# Electronic Supplementary Material for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Lisa Rosenberg' 'David R Edwards' 'Daniel J. Harrison' 'Robert McDonald' _publ_contact_author_name 'Lisa Rosenberg' _publ_contact_author_email LISAROSE@UVIC.CA _publ_section_title ; Toward selective functionalisation of oligosilanes: borane-catalysed dehydrogenative coupling of silanes with thiols ; # Attachment 'vic0302.cif' data_20 _database_code_depnum_ccdc_archive 'CCDC 684876' _audit_creation_method SHELXL-97 _chemical_name_systematic 2,3-disila-2,2,3,3-tetramethyl-1,4-benzodioxane _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O2 Si2' _chemical_formula_sum 'C10 H16 O2 Si2' _chemical_formula_weight 224.41 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.1274(6) _cell_length_b 12.8608(10) _cell_length_c 27.091(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2483.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6245 _cell_measurement_theta_min 3.168 _cell_measurement_theta_max 26.389 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8806 _exptl_absorpt_correction_T_max 0.9142 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17000 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2532 _reflns_number_gt 2241 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 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^)+(0.0629P)^2^+0.8980P] 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 2532 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Si1 Si 0.19723(6) 0.26956(3) 0.089784(15) 0.02937(15) Uani 1 1 d . . . Si2 Si 0.21278(6) 0.22765(3) 0.173523(16) 0.03345(16) Uani 1 1 d . . . O1 O -0.01432(16) 0.21685(8) 0.07716(4) 0.0359(3) Uani 1 1 d . . . O2 O 0.00631(18) 0.16499(9) 0.17912(4) 0.0441(3) Uani 1 1 d . . . C1 C -0.0639(2) 0.11995(11) 0.09433(6) 0.0309(3) Uani 1 1 d . . . C2 C -0.0543(2) 0.09446(12) 0.14437(6) 0.0337(3) Uani 1 1 d . . . C3 C -0.1140(2) -0.00312(13) 0.15997(7) 0.0414(4) Uani 1 1 d . . . H3 H -0.1085 -0.0204 0.1940 0.050 Uiso 1 1 calc R . . C4 C -0.1812(2) -0.07536(13) 0.12650(8) 0.0450(4) Uani 1 1 d . . . H4 H -0.2217 -0.1418 0.1375 0.054 Uiso 1 1 calc R . . C5 C -0.1891(2) -0.05046(14) 0.07702(8) 0.0435(4) Uani 1 1 d . . . H5 H -0.2343 -0.1000 0.0539 0.052 Uiso 1 1 calc R . . C6 C -0.1311(2) 0.04672(12) 0.06101(6) 0.0371(4) Uani 1 1 d . . . H6 H -0.1373 0.0634 0.0269 0.045 Uiso 1 1 calc R . . C7 C 0.3791(3) 0.20733(13) 0.05045(6) 0.0416(4) Uani 1 1 d . . . H7A H 0.3894 0.1335 0.0590 0.050 Uiso 1 1 calc R . . H7B H 0.5002 0.2415 0.0560 0.050 Uiso 1 1 calc R . . H7C H 0.3437 0.2141 0.0156 0.050 Uiso 1 1 calc R . . C8 C 0.1712(2) 0.40951(12) 0.07555(7) 0.0385(4) Uani 1 1 d . . . H8A H 0.0754 0.4399 0.0971 0.046 Uiso 1 1 calc R . . H8B H 0.1332 0.4179 0.0410 0.046 Uiso 1 1 calc R . . H8C H 0.2912 0.4449 0.0810 0.046 Uiso 1 1 calc R . . C9 C 0.4090(3) 0.13991(15) 0.19032(7) 0.0541(5) Uani 1 1 d . . . H9A H 0.4170 0.0832 0.1662 0.065 Uiso 1 1 calc R . . H9B H 0.3869 0.1110 0.2233 0.065 Uiso 1 1 calc R . . H9C H 0.5269 0.1791 0.1903 0.065 Uiso 1 1 calc R . . C10 C 0.1926(3) 0.33786(14) 0.21745(7) 0.0467(4) Uani 1 1 d . . . H10A H 0.0878 0.3826 0.2076 0.056 Uiso 1 1 calc R . . H10B H 0.3093 0.3782 0.2172 0.056 Uiso 1 1 calc R . . H10C H 0.1701 0.3109 0.2508 0.056 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 Si1 0.0336(3) 0.0288(2) 0.0257(2) 0.00170(14) 0.00219(15) -0.00095(15) Si2 0.0436(3) 0.0332(3) 0.0236(2) -0.00246(15) 0.00013(16) -0.00623(17) O1 0.0396(6) 0.0346(5) 0.0336(6) 0.0063(4) -0.0058(5) -0.0053(5) O2 0.0583(8) 0.0468(7) 0.0272(6) -0.0043(5) 0.0077(5) -0.0208(6) C1 0.0268(7) 0.0306(7) 0.0354(8) 0.0006(6) -0.0008(6) 0.0000(6) C2 0.0335(8) 0.0353(7) 0.0322(8) -0.0015(6) 0.0016(6) -0.0061(6) C3 0.0393(9) 0.0408(8) 0.0442(9) 0.0077(7) 0.0017(7) -0.0088(7) C4 0.0361(8) 0.0335(8) 0.0654(12) 0.0031(8) -0.0016(8) -0.0074(7) C5 0.0316(8) 0.0385(9) 0.0603(11) -0.0137(8) -0.0091(7) -0.0031(7) C6 0.0307(7) 0.0424(8) 0.0383(8) -0.0049(7) -0.0074(6) 0.0003(7) C7 0.0519(10) 0.0358(8) 0.0370(9) -0.0007(7) 0.0115(7) 0.0042(8) C8 0.0358(8) 0.0322(8) 0.0475(9) 0.0050(7) 0.0047(7) -0.0008(6) C9 0.0726(13) 0.0499(10) 0.0398(9) -0.0003(8) -0.0152(9) 0.0088(10) C10 0.0576(11) 0.0431(9) 0.0392(9) -0.0119(7) 0.0079(8) -0.0116(8) _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 Si1 O1 1.6881(12) . ? Si1 C8 1.8501(16) . ? Si1 C7 1.8591(16) . ? Si1 Si2 2.3344(6) . ? Si2 O2 1.6847(12) . ? Si2 C9 1.854(2) . ? Si2 C10 1.8563(18) . ? O1 C1 1.3763(18) . ? O2 C2 1.3769(19) . ? C1 C6 1.390(2) . ? C1 C2 1.396(2) . ? C2 C3 1.391(2) . ? C3 C4 1.384(3) . ? C4 C5 1.379(3) . ? C5 C6 1.386(2) . ? 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 O1 Si1 C8 105.00(7) . . ? O1 Si1 C7 109.51(7) . . ? C8 Si1 C7 111.67(8) . . ? O1 Si1 Si2 98.43(4) . . ? C8 Si1 Si2 115.59(6) . . ? C7 Si1 Si2 115.12(6) . . ? O2 Si2 C9 110.23(9) . . ? O2 Si2 C10 103.88(7) . . ? C9 Si2 C10 111.46(9) . . ? O2 Si2 Si1 99.00(4) . . ? C9 Si2 Si1 114.52(7) . . ? C10 Si2 Si1 116.30(7) . . ? C1 O1 Si1 121.62(10) . . ? C2 O2 Si2 121.85(10) . . ? O1 C1 C6 118.85(14) . . ? O1 C1 C2 121.88(13) . . ? C6 C1 C2 119.23(14) . . ? O2 C2 C3 118.85(14) . . ? O2 C2 C1 121.63(13) . . ? C3 C2 C1 119.47(14) . . ? C4 C3 C2 120.82(16) . . ? C5 C4 C3 119.68(16) . . ? C4 C5 C6 120.09(16) . . ? C5 C6 C1 120.70(16) . . ? 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 O1 Si1 Si2 O2 0.51(6) . . . . ? C8 Si1 Si2 O2 111.68(8) . . . . ? C7 Si1 Si2 O2 -115.74(8) . . . . ? O1 Si1 Si2 C9 117.70(9) . . . . ? C8 Si1 Si2 C9 -131.13(10) . . . . ? C7 Si1 Si2 C9 1.45(10) . . . . ? O1 Si1 Si2 C10 -109.93(8) . . . . ? C8 Si1 Si2 C10 1.24(9) . . . . ? C7 Si1 Si2 C10 133.82(9) . . . . ? C8 Si1 O1 C1 -163.83(12) . . . . ? C7 Si1 O1 C1 76.14(13) . . . . ? Si2 Si1 O1 C1 -44.37(12) . . . . ? C9 Si2 O2 C2 -77.03(14) . . . . ? C10 Si2 O2 C2 163.46(13) . . . . ? Si1 Si2 O2 C2 43.37(13) . . . . ? Si1 O1 C1 C6 -127.94(13) . . . . ? Si1 O1 C1 C2 54.21(18) . . . . ? Si2 O2 C2 C3 129.32(14) . . . . ? Si2 O2 C2 C1 -53.1(2) . . . . ? O1 C1 C2 O2 -0.4(2) . . . . ? C6 C1 C2 O2 -178.20(14) . . . . ? O1 C1 C2 C3 177.15(14) . . . . ? C6 C1 C2 C3 -0.7(2) . . . . ? O2 C2 C3 C4 178.09(15) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? O1 C1 C6 C5 -177.58(14) . . . . ? C2 C1 C6 C5 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.309 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049 #===END