# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H31 Bi N2 O3 Si2' _chemical_formula_sum 'C16 H31 Bi N2 O3 Si2' _chemical_formula_weight 564.59 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.1780(12) _cell_length_b 11.1920(10) _cell_length_c 15.8121(19) _cell_angle_alpha 90 _cell_angle_beta 105.551(6) _cell_angle_gamma 90 _cell_volume 2246.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 22306 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 7.969 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 1 0.165 -1 0 0 0.093 0 0 -1 0.097 0 0 1 0.145 0 1 0 0.054 0 -1 0 0.132 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.087 _exptl_absorpt_correction_T_max 0.309 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22262 _diffrn_reflns_av_R_equivalents 0.1517 _diffrn_reflns_av_sigmaI/netI 0.0956 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5118 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0546P)^2^+14.4027P] 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 5118 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1039 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Bi1 Bi 0.15717(3) 0.05024(3) 0.57885(2) 0.03639(15) Uani 1 1 d . . . Si2 Si 0.1436(2) -0.2507(3) 0.5243(2) 0.0430(7) Uani 1 1 d . . . Si1 Si 0.3014(2) -0.1096(3) 0.4648(2) 0.0434(7) Uani 1 1 d . . . O1 O 0.2568(6) 0.0107(7) 0.4980(5) 0.0460(18) Uani 1 1 d . . . O3 O 0.1069(7) -0.1307(7) 0.5624(5) 0.057(2) Uani 1 1 d . . . C14 C 0.3189(12) -0.0869(14) 0.3546(9) 0.067(4) Uani 1 1 d . . . H14A H 0.2585 -0.0450 0.3197 0.081 Uiso 1 1 d R . . H14B H 0.3247 -0.1629 0.3282 0.081 Uiso 1 1 d R . . H14C H 0.3812 -0.0407 0.3578 0.081 Uiso 1 1 d R . . C13 C 0.4279(10) -0.1560(14) 0.5397(10) 0.073(4) Uani 1 1 d . . . H13A H 0.4816 -0.0993 0.5369 0.087 Uiso 1 1 d R . . H13B H 0.4464 -0.2332 0.5221 0.087 Uiso 1 1 d R . . H13C H 0.4216 -0.1600 0.5987 0.087 Uiso 1 1 d R . . N2 N 0.0734(8) -0.0014(9) 0.7155(6) 0.047(2) Uani 1 1 d . . . C1 C 0.2844(8) 0.0235(9) 0.7051(6) 0.037(2) Uani 1 1 d . . . O2 O 0.2172(6) -0.2205(7) 0.4594(5) 0.051(2) Uani 1 1 d . . . N1 N 0.3004(8) 0.2312(9) 0.6055(7) 0.053(2) Uani 1 1 d . . . C10 C 0.1533(10) -0.0873(11) 0.7637(7) 0.052(3) Uani 1 1 d . . . H10A H 0.1462 -0.1619 0.7314 0.062 Uiso 1 1 d R . . H10B H 0.1434 -0.1035 0.8212 0.062 Uiso 1 1 d R . . C9 C 0.2839(11) 0.3209(12) 0.6684(10) 0.070(4) Uani 1 1 d . . . H9A H 0.2783 0.2809 0.7207 0.084 Uiso 1 1 d R . . H9B H 0.2200 0.3638 0.6429 0.084 Uiso 1 1 d R . . H9C H 0.3420 0.3758 0.6829 0.084 Uiso 1 1 d R . . C6 C 0.2615(10) -0.0355(10) 0.7729(7) 0.047(3) Uani 1 1 d . . . C7 C 0.3965(10) 0.1624(12) 0.6440(9) 0.059(3) Uani 1 1 d . . . H7A H 0.4537 0.2171 0.6691 0.071 Uiso 1 1 d R . . H7B H 0.4163 0.1151 0.5996 0.071 Uiso 1 1 d R . . C5 C 0.3395(10) -0.0482(13) 0.8510(8) 0.060(3) Uani 1 1 d . . . H5 H 0.3266 -0.0918 0.8971 0.072 Uiso 1 1 d R . . C2 C 0.3796(9) 0.0819(11) 0.7153(7) 0.048(3) Uani 1 1 d . . . C3 C 0.4565(9) 0.0707(12) 0.7936(9) 0.059(4) Uani 1 1 d . . . H3 H 0.5207 0.1100 0.8024 0.071 Uiso 1 1 d R . . C12 C -0.0302(10) -0.0596(14) 0.6877(9) 0.069(4) Uani 1 1 d . . . H12A H -0.0296 -0.1206 0.6452 0.082 Uiso 1 1 d R . . H12B H -0.0826 -0.0008 0.6623 0.082 Uiso 1 1 d R . . H12C H -0.0464 -0.0947 0.7379 0.082 Uiso 1 1 d R . . C16 C 0.0267(10) -0.3336(11) 0.4595(9) 0.061(3) Uani 1 1 d . . . H16A H -0.0260 -0.3361 0.4913 0.073 Uiso 1 1 d R . . H16B H 0.0468 -0.4136 0.4492 0.073 Uiso 1 1 d R . . H16C H -0.0013 -0.2940 0.4043 0.073 Uiso 1 1 d R . . C11 C 0.0687(12) 0.1028(14) 0.7696(9) 0.070(4) Uani 1 1 d . . . H11A H 0.0533 0.0782 0.8230 0.084 Uiso 1 1 d R . . H11B H 0.0144 0.1556 0.7378 0.084 Uiso 1 1 d R . . H11C H 0.1353 0.1435 0.7833 0.084 Uiso 1 1 d R . . C4 C 0.4359(12) 0.0029(15) 0.8610(10) 0.073(4) Uani 1 1 d . . . H4 H 0.4888 -0.0096 0.9125 0.088 Uiso 1 1 d R . . C8 C 0.3055(11) 0.2874(13) 0.5235(10) 0.073(4) Uani 1 1 d . . . H8A H 0.3676 0.3359 0.5335 0.087 Uiso 1 1 d R . . H8B H 0.2442 0.3365 0.5023 0.087 Uiso 1 1 d R . . H8C H 0.3072 0.2271 0.4808 0.087 Uiso 1 1 d R . . C15 C 0.2182(15) -0.3498(18) 0.6128(11) 0.108(7) Uani 1 1 d . . . H15A H 0.2832 -0.3116 0.6425 0.130 Uiso 1 1 d R . . H15B H 0.2329 -0.4240 0.5880 0.130 Uiso 1 1 d R . . H15C H 0.1776 -0.3650 0.6538 0.130 Uiso 1 1 d 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 Bi1 0.0383(2) 0.0349(2) 0.0340(2) 0.00015(17) 0.00633(15) 0.00370(18) Si2 0.0490(17) 0.0378(16) 0.0421(16) -0.0004(13) 0.0120(14) 0.0017(14) Si1 0.0417(16) 0.0487(19) 0.0403(16) -0.0042(14) 0.0119(13) 0.0014(14) O1 0.049(4) 0.044(4) 0.048(4) -0.004(4) 0.019(4) 0.000(4) O3 0.073(5) 0.047(5) 0.059(5) -0.015(4) 0.032(4) -0.021(5) C14 0.079(10) 0.075(9) 0.055(8) -0.009(7) 0.030(7) -0.006(8) C13 0.061(8) 0.060(9) 0.086(10) 0.008(8) 0.001(7) 0.001(7) N2 0.050(5) 0.053(6) 0.041(5) 0.002(5) 0.018(4) 0.011(5) C1 0.045(6) 0.031(5) 0.034(5) -0.004(4) 0.011(4) -0.004(5) O2 0.056(5) 0.049(5) 0.050(4) -0.016(4) 0.019(4) -0.002(4) N1 0.060(6) 0.038(5) 0.064(6) 0.001(5) 0.020(5) -0.005(5) C10 0.073(8) 0.046(6) 0.039(6) 0.002(5) 0.021(6) 0.006(6) C9 0.065(8) 0.046(8) 0.095(11) -0.021(7) 0.014(8) -0.003(7) C6 0.056(7) 0.040(6) 0.041(6) -0.006(5) 0.006(5) 0.006(6) C7 0.053(7) 0.051(8) 0.067(8) -0.007(7) 0.005(6) 0.001(6) C5 0.061(8) 0.078(9) 0.032(6) 0.009(6) -0.001(5) 0.007(7) C2 0.048(6) 0.051(7) 0.041(6) -0.009(5) 0.007(5) 0.004(6) C3 0.035(6) 0.062(9) 0.069(8) -0.008(7) -0.007(6) 0.000(6) C12 0.045(7) 0.112(13) 0.052(7) 0.012(8) 0.018(6) -0.016(8) C16 0.073(8) 0.042(7) 0.066(8) -0.014(6) 0.019(7) -0.015(7) C11 0.080(10) 0.075(10) 0.062(8) 0.008(7) 0.032(8) 0.030(8) C4 0.065(9) 0.072(10) 0.062(9) -0.005(8) -0.017(7) 0.010(8) C8 0.072(9) 0.065(9) 0.084(10) 0.004(8) 0.025(8) -0.028(8) C15 0.123(15) 0.113(15) 0.079(11) 0.044(11) 0.011(10) 0.060(13) _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 Bi1 O1 2.111(7) . ? Bi1 O3 2.125(8) . ? Bi1 C1 2.257(10) . ? Bi1 N1 2.723(10) . ? Bi1 N2 2.738(9) . ? Si2 O3 1.600(9) . ? Si2 O2 1.624(8) . ? Si2 C15 1.849(14) . ? Si2 C16 1.854(12) . ? Si1 O1 1.613(8) . ? Si1 O2 1.652(8) . ? Si1 C14 1.835(13) . ? Si1 C13 1.841(13) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9601 . ? N2 C11 1.458(17) . ? N2 C12 1.470(16) . ? N2 C10 1.478(15) . ? C1 C6 1.360(15) . ? C1 C2 1.386(16) . ? N1 C8 1.458(16) . ? N1 C7 1.468(15) . ? N1 C9 1.470(16) . ? C10 C6 1.509(17) . ? C10 H10A 0.9700 . ? C10 H10B 0.9699 . ? C9 H9A 0.9599 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C6 C5 1.386(16) . ? C7 C2 1.505(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9701 . ? C5 C4 1.36(2) . ? C5 H5 0.9300 . ? C2 C3 1.380(16) . ? C3 C4 1.39(2) . ? C3 H3 0.9299 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C16 H16A 0.9601 . ? C16 H16B 0.9599 . ? C16 H16C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9599 . ? C4 H4 0.9301 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C15 H15A 0.9599 . ? C15 H15B 0.9600 . ? C15 H15C 0.9599 . ? 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 Bi1 O3 87.2(3) . . ? O1 Bi1 C1 94.2(3) . . ? O3 Bi1 C1 96.6(4) . . ? O1 Bi1 N1 74.4(3) . . ? O3 Bi1 N1 155.3(3) . . ? C1 Bi1 N1 69.0(3) . . ? O1 Bi1 N2 151.8(3) . . ? O3 Bi1 N2 73.6(3) . . ? C1 Bi1 N2 68.6(3) . . ? N1 Bi1 N2 116.4(3) . . ? O3 Si2 O2 110.8(4) . . ? O3 Si2 C15 111.8(7) . . ? O2 Si2 C15 108.5(7) . . ? O3 Si2 C16 109.8(5) . . ? O2 Si2 C16 107.7(5) . . ? C15 Si2 C16 108.2(8) . . ? O1 Si1 O2 110.2(4) . . ? O1 Si1 C14 110.0(6) . . ? O2 Si1 C14 108.0(6) . . ? O1 Si1 C13 111.8(6) . . ? O2 Si1 C13 107.5(6) . . ? C14 Si1 C13 109.1(7) . . ? Si1 O1 Bi1 135.4(5) . . ? Si2 O3 Bi1 136.9(5) . . ? Si1 C14 H14A 108.6 . . ? Si1 C14 H14B 109.6 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 110.3 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C13 H13A 109.6 . . ? Si1 C13 H13B 108.9 . . ? H13A C13 H13B 109.5 . . ? Si1 C13 H13C 109.9 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 N2 C12 110.3(10) . . ? C11 N2 C10 110.8(10) . . ? C12 N2 C10 110.0(11) . . ? C11 N2 Bi1 112.6(8) . . ? C12 N2 Bi1 113.3(7) . . ? C10 N2 Bi1 99.3(6) . . ? C6 C1 C2 121.5(10) . . ? C6 C1 Bi1 119.5(8) . . ? C2 C1 Bi1 118.4(8) . . ? Si2 O2 Si1 129.1(5) . . ? C8 N1 C7 110.8(11) . . ? C8 N1 C9 111.0(11) . . ? C7 N1 C9 110.2(10) . . ? C8 N1 Bi1 112.2(8) . . ? C7 N1 Bi1 99.1(7) . . ? C9 N1 Bi1 113.0(8) . . ? N2 C10 C6 108.9(10) . . ? N2 C10 H10A 109.5 . . ? C6 C10 H10A 109.8 . . ? N2 C10 H10B 110.4 . . ? C6 C10 H10B 110.1 . . ? H10A C10 H10B 108.3 . . ? N1 C9 H9A 109.0 . . ? N1 C9 H9B 109.2 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 110.2 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C6 C5 119.0(12) . . ? C1 C6 C10 120.9(10) . . ? C5 C6 C10 120.1(11) . . ? N1 C7 C2 109.9(10) . . ? N1 C7 H7A 109.2 . . ? C2 C7 H7A 109.0 . . ? N1 C7 H7B 110.8 . . ? C2 C7 H7B 109.8 . . ? H7A C7 H7B 108.1 . . ? C4 C5 C6 120.3(13) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 120.3 . . ? C3 C2 C1 119.0(12) . . ? C3 C2 C7 120.4(12) . . ? C1 C2 C7 120.4(10) . . ? C2 C3 C4 119.3(12) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.0 . . ? N2 C12 H12A 110.0 . . ? N2 C12 H12B 109.2 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.2 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si2 C16 H16A 109.6 . . ? Si2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si2 C16 H16C 109.3 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C11 H11A 109.9 . . ? N2 C11 H11B 109.2 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.4 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C4 C3 120.5(12) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.9 . . ? N1 C8 H8A 109.8 . . ? N1 C8 H8B 108.8 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.8 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Si2 C15 H15A 109.1 . . ? Si2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si2 C15 H15C 109.8 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.360 _refine_diff_density_min -2.973 _refine_diff_density_rms 0.226 _database_code_depnum_ccdc_archive 'CCDC 936153' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H58 N4 O4 Sb2 Si2' _chemical_formula_sum 'C48 H58 N4 O4 Sb2 Si2' _chemical_formula_weight 1054.66 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' N N 0.0061 0.0033 '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' Sb Sb -0.5866 1.5461 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.7080(5) _cell_length_b 15.9991(10) _cell_length_c 13.7490(6) _cell_angle_alpha 90 _cell_angle_beta 113.078(4) _cell_angle_gamma 90 _cell_volume 2369.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 20112 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.237 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 -1 0.034 0 -1 1 0.115 0 1 1 0.113 0 -1 -1 0.161 1 0 0 0.011 -1 0 0 0.086 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.699 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20039 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5376 _reflns_number_gt 4424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0192P)^2^+2.7364P] 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 5376 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 Sb1 Sb -0.053802(15) -0.044561(10) 0.292794(13) 0.01754(6) Uani 1 1 d . . . Si1 Si -0.18451(6) 0.02079(4) 0.45540(6) 0.01804(15) Uani 1 1 d . . . C13 C -0.2379(2) -0.08992(17) 0.4551(2) 0.0224(6) Uani 1 1 d . . . O2 O 0.09615(17) -0.04774(12) 0.42645(14) 0.0221(4) Uani 1 1 d . . . O1 O -0.12614(16) 0.03380(11) 0.36748(14) 0.0205(4) Uani 1 1 d . . . N2 N -0.2524(2) 0.03016(14) 0.13542(18) 0.0236(5) Uani 1 1 d . . . C1 C 0.0068(2) 0.05719(15) 0.22046(19) 0.0175(5) Uani 1 1 d . . . N1 N 0.1375(2) -0.09426(14) 0.23703(18) 0.0227(5) Uani 1 1 d . . . C14 C -0.1705(3) -0.14531(17) 0.5368(2) 0.0243(6) Uani 1 1 d . . . H14 H -0.0957 -0.1280 0.5889 0.029 Uiso 1 1 d R . . C4 C 0.0905(3) 0.19394(18) 0.1407(2) 0.0289(6) Uani 1 1 d . . . H4 H 0.1203 0.2413 0.1192 0.035 Uiso 1 1 d R . . C5 C -0.0313(3) 0.19047(17) 0.1308(2) 0.0248(6) Uani 1 1 d . . . H5 H -0.0853 0.2340 0.0977 0.030 Uiso 1 1 d R . . C9 C 0.2132(3) -0.16430(18) 0.2952(2) 0.0312(7) Uani 1 1 d . . . H9A H 0.2857 -0.1686 0.2791 0.037 Uiso 1 1 d R . . H9B H 0.1660 -0.2150 0.2749 0.037 Uiso 1 1 d R . . H9C H 0.2379 -0.1554 0.3697 0.037 Uiso 1 1 d R . . C11 C -0.2594(3) 0.0005(2) 0.0330(2) 0.0356(7) Uani 1 1 d . . . H11A H -0.2810 -0.0578 0.0257 0.043 Uiso 1 1 d R . . H11B H -0.1805 0.0079 0.0281 0.043 Uiso 1 1 d R . . H11C H -0.3216 0.0316 -0.0222 0.043 Uiso 1 1 d R . . C7 C 0.2100(2) -0.01680(17) 0.2637(2) 0.0232(6) Uani 1 1 d . . . H7A H 0.2721 -0.0180 0.2333 0.028 Uiso 1 1 d R . . H7B H 0.2527 -0.0124 0.3398 0.028 Uiso 1 1 d R . . C3 C 0.1682(3) 0.12664(18) 0.1831(2) 0.0261(6) Uani 1 1 d . . . H3 H 0.2487 0.1274 0.1855 0.031 Uiso 1 1 d R . . C6 C -0.0742(2) 0.12204(17) 0.1700(2) 0.0208(5) Uani 1 1 d . . . C2 C 0.1274(2) 0.05775(16) 0.2220(2) 0.0207(6) Uani 1 1 d . . . C8 C 0.0889(3) -0.11132(19) 0.1233(2) 0.0302(6) Uani 1 1 d . . . H8A H 0.0415 -0.0642 0.0852 0.036 Uiso 1 1 d R . . H8B H 0.0366 -0.1599 0.1079 0.036 Uiso 1 1 d R . . H8C H 0.1568 -0.1211 0.1022 0.036 Uiso 1 1 d R . . C24 C -0.2993(3) 0.17833(17) 0.3993(2) 0.0238(6) Uani 1 1 d . . . H24 H -0.2243 0.1932 0.3956 0.029 Uiso 1 1 d R . . C23 C -0.3890(3) 0.23868(19) 0.3835(2) 0.0293(6) Uani 1 1 d . . . H23 H -0.3732 0.2937 0.3707 0.035 Uiso 1 1 d R . . C21 C -0.5237(3) 0.13609(19) 0.4077(2) 0.0304(7) Uani 1 1 d . . . H21 H -0.5988 0.1215 0.4113 0.037 Uiso 1 1 d R . . C20 C -0.4332(3) 0.07580(18) 0.4236(2) 0.0247(6) Uani 1 1 d . . . H20 H -0.4494 0.0209 0.4366 0.030 Uiso 1 1 d R . . C22 C -0.5024(3) 0.21716(19) 0.3873(2) 0.0323(7) Uani 1 1 d . . . H22 H -0.5635 0.2576 0.3757 0.039 Uiso 1 1 d R . . C15 C -0.2128(3) -0.22586(18) 0.5408(2) 0.0295(6) Uani 1 1 d . . . H15 H -0.1676 -0.2612 0.5963 0.035 Uiso 1 1 d R . . C19 C -0.3187(2) 0.09514(17) 0.41989(19) 0.0195(5) Uani 1 1 d . . . C10 C -0.2087(2) 0.11668(17) 0.1546(2) 0.0233(6) Uani 1 1 d . . . H10A H -0.2185 0.1376 0.2171 0.028 Uiso 1 1 d R . . H10B H -0.2584 0.1512 0.0951 0.028 Uiso 1 1 d R . . C18 C -0.3473(3) -0.12081(19) 0.3773(2) 0.0281(6) Uani 1 1 d . . . H18 H -0.3935 -0.0862 0.3213 0.034 Uiso 1 1 d R . . C16 C -0.3218(3) -0.25322(18) 0.4635(3) 0.0329(7) Uani 1 1 d . . . H16 H -0.3503 -0.3069 0.4671 0.039 Uiso 1 1 d R . . C12 C -0.3724(3) 0.0220(2) 0.1430(2) 0.0345(7) Uani 1 1 d . . . H12A H -0.4324 0.0563 0.0902 0.041 Uiso 1 1 d R . . H12B H -0.3655 0.0396 0.2119 0.041 Uiso 1 1 d R . . H12C H -0.3985 -0.0353 0.1321 0.041 Uiso 1 1 d R . . C17 C -0.3888(3) -0.20091(19) 0.3807(3) 0.0335(7) Uani 1 1 d . . . H17 H -0.4617 -0.2197 0.3275 0.040 Uiso 1 1 d 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 Sb1 0.01806(9) 0.02005(9) 0.01576(9) 0.00040(7) 0.00796(7) -0.00280(7) Si1 0.0151(3) 0.0248(4) 0.0156(3) 0.0015(3) 0.0075(3) 0.0004(3) C13 0.0240(14) 0.0265(14) 0.0223(13) -0.0025(11) 0.0151(11) -0.0004(11) O2 0.0190(9) 0.0312(10) 0.0163(9) -0.0001(8) 0.0071(7) 0.0031(8) O1 0.0188(9) 0.0272(10) 0.0180(9) 0.0013(8) 0.0098(7) 0.0026(8) N2 0.0208(12) 0.0301(13) 0.0190(11) -0.0011(9) 0.0070(9) -0.0052(10) C1 0.0209(13) 0.0199(13) 0.0130(11) -0.0019(10) 0.0081(10) -0.0034(10) N1 0.0282(13) 0.0228(12) 0.0218(12) 0.0013(9) 0.0148(10) 0.0016(9) C14 0.0257(14) 0.0267(14) 0.0228(13) -0.0024(11) 0.0118(11) 0.0055(11) C4 0.0381(17) 0.0253(14) 0.0295(15) 0.0032(12) 0.0199(13) -0.0068(13) C5 0.0316(16) 0.0208(13) 0.0235(14) 0.0025(11) 0.0122(12) 0.0030(11) C9 0.0398(18) 0.0266(15) 0.0345(16) 0.0042(13) 0.0223(14) 0.0085(13) C11 0.0385(18) 0.0428(19) 0.0242(15) -0.0097(14) 0.0108(14) -0.0106(15) C7 0.0207(14) 0.0300(14) 0.0233(14) 0.0023(11) 0.0135(11) -0.0003(11) C3 0.0247(14) 0.0313(15) 0.0272(14) 0.0005(12) 0.0152(12) -0.0059(12) C6 0.0240(14) 0.0256(14) 0.0147(12) -0.0018(10) 0.0095(10) -0.0020(11) C2 0.0233(14) 0.0248(14) 0.0161(12) -0.0011(10) 0.0101(11) -0.0013(11) C8 0.0377(17) 0.0338(16) 0.0229(14) -0.0056(12) 0.0161(13) -0.0013(13) C24 0.0204(14) 0.0324(15) 0.0204(13) -0.0001(11) 0.0099(11) -0.0025(11) C23 0.0339(17) 0.0267(15) 0.0300(15) 0.0040(12) 0.0153(13) 0.0020(12) C21 0.0194(14) 0.0429(18) 0.0335(16) 0.0029(14) 0.0152(12) 0.0036(13) C20 0.0226(14) 0.0303(14) 0.0246(14) 0.0031(12) 0.0130(12) 0.0006(11) C22 0.0308(17) 0.0357(17) 0.0348(16) 0.0059(14) 0.0177(14) 0.0120(13) C15 0.0375(17) 0.0237(14) 0.0331(16) 0.0048(12) 0.0201(14) 0.0090(13) C19 0.0162(13) 0.0283(14) 0.0140(12) 0.0007(10) 0.0059(10) 0.0018(10) C10 0.0226(14) 0.0272(14) 0.0193(13) 0.0010(11) 0.0073(11) 0.0001(11) C18 0.0271(15) 0.0329(16) 0.0246(14) 0.0013(12) 0.0102(12) -0.0009(12) C16 0.0411(18) 0.0208(14) 0.0477(19) -0.0037(13) 0.0292(16) -0.0010(13) C12 0.0241(16) 0.0491(19) 0.0281(16) -0.0011(14) 0.0079(13) -0.0096(13) C17 0.0300(17) 0.0365(17) 0.0359(17) -0.0101(14) 0.0149(14) -0.0074(13) _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 Sb1 O2 1.9831(18) . ? Sb1 O1 2.0063(17) . ? Sb1 C1 2.167(2) . ? Si1 O2 1.6055(19) 3_556 ? Si1 O1 1.6184(18) . ? Si1 C19 1.876(3) . ? Si1 C13 1.878(3) . ? C13 C18 1.399(4) . ? C13 C14 1.405(4) . ? O2 Si1 1.6055(19) 3_556 ? N2 C12 1.454(4) . ? N2 C11 1.458(4) . ? N2 C10 1.464(3) . ? C1 C6 1.393(4) . ? C1 C2 1.404(4) . ? N1 C9 1.458(4) . ? N1 C7 1.465(3) . ? N1 C8 1.465(3) . ? C14 C15 1.390(4) . ? C14 H14 0.9301 . ? C4 C5 1.380(4) . ? C4 C3 1.382(4) . ? C4 H4 0.9300 . ? C5 C6 1.398(4) . ? C5 H5 0.9301 . ? C9 H9A 0.9599 . ? C9 H9B 0.9599 . ? C9 H9C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9601 . ? C11 H11C 0.9600 . ? C7 C2 1.501(4) . ? C7 H7A 0.9699 . ? C7 H7B 0.9700 . ? C3 C2 1.389(4) . ? C3 H3 0.9301 . ? C6 C10 1.507(4) . ? C8 H8A 0.9601 . ? C8 H8B 0.9599 . ? C8 H8C 0.9600 . ? C24 C23 1.380(4) . ? C24 C19 1.398(4) . ? C24 H24 0.9300 . ? C23 C22 1.392(4) . ? C23 H23 0.9300 . ? C21 C22 1.370(4) . ? C21 C20 1.385(4) . ? C21 H21 0.9300 . ? C20 C19 1.396(4) . ? C20 H20 0.9301 . ? C22 H22 0.9300 . ? C15 C16 1.373(5) . ? C15 H15 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C18 C17 1.378(4) . ? C18 H18 0.9300 . ? C16 C17 1.383(5) . ? C16 H16 0.9299 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C17 H17 0.9300 . ? 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 O2 Sb1 O1 86.55(7) . . ? O2 Sb1 C1 96.57(9) . . ? O1 Sb1 C1 92.59(8) . . ? O2 Si1 O1 115.34(10) 3_556 . ? O2 Si1 C19 103.57(11) 3_556 . ? O1 Si1 C19 106.25(10) . . ? O2 Si1 C13 109.71(11) 3_556 . ? O1 Si1 C13 110.95(10) . . ? C19 Si1 C13 110.69(12) . . ? C18 C13 C14 116.6(3) . . ? C18 C13 Si1 122.6(2) . . ? C14 C13 Si1 120.8(2) . . ? Si1 O2 Sb1 156.35(12) 3_556 . ? Si1 O1 Sb1 133.51(11) . . ? C12 N2 C11 110.5(2) . . ? C12 N2 C10 110.6(2) . . ? C11 N2 C10 111.5(2) . . ? C6 C1 C2 119.1(2) . . ? C6 C1 Sb1 120.44(18) . . ? C2 C1 Sb1 120.41(18) . . ? C9 N1 C7 110.2(2) . . ? C9 N1 C8 109.9(2) . . ? C7 N1 C8 111.6(2) . . ? C15 C14 C13 121.3(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.5 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.8 . . ? N1 C9 H9A 109.3 . . ? N1 C9 H9B 109.4 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.6 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C11 H11A 109.3 . . ? N2 C11 H11B 109.7 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.4 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C7 C2 110.7(2) . . ? N1 C7 H7A 109.5 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.5 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.5 . . ? C1 C6 C5 119.9(2) . . ? C1 C6 C10 119.8(2) . . ? C5 C6 C10 120.3(2) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 C7 120.7(2) . . ? C1 C2 C7 119.7(2) . . ? N1 C8 H8A 109.6 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C23 C24 C19 121.6(3) . . ? C23 C24 H24 119.3 . . ? C19 C24 H24 119.1 . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 120.3 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 119.8 . . ? C21 C20 C19 121.7(3) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.2 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.1 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C20 C19 C24 117.0(2) . . ? C20 C19 Si1 124.6(2) . . ? C24 C19 Si1 118.03(19) . . ? N2 C10 C6 110.6(2) . . ? N2 C10 H10A 109.4 . . ? C6 C10 H10A 109.6 . . ? N2 C10 H10B 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C17 C18 C13 122.1(3) . . ? C17 C18 H18 119.0 . . ? C13 C18 H18 118.9 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 120.2 . . ? N2 C12 H12A 109.6 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.4 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C17 C16 119.8(3) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.975 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 936154' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H39 Bi N2 O3 Si2' _chemical_formula_sum 'C36 H39 Bi N2 O3 Si2' _chemical_formula_weight 812.85 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' N N 0.0061 0.0033 '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' Bi Bi -4.1077 10.2566 '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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 14.1440(10) _cell_length_b 20.3112(12) _cell_length_c 11.9648(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3437.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 25680 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 5.236 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.136 0 0 -1 0.149 1 0 0 0.100 -1 0 0 0.112 0 -1 0 0.191 0 1 0 0.219 0 -1 -1 0.161 0 1 -1 0.184 1 0 1 0.123 -1 0 -1 0.120 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.169 _exptl_absorpt_correction_T_max 0.384 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25644 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7029 _reflns_number_gt 6378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0287P)^2^+7.9786P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.020(6) _refine_ls_number_reflns 7029 _refine_ls_number_parameters 397 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.609951(10) 0.981471(7) 0.75133(3) 0.01716(5) Uani 1 1 d . . . Si1 Si 0.75320(13) 1.06591(8) 0.94366(15) 0.0179(3) Uani 1 1 d . . . Si2 Si 0.77861(11) 0.91894(7) 0.93791(13) 0.0175(3) Uani 1 1 d . . . O1 O 0.6739(3) 1.05881(18) 0.8486(3) 0.0231(8) Uani 1 1 d . . . C25 C 0.8940(4) 0.8896(3) 0.8774(5) 0.0211(11) Uani 1 1 d . . . O3 O 0.7910(3) 0.99400(17) 0.9865(3) 0.0202(8) Uani 1 1 d . . . C13 C 0.8576(4) 1.1136(3) 0.8906(5) 0.0212(11) Uani 1 1 d . . . C17 C 0.9866(4) 1.1903(3) 0.9181(6) 0.0347(15) Uani 1 1 d . . . H17 H 1.0194 1.2189 0.9648 0.042 Uiso 1 1 d R . . C30 C 0.9447(4) 0.8373(3) 0.9221(5) 0.0279(13) Uani 1 1 d . . . H30 H 0.9239 0.8162 0.9866 0.034 Uiso 1 1 d R . . C18 C 0.9078(4) 1.1576(3) 0.9569(5) 0.0239(12) Uani 1 1 d . . . H18 H 0.8881 1.1658 1.0297 0.029 Uiso 1 1 d R . . C15 C 0.9710(4) 1.1350(3) 0.7421(9) 0.0345(15) Uani 1 1 d . . . H15 H 0.9919 1.1268 0.6697 0.041 Uiso 1 1 d R . . O2 O 0.6993(3) 0.91501(18) 0.8431(3) 0.0220(8) Uani 1 1 d . . . C27 C 1.0144(4) 0.8990(3) 0.7324(5) 0.0309(15) Uani 1 1 d . . . H27 H 1.0381 0.9208 0.6700 0.037 Uiso 1 1 d R . . C26 C 0.9306(4) 0.9204(3) 0.7816(4) 0.0256(13) Uani 1 1 d . . . H26 H 0.8978 0.9550 0.7485 0.031 Uiso 1 1 d R . . C28 C 1.0628(5) 0.8474(3) 0.7785(5) 0.0344(17) Uani 1 1 d . . . H28 H 1.1193 0.8339 0.7461 0.041 Uiso 1 1 d R . . C14 C 0.8913(4) 1.1026(3) 0.7818(4) 0.0259(13) Uani 1 1 d . . . H14 H 0.8580 1.0736 0.7364 0.031 Uiso 1 1 d R . . C21 C 0.6534(5) 1.2095(3) 1.1640(6) 0.0363(16) Uani 1 1 d . . . H21 H 0.6392 1.2542 1.1614 0.044 Uiso 1 1 d R . . C19 C 0.7070(4) 1.1097(3) 1.0706(5) 0.0216(11) Uani 1 1 d . . . C20 C 0.6875(4) 1.1771(3) 1.0693(6) 0.0292(13) Uani 1 1 d . . . H20 H 0.7001 1.2009 1.0047 0.035 Uiso 1 1 d R . . C16 C 1.0177(5) 1.1795(3) 0.8099(6) 0.0363(16) Uani 1 1 d . . . H16 H 1.0705 1.2020 0.7839 0.044 Uiso 1 1 d R . . C29 C 1.0282(5) 0.8158(3) 0.8712(6) 0.0355(15) Uani 1 1 d . . . H29 H 1.0594 0.7791 0.8995 0.043 Uiso 1 1 d R . . C35 C 0.7407(4) 0.8395(3) 1.2563(8) 0.0301(11) Uani 1 1 d . . . H35 H 0.7514 0.8536 1.3291 0.036 Uiso 1 1 d R . . C34 C 0.7017(4) 0.7784(3) 1.2341(6) 0.0306(16) Uani 1 1 d . . . H34 H 0.6878 0.7507 1.2939 0.037 Uiso 1 1 d R . . C23 C 0.6567(5) 1.1076(4) 1.2652(7) 0.0414(17) Uani 1 1 d . . . H23 H 0.6434 1.0846 1.3305 0.050 Uiso 1 1 d R . . N1 N 0.6331(3) 0.8723(2) 0.6238(4) 0.0224(10) Uani 1 1 d . . . C22 C 0.6392(4) 1.1746(3) 1.2625(8) 0.0394(17) Uani 1 1 d . . . H22 H 0.6183 1.1972 1.3255 0.047 Uiso 1 1 d R . . C31 C 0.7482(4) 0.8642(3) 1.0587(5) 0.0206(11) Uani 1 1 d . . . N2 N 0.5699(3) 1.0937(2) 0.6466(4) 0.0258(11) Uani 1 1 d . . . C36 C 0.7638(4) 0.8818(3) 1.1698(5) 0.0243(12) Uani 1 1 d . . . H36 H 0.7902 0.9224 1.1872 0.029 Uiso 1 1 d R . . C33 C 0.6856(5) 0.7600(3) 1.1254(5) 0.0323(14) Uani 1 1 d . . . H33 H 0.6584 0.7192 1.1103 0.039 Uiso 1 1 d R . . C12 C 0.5212(5) 1.1427(3) 0.7159(6) 0.0393(17) Uani 1 1 d . . . H12A H 0.5027 1.1796 0.6706 0.047 Uiso 1 1 d R . . H12B H 0.4662 1.1232 0.7492 0.047 Uiso 1 1 d R . . H12C H 0.5633 1.1575 0.7737 0.047 Uiso 1 1 d R . . C8 C 0.5774(5) 0.8766(3) 0.5206(5) 0.0327(14) Uani 1 1 d . . . H8A H 0.5123 0.8671 0.5370 0.039 Uiso 1 1 d R . . H8B H 0.5824 0.9204 0.4911 0.039 Uiso 1 1 d R . . H8C H 0.6005 0.8457 0.4664 0.039 Uiso 1 1 d R . . C32 C 0.7086(4) 0.8020(3) 1.0377(5) 0.0266(13) Uani 1 1 d . . . H32 H 0.6983 0.7886 0.9644 0.032 Uiso 1 1 d R . . C24 C 0.6906(4) 1.0752(3) 1.1692(5) 0.0293(13) Uani 1 1 d . . . H24 H 0.7057 1.0307 1.1720 0.035 Uiso 1 1 d R . . C9 C 0.6131(5) 0.8096(3) 0.6812(5) 0.0321(14) Uani 1 1 d . . . H9A H 0.6365 0.7738 0.6368 0.039 Uiso 1 1 d R . . H9B H 0.6437 0.8093 0.7528 0.039 Uiso 1 1 d R . . H9C H 0.5461 0.8049 0.6912 0.039 Uiso 1 1 d R . . C11 C 0.5134(5) 1.0795(4) 0.5465(6) 0.0368(15) Uani 1 1 d . . . H11A H 0.5461 1.0499 0.4973 0.044 Uiso 1 1 d R . . H11B H 0.4551 1.0596 0.5702 0.044 Uiso 1 1 d R . . H11C H 0.5001 1.1199 0.5080 0.044 Uiso 1 1 d R . . C7 C 0.7352(4) 0.8765(3) 0.6011(5) 0.0220(11) Uani 1 1 d . . . H7A H 0.7514 0.8468 0.5406 0.026 Uiso 1 1 d R . . H7B H 0.7710 0.8636 0.6667 0.026 Uiso 1 1 d R . . C4 C 0.8505(5) 1.0224(3) 0.4553(6) 0.0329(14) Uani 1 1 d . . . H4 H 0.8987 1.0302 0.4041 0.040 Uiso 1 1 d R . . C1 C 0.7116(4) 0.9982(3) 0.6127(4) 0.0178(10) Uani 1 1 d . . . C2 C 0.7619(4) 0.9460(3) 0.5665(5) 0.0213(12) Uani 1 1 d . . . C10 C 0.6640(4) 1.1181(3) 0.6160(5) 0.0266(12) Uani 1 1 d . . . H10A H 0.6568 1.1525 0.5605 0.032 Uiso 1 1 d R . . H10B H 0.6927 1.1377 0.6817 0.032 Uiso 1 1 d R . . C6 C 0.7256(5) 1.0624(3) 0.5735(6) 0.0237(15) Uani 1 1 d . . . C3 C 0.8323(5) 0.9584(3) 0.4898(5) 0.0297(13) Uani 1 1 d . . . H3 H 0.8688 0.9239 0.4626 0.036 Uiso 1 1 d R . . C5 C 0.7956(5) 1.0736(3) 0.4943(5) 0.0296(13) Uani 1 1 d . . . H5 H 0.8057 1.1157 0.4662 0.035 Uiso 1 1 d 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 Bi1 0.01661(8) 0.01823(8) 0.01664(8) 0.00099(14) 0.00045(15) -0.00049(6) Si1 0.0232(8) 0.0137(7) 0.0167(7) -0.0002(6) -0.0007(7) -0.0005(6) Si2 0.0215(8) 0.0134(7) 0.0175(7) 0.0023(6) -0.0005(6) 0.0011(6) O1 0.030(2) 0.0187(18) 0.0206(19) -0.0023(15) -0.0065(18) 0.0065(17) C25 0.024(3) 0.019(2) 0.020(3) -0.003(2) 0.000(2) 0.001(2) O3 0.029(2) 0.0106(16) 0.0214(19) 0.0011(15) -0.0033(17) -0.0009(16) C13 0.026(3) 0.016(2) 0.021(3) 0.004(2) 0.001(2) 0.004(2) C17 0.023(3) 0.022(3) 0.059(4) 0.000(3) -0.008(3) -0.002(2) C30 0.029(3) 0.026(3) 0.030(3) -0.004(2) -0.003(3) 0.002(2) C18 0.025(3) 0.017(2) 0.029(3) 0.000(2) -0.003(2) 0.000(2) C15 0.034(3) 0.034(3) 0.035(4) 0.013(4) 0.016(4) 0.008(2) O2 0.027(2) 0.0167(17) 0.0223(19) 0.0008(15) -0.0046(16) -0.0032(16) C27 0.036(3) 0.041(3) 0.016(4) -0.005(3) 0.002(3) -0.007(3) C26 0.029(3) 0.024(3) 0.023(3) -0.001(2) -0.001(2) 0.000(2) C28 0.030(3) 0.036(3) 0.037(4) -0.020(3) -0.002(2) 0.004(3) C14 0.029(3) 0.024(3) 0.024(3) -0.001(2) -0.001(2) 0.005(2) C21 0.030(3) 0.030(3) 0.049(4) -0.017(3) 0.007(3) 0.001(3) C19 0.020(3) 0.024(3) 0.021(3) -0.003(2) -0.001(2) 0.001(2) C20 0.028(3) 0.021(3) 0.038(3) -0.004(3) 0.008(3) -0.002(2) C16 0.025(3) 0.023(3) 0.061(4) 0.018(3) 0.002(3) 0.001(2) C29 0.039(4) 0.027(3) 0.040(4) -0.007(3) -0.009(3) 0.011(3) C35 0.031(3) 0.040(3) 0.020(2) 0.011(4) 0.000(4) 0.003(2) C34 0.031(3) 0.032(3) 0.029(5) 0.013(3) 0.009(3) 0.003(2) C23 0.038(3) 0.064(4) 0.021(4) -0.003(4) 0.006(3) 0.006(3) N1 0.028(3) 0.017(2) 0.022(2) -0.0020(19) -0.002(2) -0.0021(19) C22 0.032(3) 0.057(4) 0.029(4) -0.017(4) 0.000(3) 0.006(3) C31 0.017(3) 0.018(2) 0.027(3) 0.005(2) -0.003(2) 0.002(2) N2 0.023(3) 0.027(3) 0.027(3) -0.001(2) 0.000(2) 0.009(2) C36 0.025(3) 0.025(3) 0.023(3) 0.002(2) 0.002(2) -0.001(2) C33 0.039(4) 0.020(3) 0.038(4) 0.008(3) 0.006(3) -0.001(3) C12 0.039(4) 0.032(3) 0.047(4) -0.007(3) 0.003(3) 0.014(3) C8 0.037(4) 0.034(3) 0.028(3) -0.002(3) -0.006(3) -0.009(3) C32 0.035(3) 0.019(3) 0.026(3) 0.005(2) -0.001(3) 0.000(2) C24 0.031(3) 0.037(3) 0.020(3) -0.003(2) -0.001(2) 0.007(3) C9 0.040(4) 0.019(3) 0.037(4) 0.002(2) -0.003(3) -0.008(3) C11 0.031(3) 0.044(4) 0.035(4) 0.000(3) -0.009(3) 0.009(3) C7 0.025(3) 0.016(2) 0.025(3) -0.002(2) 0.001(2) 0.004(2) C4 0.032(3) 0.039(3) 0.028(3) 0.005(3) 0.008(3) -0.007(3) C1 0.023(3) 0.017(2) 0.013(2) 0.0039(19) -0.007(2) -0.004(2) C2 0.023(3) 0.022(3) 0.020(3) 0.000(2) -0.002(2) -0.002(2) C10 0.035(3) 0.018(2) 0.027(3) 0.004(2) -0.001(3) 0.004(2) C6 0.029(4) 0.022(3) 0.021(3) 0.001(2) -0.010(3) -0.003(3) C3 0.031(3) 0.035(3) 0.023(3) -0.002(3) 0.001(3) 0.000(3) C5 0.036(3) 0.023(3) 0.029(3) 0.007(2) -0.001(3) -0.004(3) _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 Bi1 O2 2.151(4) . ? Bi1 O1 2.154(4) . ? Bi1 C1 2.222(6) . ? Bi1 N2 2.663(5) . ? Bi1 N1 2.711(5) . ? Si1 O1 1.604(4) . ? Si1 O3 1.638(4) . ? Si1 C13 1.877(6) . ? Si1 C19 1.877(6) . ? Si2 O2 1.597(4) . ? Si2 O3 1.641(4) . ? Si2 C31 1.873(6) . ? Si2 C25 1.882(6) . ? C25 C30 1.389(8) . ? C25 C26 1.405(8) . ? C13 C18 1.390(8) . ? C13 C14 1.404(8) . ? C17 C18 1.379(9) . ? C17 C16 1.384(10) . ? C17 H17 0.9299 . ? C30 C29 1.397(9) . ? C30 H30 0.9300 . ? C18 H18 0.9300 . ? C15 C16 1.382(11) . ? C15 C14 1.389(8) . ? C15 H15 0.9300 . ? C27 C28 1.369(9) . ? C27 C26 1.393(8) . ? C27 H27 0.9300 . ? C26 H26 0.9302 . ? C28 C29 1.372(10) . ? C28 H28 0.9300 . ? C14 H14 0.9300 . ? C21 C22 1.390(12) . ? C21 C20 1.396(9) . ? C21 H21 0.9300 . ? C19 C24 1.392(8) . ? C19 C20 1.396(8) . ? C20 H20 0.9299 . ? C16 H16 0.9301 . ? C29 H29 0.9299 . ? C35 C36 1.382(9) . ? C35 C34 1.385(8) . ? C35 H35 0.9300 . ? C34 C33 1.373(10) . ? C34 H34 0.9299 . ? C23 C22 1.384(10) . ? C23 C24 1.407(9) . ? C23 H23 0.9300 . ? N1 C8 1.468(8) . ? N1 C7 1.472(7) . ? N1 C9 1.475(7) . ? C22 H22 0.9300 . ? C31 C36 1.394(8) . ? C31 C32 1.406(8) . ? N2 C10 1.466(8) . ? N2 C12 1.467(8) . ? N2 C11 1.469(8) . ? C36 H36 0.9300 . ? C33 C32 1.391(8) . ? C33 H33 0.9299 . ? C12 H12A 0.9601 . ? C12 H12B 0.9599 . ? C12 H12C 0.9600 . ? C8 H8A 0.9601 . ? C8 H8B 0.9599 . ? C8 H8C 0.9599 . ? C32 H32 0.9300 . ? C24 H24 0.9301 . ? C9 H9A 0.9599 . ? C9 H9B 0.9599 . ? C9 H9C 0.9601 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C7 C2 1.520(8) . ? C7 H7A 0.9701 . ? C7 H7B 0.9700 . ? C4 C5 1.380(9) . ? C4 C3 1.388(9) . ? C4 H4 0.9300 . ? C1 C2 1.391(8) . ? C1 C6 1.399(8) . ? C2 C3 1.377(9) . ? C10 C6 1.516(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C6 C5 1.390(9) . ? C3 H3 0.9299 . ? C5 H5 0.9300 . ? 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 O2 Bi1 O1 86.27(14) . . ? O2 Bi1 C1 95.58(18) . . ? O1 Bi1 C1 91.16(17) . . ? O2 Bi1 N2 154.53(15) . . ? O1 Bi1 N2 73.70(14) . . ? C1 Bi1 N2 69.82(17) . . ? O2 Bi1 N1 72.73(14) . . ? O1 Bi1 N1 148.17(15) . . ? C1 Bi1 N1 68.09(17) . . ? N2 Bi1 N1 117.45(15) . . ? O1 Si1 O3 111.7(2) . . ? O1 Si1 C13 110.9(2) . . ? O3 Si1 C13 108.0(2) . . ? O1 Si1 C19 111.9(2) . . ? O3 Si1 C19 106.4(2) . . ? C13 Si1 C19 107.6(3) . . ? O2 Si2 O3 111.9(2) . . ? O2 Si2 C31 110.9(2) . . ? O3 Si2 C31 107.6(2) . . ? O2 Si2 C25 108.6(2) . . ? O3 Si2 C25 109.8(2) . . ? C31 Si2 C25 107.9(2) . . ? Si1 O1 Bi1 137.9(2) . . ? C30 C25 C26 117.7(5) . . ? C30 C25 Si2 122.8(5) . . ? C26 C25 Si2 119.5(4) . . ? Si1 O3 Si2 133.1(3) . . ? C18 C13 C14 117.2(5) . . ? C18 C13 Si1 122.7(4) . . ? C14 C13 Si1 119.9(4) . . ? C18 C17 C16 119.7(6) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.2 . . ? C25 C30 C29 120.5(6) . . ? C25 C30 H30 120.5 . . ? C29 C30 H30 119.0 . . ? C17 C18 C13 122.1(6) . . ? C17 C18 H18 118.1 . . ? C13 C18 H18 119.8 . . ? C16 C15 C14 119.8(8) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 119.4 . . ? Si2 O2 Bi1 138.1(2) . . ? C28 C27 C26 119.6(6) . . ? C28 C27 H27 120.6 . . ? C26 C27 H27 119.8 . . ? C27 C26 C25 121.3(5) . . ? C27 C26 H26 118.6 . . ? C25 C26 H26 120.0 . . ? C27 C28 C29 120.4(6) . . ? C27 C28 H28 119.1 . . ? C29 C28 H28 120.5 . . ? C15 C14 C13 121.2(6) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 118.0 . . ? C22 C21 C20 119.8(6) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 120.5 . . ? C24 C19 C20 118.0(5) . . ? C24 C19 Si1 120.4(4) . . ? C20 C19 Si1 121.7(5) . . ? C19 C20 C21 121.5(6) . . ? C19 C20 H20 118.7 . . ? C21 C20 H20 119.8 . . ? C15 C16 C17 120.1(6) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 119.3 . . ? C28 C29 C30 120.5(6) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.5 . . ? C36 C35 C34 120.5(8) . . ? C36 C35 H35 118.1 . . ? C34 C35 H35 121.4 . . ? C33 C34 C35 119.5(7) . . ? C33 C34 H34 121.9 . . ? C35 C34 H34 118.6 . . ? C22 C23 C24 120.2(8) . . ? C22 C23 H23 118.4 . . ? C24 C23 H23 121.4 . . ? C8 N1 C7 111.6(5) . . ? C8 N1 C9 109.9(5) . . ? C7 N1 C9 108.9(5) . . ? C8 N1 Bi1 111.1(4) . . ? C7 N1 Bi1 100.1(3) . . ? C9 N1 Bi1 114.9(4) . . ? C23 C22 C21 119.6(8) . . ? C23 C22 H22 121.5 . . ? C21 C22 H22 118.8 . . ? C36 C31 C32 117.6(5) . . ? C36 C31 Si2 123.3(4) . . ? C32 C31 Si2 119.2(4) . . ? C10 N2 C12 109.8(5) . . ? C10 N2 C11 111.0(5) . . ? C12 N2 C11 109.9(5) . . ? C10 N2 Bi1 102.3(3) . . ? C12 N2 Bi1 114.5(4) . . ? C11 N2 Bi1 109.3(4) . . ? C35 C36 C31 121.2(6) . . ? C35 C36 H36 118.6 . . ? C31 C36 H36 120.2 . . ? C34 C33 C32 120.6(6) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.7 . . ? N2 C12 H12A 109.7 . . ? N2 C12 H12B 109.6 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.1 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C8 H8A 109.3 . . ? N1 C8 H8B 108.9 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 110.2 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C33 C32 C31 120.7(6) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.6 . . ? C19 C24 C23 120.9(6) . . ? C19 C24 H24 118.8 . . ? C23 C24 H24 120.2 . . ? N1 C9 H9A 109.3 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C11 H11A 111.1 . . ? N2 C11 H11B 108.1 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.2 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C7 C2 110.3(5) . . ? N1 C7 H7A 109.5 . . ? C2 C7 H7A 108.4 . . ? N1 C7 H7B 110.3 . . ? C2 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? C5 C4 C3 120.1(6) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 119.5 . . ? C2 C1 C6 120.3(5) . . ? C2 C1 Bi1 120.7(4) . . ? C6 C1 Bi1 119.0(4) . . ? C3 C2 C1 119.7(6) . . ? C3 C2 C7 122.1(6) . . ? C1 C2 C7 118.3(5) . . ? N2 C10 C6 110.7(5) . . ? N2 C10 H10A 108.6 . . ? C6 C10 H10A 111.6 . . ? N2 C10 H10B 108.4 . . ? C6 C10 H10B 109.7 . . ? H10A C10 H10B 107.7 . . ? C5 C6 C1 118.8(6) . . ? C5 C6 C10 121.1(6) . . ? C1 C6 C10 120.1(6) . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 120.0 . . ? C4 C5 C6 120.5(6) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 120.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.951 _refine_diff_density_min -1.453 _refine_diff_density_rms 0.163 _database_code_depnum_ccdc_archive 'CCDC 936155' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H39 N2 O3 Sb Si2' _chemical_formula_sum 'C36 H39 N2 O3 Sb Si2' _chemical_formula_weight 725.62 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' N N 0.0061 0.0033 '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' Sb Sb -0.5866 1.5461 '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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 14.2341(16) _cell_length_b 20.3199(11) _cell_length_c 11.8500(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3427.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 16456 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.912 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.059 0 1 0 0.126 1 0 0 0.181 -1 0 0 0.124 0 0 -1 0.080 0 0 1 0.109 0 1 -1 0.065 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16428 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6646 _reflns_number_gt 5804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+5.4911P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.021(19) _refine_ls_number_reflns 6646 _refine_ls_number_parameters 397 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 Sb1 Sb 0.619672(15) 0.985087(11) 0.36045(3) 0.01810(6) Uani 1 1 d . . . Si1 Si 0.75972(9) 1.06723(7) 0.17324(11) 0.0183(3) Uani 1 1 d . . . Si2 Si 0.78271(9) 0.92151(6) 0.17985(11) 0.0182(3) Uani 1 1 d . . . O2 O 0.7050(2) 0.92188(14) 0.2771(2) 0.0207(6) Uani 1 1 d . . . O1 O 0.6825(2) 1.05781(14) 0.2705(2) 0.0220(7) Uani 1 1 d . . . C13 C 0.8630(3) 1.1145(2) 0.2281(4) 0.0205(9) Uani 1 1 d . . . N1 N 0.5760(3) 1.09496(19) 0.4634(3) 0.0282(9) Uani 1 1 d . . . N2 N 0.6326(3) 0.87571(17) 0.4860(3) 0.0255(8) Uani 1 1 d . . . C18 C 0.9123(3) 1.1603(2) 0.1621(4) 0.0260(10) Uani 1 1 d . . . H18 H 0.8921 1.1688 0.0889 0.031 Uiso 1 1 d R . . C30 C 0.9442(3) 0.8370(2) 0.1944(4) 0.0269(10) Uani 1 1 d . . . H30 H 0.9203 0.8160 0.1309 0.032 Uiso 1 1 d R . . C1 C 0.7135(3) 0.9997(2) 0.4998(3) 0.0199(9) Uani 1 1 d . . . C36 C 0.7601(3) 0.8840(2) -0.0521(4) 0.0257(10) Uani 1 1 d . . . H36 H 0.7868 0.9245 -0.0696 0.031 Uiso 1 1 d R . . C31 C 0.7479(3) 0.8664(2) 0.0605(4) 0.0214(9) Uani 1 1 d . . . C35 C 0.7340(3) 0.8422(2) -0.1394(6) 0.0311(9) Uani 1 1 d . . . H35 H 0.7418 0.8557 -0.2139 0.037 Uiso 1 1 d R . . C26 C 0.9332(3) 0.9194(2) 0.3367(4) 0.0271(12) Uani 1 1 d . . . H26 H 0.9014 0.9546 0.3690 0.033 Uiso 1 1 d R . . C25 C 0.8957(3) 0.8902(2) 0.2402(4) 0.0209(9) Uani 1 1 d . . . C4 C 0.8498(3) 1.0213(2) 0.6635(4) 0.0338(11) Uani 1 1 d . . . H4 H 0.8990 1.0292 0.7134 0.041 Uiso 1 1 d R . . C24 C 0.6932(3) 1.0790(3) -0.0527(4) 0.0315(11) Uani 1 1 d . . . H24 H 0.7076 1.0345 -0.0580 0.038 Uiso 1 1 d R . . C28 C 1.0631(3) 0.8455(2) 0.3383(4) 0.0344(14) Uani 1 1 d . . . H28 H 1.1187 0.8306 0.3706 0.041 Uiso 1 1 d R . . C33 C 0.6833(3) 0.7625(2) -0.0039(4) 0.0302(11) Uani 1 1 d . . . H33 H 0.6582 0.7214 0.0127 0.036 Uiso 1 1 d R . . O3 O 0.7976(2) 0.99572(13) 0.1283(2) 0.0200(6) Uani 1 1 d . . . C11 C 0.5741(3) 0.8814(2) 0.5882(4) 0.0322(11) Uani 1 1 d . . . H11A H 0.5850 0.8444 0.6368 0.039 Uiso 1 1 d R . . H11B H 0.5899 0.9212 0.6274 0.039 Uiso 1 1 d R . . H11C H 0.5091 0.8826 0.5667 0.039 Uiso 1 1 d R . . C19 C 0.7106(3) 1.1119(2) 0.0485(4) 0.0221(9) Uani 1 1 d . . . C6 C 0.7610(3) 0.9466(2) 0.5492(4) 0.0215(10) Uani 1 1 d . . . C7 C 0.6688(3) 1.1189(2) 0.4987(4) 0.0277(10) Uani 1 1 d . . . H7A H 0.7003 1.1393 0.4351 0.033 Uiso 1 1 d R . . H7B H 0.6617 1.1517 0.5576 0.033 Uiso 1 1 d R . . C9 C 0.5167(4) 1.0787(3) 0.5604(5) 0.0400(13) Uani 1 1 d . . . H9A H 0.4579 1.0614 0.5339 0.048 Uiso 1 1 d R . . H9B H 0.5476 1.0464 0.6062 0.048 Uiso 1 1 d R . . H9C H 0.5054 1.1176 0.6043 0.048 Uiso 1 1 d R . . C22 C 0.6410(3) 1.1777(2) -0.1411(7) 0.0411(12) Uani 1 1 d . . . H22 H 0.6187 1.1992 -0.2050 0.049 Uiso 1 1 d R . . C32 C 0.7086(3) 0.8046(2) 0.0825(4) 0.0276(10) Uani 1 1 d . . . H32 H 0.6991 0.7915 0.1568 0.033 Uiso 1 1 d R . . C12 C 0.6111(4) 0.8139(2) 0.4262(4) 0.0332(11) Uani 1 1 d . . . H12A H 0.5462 0.8136 0.4042 0.040 Uiso 1 1 d R . . H12B H 0.6500 0.8106 0.3602 0.040 Uiso 1 1 d R . . H12C H 0.6233 0.7772 0.4751 0.040 Uiso 1 1 d R . . C15 C 0.9771(3) 1.1345(2) 0.3772(5) 0.0338(13) Uani 1 1 d . . . H15 H 0.9998 1.1251 0.4490 0.041 Uiso 1 1 d R . . C2 C 0.7274(3) 1.0628(2) 0.5418(4) 0.0224(11) Uani 1 1 d . . . C3 C 0.7963(3) 1.0734(2) 0.6239(4) 0.0309(11) Uani 1 1 d . . . H3 H 0.8065 1.1157 0.6511 0.037 Uiso 1 1 d R . . C27 C 1.0161(3) 0.8981(2) 0.3857(4) 0.0314(12) Uani 1 1 d . . . H27 H 1.0400 0.9189 0.4495 0.038 Uiso 1 1 d R . . C29 C 1.0280(3) 0.8146(2) 0.2442(4) 0.0332(12) Uani 1 1 d . . . H29 H 1.0599 0.7792 0.2126 0.040 Uiso 1 1 d R . . C23 C 0.6581(3) 1.1113(3) -0.1449(7) 0.0425(12) Uani 1 1 d . . . H23 H 0.6446 1.0877 -0.2102 0.051 Uiso 1 1 d R . . C34 C 0.6960(3) 0.7813(2) -0.1154(4) 0.0300(13) Uani 1 1 d . . . H34 H 0.6792 0.7533 -0.1740 0.036 Uiso 1 1 d R . . C10 C 0.7327(3) 0.8783(2) 0.5142(4) 0.0242(10) Uani 1 1 d . . . H10A H 0.7460 0.8477 0.5749 0.029 Uiso 1 1 d R . . H10B H 0.7693 0.8652 0.4489 0.029 Uiso 1 1 d R . . C16 C 1.0227(4) 1.1794(2) 0.3099(5) 0.0392(13) Uani 1 1 d . . . H16 H 1.0753 1.2015 0.3371 0.047 Uiso 1 1 d R . . C14 C 0.8974(3) 1.1029(2) 0.3369(4) 0.0270(12) Uani 1 1 d . . . H14 H 0.8659 1.0735 0.3835 0.032 Uiso 1 1 d R . . C20 C 0.6907(3) 1.1792(2) 0.0513(5) 0.0303(11) Uani 1 1 d . . . H20 H 0.7006 1.2025 0.1178 0.036 Uiso 1 1 d R . . C21 C 0.6563(3) 1.2120(3) -0.0428(5) 0.0383(13) Uani 1 1 d . . . H21 H 0.6446 1.2570 -0.0401 0.046 Uiso 1 1 d R . . C17 C 0.9902(3) 1.1927(2) 0.2033(5) 0.0345(12) Uani 1 1 d . . . H17 H 1.0210 1.2233 0.1582 0.041 Uiso 1 1 d R . . C5 C 0.8298(3) 0.9579(3) 0.6287(4) 0.0316(11) Uani 1 1 d . . . H5 H 0.8630 0.9226 0.6588 0.038 Uiso 1 1 d R . . C8 C 0.5287(4) 1.1425(2) 0.3896(5) 0.0450(17) Uani 1 1 d . . . H8A H 0.5241 1.1844 0.4268 0.054 Uiso 1 1 d R . . H8B H 0.5641 1.1473 0.3212 0.054 Uiso 1 1 d R . . H8C H 0.4668 1.1268 0.3720 0.054 Uiso 1 1 d 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 Sb1 0.01517(11) 0.02120(10) 0.01794(11) -0.0012(2) -0.00053(18) -0.00043(11) Si1 0.0205(7) 0.0174(6) 0.0171(6) -0.0008(5) -0.0005(6) -0.0004(5) Si2 0.0211(7) 0.0170(6) 0.0167(6) -0.0004(6) -0.0007(5) -0.0001(5) O2 0.0237(16) 0.0202(15) 0.0181(15) -0.0024(13) 0.0034(12) -0.0011(13) O1 0.0227(17) 0.0219(15) 0.0214(16) 0.0025(13) 0.0022(13) 0.0001(13) C13 0.021(2) 0.019(2) 0.021(2) -0.0044(18) 0.0010(17) 0.0035(18) N1 0.027(2) 0.029(2) 0.029(2) 0.0001(18) 0.0039(17) 0.0057(18) N2 0.028(2) 0.0204(18) 0.028(2) 0.0009(16) 0.0024(17) -0.0047(16) C18 0.028(3) 0.025(2) 0.025(2) -0.002(2) 0.0008(19) 0.0032(19) C30 0.027(3) 0.026(2) 0.028(3) 0.001(2) 0.005(2) 0.0028(19) C1 0.021(2) 0.023(2) 0.0162(19) 0.0008(17) 0.0036(16) -0.0027(17) C36 0.022(2) 0.027(2) 0.028(2) -0.002(2) 0.0045(19) 0.0009(19) C31 0.018(2) 0.021(2) 0.025(2) -0.0085(19) -0.0035(18) 0.0041(17) C35 0.032(2) 0.040(2) 0.0211(19) -0.009(3) 0.001(3) -0.0008(18) C26 0.021(2) 0.032(2) 0.028(3) 0.005(2) 0.0008(18) -0.0008(18) C25 0.019(2) 0.021(2) 0.023(2) 0.0066(18) 0.0025(17) -0.0015(17) C4 0.029(3) 0.042(3) 0.030(3) -0.007(2) -0.012(2) -0.006(2) C24 0.031(3) 0.035(3) 0.029(3) -0.001(2) -0.005(2) 0.009(2) C28 0.023(2) 0.041(3) 0.040(4) 0.025(3) -0.001(2) 0.0039(19) C33 0.027(3) 0.020(2) 0.043(3) -0.009(2) -0.006(2) -0.002(2) O3 0.0247(16) 0.0142(15) 0.0211(15) -0.0004(12) 0.0015(12) -0.0001(12) C11 0.032(3) 0.036(3) 0.029(3) 0.004(2) 0.008(2) -0.005(2) C19 0.017(2) 0.028(2) 0.021(2) 0.003(2) 0.0006(18) -0.0006(18) C6 0.018(2) 0.029(3) 0.017(2) 0.001(2) 0.0038(18) -0.001(2) C7 0.035(3) 0.021(2) 0.027(2) -0.008(2) 0.001(2) 0.004(2) C9 0.034(3) 0.045(3) 0.041(3) -0.008(3) 0.010(2) 0.009(2) C22 0.031(2) 0.060(3) 0.032(2) 0.026(4) -0.011(3) 0.004(2) C32 0.034(3) 0.023(2) 0.025(3) -0.002(2) 0.001(2) -0.002(2) C12 0.037(3) 0.023(2) 0.040(3) -0.004(2) 0.005(2) -0.010(2) C15 0.034(3) 0.037(2) 0.030(4) -0.013(3) -0.010(2) 0.008(2) C2 0.021(3) 0.025(2) 0.021(2) -0.002(2) 0.004(2) 0.001(2) C3 0.032(3) 0.031(3) 0.030(3) -0.005(2) -0.001(2) -0.008(2) C27 0.027(2) 0.040(3) 0.026(3) 0.011(2) -0.0052(19) -0.007(2) C29 0.027(3) 0.031(3) 0.042(3) 0.009(2) 0.010(2) 0.011(2) C23 0.040(2) 0.066(3) 0.021(2) -0.004(4) -0.004(3) 0.013(2) C34 0.023(2) 0.037(2) 0.030(4) -0.018(2) -0.0042(19) 0.0048(19) C10 0.026(3) 0.025(2) 0.021(2) 0.0026(19) -0.0002(18) 0.000(2) C16 0.025(3) 0.035(3) 0.059(4) -0.018(3) -0.014(2) 0.003(2) C14 0.026(2) 0.026(2) 0.030(4) -0.003(2) 0.0003(18) 0.0018(17) C20 0.028(3) 0.025(2) 0.038(3) 0.003(2) -0.011(2) -0.003(2) C21 0.025(3) 0.031(3) 0.059(4) 0.016(3) -0.007(2) -0.003(2) C17 0.028(3) 0.021(2) 0.054(4) -0.005(2) 0.005(2) -0.001(2) C5 0.027(3) 0.041(3) 0.027(3) 0.002(2) -0.003(2) 0.005(2) C8 0.043(3) 0.036(3) 0.056(5) 0.006(3) 0.003(3) 0.021(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 Sb1 O2 2.025(3) . ? Sb1 O1 2.029(3) . ? Sb1 C1 2.144(4) . ? Si1 O1 1.604(3) . ? Si1 O3 1.639(3) . ? Si1 C19 1.871(5) . ? Si1 C13 1.873(4) . ? Si2 O2 1.597(3) . ? Si2 O3 1.641(3) . ? Si2 C31 1.871(4) . ? Si2 C25 1.871(4) . ? C13 C14 1.400(6) . ? C13 C18 1.403(6) . ? N1 C9 1.464(6) . ? N1 C8 1.468(6) . ? N1 C7 1.469(6) . ? N2 C10 1.464(6) . ? N2 C12 1.474(5) . ? N2 C11 1.474(6) . ? C18 C17 1.379(7) . ? C18 H18 0.9300 . ? C30 C25 1.392(6) . ? C30 C29 1.407(7) . ? C30 H30 0.9300 . ? C1 C2 1.390(6) . ? C1 C6 1.403(6) . ? C36 C35 1.389(7) . ? C36 C31 1.392(6) . ? C36 H36 0.9300 . ? C31 C32 1.400(6) . ? C35 C34 1.380(6) . ? C35 H35 0.9301 . ? C26 C27 1.385(6) . ? C26 C25 1.394(6) . ? C26 H26 0.9299 . ? C4 C5 1.383(7) . ? C4 C3 1.386(7) . ? C4 H4 0.9299 . ? C24 C23 1.368(8) . ? C24 C19 1.394(6) . ? C24 H24 0.9299 . ? C28 C29 1.373(7) . ? C28 C27 1.379(7) . ? C28 H28 0.9299 . ? C33 C32 1.381(6) . ? C33 C34 1.387(7) . ? C33 H33 0.9300 . ? C11 H11A 0.9601 . ? C11 H11B 0.9599 . ? C11 H11C 0.9601 . ? C19 C20 1.397(6) . ? C6 C5 1.378(6) . ? C6 C10 1.504(6) . ? C7 C2 1.502(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9701 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9599 . ? C22 C23 1.373(6) . ? C22 C21 1.375(10) . ? C22 H22 0.9302 . ? C32 H32 0.9300 . ? C12 H12A 0.9601 . ? C12 H12B 0.9600 . ? C12 H12C 0.9601 . ? C15 C16 1.375(7) . ? C15 C14 1.387(6) . ? C15 H15 0.9299 . ? C2 C3 1.397(7) . ? C3 H3 0.9300 . ? C27 H27 0.9299 . ? C29 H29 0.9301 . ? C23 H23 0.9301 . ? C34 H34 0.9300 . ? C10 H10A 0.9699 . ? C10 H10B 0.9700 . ? C16 C17 1.372(7) . ? C16 H16 0.9299 . ? C14 H14 0.9300 . ? C20 C21 1.388(7) . ? C20 H20 0.9299 . ? C21 H21 0.9300 . ? C17 H17 0.9300 . ? C5 H5 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9601 . ? C8 H8C 0.9600 . ? 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 O2 Sb1 O1 86.64(11) . . ? O2 Sb1 C1 95.18(14) . . ? O1 Sb1 C1 91.66(14) . . ? O1 Si1 O3 110.68(17) . . ? O1 Si1 C19 111.69(18) . . ? O3 Si1 C19 107.23(19) . . ? O1 Si1 C13 110.48(18) . . ? O3 Si1 C13 108.00(17) . . ? C19 Si1 C13 108.6(2) . . ? O2 Si2 O3 110.72(17) . . ? O2 Si2 C31 111.39(19) . . ? O3 Si2 C31 107.62(19) . . ? O2 Si2 C25 108.72(18) . . ? O3 Si2 C25 110.09(18) . . ? C31 Si2 C25 108.26(19) . . ? Si2 O2 Sb1 140.38(18) . . ? Si1 O1 Sb1 140.01(18) . . ? C14 C13 C18 116.8(4) . . ? C14 C13 Si1 120.5(3) . . ? C18 C13 Si1 122.6(3) . . ? C9 N1 C8 110.6(4) . . ? C9 N1 C7 111.7(4) . . ? C8 N1 C7 111.4(4) . . ? C10 N2 C12 110.0(4) . . ? C10 N2 C11 111.1(4) . . ? C12 N2 C11 110.1(4) . . ? C17 C18 C13 121.4(5) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.2 . . ? C25 C30 C29 120.5(5) . . ? C25 C30 H30 119.4 . . ? C29 C30 H30 120.1 . . ? C2 C1 C6 119.4(4) . . ? C2 C1 Sb1 119.5(3) . . ? C6 C1 Sb1 121.0(3) . . ? C35 C36 C31 121.6(5) . . ? C35 C36 H36 119.0 . . ? C31 C36 H36 119.5 . . ? C36 C31 C32 117.3(4) . . ? C36 C31 Si2 122.5(3) . . ? C32 C31 Si2 120.1(3) . . ? C34 C35 C36 119.9(6) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 119.7 . . ? C27 C26 C25 122.5(4) . . ? C27 C26 H26 118.9 . . ? C25 C26 H26 118.6 . . ? C30 C25 C26 117.4(4) . . ? C30 C25 Si2 122.7(4) . . ? C26 C25 Si2 119.9(3) . . ? C5 C4 C3 119.8(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 119.9 . . ? C23 C24 C19 121.5(5) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.0 . . ? C29 C28 C27 120.6(4) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C32 C33 C34 120.1(4) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 119.9 . . ? Si1 O3 Si2 130.64(19) . . ? N2 C11 H11A 109.9 . . ? N2 C11 H11B 109.3 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.2 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C24 C19 C20 117.0(4) . . ? C24 C19 Si1 120.9(4) . . ? C20 C19 Si1 122.1(4) . . ? C5 C6 C1 120.0(4) . . ? C5 C6 C10 122.2(5) . . ? C1 C6 C10 117.8(4) . . ? N1 C7 C2 110.2(4) . . ? N1 C7 H7A 109.6 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.8 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 108.2 . . ? N1 C9 H9A 109.2 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.7 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C23 C22 C21 119.8(7) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 120.4 . . ? C33 C32 C31 121.4(4) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.5 . . ? N2 C12 H12A 109.7 . . ? N2 C12 H12B 109.3 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.3 . . ? C1 C2 C3 119.5(5) . . ? C1 C2 C7 119.9(4) . . ? C3 C2 C7 120.6(4) . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 119.6 . . ? C28 C27 C26 118.9(4) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.7 . . ? C28 C29 C30 120.1(4) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 119.7 . . ? C24 C23 C22 120.6(7) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.7 . . ? C35 C34 C33 119.7(5) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 120.7 . . ? N2 C10 C6 110.9(4) . . ? N2 C10 H10A 109.7 . . ? C6 C10 H10A 109.5 . . ? N2 C10 H10B 109.3 . . ? C6 C10 H10B 109.2 . . ? H10A C10 H10B 108.1 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 120.0 . . ? C15 C14 C13 121.7(4) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.1 . . ? C21 C20 C19 121.5(5) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.2 . . ? C22 C21 C20 119.6(5) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 120.6 . . ? C16 C17 C18 120.2(5) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 119.6 . . ? C6 C5 C4 120.4(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 120.0 . . ? N1 C8 H8A 109.9 . . ? N1 C8 H8B 109.2 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.3 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.482 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 936156' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H44 N2 O3 Si2 Sn' _chemical_formula_sum 'C42 H44 N2 O3 Si2 Sn' _chemical_formula_weight 799.66 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' N N 0.0061 0.0033 '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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7320(2) _cell_length_b 13.1811(8) _cell_length_c 13.5121(8) _cell_angle_alpha 89.060(5) _cell_angle_beta 84.317(4) _cell_angle_gamma 87.989(3) _cell_volume 1900.69(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 37098 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.776 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.132 0 -1 0 0.131 0 1 0 0.176 -1 0 0 0.151 0 0 1 0.144 0 0 -1 0.118 -1 1 0 0.174 -1 -1 0 0.156 1 1 0 0.179 -1 0 -1 0.121 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.848 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_ambient_temperature 150(1) _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 Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36963 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8664 _reflns_number_gt 7598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0238P)^2^+1.3534P] 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 8664 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Sn1 Sn 0.427862(11) 0.210576(10) 0.221598(10) 0.01820(4) Uani 1 1 d . . . Si1 Si 0.68041(5) 0.34339(4) 0.14311(4) 0.01806(11) Uani 1 1 d . . . Si2 Si 0.72462(5) 0.17495(4) 0.28455(4) 0.01812(11) Uani 1 1 d . . . O1 O 0.54487(12) 0.29947(10) 0.13326(10) 0.0211(3) Uani 1 1 d . . . O2 O 0.57580(12) 0.16379(11) 0.29499(11) 0.0236(3) Uani 1 1 d . . . O3 O 0.76724(12) 0.26784(10) 0.20763(11) 0.0231(3) Uani 1 1 d . . . N1 N 0.33843(16) 0.06931(14) 0.34870(13) 0.0267(4) Uani 1 1 d . . . C37 C 0.77401(18) 0.20119(15) 0.41022(15) 0.0223(4) Uani 1 1 d . . . N2 N 0.29303(15) 0.26762(12) 0.07423(13) 0.0228(3) Uani 1 1 d . . . C8 C 0.2018(2) 0.0601(2) 0.3543(2) 0.0379(6) Uani 1 1 d . . . H8A H 0.1784 -0.0005 0.3909 0.046 Uiso 1 1 d R . . H8B H 0.1765 0.0566 0.2883 0.046 Uiso 1 1 d R . . H8C H 0.1613 0.1181 0.3874 0.046 Uiso 1 1 d R . . C25 C 0.67011(18) 0.46895(15) 0.20685(15) 0.0219(4) Uani 1 1 d . . . C31 C 0.81723(17) 0.05985(15) 0.23617(14) 0.0201(4) Uani 1 1 d . . . C13 C 0.32855(19) 0.31951(16) 0.31691(15) 0.0254(4) Uani 1 1 d . . . C21 C 0.7659(2) 0.38241(16) -0.16270(16) 0.0286(4) Uani 1 1 d . . . H21 H 0.7224 0.3837 -0.2189 0.034 Uiso 1 1 d R . . C1 C 0.38962(17) 0.08135(14) 0.14026(15) 0.0212(4) Uani 1 1 d . . . C19 C 0.76536(17) 0.36118(14) 0.01647(15) 0.0195(4) Uani 1 1 d . . . C2 C 0.38174(18) -0.01290(15) 0.18820(17) 0.0254(4) Uani 1 1 d . . . C11 C 0.3034(2) 0.37390(16) 0.04186(18) 0.0318(5) Uani 1 1 d . . . H11A H 0.3901 0.3908 0.0329 0.038 Uiso 1 1 d R . . H11B H 0.2597 0.4170 0.0914 0.038 Uiso 1 1 d R . . H11C H 0.2671 0.3835 -0.0199 0.038 Uiso 1 1 d R . . C33 C 0.9927(2) -0.01317(19) 0.13064(18) 0.0349(5) Uani 1 1 d . . . H33 H 1.0589 -0.0044 0.0817 0.042 Uiso 1 1 d R . . C10 C 0.35725(18) 0.19905(15) -0.00078(15) 0.0234(4) Uani 1 1 d . . . H10A H 0.4416 0.2213 -0.0195 0.028 Uiso 1 1 d R . . H10B H 0.3126 0.2001 -0.0598 0.028 Uiso 1 1 d R . . C3 C 0.3498(2) -0.09637(16) 0.13557(19) 0.0318(5) Uani 1 1 d . . . H3 H 0.3446 -0.1598 0.1666 0.038 Uiso 1 1 d R . . C16 C 0.2066(3) 0.4696(2) 0.4375(2) 0.0502(7) Uani 1 1 d . . . H16 H 0.1660 0.5198 0.4776 0.060 Uiso 1 1 d R . . C32 C 0.91575(19) 0.06975(17) 0.16164(16) 0.0271(4) Uani 1 1 d . . . H32 H 0.9303 0.1330 0.1320 0.033 Uiso 1 1 d R . . C20 C 0.70345(19) 0.36170(15) -0.06945(16) 0.0242(4) Uani 1 1 d . . . H20 H 0.6185 0.3482 -0.0645 0.029 Uiso 1 1 d R . . C22 C 0.8928(2) 0.40079(16) -0.17151(16) 0.0302(5) Uani 1 1 d . . . H22 H 0.9348 0.4144 -0.2336 0.036 Uiso 1 1 d R . . C24 C 0.89295(19) 0.38033(16) 0.00500(16) 0.0269(4) Uani 1 1 d . . . H24 H 0.9366 0.3810 0.0611 0.032 Uiso 1 1 d R . . C38 C 0.6924(2) 0.24659(17) 0.48468(17) 0.0311(5) Uani 1 1 d . . . H38 H 0.6110 0.2645 0.4716 0.037 Uiso 1 1 d R . . C26 C 0.7619(2) 0.49865(18) 0.26553(18) 0.0348(5) Uani 1 1 d . . . H26 H 0.8289 0.4543 0.2756 0.042 Uiso 1 1 d R . . C7 C 0.4011(2) -0.01937(16) 0.29709(18) 0.0299(5) Uani 1 1 d . . . H7A H 0.3668 -0.0815 0.3259 0.036 Uiso 1 1 d R . . H7B H 0.4900 -0.0205 0.3050 0.036 Uiso 1 1 d R . . C34 C 0.9712(2) -0.10754(19) 0.1719(2) 0.0392(6) Uani 1 1 d . . . H34 H 1.0226 -0.1629 0.1509 0.047 Uiso 1 1 d R . . C12 C 0.16048(19) 0.24224(18) 0.09093(19) 0.0322(5) Uani 1 1 d . . . H12A H 0.1240 0.2449 0.0288 0.039 Uiso 1 1 d R . . H12B H 0.1172 0.2903 0.1358 0.039 Uiso 1 1 d R . . H12C H 0.1534 0.1752 0.1193 0.039 Uiso 1 1 d R . . C6 C 0.36154(17) 0.09301(15) 0.04233(16) 0.0228(4) Uani 1 1 d . . . C39 C 0.7300(2) 0.26535(18) 0.57771(18) 0.0382(5) Uani 1 1 d . . . H39 H 0.6738 0.2955 0.6262 0.046 Uiso 1 1 d R . . C14 C 0.3959(2) 0.38805(17) 0.36474(17) 0.0329(5) Uani 1 1 d . . . H14 H 0.4830 0.3836 0.3570 0.039 Uiso 1 1 d R . . C5 C 0.33079(19) 0.00906(16) -0.00998(17) 0.0282(4) Uani 1 1 d . . . H5 H 0.3133 0.0159 -0.0759 0.034 Uiso 1 1 d R . . C36 C 0.7976(2) -0.03657(17) 0.27712(17) 0.0306(5) Uani 1 1 d . . . H36 H 0.7326 -0.0453 0.3271 0.037 Uiso 1 1 d R . . C30 C 0.5713(2) 0.53769(16) 0.19419(17) 0.0301(5) Uani 1 1 d . . . H30 H 0.5086 0.5196 0.1557 0.036 Uiso 1 1 d R . . C23 C 0.9563(2) 0.39922(18) -0.08765(18) 0.0318(5) Uani 1 1 d . . . H23 H 1.0418 0.4102 -0.0931 0.038 Uiso 1 1 d R . . C28 C 0.6555(3) 0.66000(19) 0.2957(2) 0.0439(6) Uani 1 1 d . . . H28 H 0.6502 0.7230 0.3261 0.053 Uiso 1 1 d R . . C29 C 0.5646(2) 0.63256(18) 0.2376(2) 0.0379(5) Uani 1 1 d . . . H29 H 0.4984 0.6777 0.2273 0.045 Uiso 1 1 d R . . C35 C 0.8726(2) -0.11976(18) 0.2450(2) 0.0410(6) Uani 1 1 d . . . H35 H 0.8568 -0.1837 0.2727 0.049 Uiso 1 1 d R . . C42 C 0.8938(2) 0.1748(2) 0.43408(18) 0.0396(6) Uani 1 1 d . . . H42 H 0.9501 0.1434 0.3864 0.048 Uiso 1 1 d R . . C17 C 0.1379(2) 0.4020(2) 0.3918(2) 0.0472(7) Uani 1 1 d . . . H17 H 0.0509 0.4060 0.4010 0.057 Uiso 1 1 d R . . C18 C 0.1980(2) 0.32651(19) 0.33146(19) 0.0357(5) Uani 1 1 d . . . H18 H 0.1508 0.2808 0.3007 0.043 Uiso 1 1 d R . . C41 C 0.9322(2) 0.1932(3) 0.5269(2) 0.0493(7) Uani 1 1 d . . . H41 H 1.0131 0.1747 0.5406 0.059 Uiso 1 1 d R . . C40 C 0.8503(3) 0.2393(2) 0.59867(18) 0.0393(6) Uani 1 1 d . . . H40 H 0.8759 0.2528 0.6608 0.047 Uiso 1 1 d R . . C9 C 0.3757(2) 0.0786(2) 0.44919(18) 0.0383(6) Uani 1 1 d . . . H9A H 0.3353 0.1380 0.4799 0.046 Uiso 1 1 d R . . H9B H 0.4649 0.0843 0.4460 0.046 Uiso 1 1 d R . . H9C H 0.3512 0.0195 0.4878 0.046 Uiso 1 1 d R . . C4 C 0.3266(2) -0.08548(17) 0.03709(19) 0.0328(5) Uani 1 1 d . . . H4 H 0.3076 -0.1422 0.0021 0.039 Uiso 1 1 d R . . C27 C 0.7552(3) 0.5933(2) 0.3092(2) 0.0471(7) Uani 1 1 d . . . H27 H 0.8178 0.6121 0.3474 0.056 Uiso 1 1 d R . . C15 C 0.3355(3) 0.4631(2) 0.4244(2) 0.0456(6) Uani 1 1 d . . . H15 H 0.3820 0.5092 0.4554 0.055 Uiso 1 1 d 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 0.01389(6) 0.01765(7) 0.02279(7) -0.00142(5) -0.00062(4) 0.00041(4) Si1 0.0160(2) 0.0167(2) 0.0215(3) 0.00156(19) -0.00235(19) -0.00112(19) Si2 0.0151(2) 0.0197(2) 0.0195(3) 0.00185(19) -0.00177(19) -0.00011(19) O1 0.0175(6) 0.0217(7) 0.0246(7) 0.0034(5) -0.0041(5) -0.0020(5) O2 0.0166(6) 0.0285(7) 0.0255(7) 0.0053(6) -0.0018(5) -0.0009(6) O3 0.0166(6) 0.0238(7) 0.0291(8) 0.0067(6) -0.0036(5) -0.0016(5) N1 0.0199(8) 0.0311(9) 0.0282(9) 0.0049(7) 0.0012(7) -0.0001(7) C37 0.0235(9) 0.0220(9) 0.0215(10) 0.0005(7) -0.0023(7) -0.0036(8) N2 0.0207(8) 0.0188(8) 0.0288(9) 0.0005(7) -0.0035(7) 0.0027(6) C8 0.0212(10) 0.0465(14) 0.0445(14) 0.0082(11) 0.0037(9) -0.0016(10) C25 0.0227(9) 0.0215(9) 0.0211(9) 0.0007(7) 0.0009(7) -0.0038(8) C31 0.0183(9) 0.0224(9) 0.0202(9) -0.0001(7) -0.0049(7) 0.0001(7) C13 0.0256(10) 0.0245(10) 0.0245(10) 0.0005(8) 0.0033(8) 0.0042(8) C21 0.0370(12) 0.0275(11) 0.0220(10) -0.0036(8) -0.0053(9) -0.0018(9) C1 0.0152(8) 0.0176(9) 0.0300(10) -0.0016(8) 0.0010(7) -0.0004(7) C19 0.0206(9) 0.0127(8) 0.0249(10) 0.0005(7) -0.0012(7) 0.0009(7) C2 0.0164(9) 0.0197(9) 0.0391(12) 0.0007(8) 0.0022(8) 0.0006(7) C11 0.0311(11) 0.0234(10) 0.0409(13) 0.0063(9) -0.0062(9) 0.0023(9) C33 0.0249(10) 0.0426(13) 0.0357(13) -0.0078(10) 0.0040(9) 0.0039(10) C10 0.0223(9) 0.0243(10) 0.0242(10) -0.0018(8) -0.0058(8) -0.0009(8) C3 0.0253(10) 0.0167(10) 0.0519(15) -0.0023(9) 0.0035(10) 0.0004(8) C16 0.0666(18) 0.0370(14) 0.0415(15) -0.0061(11) 0.0178(13) 0.0159(13) C32 0.0225(10) 0.0284(11) 0.0298(11) 0.0002(9) 0.0009(8) -0.0015(8) C20 0.0235(9) 0.0215(10) 0.0279(11) -0.0020(8) -0.0029(8) -0.0028(8) C22 0.0352(11) 0.0275(11) 0.0257(11) -0.0018(9) 0.0081(9) -0.0027(9) C24 0.0222(10) 0.0301(11) 0.0286(11) 0.0026(9) -0.0035(8) -0.0014(8) C38 0.0338(11) 0.0289(11) 0.0300(12) -0.0033(9) -0.0018(9) 0.0065(9) C26 0.0351(12) 0.0331(12) 0.0376(13) -0.0041(10) -0.0091(10) -0.0032(10) C7 0.0241(10) 0.0212(10) 0.0432(13) 0.0108(9) -0.0003(9) 0.0009(8) C34 0.0337(12) 0.0322(12) 0.0516(15) -0.0126(11) -0.0064(11) 0.0112(10) C12 0.0181(9) 0.0324(12) 0.0461(14) 0.0025(10) -0.0044(9) 0.0031(9) C6 0.0161(8) 0.0217(10) 0.0300(11) -0.0031(8) 0.0015(7) -0.0002(7) C39 0.0501(14) 0.0341(12) 0.0294(12) -0.0101(10) 0.0016(10) 0.0040(11) C14 0.0338(12) 0.0307(12) 0.0330(12) -0.0042(9) 0.0025(9) 0.0006(9) C5 0.0215(10) 0.0295(11) 0.0337(12) -0.0097(9) -0.0013(8) -0.0013(8) C36 0.0295(11) 0.0274(11) 0.0333(12) 0.0054(9) 0.0023(9) 0.0027(9) C30 0.0308(11) 0.0247(11) 0.0352(12) -0.0040(9) -0.0043(9) 0.0001(9) C23 0.0219(10) 0.0347(12) 0.0377(13) 0.0003(10) 0.0031(9) -0.0014(9) C28 0.0539(15) 0.0312(13) 0.0449(15) -0.0153(11) 0.0085(12) -0.0081(11) C29 0.0375(12) 0.0272(11) 0.0470(15) -0.0054(10) 0.0044(11) 0.0028(10) C35 0.0421(13) 0.0232(11) 0.0575(17) 0.0048(11) -0.0059(12) 0.0023(10) C42 0.0236(11) 0.0681(18) 0.0274(12) -0.0129(11) -0.0029(9) 0.0017(11) C17 0.0338(13) 0.0513(16) 0.0518(16) -0.0021(13) 0.0136(12) 0.0163(12) C18 0.0272(11) 0.0392(13) 0.0391(13) -0.0036(10) 0.0033(9) 0.0054(10) C41 0.0300(12) 0.083(2) 0.0376(14) -0.0123(14) -0.0129(10) -0.0011(13) C40 0.0527(15) 0.0413(13) 0.0260(12) -0.0085(10) -0.0108(10) -0.0072(12) C9 0.0348(12) 0.0485(15) 0.0304(12) 0.0131(11) 0.0004(10) -0.0026(11) C4 0.0253(10) 0.0221(10) 0.0502(14) -0.0132(10) 0.0023(10) -0.0018(8) C27 0.0493(15) 0.0454(15) 0.0501(16) -0.0135(12) -0.0166(12) -0.0127(12) C15 0.0596(17) 0.0327(13) 0.0429(15) -0.0141(11) 0.0038(12) 0.0016(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 O2 2.0267(14) . ? Sn1 O1 2.0335(13) . ? Sn1 C1 2.116(2) . ? Sn1 C13 2.130(2) . ? Si1 O1 1.6027(14) . ? Si1 O3 1.6393(14) . ? Si1 C19 1.873(2) . ? Si1 C25 1.873(2) . ? Si2 O2 1.6011(14) . ? Si2 O3 1.6407(14) . ? Si2 C37 1.869(2) . ? Si2 C31 1.875(2) . ? N1 C9 1.461(3) . ? N1 C8 1.470(3) . ? N1 C7 1.478(3) . ? C37 C42 1.388(3) . ? C37 C38 1.395(3) . ? N2 C11 1.465(3) . ? N2 C12 1.467(3) . ? N2 C10 1.472(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9599 . ? C8 H8C 0.9600 . ? C25 C30 1.392(3) . ? C25 C26 1.394(3) . ? C31 C36 1.392(3) . ? C31 C32 1.394(3) . ? C13 C14 1.384(3) . ? C13 C18 1.395(3) . ? C21 C22 1.384(3) . ? C21 C20 1.395(3) . ? C21 H21 0.9301 . ? C1 C6 1.391(3) . ? C1 C2 1.393(3) . ? C19 C20 1.393(3) . ? C19 C24 1.394(3) . ? C2 C3 1.391(3) . ? C2 C7 1.507(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9599 . ? C11 H11C 0.9601 . ? C33 C34 1.372(4) . ? C33 C32 1.391(3) . ? C33 H33 0.9301 . ? C10 C6 1.506(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C16 C17 1.369(4) . ? C16 C15 1.377(4) . ? C16 H16 0.9300 . ? C32 H32 0.9301 . ? C20 H20 0.9300 . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C24 C23 1.387(3) . ? C24 H24 0.9300 . ? C38 C39 1.386(3) . ? C38 H38 0.9300 . ? C26 C27 1.385(3) . ? C26 H26 0.9301 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C34 C35 1.386(4) . ? C34 H34 0.9299 . ? C12 H12A 0.9599 . ? C12 H12B 0.9601 . ? C12 H12C 0.9601 . ? C6 C5 1.389(3) . ? C39 C40 1.380(4) . ? C39 H39 0.9300 . ? C14 C15 1.388(3) . ? C14 H14 0.9300 . ? C5 C4 1.390(3) . ? C5 H5 0.9300 . ? C36 C35 1.387(3) . ? C36 H36 0.9300 . ? C30 C29 1.386(3) . ? C30 H30 0.9300 . ? C23 H23 0.9300 . ? C28 C29 1.373(4) . ? C28 C27 1.385(4) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C35 H35 0.9301 . ? C42 C41 1.386(3) . ? C42 H42 0.9300 . ? C17 C18 1.395(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C41 C40 1.376(4) . ? C41 H41 0.9300 . ? C40 H40 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C4 H4 0.9300 . ? C27 H27 0.9300 . ? C15 H15 0.9300 . ? 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 O2 Sn1 O1 88.72(5) . . ? O2 Sn1 C1 103.58(7) . . ? O1 Sn1 C1 108.53(7) . . ? O2 Sn1 C13 104.62(7) . . ? O1 Sn1 C13 101.87(7) . . ? C1 Sn1 C13 138.56(8) . . ? O1 Si1 O3 112.54(7) . . ? O1 Si1 C19 109.76(8) . . ? O3 Si1 C19 107.98(8) . . ? O1 Si1 C25 112.08(8) . . ? O3 Si1 C25 106.32(9) . . ? C19 Si1 C25 107.95(8) . . ? O2 Si2 O3 111.25(7) . . ? O2 Si2 C37 108.40(8) . . ? O3 Si2 C37 109.43(8) . . ? O2 Si2 C31 114.84(8) . . ? O3 Si2 C31 105.54(8) . . ? C37 Si2 C31 107.22(9) . . ? Si1 O1 Sn1 134.08(8) . . ? Si2 O2 Sn1 138.16(8) . . ? Si1 O3 Si2 129.12(9) . . ? C9 N1 C8 109.09(18) . . ? C9 N1 C7 111.73(18) . . ? C8 N1 C7 109.75(18) . . ? C42 C37 C38 116.9(2) . . ? C42 C37 Si2 121.19(16) . . ? C38 C37 Si2 121.94(16) . . ? C11 N2 C12 109.70(16) . . ? C11 N2 C10 111.02(17) . . ? C12 N2 C10 109.17(16) . . ? N1 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C30 C25 C26 117.6(2) . . ? C30 C25 Si1 120.52(16) . . ? C26 C25 Si1 121.90(16) . . ? C36 C31 C32 117.40(18) . . ? C36 C31 Si2 122.21(15) . . ? C32 C31 Si2 120.22(15) . . ? C14 C13 C18 118.3(2) . . ? C14 C13 Sn1 118.79(15) . . ? C18 C13 Sn1 122.85(17) . . ? C22 C21 C20 120.0(2) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.0 . . ? C6 C1 C2 120.72(19) . . ? C6 C1 Sn1 119.58(14) . . ? C2 C1 Sn1 119.44(16) . . ? C20 C19 C24 117.13(18) . . ? C20 C19 Si1 121.93(14) . . ? C24 C19 Si1 120.84(16) . . ? C3 C2 C1 119.0(2) . . ? C3 C2 C7 122.34(19) . . ? C1 C2 C7 118.54(19) . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.4 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C34 C33 C32 120.3(2) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 119.7 . . ? N2 C10 C6 108.92(16) . . ? N2 C10 H10A 109.8 . . ? C6 C10 H10A 110.0 . . ? N2 C10 H10B 109.9 . . ? C6 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 120.2 . . ? C33 C32 C31 121.3(2) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.4 . . ? C19 C20 C21 121.41(19) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C23 C22 C21 119.6(2) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C23 C24 C19 121.8(2) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.0 . . ? C39 C38 C37 121.4(2) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.2 . . ? C27 C26 C25 121.2(2) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.5 . . ? N1 C7 C2 109.42(16) . . ? N1 C7 H7A 109.9 . . ? C2 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C2 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C33 C34 C35 119.6(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.3 . . ? N2 C12 H12A 109.6 . . ? N2 C12 H12B 109.2 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.7 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 C6 C1 119.83(19) . . ? C5 C6 C10 122.3(2) . . ? C1 C6 C10 117.77(18) . . ? C40 C39 C38 120.3(2) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.9 . . ? C13 C14 C15 121.0(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.2 . . ? C35 C36 C31 121.5(2) . . ? C35 C36 H36 119.3 . . ? C31 C36 H36 119.2 . . ? C29 C30 C25 121.4(2) . . ? C29 C30 H30 119.4 . . ? C25 C30 H30 119.3 . . ? C22 C23 C24 120.0(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 119.8 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.1(2) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 120.0 . . ? C34 C35 C36 120.0(2) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C41 C42 C37 122.1(2) . . ? C41 C42 H42 118.9 . . ? C37 C42 H42 119.0 . . ? C16 C17 C18 120.2(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.4(2) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.8 . . ? C40 C41 C42 119.9(2) . . ? C40 C41 H41 120.0 . . ? C42 C41 H41 120.1 . . ? C41 C40 C39 119.4(2) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? N1 C9 H9A 109.6 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.3 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.8 . . ? C26 C27 C28 120.0(2) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 120.1 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.480 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 936157' ####################################################################### # # 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_compound5*0.5CH2Cl2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H68 N4 O4 Si2 Sn2, 0.5(C H2 Cl2)' _chemical_formula_sum 'C60.50 H69 Cl N4 O4 Si2 Sn2' _chemical_formula_weight 1245.21 _ccdc_journal_depnumber ? _ccdc_compound_id 5*0.5CH2Cl2 _ccdc_chemdiag_type ChemDraw _ccdc_chemdiag_records compound5.cdx _ccdc_disorder ;disordered dichloromethane molecule was removed by platon/squeeze ; 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' Cl Cl 0.1484 0.1585 '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' 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' Sn Sn -0.6537 1.4246 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.5356(3) _cell_length_b 16.2802(3) _cell_length_c 21.3586(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.403(2) _cell_angle_gamma 90.00 _cell_volume 5997.29(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18612 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 29.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2548 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device 'XcaliburS CCD Diffractometer' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w und \y scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29851 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 11137 _reflns_number_gt 8759 _reflns_threshold_expression >2sigma(I) _computing_data_collection ;CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.32.37' ; _computing_cell_refinement ;CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.32.37' ; _computing_data_reduction ;CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.32.37' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 1997)' _computing_publication_material 'enCIFer Version 1.4' _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^)+(0.0334P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11137 _refine_ls_number_parameters 657 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0587 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _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 Sn1 Sn 0.245324(8) 0.105977(10) 0.120897(7) 0.01961(5) Uani 1 1 d . . . Sn2 Sn 0.235081(8) -0.139861(10) 0.262739(7) 0.01880(5) Uani 1 1 d . . . Si1 Si 0.14592(3) 0.04626(4) 0.23271(3) 0.01848(14) Uani 1 1 d . . . Si2 Si 0.37248(3) -0.01434(4) 0.21935(3) 0.02011(15) Uani 1 1 d . . . O1 O 0.16199(8) 0.05559(10) 0.16111(7) 0.0225(4) Uani 1 1 d . . . O2 O 0.18295(8) -0.03309(9) 0.27120(7) 0.0221(4) Uani 1 1 d . . . O3 O 0.31509(8) -0.09167(9) 0.21815(7) 0.0224(4) Uani 1 1 d . . . O4 O 0.33173(8) 0.06860(10) 0.18923(7) 0.0232(4) Uani 1 1 d . . . N1 N 0.38410(11) 0.19518(13) 0.10137(10) 0.0295(5) Uani 1 1 d . . . N2 N 0.11781(10) 0.16094(12) 0.04454(9) 0.0257(5) Uani 1 1 d . . . N3 N 0.11136(10) -0.18776(12) 0.30412(10) 0.0263(5) Uani 1 1 d . . . N4 N 0.32397(11) -0.28073(13) 0.21330(10) 0.0320(5) Uani 1 1 d . . . C1 C 0.23627(13) 0.23504(15) 0.13348(11) 0.0239(6) Uani 1 1 d . . . C2 C 0.30218(14) 0.28328(15) 0.15387(12) 0.0282(6) Uani 1 1 d . . . C3 C 0.29294(17) 0.36599(17) 0.16531(13) 0.0400(7) Uani 1 1 d . . . H3A H 0.3373 0.3989 0.1801 0.048 Uiso 1 1 calc R . . C4 C 0.22020(17) 0.40143(17) 0.15550(14) 0.0460(8) Uani 1 1 d . . . H4A H 0.2144 0.4578 0.1651 0.055 Uiso 1 1 calc R . . C5 C 0.15664(16) 0.35485(17) 0.13186(14) 0.0400(7) Uani 1 1 d . . . H5A H 0.1068 0.3797 0.1237 0.048 Uiso 1 1 calc R . . C6 C 0.16386(14) 0.27197(15) 0.11957(12) 0.0298(6) Uani 1 1 d . . . C7 C 0.38059(13) 0.24453(16) 0.15846(12) 0.0312(6) Uani 1 1 d . . . H7A H 0.4208 0.2879 0.1630 0.037 Uiso 1 1 calc R . . H7B H 0.3913 0.2090 0.1967 0.037 Uiso 1 1 calc R . . C8 C 0.38096(16) 0.24843(17) 0.04581(13) 0.0415(7) Uani 1 1 d . . . H8A H 0.3329 0.2806 0.0395 0.062 Uiso 1 1 calc R . . H8B H 0.3822 0.2147 0.0080 0.062 Uiso 1 1 calc R . . H8C H 0.4256 0.2857 0.0527 0.062 Uiso 1 1 calc R . . C9 C 0.45608(14) 0.14700(17) 0.11051(14) 0.0413(7) Uani 1 1 d . . . H9A H 0.4591 0.1125 0.1485 0.062 Uiso 1 1 calc R . . H9B H 0.5007 0.1843 0.1160 0.062 Uiso 1 1 calc R . . H9C H 0.4565 0.1121 0.0732 0.062 Uiso 1 1 calc R . . C10 C 0.09440(13) 0.22093(16) 0.08878(12) 0.0313(6) Uani 1 1 d . . . H10A H 0.0724 0.1918 0.1221 0.038 Uiso 1 1 calc R . . H10B H 0.0538 0.2575 0.0655 0.038 Uiso 1 1 calc R . . C11 C 0.14001(14) 0.20049(17) -0.01110(12) 0.0349(7) Uani 1 1 d . . . H11A H 0.1547 0.1584 -0.0395 0.052 Uiso 1 1 calc R . . H11B H 0.1841 0.2373 0.0028 0.052 Uiso 1 1 calc R . . H11C H 0.0961 0.2323 -0.0338 0.052 Uiso 1 1 calc R . . C12 C 0.05534(14) 0.10161(16) 0.02376(13) 0.0376(7) Uani 1 1 d . . . H12A H 0.0730 0.0603 -0.0038 0.056 Uiso 1 1 calc R . . H12B H 0.0100 0.1303 0.0001 0.056 Uiso 1 1 calc R . . H12C H 0.0413 0.0746 0.0611 0.056 Uiso 1 1 calc R . . C13 C 0.24910(12) 0.02470(15) 0.04401(11) 0.0222(5) Uani 1 1 d . . . C14 C 0.28932(14) 0.04108(16) -0.00439(12) 0.0320(6) Uani 1 1 d . . . H14A H 0.3175 0.0910 -0.0038 0.038 Uiso 1 1 calc R . . C15 C 0.28950(15) -0.01400(18) -0.05407(13) 0.0407(7) Uani 1 1 d . . . H15A H 0.3176 -0.0020 -0.0870 0.049 Uiso 1 1 calc R . . C16 C 0.24860(16) -0.08591(18) -0.05486(14) 0.0431(8) Uani 1 1 d . . . H16A H 0.2479 -0.1238 -0.0888 0.052 Uiso 1 1 calc R . . C17 C 0.20870(16) -0.10347(17) -0.00694(14) 0.0434(8) Uani 1 1 d . . . H17A H 0.1806 -0.1535 -0.0077 0.052 Uiso 1 1 calc R . . C18 C 0.20912(14) -0.04836(16) 0.04278(12) 0.0331(6) Uani 1 1 d . . . H18A H 0.1817 -0.0611 0.0761 0.040 Uiso 1 1 calc R . . C21 C 0.16846(13) -0.21138(14) 0.18948(11) 0.0242(6) Uani 1 1 d . . . C22 C 0.08863(13) -0.21712(15) 0.18939(12) 0.0294(6) Uani 1 1 d . . . C23 C 0.04105(16) -0.25700(18) 0.13976(14) 0.0416(8) Uani 1 1 d . . . H23A H -0.0132 -0.2603 0.1391 0.050 Uiso 1 1 calc R . . C24 C 0.07211(17) -0.29139(18) 0.09201(15) 0.0494(9) Uani 1 1 d . . . H24A H 0.0388 -0.3160 0.0571 0.059 Uiso 1 1 calc R . . C25 C 0.15194(17) -0.29117(17) 0.09336(13) 0.0424(7) Uani 1 1 d . . . H25A H 0.1730 -0.3180 0.0608 0.051 Uiso 1 1 calc R . . C26 C 0.20056(14) -0.25113(15) 0.14305(12) 0.0305(6) Uani 1 1 d . . . C27 C 0.05552(13) -0.18306(16) 0.24391(12) 0.0308(6) Uani 1 1 d . . . H27A H 0.0405 -0.1250 0.2350 0.037 Uiso 1 1 calc R . . H27B H 0.0082 -0.2142 0.2481 0.037 Uiso 1 1 calc R . . C28 C 0.08503(15) -0.13821(17) 0.35309(13) 0.0377(7) Uani 1 1 d . . . H28A H 0.0347 -0.1586 0.3601 0.056 Uiso 1 1 calc R . . H28B H 0.0799 -0.0808 0.3392 0.056 Uiso 1 1 calc R . . H28C H 0.1229 -0.1420 0.3928 0.056 Uiso 1 1 calc R . . C29 C 0.12178(14) -0.27333(15) 0.32615(13) 0.0328(6) Uani 1 1 d . . . H29A H 0.0718 -0.2958 0.3322 0.049 Uiso 1 1 calc R . . H29B H 0.1585 -0.2751 0.3666 0.049 Uiso 1 1 calc R . . H29C H 0.1420 -0.3061 0.2943 0.049 Uiso 1 1 calc R . . C30 C 0.28766(14) -0.25492(16) 0.14883(12) 0.0336(6) Uani 1 1 d . . . H30A H 0.3013 -0.2943 0.1173 0.040 Uiso 1 1 calc R . . H30B H 0.3076 -0.2002 0.1396 0.040 Uiso 1 1 calc R . . C31 C 0.30603(17) -0.36712(18) 0.22315(16) 0.0526(9) Uani 1 1 d . . . H31A H 0.2497 -0.3740 0.2183 0.079 Uiso 1 1 calc R . . H31B H 0.3307 -0.3840 0.2661 0.079 Uiso 1 1 calc R . . H31C H 0.3256 -0.4012 0.1917 0.079 Uiso 1 1 calc R . . C32 C 0.40833(14) -0.26946(19) 0.22132(15) 0.0463(8) Uani 1 1 d . . . H32A H 0.4199 -0.2116 0.2144 0.070 Uiso 1 1 calc R . . H32B H 0.4288 -0.3037 0.1904 0.070 Uiso 1 1 calc R . . H32C H 0.4326 -0.2856 0.2646 0.070 Uiso 1 1 calc R . . C33 C 0.29278(12) -0.16518(15) 0.35692(11) 0.0241(6) Uani 1 1 d . . . C34 C 0.33511(13) -0.23577(17) 0.37365(12) 0.0334(6) Uani 1 1 d . . . H34A H 0.3413 -0.2745 0.3417 0.040 Uiso 1 1 calc R . . C35 C 0.36860(14) -0.2511(2) 0.43630(14) 0.0445(8) Uani 1 1 d . . . H35A H 0.3973 -0.3002 0.4469 0.053 Uiso 1 1 calc R . . C36 C 0.36074(16) -0.1963(2) 0.48272(14) 0.0504(9) Uani 1 1 d . . . H36A H 0.3841 -0.2070 0.5256 0.060 Uiso 1 1 calc R . . C37 C 0.31918(18) -0.1256(2) 0.46759(14) 0.0561(9) Uani 1 1 d . . . H37A H 0.3135 -0.0874 0.5000 0.067 Uiso 1 1 calc R . . C38 C 0.28520(15) -0.10959(19) 0.40442(13) 0.0411(7) Uani 1 1 d . . . H38A H 0.2567 -0.0603 0.3940 0.049 Uiso 1 1 calc R . . C41 C 0.03726(12) 0.03963(14) 0.22538(11) 0.0212(5) Uani 1 1 d . . . C42 C -0.00882(12) 0.00697(14) 0.17059(12) 0.0251(6) Uani 1 1 d . . . H42A H 0.0146 -0.0072 0.1353 0.030 Uiso 1 1 calc R . . C43 C -0.08793(13) -0.00514(15) 0.16680(13) 0.0308(6) Uani 1 1 d . . . H43A H -0.1181 -0.0270 0.1291 0.037 Uiso 1 1 calc R . . C44 C -0.12256(13) 0.01465(15) 0.21783(14) 0.0322(6) Uani 1 1 d . . . H44A H -0.1766 0.0058 0.2154 0.039 Uiso 1 1 calc R . . C45 C -0.07919(13) 0.04710(15) 0.27226(13) 0.0320(6) Uani 1 1 d . . . H45A H -0.1030 0.0609 0.3074 0.038 Uiso 1 1 calc R . . C46 C 0.00016(12) 0.05967(14) 0.27543(12) 0.0253(6) Uani 1 1 d . . . H46A H 0.0297 0.0827 0.3130 0.030 Uiso 1 1 calc R . . C47 C 0.18006(12) 0.13861(14) 0.28226(11) 0.0211(5) Uani 1 1 d . . . C48 C 0.24291(15) 0.13603(18) 0.33181(13) 0.0428(8) Uani 1 1 d . . . H48A H 0.2692 0.0855 0.3422 0.051 Uiso 1 1 calc R . . C49 C 0.26815(17) 0.2061(2) 0.36659(15) 0.0549(9) Uani 1 1 d . . . H49A H 0.3108 0.2025 0.4010 0.066 Uiso 1 1 calc R . . C50 C 0.23286(15) 0.27953(18) 0.35220(14) 0.0420(7) Uani 1 1 d . . . H50A H 0.2510 0.3272 0.3760 0.050 Uiso 1 1 calc R . . C51 C 0.17094(15) 0.28451(17) 0.30324(14) 0.0386(7) Uani 1 1 d . . . H51A H 0.1455 0.3355 0.2928 0.046 Uiso 1 1 calc R . . C52 C 0.14564(14) 0.21447(15) 0.26902(12) 0.0306(6) Uani 1 1 d . . . H52A H 0.1027 0.2187 0.2349 0.037 Uiso 1 1 calc R . . C61 C 0.44967(12) -0.05142(15) 0.17471(11) 0.0239(5) Uani 1 1 d . . . C62 C 0.43035(13) -0.08233(16) 0.11301(12) 0.0301(6) Uani 1 1 d . . . H62A H 0.3777 -0.0807 0.0921 0.036 Uiso 1 1 calc R . . C63 C 0.48524(14) -0.11523(18) 0.08128(13) 0.0401(7) Uani 1 1 d . . . H63A H 0.4702 -0.1342 0.0388 0.048 Uiso 1 1 calc R . . C64 C 0.56189(15) -0.1207(2) 0.11110(14) 0.0504(8) Uani 1 1 d . . . H64A H 0.5995 -0.1449 0.0899 0.060 Uiso 1 1 calc R . . C65 C 0.58266(15) -0.0907(2) 0.17180(14) 0.0561(10) Uani 1 1 d . . . H65A H 0.6351 -0.0942 0.1929 0.067 Uiso 1 1 calc R . . C66 C 0.52796(13) -0.05536(19) 0.20254(12) 0.0419(8) Uani 1 1 d . . . H66A H 0.5441 -0.0331 0.2439 0.050 Uiso 1 1 calc R . . C67 C 0.42280(12) 0.01101(15) 0.30210(11) 0.0225(5) Uani 1 1 d . . . C68 C 0.45806(13) -0.04967(17) 0.34295(11) 0.0322(6) Uani 1 1 d . . . H68A H 0.4544 -0.1053 0.3292 0.039 Uiso 1 1 calc R . . C69 C 0.49822(15) -0.03140(19) 0.40294(13) 0.0448(8) Uani 1 1 d . . . H69A H 0.5220 -0.0741 0.4299 0.054 Uiso 1 1 calc R . . C70 C 0.50379(16) 0.0485(2) 0.42373(13) 0.0489(8) Uani 1 1 d . . . H70A H 0.5315 0.0611 0.4651 0.059 Uiso 1 1 calc R . . C71 C 0.46970(17) 0.10972(18) 0.38520(13) 0.0450(8) Uani 1 1 d . . . H71A H 0.4731 0.1650 0.3998 0.054 Uiso 1 1 calc R . . C72 C 0.42980(14) 0.09122(16) 0.32431(12) 0.0340(6) Uani 1 1 d . . . H72A H 0.4069 0.1345 0.2974 0.041 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 Sn1 0.02134(9) 0.01947(10) 0.01781(9) -0.00120(7) 0.00298(6) -0.00247(7) Sn2 0.01816(8) 0.01724(9) 0.02034(9) 0.00077(7) 0.00168(6) 0.00059(7) Si1 0.0179(3) 0.0168(4) 0.0206(3) 0.0000(3) 0.0029(2) -0.0004(3) Si2 0.0181(3) 0.0241(4) 0.0179(3) -0.0021(3) 0.0024(2) -0.0024(3) O1 0.0214(8) 0.0252(10) 0.0212(9) 0.0006(7) 0.0046(6) -0.0058(7) O2 0.0218(8) 0.0172(9) 0.0278(9) 0.0021(7) 0.0061(7) 0.0023(7) O3 0.0187(8) 0.0223(10) 0.0273(9) -0.0025(7) 0.0068(6) -0.0003(7) O4 0.0221(8) 0.0246(9) 0.0211(9) 0.0015(7) -0.0006(6) -0.0022(7) N1 0.0296(11) 0.0274(13) 0.0320(13) -0.0003(10) 0.0068(9) -0.0032(10) N2 0.0227(10) 0.0244(12) 0.0289(12) 0.0025(9) 0.0015(8) -0.0023(9) N3 0.0234(10) 0.0204(12) 0.0359(13) 0.0067(9) 0.0071(9) 0.0012(9) N4 0.0296(12) 0.0278(13) 0.0383(14) 0.0000(10) 0.0057(9) 0.0009(10) C1 0.0304(13) 0.0224(14) 0.0200(13) -0.0012(10) 0.0070(10) -0.0025(11) C2 0.0357(14) 0.0238(15) 0.0255(14) -0.0044(11) 0.0063(11) -0.0078(12) C3 0.0531(18) 0.0311(17) 0.0367(17) -0.0117(13) 0.0107(13) -0.0156(14) C4 0.063(2) 0.0226(17) 0.055(2) -0.0138(14) 0.0197(15) 0.0007(15) C5 0.0435(16) 0.0291(17) 0.0507(19) -0.0021(14) 0.0177(13) 0.0085(14) C6 0.0330(14) 0.0250(15) 0.0335(15) -0.0005(12) 0.0114(11) -0.0006(12) C7 0.0316(14) 0.0303(16) 0.0298(15) -0.0033(12) 0.0007(11) -0.0144(12) C8 0.0537(18) 0.0368(18) 0.0355(17) 0.0031(13) 0.0124(13) -0.0051(14) C9 0.0282(14) 0.0423(18) 0.0541(19) 0.0001(15) 0.0095(13) -0.0045(13) C10 0.0262(13) 0.0309(16) 0.0370(16) 0.0034(12) 0.0064(11) 0.0058(12) C11 0.0334(14) 0.0389(17) 0.0307(16) 0.0095(12) 0.0009(11) -0.0002(12) C12 0.0307(14) 0.0377(17) 0.0399(17) 0.0050(13) -0.0053(12) -0.0058(13) C13 0.0239(12) 0.0235(14) 0.0174(12) -0.0019(10) -0.0011(9) 0.0018(10) C14 0.0390(15) 0.0285(15) 0.0278(15) -0.0048(12) 0.0046(11) -0.0015(12) C15 0.0465(16) 0.050(2) 0.0269(16) -0.0100(13) 0.0114(12) -0.0005(15) C16 0.0508(18) 0.0391(19) 0.0363(18) -0.0189(14) -0.0006(14) 0.0036(15) C17 0.0520(18) 0.0257(16) 0.0489(19) -0.0099(14) -0.0008(14) -0.0098(14) C18 0.0391(15) 0.0279(16) 0.0313(15) -0.0029(12) 0.0033(11) -0.0039(12) C21 0.0283(13) 0.0161(13) 0.0258(14) 0.0017(10) -0.0013(10) -0.0036(10) C22 0.0262(13) 0.0211(14) 0.0368(16) 0.0122(12) -0.0053(11) -0.0047(11) C23 0.0344(15) 0.0412(18) 0.0429(19) 0.0108(14) -0.0103(13) -0.0115(13) C24 0.053(2) 0.0429(19) 0.042(2) 0.0032(15) -0.0195(15) -0.0186(15) C25 0.063(2) 0.0342(17) 0.0268(16) -0.0055(13) 0.0006(13) -0.0089(15) C26 0.0392(15) 0.0241(15) 0.0259(14) 0.0011(11) -0.0001(11) -0.0066(12) C27 0.0196(12) 0.0254(15) 0.0451(17) 0.0119(12) -0.0003(11) 0.0004(11) C28 0.0384(15) 0.0307(16) 0.0500(18) 0.0075(13) 0.0243(13) 0.0064(13) C29 0.0326(14) 0.0223(15) 0.0428(17) 0.0129(12) 0.0051(12) -0.0005(12) C30 0.0458(16) 0.0280(16) 0.0293(15) -0.0075(12) 0.0134(12) -0.0011(12) C31 0.0527(19) 0.0346(19) 0.070(2) 0.0089(16) 0.0086(16) -0.0007(15) C32 0.0341(16) 0.050(2) 0.057(2) 0.0032(16) 0.0139(14) 0.0093(14) C33 0.0183(12) 0.0320(15) 0.0221(13) 0.0044(11) 0.0041(9) -0.0002(11) C34 0.0302(14) 0.0385(17) 0.0322(16) 0.0108(12) 0.0073(11) 0.0063(12) C35 0.0298(15) 0.063(2) 0.0399(18) 0.0220(16) 0.0028(13) 0.0095(14) C36 0.0371(16) 0.087(3) 0.0252(17) 0.0205(17) -0.0004(12) 0.0036(17) C37 0.064(2) 0.079(3) 0.0250(17) -0.0115(16) 0.0061(14) 0.0003(19) C38 0.0439(16) 0.0494(19) 0.0287(16) -0.0005(14) 0.0033(12) 0.0060(14) C41 0.0217(12) 0.0132(12) 0.0284(14) 0.0049(10) 0.0037(10) 0.0020(10) C42 0.0257(13) 0.0197(14) 0.0293(14) 0.0037(11) 0.0038(10) 0.0008(10) C43 0.0263(13) 0.0206(14) 0.0421(17) 0.0026(12) -0.0028(11) -0.0045(11) C44 0.0183(13) 0.0202(14) 0.0584(19) 0.0056(13) 0.0073(12) -0.0014(11) C45 0.0270(13) 0.0269(15) 0.0457(17) 0.0035(13) 0.0169(12) 0.0015(12) C46 0.0227(12) 0.0200(14) 0.0333(15) 0.0004(11) 0.0056(10) 0.0021(10) C47 0.0192(12) 0.0221(14) 0.0233(13) -0.0007(10) 0.0072(9) -0.0031(10) C48 0.0456(17) 0.0336(17) 0.0431(18) -0.0057(14) -0.0085(14) 0.0015(14) C49 0.0509(19) 0.047(2) 0.056(2) -0.0166(16) -0.0196(15) -0.0054(16) C50 0.0390(16) 0.0342(18) 0.056(2) -0.0254(15) 0.0180(14) -0.0158(14) C51 0.0412(16) 0.0240(16) 0.0538(19) -0.0105(14) 0.0170(14) 0.0005(13) C52 0.0283(14) 0.0268(16) 0.0361(16) -0.0069(12) 0.0042(11) 0.0026(11) C61 0.0186(12) 0.0288(15) 0.0241(13) 0.0004(11) 0.0037(9) -0.0035(10) C62 0.0235(13) 0.0388(17) 0.0272(14) -0.0047(12) 0.0023(10) -0.0013(11) C63 0.0362(16) 0.057(2) 0.0278(16) -0.0145(14) 0.0078(12) -0.0073(14) C64 0.0314(15) 0.081(3) 0.0431(19) -0.0155(17) 0.0182(13) 0.0059(15) C65 0.0205(14) 0.109(3) 0.0380(18) -0.0183(18) 0.0025(12) 0.0051(16) C66 0.0254(14) 0.074(2) 0.0257(15) -0.0119(14) 0.0045(11) -0.0031(14) C67 0.0226(12) 0.0263(15) 0.0194(13) -0.0024(10) 0.0062(9) -0.0023(11) C68 0.0346(14) 0.0334(16) 0.0264(15) -0.0027(12) -0.0003(11) 0.0036(12) C69 0.0494(17) 0.050(2) 0.0286(16) 0.0046(14) -0.0088(13) 0.0077(15) C70 0.0586(19) 0.061(2) 0.0208(15) -0.0037(14) -0.0087(13) -0.0131(16) C71 0.068(2) 0.0355(17) 0.0291(16) -0.0096(14) 0.0027(14) -0.0157(15) C72 0.0442(15) 0.0337(17) 0.0229(14) 0.0011(12) 0.0027(11) -0.0084(13) _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 1.9994(14) . ? Sn1 O1 1.9999(15) . ? Sn1 C13 2.119(2) . ? Sn1 C1 2.128(2) . ? Sn2 O2 1.9873(15) . ? Sn2 O3 1.9934(15) . ? Sn2 C33 2.123(2) . ? Sn2 C21 2.123(2) . ? Si1 O2 1.6042(16) . ? Si1 O1 1.6115(16) . ? Si1 C47 1.874(2) . ? Si1 C41 1.887(2) . ? Si2 O3 1.6091(16) . ? Si2 O4 1.6067(16) . ? Si2 C67 1.873(2) . ? Si2 C61 1.890(2) . ? N1 C8 1.463(3) . ? N1 C9 1.469(3) . ? N1 C7 1.471(3) . ? N2 C11 1.465(3) . ? N2 C10 1.468(3) . ? N2 C12 1.468(3) . ? N3 C28 1.460(3) . ? N3 C27 1.471(3) . ? N3 C29 1.471(3) . ? N4 C31 1.465(3) . ? N4 C32 1.470(3) . ? N4 C30 1.470(3) . ? C1 C6 1.388(3) . ? C1 C2 1.400(3) . ? C2 C3 1.383(4) . ? C2 C7 1.500(3) . ? C3 C4 1.381(4) . ? C3 H3A 0.9500 . ? C4 C5 1.367(4) . ? C4 H4A 0.9500 . ? C5 C6 1.385(4) . ? C5 H5A 0.9500 . ? C6 C10 1.522(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.379(3) . ? C13 C14 1.378(3) . ? C14 C15 1.390(4) . ? C14 H14A 0.9500 . ? C15 C16 1.372(4) . ? C15 H15A 0.9500 . ? C16 C17 1.370(4) . ? C16 H16A 0.9500 . ? C17 C18 1.389(4) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C21 C26 1.386(4) . ? C21 C22 1.403(3) . ? C22 C23 1.386(3) . ? C22 C27 1.498(4) . ? C23 C24 1.360(4) . ? C23 H23A 0.9500 . ? C24 C25 1.395(4) . ? C24 H24A 0.9500 . ? C25 C26 1.397(3) . ? C25 H25A 0.9500 . ? C26 C30 1.511(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.380(3) . ? C33 C38 1.384(4) . ? C34 C35 1.383(3) . ? C34 H34A 0.9500 . ? C35 C36 1.359(4) . ? C35 H35A 0.9500 . ? C36 C37 1.370(4) . ? C36 H36A 0.9500 . ? C37 C38 1.397(4) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C41 C46 1.387(3) . ? C41 C42 1.401(3) . ? C42 C43 1.389(3) . ? C42 H42A 0.9500 . ? C43 C44 1.378(4) . ? C43 H43A 0.9500 . ? C44 C45 1.375(3) . ? C44 H44A 0.9500 . ? C45 C46 1.396(3) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 C52 1.381(3) . ? C47 C48 1.384(3) . ? C48 C49 1.389(4) . ? C48 H48A 0.9500 . ? C49 C50 1.355(4) . ? C49 H49A 0.9500 . ? C50 C51 1.367(4) . ? C50 H50A 0.9500 . ? C51 C52 1.384(3) . ? C51 H51A 0.9500 . ? C52 H52A 0.9500 . ? C61 C62 1.394(3) . ? C61 C66 1.395(3) . ? C62 C63 1.381(3) . ? C62 H62A 0.9500 . ? C63 C64 1.382(3) . ? C63 H63A 0.9500 . ? C64 C65 1.372(4) . ? C64 H64A 0.9500 . ? C65 C66 1.382(4) . ? C65 H65A 0.9500 . ? C66 H66A 0.9500 . ? C67 C72 1.387(3) . ? C67 C68 1.387(3) . ? C68 C69 1.378(3) . ? C68 H68A 0.9500 . ? C69 C70 1.373(4) . ? C69 H69A 0.9500 . ? C70 C71 1.360(4) . ? C70 H70A 0.9500 . ? C71 C72 1.394(3) . ? C71 H71A 0.9500 . ? C72 H72A 0.9500 . ? 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 O1 94.47(6) . . ? O4 Sn1 C13 104.48(7) . . ? O1 Sn1 C13 101.78(8) . . ? O4 Sn1 C1 105.80(7) . . ? O1 Sn1 C1 105.89(8) . . ? C13 Sn1 C1 136.71(9) . . ? O2 Sn2 O3 94.26(6) . . ? O2 Sn2 C33 103.42(8) . . ? O3 Sn2 C33 105.84(7) . . ? O2 Sn2 C21 110.23(7) . . ? O3 Sn2 C21 101.82(8) . . ? C33 Sn2 C21 134.16(9) . . ? O2 Si1 O1 116.00(9) . . ? O2 Si1 C47 107.35(9) . . ? O1 Si1 C47 111.57(10) . . ? O2 Si1 C41 107.80(9) . . ? O1 Si1 C41 105.88(9) . . ? C47 Si1 C41 107.92(10) . . ? O3 Si2 O4 114.80(8) . . ? O3 Si2 C67 111.97(10) . . ? O4 Si2 C67 106.99(10) . . ? O3 Si2 C61 104.17(10) . . ? O4 Si2 C61 111.95(10) . . ? C67 Si2 C61 106.74(10) . . ? Si1 O1 Sn1 135.46(8) . . ? Si1 O2 Sn2 143.90(10) . . ? Si2 O3 Sn2 142.42(10) . . ? Si2 O4 Sn1 140.50(9) . . ? C8 N1 C9 109.3(2) . . ? C8 N1 C7 110.3(2) . . ? C9 N1 C7 110.18(19) . . ? C11 N2 C10 112.1(2) . . ? C11 N2 C12 109.70(19) . . ? C10 N2 C12 110.62(19) . . ? C28 N3 C27 110.53(19) . . ? C28 N3 C29 109.3(2) . . ? C27 N3 C29 110.70(19) . . ? C31 N4 C32 109.9(2) . . ? C31 N4 C30 109.9(2) . . ? C32 N4 C30 109.3(2) . . ? C6 C1 C2 119.7(2) . . ? C6 C1 Sn1 119.14(17) . . ? C2 C1 Sn1 121.12(17) . . ? C3 C2 C1 119.0(2) . . ? C3 C2 C7 122.2(2) . . ? C1 C2 C7 118.7(2) . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 119.5(2) . . ? C1 C6 C10 119.1(2) . . ? C5 C6 C10 121.4(2) . . ? N1 C7 C2 110.53(18) . . ? N1 C7 H7A 109.5 . . ? C2 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C6 110.25(19) . . ? N2 C10 H10A 109.6 . . ? C6 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C6 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 118.7(2) . . ? C18 C13 Sn1 117.81(19) . . ? C14 C13 Sn1 123.51(18) . . ? C13 C14 C15 121.3(3) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C16 C15 C14 119.1(3) . . ? C16 C15 H15A 120.4 . . ? C14 C15 H15A 120.4 . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C13 C18 C17 120.3(3) . . ? C13 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C26 C21 C22 120.1(2) . . ? C26 C21 Sn2 122.87(17) . . ? C22 C21 Sn2 116.98(19) . . ? C23 C22 C21 119.7(3) . . ? C23 C22 C27 120.2(2) . . ? C21 C22 C27 120.1(2) . . ? C24 C23 C22 119.9(3) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C25 121.3(3) . . ? C23 C24 H24A 119.4 . . ? C25 C24 H24A 119.4 . . ? C24 C25 C26 119.3(3) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C21 C26 C25 119.4(2) . . ? C21 C26 C30 119.7(2) . . ? C25 C26 C30 120.8(2) . . ? N3 C27 C22 111.72(19) . . ? N3 C27 H27A 109.3 . . ? C22 C27 H27A 109.3 . . ? N3 C27 H27B 109.3 . . ? C22 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? N3 C28 H28A 109.5 . . ? N3 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N3 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N3 C29 H29A 109.5 . . ? N3 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N3 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N4 C30 C26 110.4(2) . . ? N4 C30 H30A 109.6 . . ? C26 C30 H30A 109.6 . . ? N4 C30 H30B 109.6 . . ? C26 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? N4 C31 H31A 109.5 . . ? N4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 118.3(2) . . ? C34 C33 Sn2 123.32(19) . . ? C38 C33 Sn2 118.38(18) . . ? C33 C34 C35 121.0(3) . . ? C33 C34 H34A 119.5 . . ? C35 C34 H34A 119.5 . . ? C36 C35 C34 120.4(3) . . ? C36 C35 H35A 119.8 . . ? C34 C35 H35A 119.8 . . ? C35 C36 C37 120.0(3) . . ? C35 C36 H36A 120.0 . . ? C37 C36 H36A 120.0 . . ? C36 C37 C38 120.0(3) . . ? C36 C37 H37A 120.0 . . ? C38 C37 H37A 120.0 . . ? C33 C38 C37 120.4(3) . . ? C33 C38 H38A 119.8 . . ? C37 C38 H38A 119.8 . . ? C46 C41 C42 116.9(2) . . ? C46 C41 Si1 121.99(17) . . ? C42 C41 Si1 120.84(18) . . ? C43 C42 C41 121.5(2) . . ? C43 C42 H42A 119.3 . . ? C41 C42 H42A 119.3 . . ? C44 C43 C42 119.9(2) . . ? C44 C43 H43A 120.0 . . ? C42 C43 H43A 120.0 . . ? C45 C44 C43 120.2(2) . . ? C45 C44 H44A 119.9 . . ? C43 C44 H44A 119.9 . . ? C44 C45 C46 119.4(2) . . ? C44 C45 H45A 120.3 . . ? C46 C45 H45A 120.3 . . ? C41 C46 C45 122.0(2) . . ? C41 C46 H46A 119.0 . . ? C45 C46 H46A 119.0 . . ? C52 C47 C48 116.2(2) . . ? C52 C47 Si1 121.24(17) . . ? C48 C47 Si1 122.46(19) . . ? C47 C48 C49 121.1(3) . . ? C47 C48 H48A 119.4 . . ? C49 C48 H48A 119.4 . . ? C50 C49 C48 121.0(3) . . ? C50 C49 H49A 119.5 . . ? C48 C49 H49A 119.5 . . ? C49 C50 C51 119.5(3) . . ? C49 C50 H50A 120.2 . . ? C51 C50 H50A 120.2 . . ? C50 C51 C52 119.3(3) . . ? C50 C51 H51A 120.3 . . ? C52 C51 H51A 120.3 . . ? C47 C52 C51 122.8(2) . . ? C47 C52 H52A 118.6 . . ? C51 C52 H52A 118.6 . . ? C62 C61 C66 116.0(2) . . ? C62 C61 Si2 121.22(16) . . ? C66 C61 Si2 122.61(18) . . ? C63 C62 C61 122.1(2) . . ? C63 C62 H62A 118.9 . . ? C61 C62 H62A 118.9 . . ? C64 C63 C62 120.3(2) . . ? C64 C63 H63A 119.8 . . ? C62 C63 H63A 119.8 . . ? C65 C64 C63 118.9(3) . . ? C65 C64 H64A 120.6 . . ? C63 C64 H64A 120.6 . . ? C64 C65 C66 120.6(2) . . ? C64 C65 H65A 119.7 . . ? C66 C65 H65A 119.7 . . ? C65 C66 C61 122.1(2) . . ? C65 C66 H66A 119.0 . . ? C61 C66 H66A 119.0 . . ? C72 C67 C68 117.0(2) . . ? C72 C67 Si2 121.84(18) . . ? C68 C67 Si2 121.13(18) . . ? C69 C68 C67 121.7(3) . . ? C69 C68 H68A 119.1 . . ? C67 C68 H68A 119.1 . . ? C70 C69 C68 120.0(3) . . ? C70 C69 H69A 120.0 . . ? C68 C69 H69A 120.0 . . ? C71 C70 C69 120.1(2) . . ? C71 C70 H70A 120.0 . . ? C69 C70 H70A 120.0 . . ? C70 C71 C72 119.9(3) . . ? C70 C71 H71A 120.1 . . ? C72 C71 H71A 120.1 . . ? C67 C72 C71 121.4(2) . . ? C67 C72 H72A 119.3 . . ? C71 C72 H72A 119.3 . . ? 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 O2 Si1 O1 Sn1 -88.04(14) . . . . ? C47 Si1 O1 Sn1 35.30(16) . . . . ? C41 Si1 O1 Sn1 152.46(13) . . . . ? O4 Sn1 O1 Si1 39.74(14) . . . . ? C13 Sn1 O1 Si1 145.56(13) . . . . ? C1 Sn1 O1 Si1 -68.09(14) . . . . ? O1 Si1 O2 Sn2 -10.84(18) . . . . ? C47 Si1 O2 Sn2 -136.36(15) . . . . ? C41 Si1 O2 Sn2 107.60(16) . . . . ? O3 Sn2 O2 Si1 51.34(15) . . . . ? C33 Sn2 O2 Si1 158.75(15) . . . . ? C21 Sn2 O2 Si1 -52.92(17) . . . . ? O4 Si2 O3 Sn2 -78.45(16) . . . . ? C67 Si2 O3 Sn2 43.80(17) . . . . ? C61 Si2 O3 Sn2 158.78(14) . . . . ? O2 Sn2 O3 Si2 42.56(15) . . . . ? C33 Sn2 O3 Si2 -62.68(16) . . . . ? C21 Sn2 O3 Si2 154.26(15) . . . . ? O3 Si2 O4 Sn1 -32.57(18) . . . . ? C67 Si2 O4 Sn1 -157.47(14) . . . . ? C61 Si2 O4 Sn1 85.92(16) . . . . ? O1 Sn1 O4 Si2 64.79(16) . . . . ? C13 Sn1 O4 Si2 -38.61(17) . . . . ? C1 Sn1 O4 Si2 172.70(15) . . . . ? O4 Sn1 C1 C6 -146.28(19) . . . . ? O1 Sn1 C1 C6 -46.8(2) . . . . ? C13 Sn1 C1 C6 80.9(2) . . . . ? O4 Sn1 C1 C2 35.4(2) . . . . ? O1 Sn1 C1 C2 134.90(19) . . . . ? C13 Sn1 C1 C2 -97.4(2) . . . . ? C6 C1 C2 C3 5.9(4) . . . . ? Sn1 C1 C2 C3 -175.86(19) . . . . ? C6 C1 C2 C7 -170.2(2) . . . . ? Sn1 C1 C2 C7 8.0(3) . . . . ? C1 C2 C3 C4 -1.5(4) . . . . ? C7 C2 C3 C4 174.5(3) . . . . ? C2 C3 C4 C5 -2.5(5) . . . . ? C3 C4 C5 C6 2.2(5) . . . . ? C2 C1 C6 C5 -6.2(4) . . . . ? Sn1 C1 C6 C5 175.5(2) . . . . ? C2 C1 C6 C10 171.5(2) . . . . ? Sn1 C1 C6 C10 -6.8(3) . . . . ? C4 C5 C6 C1 2.2(4) . . . . ? C4 C5 C6 C10 -175.5(3) . . . . ? C8 N1 C7 C2 68.3(3) . . . . ? C9 N1 C7 C2 -170.9(2) . . . . ? C3 C2 C7 N1 -130.5(3) . . . . ? C1 C2 C7 N1 45.4(3) . . . . ? C11 N2 C10 C6 -67.8(2) . . . . ? C12 N2 C10 C6 169.4(2) . . . . ? C1 C6 C10 N2 -35.2(3) . . . . ? C5 C6 C10 N2 142.5(3) . . . . ? O4 Sn1 C13 C18 86.69(18) . . . . ? O1 Sn1 C13 C18 -11.13(18) . . . . ? C1 Sn1 C13 C18 -140.13(17) . . . . ? O4 Sn1 C13 C14 -93.2(2) . . . . ? O1 Sn1 C13 C14 168.96(19) . . . . ? C1 Sn1 C13 C14 40.0(2) . . . . ? C18 C13 C14 C15 0.6(4) . . . . ? Sn1 C13 C14 C15 -179.49(19) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C14 C13 C18 C17 -1.0(4) . . . . ? Sn1 C13 C18 C17 179.12(19) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? O2 Sn2 C21 C26 133.14(19) . . . . ? O3 Sn2 C21 C26 34.1(2) . . . . ? C33 Sn2 C21 C26 -92.2(2) . . . . ? O2 Sn2 C21 C22 -46.67(19) . . . . ? O3 Sn2 C21 C22 -145.75(17) . . . . ? C33 Sn2 C21 C22 88.0(2) . . . . ? C26 C21 C22 C23 -5.3(4) . . . . ? Sn2 C21 C22 C23 174.50(18) . . . . ? C26 C21 C22 C27 172.4(2) . . . . ? Sn2 C21 C22 C27 -7.8(3) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C27 C22 C23 C24 -176.7(3) . . . . ? C22 C23 C24 C25 3.3(4) . . . . ? C23 C24 C25 C26 -3.3(4) . . . . ? C22 C21 C26 C25 5.2(4) . . . . ? Sn2 C21 C26 C25 -174.56(18) . . . . ? C22 C21 C26 C30 -171.2(2) . . . . ? Sn2 C21 C26 C30 9.0(3) . . . . ? C24 C25 C26 C21 -1.0(4) . . . . ? C24 C25 C26 C30 175.4(2) . . . . ? C28 N3 C27 C22 167.2(2) . . . . ? C29 N3 C27 C22 -71.5(3) . . . . ? C23 C22 C27 N3 146.8(2) . . . . ? C21 C22 C27 N3 -30.9(3) . . . . ? C31 N4 C30 C26 69.5(3) . . . . ? C32 N4 C30 C26 -169.7(2) . . . . ? C21 C26 C30 N4 47.8(3) . . . . ? C25 C26 C30 N4 -128.5(2) . . . . ? O2 Sn2 C33 C34 178.01(19) . . . . ? O3 Sn2 C33 C34 -83.5(2) . . . . ? C21 Sn2 C33 C34 41.4(3) . . . . ? O2 Sn2 C33 C38 0.5(2) . . . . ? O3 Sn2 C33 C38 99.0(2) . . . . ? C21 Sn2 C33 C38 -136.1(2) . . . . ? C38 C33 C34 C35 0.5(4) . . . . ? Sn2 C33 C34 C35 -176.94(19) . . . . ? C33 C34 C35 C36 -0.4(4) . . . . ? C34 C35 C36 C37 0.3(5) . . . . ? C35 C36 C37 C38 -0.3(5) . . . . ? C34 C33 C38 C37 -0.6(4) . . . . ? Sn2 C33 C38 C37 177.0(2) . . . . ? C36 C37 C38 C33 0.5(5) . . . . ? O2 Si1 C41 C46 78.2(2) . . . . ? O1 Si1 C41 C46 -157.02(19) . . . . ? C47 Si1 C41 C46 -37.4(2) . . . . ? O2 Si1 C41 C42 -95.95(19) . . . . ? O1 Si1 C41 C42 28.8(2) . . . . ? C47 Si1 C41 C42 148.39(18) . . . . ? C46 C41 C42 C43 -0.3(3) . . . . ? Si1 C41 C42 C43 174.12(18) . . . . ? C41 C42 C43 C44 -0.4(4) . . . . ? C42 C43 C44 C45 0.6(4) . . . . ? C43 C44 C45 C46 -0.1(4) . . . . ? C42 C41 C46 C45 0.9(3) . . . . ? Si1 C41 C46 C45 -173.52(18) . . . . ? C44 C45 C46 C41 -0.7(4) . . . . ? O2 Si1 C47 C52 -166.0(2) . . . . ? O1 Si1 C47 C52 65.9(2) . . . . ? C41 Si1 C47 C52 -50.0(2) . . . . ? O2 Si1 C47 C48 17.2(2) . . . . ? O1 Si1 C47 C48 -110.9(2) . . . . ? C41 Si1 C47 C48 133.2(2) . . . . ? C52 C47 C48 C49 1.3(4) . . . . ? Si1 C47 C48 C49 178.2(3) . . . . ? C47 C48 C49 C50 -1.3(5) . . . . ? C48 C49 C50 C51 0.8(5) . . . . ? C49 C50 C51 C52 -0.3(4) . . . . ? C48 C47 C52 C51 -0.8(4) . . . . ? Si1 C47 C52 C51 -177.8(2) . . . . ? C50 C51 C52 C47 0.3(4) . . . . ? O3 Si2 C61 C62 55.6(2) . . . . ? O4 Si2 C61 C62 -69.1(2) . . . . ? C67 Si2 C61 C62 174.2(2) . . . . ? O3 Si2 C61 C66 -119.6(2) . . . . ? O4 Si2 C61 C66 115.8(2) . . . . ? C67 Si2 C61 C66 -1.0(3) . . . . ? C66 C61 C62 C63 0.2(4) . . . . ? Si2 C61 C62 C63 -175.2(2) . . . . ? C61 C62 C63 C64 2.0(4) . . . . ? C62 C63 C64 C65 -2.0(5) . . . . ? C63 C64 C65 C66 -0.2(5) . . . . ? C64 C65 C66 C61 2.5(5) . . . . ? C62 C61 C66 C65 -2.4(4) . . . . ? Si2 C61 C66 C65 172.9(3) . . . . ? O3 Si2 C67 C72 -135.4(2) . . . . ? O4 Si2 C67 C72 -8.8(2) . . . . ? C61 Si2 C67 C72 111.2(2) . . . . ? O3 Si2 C67 C68 47.7(2) . . . . ? O4 Si2 C67 C68 174.33(19) . . . . ? C61 Si2 C67 C68 -65.7(2) . . . . ? C72 C67 C68 C69 0.1(4) . . . . ? Si2 C67 C68 C69 177.1(2) . . . . ? C67 C68 C69 C70 0.3(4) . . . . ? C68 C69 C70 C71 0.0(5) . . . . ? C69 C70 C71 C72 -0.7(5) . . . . ? C68 C67 C72 C71 -0.8(4) . . . . ? Si2 C67 C72 C71 -177.7(2) . . . . ? C70 C71 C72 C67 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.560 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.060 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 255 45 ' ' 2 0.000 0.500 1.000 255 45 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 952148'