# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'P. Power' _publ_contact_author_address ; Department of Chemistry University of California Davis CA 95616 UNITED STATES OF AMERICA ; _publ_contact_author_email PPPOWER@UCDAVIS.EDU _publ_section_title ; Different reactivity of the heavier group 14 element alkyne analogues Ar'MMAr' (M = Ge, Sn; Ar' = C6H3-2,6(C6H3-2,6-Pri2)2) with R2NO ; loop_ _publ_author_name 'P. Power' 'James C. Fettinger' 'Yang Peng.' 'Geoffrey H. Spikes' 'Jochen Steiner' data_sad _database_code_depnum_ccdc_archive 'CCDC 284211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3 _chemical_melting_point ? _chemical_formula_moiety 'C39 H55 Ge N O' _chemical_formula_sum 'C39 H55 Ge N O' _chemical_formula_weight 626.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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 10.6934(4) _cell_length_b 11.1998(4) _cell_length_c 16.0422(6) _cell_angle_alpha 100.9760(10) _cell_angle_beta 91.3530(10) _cell_angle_gamma 108.1400(10) _cell_volume 1785.30(11) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 7476 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 30.01 _exptl_crystal_description Block _exptl_crystal_colour Yello _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.887 _exptl_absorpt_correction_type 'Empirical, SADABS (multi-scan)' _exptl_absorpt_correction_T_min 0.6269 _exptl_absorpt_correction_T_max 0.9166 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24120 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0497 _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 -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 30.04 _reflns_number_total 10297 _reflns_number_gt 8042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Version 5.054) (Bruker, 2002)' _computing_cell_refinement 'SAINT (7.16b) (Bruker, 2004)' _computing_data_reduction 'SAINT (7.16b) (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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^)+(0.0372P)^2^+0.8676P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10297 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Ge1 Ge 0.399031(18) 0.723842(18) 0.804467(11) 0.01661(6) Uani 1 1 d . . . O1 O 0.24142(12) 0.73803(12) 0.83331(7) 0.0177(2) Uani 1 1 d . . . N1 N 0.26546(14) 0.82191(13) 0.91897(8) 0.0162(3) Uani 1 1 d . . . C1 C 0.34539(16) 0.61188(16) 0.68553(10) 0.0143(3) Uani 1 1 d . . . C2 C 0.34843(15) 0.48549(16) 0.67547(10) 0.0142(3) Uani 1 1 d . . . C7 C 0.35349(17) 0.43385(16) 0.75500(10) 0.0152(3) Uani 1 1 d . . . C4 C 0.34174(17) 0.46324(17) 0.52283(10) 0.0180(3) Uani 1 1 d . . . H4A H 0.3412 0.4133 0.4678 0.022 Uiso 1 1 calc R . . C6 C 0.34013(16) 0.66267(16) 0.61222(10) 0.0149(3) Uani 1 1 d . . . C3 C 0.34569(16) 0.41143(17) 0.59461(11) 0.0169(3) Uani 1 1 d . . . H3A H 0.3465 0.3256 0.5886 0.020 Uiso 1 1 calc R . . C19 C 0.33494(18) 0.79679(16) 0.62132(10) 0.0173(3) Uani 1 1 d . . . C12 C 0.47561(17) 0.46391(17) 0.80312(11) 0.0178(3) Uani 1 1 d . . . C31 C 0.18344(18) 0.74545(17) 0.97637(11) 0.0195(3) Uani 1 1 d . . . C9 C 0.24117(19) 0.32380(17) 0.86103(11) 0.0219(4) Uani 1 1 d . . . H9A H 0.1624 0.2751 0.8809 0.026 Uiso 1 1 calc R . . C5 C 0.33850(17) 0.58793(17) 0.53164(10) 0.0178(3) Uani 1 1 d . . . H5A H 0.3351 0.6227 0.4824 0.021 Uiso 1 1 calc R . . C8 C 0.23525(17) 0.36063(16) 0.78303(11) 0.0179(3) Uani 1 1 d . . . C20 C 0.21150(19) 0.81563(18) 0.61113(11) 0.0224(4) Uani 1 1 d . . . C16 C 0.60502(17) 0.52708(18) 0.76794(12) 0.0215(4) Uani 1 1 d . . . H16A H 0.5857 0.5757 0.7258 0.026 Uiso 1 1 calc R . . C35 C 0.2472(2) 0.94537(18) 0.90963(11) 0.0227(4) Uani 1 1 d . . . C13 C 0.10401(17) 0.32381(18) 0.73028(12) 0.0215(4) Uani 1 1 d . . . H13A H 0.1237 0.3368 0.6714 0.026 Uiso 1 1 calc R . . C24 C 0.45217(19) 0.90272(18) 0.64061(11) 0.0225(4) Uani 1 1 d . . . C25 C 0.08500(19) 0.7029(2) 0.58326(13) 0.0266(4) Uani 1 1 d . . . H25A H 0.1072 0.6227 0.5843 0.032 Uiso 1 1 calc R . . C11 C 0.47604(19) 0.42532(18) 0.88100(11) 0.0229(4) Uani 1 1 d . . . H11A H 0.5572 0.4463 0.9146 0.027 Uiso 1 1 calc R . . C10 C 0.3599(2) 0.35709(18) 0.90972(11) 0.0236(4) Uani 1 1 d . . . H10A H 0.3617 0.3329 0.9633 0.028 Uiso 1 1 calc R . . C17 C 0.7110(2) 0.6218(2) 0.83524(13) 0.0315(5) Uani 1 1 d . . . H17A H 0.6756 0.6861 0.8669 0.047 Uiso 1 1 calc R . . H17B H 0.7879 0.6647 0.8073 0.047 Uiso 1 1 calc R . . H17C H 0.7377 0.5754 0.8747 0.047 Uiso 1 1 calc R . . C28 C 0.58672(19) 0.88351(19) 0.64418(12) 0.0263(4) Uani 1 1 d . . . H28A H 0.5723 0.7923 0.6482 0.032 Uiso 1 1 calc R . . C34 C 0.2597(2) 1.02760(19) 0.99985(12) 0.0272(4) Uani 1 1 d . . . H34A H 0.3526 1.0545 1.0243 0.033 Uiso 1 1 calc R . . H34B H 0.2381 1.1062 0.9958 0.033 Uiso 1 1 calc R . . C15 C 0.0227(2) 0.18218(19) 0.72299(14) 0.0313(5) Uani 1 1 d . . . H15A H 0.0777 0.1282 0.7043 0.047 Uiso 1 1 calc R . . H15B H -0.0539 0.1592 0.6814 0.047 Uiso 1 1 calc R . . H15C H -0.0076 0.1686 0.7787 0.047 Uiso 1 1 calc R . . C36 C 0.2426(2) 0.63991(19) 0.98477(12) 0.0264(4) Uani 1 1 d . . . H36A H 0.3383 0.6779 0.9987 0.040 Uiso 1 1 calc R . . H36B H 0.2244 0.5769 0.9308 0.040 Uiso 1 1 calc R . . H36C H 0.2029 0.5973 1.0302 0.040 Uiso 1 1 calc R . . C32 C 0.2023(2) 0.83616(19) 1.06390(11) 0.0245(4) Uani 1 1 d . . . H32A H 0.1447 0.7904 1.1030 0.029 Uiso 1 1 calc R . . H32B H 0.2950 0.8596 1.0878 0.029 Uiso 1 1 calc R . . C18 C 0.6561(2) 0.4218(2) 0.71968(14) 0.0324(5) Uani 1 1 d . . . H18A H 0.5891 0.3652 0.6744 0.049 Uiso 1 1 calc R . . H18B H 0.6746 0.3716 0.7593 0.049 Uiso 1 1 calc R . . H18C H 0.7374 0.4616 0.6945 0.049 Uiso 1 1 calc R . . C33 C 0.1705(2) 0.95818(19) 1.05965(12) 0.0267(4) Uani 1 1 d . . . H33A H 0.0768 0.9365 1.0385 0.032 Uiso 1 1 calc R . . H33B H 0.1851 1.0140 1.1172 0.032 Uiso 1 1 calc R . . C37 C 0.03585(19) 0.6831(2) 0.94613(14) 0.0303(4) Uani 1 1 d . . . H37A H 0.0258 0.6451 0.8851 0.045 Uiso 1 1 calc R . . H37B H -0.0084 0.7484 0.9564 0.045 Uiso 1 1 calc R . . H37C H -0.0040 0.6158 0.9777 0.045 Uiso 1 1 calc R . . C21 C 0.2075(2) 0.9410(2) 0.62355(12) 0.0306(5) Uani 1 1 d . . . H21A H 0.1250 0.9551 0.6173 0.037 Uiso 1 1 calc R . . C14 C 0.0238(2) 0.4107(2) 0.76533(15) 0.0349(5) Uani 1 1 d . . . H14A H 0.0744 0.5001 0.7651 0.052 Uiso 1 1 calc R . . H14B H 0.0052 0.4021 0.8238 0.052 Uiso 1 1 calc R . . H14C H -0.0595 0.3855 0.7296 0.052 Uiso 1 1 calc R . . C38 C 0.1185(2) 0.9329(2) 0.85999(13) 0.0366(5) Uani 1 1 d . . . H38A H 0.0440 0.9012 0.8931 0.055 Uiso 1 1 calc R . . H38B H 0.1077 0.8724 0.8054 0.055 Uiso 1 1 calc R . . H38C H 0.1213 1.0171 0.8496 0.055 Uiso 1 1 calc R . . C39 C 0.3636(3) 1.0129(2) 0.86327(14) 0.0380(5) Uani 1 1 d . . . H39A H 0.3535 0.9668 0.8038 0.057 Uiso 1 1 calc R . . H39B H 0.4463 1.0136 0.8913 0.057 Uiso 1 1 calc R . . H39C H 0.3655 1.1014 0.8650 0.057 Uiso 1 1 calc R . . C23 C 0.4423(2) 1.02599(19) 0.65182(12) 0.0309(5) Uani 1 1 d . . . H23A H 0.5205 1.0982 0.6645 0.037 Uiso 1 1 calc R . . C22 C 0.3218(2) 1.0453(2) 0.64483(13) 0.0335(5) Uani 1 1 d . . . H22A H 0.3172 1.1301 0.6546 0.040 Uiso 1 1 calc R . . C29 C 0.6513(2) 0.9040(2) 0.56177(14) 0.0384(5) Uani 1 1 d . . . H29A H 0.7348 0.8852 0.5629 0.058 Uiso 1 1 calc R . . H29B H 0.6684 0.9934 0.5566 0.058 Uiso 1 1 calc R . . H29C H 0.5920 0.8466 0.5129 0.058 Uiso 1 1 calc R . . C27 C 0.0367(3) 0.6953(3) 0.49131(14) 0.0451(6) Uani 1 1 d . . . H27A H 0.1068 0.6893 0.4541 0.068 Uiso 1 1 calc R . . H27B H 0.0138 0.7725 0.4879 0.068 Uiso 1 1 calc R . . H27C H -0.0414 0.6192 0.4731 0.068 Uiso 1 1 calc R . . C30 C 0.6786(2) 0.9693(3) 0.72147(14) 0.0488(7) Uani 1 1 d . . . H30A H 0.7589 0.9451 0.7245 0.073 Uiso 1 1 calc R . . H30B H 0.6338 0.9586 0.7734 0.073 Uiso 1 1 calc R . . H30C H 0.7021 1.0592 0.7162 0.073 Uiso 1 1 calc R . . C26 C -0.0249(2) 0.7046(3) 0.64225(15) 0.0412(5) Uani 1 1 d . . . H26A H -0.1034 0.6302 0.6204 0.062 Uiso 1 1 calc R . . H26B H -0.0469 0.7837 0.6445 0.062 Uiso 1 1 calc R . . H26C H 0.0050 0.7009 0.6996 0.062 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 0.01598(9) 0.01790(9) 0.01393(9) -0.00003(6) 0.00174(6) 0.00456(7) O1 0.0190(6) 0.0199(6) 0.0137(5) -0.0010(5) 0.0013(5) 0.0083(5) N1 0.0202(7) 0.0150(7) 0.0119(6) 0.0000(5) 0.0022(5) 0.0054(6) C1 0.0111(7) 0.0157(8) 0.0158(7) 0.0024(6) 0.0026(6) 0.0042(6) C2 0.0101(7) 0.0166(8) 0.0155(7) 0.0027(6) 0.0019(6) 0.0040(6) C7 0.0178(8) 0.0126(7) 0.0155(7) 0.0011(6) 0.0026(6) 0.0063(6) C4 0.0156(8) 0.0212(8) 0.0143(7) -0.0022(6) 0.0010(6) 0.0053(7) C6 0.0124(7) 0.0152(8) 0.0162(7) 0.0035(6) 0.0010(6) 0.0031(6) C3 0.0143(8) 0.0164(8) 0.0191(8) 0.0008(6) 0.0018(6) 0.0055(6) C19 0.0239(9) 0.0165(8) 0.0114(7) 0.0040(6) 0.0025(6) 0.0055(7) C12 0.0185(8) 0.0173(8) 0.0183(8) 0.0031(7) 0.0007(6) 0.0072(7) C31 0.0196(9) 0.0202(8) 0.0181(8) 0.0042(7) 0.0043(7) 0.0054(7) C9 0.0284(10) 0.0144(8) 0.0232(9) 0.0063(7) 0.0088(7) 0.0054(7) C5 0.0165(8) 0.0218(9) 0.0144(7) 0.0050(7) 0.0011(6) 0.0046(7) C8 0.0196(8) 0.0136(8) 0.0199(8) 0.0011(6) 0.0030(7) 0.0057(7) C20 0.0298(10) 0.0206(9) 0.0187(8) 0.0047(7) 0.0020(7) 0.0104(8) C16 0.0143(8) 0.0279(10) 0.0228(9) 0.0074(7) 0.0001(7) 0.0062(7) C35 0.0365(11) 0.0185(9) 0.0164(8) 0.0035(7) 0.0055(7) 0.0135(8) C13 0.0163(8) 0.0223(9) 0.0226(9) 0.0050(7) 0.0034(7) 0.0015(7) C24 0.0293(10) 0.0198(9) 0.0142(8) 0.0046(7) 0.0038(7) 0.0013(7) C25 0.0234(10) 0.0283(10) 0.0299(10) 0.0033(8) -0.0012(8) 0.0127(8) C11 0.0265(10) 0.0223(9) 0.0212(8) 0.0049(7) -0.0028(7) 0.0098(8) C10 0.0353(11) 0.0193(9) 0.0178(8) 0.0071(7) 0.0025(7) 0.0093(8) C17 0.0191(9) 0.0389(12) 0.0307(10) 0.0060(9) -0.0030(8) 0.0023(8) C28 0.0227(9) 0.0255(10) 0.0227(9) 0.0047(8) 0.0012(7) -0.0034(8) C34 0.0393(12) 0.0209(9) 0.0214(9) -0.0008(7) 0.0039(8) 0.0127(8) C15 0.0217(10) 0.0222(10) 0.0422(12) -0.0021(9) 0.0040(9) 0.0012(8) C36 0.0325(11) 0.0244(10) 0.0270(9) 0.0113(8) 0.0068(8) 0.0120(8) C32 0.0298(10) 0.0290(10) 0.0163(8) 0.0053(7) 0.0075(7) 0.0112(8) C18 0.0265(10) 0.0391(12) 0.0347(11) 0.0069(9) 0.0085(9) 0.0150(9) C33 0.0338(11) 0.0302(10) 0.0177(8) -0.0005(8) 0.0051(8) 0.0156(9) C37 0.0200(9) 0.0297(11) 0.0364(11) 0.0009(9) 0.0071(8) 0.0044(8) C21 0.0463(13) 0.0288(11) 0.0252(10) 0.0099(8) 0.0062(9) 0.0214(10) C14 0.0241(10) 0.0273(11) 0.0508(13) 0.0025(10) -0.0049(9) 0.0086(8) C38 0.0560(15) 0.0431(13) 0.0230(10) 0.0011(9) -0.0025(10) 0.0373(12) C39 0.0617(16) 0.0222(10) 0.0354(12) 0.0122(9) 0.0232(11) 0.0161(10) C23 0.0464(13) 0.0182(9) 0.0217(9) 0.0053(8) 0.0079(9) 0.0000(9) C22 0.0610(15) 0.0196(10) 0.0255(10) 0.0093(8) 0.0126(10) 0.0175(10) C29 0.0431(13) 0.0466(14) 0.0266(10) 0.0061(10) 0.0148(10) 0.0162(11) C27 0.0403(14) 0.0575(16) 0.0287(11) 0.0008(11) -0.0066(10) 0.0088(12) C30 0.0263(12) 0.0674(18) 0.0293(11) -0.0048(11) 0.0027(9) -0.0092(11) C26 0.0323(12) 0.0470(14) 0.0395(12) 0.0034(11) 0.0053(10) 0.0093(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 O1 1.8043(12) . ? Ge1 C1 2.0326(16) . ? O1 N1 1.4760(17) . ? N1 C35 1.489(2) . ? N1 C31 1.490(2) . ? C1 C2 1.405(2) . ? C1 C6 1.408(2) . ? C2 C3 1.395(2) . ? C2 C7 1.504(2) . ? C7 C12 1.412(2) . ? C7 C8 1.412(2) . ? C4 C5 1.388(2) . ? C4 C3 1.390(2) . ? C4 H4A 0.9500 . ? C6 C5 1.396(2) . ? C6 C19 1.500(2) . ? C3 H3A 0.9500 . ? C19 C20 1.411(3) . ? C19 C24 1.411(2) . ? C12 C11 1.398(2) . ? C12 C16 1.521(2) . ? C31 C36 1.529(3) . ? C31 C32 1.536(2) . ? C31 C37 1.537(3) . ? C9 C10 1.381(3) . ? C9 C8 1.396(2) . ? C9 H9A 0.9500 . ? C5 H5A 0.9500 . ? C8 C13 1.519(2) . ? C20 C21 1.395(3) . ? C20 C25 1.522(3) . ? C16 C17 1.528(3) . ? C16 C18 1.537(3) . ? C16 H16A 1.0000 . ? C35 C38 1.528(3) . ? C35 C39 1.532(3) . ? C35 C34 1.539(2) . ? C13 C14 1.527(3) . ? C13 C15 1.533(3) . ? C13 H13A 1.0000 . ? C24 C23 1.395(3) . ? C24 C28 1.521(3) . ? C25 C26 1.529(3) . ? C25 C27 1.529(3) . ? C25 H25A 1.0000 . ? C11 C10 1.382(3) . ? C11 H11A 0.9500 . ? C10 H10A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C28 C30 1.525(3) . ? C28 C29 1.529(3) . ? C28 H28A 1.0000 . ? C34 C33 1.517(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C32 C33 1.521(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C21 C22 1.383(3) . ? C21 H21A 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C23 C22 1.377(3) . ? C23 H23A 0.9500 . ? C22 H22A 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ge1 C1 100.15(6) . . ? N1 O1 Ge1 106.57(9) . . ? O1 N1 C35 107.52(12) . . ? O1 N1 C31 106.99(12) . . ? C35 N1 C31 119.44(14) . . ? C2 C1 C6 118.60(15) . . ? C2 C1 Ge1 116.43(12) . . ? C6 C1 Ge1 122.81(12) . . ? C3 C2 C1 120.83(15) . . ? C3 C2 C7 121.85(15) . . ? C1 C2 C7 117.32(14) . . ? C12 C7 C8 120.53(15) . . ? C12 C7 C2 119.73(14) . . ? C8 C7 C2 119.68(15) . . ? C5 C4 C3 119.96(15) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C5 C6 C1 120.04(15) . . ? C5 C6 C19 120.41(15) . . ? C1 C6 C19 119.55(14) . . ? C4 C3 C2 119.94(16) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C20 C19 C24 120.52(17) . . ? C20 C19 C6 119.21(16) . . ? C24 C19 C6 120.27(16) . . ? C11 C12 C7 118.60(16) . . ? C11 C12 C16 120.37(16) . . ? C7 C12 C16 120.84(15) . . ? N1 C31 C36 106.47(14) . . ? N1 C31 C32 106.56(14) . . ? C36 C31 C32 108.39(15) . . ? N1 C31 C37 115.67(15) . . ? C36 C31 C37 108.86(16) . . ? C32 C31 C37 110.61(15) . . ? C10 C9 C8 121.01(17) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C4 C5 C6 120.63(15) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C9 C8 C7 118.54(16) . . ? C9 C8 C13 120.47(16) . . ? C7 C8 C13 120.99(15) . . ? C21 C20 C19 118.60(18) . . ? C21 C20 C25 119.86(18) . . ? C19 C20 C25 121.49(16) . . ? C12 C16 C17 114.18(15) . . ? C12 C16 C18 108.90(16) . . ? C17 C16 C18 110.60(16) . . ? C12 C16 H16A 107.6 . . ? C17 C16 H16A 107.6 . . ? C18 C16 H16A 107.6 . . ? N1 C35 C38 115.41(16) . . ? N1 C35 C39 106.36(15) . . ? C38 C35 C39 108.80(17) . . ? N1 C35 C34 107.29(14) . . ? C38 C35 C34 110.87(16) . . ? C39 C35 C34 107.79(17) . . ? C8 C13 C14 111.34(16) . . ? C8 C13 C15 112.26(16) . . ? C14 C13 C15 110.58(16) . . ? C8 C13 H13A 107.5 . . ? C14 C13 H13A 107.5 . . ? C15 C13 H13A 107.5 . . ? C23 C24 C19 118.37(19) . . ? C23 C24 C28 120.51(18) . . ? C19 C24 C28 121.03(17) . . ? C20 C25 C26 113.72(17) . . ? C20 C25 C27 110.41(18) . . ? C26 C25 C27 110.71(18) . . ? C20 C25 H25A 107.2 . . ? C26 C25 H25A 107.2 . . ? C27 C25 H25A 107.2 . . ? C10 C11 C12 120.85(17) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C9 C10 C11 120.38(16) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C24 C28 C30 113.11(18) . . ? C24 C28 C29 110.10(17) . . ? C30 C28 C29 110.56(17) . . ? C24 C28 H28A 107.6 . . ? C30 C28 H28A 107.6 . . ? C29 C28 H28A 107.6 . . ? C33 C34 C35 113.38(16) . . ? C33 C34 H34A 108.9 . . ? C35 C34 H34A 108.9 . . ? C33 C34 H34B 108.9 . . ? C35 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C32 C31 112.79(15) . . ? C33 C32 H32A 109.0 . . ? C31 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C31 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C34 C33 C32 108.53(15) . . ? C34 C33 H33A 110.0 . . ? C32 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? C32 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C22 C21 C20 121.1(2) . . ? C22 C21 H21A 119.5 . . ? C20 C21 H21A 119.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C35 C39 H39A 109.5 . . ? C35 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C35 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C22 C23 C24 121.44(19) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? C23 C22 C21 119.93(19) . . ? C23 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.493 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.071 data_py2 _database_code_depnum_ccdc_archive 'CCDC 284212' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4 _chemical_melting_point ? _chemical_formula_moiety 'C44 H54 O Sn' _chemical_formula_sum 'C44 H54 O Sn' _chemical_formula_weight 717.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.965(5) _cell_length_b 13.328(5) _cell_length_c 13.730(9) _cell_angle_alpha 111.010(8) _cell_angle_beta 102.783(8) _cell_angle_gamma 102.983(6) _cell_volume 1879.0(16) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 5342 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_type 'Empirical, SADABS (multi-scan)' _exptl_absorpt_correction_T_min 0.6991 _exptl_absorpt_correction_T_max 0.8535 _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26243 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0612 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.54 _reflns_number_total 11343 _reflns_number_gt 9628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (1.0.27) (Bruker, 2004)' _computing_cell_refinement 'SAINT (7.16b) (Bruker, 2004)' _computing_data_reduction 'SAINT (7.16b) (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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^)+(0.0242P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11343 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0695 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 0.117375(10) 0.129285(9) 0.064993(9) 0.01654(4) Uani 1 1 d . . . O1 O 0.03390(13) -0.02543(10) -0.08393(11) 0.0208(3) Uani 1 1 d . . . H1 H 0.054(2) -0.042(2) -0.125(2) 0.044(8) Uiso 1 1 d . . . C1 C 0.01263(14) 0.22659(12) 0.00547(12) 0.0123(3) Uani 1 1 d . . . C2 C -0.04660(14) 0.28792(12) 0.06982(12) 0.0121(3) Uani 1 1 d . . . C3 C -0.10019(14) 0.35977(13) 0.03815(13) 0.0145(3) Uani 1 1 d . . . H3A H -0.1402 0.4006 0.0823 0.017 Uiso 1 1 calc R . . C4 C -0.09490(14) 0.37137(13) -0.05745(13) 0.0153(3) Uani 1 1 d . . . H4A H -0.1331 0.4184 -0.0800 0.018 Uiso 1 1 calc R . . C5 C -0.03344(15) 0.31390(13) -0.11986(13) 0.0155(3) Uani 1 1 d . . . H5A H -0.0281 0.3233 -0.1843 0.019 Uiso 1 1 calc R . . C6 C 0.02070(14) 0.24241(12) -0.08941(12) 0.0124(3) Uani 1 1 d . . . C7 C 0.09392(15) 0.18695(13) -0.15368(13) 0.0138(3) Uani 1 1 d . . . C8 C 0.03616(16) 0.08599(13) -0.25237(13) 0.0171(3) Uani 1 1 d . . . C9 C 0.10784(17) 0.03472(15) -0.30745(15) 0.0223(4) Uani 1 1 d . . . H9A H 0.0699 -0.0333 -0.3742 0.027 Uiso 1 1 calc R . . C10 C 0.23394(18) 0.08199(16) -0.26583(16) 0.0253(4) Uani 1 1 d . . . H10A H 0.2816 0.0458 -0.3036 0.030 Uiso 1 1 calc R . . C11 C 0.28943(17) 0.18083(15) -0.17025(15) 0.0223(4) Uani 1 1 d . . . H11A H 0.3756 0.2128 -0.1430 0.027 Uiso 1 1 calc R . . C12 C 0.22210(15) 0.23572(14) -0.11188(14) 0.0167(3) Uani 1 1 d . . . C13 C -0.05194(14) 0.28118(12) 0.17598(13) 0.0126(3) Uani 1 1 d . . . C14 C 0.05009(14) 0.34271(13) 0.27268(13) 0.0145(3) Uani 1 1 d . . . C15 C 0.04076(16) 0.33878(14) 0.37101(13) 0.0187(3) Uani 1 1 d . . . H15A H 0.1092 0.3795 0.4368 0.022 Uiso 1 1 calc R . . C16 C -0.06693(16) 0.27635(14) 0.37380(14) 0.0202(3) Uani 1 1 d . . . H16A H -0.0722 0.2758 0.4417 0.024 Uiso 1 1 calc R . . C17 C -0.16665(15) 0.21487(14) 0.27866(14) 0.0176(3) Uani 1 1 d . . . H17A H -0.2398 0.1718 0.2816 0.021 Uiso 1 1 calc R . . C18 C -0.16131(14) 0.21523(13) 0.17795(13) 0.0142(3) Uani 1 1 d . . . C19 C -0.10173(16) 0.03378(14) -0.29975(14) 0.0200(3) Uani 1 1 d . . . H19A H -0.1342 0.0607 -0.2375 0.024 Uiso 1 1 calc R . . C20 C 0.28621(15) 0.34947(15) -0.01019(14) 0.0208(3) Uani 1 1 d . . . H20A H 0.2296 0.3611 0.0333 0.025 Uiso 1 1 calc R . . C21 C 0.16668(15) 0.42032(14) 0.27438(13) 0.0179(3) Uani 1 1 d . . . H21A H 0.1685 0.3928 0.1969 0.021 Uiso 1 1 calc R . . C22 C -0.27188(15) 0.14670(13) 0.07433(14) 0.0162(3) Uani 1 1 d . . . H22A H -0.2435 0.1362 0.0092 0.019 Uiso 1 1 calc R . . C23 C -0.14786(18) -0.09735(15) -0.35227(15) 0.0276(4) Uani 1 1 d . . . H23A H -0.2363 -0.1254 -0.3706 0.041 Uiso 1 1 calc R . . H23B H -0.1097 -0.1239 -0.2999 0.041 Uiso 1 1 calc R . . H23C H -0.1270 -0.1264 -0.4198 0.041 Uiso 1 1 calc R . . C24 C -0.15412(19) 0.07433(17) -0.38529(16) 0.0306(4) Uani 1 1 d . . . H24A H -0.1326 0.1575 -0.3500 0.046 Uiso 1 1 calc R . . H24B H -0.2428 0.0390 -0.4150 0.046 Uiso 1 1 calc R . . H24C H -0.1205 0.0525 -0.4456 0.046 Uiso 1 1 calc R . . C25 C 0.40384(17) 0.35435(18) 0.06588(17) 0.0327(5) Uani 1 1 d . . . H25A H 0.3878 0.2891 0.0842 0.049 Uiso 1 1 calc R . . H25B H 0.4346 0.4253 0.1339 0.049 Uiso 1 1 calc R . . H25C H 0.4646 0.3518 0.0283 0.049 Uiso 1 1 calc R . . C26 C 0.31096(18) 0.44727(15) -0.04516(16) 0.0279(4) Uani 1 1 d . . . H26A H 0.2342 0.4459 -0.0902 0.042 Uiso 1 1 calc R . . H26B H 0.3661 0.4381 -0.0884 0.042 Uiso 1 1 calc R . . H26C H 0.3484 0.5202 0.0208 0.042 Uiso 1 1 calc R . . C27 C 0.28209(16) 0.41786(17) 0.34661(16) 0.0277(4) Uani 1 1 d . . . H27A H 0.3532 0.4606 0.3364 0.042 Uiso 1 1 calc R . . H27B H 0.2796 0.3387 0.3254 0.042 Uiso 1 1 calc R . . H27C H 0.2876 0.4527 0.4244 0.042 Uiso 1 1 calc R . . C28 C 0.16399(17) 0.54263(15) 0.31085(16) 0.0268(4) Uani 1 1 d . . . H28A H 0.2373 0.5913 0.3088 0.040 Uiso 1 1 calc R . . H28B H 0.1610 0.5716 0.3864 0.040 Uiso 1 1 calc R . . H28C H 0.0919 0.5431 0.2607 0.040 Uiso 1 1 calc R . . C29 C -0.36351(16) 0.21001(15) 0.06860(15) 0.0235(4) Uani 1 1 d . . . H29A H -0.4297 0.1671 -0.0025 0.035 Uiso 1 1 calc R . . H29B H -0.3227 0.2860 0.0756 0.035 Uiso 1 1 calc R . . H29C H -0.3967 0.2175 0.1290 0.035 Uiso 1 1 calc R . . C30 C -0.33587(15) 0.02765(14) 0.06351(15) 0.0203(3) Uani 1 1 d . . . H30A H -0.3989 -0.0169 -0.0093 0.030 Uiso 1 1 calc R . . H30B H -0.3732 0.0351 0.1213 0.030 Uiso 1 1 calc R . . H30C H -0.2763 -0.0112 0.0716 0.030 Uiso 1 1 calc R . . C40 C -0.44805(17) 0.00860(16) -0.29765(15) 0.0248(4) Uani 1 1 d . . . C41 C -0.41240(18) -0.06202(18) -0.25283(16) 0.0297(4) Uani 1 1 d . . . H41A H -0.3468 -0.0293 -0.1852 0.036 Uiso 1 1 calc R . . C42 C -0.4701(2) -0.17897(18) -0.30418(17) 0.0336(5) Uani 1 1 d . . . H42A H -0.4440 -0.2255 -0.2718 0.040 Uiso 1 1 calc R . . C43 C -0.56603(19) -0.22807(18) -0.40308(17) 0.0331(5) Uani 1 1 d . . . H43A H -0.6056 -0.3083 -0.4392 0.040 Uiso 1 1 calc R . . C44 C -0.60346(18) -0.15898(18) -0.44853(16) 0.0318(4) Uani 1 1 d . . . H74A H -0.6697 -0.1918 -0.5157 0.038 Uiso 1 1 calc R . . C45 C -0.54469(17) -0.04188(17) -0.39645(15) 0.0270(4) Uani 1 1 d . . . H45A H -0.5709 0.0045 -0.4289 0.032 Uiso 1 1 calc R . . C46 C -0.3859(2) 0.13595(17) -0.24139(18) 0.0363(5) Uani 1 1 d . . . H46A H -0.4308 0.1716 -0.1956 0.054 Uiso 1 1 calc R . . H46B H -0.3837 0.1651 -0.2974 0.054 Uiso 1 1 calc R . . H46C H -0.3027 0.1540 -0.1946 0.054 Uiso 1 1 calc R . . C50 C -0.68267(17) -0.64204(16) -0.35555(14) 0.0243(4) Uani 1 1 d . . . C51 C -0.64963(17) -0.53013(16) -0.34477(14) 0.0253(4) Uani 1 1 d . . . H51A H -0.5719 -0.4959 -0.3467 0.030 Uiso 1 1 calc R . . C52 C -0.72840(18) -0.46839(16) -0.33134(15) 0.0264(4) Uani 1 1 d . . . H52A H -0.7041 -0.3922 -0.3236 0.032 Uiso 1 1 calc R . . C53 C -0.84251(17) -0.51710(15) -0.32918(14) 0.0233(4) Uani 1 1 d . . . H53A H -0.8967 -0.4748 -0.3201 0.028 Uiso 1 1 calc R . . C54 C -0.87660(17) -0.62797(16) -0.34035(14) 0.0226(4) Uani 1 1 d . . . H54A H -0.9549 -0.6622 -0.3395 0.027 Uiso 1 1 calc R . . C55 C -0.79734(17) -0.68964(16) -0.35285(14) 0.0235(4) Uani 1 1 d . . . H55A H -0.8217 -0.7654 -0.3597 0.028 Uiso 1 1 calc R . . C56 C -0.5954(2) -0.7078(2) -0.36785(19) 0.0406(5) Uani 1 1 d . . . H56A H -0.6379 -0.7878 -0.3870 0.061 Uiso 1 1 calc R . . H56B H -0.5280 -0.6752 -0.2980 0.061 Uiso 1 1 calc R . . H56C H -0.5635 -0.7032 -0.4266 0.061 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 0.01536(6) 0.01556(6) 0.01940(6) 0.00897(5) 0.00328(4) 0.00646(4) O1 0.0319(8) 0.0163(6) 0.0208(7) 0.0088(5) 0.0173(6) 0.0100(5) C1 0.0104(7) 0.0116(7) 0.0124(7) 0.0041(6) 0.0024(6) 0.0021(6) C2 0.0097(7) 0.0109(7) 0.0115(7) 0.0028(6) 0.0023(6) 0.0007(6) C3 0.0138(8) 0.0130(7) 0.0157(8) 0.0046(6) 0.0051(6) 0.0051(6) C4 0.0157(8) 0.0140(7) 0.0174(8) 0.0082(7) 0.0044(7) 0.0062(6) C5 0.0173(8) 0.0166(7) 0.0130(7) 0.0076(6) 0.0042(6) 0.0048(6) C6 0.0112(7) 0.0117(7) 0.0117(7) 0.0040(6) 0.0031(6) 0.0016(6) C7 0.0183(8) 0.0156(7) 0.0140(7) 0.0097(6) 0.0084(6) 0.0086(6) C8 0.0237(9) 0.0167(8) 0.0160(8) 0.0097(7) 0.0096(7) 0.0085(7) C9 0.0347(11) 0.0193(8) 0.0199(9) 0.0094(7) 0.0159(8) 0.0133(8) C10 0.0355(11) 0.0290(9) 0.0314(10) 0.0192(9) 0.0241(9) 0.0233(9) C11 0.0204(9) 0.0297(9) 0.0294(10) 0.0192(8) 0.0141(8) 0.0149(8) C12 0.0170(8) 0.0217(8) 0.0186(8) 0.0132(7) 0.0086(7) 0.0090(7) C13 0.0136(8) 0.0114(7) 0.0137(7) 0.0047(6) 0.0052(6) 0.0061(6) C14 0.0144(8) 0.0135(7) 0.0148(8) 0.0044(6) 0.0046(6) 0.0061(6) C15 0.0186(9) 0.0206(8) 0.0132(8) 0.0054(7) 0.0028(6) 0.0055(7) C16 0.0255(9) 0.0245(9) 0.0151(8) 0.0105(7) 0.0098(7) 0.0099(7) C17 0.0171(8) 0.0183(8) 0.0205(8) 0.0090(7) 0.0108(7) 0.0057(7) C18 0.0137(8) 0.0135(7) 0.0157(8) 0.0057(6) 0.0054(6) 0.0058(6) C19 0.0228(9) 0.0176(8) 0.0145(8) 0.0032(7) 0.0059(7) 0.0041(7) C20 0.0139(8) 0.0258(9) 0.0206(9) 0.0100(8) 0.0057(7) 0.0027(7) C21 0.0132(8) 0.0212(8) 0.0140(8) 0.0044(7) 0.0032(6) 0.0028(7) C22 0.0136(8) 0.0163(7) 0.0170(8) 0.0069(7) 0.0050(6) 0.0025(6) C23 0.0328(11) 0.0199(9) 0.0188(9) 0.0018(7) 0.0060(8) 0.0017(8) C24 0.0307(11) 0.0306(10) 0.0248(10) 0.0111(9) 0.0027(8) 0.0078(9) C25 0.0209(10) 0.0369(11) 0.0348(11) 0.0202(10) -0.0007(8) 0.0015(9) C26 0.0297(11) 0.0219(9) 0.0281(10) 0.0092(8) 0.0057(8) 0.0081(8) C27 0.0154(9) 0.0333(10) 0.0277(10) 0.0105(9) 0.0024(8) 0.0047(8) C28 0.0228(10) 0.0211(9) 0.0321(10) 0.0103(8) 0.0086(8) 0.0017(7) C29 0.0165(9) 0.0221(9) 0.0289(10) 0.0118(8) 0.0032(7) 0.0038(7) C30 0.0151(8) 0.0175(8) 0.0256(9) 0.0079(7) 0.0071(7) 0.0025(7) C40 0.0204(9) 0.0318(10) 0.0224(9) 0.0095(8) 0.0099(8) 0.0100(8) C41 0.0241(10) 0.0434(12) 0.0230(10) 0.0150(9) 0.0071(8) 0.0136(9) C42 0.0386(12) 0.0416(12) 0.0362(12) 0.0247(10) 0.0194(10) 0.0213(10) C43 0.0358(12) 0.0300(10) 0.0333(11) 0.0120(9) 0.0179(10) 0.0070(9) C44 0.0269(11) 0.0391(11) 0.0219(10) 0.0087(9) 0.0065(8) 0.0065(9) C45 0.0254(10) 0.0362(11) 0.0240(10) 0.0149(9) 0.0101(8) 0.0133(9) C46 0.0336(12) 0.0335(11) 0.0347(12) 0.0093(10) 0.0091(10) 0.0097(9) C50 0.0267(10) 0.0323(10) 0.0153(8) 0.0083(8) 0.0072(7) 0.0155(8) C51 0.0195(9) 0.0316(10) 0.0195(9) 0.0076(8) 0.0060(7) 0.0049(8) C52 0.0319(11) 0.0220(9) 0.0213(9) 0.0068(8) 0.0087(8) 0.0061(8) C53 0.0282(10) 0.0263(9) 0.0174(9) 0.0079(7) 0.0093(7) 0.0133(8) C54 0.0240(10) 0.0312(9) 0.0162(8) 0.0121(8) 0.0089(7) 0.0107(8) C55 0.0298(10) 0.0252(9) 0.0181(9) 0.0111(8) 0.0082(8) 0.0107(8) C56 0.0385(13) 0.0523(14) 0.0405(13) 0.0202(11) 0.0156(11) 0.0294(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sn1 O1 2.1397(16) . ? Sn1 O1 2.1449(14) 2 ? Sn1 C1 2.2267(16) . ? O1 Sn1 2.1449(14) 2 ? O1 H1 0.65(2) . ? C1 C2 1.404(2) . ? C1 C6 1.412(2) . ? C2 C3 1.403(2) . ? C2 C13 1.506(2) . ? C3 C4 1.389(2) . ? C3 H3A 0.9500 . ? C4 C5 1.387(2) . ? C4 H4A 0.9500 . ? C5 C6 1.395(2) . ? C5 H5A 0.9500 . ? C6 C7 1.503(2) . ? C7 C8 1.409(2) . ? C7 C12 1.414(2) . ? C8 C9 1.398(2) . ? C8 C19 1.521(2) . ? C9 C10 1.390(3) . ? C9 H9A 0.9500 . ? C10 C11 1.371(3) . ? C10 H10A 0.9500 . ? C11 C12 1.399(2) . ? C11 H11A 0.9500 . ? C12 C20 1.524(2) . ? C13 C14 1.406(2) . ? C13 C18 1.415(2) . ? C14 C15 1.397(2) . ? C14 C21 1.529(2) . ? C15 C16 1.385(2) . ? C15 H15A 0.9500 . ? C16 C17 1.380(2) . ? C16 H16A 0.9500 . ? C17 C18 1.400(2) . ? C17 H17A 0.9500 . ? C18 C22 1.517(2) . ? C19 C24 1.532(2) . ? C19 C23 1.538(2) . ? C19 H19A 1.0000 . ? C20 C25 1.528(2) . ? C20 C26 1.535(2) . ? C20 H20A 1.0000 . ? C21 C27 1.526(2) . ? C21 C28 1.535(2) . ? C21 H21A 1.0000 . ? C22 C29 1.532(2) . ? C22 C30 1.536(2) . ? C22 H22A 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C40 C41 1.388(3) . ? C40 C45 1.390(3) . ? C40 C46 1.506(3) . ? C41 C42 1.384(3) . ? C41 H41A 0.9500 . ? C42 C43 1.388(3) . ? C42 H42A 0.9500 . ? C43 C44 1.383(3) . ? C43 H43A 0.9500 . ? C44 C45 1.388(3) . ? C44 H74A 0.9500 . ? C45 H45A 0.9500 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C50 C55 1.391(3) . ? C50 C51 1.398(3) . ? C50 C56 1.507(3) . ? C51 C52 1.384(3) . ? C51 H51A 0.9500 . ? C52 C53 1.386(3) . ? C52 H52A 0.9500 . ? C53 C54 1.383(2) . ? C53 H53A 0.9500 . ? C54 C55 1.388(2) . ? C54 H54A 0.9500 . ? C55 H55A 0.9500 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Sn1 O1 72.27(7) . 2 ? O1 Sn1 C1 95.33(6) . . ? O1 Sn1 C1 94.60(6) 2 . ? Sn1 O1 Sn1 107.73(7) . 2 ? Sn1 O1 H1 127(2) . . ? Sn1 O1 H1 125(2) 2 . ? C2 C1 C6 118.29(13) . . ? C2 C1 Sn1 120.97(11) . . ? C6 C1 Sn1 119.99(11) . . ? C3 C2 C1 120.67(14) . . ? C3 C2 C13 117.98(14) . . ? C1 C2 C13 121.33(13) . . ? C4 C3 C2 120.24(14) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 119.59(14) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.92(14) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 120.23(14) . . ? C5 C6 C7 120.15(13) . . ? C1 C6 C7 119.53(13) . . ? C8 C7 C12 120.38(14) . . ? C8 C7 C6 120.61(14) . . ? C12 C7 C6 118.98(14) . . ? C9 C8 C7 118.82(16) . . ? C9 C8 C19 120.13(15) . . ? C7 C8 C19 121.05(14) . . ? C10 C9 C8 120.84(17) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C11 C10 C9 119.98(16) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 121.54(17) . . ? C10 C11 H11A 119.2 . . ? C12 C11 H11A 119.2 . . ? C11 C12 C7 118.43(16) . . ? C11 C12 C20 120.11(15) . . ? C7 C12 C20 121.33(14) . . ? C14 C13 C18 120.60(14) . . ? C14 C13 C2 119.99(14) . . ? C18 C13 C2 119.38(14) . . ? C15 C14 C13 118.71(15) . . ? C15 C14 C21 119.52(14) . . ? C13 C14 C21 121.60(14) . . ? C16 C15 C14 120.86(16) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C17 C16 C15 120.44(15) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 120.77(15) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C17 C18 C13 118.59(15) . . ? C17 C18 C22 119.88(14) . . ? C13 C18 C22 121.53(14) . . ? C8 C19 C24 111.09(14) . . ? C8 C19 C23 113.47(15) . . ? C24 C19 C23 109.09(15) . . ? C8 C19 H19A 107.7 . . ? C24 C19 H19A 107.7 . . ? C23 C19 H19A 107.7 . . ? C12 C20 C25 113.63(15) . . ? C12 C20 C26 110.16(14) . . ? C25 C20 C26 110.26(14) . . ? C12 C20 H20A 107.5 . . ? C25 C20 H20A 107.5 . . ? C26 C20 H20A 107.5 . . ? C27 C21 C14 113.35(14) . . ? C27 C21 C28 110.68(15) . . ? C14 C21 C28 109.84(14) . . ? C27 C21 H21A 107.6 . . ? C14 C21 H21A 107.6 . . ? C28 C21 H21A 107.6 . . ? C18 C22 C29 111.56(14) . . ? C18 C22 C30 112.78(13) . . ? C29 C22 C30 109.43(13) . . ? C18 C22 H22A 107.6 . . ? C29 C22 H22A 107.6 . . ? C30 C22 H22A 107.6 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C21 C28 H28A 109.5 . . ? C21 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C21 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C22 C29 H29A 109.5 . . ? C22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C22 C30 H30A 109.5 . . ? C22 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C22 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C41 C40 C45 117.77(18) . . ? C41 C40 C46 121.69(18) . . ? C45 C40 C46 120.54(17) . . ? C42 C41 C40 121.67(19) . . ? C42 C41 H41A 119.2 . . ? C40 C41 H41A 119.2 . . ? C41 C42 C43 119.83(18) . . ? C41 C42 H42A 120.1 . . ? C43 C42 H42A 120.1 . . ? C44 C43 C42 119.32(19) . . ? C44 C43 H43A 120.3 . . ? C42 C43 H43A 120.3 . . ? C43 C44 C45 120.32(19) . . ? C43 C44 H74A 119.8 . . ? C45 C44 H74A 119.8 . . ? C44 C45 C40 121.08(18) . . ? C44 C45 H45A 119.5 . . ? C40 C45 H45A 119.5 . . ? C40 C46 H46A 109.5 . . ? C40 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C40 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C55 C50 C51 117.96(17) . . ? C55 C50 C56 121.37(18) . . ? C51 C50 C56 120.67(18) . . ? C52 C51 C50 121.03(17) . . ? C52 C51 H51A 119.5 . . ? C50 C51 H51A 119.5 . . ? C51 C52 C53 120.35(17) . . ? C51 C52 H52A 119.8 . . ? C53 C52 H52A 119.8 . . ? C54 C53 C52 119.22(17) . . ? C54 C53 H53A 120.4 . . ? C52 C53 H53A 120.4 . . ? C53 C54 C55 120.50(17) . . ? C53 C54 H54A 119.7 . . ? C55 C54 H54A 119.7 . . ? C54 C55 C50 120.94(17) . . ? C54 C55 H55A 119.5 . . ? C50 C55 H55A 119.5 . . ? C50 C56 H56A 109.5 . . ? C50 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C50 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.611 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.080 data_gs32 _database_code_depnum_ccdc_archive 'CCDC 284213' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5 _chemical_melting_point ? _chemical_formula_moiety 'C44 H54 Ge O' _chemical_formula_sum 'C44 H54 Ge O' _chemical_formula_weight 671.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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 11.9901(8) _cell_length_b 13.1090(9) _cell_length_c 13.7709(9) _cell_angle_alpha 110.6330(10) _cell_angle_beta 103.2580(10) _cell_angle_gamma 102.6850(10) _cell_volume 1861.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 6088 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 30.00 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max .52 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.854 _exptl_absorpt_correction_type 'Empirical, SADABS (multi-scan)' _exptl_absorpt_correction_T_min 0.6649 _exptl_absorpt_correction_T_max 0.8212 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24504 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 30.03 _reflns_number_total 10680 _reflns_number_gt 9054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Version 5.054) (Bruker, 2002)' _computing_cell_refinement 'SAINT (7.16b) (Bruker, 2004)' _computing_data_reduction 'SAINT (7.16b) (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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^)+(0.0486P)^2^+1.1744P] 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 10680 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ge1 Ge 0.397696(15) 0.379850(14) 0.445087(14) 0.02136(5) Uani 1 1 d . . . O1 O 0.47011(13) 0.52508(10) 0.58098(11) 0.0292(3) Uani 1 1 d . . . H1 H 0.437(4) 0.551(4) 0.641(4) 0.134(17) Uiso 1 1 d . . . C1 C 0.48903(12) 0.28457(11) 0.49681(11) 0.0126(2) Uani 1 1 d . . . C2 C 0.47954(12) 0.26629(11) 0.59017(11) 0.0131(2) Uani 1 1 d . . . C3 C 0.53114(12) 0.19136(12) 0.61991(11) 0.0152(2) Uani 1 1 d . . . H3 H 0.5255 0.1813 0.6839 0.018 Uiso 1 1 calc R . . C4 C 0.59066(12) 0.13125(12) 0.55674(12) 0.0157(3) Uani 1 1 d . . . H4 H 0.6276 0.0820 0.5784 0.019 Uiso 1 1 calc R . . C5 C 0.59556(12) 0.14393(11) 0.46163(11) 0.0142(2) Uani 1 1 d . . . H5 H 0.6336 0.1010 0.4169 0.017 Uiso 1 1 calc R . . C6 C 0.54504(12) 0.21920(11) 0.43119(11) 0.0124(2) Uani 1 1 d . . . C7 C 0.40770(13) 0.32183(12) 0.65549(11) 0.0149(2) Uani 1 1 d . . . C8 C 0.28004(13) 0.27189(13) 0.61631(12) 0.0186(3) Uani 1 1 d . . . C9 C 0.21414(15) 0.32512(15) 0.67753(14) 0.0240(3) Uani 1 1 d . . . H9 H 0.1282 0.2924 0.6522 0.029 Uiso 1 1 calc R . . C10 C 0.27210(16) 0.42473(15) 0.77447(14) 0.0257(3) Uani 1 1 d . . . H10 H 0.2257 0.4605 0.8142 0.031 Uiso 1 1 calc R . . C11 C 0.39777(16) 0.47258(13) 0.81378(13) 0.0231(3) Uani 1 1 d . . . H11 H 0.4368 0.5402 0.8810 0.028 Uiso 1 1 calc R . . C12 C 0.46743(14) 0.42233(12) 0.75545(12) 0.0175(3) Uani 1 1 d . . . C13 C 0.21503(14) 0.15879(14) 0.51329(13) 0.0222(3) Uani 1 1 d . . . H13 H 0.2717 0.1471 0.4704 0.027 Uiso 1 1 calc R . . C14 C 0.09922(17) 0.15917(18) 0.43810(17) 0.0358(4) Uani 1 1 d . . . H14A H 0.0392 0.1642 0.4758 0.054 Uiso 1 1 calc R . . H14B H 0.0661 0.0878 0.3700 0.054 Uiso 1 1 calc R . . H14C H 0.1183 0.2257 0.4204 0.054 Uiso 1 1 calc R . . C15 C 0.18731(18) 0.05771(15) 0.54550(16) 0.0312(4) Uani 1 1 d . . . H15A H 0.2629 0.0568 0.5906 0.047 Uiso 1 1 calc R . . H15B H 0.1496 -0.0150 0.4788 0.047 Uiso 1 1 calc R . . H15C H 0.1317 0.0668 0.5877 0.047 Uiso 1 1 calc R . . C16 C 0.60545(15) 0.47408(13) 0.80121(13) 0.0212(3) Uani 1 1 d . . . H16 H 0.6365 0.4443 0.7390 0.025 Uiso 1 1 calc R . . C17 C 0.65218(18) 0.60641(14) 0.84956(15) 0.0293(4) Uani 1 1 d . . . H17A H 0.6162 0.6317 0.7945 0.044 Uiso 1 1 calc R . . H17B H 0.7408 0.6338 0.8700 0.044 Uiso 1 1 calc R . . H17C H 0.6294 0.6383 0.9151 0.044 Uiso 1 1 calc R . . C18 C 0.65845(17) 0.43475(16) 0.88850(15) 0.0307(4) Uani 1 1 d . . . H18A H 0.6271 0.4603 0.9495 0.046 Uiso 1 1 calc R . . H18B H 0.7471 0.4684 0.9163 0.046 Uiso 1 1 calc R . . H18C H 0.6350 0.3503 0.8556 0.046 Uiso 1 1 calc R . . C19 C 0.55032(12) 0.22463(11) 0.32491(11) 0.0127(2) Uani 1 1 d . . . C20 C 0.66014(12) 0.28914(11) 0.32241(11) 0.0142(2) Uani 1 1 d . . . C21 C 0.66692(13) 0.28625(12) 0.22165(12) 0.0173(3) Uani 1 1 d . . . H21 H 0.7403 0.3290 0.2190 0.021 Uiso 1 1 calc R . . C22 C 0.56798(14) 0.22180(13) 0.12527(12) 0.0192(3) Uani 1 1 d . . . H22 H 0.5743 0.2201 0.0572 0.023 Uiso 1 1 calc R . . C23 C 0.45954(13) 0.15974(13) 0.12830(12) 0.0185(3) Uani 1 1 d . . . H23 H 0.3919 0.1168 0.0623 0.022 Uiso 1 1 calc R . . C24 C 0.44915(12) 0.15993(12) 0.22751(11) 0.0149(2) Uani 1 1 d . . . C25 C 0.77008(12) 0.35846(12) 0.42696(12) 0.0161(3) Uani 1 1 d . . . H25 H 0.7410 0.3690 0.4912 0.019 Uiso 1 1 calc R . . C26 C 0.86127(14) 0.29320(13) 0.43368(14) 0.0230(3) Uani 1 1 d . . . H26A H 0.8202 0.2165 0.4273 0.034 Uiso 1 1 calc R . . H26B H 0.9275 0.3364 0.5045 0.034 Uiso 1 1 calc R . . H26C H 0.8943 0.2850 0.3735 0.034 Uiso 1 1 calc R . . C27 C 0.83409(14) 0.47880(13) 0.43752(13) 0.0216(3) Uani 1 1 d . . . H27A H 0.8717 0.4712 0.3803 0.032 Uiso 1 1 calc R . . H27B H 0.8968 0.5236 0.5103 0.032 Uiso 1 1 calc R . . H27C H 0.7747 0.5185 0.4287 0.032 Uiso 1 1 calc R . . C28 C 0.33229(13) 0.08374(13) 0.22679(12) 0.0186(3) Uani 1 1 d . . . H28 H 0.3320 0.1114 0.3043 0.022 Uiso 1 1 calc R . . C29 C 0.33121(16) -0.04160(14) 0.18889(16) 0.0285(3) Uani 1 1 d . . . H29A H 0.3321 -0.0709 0.1131 0.043 Uiso 1 1 calc R . . H29B H 0.2578 -0.0893 0.1919 0.043 Uiso 1 1 calc R . . H29C H 0.4030 -0.0447 0.2375 0.043 Uiso 1 1 calc R . . C30 C 0.21747(14) 0.09027(17) 0.15619(16) 0.0294(4) Uani 1 1 d . . . H30A H 0.2201 0.1709 0.1810 0.044 Uiso 1 1 calc R . . H30B H 0.1459 0.0447 0.1635 0.044 Uiso 1 1 calc R . . H30C H 0.2129 0.0594 0.0789 0.044 Uiso 1 1 calc R . . C31 C 0.94549(15) 0.49188(15) 0.79533(14) 0.0251(3) Uani 1 1 d . . . C32 C 1.04162(15) 0.54117(16) 0.89481(14) 0.0268(3) Uani 1 1 d . . . H32 H 1.0664 0.4930 0.9270 0.032 Uiso 1 1 calc R . . C33 C 1.10166(17) 0.65953(17) 0.94743(15) 0.0318(4) Uani 1 1 d . . . H33 H 1.1668 0.6917 1.0152 0.038 Uiso 1 1 calc R . . C34 C 1.06677(18) 0.73083(17) 0.90140(16) 0.0336(4) Uani 1 1 d . . . H34 H 1.1077 0.8118 0.9374 0.040 Uiso 1 1 calc R . . C35 C 0.97172(19) 0.68306(18) 0.80247(17) 0.0341(4) Uani 1 1 d . . . H35 H 0.9478 0.7315 0.7702 0.041 Uiso 1 1 calc R . . C36 C 0.91113(17) 0.56461(17) 0.75015(15) 0.0310(4) Uani 1 1 d . . . H36 H 0.8455 0.5329 0.6828 0.037 Uiso 1 1 calc R . . C37 C 0.88124(19) 0.36309(17) 0.73912(17) 0.0369(4) Uani 1 1 d . . . H37A H 0.9263 0.3257 0.6949 0.055 Uiso 1 1 calc R . . H37B H 0.7991 0.3464 0.6911 0.055 Uiso 1 1 calc R . . H37C H 0.8766 0.3336 0.7948 0.055 Uiso 1 1 calc R . . C41 C 0.81584(15) 0.85709(15) 0.14323(13) 0.0249(3) Uani 1 1 d . . . C42 C 0.84871(15) 0.97135(15) 0.15650(13) 0.0255(3) Uani 1 1 d . . . H42 H 0.9262 1.0066 0.1551 0.031 Uiso 1 1 calc R . . C43 C 0.77000(16) 1.03424(14) 0.17171(14) 0.0260(3) Uani 1 1 d . . . H43 H 0.7940 1.1121 0.1810 0.031 Uiso 1 1 calc R . . C44 C 0.65629(15) 0.98362(14) 0.17330(13) 0.0237(3) Uani 1 1 d . . . H44 H 0.6024 1.0266 0.1840 0.028 Uiso 1 1 calc R . . C45 C 0.62204(15) 0.86978(14) 0.15918(13) 0.0223(3) Uani 1 1 d . . . H45 H 0.5441 0.8345 0.1597 0.027 Uiso 1 1 calc R . . C46 C 0.70116(16) 0.80700(14) 0.14430(13) 0.0241(3) Uani 1 1 d . . . H46 H 0.6768 0.7291 0.1347 0.029 Uiso 1 1 calc R . . C47 C 0.9031(2) 0.7904(2) 0.12912(19) 0.0416(5) Uani 1 1 d . . . H47A H 0.9341 0.7968 0.0708 0.062 Uiso 1 1 calc R . . H47B H 0.8611 0.7091 0.1090 0.062 Uiso 1 1 calc R . . H47C H 0.9709 0.8221 0.1984 0.062 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 0.02117(9) 0.01987(8) 0.02484(9) 0.01185(7) 0.00468(6) 0.00931(6) O1 0.0477(8) 0.0189(5) 0.0297(6) 0.0111(5) 0.0251(6) 0.0128(5) C1 0.0109(5) 0.0121(5) 0.0130(6) 0.0045(5) 0.0036(5) 0.0023(4) C2 0.0115(5) 0.0137(6) 0.0124(6) 0.0044(5) 0.0036(5) 0.0032(4) C3 0.0156(6) 0.0171(6) 0.0138(6) 0.0077(5) 0.0050(5) 0.0049(5) C4 0.0146(6) 0.0144(6) 0.0178(6) 0.0073(5) 0.0042(5) 0.0047(5) C5 0.0116(6) 0.0129(5) 0.0160(6) 0.0041(5) 0.0046(5) 0.0036(5) C6 0.0096(5) 0.0128(5) 0.0123(6) 0.0041(5) 0.0033(4) 0.0013(4) C7 0.0177(6) 0.0181(6) 0.0154(6) 0.0106(5) 0.0085(5) 0.0089(5) C8 0.0179(6) 0.0247(7) 0.0195(7) 0.0133(6) 0.0086(5) 0.0099(5) C9 0.0211(7) 0.0352(8) 0.0296(8) 0.0205(7) 0.0154(6) 0.0167(6) C10 0.0350(9) 0.0307(8) 0.0303(8) 0.0191(7) 0.0235(7) 0.0222(7) C11 0.0349(8) 0.0199(7) 0.0222(7) 0.0101(6) 0.0175(7) 0.0130(6) C12 0.0239(7) 0.0173(6) 0.0165(6) 0.0090(5) 0.0106(5) 0.0091(5) C13 0.0140(6) 0.0302(8) 0.0201(7) 0.0101(6) 0.0049(5) 0.0047(6) C14 0.0220(8) 0.0436(10) 0.0351(10) 0.0211(9) -0.0026(7) 0.0042(7) C15 0.0337(9) 0.0250(8) 0.0284(9) 0.0089(7) 0.0045(7) 0.0077(7) C16 0.0248(7) 0.0174(6) 0.0171(7) 0.0036(5) 0.0083(6) 0.0039(6) C17 0.0360(9) 0.0179(7) 0.0239(8) 0.0023(6) 0.0096(7) 0.0015(6) C18 0.0285(8) 0.0311(8) 0.0260(8) 0.0108(7) 0.0028(7) 0.0066(7) C19 0.0129(6) 0.0130(5) 0.0125(6) 0.0047(5) 0.0049(5) 0.0053(5) C20 0.0132(6) 0.0132(6) 0.0158(6) 0.0054(5) 0.0049(5) 0.0049(5) C21 0.0177(6) 0.0181(6) 0.0182(7) 0.0085(5) 0.0092(5) 0.0055(5) C22 0.0213(7) 0.0230(7) 0.0154(6) 0.0091(5) 0.0081(5) 0.0078(6) C23 0.0170(6) 0.0218(7) 0.0135(6) 0.0056(5) 0.0033(5) 0.0053(5) C24 0.0130(6) 0.0163(6) 0.0142(6) 0.0047(5) 0.0049(5) 0.0050(5) C25 0.0131(6) 0.0152(6) 0.0160(6) 0.0052(5) 0.0038(5) 0.0006(5) C26 0.0142(6) 0.0212(7) 0.0291(8) 0.0113(6) 0.0017(6) 0.0025(5) C27 0.0178(7) 0.0164(6) 0.0252(7) 0.0067(6) 0.0063(6) 0.0004(5) C28 0.0130(6) 0.0213(7) 0.0155(6) 0.0045(5) 0.0037(5) 0.0014(5) C29 0.0227(8) 0.0220(7) 0.0371(9) 0.0116(7) 0.0100(7) 0.0018(6) C30 0.0129(7) 0.0370(9) 0.0339(9) 0.0150(7) 0.0032(6) 0.0047(6) C31 0.0197(7) 0.0297(8) 0.0240(8) 0.0079(6) 0.0099(6) 0.0077(6) C32 0.0239(8) 0.0334(8) 0.0258(8) 0.0132(7) 0.0099(6) 0.0120(7) C33 0.0259(8) 0.0355(9) 0.0251(8) 0.0079(7) 0.0060(7) 0.0048(7) C34 0.0363(10) 0.0295(9) 0.0347(10) 0.0112(7) 0.0190(8) 0.0071(7) C35 0.0410(10) 0.0398(10) 0.0365(10) 0.0233(8) 0.0219(8) 0.0196(8) C36 0.0267(8) 0.0420(10) 0.0245(8) 0.0139(7) 0.0081(7) 0.0127(7) C37 0.0331(10) 0.0304(9) 0.0351(10) 0.0058(8) 0.0089(8) 0.0044(7) C41 0.0258(8) 0.0310(8) 0.0185(7) 0.0084(6) 0.0064(6) 0.0148(7) C42 0.0185(7) 0.0295(8) 0.0206(7) 0.0056(6) 0.0049(6) 0.0035(6) C43 0.0294(8) 0.0197(7) 0.0232(8) 0.0050(6) 0.0083(6) 0.0053(6) C44 0.0277(8) 0.0261(7) 0.0196(7) 0.0078(6) 0.0108(6) 0.0133(6) C45 0.0232(7) 0.0286(8) 0.0166(7) 0.0106(6) 0.0081(6) 0.0081(6) C46 0.0308(8) 0.0227(7) 0.0198(7) 0.0097(6) 0.0080(6) 0.0097(6) C47 0.0378(11) 0.0510(12) 0.0454(12) 0.0206(10) 0.0165(9) 0.0294(10) _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 O1 1.9744(13) . ? Ge1 O1 1.9756(13) 2_666 ? Ge1 C1 2.0339(14) . ? O1 H1 0.98(5) . ? O1 Ge1 1.9756(12) 2_666 ? C1 C6 1.4097(18) . ? C1 C2 1.4126(18) . ? C2 C3 1.3963(19) . ? C2 C7 1.5002(19) . ? C3 C4 1.3913(19) . ? C4 C5 1.3895(19) . ? C5 C6 1.3978(19) . ? C6 C19 1.5050(18) . ? C7 C8 1.412(2) . ? C7 C12 1.414(2) . ? C8 C9 1.398(2) . ? C8 C13 1.524(2) . ? C9 C10 1.385(3) . ? C10 C11 1.389(3) . ? C11 C12 1.398(2) . ? C12 C16 1.524(2) . ? C13 C14 1.532(2) . ? C13 C15 1.533(2) . ? C16 C18 1.531(2) . ? C16 C17 1.535(2) . ? C19 C24 1.4107(19) . ? C19 C20 1.4151(18) . ? C20 C21 1.3962(19) . ? C20 C25 1.5224(19) . ? C21 C22 1.389(2) . ? C22 C23 1.392(2) . ? C23 C24 1.399(2) . ? C24 C28 1.5274(19) . ? C25 C27 1.534(2) . ? C25 C26 1.535(2) . ? C28 C30 1.531(2) . ? C28 C29 1.535(2) . ? C31 C36 1.392(3) . ? C31 C32 1.395(2) . ? C31 C37 1.509(3) . ? C32 C33 1.389(3) . ? C33 C34 1.385(3) . ? C34 C35 1.386(3) . ? C35 C36 1.391(3) . ? C41 C46 1.393(2) . ? C41 C42 1.395(2) . ? C41 C47 1.507(3) . ? C42 C43 1.387(2) . ? C43 C44 1.388(2) . ? C44 C45 1.387(2) . ? C45 C46 1.390(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ge1 O1 75.34(6) . 2_666 ? O1 Ge1 C1 98.30(5) . . ? O1 Ge1 C1 98.31(5) 2_666 . ? H1 O1 Ge1 127(3) . . ? H1 O1 Ge1 127(3) . 2_666 ? Ge1 O1 Ge1 104.66(6) . 2_666 ? C6 C1 C2 117.80(12) . . ? C6 C1 Ge1 121.24(10) . . ? C2 C1 Ge1 120.04(10) . . ? C3 C2 C1 120.71(12) . . ? C3 C2 C7 118.66(12) . . ? C1 C2 C7 120.53(12) . . ? C4 C3 C2 120.61(13) . . ? C5 C4 C3 119.36(13) . . ? C4 C5 C6 120.66(12) . . ? C5 C6 C1 120.71(12) . . ? C5 C6 C19 117.25(12) . . ? C1 C6 C19 122.02(12) . . ? C8 C7 C12 120.58(13) . . ? C8 C7 C2 119.17(13) . . ? C12 C7 C2 120.25(12) . . ? C9 C8 C7 118.56(14) . . ? C9 C8 C13 120.14(14) . . ? C7 C8 C13 121.21(13) . . ? C10 C9 C8 121.06(15) . . ? C9 C10 C11 120.27(14) . . ? C10 C11 C12 120.69(15) . . ? C11 C12 C7 118.82(14) . . ? C11 C12 C16 120.05(14) . . ? C7 C12 C16 121.11(13) . . ? C8 C13 C14 113.14(15) . . ? C8 C13 C15 110.02(13) . . ? C14 C13 C15 110.68(14) . . ? C12 C16 C18 110.86(13) . . ? C12 C16 C17 113.47(14) . . ? C18 C16 C17 109.44(14) . . ? C24 C19 C20 120.49(12) . . ? C24 C19 C6 120.11(12) . . ? C20 C19 C6 119.27(12) . . ? C21 C20 C19 118.78(13) . . ? C21 C20 C25 120.35(12) . . ? C19 C20 C25 120.85(12) . . ? C22 C21 C20 120.99(13) . . ? C21 C22 C23 120.06(13) . . ? C22 C23 C24 120.73(13) . . ? C23 C24 C19 118.93(12) . . ? C23 C24 C28 119.47(12) . . ? C19 C24 C28 121.45(12) . . ? C20 C25 C27 112.68(12) . . ? C20 C25 C26 111.12(12) . . ? C27 C25 C26 109.65(12) . . ? C24 C28 C30 113.17(13) . . ? C24 C28 C29 109.93(12) . . ? C30 C28 C29 110.60(13) . . ? C36 C31 C32 118.21(16) . . ? C36 C31 C37 121.41(17) . . ? C32 C31 C37 120.37(17) . . ? C33 C32 C31 121.01(17) . . ? C34 C33 C32 120.17(17) . . ? C33 C34 C35 119.46(18) . . ? C34 C35 C36 120.35(18) . . ? C35 C36 C31 120.79(17) . . ? C46 C41 C42 118.34(15) . . ? C46 C41 C47 121.14(17) . . ? C42 C41 C47 120.52(17) . . ? C43 C42 C41 121.01(15) . . ? C42 C43 C44 120.12(16) . . ? C45 C44 C43 119.46(15) . . ? C44 C45 C46 120.34(15) . . ? C45 C46 C41 120.73(15) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.807 _refine_diff_density_min -1.175 _refine_diff_density_rms 0.066