data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.Dickschat S.Urban T.Pape F.Glorius E.Hahn _publ_contact_author_name 'Hahn, Ekkehardt' _publ_contact_author_email fehahn@uni-muenster.de # Attachment '- cif-2.cif' data_cif-2 _database_code_depnum_ccdc_archive 'CCDC 793577' #TrackingRef '- cif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N2 Sn' _chemical_formula_weight 461.16 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4015(3) _cell_length_b 11.3645(3) _cell_length_c 21.6208(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.3800(4) _cell_angle_gamma 90.00 _cell_volume 2063.73(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent rhombus' _exptl_crystal_colour gold-orange _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6982 _exptl_absorpt_correction_T_max 0.8545 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.834630 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24333 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 30.50 _reflns_number_total 6277 _reflns_number_gt 5589 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.9414P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6277 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0599 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.58850(17) 0.41145(13) 0.22068(7) 0.0193(3) Uani 1 1 d . . . C2 C 0.66222(18) 0.44748(13) 0.16502(7) 0.0191(3) Uani 1 1 d . . . C3 C 0.7262(2) 0.36188(15) 0.12648(7) 0.0236(3) Uani 1 1 d . . . H3 H 0.7784 0.3850 0.0899 0.028 Uiso 1 1 calc R . . C4 C 0.7142(2) 0.24305(14) 0.14112(8) 0.0269(3) Uani 1 1 d . . . H4 H 0.7602 0.1858 0.1150 0.032 Uiso 1 1 calc R . . C5 C 0.6352(2) 0.20759(14) 0.19380(8) 0.0264(3) Uani 1 1 d . . . H5 H 0.6238 0.1262 0.2027 0.032 Uiso 1 1 calc R . . C6 C 0.57276(19) 0.29162(14) 0.23352(7) 0.0233(3) Uani 1 1 d . . . H6 H 0.5192 0.2672 0.2695 0.028 Uiso 1 1 calc R . . C7 C 0.45070(18) 0.47230(13) 0.31284(7) 0.0192(3) Uani 1 1 d . . . C8 C 0.28345(19) 0.47609(14) 0.31187(7) 0.0233(3) Uani 1 1 d . . . C9 C 0.2035(2) 0.45521(15) 0.36632(8) 0.0278(3) Uani 1 1 d . . . H9 H 0.0905 0.4577 0.3659 0.033 Uiso 1 1 calc R . . C10 C 0.2858(2) 0.43070(15) 0.42149(7) 0.0280(3) Uani 1 1 d . . . C11 C 0.4502(2) 0.42245(14) 0.42077(7) 0.0259(3) Uani 1 1 d . . . H11 H 0.5068 0.4033 0.4580 0.031 Uiso 1 1 calc R . . C12 C 0.53546(19) 0.44144(13) 0.36695(7) 0.0215(3) Uani 1 1 d . . . C13 C 0.1908(2) 0.50109(19) 0.25272(8) 0.0341(4) Uani 1 1 d . . . H13A H 0.0803 0.4755 0.2571 0.051 Uiso 1 1 calc R . . H13B H 0.2388 0.4583 0.2185 0.051 Uiso 1 1 calc R . . H13C H 0.1932 0.5857 0.2441 0.051 Uiso 1 1 calc R . . C14 C 0.1972(3) 0.4150(2) 0.48075(9) 0.0450(5) Uani 1 1 d . . . H14A H 0.2621 0.3683 0.5100 0.068 Uiso 1 1 calc R . . H14B H 0.0964 0.3742 0.4720 0.068 Uiso 1 1 calc R . . H14C H 0.1756 0.4922 0.4989 0.068 Uiso 1 1 calc R . . C15 C 0.7133(2) 0.42443(15) 0.36776(8) 0.0261(3) Uani 1 1 d . . . H15A H 0.7476 0.4039 0.3261 0.039 Uiso 1 1 calc R . . H15B H 0.7423 0.3609 0.3965 0.039 Uiso 1 1 calc R . . H15C H 0.7657 0.4974 0.3812 0.039 Uiso 1 1 calc R . . C16 C 0.70081(18) 0.60757(13) 0.09273(7) 0.0190(3) Uani 1 1 d . . . C17 C 0.85959(18) 0.62032(13) 0.07573(7) 0.0208(3) Uani 1 1 d . . . C18 C 0.8914(2) 0.65933(14) 0.01588(7) 0.0239(3) Uani 1 1 d . . . H18 H 0.9990 0.6664 0.0039 0.029 Uiso 1 1 calc R . . C19 C 0.7711(2) 0.68807(14) -0.02659(7) 0.0247(3) Uani 1 1 d . . . C20 C 0.6147(2) 0.67483(14) -0.00855(8) 0.0252(3) Uani 1 1 d . . . H20 H 0.5309 0.6942 -0.0370 0.030 Uiso 1 1 calc R . . C21 C 0.57671(18) 0.63386(14) 0.05027(7) 0.0221(3) Uani 1 1 d . . . C22 C 0.9952(2) 0.59371(17) 0.12009(8) 0.0292(3) Uani 1 1 d . . . H22A H 0.9531 0.5654 0.1593 0.044 Uiso 1 1 calc R . . H22B H 1.0577 0.6653 0.1276 0.044 Uiso 1 1 calc R . . H22C H 1.0634 0.5330 0.1024 0.044 Uiso 1 1 calc R . . C23 C 0.8085(3) 0.73178(18) -0.09069(8) 0.0364(4) Uani 1 1 d . . . H23A H 0.8422 0.8142 -0.0884 0.055 Uiso 1 1 calc R . . H23B H 0.7132 0.7253 -0.1175 0.055 Uiso 1 1 calc R . . H23C H 0.8943 0.6841 -0.1077 0.055 Uiso 1 1 calc R . . C24 C 0.4048(2) 0.61714(18) 0.06676(9) 0.0312(4) Uani 1 1 d . . . H24A H 0.3710 0.6825 0.0929 0.047 Uiso 1 1 calc R . . H24B H 0.3932 0.5428 0.0892 0.047 Uiso 1 1 calc R . . H24C H 0.3386 0.6152 0.0288 0.047 Uiso 1 1 calc R . . N1 N 0.53269(16) 0.50139(11) 0.25756(6) 0.0203(2) Uani 1 1 d . . . N2 N 0.66059(16) 0.56764(11) 0.15335(6) 0.0202(2) Uani 1 1 d . . . Sn1 Sn 0.560669(13) 0.670251(9) 0.222550(5) 0.02266(4) Uani 1 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 C1 0.0220(7) 0.0183(6) 0.0177(6) 0.0005(5) 0.0026(5) 0.0006(5) C2 0.0220(7) 0.0185(6) 0.0168(6) 0.0002(5) 0.0023(5) 0.0016(5) C3 0.0293(8) 0.0245(7) 0.0171(6) -0.0018(6) 0.0047(6) 0.0023(6) C4 0.0376(9) 0.0212(7) 0.0220(7) -0.0049(6) 0.0046(6) 0.0049(6) C5 0.0369(9) 0.0173(7) 0.0249(8) -0.0011(6) 0.0027(6) 0.0009(6) C6 0.0283(8) 0.0199(7) 0.0217(7) 0.0012(6) 0.0033(6) -0.0003(6) C7 0.0244(7) 0.0168(6) 0.0168(6) 0.0005(5) 0.0061(5) 0.0020(5) C8 0.0253(7) 0.0234(7) 0.0215(7) 0.0000(6) 0.0044(6) 0.0014(6) C9 0.0269(8) 0.0299(8) 0.0272(8) -0.0026(6) 0.0104(6) -0.0001(6) C10 0.0395(9) 0.0250(8) 0.0201(7) -0.0017(6) 0.0118(6) -0.0031(7) C11 0.0399(9) 0.0219(7) 0.0161(7) 0.0005(6) 0.0025(6) 0.0003(6) C12 0.0276(7) 0.0168(6) 0.0201(7) -0.0008(5) 0.0020(6) 0.0016(6) C13 0.0268(8) 0.0459(11) 0.0294(8) 0.0037(8) -0.0010(7) 0.0033(8) C14 0.0577(13) 0.0514(12) 0.0270(9) -0.0028(9) 0.0216(9) -0.0084(10) C15 0.0289(8) 0.0231(7) 0.0264(8) 0.0002(6) -0.0012(6) 0.0046(6) C16 0.0224(7) 0.0179(6) 0.0170(6) 0.0005(5) 0.0044(5) 0.0007(5) C17 0.0212(7) 0.0210(7) 0.0202(7) 0.0006(5) 0.0024(5) 0.0012(5) C18 0.0238(7) 0.0246(7) 0.0238(7) 0.0003(6) 0.0086(6) 0.0001(6) C19 0.0340(8) 0.0210(7) 0.0193(7) 0.0018(6) 0.0057(6) 0.0023(6) C20 0.0279(8) 0.0263(8) 0.0211(7) 0.0029(6) -0.0012(6) 0.0053(6) C21 0.0211(7) 0.0222(7) 0.0232(7) 0.0001(6) 0.0028(6) 0.0010(6) C22 0.0220(7) 0.0370(9) 0.0286(8) 0.0014(7) -0.0004(6) 0.0030(7) C23 0.0502(11) 0.0356(10) 0.0238(8) 0.0090(7) 0.0121(8) 0.0076(8) C24 0.0213(8) 0.0395(10) 0.0327(9) 0.0021(7) 0.0018(6) -0.0012(7) N1 0.0264(6) 0.0179(6) 0.0169(5) 0.0007(5) 0.0080(5) 0.0020(5) N2 0.0256(6) 0.0172(6) 0.0182(6) 0.0024(5) 0.0062(5) 0.0012(5) Sn1 0.03018(6) 0.01646(6) 0.02173(6) 0.00139(4) 0.00848(4) 0.00361(4) _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 C1 N1 1.3850(19) . ? C1 C6 1.397(2) . ? C1 C2 1.427(2) . ? C2 N2 1.3886(19) . ? C2 C3 1.397(2) . ? C3 C4 1.391(2) . ? C4 C5 1.391(2) . ? C5 C6 1.395(2) . ? C7 C12 1.400(2) . ? C7 C8 1.406(2) . ? C7 N1 1.4324(18) . ? C8 C9 1.390(2) . ? C8 C13 1.508(2) . ? C9 C10 1.392(3) . ? C10 C11 1.385(3) . ? C10 C14 1.508(2) . ? C11 C12 1.398(2) . ? C12 C15 1.506(2) . ? C16 C17 1.400(2) . ? C16 C21 1.405(2) . ? C16 N2 1.4351(18) . ? C17 C18 1.400(2) . ? C17 C22 1.503(2) . ? C18 C19 1.388(2) . ? C19 C20 1.388(2) . ? C19 C23 1.512(2) . ? C20 C21 1.398(2) . ? C21 C24 1.508(2) . ? N1 Sn1 2.0783(13) . ? N2 Sn1 2.0890(12) . ? 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 N1 C1 C6 124.76(13) . . ? N1 C1 C2 115.70(13) . . ? C6 C1 C2 119.51(13) . . ? N2 C2 C3 125.35(14) . . ? N2 C2 C1 115.66(13) . . ? C3 C2 C1 118.97(14) . . ? C4 C3 C2 120.61(14) . . ? C3 C4 C5 120.39(14) . . ? C4 C5 C6 119.96(15) . . ? C5 C6 C1 120.42(14) . . ? C12 C7 C8 120.57(14) . . ? C12 C7 N1 120.67(14) . . ? C8 C7 N1 118.76(13) . . ? C9 C8 C7 119.05(15) . . ? C9 C8 C13 120.04(15) . . ? C7 C8 C13 120.91(14) . . ? C8 C9 C10 121.31(16) . . ? C11 C10 C9 118.61(14) . . ? C11 C10 C14 120.95(17) . . ? C9 C10 C14 120.44(17) . . ? C10 C11 C12 122.01(15) . . ? C11 C12 C7 118.30(15) . . ? C11 C12 C15 119.90(14) . . ? C7 C12 C15 121.77(14) . . ? C17 C16 C21 120.24(13) . . ? C17 C16 N2 121.29(13) . . ? C21 C16 N2 118.47(13) . . ? C18 C17 C16 118.67(14) . . ? C18 C17 C22 119.69(14) . . ? C16 C17 C22 121.64(14) . . ? C19 C18 C17 122.30(15) . . ? C18 C19 C20 117.88(14) . . ? C18 C19 C23 121.33(16) . . ? C20 C19 C23 120.80(16) . . ? C19 C20 C21 122.01(15) . . ? C20 C21 C16 118.87(14) . . ? C20 C21 C24 119.86(15) . . ? C16 C21 C24 121.26(14) . . ? C1 N1 C7 119.10(12) . . ? C1 N1 Sn1 115.40(9) . . ? C7 N1 Sn1 125.30(9) . . ? C2 N2 C16 118.40(12) . . ? C2 N2 Sn1 114.90(9) . . ? C16 N2 Sn1 125.81(10) . . ? N1 Sn1 N2 78.25(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.410 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.070 data_sad _database_code_depnum_ccdc_archive 'CCDC 793578' #TrackingRef '- cif-R,R-5-edited.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N2 Sn' _chemical_formula_weight 433.11 _chemical_absolute_configuration R,R 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8101(5) _cell_length_b 9.2801(6) _cell_length_c 26.2554(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1903.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent stick' _exptl_crystal_colour 'intense yellow' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.349 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8769 _exptl_absorpt_correction_T_max 0.9480 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.781203 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23451 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 31.08 _reflns_number_total 5906 _reflns_number_gt 5216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2(Bruker AXS, 2007)' _computing_cell_refinement 'APEX2(Bruker AXS, 2007)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2007 )' _computing_structure_solution ; SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_structure_refinement ; SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122 ; _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+0.3951P] 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 noref _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 -0.004(19) _refine_ls_number_reflns 5906 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.37318(3) 0.540208(19) 0.777014(7) 0.02773(5) Uani 1 1 d . . . N1 N 0.3526(3) 0.7396(2) 0.81192(7) 0.0209(4) Uani 1 1 d . . . N2 N 0.2586(3) 0.6603(2) 0.72009(8) 0.0197(4) Uani 1 1 d . . . C1 C 0.2799(3) 0.8465(2) 0.78187(9) 0.0186(4) Uani 1 1 d . . . C2 C 0.2298(3) 0.8038(2) 0.73180(9) 0.0177(5) Uani 1 1 d . . . C3 C 0.1596(3) 0.9066(3) 0.69902(9) 0.0221(5) Uani 1 1 d . . . H3 H 0.1262 0.8791 0.6656 0.027 Uiso 1 1 calc R . . C4 C 0.1380(3) 1.0485(3) 0.71450(9) 0.0232(5) Uani 1 1 d . . . H4 H 0.0895 1.1169 0.6918 0.028 Uiso 1 1 calc R . . C5 C 0.1872(3) 1.0906(3) 0.76311(10) 0.0236(5) Uani 1 1 d . . . H5 H 0.1736 1.1880 0.7735 0.028 Uiso 1 1 calc R . . C6 C 0.2560(3) 0.9905(3) 0.79651(9) 0.0217(5) Uani 1 1 d . . . H6 H 0.2876 1.0199 0.8299 0.026 Uiso 1 1 calc R . . C7 C 0.3995(3) 0.7740(3) 0.86472(9) 0.0220(5) Uani 1 1 d . . . H7 H 0.4543 0.8713 0.8649 0.026 Uiso 1 1 calc R . . C8 C 0.5298(4) 0.6660(3) 0.88478(11) 0.0292(6) Uani 1 1 d . . . H8A H 0.4776 0.5701 0.8863 0.044 Uiso 1 1 calc R . . H8B H 0.5667 0.6949 0.9190 0.044 Uiso 1 1 calc R . . H8C H 0.6291 0.6635 0.8620 0.044 Uiso 1 1 calc R . . C9 C 0.2446(3) 0.7796(3) 0.89984(9) 0.0208(5) Uani 1 1 d . . . C10 C 0.1268(4) 0.6669(3) 0.90226(9) 0.0279(5) Uani 1 1 d . . . H10 H 0.1381 0.5871 0.8799 0.034 Uiso 1 1 calc R . . C11 C -0.0068(4) 0.6704(4) 0.93714(12) 0.0351(7) Uani 1 1 d . . . H11 H -0.0863 0.5930 0.9384 0.042 Uiso 1 1 calc R . . C12 C -0.0248(4) 0.7847(4) 0.96977(11) 0.0373(7) Uani 1 1 d . . . H12 H -0.1167 0.7865 0.9934 0.045 Uiso 1 1 calc R . . C13 C 0.0909(4) 0.8973(3) 0.96819(10) 0.0337(7) Uani 1 1 d . . . H13 H 0.0792 0.9765 0.9909 0.040 Uiso 1 1 calc R . . C14 C 0.2247(4) 0.8939(3) 0.93324(10) 0.0271(6) Uani 1 1 d . . . H14 H 0.3040 0.9715 0.9323 0.032 Uiso 1 1 calc R . . C15 C 0.2015(3) 0.6034(3) 0.67102(9) 0.0213(5) Uani 1 1 d . . . H15 H 0.0850 0.6437 0.6642 0.026 Uiso 1 1 calc R . . C16 C 0.1834(4) 0.4392(3) 0.67509(11) 0.0289(6) Uani 1 1 d . . . H16A H 0.2955 0.3964 0.6824 0.043 Uiso 1 1 calc R . . H16B H 0.1397 0.4008 0.6428 0.043 Uiso 1 1 calc R . . H16C H 0.1035 0.4154 0.7026 0.043 Uiso 1 1 calc R . . C17 C 0.3163(3) 0.6461(3) 0.62635(9) 0.0216(5) Uani 1 1 d . . . C18 C 0.2691(4) 0.6050(4) 0.57740(11) 0.0394(7) Uani 1 1 d . . . H18 H 0.1650 0.5540 0.5725 0.047 Uiso 1 1 calc R . . C19 C 0.3702(5) 0.6366(4) 0.53583(10) 0.0472(8) Uani 1 1 d . . . H19 H 0.3369 0.6050 0.5029 0.057 Uiso 1 1 calc R . . C20 C 0.5197(5) 0.7140(4) 0.54204(13) 0.0462(9) Uani 1 1 d . . . H20 H 0.5887 0.7378 0.5134 0.055 Uiso 1 1 calc R . . C21 C 0.5679(4) 0.7567(3) 0.59058(12) 0.0381(7) Uani 1 1 d . . . H21 H 0.6704 0.8101 0.5953 0.046 Uiso 1 1 calc R . . C22 C 0.4671(4) 0.7219(3) 0.63230(10) 0.0265(6) Uani 1 1 d . . . H22 H 0.5023 0.7506 0.6654 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sn1 0.03822(9) 0.02093(7) 0.02405(8) 0.00338(7) 0.00255(9) 0.00872(9) N1 0.0246(11) 0.0212(9) 0.0168(9) 0.0028(7) 0.0006(8) 0.0021(9) N2 0.0240(10) 0.0160(8) 0.0192(9) -0.0005(8) 0.0004(9) 0.0011(7) C1 0.0174(10) 0.0192(10) 0.0191(11) 0.0027(9) 0.0034(9) 0.0007(8) C2 0.0173(10) 0.0175(10) 0.0184(12) 0.0034(9) 0.0026(9) 0.0003(8) C3 0.0235(14) 0.0240(11) 0.0189(11) 0.0038(9) 0.0023(9) -0.0010(9) C4 0.0224(11) 0.0219(10) 0.0253(12) 0.0067(10) 0.0018(11) 0.0023(12) C5 0.0266(12) 0.0171(10) 0.0269(13) 0.0003(9) 0.0052(10) -0.0003(9) C6 0.0245(12) 0.0211(12) 0.0194(11) -0.0012(9) 0.0036(9) -0.0033(9) C7 0.0208(13) 0.0281(12) 0.0172(10) 0.0018(9) 0.0025(9) 0.0008(10) C8 0.0249(14) 0.0398(16) 0.0230(13) 0.0066(12) -0.0013(11) 0.0046(12) C9 0.0191(12) 0.0280(13) 0.0152(11) 0.0063(10) -0.0012(9) -0.0005(10) C10 0.0266(12) 0.0323(13) 0.0249(12) 0.0046(10) 0.0027(13) -0.0052(13) C11 0.0250(14) 0.0446(17) 0.0356(16) 0.0141(14) 0.0009(12) -0.0072(13) C12 0.0313(16) 0.056(2) 0.0245(14) 0.0138(14) 0.0071(12) 0.0078(15) C13 0.0410(19) 0.0385(15) 0.0217(13) 0.0035(11) 0.0030(11) 0.0116(13) C14 0.0295(14) 0.0310(14) 0.0207(12) 0.0038(11) -0.0004(11) 0.0021(12) C15 0.0225(12) 0.0208(11) 0.0207(12) -0.0032(10) 0.0018(10) -0.0022(10) C16 0.0290(13) 0.0200(13) 0.0376(15) -0.0084(11) 0.0050(11) -0.0041(10) C17 0.0222(12) 0.0217(12) 0.0208(12) 0.0007(10) 0.0015(9) 0.0049(9) C18 0.0334(16) 0.057(2) 0.0275(15) -0.0049(14) -0.0054(13) 0.0011(15) C19 0.053(2) 0.068(2) 0.0197(13) 0.0018(13) 0.0020(16) 0.016(2) C20 0.058(2) 0.045(2) 0.0357(18) 0.0142(15) 0.0194(17) 0.0200(17) C21 0.0393(17) 0.0237(13) 0.0514(19) 0.0030(13) 0.0169(14) -0.0008(12) C22 0.0337(15) 0.0200(12) 0.0258(13) -0.0014(10) 0.0041(11) -0.0023(11) _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 N2 2.068(2) . ? Sn1 N1 2.071(2) . ? N1 C1 1.389(3) . ? N1 C7 1.469(3) . ? N2 C2 1.386(3) . ? N2 C15 1.462(3) . ? C1 C6 1.403(3) . ? C1 C2 1.428(3) . ? C2 C3 1.397(3) . ? C3 C4 1.388(4) . ? C4 C5 1.389(3) . ? C5 C6 1.386(4) . ? C7 C9 1.522(3) . ? C7 C8 1.522(4) . ? C9 C14 1.385(4) . ? C9 C10 1.395(4) . ? C10 C11 1.389(4) . ? C11 C12 1.371(5) . ? C12 C13 1.382(5) . ? C13 C14 1.391(4) . ? C15 C17 1.528(3) . ? C15 C16 1.535(4) . ? C17 C22 1.381(4) . ? C17 C18 1.390(4) . ? C18 C19 1.378(5) . ? C19 C20 1.381(6) . ? C20 C21 1.386(5) . ? C21 C22 1.387(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Sn1 N1 78.75(8) . . ? C1 N1 C7 118.9(2) . . ? C1 N1 Sn1 114.75(15) . . ? C7 N1 Sn1 126.32(15) . . ? C2 N2 C15 119.5(2) . . ? C2 N2 Sn1 115.33(16) . . ? C15 N2 Sn1 125.07(15) . . ? N1 C1 C6 125.4(2) . . ? N1 C1 C2 115.9(2) . . ? C6 C1 C2 118.7(2) . . ? N2 C2 C3 125.7(2) . . ? N2 C2 C1 115.3(2) . . ? C3 C2 C1 119.0(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C5 120.2(2) . . ? C6 C5 C4 120.0(2) . . ? C5 C6 C1 121.1(2) . . ? N1 C7 C9 112.4(2) . . ? N1 C7 C8 110.5(2) . . ? C9 C7 C8 110.2(2) . . ? C14 C9 C10 118.1(2) . . ? C14 C9 C7 120.0(2) . . ? C10 C9 C7 121.7(2) . . ? C11 C10 C9 120.6(3) . . ? C12 C11 C10 120.5(3) . . ? C11 C12 C13 120.0(3) . . ? C12 C13 C14 119.6(3) . . ? C9 C14 C13 121.3(3) . . ? N2 C15 C17 113.8(2) . . ? N2 C15 C16 109.0(2) . . ? C17 C15 C16 111.4(2) . . ? C22 C17 C18 118.0(3) . . ? C22 C17 C15 123.1(2) . . ? C18 C17 C15 118.9(2) . . ? C19 C18 C17 121.5(3) . . ? C18 C19 C20 120.1(3) . . ? C19 C20 C21 119.1(3) . . ? C20 C21 C22 120.4(3) . . ? C17 C22 C21 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 31.08 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.542 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.075