# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Cameron Jones' _publ_contact_author_address ; Chemistry Department Cardiff University PO Box 912 Park Place Cardiff CF10 3TB UNITED KINGDOM ; _publ_contact_author_email JONESCA6@CARDIFF.AC.UK _publ_section_title ; Synthetic, Structural and Theoretical Studies of Amidinate and Guanidinate Stabilised Germanium(I) Dimers ; loop_ _publ_author_name 'Cameron Jones' 'Shaun P. Green' 'Peter Junk' 'Kai-Alexander Lippert' 'Andreas Stasch' # Attachment 'compound1.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 616057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H43 Cl Ge N2' _chemical_formula_weight 527.69 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' Cl Cl 0.1484 0.1585 '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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.515(4) _cell_length_b 8.3709(17) _cell_length_c 18.448(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2859.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.707 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16795 _diffrn_reflns_av_R_equivalents 0.0845 _diffrn_reflns_av_sigmaI/netI 0.0704 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4919 _reflns_number_gt 4117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Durind the course of refinement the Cl ataom was found to be disordered over two sites. This disorder was successfully modelled. The crystal was found to be a racemic twin and the TWIN and BASF commands of Shelxl were used in the refinement of the structure. ; _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^)+(0.0319P)^2^+4.6974P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.38(2) _refine_ls_number_reflns 4919 _refine_ls_number_parameters 321 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.081 _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 0.46436(2) 0.16800(5) 0.46673(5) 0.03311(19) Uani 1 1 d D . . Cl1 Cl 0.49504(13) 0.2174(3) 0.35519(11) 0.0364(7) Uani 0.796(6) 1 d P A 1 Cl1A Cl 0.4987(5) 0.2256(12) 0.5631(5) 0.047(3) Uani 0.204(6) 1 d PD A 2 N1 N 0.45134(17) -0.0690(4) 0.4579(3) 0.0187(9) Uani 1 1 d . A . N2 N 0.36176(19) 0.0964(4) 0.4553(3) 0.0249(10) Uani 1 1 d . A . C1 C 0.3794(2) -0.0607(5) 0.4582(4) 0.0198(10) Uani 1 1 d . . . C2 C 0.3250(2) -0.1993(5) 0.4616(5) 0.0284(10) Uani 1 1 d . A . C3 C 0.2756(4) -0.1904(10) 0.3943(4) 0.042(2) Uani 1 1 d . . . H3A H 0.2436 -0.0976 0.3985 0.062 Uiso 1 1 calc R A . H3B H 0.2465 -0.2880 0.3911 0.062 Uiso 1 1 calc R . . H3C H 0.3053 -0.1799 0.3506 0.062 Uiso 1 1 calc R . . C4 C 0.2796(4) -0.1840(9) 0.5302(4) 0.0397(19) Uani 1 1 d . . . H4A H 0.3109 -0.1939 0.5728 0.059 Uiso 1 1 calc R A . H4B H 0.2431 -0.2687 0.5310 0.059 Uiso 1 1 calc R . . H4C H 0.2557 -0.0796 0.5308 0.059 Uiso 1 1 calc R . . C5 C 0.3609(2) -0.3654(5) 0.4596(5) 0.0326(12) Uani 1 1 d . . . H5A H 0.3954 -0.3697 0.4194 0.049 Uiso 1 1 calc R A . H5B H 0.3238 -0.4475 0.4527 0.049 Uiso 1 1 calc R . . H5C H 0.3863 -0.3845 0.5054 0.049 Uiso 1 1 calc R . . C6 C 0.4993(2) -0.2018(5) 0.4676(4) 0.0262(10) Uani 1 1 d . . . C7 C 0.5188(4) -0.2472(9) 0.5373(4) 0.0394(19) Uani 1 1 d . A . C8 C 0.5652(4) -0.3784(9) 0.5464(5) 0.0478(19) Uani 1 1 d . . . H8 H 0.5774 -0.4155 0.5935 0.057 Uiso 1 1 calc R A . C9 C 0.5919(4) -0.4505(9) 0.4870(4) 0.048(2) Uani 1 1 d . A . H9 H 0.6242 -0.5373 0.4940 0.058 Uiso 1 1 calc R . . C10 C 0.5761(4) -0.4086(10) 0.4177(5) 0.049(2) Uani 1 1 d . . . H10 H 0.5964 -0.4658 0.3782 0.058 Uiso 1 1 calc R A . C11 C 0.5274(4) -0.2741(10) 0.4047(4) 0.0350(18) Uani 1 1 d . A . C12 C 0.4918(4) -0.1616(8) 0.6064(3) 0.0419(19) Uani 1 1 d . . . H12 H 0.4517 -0.0885 0.5917 0.050 Uiso 1 1 calc R A . C13 C 0.4615(4) -0.2766(10) 0.6631(4) 0.057(2) Uani 1 1 d . A . H13A H 0.4247 -0.3448 0.6406 0.085 Uiso 1 1 calc R . . H13B H 0.4396 -0.2155 0.7028 0.085 Uiso 1 1 calc R . . H13C H 0.5006 -0.3433 0.6822 0.085 Uiso 1 1 calc R . . C14 C 0.5512(4) -0.0590(9) 0.6388(4) 0.058(2) Uani 1 1 d . A . H14A H 0.5377 -0.0277 0.6882 0.087 Uiso 1 1 calc R . . H14B H 0.5577 0.0370 0.6091 0.087 Uiso 1 1 calc R . . H14C H 0.5964 -0.1198 0.6400 0.087 Uiso 1 1 calc R . . C15 C 0.5129(4) -0.2145(9) 0.3307(4) 0.0426(18) Uani 1 1 d . . . H15 H 0.4760 -0.1275 0.3335 0.051 Uiso 1 1 calc R A . C16 C 0.4848(5) -0.3456(9) 0.2799(5) 0.062(2) Uani 1 1 d . A . H16A H 0.5223 -0.4271 0.2734 0.093 Uiso 1 1 calc R . . H16B H 0.4726 -0.2987 0.2328 0.093 Uiso 1 1 calc R . . H16C H 0.4417 -0.3948 0.3011 0.093 Uiso 1 1 calc R . . C17 C 0.5834(4) -0.1447(10) 0.2984(4) 0.056(2) Uani 1 1 d . A . H17A H 0.6042 -0.0677 0.3325 0.084 Uiso 1 1 calc R . . H17B H 0.5726 -0.0910 0.2525 0.084 Uiso 1 1 calc R . . H17C H 0.6179 -0.2314 0.2898 0.084 Uiso 1 1 calc R . . C18 C 0.2948(2) 0.1801(5) 0.4584(5) 0.0248(12) Uani 1 1 d . . . C19 C 0.2624(3) 0.2261(8) 0.3911(3) 0.0247(14) Uani 1 1 d . A . C20 C 0.1991(4) 0.3200(8) 0.3963(4) 0.0309(17) Uani 1 1 d . . . H20 H 0.1741 0.3475 0.3530 0.037 Uiso 1 1 calc R A . C21 C 0.1726(2) 0.3722(6) 0.4605(5) 0.0365(13) Uani 1 1 d . A . H21 H 0.1305 0.4369 0.4616 0.044 Uiso 1 1 calc R . . C22 C 0.2069(4) 0.3315(8) 0.5246(4) 0.0343(18) Uani 1 1 d . . . H22 H 0.1889 0.3708 0.5694 0.041 Uiso 1 1 calc R A . C23 C 0.2683(3) 0.2321(8) 0.5237(3) 0.0247(14) Uani 1 1 d . A . C24 C 0.2938(4) 0.1910(9) 0.3180(3) 0.0336(17) Uani 1 1 d . . . H24 H 0.3329 0.1099 0.3249 0.040 Uiso 1 1 calc R A . C25 C 0.3297(5) 0.3456(10) 0.2883(4) 0.055(2) Uani 1 1 d . A . H25A H 0.3556 0.3210 0.2433 0.082 Uiso 1 1 calc R . . H25B H 0.3637 0.3875 0.3243 0.082 Uiso 1 1 calc R . . H25C H 0.2924 0.4257 0.2785 0.082 Uiso 1 1 calc R . . C26 C 0.2394(5) 0.1214(12) 0.2641(5) 0.061(2) Uani 1 1 d . A . H26A H 0.2008 0.1993 0.2553 0.091 Uiso 1 1 calc R . . H26B H 0.2185 0.0232 0.2841 0.091 Uiso 1 1 calc R . . H26C H 0.2639 0.0971 0.2183 0.091 Uiso 1 1 calc R . . C27 C 0.3066(4) 0.1972(9) 0.5961(3) 0.0314(15) Uani 1 1 d . . . H27 H 0.3417 0.1081 0.5881 0.038 Uiso 1 1 calc R A . C28 C 0.2541(5) 0.1472(10) 0.6570(4) 0.0440(19) Uani 1 1 d . A . H28A H 0.2222 0.2369 0.6688 0.066 Uiso 1 1 calc R . . H28B H 0.2818 0.1169 0.7002 0.066 Uiso 1 1 calc R . . H28C H 0.2251 0.0560 0.6408 0.066 Uiso 1 1 calc R . . C29 C 0.3488(4) 0.3447(9) 0.6198(4) 0.0423(18) Uani 1 1 d . A . H29A H 0.3843 0.3725 0.5824 0.063 Uiso 1 1 calc R . . H29B H 0.3739 0.3221 0.6654 0.063 Uiso 1 1 calc R . . H29C H 0.3154 0.4342 0.6268 0.063 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 0.0221(2) 0.0167(2) 0.0605(4) -0.0013(4) -0.0015(4) -0.00220(19) Cl1 0.0429(13) 0.0303(11) 0.0359(11) 0.0086(9) 0.0084(9) -0.0026(10) Cl1A 0.035(5) 0.041(6) 0.066(6) -0.011(5) -0.012(4) -0.008(4) N1 0.0224(18) 0.0116(16) 0.022(2) 0.001(2) 0.001(2) 0.0006(12) N2 0.0206(18) 0.0135(17) 0.041(3) 0.001(2) -0.002(2) -0.0013(14) C1 0.020(2) 0.017(2) 0.022(3) 0.002(3) -0.003(2) 0.0017(15) C2 0.023(2) 0.017(2) 0.045(3) -0.001(4) 0.003(3) -0.0034(16) C3 0.036(4) 0.028(5) 0.060(6) -0.003(4) -0.017(4) -0.001(3) C4 0.035(4) 0.018(4) 0.067(5) 0.002(4) 0.010(3) -0.013(3) C5 0.029(2) 0.015(2) 0.054(4) 0.000(4) -0.009(4) -0.0052(17) C6 0.018(2) 0.020(2) 0.041(3) 0.000(4) 0.002(4) -0.0027(15) C7 0.028(4) 0.025(4) 0.066(5) 0.014(3) -0.012(3) -0.010(3) C8 0.039(4) 0.026(4) 0.079(5) 0.008(4) -0.011(4) 0.002(3) C9 0.034(3) 0.038(4) 0.073(6) 0.013(4) -0.010(3) 0.003(3) C10 0.034(4) 0.040(5) 0.072(6) -0.022(4) 0.007(4) -0.007(3) C11 0.016(3) 0.026(4) 0.063(4) -0.016(3) 0.007(2) -0.003(3) C12 0.057(5) 0.044(4) 0.024(3) 0.015(3) -0.011(3) -0.022(3) C13 0.080(6) 0.048(5) 0.042(4) 0.010(4) -0.001(4) -0.022(4) C14 0.058(5) 0.052(5) 0.064(5) -0.002(4) -0.011(4) -0.021(4) C15 0.043(4) 0.042(4) 0.044(4) -0.016(3) 0.016(3) -0.017(3) C16 0.080(6) 0.048(5) 0.057(5) -0.012(4) 0.012(4) -0.027(4) C17 0.054(5) 0.051(5) 0.062(5) -0.015(4) 0.020(4) -0.023(4) C18 0.021(2) 0.013(2) 0.040(3) -0.005(3) 0.003(3) -0.0017(16) C19 0.027(3) 0.013(3) 0.034(4) 0.005(3) -0.014(3) -0.004(2) C20 0.027(4) 0.023(4) 0.042(4) -0.005(3) -0.007(3) 0.002(3) C21 0.015(2) 0.029(3) 0.065(4) 0.014(4) -0.006(4) 0.0025(18) C22 0.029(4) 0.028(4) 0.046(4) -0.008(3) 0.015(3) -0.005(3) C23 0.026(3) 0.018(3) 0.029(3) 0.008(3) -0.003(2) -0.006(3) C24 0.044(4) 0.028(4) 0.028(4) 0.004(3) -0.004(3) 0.005(3) C25 0.082(6) 0.047(5) 0.035(4) 0.010(4) 0.005(4) 0.005(4) C26 0.071(6) 0.063(6) 0.048(5) -0.010(4) -0.028(4) 0.004(4) C27 0.040(3) 0.026(4) 0.029(3) 0.002(3) 0.000(3) -0.009(3) C28 0.055(5) 0.041(4) 0.035(4) 0.006(3) 0.003(3) -0.012(3) C29 0.054(4) 0.037(4) 0.036(4) -0.005(3) -0.006(3) -0.011(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 Cl1A 1.948(8) . ? Ge1 N2 2.003(4) . ? Ge1 N1 2.005(3) . ? Ge1 Cl1 2.174(2) . ? N1 C1 1.334(5) . ? N1 C6 1.434(5) . ? N2 C1 1.356(5) . ? N2 C18 1.426(5) . ? C1 C2 1.538(6) . ? C2 C4 1.523(11) . ? C2 C5 1.542(6) . ? C2 C3 1.544(10) . ? C6 C7 1.389(11) . ? C6 C11 1.409(10) . ? C7 C8 1.404(11) . ? C7 C12 1.546(11) . ? C8 C9 1.346(11) . ? C9 C10 1.357(11) . ? C10 C11 1.462(11) . ? C11 C15 1.478(11) . ? C12 C14 1.517(9) . ? C12 C13 1.528(9) . ? C15 C16 1.534(10) . ? C15 C17 1.548(9) . ? C18 C23 1.372(10) . ? C18 C19 1.431(10) . ? C19 C20 1.414(10) . ? C19 C24 1.497(9) . ? C20 C21 1.355(12) . ? C21 C22 1.384(11) . ? C22 C23 1.409(10) . ? C23 C27 1.539(9) . ? C24 C26 1.532(10) . ? C24 C25 1.555(11) . ? C27 C29 1.526(9) . ? C27 C28 1.544(9) . ? 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 Cl1A Ge1 N2 118.7(3) . . ? Cl1A Ge1 N1 111.0(4) . . ? N2 Ge1 N1 65.25(14) . . ? Cl1A Ge1 Cl1 137.0(3) . . ? N2 Ge1 Cl1 101.83(18) . . ? N1 Ge1 Cl1 98.21(18) . . ? C1 N1 C6 131.2(3) . . ? C1 N1 Ge1 93.9(2) . . ? C6 N1 Ge1 133.0(3) . . ? C1 N2 C18 133.2(4) . . ? C1 N2 Ge1 93.3(3) . . ? C18 N2 Ge1 132.4(3) . . ? N1 C1 N2 106.9(3) . . ? N1 C1 C2 128.0(3) . . ? N2 C1 C2 125.1(4) . . ? C4 C2 C1 109.4(5) . . ? C4 C2 C5 109.5(6) . . ? C1 C2 C5 113.4(3) . . ? C4 C2 C3 109.7(4) . . ? C1 C2 C3 108.6(6) . . ? C5 C2 C3 106.2(6) . . ? C7 C6 C11 123.3(5) . . ? C7 C6 N1 119.3(6) . . ? C11 C6 N1 117.3(7) . . ? C6 C7 C8 118.9(7) . . ? C6 C7 C12 123.6(6) . . ? C8 C7 C12 117.5(7) . . ? C9 C8 C7 118.6(8) . . ? C8 C9 C10 124.9(7) . . ? C9 C10 C11 119.1(7) . . ? C6 C11 C10 115.0(7) . . ? C6 C11 C15 123.3(7) . . ? C10 C11 C15 121.6(7) . . ? C14 C12 C13 110.7(6) . . ? C14 C12 C7 110.7(6) . . ? C13 C12 C7 113.0(6) . . ? C11 C15 C16 112.6(6) . . ? C11 C15 C17 109.3(7) . . ? C16 C15 C17 108.7(6) . . ? C23 C18 N2 120.1(6) . . ? C23 C18 C19 121.8(4) . . ? N2 C18 C19 117.5(6) . . ? C20 C19 C18 116.0(6) . . ? C20 C19 C24 119.5(6) . . ? C18 C19 C24 124.4(6) . . ? C21 C20 C19 122.5(6) . . ? C20 C21 C22 120.1(4) . . ? C21 C22 C23 120.4(6) . . ? C18 C23 C22 119.1(6) . . ? C18 C23 C27 122.5(5) . . ? C22 C23 C27 118.3(6) . . ? C19 C24 C26 113.8(7) . . ? C19 C24 C25 108.7(6) . . ? C26 C24 C25 111.6(6) . . ? C29 C27 C23 109.3(6) . . ? C29 C27 C28 109.4(6) . . ? C23 C27 C28 113.2(6) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.914 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.073 # Attachment 'compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 616058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H48 Cl Ge N3' _chemical_formula_weight 570.76 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' Cl Cl 0.1484 0.1585 '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.620(4) _cell_length_b 12.441(3) _cell_length_c 14.419(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.69(3) _cell_angle_gamma 90.00 _cell_volume 3106.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.853 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11700 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6076 _reflns_number_gt 5714 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. During the course of refimement the Ge and Cl atoms of the molecule were found to be disordered over two sites this disorder was successfully modelled. The crystal was found to be a racemic twin. As a result, the TWIN and BASF commands of Shelxl were used in the refinemnet of the structure. ; _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^)+(0.0124P)^2^+12.6456P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.20(2) _refine_ls_number_reflns 6076 _refine_ls_number_parameters 357 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.49042(6) 0.07377(10) 0.06537(6) 0.0308(5) Uani 0.627(6) 1 d P A 1 Cl1 Cl 0.6102(2) 0.0028(2) 0.09760(19) 0.0451(8) Uani 0.627(6) 1 d P A 1 N1 N 0.5148(3) 0.2013(3) 0.0000(3) 0.0222(9) Uani 1 1 d . . . C1 C 0.5153(4) 0.2657(3) 0.0768(5) 0.0249(7) Uani 1 1 d . A . N2 N 0.5089(3) 0.2006(4) 0.1486(3) 0.0247(9) Uani 1 1 d . . . C2 C 0.5419(3) 0.2188(4) -0.0871(4) 0.0225(10) Uani 1 1 d . A . N3 N 0.5184(4) 0.3757(2) 0.0781(5) 0.0361(9) Uani 1 1 d . . . C3 C 0.4894(3) 0.2008(4) -0.1704(4) 0.0284(12) Uani 1 1 d . . . C4 C 0.5171(4) 0.2043(5) -0.2574(4) 0.0316(12) Uani 1 1 d . A . H4 H 0.4828 0.1906 -0.3153 0.038 Uiso 1 1 calc R . . C5 C 0.5933(4) 0.2274(5) -0.2573(5) 0.0338(13) Uani 1 1 d . . . H5 H 0.6112 0.2304 -0.3156 0.041 Uiso 1 1 calc R A . C6 C 0.6430(3) 0.2457(5) -0.1766(4) 0.0312(13) Uani 1 1 d . A . H6 H 0.6950 0.2628 -0.1801 0.037 Uiso 1 1 calc R . . C7 C 0.6225(4) 0.2408(4) -0.0860(4) 0.0338(13) Uani 1 1 d . . . C8 C 0.4042(3) 0.1790(4) -0.1732(5) 0.0330(13) Uani 1 1 d . A . H8 H 0.3934 0.1938 -0.1087 0.040 Uiso 1 1 calc R . . C9 C 0.3551(4) 0.2553(7) -0.2408(5) 0.0537(19) Uani 1 1 d . . . H9A H 0.3723 0.3293 -0.2260 0.080 Uiso 1 1 calc R A . H9B H 0.3009 0.2481 -0.2346 0.080 Uiso 1 1 calc R . . H9C H 0.3604 0.2381 -0.3056 0.080 Uiso 1 1 calc R . . C10 C 0.3885(4) 0.0574(5) -0.1939(6) 0.053(2) Uani 1 1 d . . . H10A H 0.3778 0.0455 -0.2622 0.080 Uiso 1 1 calc R A . H10B H 0.3440 0.0346 -0.1670 0.080 Uiso 1 1 calc R . . H10C H 0.4341 0.0156 -0.1653 0.080 Uiso 1 1 calc R . . C11 C 0.6840(3) 0.2527(5) 0.0022(5) 0.0322(13) Uani 1 1 d . A . H11 H 0.6581 0.2546 0.0582 0.039 Uiso 1 1 calc R . . C12 C 0.7384(4) 0.1573(6) 0.0120(5) 0.054(2) Uani 1 1 d . . . H12A H 0.7083 0.0906 0.0076 0.081 Uiso 1 1 calc R A . H12B H 0.7733 0.1605 0.0734 0.081 Uiso 1 1 calc R . . H12C H 0.7686 0.1592 -0.0385 0.081 Uiso 1 1 calc R . . C13 C 0.7309(4) 0.3559(6) 0.0012(6) 0.0496(17) Uani 1 1 d . . . H13A H 0.7686 0.3616 0.0602 0.074 Uiso 1 1 calc R A . H13B H 0.6962 0.4180 -0.0050 0.074 Uiso 1 1 calc R . . H13C H 0.7581 0.3542 -0.0523 0.074 Uiso 1 1 calc R . . C14 C 0.4818(3) 0.2170(4) 0.2343(4) 0.0257(11) Uani 1 1 d . A . C15 C 0.4051(3) 0.2399(5) 0.2360(4) 0.0261(12) Uani 1 1 d . . . C16 C 0.3787(4) 0.2453(6) 0.3205(5) 0.0456(16) Uani 1 1 d . A . H16 H 0.3264 0.2627 0.3216 0.055 Uiso 1 1 calc R . . C17 C 0.4322(4) 0.2241(6) 0.4063(5) 0.0439(16) Uani 1 1 d . . . H17 H 0.4157 0.2274 0.4654 0.053 Uiso 1 1 calc R A . C18 C 0.5073(4) 0.1991(5) 0.4024(5) 0.0361(13) Uani 1 1 d . A . H18 H 0.5419 0.1821 0.4593 0.043 Uiso 1 1 calc R . . C19 C 0.5338(3) 0.1980(4) 0.3200(4) 0.0273(11) Uani 1 1 d . . . C20 C 0.3442(4) 0.2531(5) 0.1465(5) 0.0419(15) Uani 1 1 d . A . H20 H 0.3713 0.2572 0.0915 0.050 Uiso 1 1 calc R . . C21 C 0.2946(4) 0.3541(6) 0.1464(6) 0.0511(18) Uani 1 1 d . . . H21A H 0.2631 0.3642 0.0835 0.077 Uiso 1 1 calc R A . H21B H 0.3281 0.4167 0.1627 0.077 Uiso 1 1 calc R . . H21C H 0.2608 0.3459 0.1928 0.077 Uiso 1 1 calc R . . C22 C 0.2902(5) 0.1554(6) 0.1327(6) 0.063(2) Uani 1 1 d . . . H22A H 0.2664 0.1464 0.1885 0.094 Uiso 1 1 calc R A . H22B H 0.3199 0.0908 0.1239 0.094 Uiso 1 1 calc R . . H22C H 0.2498 0.1665 0.0769 0.094 Uiso 1 1 calc R . . C23 C 0.6179(4) 0.1731(6) 0.3197(4) 0.0378(14) Uani 1 1 d . A . H23 H 0.6276 0.1856 0.2544 0.045 Uiso 1 1 calc R . . C24 C 0.6728(5) 0.2480(8) 0.3881(7) 0.065(2) Uani 1 1 d . . . H24A H 0.6581 0.2471 0.4504 0.098 Uiso 1 1 calc R A . H24B H 0.6688 0.3215 0.3632 0.098 Uiso 1 1 calc R . . H24C H 0.7261 0.2227 0.3937 0.098 Uiso 1 1 calc R . . C25 C 0.6416(5) 0.0586(7) 0.3475(6) 0.076(3) Uani 1 1 d . . . H25A H 0.6243 0.0402 0.4064 0.113 Uiso 1 1 calc R A . H25B H 0.6979 0.0522 0.3567 0.113 Uiso 1 1 calc R . . H25C H 0.6177 0.0093 0.2974 0.113 Uiso 1 1 calc R . . C26 C 0.4905(4) 0.4360(5) -0.0121(6) 0.0477(19) Uani 1 1 d . A . H26 H 0.4960 0.3858 -0.0645 0.057 Uiso 1 1 calc R . . C27 C 0.4033(5) 0.4659(6) -0.0265(6) 0.0564(19) Uani 1 1 d . . . H27A H 0.3728 0.4009 -0.0221 0.085 Uiso 1 1 calc R A . H27B H 0.3872 0.4986 -0.0889 0.085 Uiso 1 1 calc R . . H27C H 0.3951 0.5171 0.0224 0.085 Uiso 1 1 calc R . . C28 C 0.5386(5) 0.5329(8) -0.0239(8) 0.082(3) Uani 1 1 d . . . H28A H 0.5331 0.5864 0.0242 0.122 Uiso 1 1 calc R A . H28B H 0.5212 0.5638 -0.0868 0.122 Uiso 1 1 calc R . . H28C H 0.5929 0.5116 -0.0170 0.122 Uiso 1 1 calc R . . C29 C 0.5462(5) 0.4286(6) 0.1703(6) 0.0519(18) Uani 1 1 d . A . H29 H 0.5462 0.3710 0.2187 0.062 Uiso 1 1 calc R . . C30 C 0.4915(4) 0.5158(7) 0.1946(7) 0.071(3) Uani 1 1 d . . . H30A H 0.5126 0.5461 0.2568 0.107 Uiso 1 1 calc R A . H30B H 0.4407 0.4842 0.1957 0.107 Uiso 1 1 calc R . . H30C H 0.4862 0.5729 0.1470 0.107 Uiso 1 1 calc R . . C31 C 0.6285(4) 0.4677(7) 0.1836(6) 0.059(2) Uani 1 1 d . . . H31A H 0.6307 0.5334 0.1466 0.089 Uiso 1 1 calc R A . H31B H 0.6609 0.4122 0.1623 0.089 Uiso 1 1 calc R . . H31C H 0.6476 0.4831 0.2505 0.089 Uiso 1 1 calc R . . Ge1A Ge 0.53315(16) 0.06445(12) 0.08080(11) 0.0255(7) Uani 0.373(6) 1 d P A 2 Cl1A Cl 0.4130(3) -0.0069(3) 0.0488(3) 0.0400(13) Uani 0.373(6) 1 d P 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 0.0428(13) 0.0217(5) 0.0294(5) 0.0023(4) 0.0106(5) -0.0032(6) Cl1 0.0465(15) 0.0460(15) 0.0462(15) 0.0124(11) 0.0174(11) 0.0206(10) N1 0.026(2) 0.023(2) 0.017(2) 0.0029(17) 0.0028(17) 0.0026(15) C1 0.0235(18) 0.0244(17) 0.0272(18) 0.001(3) 0.0060(15) 0.003(2) N2 0.024(2) 0.022(2) 0.030(3) -0.0006(19) 0.0128(18) 0.0036(16) C2 0.027(3) 0.020(2) 0.025(3) 0.000(2) 0.016(2) -0.0045(18) N3 0.057(3) 0.0187(14) 0.039(2) 0.003(2) 0.025(2) 0.004(2) C3 0.025(3) 0.026(3) 0.032(3) 0.007(2) 0.000(2) 0.001(2) C4 0.038(3) 0.036(3) 0.023(3) 0.010(2) 0.011(2) 0.005(2) C5 0.039(3) 0.031(3) 0.035(4) 0.011(3) 0.016(3) 0.012(2) C6 0.027(3) 0.038(3) 0.031(3) 0.008(2) 0.011(2) 0.016(2) C7 0.051(4) 0.017(2) 0.032(3) -0.001(2) 0.004(3) 0.001(2) C8 0.024(3) 0.023(3) 0.049(4) 0.006(2) 0.000(2) -0.007(2) C9 0.027(3) 0.088(6) 0.039(4) 0.009(4) -0.011(3) 0.006(3) C10 0.037(3) 0.037(4) 0.090(6) -0.013(3) 0.024(3) -0.029(3) C11 0.016(2) 0.037(3) 0.043(4) -0.009(3) 0.005(2) 0.002(2) C12 0.039(4) 0.058(4) 0.053(4) -0.014(3) -0.021(3) 0.018(3) C13 0.036(3) 0.050(4) 0.068(5) -0.012(4) 0.025(3) -0.011(3) C14 0.023(3) 0.022(3) 0.031(3) 0.001(2) 0.005(2) -0.0063(18) C15 0.003(2) 0.043(3) 0.034(3) -0.002(2) 0.0082(18) -0.0012(18) C16 0.036(4) 0.057(4) 0.048(4) 0.002(3) 0.022(3) 0.014(3) C17 0.050(4) 0.056(4) 0.029(4) -0.003(3) 0.016(3) -0.009(3) C18 0.037(3) 0.034(3) 0.037(4) 0.002(3) 0.006(2) -0.006(2) C19 0.035(3) 0.024(3) 0.024(3) -0.001(2) 0.010(2) -0.005(2) C20 0.037(4) 0.047(4) 0.040(4) 0.000(3) 0.002(3) 0.011(3) C21 0.042(4) 0.046(4) 0.063(5) 0.014(4) 0.002(3) 0.005(3) C22 0.060(5) 0.040(4) 0.075(6) -0.002(4) -0.021(4) 0.007(3) C23 0.028(3) 0.070(4) 0.015(3) 0.000(3) 0.004(2) -0.003(3) C24 0.048(4) 0.080(6) 0.073(6) -0.030(5) 0.024(4) -0.012(4) C25 0.085(6) 0.077(6) 0.052(5) 0.014(4) -0.022(4) 0.007(4) C26 0.068(4) 0.027(3) 0.059(4) 0.014(3) 0.040(3) 0.031(3) C27 0.066(5) 0.036(4) 0.069(5) 0.009(4) 0.016(4) 0.006(3) C28 0.067(5) 0.069(5) 0.120(7) 0.065(5) 0.049(5) 0.020(4) C29 0.086(5) 0.030(4) 0.046(4) -0.014(3) 0.029(4) -0.005(3) C30 0.055(4) 0.069(5) 0.105(6) -0.051(5) 0.052(4) -0.020(4) C31 0.053(4) 0.064(5) 0.071(5) -0.003(4) 0.036(4) 0.012(3) Ge1A 0.0370(19) 0.0113(7) 0.0298(9) 0.0031(6) 0.0102(9) 0.0103(8) Cl1A 0.062(3) 0.0170(17) 0.046(2) -0.0045(15) 0.0221(19) -0.0116(14) _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 1.934(4) . ? Ge1 N2 1.973(5) . ? Ge1 Cl1 2.255(4) . ? N1 C1 1.365(8) . ? N1 C2 1.441(7) . ? N1 Ge1A 2.055(5) . ? C1 N2 1.336(8) . ? C1 N3 1.369(4) . ? N2 C14 1.420(8) . ? N2 Ge1A 2.041(5) . ? C2 C3 1.392(8) . ? C2 C7 1.444(8) . ? N3 C29 1.482(9) . ? N3 C26 1.503(9) . ? C3 C4 1.428(8) . ? C3 C8 1.519(8) . ? C4 C5 1.374(9) . ? C5 C6 1.341(9) . ? C6 C7 1.419(9) . ? C7 C11 1.517(8) . ? C8 C9 1.512(9) . ? C8 C10 1.556(8) . ? C11 C12 1.516(8) . ? C11 C13 1.528(9) . ? C14 C15 1.386(7) . ? C14 C19 1.415(8) . ? C15 C16 1.384(9) . ? C15 C20 1.526(8) . ? C16 C17 1.434(10) . ? C17 C18 1.371(10) . ? C18 C19 1.354(9) . ? C19 C23 1.515(8) . ? C20 C21 1.530(9) . ? C20 C22 1.534(10) . ? C23 C25 1.518(11) . ? C23 C24 1.557(9) . ? C26 C28 1.501(11) . ? C26 C27 1.557(9) . ? C29 C31 1.509(11) . ? C29 C30 1.536(10) . ? Ge1A Cl1A 2.263(6) . ? 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 67.27(12) . . ? N1 Ge1 Cl1 97.92(17) . . ? N2 Ge1 Cl1 98.33(18) . . ? C1 N1 C2 131.7(4) . . ? C1 N1 Ge1 93.2(3) . . ? C2 N1 Ge1 133.5(3) . . ? C1 N1 Ge1A 92.9(3) . . ? C2 N1 Ge1A 125.2(3) . . ? Ge1 N1 Ge1A 21.50(7) . . ? N2 C1 N1 106.5(3) . . ? N2 C1 N3 127.1(6) . . ? N1 C1 N3 126.3(6) . . ? C1 N2 C14 132.7(5) . . ? C1 N2 Ge1 92.4(3) . . ? C14 N2 Ge1 126.9(3) . . ? C1 N2 Ge1A 94.4(3) . . ? C14 N2 Ge1A 132.1(4) . . ? Ge1 N2 Ge1A 21.55(7) . . ? C3 C2 N1 116.9(4) . . ? C3 C2 C7 122.4(5) . . ? N1 C2 C7 120.3(5) . . ? C1 N3 C29 117.5(6) . . ? C1 N3 C26 118.8(6) . . ? C29 N3 C26 123.7(4) . . ? C2 C3 C4 118.2(5) . . ? C2 C3 C8 123.2(6) . . ? C4 C3 C8 118.6(5) . . ? C5 C4 C3 119.9(5) . . ? C6 C5 C4 121.1(6) . . ? C5 C6 C7 123.7(6) . . ? C6 C7 C2 114.6(5) . . ? C6 C7 C11 120.2(6) . . ? C2 C7 C11 125.1(5) . . ? C9 C8 C3 110.4(5) . . ? C9 C8 C10 115.3(6) . . ? C3 C8 C10 108.5(5) . . ? C12 C11 C7 110.0(5) . . ? C12 C11 C13 109.0(5) . . ? C7 C11 C13 112.2(6) . . ? C15 C14 C19 119.6(5) . . ? C15 C14 N2 122.1(5) . . ? C19 C14 N2 117.9(5) . . ? C16 C15 C14 120.9(5) . . ? C16 C15 C20 116.2(5) . . ? C14 C15 C20 122.8(5) . . ? C15 C16 C17 118.5(6) . . ? C18 C17 C16 119.4(6) . . ? C19 C18 C17 122.0(6) . . ? C18 C19 C14 119.5(5) . . ? C18 C19 C23 120.0(5) . . ? C14 C19 C23 120.4(5) . . ? C15 C20 C21 113.7(6) . . ? C15 C20 C22 110.2(5) . . ? C21 C20 C22 108.0(6) . . ? C19 C23 C25 114.4(6) . . ? C19 C23 C24 111.7(6) . . ? C25 C23 C24 106.7(6) . . ? C28 C26 N3 113.5(7) . . ? C28 C26 C27 110.9(6) . . ? N3 C26 C27 113.0(6) . . ? N3 C29 C31 114.1(6) . . ? N3 C29 C30 113.7(7) . . ? C31 C29 C30 111.8(6) . . ? N2 Ge1A N1 63.81(12) . . ? N2 Ge1A Cl1A 98.8(2) . . ? N1 Ge1A Cl1A 99.6(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.658 _refine_diff_density_min -0.733 _refine_diff_density_rms 0.072 # Attachment 'compound3.cif' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 616059' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C62 H94 Ge2 N4 O' _chemical_formula_weight 1056.59 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.051(4) _cell_length_b 16.770(3) _cell_length_c 19.911(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.77(3) _cell_angle_gamma 90.00 _cell_volume 6329(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green-red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2264 _exptl_absorpt_coefficient_mu 0.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13324 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.06 _reflns_number_total 6871 _reflns_number_gt 4935 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. During the course of refinement a half disordered molecule of THF of crystallisation was located in the asymmetric unit. The disorder of the molecule was successfully modelled. H atoms were not placed in calculated positions but their contributions to the empirical formula and F(000) were taken into account in the final refinement. ; _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^)+(0.0545P)^2^+2.5289P] 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 6871 _refine_ls_number_parameters 321 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.041 _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 0.932636(15) 0.740678(15) 0.260131(13) 0.02448(12) Uani 1 1 d . . . O1 O 1.0064(4) 0.7595(4) 0.6721(3) 0.0838(18) Uiso 0.50 1 d P . . N1 N 0.94272(11) 0.80707(12) 0.34593(10) 0.0239(5) Uani 1 1 d . . . N2 N 0.94172(11) 0.67889(12) 0.34935(10) 0.0234(5) Uani 1 1 d . . . C1 C 0.94163(13) 0.74451(14) 0.38763(12) 0.0213(5) Uani 1 1 d . . . C2 C 0.94841(15) 0.74696(14) 0.46534(13) 0.0279(6) Uani 1 1 d . . . C3 C 0.9313(2) 0.82752(18) 0.49518(15) 0.0482(9) Uani 1 1 d . . . H3A H 0.8818 0.8410 0.4815 0.072 Uiso 1 1 calc R . . H3B H 0.9619 0.8685 0.4786 0.072 Uiso 1 1 calc R . . H3C H 0.9391 0.8249 0.5445 0.072 Uiso 1 1 calc R . . C4 C 1.0266(2) 0.7298(3) 0.48794(18) 0.0730(13) Uani 1 1 d . . . H4A H 1.0358 0.7388 0.5367 0.109 Uiso 1 1 calc R . . H4B H 1.0563 0.7655 0.4640 0.109 Uiso 1 1 calc R . . H4C H 1.0374 0.6743 0.4776 0.109 Uiso 1 1 calc R . . C5 C 0.9042(3) 0.6846(2) 0.49666(16) 0.0755(15) Uani 1 1 d . . . H5A H 0.8542 0.6933 0.4815 0.113 Uiso 1 1 calc R . . H5B H 0.9115 0.6888 0.5460 0.113 Uiso 1 1 calc R . . H5C H 0.9183 0.6314 0.4827 0.113 Uiso 1 1 calc R . . C6 C 0.92437(15) 0.88928(15) 0.35661(12) 0.0275(6) Uani 1 1 d . . . C7 C 0.97803(16) 0.94642(16) 0.36799(13) 0.0319(7) Uani 1 1 d . . . C8 C 0.9581(2) 1.02637(17) 0.37413(15) 0.0443(8) Uani 1 1 d . . . H8 H 0.9934 1.0662 0.3819 0.053 Uiso 1 1 calc R . . C9 C 0.8878(2) 1.04809(19) 0.36913(17) 0.0522(9) Uani 1 1 d . . . H9 H 0.8752 1.1025 0.3740 0.063 Uiso 1 1 calc R . . C10 C 0.8358(2) 0.99124(19) 0.35716(16) 0.0473(9) Uani 1 1 d . . . H10 H 0.7877 1.0070 0.3537 0.057 Uiso 1 1 calc R . . C11 C 0.85259(16) 0.91108(17) 0.35011(14) 0.0339(7) Uani 1 1 d . . . C12 C 1.05573(17) 0.92552(18) 0.37451(15) 0.0398(8) Uani 1 1 d . . . H12 H 1.0601 0.8662 0.3723 0.048 Uiso 1 1 calc R . . C13 C 1.09454(19) 0.9537(2) 0.44092(16) 0.0526(9) Uani 1 1 d . . . H13A H 1.0918 1.0120 0.4436 0.079 Uiso 1 1 calc R . . H13B H 1.1441 0.9374 0.4431 0.079 Uiso 1 1 calc R . . H13C H 1.0727 0.9300 0.4787 0.079 Uiso 1 1 calc R . . C14 C 1.0913(2) 0.9613(3) 0.31570(17) 0.0651(11) Uani 1 1 d . . . H14A H 1.0668 0.9430 0.2729 0.098 Uiso 1 1 calc R . . H14B H 1.1407 0.9443 0.3188 0.098 Uiso 1 1 calc R . . H14C H 1.0891 1.0197 0.3179 0.098 Uiso 1 1 calc R . . C15 C 0.79349(16) 0.85117(19) 0.33552(15) 0.0389(7) Uani 1 1 d . . . H15 H 0.8157 0.7975 0.3322 0.047 Uiso 1 1 calc R . . C16 C 0.7506(2) 0.8678(2) 0.26815(17) 0.0588(10) Uani 1 1 d . . . H16A H 0.7288 0.9207 0.2695 0.088 Uiso 1 1 calc R . . H16B H 0.7137 0.8273 0.2598 0.088 Uiso 1 1 calc R . . H16C H 0.7817 0.8663 0.2319 0.088 Uiso 1 1 calc R . . C17 C 0.7438(2) 0.8465(3) 0.39106(19) 0.0655(11) Uani 1 1 d . . . H17A H 0.7699 0.8271 0.4328 0.098 Uiso 1 1 calc R . . H17B H 0.7050 0.8098 0.3772 0.098 Uiso 1 1 calc R . . H17C H 0.7247 0.8996 0.3987 0.098 Uiso 1 1 calc R . . C18 C 0.92924(15) 0.59661(15) 0.36407(12) 0.0260(6) Uani 1 1 d . . . C19 C 0.98623(16) 0.54278(16) 0.37130(13) 0.0305(6) Uani 1 1 d . . . C20 C 0.97126(19) 0.46148(17) 0.37652(14) 0.0394(7) Uani 1 1 d . . . H20 H 1.0092 0.4244 0.3815 0.047 Uiso 1 1 calc R . . C21 C 0.9031(2) 0.43370(18) 0.37460(15) 0.0468(9) Uani 1 1 d . . . H21 H 0.8941 0.3781 0.3772 0.056 Uiso 1 1 calc R . . C22 C 0.84784(18) 0.48743(17) 0.36883(14) 0.0397(8) Uani 1 1 d . . . H22 H 0.8009 0.4681 0.3684 0.048 Uiso 1 1 calc R . . C23 C 0.85911(16) 0.56905(16) 0.36357(13) 0.0312(6) Uani 1 1 d . . . C24 C 1.06276(16) 0.56822(17) 0.37222(14) 0.0334(7) Uani 1 1 d . . . H24 H 1.0646 0.6278 0.3726 0.040 Uiso 1 1 calc R . . C25 C 1.10804(18) 0.5375(2) 0.43479(15) 0.0459(8) Uani 1 1 d . . . H25A H 1.0871 0.5544 0.4755 0.069 Uiso 1 1 calc R . . H25B H 1.1558 0.5594 0.4356 0.069 Uiso 1 1 calc R . . H25C H 1.1101 0.4792 0.4334 0.069 Uiso 1 1 calc R . . C26 C 1.09402(19) 0.5386(2) 0.30849(15) 0.0484(9) Uani 1 1 d . . . H26A H 1.0942 0.4801 0.3080 0.073 Uiso 1 1 calc R . . H26B H 1.1424 0.5583 0.3085 0.073 Uiso 1 1 calc R . . H26C H 1.0653 0.5584 0.2683 0.073 Uiso 1 1 calc R . . C27 C 0.79613(16) 0.62492(18) 0.35822(15) 0.0367(7) Uani 1 1 d . . . H27 H 0.8141 0.6800 0.3688 0.044 Uiso 1 1 calc R . . C28 C 0.74335(19) 0.6038(2) 0.40945(18) 0.0571(10) Uani 1 1 d . . . H28A H 0.7178 0.5551 0.3949 0.086 Uiso 1 1 calc R . . H28B H 0.7098 0.6477 0.4119 0.086 Uiso 1 1 calc R . . H28C H 0.7690 0.5952 0.4540 0.086 Uiso 1 1 calc R . . C29 C 0.75783(18) 0.6262(2) 0.28717(16) 0.0484(8) Uani 1 1 d . . . H29A H 0.7900 0.6455 0.2553 0.073 Uiso 1 1 calc R . . H29B H 0.7169 0.6618 0.2861 0.073 Uiso 1 1 calc R . . H29C H 0.7420 0.5722 0.2744 0.073 Uiso 1 1 calc R . . C30 C 0.9524(7) 0.7395(8) 0.7071(7) 0.104(4) Uiso 0.50 1 d PD . . C31 C 1.0436(8) 0.7378(9) 0.7258(9) 0.130(5) Uiso 0.50 1 d PD . . C32 C 0.9490(8) 0.7816(10) 0.7079(8) 0.133(6) Uiso 0.50 1 d P . . C33 C 1.0583(6) 0.7745(7) 0.7240(5) 0.079(3) Uiso 0.50 1 d P . . 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 0.02867(17) 0.02379(17) 0.02179(17) -0.00040(11) 0.00652(11) 0.00030(12) N1 0.0268(12) 0.0218(11) 0.0238(11) -0.0003(8) 0.0063(9) 0.0009(9) N2 0.0261(12) 0.0233(11) 0.0215(11) 0.0000(9) 0.0067(9) -0.0029(9) C1 0.0195(12) 0.0220(13) 0.0231(12) -0.0014(10) 0.0050(10) -0.0007(10) C2 0.0355(15) 0.0256(14) 0.0229(13) -0.0001(10) 0.0046(11) -0.0010(11) C3 0.080(3) 0.0370(18) 0.0288(16) -0.0019(13) 0.0127(17) 0.0063(17) C4 0.061(3) 0.116(4) 0.038(2) -0.013(2) -0.0132(18) 0.037(2) C5 0.142(4) 0.060(2) 0.0265(17) -0.0036(16) 0.020(2) -0.056(3) C6 0.0411(18) 0.0216(13) 0.0213(13) 0.0006(10) 0.0098(12) 0.0039(12) C7 0.0469(19) 0.0259(14) 0.0244(14) -0.0022(11) 0.0099(13) -0.0033(13) C8 0.075(3) 0.0237(15) 0.0355(17) -0.0054(12) 0.0096(17) -0.0052(15) C9 0.080(3) 0.0285(17) 0.049(2) -0.0014(14) 0.0116(19) 0.0192(18) C10 0.058(2) 0.0385(19) 0.0459(19) 0.0009(14) 0.0068(17) 0.0246(17) C11 0.0426(18) 0.0342(16) 0.0256(15) 0.0031(12) 0.0062(13) 0.0119(13) C12 0.046(2) 0.0323(16) 0.0424(18) -0.0098(13) 0.0109(15) -0.0113(14) C13 0.050(2) 0.069(2) 0.0399(19) -0.0013(16) 0.0065(16) -0.0151(18) C14 0.058(3) 0.103(3) 0.0366(19) -0.0153(19) 0.0171(18) -0.020(2) C15 0.0321(17) 0.0435(18) 0.0424(18) 0.0063(13) 0.0102(14) 0.0112(13) C16 0.058(2) 0.066(2) 0.051(2) 0.0083(18) -0.0056(18) -0.0037(19) C17 0.047(2) 0.094(3) 0.059(2) 0.002(2) 0.0250(19) 0.004(2) C18 0.0373(17) 0.0206(13) 0.0205(13) -0.0006(10) 0.0056(12) -0.0040(11) C19 0.0460(19) 0.0259(14) 0.0207(13) 0.0014(10) 0.0078(13) 0.0008(12) C20 0.060(2) 0.0254(15) 0.0333(16) 0.0019(12) 0.0044(15) 0.0037(14) C21 0.077(3) 0.0239(16) 0.0395(18) 0.0003(13) 0.0044(17) -0.0114(16) C22 0.052(2) 0.0341(17) 0.0327(16) -0.0011(12) 0.0055(15) -0.0190(15) C23 0.0408(18) 0.0315(15) 0.0220(14) -0.0021(11) 0.0076(13) -0.0091(12) C24 0.0406(18) 0.0293(15) 0.0313(15) 0.0040(11) 0.0084(13) 0.0064(12) C25 0.047(2) 0.053(2) 0.0372(18) 0.0077(14) 0.0012(15) 0.0112(16) C26 0.057(2) 0.055(2) 0.0364(18) 0.0031(15) 0.0172(16) 0.0106(17) C27 0.0303(17) 0.0379(17) 0.0429(17) -0.0052(13) 0.0077(14) -0.0093(13) C28 0.044(2) 0.071(3) 0.060(2) -0.0150(18) 0.0214(18) -0.0185(18) C29 0.039(2) 0.058(2) 0.048(2) -0.0035(16) 0.0024(16) -0.0023(16) _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 2.032(2) . ? Ge1 N2 2.049(2) . ? Ge1 Ge1 2.6380(8) 2_755 ? O1 C31 1.277(16) . ? O1 C30 1.342(14) . ? O1 C33 1.379(12) . ? O1 C32 1.413(16) . ? N1 C1 1.339(3) . ? N1 C6 1.443(3) . ? N2 C1 1.339(3) . ? N2 C18 1.435(3) . ? C1 C2 1.540(4) . ? C2 C5 1.516(4) . ? C2 C3 1.524(4) . ? C2 C4 1.539(5) . ? C6 C7 1.403(4) . ? C6 C11 1.409(4) . ? C7 C8 1.402(4) . ? C7 C12 1.514(4) . ? C8 C9 1.382(5) . ? C9 C10 1.377(5) . ? C10 C11 1.392(4) . ? C11 C15 1.515(4) . ? C12 C13 1.524(4) . ? C12 C14 1.533(4) . ? C15 C16 1.525(5) . ? C15 C17 1.528(4) . ? C18 C19 1.408(4) . ? C18 C23 1.413(4) . ? C19 C20 1.399(4) . ? C19 C24 1.518(4) . ? C20 C21 1.377(5) . ? C21 C22 1.381(5) . ? C22 C23 1.391(4) . ? C23 C27 1.518(4) . ? C24 C25 1.531(4) . ? C24 C26 1.538(4) . ? C27 C29 1.525(4) . ? C27 C28 1.544(4) . ? C30 C32 0.71(2) . ? C30 C31 1.330(19) 2_756 ? C30 C33 1.525(17) 2_756 ? C30 C31 1.741(15) . ? C31 C33 0.679(18) . ? C31 C30 1.330(19) 2_756 ? C31 C32 1.50(2) 2_756 ? C31 C32 1.95(2) . ? C31 C31 2.00(3) 2_756 ? C32 C33 1.382(17) 2_756 ? C32 C31 1.50(2) 2_756 ? C33 C32 1.382(17) 2_756 ? C33 C30 1.525(17) 2_756 ? 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 63.61(9) . . ? N1 Ge1 Ge1 96.74(7) . 2_755 ? N2 Ge1 Ge1 97.70(7) . 2_755 ? C31 O1 C30 83.3(8) . . ? C31 O1 C33 29.3(8) . . ? C30 O1 C33 100.7(9) . . ? C31 O1 C32 92.5(11) . . ? C30 O1 C32 29.7(9) . . ? C33 O1 C32 96.1(9) . . ? C1 N1 C6 129.6(2) . . ? C1 N1 Ge1 94.93(15) . . ? C6 N1 Ge1 130.04(17) . . ? C1 N2 C18 131.6(2) . . ? C1 N2 Ge1 94.19(15) . . ? C18 N2 Ge1 131.45(16) . . ? N2 C1 N1 106.9(2) . . ? N2 C1 C2 126.1(2) . . ? N1 C1 C2 126.6(2) . . ? C5 C2 C3 107.6(3) . . ? C5 C2 C4 108.2(3) . . ? C3 C2 C4 106.9(3) . . ? C5 C2 C1 113.6(2) . . ? C3 C2 C1 114.6(2) . . ? C4 C2 C1 105.6(2) . . ? C7 C6 C11 121.5(3) . . ? C7 C6 N1 119.5(2) . . ? C11 C6 N1 118.8(2) . . ? C8 C7 C6 117.9(3) . . ? C8 C7 C12 119.0(3) . . ? C6 C7 C12 123.1(2) . . ? C9 C8 C7 121.0(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C11 121.2(3) . . ? C10 C11 C6 118.1(3) . . ? C10 C11 C15 119.1(3) . . ? C6 C11 C15 122.8(2) . . ? C7 C12 C13 112.8(3) . . ? C7 C12 C14 110.3(3) . . ? C13 C12 C14 109.1(3) . . ? C11 C15 C16 111.7(3) . . ? C11 C15 C17 113.4(3) . . ? C16 C15 C17 109.3(3) . . ? C19 C18 C23 120.7(2) . . ? C19 C18 N2 119.7(2) . . ? C23 C18 N2 119.3(2) . . ? C20 C19 C18 118.1(3) . . ? C20 C19 C24 118.4(3) . . ? C18 C19 C24 123.4(2) . . ? C21 C20 C19 121.8(3) . . ? C20 C21 C22 119.4(3) . . ? C21 C22 C23 121.7(3) . . ? C22 C23 C18 118.3(3) . . ? C22 C23 C27 119.1(3) . . ? C18 C23 C27 122.6(2) . . ? C19 C24 C25 112.2(2) . . ? C19 C24 C26 110.5(3) . . ? C25 C24 C26 109.2(3) . . ? C23 C27 C29 112.0(2) . . ? C23 C27 C28 112.0(3) . . ? C29 C27 C28 109.5(3) . . ? C32 C30 C31 90(2) . 2_756 ? C32 C30 O1 80.7(19) . . ? C31 C30 O1 123.9(14) 2_756 . ? C32 C30 C33 64.8(18) . 2_756 ? C31 C30 C33 26.4(8) 2_756 2_756 ? O1 C30 C33 123.3(10) . 2_756 ? C32 C30 C31 96(2) . . ? C31 C30 C31 80.2(13) 2_756 . ? O1 C30 C31 46.8(7) . . ? C33 C30 C31 91.9(10) 2_756 . ? C33 C31 O1 84(2) . . ? C33 C31 C30 93(2) . 2_756 ? O1 C31 C30 143.7(16) . 2_756 ? C33 C31 C32 66.5(18) . 2_756 ? O1 C31 C32 126.2(14) . 2_756 ? C30 C31 C32 28.2(9) 2_756 2_756 ? C33 C31 C30 112(2) . . ? O1 C31 C30 50.0(7) . . ? C30 C31 C30 99.8(13) 2_756 . ? C32 C31 C30 100.5(11) 2_756 . ? C33 C31 C32 91(2) . . ? O1 C31 C32 46.5(7) . . ? C30 C31 C32 97.7(12) 2_756 . ? C32 C31 C32 88.8(12) 2_756 . ? C30 C31 C32 21.3(7) . . ? C33 C31 C31 113.1(19) . 2_756 ? O1 C31 C31 89.1(11) . 2_756 ? C30 C31 C31 58.9(10) 2_756 2_756 ? C32 C31 C31 65.6(11) 2_756 2_756 ? C30 C31 C31 40.9(7) . 2_756 ? C32 C31 C31 44.7(7) . 2_756 ? C30 C32 C33 87(2) . 2_756 ? C30 C32 O1 69.6(18) . . ? C33 C32 O1 129.2(13) 2_756 . ? C30 C32 C31 62.2(17) . 2_756 ? C33 C32 C31 26.8(8) 2_756 2_756 ? O1 C32 C31 107.8(12) . 2_756 ? C30 C32 C31 62.9(18) . . ? C33 C32 C31 88.3(11) 2_756 . ? O1 C32 C31 41.0(7) . . ? C31 C32 C31 69.6(11) 2_756 . ? C31 C33 O1 67.0(18) . . ? C31 C33 C32 86.7(19) . 2_756 ? O1 C33 C32 128.0(11) . 2_756 ? C31 C33 C30 60.5(18) . 2_756 ? O1 C33 C30 117.0(10) . 2_756 ? C32 C33 C30 27.7(8) 2_756 2_756 ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.588 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.068 # Attachment 'compound4.cif' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 616060' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C62 H96 Ge2 N6' _chemical_formula_weight 1070.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.818(2) _cell_length_b 14.892(3) _cell_length_c 17.589(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.72(3) _cell_angle_gamma 90.00 _cell_volume 3007.3(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour lime-green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 1.041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.857 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10393 _diffrn_reflns_av_R_equivalents 0.0960 _diffrn_reflns_av_sigmaI/netI 0.1409 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5573 _reflns_number_gt 3594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0181P)^2^+6.4333P] 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 5573 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1337 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.55446(4) 0.98878(3) 0.07513(3) 0.02233(16) Uani 1 1 d . . . N1 N 0.5911(3) 0.8548(2) 0.0658(2) 0.0193(9) Uani 1 1 d . . . N2 N 0.4424(3) 0.9003(2) 0.1075(2) 0.0183(9) Uani 1 1 d . . . N3 N 0.4804(3) 0.7393(2) 0.1119(2) 0.0209(9) Uani 1 1 d . . . C1 C 0.5020(4) 0.8271(3) 0.0965(2) 0.0177(10) Uani 1 1 d . . . C2 C 0.7010(4) 0.8103(3) 0.0754(3) 0.0200(11) Uani 1 1 d . . . C3 C 0.7772(4) 0.7991(3) 0.1505(3) 0.0243(11) Uani 1 1 d . . . C4 C 0.8865(4) 0.7615(3) 0.1556(3) 0.0332(13) Uani 1 1 d . . . H4 H 0.9389 0.7553 0.2054 0.040 Uiso 1 1 calc R . . C5 C 0.9200(4) 0.7331(3) 0.0895(3) 0.0319(13) Uani 1 1 d . . . H5 H 0.9950 0.7075 0.0941 0.038 Uiso 1 1 calc R . . C6 C 0.8452(4) 0.7418(3) 0.0172(3) 0.0261(12) Uani 1 1 d . . . H6 H 0.8685 0.7207 -0.0277 0.031 Uiso 1 1 calc R . . C7 C 0.7362(4) 0.7808(3) 0.0085(3) 0.0212(11) Uani 1 1 d . . . C8 C 0.7461(4) 0.8287(3) 0.2255(3) 0.0297(12) Uani 1 1 d . . . H8 H 0.6593 0.8329 0.2149 0.036 Uiso 1 1 calc R . . C9 C 0.7869(5) 0.7606(4) 0.2928(3) 0.0460(15) Uani 1 1 d . . . H9A H 0.7667 0.6996 0.2732 0.069 Uiso 1 1 calc R . . H9B H 0.7485 0.7738 0.3351 0.069 Uiso 1 1 calc R . . H9C H 0.8715 0.7652 0.3126 0.069 Uiso 1 1 calc R . . C10 C 0.7962(5) 0.9216(4) 0.2529(3) 0.0443(15) Uani 1 1 d . . . H10A H 0.8814 0.9195 0.2637 0.067 Uiso 1 1 calc R . . H10B H 0.7724 0.9387 0.3006 0.067 Uiso 1 1 calc R . . H10C H 0.7668 0.9660 0.2118 0.067 Uiso 1 1 calc R . . C11 C 0.6616(5) 0.7904(3) -0.0743(3) 0.0361(14) Uani 1 1 d . . . H11 H 0.5866 0.8197 -0.0716 0.043 Uiso 1 1 calc R . . C12 C 0.7227(6) 0.8503(4) -0.1235(3) 0.0530(18) Uani 1 1 d . . . H12A H 0.7409 0.9085 -0.0977 0.079 Uiso 1 1 calc R . . H12B H 0.6712 0.8591 -0.1755 0.079 Uiso 1 1 calc R . . H12C H 0.7949 0.8213 -0.1287 0.079 Uiso 1 1 calc R . . C13 C 0.6340(4) 0.6994(4) -0.1147(3) 0.0461(16) Uani 1 1 d . . . H13A H 0.7069 0.6687 -0.1161 0.069 Uiso 1 1 calc R . . H13B H 0.5877 0.7085 -0.1683 0.069 Uiso 1 1 calc R . . H13C H 0.5898 0.6627 -0.0856 0.069 Uiso 1 1 calc R . . C14 C 0.3368(4) 0.9086(3) 0.1334(3) 0.0195(11) Uani 1 1 d . . . C15 C 0.3458(4) 0.9314(3) 0.2127(3) 0.0239(11) Uani 1 1 d . . . C16 C 0.2433(5) 0.9447(3) 0.2371(3) 0.0288(12) Uani 1 1 d . . . H16 H 0.2476 0.9604 0.2900 0.035 Uiso 1 1 calc R . . C17 C 0.1358(5) 0.9354(3) 0.1861(3) 0.0325(13) Uani 1 1 d . . . H17 H 0.0669 0.9443 0.2041 0.039 Uiso 1 1 calc R . . C18 C 0.1281(4) 0.9133(3) 0.1096(3) 0.0265(12) Uani 1 1 d . . . H18 H 0.0534 0.9064 0.0752 0.032 Uiso 1 1 calc R . . C19 C 0.2275(4) 0.9006(3) 0.0807(3) 0.0212(11) Uani 1 1 d . . . C20 C 0.4627(4) 0.9406(3) 0.2705(3) 0.0291(12) Uani 1 1 d . . . H20 H 0.5224 0.9124 0.2462 0.035 Uiso 1 1 calc R . . C21 C 0.4975(5) 1.0389(3) 0.2873(3) 0.0426(15) Uani 1 1 d . . . H21A H 0.5047 1.0682 0.2388 0.064 Uiso 1 1 calc R . . H21B H 0.5723 1.0419 0.3259 0.064 Uiso 1 1 calc R . . H21C H 0.4377 1.0696 0.3078 0.064 Uiso 1 1 calc R . . C22 C 0.4675(5) 0.8916(4) 0.3480(3) 0.0478(16) Uani 1 1 d . . . H22A H 0.4167 0.9223 0.3764 0.072 Uiso 1 1 calc R . . H22B H 0.5477 0.8918 0.3798 0.072 Uiso 1 1 calc R . . H22C H 0.4411 0.8296 0.3372 0.072 Uiso 1 1 calc R . . C23 C 0.2138(4) 0.8823(3) -0.0059(3) 0.0257(12) Uani 1 1 d . . . H23 H 0.2920 0.8666 -0.0147 0.031 Uiso 1 1 calc R . . C24 C 0.1704(5) 0.9676(4) -0.0526(3) 0.0407(14) Uani 1 1 d . . . H24A H 0.1687 0.9578 -0.1079 0.061 Uiso 1 1 calc R . . H24B H 0.2229 1.0176 -0.0325 0.061 Uiso 1 1 calc R . . H24C H 0.0917 0.9819 -0.0471 0.061 Uiso 1 1 calc R . . C25 C 0.1301(5) 0.8055(4) -0.0367(3) 0.0396(14) Uani 1 1 d . . . H25A H 0.1573 0.7507 -0.0072 0.059 Uiso 1 1 calc R . . H25B H 0.1272 0.7956 -0.0922 0.059 Uiso 1 1 calc R . . H25C H 0.0522 0.8208 -0.0305 0.059 Uiso 1 1 calc R . . C26 C 0.5036(4) 0.6718(3) 0.0555(3) 0.0301(12) Uani 1 1 d . . . H26 H 0.5328 0.7067 0.0155 0.036 Uiso 1 1 calc R . . C27 C 0.6003(5) 0.6043(4) 0.0897(4) 0.0569(18) Uani 1 1 d . . . H27A H 0.6639 0.6353 0.1262 0.085 Uiso 1 1 calc R . . H27B H 0.6297 0.5776 0.0473 0.085 Uiso 1 1 calc R . . H27C H 0.5690 0.5570 0.1176 0.085 Uiso 1 1 calc R . . C28 C 0.3945(5) 0.6245(4) 0.0106(4) 0.0606(19) Uani 1 1 d . . . H28A H 0.3682 0.5819 0.0453 0.091 Uiso 1 1 calc R . . H28B H 0.4116 0.5921 -0.0339 0.091 Uiso 1 1 calc R . . H28C H 0.3332 0.6689 -0.0085 0.091 Uiso 1 1 calc R . . C29 C 0.4258(4) 0.7170(3) 0.1770(3) 0.0265(12) Uani 1 1 d . . . H29 H 0.4299 0.7729 0.2090 0.032 Uiso 1 1 calc R . . C30 C 0.4943(5) 0.6454(4) 0.2319(3) 0.0441(15) Uani 1 1 d . . . H30A H 0.4814 0.5865 0.2065 0.066 Uiso 1 1 calc R . . H30B H 0.4677 0.6441 0.2806 0.066 Uiso 1 1 calc R . . H30C H 0.5776 0.6598 0.2437 0.066 Uiso 1 1 calc R . . C31 C 0.2979(4) 0.6895(4) 0.1553(3) 0.0387(14) Uani 1 1 d . . . H31A H 0.2545 0.7302 0.1150 0.058 Uiso 1 1 calc R . . H31B H 0.2659 0.6928 0.2018 0.058 Uiso 1 1 calc R . . H31C H 0.2911 0.6279 0.1352 0.058 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 0.0240(3) 0.0170(3) 0.0286(3) -0.0006(3) 0.0114(2) 0.0004(3) N1 0.022(2) 0.013(2) 0.025(2) -0.0013(17) 0.0105(18) 0.0065(17) N2 0.022(2) 0.015(2) 0.020(2) 0.0027(17) 0.0104(18) -0.0009(17) N3 0.027(2) 0.016(2) 0.022(2) -0.0015(18) 0.0097(18) -0.0001(18) C1 0.021(3) 0.020(3) 0.014(2) -0.003(2) 0.007(2) -0.004(2) C2 0.021(3) 0.015(2) 0.026(3) 0.001(2) 0.009(2) 0.002(2) C3 0.021(3) 0.028(3) 0.025(3) 0.002(2) 0.007(2) -0.005(2) C4 0.023(3) 0.044(3) 0.031(3) 0.010(3) 0.002(2) 0.003(3) C5 0.021(3) 0.037(3) 0.040(3) 0.004(3) 0.011(3) 0.012(2) C6 0.030(3) 0.027(3) 0.025(3) 0.006(2) 0.014(2) 0.007(2) C7 0.023(3) 0.018(3) 0.023(3) 0.002(2) 0.006(2) 0.002(2) C8 0.018(3) 0.050(3) 0.022(3) -0.005(3) 0.007(2) -0.005(2) C9 0.049(4) 0.061(4) 0.029(3) 0.009(3) 0.012(3) -0.014(3) C10 0.055(4) 0.052(4) 0.026(3) -0.009(3) 0.010(3) -0.003(3) C11 0.039(3) 0.046(3) 0.024(3) 0.000(3) 0.009(3) 0.024(3) C12 0.096(5) 0.040(4) 0.026(3) 0.016(3) 0.021(3) 0.026(4) C13 0.032(3) 0.077(5) 0.030(3) -0.020(3) 0.009(3) 0.001(3) C14 0.027(3) 0.012(2) 0.022(3) 0.001(2) 0.011(2) 0.002(2) C15 0.028(3) 0.017(3) 0.029(3) 0.003(2) 0.012(2) 0.003(2) C16 0.043(3) 0.024(3) 0.025(3) 0.001(2) 0.020(3) 0.003(2) C17 0.033(3) 0.030(3) 0.041(3) 0.002(3) 0.024(3) 0.007(3) C18 0.021(3) 0.027(3) 0.033(3) 0.000(2) 0.010(2) 0.001(2) C19 0.022(3) 0.017(3) 0.027(3) 0.005(2) 0.009(2) 0.003(2) C20 0.034(3) 0.034(3) 0.023(3) -0.001(2) 0.013(2) 0.005(3) C21 0.044(4) 0.037(3) 0.043(3) -0.005(3) 0.003(3) 0.002(3) C22 0.052(4) 0.054(4) 0.036(3) 0.005(3) 0.006(3) -0.004(3) C23 0.020(3) 0.031(3) 0.029(3) -0.001(2) 0.011(2) 0.003(2) C24 0.040(3) 0.048(4) 0.037(3) 0.016(3) 0.016(3) 0.007(3) C25 0.048(4) 0.047(4) 0.026(3) 0.000(3) 0.012(3) -0.005(3) C26 0.040(3) 0.019(3) 0.032(3) -0.007(2) 0.011(3) -0.004(2) C27 0.079(5) 0.029(3) 0.068(4) -0.004(3) 0.028(4) 0.025(3) C28 0.066(5) 0.058(4) 0.062(4) -0.039(4) 0.023(4) -0.019(4) C29 0.033(3) 0.024(3) 0.024(3) 0.000(2) 0.010(2) -0.005(2) C30 0.043(4) 0.049(4) 0.040(3) 0.016(3) 0.009(3) 0.001(3) C31 0.033(3) 0.045(3) 0.040(3) 0.008(3) 0.013(3) -0.008(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 N2 2.043(3) . ? Ge1 N1 2.056(3) . ? Ge1 Ge1 2.6721(13) 3_675 ? N1 C1 1.357(5) . ? N1 C2 1.433(5) . ? N2 C1 1.337(5) . ? N2 C14 1.432(5) . ? N3 C1 1.371(5) . ? N3 C29 1.480(5) . ? N3 C26 1.483(6) . ? C2 C7 1.408(6) . ? C2 C3 1.419(6) . ? C3 C4 1.391(6) . ? C3 C8 1.518(6) . ? C4 C5 1.381(7) . ? C5 C6 1.371(6) . ? C6 C7 1.388(6) . ? C7 C11 1.520(6) . ? C8 C10 1.537(7) . ? C8 C9 1.546(7) . ? C11 C13 1.529(7) . ? C11 C12 1.536(7) . ? C14 C19 1.405(6) . ? C14 C15 1.415(6) . ? C15 C16 1.391(6) . ? C15 C20 1.515(7) . ? C16 C17 1.378(7) . ? C17 C18 1.367(7) . ? C18 C19 1.399(6) . ? C19 C23 1.518(6) . ? C20 C21 1.531(7) . ? C20 C22 1.534(7) . ? C23 C25 1.525(7) . ? C23 C24 1.533(6) . ? C26 C28 1.516(7) . ? C26 C27 1.533(7) . ? C29 C31 1.525(6) . ? C29 C30 1.535(7) . ? 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 63.84(14) . . ? N2 Ge1 Ge1 99.47(10) . 3_675 ? N1 Ge1 Ge1 95.97(10) . 3_675 ? C1 N1 C2 125.5(4) . . ? C1 N1 Ge1 93.8(2) . . ? C2 N1 Ge1 130.0(3) . . ? C1 N2 C14 130.2(4) . . ? C1 N2 Ge1 95.0(3) . . ? C14 N2 Ge1 134.8(3) . . ? C1 N3 C29 120.2(4) . . ? C1 N3 C26 116.2(4) . . ? C29 N3 C26 123.3(4) . . ? N2 C1 N1 107.1(4) . . ? N2 C1 N3 128.3(4) . . ? N1 C1 N3 124.5(4) . . ? C7 C2 C3 119.6(4) . . ? C7 C2 N1 119.0(4) . . ? C3 C2 N1 121.4(4) . . ? C4 C3 C2 118.8(4) . . ? C4 C3 C8 118.3(4) . . ? C2 C3 C8 123.0(4) . . ? C5 C4 C3 121.1(4) . . ? C6 C5 C4 120.1(4) . . ? C5 C6 C7 121.3(4) . . ? C6 C7 C2 119.2(4) . . ? C6 C7 C11 117.2(4) . . ? C2 C7 C11 123.6(4) . . ? C3 C8 C10 112.3(4) . . ? C3 C8 C9 112.3(4) . . ? C10 C8 C9 108.9(4) . . ? C7 C11 C13 111.9(4) . . ? C7 C11 C12 110.6(4) . . ? C13 C11 C12 109.2(4) . . ? C19 C14 C15 120.9(4) . . ? C19 C14 N2 121.2(4) . . ? C15 C14 N2 117.8(4) . . ? C16 C15 C14 118.1(4) . . ? C16 C15 C20 120.2(4) . . ? C14 C15 C20 121.8(4) . . ? C17 C16 C15 121.4(4) . . ? C18 C17 C16 120.1(5) . . ? C17 C18 C19 121.6(5) . . ? C18 C19 C14 118.0(4) . . ? C18 C19 C23 119.4(4) . . ? C14 C19 C23 122.6(4) . . ? C15 C20 C21 112.1(4) . . ? C15 C20 C22 112.9(4) . . ? C21 C20 C22 109.4(4) . . ? C19 C23 C25 113.4(4) . . ? C19 C23 C24 109.3(4) . . ? C25 C23 C24 108.9(4) . . ? N3 C26 C28 113.2(4) . . ? N3 C26 C27 114.9(4) . . ? C28 C26 C27 111.3(5) . . ? N3 C29 C31 117.0(4) . . ? N3 C29 C30 112.4(4) . . ? C31 C29 C30 108.3(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.727 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.090