#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/47/1504778.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_1504778
loop_
_publ_author_name
'Suzuki, Yoshitake'
'Okamoto, Toshihiro'
'Wakamiya, Atsushi'
'Yamaguchi, Shigehiro'
_publ_section_title
;
 Electronic modulation of fused oligothiophenes by chemical oxidation.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3393
_journal_page_last               3396
_journal_paper_doi               10.1021/ol801136k
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C30 H44 O4 S5 Si2'
_chemical_formula_weight         685.13
_chemical_name_common            TDTDT
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2746(4)
_cell_length_b                   16.2746(4)
_cell_length_c                   13.7437(5)
_cell_measurement_reflns_used    12045
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      1.7692
_cell_volume                     3640.19(18)
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24934
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.9596
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_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)+(0.0416P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                3264
_reflns_number_total             3398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801136k-file004.cif
_cod_data_source_block           comp5
_cod_original_sg_symbol_H-M      P-421c
_cod_database_code               1504778
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'-y, x, -z'
'y, -x, -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
S1 S 0.28752(3) 0.11676(4) 0.18821(4) 0.01179(14) Uani 1 1 d .
C1 C 0.22061(15) 0.15296(15) 0.27703(17) 0.0139(5) Uani 1 1 d .
C2 C 0.24932(15) 0.13461(15) 0.36824(18) 0.0151(5) Uani 1 1 d .
H1 H 0.2218 0.1489 0.4268 0.018 Uiso 1 1 calc R
C3 C 0.32470(14) 0.09198(14) 0.36463(17) 0.0124(5) Uani 1 1 d .
C4 C 0.35396(14) 0.07748(14) 0.27233(16) 0.0099(5) Uani 1 1 d .
C5 C 0.43340(14) 0.03597(14) 0.27172(17) 0.0105(5) Uani 1 1 d .
C6 C 0.46238(14) 0.02008(14) 0.36375(16) 0.0094(5) Uani 1 1 d .
S2 S 0.39028(3) 0.04939(4) 0.45353(4) 0.01086(13) Uani 1 1 d .
S3 S 0.5000 0.0000 0.18327(6) 0.00971(17) Uani 1 2 d S
O1 O 0.42384(10) 0.11025(10) 0.51747(11) 0.0166(4) Uani 1 1 d .
O2 O 0.35467(10) -0.02232(10) 0.49620(12) 0.0171(4) Uani 1 1 d .
Si1 Si 0.12746(4) 0.21509(4) 0.24172(5) 0.01289(15) Uani 1 1 d .
C7 C 0.09717(16) 0.18117(16) 0.11525(18) 0.0224(6) Uani 1 1 d .
H2 H 0.1487 0.1822 0.0756 0.027 Uiso 1 1 calc R
C8 C 0.06580(19) 0.09305(18) 0.1113(2) 0.0373(8) Uani 1 1 d .
H3 H 0.0111 0.0903 0.1408 0.056 Uiso 1 1 calc R
H4 H 0.1035 0.0572 0.1471 0.056 Uiso 1 1 calc R
H5 H 0.0626 0.0750 0.0434 0.056 Uiso 1 1 calc R
C9 C 0.03721(17) 0.23987(19) 0.0650(2) 0.0328(7) Uani 1 1 d .
H6 H 0.0268 0.2208 -0.0015 0.049 Uiso 1 1 calc R
H7 H 0.0610 0.2951 0.0630 0.049 Uiso 1 1 calc R
H8 H -0.0146 0.2413 0.1012 0.049 Uiso 1 1 calc R
C10 C 0.16055(15) 0.32593(15) 0.2389(2) 0.0196(6) Uani 1 1 d .
H9 H 0.1114 0.3592 0.2201 0.024 Uiso 1 1 calc R
C11 C 0.18931(17) 0.35727(17) 0.3383(2) 0.0262(7) Uani 1 1 d .
H10 H 0.2368 0.3250 0.3600 0.039 Uiso 1 1 calc R
H11 H 0.1446 0.3516 0.3856 0.039 Uiso 1 1 calc R
H12 H 0.2050 0.4152 0.3330 0.039 Uiso 1 1 calc R
C12 C 0.22747(18) 0.34205(18) 0.1620(2) 0.0302(7) Uani 1 1 d .
H13 H 0.2404 0.4008 0.1604 0.045 Uiso 1 1 calc R
H14 H 0.2075 0.3247 0.0979 0.045 Uiso 1 1 calc R
H15 H 0.2770 0.3109 0.1786 0.045 Uiso 1 1 calc R
C13 C 0.04832(15) 0.19736(15) 0.34008(17) 0.0160(5) Uani 1 1 d .
H16 H 0.0714 0.2224 0.4007 0.019 Uiso 1 1 calc R
C14 C 0.03022(18) 0.10740(17) 0.3647(2) 0.0313(7) Uani 1 1 d .
H17 H -0.0029 0.1047 0.4241 0.047 Uiso 1 1 calc R
H18 H 0.0820 0.0780 0.3748 0.047 Uiso 1 1 calc R
H19 H 0.0000 0.0820 0.3109 0.047 Uiso 1 1 calc R
C15 C -0.03211(15) 0.24319(16) 0.31925(19) 0.0221(6) Uani 1 1 d .
H20 H -0.0595 0.2182 0.2631 0.033 Uiso 1 1 calc R
H21 H -0.0201 0.3010 0.3051 0.033 Uiso 1 1 calc R
H22 H -0.0681 0.2397 0.3762 0.033 Uiso 1 1 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 0.0033 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'
Si Si 0.0817 0.0704 '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
C4 S1 C1 92.75(11) . .
C2 C1 S1 110.78(18) . .
C2 C1 Si1 128.77(18) . .
S1 C1 Si1 120.29(13) . .
C1 C2 C3 111.8(2) . .
C4 C3 C2 114.7(2) . .
C4 C3 S2 111.22(17) . .
C2 C3 S2 134.04(19) . .
C3 C4 C5 113.1(2) . .
C3 C4 S1 109.94(17) . .
C5 C4 S1 136.96(18) . .
C6 C5 C4 112.70(19) . .
C6 C5 S3 111.59(16) . .
C4 C5 S3 135.70(18) . .
C5 C6 C6 113.03(13) . 2_655
C5 C6 S2 111.33(16) . .
C6 C6 S2 135.43(8) 2_655 .
O2 S2 O1 117.88(10) . .
O2 S2 C3 111.09(11) . .
O1 S2 C3 112.58(11) . .
O2 S2 C6 109.58(11) . .
O1 S2 C6 111.20(10) . .
C3 S2 C6 91.38(11) . .
C5 S3 C5 90.76(15) 2_655 .
C10 Si1 C1 106.80(11) . .
C10 Si1 C7 109.62(12) . .
C1 Si1 C7 106.85(11) . .
C10 Si1 C13 110.84(11) . .
C1 Si1 C13 106.38(11) . .
C7 Si1 C13 115.84(12) . .
C8 C7 C9 111.0(2) . .
C8 C7 Si1 113.3(2) . .
C9 C7 Si1 113.55(18) . .
C11 C10 C12 109.9(2) . .
C11 C10 Si1 112.85(18) . .
C12 C10 Si1 112.29(18) . .
C14 C13 C15 110.0(2) . .
C14 C13 Si1 115.80(18) . .
C15 C13 Si1 111.96(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.707(2) .
S1 C1 1.739(2) .
C1 C2 1.371(3) .
C1 Si1 1.886(2) .
C2 C3 1.410(3) .
C3 C4 1.375(3) .
C3 S2 1.764(2) .
C4 C5 1.459(3) .
C5 C6 1.374(3) .
C5 S3 1.731(2) .
C6 C6 1.388(4) 2_655
C6 S2 1.768(2) .
S2 O2 1.4290(17) .
S2 O1 1.4322(17) .
S3 C5 1.731(2) 2_655
Si1 C10 1.883(3) .
Si1 C7 1.889(3) .
Si1 C13 1.889(2) .
C7 C8 1.523(4) .
C7 C9 1.531(3) .
C10 C11 1.532(4) .
C10 C12 1.541(4) .
C13 C14 1.531(4) .
C13 C15 1.534(3) .
