# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email CHISHOLM@CHEMISTRY.OHIO-STATE.EDU _publ_contact_author_name 'Prof Malcolm Chisholm' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Department of Chemistry The Ohio State University 100 West 18th Avenue Newman and Wolfrom Labs. Columbus OH UNITED STATES OF AMERICA ; _publ_section_title ; Modeling the Catalyst Resting State in Aryl Tin(IV) Polymerizations of Lactide and Estimating the Relative Rates of Transamidation, Transesterification and Chain Transfer ; loop_ _publ_author_name 'Malcolm Chisholm' 'Ewan Delbridge' 'Judith Gallucci' data_Chisholm1101 _database_code_CSD 210941 _audit_creation_method SHELXL-93 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H26 O3 Sn' _chemical_formula_weight 481.14 _chemical_melting_point ? _chemical_compound_source ? 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 triclinic _symmetry_space_group_name_H-M P_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.433(1) _cell_length_b 10.255(1) _cell_length_c 12.180(2) _cell_angle_alpha 81.66(1) _cell_angle_beta 87.44(1) _cell_angle_gamma 73.95(1) _cell_volume 1120.3(2) _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 plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method ? _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.160 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ;A combination of phi and omega scans with a frame width of one degree was used for data collection. The data collection strategy was set up to measure a hemisphere of reciprocal space with a redundancy factor of 3.0, so that 90% of the reflections were measured at least 3.0 times. Data integration was done with Denzo. Scaling and merging of the data was done with Scalepack; application of an absorption correction is inherent in this treatment and is reflected in the scale factor range of 8.43 to 10.55 for the frames. ; _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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30902 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5108 _reflns_number_observed 4503 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ;The methyl group hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded C atom). For each methyl group, the torsion angle which defines the orientation about the C-C bond was refined. The other hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq (bonded carbon atom). Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0239P)^2^+0.2721P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5108 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_obs 0.0240 _refine_ls_wR_factor_all 0.0554 _refine_ls_wR_factor_obs 0.0527 _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.100 _refine_ls_restrained_S_all 1.081 _refine_ls_restrained_S_obs 1.100 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.770 _refine_diff_density_min -0.556 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn Sn 0.100555(13) 0.193541(13) 0.299338(10) 0.03627(5) Uani 1 d . . O1 O 0.1189(2) 0.3237(2) 0.16425(13) 0.0571(4) Uani 1 d . . O2 O 0.3755(2) 0.13683(15) 0.22408(12) 0.0461(3) Uani 1 d . . O3 O 0.4926(2) 0.2056(2) 0.07275(12) 0.0498(4) Uani 1 d . . C1 C 0.2359(2) 0.3165(2) 0.0886(2) 0.0410(4) Uani 1 d . . C2 C 0.3737(2) 0.2098(2) 0.1365(2) 0.0401(4) Uani 1 d . . C3 C 0.6306(2) 0.1099(2) 0.1147(2) 0.0530(6) Uani 1 d . . H3A H 0.6225(2) 0.0147(2) 0.1236(2) 0.064 Uiso 1 calc R . H3B H 0.6542(2) 0.1301(2) 0.1877(2) 0.064 Uiso 1 calc R . C4 C 0.7488(3) 0.1269(3) 0.0317(2) 0.0691(7) Uani 1 d . . H4A H 0.8437(5) 0.0646(15) 0.0577(8) 0.104 Uiso 1 calc R . H4B H 0.7550(15) 0.2217(6) 0.0231(13) 0.104 Uiso 1 calc R . H4C H 0.7248(12) 0.1056(20) -0.0399(5) 0.104 Uiso 1 calc R . C5 C 0.1963(3) 0.2790(3) -0.0203(2) 0.0694(7) Uani 1 d . . H5A H 0.2798(9) 0.2732(20) -0.0720(6) 0.104 Uiso 1 calc R . H5B H 0.1100(14) 0.3495(11) -0.0525(9) 0.104 Uiso 1 calc R . H5C H 0.1737(22) 0.1904(10) -0.0064(3) 0.104 Uiso 1 calc R . C6 C 0.2674(3) 0.4561(2) 0.0701(2) 0.0534(6) Uani 1 d . . H6A H 0.3460(13) 0.4553(6) 0.0146(10) 0.080 Uiso 1 calc R . H6B H 0.2985(17) 0.4759(8) 0.1401(4) 0.080 Uiso 1 calc R . H6C H 0.1778(6) 0.5268(3) 0.0437(13) 0.080 Uiso 1 calc R . C7 C 0.2061(2) 0.2230(2) 0.4408(2) 0.0358(4) Uani 1 d . . C8 C 0.2989(2) 0.1128(2) 0.5066(2) 0.0390(4) Uani 1 d . . H8 H 0.3178(2) 0.0235(2) 0.4864(2) 0.047 Uiso 1 calc R . C9 C 0.3642(2) 0.1307(2) 0.6007(2) 0.0461(5) Uani 1 d . . H9 H 0.4262(2) 0.0541(2) 0.6450(2) 0.055 Uiso 1 calc R . C10 C 0.3390(2) 0.2601(3) 0.6300(2) 0.0510(5) Uani 1 d . . H10 H 0.3847(2) 0.2727(3) 0.6941(2) 0.061 Uiso 1 calc R . C11 C 0.2477(2) 0.3714(2) 0.5665(2) 0.0521(5) Uani 1 d . . H11 H 0.2307(2) 0.4606(2) 0.5867(2) 0.063 Uiso 1 calc R . C12 C 0.1805(2) 0.3527(2) 0.4731(2) 0.0456(5) Uani 1 d . . H12 H 0.1162(2) 0.4295(2) 0.4305(2) 0.055 Uiso 1 calc R . C13 C 0.1257(2) -0.0165(2) 0.28230(15) 0.0366(4) Uani 1 d . . C14 C 0.2602(2) -0.1164(2) 0.2822(2) 0.0464(5) Uani 1 d . . H14 H 0.3493(2) -0.0910(2) 0.2851(2) 0.056 Uiso 1 calc R . C15 C 0.2663(3) -0.2517(2) 0.2778(2) 0.0557(6) Uani 1 d . . H15 H 0.3592(3) -0.3182(2) 0.2784(2) 0.067 Uiso 1 calc R . C16 C 0.1391(3) -0.2905(2) 0.2726(2) 0.0570(6) Uani 1 d . . H16 H 0.1437(3) -0.3835(2) 0.2690(2) 0.068 Uiso 1 calc R . C17 C 0.0056(3) -0.1946(3) 0.2727(2) 0.0612(6) Uani 1 d . . H17 H -0.0827(3) -0.2210(3) 0.2688(2) 0.073 Uiso 1 calc R . C18 C -0.0015(2) -0.0591(2) 0.2786(2) 0.0502(5) Uani 1 d . . H18 H -0.0951(2) 0.0061(2) 0.2801(2) 0.060 Uiso 1 calc R . C19 C -0.1329(2) 0.2812(2) 0.3155(2) 0.0353(4) Uani 1 d . . C20 C -0.2072(2) 0.2442(2) 0.4109(2) 0.0475(5) Uani 1 d . . H20 H -0.1527(2) 0.1842(2) 0.4707(2) 0.057 Uiso 1 calc R . C21 C -0.3595(2) 0.2929(2) 0.4207(2) 0.0525(6) Uani 1 d . . H21 H -0.4081(2) 0.2650(2) 0.4862(2) 0.063 Uiso 1 calc R . C22 C -0.4396(2) 0.3817(2) 0.3353(2) 0.0483(5) Uani 1 d . . H22 H -0.5437(2) 0.4152(2) 0.3416(2) 0.058 Uiso 1 calc R . C23 C -0.3682(2) 0.4217(2) 0.2408(2) 0.0491(5) Uani 1 d . . H23 H -0.4232(2) 0.4835(2) 0.1821(2) 0.059 Uiso 1 calc R . C24 C -0.2159(2) 0.3722(2) 0.2308(2) 0.0415(5) Uani 1 d . . H24 H -0.1679(2) 0.4008(2) 0.1652(2) 0.050 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 Sn 0.03204(8) 0.03360(8) 0.03614(8) 0.00285(5) -0.00029(5) -0.00124(5) O1 0.0399(8) 0.0555(9) 0.0545(9) 0.0209(7) 0.0111(7) 0.0059(7) O2 0.0394(8) 0.0431(8) 0.0444(8) 0.0088(6) 0.0055(6) -0.0011(6) O3 0.0420(8) 0.0509(9) 0.0437(8) 0.0052(7) 0.0112(6) 0.0006(7) C1 0.0401(11) 0.0426(11) 0.0337(10) 0.0025(8) 0.0020(8) -0.0048(9) C2 0.0404(11) 0.0377(11) 0.0379(10) -0.0032(8) 0.0051(8) -0.0055(8) C3 0.0422(12) 0.0496(13) 0.0541(13) 0.0024(10) 0.0083(10) 0.0029(10) C4 0.0532(15) 0.077(2) 0.063(2) -0.0023(13) 0.0193(12) -0.0013(13) C5 0.066(2) 0.078(2) 0.062(2) -0.0222(14) -0.0149(13) -0.0079(14) C6 0.0513(13) 0.0427(12) 0.0585(14) 0.0021(10) 0.0000(11) -0.0045(10) C7 0.0313(9) 0.0332(10) 0.0402(10) -0.0005(8) 0.0044(8) -0.0073(8) C8 0.0363(10) 0.0344(10) 0.0425(11) -0.0034(8) 0.0000(8) -0.0043(8) C9 0.0356(10) 0.0545(13) 0.0424(11) -0.0016(10) -0.0015(9) -0.0050(9) C10 0.0402(11) 0.067(2) 0.0498(13) -0.0187(11) 0.0024(10) -0.0161(11) C11 0.0521(13) 0.0463(13) 0.0637(14) -0.0219(11) 0.0108(11) -0.0173(10) C12 0.0436(11) 0.0324(10) 0.0560(13) -0.0016(9) 0.0053(9) -0.0056(9) C13 0.0371(10) 0.0386(10) 0.0290(9) -0.0011(8) -0.0006(7) -0.0035(8) C14 0.0392(11) 0.0404(12) 0.0547(13) -0.0061(10) -0.0022(9) -0.0026(9) C15 0.0534(14) 0.0390(12) 0.0650(15) -0.0060(10) 0.0061(11) 0.0018(10) C16 0.073(2) 0.0408(12) 0.0581(14) -0.0106(10) 0.0191(12) -0.0185(12) C17 0.0545(14) 0.0559(15) 0.079(2) -0.0169(13) 0.0140(12) -0.0229(12) C18 0.0384(11) 0.0482(13) 0.0602(14) -0.0082(10) 0.0052(10) -0.0059(9) C19 0.0347(10) 0.0295(9) 0.0376(10) -0.0024(8) 0.0009(8) -0.0034(8) C20 0.0448(12) 0.0402(11) 0.0459(12) 0.0074(9) 0.0036(9) 0.0004(9) C21 0.0464(12) 0.0486(13) 0.0550(13) 0.0030(10) 0.0169(10) -0.0087(10) C22 0.0332(10) 0.0468(12) 0.0617(14) -0.0086(10) 0.0052(10) -0.0058(9) C23 0.0369(11) 0.0526(13) 0.0491(12) 0.0004(10) -0.0073(9) -0.0005(9) C24 0.0361(10) 0.0449(11) 0.0379(10) 0.0003(9) 0.0026(8) -0.0052(9) _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 Sn O1 1.9962(14) . ? Sn C7 2.126(2) . ? Sn C13 2.141(2) . ? Sn C19 2.148(2) . ? O1 C1 1.398(2) . ? O2 C2 1.209(2) . ? O3 C2 1.330(2) . ? O3 C3 1.458(3) . ? C1 C5 1.522(3) . ? C1 C2 1.524(3) . ? C1 C6 1.525(3) . ? C3 C4 1.500(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 C8 1.392(3) . ? C7 C12 1.396(3) . ? C8 C9 1.383(3) . ? C8 H8 0.95 . ? C9 C10 1.379(3) . ? C9 H9 0.95 . ? C10 C11 1.379(3) . ? C10 H10 0.95 . ? C11 C12 1.388(3) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 C18 1.390(3) . ? C13 C14 1.393(3) . ? C14 C15 1.381(3) . ? C14 H14 0.95 . ? C15 C16 1.371(3) . ? C15 H15 0.95 . ? C16 C17 1.367(3) . ? C16 H16 0.95 . ? C17 C18 1.384(3) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C20 1.390(3) . ? C19 C24 1.391(3) . ? C20 C21 1.390(3) . ? C20 H20 0.95 . ? C21 C22 1.378(3) . ? C21 H21 0.95 . ? C22 C23 1.376(3) . ? C22 H22 0.95 . ? C23 C24 1.391(3) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? 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 Sn C7 113.25(7) . . ? O1 Sn C13 118.73(7) . . ? C7 Sn C13 114.44(7) . . ? O1 Sn C19 93.86(6) . . ? C7 Sn C19 108.47(7) . . ? C13 Sn C19 105.05(7) . . ? C1 O1 Sn 129.16(12) . . ? C2 O3 C3 116.8(2) . . ? O1 C1 C5 110.5(2) . . ? O1 C1 C2 110.1(2) . . ? C5 C1 C2 109.5(2) . . ? O1 C1 C6 107.7(2) . . ? C5 C1 C6 110.6(2) . . ? C2 C1 C6 108.4(2) . . ? O2 C2 O3 123.2(2) . . ? O2 C2 C1 123.6(2) . . ? O3 C2 C1 113.3(2) . . ? O3 C3 C4 107.2(2) . . ? O3 C3 H3A 110.27(12) . . ? C4 C3 H3A 110.27(15) . . ? O3 C3 H3B 110.27(12) . . ? C4 C3 H3B 110.3(2) . . ? H3A C3 H3B 108.5 . . ? C3 C4 H4A 109.47(13) . . ? C3 C4 H4B 109.47(15) . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5(2) . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C5 H5A 109.47(13) . . ? C1 C5 H5B 109.47(13) . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.47(14) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C6 H6A 109.47(12) . . ? C1 C6 H6B 109.47(12) . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.47(11) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 117.7(2) . . ? C8 C7 Sn 121.09(14) . . ? C12 C7 Sn 121.13(14) . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.32(12) . . ? C7 C8 H8 119.32(12) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.09(13) . . ? C8 C9 H9 120.09(12) . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.88(13) . . ? C11 C10 H10 119.88(13) . . ? C10 C11 C12 119.8(2) . . ? C10 C11 H11 120.11(13) . . ? C12 C11 H11 120.11(13) . . ? C11 C12 C7 121.0(2) . . ? C11 C12 H12 119.48(13) . . ? C7 C12 H12 119.48(12) . . ? C18 C13 C14 117.2(2) . . ? C18 C13 Sn 117.84(14) . . ? C14 C13 Sn 124.9(2) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.40(13) . . ? C13 C14 H14 119.40(13) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.80(14) . . ? C14 C15 H15 119.80(13) . . ? C17 C16 C15 119.6(2) . . ? C17 C16 H16 120.20(15) . . ? C15 C16 H16 120.20(14) . . ? C16 C17 C18 120.3(2) . . ? C16 C17 H17 119.84(15) . . ? C18 C17 H17 119.84(14) . . ? C17 C18 C13 121.3(2) . . ? C17 C18 H18 119.35(14) . . ? C13 C18 H18 119.35(12) . . ? C20 C19 C24 117.6(2) . . ? C20 C19 Sn 120.33(14) . . ? C24 C19 Sn 121.99(14) . . ? C19 C20 C21 121.5(2) . . ? C19 C20 H20 119.25(12) . . ? C21 C20 H20 119.25(13) . . ? C22 C21 C20 119.8(2) . . ? C22 C21 H21 120.08(12) . . ? C20 C21 H21 120.08(13) . . ? C23 C22 C21 119.7(2) . . ? C23 C22 H22 120.16(12) . . ? C21 C22 H22 120.16(12) . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 119.81(12) . . ? C24 C23 H23 119.81(12) . . ? C23 C24 C19 120.9(2) . . ? C23 C24 H24 119.54(12) . . ? C19 C24 H24 119.54(11) . . ? 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 C7 Sn O1 C1 82.2(2) . . . . ? C13 Sn O1 C1 -56.3(2) . . . . ? C19 Sn O1 C1 -165.8(2) . . . . ? Sn O1 C1 C5 106.6(2) . . . . ? Sn O1 C1 C2 -14.5(3) . . . . ? Sn O1 C1 C6 -132.5(2) . . . . ? C3 O3 C2 O2 -1.8(3) . . . . ? C3 O3 C2 C1 177.7(2) . . . . ? O1 C1 C2 O2 4.8(3) . . . . ? C5 C1 C2 O2 -116.9(2) . . . . ? C6 C1 C2 O2 122.4(2) . . . . ? O1 C1 C2 O3 -174.7(2) . . . . ? C5 C1 C2 O3 63.7(2) . . . . ? C6 C1 C2 O3 -57.1(2) . . . . ? C2 O3 C3 C4 -177.9(2) . . . . ? O1 Sn C7 C8 -132.33(15) . . . . ? C13 Sn C7 C8 8.0(2) . . . . ? C19 Sn C7 C8 124.9(2) . . . . ? O1 Sn C7 C12 50.0(2) . . . . ? C13 Sn C7 C12 -169.68(15) . . . . ? C19 Sn C7 C12 -52.8(2) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? Sn C7 C8 C9 -177.92(15) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 -1.2(3) . . . . ? C8 C7 C12 C11 1.2(3) . . . . ? Sn C7 C12 C11 178.9(2) . . . . ? O1 Sn C13 C18 -100.0(2) . . . . ? C7 Sn C13 C18 122.0(2) . . . . ? C19 Sn C13 C18 3.1(2) . . . . ? O1 Sn C13 C14 84.6(2) . . . . ? C7 Sn C13 C14 -53.5(2) . . . . ? C19 Sn C13 C14 -172.3(2) . . . . ? C18 C13 C14 C15 0.4(3) . . . . ? Sn C13 C14 C15 175.8(2) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? C16 C17 C18 C13 1.3(4) . . . . ? C14 C13 C18 C17 -1.3(3) . . . . ? Sn C13 C18 C17 -177.0(2) . . . . ? O1 Sn C19 C20 -169.2(2) . . . . ? C7 Sn C19 C20 -53.1(2) . . . . ? C13 Sn C19 C20 69.7(2) . . . . ? O1 Sn C19 C24 13.1(2) . . . . ? C7 Sn C19 C24 129.2(2) . . . . ? C13 Sn C19 C24 -108.0(2) . . . . ? C24 C19 C20 C21 1.8(3) . . . . ? Sn C19 C20 C21 -176.1(2) . . . . ? C19 C20 C21 C22 -1.1(4) . . . . ? C20 C21 C22 C23 -0.1(4) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? C22 C23 C24 C19 0.2(3) . . . . ? C20 C19 C24 C23 -1.3(3) . . . . ? Sn C19 C24 C23 176.4(2) . . . . ? #END OF CIF data_Chisholm1111 _database_code_CSD 210942 _audit_creation_method SHELXL-93 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H34 N2 O4 Sn' _chemical_formula_weight 533.22 _chemical_melting_point ? _chemical_compound_source ? 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' N N 0.0061 0.0033 '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 2(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 11.554(1) _cell_length_b 11.075(1) _cell_length_c 19.704(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.947(4) _cell_angle_gamma 90.00 _cell_volume 2490.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method ? _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.056 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ;A combination of phi and omega scans with a frame width of one degree was used for data collection. The data collection strategy was set up to measure a quadrant of reciprocal space with a redundancy factor of 3.7, so that 90% of the reflections were measured at least 3.7 times. Data integration was done with Denzo. Scaling and merging of the data was done with Scalepack; application of an absorption correction is inherent in this treatment and is reflected in the scale factor range of 9.30 to 10.28 for the frames. ; _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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44002 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5704 _reflns_number_observed 4678 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ;One of the phenyl rings is rotationally disordered about the Sn-C(19) bond. The disorder is modeled with two orientations for this ring. The C(19) and C(22) atoms are common to both orientations, while the other four carbon atoms of the ring are disordered over two sites each. Only the C(19) atom of this phenyl group is refined anisotropically; the other carbon atoms are kept isotropic. The occupancy factors for the two orientations refined to 0.529(8) and 0.471(8). The methyl group hydrogen atoms were added at calculated positions using a riding model with U(H) = 1.5 * Ueq(bonded C atom). For each methyl group, the torsion angle which defines the orientation about the C-C of N-C bond was refined. The other hydrogen atoms were included in the model at calculated positions using a riding model with U(H) = 1.2 * Ueq (bonded carbon atom). Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0503P)^2^+2.1099P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5704 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_obs 0.0349 _refine_ls_wR_factor_all 0.0979 _refine_ls_wR_factor_obs 0.0926 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.087 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.087 _refine_ls_shift/esd_max -0.047 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.706 _refine_diff_density_min -0.911 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn Sn 0.21156(2) 0.20906(2) 0.155213(10) 0.04359(9) Uani 1 d . . O1 O 0.1386(2) 0.2101(2) 0.25557(11) 0.0476(5) Uani 1 d . . O2 O 0.2637(2) 0.3682(2) 0.20202(11) 0.0484(5) Uani 1 d . . O3 O 0.3583(2) 0.1262(2) 0.22978(10) 0.0455(5) Uani 1 d . . O4 O 0.1815(2) 0.0289(2) 0.15269(12) 0.0579(6) Uani 1 d . . N1 N 0.1353(3) 0.2999(3) 0.35583(15) 0.0584(7) Uani 1 d . . N2 N 0.4167(2) -0.0319(2) 0.29495(14) 0.0509(6) Uani 1 d . . C1 C 0.1679(3) 0.2984(3) 0.2938(2) 0.0449(7) Uani 1 d . . C2 C 0.2425(3) 0.3997(3) 0.2674(2) 0.0467(7) Uani 1 d . . C3 C 0.1760(3) 0.5197(3) 0.2614(2) 0.0620(9) Uani 1 d . . H3A H 0.1636(21) 0.5463(12) 0.3072(3) 0.093 Uiso 1 calc R . H3B H 0.1001(10) 0.5091(7) 0.2321(11) 0.093 Uiso 1 calc R . H3C H 0.2218(11) 0.5807(7) 0.2412(13) 0.093 Uiso 1 calc R . C4 C 0.3612(3) 0.4078(4) 0.3145(2) 0.0647(9) Uani 1 d . . H4A H 0.3485(3) 0.4238(26) 0.3617(3) 0.097 Uiso 1 calc R . H4B H 0.4075(10) 0.4734(17) 0.2989(9) 0.097 Uiso 1 calc R . H4C H 0.4033(11) 0.3313(10) 0.3130(11) 0.097 Uiso 1 calc R . C5 C 0.1538(5) 0.3913(5) 0.4086(2) 0.0915(14) Uani 1 d . . H5A H 0.2022(27) 0.3581(11) 0.4497(7) 0.137 Uiso 1 calc R . H5B H 0.0781(5) 0.4170(25) 0.4201(14) 0.137 Uiso 1 calc R . H5C H 0.1937(30) 0.4608(15) 0.3919(7) 0.137 Uiso 1 calc R . C6 C 0.0691(4) 0.1950(4) 0.3759(2) 0.0749(11) Uani 1 d . . H6A H 0.0316(24) 0.2165(10) 0.4155(11) 0.112 Uiso 1 calc R . H6B H 0.1228(6) 0.1272(10) 0.3881(16) 0.112 Uiso 1 calc R . H6C H 0.0091(19) 0.1717(19) 0.3374(6) 0.112 Uiso 1 calc R . C7 C 0.3438(2) 0.0174(3) 0.2443(2) 0.0437(6) Uani 1 d . . C8 C 0.2399(3) -0.0508(3) 0.2014(2) 0.0522(7) Uani 1 d . . C9 C 0.1527(3) -0.0954(3) 0.2472(2) 0.0681(10) Uani 1 d . . H9A H 0.1275(20) -0.0272(6) 0.2731(12) 0.102 Uiso 1 calc R . H9B H 0.1906(9) -0.1563(20) 0.2793(11) 0.102 Uiso 1 calc R . H9C H 0.0844(12) -0.1311(24) 0.2185(3) 0.102 Uiso 1 calc R . C10 C 0.2876(3) -0.1550(3) 0.1611(2) 0.0695(10) Uani 1 d . . H10A H 0.3284(24) -0.2138(14) 0.1935(2) 0.104 Uiso 1 calc R . H10B H 0.3422(21) -0.1224(5) 0.1324(12) 0.104 Uiso 1 calc R . H10C H 0.2222(5) -0.1948(18) 0.1319(12) 0.104 Uiso 1 calc R . C11 C 0.5114(3) 0.0402(3) 0.3324(2) 0.0606(8) Uani 1 d . . H11A H 0.5867(3) 0.0012(13) 0.3298(12) 0.091 Uiso 1 calc R . H11B H 0.5005(13) 0.0469(20) 0.3806(4) 0.091 Uiso 1 calc R . H11C H 0.5105(15) 0.1210(9) 0.3121(9) 0.091 Uiso 1 calc R . C12 C 0.4183(4) -0.1577(4) 0.3189(2) 0.0756(11) Uani 1 d . . H12A H 0.4126(30) -0.1592(4) 0.3680(5) 0.113 Uiso 1 calc R . H12B H 0.4916(14) -0.1963(10) 0.3113(16) 0.113 Uiso 1 calc R . H12C H 0.3517(17) -0.2014(9) 0.2932(12) 0.113 Uiso 1 calc R . C13 C 0.3279(3) 0.2289(3) 0.0808(2) 0.0479(7) Uani 1 d . . C14 C 0.4125(3) 0.1435(3) 0.0703(2) 0.0577(8) Uani 1 d . . H14 H 0.4191(3) 0.0712(3) 0.0965(2) 0.069 Uiso 1 calc R . C15 C 0.4874(3) 0.1619(4) 0.0222(2) 0.0680(10) Uani 1 d . . H15 H 0.5461(3) 0.1039(4) 0.0173(2) 0.082 Uiso 1 calc R . C16 C 0.4767(4) 0.2627(4) -0.0177(2) 0.0760(11) Uani 1 d . . H16 H 0.5265(4) 0.2737(4) -0.0512(2) 0.091 Uiso 1 calc R . C17 C 0.3935(4) 0.3493(5) -0.0097(2) 0.0809(12) Uani 1 d . . H17 H 0.3864(4) 0.4201(5) -0.0371(2) 0.097 Uiso 1 calc R . C18 C 0.3208(4) 0.3308(4) 0.0391(2) 0.0691(10) Uani 1 d . . H18 H 0.2636(4) 0.3904(4) 0.0443(2) 0.083 Uiso 1 calc R . C19 C 0.0432(3) 0.2525(4) 0.0979(2) 0.0593(8) Uani 1 d . . C20A C -0.0151(5) 0.1571(6) 0.0529(3) 0.048(2) Uiso 0.529(8) d P 1 H20A H 0.0216(5) 0.0804(6) 0.0527(3) 0.057 Uiso 0.529(8) calc PR 1 C21A C -0.1208(6) 0.1749(7) 0.0111(4) 0.061(2) Uiso 0.529(8) d P 1 H21A H -0.1574(6) 0.1144(7) -0.0191(4) 0.073 Uiso 0.529(8) calc PR 1 C23A C -0.1311(8) 0.3696(9) 0.0565(5) 0.082(3) Uiso 0.529(8) d P 1 H23A H -0.1702(8) 0.4441(9) 0.0603(5) 0.099 Uiso 0.529(8) calc PR 1 C24A C -0.0192(8) 0.3478(8) 0.1000(5) 0.076(2) Uiso 0.529(8) d P 1 H24A H 0.0097(8) 0.4086(8) 0.1322(5) 0.091 Uiso 0.529(8) calc PR 1 C20 C -0.0424(11) 0.1916(12) 0.0849(7) 0.098(4) Uiso 0.471(8) d P 2 H20 H -0.0356(11) 0.1129(12) 0.1043(7) 0.118 Uiso 0.471(8) calc PR 2 C21 C -0.1572(14) 0.2184(15) 0.0435(9) 0.124(5) Uiso 0.471(8) d P 2 H21 H -0.2177(14) 0.1599(15) 0.0412(9) 0.149 Uiso 0.471(8) calc PR 2 C23 C -0.0861(8) 0.4133(9) 0.0362(5) 0.072(2) Uiso 0.471(8) d P 2 H23 H -0.1062(8) 0.4932(9) 0.0213(5) 0.086 Uiso 0.471(8) calc PR 2 C24 C 0.0207(7) 0.3844(8) 0.0761(4) 0.062(2) Uiso 0.471(8) d P 2 H24 H 0.0781(7) 0.4448(8) 0.0894(4) 0.074 Uiso 0.471(8) calc PR 2 C22 C -0.1741(6) 0.2981(6) 0.0171(4) 0.112(2) Uiso 1 d . . H22A H -0.2449(6) 0.3179(6) -0.0121(4) 0.134 Uiso 0.529(8) calc PR 1 H22 H -0.2401(6) 0.3049(6) -0.0180(4) 0.134 Uiso 0.471(8) calc PR 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 Sn 0.03571(12) 0.04823(13) 0.04384(13) -0.00144(9) -0.00321(8) 0.00496(8) O1 0.0481(11) 0.0442(11) 0.0493(12) 0.0010(9) 0.0037(9) -0.0007(9) O2 0.0526(11) 0.0446(11) 0.0472(11) 0.0001(9) 0.0049(9) 0.0000(9) O3 0.0382(10) 0.0435(11) 0.0514(11) 0.0010(9) -0.0036(8) 0.0021(8) O4 0.0477(11) 0.0535(13) 0.0664(14) -0.0103(11) -0.0105(10) 0.0007(10) N1 0.057(2) 0.068(2) 0.050(2) -0.0067(13) 0.0080(13) 0.0022(13) N2 0.0449(13) 0.0468(14) 0.059(2) 0.0058(12) 0.0029(11) 0.0070(11) C1 0.0370(14) 0.047(2) 0.049(2) 0.0023(13) 0.0005(12) 0.0070(12) C2 0.0422(15) 0.045(2) 0.051(2) -0.0053(13) 0.0025(12) -0.0011(12) C3 0.065(2) 0.043(2) 0.080(2) -0.001(2) 0.017(2) 0.004(2) C4 0.049(2) 0.087(3) 0.056(2) -0.004(2) -0.0016(15) -0.012(2) C5 0.118(4) 0.093(3) 0.070(3) -0.018(2) 0.032(3) -0.015(3) C6 0.081(3) 0.085(3) 0.062(2) 0.010(2) 0.020(2) -0.010(2) C7 0.0349(13) 0.044(2) 0.053(2) -0.0015(13) 0.0086(12) 0.0071(11) C8 0.0412(15) 0.044(2) 0.069(2) -0.0075(15) 0.0024(14) 0.0018(13) C9 0.047(2) 0.058(2) 0.100(3) -0.003(2) 0.016(2) -0.006(2) C10 0.066(2) 0.049(2) 0.093(3) -0.021(2) 0.011(2) 0.001(2) C11 0.057(2) 0.065(2) 0.054(2) -0.003(2) -0.0073(15) 0.008(2) C12 0.074(2) 0.056(2) 0.093(3) 0.017(2) 0.002(2) 0.008(2) C13 0.0403(15) 0.059(2) 0.041(2) 0.0016(14) -0.0022(12) 0.0045(13) C14 0.057(2) 0.058(2) 0.057(2) -0.004(2) 0.0075(15) 0.006(2) C15 0.065(2) 0.072(2) 0.069(2) -0.011(2) 0.018(2) 0.009(2) C16 0.078(3) 0.092(3) 0.059(2) 0.004(2) 0.016(2) 0.010(2) C17 0.083(3) 0.094(3) 0.067(2) 0.024(2) 0.015(2) 0.012(2) C18 0.067(2) 0.081(2) 0.058(2) 0.009(2) 0.003(2) 0.010(2) C19 0.044(2) 0.083(2) 0.048(2) 0.002(2) -0.0032(13) 0.014(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 Sn O4 2.024(2) . ? Sn O2 2.037(2) . ? Sn C19 2.146(3) . ? Sn C13 2.149(3) . ? Sn O3 2.258(2) . ? Sn O1 2.267(2) . ? O1 C1 1.249(4) . ? O2 C2 1.393(4) . ? O3 C7 1.256(4) . ? O4 C8 1.399(4) . ? N1 C1 1.334(4) . ? N1 C5 1.444(5) . ? N1 C6 1.478(5) . ? N2 C7 1.321(4) . ? N2 C11 1.459(4) . ? N2 C12 1.470(5) . ? C1 C2 1.553(4) . ? C2 C3 1.530(4) . ? C2 C4 1.534(4) . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 C8 1.552(4) . ? C8 C9 1.535(5) . ? C8 C10 1.550(5) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C18 1.391(5) . ? C13 C14 1.399(5) . ? C14 C15 1.394(5) . ? C14 H14 0.95 . ? C15 C16 1.359(6) . ? C15 H15 0.95 . ? C16 C17 1.384(6) . ? C16 H16 0.95 . ? C17 C18 1.388(6) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? C19 C20 1.192(13) . ? C19 C24A 1.283(9) . ? C19 C20A 1.474(8) . ? C19 C24 1.534(9) . ? C20A C21A 1.376(9) . ? C20A H20A 0.95 . ? C21A C22 1.509(10) . ? C21A H21A 0.95 . ? C23A C22 1.164(10) . ? C23A C24A 1.456(12) . ? C23A H23A 0.95 . ? C24A H24A 0.95 . ? C20 C21 1.47(2) . ? C20 H20 0.95 . ? C21 C22 1.027(15) . ? C21 H21 0.95 . ? C23 C24 1.393(12) . ? C23 C22 1.638(12) . ? C23 H23 0.95 . ? C24 H24 0.95 . ? C22 H22A 0.95 . ? C22 H22 0.95 . ? 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 Sn O2 154.38(9) . . ? O4 Sn C19 93.99(13) . . ? O2 Sn C19 102.97(13) . . ? O4 Sn C13 101.96(11) . . ? O2 Sn C13 92.76(11) . . ? C19 Sn C13 103.30(12) . . ? O4 Sn O3 73.99(8) . . ? O2 Sn O3 85.29(8) . . ? C19 Sn O3 163.84(12) . . ? C13 Sn O3 89.97(9) . . ? O4 Sn O1 86.59(9) . . ? O2 Sn O1 74.02(8) . . ? C19 Sn O1 91.61(11) . . ? C13 Sn O1 162.09(10) . . ? O3 Sn O1 77.18(8) . . ? C1 O1 Sn 115.3(2) . . ? C2 O2 Sn 123.6(2) . . ? C7 O3 Sn 115.1(2) . . ? C8 O4 Sn 122.9(2) . . ? C1 N1 C5 129.6(3) . . ? C1 N1 C6 117.8(3) . . ? C5 N1 C6 112.5(3) . . ? C7 N2 C11 119.7(3) . . ? C7 N2 C12 127.5(3) . . ? C11 N2 C12 112.7(3) . . ? O1 C1 N1 118.3(3) . . ? O1 C1 C2 118.5(3) . . ? N1 C1 C2 123.2(3) . . ? O2 C2 C3 107.7(3) . . ? O2 C2 C4 107.7(2) . . ? C3 C2 C4 112.8(3) . . ? O2 C2 C1 108.4(2) . . ? C3 C2 C1 110.8(2) . . ? C4 C2 C1 109.3(3) . . ? C2 C3 H3A 109.5(2) . . ? C2 C3 H3B 109.5(2) . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5(2) . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5(2) . . ? C2 C4 H4B 109.5(2) . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5(2) . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5(2) . . ? N1 C5 H5B 109.5(2) . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5(2) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5(2) . . ? N1 C6 H6B 109.5(2) . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5(2) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 N2 118.5(3) . . ? O3 C7 C8 117.6(3) . . ? N2 C7 C8 123.9(3) . . ? O4 C8 C9 108.4(3) . . ? O4 C8 C10 106.9(3) . . ? C9 C8 C10 112.3(3) . . ? O4 C8 C7 108.4(2) . . ? C9 C8 C7 111.0(3) . . ? C10 C8 C7 109.6(3) . . ? C8 C9 H9A 109.5(2) . . ? C8 C9 H9B 109.5(2) . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5(2) . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5(2) . . ? C8 C10 H10B 109.5(2) . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5(2) . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 H11A 109.5(2) . . ? N2 C11 H11B 109.5(2) . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5(2) . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5(2) . . ? N2 C12 H12B 109.5(2) . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5(2) . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 116.1(3) . . ? C18 C13 Sn 120.0(3) . . ? C14 C13 Sn 123.9(2) . . ? C15 C14 C13 121.6(3) . . ? C15 C14 H14 119.2(2) . . ? C13 C14 H14 119.2(2) . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9(2) . . ? C14 C15 H15 119.9(2) . . ? C15 C16 C17 120.4(4) . . ? C15 C16 H16 119.8(2) . . ? C17 C16 H16 119.8(3) . . ? C16 C17 C18 118.9(4) . . ? C16 C17 H17 120.6(3) . . ? C18 C17 H17 120.6(3) . . ? C17 C18 C13 122.8(4) . . ? C17 C18 H18 118.6(3) . . ? C13 C18 H18 118.6(2) . . ? C24A C19 C20A 113.7(5) . . ? C20 C19 C24 112.3(7) . . ? C20 C19 Sn 129.8(7) . . ? C24A C19 Sn 129.5(5) . . ? C20A C19 Sn 116.7(3) . . ? C24 C19 Sn 117.5(4) . . ? C21A C20A C19 122.5(6) . . ? C21A C20A H20A 118.7(4) . . ? C19 C20A H20A 118.7(3) . . ? C20A C21A C22 114.7(7) . . ? C20A C21A H21A 122.7(4) . . ? C22 C21A H21A 122.7(4) . . ? C22 C23A C24A 121.8(9) . . ? C22 C23A H23A 119.1(6) . . ? C24A C23A H23A 119.1(5) . . ? C19 C24A C23A 124.7(8) . . ? C19 C24A H24A 117.6(4) . . ? C23A C24A H24A 117.6(5) . . ? C19 C20 C21 130.5(12) . . ? C19 C20 H20 114.7(6) . . ? C21 C20 H20 114.7(8) . . ? C22 C21 C20 122.5(16) . . ? C22 C21 H21 118.8(11) . . ? C20 C21 H21 118.8(8) . . ? C24 C23 C22 114.5(8) . . ? C24 C23 H23 122.8(5) . . ? C22 C23 H23 122.8(4) . . ? C23 C24 C19 118.3(7) . . ? C23 C24 H24 120.9(5) . . ? C19 C24 H24 120.9(3) . . ? C23A C22 C21A 122.0(8) . . ? C21 C22 C23 119.3(12) . . ? C23A C22 H22A 119.0(6) . . ? C21A C22 H22A 119.0(4) . . ? C21 C22 H22 120.3(11) . . ? C23 C22 H22 120.3(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 O4 Sn O1 C1 158.8(2) . . . . ? O2 Sn O1 C1 -4.2(2) . . . . ? C19 Sn O1 C1 -107.3(2) . . . . ? C13 Sn O1 C1 39.4(4) . . . . ? O3 Sn O1 C1 84.5(2) . . . . ? O4 Sn O2 C2 -38.0(3) . . . . ? C19 Sn O2 C2 92.2(2) . . . . ? C13 Sn O2 C2 -163.5(2) . . . . ? O3 Sn O2 C2 -73.8(2) . . . . ? O1 Sn O2 C2 4.2(2) . . . . ? O4 Sn O3 C7 -11.9(2) . . . . ? O2 Sn O3 C7 152.9(2) . . . . ? C19 Sn O3 C7 31.2(5) . . . . ? C13 Sn O3 C7 -114.3(2) . . . . ? O1 Sn O3 C7 78.2(2) . . . . ? O2 Sn O4 C8 -24.4(4) . . . . ? C19 Sn O4 C8 -156.1(2) . . . . ? C13 Sn O4 C8 99.4(2) . . . . ? O3 Sn O4 C8 12.9(2) . . . . ? O1 Sn O4 C8 -64.7(2) . . . . ? Sn O1 C1 N1 -175.0(2) . . . . ? Sn O1 C1 C2 3.8(3) . . . . ? C5 N1 C1 O1 -177.8(4) . . . . ? C6 N1 C1 O1 1.5(5) . . . . ? C5 N1 C1 C2 3.5(6) . . . . ? C6 N1 C1 C2 -177.2(3) . . . . ? Sn O2 C2 C3 -123.6(2) . . . . ? Sn O2 C2 C4 114.5(2) . . . . ? Sn O2 C2 C1 -3.6(3) . . . . ? O1 C1 C2 O2 -0.6(4) . . . . ? N1 C1 C2 O2 178.1(3) . . . . ? O1 C1 C2 C3 117.4(3) . . . . ? N1 C1 C2 C3 -63.9(4) . . . . ? O1 C1 C2 C4 -117.7(3) . . . . ? N1 C1 C2 C4 61.0(4) . . . . ? Sn O3 C7 N2 -170.0(2) . . . . ? Sn O3 C7 C8 9.6(3) . . . . ? C11 N2 C7 O3 -0.1(4) . . . . ? C12 N2 C7 O3 -177.8(3) . . . . ? C11 N2 C7 C8 -179.6(3) . . . . ? C12 N2 C7 C8 2.6(5) . . . . ? Sn O4 C8 C9 108.8(3) . . . . ? Sn O4 C8 C10 -129.9(2) . . . . ? Sn O4 C8 C7 -11.8(3) . . . . ? O3 C7 C8 O4 0.1(4) . . . . ? N2 C7 C8 O4 179.7(3) . . . . ? O3 C7 C8 C9 -118.8(3) . . . . ? N2 C7 C8 C9 60.8(4) . . . . ? O3 C7 C8 C10 116.5(3) . . . . ? N2 C7 C8 C10 -63.9(4) . . . . ? O4 Sn C13 C18 144.2(3) . . . . ? O2 Sn C13 C18 -56.9(3) . . . . ? C19 Sn C13 C18 47.2(3) . . . . ? O3 Sn C13 C18 -142.1(3) . . . . ? O1 Sn C13 C18 -98.5(4) . . . . ? O4 Sn C13 C14 -35.1(3) . . . . ? O2 Sn C13 C14 123.8(3) . . . . ? C19 Sn C13 C14 -132.2(3) . . . . ? O3 Sn C13 C14 38.5(3) . . . . ? O1 Sn C13 C14 82.2(4) . . . . ? C18 C13 C14 C15 1.9(5) . . . . ? Sn C13 C14 C15 -178.7(3) . . . . ? C13 C14 C15 C16 -2.4(6) . . . . ? C14 C15 C16 C17 1.7(7) . . . . ? C15 C16 C17 C18 -0.6(7) . . . . ? C16 C17 C18 C13 0.2(7) . . . . ? C14 C13 C18 C17 -0.9(6) . . . . ? Sn C13 C18 C17 179.8(3) . . . . ? O4 Sn C19 C20 14.6(10) . . . . ? O2 Sn C19 C20 -146.0(9) . . . . ? C13 Sn C19 C20 117.9(9) . . . . ? O3 Sn C19 C20 -26.6(11) . . . . ? O1 Sn C19 C20 -72.1(10) . . . . ? O4 Sn C19 C24A 150.8(7) . . . . ? O2 Sn C19 C24A -9.8(7) . . . . ? C13 Sn C19 C24A -105.9(6) . . . . ? O3 Sn C19 C24A 109.6(7) . . . . ? O1 Sn C19 C24A 64.1(7) . . . . ? O4 Sn C19 C20A -24.2(4) . . . . ? O2 Sn C19 C20A 175.1(3) . . . . ? C13 Sn C19 C20A 79.1(4) . . . . ? O3 Sn C19 C20A -65.4(6) . . . . ? O1 Sn C19 C20A -110.9(3) . . . . ? O4 Sn C19 C24 -173.1(4) . . . . ? O2 Sn C19 C24 26.2(4) . . . . ? C13 Sn C19 C24 -69.8(4) . . . . ? O3 Sn C19 C24 145.7(5) . . . . ? O1 Sn C19 C24 100.2(4) . . . . ? C20 C19 C20A C21A 60.6(12) . . . . ? C24A C19 C20A C21A 7.1(9) . . . . ? C24 C19 C20A C21A -28.4(8) . . . . ? Sn C19 C20A C21A -177.1(5) . . . . ? C19 C20A C21A C22 -2.2(9) . . . . ? C20 C19 C24A C23A -34.6(11) . . . . ? C20A C19 C24A C23A -7.3(11) . . . . ? C24 C19 C24A C23A 98.4(13) . . . . ? Sn C19 C24A C23A 177.5(6) . . . . ? C22 C23A C24A C19 2.2(15) . . . . ? C24A C19 C20 C21 34.9(16) . . . . ? C20A C19 C20 C21 -97.7(19) . . . . ? C24 C19 C20 C21 10.0(18) . . . . ? Sn C19 C20 C21 -177.4(11) . . . . ? C19 C20 C21 C22 4.1(27) . . . . ? C22 C23 C24 C19 -0.7(10) . . . . ? C20 C19 C24 C23 -9.3(11) . . . . ? C24A C19 C24 C23 -61.6(10) . . . . ? C20A C19 C24 C23 28.7(9) . . . . ? Sn C19 C24 C23 177.2(6) . . . . ? C20 C21 C22 C23A -43.0(19) . . . . ? C20 C21 C22 C21A 83.4(19) . . . . ? C20 C21 C22 C23 -16.4(22) . . . . ? C24A C23A C22 C21 39.8(16) . . . . ? C24A C23A C22 C21A 3.7(14) . . . . ? C24A C23A C22 C23 -88.4(14) . . . . ? C20A C21A C22 C21 -71.4(17) . . . . ? C20A C21A C22 C23A -3.5(12) . . . . ? C20A C21A C22 C23 30.9(10) . . . . ? C24 C23 C22 C21 14.5(16) . . . . ? C24 C23 C22 C23A 76.1(13) . . . . ? C24 C23 C22 C21A -29.5(11) . . . . ? #END OF CIF