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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/4/10/18/4101804.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_4101804
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         'C28 H36 S6 Si4'
_chemical_formula_sum            'C28 H36 S6 Si4'
_chemical_formula_weight         677.29
_chemical_name_common            2b
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 101.261(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.522(2)
_cell_length_b                   6.2465(8)
_cell_length_c                   16.655(2)
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.49
_cell_volume                     1685.8(4)
_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      298(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5874
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0634P)²+0.5464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                2081
_reflns_number_total             2358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja908161r_si_003.cif
_cod_data_source_block           2b
_cod_database_code               4101804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Si6 Si 0.92104(5) 0.17543(13) 0.74765(5) 0.0380(3) Uani 1 1 d . . .
S2 S 1.04636(5) -0.15650(13) 0.83996(5) 0.0421(3) Uani 1 1 d . . .
S3 S 0.82344(5) -0.49776(13) 1.09865(5) 0.0422(3) Uani 1 1 d . . .
S4 S 0.82633(5) -0.00523(12) 0.92356(5) 0.0415(3) Uani 1 1 d . . .
Si5 Si 0.68806(5) -0.14658(14) 1.07273(6) 0.0405(3) Uani 1 1 d . . .
C5 C 0.90743(16) -0.3430(4) 0.99948(17) 0.0325(7) Uani 1 1 d . . .
C1 C 0.95753(16) -0.2657(5) 0.94252(17) 0.0315(7) Uani 1 1 d . . .
C2 C 0.91931(17) -0.0873(5) 0.89616(18) 0.0351(7) Uani 1 1 d . . .
C6 C 0.83440(17) -0.2154(5) 0.99454(17) 0.0347(7) Uani 1 1 d . . .
C3 C 1.02966(17) -0.3238(5) 0.91821(18) 0.0345(7) Uani 1 1 d . . .
C7 C 0.78158(17) -0.2732(5) 1.04530(18) 0.0375(7) Uani 1 1 d . . .
C8 C 0.91033(17) -0.5072(4) 1.05489(18) 0.0334(7) Uani 1 1 d . . .
C4 C 0.95763(18) -0.0074(5) 0.83615(19) 0.0383(8) Uani 1 1 d . . .
C12 C 0.7207(2) -0.0141(6) 1.1735(2) 0.0599(10) Uani 1 1 d . . .
H1 H 0.7639 0.0867 1.1705 0.090 Uiso 1 1 calc R . .
H2 H 0.7407 -0.1200 1.2144 0.090 Uiso 1 1 calc R . .
H3 H 0.6745 0.0595 1.1878 0.090 Uiso 1 1 calc R . .
C9 C 1.0127(2) 0.2941(6) 0.7153(2) 0.0566(9) Uani 1 1 d . . .
H4 H 0.9953 0.3762 0.6662 0.085 Uiso 1 1 calc R . .
H5 H 1.0491 0.1818 0.7051 0.085 Uiso 1 1 calc R . .
H6 H 1.0412 0.3857 0.7579 0.085 Uiso 1 1 calc R . .
C10 C 0.8637(3) 0.0084(6) 0.6632(2) 0.0646(11) Uani 1 1 d . . .
H7 H 0.8179 -0.0590 0.6806 0.097 Uiso 1 1 calc R . .
H8 H 0.8998 -0.0993 0.6488 0.097 Uiso 1 1 calc R . .
H9 H 0.8438 0.0972 0.6164 0.097 Uiso 1 1 calc R . .
C13 C 0.6443(2) 0.0504(6) 0.9929(3) 0.0636(10) Uani 1 1 d . . .
H10 H 0.6833 0.1638 0.9919 0.095 Uiso 1 1 calc R . .
H11 H 0.5942 0.1085 1.0049 0.095 Uiso 1 1 calc R . .
H12 H 0.6328 -0.0190 0.9405 0.095 Uiso 1 1 calc R . .
C11 C 0.8532(2) 0.3843(6) 0.7771(2) 0.0631(10) Uani 1 1 d . . .
H13 H 0.8033 0.3196 0.7869 0.095 Uiso 1 1 calc R . .
H14 H 0.8400 0.4872 0.7338 0.095 Uiso 1 1 calc R . .
H15 H 0.8811 0.4545 0.8261 0.095 Uiso 1 1 calc R . .
C14 C 0.6115(2) -0.3585(6) 1.0810(3) 0.0788(14) Uani 1 1 d . . .
H16 H 0.5668 -0.2981 1.1026 0.118 Uiso 1 1 calc R . .
H17 H 0.6375 -0.4696 1.1168 0.118 Uiso 1 1 calc R . .
H18 H 0.5906 -0.4174 1.0277 0.118 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
C11 Si6 C10 110.63(19) . . ?
C11 Si6 C9 111.49(19) . . ?
C10 Si6 C9 109.18(19) . . ?
C11 Si6 C4 109.95(16) . . ?
C10 Si6 C4 107.05(17) . . ?
C9 Si6 C4 108.42(15) . . ?
C4 S2 C3 95.41(14) . . ?
C7 S3 C8 95.30(14) . . ?
C6 S4 C2 90.08(14) . . ?
C13 Si5 C14 110.6(2) . . ?
C13 Si5 C12 110.93(19) . . ?
C14 Si5 C12 109.5(2) . . ?
C13 Si5 C7 109.32(16) . . ?
C14 Si5 C7 108.91(16) . . ?
C12 Si5 C7 107.55(16) . . ?
C8 C5 C6 111.8(3) . . ?
C8 C5 C1 137.3(3) . . ?
C6 C5 C1 110.9(2) . . ?
C3 C1 C2 111.2(2) . . ?
C3 C1 C5 137.4(3) . . ?
C2 C1 C5 111.2(2) . . ?
C4 C2 C1 117.2(3) . . ?
C4 C2 S4 129.1(2) . . ?
C1 C2 S4 113.7(2) . . ?
C7 C6 C5 116.5(3) . . ?
C7 C6 S4 129.5(2) . . ?
C5 C6 S4 114.0(2) . . ?
C1 C3 C8 132.4(3) . 3_747 ?
C1 C3 S2 109.6(2) . . ?
C8 C3 S2 118.0(2) 3_747 . ?
C6 C7 S3 106.9(2) . . ?
C6 C7 Si5 133.8(2) . . ?
S3 C7 Si5 118.93(17) . . ?
C5 C8 C3 132.8(3) . 3_747 ?
C5 C8 S3 109.5(2) . . ?
C3 C8 S3 117.7(2) 3_747 . ?
C2 C4 S2 106.5(2) . . ?
C2 C4 Si6 132.1(2) . . ?
S2 C4 Si6 119.99(17) . . ?
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
Si6 C11 1.847(4) . ?
Si6 C10 1.856(4) . ?
Si6 C9 1.858(3) . ?
Si6 C4 1.869(3) . ?
S2 C4 1.728(3) . ?
S2 C3 1.734(3) . ?
S3 C7 1.731(3) . ?
S3 C8 1.733(3) . ?
S4 C6 1.754(3) . ?
S4 C2 1.762(3) . ?
Si5 C13 1.852(4) . ?
Si5 C14 1.854(4) . ?
Si5 C12 1.855(4) . ?
Si5 C7 1.870(3) . ?
C5 C8 1.374(4) . ?
C5 C6 1.435(4) . ?
C5 C1 1.458(4) . ?
C1 C3 1.380(4) . ?
C1 C2 1.431(4) . ?
C2 C4 1.377(4) . ?
C6 C7 1.377(4) . ?
C3 C8 1.458(4) 3_747 ?
C8 C3 1.458(4) 3_747 ?
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
C8 C5 C1 C3 0.8(6) . . . . ?
C6 C5 C1 C3 -177.3(3) . . . . ?
C8 C5 C1 C2 176.8(3) . . . . ?
C6 C5 C1 C2 -1.3(3) . . . . ?
C3 C1 C2 C4 1.2(4) . . . . ?
C5 C1 C2 C4 -175.9(3) . . . . ?
C3 C1 C2 S4 179.6(2) . . . . ?
C5 C1 C2 S4 2.6(3) . . . . ?
C6 S4 C2 C4 175.8(3) . . . . ?
C6 S4 C2 C1 -2.4(2) . . . . ?
C8 C5 C6 C7 1.1(4) . . . . ?
C1 C5 C6 C7 179.7(3) . . . . ?
C8 C5 C6 S4 -179.1(2) . . . . ?
C1 C5 C6 S4 -0.5(3) . . . . ?
C2 S4 C6 C7 -178.6(3) . . . . ?
C2 S4 C6 C5 1.6(2) . . . . ?
C2 C1 C3 C8 -179.3(3) . . . 3_747 ?
C5 C1 C3 C8 -3.4(6) . . . 3_747 ?
C2 C1 C3 S2 0.0(3) . . . . ?
C5 C1 C3 S2 175.9(3) . . . . ?
C4 S2 C3 C1 -0.8(2) . . . . ?
C4 S2 C3 C8 178.6(2) . . . 3_747 ?
C5 C6 C7 S3 -1.5(3) . . . . ?
S4 C6 C7 S3 178.68(19) . . . . ?
C5 C6 C7 Si5 170.9(2) . . . . ?
S4 C6 C7 Si5 -8.9(5) . . . . ?
C8 S3 C7 C6 1.2(2) . . . . ?
C8 S3 C7 Si5 -172.52(18) . . . . ?
C13 Si5 C7 C6 20.3(4) . . . . ?
C14 Si5 C7 C6 141.1(4) . . . . ?
C12 Si5 C7 C6 -100.3(4) . . . . ?
C13 Si5 C7 S3 -168.0(2) . . . . ?
C14 Si5 C7 S3 -47.1(3) . . . . ?
C12 Si5 C7 S3 71.5(2) . . . . ?
C6 C5 C8 C3 -179.7(3) . . . 3_747 ?
C1 C5 C8 C3 2.3(6) . . . 3_747 ?
C6 C5 C8 S3 -0.1(3) . . . . ?
C1 C5 C8 S3 -178.1(3) . . . . ?
C7 S3 C8 C5 -0.7(2) . . . . ?
C7 S3 C8 C3 179.0(2) . . . 3_747 ?
C1 C2 C4 S2 -1.7(3) . . . . ?
S4 C2 C4 S2 -179.9(2) . . . . ?
C1 C2 C4 Si6 164.4(2) . . . . ?
S4 C2 C4 Si6 -13.7(5) . . . . ?
C3 S2 C4 C2 1.4(2) . . . . ?
C3 S2 C4 Si6 -166.74(19) . . . . ?
C11 Si6 C4 C2 37.4(4) . . . . ?
C10 Si6 C4 C2 -82.8(4) . . . . ?
C9 Si6 C4 C2 159.5(3) . . . . ?
C11 Si6 C4 S2 -158.0(2) . . . . ?
C10 Si6 C4 S2 81.8(2) . . . . ?
C9 Si6 C4 S2 -35.9(2) . . . . ?
