# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mak1027 _database_code_depnum_ccdc_archive 'CCDC 923201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,5'-Di(5''-tert-butyldimethylsilyl-2''-thienyl)- 3,3'-bi[thiophen-3(2H)-ylidene]-2,2'-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 O2 S4 Si2' _chemical_formula_weight 588.99 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.472(6) _cell_length_b 7.017(6) _cell_length_c 16.835(16) _cell_angle_alpha 82.70(4) _cell_angle_beta 84.68(4) _cell_angle_gamma 78.40(4) _cell_volume 741.0(11) _cell_formula_units_Z 1 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 1039 _cell_measurement_theta_min 2.4449 _cell_measurement_theta_max 31.5050 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9196 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'Jacobson, R. (1998) Provate communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5112 _diffrn_reflns_av_R_equivalents 0.1162 _diffrn_reflns_av_sigmaI/netI 0.1871 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2544 _reflns_number_gt 1256 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1854P)^2^+0.0000P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 2544 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1956 _refine_ls_R_factor_gt 0.1126 _refine_ls_wR_factor_ref 0.3482 _refine_ls_wR_factor_gt 0.2762 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.6358(4) 0.2371(3) 0.37486(16) 0.0263(7) Uani 1 1 d . . . C1 C 0.8512(15) 0.2253(13) 0.4343(6) 0.028(2) Uani 1 1 d . . . C2 C 0.9165(14) 0.0218(12) 0.4758(6) 0.020(2) Uani 1 1 d . . . C3 C 0.7856(15) -0.0994(13) 0.4546(6) 0.022(2) Uani 1 1 d . . . H1 H 0.8036 -0.2346 0.4738 0.027 Uiso 1 1 calc R . . C4 C 0.6329(14) -0.0109(12) 0.4052(6) 0.021(2) Uani 1 1 d . . . O1 O 0.9348(11) 0.3724(9) 0.4357(4) 0.0285(17) Uani 1 1 d . . . S2 S 0.3391(4) 0.0115(3) 0.29190(15) 0.0236(7) Uani 1 1 d . . . C5 C 0.4806(15) -0.0969(14) 0.3738(6) 0.027(2) Uani 1 1 d . . . C6 C 0.4261(15) -0.2838(12) 0.3972(6) 0.022(2) Uani 1 1 d . . . H2 H 0.4865 -0.3706 0.4407 0.027 Uiso 1 1 calc R . . C7 C 0.2782(16) -0.3296(13) 0.3518(6) 0.028(2) Uani 1 1 d . . . H3 H 0.2243 -0.4473 0.3627 0.034 Uiso 1 1 calc R . . C8 C 0.2158(16) -0.1864(13) 0.2885(7) 0.033(3) Uani 1 1 d . . . Si1 Si 0.0535(4) -0.2050(4) 0.20456(16) 0.0217(7) Uani 1 1 d . . . C9 C 0.2352(15) -0.3021(14) 0.1192(6) 0.026(2) Uani 1 1 d . . . C10 C 0.1070(18) -0.3208(17) 0.0488(7) 0.039(3) Uani 1 1 d . . . H4 H 0.2040 -0.3662 0.0039 0.059 Uiso 1 1 calc R . . H5 H 0.0211 -0.1929 0.0316 0.059 Uiso 1 1 calc R . . H6 H 0.0143 -0.4150 0.0661 0.059 Uiso 1 1 calc R . . C11 C 0.3643(17) -0.5026(14) 0.1447(7) 0.036(3) Uani 1 1 d . . . H7 H 0.4435 -0.5571 0.0977 0.054 Uiso 1 1 calc R . . H8 H 0.2696 -0.5896 0.1695 0.054 Uiso 1 1 calc R . . H9 H 0.4634 -0.4906 0.1836 0.054 Uiso 1 1 calc R . . C12 C 0.3895(18) -0.1638(16) 0.0873(7) 0.042(3) Uani 1 1 d . . . H10 H 0.4924 -0.1691 0.1271 0.063 Uiso 1 1 calc R . . H11 H 0.3101 -0.0295 0.0774 0.063 Uiso 1 1 calc R . . H12 H 0.4640 -0.2049 0.0371 0.063 Uiso 1 1 calc R . . C13 C -0.0956(16) 0.0447(13) 0.1715(6) 0.032(2) Uani 1 1 d . . . H13 H -0.1884 0.0363 0.1298 0.047 Uiso 1 1 calc R . . H14 H 0.0043 0.1295 0.1499 0.047 Uiso 1 1 calc R . . H15 H -0.1809 0.0993 0.2174 0.047 Uiso 1 1 calc R . . C14 C -0.1214(17) -0.3799(16) 0.2418(7) 0.042(3) Uani 1 1 d . . . H16 H -0.1936 -0.4071 0.1971 0.064 Uiso 1 1 calc R . . H17 H -0.2265 -0.3233 0.2824 0.064 Uiso 1 1 calc R . . H18 H -0.0369 -0.5020 0.2658 0.064 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 0.0244(14) 0.0197(12) 0.0363(16) -0.0037(11) -0.0139(11) -0.0019(10) C1 0.018(5) 0.023(5) 0.044(7) -0.004(5) -0.010(5) 0.001(4) C2 0.013(5) 0.016(4) 0.030(6) -0.008(4) 0.004(4) 0.004(4) C3 0.022(5) 0.019(5) 0.026(6) 0.001(4) -0.008(4) -0.004(4) C4 0.013(5) 0.018(5) 0.035(6) -0.010(4) 0.006(4) -0.006(4) O1 0.031(4) 0.026(4) 0.030(4) 0.003(3) -0.013(3) -0.008(3) S2 0.0188(13) 0.0181(12) 0.0347(15) -0.0013(10) -0.0077(10) -0.0037(10) C5 0.016(5) 0.035(6) 0.032(6) -0.011(5) -0.003(4) -0.003(4) C6 0.028(6) 0.014(4) 0.027(5) 0.000(4) -0.004(4) -0.009(4) C7 0.025(6) 0.016(4) 0.040(6) 0.003(4) -0.010(5) 0.003(4) C8 0.023(6) 0.018(5) 0.056(8) 0.002(5) -0.001(5) -0.003(4) Si1 0.0157(14) 0.0228(14) 0.0265(16) -0.0019(12) -0.0041(11) -0.0024(11) C9 0.017(5) 0.035(5) 0.026(6) -0.006(5) 0.000(4) -0.005(4) C10 0.041(7) 0.046(6) 0.036(7) -0.018(5) 0.000(5) -0.014(6) C11 0.032(6) 0.036(6) 0.035(7) -0.004(5) 0.003(5) 0.003(5) C12 0.038(7) 0.047(7) 0.044(7) -0.018(6) 0.024(6) -0.021(6) C13 0.028(6) 0.024(5) 0.040(7) -0.007(5) -0.004(5) 0.006(4) C14 0.025(6) 0.052(7) 0.051(8) -0.009(6) 0.002(5) -0.010(6) _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 1.753(9) . ? S1 C1 1.773(10) . ? C1 O1 1.262(10) . ? C1 C2 1.505(13) . ? C2 C2 1.375(18) 2_756 ? C2 C3 1.412(12) . ? C3 C4 1.352(13) . ? C4 C5 1.426(13) . ? S2 C5 1.734(10) . ? S2 C8 1.744(9) . ? C5 C6 1.424(12) . ? C6 C7 1.388(13) . ? C7 C8 1.398(14) . ? C8 Si1 1.869(12) . ? Si1 C14 1.847(10) . ? Si1 C13 1.866(10) . ? Si1 C9 1.878(10) . ? C9 C11 1.517(13) . ? C9 C10 1.542(13) . ? C9 C12 1.545(12) . ? 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 90.4(4) . . ? O1 C1 C2 128.2(9) . . ? O1 C1 S1 121.2(7) . . ? C2 C1 S1 110.6(6) . . ? C2 C2 C3 130.2(11) 2_756 . ? C2 C2 C1 120.6(10) 2_756 . ? C3 C2 C1 109.2(8) . . ? C4 C3 C2 115.8(8) . . ? C3 C4 C5 127.9(9) . . ? C3 C4 S1 114.0(7) . . ? C5 C4 S1 118.1(8) . . ? C5 S2 C8 94.4(5) . . ? C6 C5 C4 128.8(9) . . ? C6 C5 S2 107.7(7) . . ? C4 C5 S2 123.4(7) . . ? C7 C6 C5 115.0(8) . . ? C6 C7 C8 113.7(8) . . ? C7 C8 S2 109.1(8) . . ? C7 C8 Si1 127.5(7) . . ? S2 C8 Si1 123.0(6) . . ? C14 Si1 C13 112.9(5) . . ? C14 Si1 C8 107.7(5) . . ? C13 Si1 C8 108.4(4) . . ? C14 Si1 C9 109.3(5) . . ? C13 Si1 C9 109.8(5) . . ? C8 Si1 C9 108.8(5) . . ? C11 C9 C10 108.1(9) . . ? C11 C9 C12 108.2(8) . . ? C10 C9 C12 107.4(9) . . ? C11 C9 Si1 111.2(7) . . ? C10 C9 Si1 110.4(7) . . ? C12 C9 Si1 111.3(7) . . ? 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 O1 178.2(9) . . . . ? C4 S1 C1 C2 0.9(8) . . . . ? O1 C1 C2 C2 1.8(19) . . . 2_756 ? S1 C1 C2 C2 178.9(10) . . . 2_756 ? O1 C1 C2 C3 -177.0(10) . . . . ? S1 C1 C2 C3 0.1(10) . . . . ? C2 C2 C3 C4 180.0(12) 2_756 . . . ? C1 C2 C3 C4 -1.3(12) . . . . ? C2 C3 C4 C5 179.4(9) . . . . ? C2 C3 C4 S1 2.1(12) . . . . ? C1 S1 C4 C3 -1.7(8) . . . . ? C1 S1 C4 C5 -179.3(8) . . . . ? C3 C4 C5 C6 12.6(17) . . . . ? S1 C4 C5 C6 -170.2(8) . . . . ? C3 C4 C5 S2 -162.6(8) . . . . ? S1 C4 C5 S2 14.6(12) . . . . ? C8 S2 C5 C6 -0.8(8) . . . . ? C8 S2 C5 C4 175.3(9) . . . . ? C4 C5 C6 C7 -176.7(10) . . . . ? S2 C5 C6 C7 -0.9(11) . . . . ? C5 C6 C7 C8 2.7(13) . . . . ? C6 C7 C8 S2 -3.1(12) . . . . ? C6 C7 C8 Si1 170.1(8) . . . . ? C5 S2 C8 C7 2.2(9) . . . . ? C5 S2 C8 Si1 -171.4(7) . . . . ? C7 C8 Si1 C14 28.3(11) . . . . ? S2 C8 Si1 C14 -159.3(7) . . . . ? C7 C8 Si1 C13 150.7(10) . . . . ? S2 C8 Si1 C13 -36.9(8) . . . . ? C7 C8 Si1 C9 -90.0(10) . . . . ? S2 C8 Si1 C9 82.4(7) . . . . ? C14 Si1 C9 C11 -57.6(8) . . . . ? C13 Si1 C9 C11 178.2(7) . . . . ? C8 Si1 C9 C11 59.7(8) . . . . ? C14 Si1 C9 C10 62.4(8) . . . . ? C13 Si1 C9 C10 -61.8(8) . . . . ? C8 Si1 C9 C10 179.7(6) . . . . ? C14 Si1 C9 C12 -178.4(8) . . . . ? C13 Si1 C9 C12 57.4(8) . . . . ? C8 Si1 C9 C12 -61.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.186 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.170