#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/70/1517099.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_1517099
loop_
_publ_author_name
'Shi, Xueliang'
'Burrezo, Paula Mayorga'
'Lee, Sangsu'
'Zhang, Wenhua'
'Zheng, Bin'
'Dai, Gaole'
'Chang, Jingjing'
'López Navarrete, Juan T.'
'Huang, Kuo-Wei'
'Kim, Dongho'
'Casado, Juan'
'Chi, Chunyan'
_publ_section_title
;
 Antiaromatic bisindeno-[n]thienoacenes with small singlet biradical
 characters: syntheses, structures and chain length dependent physical
 properties
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              4490
_journal_paper_doi               10.1039/C4SC01769B
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C40 H50 S Si2'
_chemical_formula_sum            'C40 H50 S Si2'
_chemical_formula_weight         619.04
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-05-19 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.724(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8584(12)
_cell_length_b                   12.3701(8)
_cell_length_c                   15.9959(11)
_cell_measurement_reflns_used    2669
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      67.7
_cell_measurement_theta_min      4.32
_cell_volume                     3609.0(4)
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11612
_diffrn_reflns_theta_full        65.08
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         4.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_T_max  0.9383
_exptl_absorpt_correction_T_min  0.5650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0532
_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)+(0.1007P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                2409
_reflns_number_total             3024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc01769b2.cif
_cod_data_source_block           si
_cod_depositor_comments
'Adding full bibliography for 1517099--1517103.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1517099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S1 S 0.0000 0.72892(6) 0.7500 0.0366(3) Uani 1 2 d S
Si1 Si 0.16747(4) 0.57361(5) 1.09910(4) 0.0290(2) Uani 1 1 d .
C1 C 0.02938(15) 0.82962(18) 0.82792(16) 0.0321(5) Uani 1 1 d .
C2 C 0.01598(14) 0.93845(18) 0.79340(16) 0.0303(5) Uani 1 1 d .
C3 C 0.04305(13) 1.01176(19) 0.86596(15) 0.0301(5) Uani 1 1 d .
C4 C 0.04429(15) 1.1235(2) 0.87286(16) 0.0346(6) Uani 1 1 d .
H4 H 0.0259 1.1675 0.8234 0.042 Uiso 1 1 calc R
C5 C 0.07293(17) 1.1698(2) 0.95357(17) 0.0408(6) Uani 1 1 d .
H5 H 0.0743 1.2463 0.9592 0.049 Uiso 1 1 calc R
C6 C 0.09937(16) 1.1062(2) 1.02569(16) 0.0402(6) Uani 1 1 d .
H6 H 0.1179 1.1396 1.0804 0.048 Uiso 1 1 calc R
C7 C 0.09930(15) 0.9938(2) 1.01963(16) 0.0360(6) Uani 1 1 d .
H7 H 0.1181 0.9502 1.0692 0.043 Uiso 1 1 calc R
C8 C 0.07121(14) 0.94776(19) 0.93969(16) 0.0320(5) Uani 1 1 d .
C9 C 0.06346(14) 0.83192(19) 0.91419(15) 0.0319(5) Uani 1 1 d .
C10 C 0.09090(15) 0.74519(19) 0.97085(15) 0.0327(6) Uani 1 1 d .
C11 C 0.11881(14) 0.67507(19) 1.02106(15) 0.0329(5) Uani 1 1 d .
C12 C 0.11067(15) 0.5559(2) 1.17950(16) 0.0349(6) Uani 1 1 d .
H12 H 0.1348 0.4999 1.2225 0.042 Uiso 1 1 calc R
C13 C 0.03335(17) 0.5154(2) 1.13368(19) 0.0457(7) Uani 1 1 d .
H13A H 0.0036 0.5101 1.1756 0.069 Uiso 1 1 calc R
H13B H 0.0369 0.4441 1.1084 0.069 Uiso 1 1 calc R
H13C H 0.0103 0.5663 1.0879 0.069 Uiso 1 1 calc R
C14 C 0.10576(17) 0.6611(2) 1.22853(18) 0.0442(7) Uani 1 1 d .
H14A H 0.0860 0.7187 1.1871 0.066 Uiso 1 1 calc R
H14B H 0.1548 0.6815 1.2628 0.066 Uiso 1 1 calc R
H14C H 0.0734 0.6503 1.2670 0.066 Uiso 1 1 calc R
C15 C 0.26280(15) 0.6272(2) 1.14912(17) 0.0388(6) Uani 1 1 d .
H15 H 0.2941 0.6036 1.1105 0.047 Uiso 1 1 calc R
C16 C 0.29711(18) 0.5779(3) 1.23818(19) 0.0534(8) Uani 1 1 d .
H16A H 0.3484 0.6010 1.2580 0.080 Uiso 1 1 calc R
H16B H 0.2950 0.4989 1.2340 0.080 Uiso 1 1 calc R
H16C H 0.2699 0.6023 1.2794 0.080 Uiso 1 1 calc R
C17 C 0.26735(19) 0.7509(3) 1.1531(2) 0.0521(8) Uani 1 1 d .
H17A H 0.2364 0.7782 1.1892 0.078 Uiso 1 1 calc R
H17B H 0.2503 0.7806 1.0946 0.078 Uiso 1 1 calc R
H17C H 0.3183 0.7730 1.1781 0.078 Uiso 1 1 calc R
C18 C 0.17076(16) 0.44435(19) 1.03752(17) 0.0365(6) Uani 1 1 d .
H18 H 0.1199 0.4143 1.0210 0.044 Uiso 1 1 calc R
C19 C 0.2198(2) 0.3592(2) 1.0932(2) 0.0560(8) Uani 1 1 d .
H19A H 0.2147 0.2904 1.0618 0.084 Uiso 1 1 calc R
H19B H 0.2051 0.3495 1.1473 0.084 Uiso 1 1 calc R
H19C H 0.2710 0.3830 1.1063 0.084 Uiso 1 1 calc R
C20 C 0.1941(2) 0.4632(3) 0.95373(19) 0.0508(7) Uani 1 1 d .
H20A H 0.2437 0.4936 0.9674 0.076 Uiso 1 1 calc R
H20B H 0.1600 0.5137 0.9168 0.076 Uiso 1 1 calc R
H20C H 0.1936 0.3943 0.9233 0.076 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 0.0181 0.0091 '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 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 S1 C1 89.21(16) 2_556
C11 Si1 C12 105.68(12) .
C11 Si1 C18 107.48(11) .
C12 Si1 C18 110.94(12) .
C11 Si1 C15 107.69(12) .
C12 Si1 C15 113.33(12) .
C18 Si1 C15 111.34(12) .
C9 C1 C2 110.9(2) .
C9 C1 S1 135.79(19) .
C2 C1 S1 113.33(18) .
C2 C2 C1 112.06(14) 2_556
C2 C2 C3 141.57(13) 2_556
C1 C2 C3 106.4(2) .
C4 C3 C8 119.9(2) .
C4 C3 C2 132.7(2) .
C8 C3 C2 107.3(2) .
C3 C4 C5 118.7(2) .
C3 C4 H4 120.7 .
C5 C4 H4 120.7 .
C6 C5 C4 120.9(2) .
C6 C5 H5 119.6 .
C4 C5 H5 119.6 .
C5 C6 C7 121.1(2) .
C5 C6 H6 119.4 .
C7 C6 H6 119.4 .
C8 C7 C6 118.1(2) .
C8 C7 H7 121.0 .
C6 C7 H7 121.0 .
C7 C8 C3 121.3(2) .
C7 C8 C9 129.9(2) .
C3 C8 C9 108.8(2) .
C1 C9 C10 129.2(2) .
C1 C9 C8 106.6(2) .
C10 C9 C8 124.1(2) .
C11 C10 C9 175.5(3) .
C10 C11 Si1 175.9(2) .
C14 C12 C13 110.2(2) .
C14 C12 Si1 111.63(18) .
C13 C12 Si1 110.29(17) .
C14 C12 H12 108.2 .
C13 C12 H12 108.2 .
Si1 C12 H12 108.2 .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C12 C14 H14A 109.5 .
C12 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C12 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C17 C15 C16 110.6(2) .
C17 C15 Si1 113.9(2) .
C16 C15 Si1 112.6(2) .
C17 C15 H15 106.4 .
C16 C15 H15 106.4 .
Si1 C15 H15 106.4 .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C15 C17 H17A 109.5 .
C15 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C15 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C19 C18 C20 110.4(3) .
C19 C18 Si1 112.00(19) .
C20 C18 Si1 112.51(18) .
C19 C18 H18 107.2 .
C20 C18 H18 107.2 .
Si1 C18 H18 107.2 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C18 C20 H20A 109.5 .
C18 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C18 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.750(2) 2_556
S1 C1 1.750(2) .
Si1 C11 1.842(2) .
Si1 C12 1.884(3) .
Si1 C18 1.887(2) .
Si1 C15 1.892(3) .
C1 C9 1.366(4) .
C1 C2 1.453(3) .
C2 C2 1.366(5) 2_556
C2 C3 1.459(3) .
C3 C4 1.386(4) .
C3 C8 1.408(3) .
C4 C5 1.390(4) .
C4 H4 0.9500 .
C5 C6 1.381(4) .
C5 H5 0.9500 .
C6 C7 1.394(4) .
C6 H6 0.9500 .
C7 C8 1.377(4) .
C7 H7 0.9500 .
C8 C9 1.487(3) .
C9 C10 1.415(3) .
C10 C11 1.208(4) .
C12 C14 1.535(4) .
C12 C13 1.540(4) .
C12 H12 1.0000 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C17 1.533(4) .
C15 C16 1.534(4) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.530(4) .
C18 C20 1.531(4) .
C18 H18 1.0000 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
