# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 loop_ _publ_author_name 'Yali Qiao.' 'Zhongming Wei.' 'Chad Risko' 'Hong Li.' 'Jean-Luc Bridas' 'Wei Xu.' 'Daoben Zhu.' #TrackingRef 'Compd._DBT-CM.cif' _publ_contact_author 'Yali Qiao' _publ_contact_author_email qiaoyl@iccas.ac.cn data_r90106g _database_code_depnum_ccdc_archive 'CCDC 838083' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z, Z)-cyclo[2](dibenzo[b,d]thiophen-2, 8-yl-ethylene) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H16 S2' _chemical_formula_weight 416.53 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.339(3) _cell_length_b 4.7480(9) _cell_length_c 16.949(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.06(3) _cell_angle_gamma 90.00 _cell_volume 932.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3095 _cell_measurement_theta_min 1.757 _cell_measurement_theta_max 27.876 _exptl_crystal_description rod-like _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8817 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1653 _reflns_number_gt 1550 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.3649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1653 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.05482(3) 0.54416(9) 0.41909(3) 0.02532(17) Uani 1 1 d . . . C1 C 0.14683(14) 0.3784(4) 0.37470(10) 0.0219(4) Uani 1 1 d . . . C2 C 0.26181(14) 0.4702(3) 0.41029(10) 0.0187(4) Uani 1 1 d . . . C3 C 0.27523(13) 0.6770(3) 0.47637(9) 0.0185(4) Uani 1 1 d . . . C4 C 0.17050(14) 0.7292(3) 0.48920(10) 0.0221(4) Uani 1 1 d . . . C5 C 0.16704(15) 0.9096(4) 0.55351(11) 0.0244(4) Uani 1 1 d . . . H5 H 0.0975 0.9513 0.5608 0.029 Uiso 1 1 calc R . . C6 C 0.26863(15) 1.0236(3) 0.60561(11) 0.0237(4) Uani 1 1 d . . . H6 H 0.2666 1.1415 0.6489 0.028 Uiso 1 1 calc R . . C7 C 0.37708(14) 0.9689(3) 0.59618(10) 0.0197(4) Uani 1 1 d . . . C8 C 0.37630(13) 0.8041(3) 0.52823(9) 0.0189(4) Uani 1 1 d . . . H8 H 0.4444 0.7782 0.5172 0.023 Uiso 1 1 calc R . . C9 C 0.47772(15) 1.0943(3) 0.66078(10) 0.0221(4) Uani 1 1 d . . . H9 H 0.4558 1.2394 0.6890 0.026 Uiso 1 1 calc R . . C10 C 0.59336(15) 1.0568(3) 0.69052(10) 0.0214(4) Uani 1 1 d . . . H10 H 0.6288 1.1729 0.7363 0.026 Uiso 1 1 calc R . . C11 C 0.67804(14) 0.8816(3) 0.66974(9) 0.0198(4) Uani 1 1 d . . . C12 C 0.79569(15) 0.9585(3) 0.70731(10) 0.0221(4) Uani 1 1 d . . . H12 H 0.8149 1.1003 0.7476 0.027 Uiso 1 1 calc R . . C13 C 0.88270(14) 0.8314(4) 0.68637(10) 0.0232(4) Uani 1 1 d . . . H13 H 0.9592 0.8846 0.7124 0.028 Uiso 1 1 calc R . . C14 C 0.65279(14) 0.6546(3) 0.61419(9) 0.0190(4) Uani 1 1 d . . . H14 H 0.5778 0.5857 0.5932 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0196(3) 0.0284(3) 0.0251(3) -0.00073(17) 0.00401(19) 0.00079(17) C1 0.0231(8) 0.0212(8) 0.0182(8) 0.0045(7) 0.0030(7) 0.0016(7) C2 0.0226(8) 0.0157(8) 0.0160(8) 0.0042(6) 0.0042(6) -0.0014(6) C3 0.0238(8) 0.0152(8) 0.0159(8) 0.0034(6) 0.0059(6) 0.0016(6) C4 0.0213(8) 0.0212(8) 0.0214(8) 0.0044(7) 0.0042(7) 0.0020(7) C5 0.0246(9) 0.0258(9) 0.0245(9) 0.0030(7) 0.0107(7) 0.0065(7) C6 0.0319(9) 0.0201(8) 0.0206(8) 0.0003(7) 0.0109(7) 0.0040(7) C7 0.0269(9) 0.0142(8) 0.0183(8) 0.0024(6) 0.0080(7) 0.0002(7) C8 0.0223(8) 0.0165(8) 0.0185(8) 0.0022(6) 0.0078(6) 0.0007(7) C9 0.0329(9) 0.0172(8) 0.0185(8) -0.0027(7) 0.0119(7) -0.0013(7) C10 0.0307(9) 0.0180(8) 0.0155(8) -0.0038(6) 0.0078(7) -0.0061(7) C11 0.0266(9) 0.0181(8) 0.0136(7) 0.0043(6) 0.0053(6) -0.0013(7) C12 0.0290(9) 0.0180(8) 0.0147(8) 0.0004(6) 0.0016(7) -0.0038(7) C13 0.0220(8) 0.0225(9) 0.0192(8) 0.0025(7) -0.0006(6) -0.0029(7) C14 0.0221(8) 0.0173(8) 0.0156(7) 0.0028(6) 0.0039(6) -0.0024(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S1 C4 1.7486(17) . ? S1 C1 1.7494(18) . ? C1 C13 1.392(2) 3_666 ? C1 C2 1.407(2) . ? C2 C14 1.390(2) 3_666 ? C2 C3 1.455(2) . ? C3 C8 1.393(2) . ? C3 C4 1.404(2) . ? C4 C5 1.398(2) . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C6 C7 1.425(2) . ? C6 H6 0.9300 . ? C7 C8 1.390(2) . ? C7 C9 1.471(2) . ? C8 H8 0.9300 . ? C9 C10 1.352(2) . ? C9 H9 0.9300 . ? C10 C11 1.470(2) . ? C10 H10 0.9300 . ? C11 C14 1.394(2) . ? C11 C12 1.419(2) . ? C12 C13 1.380(2) . ? C12 H12 0.9300 . ? C13 C1 1.392(2) 3_666 ? C13 H13 0.9300 . ? C14 C2 1.391(2) 3_666 ? C14 H14 0.9300 . ? 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 C4 S1 C1 91.11(8) . . ? C13 C1 C2 120.58(16) 3_666 . ? C13 C1 S1 126.78(13) 3_666 . ? C2 C1 S1 112.58(12) . . ? C14 C2 C1 119.74(15) 3_666 . ? C14 C2 C3 128.25(15) 3_666 . ? C1 C2 C3 111.76(15) . . ? C8 C3 C4 119.87(14) . . ? C8 C3 C2 128.23(14) . . ? C4 C3 C2 111.74(14) . . ? C5 C4 C3 120.31(15) . . ? C5 C4 S1 126.97(13) . . ? C3 C4 S1 112.71(12) . . ? C6 C5 C4 118.54(15) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 122.78(16) . . ? C5 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C8 C7 C6 117.11(15) . . ? C8 C7 C9 127.52(15) . . ? C6 C7 C9 115.37(15) . . ? C7 C8 C3 121.15(15) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C10 C9 C7 137.56(15) . . ? C10 C9 H9 111.2 . . ? C7 C9 H9 111.2 . . ? C9 C10 C11 136.99(15) . . ? C9 C10 H10 111.5 . . ? C11 C10 H10 111.5 . . ? C14 C11 C12 117.36(15) . . ? C14 C11 C10 125.93(15) . . ? C12 C11 C10 116.66(14) . . ? C13 C12 C11 122.58(15) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C12 C13 C1 118.42(15) . 3_666 ? C12 C13 H13 120.8 . . ? C1 C13 H13 120.8 3_666 . ? C2 C14 C11 120.94(15) 3_666 . ? C2 C14 H14 119.5 3_666 . ? C11 C14 H14 119.5 . . ? 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 C4 S1 C1 C13 174.97(15) . . . 3_666 ? C4 S1 C1 C2 -2.24(13) . . . . ? C13 C1 C2 C14 -1.6(2) 3_666 . . 3_666 ? S1 C1 C2 C14 175.78(12) . . . 3_666 ? C13 C1 C2 C3 -176.36(14) 3_666 . . . ? S1 C1 C2 C3 1.05(17) . . . . ? C14 C2 C3 C8 2.4(3) 3_666 . . . ? C1 C2 C3 C8 176.58(15) . . . . ? C14 C2 C3 C4 -173.04(15) 3_666 . . . ? C1 C2 C3 C4 1.14(19) . . . . ? C8 C3 C4 C5 0.4(2) . . . . ? C2 C3 C4 C5 176.23(14) . . . . ? C8 C3 C4 S1 -178.71(12) . . . . ? C2 C3 C4 S1 -2.83(17) . . . . ? C1 S1 C4 C5 -176.08(15) . . . . ? C1 S1 C4 C3 2.91(13) . . . . ? C3 C4 C5 C6 -2.8(2) . . . . ? S1 C4 C5 C6 176.16(13) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C8 3.3(2) . . . . ? C5 C6 C7 C9 -176.31(15) . . . . ? C6 C7 C8 C3 -5.8(2) . . . . ? C9 C7 C8 C3 173.82(15) . . . . ? C4 C3 C8 C7 4.1(2) . . . . ? C2 C3 C8 C7 -171.04(15) . . . . ? C8 C7 C9 C10 -18.3(3) . . . . ? C6 C7 C9 C10 161.28(19) . . . . ? C7 C9 C10 C11 4.6(4) . . . . ? C9 C10 C11 C14 -11.2(3) . . . . ? C9 C10 C11 C12 166.14(19) . . . . ? C14 C11 C12 C13 4.7(2) . . . . ? C10 C11 C12 C13 -172.91(15) . . . . ? C11 C12 C13 C1 0.7(2) . . . 3_666 ? C12 C11 C14 C2 -7.0(2) . . . 3_666 ? C10 C11 C14 C2 170.36(15) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.208 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.048 data_a _database_code_depnum_ccdc_archive 'CCDC 838084' _audit_creation_method SHELXL-97 _chemical_name_systematic '(Z)-1, 2-bis(dibenzo[b,d]thiophen-2-yl)ethene' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H16 S2' _chemical_formula_weight 392.51 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.924(4) _cell_length_b 6.2925(13) _cell_length_c 7.9164(16) _cell_angle_alpha 90.00 _cell_angle_beta 99.48(3) _cell_angle_gamma 90.00 _cell_volume 929.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2406 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7994 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2127 _reflns_number_gt 1775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELX-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+1.0701P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2127 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.27290(5) 0.46520(13) 0.25228(10) 0.0385(2) Uani 1 1 d . . . C1 C 0.32741(16) 0.6512(5) 0.3762(4) 0.0332(7) Uani 1 1 d . . . C2 C 0.40012(18) 0.6294(6) 0.4367(4) 0.0440(8) Uani 1 1 d . . . H2 H 0.4256 0.5072 0.4097 0.053 Uiso 1 1 calc R . . C3 C 0.43442(18) 0.7896(6) 0.5371(4) 0.0478(9) Uani 1 1 d . . . H3 H 0.4841 0.7770 0.5808 0.057 Uiso 1 1 calc R . . C4 C 0.39716(17) 0.9703(5) 0.5757(4) 0.0420(8) Uani 1 1 d . . . H4 H 0.4217 1.0790 0.6453 0.050 Uiso 1 1 calc R . . C5 C 0.32539(16) 0.9916(5) 0.5135(4) 0.0334(7) Uani 1 1 d . . . H5 H 0.3005 1.1156 0.5393 0.040 Uiso 1 1 calc R . . C6 C 0.28894(15) 0.8323(4) 0.4128(3) 0.0281(6) Uani 1 1 d . . . C7 C 0.21412(15) 0.8186(4) 0.3383(3) 0.0290(6) Uani 1 1 d . . . C8 C 0.19782(16) 0.6269(5) 0.2482(4) 0.0318(6) Uani 1 1 d . . . C9 C 0.12887(17) 0.5839(5) 0.1629(4) 0.0361(7) Uani 1 1 d . . . H9 H 0.1188 0.4563 0.0993 0.043 Uiso 1 1 calc R . . C10 C 0.07556(16) 0.7308(5) 0.1729(4) 0.0352(7) Uani 1 1 d . . . H10 H 0.0282 0.7012 0.1172 0.042 Uiso 1 1 calc R . . C11 C 0.08922(15) 0.9232(5) 0.2632(4) 0.0317(6) Uani 1 1 d . . . C12 C 0.15905(15) 0.9648(4) 0.3443(4) 0.0295(6) Uani 1 1 d . . . H12 H 0.1693 1.0947 0.4045 0.035 Uiso 1 1 calc R . . C13 C 0.03573(15) 1.0935(5) 0.2602(4) 0.0374(7) Uani 1 1 d . . . H13 H 0.0562 1.2314 0.2761 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0485(5) 0.0309(4) 0.0393(4) -0.0016(3) 0.0161(4) 0.0098(3) C1 0.0411(17) 0.0339(16) 0.0263(14) 0.0068(12) 0.0104(12) 0.0119(13) C2 0.0438(19) 0.050(2) 0.0392(17) 0.0084(16) 0.0099(15) 0.0219(16) C3 0.0343(18) 0.066(2) 0.0407(19) 0.0028(17) 0.0000(14) 0.0177(17) C4 0.0408(18) 0.049(2) 0.0331(17) -0.0002(14) -0.0016(13) 0.0080(15) C5 0.0348(16) 0.0359(17) 0.0301(15) 0.0015(12) 0.0069(12) 0.0079(12) C6 0.0326(15) 0.0311(15) 0.0218(13) 0.0050(11) 0.0084(11) 0.0066(12) C7 0.0351(16) 0.0277(14) 0.0254(14) 0.0030(11) 0.0082(12) 0.0013(12) C8 0.0399(17) 0.0263(15) 0.0328(15) 0.0026(12) 0.0163(13) 0.0031(12) C9 0.0475(18) 0.0312(16) 0.0329(15) -0.0033(13) 0.0162(13) -0.0058(13) C10 0.0334(16) 0.0350(16) 0.0386(17) -0.0023(13) 0.0097(13) -0.0065(13) C11 0.0285(15) 0.0325(16) 0.0361(15) 0.0039(13) 0.0109(12) 0.0008(12) C12 0.0327(15) 0.0242(14) 0.0325(15) -0.0004(12) 0.0076(12) -0.0011(11) C13 0.0332(16) 0.0330(16) 0.0464(17) -0.0009(14) 0.0080(14) -0.0005(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S1 C8 1.744(3) . ? S1 C1 1.750(3) . ? C1 C2 1.387(4) . ? C1 C6 1.408(4) . ? C2 C3 1.378(5) . ? C2 H2 0.9500 . ? C3 C4 1.398(4) . ? C3 H3 0.9500 . ? C4 C5 1.373(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.444(4) . ? C7 C12 1.397(4) . ? C7 C8 1.409(4) . ? C8 C9 1.393(4) . ? C9 C10 1.380(4) . ? C9 H9 0.9500 . ? C10 C11 1.408(4) . ? C10 H10 0.9500 . ? C11 C12 1.395(4) . ? C11 C13 1.472(4) . ? C12 H12 0.9500 . ? C13 C13 1.335(6) 2 ? C13 H13 0.9500 . ? 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 C8 S1 C1 91.34(14) . . ? C2 C1 C6 121.7(3) . . ? C2 C1 S1 125.9(2) . . ? C6 C1 S1 112.3(2) . . ? C3 C2 C1 118.2(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 118.5(3) . . ? C5 C6 C7 129.6(3) . . ? C1 C6 C7 111.9(3) . . ? C12 C7 C8 118.6(3) . . ? C12 C7 C6 129.3(3) . . ? C8 C7 C6 112.1(3) . . ? C9 C8 C7 121.4(3) . . ? C9 C8 S1 126.2(2) . . ? C7 C8 S1 112.4(2) . . ? C10 C9 C8 118.5(3) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 122.0(3) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C12 C11 C10 118.4(3) . . ? C12 C11 C13 117.9(3) . . ? C10 C11 C13 123.4(3) . . ? C11 C12 C7 121.1(3) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? C13 C13 C11 133.01(17) 2 . ? C13 C13 H13 113.5 2 . ? C11 C13 H13 113.5 . . ? 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 S1 C1 C2 179.0(3) . . . . ? C8 S1 C1 C6 -0.2(2) . . . . ? C6 C1 C2 C3 0.9(5) . . . . ? S1 C1 C2 C3 -178.1(3) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C4 C5 C6 C7 178.2(3) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? S1 C1 C6 C5 178.7(2) . . . . ? C2 C1 C6 C7 -179.3(3) . . . . ? S1 C1 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C12 1.9(5) . . . . ? C1 C6 C7 C12 -179.5(3) . . . . ? C5 C6 C7 C8 -178.3(3) . . . . ? C1 C6 C7 C8 0.4(3) . . . . ? C12 C7 C8 C9 1.4(4) . . . . ? C6 C7 C8 C9 -178.4(3) . . . . ? C12 C7 C8 S1 179.4(2) . . . . ? C6 C7 C8 S1 -0.5(3) . . . . ? C1 S1 C8 C9 178.2(3) . . . . ? C1 S1 C8 C7 0.4(2) . . . . ? C7 C8 C9 C10 -2.1(4) . . . . ? S1 C8 C9 C10 -179.8(2) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C9 C10 C11 C13 172.8(3) . . . . ? C10 C11 C12 C7 -0.8(4) . . . . ? C13 C11 C12 C7 -173.9(3) . . . . ? C8 C7 C12 C11 0.1(4) . . . . ? C6 C7 C12 C11 179.9(3) . . . . ? C12 C11 C13 C13 -158.3(5) . . . 2 ? C10 C11 C13 C13 29.0(7) . . . 2 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.276 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.060 data_sa441 _database_code_depnum_ccdc_archive 'CCDC 838085' _audit_creation_method SHELXL-97 _chemical_name_systematic '(E)-1, 2-bis(dibenzo[b,d]thiophen-2-yl)ethene' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 S2' _chemical_formula_sum 'C26 H16 S2' _chemical_formula_weight 392.51 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7920(15) _cell_length_b 10.677(2) _cell_length_c 12.729(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.719(4) _cell_angle_gamma 90.00 _cell_volume 914.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 697 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9127 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11960 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2101 _reflns_number_gt 2007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+0.9357P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2101 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 S1 S 0.71929(9) 0.20509(6) 0.60242(5) 0.02886(18) Uani 1 1 d . . . C1 C 0.6945(3) 0.3099(2) 0.70546(19) 0.0261(5) Uani 1 1 d . . . C2 C 0.5424(4) 0.3101(2) 0.7689(2) 0.0306(6) Uani 1 1 d . . . H2A H 0.4428 0.2470 0.7613 0.037 Uiso 1 1 calc R . . C3 C 0.5404(4) 0.4044(3) 0.8431(2) 0.0331(6) Uani 1 1 d . . . H3A H 0.4379 0.4061 0.8870 0.040 Uiso 1 1 calc R . . C4 C 0.6863(4) 0.4969(3) 0.8544(2) 0.0329(6) Uani 1 1 d . . . H4A H 0.6823 0.5608 0.9060 0.040 Uiso 1 1 calc R . . C5 C 0.8371(4) 0.4967(2) 0.7913(2) 0.0297(5) Uani 1 1 d . . . H5A H 0.9358 0.5602 0.7994 0.036 Uiso 1 1 calc R . . C6 C 0.8433(3) 0.4026(2) 0.71571(18) 0.0252(5) Uani 1 1 d . . . C7 C 0.9821(3) 0.3858(2) 0.64018(18) 0.0241(5) Uani 1 1 d . . . C8 C 0.9316(3) 0.2836(2) 0.57260(19) 0.0250(5) Uani 1 1 d . . . C9 C 1.0422(4) 0.2539(2) 0.4917(2) 0.0285(5) Uani 1 1 d . . . H9A H 1.0058 0.1852 0.4458 0.034 Uiso 1 1 calc R . . C10 C 1.2059(3) 0.3264(2) 0.47954(19) 0.0281(5) Uani 1 1 d . . . H10A H 1.2825 0.3063 0.4247 0.034 Uiso 1 1 calc R . . C11 C 1.2629(3) 0.4297(2) 0.54630(18) 0.0240(5) Uani 1 1 d . . . C12 C 1.1484(3) 0.4577(2) 0.62587(19) 0.0256(5) Uani 1 1 d . . . H12A H 1.1838 0.5269 0.6714 0.031 Uiso 1 1 calc R . . C13 C 1.4366(3) 0.5070(2) 0.53531(19) 0.0272(5) Uani 1 1 d . . . H13A H 1.4619 0.5745 0.5838 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0259(3) 0.0284(3) 0.0335(4) -0.0006(3) 0.0083(2) -0.0042(2) C1 0.0241(11) 0.0282(12) 0.0259(12) 0.0048(10) 0.0027(9) 0.0002(9) C2 0.0260(12) 0.0334(14) 0.0328(14) 0.0058(11) 0.0059(10) -0.0012(10) C3 0.0300(13) 0.0418(15) 0.0290(13) 0.0062(11) 0.0097(10) 0.0020(11) C4 0.0339(13) 0.0366(14) 0.0293(14) -0.0015(11) 0.0077(11) 0.0029(11) C5 0.0272(12) 0.0314(13) 0.0304(13) 0.0009(10) 0.0033(10) 0.0002(10) C6 0.0223(11) 0.0287(12) 0.0242(12) 0.0049(10) 0.0022(9) 0.0012(9) C7 0.0222(11) 0.0252(12) 0.0249(12) 0.0022(9) 0.0030(9) 0.0022(9) C8 0.0218(11) 0.0249(12) 0.0286(12) 0.0040(10) 0.0048(9) -0.0003(9) C9 0.0307(13) 0.0235(12) 0.0321(13) -0.0026(10) 0.0061(10) -0.0022(10) C10 0.0254(12) 0.0316(13) 0.0285(13) 0.0012(10) 0.0082(10) 0.0024(10) C11 0.0213(11) 0.0255(12) 0.0251(12) 0.0054(9) 0.0032(9) 0.0008(9) C12 0.0238(11) 0.0262(12) 0.0265(12) 0.0015(10) 0.0023(9) -0.0002(9) C13 0.0256(12) 0.0267(12) 0.0290(13) 0.0012(9) 0.0026(9) 0.0003(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S1 C1 1.749(3) . ? S1 C8 1.753(2) . ? C1 C2 1.394(3) . ? C1 C6 1.409(3) . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.393(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(3) . ? C4 H4A 0.9500 . ? C5 C6 1.395(3) . ? C5 H5A 0.9500 . ? C6 C7 1.445(3) . ? C7 C12 1.397(3) . ? C7 C8 1.404(3) . ? C8 C9 1.390(3) . ? C9 C10 1.380(3) . ? C9 H9A 0.9500 . ? C10 C11 1.414(3) . ? C10 H10A 0.9500 . ? C11 C12 1.390(3) . ? C11 C13 1.462(3) . ? C12 H12A 0.9500 . ? C13 C13 1.334(5) 3_866 ? C13 H13A 0.9500 . ? 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 C1 S1 C8 91.24(11) . . ? C2 C1 C6 121.6(2) . . ? C2 C1 S1 126.1(2) . . ? C6 C1 S1 112.26(17) . . ? C3 C2 C1 118.3(2) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.7(2) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 129.1(2) . . ? C1 C6 C7 112.0(2) . . ? C12 C7 C8 118.8(2) . . ? C12 C7 C6 129.0(2) . . ? C8 C7 C6 112.1(2) . . ? C9 C8 C7 121.3(2) . . ? C9 C8 S1 126.39(19) . . ? C7 C8 S1 112.30(17) . . ? C10 C9 C8 118.6(2) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C9 C10 C11 122.0(2) . . ? C9 C10 H10A 119.0 . . ? C11 C10 H10A 119.0 . . ? C12 C11 C10 118.1(2) . . ? C12 C11 C13 119.1(2) . . ? C10 C11 C13 122.8(2) . . ? C11 C12 C7 121.2(2) . . ? C11 C12 H12A 119.4 . . ? C7 C12 H12A 119.4 . . ? C13 C13 C11 127.2(3) 3_866 . ? C13 C13 H13A 116.4 3_866 . ? C11 C13 H13A 116.4 . . ? 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 S1 C1 C2 177.4(2) . . . . ? C8 S1 C1 C6 0.58(18) . . . . ? C6 C1 C2 C3 0.0(4) . . . . ? S1 C1 C2 C3 -176.48(19) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C4 C5 C6 C7 178.2(2) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? S1 C1 C6 C5 176.89(18) . . . . ? C2 C1 C6 C7 -178.5(2) . . . . ? S1 C1 C6 C7 -1.5(3) . . . . ? C5 C6 C7 C12 2.0(4) . . . . ? C1 C6 C7 C12 -179.8(2) . . . . ? C5 C6 C7 C8 -176.3(2) . . . . ? C1 C6 C7 C8 1.9(3) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C6 C7 C8 C9 177.7(2) . . . . ? C12 C7 C8 S1 -179.93(18) . . . . ? C6 C7 C8 S1 -1.5(3) . . . . ? C1 S1 C8 C9 -178.6(2) . . . . ? C1 S1 C8 C7 0.52(18) . . . . ? C7 C8 C9 C10 0.8(4) . . . . ? S1 C8 C9 C10 179.91(19) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C9 C10 C11 C13 179.5(2) . . . . ? C10 C11 C12 C7 0.3(3) . . . . ? C13 C11 C12 C7 -179.4(2) . . . . ? C8 C7 C12 C11 0.2(3) . . . . ? C6 C7 C12 C11 -178.0(2) . . . . ? C12 C11 C13 C13 179.3(3) . . . 3_866 ? C10 C11 C13 C13 -0.4(5) . . . 3_866 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.331 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.055