3) 0.4035(12) 0.048(6) Uani 1.00 1 d .
C(3) C 0.6146(13) 0.535(3) 0.4675(12) 0.050(6) Uani 1.00 1 d .
C(4) C 0.5166(13) 0.459(3) 0.4660(11) 0.048(6) Uani 1.00 1 d .
C(5) C 0.4607(13) 0.285(3) 0.4028(13) 0.054(6) Uani 1.00 1 d .
C(6) C 0.4975(13) 0.193(3) 0.3422(11) 0.046(6) Uani 1.00 1 d .
C(7) C 0.6694(15) 0.689(3) 0.5348(15) 0.067(8) Uani 1.00 1 d .
C(8) C 0.6410(12) 0.768(3) 0.5968(14) 0.060(6) Uani 1.00 1 d .
C(9) C 0.7395(13) 0.548(4) 0.3962(12) 0.060(7) Uani 1.00 1 d .
C(10) C 0.7618(13) 0.772(3) 0.3909(14) 0.057(7) Uani 1.00 1 d .
C(11) C 0.858(2) 0.768(5) 0.379(2) 0.110(12) Uani 1.00 1 d .
C(12) C 0.8941(17) 0.578(5) 0.3747(15) 0.091(9) Uani 1.00 1 d .
C(13) C 0.4412(14) 0.020(3) 0.2769(13) 0.057(6) Uani 1.00 1 d .
C(14) C 0.3979(13) -0.167(3) 0.2897(15) 0.055(5) Uiso 1.00 1 d .
C(15) C 0.3582(17) -0.299(4) 0.2141(19) 0.087(10) Uani 1.00 1 d .
C(16) C 0.3634(13) -0.212(3) 0.1394(17) 0.076(8) Uani 1.00 1 d .
H(1) H 0.6147 0.2301 0.3052 0.068 Uiso 1.00 1 c R
H(2) H 0.7325 0.7380 0.5373 0.093 Uiso 1.00 1 c R
H(3) H 0.6839 0.8658 0.6422 0.065 Uiso 1.00 1 c R
H(4) H 0.7239 0.8932 0.3936 0.085 Uiso 1.00 1 c R
H(5) H 0.8914 0.8952 0.3757 0.132 Uiso 1.00 1 c R
H(6) H 0.9547 0.5579 0.3667 0.108 Uiso 1.00 1 c R
H(7) H 0.3983 -0.2084 0.3461 0.066 Uiso 1.00 1 c R
H(8) H 0.3275 -0.4337 0.2119 0.113 Uiso 1.00 1 c R
H(9) H 0.3377 -0.2758 0.0804 0.078 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 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
C(9) S(1) C(12) 89.4(13) . .
C(13) S(2) C(16) 90.6(12) . .
C(2) C(1) C(6) 124(2) . .
C(1) C(2) C(3) 121.7(19) . .
C(1) C(2) C(9) 119(2) . .
C(3) C(2) C(9) 119.4(17) . .
C(2) C(3) C(4) 118.2(17) . .
C(2) C(3) C(7) 126(2) . .
C(4) C(3) C(7) 116(2) . .
C(3) C(4) C(4) 120.0(16) . 66603
C(3) C(4) C(5) 118.5(19) . .
C(4) C(4) C(5) 121.2(19) 66603 .
C(4) C(5) C(6) 121.3(18) . .
C(4) C(5) C(8) 113.5(19) . 66603
C(6) C(5) C(8) 124.9(16) . 66603
C(1) C(6) C(5) 115.5(17) . .
C(1) C(6) C(13) 122(2) . .
C(5) C(6) C(13) 122.1(19) . .
C(3) C(7) C(8) 126(2) . .
C(5) C(8) C(7) 122.9(17) 66603 .
S(1) C(9) C(2) 117.8(17) . .
S(1) C(9) C(10) 115.3(16) . .
C(2) C(9) C(10) 126.8(19) . .
C(9) C(10) C(11) 104(2) . .
C(10) C(11) C(12) 116(2) . .
S(1) C(12) C(11) 115(2) . .
S(2) C(13) C(6) 118.8(17) . .
S(2) C(13) C(14) 110.4(15) . .
C(6) C(13) C(14) 131(2) . .
C(13) C(14) C(15) 114(2) . .
C(14) C(15) C(16) 113(2) . .
S(2) C(16) C(15) 111.6(18) . .
C(2) C(1) H(1) 119(2) . .
C(6) C(1) H(1) 117(2) . .
C(3) C(7) H(2) 117(2) . .
C(8) C(7) H(2) 117(2) . .
C(5) C(8) H(3) 116(2) 66603 .
C(7) C(8) H(3) 121(2) . .
C(9) C(10) H(4) 128.5 . .
C(11) C(10) H(4) 127.9 . .
C(10) C(11) H(5) 121.8 . .
C(12) C(11) H(5) 121.9 . .
S(1) C(12) H(6) 121.8 . .
C(11) C(12) H(6) 122.9 . .
C(13) C(14) H(7) 124.2 . .
C(15) C(14) H(7) 121.5 . .
C(14) C(15) H(8) 124.7 . .
C(16) C(15) H(8) 122.1 . .
S(2) C(16) H(9) 122.8 . .
C(15) C(16) H(9) 125.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S(1) C(9) 1.71(2) .
S(1) C(12) 1.66(3) .
S(2) C(13) 1.70(2) .
S(2) C(16) 1.72(2) .
C(1) C(2) 1.36(2) .
C(1) C(6) 1.41(2) .
C(2) C(3) 1.35(3) .
C(2) C(9) 1.53(2) .
C(3) C(4) 1.46(2) .
C(3) C(7) 1.38(2) .
C(4) C(4) 1.45(3) 66603
C(4) C(5) 1.44(2) .
C(5) C(6) 1.40(3) .
C(5) C(8) 1.48(2) 66603
C(6) C(13) 1.46(2) .
C(7) C(8) 1.31(3) .
C(9) C(10) 1.42(3) .
C(10) C(11) 1.45(4) .
C(11) C(12) 1.29(4) .
C(13) C(14) 1.36(3) .
C(14) C(15) 1.35(3) .
C(15) C(16) 1.33(4) .
C(1) H(1) 0.93(3) .
C(7) H(2) 0.93(3) .
C(8) H(3) 0.93(2) .
C(10) H(4) 0.930 .
C(11) H(5) 0.930 .
C(12) H(6) 0.930 .
C(14) H(7) 0.930 .
C(15) H(8) 0.930 .
C(16) H(9) 0.930 .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
C(4) C(14) 3.43(2) 56501
C(14) C(4) 3.43(2) 54501
S(1) H(1) 3.60(2) 65502
S(1) H(4) 3.287 54501
S(1) H(5) 3.074 54501
S(1) H(9) 3.072 55504
S(2) H(2) 2.942(19) 46404
S(2) H(3) 3.34(2) 46404
S(2) H(5) 3.064 64502
S(2) H(6) 3.534 64502
C(1) H(4) 2.980 54501
C(1) H(6) 3.545 65502
C(2) H(9) 3.142 55504
C(3) H(7) 3.224 56501
C(3) H(9) 3.282 55504
C(4) H(7) 2.791 56501
C(4) H(7) 3.095 65603
C(5) H(7) 3.247 56501
C(5) H(8) 3.273 56501
C(6) H(4) 3.473 54501
C(6) H(8) 3.310 56501
C(7) H(8) 3.138 55504
C(7) H(9) 3.334 55504
C(8) H(8) 3.531 65603
C(8) H(8) 3.209 55504
C(9) H(9) 3.118 55504
C(10) H(1) 3.41(2) 56501
C(12) H(1) 3.53(3) 65502
C(13) H(3) 3.39(2) 46404
C(14) H(3) 3.44(2) 46404
C(14) H(8) 3.581 55502
C(15) H(3) 3.46(3) 46404
C(15) H(6) 3.535 64502
C(15) H(7) 3.377 55502
C(15) H(8) 3.428 55502
C(16) H(2) 3.45(3) 46404
C(16) H(3) 3.33(3) 46404
C(16) H(6) 2.982 64502
H(1) S(1) 3.60(2) 65502
H(1) C(10) 3.41(2) 54501
H(1) C(12) 3.53(3) 65502
H(1) H(4) 2.594 54501
H(1) H(5) 3.506 64502
H(1) H(6) 3.182 65502
H(2) S(2) 2.942(19) 56504
H(2) C(16) 3.45(3) 56504
H(2) H(8) 3.119 55504
H(2) H(9) 3.137 55504
H(2) H(9) 3.561 56504
H(3) S(2) 3.34(2) 56504
H(3) C(13) 3.39(2) 56504
H(3) C(14) 3.44(2) 56504
H(3) C(15) 3.46(3) 56504
H(3) C(16) 3.33(3) 56504
H(3) H(3) 3.10(2) 65602
H(3) H(8) 3.573 65603
H(3) H(8) 3.227 55504
H(4) S(1) 3.287 56501
H(4) C(1) 2.980 56501
H(4) C(6) 3.473 56501
H(4) H(1) 2.594 56501
H(4) H(9) 3.567 56504
H(5) S(1) 3.074 56501
H(5) S(2) 3.064 66502
H(5) H(1) 3.506 66502
H(6) S(2) 3.534 66502
H(6) C(1) 3.545 65502
H(6) C(15) 3.535 66502
H(6) C(16) 2.982 66502
H(6) H(1) 3.182 65502
H(6) H(9) 2.871 66502
H(7) C(3) 3.224 54501
H(7) C(4) 2.791 54501
H(7) C(4) 3.095 65603
H(7) C(5) 3.247 54501
H(7) C(15) 3.377 55502
H(7) H(8) 3.228 55502
H(8) C(5) 3.273 54501
H(8) C(6) 3.310 54501
H(8) C(7) 3.138 45404
H(8) C(8) 3.531 65603
H(8) C(8) 3.209 45404
H(8) C(14) 3.581 55502
H(8) C(15) 3.428 55502
H(8) H(2) 3.119 45404
H(8) H(3) 3.573 65603
H(8) H(3) 3.227 45404
H(8) H(7) 3.228 55502
H(8) H(8) 2.941 55502
H(9) S(1) 3.072 45404
H(9) C(2) 3.142 45404
H(9) C(3) 3.282 45404
H(9) C(7) 3.334 45404
H(9) C(9) 3.118 45404
H(9) H(2) 3.137 45404
H(9) H(2) 3.561 46404
H(9) H(4) 3.567 46404
H(9) H(6) 2.871 64502
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_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C(9) S(1) C(12) C(11) 1(2) . . .
C(12) S(1) C(9) C(2) 176.1(14) . . .
C(12) S(1) C(9) C(10) -0.4(9) . . .
C(13) S(2) C(16) C(15) -1.1(18) . . .
C(16) S(2) C(13) C(6) 177.6(17) . . .
C(16) S(2) C(13) C(14) -1.0(16) . . .
C(2) C(1) C(6) C(5) 3(2) . . .
C(2) C(1) C(6) C(13) 179.3(17) . . .
C(6) C(1) C(2) C(3) 1(2) . . .
C(6) C(1) C(2) C(9) -178.1(17) . . .
C(1) C(2) C(3) C(4) -6(2) . . .
C(1) C(2) C(3) C(7) 174.6(19) . . .
C(1) C(2) C(9) S(1) -45(2) . . .
C(1) C(2) C(9) C(10) 131(2) . . .
C(3) C(2) C(9) S(1) 135.3(17) . . .
C(3) C(2) C(9) C(10) -49(2) . . .
C(9) C(2) C(3) C(4) 173.3(16) . . .
C(9) C(2) C(3) C(7) -6(3) . . .
C(2) C(3) C(4) C(5) 6(2) . . .
C(2) C(3) C(4) C(4) 179.4(16) . . 66603
C(2) C(3) C(7) C(8) 179.8(16) . . .
C(4) C(3) C(7) C(8) 1(2) . . .
C(7) C(3) C(4) C(5) -174.6(17) . . .
C(7) C(3) C(4) C(4) -1(2) . . 66603
C(3) C(4) C(4) C(5) 7(2) . 66603 66603
C(3) C(4) C(5) C(6) -1(2) . . .
C(3) C(4) C(5) C(8) -176.2(16) . . 66603
C(4) C(4) C(5) C(6) -174.6(16) 66603 . .
C(4) C(4) C(5) C(8) 11(2) 66603 . 66603
C(5) C(4) C(4) C(3) -7(2) . 66603 66603
C(4) C(5) C(6) C(1) -3(2) . . .
C(4) C(5) C(6) C(13) -179.1(17) . . .
C(4) C(5) C(8) C(7) -10(2) . 66603 66603
C(6) C(5) C(8) C(7) 175.4(19) . 66603 66603
C(8) C(5) C(6) C(1) 171.1(17) 66603 . .
C(8) C(5) C(6) C(13) -5(2) 66603 . .
C(1) C(6) C(13) S(2) -41(2) . . .
C(1) C(6) C(13) C(14) 138(2) . . .
C(5) C(6) C(13) S(2) 135.1(17) . . .
C(5) C(6) C(13) C(14) -47(3) . . .
C(3) C(7) C(8) C(5) -5(3) . . 66603
S(1) C(9) C(10) C(11) -0.5(16) . . .
C(2) C(9) C(10) C(11) -176.7(18) . . .
C(9) C(10) C(11) C(12) 2(2) . . .
C(10) C(11) C(12) S(1) -2(3) . . .
S(2) C(13) C(14) C(15) 3(2) . . .
C(6) C(13) C(14) C(15) -175(2) . . .
C(13) C(14) C(15) C(16) -4(2) . . .
C(14) C(15) C(16) S(2) 3(2) . . .
