# 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_sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 N2' _chemical_formula_weight 376.57 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' _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 11.7125(6) _cell_length_b 6.5108(3) _cell_length_c 27.4895(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.9330(10) _cell_angle_gamma 90.00 _cell_volume 2050.99(17) _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 needle' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9895 _exptl_absorpt_correction_T_max 0.9986 _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 = 0.904775 ; _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 20971 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.52 _reflns_number_total 5193 _reflns_number_gt 3861 _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. The maximum residual electron density was determined to be 0.746 e/cub Ang (minimum residual electron density -0.689 e/cub Ang). Te maximum and minimum electron densities are located 0.97 Ang from atom N1 and 0.94 Ang from Atom N2, respectively. These peaks cannot be assigned meanigfully to any chemical entity. ; _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^)+(0.0892P)^2^+0.8118P] 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 5193 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.55136(13) 0.7493(2) 0.20341(6) 0.0177(3) Uani 1 1 d . . . C2 C 0.59504(13) 0.5965(2) 0.17519(6) 0.0177(3) Uani 1 1 d . . . C3 C 0.64219(14) 0.4172(3) 0.19961(6) 0.0209(3) Uani 1 1 d . . . H3 H 0.6688 0.3105 0.1811 0.025 Uiso 1 1 calc R . . C4 C 0.65054(14) 0.3934(3) 0.25052(6) 0.0237(4) Uani 1 1 d . . . H4 H 0.6828 0.2709 0.2664 0.028 Uiso 1 1 calc R . . C5 C 0.61238(14) 0.5463(3) 0.27814(6) 0.0251(4) Uani 1 1 d . . . H5 H 0.6200 0.5309 0.3130 0.030 Uiso 1 1 calc R . . C6 C 0.56259(14) 0.7232(3) 0.25433(6) 0.0224(3) Uani 1 1 d . . . H6 H 0.5358 0.8281 0.2733 0.027 Uiso 1 1 calc R . . C7 C 0.37638(13) 0.9574(2) 0.16382(6) 0.0168(3) Uani 1 1 d . . . C8 C 0.31994(13) 0.7682(2) 0.13547(6) 0.0192(3) Uani 1 1 d . . . H8A H 0.3352 0.6457 0.1572 0.023 Uiso 1 1 calc R . . H8B H 0.3545 0.7442 0.1060 0.023 Uiso 1 1 calc R . . C9 C 0.18757(14) 0.8010(2) 0.11882(6) 0.0205(3) Uani 1 1 d . . . H9 H 0.1516 0.6771 0.1003 0.025 Uiso 1 1 calc R . . C10 C 0.13396(14) 0.8347(3) 0.16464(6) 0.0224(3) Uani 1 1 d . . . H10A H 0.0486 0.8545 0.1541 0.027 Uiso 1 1 calc R . . H10B H 0.1479 0.7123 0.1865 0.027 Uiso 1 1 calc R . . C11 C 0.18905(14) 1.0242(2) 0.19321(6) 0.0215(3) Uani 1 1 d . . . H11 H 0.1545 1.0459 0.2232 0.026 Uiso 1 1 calc R . . C12 C 0.32105(14) 0.9921(3) 0.20929(6) 0.0205(3) Uani 1 1 d . . . H12A H 0.3367 0.8717 0.2317 0.025 Uiso 1 1 calc R . . H12B H 0.3568 1.1142 0.2279 0.025 Uiso 1 1 calc R . . C13 C 0.35155(14) 1.1462(2) 0.12972(6) 0.0212(3) Uani 1 1 d . . . H13A H 0.3859 1.1256 0.1001 0.025 Uiso 1 1 calc R . . H13B H 0.3881 1.2692 0.1476 0.025 Uiso 1 1 calc R . . C14 C 0.21917(15) 1.1801(3) 0.11336(6) 0.0239(4) Uani 1 1 d . . . H14 H 0.2039 1.3033 0.0913 0.029 Uiso 1 1 calc R . . C15 C 0.16405(15) 0.9898(3) 0.08493(6) 0.0238(3) Uani 1 1 d . . . H15A H 0.0789 1.0103 0.0739 0.029 Uiso 1 1 calc R . . H15B H 0.1976 0.9683 0.0551 0.029 Uiso 1 1 calc R . . C16 C 0.16593(15) 1.2133(3) 0.15925(7) 0.0255(4) Uani 1 1 d . . . H16A H 0.0808 1.2361 0.1488 0.031 Uiso 1 1 calc R . . H16B H 0.2009 1.3365 0.1776 0.031 Uiso 1 1 calc R . . C17 C 0.67001(13) 0.5682(2) 0.09457(6) 0.0174(3) Uani 1 1 d . . . C18 C 0.64197(14) 0.3517(2) 0.07303(6) 0.0206(3) Uani 1 1 d . . . H18A H 0.5597 0.3461 0.0549 0.025 Uiso 1 1 calc R . . H18B H 0.6523 0.2502 0.1004 0.025 Uiso 1 1 calc R . . C19 C 0.72319(15) 0.2980(2) 0.03750(6) 0.0234(3) Uani 1 1 d . . . H19 H 0.7044 0.1570 0.0238 0.028 Uiso 1 1 calc R . . C20 C 0.85023(16) 0.3041(3) 0.06612(7) 0.0273(4) Uani 1 1 d . . . H20A H 0.9030 0.2666 0.0437 0.033 Uiso 1 1 calc R . . H20B H 0.8616 0.2036 0.0937 0.033 Uiso 1 1 calc R . . C21 C 0.87955(15) 0.5211(3) 0.08692(7) 0.0259(4) Uani 1 1 d . . . H21 H 0.9626 0.5250 0.1054 0.031 Uiso 1 1 calc R . . C22 C 0.79873(14) 0.5766(3) 0.12253(6) 0.0222(3) Uani 1 1 d . . . H22A H 0.8174 0.7164 0.1360 0.027 Uiso 1 1 calc R . . H22B H 0.8111 0.4789 0.1507 0.027 Uiso 1 1 calc R . . C23 C 0.65479(15) 0.7208(3) 0.05124(6) 0.0220(3) Uani 1 1 d . . . H23A H 0.5727 0.7182 0.0328 0.026 Uiso 1 1 calc R . . H23B H 0.6723 0.8613 0.0645 0.026 Uiso 1 1 calc R . . C24 C 0.73543(15) 0.6687(3) 0.01567(6) 0.0235(4) Uani 1 1 d . . . H24 H 0.7236 0.7704 -0.0122 0.028 Uiso 1 1 calc R . . C25 C 0.70691(16) 0.4527(3) -0.00527(6) 0.0252(4) Uani 1 1 d . . . H25A H 0.6253 0.4481 -0.0243 0.030 Uiso 1 1 calc R . . H25B H 0.7591 0.4171 -0.0281 0.030 Uiso 1 1 calc R . . C26 C 0.86268(16) 0.6756(3) 0.04401(7) 0.0284(4) Uani 1 1 d . . . H26A H 0.9153 0.6412 0.0213 0.034 Uiso 1 1 calc R . . H26B H 0.8822 0.8156 0.0572 0.034 Uiso 1 1 calc R . . N1 N 0.50527(11) 0.9338(2) 0.17784(5) 0.0190(3) Uani 1 1 d . . . H1N H 0.5520 1.0300 0.1707 0.023 Uiso 1 1 calc R . . N2 N 0.58685(12) 0.6357(2) 0.12490(5) 0.0206(3) Uani 1 1 d . . . H2N H 0.5263 0.7076 0.1097 0.025 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 C1 0.0142(7) 0.0188(7) 0.0202(8) -0.0003(6) 0.0038(6) -0.0014(6) C2 0.0153(7) 0.0200(7) 0.0185(7) 0.0001(6) 0.0049(6) -0.0022(6) C3 0.0189(7) 0.0203(8) 0.0241(8) 0.0014(6) 0.0061(6) 0.0012(6) C4 0.0166(7) 0.0281(9) 0.0261(8) 0.0088(7) 0.0035(6) 0.0007(6) C5 0.0202(8) 0.0385(10) 0.0167(7) 0.0051(7) 0.0039(6) -0.0004(7) C6 0.0177(7) 0.0293(9) 0.0206(8) -0.0026(6) 0.0051(6) -0.0014(6) C7 0.0177(7) 0.0146(7) 0.0190(7) -0.0006(5) 0.0060(6) 0.0009(5) C8 0.0189(7) 0.0167(7) 0.0232(8) -0.0026(6) 0.0070(6) 0.0010(6) C9 0.0190(7) 0.0197(8) 0.0236(8) -0.0036(6) 0.0065(6) -0.0010(6) C10 0.0206(8) 0.0207(8) 0.0280(8) 0.0005(6) 0.0098(6) 0.0000(6) C11 0.0226(8) 0.0226(8) 0.0217(8) -0.0009(6) 0.0101(6) 0.0043(6) C12 0.0226(8) 0.0228(8) 0.0175(7) -0.0012(6) 0.0075(6) 0.0017(6) C13 0.0238(8) 0.0169(7) 0.0239(8) 0.0035(6) 0.0076(6) -0.0008(6) C14 0.0269(9) 0.0195(8) 0.0261(8) 0.0069(6) 0.0071(7) 0.0050(6) C15 0.0217(8) 0.0287(9) 0.0204(8) 0.0013(7) 0.0034(6) 0.0034(7) C16 0.0256(8) 0.0198(8) 0.0315(9) -0.0009(7) 0.0070(7) 0.0075(6) C17 0.0180(7) 0.0177(7) 0.0174(7) 0.0000(6) 0.0057(6) 0.0008(6) C18 0.0225(8) 0.0186(7) 0.0212(8) -0.0002(6) 0.0059(6) -0.0026(6) C19 0.0301(9) 0.0170(7) 0.0248(8) -0.0034(6) 0.0099(7) -0.0005(6) C20 0.0277(9) 0.0260(9) 0.0306(9) 0.0021(7) 0.0119(7) 0.0084(7) C21 0.0164(7) 0.0317(9) 0.0300(9) -0.0010(7) 0.0058(6) -0.0005(7) C22 0.0204(8) 0.0244(8) 0.0211(8) -0.0032(6) 0.0030(6) -0.0025(6) C23 0.0262(8) 0.0197(8) 0.0216(8) 0.0018(6) 0.0086(6) 0.0028(6) C24 0.0319(9) 0.0205(8) 0.0209(8) 0.0037(6) 0.0124(7) 0.0015(7) C25 0.0302(9) 0.0268(9) 0.0207(8) -0.0040(6) 0.0098(7) -0.0002(7) C26 0.0280(9) 0.0267(9) 0.0349(10) -0.0020(7) 0.0163(7) -0.0059(7) N1 0.0166(6) 0.0165(6) 0.0249(7) 0.0007(5) 0.0068(5) -0.0025(5) N2 0.0211(7) 0.0240(7) 0.0179(6) 0.0034(5) 0.0065(5) 0.0079(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 C1 C6 1.389(2) . ? C1 C2 1.420(2) . ? C1 N1 1.439(2) . ? C2 N2 1.389(2) . ? C2 C3 1.402(2) . ? C3 C4 1.391(2) . ? C4 C5 1.381(3) . ? C5 C6 1.392(2) . ? C7 N1 1.4868(19) . ? C7 C8 1.532(2) . ? C7 C13 1.537(2) . ? C7 C12 1.539(2) . ? C8 C9 1.538(2) . ? C9 C15 1.532(2) . ? C9 C10 1.535(2) . ? C10 C11 1.532(2) . ? C11 C12 1.532(2) . ? C11 C16 1.535(2) . ? C13 C14 1.538(2) . ? C14 C16 1.534(2) . ? C14 C15 1.535(2) . ? C17 N2 1.4743(19) . ? C17 C23 1.533(2) . ? C17 C18 1.537(2) . ? C17 C22 1.545(2) . ? C18 C19 1.538(2) . ? C19 C25 1.530(2) . ? C19 C20 1.533(2) . ? C20 C21 1.536(2) . ? C21 C26 1.532(3) . ? C21 C22 1.539(2) . ? C23 C24 1.531(2) . ? C24 C25 1.530(2) . ? C24 C26 1.533(3) . ? 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 C6 C1 C2 119.66(15) . . ? C6 C1 N1 122.81(14) . . ? C2 C1 N1 117.33(13) . . ? N2 C2 C3 124.66(14) . . ? N2 C2 C1 117.14(14) . . ? C3 C2 C1 118.20(14) . . ? C4 C3 C2 120.87(15) . . ? C5 C4 C3 120.64(16) . . ? C4 C5 C6 119.32(15) . . ? C1 C6 C5 121.21(16) . . ? N1 C7 C8 110.93(12) . . ? N1 C7 C13 107.12(12) . . ? C8 C7 C13 108.99(13) . . ? N1 C7 C12 112.34(12) . . ? C8 C7 C12 108.74(12) . . ? C13 C7 C12 108.63(12) . . ? C7 C8 C9 110.02(12) . . ? C15 C9 C10 109.36(13) . . ? C15 C9 C8 109.61(13) . . ? C10 C9 C8 109.50(13) . . ? C11 C10 C9 109.60(13) . . ? C10 C11 C12 109.34(13) . . ? C10 C11 C16 109.37(14) . . ? C12 C11 C16 108.99(13) . . ? C11 C12 C7 110.80(13) . . ? C7 C13 C14 110.19(13) . . ? C16 C14 C15 109.44(14) . . ? C16 C14 C13 109.67(14) . . ? C15 C14 C13 108.99(13) . . ? C9 C15 C14 109.54(13) . . ? C14 C16 C11 109.67(13) . . ? N2 C17 C23 105.18(12) . . ? N2 C17 C18 112.19(13) . . ? C23 C17 C18 108.28(13) . . ? N2 C17 C22 113.50(12) . . ? C23 C17 C22 107.95(13) . . ? C18 C17 C22 109.45(13) . . ? C17 C18 C19 110.00(13) . . ? C25 C19 C20 109.33(14) . . ? C25 C19 C18 110.07(14) . . ? C20 C19 C18 109.28(14) . . ? C19 C20 C21 109.47(13) . . ? C26 C21 C20 109.52(14) . . ? C26 C21 C22 109.71(14) . . ? C20 C21 C22 109.46(14) . . ? C21 C22 C17 109.91(13) . . ? C24 C23 C17 111.38(13) . . ? C25 C24 C23 109.16(14) . . ? C25 C24 C26 109.39(14) . . ? C23 C24 C26 109.41(14) . . ? C19 C25 C24 109.46(13) . . ? C21 C26 C24 109.21(13) . . ? C1 N1 C7 118.09(12) . . ? C2 N2 C17 126.18(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.746 _refine_diff_density_min -0.698 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 949605' ####################################################################### # # 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_sad2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 N2' _chemical_formula_weight 428.64 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.2811(4) _cell_length_b 12.3784(4) _cell_length_c 17.0783(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.7570(10) _cell_angle_gamma 90.00 _cell_volume 2572.49(14) _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 prism' _exptl_crystal_colour 'pale pink' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9868 _exptl_absorpt_correction_T_max 0.9943 _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 = 0.853303 ; _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 27712 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 29.50 _reflns_number_total 7152 _reflns_number_gt 5849 _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^)+(0.0800P)^2^+0.5199P] 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 7152 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C1 C 0.23782(7) 0.48775(8) 0.15092(5) 0.02058(18) Uani 1 1 d . . . C2 C 0.27479(7) 0.37943(8) 0.15335(5) 0.02081(18) Uani 1 1 d . . . C3 C 0.34956(8) 0.34682(9) 0.10387(6) 0.0259(2) Uani 1 1 d . . . H3 H 0.3773 0.2751 0.1071 0.031 Uiso 1 1 calc R . . C4 C 0.38416(8) 0.41896(9) 0.04943(6) 0.0291(2) Uani 1 1 d . . . H4 H 0.4354 0.3963 0.0158 0.035 Uiso 1 1 calc R . . C5 C 0.34392(8) 0.52313(9) 0.04458(6) 0.0283(2) Uani 1 1 d . . . H5 H 0.3654 0.5712 0.0061 0.034 Uiso 1 1 calc R . . C6 C 0.27197(8) 0.55845(8) 0.09572(6) 0.0250(2) Uani 1 1 d . . . H6 H 0.2462 0.6309 0.0929 0.030 Uiso 1 1 calc R . . C7 C 0.13735(8) 0.62695(8) 0.21798(6) 0.02225(19) Uani 1 1 d . . . C8 C 0.05406(8) 0.67434(8) 0.16457(6) 0.0261(2) Uani 1 1 d . . . C9 C 0.02029(10) 0.77899(9) 0.18064(7) 0.0334(2) Uani 1 1 d . . . H9 H -0.0355 0.8127 0.1450 0.040 Uiso 1 1 calc R . . C10 C 0.06622(10) 0.83421(9) 0.24706(8) 0.0359(3) Uani 1 1 d . . . H10 H 0.0413 0.9049 0.2571 0.043 Uiso 1 1 calc R . . C11 C 0.14883(10) 0.78662(9) 0.29922(7) 0.0318(2) Uani 1 1 d . . . H11 H 0.1804 0.8254 0.3447 0.038 Uiso 1 1 calc R . . C12 C 0.18620(8) 0.68279(8) 0.28589(6) 0.0247(2) Uani 1 1 d . . . C13 C -0.00374(9) 0.61342(9) 0.09383(7) 0.0315(2) Uani 1 1 d . . . H13 H 0.0365 0.5439 0.0894 0.038 Uiso 1 1 calc R . . C14 C -0.12174(11) 0.58575(12) 0.10633(9) 0.0459(3) Uani 1 1 d . . . H14A H -0.1210 0.5470 0.1564 0.069 Uiso 1 1 calc R . . H14B H -0.1554 0.5401 0.0628 0.069 Uiso 1 1 calc R . . H14C H -0.1643 0.6525 0.1078 0.069 Uiso 1 1 calc R . . C15 C -0.00229(14) 0.67552(13) 0.01682(8) 0.0526(4) Uani 1 1 d . . . H15A H -0.0406 0.7445 0.0198 0.079 Uiso 1 1 calc R . . H15B H -0.0392 0.6329 -0.0273 0.079 Uiso 1 1 calc R . . H15C H 0.0739 0.6891 0.0085 0.079 Uiso 1 1 calc R . . C16 C 0.27588(9) 0.63065(9) 0.34394(6) 0.0293(2) Uani 1 1 d . . . H16 H 0.2546 0.5534 0.3497 0.035 Uiso 1 1 calc R . . C17 C 0.38567(10) 0.63087(13) 0.31194(8) 0.0444(3) Uani 1 1 d . . . H17A H 0.3768 0.5974 0.2595 0.067 Uiso 1 1 calc R . . H17B H 0.4397 0.5899 0.3477 0.067 Uiso 1 1 calc R . . H17C H 0.4112 0.7054 0.3081 0.067 Uiso 1 1 calc R . . C18 C 0.28885(13) 0.68082(12) 0.42643(8) 0.0459(3) Uani 1 1 d . . . H18A H 0.3180 0.7543 0.4241 0.069 Uiso 1 1 calc R . . H18B H 0.3398 0.6370 0.4625 0.069 Uiso 1 1 calc R . . H18C H 0.2172 0.6833 0.4456 0.069 Uiso 1 1 calc R . . C19 C 0.28611(8) 0.20811(8) 0.22925(6) 0.02259(19) Uani 1 1 d . . . C20 C 0.25007(8) 0.11367(8) 0.18802(6) 0.0247(2) Uani 1 1 d . . . C21 C 0.29548(9) 0.01516(9) 0.21599(7) 0.0304(2) Uani 1 1 d . . . H21 H 0.2704 -0.0500 0.1902 0.036 Uiso 1 1 calc R . . C22 C 0.37645(9) 0.01129(9) 0.28066(7) 0.0336(2) Uani 1 1 d . . . H22 H 0.4055 -0.0564 0.2995 0.040 Uiso 1 1 calc R . . C23 C 0.41521(9) 0.10565(9) 0.31792(7) 0.0310(2) Uani 1 1 d . . . H23 H 0.4727 0.1022 0.3610 0.037 Uiso 1 1 calc R . . C24 C 0.37123(8) 0.20583(8) 0.29323(6) 0.0253(2) Uani 1 1 d . . . C25 C 0.16403(9) 0.11875(9) 0.11534(6) 0.0277(2) Uani 1 1 d . . . H25 H 0.1677 0.1924 0.0918 0.033 Uiso 1 1 calc R . . C26 C 0.18505(13) 0.03640(14) 0.05203(8) 0.0522(4) Uani 1 1 d . . . H26A H 0.2615 0.0422 0.0418 0.078 Uiso 1 1 calc R . . H26B H 0.1356 0.0510 0.0032 0.078 Uiso 1 1 calc R . . H26C H 0.1716 -0.0367 0.0706 0.078 Uiso 1 1 calc R . . C27 C 0.04856(10) 0.10358(11) 0.13657(8) 0.0388(3) Uani 1 1 d . . . H27A H 0.0406 0.0299 0.1559 0.058 Uiso 1 1 calc R . . H27B H -0.0053 0.1158 0.0896 0.058 Uiso 1 1 calc R . . H27C H 0.0360 0.1553 0.1779 0.058 Uiso 1 1 calc R . . C28 C 0.41087(9) 0.30965(9) 0.33545(6) 0.0297(2) Uani 1 1 d . . . H28 H 0.4017 0.3694 0.2957 0.036 Uiso 1 1 calc R . . C29 C 0.53225(11) 0.30601(11) 0.37072(8) 0.0432(3) Uani 1 1 d . . . H29A H 0.5421 0.2542 0.4145 0.065 Uiso 1 1 calc R . . H29B H 0.5557 0.3779 0.3903 0.065 Uiso 1 1 calc R . . H29C H 0.5766 0.2836 0.3300 0.065 Uiso 1 1 calc R . . C30 C 0.33993(12) 0.33661(10) 0.39969(7) 0.0398(3) Uani 1 1 d . . . H30A H 0.2630 0.3435 0.3759 0.060 Uiso 1 1 calc R . . H30B H 0.3648 0.4049 0.4251 0.060 Uiso 1 1 calc R . . H30C H 0.3464 0.2787 0.4392 0.060 Uiso 1 1 calc R . . H1N H 0.1810(12) 0.4806(12) 0.2488(9) 0.038(4) Uiso 1 1 d . . . H2N H 0.1638(12) 0.3086(11) 0.2061(9) 0.036(4) Uiso 1 1 d . . . N1 N 0.16722(7) 0.51716(7) 0.20544(5) 0.02232(17) Uani 1 1 d . . . N2 N 0.23489(7) 0.31059(7) 0.20904(5) 0.02272(17) 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 0.0189(4) 0.0218(4) 0.0199(4) 0.0002(3) -0.0015(3) -0.0015(3) C2 0.0201(4) 0.0219(4) 0.0196(4) 0.0003(3) -0.0005(3) -0.0017(3) C3 0.0250(4) 0.0255(5) 0.0271(5) -0.0026(4) 0.0033(4) 0.0003(4) C4 0.0256(5) 0.0364(6) 0.0264(5) -0.0035(4) 0.0074(4) -0.0041(4) C5 0.0265(5) 0.0340(5) 0.0241(5) 0.0029(4) 0.0029(4) -0.0079(4) C6 0.0249(4) 0.0239(5) 0.0252(5) 0.0030(4) -0.0004(4) -0.0025(4) C7 0.0229(4) 0.0186(4) 0.0254(5) 0.0016(3) 0.0036(3) -0.0001(3) C8 0.0260(5) 0.0233(5) 0.0282(5) 0.0028(4) 0.0005(4) 0.0012(4) C9 0.0344(5) 0.0249(5) 0.0392(6) 0.0046(4) -0.0012(4) 0.0068(4) C10 0.0425(6) 0.0198(5) 0.0448(7) -0.0001(4) 0.0041(5) 0.0049(4) C11 0.0374(6) 0.0230(5) 0.0344(6) -0.0038(4) 0.0024(4) -0.0028(4) C12 0.0251(4) 0.0225(5) 0.0260(5) 0.0010(4) 0.0022(4) -0.0022(4) C13 0.0316(5) 0.0288(5) 0.0311(5) -0.0002(4) -0.0067(4) 0.0040(4) C14 0.0345(6) 0.0470(7) 0.0528(8) -0.0050(6) -0.0059(5) -0.0062(5) C15 0.0664(9) 0.0565(9) 0.0311(6) 0.0067(6) -0.0066(6) -0.0024(7) C16 0.0316(5) 0.0271(5) 0.0273(5) 0.0001(4) -0.0033(4) -0.0011(4) C17 0.0289(6) 0.0616(9) 0.0405(7) -0.0034(6) -0.0031(5) 0.0029(5) C18 0.0538(8) 0.0514(8) 0.0294(6) -0.0043(5) -0.0049(5) 0.0016(6) C19 0.0226(4) 0.0209(4) 0.0244(4) 0.0025(3) 0.0035(3) 0.0021(3) C20 0.0238(4) 0.0238(5) 0.0265(5) 0.0006(4) 0.0035(4) 0.0006(3) C21 0.0310(5) 0.0223(5) 0.0378(6) -0.0005(4) 0.0045(4) 0.0012(4) C22 0.0319(5) 0.0253(5) 0.0429(6) 0.0074(4) 0.0026(5) 0.0065(4) C23 0.0267(5) 0.0318(6) 0.0329(5) 0.0071(4) -0.0021(4) 0.0037(4) C24 0.0246(4) 0.0252(5) 0.0257(5) 0.0025(4) 0.0018(4) -0.0001(4) C25 0.0302(5) 0.0268(5) 0.0253(5) -0.0011(4) 0.0006(4) -0.0014(4) C26 0.0605(9) 0.0611(9) 0.0343(7) -0.0147(6) 0.0034(6) 0.0086(7) C27 0.0278(5) 0.0498(7) 0.0370(6) 0.0051(5) -0.0015(4) -0.0015(5) C28 0.0334(5) 0.0270(5) 0.0267(5) 0.0022(4) -0.0035(4) -0.0031(4) C29 0.0380(6) 0.0426(7) 0.0445(7) -0.0033(5) -0.0104(5) -0.0079(5) C30 0.0525(7) 0.0328(6) 0.0340(6) -0.0020(5) 0.0061(5) 0.0002(5) N1 0.0257(4) 0.0187(4) 0.0226(4) 0.0024(3) 0.0032(3) 0.0022(3) N2 0.0219(4) 0.0206(4) 0.0256(4) 0.0042(3) 0.0032(3) 0.0025(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 C1 C6 1.3918(13) . ? C1 N1 1.4034(13) . ? C1 C2 1.4144(13) . ? C2 C3 1.3891(14) . ? C2 N2 1.4130(12) . ? C3 C4 1.3961(15) . ? C4 C5 1.3794(16) . ? C5 C6 1.3939(15) . ? C7 C8 1.4038(13) . ? C7 C12 1.4125(14) . ? C7 N1 1.4312(12) . ? C8 C9 1.3985(15) . ? C8 C13 1.5169(15) . ? C9 C10 1.3782(17) . ? C10 C11 1.3877(16) . ? C11 C12 1.3937(15) . ? C12 C16 1.5224(14) . ? C13 C15 1.5255(18) . ? C13 C14 1.5318(18) . ? C16 C17 1.5217(17) . ? C16 C18 1.5282(16) . ? C19 C20 1.4051(14) . ? C19 C24 1.4068(13) . ? C19 N2 1.4370(12) . ? C20 C21 1.3979(14) . ? C20 C25 1.5190(14) . ? C21 C22 1.3837(16) . ? C22 C23 1.3834(16) . ? C23 C24 1.3949(14) . ? C24 C28 1.5211(15) . ? C25 C27 1.5220(16) . ? C25 C26 1.5330(17) . ? C28 C30 1.5271(17) . ? C28 C29 1.5312(16) . ? 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 C6 C1 N1 123.78(9) . . ? C6 C1 C2 119.41(9) . . ? N1 C1 C2 116.81(8) . . ? C3 C2 N2 123.50(9) . . ? C3 C2 C1 119.57(9) . . ? N2 C2 C1 116.90(8) . . ? C2 C3 C4 120.32(10) . . ? C5 C4 C3 119.95(10) . . ? C4 C5 C6 120.52(10) . . ? C1 C6 C5 120.10(10) . . ? C8 C7 C12 121.36(9) . . ? C8 C7 N1 118.60(9) . . ? C12 C7 N1 119.90(9) . . ? C9 C8 C7 117.97(10) . . ? C9 C8 C13 119.83(9) . . ? C7 C8 C13 122.10(9) . . ? C10 C9 C8 121.44(10) . . ? C9 C10 C11 120.02(10) . . ? C10 C11 C12 121.00(10) . . ? C11 C12 C7 118.21(9) . . ? C11 C12 C16 120.66(9) . . ? C7 C12 C16 121.13(9) . . ? C8 C13 C15 112.18(10) . . ? C8 C13 C14 110.48(10) . . ? C15 C13 C14 110.74(11) . . ? C17 C16 C12 111.32(9) . . ? C17 C16 C18 110.07(10) . . ? C12 C16 C18 113.84(10) . . ? C20 C19 C24 121.55(9) . . ? C20 C19 N2 121.06(9) . . ? C24 C19 N2 117.36(9) . . ? C21 C20 C19 118.06(9) . . ? C21 C20 C25 121.11(9) . . ? C19 C20 C25 120.83(9) . . ? C22 C21 C20 120.90(10) . . ? C23 C22 C21 120.23(10) . . ? C22 C23 C24 121.09(10) . . ? C23 C24 C19 118.00(9) . . ? C23 C24 C28 121.45(9) . . ? C19 C24 C28 120.52(9) . . ? C20 C25 C27 111.59(9) . . ? C20 C25 C26 112.59(10) . . ? C27 C25 C26 109.70(11) . . ? C24 C28 C30 110.37(9) . . ? C24 C28 C29 113.20(10) . . ? C30 C28 C29 110.08(10) . . ? C1 N1 C7 122.64(8) . . ? C2 N2 C19 120.92(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.400 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 949606' ####################################################################### # # 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_sad3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Ge N2' _chemical_formula_weight 499.21 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' Ge Ge 0.1547 1.8001 '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)/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 9.0671(15) _cell_length_b 10.9479(18) _cell_length_c 27.971(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.713(3) _cell_angle_gamma 90.00 _cell_volume 2775.4(8) _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 colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8678 _exptl_absorpt_correction_T_max 0.9671 _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 = 0.827479 ; _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 25109 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 30.00 _reflns_number_total 8008 _reflns_number_gt 5528 _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^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8008 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0953 _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 Ge1 Ge 0.46738(3) 0.07888(2) 0.121769(7) 0.02906(8) Uani 1 1 d . . . N1 N 0.43122(18) 0.22149(14) 0.08743(5) 0.0242(4) Uani 1 1 d . . . N2 N 0.33580(18) 0.14450(15) 0.16472(5) 0.0247(4) Uani 1 1 d . . . C1 C 0.3340(2) 0.30257(17) 0.10848(6) 0.0233(4) Uani 1 1 d . . . C2 C 0.2806(2) 0.25916(17) 0.15227(6) 0.0228(4) Uani 1 1 d . . . C3 C 0.1836(2) 0.33045(19) 0.17790(7) 0.0282(4) Uani 1 1 d . . . H3 H 0.1477 0.3021 0.2075 0.034 Uiso 1 1 calc R . . C4 C 0.1397(2) 0.44300(19) 0.15995(8) 0.0314(5) Uani 1 1 d . . . H4 H 0.0738 0.4920 0.1774 0.038 Uiso 1 1 calc R . . C5 C 0.1913(2) 0.48523(19) 0.11651(8) 0.0325(5) Uani 1 1 d . . . H5 H 0.1595 0.5623 0.1045 0.039 Uiso 1 1 calc R . . C6 C 0.2888(2) 0.41521(17) 0.09067(7) 0.0281(4) Uani 1 1 d . . . H6 H 0.3241 0.4442 0.0611 0.034 Uiso 1 1 calc R . . C7 C 0.4840(2) 0.24588(17) 0.04025(6) 0.0233(4) Uani 1 1 d . . . C8 C 0.6214(2) 0.30218(17) 0.03516(7) 0.0253(4) Uani 1 1 d . . . C9 C 0.6721(2) 0.31794(18) -0.01105(7) 0.0280(4) Uani 1 1 d . . . H9 H 0.7658 0.3545 -0.0155 0.034 Uiso 1 1 calc R . . C10 C 0.5881(2) 0.28113(18) -0.05046(7) 0.0296(5) Uani 1 1 d . . . H10 H 0.6245 0.2926 -0.0816 0.036 Uiso 1 1 calc R . . C11 C 0.4516(2) 0.22783(18) -0.04493(7) 0.0285(4) Uani 1 1 d . . . H11 H 0.3948 0.2033 -0.0724 0.034 Uiso 1 1 calc R . . C12 C 0.3962(2) 0.20961(17) 0.00057(7) 0.0247(4) Uani 1 1 d . . . C13 C 0.7146(2) 0.34479(18) 0.07794(7) 0.0294(4) Uani 1 1 d . . . H13 H 0.6510 0.3424 0.1065 0.035 Uiso 1 1 calc R . . C14 C 0.7677(3) 0.4759(2) 0.07215(10) 0.0507(7) Uani 1 1 d . . . H14A H 0.8186 0.5026 0.1017 0.076 Uiso 1 1 calc R . . H14B H 0.6829 0.5293 0.0654 0.076 Uiso 1 1 calc R . . H14C H 0.8358 0.4802 0.0456 0.076 Uiso 1 1 calc R . . C15 C 0.8433(3) 0.2599(2) 0.08768(9) 0.0501(7) Uani 1 1 d . . . H15A H 0.8066 0.1769 0.0928 0.075 Uiso 1 1 calc R . . H15B H 0.8988 0.2874 0.1163 0.075 Uiso 1 1 calc R . . H15C H 0.9080 0.2603 0.0602 0.075 Uiso 1 1 calc R . . C16 C 0.2452(2) 0.15107(18) 0.00578(7) 0.0284(4) Uani 1 1 d . . . H16 H 0.2218 0.1519 0.0405 0.034 Uiso 1 1 calc R . . C17 C 0.2477(3) 0.0182(2) -0.01060(11) 0.0545(7) Uani 1 1 d . . . H17A H 0.2727 0.0147 -0.0444 0.082 Uiso 1 1 calc R . . H17B H 0.1503 -0.0184 -0.0065 0.082 Uiso 1 1 calc R . . H17C H 0.3217 -0.0270 0.0085 0.082 Uiso 1 1 calc R . . C18 C 0.1246(3) 0.2231(2) -0.02127(9) 0.0471(6) Uani 1 1 d . . . H18A H 0.1209 0.3065 -0.0087 0.071 Uiso 1 1 calc R . . H18B H 0.0291 0.1832 -0.0171 0.071 Uiso 1 1 calc R . . H18C H 0.1465 0.2256 -0.0553 0.071 Uiso 1 1 calc R . . C19 C 0.2912(2) 0.08420(18) 0.20772(7) 0.0261(4) Uani 1 1 d . . . C20 C 0.3709(2) 0.10453(18) 0.25031(7) 0.0294(5) Uani 1 1 d . . . C21 C 0.3356(3) 0.0350(2) 0.29006(8) 0.0379(5) Uani 1 1 d . . . H21 H 0.3896 0.0466 0.3193 0.045 Uiso 1 1 calc R . . C22 C 0.2239(3) -0.0502(2) 0.28772(8) 0.0413(6) Uani 1 1 d . . . H22 H 0.2031 -0.0983 0.3150 0.050 Uiso 1 1 calc R . . C23 C 0.1421(3) -0.0656(2) 0.24572(8) 0.0363(5) Uani 1 1 d . . . H23 H 0.0635 -0.1230 0.2447 0.044 Uiso 1 1 calc R . . C24 C 0.1729(2) 0.00166(19) 0.20477(7) 0.0301(5) Uani 1 1 d . . . C25 C 0.4961(3) 0.1963(2) 0.25392(7) 0.0342(5) Uani 1 1 d . . . H25 H 0.4938 0.2452 0.2237 0.041 Uiso 1 1 calc R . . C26 C 0.4796(3) 0.2850(3) 0.29528(10) 0.0567(7) Uani 1 1 d . . . H26A H 0.3835 0.3256 0.2923 0.085 Uiso 1 1 calc R . . H26B H 0.5583 0.3463 0.2946 0.085 Uiso 1 1 calc R . . H26C H 0.4865 0.2401 0.3256 0.085 Uiso 1 1 calc R . . C27 C 0.6433(3) 0.1309(3) 0.25723(13) 0.0644(8) Uani 1 1 d . . . H27A H 0.6479 0.0801 0.2861 0.097 Uiso 1 1 calc R . . H27B H 0.7233 0.1911 0.2587 0.097 Uiso 1 1 calc R . . H27C H 0.6541 0.0790 0.2290 0.097 Uiso 1 1 calc R . . C28 C 0.0842(2) -0.0205(2) 0.15890(8) 0.0364(5) Uani 1 1 d . . . H28 H 0.1052 0.0484 0.1366 0.044 Uiso 1 1 calc R . . C29 C 0.1333(4) -0.1385(3) 0.13492(11) 0.0684(9) Uani 1 1 d . . . H29A H 0.2402 -0.1362 0.1307 0.103 Uiso 1 1 calc R . . H29B H 0.0828 -0.1465 0.1036 0.103 Uiso 1 1 calc R . . H29C H 0.1085 -0.2084 0.1550 0.103 Uiso 1 1 calc R . . C30 C -0.0814(3) -0.0217(3) 0.16655(11) 0.0617(8) Uani 1 1 d . . . H30A H -0.1061 -0.0909 0.1871 0.092 Uiso 1 1 calc R . . H30B H -0.1340 -0.0298 0.1356 0.092 Uiso 1 1 calc R . . H30C H -0.1105 0.0547 0.1819 0.092 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 Ge1 0.03341(14) 0.02993(12) 0.02440(11) 0.00554(9) 0.01035(9) 0.00645(10) N1 0.0272(9) 0.0268(8) 0.0189(7) 0.0016(6) 0.0077(7) 0.0014(7) N2 0.0242(9) 0.0303(8) 0.0199(7) 0.0047(6) 0.0056(7) 0.0021(7) C1 0.0231(10) 0.0252(9) 0.0217(9) 0.0000(7) 0.0019(8) -0.0028(8) C2 0.0210(10) 0.0275(9) 0.0199(8) -0.0010(7) 0.0010(7) -0.0021(8) C3 0.0249(11) 0.0370(11) 0.0229(9) -0.0015(8) 0.0051(8) -0.0008(9) C4 0.0267(11) 0.0339(11) 0.0338(11) -0.0048(9) 0.0045(9) 0.0025(9) C5 0.0331(12) 0.0275(10) 0.0369(11) 0.0006(9) 0.0027(10) 0.0023(9) C6 0.0288(11) 0.0288(10) 0.0269(10) 0.0014(8) 0.0041(8) -0.0020(9) C7 0.0289(11) 0.0224(9) 0.0191(8) 0.0022(7) 0.0070(8) 0.0029(8) C8 0.0280(11) 0.0235(9) 0.0247(9) 0.0027(7) 0.0037(8) 0.0010(8) C9 0.0247(11) 0.0301(10) 0.0295(10) 0.0050(8) 0.0069(8) -0.0021(8) C10 0.0346(12) 0.0328(10) 0.0219(9) 0.0035(8) 0.0086(9) 0.0027(9) C11 0.0333(12) 0.0307(10) 0.0216(9) 0.0000(8) 0.0015(8) 0.0003(9) C12 0.0271(11) 0.0243(9) 0.0227(9) 0.0014(7) 0.0034(8) 0.0010(8) C13 0.0312(12) 0.0310(10) 0.0260(10) -0.0018(8) 0.0038(9) -0.0044(9) C14 0.0665(19) 0.0349(13) 0.0500(15) 0.0006(11) -0.0114(14) -0.0077(13) C15 0.0548(18) 0.0463(14) 0.0479(15) -0.0112(12) -0.0188(13) 0.0080(13) C16 0.0283(11) 0.0309(10) 0.0263(10) -0.0001(8) 0.0045(8) -0.0047(9) C17 0.0507(17) 0.0363(13) 0.078(2) -0.0079(13) 0.0192(15) -0.0141(12) C18 0.0316(14) 0.0534(15) 0.0562(16) 0.0126(12) -0.0013(12) -0.0079(11) C19 0.0262(11) 0.0318(10) 0.0207(9) 0.0042(8) 0.0067(8) 0.0044(9) C20 0.0300(12) 0.0340(11) 0.0242(10) 0.0013(8) 0.0032(8) 0.0017(9) C21 0.0445(15) 0.0484(13) 0.0207(10) 0.0058(9) -0.0005(9) -0.0002(11) C22 0.0499(16) 0.0477(14) 0.0269(11) 0.0124(9) 0.0108(10) -0.0022(11) C23 0.0330(12) 0.0433(12) 0.0333(11) 0.0049(9) 0.0119(10) -0.0067(10) C24 0.0267(11) 0.0371(11) 0.0268(10) 0.0009(8) 0.0057(9) -0.0001(9) C25 0.0351(13) 0.0397(12) 0.0277(11) -0.0001(9) -0.0020(9) -0.0024(10) C26 0.0595(19) 0.0572(16) 0.0539(16) -0.0205(13) 0.0075(14) -0.0140(14) C27 0.0335(16) 0.0513(16) 0.108(3) -0.0051(17) 0.0000(16) 0.0001(13) C28 0.0271(12) 0.0493(13) 0.0328(11) 0.0031(10) -0.0011(9) -0.0040(10) C29 0.066(2) 0.078(2) 0.0601(18) -0.0302(17) -0.0219(16) 0.0126(17) C30 0.0308(15) 0.086(2) 0.0679(19) 0.0133(17) -0.0029(13) 0.0000(15) _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 Ge1 N1 1.8571(16) . ? Ge1 N2 1.8624(15) . ? N1 C1 1.394(2) . ? N1 C7 1.442(2) . ? N2 C2 1.392(2) . ? N2 C19 1.440(2) . ? C1 C6 1.387(3) . ? C1 C2 1.413(2) . ? C2 C3 1.391(3) . ? C3 C4 1.385(3) . ? C4 C5 1.394(3) . ? C5 C6 1.389(3) . ? C7 C8 1.401(3) . ? C7 C12 1.404(3) . ? C8 C9 1.396(3) . ? C8 C13 1.518(3) . ? C9 C10 1.382(3) . ? C10 C11 1.381(3) . ? C11 C12 1.397(2) . ? C12 C16 1.522(3) . ? C13 C15 1.510(3) . ? C13 C14 1.524(3) . ? C16 C17 1.525(3) . ? C16 C18 1.530(3) . ? C19 C20 1.392(3) . ? C19 C24 1.403(3) . ? C20 C21 1.392(3) . ? C20 C25 1.517(3) . ? C21 C22 1.377(3) . ? C22 C23 1.381(3) . ? C23 C24 1.397(3) . ? C24 C28 1.513(3) . ? C25 C27 1.515(3) . ? C25 C26 1.521(3) . ? C28 C30 1.523(3) . ? C28 C29 1.528(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 N1 Ge1 N2 84.41(7) . . ? C1 N1 C7 120.01(15) . . ? C1 N1 Ge1 114.90(12) . . ? C7 N1 Ge1 124.79(12) . . ? C2 N2 C19 120.96(15) . . ? C2 N2 Ge1 114.77(11) . . ? C19 N2 Ge1 124.26(13) . . ? C6 C1 N1 126.74(16) . . ? C6 C1 C2 120.35(17) . . ? N1 C1 C2 112.91(16) . . ? C3 C2 N2 127.25(17) . . ? C3 C2 C1 119.76(18) . . ? N2 C2 C1 112.99(16) . . ? C4 C3 C2 119.45(18) . . ? C3 C4 C5 120.75(19) . . ? C6 C5 C4 120.37(19) . . ? C1 C6 C5 119.31(18) . . ? C8 C7 C12 121.96(16) . . ? C8 C7 N1 119.67(17) . . ? C12 C7 N1 118.35(17) . . ? C9 C8 C7 117.87(18) . . ? C9 C8 C13 120.04(18) . . ? C7 C8 C13 122.09(16) . . ? C10 C9 C8 120.90(19) . . ? C11 C10 C9 120.58(18) . . ? C10 C11 C12 120.69(19) . . ? C11 C12 C7 117.96(18) . . ? C11 C12 C16 119.76(18) . . ? C7 C12 C16 122.28(16) . . ? C15 C13 C8 111.24(17) . . ? C15 C13 C14 110.7(2) . . ? C8 C13 C14 112.09(18) . . ? C12 C16 C17 110.55(17) . . ? C12 C16 C18 111.55(17) . . ? C17 C16 C18 111.1(2) . . ? C20 C19 C24 121.97(17) . . ? C20 C19 N2 119.32(18) . . ? C24 C19 N2 118.63(18) . . ? C19 C20 C21 118.0(2) . . ? C19 C20 C25 122.07(17) . . ? C21 C20 C25 119.9(2) . . ? C22 C21 C20 121.2(2) . . ? C21 C22 C23 119.9(2) . . ? C22 C23 C24 121.2(2) . . ? C23 C24 C19 117.5(2) . . ? C23 C24 C28 119.8(2) . . ? C19 C24 C28 122.60(18) . . ? C27 C25 C20 110.33(19) . . ? C27 C25 C26 111.2(2) . . ? C20 C25 C26 112.50(19) . . ? C24 C28 C30 112.54(19) . . ? C24 C28 C29 110.7(2) . . ? C30 C28 C29 110.8(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.513 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 949607' ####################################################################### # # 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_sad4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 N2 Sn' _chemical_formula_sum 'C14 H22 N2 Sn' _chemical_formula_weight 337.03 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 Cmcm _symmetry_space_group_name_Hall '-C 2c 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 6.7920(3) _cell_length_b 10.7367(4) _cell_length_c 19.9685(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1456.18(10) _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 prism' _exptl_crystal_colour 'intense yellow' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8186 _exptl_absorpt_correction_T_max 0.9029 _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 = 0.847027 ; _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 8755 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0101 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 30.98 _reflns_number_total 1279 _reflns_number_gt 1228 _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^)+(0.0294P)^2^+0.6123P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1279 _refine_ls_number_parameters 57 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0184 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0480 _refine_ls_wR_factor_gt 0.0475 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _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 0.0000 0.190800(13) 0.7500 0.02106(6) Uani 1 4 d S . . N1 N 0.0000 0.34071(14) 0.68337(7) 0.0180(2) Uani 1 2 d S . . C1 C 0.0000 0.45660(15) 0.71384(8) 0.0178(3) Uani 1 2 d S . . C2 C 0.0000 0.57220(16) 0.68066(8) 0.0211(3) Uani 1 2 d S . . H2 H 0.0000 0.5734 0.6331 0.025 Uiso 1 2 calc SR . . C3 C 0.0000 0.68488(15) 0.71517(10) 0.0232(3) Uani 1 2 d S . . H3 H 0.0000 0.7614 0.6913 0.028 Uiso 1 2 calc SR . . C4 C 0.0000 0.32433(16) 0.60962(8) 0.0196(3) Uani 1 2 d S . . C5 C 0.1875(2) 0.37711(14) 0.57714(6) 0.0295(3) Uani 1 1 d . . . H5A H 0.1942 0.4671 0.5851 0.044 Uiso 1 1 calc . . . H5B H 0.1845 0.3611 0.5288 0.044 Uiso 1 1 calc . . . H5C H 0.3033 0.3368 0.5968 0.044 Uiso 1 1 calc . . . C6 C 0.0000 0.18405(16) 0.59515(10) 0.0271(4) Uani 1 2 d S . . H6A H 0.120(3) 0.1435(18) 0.6110(9) 0.029(4) Uiso 1 1 d . . . H6B H 0.0000 0.165(3) 0.5466(17) 0.039(8) Uiso 1 2 d S . . 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 0.02896(10) 0.01610(9) 0.01812(9) 0.000 0.000 0.000 N1 0.0210(6) 0.0186(6) 0.0143(6) -0.0006(5) 0.000 0.000 C1 0.0176(6) 0.0184(6) 0.0173(7) 0.0003(5) 0.000 0.000 C2 0.0254(7) 0.0203(7) 0.0178(7) 0.0033(6) 0.000 0.000 C3 0.0276(8) 0.0186(7) 0.0233(9) 0.0028(5) 0.000 0.000 C4 0.0222(7) 0.0217(7) 0.0151(7) -0.0019(5) 0.000 0.000 C5 0.0309(6) 0.0349(6) 0.0226(5) -0.0022(5) 0.0079(5) -0.0053(5) C6 0.0363(10) 0.0237(8) 0.0212(8) -0.0056(6) 0.000 0.000 _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 N1 2.0883(14) 10_557 ? Sn1 N1 2.0883(14) . ? N1 C1 1.385(2) . ? N1 C4 1.483(2) . ? C1 C2 1.407(2) . ? C1 C1 1.444(3) 10_557 ? C2 C3 1.392(2) . ? C3 C3 1.391(4) 10_557 ? C4 C6 1.534(2) . ? C4 C5 1.5374(16) 12 ? C4 C5 1.5374(16) . ? 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 Sn1 N1 79.16(8) 10_557 . ? C1 N1 C4 122.87(14) . . ? C1 N1 Sn1 114.36(10) . . ? C4 N1 Sn1 122.77(11) . . ? N1 C1 C2 125.85(14) . . ? N1 C1 C1 116.06(9) . 10_557 ? C2 C1 C1 118.09(9) . 10_557 ? C3 C2 C1 122.24(15) . . ? C3 C3 C2 119.67(10) 10_557 . ? N1 C4 C6 107.66(14) . . ? N1 C4 C5 112.04(9) . 12 ? C6 C4 C5 106.41(10) . 12 ? N1 C4 C5 112.04(9) . . ? C6 C4 C5 106.41(10) . . ? C5 C4 C5 111.86(15) 12 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.853 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 949608' ####################################################################### # # 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_sad5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N2 Sn' _chemical_formula_weight 377.00 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 Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 24.0650(9) _cell_length_b 9.4662(3) _cell_length_c 6.1652(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1404.46(8) _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 'dark red' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 1.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6806 _exptl_absorpt_correction_T_max 0.9310 _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 = 0.822576 ; _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 8236 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2173 _reflns_number_gt 2151 _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^)+(0.0354P)^2^+0.3576P] 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 -0.015(19) _refine_ls_number_reflns 2173 _refine_ls_number_parameters 97 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0178 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0462 _refine_ls_wR_factor_gt 0.0460 _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 Sn1 Sn 0.5000 0.894867(12) 0.70706(2) 0.01553(5) Uani 1 2 d S . . N1 N 0.55492(6) 0.80778(15) 0.4767(2) 0.0149(2) Uani 1 1 d . . . C1 C 0.53000(7) 0.74837(16) 0.2964(3) 0.0137(3) Uani 1 1 d . . . C2 C 0.55799(7) 0.69379(17) 0.1160(3) 0.0166(3) Uani 1 1 d . . . H2 H 0.5974 0.6971 0.1118 0.020 Uiso 1 1 calc R . . C3 C 0.52919(8) 0.63486(19) -0.0573(3) 0.0177(3) Uani 1 1 d . . . H3 H 0.5490 0.5946 -0.1756 0.021 Uiso 1 1 calc R . . C4 C 0.61049(7) 0.77995(17) 0.5398(3) 0.0149(3) Uani 1 1 d . . . C5 C 0.63541(7) 0.6473(2) 0.5154(3) 0.0174(3) Uani 1 1 d . . . H5 H 0.6167 0.5753 0.4367 0.021 Uiso 1 1 calc R . . C6 C 0.68744(9) 0.6199(2) 0.6057(3) 0.0214(4) Uani 1 1 d . . . H6 H 0.7041 0.5298 0.5868 0.026 Uiso 1 1 calc R . . C7 C 0.71510(7) 0.7234(2) 0.7229(5) 0.0243(3) Uani 1 1 d . . . H7 H 0.7502 0.7035 0.7869 0.029 Uiso 1 1 calc R . . C8 C 0.69126(8) 0.8561(2) 0.7463(3) 0.0237(4) Uani 1 1 d . . . H8 H 0.7103 0.9277 0.8248 0.028 Uiso 1 1 calc R . . C9 C 0.63912(9) 0.88479(18) 0.6542(3) 0.0200(4) Uani 1 1 d . . . H9 H 0.6232 0.9760 0.6696 0.024 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 0.01656(7) 0.01540(7) 0.01464(7) -0.00448(7) 0.000 0.000 N1 0.0143(6) 0.0168(6) 0.0136(6) -0.0017(4) -0.0011(5) 0.0009(5) C1 0.0144(7) 0.0137(7) 0.0130(6) 0.0005(5) -0.0007(5) 0.0007(5) C2 0.0173(7) 0.0188(7) 0.0138(7) 0.0013(6) 0.0008(6) 0.0024(6) C3 0.0241(9) 0.0158(6) 0.0131(7) 0.0002(6) 0.0016(6) 0.0014(6) C4 0.0142(7) 0.0174(7) 0.0132(7) 0.0014(5) 0.0005(5) -0.0004(5) C5 0.0163(7) 0.0169(7) 0.0189(7) 0.0015(6) -0.0007(6) -0.0008(6) C6 0.0179(8) 0.0256(8) 0.0207(9) 0.0014(6) -0.0001(7) 0.0028(6) C7 0.0162(6) 0.0348(8) 0.0218(9) -0.0025(10) -0.0039(9) 0.0016(5) C8 0.0190(7) 0.0296(8) 0.0223(13) -0.0035(7) -0.0031(6) -0.0053(6) C9 0.0184(8) 0.0208(8) 0.0207(10) -0.0017(5) -0.0011(6) -0.0024(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 N1 2.1077(14) 4_655 ? Sn1 N1 2.1077(14) . ? N1 C1 1.383(2) . ? N1 C4 1.417(2) . ? C1 C2 1.399(2) . ? C1 C1 1.444(3) 4_655 ? C2 C3 1.390(2) . ? C3 C3 1.405(4) 4_655 ? C4 C9 1.399(2) . ? C4 C5 1.400(2) . ? C5 C6 1.394(3) . ? C6 C7 1.387(3) . ? C7 C8 1.389(3) . ? C8 C9 1.404(3) . ? 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 Sn1 N1 77.66(7) 4_655 . ? C1 N1 C4 123.64(14) . . ? C1 N1 Sn1 115.39(10) . . ? C4 N1 Sn1 118.67(10) . . ? N1 C1 C2 125.49(14) . . ? N1 C1 C1 115.70(9) . 4_655 ? C2 C1 C1 118.77(9) . 4_655 ? C3 C2 C1 121.27(15) . . ? C2 C3 C3 119.90(10) . 4_655 ? C9 C4 C5 118.65(16) . . ? C9 C4 N1 118.10(15) . . ? C5 C4 N1 122.80(14) . . ? C6 C5 C4 120.56(17) . . ? C7 C6 C5 120.52(17) . . ? C6 C7 C8 119.63(17) . . ? C7 C8 C9 120.15(17) . . ? C4 C9 C8 120.47(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.745 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 949609' ####################################################################### # # 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_sad6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 N2 Sn' _chemical_formula_weight 545.31 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.6500(5) _cell_length_b 21.5505(9) _cell_length_c 10.9679(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2753.6(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 rhombus' _exptl_crystal_colour 'dark orange-brown' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7579 _exptl_absorpt_correction_T_max 0.8789 _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 = 0.839460 ; _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 23836 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4112 _reflns_number_gt 3691 _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^)+(0.0369P)^2^+0.9668P] 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 4112 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.220633(11) 0.2500 0.829903(12) 0.01958(5) Uani 1 2 d S . . N1 N 0.08923(10) 0.31074(5) 0.87763(10) 0.0181(2) Uani 1 1 d . . . C1 C -0.01296(12) 0.28305(6) 0.91207(12) 0.0186(3) Uani 1 1 d . . . C2 C -0.11180(13) 0.31467(7) 0.94914(14) 0.0245(3) Uani 1 1 d . . . H2 H -0.1124 0.3587 0.9495 0.029 Uiso 1 1 calc R . . C3 C -0.20885(13) 0.28245(8) 0.98528(16) 0.0306(3) Uani 1 1 d . . . H3 H -0.2755 0.3045 1.0101 0.037 Uiso 1 1 calc R . . C4 C 0.10368(11) 0.37606(6) 0.89852(12) 0.0180(2) Uani 1 1 d . . . C5 C 0.07968(12) 0.41870(6) 0.80548(13) 0.0202(3) Uani 1 1 d . . . C6 C 0.10178(14) 0.48163(7) 0.82786(14) 0.0256(3) Uani 1 1 d . . . H6 H 0.0871 0.5112 0.7656 0.031 Uiso 1 1 calc R . . C7 C 0.14436(13) 0.50133(7) 0.93850(15) 0.0285(3) Uani 1 1 d . . . H7 H 0.1603 0.5441 0.9513 0.034 Uiso 1 1 calc R . . C8 C 0.16393(13) 0.45898(7) 1.03091(14) 0.0266(3) Uani 1 1 d . . . H8 H 0.1913 0.4732 1.1076 0.032 Uiso 1 1 calc R . . C9 C 0.14408(12) 0.39584(7) 1.01338(13) 0.0211(3) Uani 1 1 d . . . C10 C 0.02753(14) 0.39927(7) 0.68516(13) 0.0256(3) Uani 1 1 d . . . H10 H 0.0239 0.3529 0.6833 0.031 Uiso 1 1 calc R . . C11 C 0.09929(17) 0.42088(9) 0.57648(15) 0.0376(4) Uani 1 1 d . . . H11A H 0.0991 0.4663 0.5730 0.056 Uiso 1 1 calc R . . H11B H 0.0665 0.4042 0.5010 0.056 Uiso 1 1 calc R . . H11C H 0.1783 0.4060 0.5857 0.056 Uiso 1 1 calc R . . C12 C -0.09496(17) 0.42436(12) 0.67406(17) 0.0447(5) Uani 1 1 d . . . H12A H -0.1420 0.4078 0.7407 0.067 Uiso 1 1 calc R . . H12B H -0.1277 0.4115 0.5957 0.067 Uiso 1 1 calc R . . H12C H -0.0936 0.4698 0.6787 0.067 Uiso 1 1 calc R . . C13 C 0.16525(14) 0.35052(8) 1.11720(14) 0.0275(3) Uani 1 1 d . . . H13 H 0.1414 0.3084 1.0884 0.033 Uiso 1 1 calc R . . C14 C 0.29133(19) 0.34683(14) 1.1517(2) 0.0542(6) Uani 1 1 d . . . H14A H 0.3365 0.3349 1.0801 0.081 Uiso 1 1 calc R . . H14B H 0.3016 0.3158 1.2161 0.081 Uiso 1 1 calc R . . H14C H 0.3172 0.3874 1.1813 0.081 Uiso 1 1 calc R . . C15 C 0.0924(2) 0.36632(13) 1.22827(19) 0.0654(8) Uani 1 1 d . . . H15A H 0.1187 0.4057 1.2633 0.098 Uiso 1 1 calc R . . H15B H 0.0999 0.3333 1.2892 0.098 Uiso 1 1 calc R . . H15C H 0.0118 0.3702 1.2038 0.098 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 0.01760(8) 0.01702(7) 0.02413(8) 0.000 0.00378(5) 0.000 N1 0.0190(5) 0.0147(5) 0.0206(5) -0.0014(4) 0.0014(4) -0.0011(4) C1 0.0194(6) 0.0168(6) 0.0195(6) -0.0013(5) 0.0012(5) -0.0009(5) C2 0.0232(7) 0.0183(6) 0.0319(7) -0.0033(5) 0.0044(6) 0.0017(5) C3 0.0233(7) 0.0284(8) 0.0400(9) -0.0036(7) 0.0106(6) 0.0031(6) C4 0.0160(6) 0.0151(6) 0.0229(6) -0.0025(5) 0.0015(5) -0.0009(5) C5 0.0186(6) 0.0162(6) 0.0258(6) -0.0007(5) -0.0004(5) 0.0004(5) C6 0.0250(7) 0.0159(6) 0.0361(8) 0.0007(5) -0.0003(6) 0.0008(5) C7 0.0279(7) 0.0163(6) 0.0414(8) -0.0084(6) 0.0008(6) -0.0023(6) C8 0.0242(7) 0.0259(7) 0.0296(7) -0.0109(6) 0.0006(6) -0.0019(6) C9 0.0185(6) 0.0216(6) 0.0232(6) -0.0034(5) 0.0007(5) -0.0007(5) C10 0.0298(8) 0.0213(7) 0.0258(7) 0.0011(5) -0.0055(6) -0.0013(6) C11 0.0421(10) 0.0429(10) 0.0279(8) -0.0002(7) 0.0035(7) 0.0014(8) C12 0.0284(9) 0.0655(14) 0.0403(10) -0.0013(9) -0.0093(7) 0.0007(9) C13 0.0310(8) 0.0297(7) 0.0219(7) -0.0019(6) -0.0025(6) -0.0011(6) C14 0.0365(11) 0.0623(15) 0.0638(14) 0.0231(12) -0.0154(9) -0.0015(10) C15 0.0806(18) 0.0808(17) 0.0347(11) 0.0186(11) 0.0243(11) 0.0296(15) _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 N1 2.0811(12) 7_565 ? Sn1 N1 2.0811(12) . ? N1 C1 1.3842(17) . ? N1 C4 1.4362(17) . ? C1 C2 1.3984(19) . ? C1 C1 1.424(3) 7_565 ? C2 C3 1.385(2) . ? C3 C3 1.399(3) 7_565 ? C4 C5 1.4013(19) . ? C4 C9 1.4108(19) . ? C5 C6 1.402(2) . ? C5 C10 1.512(2) . ? C6 C7 1.378(2) . ? C7 C8 1.383(2) . ? C8 C9 1.394(2) . ? C9 C13 1.520(2) . ? C10 C11 1.529(2) . ? C10 C12 1.531(3) . ? C13 C14 1.519(3) . ? C13 C15 1.523(3) . ? 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 Sn1 N1 77.95(6) 7_565 . ? C1 N1 C4 118.68(11) . . ? C1 N1 Sn1 115.48(9) . . ? C4 N1 Sn1 124.78(9) . . ? N1 C1 C2 125.27(12) . . ? N1 C1 C1 115.54(7) . 7_565 ? C2 C1 C1 119.16(8) . 7_565 ? C3 C2 C1 120.74(13) . . ? C2 C3 C3 120.10(9) . 7_565 ? C5 C4 C9 121.25(12) . . ? C5 C4 N1 120.21(12) . . ? C9 C4 N1 118.54(12) . . ? C4 C5 C6 118.04(13) . . ? C4 C5 C10 122.29(13) . . ? C6 C5 C10 119.63(13) . . ? C7 C6 C5 121.22(14) . . ? C6 C7 C8 120.10(14) . . ? C7 C8 C9 121.06(14) . . ? C8 C9 C4 118.27(13) . . ? C8 C9 C13 119.81(13) . . ? C4 C9 C13 121.92(13) . . ? C5 C10 C11 112.12(13) . . ? C5 C10 C12 110.25(13) . . ? C11 C10 C12 109.89(14) . . ? C14 C13 C9 112.16(15) . . ? C14 C13 C15 110.55(17) . . ? C9 C13 C15 111.40(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.999 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 949610' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H59 Li N2 O2 Sn' _chemical_formula_sum 'C38 H59 Li N2 O2 Sn' _chemical_formula_weight 701.50 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' Li Li -0.0003 0.0001 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7805(4) _cell_length_b 11.2513(4) _cell_length_c 14.5939(6) _cell_angle_alpha 97.0290(10) _cell_angle_beta 95.4150(10) _cell_angle_gamma 94.3510(10) _cell_volume 1742.16(11) _cell_formula_units_Z 2 _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 plate' _exptl_crystal_colour 'intens orange' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.768 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 0.9773 _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 = 0.826233 ; _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 20483 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10073 _reflns_number_gt 9091 _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. The n-Bu group is disorderd. The disorder has been resolved leading to reasonable values for the bond distances and ADPs. The first atom of the n-Bu group bond to Sn (C35) has been refined with SOF = 1.0 (anisotropic thermal parameters). For the remaining three atoms (C36-C38) three sets of positional parameters have been identified with SOF = 0.5, 0.3 and 0.2. The positional parametes for the set with SOF = 0.5 were refined with anisotropic displacement factors, those with SOF = 0.3 and 0.2 with isotropic thermal parameters. No hydrogen positons have been calculated for disordered atoms. The maximum residual electron density measures 4.596 e/cub Ang. This electron density is located less than 1 Ang from the tin atom and cannot be assigned meanigfully to any chemical entity (possibly free electron pair at the tin atom). Due to the improved refinement the refine_diff_density_min dropped to -0.285 e/cub Ang. this now lead to a ratio of max/min eletron density of 16.13 and an A alert which cannot be addressed any further. ; _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^)+(0.0651P)^2^+1.5245P] 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 10073 _refine_ls_number_parameters 431 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.722202(14) 0.575558(13) 0.723880(10) 0.02040(6) Uani 1 1 d . C . Li1 Li 0.6314(4) 0.8232(4) 0.7798(3) 0.0258(8) Uani 1 1 d . . . O1 O 0.44824(16) 0.79248(17) 0.77479(14) 0.0289(4) Uani 1 1 d . . . O2 O 0.64099(19) 0.99894(17) 0.82048(14) 0.0319(4) Uani 1 1 d . B . N1 N 0.73289(17) 0.75033(17) 0.66967(12) 0.0186(3) Uani 1 1 d . . . N2 N 0.76936(17) 0.71960(17) 0.84227(12) 0.0184(3) Uani 1 1 d . . . C1 C 0.8407(2) 0.8165(2) 0.71726(15) 0.0188(4) Uani 1 1 d . . . C2 C 0.8587(2) 0.8023(2) 0.81508(15) 0.0188(4) Uani 1 1 d . . . C3 C 0.9566(2) 0.8728(2) 0.87016(16) 0.0236(4) Uani 1 1 d . . . H3 H 0.9663 0.8689 0.9351 0.028 Uiso 1 1 calc R . . C4 C 1.0408(2) 0.9491(2) 0.83267(18) 0.0270(5) Uani 1 1 d . . . H4 H 1.1079 0.9944 0.8717 0.032 Uiso 1 1 calc R . . C5 C 1.0268(2) 0.9588(2) 0.73920(18) 0.0283(5) Uani 1 1 d . . . H5 H 1.0845 1.0102 0.7137 0.034 Uiso 1 1 calc R . . C6 C 0.9274(2) 0.8929(2) 0.68198(17) 0.0240(4) Uani 1 1 d . . . H6 H 0.9185 0.9001 0.6176 0.029 Uiso 1 1 calc R . . C7 C 0.6930(2) 0.7574(2) 0.57125(14) 0.0188(4) Uani 1 1 d . . . C8 C 0.5670(2) 0.6796(2) 0.54676(16) 0.0239(4) Uani 1 1 d . . . H8A H 0.5794 0.5957 0.5568 0.029 Uiso 1 1 calc R . . H8B H 0.5063 0.7097 0.5889 0.029 Uiso 1 1 calc R . . C9 C 0.5130(3) 0.6815(3) 0.44609(17) 0.0295(5) Uani 1 1 d . . . H9 H 0.4317 0.6304 0.4334 0.035 Uiso 1 1 calc R . . C10 C 0.4922(3) 0.8093(3) 0.42941(19) 0.0349(6) Uani 1 1 d . . . H10A H 0.4298 0.8412 0.4694 0.042 Uiso 1 1 calc R . . H10B H 0.4596 0.8104 0.3638 0.042 Uiso 1 1 calc R . . C11 C 0.6160(3) 0.8880(3) 0.45161(18) 0.0323(5) Uani 1 1 d . . . H11 H 0.6021 0.9725 0.4414 0.039 Uiso 1 1 calc R . . C12 C 0.6663(2) 0.8856(2) 0.55336(16) 0.0246(4) Uani 1 1 d . . . H12A H 0.6043 0.9155 0.5944 0.029 Uiso 1 1 calc R . . H12B H 0.7443 0.9397 0.5685 0.029 Uiso 1 1 calc R . . C13 C 0.7831(2) 0.7054(2) 0.50382(16) 0.0258(5) Uani 1 1 d . . . H13A H 0.8657 0.7523 0.5169 0.031 Uiso 1 1 calc R . . H13B H 0.7948 0.6211 0.5133 0.031 Uiso 1 1 calc R . . C14 C 0.7311(3) 0.7096(3) 0.40237(17) 0.0315(5) Uani 1 1 d . . . H14 H 0.7918 0.6780 0.3598 0.038 Uiso 1 1 calc R . . C15 C 0.6058(3) 0.6316(3) 0.38128(18) 0.0343(6) Uani 1 1 d . . . H15A H 0.5723 0.6324 0.3158 0.041 Uiso 1 1 calc R . . H15B H 0.6184 0.5475 0.3906 0.041 Uiso 1 1 calc R . . C16 C 0.7114(3) 0.8402(3) 0.38859(18) 0.0370(6) Uani 1 1 d . . . H16A H 0.7918 0.8906 0.4035 0.044 Uiso 1 1 calc R . . H16B H 0.6810 0.8442 0.3229 0.044 Uiso 1 1 calc R . . C17 C 0.7756(2) 0.6911(2) 0.93874(15) 0.0191(4) Uani 1 1 d . . . C18 C 0.7425(2) 0.7984(2) 1.00546(16) 0.0242(4) Uani 1 1 d . . . H18A H 0.8044 0.8680 1.0051 0.029 Uiso 1 1 calc R . . H18B H 0.6590 0.8216 0.9839 0.029 Uiso 1 1 calc R . . C19 C 0.7420(3) 0.7663(3) 1.10482(17) 0.0300(5) Uani 1 1 d . . . H19 H 0.7238 0.8383 1.1472 0.036 Uiso 1 1 calc R . . C20 C 0.8696(3) 0.7271(3) 1.13756(17) 0.0308(5) Uani 1 1 d . . . H20A H 0.9352 0.7934 1.1367 0.037 Uiso 1 1 calc R . . H20B H 0.8699 0.7084 1.2021 0.037 Uiso 1 1 calc R . . C21 C 0.8978(2) 0.6164(2) 1.07434(18) 0.0281(5) Uani 1 1 d . . . H21 H 0.9809 0.5908 1.0969 0.034 Uiso 1 1 calc R . . C22 C 0.9012(2) 0.6461(2) 0.97423(16) 0.0236(4) Uani 1 1 d . . . H22A H 0.9173 0.5734 0.9332 0.028 Uiso 1 1 calc R . . H22B H 0.9701 0.7089 0.9724 0.028 Uiso 1 1 calc R . . C23 C 0.6743(2) 0.5875(2) 0.94213(17) 0.0267(5) Uani 1 1 d . . . H23A H 0.5915 0.6119 0.9199 0.032 Uiso 1 1 calc R . . H23B H 0.6915 0.5162 0.9000 0.032 Uiso 1 1 calc R . . C24 C 0.6705(3) 0.5539(3) 1.04104(18) 0.0322(5) Uani 1 1 d . . . H24 H 0.6039 0.4868 1.0405 0.039 Uiso 1 1 calc R . . C25 C 0.6409(3) 0.6640(3) 1.10604(19) 0.0369(6) Uani 1 1 d . . . H25A H 0.5580 0.6891 1.0850 0.044 Uiso 1 1 calc R . . H25B H 0.6387 0.6435 1.1700 0.044 Uiso 1 1 calc R . . C26 C 0.7968(3) 0.5142(3) 1.0757(2) 0.0347(6) Uani 1 1 d . . . H26A H 0.8154 0.4418 1.0354 0.042 Uiso 1 1 calc R . . H26B H 0.7947 0.4938 1.1397 0.042 Uiso 1 1 calc R . . C27 C 0.3645(3) 0.8655(3) 0.7286(3) 0.0424(7) Uani 1 1 d . . . H27A H 0.4099 0.9162 0.6895 0.051 Uiso 1 1 calc R . . H27B H 0.3244 0.9182 0.7743 0.051 Uiso 1 1 calc R . . C28 C 0.2686(3) 0.7773(4) 0.6697(2) 0.0492(9) Uani 1 1 d . . . H28A H 0.3001 0.7451 0.6110 0.059 Uiso 1 1 calc R . . H28B H 0.1897 0.8142 0.6555 0.059 Uiso 1 1 calc R . . C29 C 0.2509(3) 0.6812(4) 0.7317(3) 0.0553(9) Uani 1 1 d . . . H29A H 0.2240 0.6021 0.6947 0.066 Uiso 1 1 calc R . . H29B H 0.1880 0.7011 0.7751 0.066 Uiso 1 1 calc R . . C30 C 0.3796(3) 0.6805(3) 0.7839(2) 0.0356(6) Uani 1 1 d . . . H30A H 0.3723 0.6733 0.8502 0.043 Uiso 1 1 calc R . . H30B H 0.4227 0.6119 0.7571 0.043 Uiso 1 1 calc R . . C31 C 0.7358(3) 1.0900(3) 0.8049(2) 0.0372(6) Uani 1 1 d . . . H31A H 0.7023 1.1440 0.7617 0.045 Uiso 0.50 1 calc PR A 3 H31B H 0.8091 1.0540 0.7807 0.045 Uiso 0.50 1 calc PR A 3 H31C H 0.7231 1.1076 0.7400 0.045 Uiso 0.50 1 d PR A 4 H31D H 0.8197 1.0608 0.8152 0.045 Uiso 0.50 1 d PR A 4 C32 C 0.7691(10) 1.1580(10) 0.9071(7) 0.067(3) Uani 0.50 1 d P B 3 H32A H 0.8421 1.1254 0.9385 0.081 Uiso 0.50 1 calc PR B 3 H32B H 0.7893 1.2450 0.9056 0.081 Uiso 0.50 1 calc PR B 3 C32A C 0.7275(8) 1.1994(7) 0.8698(7) 0.052(2) Uani 0.50 1 d P B 4 H32C H 0.6733 1.2556 0.8420 0.063 Uiso 0.50 1 calc PR B 4 H32D H 0.8110 1.2414 0.8915 0.063 Uiso 0.50 1 calc PR B 4 C33 C 0.6635(4) 1.1391(4) 0.9542(3) 0.0639(12) Uani 1 1 d . . . H33A H 0.6256 1.2158 0.9687 0.077 Uiso 0.50 1 calc PR B 3 H33B H 0.6872 1.1075 1.0132 0.077 Uiso 0.50 1 calc PR B 3 H33C H 0.7244 1.1001 0.9931 0.077 Uiso 0.50 1 d PR B 4 H33D H 0.6214 1.1980 0.9938 0.077 Uiso 0.50 1 d PR B 4 C34 C 0.5722(3) 1.0504(3) 0.8926(2) 0.0436(7) Uani 1 1 d . B . H34A H 0.5389 0.9874 0.9278 0.052 Uiso 1 1 calc R . . H34B H 0.5015 1.0909 0.8662 0.052 Uiso 1 1 calc R . . C35 C 0.9197(2) 0.5382(3) 0.7074(2) 0.0351(6) Uani 1 1 d D . . C36 C 0.9267(5) 0.4331(4) 0.6310(4) 0.0369(12) Uani 0.50 1 d PD C 1 C37 C 0.8739(5) 0.3144(5) 0.6599(4) 0.0344(11) Uani 0.50 1 d PD C 1 C38 C 0.8955(12) 0.2037(6) 0.5929(8) 0.041(2) Uani 0.50 1 d PD C 1 C36B C 0.9351(8) 0.4038(5) 0.6879(5) 0.0306(17) Uiso 0.30 1 d PD C 2 C37B C 0.8826(8) 0.3455(9) 0.5905(5) 0.0301(17) Uiso 0.30 1 d PD C 2 C38B C 0.879(2) 0.2081(10) 0.5732(13) 0.041(5) Uiso 0.30 1 d PD C 2 C36C C 0.9714(12) 0.4903(12) 0.6179(6) 0.037(3) Uiso 0.20 1 d PD C 3 C37C C 0.8853(12) 0.3870(10) 0.5623(9) 0.029(2) Uiso 0.20 1 d PD C 3 C38C C 0.8756(18) 0.2717(16) 0.6081(15) 0.048(4) Uiso 0.20 1 d PD C 3 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 0.01972(8) 0.02165(8) 0.01894(8) 0.00114(5) 0.00083(5) -0.00010(5) Li1 0.0243(19) 0.028(2) 0.025(2) 0.0026(16) 0.0041(15) 0.0041(16) O1 0.0204(8) 0.0326(9) 0.0353(10) 0.0103(8) 0.0027(7) 0.0036(7) O2 0.0325(9) 0.0280(9) 0.0358(10) -0.0006(8) 0.0128(8) 0.0030(7) N1 0.0183(8) 0.0239(9) 0.0132(8) 0.0026(6) 0.0016(6) -0.0008(7) N2 0.0198(8) 0.0209(8) 0.0138(8) 0.0016(6) 0.0019(6) -0.0011(7) C1 0.0184(9) 0.0219(10) 0.0159(9) 0.0022(7) 0.0024(7) 0.0011(8) C2 0.0185(9) 0.0218(10) 0.0162(9) 0.0021(7) 0.0032(7) 0.0016(8) C3 0.0238(10) 0.0253(11) 0.0203(10) 0.0025(8) -0.0011(8) -0.0015(9) C4 0.0222(10) 0.0282(12) 0.0281(12) 0.0015(9) -0.0012(9) -0.0048(9) C5 0.0237(11) 0.0301(12) 0.0307(12) 0.0049(10) 0.0056(9) -0.0063(9) C6 0.0236(10) 0.0281(11) 0.0211(10) 0.0052(8) 0.0056(8) -0.0009(9) C7 0.0206(9) 0.0236(10) 0.0126(8) 0.0019(7) 0.0028(7) 0.0028(8) C8 0.0231(10) 0.0307(12) 0.0162(9) 0.0005(8) -0.0002(8) -0.0016(9) C9 0.0302(12) 0.0386(14) 0.0175(10) 0.0006(9) -0.0028(9) 0.0003(10) C10 0.0359(14) 0.0437(15) 0.0247(12) 0.0065(11) -0.0061(10) 0.0090(12) C11 0.0423(14) 0.0330(13) 0.0232(11) 0.0095(10) -0.0001(10) 0.0084(11) C12 0.0293(11) 0.0251(11) 0.0198(10) 0.0035(8) 0.0022(8) 0.0057(9) C13 0.0281(11) 0.0324(12) 0.0184(10) 0.0019(9) 0.0080(8) 0.0072(9) C14 0.0373(13) 0.0413(14) 0.0170(10) 0.0012(10) 0.0099(9) 0.0059(11) C15 0.0447(15) 0.0388(14) 0.0170(10) -0.0045(10) 0.0026(10) 0.0033(12) C16 0.0499(16) 0.0450(16) 0.0181(11) 0.0111(10) 0.0072(11) 0.0014(13) C17 0.0202(9) 0.0219(10) 0.0153(9) 0.0028(7) 0.0019(7) 0.0016(8) C18 0.0285(11) 0.0272(11) 0.0179(10) 0.0020(8) 0.0039(8) 0.0088(9) C19 0.0356(13) 0.0395(14) 0.0165(10) 0.0026(9) 0.0064(9) 0.0100(11) C20 0.0365(13) 0.0371(13) 0.0180(10) 0.0062(9) -0.0034(9) 0.0027(11) C21 0.0300(12) 0.0298(12) 0.0250(11) 0.0089(9) -0.0041(9) 0.0054(10) C22 0.0234(10) 0.0252(11) 0.0232(10) 0.0048(8) 0.0018(8) 0.0065(8) C23 0.0275(11) 0.0306(12) 0.0219(10) 0.0084(9) 0.0010(9) -0.0041(9) C24 0.0335(13) 0.0389(14) 0.0247(11) 0.0143(10) 0.0018(10) -0.0072(11) C25 0.0349(14) 0.0566(18) 0.0226(12) 0.0134(12) 0.0102(10) 0.0044(13) C26 0.0431(15) 0.0328(13) 0.0295(13) 0.0151(11) -0.0023(11) 0.0002(11) C27 0.0312(14) 0.0462(17) 0.0553(19) 0.0233(15) 0.0048(13) 0.0113(12) C28 0.0317(14) 0.080(3) 0.0368(16) 0.0064(16) -0.0004(12) 0.0205(16) C29 0.0300(15) 0.056(2) 0.076(3) 0.0062(19) -0.0085(16) -0.0038(14) C30 0.0291(13) 0.0356(14) 0.0425(15) 0.0093(12) 0.0034(11) -0.0016(11) C31 0.0377(14) 0.0260(12) 0.0476(17) 0.0027(11) 0.0101(12) -0.0015(11) C32 0.059(6) 0.065(6) 0.066(6) -0.027(5) 0.009(4) -0.026(5) C32A 0.046(4) 0.032(4) 0.073(6) -0.013(3) 0.010(4) -0.004(3) C33 0.065(2) 0.072(3) 0.048(2) -0.0241(19) -0.0007(18) 0.025(2) C34 0.0478(17) 0.0386(16) 0.0470(17) -0.0015(13) 0.0231(14) 0.0097(13) C35 0.0225(11) 0.0328(13) 0.0479(16) -0.0043(12) 0.0034(11) 0.0053(10) C36 0.036(3) 0.039(3) 0.041(3) 0.008(2) 0.017(2) 0.015(2) C37 0.035(3) 0.033(3) 0.036(3) 0.006(2) 0.006(2) 0.005(2) C38 0.057(6) 0.029(3) 0.037(5) -0.002(3) 0.002(4) 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 N1 2.2067(19) . ? Sn1 N2 2.2122(18) . ? Sn1 C35 2.230(3) . ? Sn1 Li1 3.066(4) . ? Li1 O1 1.972(5) . ? Li1 O2 1.985(5) . ? Li1 N1 2.144(5) . ? Li1 N2 2.161(5) . ? Li1 C2 2.491(5) . ? Li1 C1 2.516(5) . ? O1 C30 1.440(3) . ? O1 C27 1.442(3) . ? O2 C34 1.434(3) . ? O2 C31 1.445(3) . ? N1 C1 1.406(3) . ? N1 C7 1.473(3) . ? N2 C2 1.407(3) . ? N2 C17 1.478(3) . ? C1 C6 1.398(3) . ? C1 C2 1.452(3) . ? C2 C3 1.395(3) . ? C3 C4 1.396(3) . ? C4 C5 1.377(4) . ? C5 C6 1.399(3) . ? C7 C12 1.541(3) . ? C7 C13 1.543(3) . ? C7 C8 1.546(3) . ? C8 C9 1.532(3) . ? C9 C10 1.518(4) . ? C9 C15 1.531(4) . ? C10 C11 1.529(4) . ? C11 C16 1.528(4) . ? C11 C12 1.536(3) . ? C13 C14 1.541(3) . ? C14 C16 1.535(4) . ? C14 C15 1.538(4) . ? C17 C18 1.541(3) . ? C17 C23 1.545(3) . ? C17 C22 1.546(3) . ? C18 C19 1.537(3) . ? C19 C25 1.527(4) . ? C19 C20 1.528(4) . ? C20 C21 1.525(4) . ? C21 C26 1.526(4) . ? C21 C22 1.541(3) . ? C23 C24 1.540(3) . ? C24 C26 1.526(4) . ? C24 C25 1.538(4) . ? C27 C28 1.503(5) . ? C28 C29 1.505(6) . ? C29 C30 1.519(4) . ? C31 C32A 1.472(8) . ? C31 C32 1.587(10) . ? C32 C33 1.400(11) . ? C32A C33 1.657(11) . ? C33 C34 1.495(6) . ? C35 C36C 1.523(5) . ? C35 C36B 1.529(5) . ? C35 C36 1.534(4) . ? C36 C37 1.534(5) . ? C37 C38 1.532(7) . ? C36B C37B 1.528(5) . ? C37B C38B 1.532(8) . ? C36C C37C 1.528(5) . ? C37C C38C 1.532(8) . ? 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 Sn1 N2 71.50(7) . . ? N1 Sn1 C35 96.15(10) . . ? N2 Sn1 C35 95.34(9) . . ? N1 Sn1 Li1 44.38(9) . . ? N2 Sn1 Li1 44.82(10) . . ? C35 Sn1 Li1 125.76(11) . . ? O1 Li1 O2 97.0(2) . . ? O1 Li1 N1 121.7(2) . . ? O2 Li1 N1 121.4(2) . . ? O1 Li1 N2 126.4(2) . . ? O2 Li1 N2 118.6(2) . . ? N1 Li1 N2 73.69(15) . . ? O1 Li1 C2 160.6(2) . . ? O2 Li1 C2 96.05(19) . . ? N1 Li1 C2 61.58(13) . . ? N2 Li1 C2 34.28(9) . . ? O1 Li1 C1 155.4(2) . . ? O2 Li1 C1 97.92(19) . . ? N1 Li1 C1 33.96(9) . . ? N2 Li1 C1 61.03(13) . . ? C2 Li1 C1 33.72(9) . . ? O1 Li1 Sn1 104.42(18) . . ? O2 Li1 Sn1 158.5(2) . . ? N1 Li1 Sn1 46.04(10) . . ? N2 Li1 Sn1 46.18(10) . . ? C2 Li1 Sn1 63.03(11) . . ? C1 Li1 Sn1 62.28(11) . . ? C30 O1 C27 108.2(2) . . ? C30 O1 Li1 126.6(2) . . ? C27 O1 Li1 121.7(2) . . ? C34 O2 C31 107.5(2) . . ? C34 O2 Li1 122.6(2) . . ? C31 O2 Li1 127.8(2) . . ? C1 N1 C7 122.42(18) . . ? C1 N1 Li1 87.66(17) . . ? C7 N1 Li1 122.43(18) . . ? C1 N1 Sn1 105.94(13) . . ? C7 N1 Sn1 120.37(14) . . ? Li1 N1 Sn1 89.58(14) . . ? C2 N2 C17 121.12(18) . . ? C2 N2 Li1 85.81(17) . . ? C17 N2 Li1 125.04(18) . . ? C2 N2 Sn1 106.85(13) . . ? C17 N2 Sn1 120.54(14) . . ? Li1 N2 Sn1 89.00(13) . . ? C6 C1 N1 127.9(2) . . ? C6 C1 C2 118.5(2) . . ? N1 C1 C2 113.54(19) . . ? C6 C1 Li1 138.9(2) . . ? N1 C1 Li1 58.39(15) . . ? C2 C1 Li1 72.21(16) . . ? C3 C2 N2 128.3(2) . . ? C3 C2 C1 117.9(2) . . ? N2 C2 C1 113.75(19) . . ? C3 C2 Li1 134.16(19) . . ? N2 C2 Li1 59.92(15) . . ? C1 C2 Li1 74.07(16) . . ? C2 C3 C4 121.9(2) . . ? C5 C4 C3 120.1(2) . . ? C4 C5 C6 119.8(2) . . ? C1 C6 C5 121.6(2) . . ? N1 C7 C12 112.50(18) . . ? N1 C7 C13 113.96(18) . . ? C12 C7 C13 110.54(19) . . ? N1 C7 C8 106.80(17) . . ? C12 C7 C8 106.00(19) . . ? C13 C7 C8 106.46(19) . . ? C9 C8 C7 112.3(2) . . ? C10 C9 C15 109.2(2) . . ? C10 C9 C8 110.0(2) . . ? C15 C9 C8 108.8(2) . . ? C9 C10 C11 109.4(2) . . ? C16 C11 C10 109.8(2) . . ? C16 C11 C12 109.2(2) . . ? C10 C11 C12 109.5(2) . . ? C11 C12 C7 111.1(2) . . ? C14 C13 C7 110.7(2) . . ? C16 C14 C15 109.9(2) . . ? C16 C14 C13 109.2(2) . . ? C15 C14 C13 109.1(2) . . ? C9 C15 C14 109.2(2) . . ? C11 C16 C14 109.8(2) . . ? N2 C17 C18 111.00(18) . . ? N2 C17 C23 107.75(18) . . ? C18 C17 C23 106.26(19) . . ? N2 C17 C22 114.36(18) . . ? C18 C17 C22 110.89(18) . . ? C23 C17 C22 106.09(19) . . ? C19 C18 C17 111.0(2) . . ? C25 C19 C20 109.6(2) . . ? C25 C19 C18 109.2(2) . . ? C20 C19 C18 109.7(2) . . ? C21 C20 C19 110.0(2) . . ? C20 C21 C26 109.7(2) . . ? C20 C21 C22 109.8(2) . . ? C26 C21 C22 109.4(2) . . ? C21 C22 C17 110.56(19) . . ? C24 C23 C17 111.7(2) . . ? C26 C24 C25 109.4(2) . . ? C26 C24 C23 109.9(2) . . ? C25 C24 C23 109.3(2) . . ? C19 C25 C24 108.8(2) . . ? C24 C26 C21 108.9(2) . . ? O1 C27 C28 105.0(3) . . ? C27 C28 C29 101.8(3) . . ? C28 C29 C30 103.8(3) . . ? O1 C30 C29 106.7(3) . . ? O2 C31 C32A 108.9(4) . . ? O2 C31 C32 100.6(4) . . ? C32A C31 C32 32.9(5) . . ? C33 C32 C31 106.7(6) . . ? C31 C32A C33 99.9(5) . . ? C32 C33 C34 107.8(4) . . ? C32 C33 C32A 31.8(5) . . ? C34 C33 C32A 96.4(4) . . ? O2 C34 C33 105.7(3) . . ? C36C C35 C36B 61.1(6) . . ? C36C C35 C36 31.4(5) . . ? C36B C35 C36 35.4(4) . . ? C36C C35 Sn1 126.6(5) . . ? C36B C35 Sn1 112.6(4) . . ? C36 C35 Sn1 111.5(3) . . ? C37 C36 C35 110.9(4) . . ? C38 C37 C36 113.4(6) . . ? C37B C36B C35 114.5(6) . . ? C36B C37B C38B 115.8(10) . . ? C35 C36C C37C 111.9(9) . . ? C36C C37C C38C 114.7(14) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 4.596 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.115 # end of data set 1 _database_code_depnum_ccdc_archive 'CCDC 949611'