# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_publication_text _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Matthias Driess' _publ_contact_author_address ;Technische Universit\"at Berlin, Institute of Chemistry Strasse des 17. Juni 136, D-10623 Berlin, Germany ; _publ_contact_author_email matthias.driess@tu-berlin.de _publ_contact_author_phone +49(0)30-314-29731 _publ_contact_author_fax +49(0)30-314-29732 _publ_section_title ;Striking Reactivity of a Ylide-like Germylene toward Terminal Alkynes: [2+4] Cycloaddition versus C-H Bond Activation ; loop_ _publ_author_name _publ_author_address S.Yao ;Technische Universit\"at Berlin, Institute of Chemistry Strasse des 17. Juni 136, D-10623 Berlin, Germany ; 'C.van Wuellen' ;Technische Universit\"at Kaiserslautern, Fachbereich fuer Chemie Erwin-Schroedinger-Strasse, D-67663 Kaiserslautern, Germany ; M.Driess ;Technische Universit\"at Berlin, Institute of Chemistry Strasse des 17. Juni 136, D-10623 Berlin, Germany ; data_CCDC695015 _database_code_depnum_ccdc_archive 'CCDC 695015' _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 'C31 H42 Ge N2' _chemical_formula_weight 515.26 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5367(4) _cell_length_b 12.4840(5) _cell_length_c 42.662(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5611.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3271 _cell_measurement_theta_min 2.8912 _cell_measurement_theta_max 32.3930 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 1.112 _exptl_absorpt_correction_T_min 0.85057 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) 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 33432 _diffrn_reflns_av_R_equivalents 0.1403 _diffrn_reflns_av_sigmaI/netI 0.2137 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4942 _reflns_number_gt 1916 _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^)+(0.0220P)^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 4942 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 0.721 _refine_ls_restrained_S_all 0.721 _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 0.18709(4) 0.22170(3) 0.121684(10) 0.04184(14) Uani 1 1 d . . . N1 N 0.0796(3) 0.1863(2) 0.15846(7) 0.0293(8) Uani 1 1 d . . . C1 C -0.0169(4) 0.0462(3) 0.19031(9) 0.0468(12) Uani 1 1 d . . . H1A H -0.0547 0.0954 0.2045 0.056 Uiso 1 1 calc R . . H1B H -0.0285 -0.0287 0.1932 0.056 Uiso 1 1 calc R . . N2 N 0.0998(3) 0.1015(2) 0.09653(7) 0.0287(8) Uani 1 1 d . . . C2 C 0.0545(4) 0.0831(3) 0.16566(9) 0.0317(10) Uani 1 1 d . . . C3 C 0.1187(4) 0.0023(3) 0.14459(9) 0.0410(12) Uani 1 1 d . . . H3 H 0.1001 -0.0715 0.1525 0.049 Uiso 1 1 calc R . . C4 C 0.0786(3) 0.0104(3) 0.11062(9) 0.0316(10) Uani 1 1 d . . . C5 C 0.0231(3) -0.0843(3) 0.09621(8) 0.0442(11) Uani 1 1 d . . . H5A H -0.0158 -0.0646 0.0762 0.066 Uiso 1 1 calc R . . H5B H -0.0418 -0.1142 0.1101 0.066 Uiso 1 1 calc R . . H5C H 0.0895 -0.1379 0.0926 0.066 Uiso 1 1 calc R . . C6 C 0.0555(4) 0.2672(3) 0.18199(8) 0.0313(10) Uani 1 1 d . . . C7 C -0.0436(4) 0.3399(3) 0.17836(9) 0.0391(11) Uani 1 1 d . . . C8 C -0.0615(4) 0.4189(3) 0.20078(11) 0.0555(13) Uani 1 1 d . . . H8 H -0.1296 0.4682 0.1986 0.067 Uiso 1 1 calc R . . C9 C 0.0176(5) 0.4265(3) 0.22603(10) 0.0622(14) Uani 1 1 d . . . H9 H 0.0048 0.4817 0.2410 0.075 Uiso 1 1 calc R . . C10 C 0.1152(4) 0.3553(3) 0.22996(10) 0.0534(13) Uani 1 1 d . . . H10 H 0.1692 0.3619 0.2477 0.064 Uiso 1 1 calc R . . C11 C 0.1366(3) 0.2738(3) 0.20851(9) 0.0348(10) Uani 1 1 d . . . C12 C 0.2448(4) 0.1985(3) 0.21391(9) 0.0412(11) Uani 1 1 d . . . H12 H 0.2330 0.1362 0.1995 0.049 Uiso 1 1 calc R . . C13 C 0.3724(4) 0.2501(3) 0.20595(10) 0.0699(15) Uani 1 1 d . . . H13A H 0.3729 0.2715 0.1838 0.105 Uiso 1 1 calc R . . H13B H 0.4409 0.1986 0.2097 0.105 Uiso 1 1 calc R . . H13C H 0.3852 0.3135 0.2192 0.105 Uiso 1 1 calc R . . C14 C 0.2464(4) 0.1548(3) 0.24737(9) 0.0714(15) Uani 1 1 d . . . H14A H 0.2677 0.2127 0.2620 0.107 Uiso 1 1 calc R . . H14B H 0.3101 0.0979 0.2490 0.107 Uiso 1 1 calc R . . H14C H 0.1626 0.1259 0.2526 0.107 Uiso 1 1 calc R . . C15 C -0.1323(4) 0.3343(3) 0.15043(10) 0.0553(13) Uani 1 1 d . . . H15 H -0.0854 0.2985 0.1329 0.066 Uiso 1 1 calc R . . C16 C -0.2473(4) 0.2660(3) 0.15800(10) 0.0816(16) Uani 1 1 d . . . H16A H -0.2196 0.1943 0.1643 0.122 Uiso 1 1 calc R . . H16B H -0.3016 0.2605 0.1394 0.122 Uiso 1 1 calc R . . H16C H -0.2952 0.2991 0.1752 0.122 Uiso 1 1 calc R . . C17 C -0.1749(4) 0.4431(3) 0.13880(10) 0.0845(16) Uani 1 1 d . . . H17A H -0.2224 0.4346 0.1192 0.127 Uiso 1 1 calc R . . H17B H -0.1004 0.4884 0.1351 0.127 Uiso 1 1 calc R . . H17C H -0.2294 0.4768 0.1546 0.127 Uiso 1 1 calc R . . C18 C 0.0840(4) 0.1102(3) 0.06275(9) 0.0302(10) Uani 1 1 d . . . C19 C -0.0248(4) 0.1604(3) 0.05097(10) 0.0350(11) Uani 1 1 d . . . C20 C -0.0344(4) 0.1741(3) 0.01878(10) 0.0454(12) Uani 1 1 d . . . H20 H -0.1076 0.2076 0.0103 0.054 Uiso 1 1 calc R . . C21 C 0.0607(5) 0.1401(3) -0.00098(10) 0.0508(13) Uani 1 1 d . . . H21 H 0.0533 0.1512 -0.0229 0.061 Uiso 1 1 calc R . . C22 C 0.1663(4) 0.0900(3) 0.01101(9) 0.0467(12) Uani 1 1 d . . . H22 H 0.2306 0.0661 -0.0029 0.056 Uiso 1 1 calc R . . C23 C 0.1816(4) 0.0731(3) 0.04341(9) 0.0371(10) Uani 1 1 d . . . C24 C -0.1346(4) 0.1942(3) 0.07183(9) 0.0413(12) Uani 1 1 d . . . H24 H -0.1038 0.1920 0.0940 0.050 Uiso 1 1 calc R . . C25 C -0.1782(4) 0.3059(3) 0.06532(11) 0.0999(18) Uani 1 1 d . . . H25A H -0.2027 0.3121 0.0432 0.150 Uiso 1 1 calc R . . H25B H -0.1091 0.3562 0.0698 0.150 Uiso 1 1 calc R . . H25C H -0.2513 0.3227 0.0786 0.150 Uiso 1 1 calc R . . C26 C -0.2443(4) 0.1195(3) 0.06943(12) 0.104(2) Uani 1 1 d . . . H26A H -0.3061 0.1363 0.0859 0.156 Uiso 1 1 calc R . . H26B H -0.2146 0.0457 0.0720 0.156 Uiso 1 1 calc R . . H26C H -0.2845 0.1275 0.0488 0.156 Uiso 1 1 calc R . . C27 C 0.2998(4) 0.0174(3) 0.05542(9) 0.0436(11) Uani 1 1 d . . . H27 H 0.2861 0.0011 0.0781 0.052 Uiso 1 1 calc R . . C28 C 0.4134(4) 0.0916(3) 0.05308(11) 0.0758(15) Uani 1 1 d . . . H28A H 0.4339 0.1040 0.0310 0.114 Uiso 1 1 calc R . . H28B H 0.4864 0.0588 0.0636 0.114 Uiso 1 1 calc R . . H28C H 0.3933 0.1601 0.0632 0.114 Uiso 1 1 calc R . . C29 C 0.3215(4) -0.0888(3) 0.03853(9) 0.0708(14) Uani 1 1 d . . . H29A H 0.2451 -0.1332 0.0402 0.106 Uiso 1 1 calc R . . H29B H 0.3933 -0.1264 0.0482 0.106 Uiso 1 1 calc R . . H29C H 0.3401 -0.0751 0.0164 0.106 Uiso 1 1 calc R . . C30 C 0.3142(4) 0.1135(3) 0.13543(9) 0.0491(12) Uani 1 1 d . . . H30 H 0.4030 0.1264 0.1345 0.059 Uiso 1 1 calc R . . C31 C 0.2665(5) 0.0225(4) 0.14590(9) 0.0550(13) Uani 1 1 d . . . H31 H 0.3211 -0.0309 0.1542 0.066 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 0.0441(3) 0.0407(2) 0.0406(3) 0.0007(3) 0.0034(3) -0.0061(3) N1 0.036(2) 0.027(2) 0.026(2) 0.0020(17) 0.0000(16) 0.0012(16) C1 0.067(3) 0.035(3) 0.039(3) 0.005(2) 0.014(3) -0.007(2) N2 0.034(2) 0.0263(19) 0.026(2) -0.0016(17) 0.0008(17) 0.0027(16) C2 0.039(3) 0.036(3) 0.020(3) 0.002(2) -0.008(2) 0.004(2) C3 0.067(4) 0.030(3) 0.026(3) 0.005(2) -0.005(2) 0.006(3) C4 0.039(3) 0.028(2) 0.028(3) -0.006(2) -0.008(2) 0.008(2) C5 0.048(3) 0.044(3) 0.041(3) 0.002(2) -0.001(2) -0.005(2) C6 0.038(3) 0.029(2) 0.027(3) 0.005(2) 0.003(2) -0.001(2) C7 0.048(3) 0.045(3) 0.024(3) -0.001(2) -0.001(2) 0.005(3) C8 0.067(4) 0.054(3) 0.046(3) -0.007(3) -0.004(3) 0.019(3) C9 0.104(5) 0.046(3) 0.036(3) -0.017(3) 0.003(3) 0.011(3) C10 0.089(4) 0.039(3) 0.032(3) -0.011(3) -0.004(3) 0.001(3) C11 0.047(3) 0.029(2) 0.029(3) 0.000(2) -0.004(2) -0.004(2) C12 0.052(3) 0.046(3) 0.026(3) -0.002(2) -0.012(2) -0.004(2) C13 0.054(3) 0.076(4) 0.079(4) -0.004(3) -0.018(3) -0.004(3) C14 0.105(4) 0.073(3) 0.035(3) 0.008(3) -0.013(3) 0.013(3) C15 0.057(3) 0.060(3) 0.050(3) -0.012(3) -0.003(3) 0.027(3) C16 0.092(4) 0.065(3) 0.088(4) 0.007(3) -0.047(3) -0.011(3) C17 0.079(4) 0.095(4) 0.080(4) 0.033(3) -0.017(3) -0.007(3) C18 0.039(3) 0.030(3) 0.021(3) 0.001(2) -0.012(2) -0.002(2) C19 0.048(3) 0.032(2) 0.026(3) -0.002(2) -0.008(2) -0.010(2) C20 0.055(3) 0.045(3) 0.036(3) 0.000(2) -0.013(3) 0.003(2) C21 0.089(4) 0.041(3) 0.022(3) 0.000(2) -0.009(3) 0.000(3) C22 0.071(4) 0.049(3) 0.021(3) 0.003(2) 0.008(3) 0.005(3) C23 0.046(3) 0.038(3) 0.028(3) -0.003(2) 0.006(3) -0.004(3) C24 0.030(3) 0.061(4) 0.033(3) -0.005(2) -0.014(2) 0.003(2) C25 0.090(4) 0.078(4) 0.132(5) 0.035(3) 0.047(4) 0.045(3) C26 0.094(5) 0.090(4) 0.128(5) -0.015(4) 0.050(4) -0.030(3) C27 0.043(3) 0.049(3) 0.038(3) -0.005(2) 0.005(3) 0.011(3) C28 0.036(3) 0.103(4) 0.089(4) 0.004(3) -0.004(3) 0.006(3) C29 0.082(4) 0.077(3) 0.054(3) -0.006(3) -0.005(3) 0.035(3) C30 0.039(3) 0.065(3) 0.043(3) -0.011(2) 0.001(3) -0.014(3) C31 0.050(4) 0.075(4) 0.040(3) -0.013(3) -0.013(3) 0.035(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 1.985(3) . ? Ge1 C30 1.991(4) . ? Ge1 N2 2.061(3) . ? N1 C2 1.351(4) . ? N1 C6 1.446(4) . ? C1 C2 1.373(4) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? N2 C4 1.306(4) . ? N2 C18 1.455(4) . ? C2 C3 1.511(5) . ? C3 C4 1.513(5) . ? C3 C31 1.578(5) . ? C3 H3 1.0000 . ? C4 C5 1.455(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.393(4) . ? C6 C11 1.420(4) . ? C7 C8 1.387(5) . ? C7 C15 1.516(5) . ? C8 C9 1.365(5) . ? C8 H8 0.9500 . ? C9 C10 1.370(5) . ? C9 H9 0.9500 . ? C10 C11 1.387(5) . ? C10 H10 0.9500 . ? C11 C12 1.496(5) . ? C12 C14 1.528(4) . ? C12 C13 1.530(4) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.514(5) . ? C15 C16 1.517(5) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.398(5) . ? C18 C19 1.400(5) . ? C19 C20 1.387(5) . ? C19 C24 1.519(5) . ? C20 C21 1.376(5) . ? C20 H20 0.9500 . ? C21 C22 1.376(5) . ? C21 H21 0.9500 . ? C22 C23 1.407(5) . ? C22 H22 0.9500 . ? C23 C27 1.516(5) . ? C24 C26 1.488(5) . ? C24 C25 1.495(4) . ? C24 H24 1.0000 . ? 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 C28 1.517(5) . ? C27 C29 1.526(4) . ? C27 H27 1.0000 . ? 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 C31 1.321(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? 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 C30 90.01(14) . . ? N1 Ge1 N2 89.71(12) . . ? C30 Ge1 N2 87.69(14) . . ? C2 N1 C6 118.3(3) . . ? C2 N1 Ge1 120.2(2) . . ? C6 N1 Ge1 119.6(2) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C4 N2 C18 120.1(3) . . ? C4 N2 Ge1 118.1(3) . . ? C18 N2 Ge1 120.8(2) . . ? N1 C2 C1 127.0(4) . . ? N1 C2 C3 114.5(3) . . ? C1 C2 C3 118.4(4) . . ? C2 C3 C4 113.6(3) . . ? C2 C3 C31 108.3(3) . . ? C4 C3 C31 107.4(3) . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C31 C3 H3 109.2 . . ? N2 C4 C5 125.6(3) . . ? N2 C4 C3 116.8(3) . . ? C5 C4 C3 117.6(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 120.1(4) . . ? C7 C6 N1 120.6(3) . . ? C11 C6 N1 119.2(4) . . ? C8 C7 C6 119.3(4) . . ? C8 C7 C15 119.4(4) . . ? C6 C7 C15 121.3(4) . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 121.1(4) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C6 118.1(4) . . ? C10 C11 C12 118.9(4) . . ? C6 C11 C12 123.0(4) . . ? C11 C12 C14 112.2(3) . . ? C11 C12 C13 111.7(3) . . ? C14 C12 C13 110.3(3) . . ? C11 C12 H12 107.5 . . ? C14 C12 H12 107.5 . . ? C13 C12 H12 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C15 C7 113.5(4) . . ? C17 C15 C16 109.7(3) . . ? C7 C15 C16 110.6(4) . . ? C17 C15 H15 107.6 . . ? C7 C15 H15 107.6 . . ? C16 C15 H15 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 122.6(4) . . ? C23 C18 N2 118.4(3) . . ? C19 C18 N2 118.9(4) . . ? C20 C19 C18 118.1(4) . . ? C20 C19 C24 119.4(4) . . ? C18 C19 C24 122.5(4) . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 120.1(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 121.7(4) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C18 C23 C22 116.5(4) . . ? C18 C23 C27 123.9(4) . . ? C22 C23 C27 119.7(4) . . ? C26 C24 C25 109.4(3) . . ? C26 C24 C19 112.2(3) . . ? C25 C24 C19 112.6(3) . . ? C26 C24 H24 107.5 . . ? C25 C24 H24 107.5 . . ? C19 C24 H24 107.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 C28 110.2(3) . . ? C23 C27 C29 111.2(3) . . ? C28 C27 C29 112.4(4) . . ? C23 C27 H27 107.6 . . ? C28 C27 H27 107.6 . . ? C29 C27 H27 107.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 Ge1 115.3(3) . . ? C31 C30 H30 122.4 . . ? Ge1 C30 H30 122.4 . . ? C30 C31 C3 120.1(4) . . ? C30 C31 H31 120.0 . . ? C3 C31 H31 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.541 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.053 # Attachment 'CCDC695016.CIF' data_CCDC695016 _database_code_depnum_ccdc_archive 'CCDC 695016' _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 'C37 H46 Ge N2' _chemical_formula_weight 591.35 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 8.7780(3) _cell_length_b 10.3884(3) _cell_length_c 18.0841(6) _cell_angle_alpha 83.171(3) _cell_angle_beta 88.937(2) _cell_angle_gamma 88.879(3) _cell_volume 1636.85(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 3.0086 _cell_measurement_theta_max 32.3913 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 15397 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5751 _reflns_number_gt 4906 _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^)+(0.0301P)^2^+0.1368P] 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 5751 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.03839(2) 0.352709(19) 0.805208(10) 0.01949(7) Uani 1 1 d . . . N1 N 0.03158(15) 0.45523(14) 0.70715(8) 0.0178(3) Uani 1 1 d . . . C1 C -0.1075(2) 0.50586(18) 0.59173(10) 0.0268(4) Uani 1 1 d . . . H1A H -0.0245 0.5510 0.5670 0.032 Uiso 1 1 calc R . . H1B H -0.2000 0.4983 0.5662 0.032 Uiso 1 1 calc R . . N2 N -0.18482(15) 0.41635(13) 0.82666(8) 0.0176(3) Uani 1 1 d . . . C2 C -0.09420(18) 0.45272(16) 0.66284(9) 0.0176(4) Uani 1 1 d . . . C3 C -0.22561(18) 0.37467(16) 0.70028(9) 0.0176(4) Uani 1 1 d . . . H3 H -0.3129 0.3802 0.6652 0.021 Uiso 1 1 calc R . . C4 C -0.28014(19) 0.42107(16) 0.77292(9) 0.0189(4) Uani 1 1 d . . . C5 C -0.4430(2) 0.4612(2) 0.77825(10) 0.0282(4) Uani 1 1 d . . . H5A H -0.4635 0.4913 0.8269 0.042 Uiso 1 1 calc R . . H5B H -0.5076 0.3871 0.7727 0.042 Uiso 1 1 calc R . . H5C H -0.4653 0.5315 0.7387 0.042 Uiso 1 1 calc R . . C6 C 0.16949(18) 0.50164(17) 0.66952(9) 0.0183(4) Uani 1 1 d . . . C7 C 0.26244(19) 0.41555(17) 0.63322(9) 0.0196(4) Uani 1 1 d . . . C8 C 0.39447(19) 0.46248(18) 0.59623(10) 0.0238(4) Uani 1 1 d . . . H8 H 0.4589 0.4050 0.5723 0.029 Uiso 1 1 calc R . . C9 C 0.4333(2) 0.59159(19) 0.59371(10) 0.0260(4) Uani 1 1 d . . . H9 H 0.5237 0.6223 0.5684 0.031 Uiso 1 1 calc R . . C10 C 0.3399(2) 0.67491(18) 0.62810(10) 0.0252(4) Uani 1 1 d . . . H10 H 0.3669 0.7634 0.6260 0.030 Uiso 1 1 calc R . . C11 C 0.20702(19) 0.63333(17) 0.66590(10) 0.0213(4) Uani 1 1 d . . . C12 C 0.1053(2) 0.73142(18) 0.69969(11) 0.0287(4) Uani 1 1 d . . . H12 H 0.0147 0.6849 0.7232 0.034 Uiso 1 1 calc R . . C13 C 0.1884(3) 0.7923(2) 0.76063(12) 0.0435(6) Uani 1 1 d . . . H13A H 0.2208 0.7239 0.7995 0.065 Uiso 1 1 calc R . . H13B H 0.1195 0.8534 0.7824 0.065 Uiso 1 1 calc R . . H13C H 0.2780 0.8383 0.7388 0.065 Uiso 1 1 calc R . . C14 C 0.0480(2) 0.8376(2) 0.64021(13) 0.0435(6) Uani 1 1 d . . . H14A H 0.1348 0.8865 0.6175 0.065 Uiso 1 1 calc R . . H14B H -0.0221 0.8963 0.6632 0.065 Uiso 1 1 calc R . . H14C H -0.0053 0.7979 0.6018 0.065 Uiso 1 1 calc R . . C15 C 0.2222(2) 0.27344(17) 0.63450(10) 0.0229(4) Uani 1 1 d . . . H15 H 0.1113 0.2653 0.6475 0.028 Uiso 1 1 calc R . . C16 C 0.3103(2) 0.18884(19) 0.69449(11) 0.0337(5) Uani 1 1 d . . . H16A H 0.4196 0.1933 0.6827 0.051 Uiso 1 1 calc R . . H16B H 0.2773 0.0989 0.6965 0.051 Uiso 1 1 calc R . . H16C H 0.2905 0.2200 0.7429 0.051 Uiso 1 1 calc R . . C17 C 0.2481(3) 0.2223(2) 0.55924(11) 0.0366(5) Uani 1 1 d . . . H17A H 0.3576 0.2189 0.5479 0.055 Uiso 1 1 calc R . . H17B H 0.1968 0.2801 0.5203 0.055 Uiso 1 1 calc R . . H17C H 0.2064 0.1351 0.5614 0.055 Uiso 1 1 calc R . . C18 C -0.23656(19) 0.42775(17) 0.90236(9) 0.0197(4) Uani 1 1 d . . . C19 C -0.3160(2) 0.32363(18) 0.94088(10) 0.0246(4) Uani 1 1 d . . . C20 C -0.3555(2) 0.3328(2) 1.01527(10) 0.0311(5) Uani 1 1 d . . . H20 H -0.4101 0.2644 1.0428 0.037 Uiso 1 1 calc R . . C21 C -0.3169(2) 0.4388(2) 1.04952(11) 0.0332(5) Uani 1 1 d . . . H21 H -0.3442 0.4425 1.1003 0.040 Uiso 1 1 calc R . . C22 C -0.2390(2) 0.53935(19) 1.01065(10) 0.0293(5) Uani 1 1 d . . . H22 H -0.2132 0.6118 1.0351 0.035 Uiso 1 1 calc R . . C23 C -0.1970(2) 0.53719(18) 0.93602(10) 0.0224(4) Uani 1 1 d . . . C24 C -0.1158(2) 0.65016(17) 0.89241(10) 0.0249(4) Uani 1 1 d . . . H24 H -0.0330 0.6137 0.8619 0.030 Uiso 1 1 calc R . . C25 C -0.2241(2) 0.72974(19) 0.83885(11) 0.0355(5) Uani 1 1 d . . . H25A H -0.2631 0.6746 0.8034 0.053 Uiso 1 1 calc R . . H25B H -0.1693 0.8024 0.8117 0.053 Uiso 1 1 calc R . . H25C H -0.3094 0.7631 0.8671 0.053 Uiso 1 1 calc R . . C26 C -0.0419(2) 0.74005(19) 0.94219(11) 0.0336(5) Uani 1 1 d . . . H26A H -0.1216 0.7863 0.9677 0.050 Uiso 1 1 calc R . . H26B H 0.0216 0.8028 0.9115 0.050 Uiso 1 1 calc R . . H26C H 0.0215 0.6885 0.9792 0.050 Uiso 1 1 calc R . . C27 C -0.3524(2) 0.20024(19) 0.90759(11) 0.0297(5) Uani 1 1 d . . . H27 H -0.3310 0.2164 0.8528 0.036 Uiso 1 1 calc R . . C28 C -0.2471(3) 0.0889(2) 0.93952(12) 0.0419(5) Uani 1 1 d . . . H28A H -0.1408 0.1120 0.9282 0.063 Uiso 1 1 calc R . . H28B H -0.2707 0.0103 0.9172 0.063 Uiso 1 1 calc R . . H28C H -0.2625 0.0730 0.9936 0.063 Uiso 1 1 calc R . . C29 C -0.5211(2) 0.1644(2) 0.91825(13) 0.0483(6) Uani 1 1 d . . . H29A H -0.5451 0.1459 0.9716 0.072 Uiso 1 1 calc R . . H29B H -0.5406 0.0874 0.8935 0.072 Uiso 1 1 calc R . . H29C H -0.5852 0.2369 0.8965 0.072 Uiso 1 1 calc R . . C30 C -0.06325(19) 0.20338(17) 0.76537(9) 0.0195(4) Uani 1 1 d . . . H30 H -0.0325 0.1162 0.7806 0.023 Uiso 1 1 calc R . . C31 C -0.17454(19) 0.23107(16) 0.71714(9) 0.0188(4) Uani 1 1 d . . . C32 C -0.24903(18) 0.13612(17) 0.67476(10) 0.0199(4) Uani 1 1 d . . . C33 C -0.3059(2) 0.02158(17) 0.71200(10) 0.0243(4) Uani 1 1 d . . . H33 H -0.3011 0.0064 0.7648 0.029 Uiso 1 1 calc R . . C34 C -0.3693(2) -0.07068(18) 0.67292(11) 0.0284(4) Uani 1 1 d . . . H34 H -0.4083 -0.1482 0.6990 0.034 Uiso 1 1 calc R . . C35 C -0.3758(2) -0.05004(19) 0.59631(11) 0.0307(5) Uani 1 1 d . . . H35 H -0.4175 -0.1139 0.5695 0.037 Uiso 1 1 calc R . . C36 C -0.3214(2) 0.0636(2) 0.55877(11) 0.0319(5) Uani 1 1 d . . . H36 H -0.3267 0.0782 0.5060 0.038 Uiso 1 1 calc R . . C37 C -0.2590(2) 0.15675(19) 0.59749(10) 0.0266(4) Uani 1 1 d . . . H37 H -0.2228 0.2351 0.5711 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ge1 0.02002(11) 0.01937(11) 0.01932(10) -0.00306(8) -0.00146(7) -0.00037(7) N1 0.0163(7) 0.0178(8) 0.0190(7) -0.0016(6) 0.0014(6) -0.0009(6) C1 0.0231(10) 0.0333(11) 0.0233(10) -0.0001(9) -0.0011(8) -0.0029(9) N2 0.0216(8) 0.0137(8) 0.0172(7) -0.0011(6) 0.0017(6) -0.0007(6) C2 0.0182(9) 0.0139(9) 0.0214(9) -0.0050(7) 0.0013(7) 0.0017(7) C3 0.0169(9) 0.0185(9) 0.0179(9) -0.0038(7) -0.0023(7) 0.0004(7) C4 0.0207(9) 0.0140(9) 0.0218(9) -0.0007(7) 0.0017(8) -0.0026(7) C5 0.0226(10) 0.0375(12) 0.0250(10) -0.0069(9) 0.0002(8) 0.0060(9) C6 0.0169(9) 0.0210(10) 0.0166(9) 0.0002(8) -0.0022(7) -0.0013(7) C7 0.0183(9) 0.0214(10) 0.0190(9) -0.0015(8) -0.0034(7) 0.0014(8) C8 0.0200(9) 0.0286(11) 0.0230(10) -0.0044(8) 0.0009(8) 0.0020(8) C9 0.0195(9) 0.0324(11) 0.0250(10) 0.0008(9) 0.0030(8) -0.0048(8) C10 0.0253(10) 0.0217(10) 0.0280(10) 0.0003(8) 0.0000(8) -0.0055(8) C11 0.0222(9) 0.0191(10) 0.0224(9) -0.0012(8) -0.0003(8) -0.0020(8) C12 0.0303(11) 0.0188(10) 0.0369(11) -0.0045(9) 0.0112(9) -0.0031(8) C13 0.0585(15) 0.0333(13) 0.0408(13) -0.0141(11) 0.0066(11) -0.0040(11) C14 0.0401(13) 0.0317(13) 0.0574(15) -0.0026(11) 0.0042(11) 0.0119(10) C15 0.0222(9) 0.0198(10) 0.0271(10) -0.0044(8) 0.0033(8) 0.0006(8) C16 0.0352(11) 0.0256(11) 0.0389(12) 0.0014(10) 0.0020(10) 0.0016(9) C17 0.0521(13) 0.0266(11) 0.0324(11) -0.0099(9) 0.0041(10) -0.0024(10) C18 0.0184(9) 0.0233(10) 0.0172(9) -0.0026(8) 0.0007(7) 0.0051(8) C19 0.0215(9) 0.0271(11) 0.0245(10) -0.0007(8) 0.0027(8) 0.0030(8) C20 0.0293(11) 0.0367(12) 0.0254(10) 0.0030(9) 0.0082(9) 0.0037(9) C21 0.0359(11) 0.0433(13) 0.0197(10) -0.0033(10) 0.0047(9) 0.0135(10) C22 0.0359(11) 0.0294(11) 0.0238(10) -0.0097(9) -0.0016(9) 0.0111(9) C23 0.0224(9) 0.0218(10) 0.0229(9) -0.0030(8) -0.0016(8) 0.0091(8) C24 0.0309(10) 0.0204(10) 0.0243(10) -0.0063(8) -0.0020(8) 0.0037(8) C25 0.0489(13) 0.0226(11) 0.0348(11) -0.0022(9) -0.0094(10) 0.0030(10) C26 0.0398(12) 0.0267(11) 0.0360(11) -0.0104(10) -0.0047(9) 0.0008(9) C27 0.0332(11) 0.0271(11) 0.0282(10) -0.0013(9) 0.0075(9) -0.0058(9) C28 0.0538(14) 0.0269(12) 0.0445(13) -0.0030(10) 0.0048(11) -0.0017(10) C29 0.0422(13) 0.0503(15) 0.0525(15) -0.0062(12) 0.0113(11) -0.0172(11) C30 0.0215(9) 0.0158(9) 0.0204(9) 0.0003(8) 0.0017(8) 0.0007(7) C31 0.0209(9) 0.0158(9) 0.0199(9) -0.0031(8) 0.0060(8) -0.0030(7) C32 0.0149(9) 0.0194(10) 0.0263(10) -0.0076(8) 0.0022(8) 0.0019(7) C33 0.0244(10) 0.0221(10) 0.0267(10) -0.0035(8) -0.0015(8) -0.0002(8) C34 0.0273(10) 0.0190(10) 0.0394(12) -0.0047(9) -0.0001(9) -0.0051(8) C35 0.0273(10) 0.0301(12) 0.0381(12) -0.0165(10) -0.0033(9) -0.0064(9) C36 0.0363(11) 0.0370(12) 0.0240(10) -0.0094(9) -0.0016(9) -0.0054(10) C37 0.0304(10) 0.0248(11) 0.0249(10) -0.0040(8) 0.0023(8) -0.0067(8) _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 1.9583(14) . ? Ge1 C30 2.0162(17) . ? Ge1 N2 2.0997(14) . ? N1 C2 1.379(2) . ? N1 C6 1.441(2) . ? C1 C2 1.344(2) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? N2 C4 1.290(2) . ? N2 C18 1.452(2) . ? C2 C3 1.524(2) . ? C3 C4 1.518(2) . ? C3 C31 1.546(2) . ? C3 H3 1.0000 . ? C4 C5 1.486(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.407(2) . ? C6 C7 1.410(2) . ? C7 C8 1.394(2) . ? C7 C15 1.522(2) . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C11 C12 1.517(2) . ? C12 C14 1.530(3) . ? C12 C13 1.536(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.525(3) . ? C15 C17 1.530(2) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.404(2) . ? C18 C19 1.405(2) . ? C19 C20 1.397(3) . ? C19 C27 1.521(3) . ? C20 C21 1.378(3) . ? C20 H20 0.9500 . ? C21 C22 1.374(3) . ? C21 H21 0.9500 . ? C22 C23 1.395(2) . ? C22 H22 0.9500 . ? C23 C24 1.516(3) . ? C24 C25 1.529(3) . ? C24 C26 1.532(2) . ? C24 H24 1.0000 . ? 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 C28 1.531(3) . ? C27 C29 1.537(3) . ? C27 H27 1.0000 . ? 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 C31 1.326(2) . ? C30 H30 0.9500 . ? C31 C32 1.487(2) . ? C32 C33 1.392(2) . ? C32 C37 1.392(2) . ? C33 C34 1.387(2) . ? C33 H33 0.9500 . ? C34 C35 1.378(3) . ? C34 H34 0.9500 . ? C35 C36 1.379(3) . ? C35 H35 0.9500 . ? C36 C37 1.387(3) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? 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 C30 91.05(6) . . ? N1 Ge1 N2 89.09(5) . . ? C30 Ge1 N2 84.81(6) . . ? C2 N1 C6 115.75(13) . . ? C2 N1 Ge1 120.68(11) . . ? C6 N1 Ge1 120.82(11) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C4 N2 C18 121.04(14) . . ? C4 N2 Ge1 117.18(11) . . ? C18 N2 Ge1 120.54(11) . . ? C1 C2 N1 126.91(16) . . ? C1 C2 C3 119.20(15) . . ? N1 C2 C3 113.82(14) . . ? C4 C3 C2 113.57(13) . . ? C4 C3 C31 107.92(14) . . ? C2 C3 C31 109.20(13) . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C31 C3 H3 108.7 . . ? N2 C4 C5 124.71(16) . . ? N2 C4 C3 118.04(15) . . ? C5 C4 C3 117.14(15) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 120.29(15) . . ? C11 C6 N1 120.15(15) . . ? C7 C6 N1 119.48(15) . . ? C8 C7 C6 118.74(16) . . ? C8 C7 C15 119.90(16) . . ? C6 C7 C15 121.36(15) . . ? C9 C8 C7 121.12(17) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 119.45(17) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.87(17) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C10 C11 C6 118.50(16) . . ? C10 C11 C12 119.24(16) . . ? C6 C11 C12 122.24(15) . . ? C11 C12 C14 111.41(16) . . ? C11 C12 C13 111.11(16) . . ? C14 C12 C13 110.08(17) . . ? C11 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 C16 111.04(15) . . ? C7 C15 C17 113.17(15) . . ? C16 C15 C17 109.71(16) . . ? C7 C15 H15 107.6 . . ? C16 C15 H15 107.6 . . ? C17 C15 H15 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 122.44(16) . . ? C23 C18 N2 119.32(15) . . ? C19 C18 N2 118.09(15) . . ? C20 C19 C18 117.14(17) . . ? C20 C19 C27 118.96(17) . . ? C18 C19 C27 123.80(16) . . ? C21 C20 C19 121.36(18) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C22 C21 C20 120.37(17) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 121.34(18) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 117.34(17) . . ? C22 C23 C24 121.31(17) . . ? C18 C23 C24 121.33(15) . . ? C23 C24 C25 111.08(15) . . ? C23 C24 C26 113.23(15) . . ? C25 C24 C26 109.19(15) . . ? C23 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? C26 C24 H24 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 C28 110.22(16) . . ? C19 C27 C29 112.28(16) . . ? C28 C27 C29 111.53(18) . . ? C19 C27 H27 107.5 . . ? C28 C27 H27 107.5 . . ? C29 C27 H27 107.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 Ge1 117.68(13) . . ? C31 C30 H30 121.2 . . ? Ge1 C30 H30 121.2 . . ? C30 C31 C32 125.29(16) . . ? C30 C31 C3 117.59(15) . . ? C32 C31 C3 117.04(14) . . ? C33 C32 C37 118.53(16) . . ? C33 C32 C31 120.06(15) . . ? C37 C32 C31 121.37(16) . . ? C34 C33 C32 120.74(17) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C35 C34 C33 120.09(18) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 119.77(17) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C35 C36 C37 120.46(18) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C36 C37 C32 120.38(17) . . ? C36 C37 H37 119.8 . . ? C32 C37 H37 119.8 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.306 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.042 # Attachment 'CCDC695017.CIF' data_CCDC695017 _database_code_depnum_ccdc_archive 'CCDC 695017' _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 'C37 H46 Ge N2' _chemical_formula_weight 591.35 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 14.1420(3) _cell_length_b 20.5933(6) _cell_length_c 11.1905(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3259.01(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5482 _cell_measurement_theta_min 2.9618 _cell_measurement_theta_max 32.4278 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_T_min 0.94891 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) 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 23042 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2959 _reflns_number_gt 1951 _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^)+(0.0421P)^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 2959 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 0.11141(2) 0.7500 0.14614(3) 0.02969(14) Uani 1 2 d S . . N1 N 0.18256(12) 0.68109(9) 0.23149(17) 0.0269(5) Uani 1 1 d . . . C1 C 0.32895(17) 0.63146(11) 0.3089(2) 0.0410(7) Uani 1 1 d . . . H1A H 0.2979 0.6120 0.3785 0.061 Uiso 1 1 calc R . . H1B H 0.3929 0.6454 0.3308 0.061 Uiso 1 1 calc R . . H1C H 0.3326 0.5993 0.2444 0.061 Uiso 1 1 calc R . . C2 C 0.27264(15) 0.68934(11) 0.2670(2) 0.0287(6) Uani 1 1 d . . . C3 C 0.3156(2) 0.7500 0.2724(3) 0.0315(9) Uani 1 2 d S . . H3 H 0.3824 0.7500 0.2808 0.038 Uiso 1 2 calc SR . . C4 C 0.13592(15) 0.61878(11) 0.2449(2) 0.0300(6) Uani 1 1 d . . . C5 C 0.08030(17) 0.60759(13) 0.3468(3) 0.0388(7) Uani 1 1 d . . . C6 C 0.03399(18) 0.54802(13) 0.3550(3) 0.0487(8) Uani 1 1 d . . . H6 H -0.0034 0.5391 0.4236 0.058 Uiso 1 1 calc R . . C7 C 0.04072(19) 0.50215(14) 0.2672(3) 0.0531(8) Uani 1 1 d . . . H7 H 0.0086 0.4619 0.2754 0.064 Uiso 1 1 calc R . . C8 C 0.09377(19) 0.51436(14) 0.1676(3) 0.0491(8) Uani 1 1 d . . . H8 H 0.0977 0.4823 0.1067 0.059 Uiso 1 1 calc R . . C9 C 0.14207(16) 0.57263(12) 0.1535(2) 0.0366(6) Uani 1 1 d . . . C10 C 0.19631(18) 0.58413(13) 0.0380(3) 0.0452(7) Uani 1 1 d . . . H10 H 0.2330 0.6254 0.0468 0.054 Uiso 1 1 calc R . . C11 C 0.2659(2) 0.52958(14) 0.0119(3) 0.0780(11) Uani 1 1 d . . . H11A H 0.3088 0.5243 0.0800 0.117 Uiso 1 1 calc R . . H11B H 0.3026 0.5403 -0.0597 0.117 Uiso 1 1 calc R . . H11C H 0.2311 0.4891 -0.0013 0.117 Uiso 1 1 calc R . . C12 C 0.1271(2) 0.59258(17) -0.0654(3) 0.0719(10) Uani 1 1 d . . . H12A H 0.0897 0.5529 -0.0749 0.108 Uiso 1 1 calc R . . H12B H 0.1624 0.6012 -0.1391 0.108 Uiso 1 1 calc R . . H12C H 0.0849 0.6292 -0.0486 0.108 Uiso 1 1 calc R . . C13 C 0.0703(2) 0.65782(14) 0.4464(3) 0.0563(9) Uani 1 1 d . . . H13 H 0.0880 0.7011 0.4125 0.068 Uiso 1 1 calc R . . C14 C -0.0296(2) 0.6629(2) 0.4923(3) 0.0947(14) Uani 1 1 d . . . H14A H -0.0486 0.6213 0.5277 0.142 Uiso 1 1 calc R . . H14B H -0.0722 0.6735 0.4260 0.142 Uiso 1 1 calc R . . H14C H -0.0331 0.6971 0.5531 0.142 Uiso 1 1 calc R . . C15 C 0.1350(2) 0.6446(2) 0.5496(4) 0.1091(16) Uani 1 1 d . . . H15A H 0.1239 0.6005 0.5794 0.164 Uiso 1 1 calc R . . H15B H 0.1225 0.6760 0.6136 0.164 Uiso 1 1 calc R . . H15C H 0.2008 0.6487 0.5234 0.164 Uiso 1 1 calc R . . C16 C 0.1988(2) 0.7500 0.0084(3) 0.0352(9) Uani 1 2 d S . . C17 C 0.2415(3) 0.7500 -0.0862(4) 0.0439(10) Uani 1 2 d S . . C18 C 0.2980(2) 0.7500 -0.1955(3) 0.0412(10) Uani 1 2 d S . . C19 C 0.32627(19) 0.69219(15) -0.2476(3) 0.0555(8) Uani 1 1 d . . . H19 H 0.3069 0.6521 -0.2137 0.067 Uiso 1 1 calc R . . C20 C 0.3820(2) 0.69241(17) -0.3478(3) 0.0642(9) Uani 1 1 d . . . H20 H 0.4014 0.6525 -0.3826 0.077 Uiso 1 1 calc R . . C21 C 0.4099(3) 0.7500 -0.3981(4) 0.0708(14) Uani 1 2 d S . . H21 H 0.4485 0.7500 -0.4676 0.085 Uiso 1 2 calc SR . . 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 0.0237(2) 0.0367(2) 0.0287(2) 0.000 -0.00143(19) 0.000 N1 0.0199(10) 0.0309(12) 0.0299(12) 0.0018(10) 0.0006(9) -0.0013(8) C1 0.0313(14) 0.0390(16) 0.0526(19) 0.0046(13) -0.0040(13) 0.0063(13) C2 0.0231(13) 0.0371(15) 0.0259(15) 0.0008(12) 0.0037(11) 0.0042(11) C3 0.0166(17) 0.043(2) 0.035(2) 0.000 0.0033(16) 0.000 C4 0.0235(12) 0.0322(14) 0.0342(16) 0.0054(13) -0.0047(11) -0.0007(11) C5 0.0342(14) 0.0384(15) 0.0439(18) 0.0129(15) 0.0022(14) 0.0010(12) C6 0.0397(16) 0.0480(18) 0.059(2) 0.0227(18) 0.0026(16) -0.0043(14) C7 0.0473(18) 0.0425(19) 0.069(2) 0.0137(18) -0.0162(18) -0.0177(15) C8 0.0537(19) 0.0417(17) 0.052(2) -0.0021(15) -0.0113(17) -0.0134(14) C9 0.0295(14) 0.0353(15) 0.0451(18) 0.0005(15) -0.0075(13) -0.0076(11) C10 0.0454(17) 0.0435(17) 0.0466(19) -0.0155(14) 0.0002(15) -0.0134(14) C11 0.073(2) 0.058(2) 0.104(3) -0.037(2) 0.025(2) -0.0113(18) C12 0.074(2) 0.100(3) 0.0411(19) -0.0054(19) -0.0048(18) -0.040(2) C13 0.075(2) 0.0392(17) 0.055(2) 0.0089(16) 0.0377(19) 0.0009(15) C14 0.070(2) 0.151(4) 0.063(3) -0.007(2) 0.008(2) 0.044(2) C15 0.058(2) 0.166(4) 0.103(3) -0.083(3) -0.015(2) 0.013(2) C16 0.038(2) 0.041(2) 0.026(2) 0.000 -0.0047(19) 0.000 C17 0.042(2) 0.049(3) 0.040(3) 0.000 -0.006(2) 0.000 C18 0.030(2) 0.064(3) 0.030(2) 0.000 -0.0009(18) 0.000 C19 0.0491(17) 0.071(2) 0.047(2) -0.0081(17) 0.0095(17) -0.0069(16) C20 0.0593(19) 0.082(2) 0.052(2) -0.0207(19) 0.0134(19) -0.0034(18) C21 0.059(3) 0.110(5) 0.043(3) 0.000 0.018(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 C16 1.976(4) . ? Ge1 N1 1.9846(18) . ? Ge1 N1 1.9847(18) 8_575 ? N1 C2 1.345(3) . ? N1 C4 1.451(3) . ? C1 C2 1.508(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.390(3) . ? C3 C2 1.390(3) 8_575 ? C3 H3 0.9500 . ? C4 C9 1.399(3) . ? C4 C5 1.405(3) . ? C5 C6 1.394(3) . ? C5 C13 1.527(4) . ? C6 C7 1.366(4) . ? C6 H6 0.9500 . ? C7 C8 1.367(4) . ? C7 H7 0.9500 . ? C8 C9 1.390(4) . ? C8 H8 0.9500 . ? C9 C10 1.521(4) . ? C10 C11 1.522(4) . ? C10 C12 1.526(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.497(5) . ? C13 C14 1.508(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.219(5) . ? C17 C18 1.461(5) . ? C18 C19 1.385(3) . ? C18 C19 1.385(3) 8_575 ? C19 C20 1.371(4) . ? C19 H19 0.9500 . ? C20 C21 1.371(4) . ? C20 H20 0.9500 . ? C21 C20 1.371(4) 8_575 ? C21 H21 0.9500 . ? 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 C16 Ge1 N1 93.35(9) . . ? C16 Ge1 N1 93.35(9) . 8_575 ? N1 Ge1 N1 91.30(11) . 8_575 ? C2 N1 C4 120.78(18) . . ? C2 N1 Ge1 122.15(15) . . ? C4 N1 Ge1 116.85(13) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.7(2) . . ? N1 C2 C1 119.5(2) . . ? C3 C2 C1 117.8(2) . . ? C2 C3 C2 127.9(3) . 8_575 ? C2 C3 H3 116.0 . . ? C2 C3 H3 116.0 8_575 . ? C9 C4 C5 121.1(2) . . ? C9 C4 N1 119.8(2) . . ? C5 C4 N1 118.9(2) . . ? C6 C5 C4 117.4(3) . . ? C6 C5 C13 120.3(3) . . ? C4 C5 C13 122.2(2) . . ? C7 C6 C5 121.9(3) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 121.4(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 118.2(2) . . ? C8 C9 C10 118.6(2) . . ? C4 C9 C10 123.1(2) . . ? C9 C10 C11 112.0(2) . . ? C9 C10 C12 109.8(2) . . ? C11 C10 C12 110.7(3) . . ? C9 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? C12 C10 H10 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C14 108.8(3) . . ? C15 C13 C5 112.6(2) . . ? C14 C13 C5 112.5(3) . . ? C15 C13 H13 107.6 . . ? C14 C13 H13 107.6 . . ? C5 C13 H13 107.6 . . ? 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 . . ? 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 . . ? C17 C16 Ge1 171.0(3) . . ? C16 C17 C18 176.6(4) . . ? C19 C18 C19 118.6(4) . 8_575 ? C19 C18 C17 120.70(19) . . ? C19 C18 C17 120.70(19) 8_575 . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.3(3) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C20 119.8(4) 8_575 . ? C20 C21 H21 120.1 8_575 . ? C20 C21 H21 120.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.480 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.049