Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # 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_so19feb _database_code_depnum_ccdc_archive 'CCDC 640193' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H32 N2 S2 Si' _chemical_formula_weight 380.68 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' N N 0.0311 0.0180 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.535(3) _cell_length_b 14.525(3) _cell_length_c 13.464(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.28(1) _cell_angle_gamma 90.00 _cell_volume 2142.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8488 _cell_measurement_theta_min 8.064 _cell_measurement_theta_max 117.810 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 2.798 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5635 _exptl_absorpt_correction_T_max 0.7516 _exptl_absorpt_process_details SADABS-2006/4 _exptl_special_details ; Intensities were measured with a SMART 6000 area detector ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'mirror system' _diffrn_measurement_device_type 'Bruker three circle diffractometer' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean 5.602 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22537 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 59.08 _reflns_number_total 3066 _reflns_number_gt 2871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Proteum (v 1.40, Bruker 2002)' _computing_cell_refinement 'Bruker AXS SAINT (v 7.01A, Bruker 2003)' _computing_data_reduction 'Bruker AXS SAINT (v 7.01A, Bruker 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS SHELXTL (v 6.12)' _computing_publication_material 'SHELXL-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^)+(0.0387P)^2^+1.3765P] 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 'rigid methyls, others riding' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00132(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3066 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _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 0.51132(4) 0.05819(3) 0.75403(4) 0.02638(15) Uani 1 1 d . . . S2 S 0.20466(4) 0.15700(3) 0.67365(4) 0.03274(16) Uani 1 1 d . . . Si1 Si 0.33095(4) 0.04539(3) 0.70650(4) 0.01954(15) Uani 1 1 d . . . N1 N 0.26194(12) -0.04261(9) 0.76724(10) 0.0191(3) Uani 1 1 d . . . N2 N 0.25948(13) -0.04061(10) 0.60771(11) 0.0211(3) Uani 1 1 d . . . C1 C 0.22877(14) -0.09136(12) 0.67847(12) 0.0183(4) Uani 1 1 d . . . C2 C 0.17056(15) -0.18394(12) 0.66271(12) 0.0184(4) Uani 1 1 d . . . C3 C 0.04372(16) -0.19129(13) 0.62864(13) 0.0243(4) Uani 1 1 d . . . H3A H -0.0053 -0.1374 0.6137 0.029 Uiso 1 1 calc R . . C4 C -0.01067(16) -0.27706(13) 0.61663(14) 0.0271(4) Uani 1 1 d . . . H4A H -0.0972 -0.2820 0.5939 0.033 Uiso 1 1 calc R . . C5 C 0.06005(16) -0.35550(13) 0.63748(13) 0.0255(4) Uani 1 1 d . . . H5A H 0.0222 -0.4143 0.6290 0.031 Uiso 1 1 calc R . . C6 C 0.18654(16) -0.34866(12) 0.67080(13) 0.0238(4) Uani 1 1 d . . . H6A H 0.2352 -0.4028 0.6848 0.029 Uiso 1 1 calc R . . C7 C 0.24180(15) -0.26296(12) 0.68367(12) 0.0207(4) Uani 1 1 d . . . H7A H 0.3283 -0.2582 0.7068 0.025 Uiso 1 1 calc R . . C8 C 0.26357(15) -0.06466(12) 0.87537(13) 0.0209(4) Uani 1 1 d . . . C9 C 0.14674(17) -0.11293(14) 0.87695(14) 0.0318(5) Uani 1 1 d . . . H9A H 0.1447 -0.1753 0.8487 0.048 Uiso 1 1 calc R . . H9B H 0.0758 -0.0782 0.8341 0.048 Uiso 1 1 calc R . . H9C H 0.1446 -0.1163 0.9491 0.048 Uiso 1 1 calc R . . C10 C 0.37595(17) -0.12298(13) 0.92840(13) 0.0288(4) Uani 1 1 d . . . H10A H 0.3688 -0.1826 0.8929 0.043 Uiso 1 1 calc R . . H10B H 0.3819 -0.1327 1.0019 0.043 Uiso 1 1 calc R . . H10C H 0.4493 -0.0911 0.9245 0.043 Uiso 1 1 calc R . . C11 C 0.27501(17) 0.02764(13) 0.93211(14) 0.0276(4) Uani 1 1 d . . . H11A H 0.2034 0.0657 0.8980 0.041 Uiso 1 1 calc R . . H11B H 0.3490 0.0593 0.9295 0.041 Uiso 1 1 calc R . . H11C H 0.2799 0.0171 1.0052 0.041 Uiso 1 1 calc R . . C12 C 0.25081(16) -0.05891(12) 0.49698(13) 0.0219(4) Uani 1 1 d . . . C13 C 0.3358(2) -0.13623(16) 0.49105(16) 0.0438(6) Uani 1 1 d . . . H13A H 0.4189 -0.1216 0.5354 0.066 Uiso 1 1 calc R . . H13B H 0.3351 -0.1438 0.4185 0.066 Uiso 1 1 calc R . . H13C H 0.3088 -0.1935 0.5154 0.066 Uiso 1 1 calc R . . C14 C 0.2898(2) 0.02960(14) 0.45605(15) 0.0371(5) Uani 1 1 d . . . H14A H 0.3729 0.0458 0.4992 0.056 Uiso 1 1 calc R . . H14B H 0.2337 0.0794 0.4592 0.056 Uiso 1 1 calc R . . H14C H 0.2881 0.0207 0.3834 0.056 Uiso 1 1 calc R . . C15 C 0.11959(18) -0.08125(17) 0.43204(15) 0.0409(5) Uani 1 1 d . . . H15A H 0.0966 -0.1414 0.4531 0.061 Uiso 1 1 calc R . . H15B H 0.1132 -0.0828 0.3577 0.061 Uiso 1 1 calc R . . H15C H 0.0647 -0.0339 0.4436 0.061 Uiso 1 1 calc R . . C16 C 0.28918(16) 0.26758(12) 0.70403(14) 0.0238(4) Uani 1 1 d . . . C17 C 0.3667(2) 0.28165(15) 0.63302(18) 0.0421(5) Uani 1 1 d . . . H17A H 0.4049 0.3426 0.6458 0.063 Uiso 1 1 calc R . . H17B H 0.3152 0.2772 0.5599 0.063 Uiso 1 1 calc R . . H17C H 0.4302 0.2342 0.6474 0.063 Uiso 1 1 calc R . . C18 C 0.18832(17) 0.34025(13) 0.68136(15) 0.0303(4) Uani 1 1 d . . . H18A H 0.2251 0.4017 0.6937 0.045 Uiso 1 1 calc R . . H18B H 0.1385 0.3304 0.7275 0.045 Uiso 1 1 calc R . . H18C H 0.1367 0.3352 0.6083 0.045 Uiso 1 1 calc R . . C19 C 0.3654(2) 0.27181(15) 0.81848(16) 0.0423(5) Uani 1 1 d . . . H19A H 0.4051 0.3321 0.8338 0.063 Uiso 1 1 calc R . . H19B H 0.4277 0.2234 0.8334 0.063 Uiso 1 1 calc R . . H19C H 0.3125 0.2627 0.8622 0.063 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 0.0192(2) 0.0254(3) 0.0341(3) -0.00098(19) 0.00777(19) -0.00259(17) S2 0.0195(3) 0.0205(3) 0.0530(3) 0.0003(2) 0.0040(2) -0.00140(18) Si1 0.0195(3) 0.0174(3) 0.0217(3) -0.00060(18) 0.00646(19) -0.00178(18) N1 0.0196(7) 0.0192(8) 0.0182(7) -0.0011(6) 0.0053(6) -0.0015(6) N2 0.0242(8) 0.0209(8) 0.0190(7) -0.0004(6) 0.0079(6) -0.0044(6) C1 0.0139(8) 0.0209(9) 0.0195(9) 0.0006(7) 0.0042(7) 0.0016(7) C2 0.0205(9) 0.0218(9) 0.0133(8) -0.0007(7) 0.0058(7) -0.0027(7) C3 0.0203(9) 0.0252(10) 0.0264(9) 0.0005(8) 0.0058(7) 0.0022(7) C4 0.0189(9) 0.0319(11) 0.0293(10) -0.0026(8) 0.0057(8) -0.0069(8) C5 0.0284(10) 0.0230(10) 0.0251(9) -0.0019(8) 0.0085(8) -0.0081(8) C6 0.0287(10) 0.0202(10) 0.0231(9) 0.0007(7) 0.0089(8) 0.0010(7) C7 0.0187(9) 0.0260(10) 0.0174(8) 0.0001(7) 0.0059(7) -0.0018(7) C8 0.0236(9) 0.0234(10) 0.0173(9) -0.0020(7) 0.0086(7) -0.0010(7) C9 0.0325(11) 0.0413(12) 0.0258(10) -0.0053(9) 0.0153(8) -0.0110(9) C10 0.0343(11) 0.0295(11) 0.0212(9) 0.0018(8) 0.0067(8) 0.0045(8) C11 0.0306(10) 0.0285(10) 0.0252(9) -0.0050(8) 0.0110(8) -0.0011(8) C12 0.0261(9) 0.0229(10) 0.0173(9) 0.0006(7) 0.0076(7) -0.0012(7) C13 0.0621(15) 0.0466(14) 0.0324(11) 0.0122(10) 0.0287(11) 0.0243(11) C14 0.0540(13) 0.0352(12) 0.0247(10) 0.0014(9) 0.0160(9) -0.0103(10) C15 0.0340(11) 0.0658(15) 0.0208(10) 0.0001(10) 0.0054(8) -0.0098(10) C16 0.0243(9) 0.0189(9) 0.0272(9) -0.0013(7) 0.0066(7) -0.0011(7) C17 0.0438(12) 0.0334(12) 0.0590(14) 0.0138(10) 0.0303(11) 0.0072(10) C18 0.0317(10) 0.0231(10) 0.0339(11) 0.0000(8) 0.0074(8) 0.0033(8) C19 0.0414(12) 0.0387(13) 0.0359(11) -0.0127(10) -0.0037(9) 0.0110(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 Si1 1.9844(8) . ? S2 C16 1.8568(18) . ? S2 Si1 2.1311(7) . ? Si1 N2 1.8224(15) . ? Si1 N1 1.8289(14) . ? Si1 C1 2.2799(18) . ? N1 C1 1.338(2) . ? N1 C8 1.485(2) . ? N2 C1 1.337(2) . ? N2 C12 1.487(2) . ? C1 C2 1.488(2) . ? C2 C7 1.388(2) . ? C2 C3 1.393(2) . ? C3 C4 1.381(3) . ? C4 C5 1.378(3) . ? C5 C6 1.389(3) . ? C6 C7 1.384(3) . ? C8 C9 1.525(2) . ? C8 C10 1.525(2) . ? C8 C11 1.528(2) . ? C12 C13 1.510(3) . ? C12 C14 1.521(3) . ? C12 C15 1.527(3) . ? C16 C17 1.514(3) . ? C16 C19 1.517(3) . ? C16 C18 1.529(3) . ? 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 C16 S2 Si1 109.56(6) . . ? N2 Si1 N1 71.74(6) . . ? N2 Si1 S1 119.22(5) . . ? N1 Si1 S1 118.73(5) . . ? N2 Si1 S2 104.28(5) . . ? N1 Si1 S2 105.03(5) . . ? S1 Si1 S2 125.10(3) . . ? N2 Si1 C1 35.90(6) . . ? N1 Si1 C1 35.92(6) . . ? S1 Si1 C1 124.77(5) . . ? S2 Si1 C1 110.13(5) . . ? C1 N1 C8 132.38(14) . . ? C1 N1 Si1 90.74(10) . . ? C8 N1 Si1 135.70(11) . . ? C1 N2 C12 131.79(14) . . ? C1 N2 Si1 91.04(10) . . ? C12 N2 Si1 136.65(11) . . ? N2 C1 N1 106.22(14) . . ? N2 C1 C2 127.23(14) . . ? N1 C1 C2 126.54(14) . . ? N2 C1 Si1 53.06(8) . . ? N1 C1 Si1 53.33(8) . . ? C2 C1 Si1 175.96(12) . . ? C7 C2 C3 119.81(16) . . ? C7 C2 C1 120.42(15) . . ? C3 C2 C1 119.76(15) . . ? C4 C3 C2 119.94(16) . . ? C5 C4 C3 120.24(16) . . ? C4 C5 C6 120.10(16) . . ? C7 C6 C5 120.03(16) . . ? C6 C7 C2 119.87(16) . . ? N1 C8 C9 111.92(14) . . ? N1 C8 C10 109.04(13) . . ? C9 C8 C10 111.29(15) . . ? N1 C8 C11 105.87(14) . . ? C9 C8 C11 109.54(15) . . ? C10 C8 C11 109.01(15) . . ? N2 C12 C13 110.22(14) . . ? N2 C12 C14 106.13(14) . . ? C13 C12 C14 109.78(16) . . ? N2 C12 C15 110.80(14) . . ? C13 C12 C15 110.83(17) . . ? C14 C12 C15 108.97(16) . . ? C17 C16 C19 111.55(17) . . ? C17 C16 C18 110.12(16) . . ? C19 C16 C18 109.69(15) . . ? C17 C16 S2 110.55(14) . . ? C19 C16 S2 110.84(14) . . ? C18 C16 S2 103.83(12) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 59.08 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.247 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.048