Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' # 1. SUBMISSION DETAILS _journal_coden_Cambridge 0222 _publ_contact_author ; Dr. Danielle Ballivet-Tkatchenko LSEO UMR 5188 CNRS-Universit\'e de Bourgogne UFR Sciences et Techniques BP 47870 21078-Dijon Cedex France ; _publ_contact_author_phone '+33 380 393 770' _publ_contact_author_fax '+33 380 393 772' _publ_contact_author_email ballivet@u-bourgogne.fr _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Insertion reaction of carbon dioxide into Sn-OR bond. Synthesis, structure, and DFT calculations of di- and tetranuclear isoproxycarbonato tin(IV) complexes ; loop_ _publ_author_name _publ_author_address D.Ballivet-Tkatchenko ; UFR Sciences et Techniques CNRS-Universit\'e de Bourgogne BP 47870 21078 Dijon Cedex France ; H.Chermette ; Laboratoire de Chimie-Physique Th\'eorique Universit\'e Claude Bernard Lyon-1 43 Bd du 11 novembre 1918 69622 Villeurbanne Cedex France ; L.Plasseraud ; UFR Sciences et Techniques CNRS-Universit\'e de Bourgogne BP 47870 21078 Dijon Cedex France ; O.Walter ; ITC-CPV Forschungszentrum Karlsruhe Postfach 3640 76021 Karlsruhe Germany ; _publ_contact_author_name 'Dr. Danielle Ballivet-Tkatchenko' #============================================================================== data_dbt1 _database_code_depnum_ccdc_archive 'CCDC 614750' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H32 O4 Sn' _chemical_formula_weight 395.10 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5802(5) _cell_length_b 10.4989(6) _cell_length_c 10.5781(6) _cell_angle_alpha 88.5050(10) _cell_angle_beta 79.4410(10) _cell_angle_gamma 84.9510(10) _cell_volume 933.08(9) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 1.379 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _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 9690 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4337 _reflns_number_gt 4089 _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 w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+0.4349P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4337 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0189 _refine_ls_wR_factor_ref 0.0482 _refine_ls_wR_factor_gt 0.0473 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.003 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.697534(12) 0.545543(10) 0.975665(10) 0.02298(4) Uani 1 d . . . O1 O 0.78244(14) 0.72202(12) 0.88909(12) 0.0299(3) Uani 1 d . . . O2 O 1.01409(16) 0.63641(13) 0.93317(14) 0.0377(3) Uani 1 d . . . O3 O 1.00334(16) 0.82849(13) 0.84498(15) 0.0400(3) Uani 1 d . . . O5 O 0.47206(14) 0.60837(11) 0.94898(12) 0.0269(2) Uani 1 d . . . C1 C 0.9321(2) 0.72293(16) 0.89122(17) 0.0285(3) Uani 1 d . . . C2 C 0.9107(3) 0.9326(2) 0.7922(2) 0.0476(5) Uani 1 d . . . H2 H 0.8025 0.9413 0.8424 0.049(7) Uiso 1 calc R . . C3 C 0.9936(4) 1.0510(2) 0.8077(4) 0.0798(10) Uani 1 d . . . H3A H 0.9907 1.0652 0.8974 0.092(5) Uiso 1 calc R . . H3B H 0.9405 1.1235 0.7715 0.092(5) Uiso 1 calc R . . H3C H 1.1022 1.0396 0.7641 0.092(5) Uiso 1 calc R . . C4 C 0.9047(4) 0.9045(3) 0.6547(3) 0.0725(9) Uani 1 d . . . H4A H 1.0102 0.9017 0.6044 0.092(5) Uiso 1 calc R . . H4B H 0.8379 0.9703 0.6214 0.092(5) Uiso 1 calc R . . H4C H 0.8623 0.8234 0.6503 0.092(5) Uiso 1 calc R . . C5 C 0.4028(2) 0.72301(17) 0.89279(19) 0.0320(4) Uani 1 d . . . H5 H 0.2893 0.7128 0.8980 0.029(5) Uiso 1 calc R . . C6 C 0.4740(3) 0.7378(2) 0.7524(2) 0.0425(5) Uani 1 d . . . H6A H 0.5835 0.7550 0.7441 0.049(3) Uiso 1 calc R . . H6B H 0.4165 0.8074 0.7156 0.049(3) Uiso 1 calc R . . H6C H 0.4675 0.6603 0.7082 0.049(3) Uiso 1 calc R . . C7 C 0.4150(3) 0.84163(18) 0.9680(2) 0.0429(5) Uani 1 d . . . H7A H 0.3691 0.8290 1.0568 0.049(3) Uiso 1 calc R . . H7B H 0.3587 0.9137 0.9338 0.049(3) Uiso 1 calc R . . H7C H 0.5248 0.8572 0.9609 0.049(3) Uiso 1 calc R . . C8 C 0.7163(2) 0.59015(17) 1.16639(17) 0.0308(4) Uani 1 d . . . H8A H 0.6696 0.5244 1.2236 0.063(3) Uiso 1 calc R . . H8B H 0.8283 0.5867 1.1718 0.063(3) Uiso 1 calc R . . C9 C 0.6387(3) 0.7182(2) 1.2143(2) 0.0434(5) Uani 1 d . . . H9A H 0.5263 0.7220 1.2102 0.063(3) Uiso 1 calc R . . H9B H 0.6850 0.7845 1.1577 0.063(3) Uiso 1 calc R . . C10 C 0.6562(3) 0.7455(2) 1.3507(2) 0.0485(5) Uani 1 d . . . H10A H 0.6155 0.6766 1.4066 0.063(3) Uiso 1 calc R . . H10B H 0.7684 0.7468 1.3538 0.063(3) Uiso 1 calc R . . C11 C 0.5699(5) 0.8709(3) 1.4010(3) 0.0752(9) Uani 1 d . . . H11A H 0.6099 0.9397 1.3463 0.097(7) Uiso 1 calc R . . H11B H 0.5868 0.8837 1.4868 0.097(7) Uiso 1 calc R . . H11C H 0.4580 0.8690 1.4017 0.097(7) Uiso 1 calc R . . C12 C 0.8071(2) 0.42470(18) 0.82086(17) 0.0321(4) Uani 1 d . . . H12A H 0.9215 0.4238 0.8140 0.069(4) Uiso 1 calc R . . H12B H 0.7787 0.3384 0.8426 0.069(4) Uiso 1 calc R . . C13 C 0.7674(3) 0.4582(2) 0.6916(2) 0.0487(5) Uani 1 d . . . H13A H 0.8048 0.5410 0.6651 0.069(4) Uiso 1 calc R . . H13B H 0.6526 0.4658 0.6988 0.069(4) Uiso 1 calc R . . C14 C 0.8389(4) 0.3615(3) 0.5881(2) 0.0590(7) Uani 1 d . . . H14A H 0.9539 0.3564 0.5782 0.069(4) Uiso 1 calc R . . H14B H 0.8047 0.2780 0.6158 0.069(4) Uiso 1 calc R . . C15 C 0.7925(5) 0.3943(4) 0.4602(3) 0.0871(12) Uani 1 d . . . H15A H 0.6787 0.4080 0.4709 0.130(9) Uiso 1 calc R . . H15B H 0.8298 0.3252 0.4017 0.130(9) Uiso 1 calc R . . H15C H 0.8393 0.4707 0.4263 0.130(9) Uiso 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 Sn1 0.02151(6) 0.02192(6) 0.02628(7) -0.00082(4) -0.00609(4) -0.00238(4) O1 0.0240(6) 0.0277(6) 0.0386(7) 0.0049(5) -0.0074(5) -0.0040(5) O2 0.0321(7) 0.0316(7) 0.0508(8) 0.0085(6) -0.0127(6) -0.0025(5) O3 0.0293(7) 0.0292(7) 0.0605(9) 0.0108(6) -0.0052(6) -0.0067(5) O5 0.0224(6) 0.0221(5) 0.0375(6) 0.0047(5) -0.0097(5) -0.0022(4) C1 0.0276(8) 0.0253(8) 0.0327(9) 0.0005(7) -0.0045(7) -0.0048(7) C2 0.0392(11) 0.0308(10) 0.0661(14) 0.0174(10) 0.0032(10) 0.0012(8) C3 0.073(2) 0.0329(12) 0.128(3) 0.0207(15) -0.0027(19) -0.0128(12) C4 0.076(2) 0.0714(19) 0.0639(17) 0.0317(15) -0.0052(14) 0.0030(15) C5 0.0250(8) 0.0249(8) 0.0480(11) 0.0073(7) -0.0135(8) -0.0010(6) C6 0.0477(12) 0.0376(10) 0.0461(11) 0.0124(9) -0.0195(9) -0.0055(9) C7 0.0403(11) 0.0261(9) 0.0616(13) -0.0002(9) -0.0098(10) 0.0021(8) C8 0.0345(9) 0.0304(9) 0.0292(8) -0.0030(7) -0.0098(7) -0.0029(7) C9 0.0576(13) 0.0342(10) 0.0383(10) -0.0063(8) -0.0113(9) 0.0039(9) C10 0.0690(16) 0.0383(11) 0.0376(11) -0.0099(9) -0.0101(10) 0.0024(10) C11 0.114(3) 0.0509(15) 0.0556(16) -0.0207(13) -0.0084(16) 0.0153(16) C12 0.0337(9) 0.0313(9) 0.0307(9) -0.0043(7) -0.0061(7) 0.0015(7) C13 0.0608(15) 0.0463(12) 0.0383(11) -0.0068(9) -0.0155(10) 0.0142(11) C14 0.0776(18) 0.0577(15) 0.0407(12) -0.0148(11) -0.0212(12) 0.0255(13) C15 0.112(3) 0.093(2) 0.0586(17) -0.0283(16) -0.0396(18) 0.040(2) _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 Sn1 O5 2.0551(12) . ? Sn1 C8 2.1207(17) . ? Sn1 C12 2.1235(18) . ? Sn1 O1 2.1696(12) . ? Sn1 O5 2.2990(12) 2_667 ? O1 C1 1.290(2) . ? O2 C1 1.224(2) . ? O3 C1 1.350(2) . ? O3 C2 1.455(2) . ? O5 C5 1.456(2) . ? O5 Sn1 2.2990(12) 2_667 ? C2 C4 1.503(4) . ? C2 C3 1.512(3) . ? C5 C6 1.508(3) . ? C5 C7 1.516(3) . ? C8 C9 1.504(3) . ? C9 C10 1.515(3) . ? C10 C11 1.512(3) . ? C12 C13 1.495(3) . ? C13 C14 1.519(3) . ? C14 C15 1.502(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 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Sn1 C8 107.84(6) . . ? O5 Sn1 C12 108.85(6) . . ? C8 Sn1 C12 141.27(7) . . ? O5 Sn1 O1 89.28(5) . . ? C8 Sn1 O1 95.96(6) . . ? C12 Sn1 O1 96.47(6) . . ? O5 Sn1 O5 71.06(5) . 2_667 ? C8 Sn1 O5 90.66(6) . 2_667 ? C12 Sn1 O5 89.74(6) . 2_667 ? O1 Sn1 O5 160.34(4) . 2_667 ? C1 O1 Sn1 109.43(10) . . ? C1 O3 C2 119.24(15) . . ? C5 O5 Sn1 134.40(10) . . ? C5 O5 Sn1 116.64(10) . 2_667 ? Sn1 O5 Sn1 108.94(5) . 2_667 ? O2 C1 O1 125.19(16) . . ? O2 C1 O3 117.53(16) . . ? O1 C1 O3 117.27(15) . . ? O3 C2 C4 109.4(2) . . ? O3 C2 C3 105.1(2) . . ? C4 C2 C3 113.5(2) . . ? O5 C5 C6 111.59(15) . . ? O5 C5 C7 111.73(16) . . ? C6 C5 C7 111.55(17) . . ? C9 C8 Sn1 115.66(13) . . ? C8 C9 C10 113.49(18) . . ? C11 C10 C9 113.2(2) . . ? C13 C12 Sn1 116.89(13) . . ? C12 C13 C14 113.89(18) . . ? C15 C14 C13 113.1(2) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.808 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.058 # Attachment 'B610812A 2.cif' #============================================================================== data_dbt2 _database_code_depnum_ccdc_archive 'CCDC 614751' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H50 O5 Sn2' _chemical_formula_weight 644.01 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5317(13) _cell_length_b 12.1100(15) _cell_length_c 13.0076(16) _cell_angle_alpha 87.6506(18) _cell_angle_beta 72.5313(17) _cell_angle_gamma 74.8235(16) _cell_volume 1526.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.662 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _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 16410 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7237 _reflns_number_gt 4678 _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 w=1/[\s^2^(Fo^2^)+(0.0834P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7237 _refine_ls_number_parameters 306 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 0.01934(4) 0.26278(3) 0.45944(4) 0.03488(14) Uani 1 d . . . Sn2 Sn -0.14262(4) 0.00749(3) 0.46508(4) 0.03395(14) Uani 1 d . . . O1 O -0.1689(4) 0.2826(3) 0.4181(4) 0.0397(10) Uani 1 d . . . O2 O -0.1623(5) 0.4641(3) 0.3826(4) 0.0475(11) Uani 1 d . . . O3 O -0.3280(4) 0.3913(3) 0.3569(4) 0.0478(11) Uani 1 d . . . O4 O -0.0070(4) 0.1032(3) 0.4853(3) 0.0352(9) Uani 1 d . . . O5 O 0.1901(4) 0.1572(3) 0.5199(4) 0.0416(10) Uani 1 d . . . C1 C -0.2147(6) 0.3836(5) 0.3860(5) 0.0362(13) Uani 1 d . . . C2 C -0.3855(7) 0.5010(6) 0.3147(7) 0.0544(19) Uani 1 d . . . H2 H -0.3716 0.5631 0.3524 0.11(3) Uiso 1 calc R . . C3 C -0.5362(9) 0.5132(8) 0.3394(9) 0.093(3) Uani 1 d . . . H3A H -0.5507 0.4560 0.2984 0.150(19) Uiso 1 calc R . . H3B H -0.5801 0.5880 0.3207 0.150(19) Uiso 1 calc R . . H3C H -0.5751 0.5036 0.4150 0.150(19) Uiso 1 calc R . . C4 C -0.3119(10) 0.5008(9) 0.1986(8) 0.095(3) Uani 1 d . . . H4A H -0.2154 0.4909 0.1888 0.150(19) Uiso 1 calc R . . H4B H -0.3484 0.5724 0.1700 0.150(19) Uiso 1 calc R . . H4C H -0.3239 0.4392 0.1614 0.150(19) Uiso 1 calc R . . C5 C 0.3060(6) 0.1781(5) 0.5467(7) 0.053(2) Uani 1 d . . . H5 H 0.3736 0.1040 0.5423 0.07(2) Uiso 1 calc R . . C6 C 0.3749(8) 0.2532(7) 0.4676(8) 0.081(3) Uani 1 d . . . H6A H 0.4080 0.2170 0.3968 0.091(12) Uiso 1 calc R . . H6B H 0.4509 0.2653 0.4876 0.091(12) Uiso 1 calc R . . H6C H 0.3099 0.3255 0.4675 0.091(12) Uiso 1 calc R . . C7 C 0.2641(8) 0.2261(6) 0.6605(6) 0.057(2) Uani 1 d . . . H7A H 0.1951 0.2976 0.6682 0.091(12) Uiso 1 calc R . . H7B H 0.3431 0.2383 0.6759 0.091(12) Uiso 1 calc R . . H7C H 0.2273 0.1731 0.7098 0.091(12) Uiso 1 calc R . . C8 C -0.0654(6) 0.3771(4) 0.5974(5) 0.0391(14) Uani 1 d . . . H8A H 0.0050 0.4112 0.6053 0.073(12) Uiso 1 calc R . . H8B H -0.1400 0.4383 0.5864 0.073(12) Uiso 1 calc R . . C9 C -0.1202(7) 0.3181(6) 0.7011(6) 0.0513(17) Uani 1 d . . . H9A H -0.0499 0.2502 0.7069 0.073(12) Uiso 1 calc R . . H9B H -0.1999 0.2941 0.6978 0.073(12) Uiso 1 calc R . . C10 C -0.1612(11) 0.3973(7) 0.8017(7) 0.082(3) Uani 1 d . . . H10A H -0.0819 0.4226 0.8036 0.14(2) Uiso 1 calc R . . H10B H -0.2326 0.4645 0.7960 0.14(2) Uiso 1 calc R . . C11 C -0.2107(19) 0.3435(13) 0.9009(10) 0.179(8) Uani 1 d . . . H11D H -0.2827 0.3106 0.8966 0.14(2) Uiso 1 calc R . . H11E H -0.2462 0.3995 0.9596 0.14(2) Uiso 1 calc R . . H11F H -0.1363 0.2843 0.9129 0.14(2) Uiso 1 calc R . . C12 C 0.1520(7) 0.2813(5) 0.3037(6) 0.0481(16) Uani 1 d . . . H12A H 0.1696 0.3561 0.3028 0.101(16) Uiso 1 calc R . . H12B H 0.2394 0.2247 0.2940 0.101(16) Uiso 1 calc R . . C13 C 0.1035(9) 0.2698(8) 0.2073(7) 0.078(3) Uani 1 d . . . H13A H 0.0824 0.1963 0.2092 0.101(16) Uiso 1 calc R . . H13B H 0.0184 0.3287 0.2147 0.101(16) Uiso 1 calc R . . C14 C 0.2022(12) 0.2785(8) 0.0994(7) 0.090(3) Uani 1 d D . . H14A H 0.2768 0.2089 0.0821 0.094(18) Uiso 0.55 calc PR A 1 H14B H 0.2417 0.3419 0.1017 0.094(18) Uiso 0.55 calc PR A 1 H14C H 0.2932 0.2352 0.1010 0.094(18) Uiso 0.45 calc PR A 2 H14D H 0.2044 0.3581 0.0919 0.094(18) Uiso 0.45 calc PR A 2 C15 C 0.132(3) 0.296(3) 0.0131(18) 0.130(12) Uani 0.55 d PD B 1 H15A H 0.0655 0.2522 0.0273 0.094(18) Uiso 0.55 calc PR B 1 H15B H 0.1993 0.2724 -0.0558 0.094(18) Uiso 0.55 calc PR B 1 H15C H 0.0862 0.3761 0.0125 0.094(18) Uiso 0.55 calc PR B 1 C15X C 0.182(3) 0.241(3) -0.0013(16) 0.083(8) Uani 0.45 d PD B 2 H15D H 0.1797 0.1618 0.0031 0.094(18) Uiso 0.45 calc PR B 2 H15E H 0.2562 0.2492 -0.0625 0.094(18) Uiso 0.45 calc PR B 2 H15F H 0.0960 0.2868 -0.0089 0.094(18) Uiso 0.45 calc PR B 2 C16 C -0.3170(6) 0.0907(5) 0.5933(6) 0.0461(17) Uani 1 d . . . H16A H -0.3337 0.1729 0.5862 0.062(11) Uiso 1 calc R . . H16B H -0.3974 0.0691 0.5882 0.062(11) Uiso 1 calc R . . C17 C -0.2978(8) 0.0604(6) 0.7035(7) 0.062(2) Uani 1 d . . . H17A H -0.2818 -0.0218 0.7105 0.062(11) Uiso 1 calc R . . H17B H -0.2165 0.0810 0.7079 0.062(11) Uiso 1 calc R . . C18 C -0.4206(10) 0.1200(8) 0.7966(8) 0.083(3) Uani 1 d . . . H18A H -0.4336 0.2021 0.7922 0.128(18) Uiso 1 calc R . . H18B H -0.5029 0.1026 0.7904 0.128(18) Uiso 1 calc R . . C19 C -0.4034(17) 0.0858(14) 0.8987(11) 0.168(7) Uani 1 d . . . H19A H -0.4702 0.1386 0.9542 0.128(18) Uiso 1 calc R . . H19B H -0.3122 0.0855 0.8988 0.128(18) Uiso 1 calc R . . H19C H -0.4164 0.0103 0.9119 0.128(18) Uiso 1 calc R . . C20 C -0.1145(8) 0.0277(5) 0.2977(6) 0.0479(17) Uani 1 d . . . H20A H -0.0482 0.0724 0.2698 0.081(13) Uiso 1 calc R . . H20B H -0.0769 -0.0470 0.2606 0.081(13) Uiso 1 calc R . . C21 C -0.2503(9) 0.0876(6) 0.2738(7) 0.070(2) Uani 1 d . . . H21A H -0.3138 0.0397 0.2969 0.081(13) Uiso 1 calc R . . H21B H -0.2915 0.1592 0.3160 0.081(13) Uiso 1 calc R . . C22 C -0.2328(16) 0.1121(11) 0.1559(10) 0.143(6) Uani 1 d D . . H22A H -0.1969 0.0417 0.1117 0.12(2) Uiso 0.70 calc PR C 1 H22B H -0.1709 0.1610 0.1303 0.12(2) Uiso 0.70 calc PR C 1 H22C H -0.2197 0.1886 0.1453 0.12(2) Uiso 0.30 calc PR C 2 H22D H -0.3194 0.1144 0.1428 0.12(2) Uiso 0.30 calc PR C 2 C23 C -0.3931(18) 0.1789(15) 0.1537(14) 0.123(6) Uani 0.70 d PD D 1 H23A H -0.4542 0.1321 0.1860 0.12(2) Uiso 0.70 calc PR D 1 H23B H -0.3931 0.1919 0.0804 0.12(2) Uiso 0.70 calc PR D 1 H23C H -0.4237 0.2510 0.1934 0.12(2) Uiso 0.70 calc PR D 1 C23X C -0.107(5) 0.025(4) 0.060(4) 0.18(2) Uiso 0.30 d PD D 2 H23F H -0.0405 -0.0216 0.0907 0.12(2) Uiso 0.30 calc PR D 2 H23D H -0.0627 0.0706 0.0051 0.12(2) Uiso 0.30 calc PR D 2 H23E H -0.1457 -0.0225 0.0276 0.12(2) Uiso 0.30 calc PR D 2 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 Sn1 0.0329(2) 0.0211(2) 0.0545(3) 0.00270(17) -0.0156(2) -0.01094(16) Sn2 0.0285(2) 0.0236(2) 0.0555(3) 0.00282(17) -0.01935(19) -0.00887(15) O1 0.039(2) 0.0262(19) 0.062(3) 0.0048(18) -0.025(2) -0.0123(17) O2 0.051(3) 0.027(2) 0.078(3) 0.011(2) -0.032(2) -0.0182(19) O3 0.047(3) 0.032(2) 0.078(3) 0.015(2) -0.036(2) -0.0158(19) O4 0.031(2) 0.0212(17) 0.061(3) 0.0055(17) -0.0216(19) -0.0118(16) O5 0.034(2) 0.027(2) 0.076(3) 0.0028(19) -0.028(2) -0.0164(17) C1 0.030(3) 0.029(3) 0.054(4) 0.001(3) -0.017(3) -0.009(2) C2 0.054(4) 0.036(3) 0.083(6) 0.023(4) -0.037(4) -0.014(3) C3 0.052(5) 0.086(7) 0.142(9) 0.038(6) -0.045(6) -0.004(4) C4 0.091(7) 0.096(8) 0.102(8) 0.036(6) -0.040(6) -0.023(6) C5 0.036(3) 0.033(3) 0.106(6) 0.004(4) -0.035(4) -0.018(3) C6 0.055(5) 0.079(6) 0.135(9) 0.039(6) -0.047(5) -0.048(4) C7 0.066(5) 0.043(4) 0.083(6) 0.010(4) -0.043(4) -0.027(3) C8 0.037(3) 0.022(3) 0.065(4) 0.000(3) -0.024(3) -0.008(2) C9 0.055(4) 0.042(4) 0.057(5) 0.000(3) -0.018(4) -0.013(3) C10 0.130(9) 0.062(5) 0.050(5) -0.004(4) -0.018(5) -0.027(5) C11 0.30(2) 0.138(13) 0.077(9) -0.017(9) -0.033(12) -0.041(13) C12 0.049(4) 0.035(3) 0.060(5) 0.007(3) -0.011(3) -0.016(3) C13 0.076(6) 0.085(7) 0.072(6) 0.008(5) -0.007(5) -0.038(5) C14 0.132(9) 0.070(6) 0.059(6) 0.003(5) -0.009(6) -0.034(6) C15 0.13(2) 0.15(3) 0.076(17) -0.060(17) 0.031(16) -0.04(2) C15X 0.11(2) 0.093(19) 0.026(11) -0.015(11) -0.001(12) -0.005(15) C16 0.027(3) 0.036(3) 0.075(5) -0.004(3) -0.010(3) -0.012(2) C17 0.055(5) 0.043(4) 0.078(6) -0.008(4) -0.006(4) -0.011(3) C18 0.074(6) 0.083(6) 0.075(7) 0.003(5) -0.002(5) -0.015(5) C19 0.172(15) 0.157(15) 0.112(12) 0.012(10) 0.025(11) -0.016(11) C20 0.067(5) 0.036(3) 0.051(4) 0.001(3) -0.028(4) -0.018(3) C21 0.102(7) 0.043(4) 0.087(6) 0.008(4) -0.057(5) -0.022(4) C22 0.228(16) 0.125(10) 0.127(11) 0.039(8) -0.136(11) -0.044(10) C23 0.150(17) 0.124(15) 0.128(15) 0.050(12) -0.093(13) -0.038(12) _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 Sn1 O4 2.024(3) . ? Sn1 C8 2.128(6) . ? Sn1 C12 2.129(7) . ? Sn1 O1 2.159(4) . ? Sn1 O5 2.247(4) . ? Sn2 O4 2.032(4) 2_556 ? Sn2 C20 2.120(7) . ? Sn2 C16 2.121(6) . ? Sn2 O4 2.138(3) . ? Sn2 O5 2.168(4) 2_556 ? O1 C1 1.293(6) . ? O2 C1 1.233(6) . ? O3 C1 1.336(7) . ? O3 C2 1.466(7) . ? O4 Sn2 2.032(4) 2_556 ? O5 C5 1.448(7) . ? O5 Sn2 2.168(4) 2_556 ? C2 C4 1.477(12) . ? C2 C3 1.490(10) . ? C5 C6 1.494(10) . ? C5 C7 1.506(10) . ? C8 C9 1.527(9) . ? C9 C10 1.538(10) . ? C10 C11 1.438(15) . ? C12 C13 1.512(11) . ? C13 C14 1.494(11) . ? C14 C15X 1.497(16) . ? C14 C15 1.499(16) . ? C16 C17 1.524(10) . ? C17 C18 1.518(11) . ? C18 C19 1.423(16) . ? C20 C21 1.541(10) . ? C21 C22 1.515(13) . ? C22 C23X 1.68(2) . ? C22 C23 1.679(19) . ? 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 O4 Sn1 C8 115.2(2) . . ? O4 Sn1 C12 114.0(2) . . ? C8 Sn1 C12 130.2(2) . . ? O4 Sn1 O1 79.70(14) . . ? C8 Sn1 O1 97.19(19) . . ? C12 Sn1 O1 98.7(2) . . ? O4 Sn1 O5 71.35(14) . . ? C8 Sn1 O5 93.65(19) . . ? C12 Sn1 O5 94.6(2) . . ? O1 Sn1 O5 151.00(14) . . ? O4 Sn2 C20 119.4(2) 2_556 . ? O4 Sn2 C16 113.8(2) 2_556 . ? C20 Sn2 C16 126.8(3) . . ? O4 Sn2 O4 73.14(15) 2_556 . ? C20 Sn2 O4 98.8(2) . . ? C16 Sn2 O4 96.79(19) . . ? O4 Sn2 O5 72.88(14) 2_556 2_556 ? C20 Sn2 O5 99.1(2) . 2_556 ? C16 Sn2 O5 95.3(2) . 2_556 ? O4 Sn2 O5 145.98(15) . 2_556 ? C1 O1 Sn1 113.3(3) . . ? C1 O3 C2 116.3(5) . . ? Sn1 O4 Sn2 114.52(17) . 2_556 ? Sn1 O4 Sn2 138.44(19) . . ? Sn2 O4 Sn2 106.86(15) 2_556 . ? C5 O5 Sn2 123.3(3) . 2_556 ? C5 O5 Sn1 135.5(3) . . ? Sn2 O5 Sn1 101.17(15) 2_556 . ? O2 C1 O1 125.1(5) . . ? O2 C1 O3 123.3(5) . . ? O1 C1 O3 111.6(5) . . ? O3 C2 C4 108.6(6) . . ? O3 C2 C3 106.6(6) . . ? C4 C2 C3 114.2(8) . . ? O5 C5 C6 111.6(6) . . ? O5 C5 C7 111.5(6) . . ? C6 C5 C7 111.4(6) . . ? C9 C8 Sn1 112.7(4) . . ? C8 C9 C10 112.0(6) . . ? C11 C10 C9 113.3(9) . . ? C13 C12 Sn1 117.8(5) . . ? C14 C13 C12 116.0(8) . . ? C13 C14 C15X 120.6(16) . . ? C13 C14 C15 111.3(15) . . ? C15X C14 C15 28.1(12) . . ? C17 C16 Sn2 112.3(4) . . ? C18 C17 C16 113.3(7) . . ? C19 C18 C17 112.3(10) . . ? C21 C20 Sn2 112.2(5) . . ? C22 C21 C20 113.8(8) . . ? C21 C22 C23X 120(2) . . ? C21 C22 C23 103.7(11) . . ? C23X C22 C23 128(2) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.984 _refine_diff_density_min -1.891 _refine_diff_density_rms 0.162