# 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 _database_code_depnum_ccdc_archive 'CCDC 921170' #TrackingRef 'az080520Sn1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H29 Cl N2 O2 Sn, 2(C6 H6)' _chemical_formula_sum 'C37 H41 Cl N2 O2 Sn' _chemical_formula_weight 699.86 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' Cl Cl 0.1484 0.1585 '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 P21/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 12.6721(5) _cell_length_b 21.1300(18) _cell_length_c 16.1630(9) _cell_angle_alpha 90 _cell_angle_beta 127.645(4) _cell_angle_gamma 90 _cell_volume 3426.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 35304 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.857 # 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 0.161 0 1 0 0.069 0 0 -1 0.133 1 0 1 0.079 0 0 1 0.119 -1 1 -1 0.124 -1 1 1 0.085 1 -1 -1 0.109 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.920 _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 35184 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7459 _reflns_number_gt 5162 _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, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0146P)^2^+4.1492P] 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 7459 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.46983(2) 0.251821(11) 0.270215(17) 0.03534(7) Uani 1 1 d . . . Cl1 Cl 0.35582(10) 0.20314(5) 0.09923(7) 0.0538(2) Uani 1 1 d . . . O1 O 0.6506(2) 0.24179(11) 0.2966(2) 0.0466(6) Uani 1 1 d . . . O2 O 0.6580(3) 0.13661(13) 0.3095(2) 0.0608(7) Uani 1 1 d . . . C10 C 0.4413(3) 0.18270(16) 0.3496(3) 0.0391(8) Uani 1 1 d . . . N1 N 0.2331(3) 0.28872(14) 0.1965(2) 0.0447(7) Uani 1 1 d . . . N2 N 0.6212(3) 0.28405(15) 0.4681(2) 0.0469(7) Uani 1 1 d . . . C20 C 0.8308(3) 0.18937(18) 0.3194(3) 0.0430(8) Uani 1 1 d . . . C19 C 0.7046(3) 0.18666(18) 0.3079(3) 0.0448(8) Uani 1 1 d . . . C21 C 0.8908(4) 0.24647(19) 0.3288(3) 0.0508(9) Uani 1 1 d . . . H21 H 0.8514 0.2843 0.3264 0.061 Uiso 1 1 d R . . C9 C 0.2363(4) 0.3173(2) 0.2807(3) 0.0573(10) Uani 1 1 d . . . H9A H 0.3065 0.3481 0.3163 0.069 Uiso 1 1 d R . . H9B H 0.2529 0.2850 0.3291 0.069 Uiso 1 1 d R . . H9C H 0.1526 0.3374 0.2524 0.069 Uiso 1 1 d R . . C1 C 0.4574(3) 0.34905(16) 0.2319(3) 0.0398(8) Uani 1 1 d . . . C18 C 0.7493(4) 0.2513(2) 0.5205(3) 0.0639(11) Uani 1 1 d . . . H18A H 0.8011 0.2566 0.5947 0.077 Uiso 1 1 d R . . H18B H 0.7970 0.2686 0.4971 0.077 Uiso 1 1 d R . . H18C H 0.7336 0.2070 0.5038 0.077 Uiso 1 1 d R . . C2 C 0.3335(4) 0.37711(18) 0.1693(3) 0.0479(9) Uani 1 1 d . . . C16 C 0.5472(4) 0.2569(2) 0.5027(3) 0.0560(10) Uani 1 1 d . . . H16A H 0.4811 0.2872 0.4897 0.067 Uiso 1 1 d R . . H16B H 0.6081 0.2492 0.5774 0.067 Uiso 1 1 d R . . C3 C 0.3236(5) 0.4414(2) 0.1466(3) 0.0625(11) Uani 1 1 d . . . H3 H 0.2402 0.4605 0.1045 0.075 Uiso 1 1 d R . . C22 C 1.0091(4) 0.2474(2) 0.3423(3) 0.0652(11) Uani 1 1 d . . . H22 H 1.0490 0.2859 0.3486 0.078 Uiso 1 1 d R . . C6 C 0.5706(4) 0.38533(18) 0.2688(3) 0.0505(9) Uani 1 1 d . . . H6 H 0.6545 0.3666 0.3088 0.061 Uiso 1 1 d R . . C8 C 0.1257(4) 0.2414(2) 0.1422(4) 0.0662(12) Uani 1 1 d . . . H8A H 0.0421 0.2619 0.1128 0.079 Uiso 1 1 d R . . H8B H 0.1413 0.2096 0.1911 0.079 Uiso 1 1 d R . . H8C H 0.1232 0.2218 0.0874 0.079 Uiso 1 1 d R . . C13 C 0.3826(5) 0.0974(2) 0.4451(4) 0.0751(15) Uani 1 1 d . . . H13 H 0.3623 0.0690 0.4774 0.090 Uiso 1 1 d R . . C11 C 0.4789(4) 0.19585(19) 0.4478(3) 0.0473(9) Uani 1 1 d . . . C25 C 0.8905(4) 0.1344(2) 0.3223(3) 0.0571(10) Uani 1 1 d . . . H25 H 0.8515 0.0957 0.3164 0.068 Uiso 1 1 d R . . C12 C 0.4493(5) 0.1520(2) 0.4956(3) 0.0661(13) Uani 1 1 d . . . H12 H 0.4748 0.1602 0.5620 0.079 Uiso 1 1 d R . . C7 C 0.2106(4) 0.33765(19) 0.1230(3) 0.0539(10) Uani 1 1 d . . . H7A H 0.1370 0.3645 0.1044 0.065 Uiso 1 1 d R . . H7B H 0.1869 0.3177 0.0597 0.065 Uiso 1 1 d R . . C32 C 0.9878(12) 0.4418(4) 0.5286(6) 0.130(3) Uani 1 1 d . . . H32 H 0.9798 0.4015 0.5474 0.156 Uiso 1 1 d R . . C23 C 1.0677(4) 0.1922(3) 0.3456(3) 0.0685(12) Uani 1 1 d . . . H23 H 1.1477 0.1932 0.3548 0.082 Uiso 1 1 d R . . C15 C 0.3754(4) 0.12637(18) 0.3004(3) 0.0537(10) Uani 1 1 d . . . H15 H 0.3506 0.1172 0.2344 0.064 Uiso 1 1 d R . . C5 C 0.5584(5) 0.4492(2) 0.2449(3) 0.0635(12) Uani 1 1 d . . . H5 H 0.6336 0.4733 0.2692 0.076 Uiso 1 1 d R . . C24 C 1.0086(4) 0.1359(2) 0.3350(4) 0.0686(12) Uani 1 1 d . . . H24 H 1.0480 0.0984 0.3364 0.082 Uiso 1 1 d R . . C14 C 0.3462(5) 0.0839(2) 0.3488(4) 0.0702(13) Uani 1 1 d . . . H14 H 0.3020 0.0463 0.3156 0.084 Uiso 1 1 d R . . C17 C 0.6475(5) 0.3517(2) 0.4977(3) 0.0741(13) Uani 1 1 d . . . H17A H 0.5644 0.3736 0.4652 0.089 Uiso 1 1 d R . . H17B H 0.6952 0.3699 0.4749 0.089 Uiso 1 1 d R . . H17C H 0.6999 0.3556 0.5723 0.089 Uiso 1 1 d R . . C4 C 0.4350(6) 0.4768(2) 0.1850(4) 0.0698(13) Uani 1 1 d . . . H4 H 0.4270 0.5200 0.1711 0.084 Uiso 1 1 d R . . C28 C 1.2219(6) 0.5791(3) 0.8521(5) 0.0959(18) Uani 1 1 d . . . H28 H 1.2922 0.5921 0.8522 0.115 Uiso 1 1 d R . . C27 C 1.1066(6) 0.5603(3) 0.7624(5) 0.1009(19) Uani 1 1 d . . . H27 H 1.0991 0.5592 0.7015 0.121 Uiso 1 1 d R . . C33 C 0.8935(8) 0.4856(5) 0.4976(5) 0.112(2) Uani 1 1 d . . . H33 H 0.8209 0.4760 0.4963 0.135 Uiso 1 1 d R . . C30 C 1.1305(8) 0.5631(2) 0.9407(5) 0.0946(19) Uani 1 1 d . . . H30 H 1.1397 0.5650 1.0023 0.113 Uiso 1 1 d R . . C35 C 0.6011(6) 0.5386(3) 0.5234(6) 0.0913(17) Uani 1 1 d . . . H35 H 0.6695 0.5652 0.5391 0.110 Uiso 1 1 d R . . C34 C 0.9051(8) 0.5441(5) 0.4690(5) 0.121(3) Uani 1 1 d . . . H34 H 0.8400 0.5746 0.4474 0.145 Uiso 1 1 d R . . C29 C 1.2331(6) 0.5800(2) 0.9398(5) 0.0912(18) Uani 1 1 d . . . H29 H 1.3139 0.5922 1.0017 0.109 Uiso 1 1 d R . . C31 C 1.0121(6) 0.5431(3) 0.8482(6) 0.0980(19) Uani 1 1 d . . . H31 H 0.9405 0.5303 0.8464 0.118 Uiso 1 1 d R . . C37 C 0.5108(7) 0.4668(3) 0.5768(5) 0.0923(17) Uani 1 1 d . . . H37 H 0.5185 0.4445 0.6298 0.111 Uiso 1 1 d R . . C36 C 0.6119(6) 0.5055(3) 0.5999(5) 0.0961(19) Uani 1 1 d . . . H36 H 0.6886 0.5091 0.6686 0.115 Uiso 1 1 d R . . C26 C 1.0021(6) 0.5418(3) 0.7596(6) 0.112(2) Uani 1 1 d . . . H26 H 0.9235 0.5290 0.6965 0.135 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 0.03758(12) 0.03888(12) 0.03770(13) -0.00055(10) 0.02716(11) -0.00189(11) Cl1 0.0602(6) 0.0648(6) 0.0436(5) -0.0109(4) 0.0354(5) -0.0097(5) O1 0.0420(13) 0.0522(15) 0.0576(15) -0.0007(12) 0.0366(12) 0.0016(11) O2 0.0587(17) 0.0538(17) 0.085(2) 0.0021(14) 0.0513(17) -0.0026(13) C10 0.0393(18) 0.0467(19) 0.044(2) 0.0094(15) 0.0316(17) 0.0076(15) N1 0.0375(15) 0.0513(18) 0.0475(18) 0.0041(14) 0.0270(15) -0.0017(13) N2 0.0433(17) 0.0573(19) 0.0375(17) -0.0022(14) 0.0234(15) 0.0038(14) C20 0.0405(19) 0.057(2) 0.0346(19) 0.0006(16) 0.0248(17) 0.0040(16) C19 0.0388(19) 0.058(2) 0.040(2) -0.0025(16) 0.0247(17) 0.0003(17) C21 0.0448(19) 0.058(2) 0.055(2) 0.0028(19) 0.0337(19) 0.0016(19) C9 0.059(2) 0.068(3) 0.064(3) 0.008(2) 0.047(2) 0.009(2) C1 0.046(2) 0.0452(19) 0.0338(18) -0.0010(14) 0.0275(17) -0.0010(15) C18 0.044(2) 0.092(3) 0.044(2) 0.000(2) 0.0205(19) 0.009(2) C2 0.058(2) 0.052(2) 0.043(2) 0.0066(16) 0.035(2) 0.0059(18) C16 0.055(2) 0.081(3) 0.036(2) -0.0021(19) 0.0301(19) 0.008(2) C3 0.078(3) 0.057(3) 0.065(3) 0.020(2) 0.050(3) 0.018(2) C22 0.051(2) 0.084(3) 0.068(3) 0.011(2) 0.040(2) -0.007(2) C6 0.060(2) 0.051(2) 0.048(2) -0.0060(17) 0.037(2) -0.0114(18) C8 0.040(2) 0.081(3) 0.076(3) -0.002(2) 0.034(2) -0.013(2) C13 0.095(4) 0.068(3) 0.105(4) 0.038(3) 0.083(4) 0.026(3) C11 0.044(2) 0.064(2) 0.043(2) 0.0145(17) 0.0310(18) 0.0150(18) C25 0.051(2) 0.064(3) 0.063(3) -0.001(2) 0.038(2) 0.0046(19) C12 0.073(3) 0.088(3) 0.063(3) 0.030(2) 0.055(3) 0.031(3) C7 0.046(2) 0.066(3) 0.050(2) 0.0131(19) 0.029(2) 0.0120(19) C32 0.147(7) 0.095(5) 0.104(6) 0.003(4) 0.054(6) -0.007(6) C23 0.047(2) 0.098(4) 0.072(3) 0.014(3) 0.043(2) 0.011(2) C15 0.066(3) 0.048(2) 0.066(3) 0.0061(18) 0.051(2) 0.0006(18) C5 0.087(3) 0.051(2) 0.064(3) -0.009(2) 0.052(3) -0.024(2) C24 0.060(3) 0.079(3) 0.080(3) 0.009(2) 0.050(3) 0.022(2) C14 0.083(3) 0.048(2) 0.114(4) 0.013(2) 0.078(3) 0.003(2) C17 0.093(4) 0.068(3) 0.049(3) -0.016(2) 0.037(3) -0.009(3) C4 0.106(4) 0.043(2) 0.076(3) 0.006(2) 0.064(3) -0.002(2) C28 0.088(4) 0.086(4) 0.094(5) -0.021(3) 0.045(4) -0.008(3) C27 0.088(4) 0.114(5) 0.080(4) -0.023(3) 0.040(4) 0.012(4) C33 0.099(5) 0.133(6) 0.081(4) -0.021(4) 0.043(4) -0.029(5) C30 0.134(6) 0.053(3) 0.086(4) 0.010(3) 0.061(4) 0.023(3) C35 0.085(4) 0.100(4) 0.100(5) -0.025(4) 0.063(4) -0.007(3) C34 0.094(5) 0.132(7) 0.073(4) -0.004(4) 0.018(4) 0.024(5) C29 0.084(4) 0.066(3) 0.082(4) -0.009(3) 0.029(3) -0.009(3) C31 0.085(4) 0.084(4) 0.130(6) -0.007(4) 0.068(5) 0.008(3) C37 0.120(5) 0.092(4) 0.086(4) 0.000(3) 0.073(4) 0.023(4) C36 0.073(4) 0.113(5) 0.068(4) -0.018(3) 0.026(3) 0.017(4) C26 0.061(3) 0.125(5) 0.099(5) -0.040(4) 0.022(3) 0.012(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 Sn1 O1 2.070(2) . ? Sn1 C10 2.116(3) . ? Sn1 C1 2.124(3) . ? Sn1 Cl1 2.4302(9) . ? Sn1 N1 2.581(3) . ? O1 C19 1.305(4) . ? O2 C19 1.219(4) . ? C10 C11 1.377(5) . ? C10 C15 1.391(5) . ? N1 C7 1.465(5) . ? N1 C9 1.468(5) . ? N1 C8 1.471(5) . ? N2 C18 1.468(5) . ? N2 C16 1.469(5) . ? N2 C17 1.480(5) . ? C20 C25 1.372(5) . ? C20 C21 1.384(5) . ? C20 C19 1.494(5) . ? C21 C22 1.377(5) . ? C21 H21 0.9301 . ? C9 H9A 0.9599 . ? C9 H9B 0.9601 . ? C9 H9C 0.9600 . ? C1 C2 1.378(5) . ? C1 C6 1.399(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C2 C3 1.392(5) . ? C2 C7 1.502(5) . ? C16 C11 1.505(6) . ? C16 H16A 0.9699 . ? C16 H16B 0.9700 . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C22 C23 1.367(6) . ? C22 H22 0.9300 . ? C6 C5 1.386(5) . ? C6 H6 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9601 . ? C8 H8C 0.9599 . ? C13 C14 1.355(7) . ? C13 C12 1.367(7) . ? C13 H13 0.9300 . ? C11 C12 1.396(5) . ? C25 C24 1.381(6) . ? C25 H25 0.9299 . ? C12 H12 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9698 . ? C32 C33 1.343(10) . ? C32 C34 1.367(11) 3_766 ? C32 H32 0.9301 . ? C23 C24 1.360(6) . ? C23 H23 0.9300 . ? C15 C14 1.382(5) . ? C15 H15 0.9301 . ? C5 C4 1.369(6) . ? C5 H5 0.9299 . ? C24 H24 0.9299 . ? C14 H14 0.9299 . ? C17 H17A 0.9600 . ? C17 H17B 0.9602 . ? C17 H17C 0.9599 . ? C4 H4 0.9301 . ? C28 C29 1.336(8) . ? C28 C27 1.344(8) . ? C28 H28 0.9301 . ? C27 C26 1.355(9) . ? C27 H27 0.9299 . ? C33 C34 1.358(10) . ? C33 H33 0.9301 . ? C30 C29 1.356(8) . ? C30 C31 1.388(8) . ? C30 H30 0.9299 . ? C35 C36 1.353(8) . ? C35 C37 1.357(8) 3_666 ? C35 H35 0.9299 . ? C34 C32 1.367(11) 3_766 ? C34 H34 0.9300 . ? C29 H29 0.9300 . ? C31 C26 1.357(9) . ? C31 H31 0.9300 . ? C37 C35 1.357(8) 3_666 ? C37 C36 1.364(8) . ? C37 H37 0.9301 . ? C36 H36 0.9300 . ? C26 H26 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 O1 Sn1 C10 112.47(11) . . ? O1 Sn1 C1 91.99(12) . . ? C10 Sn1 C1 146.61(13) . . ? O1 Sn1 Cl1 90.29(7) . . ? C10 Sn1 Cl1 101.22(10) . . ? C1 Sn1 Cl1 101.01(9) . . ? O1 Sn1 N1 162.63(9) . . ? C10 Sn1 N1 84.71(11) . . ? C1 Sn1 N1 73.42(11) . . ? Cl1 Sn1 N1 83.49(7) . . ? C19 O1 Sn1 122.6(2) . . ? C11 C10 C15 119.7(3) . . ? C11 C10 Sn1 119.5(3) . . ? C15 C10 Sn1 120.6(3) . . ? C7 N1 C9 110.1(3) . . ? C7 N1 C8 110.2(3) . . ? C9 N1 C8 108.9(3) . . ? C7 N1 Sn1 100.6(2) . . ? C9 N1 Sn1 109.3(2) . . ? C8 N1 Sn1 117.4(2) . . ? C18 N2 C16 109.5(3) . . ? C18 N2 C17 108.6(3) . . ? C16 N2 C17 108.9(3) . . ? C25 C20 C21 118.7(3) . . ? C25 C20 C19 119.9(4) . . ? C21 C20 C19 121.5(3) . . ? O2 C19 O1 124.0(3) . . ? O2 C19 C20 121.7(3) . . ? O1 C19 C20 114.3(3) . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? N1 C9 H9A 109.0 . . ? N1 C9 H9B 109.4 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 110.1 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C1 C6 119.3(3) . . ? C2 C1 Sn1 118.6(3) . . ? C6 C1 Sn1 122.1(3) . . ? N2 C18 H18A 109.6 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.4 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 C2 C3 119.4(4) . . ? C1 C2 C7 119.7(3) . . ? C3 C2 C7 120.8(4) . . ? N2 C16 C11 112.4(3) . . ? N2 C16 H16A 109.1 . . ? C11 C16 H16A 109.2 . . ? N2 C16 H16B 109.4 . . ? C11 C16 H16B 108.9 . . ? H16A C16 H16B 107.8 . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.7 . . ? C23 C22 C21 120.4(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C5 C6 C1 120.2(4) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 120.1 . . ? N1 C8 H8A 109.1 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.8 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C10 C11 C12 118.8(4) . . ? C10 C11 C16 121.5(3) . . ? C12 C11 C16 119.6(4) . . ? C20 C25 C24 120.7(4) . . ? C20 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C13 C12 C11 120.4(4) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.7 . . ? N1 C7 C2 111.0(3) . . ? N1 C7 H7A 109.8 . . ? C2 C7 H7A 109.7 . . ? N1 C7 H7B 109.3 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 108.0 . . ? C33 C32 C34 120.2(8) . 3_766 ? C33 C32 H32 120.3 . . ? C34 C32 H32 119.6 3_766 . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.0 . . ? C14 C15 C10 120.4(4) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.9 . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 120.2 . . ? C23 C24 C25 120.1(4) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 120.1 . . ? C13 C14 C15 119.5(5) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.2 . . ? N2 C17 H17A 109.4 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.6 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.9 . . ? C29 C28 C27 119.3(7) . . ? C29 C28 H28 120.8 . . ? C27 C28 H28 119.9 . . ? C28 C27 C26 121.2(7) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.5 . . ? C32 C33 C34 119.9(8) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.2 . . ? C29 C30 C31 118.8(6) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.8 . . ? C36 C35 C37 119.7(6) . 3_666 ? C36 C35 H35 120.5 . . ? C37 C35 H35 119.8 3_666 . ? C33 C34 C32 120.0(8) . 3_766 ? C33 C34 H34 120.2 . . ? C32 C34 H34 119.9 3_766 . ? C28 C29 C30 121.8(6) . . ? C28 C29 H29 118.6 . . ? C30 C29 H29 119.6 . . ? C26 C31 C30 119.0(6) . . ? C26 C31 H31 120.0 . . ? C30 C31 H31 120.9 . . ? C35 C37 C36 119.9(6) 3_666 . ? C35 C37 H37 120.1 3_666 . ? C36 C37 H37 119.9 . . ? C35 C36 C37 120.3(6) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.9 . . ? C27 C26 C31 119.9(6) . . ? C27 C26 H26 119.3 . . ? C31 C26 H26 120.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.455 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.074 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 921171' #TrackingRef 'az090128I1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H48 Cl2 N4 O Sn2' _chemical_formula_sum 'C36 H48 Cl2 N4 O Sn2' _chemical_formula_weight 861.06 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' 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' Cl Cl 0.1484 0.1585 '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 9.5180(12) _cell_length_b 9.5810(5) _cell_length_c 23.3921(12) _cell_angle_alpha 78.972(4) _cell_angle_beta 81.579(6) _cell_angle_gamma 60.585(7) _cell_volume 1820.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 34608 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.552 # 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 0.021 0 0 -1 0.075 0 1 0 0.121 0 -1 0 0.098 1 0 0 0.087 -1 0 0 0.113 1 1 0 0.086 -1 -1 0 0.107 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.735 _exptl_absorpt_correction_T_max 0.860 _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 34529 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8281 _reflns_number_gt 5607 _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, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0171P)^2^+0.9460P] 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 8281 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0625 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn -0.23911(3) 0.20543(3) 0.332097(10) 0.02703(7) Uani 1 1 d . . . Sn2 Sn -0.18891(3) 0.21758(3) 0.172747(10) 0.02879(7) Uani 1 1 d . . . Cl2 Cl -0.21157(11) 0.48729(11) 0.17088(4) 0.0406(2) Uani 1 1 d . . . Cl1 Cl -0.50144(11) 0.21523(11) 0.32464(4) 0.0418(2) Uani 1 1 d . . . C28 C -0.4349(4) 0.2979(4) 0.16088(15) 0.0315(8) Uani 1 1 d . . . O1 O -0.1430(3) 0.1398(3) 0.25529(10) 0.0329(5) Uani 1 1 d . . . C1 C -0.3350(4) 0.4578(4) 0.33192(14) 0.0280(8) Uani 1 1 d . . . C5 C -0.5434(5) 0.7339(4) 0.31188(18) 0.0471(10) Uani 1 1 d . . . H5 H -0.6442 0.8084 0.2980 0.057 Uiso 1 1 d R . . N3 N -0.2121(3) -0.0440(3) 0.17624(13) 0.0364(7) Uani 1 1 d . . . N1 N 0.0004(3) 0.2449(3) 0.34586(12) 0.0321(7) Uani 1 1 d . . . C29 C -0.4918(4) 0.1861(4) 0.17248(15) 0.0348(9) Uani 1 1 d . . . N2 N -0.3633(3) 0.2196(3) 0.45121(13) 0.0368(7) Uani 1 1 d . . . C35 C -0.1884(5) -0.0933(5) 0.11863(18) 0.0572(12) Uani 1 1 d . . . H35A H -0.1960 -0.1910 0.1225 0.069 Uiso 1 1 d R . . H35B H -0.0835 -0.1121 0.1016 0.069 Uiso 1 1 d R . . H35C H -0.2699 -0.0094 0.0940 0.069 Uiso 1 1 d R . . C15 C 0.0127(4) -0.1498(4) 0.35929(16) 0.0341(8) Uani 1 1 d . . . H15 H 0.0548 -0.1262 0.3225 0.041 Uiso 1 1 d R . . C27 C -0.2944(5) 0.5030(5) 0.02791(19) 0.0643(13) Uani 1 1 d . . . H27A H -0.2917 0.5722 0.0520 0.077 Uiso 1 1 d R . . H27B H -0.4021 0.5176 0.0296 0.077 Uiso 1 1 d R . . H27C H -0.2621 0.5299 -0.0117 0.077 Uiso 1 1 d R . . C19 C 0.0493(4) 0.0981(4) 0.13321(15) 0.0336(8) Uani 1 1 d . . . C14 C 0.0913(4) -0.3045(4) 0.38948(17) 0.0385(9) Uani 1 1 d . . . H14 H 0.1848 -0.3840 0.3731 0.046 Uiso 1 1 d R . . N4 N -0.1837(4) 0.3340(4) 0.04848(14) 0.0458(8) Uani 1 1 d . . . C7 C -0.0766(4) 0.3923(4) 0.37358(16) 0.0388(9) Uani 1 1 d . . . H7A H -0.0077 0.4428 0.3668 0.047 Uiso 1 1 d R . . H7B H -0.0877 0.3621 0.4153 0.047 Uiso 1 1 d R . . C10 C -0.1263(4) -0.0291(4) 0.38274(14) 0.0278(8) Uani 1 1 d . . . C17 C -0.2672(5) 0.2313(5) 0.49142(17) 0.0481(10) Uani 1 1 d . . . H17A H -0.2722 0.3357 0.4831 0.058 Uiso 1 1 d R . . H17B H -0.1570 0.1487 0.4870 0.058 Uiso 1 1 d R . . H17C H -0.3088 0.2166 0.5307 0.058 Uiso 1 1 d R . . C13 C 0.0284(4) -0.3389(4) 0.44344(17) 0.0414(10) Uani 1 1 d . . . H13 H 0.0809 -0.4420 0.4642 0.050 Uiso 1 1 d R . . C12 C -0.1117(4) -0.2219(4) 0.46723(16) 0.0385(9) Uani 1 1 d . . . H12 H -0.1537 -0.2470 0.5038 0.046 Uiso 1 1 d R . . C32 C -0.7034(4) 0.5086(5) 0.14006(17) 0.0459(10) Uani 1 1 d . . . H32 H -0.7752 0.6176 0.1300 0.055 Uiso 1 1 d R . . C2 C -0.2423(4) 0.5128(4) 0.35205(15) 0.0320(8) Uani 1 1 d . . . C24 C 0.1653(4) -0.0368(4) 0.16628(18) 0.0406(9) Uani 1 1 d . . . H24 H 0.1359 -0.0705 0.2039 0.049 Uiso 1 1 d R . . C23 C 0.3226(5) -0.1204(5) 0.1439(2) 0.0529(11) Uani 1 1 d . . . H23 H 0.3989 -0.2086 0.1667 0.064 Uiso 1 1 d R . . C8 C 0.1306(4) 0.1158(4) 0.38154(17) 0.0446(10) Uani 1 1 d . . . H8A H 0.2059 0.1513 0.3866 0.054 Uiso 1 1 d R . . H8B H 0.1855 0.0212 0.3622 0.054 Uiso 1 1 d R . . H8C H 0.0856 0.0904 0.4190 0.054 Uiso 1 1 d R . . C25 C -0.0188(5) 0.3069(5) 0.04312(17) 0.0505(11) Uani 1 1 d . . . H25A H -0.0167 0.3960 0.0561 0.061 Uiso 1 1 d R . . H25B H 0.0187 0.3056 0.0023 0.061 Uiso 1 1 d R . . C16 C -0.3495(4) 0.0578(4) 0.46224(15) 0.0375(9) Uani 1 1 d . . . H16A H -0.4379 0.0609 0.4451 0.045 Uiso 1 1 d R . . H16B H -0.3585 0.0259 0.5040 0.045 Uiso 1 1 d R . . C30 C -0.6533(4) 0.2375(5) 0.16658(17) 0.0451(10) Uani 1 1 d . . . H30 H -0.6908 0.1622 0.1735 0.054 Uiso 1 1 d R . . C20 C 0.0960(5) 0.1503(5) 0.07747(17) 0.0421(9) Uani 1 1 d . . . C3 C -0.3022(5) 0.6762(4) 0.35282(17) 0.0434(10) Uani 1 1 d . . . H3 H -0.2401 0.7123 0.3663 0.052 Uiso 1 1 d R . . C11 C -0.1914(4) -0.0659(4) 0.43716(15) 0.0307(8) Uani 1 1 d . . . C22 C 0.3660(5) -0.0722(6) 0.0887(2) 0.0646(13) Uani 1 1 d . . . H22 H 0.4704 -0.1311 0.0729 0.078 Uiso 1 1 d R . . C9 C 0.0693(5) 0.2766(5) 0.28760(16) 0.0498(11) Uani 1 1 d . . . H9A H -0.0147 0.3628 0.2644 0.060 Uiso 1 1 d R . . H9B H 0.1186 0.1808 0.2690 0.060 Uiso 1 1 d R . . H9C H 0.1493 0.3072 0.2913 0.060 Uiso 1 1 d R . . C33 C -0.5425(4) 0.4593(4) 0.14463(16) 0.0410(9) Uani 1 1 d . . . H33 H -0.5056 0.5351 0.1363 0.049 Uiso 1 1 d R . . C34 C -0.3819(4) 0.0141(4) 0.19813(17) 0.0431(10) Uani 1 1 d . . . H34A H -0.3890 0.0071 0.2403 0.052 Uiso 1 1 d R . . H34B H -0.4192 -0.0561 0.1887 0.052 Uiso 1 1 d R . . C26 C -0.1994(6) 0.2290(5) 0.01471(19) 0.0652(13) Uani 1 1 d . . . H26A H -0.1904 0.2658 -0.0261 0.078 Uiso 1 1 d R . . H26B H -0.3028 0.2330 0.0244 0.078 Uiso 1 1 d R . . H26C H -0.1153 0.1198 0.0236 0.078 Uiso 1 1 d R . . C4 C -0.4526(5) 0.7864(4) 0.33315(18) 0.0494(11) Uani 1 1 d . . . H4 H -0.4933 0.8961 0.3344 0.059 Uiso 1 1 d R . . C6 C -0.4850(4) 0.5705(4) 0.31130(16) 0.0384(9) Uani 1 1 d . . . H6 H -0.5472 0.5362 0.2969 0.046 Uiso 1 1 d R . . C31 C -0.7587(5) 0.3982(5) 0.15067(18) 0.0513(11) Uani 1 1 d . . . H31 H -0.8671 0.4313 0.1471 0.062 Uiso 1 1 d R . . C36 C -0.1082(5) -0.1841(4) 0.21681(18) 0.0517(11) Uani 1 1 d . . . H36A H -0.1189 -0.1519 0.2543 0.062 Uiso 1 1 d R . . H36B H 0.0022 -0.2259 0.2018 0.062 Uiso 1 1 d R . . H36C H -0.1402 -0.2663 0.2207 0.062 Uiso 1 1 d R . . C18 C -0.5317(4) 0.3436(5) 0.45846(18) 0.0509(11) Uani 1 1 d . . . H18A H -0.5733 0.3258 0.4975 0.061 Uiso 1 1 d R . . H18B H -0.5946 0.3380 0.4313 0.061 Uiso 1 1 d R . . H18C H -0.5379 0.4485 0.4513 0.061 Uiso 1 1 d R . . C21 C 0.2538(5) 0.0635(6) 0.0558(2) 0.0588(12) Uani 1 1 d . . . H21 H 0.2853 0.0971 0.0185 0.071 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 0.02665(14) 0.02374(13) 0.03157(15) -0.00395(10) -0.00248(11) -0.01247(11) Sn2 0.02695(14) 0.02992(14) 0.03240(15) -0.00526(11) -0.00186(11) -0.01545(11) Cl2 0.0464(5) 0.0352(5) 0.0488(6) -0.0034(4) -0.0091(5) -0.0253(4) Cl1 0.0366(5) 0.0488(6) 0.0505(6) -0.0106(5) -0.0044(4) -0.0267(5) C28 0.0291(19) 0.032(2) 0.035(2) -0.0066(16) -0.0008(16) -0.0154(16) O1 0.0376(13) 0.0305(13) 0.0292(13) -0.0054(10) -0.0021(11) -0.0148(11) C1 0.0288(18) 0.0252(19) 0.0286(19) -0.0039(15) 0.0010(15) -0.0124(15) C5 0.036(2) 0.029(2) 0.062(3) -0.0019(19) 0.001(2) -0.0066(17) N3 0.0399(18) 0.0293(17) 0.0410(19) -0.0064(14) 0.0002(15) -0.0175(14) N1 0.0273(16) 0.0346(17) 0.0350(18) -0.0057(13) -0.0032(13) -0.0147(13) C29 0.035(2) 0.042(2) 0.036(2) -0.0127(17) 0.0049(17) -0.0236(18) N2 0.0343(17) 0.0324(18) 0.0378(19) -0.0063(14) 0.0009(14) -0.0117(14) C35 0.075(3) 0.058(3) 0.047(3) -0.019(2) 0.003(2) -0.037(2) C15 0.032(2) 0.034(2) 0.038(2) -0.0049(17) -0.0017(17) -0.0176(17) C27 0.070(3) 0.062(3) 0.050(3) 0.008(2) -0.015(2) -0.026(3) C19 0.033(2) 0.036(2) 0.039(2) -0.0137(17) 0.0011(17) -0.0201(17) C14 0.030(2) 0.026(2) 0.055(3) -0.0073(18) -0.0070(18) -0.0076(16) N4 0.050(2) 0.051(2) 0.037(2) -0.0029(16) -0.0019(16) -0.0257(18) C7 0.040(2) 0.038(2) 0.046(2) -0.0075(18) -0.0064(18) -0.0226(18) C10 0.0308(19) 0.0229(18) 0.033(2) -0.0025(15) -0.0054(16) -0.0152(15) C17 0.046(2) 0.048(3) 0.053(3) -0.015(2) -0.001(2) -0.022(2) C13 0.045(2) 0.030(2) 0.050(3) 0.0034(18) -0.016(2) -0.0190(19) C12 0.050(2) 0.041(2) 0.032(2) 0.0036(17) -0.0074(18) -0.029(2) C32 0.027(2) 0.052(3) 0.048(3) -0.0077(19) -0.0042(18) -0.0091(18) C2 0.036(2) 0.031(2) 0.031(2) -0.0044(16) 0.0006(16) -0.0188(17) C24 0.035(2) 0.037(2) 0.054(3) -0.0121(19) -0.0025(19) -0.0182(18) C23 0.035(2) 0.037(2) 0.088(4) -0.025(2) -0.003(2) -0.0119(19) C8 0.036(2) 0.043(2) 0.054(3) -0.0045(19) -0.0105(19) -0.0169(18) C25 0.056(3) 0.066(3) 0.036(2) -0.003(2) 0.007(2) -0.038(2) C16 0.036(2) 0.045(2) 0.032(2) -0.0022(17) 0.0032(17) -0.0224(18) C30 0.039(2) 0.060(3) 0.053(3) -0.019(2) 0.0048(19) -0.035(2) C20 0.041(2) 0.056(3) 0.042(2) -0.017(2) 0.0071(19) -0.032(2) C3 0.049(2) 0.036(2) 0.055(3) -0.0114(19) 0.004(2) -0.029(2) C11 0.0296(19) 0.031(2) 0.037(2) -0.0051(16) -0.0020(16) -0.0185(16) C22 0.036(3) 0.069(3) 0.096(4) -0.050(3) 0.021(3) -0.023(2) C9 0.042(2) 0.075(3) 0.044(3) -0.011(2) 0.0035(19) -0.037(2) C33 0.036(2) 0.045(2) 0.044(2) -0.0042(18) -0.0002(18) -0.0221(19) C34 0.051(2) 0.045(2) 0.046(2) -0.0121(19) 0.0043(19) -0.033(2) C26 0.083(4) 0.076(3) 0.051(3) -0.008(2) -0.012(3) -0.046(3) C4 0.052(3) 0.024(2) 0.068(3) -0.0073(19) 0.010(2) -0.0176(19) C6 0.033(2) 0.034(2) 0.049(2) -0.0056(17) -0.0015(18) -0.0163(17) C31 0.032(2) 0.073(3) 0.052(3) -0.016(2) -0.0023(19) -0.024(2) C36 0.062(3) 0.041(2) 0.060(3) -0.004(2) -0.008(2) -0.030(2) C18 0.041(2) 0.046(3) 0.051(3) -0.014(2) 0.003(2) -0.0082(19) C21 0.056(3) 0.079(3) 0.057(3) -0.028(3) 0.021(2) -0.044(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 Sn1 O1 1.961(2) . ? Sn1 C1 2.123(3) . ? Sn1 C10 2.142(3) . ? Sn1 Cl1 2.4828(9) . ? Sn1 N1 2.560(3) . ? Sn2 O1 1.962(2) . ? Sn2 C28 2.119(3) . ? Sn2 C19 2.132(3) . ? Sn2 Cl2 2.4774(9) . ? C28 C33 1.384(4) . ? C28 C29 1.390(4) . ? C1 C6 1.388(4) . ? C1 C2 1.397(4) . ? C5 C4 1.377(5) . ? C5 C6 1.382(5) . ? C5 H5 0.9299 . ? N3 C35 1.463(5) . ? N3 C36 1.471(4) . ? N3 C34 1.473(4) . ? N1 C7 1.466(4) . ? N1 C9 1.468(4) . ? N1 C8 1.471(4) . ? C29 C30 1.385(5) . ? C29 C34 1.510(5) . ? N2 C17 1.458(4) . ? N2 C18 1.462(4) . ? N2 C16 1.464(4) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C15 C10 1.384(5) . ? C15 C14 1.386(4) . ? C15 H15 0.9300 . ? C27 N4 1.462(5) . ? C27 H27A 0.9599 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C19 C20 1.396(5) . ? C19 C24 1.398(5) . ? C14 C13 1.368(5) . ? C14 H14 0.9299 . ? N4 C25 1.449(5) . ? N4 C26 1.465(5) . ? C7 C2 1.515(5) . ? C7 H7A 0.9699 . ? C7 H7B 0.9699 . ? C10 C11 1.393(4) . ? C17 H17A 0.9599 . ? C17 H17B 0.9600 . ? C17 H17C 0.9599 . ? C13 C12 1.377(5) . ? C13 H13 0.9300 . ? C12 C11 1.395(4) . ? C12 H12 0.9300 . ? C32 C31 1.366(5) . ? C32 C33 1.377(5) . ? C32 H32 0.9300 . ? C2 C3 1.381(5) . ? C24 C23 1.382(5) . ? C24 H24 0.9300 . ? C23 C22 1.362(6) . ? C23 H23 0.9300 . ? C8 H8A 0.9601 . ? C8 H8B 0.9599 . ? C8 H8C 0.9601 . ? C25 C20 1.508(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9699 . ? C16 C11 1.506(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C30 C31 1.374(5) . ? C30 H30 0.9300 . ? C20 C21 1.384(5) . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C22 C21 1.385(6) . ? C22 H22 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9601 . ? C33 H33 0.9299 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C26 H26A 0.9601 . ? C26 H26B 0.9601 . ? C26 H26C 0.9600 . ? C4 H4 0.9300 . ? C6 H6 0.9300 . ? C31 H31 0.9300 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C21 H21 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 O1 Sn1 C1 112.17(11) . . ? O1 Sn1 C10 97.78(11) . . ? C1 Sn1 C10 145.40(13) . . ? O1 Sn1 Cl1 96.99(7) . . ? C1 Sn1 Cl1 96.07(9) . . ? C10 Sn1 Cl1 97.10(8) . . ? O1 Sn1 N1 89.90(9) . . ? C1 Sn1 N1 74.26(11) . . ? C10 Sn1 N1 89.41(10) . . ? Cl1 Sn1 N1 169.77(7) . . ? O1 Sn2 C28 110.64(11) . . ? O1 Sn2 C19 100.00(11) . . ? C28 Sn2 C19 143.02(13) . . ? O1 Sn2 Cl2 96.79(7) . . ? C28 Sn2 Cl2 97.29(9) . . ? C19 Sn2 Cl2 99.18(9) . . ? C33 C28 C29 118.9(3) . . ? C33 C28 Sn2 122.2(2) . . ? C29 C28 Sn2 118.8(2) . . ? Sn1 O1 Sn2 138.97(12) . . ? C6 C1 C2 118.7(3) . . ? C6 C1 Sn1 122.4(3) . . ? C2 C1 Sn1 118.9(2) . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C35 N3 C36 109.1(3) . . ? C35 N3 C34 109.9(3) . . ? C36 N3 C34 109.0(3) . . ? C7 N1 C9 109.3(3) . . ? C7 N1 C8 109.2(3) . . ? C9 N1 C8 109.2(3) . . ? C7 N1 Sn1 102.82(19) . . ? C9 N1 Sn1 107.5(2) . . ? C8 N1 Sn1 118.4(2) . . ? C30 C29 C28 119.5(3) . . ? C30 C29 C34 120.5(3) . . ? C28 C29 C34 119.6(3) . . ? C17 N2 C18 109.4(3) . . ? C17 N2 C16 109.7(3) . . ? C18 N2 C16 110.8(3) . . ? N3 C35 H35A 109.4 . . ? N3 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N3 C35 H35C 109.6 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C10 C15 C14 121.6(3) . . ? C10 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? N4 C27 H27A 109.9 . . ? N4 C27 H27B 109.4 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.2 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C20 C19 C24 118.8(3) . . ? C20 C19 Sn2 123.7(3) . . ? C24 C19 Sn2 117.5(3) . . ? C13 C14 C15 119.0(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.4 . . ? C25 N4 C27 110.4(3) . . ? C25 N4 C26 110.6(3) . . ? C27 N4 C26 109.3(3) . . ? N1 C7 C2 112.8(3) . . ? N1 C7 H7A 109.6 . . ? C2 C7 H7A 109.5 . . ? N1 C7 H7B 108.3 . . ? C2 C7 H7B 108.6 . . ? H7A C7 H7B 107.8 . . ? C15 C10 C11 119.0(3) . . ? C15 C10 Sn1 118.5(2) . . ? C11 C10 Sn1 122.4(2) . . ? N2 C17 H17A 109.8 . . ? N2 C17 H17B 109.2 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.8 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.5 . . ? C31 C32 C33 120.3(4) . . ? C31 C32 H32 119.6 . . ? C33 C32 H32 120.1 . . ? C3 C2 C1 120.1(3) . . ? C3 C2 C7 120.2(3) . . ? C1 C2 C7 119.7(3) . . ? C23 C24 C19 121.0(4) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.3 . . ? C22 C23 C24 119.9(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.3 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C25 C20 113.4(3) . . ? N4 C25 H25A 109.2 . . ? C20 C25 H25A 109.0 . . ? N4 C25 H25B 108.7 . . ? C20 C25 H25B 108.6 . . ? H25A C25 H25B 107.8 . . ? N2 C16 C11 111.9(3) . . ? N2 C16 H16A 109.0 . . ? C11 C16 H16A 109.3 . . ? N2 C16 H16B 109.4 . . ? C11 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.5 . . ? C21 C20 C19 119.1(4) . . ? C21 C20 C25 119.9(4) . . ? C19 C20 C25 120.8(3) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.8 . . ? C10 C11 C12 119.0(3) . . ? C10 C11 C16 120.9(3) . . ? C12 C11 C16 120.1(3) . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 119.9 . . ? N1 C9 H9A 109.6 . . ? N1 C9 H9B 109.6 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.2 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C32 C33 C28 120.7(3) . . ? C32 C33 H33 119.6 . . ? C28 C33 H33 119.7 . . ? N3 C34 C29 112.9(3) . . ? N3 C34 H34A 109.3 . . ? C29 C34 H34A 109.0 . . ? N3 C34 H34B 108.8 . . ? C29 C34 H34B 108.9 . . ? H34A C34 H34B 107.8 . . ? N4 C26 H26A 109.2 . . ? N4 C26 H26B 109.6 . . ? H26A C26 H26B 109.5 . . ? N4 C26 H26C 109.6 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 120.2 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.8 . . ? C32 C31 C30 119.7(4) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.0 . . ? N3 C36 H36A 109.8 . . ? N3 C36 H36B 109.4 . . ? H36A C36 H36B 109.5 . . ? N3 C36 H36C 109.2 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.4 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C21 C22 121.2(4) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.3 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.520 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.111 data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 921172' #TrackingRef 'az090416Si1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H39 Cl N2 O Si Sn' _chemical_formula_sum 'C36 H39 Cl N2 O Si Sn' _chemical_formula_weight 697.92 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' Sn Sn -0.6537 1.4246 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.1550(6) _cell_length_b 9.4191(5) _cell_length_c 11.4639(9) _cell_angle_alpha 66.266(5) _cell_angle_beta 79.640(5) _cell_angle_gamma 63.335(4) _cell_volume 808.70(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 15578 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.489 _exptl_crystal_size_mid 0.329 _exptl_crystal_size_min 0.094 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 0.941 # 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 0.044 -1 0 0 0.047 0 0 1 0.102 0 -1 -1 0.052 0 0 -1 0.198 1 1 1 0.109 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.725 _exptl_absorpt_correction_T_max 0.924 _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 15546 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6923 _reflns_number_gt 6852 _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^)+(0.0367P)^2^+0.6477P] 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 -0.010(16) _refine_ls_number_reflns 6923 _refine_ls_number_parameters 379 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Sn1 Sn 0.774000(4) 1.060000(4) 0.797000(4) 0.02497(7) Uani 1 1 d . . . Si1 Si 0.83794(16) 0.89273(16) 1.12211(13) 0.0221(3) Uani 1 1 d . . . N1 N 0.4862(6) 1.0639(6) 0.8248(4) 0.0398(11) Uani 1 1 d . . . Cl1 Cl 1.02510(15) 1.08781(17) 0.79972(13) 0.0386(3) Uani 1 1 d . . . C31 C 1.0322(4) 0.6945(5) 1.1729(4) 0.0273(7) Uani 1 1 d . . . C1 C 0.6076(4) 1.3116(5) 0.7793(4) 0.0280(7) Uani 1 1 d . . . O1 O 0.7797(3) 0.9291(3) 0.9846(3) 0.0266(5) Uani 1 1 d . . . C20 C 1.0247(5) 1.0456(5) 1.1636(4) 0.0329(8) Uani 1 1 d . . . H20 H 1.1083 0.9361 1.1889 0.039 Uiso 1 1 d R . . C25 C 0.6733(4) 0.8592(5) 1.2394(3) 0.0252(7) Uani 1 1 d . . . C24 C 0.7541(5) 1.2368(5) 1.0894(4) 0.0305(8) Uani 1 1 d . . . H24 H 0.6530 1.2580 1.0641 0.037 Uiso 1 1 d R . . C19 C 0.8760(4) 1.0713(5) 1.1264(3) 0.0255(7) Uani 1 1 d . . . C21 C 1.0510(7) 1.1803(7) 1.1631(5) 0.0402(12) Uani 1 1 d . . . H21 H 1.1519 1.1594 1.1887 0.048 Uiso 1 1 d R . . C27 C 0.4802(6) 0.7297(6) 1.3176(5) 0.0424(10) Uani 1 1 d . . . H27 H 0.4392 0.6569 1.3150 0.051 Uiso 1 1 d R . . C2 C 0.4488(5) 1.3398(5) 0.8250(4) 0.0329(8) Uani 1 1 d . . . C10 C 0.8717(5) 0.8524(5) 0.7326(4) 0.0290(8) Uani 1 1 d . . . C5 C 0.5384(6) 1.6114(6) 0.7234(5) 0.0426(10) Uani 1 1 d . . . H5 H 0.5685 1.7023 0.6892 0.051 Uiso 1 1 d R . . C4 C 0.3823(6) 1.6373(6) 0.7681(5) 0.0431(10) Uani 1 1 d . . . H4 H 0.3071 1.7459 0.7640 0.052 Uiso 1 1 d R . . C36 C 1.0637(5) 0.5860(5) 1.2995(4) 0.0321(8) Uani 1 1 d . . . H36 H 0.9830 0.6079 1.3601 0.039 Uiso 1 1 d R . . C7 C 0.4025(5) 1.1897(6) 0.8876(4) 0.0361(9) Uani 1 1 d . . . H7A H 0.2853 1.2304 0.8810 0.043 Uiso 1 1 d R . . H7B H 0.4313 1.1357 0.9772 0.043 Uiso 1 1 d R . . C32 C 1.1560(5) 0.6572(6) 1.0842(4) 0.0375(9) Uani 1 1 d . . . H32 H 1.1381 0.7272 0.9986 0.045 Uiso 1 1 d R . . C14 C 0.9366(5) 0.5572(5) 0.7743(4) 0.0336(8) Uani 1 1 d . . . H14 H 0.9352 0.4533 0.8288 0.040 Uiso 1 1 d R . . C12 C 1.0039(6) 0.7300(6) 0.5738(5) 0.0418(10) Uani 1 1 d . . . H12 H 1.0479 0.7416 0.4925 0.050 Uiso 1 1 d R . . C22 C 0.9283(6) 1.3429(6) 1.1257(4) 0.0392(9) Uani 1 1 d . . . H22 H 0.9459 1.4332 1.1248 0.047 Uiso 1 1 d R . . C26 C 0.6071(5) 0.7518(5) 1.2385(4) 0.0361(9) Uani 1 1 d . . . H26 H 0.6505 0.6932 1.1828 0.043 Uiso 1 1 d R . . C13 C 1.0003(5) 0.5753(6) 0.6538(5) 0.0405(10) Uani 1 1 d . . . H13 H 1.0411 0.4843 0.6261 0.049 Uiso 1 1 d R . . C35 C 1.2125(6) 0.4466(6) 1.3376(5) 0.0465(11) Uani 1 1 d . . . H35 H 1.2303 0.3759 1.4230 0.056 Uiso 1 1 d R . . C30 C 0.6055(6) 0.9427(6) 1.3245(4) 0.0407(10) Uani 1 1 d . . . H30 H 0.6475 1.0143 1.3282 0.049 Uiso 1 1 d R . . C11 C 0.9423(5) 0.8684(6) 0.6132(4) 0.0358(9) Uani 1 1 d . . . C9 C 0.4150(6) 1.1272(7) 0.6983(5) 0.0473(11) Uani 1 1 d . . . H9A H 0.3039 1.1399 0.7088 0.057 Uiso 1 1 d R . . H9B H 0.4174 1.2358 0.6477 0.057 Uiso 1 1 d R . . H9C H 0.4765 1.0478 0.6564 0.057 Uiso 1 1 d R . . C15 C 0.8727(6) 0.6940(6) 0.8151(5) 0.0308(10) Uani 1 1 d . . . H15 H 0.8309 0.6808 0.8971 0.037 Uiso 1 1 d R . . C6 C 0.6518(6) 1.4491(6) 0.7296(5) 0.0315(10) Uani 1 1 d . . . H6 H 0.7578 1.4318 0.7005 0.038 Uiso 1 1 d R . . C33 C 1.3051(5) 0.5166(7) 1.1223(5) 0.0473(11) Uani 1 1 d . . . H33 H 1.3855 0.4926 1.0620 0.057 Uiso 1 1 d R . . C8 C 0.4723(6) 0.9043(6) 0.9051(5) 0.0451(10) Uani 1 1 d . . . H8A H 0.5343 0.8190 0.8683 0.054 Uiso 1 1 d R . . H8B H 0.5138 0.8661 0.9886 0.054 Uiso 1 1 d R . . H8C H 0.3596 0.9232 0.9111 0.054 Uiso 1 1 d R . . C28 C 0.4140(6) 0.8154(7) 1.4002(5) 0.0475(11) Uani 1 1 d . . . H28 H 0.3268 0.8022 1.4522 0.057 Uiso 1 1 d R . . N2 N 0.8237(5) 1.1823(5) 0.5419(3) 0.0357(7) Uani 1 1 d . . . C16 C 0.9627(6) 1.0298(6) 0.5316(4) 0.0379(9) Uani 1 1 d . . . H16A H 0.9746 1.0390 0.4433 0.045 Uiso 1 1 d R . . H16B H 1.0618 1.0235 0.5565 0.045 Uiso 1 1 d R . . C23 C 0.7794(6) 1.3711(5) 1.0896(4) 0.0375(9) Uani 1 1 d . . . H23 H 0.6955 1.4805 1.0651 0.045 Uiso 1 1 d R . . C18 C 0.8681(7) 1.3284(6) 0.4864(4) 0.0454(11) Uani 1 1 d . . . H18A H 0.9057 1.3409 0.4006 0.054 Uiso 1 1 d R . . H18B H 0.7740 1.4303 0.4863 0.054 Uiso 1 1 d R . . H18C H 0.9533 1.3094 0.5364 0.054 Uiso 1 1 d R . . C34 C 1.3343(6) 0.4126(6) 1.2480(5) 0.0475(11) Uani 1 1 d . . . H34 H 1.4349 0.3201 1.2736 0.057 Uiso 1 1 d R . . C29 C 0.4756(8) 0.9222(9) 1.4049(6) 0.0555(17) Uani 1 1 d . . . H29 H 0.4328 0.9785 1.4621 0.067 Uiso 1 1 d R . . C17 C 0.6861(10) 1.2199(11) 0.4680(7) 0.0550(19) Uani 1 1 d . . . H17A H 0.6594 1.1232 0.4998 0.066 Uiso 1 1 d R . . H17B H 0.5935 1.3171 0.4778 0.066 Uiso 1 1 d R . . H17C H 0.7144 1.2443 0.3795 0.066 Uiso 1 1 d R . . C3 C 0.3372(5) 1.5022(6) 0.8182(5) 0.0403(10) Uani 1 1 d . . . H3 H 0.2313 1.5199 0.8478 0.048 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 0.02967(11) 0.02519(11) 0.02102(10) -0.01050(8) 0.00081(7) -0.01077(8) Si1 0.0254(6) 0.0197(6) 0.0207(6) -0.0097(5) 0.0016(4) -0.0075(4) N1 0.052(3) 0.038(2) 0.036(2) -0.0117(18) -0.0055(19) -0.025(2) Cl1 0.0379(6) 0.0418(7) 0.0381(7) -0.0149(5) -0.0019(5) -0.0172(5) C31 0.0292(17) 0.0277(19) 0.0301(19) -0.0165(15) 0.0002(14) -0.0109(15) C1 0.0285(18) 0.0283(19) 0.0236(18) -0.0107(14) -0.0026(13) -0.0068(14) O1 0.0355(14) 0.0269(13) 0.0182(13) -0.0082(10) -0.0013(10) -0.0133(11) C20 0.039(2) 0.032(2) 0.032(2) -0.0145(16) 0.0003(15) -0.0153(17) C25 0.0280(17) 0.0245(18) 0.0181(16) -0.0065(13) 0.0018(12) -0.0086(14) C24 0.037(2) 0.0254(19) 0.031(2) -0.0128(15) 0.0015(15) -0.0130(16) C19 0.0342(18) 0.0244(18) 0.0189(16) -0.0096(13) 0.0058(13) -0.0137(15) C21 0.049(3) 0.048(3) 0.035(3) -0.014(2) 0.0003(19) -0.029(2) C27 0.041(2) 0.041(2) 0.047(3) -0.0102(19) -0.0038(19) -0.0227(19) C2 0.035(2) 0.035(2) 0.033(2) -0.0193(17) -0.0009(15) -0.0127(17) C10 0.0350(19) 0.029(2) 0.0272(19) -0.0151(15) 0.0058(15) -0.0147(16) C5 0.052(3) 0.030(2) 0.047(3) -0.0138(19) -0.008(2) -0.0153(19) C4 0.042(2) 0.031(2) 0.055(3) -0.024(2) -0.0117(19) -0.0035(18) C36 0.0337(19) 0.030(2) 0.0301(19) -0.0110(15) 0.0001(15) -0.0117(16) C7 0.0280(19) 0.042(2) 0.041(2) -0.0207(18) 0.0089(16) -0.0145(17) C32 0.037(2) 0.035(2) 0.031(2) -0.0149(17) 0.0008(16) -0.0046(17) C14 0.039(2) 0.024(2) 0.040(2) -0.0138(16) -0.0015(16) -0.0129(17) C12 0.048(2) 0.050(3) 0.041(2) -0.032(2) 0.0168(19) -0.025(2) C22 0.063(3) 0.038(2) 0.031(2) -0.0134(17) 0.0053(18) -0.034(2) C26 0.044(2) 0.034(2) 0.035(2) -0.0146(17) 0.0006(17) -0.0183(18) C13 0.040(2) 0.047(3) 0.053(3) -0.037(2) 0.0092(19) -0.0204(19) C35 0.047(3) 0.040(3) 0.035(2) -0.0008(18) -0.0106(19) -0.011(2) C30 0.052(3) 0.040(2) 0.040(2) -0.0254(19) 0.0187(19) -0.025(2) C11 0.046(2) 0.041(2) 0.031(2) -0.0204(17) 0.0092(16) -0.0228(19) C9 0.048(3) 0.059(3) 0.044(3) -0.020(2) -0.006(2) -0.028(2) C15 0.034(2) 0.031(2) 0.026(2) -0.0119(19) 0.0014(17) -0.0123(18) C6 0.034(2) 0.027(2) 0.034(3) -0.0120(19) -0.0047(18) -0.0108(17) C33 0.033(2) 0.050(3) 0.044(3) -0.024(2) 0.0001(18) 0.0018(19) C8 0.048(3) 0.048(3) 0.047(3) -0.017(2) -0.002(2) -0.026(2) C28 0.040(2) 0.052(3) 0.041(3) -0.009(2) 0.0134(19) -0.023(2) N2 0.050(2) 0.039(2) 0.0236(17) -0.0103(14) 0.0035(15) -0.0256(17) C16 0.048(2) 0.047(3) 0.027(2) -0.0195(18) 0.0126(17) -0.027(2) C23 0.052(2) 0.023(2) 0.035(2) -0.0122(16) 0.0019(17) -0.0127(17) C18 0.067(3) 0.039(3) 0.031(2) -0.0101(18) 0.005(2) -0.027(2) C34 0.037(2) 0.036(2) 0.055(3) -0.017(2) -0.006(2) -0.0017(18) C29 0.060(4) 0.062(4) 0.051(4) -0.033(3) 0.032(3) -0.033(3) C17 0.065(4) 0.074(5) 0.029(3) -0.013(3) -0.005(3) -0.036(3) C3 0.0303(19) 0.045(3) 0.051(3) -0.031(2) -0.0034(17) -0.0079(17) _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 O1 1.999(3) . ? Sn1 C1 2.112(4) . ? Sn1 C10 2.127(4) . ? Sn1 Cl1 2.4345(13) . ? Sn1 N1 2.582(5) . ? Si1 O1 1.609(3) . ? Si1 C31 1.872(4) . ? Si1 C25 1.880(4) . ? Si1 C19 1.885(4) . ? N1 C8 1.462(6) . ? N1 C9 1.476(6) . ? N1 C7 1.477(6) . ? C31 C36 1.388(5) . ? C31 C32 1.400(5) . ? C1 C2 1.397(6) . ? C1 C6 1.400(6) . ? C20 C19 1.386(6) . ? C20 C21 1.392(6) . ? C20 H20 0.9300 . ? C25 C30 1.386(5) . ? C25 C26 1.397(5) . ? C24 C23 1.386(6) . ? C24 C19 1.390(6) . ? C24 H24 0.9301 . ? C21 C22 1.375(8) . ? C21 H21 0.9301 . ? C27 C28 1.373(7) . ? C27 C26 1.380(6) . ? C27 H27 0.9300 . ? C2 C3 1.385(6) . ? C2 C7 1.518(6) . ? C10 C11 1.385(5) . ? C10 C15 1.406(6) . ? C5 C4 1.374(7) . ? C5 C6 1.391(7) . ? C5 H5 0.9300 . ? C4 C3 1.384(7) . ? C4 H4 0.9300 . ? C36 C35 1.384(6) . ? C36 H36 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C32 C33 1.390(6) . ? C32 H32 0.9300 . ? C14 C13 1.374(6) . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C12 C13 1.386(7) . ? C12 C11 1.395(6) . ? C12 H12 0.9299 . ? C22 C23 1.374(7) . ? C22 H22 0.9300 . ? C26 H26 0.9300 . ? C13 H13 0.9299 . ? C35 C34 1.391(7) . ? C35 H35 0.9300 . ? C30 C29 1.404(7) . ? C30 H30 0.9300 . ? C11 C16 1.506(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C15 H15 0.9300 . ? C6 H6 0.9300 . ? C33 C34 1.369(7) . ? C33 H33 0.9300 . ? C8 H8A 0.9601 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C28 C29 1.377(8) . ? C28 H28 0.9300 . ? N2 C16 1.463(6) . ? N2 C18 1.472(6) . ? N2 C17 1.473(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C23 H23 0.9300 . ? C18 H18A 0.9601 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C34 H34 0.9300 . ? C29 H29 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C3 H3 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 O1 Sn1 C1 103.40(13) . . ? O1 Sn1 C10 98.90(13) . . ? C1 Sn1 C10 151.13(15) . . ? O1 Sn1 Cl1 93.56(8) . . ? C1 Sn1 Cl1 97.88(11) . . ? C10 Sn1 Cl1 98.81(11) . . ? O1 Sn1 N1 80.85(13) . . ? C1 Sn1 N1 73.84(15) . . ? C10 Sn1 N1 92.08(14) . . ? Cl1 Sn1 N1 168.44(9) . . ? O1 Si1 C31 111.01(16) . . ? O1 Si1 C25 107.21(17) . . ? C31 Si1 C25 108.37(17) . . ? O1 Si1 C19 113.33(16) . . ? C31 Si1 C19 107.00(17) . . ? C25 Si1 C19 109.84(16) . . ? C8 N1 C9 109.4(4) . . ? C8 N1 C7 109.3(4) . . ? C9 N1 C7 111.3(4) . . ? C8 N1 Sn1 117.2(3) . . ? C9 N1 Sn1 109.4(3) . . ? C7 N1 Sn1 99.9(3) . . ? C36 C31 C32 117.6(4) . . ? C36 C31 Si1 121.9(3) . . ? C32 C31 Si1 120.4(3) . . ? C2 C1 C6 118.8(4) . . ? C2 C1 Sn1 118.3(3) . . ? C6 C1 Sn1 122.9(3) . . ? Si1 O1 Sn1 146.36(17) . . ? C19 C20 C21 121.3(4) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.6 . . ? C30 C25 C26 116.6(4) . . ? C30 C25 Si1 123.6(3) . . ? C26 C25 Si1 119.6(3) . . ? C23 C24 C19 121.6(4) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.3 . . ? C20 C19 C24 117.3(3) . . ? C20 C19 Si1 122.4(3) . . ? C24 C19 Si1 120.3(3) . . ? C22 C21 C20 120.1(5) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 119.5 . . ? C28 C27 C26 120.2(4) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 120.0 . . ? C3 C2 C1 120.1(4) . . ? C3 C2 C7 120.6(4) . . ? C1 C2 C7 119.3(4) . . ? C11 C10 C15 119.5(4) . . ? C11 C10 Sn1 120.9(3) . . ? C15 C10 Sn1 119.5(3) . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 119.9 . . ? C5 C4 C3 120.1(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 120.2 . . ? C35 C36 C31 121.5(4) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.1 . . ? N1 C7 C2 110.8(3) . . ? N1 C7 H7A 109.0 . . ? C2 C7 H7A 109.3 . . ? N1 C7 H7B 109.8 . . ? C2 C7 H7B 109.8 . . ? H7A C7 H7B 108.1 . . ? C33 C32 C31 120.9(4) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.5 . . ? C13 C14 C15 120.4(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 119.7 . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.5 . . ? C23 C22 C21 119.6(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.3 . . ? C27 C26 C25 122.1(4) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 118.8 . . ? C14 C13 C12 119.6(4) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.1 . . ? C36 C35 C34 120.0(4) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 120.3 . . ? C25 C30 C29 121.8(4) . . ? C25 C30 H30 118.8 . . ? C29 C30 H30 119.4 . . ? C10 C11 C12 119.3(4) . . ? C10 C11 C16 119.8(3) . . ? C12 C11 C16 120.8(4) . . ? N1 C9 H9A 109.1 . . ? N1 C9 H9B 109.4 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 110.0 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C14 C15 C10 120.1(4) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 119.9 . . ? C5 C6 C1 120.5(4) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.8 . . ? C34 C33 C32 120.6(4) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.8 . . ? N1 C8 H8A 109.6 . . ? N1 C8 H8B 109.4 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C27 C28 C29 119.9(4) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.2 . . ? C16 N2 C18 109.3(4) . . ? C16 N2 C17 108.7(4) . . ? C18 N2 C17 108.2(4) . . ? N2 C16 C11 112.3(3) . . ? N2 C16 H16A 108.9 . . ? C11 C16 H16A 109.1 . . ? N2 C16 H16B 109.4 . . ? C11 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C22 C23 C24 120.1(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 119.8 . . ? N2 C18 H18A 109.7 . . ? N2 C18 H18B 109.3 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C33 C34 C35 119.5(4) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.0 . . ? C28 C29 C30 119.5(5) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.3 . . ? N2 C17 H17A 109.4 . . ? N2 C17 H17B 108.7 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 110.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 120.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.684 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.074 data_shelxl4 _database_code_depnum_ccdc_archive 'CCDC 921173' #TrackingRef 'ps080115Sn1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H29 Cl N2 O Sn' _chemical_formula_sum 'C25 H29 Cl N2 O Sn' _chemical_formula_weight 527.64 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' Cl Cl 0.1484 0.1585 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7460(8) _cell_length_b 9.9541(8) _cell_length_c 18.3250(14) _cell_angle_alpha 90 _cell_angle_beta 94.748(5) _cell_angle_gamma 90 _cell_volume 2317.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 18190 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _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 0 1 0.072 0 0 -1 0.092 0 -1 1 0.070 0 -1 -1 0.069 0 1 1 0.113 0 1 -1 0.111 -1 0 0 0.050 1 0 0 0.050 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.891 _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 18128 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 27.40 _reflns_number_total 5196 _reflns_number_gt 4335 _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, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0116P)^2^+2.9445P] 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 5196 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0605 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.002 _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 0.279540(13) 0.226085(17) 0.628997(9) 0.01776(6) Uani 1 1 d . . . Cl1 Cl 0.28159(5) 0.27621(7) 0.49498(3) 0.02914(14) Uani 1 1 d . . . C10 C 0.14831(19) 0.0919(2) 0.61449(13) 0.0195(5) Uani 1 1 d . . . O1 O 0.42040(15) -0.01193(19) 0.65862(11) 0.0311(4) Uani 1 1 d . . . N1 N 0.28674(16) 0.2142(2) 0.76271(11) 0.0212(4) Uani 1 1 d . . . C4 C 0.3158(2) 0.6873(3) 0.72038(15) 0.0310(6) Uani 1 1 d . . . H4 H 0.3222 0.7739 0.7392 0.037 Uiso 1 1 d R . . C1 C 0.29243(19) 0.4302(2) 0.66329(14) 0.0198(5) Uani 1 1 d . . . C25 C 0.5417(2) 0.2816(3) 0.59407(14) 0.0268(6) Uani 1 1 d . . . H25 H 0.4970 0.3440 0.6131 0.032 Uiso 1 1 d R . . C22 C 0.6712(2) 0.0957(3) 0.53399(14) 0.0311(7) Uani 1 1 d . . . H22 H 0.7138 0.0338 0.5125 0.037 Uiso 1 1 d R . . C14 C 0.0894(2) -0.1394(3) 0.61400(14) 0.0269(6) Uani 1 1 d . . . H14 H 0.1048 -0.2302 0.6201 0.032 Uiso 1 1 d R . . N2 N 0.03299(18) 0.3584(2) 0.64410(13) 0.0276(5) Uani 1 1 d . . . C6 C 0.3266(2) 0.5337(3) 0.62061(14) 0.0236(5) Uani 1 1 d . . . H6 H 0.3409 0.5172 0.5725 0.028 Uiso 1 1 d R . . C20 C 0.51801(19) 0.1459(3) 0.59661(13) 0.0217(5) Uani 1 1 d . . . C17 C 0.0280(3) 0.5014(3) 0.62547(19) 0.0408(8) Uani 1 1 d . . . H17A H -0.0402 0.5224 0.6021 0.049 Uiso 1 1 d R . . H17B H 0.0809 0.5216 0.5927 0.049 Uiso 1 1 d R . . H17C H 0.0403 0.5539 0.6693 0.049 Uiso 1 1 d R . . C16 C 0.0200(2) 0.2772(3) 0.57786(14) 0.0260(6) Uani 1 1 d . . . H16A H 0.0659 0.3112 0.5425 0.031 Uiso 1 1 d R . . H16B H -0.0520 0.2848 0.5566 0.031 Uiso 1 1 d R . . C5 C 0.3397(2) 0.6623(3) 0.64976(15) 0.0277(6) Uani 1 1 d . . . H5 H 0.3651 0.7309 0.6216 0.033 Uiso 1 1 d R . . C2 C 0.27066(19) 0.4550(3) 0.73508(14) 0.0223(5) Uani 1 1 d . . . C11 C 0.0448(2) 0.1321(3) 0.59277(13) 0.0221(5) Uani 1 1 d . . . C19 C 0.42339(19) 0.0998(3) 0.63174(14) 0.0227(5) Uani 1 1 d . . . C21 C 0.5840(2) 0.0523(3) 0.56697(14) 0.0247(6) Uani 1 1 d . . . H21 H 0.5692 -0.0389 0.5698 0.030 Uiso 1 1 d R . . C24 C 0.6317(2) 0.3240(3) 0.56332(15) 0.0328(6) Uani 1 1 d . . . H24 H 0.6491 0.4148 0.5635 0.039 Uiso 1 1 d R . . C8 C 0.3970(2) 0.2169(3) 0.79498(14) 0.0278(6) Uani 1 1 d . . . H8A H 0.3978 0.2237 0.8473 0.033 Uiso 1 1 d R . . H8B H 0.4326 0.2929 0.7763 0.033 Uiso 1 1 d R . . H8C H 0.4321 0.1358 0.7824 0.033 Uiso 1 1 d R . . C15 C 0.1691(2) -0.0447(3) 0.62461(14) 0.0226(5) Uani 1 1 d . . . H15 H 0.2373 -0.0727 0.6388 0.027 Uiso 1 1 d R . . C23 C 0.6952(2) 0.2311(3) 0.53270(15) 0.0332(7) Uani 1 1 d . . . H23 H 0.7546 0.2596 0.5109 0.040 Uiso 1 1 d R . . C3 C 0.2810(2) 0.5841(3) 0.76297(15) 0.0277(6) Uani 1 1 d . . . H3 H 0.2651 0.6014 0.8107 0.033 Uiso 1 1 d R . . C13 C -0.0123(2) -0.0992(3) 0.59457(15) 0.0295(6) Uani 1 1 d . . . H13 H -0.0661 -0.1624 0.5884 0.035 Uiso 1 1 d R . . C7 C 0.2339(2) 0.3411(3) 0.78065(14) 0.0238(6) Uani 1 1 d . . . H7A H 0.2497 0.3616 0.8321 0.029 Uiso 1 1 d R . . H7B H 0.1582 0.3307 0.7717 0.029 Uiso 1 1 d R . . C12 C -0.0340(2) 0.0362(3) 0.58422(15) 0.0284(6) Uani 1 1 d . . . H12 H -0.1028 0.0632 0.5712 0.034 Uiso 1 1 d R . . C9 C 0.2320(2) 0.0998(3) 0.79278(15) 0.0306(6) Uani 1 1 d . . . H9A H 0.2669 0.0178 0.7815 0.037 Uiso 1 1 d R . . H9B H 0.1606 0.0975 0.7717 0.037 Uiso 1 1 d R . . H9C H 0.2327 0.1095 0.8449 0.037 Uiso 1 1 d R . . C18 C -0.0467(2) 0.3250(3) 0.69329(16) 0.0373(7) Uani 1 1 d . . . H18A H -0.0381 0.3816 0.7358 0.045 Uiso 1 1 d R . . H18B H -0.0396 0.2326 0.7079 0.045 Uiso 1 1 d R . . H18C H -0.1153 0.3392 0.6687 0.045 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 0.01852(8) 0.01636(9) 0.01859(9) -0.00009(7) 0.00264(6) -0.00132(7) Cl1 0.0367(3) 0.0321(4) 0.0189(3) 0.0014(3) 0.0039(2) -0.0030(3) C10 0.0205(12) 0.0206(13) 0.0179(12) -0.0012(10) 0.0045(9) -0.0011(10) O1 0.0274(10) 0.0221(11) 0.0444(12) 0.0064(9) 0.0062(8) 0.0014(8) N1 0.0216(10) 0.0217(11) 0.0201(10) 0.0024(9) 0.0012(8) -0.0020(9) C4 0.0378(16) 0.0200(14) 0.0333(16) -0.0044(11) -0.0099(12) 0.0034(12) C1 0.0191(12) 0.0170(13) 0.0231(13) -0.0006(10) 0.0002(10) 0.0010(10) C25 0.0230(12) 0.0308(15) 0.0269(14) 0.0018(12) 0.0036(10) 0.0003(12) C22 0.0206(13) 0.050(2) 0.0225(14) -0.0039(12) 0.0002(10) 0.0078(13) C14 0.0360(15) 0.0186(14) 0.0268(14) -0.0035(11) 0.0078(11) -0.0051(12) N2 0.0275(12) 0.0215(12) 0.0335(13) -0.0030(10) 0.0003(10) 0.0013(10) C6 0.0231(13) 0.0223(14) 0.0253(14) 0.0007(10) 0.0017(10) 0.0006(11) C20 0.0170(12) 0.0280(15) 0.0199(13) -0.0004(10) -0.0008(9) -0.0006(10) C17 0.0422(18) 0.0217(16) 0.058(2) 0.0026(14) 0.0036(15) 0.0015(13) C16 0.0218(12) 0.0302(15) 0.0261(13) 0.0026(11) 0.0030(10) 0.0043(12) C5 0.0285(14) 0.0191(14) 0.0342(16) 0.0054(11) -0.0060(11) 0.0002(11) C2 0.0194(12) 0.0225(14) 0.0243(13) -0.0011(10) -0.0016(10) 0.0038(10) C11 0.0224(12) 0.0263(14) 0.0180(12) -0.0026(10) 0.0040(10) 0.0001(11) C19 0.0198(12) 0.0261(15) 0.0221(13) -0.0039(11) 0.0007(10) -0.0021(11) C21 0.0220(13) 0.0312(15) 0.0198(13) -0.0022(11) -0.0050(10) 0.0008(11) C24 0.0283(14) 0.0359(16) 0.0340(16) 0.0049(13) 0.0016(12) -0.0084(13) C8 0.0262(13) 0.0311(15) 0.0251(14) -0.0003(12) -0.0030(10) 0.0005(12) C15 0.0220(12) 0.0234(14) 0.0229(13) -0.0014(10) 0.0039(10) -0.0010(11) C23 0.0202(12) 0.055(2) 0.0248(14) 0.0054(13) 0.0029(10) -0.0032(13) C3 0.0315(14) 0.0286(15) 0.0218(14) -0.0053(11) -0.0047(11) 0.0081(12) C13 0.0290(14) 0.0334(17) 0.0271(15) -0.0062(12) 0.0090(11) -0.0129(12) C7 0.0241(13) 0.0292(15) 0.0185(13) -0.0008(10) 0.0045(10) -0.0007(11) C12 0.0196(13) 0.0382(17) 0.0276(14) -0.0034(12) 0.0038(10) 0.0003(12) C9 0.0401(16) 0.0289(16) 0.0227(14) 0.0042(11) 0.0035(12) -0.0106(13) C18 0.0440(17) 0.0362(17) 0.0332(16) -0.0038(13) 0.0126(13) 0.0074(14) _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 C1 2.129(2) . ? Sn1 C10 2.140(2) . ? Sn1 C19 2.220(3) . ? Sn1 N1 2.447(2) . ? Sn1 Cl1 2.5084(7) . ? C10 C15 1.394(4) . ? C10 C11 1.404(3) . ? O1 C19 1.218(3) . ? N1 C9 1.466(3) . ? N1 C8 1.479(3) . ? N1 C7 1.481(3) . ? C4 C5 1.377(4) . ? C4 C3 1.385(4) . ? C4 H4 0.9300 . ? C1 C6 1.386(4) . ? C1 C2 1.389(3) . ? C25 C20 1.386(4) . ? C25 C24 1.386(4) . ? C25 H25 0.9300 . ? C22 C21 1.377(4) . ? C22 C23 1.382(4) . ? C22 H22 0.9301 . ? C14 C13 1.376(4) . ? C14 C15 1.387(4) . ? C14 H14 0.9300 . ? N2 C18 1.451(4) . ? N2 C16 1.456(3) . ? N2 C17 1.464(4) . ? C6 C5 1.392(4) . ? C6 H6 0.9300 . ? C20 C21 1.395(4) . ? C20 C19 1.486(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9601 . ? C17 H17C 0.9600 . ? C16 C11 1.498(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C5 H5 0.9299 . ? C2 C3 1.385(4) . ? C2 C7 1.506(4) . ? C11 C12 1.385(4) . ? C21 H21 0.9300 . ? C24 C23 1.379(4) . ? C24 H24 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9599 . ? C8 H8C 0.9600 . ? C15 H15 0.9300 . ? C23 H23 0.9300 . ? C3 H3 0.9298 . ? C13 C12 1.386(4) . ? C13 H13 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C12 H12 0.9300 . ? C9 H9A 0.9601 . ? C9 H9B 0.9600 . ? C9 H9C 0.9599 . ? C18 H18A 0.9601 . ? C18 H18B 0.9601 . ? C18 H18C 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 C1 Sn1 C10 132.28(9) . . ? C1 Sn1 C19 119.36(9) . . ? C10 Sn1 C19 106.55(9) . . ? C1 Sn1 N1 75.81(8) . . ? C10 Sn1 N1 93.35(8) . . ? C19 Sn1 N1 89.28(8) . . ? C1 Sn1 Cl1 95.30(7) . . ? C10 Sn1 Cl1 94.24(7) . . ? C19 Sn1 Cl1 93.40(7) . . ? N1 Sn1 Cl1 170.88(5) . . ? C15 C10 C11 118.6(2) . . ? C15 C10 Sn1 117.02(18) . . ? C11 C10 Sn1 124.31(19) . . ? C9 N1 C8 109.2(2) . . ? C9 N1 C7 109.85(19) . . ? C8 N1 C7 109.3(2) . . ? C9 N1 Sn1 115.73(16) . . ? C8 N1 Sn1 110.80(15) . . ? C7 N1 Sn1 101.59(14) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 120.1 . . ? C6 C1 C2 119.9(2) . . ? C6 C1 Sn1 124.28(19) . . ? C2 C1 Sn1 115.67(18) . . ? C20 C25 C24 120.1(3) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 120.1 . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 120.1 . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 120.0 . . ? C18 N2 C16 110.7(2) . . ? C18 N2 C17 110.4(2) . . ? C16 N2 C17 110.2(2) . . ? C1 C6 C5 120.0(2) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 119.9 . . ? C25 C20 C21 119.9(2) . . ? C25 C20 C19 120.2(2) . . ? C21 C20 C19 120.0(2) . . ? N2 C17 H17A 109.6 . . ? N2 C17 H17B 109.3 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C16 C11 112.0(2) . . ? N2 C16 H16A 109.3 . . ? C11 C16 H16A 109.2 . . ? N2 C16 H16B 109.2 . . ? C11 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 119.9 . . ? C3 C2 C1 119.6(2) . . ? C3 C2 C7 121.2(2) . . ? C1 C2 C7 119.1(2) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 C16 120.2(2) . . ? C10 C11 C16 120.3(2) . . ? O1 C19 C20 120.7(2) . . ? O1 C19 Sn1 118.21(18) . . ? C20 C19 Sn1 120.89(18) . . ? C22 C21 C20 119.7(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 119.9 . . ? C23 C24 C25 119.6(3) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.1 . . ? N1 C8 H8A 109.4 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.6 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C15 C10 121.0(2) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.5 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.6 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.4 . . ? N1 C7 C2 110.53(19) . . ? N1 C7 H7A 109.5 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.6 . . ? C2 C7 H7B 109.7 . . ? H7A C7 H7B 108.1 . . ? C11 C12 C13 121.4(3) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? N1 C9 H9A 109.7 . . ? N1 C9 H9B 109.4 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.3 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C18 H18A 109.3 . . ? N2 C18 H18B 109.7 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.4 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.668 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.088 data_shelxl5 _database_code_depnum_ccdc_archive 'CCDC 921174' #TrackingRef 'zp110608Sn1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C72 H60 Ge4 O8 Sn6' _chemical_formula_sum 'C72 H60 Ge4 O8 Sn6' _chemical_formula_weight 2055.70 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' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M 'P 63' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' '-x+y, -x, z' 'x-y, x, z+1/2' 'y, -x+y, z+1/2' _cell_length_a 16.0010(7) _cell_length_b 16.0010(7) _cell_length_c 17.4671(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 3873.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 24025 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 3.476 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 1 0 0.062 1 -1 0 0.108 0 1 0 0.097 0 -1 0 0.115 0 0 1 0.060 0 0 -1 0.060 -1 0 0 0.130 1 0 0 0.153 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.460 _exptl_absorpt_correction_T_max 0.675 _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 23910 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5862 _reflns_number_gt 5053 _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^)+(0.0252P)^2^+5.5113P] 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 0.010(14) _refine_ls_number_reflns 5862 _refine_ls_number_parameters 271 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.64583(2) 0.19694(2) 0.25851(2) 0.02401(8) Uani 1 1 d . . . Sn2 Sn 0.52938(2) 0.22053(2) 0.094145(19) 0.02536(9) Uani 1 1 d . . . Ge2 Ge 0.6667 0.3333 -0.08387(6) 0.02239(19) Uani 1 3 d S . . Ge1 Ge 0.37721(3) 0.09361(3) 0.25482(3) 0.02308(11) Uani 1 1 d . . . O3 O 0.6667 0.3333 0.2842(3) 0.0212(13) Uani 1 3 d S . . O2 O 0.6447(2) 0.2139(2) 0.1399(2) 0.0222(7) Uani 1 1 d . . . O4 O 0.6667 0.3333 0.0187(3) 0.0268(14) Uani 1 3 d S . . O1 O 0.4927(2) 0.1926(2) 0.2294(2) 0.0258(8) Uani 1 1 d . . . C1 C 0.3543(4) -0.0140(4) 0.1889(3) 0.0278(11) Uani 1 1 d . . . C14 C 0.2075(4) 0.1080(4) 0.2921(4) 0.0368(13) Uani 1 1 d . . . H14 H 0.2080 0.0780 0.3375 0.044 Uiso 1 1 d R . . C8 C 0.3063(5) -0.0320(4) 0.3854(4) 0.0382(14) Uani 1 1 d . . . H8 H 0.2602 -0.0750 0.3513 0.046 Uiso 1 1 d R . . C7 C 0.3772(4) 0.0585(4) 0.3612(3) 0.0299(12) Uani 1 1 d . . . C13 C 0.2800(3) 0.1306(4) 0.2380(3) 0.0265(11) Uani 1 1 d . . . C20 C 0.8726(4) 0.3913(4) -0.0928(3) 0.0320(12) Uani 1 1 d . . . H20 H 0.8817 0.4341 -0.0533 0.038 Uiso 1 1 d R . . C6 C 0.4034(5) -0.0641(4) 0.2012(3) 0.0399(14) Uani 1 1 d . . . H6 H 0.4447 -0.0483 0.2429 0.048 Uiso 1 1 d R . . C15 C 0.1344(4) 0.1283(4) 0.2808(4) 0.0415(16) Uani 1 1 d . . . H15 H 0.0854 0.1104 0.3168 0.050 Uiso 1 1 d R . . C21 C 0.9505(4) 0.3882(4) -0.1220(4) 0.0387(14) Uani 1 1 d . . . H21 H 1.0117 0.4289 -0.1023 0.046 Uiso 1 1 d R . . C2 C 0.2897(4) -0.0426(5) 0.1272(4) 0.0400(15) Uani 1 1 d . . . H2 H 0.2560 -0.0104 0.1172 0.048 Uiso 1 1 d R . . C19 C 0.7800(4) 0.3316(4) -0.1212(3) 0.0248(11) Uani 1 1 d . . . C23 C 0.8491(4) 0.2688(4) -0.2129(4) 0.0455(16) Uani 1 1 d . . . H23 H 0.8416 0.2284 -0.2538 0.055 Uiso 1 1 d R . . C12 C 0.4464(4) 0.1191(5) 0.4130(4) 0.0420(14) Uani 1 1 d . . . H12 H 0.4965 0.1792 0.3980 0.050 Uiso 1 1 d R . . C16 C 0.1341(5) 0.1740(5) 0.2127(4) 0.0457(16) Uani 1 1 d . . . H16 H 0.0849 0.1878 0.2039 0.055 Uiso 1 1 d R . . C17 C 0.2052(5) 0.2002(5) 0.1612(4) 0.0448(15) Uani 1 1 d . . . H17 H 0.2053 0.2340 0.1178 0.054 Uiso 1 1 d R . . C22 C 0.9386(5) 0.3262(5) -0.1810(4) 0.0460(17) Uani 1 1 d . . . H22 H 0.9913 0.3230 -0.1997 0.055 Uiso 1 1 d R . . C18 C 0.2776(4) 0.1785(4) 0.1717(3) 0.0389(14) Uani 1 1 d . . . H18 H 0.3248 0.1959 0.1343 0.047 Uiso 1 1 d R . . C5 C 0.3901(5) -0.1389(5) 0.1547(4) 0.0489(17) Uani 1 1 d . . . H5 H 0.4254 -0.1702 0.1613 0.059 Uiso 1 1 d R . . C4 C 0.3255(5) -0.1663(4) 0.0936(5) 0.0544(17) Uani 1 1 d . . . H4 H 0.3136 -0.2192 0.0636 0.065 Uiso 1 1 d R . . C24 C 0.7701(4) 0.2703(4) -0.1816(4) 0.0376(14) Uani 1 1 d . . . H24 H 0.7092 0.2302 -0.2022 0.045 Uiso 1 1 d R . . C9 C 0.3037(6) -0.0597(6) 0.4629(4) 0.0525(18) Uani 1 1 d . . . H9 H 0.2552 -0.1197 0.4796 0.063 Uiso 1 1 d R . . C11 C 0.4425(6) 0.0899(6) 0.4885(4) 0.058(2) Uani 1 1 d . . . H11 H 0.4869 0.1320 0.5240 0.069 Uiso 1 1 d R . . C3 C 0.2768(5) -0.1178(5) 0.0810(4) 0.0545(19) Uani 1 1 d . . . H3 H 0.2348 -0.1356 0.0396 0.065 Uiso 1 1 d R . . C10 C 0.3713(6) -0.0005(6) 0.5120(4) 0.059(2) Uani 1 1 d . . . H10 H 0.3705 -0.0199 0.5623 0.071 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 0.03100(17) 0.02036(15) 0.02189(15) 0.00284(16) 0.00130(17) 0.01377(13) Sn2 0.02229(16) 0.02364(16) 0.02905(18) -0.00570(18) -0.00758(18) 0.01065(13) Ge2 0.0247(4) 0.023 0.0189(4) 0.000 0.000 0.012 Ge1 0.0207(2) 0.0210(2) 0.0235(2) 0.0018(3) 0.0016(3) 0.00744(18) O3 0.020(3) 0.017 0.025(3) 0.000 0.000 0.009 O2 0.0232(17) 0.0222(17) 0.0210(17) 0.0008(14) -0.0009(14) 0.0113(15) O4 0.031(3) 0.031 0.018(3) 0.000 0.000 0.016 O1 0.0218(17) 0.0244(17) 0.0253(18) 0.0029(14) 0.0038(14) 0.0071(15) C1 0.024(2) 0.023(3) 0.028(3) 0.000(2) 0.002(2) 0.005(2) C14 0.036(3) 0.035(3) 0.037(3) 0.008(3) 0.002(3) 0.015(3) C8 0.041(3) 0.037(3) 0.038(3) 0.012(3) 0.004(3) 0.021(3) C7 0.032(3) 0.028(3) 0.035(3) 0.003(2) 0.000(2) 0.018(2) C13 0.022(2) 0.025(2) 0.028(3) -0.005(2) -0.005(2) 0.008(2) C20 0.027(3) 0.024(3) 0.036(3) 0.005(2) 0.005(2) 0.006(2) C6 0.053(4) 0.045(4) 0.028(3) -0.001(3) 0.003(3) 0.029(3) C15 0.022(3) 0.047(4) 0.051(4) 0.012(3) 0.013(3) 0.014(3) C21 0.026(3) 0.034(3) 0.051(4) 0.007(3) 0.002(3) 0.011(2) C2 0.033(3) 0.038(3) 0.040(3) -0.008(3) -0.010(3) 0.011(3) C19 0.029(3) 0.023(2) 0.022(3) 0.007(2) 0.008(2) 0.013(2) C23 0.038(3) 0.036(3) 0.059(4) -0.013(3) 0.014(3) 0.017(3) C12 0.044(3) 0.049(4) 0.036(3) -0.007(3) -0.003(3) 0.025(3) C16 0.037(3) 0.052(4) 0.058(4) 0.001(3) -0.006(3) 0.029(3) C17 0.049(4) 0.056(4) 0.038(3) 0.006(3) -0.006(3) 0.032(3) C22 0.041(4) 0.032(3) 0.067(5) 0.011(3) 0.026(3) 0.021(3) C18 0.034(3) 0.049(4) 0.033(3) 0.003(3) 0.001(3) 0.021(3) C5 0.053(4) 0.041(4) 0.052(4) -0.005(3) 0.011(3) 0.023(3) C4 0.059(4) 0.042(3) 0.052(4) -0.021(4) 0.002(4) 0.017(3) C24 0.027(3) 0.035(3) 0.051(4) -0.009(3) 0.002(3) 0.016(3) C9 0.068(5) 0.063(5) 0.043(4) 0.016(4) 0.014(4) 0.044(4) C11 0.078(5) 0.096(6) 0.026(3) -0.012(4) -0.011(4) 0.063(5) C3 0.043(4) 0.058(4) 0.052(5) -0.031(4) -0.019(3) 0.018(3) C10 0.086(6) 0.085(6) 0.034(4) 0.024(4) 0.016(4) 0.063(5) _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 O3 2.0844(14) . ? Sn1 O2 2.090(4) . ? Sn1 O1 2.323(3) 3_655 ? Sn1 O1 2.469(3) . ? Sn2 O2 2.063(3) . ? Sn2 O2 2.079(3) 4_665 ? Sn2 O4 2.420(3) . ? Sn2 O1 2.422(3) . ? Ge2 O4 1.791(6) . ? Ge2 C19 1.940(5) . ? Ge2 C19 1.941(5) 4_665 ? Ge2 C19 1.941(5) 3_655 ? Ge1 O1 1.787(3) . ? Ge1 C7 1.941(6) . ? Ge1 C13 1.943(5) . ? Ge1 C1 1.947(5) . ? O3 Sn1 2.0849(14) 3_655 ? O3 Sn1 2.0859(14) 4_665 ? O2 Sn2 2.079(3) 3_655 ? O4 Sn2 2.419(3) 3_655 ? O4 Sn2 2.420(3) 4_665 ? O1 Sn1 2.323(3) 4_665 ? C1 C6 1.390(8) . ? C1 C2 1.403(8) . ? C14 C15 1.377(8) . ? C14 C13 1.396(8) . ? C14 H14 0.9301 . ? C8 C7 1.385(8) . ? C8 C9 1.419(9) . ? C8 H8 0.9301 . ? C7 C12 1.383(8) . ? C13 C18 1.400(8) . ? C20 C21 1.371(8) . ? C20 C19 1.393(7) . ? C20 H20 0.9301 . ? C6 C5 1.373(8) . ? C6 H6 0.9300 . ? C15 C16 1.398(9) . ? C15 H15 0.9301 . ? C21 C22 1.375(9) . ? C21 H21 0.9300 . ? C2 C3 1.375(9) . ? C2 H2 0.9300 . ? C19 C24 1.394(8) . ? C23 C22 1.374(9) . ? C23 C24 1.390(8) . ? C23 H23 0.9300 . ? C12 C11 1.389(9) . ? C12 H12 0.9301 . ? C16 C17 1.342(9) . ? C16 H16 0.9300 . ? C17 C18 1.379(8) . ? C17 H17 0.9301 . ? C22 H22 0.9299 . ? C18 H18 0.9299 . ? C5 C4 1.394(10) . ? C5 H5 0.9300 . ? C4 C3 1.366(10) . ? C4 H4 0.9301 . ? C24 H24 0.9300 . ? C9 C10 1.334(11) . ? C9 H9 0.9299 . ? C11 C10 1.383(11) . ? C11 H11 0.9300 . ? C3 H3 0.9299 . ? C10 H10 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 O3 Sn1 O2 94.86(19) . . ? O3 Sn1 O1 76.36(10) . 3_655 ? O2 Sn1 O1 76.69(12) . 3_655 ? O3 Sn1 O1 73.20(9) . . ? O2 Sn1 O1 74.18(12) . . ? O1 Sn1 O1 135.31(14) 3_655 . ? O2 Sn2 O2 94.97(18) . 4_665 ? O2 Sn2 O4 75.37(12) . . ? O2 Sn2 O4 75.13(12) 4_665 . ? O2 Sn2 O1 75.67(13) . . ? O2 Sn2 O1 74.70(13) 4_665 . ? O4 Sn2 O1 135.62(15) . . ? O4 Ge2 C19 109.64(16) . . ? O4 Ge2 C19 109.63(16) . 4_665 ? C19 Ge2 C19 109.34(16) . 4_665 ? O4 Ge2 C19 109.62(16) . 3_655 ? C19 Ge2 C19 109.31(16) . 3_655 ? C19 Ge2 C19 109.28(16) 4_665 3_655 ? O1 Ge1 C7 110.1(2) . . ? O1 Ge1 C13 108.85(19) . . ? C7 Ge1 C13 110.4(2) . . ? O1 Ge1 C1 106.91(19) . . ? C7 Ge1 C1 109.7(2) . . ? C13 Ge1 C1 110.8(2) . . ? Sn1 O3 Sn1 115.54(12) . 3_655 ? Sn1 O3 Sn1 115.50(11) . 4_665 ? Sn1 O3 Sn1 115.48(11) 3_655 4_665 ? Sn2 O2 Sn2 116.15(16) . 3_655 ? Sn2 O2 Sn1 117.17(16) . . ? Sn2 O2 Sn1 113.79(15) 3_655 . ? Ge2 O4 Sn2 123.01(12) . 3_655 ? Ge2 O4 Sn2 123.00(12) . . ? Sn2 O4 Sn2 93.17(16) 3_655 . ? Ge2 O4 Sn2 122.99(12) . 4_665 ? Sn2 O4 Sn2 93.16(16) 3_655 4_665 ? Sn2 O4 Sn2 93.14(16) . 4_665 ? Ge1 O1 Sn1 126.46(17) . 4_665 ? Ge1 O1 Sn2 116.95(17) . . ? Sn1 O1 Sn2 94.73(12) 4_665 . ? Ge1 O1 Sn1 123.08(16) . . ? Sn1 O1 Sn1 94.73(12) 4_665 . ? Sn2 O1 Sn1 92.87(11) . . ? C6 C1 C2 117.8(5) . . ? C6 C1 Ge1 120.5(4) . . ? C2 C1 Ge1 121.7(4) . . ? C15 C14 C13 122.5(6) . . ? C15 C14 H14 118.1 . . ? C13 C14 H14 119.4 . . ? C7 C8 C9 119.9(7) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 119.5 . . ? C8 C7 C12 118.9(6) . . ? C8 C7 Ge1 118.4(5) . . ? C12 C7 Ge1 122.6(4) . . ? C14 C13 C18 117.0(5) . . ? C14 C13 Ge1 120.5(4) . . ? C18 C13 Ge1 122.5(4) . . ? C21 C20 C19 121.1(5) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.4 . . ? C5 C6 C1 121.8(6) . . ? C5 C6 H6 118.6 . . ? C1 C6 H6 119.6 . . ? C14 C15 C16 118.0(6) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C20 C21 C22 120.3(6) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 120.0 . . ? C3 C2 C1 120.0(6) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C20 C19 C24 117.4(5) . . ? C20 C19 Ge2 123.5(4) . . ? C24 C19 Ge2 119.1(4) . . ? C22 C23 C24 118.7(6) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.8 . . ? C7 C12 C11 119.9(6) . . ? C7 C12 H12 120.9 . . ? C11 C12 H12 119.1 . . ? C17 C16 C15 120.7(6) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 121.3(6) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 119.8 . . ? C23 C22 C21 120.6(6) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 120.0 . . ? C17 C18 C13 120.4(6) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 120.3 . . ? C6 C5 C4 119.6(6) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 118.6 . . ? C3 C4 C5 119.2(6) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.0 . . ? C23 C24 C19 121.7(6) . . ? C23 C24 H24 118.9 . . ? C19 C24 H24 119.3 . . ? C10 C9 C8 120.4(7) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 120.1 . . ? C10 C11 C12 120.6(7) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 120.0 . . ? C4 C3 C2 121.6(7) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 119.6 . . ? C9 C10 C11 120.2(7) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 119.8 . . ? # SQUEEZE RESULTS (APPEND TO CIF) 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 1 0.000 0.000 -0.012 236.6 99.5 2 0.000 0.000 0.488 236.7 97.9 3 0.333 0.667 0.956 19.5 -0.2 4 0.333 0.667 0.214 7.3 -0.1 5 0.667 0.333 0.456 19.5 0.6 6 0.667 0.333 0.714 7.3 0.2 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.494 _refine_diff_density_min -0.805 _refine_diff_density_rms 0.097