# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Matthias Driess' _publ_contact_author_email MATTHIAS.DRIESS@TU-BERLIN.DE _publ_section_title ; From NHC-Germylenes to Stable NHC-Germanone Complexes ; loop_ _publ_author_name 'Matthias Driess' 'Yun Xiong.' 'Shenglai Yao.' # Attachment '2a.CIF' data_2a _database_code_depnum_ccdc_archive 'CCDC 731869' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 Ge N4' _chemical_formula_weight 613.41 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 P21/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 12.5971(6) _cell_length_b 16.7102(6) _cell_length_c 17.2809(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.778(4) _cell_angle_gamma 90.00 _cell_volume 3500.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3666 _cell_measurement_theta_min 2.9531 _cell_measurement_theta_max 28.8615 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_T_min 0.95990 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15170 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.1390 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6140 _reflns_number_gt 3688 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6140 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 0.90870(3) 0.38161(2) 0.12949(2) 0.02280(12) Uani 1 1 d . . . N1 N 0.8155(2) 0.34100(17) 0.19235(14) 0.0236(8) Uani 1 1 d . . . N2 N 1.0240(2) 0.30355(16) 0.16742(14) 0.0238(8) Uani 1 1 d . . . N3 N 1.0433(3) 0.47742(18) 0.28835(16) 0.0298(8) Uani 1 1 d . . . N4 N 0.9803(2) 0.55258(18) 0.18646(16) 0.0261(8) Uani 1 1 d . . . C1 C 0.7519(3) 0.2449(2) 0.27441(19) 0.0400(11) Uani 1 1 d . . . H1A H 0.6834 0.2721 0.2653 0.048 Uiso 1 1 calc R . . H1B H 0.7655 0.1982 0.3070 0.048 Uiso 1 1 calc R . . C2 C 0.8316(3) 0.2732(2) 0.24029(18) 0.0259(10) Uani 1 1 d . . . C3 C 0.9351(3) 0.2325(2) 0.25551(18) 0.0258(9) Uani 1 1 d . . . H3 H 0.9454 0.1914 0.2948 0.031 Uiso 1 1 calc R . . C4 C 1.0211(3) 0.2427(2) 0.22312(18) 0.0263(10) Uani 1 1 d . . . C5 C 1.1191(3) 0.1912(2) 0.24846(19) 0.0386(11) Uani 1 1 d . . . H5A H 1.1089 0.1528 0.2887 0.058 Uiso 1 1 calc R . . H5B H 1.1842 0.2242 0.2718 0.058 Uiso 1 1 calc R . . H5C H 1.1295 0.1622 0.2018 0.058 Uiso 1 1 calc R . . C6 C 0.7120(3) 0.3819(2) 0.17360(19) 0.0275(9) Uani 1 1 d . . . C7 C 0.6923(3) 0.4433(2) 0.2238(2) 0.0316(10) Uani 1 1 d . . . C8 C 0.5984(4) 0.4900(2) 0.1981(3) 0.0461(12) Uani 1 1 d . . . H8 H 0.5850 0.5315 0.2318 0.055 Uiso 1 1 calc R . . C9 C 0.5238(4) 0.4770(3) 0.1238(3) 0.0552(14) Uani 1 1 d . . . H9 H 0.4616 0.5111 0.1058 0.066 Uiso 1 1 calc R . . C10 C 0.5400(4) 0.4150(3) 0.0767(2) 0.0471(13) Uani 1 1 d . . . H10 H 0.4870 0.4053 0.0268 0.056 Uiso 1 1 calc R . . C11 C 0.6326(3) 0.3655(2) 0.1002(2) 0.0344(11) Uani 1 1 d . . . C12 C 0.6429(3) 0.2949(3) 0.04852(19) 0.0393(11) Uani 1 1 d . . . H12 H 0.7188 0.2724 0.0702 0.047 Uiso 1 1 calc R . . C13 C 0.6298(4) 0.3182(3) -0.0397(2) 0.0695(16) Uani 1 1 d . . . H13A H 0.5553 0.3391 -0.0632 0.104 Uiso 1 1 calc R . . H13B H 0.6416 0.2710 -0.0700 0.104 Uiso 1 1 calc R . . H13C H 0.6842 0.3594 -0.0422 0.104 Uiso 1 1 calc R . . C14 C 0.5612(4) 0.2293(3) 0.0533(2) 0.0689(15) Uani 1 1 d . . . H14A H 0.5715 0.2140 0.1096 0.103 Uiso 1 1 calc R . . H14B H 0.5737 0.1826 0.0225 0.103 Uiso 1 1 calc R . . H14C H 0.4859 0.2490 0.0308 0.103 Uiso 1 1 calc R . . C15 C 0.7677(4) 0.4573(2) 0.3076(2) 0.0403(12) Uani 1 1 d . . . H15 H 0.8350 0.4236 0.3134 0.048 Uiso 1 1 calc R . . C16 C 0.8054(4) 0.5443(2) 0.3233(2) 0.0573(14) Uani 1 1 d . . . H16A H 0.8374 0.5625 0.2806 0.086 Uiso 1 1 calc R . . H16B H 0.8609 0.5481 0.3753 0.086 Uiso 1 1 calc R . . H16C H 0.7420 0.5780 0.3239 0.086 Uiso 1 1 calc R . . C17 C 0.7112(4) 0.4295(3) 0.3715(2) 0.0655(16) Uani 1 1 d . . . H17A H 0.6422 0.4592 0.3649 0.098 Uiso 1 1 calc R . . H17B H 0.7602 0.4396 0.4252 0.098 Uiso 1 1 calc R . . H17C H 0.6952 0.3721 0.3650 0.098 Uiso 1 1 calc R . . C18 C 1.0917(3) 0.2902(2) 0.11390(18) 0.0233(9) Uani 1 1 d . . . C19 C 1.0603(3) 0.2306(2) 0.05356(19) 0.0290(10) Uani 1 1 d . . . C20 C 1.1281(3) 0.2179(2) 0.0036(2) 0.0352(11) Uani 1 1 d . . . H20 H 1.1084 0.1777 -0.0366 0.042 Uiso 1 1 calc R . . C21 C 1.2223(4) 0.2613(2) 0.0103(2) 0.0358(11) Uani 1 1 d . . . H21 H 1.2679 0.2505 -0.0242 0.043 Uiso 1 1 calc R . . C22 C 1.2505(3) 0.3208(2) 0.06740(19) 0.0335(10) Uani 1 1 d . . . H22 H 1.3149 0.3520 0.0713 0.040 Uiso 1 1 calc R . . C23 C 1.1853(3) 0.3359(2) 0.11968(19) 0.0274(10) Uani 1 1 d . . . C24 C 1.2180(3) 0.4050(2) 0.1790(2) 0.0338(11) Uani 1 1 d . . . H24 H 1.1633 0.4064 0.2114 0.041 Uiso 1 1 calc R . . C25 C 1.3321(3) 0.3940(2) 0.2382(2) 0.0457(12) Uani 1 1 d . . . H25A H 1.3325 0.3452 0.2698 0.069 Uiso 1 1 calc R . . H25B H 1.3489 0.4403 0.2744 0.069 Uiso 1 1 calc R . . H25C H 1.3878 0.3896 0.2084 0.069 Uiso 1 1 calc R . . C26 C 1.2104(3) 0.4854(2) 0.1355(2) 0.0444(12) Uani 1 1 d . . . H26A H 1.2652 0.4872 0.1047 0.067 Uiso 1 1 calc R . . H26B H 1.2249 0.5289 0.1751 0.067 Uiso 1 1 calc R . . H26C H 1.1364 0.4918 0.0990 0.067 Uiso 1 1 calc R . . C27 C 0.9553(4) 0.1825(2) 0.0411(2) 0.0412(12) Uani 1 1 d . . . H27 H 0.9192 0.1986 0.0837 0.049 Uiso 1 1 calc R . . C28 C 0.9774(5) 0.0931(3) 0.0490(3) 0.098(2) Uani 1 1 d . . . H28A H 1.0049 0.0747 0.0042 0.147 Uiso 1 1 calc R . . H28B H 0.9089 0.0648 0.0480 0.147 Uiso 1 1 calc R . . H28C H 1.0328 0.0821 0.0999 0.147 Uiso 1 1 calc R . . C29 C 0.8761(4) 0.2014(3) -0.0400(2) 0.0836(19) Uani 1 1 d . . . H29A H 0.9080 0.1836 -0.0829 0.125 Uiso 1 1 calc R . . H29B H 0.8630 0.2593 -0.0446 0.125 Uiso 1 1 calc R . . H29C H 0.8060 0.1736 -0.0451 0.125 Uiso 1 1 calc R . . C30 C 0.9804(3) 0.4758(2) 0.2118(2) 0.0245(9) Uani 1 1 d . . . C31 C 1.0436(3) 0.6010(2) 0.2463(2) 0.0343(10) Uani 1 1 d . . . C32 C 1.0832(3) 0.5538(3) 0.3103(2) 0.0395(11) Uani 1 1 d . . . C33 C 1.0677(3) 0.4083(2) 0.34147(18) 0.0429(12) Uani 1 1 d . . . H33A H 1.0249 0.3622 0.3149 0.064 Uiso 1 1 calc R . . H33B H 1.0480 0.4203 0.3914 0.064 Uiso 1 1 calc R . . H33C H 1.1466 0.3960 0.3540 0.064 Uiso 1 1 calc R . . C34 C 0.9203(3) 0.5823(2) 0.1078(2) 0.0460(12) Uani 1 1 d . . . H34A H 0.8811 0.5380 0.0751 0.069 Uiso 1 1 calc R . . H34B H 0.9723 0.6061 0.0812 0.069 Uiso 1 1 calc R . . H34C H 0.8671 0.6229 0.1139 0.069 Uiso 1 1 calc R . . C35 C 1.0595(4) 0.6880(2) 0.2345(2) 0.0561(13) Uani 1 1 d . . . H35A H 1.1091 0.7105 0.2835 0.084 Uiso 1 1 calc R . . H35B H 0.9881 0.7154 0.2229 0.084 Uiso 1 1 calc R . . H35C H 1.0917 0.6955 0.1894 0.084 Uiso 1 1 calc R . . C36 C 1.1557(4) 0.5721(3) 0.3920(2) 0.0693(15) Uani 1 1 d . . . H36A H 1.1744 0.6291 0.3955 0.104 Uiso 1 1 calc R . . H36B H 1.2234 0.5403 0.4018 0.104 Uiso 1 1 calc R . . H36C H 1.1169 0.5589 0.4324 0.104 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 0.0258(2) 0.0223(2) 0.01922(19) 0.0018(2) 0.00422(15) -0.0016(3) N1 0.0246(19) 0.0245(19) 0.0208(15) 0.0030(14) 0.0045(14) 0.0046(16) N2 0.033(2) 0.0190(18) 0.0231(15) 0.0039(14) 0.0135(15) 0.0031(17) N3 0.034(2) 0.027(2) 0.0239(17) -0.0019(16) -0.0012(16) 0.0041(18) N4 0.025(2) 0.0173(18) 0.0351(18) 0.0045(16) 0.0071(16) 0.0022(17) C1 0.039(3) 0.035(3) 0.050(2) 0.016(2) 0.019(2) 0.003(2) C2 0.036(3) 0.021(2) 0.0201(19) 0.0025(18) 0.0065(19) -0.001(2) C3 0.038(3) 0.017(2) 0.0236(19) 0.0045(17) 0.010(2) 0.002(2) C4 0.035(3) 0.020(2) 0.022(2) 0.0002(17) 0.0048(19) 0.005(2) C5 0.053(3) 0.026(2) 0.039(2) 0.0134(19) 0.016(2) 0.016(2) C6 0.029(2) 0.027(2) 0.030(2) 0.012(2) 0.0147(19) -0.002(2) C7 0.036(3) 0.021(2) 0.046(3) 0.007(2) 0.026(2) 0.001(2) C8 0.055(3) 0.033(3) 0.064(3) 0.013(2) 0.040(3) 0.014(3) C9 0.038(3) 0.063(4) 0.074(3) 0.036(3) 0.031(3) 0.010(3) C10 0.028(3) 0.059(3) 0.051(3) 0.022(3) 0.004(2) 0.000(3) C11 0.027(2) 0.038(3) 0.037(2) 0.013(2) 0.007(2) -0.005(2) C12 0.031(3) 0.048(3) 0.032(2) 0.002(2) -0.002(2) -0.004(2) C13 0.097(4) 0.063(4) 0.039(3) -0.004(2) 0.004(3) -0.009(4) C14 0.063(4) 0.052(3) 0.091(3) 0.000(3) 0.020(3) -0.014(3) C15 0.062(3) 0.027(3) 0.040(2) -0.005(2) 0.026(2) 0.004(3) C16 0.077(4) 0.036(3) 0.068(3) -0.012(2) 0.034(3) -0.002(3) C17 0.107(5) 0.055(3) 0.053(3) 0.000(3) 0.054(3) -0.003(3) C18 0.029(2) 0.019(2) 0.0239(19) 0.0045(18) 0.0108(19) 0.001(2) C19 0.038(3) 0.026(2) 0.025(2) 0.0044(18) 0.012(2) 0.007(2) C20 0.048(3) 0.029(3) 0.030(2) -0.0004(19) 0.013(2) 0.007(2) C21 0.046(3) 0.039(3) 0.030(2) 0.014(2) 0.024(2) 0.022(3) C22 0.030(3) 0.034(3) 0.036(2) 0.011(2) 0.010(2) 0.006(2) C23 0.031(3) 0.026(2) 0.027(2) 0.0078(18) 0.0089(19) 0.009(2) C24 0.028(3) 0.034(3) 0.041(2) -0.002(2) 0.012(2) -0.006(2) C25 0.051(3) 0.039(3) 0.046(2) 0.000(2) 0.010(2) 0.001(3) C26 0.035(3) 0.036(3) 0.064(3) 0.001(2) 0.017(2) 0.001(2) C27 0.054(3) 0.037(3) 0.042(3) -0.014(2) 0.029(2) -0.013(3) C28 0.137(6) 0.032(3) 0.146(5) -0.020(3) 0.075(5) -0.029(4) C29 0.066(4) 0.130(5) 0.047(3) -0.025(3) 0.001(3) -0.047(4) C30 0.025(2) 0.018(2) 0.030(2) 0.0043(18) 0.0056(19) 0.002(2) C31 0.029(3) 0.020(3) 0.053(3) -0.007(2) 0.010(2) -0.001(2) C32 0.034(3) 0.030(3) 0.051(3) -0.020(2) 0.006(2) -0.009(2) C33 0.053(3) 0.040(3) 0.026(2) -0.0001(19) -0.006(2) 0.003(2) C34 0.050(3) 0.028(2) 0.058(3) 0.020(2) 0.013(2) 0.008(3) C35 0.055(3) 0.025(3) 0.093(3) -0.010(2) 0.029(3) -0.006(3) C36 0.065(4) 0.053(3) 0.071(3) -0.025(3) -0.014(3) -0.007(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 Ge1 N1 1.927(3) . ? Ge1 N2 1.929(3) . ? Ge1 C30 2.149(3) . ? N1 C2 1.385(4) . ? N1 C6 1.429(4) . ? N2 C4 1.407(4) . ? N2 C18 1.436(4) . ? N3 C30 1.345(4) . ? N3 C32 1.386(5) . ? N3 C33 1.455(4) . ? N4 C30 1.355(4) . ? N4 C31 1.383(4) . ? N4 C34 1.452(4) . ? C1 C2 1.379(5) . ? C2 C3 1.430(5) . ? C3 C4 1.359(5) . ? C4 C5 1.471(5) . ? C6 C7 1.408(5) . ? C6 C11 1.412(5) . ? C7 C8 1.386(5) . ? C7 C15 1.519(5) . ? C8 C9 1.386(5) . ? C9 C10 1.367(5) . ? C10 C11 1.398(5) . ? C11 C12 1.507(5) . ? C12 C14 1.521(5) . ? C12 C13 1.539(4) . ? C15 C16 1.531(5) . ? C15 C17 1.539(5) . ? C18 C23 1.386(5) . ? C18 C19 1.418(4) . ? C19 C20 1.386(5) . ? C19 C27 1.512(5) . ? C20 C21 1.370(5) . ? C21 C22 1.378(5) . ? C22 C23 1.400(4) . ? C23 C24 1.523(5) . ? C24 C26 1.530(5) . ? C24 C25 1.532(5) . ? C27 C29 1.517(5) . ? C27 C28 1.519(6) . ? C31 C32 1.340(5) . ? C31 C35 1.489(5) . ? C32 C36 1.490(5) . ? 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 95.06(12) . . ? N1 Ge1 C30 95.48(12) . . ? N2 Ge1 C30 97.39(12) . . ? C2 N1 C6 120.2(3) . . ? C2 N1 Ge1 127.7(3) . . ? C6 N1 Ge1 111.2(2) . . ? C4 N2 C18 117.3(3) . . ? C4 N2 Ge1 124.3(2) . . ? C18 N2 Ge1 114.2(2) . . ? C30 N3 C32 111.1(3) . . ? C30 N3 C33 124.9(3) . . ? C32 N3 C33 124.0(3) . . ? C30 N4 C31 111.3(3) . . ? C30 N4 C34 125.5(3) . . ? C31 N4 C34 123.2(3) . . ? C1 C2 N1 122.0(4) . . ? C1 C2 C3 119.4(3) . . ? N1 C2 C3 118.5(3) . . ? C4 C3 C2 130.8(3) . . ? C3 C4 N2 123.0(3) . . ? C3 C4 C5 120.1(3) . . ? N2 C4 C5 116.8(3) . . ? C7 C6 C11 119.6(4) . . ? C7 C6 N1 120.8(3) . . ? C11 C6 N1 119.4(3) . . ? C8 C7 C6 119.4(4) . . ? C8 C7 C15 118.5(4) . . ? C6 C7 C15 122.0(4) . . ? C9 C8 C7 120.9(4) . . ? C10 C9 C8 119.8(4) . . ? C9 C10 C11 121.6(4) . . ? C10 C11 C6 118.5(4) . . ? C10 C11 C12 119.4(4) . . ? C6 C11 C12 122.0(4) . . ? C11 C12 C14 111.3(3) . . ? C11 C12 C13 112.7(3) . . ? C14 C12 C13 110.1(3) . . ? C7 C15 C16 113.5(3) . . ? C7 C15 C17 110.2(3) . . ? C16 C15 C17 109.9(3) . . ? C23 C18 C19 120.1(3) . . ? C23 C18 N2 120.7(3) . . ? C19 C18 N2 119.2(3) . . ? C20 C19 C18 118.0(4) . . ? C20 C19 C27 119.6(3) . . ? C18 C19 C27 122.4(3) . . ? C21 C20 C19 122.3(4) . . ? C20 C21 C22 119.4(4) . . ? C21 C22 C23 120.7(4) . . ? C18 C23 C22 119.5(3) . . ? C18 C23 C24 122.4(3) . . ? C22 C23 C24 118.1(4) . . ? C23 C24 C26 111.5(3) . . ? C23 C24 C25 113.1(3) . . ? C26 C24 C25 110.8(3) . . ? C19 C27 C29 110.5(3) . . ? C19 C27 C28 112.2(4) . . ? C29 C27 C28 110.3(4) . . ? N3 C30 N4 104.3(3) . . ? N3 C30 Ge1 134.0(3) . . ? N4 C30 Ge1 121.1(2) . . ? C32 C31 N4 106.4(3) . . ? C32 C31 C35 130.9(4) . . ? N4 C31 C35 122.7(4) . . ? C31 C32 N3 106.9(3) . . ? C31 C32 C36 131.0(4) . . ? N3 C32 C36 122.1(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.643 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.062 # Attachment '2b.CIF' data_2b _database_code_depnum_ccdc_archive 'CCDC 731870' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H68 Ge N4' _chemical_formula_weight 761.64 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1525(4) _cell_length_b 14.2463(5) _cell_length_c 14.3356(6) _cell_angle_alpha 74.438(3) _cell_angle_beta 80.643(3) _cell_angle_gamma 87.108(3) _cell_volume 2164.92(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5773 _cell_measurement_theta_min 2.9599 _cell_measurement_theta_max 32.3408 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_T_min 0.97301 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16315 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7585 _reflns_number_gt 5513 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0251P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7585 _refine_ls_number_parameters 485 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.013 _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 0.40885(3) 0.19553(2) 0.82367(2) 0.01531(9) Uani 1 1 d . . . N1 N 0.32778(19) 0.23966(14) 0.70921(15) 0.0166(5) Uani 1 1 d . . . N2 N 0.40796(19) 0.32025(14) 0.85003(16) 0.0168(5) Uani 1 1 d . . . N3 N 0.6370(2) 0.09733(15) 0.74110(16) 0.0202(5) Uani 1 1 d . . . N4 N 0.6727(2) 0.25043(15) 0.67818(16) 0.0207(6) Uani 1 1 d . . . C1 C 0.1998(3) 0.3538(2) 0.6117(2) 0.0301(8) Uani 1 1 d . . . H1A H 0.1682 0.3031 0.5914 0.036 Uiso 1 1 calc R . . H1B H 0.1727 0.4190 0.5891 0.036 Uiso 1 1 calc R . . C2 C 0.2838(2) 0.33301(18) 0.6731(2) 0.0195(7) Uani 1 1 d . . . C3 C 0.3290(2) 0.41197(18) 0.7047(2) 0.0208(7) Uani 1 1 d . . . H3 H 0.3213 0.4754 0.6628 0.025 Uiso 1 1 calc R . . C4 C 0.3803(2) 0.40782(18) 0.7847(2) 0.0200(7) Uani 1 1 d . . . C5 C 0.4144(3) 0.49924(18) 0.8067(2) 0.0298(8) Uani 1 1 d . . . H5A H 0.3930 0.5560 0.7560 0.045 Uiso 1 1 calc R . . H5B H 0.5020 0.4989 0.8078 0.045 Uiso 1 1 calc R . . H5C H 0.3704 0.5026 0.8708 0.045 Uiso 1 1 calc R . . C6 C 0.2903(2) 0.16483(18) 0.67126(19) 0.0177(6) Uani 1 1 d . . . C7 C 0.3488(2) 0.15383(19) 0.5790(2) 0.0207(7) Uani 1 1 d . . . C8 C 0.3103(3) 0.0804(2) 0.5441(2) 0.0280(8) Uani 1 1 d . . . H8 H 0.3485 0.0733 0.4821 0.034 Uiso 1 1 calc R . . C9 C 0.2188(3) 0.0179(2) 0.5961(2) 0.0321(8) Uani 1 1 d . . . H9 H 0.1939 -0.0316 0.5705 0.039 Uiso 1 1 calc R . . C10 C 0.1633(3) 0.0280(2) 0.6865(2) 0.0288(8) Uani 1 1 d . . . H10 H 0.1010 -0.0161 0.7233 0.035 Uiso 1 1 calc R . . C11 C 0.1961(2) 0.10071(19) 0.7247(2) 0.0213(7) Uani 1 1 d . . . C12 C 0.1289(2) 0.10796(19) 0.8240(2) 0.0234(7) Uani 1 1 d . . . H12 H 0.1648 0.1631 0.8407 0.028 Uiso 1 1 calc R . . C13 C 0.1469(3) 0.0155(2) 0.9031(2) 0.0385(9) Uani 1 1 d . . . H13A H 0.1068 -0.0389 0.8912 0.058 Uiso 1 1 calc R . . H13B H 0.1117 0.0244 0.9674 0.058 Uiso 1 1 calc R . . H13C H 0.2340 0.0013 0.9017 0.058 Uiso 1 1 calc R . . C14 C -0.0056(3) 0.1304(2) 0.8205(2) 0.0440(9) Uani 1 1 d . . . H14A H -0.0146 0.1922 0.7715 0.066 Uiso 1 1 calc R . . H14B H -0.0460 0.1355 0.8850 0.066 Uiso 1 1 calc R . . H14C H -0.0428 0.0780 0.8029 0.066 Uiso 1 1 calc R . . C15 C 0.4512(3) 0.2191(2) 0.5190(2) 0.0273(7) Uani 1 1 d . . . H15 H 0.4733 0.2601 0.5603 0.033 Uiso 1 1 calc R . . C16 C 0.5652(3) 0.1624(2) 0.4908(2) 0.0360(8) Uani 1 1 d . . . H16A H 0.5898 0.1186 0.5501 0.054 Uiso 1 1 calc R . . H16B H 0.6310 0.2081 0.4572 0.054 Uiso 1 1 calc R . . H16C H 0.5479 0.1241 0.4471 0.054 Uiso 1 1 calc R . . C17 C 0.4145(3) 0.2878(2) 0.4270(2) 0.0458(9) Uani 1 1 d . . . H17A H 0.3947 0.2499 0.3838 0.069 Uiso 1 1 calc R . . H17B H 0.4819 0.3318 0.3929 0.069 Uiso 1 1 calc R . . H17C H 0.3432 0.3260 0.4450 0.069 Uiso 1 1 calc R . . C18 C 0.3955(2) 0.31902(17) 0.95266(19) 0.0166(6) Uani 1 1 d . . . C19 C 0.4983(3) 0.31579(18) 0.9968(2) 0.0211(7) Uani 1 1 d . . . C20 C 0.4841(3) 0.31528(19) 1.0954(2) 0.0259(7) Uani 1 1 d . . . H20 H 0.5538 0.3125 1.1264 0.031 Uiso 1 1 calc R . . C21 C 0.3699(3) 0.31872(18) 1.1484(2) 0.0274(8) Uani 1 1 d . . . H21 H 0.3611 0.3197 1.2152 0.033 Uiso 1 1 calc R . . C22 C 0.2689(3) 0.32079(19) 1.1045(2) 0.0268(7) Uani 1 1 d . . . H22 H 0.1907 0.3231 1.1417 0.032 Uiso 1 1 calc R . . C23 C 0.2784(2) 0.31956(17) 1.0063(2) 0.0192(7) Uani 1 1 d . . . C24 C 0.1634(2) 0.31847(19) 0.9638(2) 0.0259(7) Uani 1 1 d . . . H24 H 0.1868 0.3130 0.8951 0.031 Uiso 1 1 calc R . . C25 C 0.0847(3) 0.2307(2) 1.0217(2) 0.0388(9) Uani 1 1 d . . . H25A H 0.1326 0.1707 1.0243 0.058 Uiso 1 1 calc R . . H25B H 0.0142 0.2288 0.9895 0.058 Uiso 1 1 calc R . . H25C H 0.0571 0.2363 1.0885 0.058 Uiso 1 1 calc R . . C26 C 0.0900(3) 0.4124(2) 0.9604(3) 0.0482(10) Uani 1 1 d . . . H26A H 0.0637 0.4182 1.0273 0.072 Uiso 1 1 calc R . . H26B H 0.0186 0.4110 0.9290 0.072 Uiso 1 1 calc R . . H26C H 0.1407 0.4683 0.9228 0.072 Uiso 1 1 calc R . . C27 C 0.6260(3) 0.3122(2) 0.9417(2) 0.0296(8) Uani 1 1 d . . . H27 H 0.6193 0.3260 0.8705 0.036 Uiso 1 1 calc R . . C28 C 0.6807(3) 0.2107(2) 0.9721(3) 0.0504(10) Uani 1 1 d . . . H28A H 0.6889 0.1948 1.0416 0.076 Uiso 1 1 calc R . . H28B H 0.7609 0.2087 0.9328 0.076 Uiso 1 1 calc R . . H28C H 0.6274 0.1631 0.9614 0.076 Uiso 1 1 calc R . . C29 C 0.7100(3) 0.3891(2) 0.9524(3) 0.0461(9) Uani 1 1 d . . . H29A H 0.6737 0.4540 0.9313 0.069 Uiso 1 1 calc R . . H29B H 0.7890 0.3864 0.9117 0.069 Uiso 1 1 calc R . . H29C H 0.7210 0.3763 1.0212 0.069 Uiso 1 1 calc R . . C30 C 0.5898(2) 0.18735(18) 0.7394(2) 0.0182(6) Uani 1 1 d . . . C31 C 0.7490(2) 0.1046(2) 0.6796(2) 0.0243(7) Uani 1 1 d . . . C32 C 0.7709(3) 0.2003(2) 0.6406(2) 0.0254(7) Uani 1 1 d . . . C33 C 0.6588(3) 0.35702(19) 0.6602(2) 0.0289(8) Uani 1 1 d . . . H33 H 0.5837 0.3690 0.7041 0.035 Uiso 1 1 calc R . . C34 C 0.6398(3) 0.4077(2) 0.5562(2) 0.0469(10) Uani 1 1 d . . . H34A H 0.7046 0.3884 0.5099 0.070 Uiso 1 1 calc R . . H34B H 0.6415 0.4784 0.5462 0.070 Uiso 1 1 calc R . . H34C H 0.5609 0.3890 0.5452 0.070 Uiso 1 1 calc R . . C35 C 0.7636(3) 0.4024(2) 0.6886(2) 0.0438(9) Uani 1 1 d . . . H35A H 0.7894 0.3581 0.7471 0.066 Uiso 1 1 calc R . . H35B H 0.7370 0.4645 0.7024 0.066 Uiso 1 1 calc R . . H35C H 0.8319 0.4136 0.6345 0.066 Uiso 1 1 calc R . . C36 C 0.5775(3) 0.00626(19) 0.8028(2) 0.0288(8) Uani 1 1 d . . . H36 H 0.5045 0.0269 0.8432 0.035 Uiso 1 1 calc R . . C37 C 0.5294(3) -0.0527(2) 0.7433(2) 0.0466(9) Uani 1 1 d . . . H37A H 0.4790 -0.0108 0.6987 0.070 Uiso 1 1 calc R . . H37B H 0.4805 -0.1067 0.7876 0.070 Uiso 1 1 calc R . . H37C H 0.5978 -0.0787 0.7053 0.070 Uiso 1 1 calc R . . C38 C 0.6552(3) -0.0523(2) 0.8748(2) 0.0520(10) Uani 1 1 d . . . H38A H 0.7242 -0.0806 0.8396 0.078 Uiso 1 1 calc R . . H38B H 0.6067 -0.1047 0.9222 0.078 Uiso 1 1 calc R . . H38C H 0.6853 -0.0098 0.9094 0.078 Uiso 1 1 calc R . . C39 C 0.8234(3) 0.0200(2) 0.6595(2) 0.0392(9) Uani 1 1 d . . . H39A H 0.8953 0.0439 0.6111 0.059 Uiso 1 1 calc R . . H39B H 0.7748 -0.0199 0.6338 0.059 Uiso 1 1 calc R . . H39C H 0.8489 -0.0195 0.7203 0.059 Uiso 1 1 calc R . . C40 C 0.8785(3) 0.2459(2) 0.5693(2) 0.0441(9) Uani 1 1 d . . . H40A H 0.9319 0.1948 0.5511 0.066 Uiso 1 1 calc R . . H40B H 0.9231 0.2844 0.5994 0.066 Uiso 1 1 calc R . . H40C H 0.8511 0.2884 0.5106 0.066 Uiso 1 1 calc R . . C41 C 0.1930(3) 0.7500(2) 0.7662(3) 0.0482(10) Uani 1 1 d . . . H41A H 0.2130 0.8178 0.7310 0.072 Uiso 1 1 calc R . . H41B H 0.2656 0.7090 0.7601 0.072 Uiso 1 1 calc R . . H41C H 0.1646 0.7456 0.8356 0.072 Uiso 1 1 calc R . . C42 C 0.0949(3) 0.7156(2) 0.7231(2) 0.0302(8) Uani 1 1 d . . . C43 C 0.0074(3) 0.7787(2) 0.6830(2) 0.0308(8) Uani 1 1 d . . . H43 H 0.0095 0.8455 0.6824 0.037 Uiso 1 1 calc R . . C44 C -0.0824(3) 0.7469(2) 0.6440(2) 0.0341(8) Uani 1 1 d . . . H44 H -0.1420 0.7917 0.6174 0.041 Uiso 1 1 calc R . . C45 C -0.0871(3) 0.6511(2) 0.6431(2) 0.0401(9) Uani 1 1 d . . . H45 H -0.1487 0.6293 0.6154 0.048 Uiso 1 1 calc R . . C46 C -0.0010(3) 0.5871(2) 0.6831(3) 0.0463(10) Uani 1 1 d . . . H46 H -0.0039 0.5203 0.6839 0.056 Uiso 1 1 calc R . . C47 C 0.0888(3) 0.6188(2) 0.7218(2) 0.0419(9) Uani 1 1 d . . . H47 H 0.1482 0.5737 0.7482 0.050 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 0.01707(18) 0.01572(16) 0.01266(16) -0.00402(12) -0.00052(12) 0.00007(12) N1 0.0207(14) 0.0161(12) 0.0154(13) -0.0068(10) -0.0052(10) 0.0014(10) N2 0.0177(13) 0.0177(12) 0.0159(13) -0.0053(10) -0.0044(10) 0.0017(10) N3 0.0215(14) 0.0225(13) 0.0172(13) -0.0069(11) -0.0033(11) 0.0050(11) N4 0.0188(14) 0.0250(13) 0.0174(13) -0.0050(11) 0.0001(11) -0.0048(11) C1 0.035(2) 0.0249(16) 0.0335(19) -0.0094(14) -0.0137(16) 0.0070(14) C2 0.0220(17) 0.0191(15) 0.0146(15) -0.0012(12) -0.0008(13) 0.0014(13) C3 0.0274(18) 0.0153(15) 0.0179(16) -0.0009(12) -0.0052(14) 0.0048(13) C4 0.0213(17) 0.0167(15) 0.0196(17) -0.0037(13) 0.0014(13) 0.0010(12) C5 0.044(2) 0.0211(16) 0.0248(18) -0.0054(14) -0.0059(15) -0.0007(14) C6 0.0218(17) 0.0159(14) 0.0167(16) -0.0040(12) -0.0079(13) 0.0032(12) C7 0.0220(17) 0.0214(15) 0.0190(16) -0.0056(13) -0.0041(13) 0.0022(13) C8 0.038(2) 0.0316(18) 0.0184(17) -0.0134(14) -0.0037(15) -0.0012(15) C9 0.036(2) 0.0342(18) 0.035(2) -0.0208(16) -0.0073(16) -0.0099(16) C10 0.0261(19) 0.0309(18) 0.030(2) -0.0105(15) 0.0003(15) -0.0085(15) C11 0.0208(17) 0.0232(16) 0.0217(17) -0.0090(13) -0.0031(14) -0.0005(13) C12 0.0213(18) 0.0273(16) 0.0219(17) -0.0089(13) 0.0012(14) -0.0045(13) C13 0.043(2) 0.0389(19) 0.028(2) -0.0059(16) 0.0072(17) -0.0080(16) C14 0.027(2) 0.072(2) 0.040(2) -0.0290(19) -0.0014(17) 0.0036(18) C15 0.0313(19) 0.0323(17) 0.0193(17) -0.0108(14) 0.0017(14) -0.0063(15) C16 0.0291(19) 0.053(2) 0.0257(19) -0.0114(16) -0.0020(15) -0.0026(16) C17 0.048(2) 0.049(2) 0.027(2) 0.0065(16) 0.0018(18) 0.0008(18) C18 0.0226(17) 0.0108(14) 0.0170(16) -0.0047(12) -0.0027(13) -0.0008(12) C19 0.0257(18) 0.0173(15) 0.0213(17) -0.0060(13) -0.0052(14) -0.0001(13) C20 0.033(2) 0.0244(16) 0.0230(18) -0.0066(14) -0.0120(15) -0.0010(14) C21 0.044(2) 0.0265(17) 0.0131(16) -0.0083(13) -0.0030(16) -0.0005(15) C22 0.032(2) 0.0260(17) 0.0224(18) -0.0098(14) 0.0014(15) 0.0013(14) C23 0.0233(18) 0.0158(15) 0.0194(17) -0.0063(12) -0.0034(13) 0.0014(12) C24 0.0189(17) 0.0356(18) 0.0229(18) -0.0097(14) -0.0004(14) 0.0047(14) C25 0.030(2) 0.054(2) 0.036(2) -0.0172(17) -0.0011(17) -0.0090(17) C26 0.038(2) 0.051(2) 0.060(3) -0.0173(19) -0.0179(19) 0.0149(18) C27 0.0231(18) 0.0418(19) 0.0261(19) -0.0121(15) -0.0042(15) -0.0011(15) C28 0.034(2) 0.059(2) 0.063(3) -0.028(2) -0.0065(19) 0.0169(18) C29 0.032(2) 0.067(2) 0.043(2) -0.0194(19) -0.0077(18) -0.0111(18) C30 0.0200(17) 0.0193(15) 0.0175(16) -0.0064(13) -0.0065(13) 0.0006(13) C31 0.0182(17) 0.0390(19) 0.0196(17) -0.0151(15) -0.0036(14) 0.0069(14) C32 0.0158(17) 0.046(2) 0.0183(17) -0.0161(15) -0.0018(14) 0.0029(15) C33 0.0273(19) 0.0256(17) 0.0293(19) -0.0022(14) 0.0027(15) -0.0074(14) C34 0.059(3) 0.0334(19) 0.042(2) 0.0035(17) -0.0096(19) -0.0134(17) C35 0.043(2) 0.045(2) 0.043(2) -0.0167(17) 0.0084(18) -0.0224(17) C36 0.038(2) 0.0182(16) 0.0266(18) -0.0045(14) 0.0002(15) 0.0048(14) C37 0.057(3) 0.0338(19) 0.048(2) -0.0023(17) -0.018(2) -0.0054(17) C38 0.085(3) 0.037(2) 0.036(2) -0.0063(17) -0.024(2) 0.0033(19) C39 0.029(2) 0.055(2) 0.042(2) -0.0299(18) -0.0043(17) 0.0119(16) C40 0.029(2) 0.065(2) 0.035(2) -0.0151(18) 0.0088(17) -0.0073(17) C41 0.048(2) 0.056(2) 0.044(2) -0.0162(19) -0.0159(19) 0.0069(19) C42 0.029(2) 0.037(2) 0.0239(18) -0.0088(15) 0.0000(15) 0.0018(15) C43 0.031(2) 0.0299(17) 0.0309(19) -0.0106(15) 0.0011(16) 0.0010(15) C44 0.0253(19) 0.041(2) 0.031(2) -0.0035(16) -0.0008(16) 0.0024(16) C45 0.033(2) 0.048(2) 0.038(2) -0.0120(18) 0.0032(17) -0.0121(18) C46 0.053(3) 0.032(2) 0.053(3) -0.0132(18) -0.002(2) -0.0046(19) C47 0.041(2) 0.035(2) 0.042(2) -0.0031(17) -0.0009(18) 0.0071(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 N2 1.912(2) . ? Ge1 N1 1.943(2) . ? Ge1 C30 2.192(3) . ? N1 C2 1.387(3) . ? N1 C6 1.427(3) . ? N2 C4 1.399(3) . ? N2 C18 1.450(3) . ? N3 C30 1.357(3) . ? N3 C31 1.398(3) . ? N3 C36 1.478(3) . ? N4 C30 1.353(3) . ? N4 C32 1.391(3) . ? N4 C33 1.475(3) . ? C1 C2 1.356(4) . ? C2 C3 1.459(4) . ? C3 C4 1.350(4) . ? C4 C5 1.500(3) . ? C6 C11 1.409(4) . ? C6 C7 1.421(4) . ? C7 C8 1.387(4) . ? C7 C15 1.506(4) . ? C8 C9 1.370(4) . ? C9 C10 1.383(4) . ? C10 C11 1.383(4) . ? C11 C12 1.524(4) . ? C12 C13 1.520(4) . ? C12 C14 1.524(4) . ? C15 C17 1.519(4) . ? C15 C16 1.528(4) . ? C18 C19 1.390(4) . ? C18 C23 1.404(3) . ? C19 C20 1.395(4) . ? C19 C27 1.518(4) . ? C20 C21 1.379(4) . ? C21 C22 1.372(4) . ? C22 C23 1.399(4) . ? C23 C24 1.509(4) . ? C24 C26 1.526(4) . ? C24 C25 1.530(4) . ? C27 C28 1.520(4) . ? C27 C29 1.531(4) . ? C31 C32 1.345(4) . ? C31 C39 1.494(4) . ? C32 C40 1.494(4) . ? C33 C34 1.516(4) . ? C33 C35 1.524(4) . ? C36 C38 1.506(4) . ? C36 C37 1.516(4) . ? C41 C42 1.502(4) . ? C42 C43 1.382(4) . ? C42 C47 1.388(4) . ? C43 C44 1.373(4) . ? C44 C45 1.372(4) . ? C45 C46 1.375(4) . ? C46 C47 1.370(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ge1 N1 95.35(9) . . ? N2 Ge1 C30 103.29(9) . . ? N1 Ge1 C30 94.85(9) . . ? C2 N1 C6 117.0(2) . . ? C2 N1 Ge1 126.06(17) . . ? C6 N1 Ge1 115.74(15) . . ? C4 N2 C18 117.0(2) . . ? C4 N2 Ge1 124.12(18) . . ? C18 N2 Ge1 115.69(15) . . ? C30 N3 C31 110.3(2) . . ? C30 N3 C36 123.4(2) . . ? C31 N3 C36 126.2(2) . . ? C30 N4 C32 110.5(2) . . ? C30 N4 C33 122.6(2) . . ? C32 N4 C33 126.8(2) . . ? C1 C2 N1 123.3(3) . . ? C1 C2 C3 118.8(2) . . ? N1 C2 C3 117.9(2) . . ? C4 C3 C2 129.3(2) . . ? C3 C4 N2 123.2(2) . . ? C3 C4 C5 120.8(2) . . ? N2 C4 C5 116.0(2) . . ? C11 C6 C7 119.2(2) . . ? C11 C6 N1 120.7(2) . . ? C7 C6 N1 120.1(2) . . ? C8 C7 C6 118.7(3) . . ? C8 C7 C15 119.5(2) . . ? C6 C7 C15 121.8(2) . . ? C9 C8 C7 122.1(3) . . ? C8 C9 C10 119.1(3) . . ? C9 C10 C11 121.7(3) . . ? C10 C11 C6 119.3(3) . . ? C10 C11 C12 118.4(3) . . ? C6 C11 C12 122.3(2) . . ? C13 C12 C14 111.3(2) . . ? C13 C12 C11 110.6(2) . . ? C14 C12 C11 111.4(2) . . ? C7 C15 C17 112.4(3) . . ? C7 C15 C16 112.9(2) . . ? C17 C15 C16 109.2(2) . . ? C19 C18 C23 121.1(3) . . ? C19 C18 N2 120.1(2) . . ? C23 C18 N2 118.9(2) . . ? C18 C19 C20 119.1(3) . . ? C18 C19 C27 122.3(3) . . ? C20 C19 C27 118.6(3) . . ? C21 C20 C19 120.6(3) . . ? C22 C21 C20 119.8(3) . . ? C21 C22 C23 121.7(3) . . ? C22 C23 C18 117.7(3) . . ? C22 C23 C24 118.8(3) . . ? C18 C23 C24 123.6(3) . . ? C23 C24 C26 111.5(2) . . ? C23 C24 C25 111.2(2) . . ? C26 C24 C25 109.9(2) . . ? C19 C27 C28 110.7(2) . . ? C19 C27 C29 113.1(2) . . ? C28 C27 C29 110.9(3) . . ? N4 C30 N3 105.4(2) . . ? N4 C30 Ge1 137.18(18) . . ? N3 C30 Ge1 117.39(18) . . ? C32 C31 N3 106.7(2) . . ? C32 C31 C39 128.4(3) . . ? N3 C31 C39 124.9(3) . . ? C31 C32 N4 107.1(2) . . ? C31 C32 C40 127.4(3) . . ? N4 C32 C40 125.5(3) . . ? N4 C33 C34 113.2(2) . . ? N4 C33 C35 112.0(2) . . ? C34 C33 C35 111.1(2) . . ? N3 C36 C38 112.4(3) . . ? N3 C36 C37 112.8(2) . . ? C38 C36 C37 113.5(2) . . ? C43 C42 C47 117.3(3) . . ? C43 C42 C41 121.5(3) . . ? C47 C42 C41 121.2(3) . . ? C44 C43 C42 121.3(3) . . ? C45 C44 C43 120.7(3) . . ? C44 C45 C46 118.8(3) . . ? C47 C46 C45 120.5(3) . . ? C46 C47 C42 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.566 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.057 # Attachment '3a.CIF' data_3a _database_code_depnum_ccdc_archive 'CCDC 731871' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H64 Cl2 Ge N4 O2' _chemical_formula_weight 788.45 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6635(3) _cell_length_b 24.5936(7) _cell_length_c 15.6283(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.959(2) _cell_angle_gamma 90.00 _cell_volume 4368.76(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8726 _cell_measurement_theta_min 2.9617 _cell_measurement_theta_max 32.3107 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.860 _exptl_absorpt_correction_T_min 0.97579 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18717 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7646 _reflns_number_gt 5710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.One of the isopropyl groups was disordered and thus was refined with restraints for the anisotropic displacement parameters. Additionally, strongly disordered diethyl ether molecules were removed using the squeeze command in the Platon Software package, except a disordered diethyl ether molecule which was refined with distance restraints and restraints for the anisotropic displacement parameters. ; _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^)+(0.0939P)^2^+6.4070P] 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 7646 _refine_ls_number_parameters 496 _refine_ls_number_restraints 76 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.019 _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 0.63740(4) 0.131877(18) 0.21633(3) 0.01949(15) Uani 1 1 d . . . Cl1 Cl 0.96720(17) 0.25913(9) -0.09285(11) 0.0880(7) Uani 1 1 d . . . Cl2 Cl 1.04930(19) 0.35932(12) -0.00459(13) 0.1093(9) Uani 1 1 d . . . O1 O 0.7010(3) 0.15914(13) 0.31335(18) 0.0269(7) Uani 1 1 d . . . O2 O 0.8600(7) 0.3882(2) 0.2623(5) 0.116(2) Uani 1 1 d DU . . N1 N 0.4793(3) 0.11333(16) 0.1985(2) 0.0260(8) Uani 1 1 d . . . N2 N 0.7000(3) 0.06660(14) 0.1888(2) 0.0235(8) Uani 1 1 d . . . N3 N 0.6158(3) 0.17734(16) 0.0311(2) 0.0324(9) Uani 1 1 d . . . N4 N 0.7072(3) 0.23189(14) 0.1291(2) 0.0256(8) Uani 1 1 d . . . C1 C 0.3121(5) 0.0576(3) 0.1294(3) 0.0522(16) Uani 1 1 d . . . H1A H 0.2600 0.0831 0.1464 0.063 Uiso 1 1 calc R . . H1B H 0.2817 0.0259 0.0975 0.063 Uiso 1 1 calc R . . C2 C 0.4332(4) 0.0668(2) 0.1515(3) 0.0335(11) Uani 1 1 d . . . C3 C 0.5091(4) 0.0278(2) 0.1266(3) 0.0339(11) Uani 1 1 d . . . H3 H 0.4699 -0.0011 0.0915 0.041 Uiso 1 1 calc R . . C4 C 0.6303(4) 0.02469(19) 0.1448(3) 0.0301(10) Uani 1 1 d . . . C5 C 0.6877(5) -0.0214(2) 0.1156(4) 0.0494(14) Uani 1 1 d . . . H5A H 0.6283 -0.0469 0.0844 0.074 Uiso 1 1 calc R . . H5B H 0.7373 -0.0395 0.1664 0.074 Uiso 1 1 calc R . . H5C H 0.7366 -0.0090 0.0759 0.074 Uiso 1 1 calc R . . C6 C 0.4009(4) 0.14760(19) 0.2335(3) 0.0291(10) Uani 1 1 d . A . C7 C 0.3357(5) 0.1882(3) 0.1805(4) 0.0579(17) Uani 1 1 d . . . C8 C 0.2570(6) 0.2193(3) 0.2138(6) 0.076(2) Uani 1 1 d . A . H8 H 0.2128 0.2468 0.1783 0.091 Uiso 1 1 calc R . . C9 C 0.2420(5) 0.2109(3) 0.2975(5) 0.0658(19) Uani 1 1 d . . . H9 H 0.1869 0.2323 0.3191 0.079 Uiso 1 1 calc R A . C10 C 0.3060(5) 0.1720(3) 0.3495(4) 0.0506(15) Uani 1 1 d . A . H10 H 0.2945 0.1668 0.4073 0.061 Uiso 1 1 calc R . . C11 C 0.3882(4) 0.1396(2) 0.3200(3) 0.0336(11) Uani 1 1 d . . . C12 C 0.4604(4) 0.0985(2) 0.3796(3) 0.0388(12) Uani 1 1 d . A . H12 H 0.5382 0.0964 0.3629 0.047 Uiso 1 1 calc R . . C13 C 0.4856(6) 0.1146(3) 0.4771(4) 0.0669(19) Uani 1 1 d . . . H13A H 0.5179 0.1515 0.4842 0.100 Uiso 1 1 calc R A . H13B H 0.5425 0.0892 0.5114 0.100 Uiso 1 1 calc R . . H13C H 0.4123 0.1134 0.4979 0.100 Uiso 1 1 calc R . . C14 C 0.4075(7) 0.0419(3) 0.3674(4) 0.0679(19) Uani 1 1 d . . . H14A H 0.3287 0.0425 0.3795 0.102 Uiso 1 1 calc R A . H14B H 0.4575 0.0167 0.4079 0.102 Uiso 1 1 calc R . . H14C H 0.4022 0.0299 0.3068 0.102 Uiso 1 1 calc R . . C18 C 0.8207(4) 0.0547(2) 0.2325(3) 0.0369(12) Uani 1 1 d . . . C19 C 0.9129(5) 0.0681(3) 0.1948(4) 0.0521(15) Uani 1 1 d . . . C20 C 1.0292(6) 0.0562(4) 0.2447(6) 0.093(3) Uani 1 1 d . . . H20 H 1.0963 0.0674 0.2241 0.112 Uiso 1 1 calc R . . C21 C 1.0423(8) 0.0286(5) 0.3225(5) 0.120(4) Uani 1 1 d . . . H21 H 1.1195 0.0186 0.3527 0.143 Uiso 1 1 calc R . . C22 C 0.9533(7) 0.0150(5) 0.3579(5) 0.113(4) Uani 1 1 d . . . H22 H 0.9681 -0.0034 0.4128 0.136 Uiso 1 1 calc R . . C23 C 0.8389(6) 0.0273(3) 0.3156(4) 0.0609(18) Uani 1 1 d . . . C24 C 0.7425(6) 0.0117(3) 0.3593(4) 0.0648(19) Uani 1 1 d . . . H24 H 0.6682 0.0272 0.3229 0.078 Uiso 1 1 calc R . . C25 C 0.7596(7) 0.0372(4) 0.4496(4) 0.094(3) Uani 1 1 d . . . H25A H 0.8303 0.0221 0.4883 0.141 Uiso 1 1 calc R . . H25B H 0.6910 0.0294 0.4741 0.141 Uiso 1 1 calc R . . H25C H 0.7685 0.0766 0.4449 0.141 Uiso 1 1 calc R . . C26 C 0.7253(12) -0.0495(4) 0.3614(8) 0.154(5) Uani 1 1 d . . . H26A H 0.7052 -0.0636 0.3012 0.231 Uiso 1 1 calc R . . H26B H 0.6615 -0.0578 0.3908 0.231 Uiso 1 1 calc R . . H26C H 0.7982 -0.0667 0.3935 0.231 Uiso 1 1 calc R . . C27 C 0.8950(6) 0.0957(3) 0.1088(5) 0.0617(18) Uani 1 1 d . . . H27 H 0.8083 0.1002 0.0858 0.074 Uiso 1 1 calc R . . C28 C 0.9427(8) 0.0604(4) 0.0415(5) 0.099(3) Uani 1 1 d . . . H28A H 1.0213 0.0469 0.0691 0.149 Uiso 1 1 calc R . . H28B H 0.9469 0.0826 -0.0098 0.149 Uiso 1 1 calc R . . H28C H 0.8897 0.0296 0.0231 0.149 Uiso 1 1 calc R . . C29 C 0.9501(8) 0.1516(3) 0.1137(8) 0.122(4) Uani 1 1 d . . . H29A H 0.9198 0.1741 0.1555 0.183 Uiso 1 1 calc R . . H29B H 0.9305 0.1686 0.0555 0.183 Uiso 1 1 calc R . . H29C H 1.0358 0.1484 0.1332 0.183 Uiso 1 1 calc R . . C30 C 0.6539(4) 0.18302(17) 0.1186(3) 0.0228(9) Uani 1 1 d . . . C31 C 0.6427(5) 0.2227(2) -0.0131(3) 0.0364(12) Uani 1 1 d . . . C32 C 0.7027(4) 0.25731(19) 0.0491(3) 0.0300(10) Uani 1 1 d . . . C33 C 0.7672(6) 0.2562(2) 0.2125(3) 0.0488(15) Uani 1 1 d . . . H33A H 0.7578 0.2326 0.2610 0.073 Uiso 1 1 calc R . . H33B H 0.7330 0.2920 0.2188 0.073 Uiso 1 1 calc R . . H33C H 0.8511 0.2603 0.2135 0.073 Uiso 1 1 calc R . . C34 C 0.5563(6) 0.1298(2) -0.0138(3) 0.0569(18) Uani 1 1 d . . . H34A H 0.6072 0.1122 -0.0476 0.085 Uiso 1 1 calc R . . H34B H 0.4827 0.1410 -0.0535 0.085 Uiso 1 1 calc R . . H34C H 0.5390 0.1041 0.0296 0.085 Uiso 1 1 calc R . . C35 C 0.6080(6) 0.2287(3) -0.1100(3) 0.0628(19) Uani 1 1 d . . . H35A H 0.5231 0.2227 -0.1298 0.094 Uiso 1 1 calc R . . H35B H 0.6503 0.2019 -0.1376 0.094 Uiso 1 1 calc R . . H35C H 0.6276 0.2654 -0.1265 0.094 Uiso 1 1 calc R . . C36 C 0.7578(5) 0.3107(2) 0.0401(3) 0.0466(14) Uani 1 1 d . . . H36A H 0.7367 0.3223 -0.0214 0.070 Uiso 1 1 calc R . . H36B H 0.8435 0.3074 0.0589 0.070 Uiso 1 1 calc R . . H36C H 0.7296 0.3376 0.0768 0.070 Uiso 1 1 calc R . . C37 C 0.9716(5) 0.3306(3) -0.1033(4) 0.067(2) Uani 1 1 d . . . H37A H 1.0105 0.3403 -0.1514 0.080 Uiso 1 1 calc R . . H37B H 0.8905 0.3453 -0.1181 0.080 Uiso 1 1 calc R . . C38 C 1.0599(11) 0.3541(3) 0.2459(7) 0.124(4) Uani 1 1 d . . . H38A H 1.0310 0.3169 0.2481 0.186 Uiso 1 1 calc R . . H38B H 1.1424 0.3560 0.2776 0.186 Uiso 1 1 calc R . . H38C H 1.0534 0.3648 0.1846 0.186 Uiso 1 1 calc R . . C39 C 0.9872(13) 0.3922(6) 0.2881(12) 0.198(5) Uani 1 1 d DU . . H39A H 1.0106 0.3866 0.3524 0.238 Uiso 1 1 calc R . . H39B H 1.0093 0.4299 0.2764 0.238 Uiso 1 1 calc R . . C40 C 0.7535(13) 0.4183(5) 0.2670(12) 0.205(6) Uani 1 1 d DU . . H40A H 0.7709 0.4319 0.3281 0.246 Uiso 1 1 calc R . . H40B H 0.7579 0.4508 0.2303 0.246 Uiso 1 1 calc R . . C41 C 0.6274(7) 0.4071(3) 0.2495(5) 0.075(2) Uani 1 1 d . . . H41A H 0.6082 0.3778 0.2061 0.112 Uiso 1 1 calc R . . H41B H 0.5835 0.4399 0.2265 0.112 Uiso 1 1 calc R . . H41C H 0.6059 0.3960 0.3040 0.112 Uiso 1 1 calc R . . C15A C 0.359(2) 0.2174(12) 0.110(2) 0.069(5) Uani 0.32 1 d PU A 1 H15A H 0.4089 0.1927 0.0833 0.082 Uiso 0.32 1 calc PR A 1 C16A C 0.243(2) 0.2215(12) 0.0412(17) 0.083(6) Uani 0.32 1 d PU A 1 H16A H 0.2085 0.1852 0.0290 0.124 Uiso 0.32 1 calc PR A 1 H16B H 0.2576 0.2372 -0.0129 0.124 Uiso 0.32 1 calc PR A 1 H16C H 0.1877 0.2448 0.0634 0.124 Uiso 0.32 1 calc PR A 1 C17A C 0.429(2) 0.2721(11) 0.1266(19) 0.080(6) Uani 0.32 1 d PU A 1 H17A H 0.3816 0.2999 0.1471 0.121 Uiso 0.32 1 calc PR A 1 H17B H 0.4488 0.2842 0.0718 0.121 Uiso 0.32 1 calc PR A 1 H17C H 0.5022 0.2664 0.1712 0.121 Uiso 0.32 1 calc PR A 1 C15B C 0.3463(10) 0.1927(5) 0.0807(7) 0.062(3) Uani 0.68 1 d PU A 2 H15B H 0.4074 0.1662 0.0713 0.074 Uiso 0.68 1 calc PR A 2 C16B C 0.2318(9) 0.1806(6) 0.0134(7) 0.080(4) Uani 0.68 1 d PU A 2 H16D H 0.1694 0.2047 0.0239 0.120 Uiso 0.68 1 calc PR A 2 H16E H 0.2090 0.1426 0.0194 0.120 Uiso 0.68 1 calc PR A 2 H16F H 0.2436 0.1866 -0.0460 0.120 Uiso 0.68 1 calc PR A 2 C17B C 0.3895(9) 0.2500(5) 0.0672(9) 0.077(3) Uani 0.68 1 d PU A 2 H17D H 0.4028 0.2533 0.0077 0.115 Uiso 0.68 1 calc PR A 2 H17E H 0.4632 0.2570 0.1101 0.115 Uiso 0.68 1 calc PR A 2 H17F H 0.3301 0.2766 0.0751 0.115 Uiso 0.68 1 calc PR A 2 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 0.0162(2) 0.0250(3) 0.0182(2) -0.00046(19) 0.00574(15) -0.0044(2) Cl1 0.0706(12) 0.1189(17) 0.0637(10) 0.0044(10) -0.0074(9) 0.0497(12) Cl2 0.0715(13) 0.183(3) 0.0618(11) -0.0114(13) -0.0090(9) -0.0445(15) O1 0.0244(17) 0.0331(18) 0.0232(14) -0.0050(13) 0.0052(12) -0.0038(13) O2 0.170(6) 0.049(3) 0.143(5) 0.006(3) 0.067(5) 0.000(4) N1 0.0141(18) 0.039(2) 0.0256(18) 0.0050(16) 0.0059(14) -0.0038(16) N2 0.0199(19) 0.024(2) 0.0268(18) -0.0046(15) 0.0053(14) -0.0044(15) N3 0.040(2) 0.036(2) 0.0229(18) 0.0008(17) 0.0096(16) -0.0186(19) N4 0.029(2) 0.023(2) 0.0269(18) -0.0043(15) 0.0110(15) -0.0063(16) C1 0.030(3) 0.085(5) 0.042(3) -0.014(3) 0.009(2) -0.025(3) C2 0.029(3) 0.051(3) 0.021(2) 0.006(2) 0.0051(18) -0.014(2) C3 0.038(3) 0.033(3) 0.030(2) -0.003(2) 0.007(2) -0.023(2) C4 0.037(3) 0.026(3) 0.027(2) -0.0032(19) 0.0080(19) -0.009(2) C5 0.064(4) 0.031(3) 0.053(3) -0.010(3) 0.014(3) -0.014(3) C6 0.018(2) 0.032(3) 0.039(2) 0.009(2) 0.0081(19) -0.0019(19) C7 0.021(3) 0.063(4) 0.093(4) 0.041(4) 0.021(3) 0.008(3) C8 0.036(4) 0.056(4) 0.140(7) 0.038(4) 0.028(4) 0.014(3) C9 0.026(3) 0.052(4) 0.122(6) -0.018(4) 0.024(3) 0.005(3) C10 0.039(3) 0.060(4) 0.058(3) -0.023(3) 0.023(3) -0.011(3) C11 0.025(2) 0.040(3) 0.040(2) -0.003(2) 0.015(2) -0.006(2) C12 0.034(3) 0.053(3) 0.032(2) 0.010(2) 0.014(2) -0.005(2) C13 0.079(5) 0.075(5) 0.040(3) -0.002(3) 0.001(3) -0.013(4) C14 0.092(5) 0.054(4) 0.051(3) 0.010(3) 0.000(3) -0.013(4) C18 0.026(3) 0.040(3) 0.045(3) -0.015(2) 0.008(2) 0.008(2) C19 0.038(3) 0.059(4) 0.066(4) -0.026(3) 0.025(3) -0.004(3) C20 0.045(4) 0.134(8) 0.116(7) 0.000(6) 0.051(4) 0.022(5) C21 0.056(5) 0.231(13) 0.067(5) 0.019(6) 0.005(4) 0.025(6) C22 0.057(5) 0.215(11) 0.067(5) 0.022(6) 0.013(4) 0.070(6) C23 0.055(4) 0.077(5) 0.046(3) 0.005(3) 0.001(3) 0.036(3) C24 0.085(5) 0.065(4) 0.049(3) 0.028(3) 0.026(3) 0.035(4) C25 0.081(5) 0.158(8) 0.041(3) 0.015(4) 0.012(3) 0.048(5) C26 0.267(16) 0.069(6) 0.167(10) 0.051(6) 0.137(11) 0.057(8) C27 0.054(4) 0.054(4) 0.094(5) -0.010(3) 0.053(4) 0.002(3) C28 0.110(7) 0.117(7) 0.096(6) 0.003(5) 0.077(5) 0.025(6) C29 0.091(7) 0.069(5) 0.242(12) 0.009(7) 0.112(8) -0.009(5) C30 0.023(2) 0.022(2) 0.026(2) -0.0010(18) 0.0124(17) -0.0052(19) C31 0.045(3) 0.040(3) 0.028(2) 0.004(2) 0.017(2) -0.012(2) C32 0.034(3) 0.027(3) 0.034(2) 0.004(2) 0.019(2) -0.004(2) C33 0.083(4) 0.027(3) 0.035(3) -0.011(2) 0.008(3) -0.021(3) C34 0.081(4) 0.062(4) 0.024(2) -0.004(3) 0.006(3) -0.048(3) C35 0.093(5) 0.066(4) 0.029(3) 0.013(3) 0.015(3) -0.034(4) C36 0.066(4) 0.032(3) 0.047(3) 0.006(2) 0.024(3) -0.012(3) C37 0.035(3) 0.117(6) 0.043(3) 0.007(3) -0.003(3) 0.011(4) C38 0.184(12) 0.056(6) 0.153(9) 0.010(6) 0.086(8) -0.032(6) C39 0.189(7) 0.139(10) 0.280(14) -0.047(11) 0.081(12) -0.052(9) C40 0.247(10) 0.071(7) 0.306(14) -0.069(9) 0.083(12) 0.049(8) C41 0.122(7) 0.029(3) 0.072(4) 0.019(3) 0.020(4) 0.041(4) C15A 0.033(6) 0.090(10) 0.086(9) 0.057(8) 0.018(7) 0.021(8) C16A 0.049(8) 0.110(12) 0.086(11) 0.057(10) 0.006(7) 0.031(9) C17A 0.058(10) 0.090(12) 0.100(13) 0.056(11) 0.033(9) 0.010(8) C15B 0.028(4) 0.089(7) 0.073(7) 0.061(6) 0.021(4) 0.018(5) C16B 0.043(5) 0.125(9) 0.070(7) 0.060(7) 0.008(4) 0.016(6) C17B 0.048(6) 0.083(7) 0.108(8) 0.064(6) 0.035(5) 0.027(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 O1 1.672(3) . ? Ge1 N2 1.854(4) . ? Ge1 N1 1.859(3) . ? Ge1 C30 2.020(4) . ? Cl1 C37 1.768(8) . ? Cl2 C37 1.753(6) . ? O2 C39 1.451(12) . ? O2 C40 1.462(11) . ? N1 C2 1.401(6) . ? N1 C6 1.438(6) . ? N2 C4 1.395(6) . ? N2 C18 1.450(6) . ? N3 C30 1.347(5) . ? N3 C31 1.384(6) . ? N3 C34 1.458(6) . ? N4 C30 1.346(5) . ? N4 C32 1.389(5) . ? N4 C33 1.461(6) . ? C1 C2 1.395(7) . ? C2 C3 1.417(7) . ? C3 C4 1.380(7) . ? C4 C5 1.441(7) . ? C6 C7 1.407(7) . ? C6 C11 1.406(6) . ? C7 C8 1.381(9) . ? C7 C15A 1.39(3) . ? C7 C15B 1.597(13) . ? C8 C9 1.373(10) . ? C9 C10 1.364(9) . ? C10 C11 1.403(7) . ? C11 C12 1.499(7) . ? C12 C14 1.517(8) . ? C12 C13 1.538(7) . ? C18 C19 1.378(7) . ? C18 C23 1.435(8) . ? C19 C20 1.436(9) . ? C19 C27 1.477(9) . ? C20 C21 1.372(11) . ? C21 C22 1.324(12) . ? C22 C23 1.383(9) . ? C23 C24 1.491(9) . ? C24 C26 1.520(11) . ? C24 C25 1.517(9) . ? C27 C29 1.513(10) . ? C27 C28 1.559(8) . ? C31 C32 1.361(7) . ? C31 C35 1.485(6) . ? C32 C36 1.481(7) . ? C38 C39 1.510(17) . ? C40 C41 1.461(15) . ? C15A C16A 1.53(3) . ? C15A C17A 1.57(4) . ? C15B C17B 1.528(15) . ? C15B C16B 1.533(14) . ? 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 N2 116.12(15) . . ? O1 Ge1 N1 117.25(15) . . ? N2 Ge1 N1 100.48(16) . . ? O1 Ge1 C30 109.72(16) . . ? N2 Ge1 C30 104.72(16) . . ? N1 Ge1 C30 107.41(16) . . ? C39 O2 C40 141.2(10) . . ? C2 N1 C6 118.5(4) . . ? C2 N1 Ge1 122.0(3) . . ? C6 N1 Ge1 119.5(3) . . ? C4 N2 C18 118.7(4) . . ? C4 N2 Ge1 122.5(3) . . ? C18 N2 Ge1 117.2(3) . . ? C30 N3 C31 111.3(4) . . ? C30 N3 C34 125.8(4) . . ? C31 N3 C34 122.9(4) . . ? C30 N4 C32 111.6(3) . . ? C30 N4 C33 126.2(4) . . ? C32 N4 C33 122.2(4) . . ? C1 C2 N1 120.6(5) . . ? C1 C2 C3 118.9(5) . . ? N1 C2 C3 120.4(4) . . ? C4 C3 C2 131.0(4) . . ? C3 C4 N2 121.2(4) . . ? C3 C4 C5 120.4(4) . . ? N2 C4 C5 118.4(4) . . ? C7 C6 C11 120.3(5) . . ? C7 C6 N1 120.0(4) . . ? C11 C6 N1 119.7(4) . . ? C8 C7 C15A 105.9(14) . . ? C8 C7 C6 119.3(6) . . ? C15A C7 C6 131.1(13) . . ? C8 C7 C15B 122.3(7) . . ? C15A C7 C15B 28.3(13) . . ? C6 C7 C15B 118.2(6) . . ? C9 C8 C7 120.8(6) . . ? C10 C9 C8 120.3(6) . . ? C9 C10 C11 121.6(6) . . ? C10 C11 C6 117.7(5) . . ? C10 C11 C12 120.6(5) . . ? C6 C11 C12 121.8(4) . . ? C11 C12 C14 112.6(4) . . ? C11 C12 C13 113.5(5) . . ? C14 C12 C13 110.1(4) . . ? C19 C18 C23 121.9(5) . . ? C19 C18 N2 121.2(5) . . ? C23 C18 N2 116.9(5) . . ? C18 C19 C20 116.9(6) . . ? C18 C19 C27 122.3(5) . . ? C20 C19 C27 120.8(6) . . ? C21 C20 C19 119.1(7) . . ? C22 C21 C20 123.6(8) . . ? C21 C22 C23 120.5(8) . . ? C22 C23 C18 117.8(7) . . ? C22 C23 C24 118.0(6) . . ? C18 C23 C24 124.1(5) . . ? C23 C24 C26 112.5(6) . . ? C23 C24 C25 111.3(6) . . ? C26 C24 C25 112.4(7) . . ? C19 C27 C29 113.6(7) . . ? C19 C27 C28 111.0(6) . . ? C29 C27 C28 109.2(6) . . ? N4 C30 N3 104.7(3) . . ? N4 C30 Ge1 125.7(3) . . ? N3 C30 Ge1 129.6(3) . . ? C32 C31 N3 106.6(4) . . ? C32 C31 C35 130.2(4) . . ? N3 C31 C35 123.2(4) . . ? C31 C32 N4 105.7(4) . . ? C31 C32 C36 130.6(4) . . ? N4 C32 C36 123.7(4) . . ? Cl2 C37 Cl1 109.8(3) . . ? O2 C39 C38 118.4(12) . . ? C41 C40 O2 136.5(9) . . ? C7 C15A C16A 107(2) . . ? C7 C15A C17A 120(2) . . ? C16A C15A C17A 114(2) . . ? C17B C15B C16B 110.4(9) . . ? C17B C15B C7 107.4(10) . . ? C16B C15B C7 114.2(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.977 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.084 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.378 0.340 0.256 25 7 ' ' 2 0.378 0.160 0.756 25 8 ' ' 3 0.621 0.840 0.244 25 7 ' ' 4 0.621 0.660 0.744 25 6 ' ' _platon_squeeze_details ; ; # Attachment '3b.CIF' data_3b _database_code_depnum_ccdc_archive 'CCDC 731872' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H60 Ge N4 O' _chemical_formula_weight 685.51 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.2684(5) _cell_length_b 16.9410(4) _cell_length_c 21.6339(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.333(2) _cell_angle_gamma 90.00 _cell_volume 7772.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18973 _cell_measurement_theta_min 3.0395 _cell_measurement_theta_max 32.3558 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.822 _exptl_absorpt_correction_T_min 0.88750 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 71416 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0818 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 13672 _reflns_number_gt 9650 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One of the isopropyl groups is disordered and refined with restraints for the anisotropic displacement parameters ; _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^)+(0.0307P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13672 _refine_ls_number_parameters 859 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0757 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.963 _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 0.088088(13) 0.564395(16) 0.258043(12) 0.01403(7) Uani 1 1 d . . . Ge2 Ge 0.416184(13) 0.111085(16) 0.263482(13) 0.01628(8) Uani 1 1 d . . . O1 O 0.06759(8) 0.65811(9) 0.24349(8) 0.0207(4) Uani 1 1 d . . . O2 O 0.43581(8) 0.01644(10) 0.25748(8) 0.0266(5) Uani 1 1 d . . . N1 N 0.16156(9) 0.52599(11) 0.22629(9) 0.0154(5) Uani 1 1 d . . . N2 N 0.10382(10) 0.53930(12) 0.34110(9) 0.0170(5) Uani 1 1 d . . . N3 N -0.01682(9) 0.51380(11) 0.16569(10) 0.0164(5) Uani 1 1 d . . . N4 N 0.01045(10) 0.41441(11) 0.22481(10) 0.0182(5) Uani 1 1 d . . . N5 N 0.34460(10) 0.13707(11) 0.30404(9) 0.0173(5) Uani 1 1 d . . . N6 N 0.39782(10) 0.16063(12) 0.18790(10) 0.0191(5) Uani 1 1 d . . . N7 N 0.52993(10) 0.13333(12) 0.35426(10) 0.0219(5) Uani 1 1 d . . . N8 N 0.50018(10) 0.24811(13) 0.31859(10) 0.0241(6) Uani 1 1 d . . . C1 C 0.26359(13) 0.46343(16) 0.24199(13) 0.0302(7) Uani 1 1 d . . . H1A H 0.2747 0.4810 0.2026 0.036 Uiso 1 1 calc R . . H1B H 0.2926 0.4331 0.2677 0.036 Uiso 1 1 calc R . . C2 C 0.20651(12) 0.48162(15) 0.26158(12) 0.0184(6) Uani 1 1 d . . . C3 C 0.19070(12) 0.45259(15) 0.32204(12) 0.0214(7) Uani 1 1 d . . . H3 H 0.2148 0.4087 0.3377 0.026 Uiso 1 1 calc R . . C4 C 0.14703(13) 0.47891(15) 0.35879(12) 0.0205(7) Uani 1 1 d . . . C5 C 0.13921(13) 0.44124(16) 0.42064(12) 0.0301(7) Uani 1 1 d . . . H5A H 0.1709 0.3997 0.4282 0.045 Uiso 1 1 calc R . . H5B H 0.0969 0.4182 0.4207 0.045 Uiso 1 1 calc R . . H5C H 0.1447 0.4813 0.4533 0.045 Uiso 1 1 calc R . . C6 C 0.17604(12) 0.55122(15) 0.16539(12) 0.0180(6) Uani 1 1 d . . . C7 C 0.16677(12) 0.49914(15) 0.11451(12) 0.0186(6) Uani 1 1 d . . . C8 C 0.18115(12) 0.52529(17) 0.05639(13) 0.0256(7) Uani 1 1 d . . . H8 H 0.1765 0.4900 0.0222 0.031 Uiso 1 1 calc R . . C9 C 0.20195(13) 0.60112(18) 0.04703(13) 0.0304(7) Uani 1 1 d . . . H9 H 0.2104 0.6183 0.0067 0.037 Uiso 1 1 calc R . . C10 C 0.21032(13) 0.65156(17) 0.09662(14) 0.0300(7) Uani 1 1 d . . . H10 H 0.2242 0.7040 0.0899 0.036 Uiso 1 1 calc R . . C11 C 0.19909(12) 0.62810(15) 0.15637(13) 0.0210(7) Uani 1 1 d . . . C12 C 0.21539(13) 0.68493(15) 0.20963(13) 0.0266(7) Uani 1 1 d . . . H12 H 0.1972 0.6630 0.2473 0.032 Uiso 1 1 calc R . . C13 C 0.28677(14) 0.68879(19) 0.22304(16) 0.0486(9) Uani 1 1 d . . . H13A H 0.3058 0.7127 0.1877 0.073 Uiso 1 1 calc R . . H13B H 0.3035 0.6353 0.2299 0.073 Uiso 1 1 calc R . . H13C H 0.2969 0.7208 0.2602 0.073 Uiso 1 1 calc R . . C14 C 0.18753(15) 0.76653(16) 0.19811(16) 0.0449(9) Uani 1 1 d . . . H14A H 0.2069 0.7912 0.1633 0.067 Uiso 1 1 calc R . . H14B H 0.1958 0.7990 0.2353 0.067 Uiso 1 1 calc R . . H14C H 0.1419 0.7621 0.1883 0.067 Uiso 1 1 calc R . . C15 C 0.14257(14) 0.41523(15) 0.12079(13) 0.0271(7) Uani 1 1 d . . . H15 H 0.1273 0.4096 0.1632 0.033 Uiso 1 1 calc R . . C16 C 0.19498(16) 0.35478(18) 0.11462(17) 0.0576(11) Uani 1 1 d . . . H16A H 0.2114 0.3598 0.0737 0.086 Uiso 1 1 calc R . . H16B H 0.1781 0.3015 0.1194 0.086 Uiso 1 1 calc R . . H16C H 0.2290 0.3643 0.1468 0.086 Uiso 1 1 calc R . . C17 C 0.08782(13) 0.39549(17) 0.07382(14) 0.0371(8) Uani 1 1 d . . . H17A H 0.0562 0.4375 0.0736 0.056 Uiso 1 1 calc R . . H17B H 0.0688 0.3454 0.0851 0.056 Uiso 1 1 calc R . . H17C H 0.1033 0.3909 0.0325 0.056 Uiso 1 1 calc R . . C18 C 0.08672(13) 0.59392(15) 0.38842(12) 0.0203(7) Uani 1 1 d . . . C19 C 0.13389(14) 0.64173(16) 0.41889(12) 0.0279(7) Uani 1 1 d . . . C20 C 0.11670(18) 0.68953(17) 0.46707(14) 0.0425(9) Uani 1 1 d . . . H20 H 0.1480 0.7204 0.4895 0.051 Uiso 1 1 calc R . . C21 C 0.0553(2) 0.69305(19) 0.48283(15) 0.0507(10) Uani 1 1 d . . . H21 H 0.0448 0.7263 0.5159 0.061 Uiso 1 1 calc R . . C22 C 0.00938(16) 0.64918(18) 0.45140(14) 0.0419(9) Uani 1 1 d . . . H22 H -0.0331 0.6539 0.4616 0.050 Uiso 1 1 calc R . . C23 C 0.02428(14) 0.59745(16) 0.40441(12) 0.0270(7) Uani 1 1 d . . . C24 C -0.02823(13) 0.54860(17) 0.37139(13) 0.0303(8) Uani 1 1 d . . . H24 H -0.0076 0.5074 0.3467 0.036 Uiso 1 1 calc R . . C25 C -0.06841(15) 0.50516(19) 0.41642(15) 0.0469(9) Uani 1 1 d . . . H25A H -0.0413 0.4709 0.4435 0.070 Uiso 1 1 calc R . . H25B H -0.1002 0.4731 0.3929 0.070 Uiso 1 1 calc R . . H25C H -0.0894 0.5437 0.4417 0.070 Uiso 1 1 calc R . . C26 C -0.06966(14) 0.59825(18) 0.32574(14) 0.0431(9) Uani 1 1 d . . . H26A H -0.0908 0.6394 0.3483 0.065 Uiso 1 1 calc R . . H26B H -0.1014 0.5644 0.3038 0.065 Uiso 1 1 calc R . . H26C H -0.0434 0.6228 0.2957 0.065 Uiso 1 1 calc R . . C27 C 0.20126(14) 0.64414(17) 0.40061(14) 0.0335(8) Uani 1 1 d U . . H27 H 0.2035 0.6107 0.3627 0.040 Uiso 1 1 calc R . . C28 C 0.24829(17) 0.6105(2) 0.45072(17) 0.0670(11) Uani 1 1 d U . . H28A H 0.2446 0.6393 0.4896 0.101 Uiso 1 1 calc R . . H28B H 0.2912 0.6163 0.4377 0.101 Uiso 1 1 calc R . . H28C H 0.2392 0.5545 0.4570 0.101 Uiso 1 1 calc R . . C29 C 0.22133(16) 0.72783(17) 0.38412(15) 0.0489(9) Uani 1 1 d U . . H29A H 0.1921 0.7488 0.3509 0.073 Uiso 1 1 calc R . . H29B H 0.2641 0.7266 0.3701 0.073 Uiso 1 1 calc R . . H29C H 0.2207 0.7618 0.4208 0.073 Uiso 1 1 calc R . . C30 C 0.02030(11) 0.49274(14) 0.21660(12) 0.0153(6) Uani 1 1 d . . . C31 C -0.04936(12) 0.44835(15) 0.14123(12) 0.0206(6) Uani 1 1 d . . . C32 C -0.03293(12) 0.38643(16) 0.17860(12) 0.0226(6) Uani 1 1 d . . . C33 C 0.03841(13) 0.36877(15) 0.27833(12) 0.0235(7) Uani 1 1 d . . . H33 H 0.0639 0.4068 0.3053 0.028 Uiso 1 1 calc R . . C34 C -0.01189(13) 0.33501(16) 0.31765(13) 0.0322(8) Uani 1 1 d . . . H34A H -0.0453 0.3742 0.3212 0.048 Uiso 1 1 calc R . . H34B H 0.0072 0.3220 0.3590 0.048 Uiso 1 1 calc R . . H34C H -0.0298 0.2872 0.2979 0.048 Uiso 1 1 calc R . . C35 C 0.08378(15) 0.30526(17) 0.25916(15) 0.0440(9) Uani 1 1 d . . . H35A H 0.0601 0.2639 0.2358 0.066 Uiso 1 1 calc R . . H35B H 0.1059 0.2822 0.2962 0.066 Uiso 1 1 calc R . . H35C H 0.1145 0.3288 0.2331 0.066 Uiso 1 1 calc R . . C36 C -0.02151(12) 0.59655(15) 0.14142(12) 0.0214(7) Uani 1 1 d . . . H36 H 0.0009 0.6310 0.1735 0.026 Uiso 1 1 calc R . . C37 C 0.01258(13) 0.60605(17) 0.08273(13) 0.0320(7) Uani 1 1 d . . . H37A H 0.0569 0.5912 0.0911 0.048 Uiso 1 1 calc R . . H37B H 0.0099 0.6612 0.0690 0.048 Uiso 1 1 calc R . . H37C H -0.0071 0.5719 0.0502 0.048 Uiso 1 1 calc R . . C38 C -0.08974(12) 0.62449(16) 0.13442(13) 0.0299(7) Uani 1 1 d . . . H38A H -0.1124 0.5962 0.1000 0.045 Uiso 1 1 calc R . . H38B H -0.0909 0.6813 0.1259 0.045 Uiso 1 1 calc R . . H38C H -0.1099 0.6139 0.1728 0.045 Uiso 1 1 calc R . . C39 C -0.09195(13) 0.44711(16) 0.08347(12) 0.0313(7) Uani 1 1 d . . . H39A H -0.0968 0.3927 0.0685 0.047 Uiso 1 1 calc R . . H39B H -0.0738 0.4795 0.0518 0.047 Uiso 1 1 calc R . . H39C H -0.1333 0.4683 0.0921 0.047 Uiso 1 1 calc R . . C40 C -0.05265(15) 0.30199(16) 0.17006(14) 0.0448(9) Uani 1 1 d . . . H40A H -0.0703 0.2829 0.2079 0.067 Uiso 1 1 calc R . . H40B H -0.0159 0.2699 0.1616 0.067 Uiso 1 1 calc R . . H40C H -0.0846 0.2979 0.1351 0.067 Uiso 1 1 calc R . . C41 C 0.24319(13) 0.20207(17) 0.30489(13) 0.0330(8) Uani 1 1 d . . . H41A H 0.2332 0.1723 0.3401 0.040 Uiso 1 1 calc R . . H41B H 0.2139 0.2395 0.2871 0.040 Uiso 1 1 calc R . . C42 C 0.29927(13) 0.19116(15) 0.28014(12) 0.0200(6) Uani 1 1 d . . . C43 C 0.31365(12) 0.23893(15) 0.22658(12) 0.0202(6) Uani 1 1 d . . . H43 H 0.2904 0.2866 0.2212 0.024 Uiso 1 1 calc R . . C44 C 0.35519(12) 0.22485(15) 0.18378(12) 0.0203(6) Uani 1 1 d . . . C45 C 0.36104(13) 0.27857(15) 0.13009(13) 0.0302(7) Uani 1 1 d . . . H45A H 0.3339 0.3247 0.1342 0.045 Uiso 1 1 calc R . . H45B H 0.3481 0.2506 0.0916 0.045 Uiso 1 1 calc R . . H45C H 0.4050 0.2958 0.1292 0.045 Uiso 1 1 calc R . . C46 C 0.33342(12) 0.09731(16) 0.36114(12) 0.0208(7) Uani 1 1 d . . . C47 C 0.30882(13) 0.02007(16) 0.35970(14) 0.0269(7) Uani 1 1 d . . . C48 C 0.30053(14) -0.01695(19) 0.41564(16) 0.0406(9) Uani 1 1 d . . . H48 H 0.2851 -0.0696 0.4154 0.049 Uiso 1 1 calc R . . C49 C 0.31408(15) 0.0206(2) 0.47153(16) 0.0460(9) Uani 1 1 d . . . H49 H 0.3079 -0.0060 0.5093 0.055 Uiso 1 1 calc R . . C50 C 0.33664(14) 0.0969(2) 0.47242(14) 0.0401(8) Uani 1 1 d . . . H50 H 0.3457 0.1227 0.5111 0.048 Uiso 1 1 calc R . . C51 C 0.34642(13) 0.13687(17) 0.41773(13) 0.0291(7) Uani 1 1 d . . . C52 C 0.36897(15) 0.22175(18) 0.42114(14) 0.0399(9) Uani 1 1 d . . . H52 H 0.3779 0.2383 0.3783 0.048 Uiso 1 1 calc R . . C53 C 0.43034(15) 0.2300(2) 0.46251(15) 0.0533(10) Uani 1 1 d . . . H53A H 0.4222 0.2184 0.5056 0.080 Uiso 1 1 calc R . . H53B H 0.4464 0.2839 0.4597 0.080 Uiso 1 1 calc R . . H53C H 0.4617 0.1927 0.4488 0.080 Uiso 1 1 calc R . . C54 C 0.31855(16) 0.2775(2) 0.44310(16) 0.0596(11) Uani 1 1 d . . . H54A H 0.2810 0.2752 0.4140 0.089 Uiso 1 1 calc R . . H54B H 0.3350 0.3316 0.4449 0.089 Uiso 1 1 calc R . . H54C H 0.3075 0.2614 0.4844 0.089 Uiso 1 1 calc R . . C55 C 0.28848(14) -0.02226(16) 0.30009(14) 0.0316(8) Uani 1 1 d . . . H55 H 0.3013 0.0111 0.2651 0.038 Uiso 1 1 calc R . . C56 C 0.32083(15) -0.10255(17) 0.29530(16) 0.0481(9) Uani 1 1 d . . . H56A H 0.3666 -0.0957 0.3015 0.072 Uiso 1 1 calc R . . H56B H 0.3100 -0.1252 0.2542 0.072 Uiso 1 1 calc R . . H56C H 0.3066 -0.1381 0.3271 0.072 Uiso 1 1 calc R . . C57 C 0.21682(14) -0.03106(19) 0.29260(16) 0.0465(9) Uani 1 1 d . . . H57A H 0.2031 -0.0667 0.3246 0.070 Uiso 1 1 calc R . . H57B H 0.2043 -0.0529 0.2515 0.070 Uiso 1 1 calc R . . H57C H 0.1971 0.0207 0.2968 0.070 Uiso 1 1 calc R . . C58 C 0.40792(13) 0.11988(15) 0.13116(12) 0.0210(6) Uani 1 1 d . . . C59 C 0.35721(13) 0.07887(16) 0.09995(13) 0.0255(7) Uani 1 1 d . . . C60 C 0.36670(15) 0.04568(17) 0.04277(14) 0.0345(8) Uani 1 1 d . . . H60 H 0.3327 0.0190 0.0207 0.041 Uiso 1 1 calc R . . C61 C 0.42335(16) 0.05015(18) 0.01729(14) 0.0398(9) Uani 1 1 d . . . H61 H 0.4283 0.0276 -0.0223 0.048 Uiso 1 1 calc R . . C62 C 0.47359(15) 0.08762(17) 0.04935(14) 0.0336(8) Uani 1 1 d . . . H62 H 0.5133 0.0894 0.0320 0.040 Uiso 1 1 calc R . . C63 C 0.46692(13) 0.12278(15) 0.10668(13) 0.0247(7) Uani 1 1 d . . . C64 C 0.52339(13) 0.16114(17) 0.14090(14) 0.0315(8) Uani 1 1 d . . . H64 H 0.5075 0.1929 0.1754 0.038 Uiso 1 1 calc R . . C65 C 0.55916(15) 0.2179(2) 0.10070(17) 0.0577(11) Uani 1 1 d . . . H65A H 0.5778 0.1881 0.0678 0.087 Uiso 1 1 calc R . . H65B H 0.5926 0.2444 0.1265 0.087 Uiso 1 1 calc R . . H65C H 0.5299 0.2574 0.0821 0.087 Uiso 1 1 calc R . . C66 C 0.56782(14) 0.09875(19) 0.17032(15) 0.0497(9) Uani 1 1 d . . . H66A H 0.5442 0.0632 0.1958 0.075 Uiso 1 1 calc R . . H66B H 0.6015 0.1246 0.1964 0.075 Uiso 1 1 calc R . . H66C H 0.5863 0.0684 0.1377 0.075 Uiso 1 1 calc R . . C67 C 0.29317(13) 0.06958(17) 0.12608(13) 0.0298(7) Uani 1 1 d . . . H67 H 0.2967 0.0909 0.1693 0.036 Uiso 1 1 calc R . . C68 C 0.27502(16) -0.01814(17) 0.12971(15) 0.0457(9) Uani 1 1 d . . . H68A H 0.2701 -0.0404 0.0878 0.069 Uiso 1 1 calc R . . H68B H 0.2352 -0.0231 0.1494 0.069 Uiso 1 1 calc R . . H68C H 0.3082 -0.0468 0.1543 0.069 Uiso 1 1 calc R . . C69 C 0.24195(13) 0.11625(19) 0.08922(15) 0.0459(9) Uani 1 1 d . . . H69A H 0.2529 0.1724 0.0902 0.069 Uiso 1 1 calc R . . H69B H 0.2016 0.1087 0.1076 0.069 Uiso 1 1 calc R . . H69C H 0.2383 0.0977 0.0462 0.069 Uiso 1 1 calc R . . C70 C 0.48755(12) 0.16947(15) 0.31375(12) 0.0196(6) Uani 1 1 d . . . C71 C 0.56841(13) 0.18910(18) 0.38512(13) 0.0284(7) Uani 1 1 d . . . C72 C 0.55044(13) 0.26078(18) 0.36238(13) 0.0291(7) Uani 1 1 d . . . C73 C 0.46793(14) 0.30888(16) 0.27836(15) 0.0372(8) Uani 1 1 d . . . H73 H 0.4338 0.2811 0.2526 0.045 Uiso 1 1 calc R . . C74 C 0.51198(17) 0.34353(18) 0.23366(16) 0.0554(10) Uani 1 1 d . . . H74A H 0.5357 0.3873 0.2537 0.083 Uiso 1 1 calc R . . H74B H 0.4873 0.3630 0.1967 0.083 Uiso 1 1 calc R . . H74C H 0.5414 0.3027 0.2217 0.083 Uiso 1 1 calc R . . C75 C 0.43578(15) 0.37270(18) 0.31451(18) 0.0571(11) Uani 1 1 d . . . H75A H 0.4074 0.3479 0.3425 0.086 Uiso 1 1 calc R . . H75B H 0.4115 0.4075 0.2855 0.086 Uiso 1 1 calc R . . H75C H 0.4678 0.4036 0.3388 0.086 Uiso 1 1 calc R . . C76 C 0.53414(13) 0.04555(16) 0.36121(13) 0.0292(7) Uani 1 1 d . . . H76 H 0.5041 0.0225 0.3282 0.035 Uiso 1 1 calc R . . C77 C 0.51213(16) 0.01847(19) 0.42281(15) 0.0501(10) Uani 1 1 d . . . H77A H 0.5406 0.0393 0.4567 0.075 Uiso 1 1 calc R . . H77B H 0.5122 -0.0393 0.4244 0.075 Uiso 1 1 calc R . . H77C H 0.4693 0.0380 0.4272 0.075 Uiso 1 1 calc R . . C78 C 0.59945(13) 0.01581(17) 0.34863(14) 0.0387(8) Uani 1 1 d . . . H78A H 0.6108 0.0359 0.3085 0.058 Uiso 1 1 calc R . . H78B H 0.5994 -0.0420 0.3479 0.058 Uiso 1 1 calc R . . H78C H 0.6302 0.0344 0.3814 0.058 Uiso 1 1 calc R . . C79 C 0.61837(14) 0.1722(2) 0.43574(14) 0.0459(9) Uani 1 1 d . . . H79A H 0.6334 0.2220 0.4547 0.069 Uiso 1 1 calc R . . H79B H 0.6536 0.1448 0.4185 0.069 Uiso 1 1 calc R . . H79C H 0.6009 0.1389 0.4672 0.069 Uiso 1 1 calc R . . C80 C 0.57663(15) 0.34059(18) 0.38057(16) 0.0518(10) Uani 1 1 d . . . H80A H 0.5492 0.3660 0.4091 0.078 Uiso 1 1 calc R . . H80B H 0.5787 0.3734 0.3434 0.078 Uiso 1 1 calc R . . H80C H 0.6191 0.3345 0.4010 0.078 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 0.01553(15) 0.01171(15) 0.01466(16) -0.00002(12) -0.00014(11) 0.00103(13) Ge2 0.01630(16) 0.01454(15) 0.01804(17) 0.00123(13) 0.00143(12) 0.00062(13) O1 0.0227(11) 0.0139(10) 0.0251(12) -0.0003(8) -0.0007(8) 0.0015(8) O2 0.0268(12) 0.0183(11) 0.0351(13) 0.0025(9) 0.0043(9) 0.0047(9) N1 0.0167(13) 0.0151(12) 0.0145(13) 0.0019(9) 0.0020(10) 0.0036(10) N2 0.0192(13) 0.0153(12) 0.0163(13) -0.0017(9) -0.0005(10) 0.0030(10) N3 0.0177(13) 0.0134(12) 0.0178(13) 0.0004(10) 0.0001(10) -0.0006(10) N4 0.0220(13) 0.0115(12) 0.0206(13) 0.0028(9) -0.0013(10) -0.0027(10) N5 0.0186(13) 0.0166(12) 0.0172(13) 0.0022(10) 0.0044(10) 0.0016(10) N6 0.0215(13) 0.0179(13) 0.0178(14) 0.0009(10) 0.0005(10) 0.0030(11) N7 0.0181(13) 0.0258(14) 0.0216(14) 0.0000(10) -0.0004(10) 0.0023(11) N8 0.0180(14) 0.0186(13) 0.0350(16) -0.0015(11) -0.0023(11) -0.0024(11) C1 0.0264(18) 0.0353(18) 0.0287(19) 0.0053(14) 0.0002(14) 0.0128(15) C2 0.0141(15) 0.0160(15) 0.0244(17) -0.0007(12) -0.0021(12) 0.0039(12) C3 0.0239(17) 0.0161(15) 0.0234(17) 0.0029(12) -0.0039(13) 0.0043(13) C4 0.0241(17) 0.0162(15) 0.0198(17) 0.0023(12) -0.0069(13) 0.0009(13) C5 0.0379(19) 0.0278(17) 0.0241(18) 0.0051(14) 0.0001(14) 0.0063(15) C6 0.0122(15) 0.0205(16) 0.0214(17) 0.0023(12) 0.0028(12) 0.0049(12) C7 0.0146(15) 0.0226(16) 0.0188(17) 0.0016(12) 0.0013(12) 0.0078(13) C8 0.0192(17) 0.0389(19) 0.0185(18) -0.0007(14) -0.0003(13) 0.0058(15) C9 0.0242(17) 0.045(2) 0.0229(18) 0.0117(16) 0.0065(13) -0.0006(16) C10 0.0245(18) 0.0303(18) 0.035(2) 0.0129(15) 0.0023(14) -0.0048(14) C11 0.0115(15) 0.0239(17) 0.0273(18) 0.0042(13) -0.0012(12) 0.0031(13) C12 0.0298(18) 0.0202(16) 0.0302(19) 0.0003(13) 0.0049(14) -0.0082(14) C13 0.041(2) 0.042(2) 0.060(3) -0.0159(18) -0.0132(18) 0.0027(18) C14 0.037(2) 0.0271(19) 0.070(3) -0.0097(17) 0.0022(18) -0.0012(16) C15 0.043(2) 0.0202(16) 0.0187(17) -0.0015(12) 0.0057(14) 0.0039(14) C16 0.062(3) 0.031(2) 0.075(3) -0.0061(18) -0.025(2) 0.0159(19) C17 0.0346(19) 0.0291(18) 0.048(2) -0.0092(16) 0.0052(16) -0.0040(16) C18 0.0310(18) 0.0170(15) 0.0125(15) 0.0024(11) -0.0009(13) 0.0067(13) C19 0.049(2) 0.0171(16) 0.0164(17) 0.0020(13) -0.0083(14) 0.0042(15) C20 0.073(3) 0.0268(19) 0.025(2) -0.0040(15) -0.0086(18) 0.0025(18) C21 0.093(3) 0.033(2) 0.028(2) -0.0120(16) 0.014(2) 0.013(2) C22 0.056(2) 0.038(2) 0.033(2) -0.0015(16) 0.0149(17) 0.0176(19) C23 0.040(2) 0.0239(17) 0.0181(17) 0.0028(13) 0.0057(14) 0.0070(15) C24 0.0273(18) 0.0346(19) 0.0310(19) 0.0031(14) 0.0150(14) 0.0063(15) C25 0.040(2) 0.057(2) 0.046(2) 0.0134(18) 0.0154(17) 0.0047(18) C26 0.036(2) 0.050(2) 0.043(2) 0.0097(17) 0.0042(16) 0.0064(17) C27 0.0344(14) 0.0313(14) 0.0332(14) -0.0013(12) -0.0075(12) -0.0030(12) C28 0.0608(17) 0.0672(17) 0.0701(18) 0.0122(15) -0.0137(14) -0.0025(15) C29 0.0529(17) 0.0423(15) 0.0510(17) -0.0022(13) 0.0009(14) -0.0058(14) C30 0.0146(15) 0.0138(14) 0.0174(16) 0.0009(11) 0.0006(12) 0.0006(12) C31 0.0232(16) 0.0212(16) 0.0173(16) -0.0025(12) 0.0009(12) -0.0062(13) C32 0.0286(17) 0.0199(15) 0.0189(16) -0.0027(13) -0.0009(13) -0.0093(14) C33 0.0281(17) 0.0159(16) 0.0252(17) 0.0045(12) -0.0055(13) -0.0032(13) C34 0.0393(19) 0.0286(17) 0.0284(19) 0.0079(14) 0.0004(15) -0.0039(15) C35 0.047(2) 0.0283(18) 0.058(2) 0.0183(17) 0.0106(18) 0.0092(17) C36 0.0248(17) 0.0154(15) 0.0229(17) 0.0019(12) -0.0051(13) 0.0000(13) C37 0.0294(18) 0.0314(18) 0.0348(19) 0.0146(15) -0.0012(14) -0.0014(15) C38 0.0304(18) 0.0268(17) 0.0315(19) 0.0003(14) -0.0038(14) 0.0100(14) C39 0.0382(19) 0.0294(18) 0.0249(18) -0.0007(14) -0.0065(14) -0.0105(15) C40 0.065(2) 0.0245(18) 0.042(2) 0.0047(15) -0.0161(18) -0.0185(17) C41 0.0243(18) 0.0414(19) 0.033(2) 0.0065(15) 0.0030(14) 0.0112(15) C42 0.0218(16) 0.0189(15) 0.0192(17) -0.0022(12) 0.0009(12) 0.0011(13) C43 0.0191(16) 0.0140(15) 0.0272(17) -0.0010(12) -0.0012(13) 0.0037(12) C44 0.0203(16) 0.0165(15) 0.0233(17) 0.0012(12) -0.0032(13) 0.0024(13) C45 0.0342(19) 0.0240(17) 0.0323(19) 0.0071(14) 0.0019(14) 0.0045(14) C46 0.0160(15) 0.0284(17) 0.0186(17) 0.0041(13) 0.0043(12) 0.0037(13) C47 0.0230(17) 0.0269(18) 0.032(2) 0.0068(14) 0.0098(14) 0.0015(14) C48 0.041(2) 0.040(2) 0.043(2) 0.0171(17) 0.0118(17) -0.0024(17) C49 0.035(2) 0.073(3) 0.032(2) 0.026(2) 0.0098(16) 0.002(2) C50 0.032(2) 0.067(2) 0.0214(19) 0.0047(17) 0.0063(14) -0.0016(18) C51 0.0207(17) 0.043(2) 0.0244(19) -0.0007(15) 0.0055(13) 0.0013(15) C52 0.049(2) 0.046(2) 0.0248(19) -0.0143(15) 0.0068(16) -0.0088(18) C53 0.045(2) 0.073(3) 0.043(2) -0.0243(19) 0.0126(18) -0.016(2) C54 0.063(3) 0.059(3) 0.055(3) -0.026(2) -0.004(2) 0.006(2) C55 0.037(2) 0.0195(16) 0.039(2) -0.0018(14) 0.0127(15) -0.0080(15) C56 0.046(2) 0.0262(19) 0.074(3) -0.0041(18) 0.0202(19) -0.0022(17) C57 0.040(2) 0.042(2) 0.058(3) -0.0114(17) 0.0049(18) -0.0048(17) C58 0.0262(17) 0.0203(16) 0.0170(16) 0.0034(12) 0.0037(13) 0.0081(14) C59 0.0315(18) 0.0229(16) 0.0216(17) -0.0030(13) -0.0006(13) 0.0027(14) C60 0.040(2) 0.035(2) 0.0273(19) -0.0083(14) -0.0044(15) 0.0053(16) C61 0.057(2) 0.040(2) 0.0226(19) -0.0060(15) 0.0068(17) 0.0193(18) C62 0.035(2) 0.0379(19) 0.030(2) 0.0040(14) 0.0151(15) 0.0127(16) C63 0.0270(17) 0.0227(16) 0.0247(18) 0.0067(13) 0.0041(13) 0.0084(14) C64 0.0267(18) 0.0339(18) 0.035(2) 0.0009(15) 0.0097(15) 0.0013(15) C65 0.043(2) 0.064(3) 0.069(3) 0.017(2) 0.017(2) -0.008(2) C66 0.037(2) 0.054(2) 0.057(2) 0.0027(19) -0.0110(17) 0.0006(18) C67 0.0287(18) 0.0297(18) 0.0305(18) -0.0066(15) -0.0020(14) -0.0027(15) C68 0.056(2) 0.039(2) 0.043(2) -0.0115(16) 0.0050(18) -0.0148(18) C69 0.0268(19) 0.060(2) 0.050(2) 0.0010(18) -0.0015(16) 0.0022(18) C70 0.0168(16) 0.0202(15) 0.0222(17) -0.0016(12) 0.0045(13) -0.0014(13) C71 0.0193(17) 0.041(2) 0.0251(18) -0.0064(15) 0.0002(13) 0.0003(15) C72 0.0189(17) 0.0344(19) 0.034(2) -0.0114(15) -0.0004(14) -0.0055(15) C73 0.035(2) 0.0184(17) 0.055(2) 0.0050(16) -0.0128(17) -0.0086(15) C74 0.077(3) 0.0241(19) 0.064(3) 0.0082(17) 0.000(2) -0.0131(19) C75 0.040(2) 0.030(2) 0.101(3) 0.004(2) 0.001(2) 0.0060(17) C76 0.0313(18) 0.0270(18) 0.0288(19) 0.0069(13) -0.0010(14) 0.0064(14) C77 0.053(2) 0.054(2) 0.044(2) 0.0234(18) 0.0117(18) 0.0076(19) C78 0.033(2) 0.039(2) 0.044(2) -0.0008(16) 0.0004(16) 0.0125(16) C79 0.032(2) 0.063(2) 0.040(2) -0.0060(18) -0.0127(16) 0.0003(18) C80 0.040(2) 0.045(2) 0.068(3) -0.0200(19) -0.0076(18) -0.0116(18) _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 1.6700(16) . ? Ge1 N2 1.852(2) . ? Ge1 N1 1.871(2) . ? Ge1 C30 2.040(2) . ? Ge2 O2 1.6643(17) . ? Ge2 N6 1.853(2) . ? Ge2 N5 1.866(2) . ? Ge2 C70 2.053(3) . ? N1 C2 1.397(3) . ? N1 C6 1.440(3) . ? N2 C4 1.409(3) . ? N2 C18 1.447(3) . ? N3 C30 1.354(3) . ? N3 C31 1.390(3) . ? N3 C36 1.498(3) . ? N4 C30 1.357(3) . ? N4 C32 1.391(3) . ? N4 C33 1.479(3) . ? N5 C42 1.400(3) . ? N5 C46 1.443(3) . ? N6 C44 1.415(3) . ? N6 C58 1.438(3) . ? N7 C70 1.355(3) . ? N7 C71 1.388(3) . ? N7 C76 1.497(3) . ? N8 C70 1.361(3) . ? N8 C72 1.390(3) . ? N8 C73 1.482(3) . ? C1 C2 1.351(3) . ? C2 C3 1.460(3) . ? C3 C4 1.343(3) . ? C4 C5 1.503(3) . ? C6 C11 1.411(3) . ? C6 C7 1.413(3) . ? C7 C8 1.389(3) . ? C7 C15 1.521(4) . ? C8 C9 1.379(4) . ? C9 C10 1.372(4) . ? C10 C11 1.390(4) . ? C11 C12 1.521(4) . ? C12 C14 1.517(4) . ? C12 C13 1.525(4) . ? C15 C17 1.524(4) . ? C15 C16 1.527(4) . ? C18 C23 1.398(4) . ? C18 C19 1.413(4) . ? C19 C20 1.391(4) . ? C19 C27 1.515(4) . ? C20 C21 1.375(4) . ? C21 C22 1.367(4) . ? C22 C23 1.397(4) . ? C23 C24 1.524(4) . ? C24 C26 1.526(4) . ? C24 C25 1.532(4) . ? C27 C28 1.528(4) . ? C27 C29 1.531(4) . ? C31 C32 1.354(3) . ? C31 C39 1.487(4) . ? C32 C40 1.498(3) . ? C33 C35 1.523(4) . ? C33 C34 1.527(4) . ? C36 C37 1.517(4) . ? C36 C38 1.523(3) . ? C41 C42 1.356(3) . ? C42 C43 1.464(3) . ? C43 C44 1.348(3) . ? C44 C45 1.488(3) . ? C46 C51 1.405(4) . ? C46 C47 1.409(4) . ? C47 C48 1.386(4) . ? C47 C55 1.510(4) . ? C48 C49 1.377(4) . ? C49 C50 1.378(4) . ? C50 C51 1.393(4) . ? C51 C52 1.516(4) . ? C52 C54 1.531(4) . ? C52 C53 1.532(4) . ? C55 C57 1.528(4) . ? C55 C56 1.531(4) . ? C58 C63 1.399(4) . ? C58 C59 1.411(4) . ? C59 C60 1.387(4) . ? C59 C67 1.522(4) . ? C60 C61 1.364(4) . ? C61 C62 1.383(4) . ? C62 C63 1.393(4) . ? C63 C64 1.510(4) . ? C64 C66 1.524(4) . ? C64 C65 1.536(4) . ? C67 C69 1.522(4) . ? C67 C68 1.539(4) . ? C71 C72 1.354(4) . ? C71 C79 1.495(4) . ? C72 C80 1.503(4) . ? C73 C74 1.515(4) . ? C73 C75 1.526(4) . ? C76 C77 1.517(4) . ? C76 C78 1.521(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 O1 Ge1 N2 115.25(8) . . ? O1 Ge1 N1 118.35(8) . . ? N2 Ge1 N1 100.47(9) . . ? O1 Ge1 C30 108.48(9) . . ? N2 Ge1 C30 111.08(9) . . ? N1 Ge1 C30 102.36(9) . . ? O2 Ge2 N6 113.88(9) . . ? O2 Ge2 N5 118.83(9) . . ? N6 Ge2 N5 100.54(9) . . ? O2 Ge2 C70 109.01(10) . . ? N6 Ge2 C70 110.32(10) . . ? N5 Ge2 C70 103.54(10) . . ? C2 N1 C6 118.3(2) . . ? C2 N1 Ge1 122.86(17) . . ? C6 N1 Ge1 118.36(15) . . ? C4 N2 C18 117.8(2) . . ? C4 N2 Ge1 119.78(17) . . ? C18 N2 Ge1 120.21(16) . . ? C30 N3 C31 110.0(2) . . ? C30 N3 C36 123.5(2) . . ? C31 N3 C36 126.5(2) . . ? C30 N4 C32 109.9(2) . . ? C30 N4 C33 123.8(2) . . ? C32 N4 C33 126.1(2) . . ? C42 N5 C46 117.9(2) . . ? C42 N5 Ge2 122.96(17) . . ? C46 N5 Ge2 119.05(16) . . ? C44 N6 C58 116.8(2) . . ? C44 N6 Ge2 119.68(17) . . ? C58 N6 Ge2 120.03(16) . . ? C70 N7 C71 110.1(2) . . ? C70 N7 C76 123.1(2) . . ? C71 N7 C76 126.8(2) . . ? C70 N8 C72 109.9(2) . . ? C70 N8 C73 123.7(2) . . ? C72 N8 C73 126.2(2) . . ? C1 C2 N1 123.0(2) . . ? C1 C2 C3 118.5(2) . . ? N1 C2 C3 118.4(2) . . ? C4 C3 C2 129.4(2) . . ? C3 C4 N2 123.1(2) . . ? C3 C4 C5 120.9(2) . . ? N2 C4 C5 115.9(2) . . ? C11 C6 C7 119.9(2) . . ? C11 C6 N1 120.1(2) . . ? C7 C6 N1 120.0(2) . . ? C8 C7 C6 118.6(2) . . ? C8 C7 C15 118.6(2) . . ? C6 C7 C15 122.8(2) . . ? C9 C8 C7 121.7(3) . . ? C10 C9 C8 119.3(3) . . ? C9 C10 C11 121.8(3) . . ? C10 C11 C6 118.6(3) . . ? C10 C11 C12 118.6(2) . . ? C6 C11 C12 122.8(2) . . ? C14 C12 C11 112.9(2) . . ? C14 C12 C13 111.3(2) . . ? C11 C12 C13 109.7(2) . . ? C7 C15 C17 113.1(2) . . ? C7 C15 C16 111.4(2) . . ? C17 C15 C16 108.7(2) . . ? C23 C18 C19 120.9(2) . . ? C23 C18 N2 119.8(2) . . ? C19 C18 N2 119.3(2) . . ? C20 C19 C18 117.8(3) . . ? C20 C19 C27 119.2(3) . . ? C18 C19 C27 123.1(2) . . ? C21 C20 C19 121.3(3) . . ? C22 C21 C20 120.6(3) . . ? C21 C22 C23 120.7(3) . . ? C22 C23 C18 118.6(3) . . ? C22 C23 C24 118.9(3) . . ? C18 C23 C24 122.5(2) . . ? C23 C24 C26 111.8(2) . . ? C23 C24 C25 112.8(3) . . ? C26 C24 C25 110.7(2) . . ? C19 C27 C28 112.7(3) . . ? C19 C27 C29 111.8(2) . . ? C28 C27 C29 109.3(3) . . ? N3 C30 N4 106.1(2) . . ? N3 C30 Ge1 123.38(17) . . ? N4 C30 Ge1 129.44(18) . . ? C32 C31 N3 107.0(2) . . ? C32 C31 C39 127.2(2) . . ? N3 C31 C39 125.8(2) . . ? C31 C32 N4 107.0(2) . . ? C31 C32 C40 127.5(3) . . ? N4 C32 C40 125.3(2) . . ? N4 C33 C35 112.4(2) . . ? N4 C33 C34 112.0(2) . . ? C35 C33 C34 111.8(2) . . ? N3 C36 C37 111.7(2) . . ? N3 C36 C38 111.3(2) . . ? C37 C36 C38 113.3(2) . . ? C41 C42 N5 123.0(2) . . ? C41 C42 C43 118.7(2) . . ? N5 C42 C43 118.3(2) . . ? C44 C43 C42 129.2(2) . . ? C43 C44 N6 122.9(2) . . ? C43 C44 C45 121.7(2) . . ? N6 C44 C45 115.4(2) . . ? C51 C46 C47 120.7(2) . . ? C51 C46 N5 119.3(2) . . ? C47 C46 N5 120.0(2) . . ? C48 C47 C46 118.2(3) . . ? C48 C47 C55 118.9(3) . . ? C46 C47 C55 122.8(2) . . ? C49 C48 C47 121.7(3) . . ? C48 C49 C50 119.7(3) . . ? C49 C50 C51 121.2(3) . . ? C50 C51 C46 118.4(3) . . ? C50 C51 C52 119.1(3) . . ? C46 C51 C52 122.4(3) . . ? C51 C52 C54 111.9(3) . . ? C51 C52 C53 111.5(3) . . ? C54 C52 C53 110.4(3) . . ? C47 C55 C57 110.9(2) . . ? C47 C55 C56 112.2(3) . . ? C57 C55 C56 110.8(2) . . ? C63 C58 C59 120.7(2) . . ? C63 C58 N6 120.1(2) . . ? C59 C58 N6 119.1(2) . . ? C60 C59 C58 117.9(3) . . ? C60 C59 C67 118.9(3) . . ? C58 C59 C67 123.1(2) . . ? C61 C60 C59 122.0(3) . . ? C60 C61 C62 119.7(3) . . ? C61 C62 C63 121.1(3) . . ? C62 C63 C58 118.5(3) . . ? C62 C63 C64 119.3(3) . . ? C58 C63 C64 122.2(2) . . ? C63 C64 C66 110.6(2) . . ? C63 C64 C65 113.7(3) . . ? C66 C64 C65 110.6(2) . . ? C59 C67 C69 112.1(2) . . ? C59 C67 C68 110.7(2) . . ? C69 C67 C68 110.8(2) . . ? N7 C70 N8 105.9(2) . . ? N7 C70 Ge2 123.63(18) . . ? N8 C70 Ge2 130.23(19) . . ? C72 C71 N7 107.2(2) . . ? C72 C71 C79 127.1(3) . . ? N7 C71 C79 125.7(3) . . ? C71 C72 N8 106.9(2) . . ? C71 C72 C80 128.5(3) . . ? N8 C72 C80 124.6(3) . . ? N8 C73 C74 111.3(3) . . ? N8 C73 C75 113.4(3) . . ? C74 C73 C75 112.0(3) . . ? N7 C76 C77 111.6(2) . . ? N7 C76 C78 111.1(2) . . ? C77 C76 C78 113.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.592 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.052