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#$Date: 2016-03-21 17:00:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178764 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/18/4101802.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_4101802
loop_
_publ_author_name
'Takeshi Ohmae'
'Tohru Nishinaga'
'Mo Wu'
'Masahiko Iyoda'
_publ_section_title
;
 Cyclic Tetrathiophenes Planarized by Silicon and Sulfur Bridges Bearing
 Antiaromatic Cyclooctatetraene Core: Syntheses, Structures, and
 Properties
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1066
_journal_page_last               1074
_journal_paper_doi               10.1021/ja908161r
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C20 H16 S4 Si2'
_chemical_formula_sum            'C20 H16 S4 Si2'
_chemical_formula_weight         440.75
_chemical_name_common            1
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                   9.0402(4)
_cell_length_b                   9.0402(4)
_cell_length_c                   25.260(3)
_cell_measurement_reflns_used    4966
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.21
_cell_measurement_theta_min      2.39
_cell_volume                     2064.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD aarea detector'
_diffrn_measurement_method       'phi and omega 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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8842
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0280
_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)+(0.0427P)²+0.5198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                1405
_reflns_number_total             1480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja908161r_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        2064.4(2)
_cod_database_code               4101802
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
Si1 Si 0.94954(8) 0.49632(8) 0.10248(3) 0.0485(2) Uani 1 1 d . . .
S2 S 0.91641(8) 0.02764(8) 0.05427(3) 0.0635(2) Uani 1 1 d . . .
S3 S 1.35691(9) 0.59077(8) 0.01307(3) 0.0684(3) Uani 1 1 d . . .
C1 C 1.1655(3) 0.3927(3) 0.03546(8) 0.0400(5) Uani 1 1 d . . .
C2 C 1.0680(3) 0.2651(3) 0.04521(8) 0.0424(6) Uani 1 1 d . . .
C3 C 1.3021(3) 0.4064(3) 0.01138(9) 0.0450(6) Uani 1 1 d . . .
C4 C 1.1143(3) 0.5278(3) 0.05916(9) 0.0460(6) Uani 1 1 d . . .
C9 C 0.7800(3) 0.5953(4) 0.08059(13) 0.0733(9) Uani 1 1 d . . .
H1 H 0.7888 0.6985 0.0890 0.110 Uiso 1 1 calc R . .
H2 H 0.6954 0.5548 0.0984 0.110 Uiso 1 1 calc R . .
H3 H 0.7682 0.5838 0.0431 0.110 Uiso 1 1 calc R . .
C5 C 0.9549(3) 0.2953(3) 0.08451(10) 0.0512(6) Uani 1 1 d . . .
C6 C 1.0559(3) 0.1274(3) 0.02259(9) 0.0423(5) Uani 1 1 d . . .
C7 C 0.8676(3) 0.1758(3) 0.09294(12) 0.0651(8) Uani 1 1 d . . .
H4 H 0.7899 0.1742 0.1170 0.078 Uiso 1 1 calc R . .
C10 C 0.9879(3) 0.5399(3) 0.17305(10) 0.0627(8) Uani 1 1 d . . .
H5 H 1.0610 0.4726 0.1865 0.094 Uiso 1 1 calc R . .
H6 H 0.8985 0.5303 0.1932 0.094 Uiso 1 1 calc R . .
H7 H 1.0242 0.6395 0.1758 0.094 Uiso 1 1 calc R . .
C8 C 1.2061(3) 0.6432(3) 0.04906(11) 0.0606(7) Uani 1 1 d . . .
H8 H 1.1888 0.7395 0.0604 0.073 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'
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
_geom_angle_publ_flag
C10 Si1 C9 109.70(14) . . ?
C10 Si1 C4 112.34(12) . . ?
C9 Si1 C4 114.19(14) . . ?
C10 Si1 C5 115.68(13) . . ?
C9 Si1 C5 114.58(13) . . ?
C4 Si1 C5 89.16(11) . . ?
C7 S2 C6 92.49(12) . . ?
C8 S3 C3 92.96(12) . . ?
C3 C1 C4 113.3(2) . . ?
C3 C1 C2 132.7(2) . . ?
C4 C1 C2 113.8(2) . . ?
C6 C2 C5 113.5(2) . . ?
C6 C2 C1 133.5(2) . . ?
C5 C2 C1 112.9(2) . . ?
C1 C3 C3 134.13(15) . 7_645 ?
C1 C3 S3 109.23(18) . . ?
C3 C3 S3 116.55(9) 7_645 . ?
C8 C4 C1 112.3(2) . . ?
C8 C4 Si1 135.53(19) . . ?
C1 C4 Si1 111.78(17) . . ?
C7 C5 C2 111.6(2) . . ?
C7 C5 Si1 136.1(2) . . ?
C2 C5 Si1 111.47(18) . . ?
C2 C6 C6 133.63(14) . 7_645 ?
C2 C6 S2 109.59(17) . . ?
C6 C6 S2 116.67(10) 7_645 . ?
C5 C7 S2 112.6(2) . . ?
C4 C8 S3 112.0(2) . . ?
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
Si1 C10 1.858(2) . ?
Si1 C9 1.859(3) . ?
Si1 C4 1.870(3) . ?
Si1 C5 1.874(3) . ?
S2 C7 1.715(3) . ?
S2 C6 1.745(2) . ?
S3 C8 1.706(3) . ?
S3 C3 1.740(2) . ?
C1 C3 1.382(3) . ?
C1 C4 1.436(3) . ?
C1 C2 1.472(3) . ?
C2 C6 1.374(3) . ?
C2 C5 1.451(3) . ?
C3 C3 1.452(5) 7_645 ?
C4 C8 1.357(4) . ?
C5 C7 1.354(4) . ?
C6 C6 1.462(5) 7_645 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C6 -21.1(5) . . . . ?
C4 C1 C2 C6 164.6(3) . . . . ?
C3 C1 C2 C5 163.8(2) . . . . ?
C4 C1 C2 C5 -10.5(3) . . . . ?
C4 C1 C3 C3 170.8(3) . . . 7_645 ?
C2 C1 C3 C3 -3.5(5) . . . 7_645 ?
C4 C1 C3 S3 -5.6(2) . . . . ?
C2 C1 C3 S3 -179.9(2) . . . . ?
C8 S3 C3 C1 3.84(19) . . . . ?
C8 S3 C3 C3 -173.3(2) . . . 7_645 ?
C3 C1 C4 C8 5.0(3) . . . . ?
C2 C1 C4 C8 -179.5(2) . . . . ?
C3 C1 C4 Si1 -168.60(16) . . . . ?
C2 C1 C4 Si1 6.8(2) . . . . ?
C10 Si1 C4 C8 -55.4(3) . . . . ?
C9 Si1 C4 C8 70.4(3) . . . . ?
C5 Si1 C4 C8 -172.9(3) . . . . ?
C10 Si1 C4 C1 116.19(18) . . . . ?
C9 Si1 C4 C1 -118.06(19) . . . . ?
C5 Si1 C4 C1 -1.36(18) . . . . ?
C6 C2 C5 C7 4.4(3) . . . . ?
C1 C2 C5 C7 -179.6(2) . . . . ?
C6 C2 C5 Si1 -166.93(18) . . . . ?
C1 C2 C5 Si1 9.1(3) . . . . ?
C10 Si1 C5 C7 72.8(4) . . . . ?
C9 Si1 C5 C7 -56.4(4) . . . . ?
C4 Si1 C5 C7 -172.7(3) . . . . ?
C10 Si1 C5 C2 -118.93(19) . . . . ?
C9 Si1 C5 C2 111.9(2) . . . . ?
C4 Si1 C5 C2 -4.42(19) . . . . ?
C5 C2 C6 C6 169.9(3) . . . 7_645 ?
C1 C2 C6 C6 -5.1(6) . . . 7_645 ?
C5 C2 C6 S2 -5.9(3) . . . . ?
C1 C2 C6 S2 179.1(2) . . . . ?
C7 S2 C6 C2 4.6(2) . . . . ?
C7 S2 C6 C6 -171.9(3) . . . 7_645 ?
C2 C5 C7 S2 -0.7(3) . . . . ?
Si1 C5 C7 S2 167.6(2) . . . . ?
C6 S2 C7 C5 -2.2(3) . . . . ?
C1 C4 C8 S3 -1.9(3) . . . . ?
Si1 C4 C8 S3 169.58(18) . . . . ?
C3 S3 C8 C4 -1.1(2) . . . . ?
