# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1798 data_97kcm9 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H35 N5 O2 Sn' _chemical_formula_weight 472.20 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' '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 10.120(2) _cell_length_b 14.269(2) _cell_length_c 16.788(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.31(2) _cell_angle_gamma 90.00 _cell_volume 2377.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method ? _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3953 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 23.93 _reflns_number_total 3722 _reflns_number_observed 2065 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+2.1686P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3712 _refine_ls_number_parameters 239 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_obs 0.0491 _refine_ls_wR_factor_all 0.1420 _refine_ls_wR_factor_obs 0.1079 _refine_ls_goodness_of_fit_all 1.134 _refine_ls_goodness_of_fit_obs 1.201 _refine_ls_restrained_S_all 1.154 _refine_ls_restrained_S_obs 1.210 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn1 Sn 0.56565(5) 0.18469(4) 0.80880(3) 0.0924(3) Uani 1 d . . N1 N 0.6717(6) 0.2933(4) 0.9068(4) 0.097(2) Uani 1 d . . N2 N 0.8040(6) 0.2955(4) 0.9355(4) 0.092(2) Uani 1 d . . N3 N 0.6096(6) 0.3535(5) 0.9464(4) 0.098(2) Uani 1 d . . N4 N 0.7012(6) 0.3964(4) 1.0021(3) 0.088(2) Uani 1 d . . N5 N 1.2011(7) 0.4319(5) 1.1370(4) 0.096(2) Uani 1 d . . C1 C 0.8184(7) 0.3598(5) 0.9941(4) 0.076(2) Uani 1 d . . C2 C 0.9495(6) 0.3857(5) 1.0436(4) 0.075(2) Uani 1 d . . C3 C 1.0661(8) 0.3494(6) 1.0263(5) 0.105(3) Uani 1 d . . H3 H 1.0632(8) 0.3081(6) 0.9832(5) 0.126 Uiso 1 calc R . C4 C 0.9626(7) 0.4460(5) 1.1065(5) 0.092(2) Uani 1 d . . H4 H 0.8862(7) 0.4736(5) 1.1194(5) 0.110 Uiso 1 calc R . C5 C 1.1889(8) 0.3752(7) 1.0743(6) 0.112(3) Uani 1 d . . H5 H 1.2672(8) 0.3509(7) 1.0611(6) 0.135 Uiso 1 calc R . C6 C 1.0888(8) 0.4675(6) 1.1522(5) 0.102(2) Uani 1 d . . H6 H 1.0941(8) 0.5089(6) 1.1954(5) 0.122 Uiso 1 calc R . C7 C 0.7453(10) 0.1078(9) 0.8178(9) 0.196(7) Uani 1 d . . H7A H 0.7583(10) 0.0938(9) 0.7633(9) 0.236 Uiso 1 calc R . H7B H 0.8197(10) 0.1471(9) 0.8434(9) 0.236 Uiso 1 calc R . C8 C 0.7513(16) 0.0203(12) 0.8629(11) 0.266(10) Uani 1 d . . H8A H 0.7349(16) 0.0350(12) 0.9166(11) 0.320 Uiso 1 calc R . H8B H 0.6771(16) -0.0186(12) 0.8364(11) 0.320 Uiso 1 calc R . C9 C 0.8649(23) -0.0323(17) 0.8728(15) 0.333(13) Uani 1 d . . H9A H 0.9425(23) 0.0067(17) 0.8936(15) 0.400 Uiso 1 calc R . H9B H 0.8755(23) -0.0573(17) 0.8207(15) 0.400 Uiso 1 calc R . C10 C 0.8588(24) -0.1063(15) 0.9269(15) 0.351(15) Uani 1 d . . H10A H 0.8753(286) -0.0828(36) 0.9815(20) 0.526 Uiso 1 calc R . H10B H 0.9258(194) -0.1523(97) 0.9216(123) 0.526 Uiso 1 calc R . H10C H 0.7710(96) -0.1346(129) 0.9146(112) 0.526 Uiso 1 calc R . C11 C 0.5173(18) 0.2924(10) 0.7223(9) 0.203(6) Uani 1 d D . H11A H 0.4218(18) 0.2879(10) 0.6992(9) 0.244 Uiso 1 calc R . H11B H 0.5314(18) 0.3518(10) 0.7509(9) 0.244 Uiso 1 calc R . C12 C 0.5962(35) 0.2958(18) 0.6496(16) 0.380(20) Uani 1 d D . H12A H 0.6280(35) 0.2344(18) 0.6372(16) 0.457 Uiso 1 calc R . H12B H 0.5424(35) 0.3232(18) 0.6009(16) 0.457 Uiso 1 calc R . C13 C 0.6979(26) 0.3524(25) 0.6841(16) 0.427(29) Uani 1 d D . H13A H 0.7659(26) 0.3200(25) 0.7232(16) 0.512 Uiso 1 calc R . H13B H 0.6669(26) 0.4076(25) 0.7086(16) 0.512 Uiso 1 calc R . C14 C 0.7452(32) 0.3743(19) 0.6044(12) 0.360(17) Uani 1 d D . H14A H 0.8306(137) 0.3447(172) 0.6051(75) 0.539 Uiso 1 calc R . H14B H 0.7544(292) 0.4409(23) 0.5992(88) 0.539 Uiso 1 calc R . H14C H 0.6802(141) 0.3511(180) 0.5593(16) 0.539 Uiso 1 calc R . C15 C 0.4194(13) 0.1575(10) 0.8782(8) 0.196(6) Uani 1 d . . H15A H 0.4185(13) 0.0899(10) 0.8844(8) 0.235 Uiso 1 calc R . H15B H 0.4556(13) 0.1826(10) 0.9317(8) 0.235 Uiso 1 calc R . C16 C 0.2787(24) 0.1857(22) 0.8601(15) 0.335(18) Uani 1 d . . H16A H 0.2292(24) 0.1294(22) 0.8403(15) 0.402 Uiso 1 calc R . H16B H 0.2559(24) 0.1991(22) 0.9124(15) 0.402 Uiso 1 calc R . C17 C 0.2314(38) 0.2419(20) 0.8199(16) 0.382(25) Uani 1 d . . H17A H 0.2543(38) 0.2295(20) 0.7674(16) 0.459 Uiso 1 calc R . H17B H 0.2787(38) 0.2989(20) 0.8400(16) 0.459 Uiso 1 calc R . C18 C 0.0804(15) 0.2671(17) 0.8024(11) 0.248(9) Uani 1 d . . H18A H 0.0459(44) 0.2645(125) 0.7450(15) 0.371 Uiso 1 calc R . H18B H 0.0689(22) 0.3293(48) 0.8218(97) 0.371 Uiso 1 calc R . H18C H 0.0323(31) 0.2233(74) 0.8296(90) 0.371 Uiso 1 calc R . O1 O 0.4675(4) 0.0705(4) 0.7158(3) 0.106(2) Uani 1 d . . O2 O 0.6069(5) -0.0140(4) 0.6148(3) 0.101(2) Uani 1 d . . 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 0.0717(3) 0.0894(4) 0.1067(4) -0.0093(3) -0.0052(2) 0.0015(3) N1 0.075(4) 0.086(4) 0.120(5) -0.016(4) -0.007(4) 0.005(3) N2 0.070(4) 0.092(4) 0.107(4) -0.017(4) -0.001(3) 0.007(3) N3 0.074(4) 0.092(4) 0.118(5) -0.016(4) -0.002(4) 0.010(3) N4 0.077(4) 0.079(4) 0.099(4) -0.011(3) -0.002(3) 0.005(3) N5 0.086(4) 0.101(5) 0.093(4) 0.009(4) -0.005(4) -0.005(4) C1 0.069(4) 0.071(4) 0.083(5) 0.003(4) 0.006(4) 0.006(4) C2 0.067(4) 0.069(4) 0.080(4) 0.006(4) -0.003(3) 0.004(3) C3 0.080(5) 0.118(6) 0.107(6) -0.019(5) -0.008(4) 0.013(5) C4 0.066(4) 0.096(5) 0.104(5) -0.009(5) -0.003(4) 0.003(4) C5 0.073(5) 0.131(7) 0.125(7) 0.004(6) 0.001(5) 0.015(5) C6 0.091(6) 0.106(6) 0.100(6) -0.012(5) 0.003(5) 0.003(5) C7 0.094(7) 0.154(10) 0.304(17) -0.100(11) -0.053(8) 0.037(7) C8 0.223(17) 0.182(14) 0.344(22) 0.036(14) -0.066(15) 0.120(13) C9 0.333(29) 0.240(23) 0.376(33) 0.041(22) -0.052(24) 0.034(23) C10 0.418(33) 0.225(20) 0.365(29) 0.153(22) -0.032(24) -0.007(21) C11 0.250(18) 0.192(13) 0.151(11) 0.001(10) -0.005(12) -0.016(12) C12 0.628(68) 0.269(27) 0.240(26) -0.046(23) 0.077(39) -0.049(30) C13 0.254(27) 0.551(55) 0.431(50) -0.312(49) -0.038(28) -0.014(29) C14 0.602(51) 0.295(26) 0.218(21) 0.001(20) 0.170(27) 0.050(30) C15 0.152(11) 0.220(13) 0.225(14) -0.081(11) 0.062(10) -0.079(10) C16 0.192(20) 0.555(53) 0.276(25) 0.130(26) 0.094(19) -0.042(24) C17 0.471(54) 0.288(29) 0.290(30) -0.023(23) -0.165(34) 0.097(32) C18 0.151(13) 0.365(27) 0.240(18) -0.053(17) 0.070(13) 0.020(14) O1 0.080(3) 0.110(4) 0.116(4) -0.026(3) -0.011(3) -0.009(3) O2 0.086(3) 0.108(4) 0.105(4) -0.003(3) 0.007(3) -0.013(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 C15 2.091(12) . ? Sn1 C7 2.103(10) . ? Sn1 C11 2.105(14) . ? Sn1 O1 2.340(5) . ? Sn1 N1 2.360(6) . ? N1 N3 1.319(8) . ? N1 N2 1.331(8) . ? N2 C1 1.332(8) . ? N3 N4 1.330(7) . ? N4 C1 1.327(8) . ? N5 C5 1.314(10) . ? N5 C6 1.315(9) . ? C1 C2 1.468(9) . ? C2 C4 1.348(9) . ? C2 C3 1.371(9) . ? C3 C5 1.391(11) . ? C4 C6 1.389(9) . ? C7 C8 1.46(2) . ? C8 C9 1.36(2) . ? C9 C10 1.40(2) . ? C11 C12 1.59(2) . ? C12 C13 1.35(2) . ? C13 C14 1.54(2) . ? C15 C16 1.45(2) . ? C16 C17 1.10(3) . ? C17 C18 1.54(3) . ? O1 O2 2.694(7) . ? O1 N5 2.760(8) 4_465 ? O2 N4 2.831(8) 4_565 ? O2 N3 2.923(8) 2_646 ? 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 C15 Sn1 C7 124.0(7) . . ? C15 Sn1 C11 115.2(7) . . ? C7 Sn1 C11 120.8(7) . . ? C15 Sn1 O1 89.3(4) . . ? C7 Sn1 O1 86.1(3) . . ? C11 Sn1 O1 92.1(5) . . ? C15 Sn1 N1 90.5(4) . . ? C7 Sn1 N1 91.4(3) . . ? C11 Sn1 N1 90.8(5) . . ? O1 Sn1 N1 176.9(2) . . ? N3 N1 N2 110.4(6) . . ? N3 N1 Sn1 125.6(5) . . ? N2 N1 Sn1 123.7(5) . . ? N1 N2 C1 103.9(6) . . ? N1 N3 N4 108.6(6) . . ? C1 N4 N3 105.1(6) . . ? C5 N5 C6 116.4(7) . . ? N4 C1 N2 112.1(6) . . ? N4 C1 C2 124.7(7) . . ? N2 C1 C2 123.2(6) . . ? C4 C2 C3 116.8(6) . . ? C4 C2 C1 122.9(6) . . ? C3 C2 C1 120.3(7) . . ? C2 C3 C5 119.1(8) . . ? C2 C4 C6 120.8(7) . . ? N5 C5 C3 124.0(8) . . ? N5 C6 C4 123.0(8) . . ? C8 C7 Sn1 115.6(11) . . ? C9 C8 C7 119.1(20) . . ? C8 C9 C10 110.6(25) . . ? C12 C11 Sn1 118.0(15) . . ? C13 C12 C11 98.3(21) . . ? C12 C13 C14 95.2(23) . . ? C16 C15 Sn1 127.1(13) . . ? C17 C16 C15 128.6(31) . . ? C16 C17 C18 125.8(39) . . ? Sn1 O1 O2 121.7(2) . . ? Sn1 O1 N5 125.1(2) . 4_465 ? O2 O1 N5 106.0(2) . 4_465 ? O1 O2 N4 116.2(2) . 4_565 ? O1 O2 N3 93.5(2) . 2_646 ? N4 O2 N3 118.4(2) 4_565 2_646 ? _refine_diff_density_max 0.480 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.070 data_95kcm9 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H19 N5 Sn' _chemical_formula_weight 352.01 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 8.2630(10) _cell_length_b 8.2630(10) _cell_length_c 38.991(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2305.5(5) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method ? _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.655 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3933 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 23.92 _reflns_number_total 1226 _reflns_number_observed 1090 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0273P)^2^+0.2266P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 1226 _refine_ls_number_parameters 169 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_obs 0.0188 _refine_ls_wR_factor_all 0.0467 _refine_ls_wR_factor_obs 0.0426 _refine_ls_goodness_of_fit_all 1.132 _refine_ls_goodness_of_fit_obs 1.107 _refine_ls_restrained_S_all 1.132 _refine_ls_restrained_S_obs 1.106 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn1 Sn 0.57212(5) 0.40118(4) 0.122350(10) 0.04491(13) Uani 1 d . . N1 N 0.3502(7) 0.1497(7) 0.08966(13) 0.0508(13) Uani 1 d . . N2 N 0.3903(7) 0.0391(8) 0.0721(2) 0.0642(14) Uani 1 d . . N3 N 0.2601(7) -0.0465(8) 0.04843(15) 0.0660(15) Uani 1 d . . N4 N 0.1927(7) 0.1388(7) 0.07835(13) 0.0519(12) Uani 1 d . . N5 N -0.3373(7) -0.1324(7) -0.00937(14) 0.0543(14) Uani 1 d . . C1 C 0.3706(9) 0.4853(9) 0.1330(2) 0.068(2) Uani 1 d . . H1A H 0.2479(9) 0.3844(9) 0.1266(2) 0.081 Uiso 1 calc R . H1B H 0.3691(9) 0.5044(9) 0.1575(2) 0.081 Uiso 1 calc R . C2 C 0.4042(19) 0.6562(18) 0.1153(5) 0.174(7) Uani 1 d . . H2A H 0.3528(167) 0.7176(100) 0.1286(17) 0.261 Uiso 1 calc R . H2B H 0.3455(163) 0.6244(27) 0.0931(15) 0.261 Uiso 1 calc R . H2C H 0.5362(20) 0.7382(85) 0.1125(32) 0.261 Uiso 1 calc R . C3 C 0.6201(10) 0.2171(10) 0.1535(2) 0.068(2) Uani 1 d . . H3A H 0.5699(10) 0.2135(10) 0.1762(2) 0.082 Uiso 1 calc R . H3B H 0.5497(10) 0.0924(10) 0.1439(2) 0.082 Uiso 1 calc R . C4 C 0.8133(17) 0.2628(20) 0.1573(5) 0.186(8) Uani 1 d . . H4A H 0.8708(60) 0.2848(197) 0.1351(5) 0.279 Uiso 1 calc R . H4B H 0.8173(20) 0.1607(88) 0.1682(34) 0.279 Uiso 1 calc R . H4C H 0.8793(54) 0.3731(121) 0.1711(31) 0.279 Uiso 1 calc R . C5 C 0.7339(13) 0.5205(11) 0.0773(2) 0.087(2) Uani 1 d . . H5A H 0.6487(13) 0.5207(11) 0.0602(2) 0.104 Uiso 1 calc R . H5B H 0.8207(13) 0.6504(11) 0.0826(2) 0.104 Uiso 1 calc R . C6 C 0.8307(29) 0.4579(18) 0.0620(6) 0.325(22) Uani 1 d . . H6A H 0.9231(309) 0.4624(440) 0.0775(29) 0.487 Uiso 1 calc R . H6B H 0.8915(386) 0.5338(292) 0.0423(50) 0.487 Uiso 1 calc R . H6C H 0.7494(71) 0.3312(162) 0.0549(77) 0.487 Uiso 1 calc R . C7 C 0.1422(8) 0.0167(8) 0.05255(15) 0.0458(12) Uani 1 d . . C8 C -0.0250(7) -0.0382(7) 0.03175(13) 0.0450(15) Uani 1 d . . C9 C -0.0444(8) -0.1179(9) -0.0005(2) 0.057(2) Uani 1 d . . H9 H 0.0463(8) -0.1432(9) -0.0087(2) 0.069 Uiso 1 calc R . C10 C -0.1973(8) -0.1588(10) -0.0199(2) 0.063(2) Uani 1 d . . H10 H -0.2052(8) -0.2077(10) -0.0418(2) 0.065(16) Uiso 1 calc R . C11 C -0.3209(9) -0.0617(9) 0.0216(2) 0.058(2) Uani 1 d . . H11 H -0.4172(9) -0.0447(9) 0.0298(2) 0.062(18) Uiso 1 calc R . C12 C -0.1680(9) -0.0115(8) 0.04274(15) 0.0543(14) Uani 1 d . . H12 H -0.1622(9) 0.0400(8) 0.06423(15) 0.065 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0450(2) 0.0415(2) 0.0460(2) -0.0009(2) -0.0027(2) 0.0199(2) N1 0.048(3) 0.056(3) 0.047(3) -0.007(2) -0.007(2) 0.025(3) N2 0.056(3) 0.070(3) 0.076(4) -0.025(3) -0.020(3) 0.038(3) N3 0.064(3) 0.077(4) 0.073(4) -0.029(3) -0.019(3) 0.048(3) N4 0.053(3) 0.054(3) 0.052(3) -0.010(2) -0.007(2) 0.029(2) N5 0.052(3) 0.062(3) 0.057(3) -0.010(2) -0.008(2) 0.034(3) C1 0.070(4) 0.065(4) 0.083(5) -0.019(3) -0.019(4) 0.044(3) C2 0.167(12) 0.131(9) 0.275(23) 0.076(12) 0.034(12) 0.114(10) C3 0.077(5) 0.065(4) 0.071(4) 0.007(3) -0.008(4) 0.042(3) C4 0.112(9) 0.170(12) 0.312(23) 0.069(13) -0.025(11) 0.098(9) C5 0.106(6) 0.067(5) 0.054(4) 0.008(4) 0.019(4) 0.019(5) C6 0.466(39) 0.109(10) 0.344(30) 0.064(12) 0.344(32) 0.103(14) C7 0.050(3) 0.039(3) 0.046(3) -0.003(2) -0.003(3) 0.020(3) C8 0.040(3) 0.037(3) 0.051(5) 0.000(3) -0.004(2) 0.015(2) C9 0.052(3) 0.072(4) 0.058(4) -0.015(3) -0.004(3) 0.039(3) C10 0.058(4) 0.088(5) 0.051(4) -0.024(3) -0.010(3) 0.043(4) C11 0.058(4) 0.079(4) 0.055(4) -0.006(3) 0.001(3) 0.048(3) C12 0.066(4) 0.065(3) 0.043(3) -0.012(3) -0.007(3) 0.041(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 C5 2.129(7) . ? Sn1 C3 2.133(7) . ? Sn1 C1 2.141(6) . ? Sn1 N1 2.344(5) . ? Sn1 N5 2.437(5) 6_665 ? N1 N2 1.310(7) . ? N1 N4 1.333(7) . ? N2 N3 1.323(7) . ? N3 C7 1.326(7) . ? N4 C7 1.335(7) . ? N5 C11 1.320(8) . ? N5 C10 1.344(8) . ? N5 Sn1 2.437(5) 5_454 ? C1 C2 1.468(13) . ? C3 C4 1.452(13) . ? C5 C6 1.29(2) . ? C7 C8 1.465(7) . ? C8 C12 1.374(8) . ? C8 C9 1.391(8) . ? C9 C10 1.363(8) . ? C11 C12 1.386(9) . ? 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 C5 Sn1 C3 120.2(3) . . ? C5 Sn1 C1 114.8(3) . . ? C3 Sn1 C1 125.0(3) . . ? C5 Sn1 N1 89.6(3) . . ? C3 Sn1 N1 91.1(2) . . ? C1 Sn1 N1 90.1(2) . . ? C5 Sn1 N5 91.7(3) . 6_665 ? C3 Sn1 N5 89.2(2) . 6_665 ? C1 Sn1 N5 88.3(2) . 6_665 ? N1 Sn1 N5 178.2(2) . 6_665 ? N2 N1 N4 111.0(5) . . ? N2 N1 Sn1 122.9(4) . . ? N4 N1 Sn1 123.0(4) . . ? N1 N2 N3 108.4(4) . . ? N2 N3 C7 105.4(5) . . ? N1 N4 C7 103.1(5) . . ? C11 N5 C10 116.5(5) . . ? C11 N5 Sn1 117.3(4) . 5_454 ? C10 N5 Sn1 125.9(4) . 5_454 ? C2 C1 Sn1 114.7(6) . . ? C4 C3 Sn1 116.4(7) . . ? C6 C5 Sn1 124.4(9) . . ? N3 C7 N4 112.0(5) . . ? N3 C7 C8 125.2(5) . . ? N4 C7 C8 122.8(5) . . ? C12 C8 C9 116.9(5) . . ? C12 C8 C7 122.1(5) . . ? C9 C8 C7 121.0(5) . . ? C10 C9 C8 119.5(5) . . ? N5 C10 C9 123.8(6) . . ? N5 C11 C12 123.6(6) . . ? C8 C12 C11 119.6(5) . . ? _refine_diff_density_max 0.276 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.050 data_96kcm1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H21 N5 O Sn' _chemical_formula_weight 370.03 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' 'Sn' 'Sn' -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z' 'x-1/2, y, -z-1/2' _cell_length_a 13.781(2) _cell_length_b 14.764(2) _cell_length_c 16.227(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3301.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method ? _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.549 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2589 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 23.91 _reflns_number_total 2589 _reflns_number_observed 1858 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+4.1402P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2582 _refine_ls_number_parameters 184 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_obs 0.0450 _refine_ls_wR_factor_all 0.1351 _refine_ls_wR_factor_obs 0.1097 _refine_ls_goodness_of_fit_all 1.135 _refine_ls_goodness_of_fit_obs 1.116 _refine_ls_restrained_S_all 1.148 _refine_ls_restrained_S_obs 1.116 _refine_ls_shift/esd_max 0.191 _refine_ls_shift/esd_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Sn1 Sn 0.03388(4) 0.21565(3) 0.21725(3) 0.0691(3) Uani 1 d . . O1 O 0.1599(4) 0.1176(3) 0.2549(3) 0.0748(12) Uani 1 d D . H1A H 0.1662(45) 0.0596(24) 0.2302(32) 0.067(18) Uiso 1 d D . H1B H 0.1719(43) 0.1060(38) 0.3133(19) 0.064(17) Uiso 1 d D . N1 N -0.0870(5) 0.3196(4) 0.1828(3) 0.077(2) Uani 1 d . . N2 N -0.1393(4) 0.3216(4) 0.1136(3) 0.0735(15) Uani 1 d . . N3 N -0.1612(4) 0.4458(3) 0.1867(3) 0.0677(14) Uani 1 d . . N4 N -0.0996(5) 0.3920(4) 0.2275(3) 0.074(2) Uani 1 d . . N5 N -0.3170(4) 0.4248(4) -0.0807(3) 0.0717(14) Uani 1 d . . C1 C -0.1846(4) 0.4011(4) 0.1180(4) 0.0574(14) Uani 1 d . . C2 C -0.2498(4) 0.4365(4) 0.0547(3) 0.0579(15) Uani 1 d . . C3 C -0.3034(5) 0.5150(5) 0.0677(4) 0.081(2) Uani 1 d . . H3 H -0.2992(5) 0.5457(5) 0.1176(4) 0.097 Uiso 1 calc R . C4 C -0.3627(6) 0.5467(5) 0.0062(5) 0.093(2) Uani 1 d . . H4 H -0.3997(6) 0.5987(5) 0.0137(5) 0.112 Uiso 1 calc R . C5 C -0.3660(5) 0.5003(6) -0.0659(5) 0.085(2) Uani 1 d . . H5 H -0.4052(5) 0.5229(6) -0.1077(5) 0.102 Uiso 1 calc R . C6 C -0.2604(5) 0.3940(4) -0.0204(3) 0.0609(15) Uani 1 d . . H6 H -0.2260(5) 0.3407(4) -0.0295(3) 0.073 Uiso 1 calc R . C7 C -0.0027(10) 0.2365(10) 0.3504(8) 0.151(4) Uani 1 d . . H7A H -0.0684(10) 0.2592(10) 0.3564(8) 0.181 Uiso 1 calc R . H7B H 0.0031(10) 0.1801(10) 0.3808(8) 0.181 Uiso 1 calc R . C8 C 0.0620(11) 0.2976(9) 0.3778(14) 0.222(10) Uani 1 d . . H8A H 0.1071(74) 0.2686(26) 0.4143(82) 0.333 Uiso 1 calc R . H8B H 0.0286(17) 0.3450(60) 0.4068(89) 0.333 Uiso 1 calc R . H8C H 0.0964(84) 0.3230(81) 0.3318(16) 0.333 Uiso 1 calc R . C9 C -0.0532(14) 0.0987(11) 0.1711(13) 0.237(11) Uani 1 d . . H9A H -0.0426(14) 0.0459(11) 0.2055(13) 0.285 Uiso 1 calc R . H9B H -0.1218(14) 0.1133(11) 0.1719(13) 0.285 Uiso 1 calc R . C10 C -0.0229(16) 0.0817(16) 0.0911(19) 0.333(18) Uani 1 d . . H10A H -0.0592(169) 0.1188(163) 0.0536(25) 0.499 Uiso 1 calc R . H10B H -0.0334(218) 0.0190(53) 0.0783(71) 0.499 Uiso 1 calc R . H10C H 0.0449(59) 0.0955(210) 0.0862(56) 0.499 Uiso 1 calc R . C11 C 0.1299(14) 0.2853(17) 0.1475(18) 0.366(22) Uani 1 d . . H11A H 0.0888(14) 0.2891(17) 0.0990(18) 0.439 Uiso 1 calc R . H11B H 0.1198(14) 0.3432(17) 0.1744(18) 0.439 Uiso 1 calc R . C12 C 0.1880(21) 0.3018(26) 0.1204(18) 0.468(28) Uani 1 d . . H12A H 0.1738(63) 0.3445(315) 0.0774(253) 0.702 Uiso 1 calc R . H12B H 0.2176(229) 0.2488(63) 0.0970(324) 0.702 Uiso 1 calc R . H12C H 0.2317(179) 0.3288(386) 0.1594(83) 0.702 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.0897(4) 0.0627(3) 0.0548(3) -0.0063(2) -0.0124(2) 0.0108(2) O1 0.103(3) 0.057(3) 0.065(3) -0.003(2) -0.016(3) 0.017(3) N1 0.102(4) 0.065(3) 0.065(3) -0.006(3) -0.016(3) 0.023(3) N2 0.095(4) 0.068(3) 0.057(3) -0.003(3) -0.014(3) 0.016(3) N3 0.083(4) 0.063(3) 0.057(3) -0.009(3) -0.012(3) 0.006(3) N4 0.095(4) 0.068(3) 0.060(3) -0.005(3) -0.018(3) 0.012(3) N5 0.081(4) 0.071(4) 0.064(3) -0.001(3) -0.009(3) 0.000(3) C1 0.062(3) 0.051(3) 0.059(3) -0.003(3) -0.004(3) -0.001(3) C2 0.063(4) 0.052(3) 0.058(3) -0.002(3) -0.001(3) 0.002(3) C3 0.097(5) 0.074(5) 0.072(4) -0.008(3) -0.003(4) 0.018(4) C4 0.102(6) 0.081(5) 0.096(6) -0.012(5) -0.018(5) 0.041(4) C5 0.085(5) 0.078(5) 0.091(5) 0.013(4) -0.023(4) 0.007(4) C6 0.069(4) 0.056(3) 0.058(3) 0.001(3) -0.005(3) -0.003(3) C7 0.132(8) 0.175(12) 0.145(10) 0.053(9) -0.015(9) 0.039(9) C8 0.177(13) 0.135(11) 0.354(27) -0.059(13) -0.141(16) 0.048(10) C9 0.264(20) 0.187(15) 0.262(19) -0.108(15) -0.168(18) 0.140(14) C10 0.268(24) 0.295(25) 0.435(40) -0.181(28) -0.203(29) 0.150(21) C11 0.176(15) 0.385(32) 0.537(44) 0.358(34) 0.174(23) 0.089(18) C12 0.353(36) 0.686(69) 0.364(35) 0.033(37) 0.153(30) -0.312(43) _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 C11 2.022(15) . ? Sn1 C9 2.23(2) . ? Sn1 C7 2.240(14) . ? Sn1 N1 2.333(6) . ? Sn1 O1 2.342(4) . ? N1 N4 1.303(7) . ? N1 N2 1.335(7) . ? N2 C1 1.331(7) . ? N3 C1 1.334(7) . ? N3 N4 1.338(7) . ? N5 C5 1.325(9) . ? N5 C6 1.331(7) . ? C1 C2 1.463(8) . ? C2 C6 1.379(8) . ? C2 C3 1.390(9) . ? C3 C4 1.371(9) . ? C4 C5 1.357(10) . ? C7 C8 1.34(2) . ? C9 C10 1.39(3) . ? C11 C12 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Sn1 C9 123.8(12) . . ? C11 Sn1 C7 128.2(11) . . ? C9 Sn1 C7 108.0(8) . . ? C11 Sn1 N1 89.9(5) . . ? C9 Sn1 N1 92.6(4) . . ? C7 Sn1 N1 88.8(3) . . ? C11 Sn1 O1 88.6(5) . . ? C9 Sn1 O1 90.5(4) . . ? C7 Sn1 O1 90.0(3) . . ? N1 Sn1 O1 177.0(2) . . ? N4 N1 N2 112.2(5) . . ? N4 N1 Sn1 120.1(4) . . ? N2 N1 Sn1 127.0(4) . . ? C1 N2 N1 103.1(5) . . ? C1 N3 N4 105.8(5) . . ? N1 N4 N3 107.2(5) . . ? C5 N5 C6 116.9(6) . . ? N2 C1 N3 111.6(5) . . ? N2 C1 C2 124.4(5) . . ? N3 C1 C2 123.9(5) . . ? C6 C2 C3 117.2(6) . . ? C6 C2 C1 121.5(5) . . ? C3 C2 C1 121.2(5) . . ? C4 C3 C2 119.4(6) . . ? C5 C4 C3 118.3(7) . . ? N5 C5 C4 124.4(7) . . ? N5 C6 C2 123.7(6) . . ? C8 C7 Sn1 105.2(13) . . ? C10 C9 Sn1 107.0(19) . . ? C12 C11 Sn1 161.0(31) . . ? _refine_diff_density_max 0.639 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.095