# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Sergey Karlov' _publ_contact_author_email SERGEJ@ORG.CHEM.MSU.RU _publ_section_title ; Novel derivatives of hypervalent germanium: synthesis, structure, and stability ; loop_ _publ_author_name 'Sergey Karlov' 'Andrei Churakov' 'Judith Howard' 'MengMeng Huan' 'Elmira Kh. Lermontova' ; M.V.Zabalov ; 'Galina S. Zaitseva' # Attachment 'COMB-new.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 718433' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H11 Cl2 F10 Ge N3, 1.5 (C7 H8)' _chemical_formula_sum 'C27.50 H23 Cl2 F10 Ge N3' _chemical_formula_weight 728.98 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' F F 0.0171 0.0103 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4562(6) _cell_length_b 22.0794(17) _cell_length_c 17.7878(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.241(2) _cell_angle_gamma 90.00 _cell_volume 2928.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5342 _cell_measurement_theta_min 2.470 _cell_measurement_theta_max 28.590 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1460 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7605 _exptl_absorpt_correction_T_max 0.8580 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19274 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6279 _reflns_number_gt 5240 _reflns_threshold_expression I>2\s(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^)+(0.0451P)^2^+0.5303P] 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 6279 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Ge Ge 0.06171(3) 0.732786(9) 0.802903(11) 0.02010(7) Uani 1 1 d . . . Cl1 Cl 0.28408(7) 0.66529(2) 0.81559(3) 0.02995(13) Uani 1 1 d . . . Cl2 Cl 0.21666(9) 0.79084(3) 0.72902(3) 0.04323(17) Uani 1 1 d . . . N3 N -0.1650(3) 0.79040(8) 0.79641(10) 0.0294(4) Uani 1 1 d . . . C1 C -0.1947(4) 0.82306(13) 0.72470(15) 0.0499(7) Uani 1 1 d . . . H1A H -0.3125 0.8427 0.7256 0.075 Uiso 1 1 calc R . . H1B H -0.1902 0.7943 0.6828 0.075 Uiso 1 1 calc R . . H1C H -0.1012 0.8538 0.7183 0.075 Uiso 1 1 calc R . . N1 N -0.0943(2) 0.67824(8) 0.76077(10) 0.0249(4) Uani 1 1 d . . . C11 C -0.3124(3) 0.74657(11) 0.80990(17) 0.0407(6) Uani 1 1 d . . . H11A H -0.4300 0.7659 0.7999 0.049 Uiso 1 1 calc R . . H11B H -0.3099 0.7326 0.8628 0.049 Uiso 1 1 calc R . . C12 C -0.2841(3) 0.69331(11) 0.75686(16) 0.0422(7) Uani 1 1 d . . . H12A H -0.3578 0.6583 0.7726 0.051 Uiso 1 1 calc R . . H12B H -0.3183 0.7046 0.7049 0.051 Uiso 1 1 calc R . . C13 C -0.0412(3) 0.62573(9) 0.72186(12) 0.0224(4) Uani 1 1 d . . . C14 C 0.0111(3) 0.62804(9) 0.64727(12) 0.0255(5) Uani 1 1 d . . . C15 C 0.0615(3) 0.57671(10) 0.60823(12) 0.0278(5) Uani 1 1 d . . . C16 C 0.0626(3) 0.52175(9) 0.64374(12) 0.0282(5) Uani 1 1 d . . . C17 C 0.0104(3) 0.51782(9) 0.71786(13) 0.0296(5) Uani 1 1 d . . . C18 C -0.0426(3) 0.56910(10) 0.75556(12) 0.0279(5) Uani 1 1 d . . . N2 N 0.0656(3) 0.75791(8) 0.90144(9) 0.0263(4) Uani 1 1 d . . . C21 C -0.1434(3) 0.83393(10) 0.85932(13) 0.0328(5) Uani 1 1 d . . . H21A H -0.2604 0.8527 0.8713 0.039 Uiso 1 1 calc R . . H21B H -0.0590 0.8665 0.8448 0.039 Uiso 1 1 calc R . . C22 C -0.0720(3) 0.80054(10) 0.92695(13) 0.0325(5) Uani 1 1 d . . . H22A H -0.0196 0.8295 0.9634 0.039 Uiso 1 1 calc R . . H22B H -0.1703 0.7784 0.9521 0.039 Uiso 1 1 calc R . . C23 C 0.1591(3) 0.72620(9) 0.95814(11) 0.0255(5) Uani 1 1 d . . . C24 C 0.0853(3) 0.67682(11) 0.99511(12) 0.0337(5) Uani 1 1 d . . . C25 C 0.1789(4) 0.64399(11) 1.04819(13) 0.0393(6) Uani 1 1 d . . . C26 C 0.3517(4) 0.66049(12) 1.06607(12) 0.0385(6) Uani 1 1 d . . . C27 C 0.4280(3) 0.70997(12) 1.03211(13) 0.0357(6) Uani 1 1 d . . . C28 C 0.3323(3) 0.74236(10) 0.97919(12) 0.0297(5) Uani 1 1 d . . . F14 F 0.0136(2) 0.68151(5) 0.61104(7) 0.0390(3) Uani 1 1 d . . . F15 F 0.1086(2) 0.58049(6) 0.53555(7) 0.0444(4) Uani 1 1 d . . . F16 F 0.1128(2) 0.47199(6) 0.60591(8) 0.0406(4) Uani 1 1 d . . . F17 F 0.0137(2) 0.46372(6) 0.75233(8) 0.0475(4) Uani 1 1 d . . . F18 F -0.0935(2) 0.56414(6) 0.82701(7) 0.0448(4) Uani 1 1 d . . . F24 F -0.0819(2) 0.65922(7) 0.97666(9) 0.0477(4) Uani 1 1 d . . . F25 F 0.1028(3) 0.59687(7) 1.08274(9) 0.0590(5) Uani 1 1 d . . . F26 F 0.4457(2) 0.62906(7) 1.11742(8) 0.0534(4) Uani 1 1 d . . . F27 F 0.5955(2) 0.72687(8) 1.05085(9) 0.0526(4) Uani 1 1 d . . . F28 F 0.4121(2) 0.78979(6) 0.94592(8) 0.0397(3) Uani 1 1 d . . . C2 C 0.4831(4) 0.98903(15) 0.77020(16) 0.0530(8) Uani 1 1 d . . . H2 H 0.5245 0.9860 0.7199 0.064 Uiso 1 1 calc R . . C3 C 0.4072(4) 0.94014(13) 0.80427(17) 0.0488(7) Uani 1 1 d . . . H3 H 0.3955 0.9030 0.7777 0.059 Uiso 1 1 calc R . . C4 C 0.3480(4) 0.94442(11) 0.87647(15) 0.0408(6) Uani 1 1 d . . . H4 H 0.2957 0.9101 0.9000 0.049 Uiso 1 1 calc R . . C5 C 0.3635(3) 0.99809(11) 0.91560(14) 0.0355(6) Uani 1 1 d . . . H5 H 0.3222 1.0003 0.9660 0.043 Uiso 1 1 calc R . . C6 C 0.4384(3) 1.04873(11) 0.88260(15) 0.0366(6) Uani 1 1 d . . . C7 C 0.4999(4) 1.04330(13) 0.80923(16) 0.0477(7) Uani 1 1 d . . . H7 H 0.5542 1.0771 0.7854 0.057 Uiso 1 1 calc R . . C8 C 0.4528(5) 1.10763(12) 0.9252(2) 0.0647(10) Uani 1 1 d . . . H8A H 0.5041 1.1000 0.9751 0.097 Uiso 1 1 calc R . . H8B H 0.3333 1.1255 0.9305 0.097 Uiso 1 1 calc R . . H8C H 0.5304 1.1356 0.8976 0.097 Uiso 1 1 calc R . . C31 C 0.3834(9) 0.5030(3) 0.9678(4) 0.0469(14) Uiso 0.50 1 d P A -1 C32 C 0.5453(10) 0.5355(2) 0.9543(4) 0.0371(12) Uiso 0.50 1 d P A -1 H32 H 0.5506 0.5646 0.9151 0.044 Uiso 0.50 1 calc PR A -1 C33 C 0.7009(13) 0.5241(4) 1.0006(5) 0.075(2) Uiso 0.50 1 d P A -1 H33 H 0.8127 0.5437 0.9929 0.090 Uiso 0.50 1 calc PR A -1 C34 C 0.6737(13) 0.4823(4) 1.0567(5) 0.0649(19) Uiso 0.50 1 d P A -1 H34 H 0.7713 0.4731 1.0893 0.078 Uiso 0.50 1 calc PR A -1 C35 C 0.5248(11) 0.4552(3) 1.0676(4) 0.0580(18) Uiso 0.50 1 d P A -1 H35 H 0.5195 0.4270 1.1079 0.070 Uiso 0.50 1 calc PR A -1 C36 C 0.3671(12) 0.4640(3) 1.0245(4) 0.0480(15) Uiso 0.50 1 d P A -1 H36 H 0.2579 0.4436 1.0352 0.058 Uiso 0.50 1 calc PR A -1 C37 C 0.2238(11) 0.5126(4) 0.9190(5) 0.077(2) Uiso 0.50 1 d P A -1 H37A H 0.1192 0.5213 0.9503 0.116 Uiso 0.50 1 calc PR A -1 H37B H 0.2012 0.4760 0.8893 0.116 Uiso 0.50 1 calc PR A -1 H37C H 0.2458 0.5468 0.8852 0.116 Uiso 0.50 1 calc PR A -1 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 Ge 0.01970(13) 0.02284(12) 0.01775(11) -0.00277(8) 0.00015(8) -0.00336(9) Cl1 0.0223(3) 0.0369(3) 0.0307(3) -0.0100(2) -0.0018(2) 0.0047(2) Cl2 0.0427(4) 0.0538(4) 0.0331(3) 0.0139(3) 0.0004(3) -0.0197(3) N3 0.0297(11) 0.0260(9) 0.0324(10) -0.0079(8) -0.0102(8) 0.0047(8) C1 0.065(2) 0.0465(15) 0.0378(14) -0.0033(12) -0.0207(14) 0.0214(14) N1 0.0162(9) 0.0273(9) 0.0313(9) -0.0132(7) 0.0004(7) -0.0020(7) C11 0.0214(13) 0.0388(13) 0.0620(17) -0.0233(12) 0.0009(12) 0.0019(10) C12 0.0196(13) 0.0414(14) 0.0655(18) -0.0283(13) -0.0043(12) 0.0010(10) C13 0.0176(11) 0.0238(10) 0.0259(10) -0.0074(8) -0.0017(8) -0.0019(8) C14 0.0304(13) 0.0209(10) 0.0251(11) -0.0012(8) -0.0032(9) 0.0034(9) C15 0.0331(13) 0.0305(11) 0.0199(10) -0.0054(8) -0.0010(9) 0.0019(10) C16 0.0310(13) 0.0217(10) 0.0319(11) -0.0093(8) -0.0020(10) 0.0021(9) C17 0.0329(14) 0.0193(10) 0.0366(12) 0.0033(9) -0.0020(10) -0.0035(9) C18 0.0263(12) 0.0337(12) 0.0237(11) -0.0025(9) 0.0040(9) -0.0044(10) N2 0.0302(11) 0.0301(9) 0.0184(8) -0.0060(7) -0.0029(8) 0.0053(8) C21 0.0370(14) 0.0252(11) 0.0362(12) -0.0122(9) -0.0072(11) 0.0043(10) C22 0.0353(14) 0.0317(12) 0.0306(12) -0.0113(9) 0.0008(10) 0.0043(10) C23 0.0299(13) 0.0294(11) 0.0172(10) -0.0052(8) -0.0020(9) 0.0030(9) C24 0.0376(15) 0.0380(13) 0.0255(11) -0.0028(10) 0.0006(10) 0.0005(11) C25 0.0571(19) 0.0336(12) 0.0273(12) 0.0047(10) 0.0083(12) 0.0016(12) C26 0.0503(17) 0.0464(14) 0.0186(11) -0.0027(10) -0.0020(11) 0.0188(13) C27 0.0316(14) 0.0510(14) 0.0245(11) -0.0113(10) -0.0057(10) 0.0074(12) C28 0.0359(14) 0.0323(12) 0.0207(10) -0.0051(9) 0.0012(10) 0.0018(10) F14 0.0648(10) 0.0239(6) 0.0283(7) 0.0025(5) 0.0008(7) 0.0057(6) F15 0.0720(11) 0.0387(8) 0.0226(7) -0.0051(6) 0.0085(7) 0.0094(7) F16 0.0523(10) 0.0251(7) 0.0445(8) -0.0123(6) 0.0011(7) 0.0075(6) F17 0.0695(12) 0.0250(7) 0.0479(9) 0.0079(6) 0.0041(8) -0.0015(7) F18 0.0629(11) 0.0414(8) 0.0302(7) 0.0021(6) 0.0171(7) -0.0075(7) F24 0.0426(9) 0.0490(9) 0.0515(9) 0.0070(7) -0.0028(7) -0.0155(7) F25 0.0848(14) 0.0462(9) 0.0462(9) 0.0171(7) 0.0077(9) -0.0036(9) F26 0.0729(12) 0.0599(10) 0.0273(7) 0.0024(7) -0.0077(7) 0.0301(9) F27 0.0369(9) 0.0769(11) 0.0439(9) -0.0034(8) -0.0147(7) 0.0045(8) F28 0.0379(9) 0.0441(8) 0.0371(8) 0.0003(6) -0.0030(6) -0.0098(7) C2 0.0436(18) 0.079(2) 0.0365(14) 0.0051(14) 0.0065(13) 0.0174(16) C3 0.0428(17) 0.0470(15) 0.0564(18) -0.0111(13) -0.0091(14) 0.0113(13) C4 0.0352(15) 0.0342(13) 0.0529(16) 0.0093(12) -0.0074(12) -0.0018(11) C5 0.0328(14) 0.0436(14) 0.0302(12) 0.0068(10) -0.0025(10) 0.0027(11) C6 0.0307(14) 0.0317(12) 0.0472(14) 0.0059(11) -0.0172(11) 0.0026(10) C7 0.0300(15) 0.0564(17) 0.0568(17) 0.0338(14) -0.0037(13) -0.0004(13) C8 0.069(2) 0.0365(15) 0.088(2) -0.0072(15) -0.0411(19) 0.0074(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge N1 1.8325(17) . ? Ge N2 1.8385(17) . ? Ge N3 2.1182(19) . ? Ge Cl2 2.1719(6) . ? Ge Cl1 2.2400(6) . ? N3 C1 1.481(3) . ? N3 C21 1.483(3) . ? N3 C11 1.485(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N1 C13 1.408(2) . ? N1 C12 1.455(3) . ? C11 C12 1.523(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.385(3) . ? C13 C18 1.387(3) . ? C14 F14 1.345(2) . ? C14 C15 1.382(3) . ? C15 F15 1.344(2) . ? C15 C16 1.368(3) . ? C16 F16 1.343(2) . ? C16 C17 1.379(3) . ? C17 F17 1.343(2) . ? C17 C18 1.375(3) . ? C18 F18 1.332(2) . ? N2 C23 1.410(3) . ? N2 C22 1.465(3) . ? C21 C22 1.506(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.388(3) . ? C23 C28 1.389(3) . ? C24 F24 1.346(3) . ? C24 C25 1.378(3) . ? C25 F25 1.336(3) . ? C25 C26 1.375(4) . ? C26 F26 1.342(3) . ? C26 C27 1.373(4) . ? C27 F27 1.344(3) . ? C27 C28 1.379(3) . ? C28 F28 1.343(3) . ? C2 C3 1.362(4) . ? C2 C7 1.390(4) . ? C2 H2 0.9500 . ? C3 C4 1.363(4) . ? C3 H3 0.9500 . ? C4 C5 1.379(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.390(4) . ? C6 C8 1.509(4) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C31 C36 1.332(10) . ? C31 C32 1.427(9) . ? C31 C37 1.485(10) . ? C32 C33 1.442(11) . ? C32 H32 0.9500 . ? C33 C34 1.375(12) . ? C33 H33 0.9500 . ? C34 C35 1.276(10) . ? C34 H34 0.9500 . ? C35 C36 1.414(10) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ge N2 126.55(8) . . ? N1 Ge N3 82.37(8) . . ? N2 Ge N3 83.11(8) . . ? N1 Ge Cl2 118.60(6) . . ? N2 Ge Cl2 113.11(6) . . ? N3 Ge Cl2 92.24(6) . . ? N1 Ge Cl1 94.15(6) . . ? N2 Ge Cl1 95.52(6) . . ? N3 Ge Cl1 174.35(6) . . ? Cl2 Ge Cl1 93.34(3) . . ? C1 N3 C21 110.46(18) . . ? C1 N3 C11 110.4(2) . . ? C21 N3 C11 112.24(19) . . ? C1 N3 Ge 117.12(16) . . ? C21 N3 Ge 105.29(14) . . ? C11 N3 Ge 101.01(13) . . ? N3 C1 H1A 109.5 . . ? N3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C13 N1 C12 116.12(17) . . ? C13 N1 Ge 124.25(14) . . ? C12 N1 Ge 119.00(14) . . ? N3 C11 C12 107.4(2) . . ? N3 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? N3 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N1 C12 C11 106.52(19) . . ? N1 C12 H12A 110.4 . . ? C11 C12 H12A 110.4 . . ? N1 C12 H12B 110.4 . . ? C11 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C14 C13 C18 116.73(18) . . ? C14 C13 N1 121.42(19) . . ? C18 C13 N1 121.83(19) . . ? F14 C14 C15 118.34(19) . . ? F14 C14 C13 119.71(18) . . ? C15 C14 C13 121.96(19) . . ? F15 C15 C16 119.89(18) . . ? F15 C15 C14 120.35(19) . . ? C16 C15 C14 119.76(19) . . ? F16 C16 C15 119.71(19) . . ? F16 C16 C17 120.53(19) . . ? C15 C16 C17 119.76(19) . . ? F17 C17 C18 121.0(2) . . ? F17 C17 C16 119.21(19) . . ? C18 C17 C16 119.82(19) . . ? F18 C18 C17 118.8(2) . . ? F18 C18 C13 119.28(19) . . ? C17 C18 C13 121.94(19) . . ? C23 N2 C22 116.24(17) . . ? C23 N2 Ge 122.53(14) . . ? C22 N2 Ge 118.74(14) . . ? N3 C21 C22 108.80(17) . . ? N3 C21 H21A 109.9 . . ? C22 C21 H21A 109.9 . . ? N3 C21 H21B 109.9 . . ? C22 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? N2 C22 C21 108.20(18) . . ? N2 C22 H22A 110.1 . . ? C21 C22 H22A 110.1 . . ? N2 C22 H22B 110.1 . . ? C21 C22 H22B 110.1 . . ? H22A C22 H22B 108.4 . . ? C24 C23 C28 116.3(2) . . ? C24 C23 N2 122.2(2) . . ? C28 C23 N2 121.4(2) . . ? F24 C24 C25 118.8(2) . . ? F24 C24 C23 118.7(2) . . ? C25 C24 C23 122.5(2) . . ? F25 C25 C26 119.9(2) . . ? F25 C25 C24 120.7(3) . . ? C26 C25 C24 119.4(2) . . ? F26 C26 C27 119.6(3) . . ? F26 C26 C25 120.4(2) . . ? C27 C26 C25 119.9(2) . . ? F27 C27 C26 119.9(2) . . ? F27 C27 C28 120.2(2) . . ? C26 C27 C28 119.9(2) . . ? F28 C28 C27 118.4(2) . . ? F28 C28 C23 119.6(2) . . ? C27 C28 C23 121.9(2) . . ? C3 C2 C7 119.8(3) . . ? C3 C2 H2 120.1 . . ? C7 C2 H2 120.1 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 117.7(2) . . ? C5 C6 C8 120.8(3) . . ? C7 C6 C8 121.5(3) . . ? C2 C7 C6 120.9(2) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C36 C31 C32 122.2(7) . . ? C36 C31 C37 117.4(7) . . ? C32 C31 C37 120.4(7) . . ? C31 C32 C33 119.7(6) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C34 C33 C32 114.3(9) . . ? C34 C33 H33 122.8 . . ? C32 C33 H33 122.8 . . ? C35 C34 C33 123.7(10) . . ? C35 C34 H34 118.1 . . ? C33 C34 H34 118.1 . . ? C34 C35 C36 125.1(8) . . ? C34 C35 H35 117.4 . . ? C36 C35 H35 117.4 . . ? C31 C36 C35 114.9(7) . . ? C31 C36 H36 122.6 . . ? C35 C36 H36 122.6 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.564 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.066 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 718434' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H11 Br2 F10 Ge N3, 1.5 (C7 H8)' _chemical_formula_sum 'C27.50 H23 Br2 F10 Ge N3' _chemical_formula_weight 817.90 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' F F 0.0171 0.0103 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.4325(5) _cell_length_b 21.6686(8) _cell_length_c 19.2039(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6005.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6049 _cell_measurement_theta_min 2.545 _cell_measurement_theta_max 29.973 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3208 _exptl_absorpt_coefficient_mu 3.768 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5195 _exptl_absorpt_correction_T_max 0.8639 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35449 _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5583 _reflns_number_gt 4173 _reflns_threshold_expression I>2\s(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^)+(0.0520P)^2^+16.6300P] 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 5583 _refine_ls_number_parameters 374 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1709 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 0.30604(5) 0.25052(3) 0.05320(5) 0.0311(2) Uani 1 1 d . . . Br1 Br 0.19932(5) 0.18834(4) 0.11986(6) 0.0488(3) Uani 1 1 d . . . Br2 Br 0.24957(6) 0.21343(4) -0.05267(5) 0.0470(3) Uani 1 1 d . . . N1 N 0.4046(4) 0.3086(3) 0.0028(3) 0.0308(14) Uani 1 1 d . . . C1 C 0.4469(6) 0.2854(4) -0.0623(4) 0.043(2) Uani 1 1 d . . . H1A H 0.5041 0.3082 -0.0718 0.065 Uiso 1 1 calc R . . H1B H 0.4035 0.2911 -0.1010 0.065 Uiso 1 1 calc R . . H1C H 0.4612 0.2414 -0.0572 0.065 Uiso 1 1 calc R . . N2 N 0.2562(4) 0.3258(3) 0.0784(4) 0.0383(16) Uani 1 1 d . . . C21 C 0.3569(5) 0.3678(4) -0.0102(4) 0.0378(18) Uani 1 1 d . . . H21A H 0.3162 0.3641 -0.0515 0.045 Uiso 1 1 calc R . . H21B H 0.4029 0.4007 -0.0192 0.045 Uiso 1 1 calc R . . C22 C 0.2992(5) 0.3839(3) 0.0540(4) 0.0376(18) Uani 1 1 d . . . H22A H 0.3392 0.4016 0.0908 0.045 Uiso 1 1 calc R . . H22B H 0.2509 0.4145 0.0419 0.045 Uiso 1 1 calc R . . C23 C 0.1864(5) 0.3342(3) 0.1288(4) 0.0339(18) Uani 1 1 d . . . C24 C 0.0966(5) 0.3496(3) 0.1113(4) 0.0297(16) Uani 1 1 d . . . C25 C 0.0268(5) 0.3576(3) 0.1570(4) 0.0321(17) Uani 1 1 d . . . C26 C 0.0452(5) 0.3508(4) 0.2268(5) 0.0389(19) Uani 1 1 d . . . C27 C 0.1334(6) 0.3366(5) 0.2474(4) 0.049(2) Uani 1 1 d . . . C28 C 0.2018(5) 0.3274(4) 0.1991(5) 0.047(2) Uani 1 1 d . . . N3 N 0.4107(4) 0.2172(3) 0.0922(3) 0.0300(14) Uani 1 1 d . . . C31 C 0.4775(5) 0.3137(3) 0.0570(4) 0.0331(17) Uani 1 1 d . . . H31A H 0.4551 0.3391 0.0964 0.040 Uiso 1 1 calc R . . H31B H 0.5336 0.3334 0.0374 0.040 Uiso 1 1 calc R . . C32 C 0.4997(5) 0.2491(3) 0.0818(5) 0.0367(19) Uani 1 1 d . . . H32A H 0.5375 0.2271 0.0466 0.044 Uiso 1 1 calc R . . H32B H 0.5350 0.2506 0.1259 0.044 Uiso 1 1 calc R . . C33 C 0.4166(4) 0.1610(3) 0.1298(4) 0.0290(16) Uani 1 1 d . . . C34 C 0.4051(5) 0.1042(3) 0.0972(4) 0.0341(17) Uani 1 1 d . . . C35 C 0.4147(5) 0.0496(3) 0.1330(5) 0.0388(19) Uani 1 1 d . . . C36 C 0.4385(5) 0.0498(4) 0.2021(5) 0.0393(19) Uani 1 1 d . . . C37 C 0.4503(5) 0.1055(4) 0.2355(4) 0.0382(18) Uani 1 1 d . . . F24 F 0.0770(3) 0.3562(2) 0.0421(2) 0.0441(11) Uani 1 1 d . . . F25 F -0.0590(3) 0.3709(3) 0.1364(3) 0.0542(14) Uani 1 1 d . . . F26 F -0.0215(3) 0.3605(3) 0.2740(3) 0.0573(14) Uani 1 1 d . . . F27 F 0.1508(4) 0.3309(4) 0.3159(3) 0.086(2) Uani 1 1 d . . . F28 F 0.2872(3) 0.3124(3) 0.2214(3) 0.0709(18) Uani 1 1 d . . . F34 F 0.3839(3) 0.1016(2) 0.0291(3) 0.0444(11) Uani 1 1 d . . . F35 F 0.4032(4) -0.0047(2) 0.1005(3) 0.0534(13) Uani 1 1 d . . . F36 F 0.4496(4) -0.0030(2) 0.2373(3) 0.0553(14) Uani 1 1 d . . . F37 F 0.4727(4) 0.1065(2) 0.3037(3) 0.0602(15) Uani 1 1 d . . . C38 C 0.4387(5) 0.1603(3) 0.2000(4) 0.0374(18) Uani 1 1 d . . . F38 F 0.4507(4) 0.2129(2) 0.2346(3) 0.0491(12) Uani 1 1 d . . . C11 C 0.6936(7) 0.0169(6) 0.2067(7) 0.078(4) Uani 1 1 d . . . C12 C 0.6645(6) 0.0065(5) 0.1359(6) 0.056(3) Uani 1 1 d . . . H12 H 0.6566 -0.0341 0.1180 0.068 Uiso 1 1 calc R . . C13 C 0.6491(7) 0.0560(7) 0.0965(8) 0.079(4) Uani 1 1 d . . . H13 H 0.6295 0.0494 0.0498 0.095 Uiso 1 1 calc R . . C14 C 0.6593(7) 0.1143(7) 0.1178(7) 0.076(4) Uani 1 1 d . . . H14 H 0.6466 0.1477 0.0872 0.091 Uiso 1 1 calc R . . C15 C 0.6882(6) 0.1252(7) 0.1844(6) 0.071(3) Uani 1 1 d . . . H15 H 0.6972 0.1664 0.1997 0.085 Uiso 1 1 calc R . . C16 C 0.7045(6) 0.0773(5) 0.2298(6) 0.060(3) Uani 1 1 d . . . H16 H 0.7231 0.0853 0.2764 0.072 Uiso 1 1 calc R . . C17 C 0.7089(10) -0.0302(8) 0.2546(9) 0.118(6) Uani 1 1 d . . . H17A H 0.7269 -0.0123 0.2995 0.177 Uiso 1 1 calc R . . H17B H 0.7587 -0.0571 0.2376 0.177 Uiso 1 1 calc R . . H17C H 0.6521 -0.0543 0.2604 0.177 Uiso 1 1 calc R . . C3 C 0.9799(10) 0.9947(8) 0.9296(7) 0.075(3) Uiso 0.50 1 d PGD A -1 H3 H 0.9518 0.9851 0.8862 0.090 Uiso 0.50 1 calc PR A -1 C2 C 1.0640(10) 1.0260(7) 0.9313(7) 0.075(3) Uiso 0.50 1 d PG A -1 H2 H 1.0933 1.0378 0.8891 0.090 Uiso 0.50 1 calc PR A -1 C4 C 1.1050(8) 1.0401(7) 0.9948(9) 0.075(3) Uiso 0.50 1 d PG A -1 H4 H 1.1625 1.0615 0.9960 0.090 Uiso 0.50 1 calc PR A -1 C6 C 1.0621(10) 1.0228(8) 1.0566(7) 0.075(3) Uiso 0.50 1 d PG A -1 H6 H 1.0902 1.0324 1.1000 0.090 Uiso 0.50 1 calc PR A -1 C5 C 0.9781(10) 0.9915(8) 1.0549(7) 0.075(3) Uiso 0.50 1 d PGD A -1 H5 H 0.9487 0.9797 1.0971 0.090 Uiso 0.50 1 calc PR A -1 C7 C 0.9370(8) 0.9774(8) 0.9914(8) 0.075(3) Uiso 0.50 1 d PGD A -1 C8 C 0.8470(15) 0.9517(11) 0.9932(12) 0.075(3) Uiso 0.50 1 d PD A -1 H8A H 0.8304 0.9420 1.0415 0.113 Uiso 0.50 1 calc PR A -1 H8B H 0.8457 0.9139 0.9652 0.113 Uiso 0.50 1 calc PR A -1 H8C H 0.8025 0.9814 0.9742 0.113 Uiso 0.50 1 calc PR A -1 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 0.0188(3) 0.0268(4) 0.0477(5) 0.0059(3) -0.0022(3) -0.0026(3) Br1 0.0244(4) 0.0367(4) 0.0854(7) 0.0214(4) 0.0046(4) -0.0054(3) Br2 0.0330(4) 0.0464(5) 0.0615(6) -0.0031(4) -0.0181(4) -0.0033(4) N1 0.019(3) 0.030(3) 0.044(4) 0.004(3) -0.001(3) -0.004(2) C1 0.037(4) 0.048(5) 0.044(5) 0.001(4) 0.008(4) -0.001(4) N2 0.027(3) 0.027(3) 0.060(5) 0.011(3) 0.014(3) -0.004(3) C21 0.025(3) 0.038(4) 0.050(5) 0.007(4) 0.003(4) -0.004(3) C22 0.030(4) 0.030(4) 0.054(5) 0.014(4) 0.007(4) -0.003(3) C23 0.026(4) 0.022(3) 0.054(5) 0.008(3) 0.008(4) 0.004(3) C24 0.032(4) 0.027(4) 0.030(4) -0.001(3) -0.006(3) 0.001(3) C25 0.026(3) 0.024(3) 0.046(5) 0.008(3) -0.004(3) 0.005(3) C26 0.031(4) 0.041(4) 0.045(5) 0.013(4) 0.008(4) -0.004(3) C27 0.040(5) 0.076(6) 0.031(5) 0.018(4) -0.006(4) -0.013(4) C28 0.022(4) 0.063(6) 0.055(6) 0.026(5) -0.007(4) -0.007(4) N3 0.021(3) 0.028(3) 0.041(4) 0.009(3) -0.003(3) -0.005(2) C31 0.024(3) 0.027(4) 0.049(5) 0.006(4) -0.001(3) -0.006(3) C32 0.022(3) 0.032(4) 0.056(5) 0.004(4) -0.016(4) -0.006(3) C33 0.018(3) 0.025(3) 0.044(5) 0.007(3) -0.003(3) 0.002(3) C34 0.027(4) 0.031(4) 0.044(5) -0.001(3) -0.001(3) 0.000(3) C35 0.032(4) 0.021(4) 0.062(6) 0.002(4) 0.001(4) 0.001(3) C36 0.037(4) 0.031(4) 0.050(5) 0.012(4) 0.000(4) 0.000(3) C37 0.038(4) 0.039(4) 0.037(5) 0.011(4) 0.000(4) -0.002(4) F24 0.046(3) 0.049(3) 0.038(3) -0.001(2) -0.002(2) 0.008(2) F25 0.026(2) 0.073(3) 0.063(3) -0.005(3) -0.006(2) 0.020(2) F26 0.042(3) 0.070(3) 0.059(3) -0.004(3) 0.021(3) -0.005(3) F27 0.052(3) 0.169(7) 0.038(3) 0.032(4) -0.003(3) -0.005(4) F28 0.025(2) 0.122(5) 0.065(4) 0.035(4) -0.010(2) 0.005(3) F34 0.051(3) 0.038(2) 0.044(3) 0.000(2) -0.006(2) -0.004(2) F35 0.068(3) 0.027(2) 0.066(4) -0.003(2) -0.007(3) -0.001(2) F36 0.059(3) 0.035(2) 0.072(4) 0.024(2) 0.000(3) 0.006(2) F37 0.081(4) 0.057(3) 0.043(3) 0.007(3) -0.019(3) 0.002(3) C38 0.037(4) 0.027(4) 0.048(5) -0.004(4) -0.008(4) -0.002(3) F38 0.062(3) 0.037(2) 0.049(3) -0.003(2) -0.008(3) -0.004(2) C11 0.039(5) 0.083(8) 0.111(11) 0.031(8) 0.016(6) 0.000(5) C12 0.040(5) 0.059(6) 0.070(8) -0.016(5) 0.005(5) -0.016(4) C13 0.045(6) 0.096(9) 0.096(10) 0.027(8) 0.016(6) -0.002(6) C14 0.036(5) 0.100(10) 0.091(10) 0.035(8) 0.014(6) 0.004(6) C15 0.034(5) 0.125(10) 0.054(7) 0.003(7) -0.002(5) 0.011(6) C16 0.039(5) 0.066(6) 0.074(7) -0.022(6) 0.007(5) -0.008(5) C17 0.069(8) 0.151(15) 0.135(14) 0.029(13) -0.009(9) 0.014(9) _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 N3 1.834(6) . ? Ge1 N2 1.848(6) . ? Ge1 N1 2.132(6) . ? Ge1 Br2 2.3331(12) . ? Ge1 Br1 2.4140(11) . ? N1 C31 1.484(9) . ? N1 C21 1.477(9) . ? N1 C1 1.479(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N2 C23 1.409(10) . ? N2 C22 1.480(9) . ? C21 C22 1.528(11) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.379(10) . ? C23 C28 1.376(12) . ? C24 C25 1.347(11) . ? C24 F24 1.367(8) . ? C25 F25 1.332(8) . ? C25 C26 1.375(12) . ? C26 F26 1.339(9) . ? C26 C27 1.368(11) . ? C27 F27 1.344(10) . ? C27 C28 1.370(13) . ? C28 F28 1.344(9) . ? N3 C33 1.419(9) . ? N3 C32 1.472(9) . ? C31 C32 1.513(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C38 1.386(11) . ? C33 C34 1.391(10) . ? C34 F34 1.344(9) . ? C34 C35 1.374(11) . ? C35 F35 1.343(9) . ? C35 C36 1.370(12) . ? C36 F36 1.337(9) . ? C36 C37 1.379(11) . ? C37 F37 1.349(9) . ? C37 C38 1.379(11) . ? C38 F38 1.331(9) . ? C11 C17 1.390(18) . ? C11 C16 1.390(16) . ? C11 C12 1.442(17) . ? C12 C13 1.332(16) . ? C12 H12 0.9500 . ? C13 C14 1.336(17) . ? C13 H13 0.9500 . ? C14 C15 1.366(17) . ? C14 H14 0.9500 . ? C15 C16 1.375(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C3 C2 1.3900 . ? C3 C7 1.3900 . ? C3 H3 0.9500 . ? C2 C4 1.3900 . ? C2 H2 0.9500 . ? C4 C6 1.3900 . ? C4 H4 0.9500 . ? C6 C5 1.3900 . ? C6 H6 0.9500 . ? C5 C7 1.3900 . ? C5 H5 0.9500 . ? C7 C8 1.41(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Ge1 N2 124.1(3) . . ? N3 Ge1 N1 82.4(2) . . ? N2 Ge1 N1 81.8(2) . . ? N3 Ge1 Br2 120.5(2) . . ? N2 Ge1 Br2 113.4(2) . . ? N1 Ge1 Br2 92.34(17) . . ? N3 Ge1 Br1 95.13(18) . . ? N2 Ge1 Br1 96.06(19) . . ? N1 Ge1 Br1 174.97(18) . . ? Br2 Ge1 Br1 92.69(4) . . ? C31 N1 C21 112.6(6) . . ? C31 N1 C1 109.0(6) . . ? C21 N1 C1 110.2(6) . . ? C31 N1 Ge1 101.4(4) . . ? C21 N1 Ge1 106.1(4) . . ? C1 N1 Ge1 117.3(5) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C23 N2 C22 114.1(6) . . ? C23 N2 Ge1 124.9(5) . . ? C22 N2 Ge1 120.3(5) . . ? N1 C21 C22 108.4(6) . . ? N1 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? N1 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? N2 C22 C21 106.9(6) . . ? N2 C22 H22A 110.3 . . ? C21 C22 H22A 110.3 . . ? N2 C22 H22B 110.3 . . ? C21 C22 H22B 110.3 . . ? H22A C22 H22B 108.6 . . ? C24 C23 C28 114.6(7) . . ? C24 C23 N2 122.4(7) . . ? C28 C23 N2 122.9(7) . . ? C25 C24 F24 117.7(6) . . ? C25 C24 C23 125.1(7) . . ? F24 C24 C23 117.2(7) . . ? C24 C25 F25 122.0(7) . . ? C24 C25 C26 118.5(7) . . ? F25 C25 C26 119.4(7) . . ? F26 C26 C27 120.5(8) . . ? F26 C26 C25 120.4(7) . . ? C27 C26 C25 119.1(7) . . ? F27 C27 C26 118.5(8) . . ? F27 C27 C28 120.9(8) . . ? C26 C27 C28 120.5(8) . . ? F28 C28 C27 118.7(8) . . ? F28 C28 C23 119.2(8) . . ? C27 C28 C23 122.1(7) . . ? C33 N3 C32 114.7(5) . . ? C33 N3 Ge1 126.5(4) . . ? C32 N3 Ge1 118.6(5) . . ? N1 C31 C32 107.6(6) . . ? N1 C31 H31A 110.2 . . ? C32 C31 H31A 110.2 . . ? N1 C31 H31B 110.2 . . ? C32 C31 H31B 110.2 . . ? H31A C31 H31B 108.5 . . ? N3 C32 C31 106.9(6) . . ? N3 C32 H32A 110.3 . . ? C31 C32 H32A 110.3 . . ? N3 C32 H32B 110.3 . . ? C31 C32 H32B 110.3 . . ? H32A C32 H32B 108.6 . . ? C38 C33 C34 117.1(7) . . ? C38 C33 N3 121.2(7) . . ? C34 C33 N3 121.6(7) . . ? F34 C34 C35 118.3(7) . . ? F34 C34 C33 120.1(7) . . ? C35 C34 C33 121.6(8) . . ? F35 C35 C34 120.6(8) . . ? F35 C35 C36 118.9(7) . . ? C34 C35 C36 120.5(7) . . ? F36 C36 C37 119.9(8) . . ? F36 C36 C35 121.2(7) . . ? C37 C36 C35 118.9(7) . . ? F37 C37 C36 119.7(7) . . ? F37 C37 C38 119.7(7) . . ? C36 C37 C38 120.6(7) . . ? F38 C38 C37 118.4(7) . . ? F38 C38 C33 120.3(7) . . ? C37 C38 C33 121.2(7) . . ? C17 C11 C16 117.5(14) . . ? C17 C11 C12 123.8(13) . . ? C16 C11 C12 118.7(11) . . ? C13 C12 C11 117.3(11) . . ? C13 C12 H12 121.3 . . ? C11 C12 H12 121.3 . . ? C12 C13 C14 124.7(14) . . ? C12 C13 H13 117.7 . . ? C14 C13 H13 117.7 . . ? C13 C14 C15 119.0(13) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C16 121.0(13) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 119.3(12) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 C3 C7 120.0 . . ? C2 C3 H3 120.0 . . ? C7 C3 H3 120.0 . . ? C3 C2 C4 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C2 H2 120.0 . . ? C6 C4 C2 120.0 . . ? C6 C4 H4 120.0 . . ? C2 C4 H4 120.0 . . ? C4 C6 C5 120.0 . . ? C4 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C7 C5 C6 120.0 . . ? C7 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C7 C3 120.0 . . ? C5 C7 C8 117.2(13) . . ? C3 C7 C8 122.5(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.087 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.124 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 718435' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Cl2 F10 Ge N3, 1.5 (C7 H8)' _chemical_formula_sum 'C33.50 H27 Cl2 F10 Ge N3' _chemical_formula_weight 805.07 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' F F 0.0171 0.0103 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3340(5) _cell_length_b 19.8573(12) _cell_length_c 22.7800(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.994(2) _cell_angle_gamma 90.00 _cell_volume 3317.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3369 _cell_measurement_theta_min 2.720 _cell_measurement_theta_max 34.190 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1620 _exptl_absorpt_coefficient_mu 1.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6516 _exptl_absorpt_correction_T_max 0.7202 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17319 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7198 _reflns_number_gt 5771 _reflns_threshold_expression I>2\s(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^)+(0.0501P)^2^+2.2152P] 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 7198 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1054 _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 Ge Ge 0.58555(4) 0.214324(14) 0.254797(12) 0.01826(9) Uani 1 1 d . . . Cl1 Cl 0.75669(10) 0.13675(4) 0.21160(3) 0.02410(16) Uani 1 1 d . . . Cl2 Cl 0.78256(10) 0.29435(4) 0.23953(4) 0.03106(18) Uani 1 1 d . . . N1 N 0.4086(3) 0.28538(11) 0.29722(10) 0.0206(5) Uani 1 1 d . . . C1 C 0.4129(4) 0.35633(14) 0.27360(13) 0.0232(6) Uani 1 1 d . . . H1A H 0.5372 0.3746 0.2801 0.028 Uiso 1 1 calc R . . H1B H 0.3905 0.3545 0.2306 0.028 Uiso 1 1 calc R . . C2 C 0.2787(4) 0.40461(14) 0.29961(13) 0.0238(6) Uani 1 1 d . . . C3 C 0.1111(4) 0.41772(15) 0.27269(14) 0.0275(7) Uani 1 1 d . . . H3 H 0.0778 0.3946 0.2376 0.033 Uiso 1 1 calc R . . C4 C -0.0086(5) 0.46429(15) 0.29637(15) 0.0329(7) Uani 1 1 d . . . H4 H -0.1234 0.4725 0.2778 0.039 Uiso 1 1 calc R . . C5 C 0.0408(5) 0.49863(16) 0.34717(15) 0.0347(8) Uani 1 1 d . . . H5 H -0.0399 0.5307 0.3635 0.042 Uiso 1 1 calc R . . C6 C 0.2073(5) 0.48609(15) 0.37406(14) 0.0330(7) Uani 1 1 d . . . H6 H 0.2401 0.5093 0.4092 0.040 Uiso 1 1 calc R . . C7 C 0.3271(5) 0.44012(15) 0.35041(13) 0.0278(7) Uani 1 1 d . . . H7 H 0.4426 0.4327 0.3688 0.033 Uiso 1 1 calc R . . N2 N 0.3871(3) 0.20418(12) 0.20567(10) 0.0218(5) Uani 1 1 d . . . C21 C 0.2281(4) 0.25351(14) 0.28574(12) 0.0218(6) Uani 1 1 d . . . H21A H 0.1293 0.2850 0.2962 0.026 Uiso 1 1 calc R . . H21B H 0.2160 0.2123 0.3099 0.026 Uiso 1 1 calc R . . C22 C 0.2136(4) 0.23585(15) 0.22136(13) 0.0234(6) Uani 1 1 d . . . H22A H 0.1110 0.2043 0.2142 0.028 Uiso 1 1 calc R . . H22B H 0.1924 0.2769 0.1976 0.028 Uiso 1 1 calc R . . C23 C 0.3954(4) 0.17846(14) 0.14800(12) 0.0205(6) Uani 1 1 d . . . C24 C 0.4148(4) 0.22076(14) 0.10001(13) 0.0252(6) Uani 1 1 d . . . C25 C 0.4170(4) 0.19645(16) 0.04352(13) 0.0294(7) Uani 1 1 d . . . C26 C 0.4004(4) 0.12877(17) 0.03333(13) 0.0293(7) Uani 1 1 d . . . C27 C 0.3813(4) 0.08553(15) 0.07983(14) 0.0299(7) Uani 1 1 d . . . C28 C 0.3783(4) 0.11026(15) 0.13607(12) 0.0233(6) Uani 1 1 d . . . N3 N 0.6005(4) 0.17781(11) 0.32878(10) 0.0243(5) Uani 1 1 d . . . C31 C 0.4634(4) 0.28292(14) 0.36013(12) 0.0258(6) Uani 1 1 d . . . H31A H 0.3646 0.3013 0.3845 0.031 Uiso 1 1 calc R . . H31B H 0.5742 0.3105 0.3669 0.031 Uiso 1 1 calc R . . C32 C 0.5012(5) 0.21002(15) 0.37701(13) 0.0290(7) Uani 1 1 d . . . H32A H 0.5753 0.2082 0.4137 0.035 Uiso 1 1 calc R . . H32B H 0.3850 0.1860 0.3836 0.035 Uiso 1 1 calc R . . C33 C 0.6366(4) 0.10856(14) 0.33769(12) 0.0228(6) Uani 1 1 d . . . C34 C 0.8096(4) 0.08560(15) 0.35211(13) 0.0255(6) Uani 1 1 d . . . C35 C 0.8466(5) 0.01830(16) 0.36107(14) 0.0302(7) Uani 1 1 d . . . C36 C 0.7065(5) -0.02781(14) 0.35699(13) 0.0302(7) Uani 1 1 d . . . C37 C 0.5324(5) -0.00689(15) 0.34275(14) 0.0302(7) Uani 1 1 d . . . C38 C 0.4997(4) 0.06035(15) 0.33337(13) 0.0266(7) Uani 1 1 d . . . F24 F 0.4327(3) 0.28693(8) 0.10864(8) 0.0368(5) Uani 1 1 d . . . F25 F 0.4364(3) 0.23916(11) -0.00171(8) 0.0483(6) Uani 1 1 d . . . F26 F 0.4045(3) 0.10496(11) -0.02156(8) 0.0458(5) Uani 1 1 d . . . F27 F 0.3629(3) 0.01915(9) 0.06934(9) 0.0418(5) Uani 1 1 d . . . F28 F 0.3571(3) 0.06649(9) 0.18049(8) 0.0346(4) Uani 1 1 d . . . F34 F 0.9499(3) 0.12949(9) 0.35627(8) 0.0353(4) Uani 1 1 d . . . F35 F 1.0158(3) -0.00283(9) 0.37456(9) 0.0450(5) Uani 1 1 d . . . F36 F 0.7413(3) -0.09337(8) 0.36642(8) 0.0413(5) Uani 1 1 d . . . F37 F 0.3974(3) -0.05221(9) 0.33743(9) 0.0445(5) Uani 1 1 d . . . F38 F 0.3292(3) 0.07986(10) 0.31885(9) 0.0394(5) Uani 1 1 d . . . C8 C 0.9168(5) 0.2383(2) 1.03165(19) 0.0538(11) Uani 1 1 d . . . C9 C 0.9050(6) 0.1672(3) 1.0397(2) 0.0661(13) Uani 1 1 d . . . H9 H 0.8931 0.1484 1.0778 0.079 Uiso 1 1 calc R . . C10 C 0.9114(7) 0.1258(2) 0.9900(2) 0.0647(13) Uani 1 1 d . . . H10 H 0.9035 0.0782 0.9940 0.078 Uiso 1 1 calc R . . C11 C 0.9288(7) 0.1539(2) 0.9363(2) 0.0652(13) Uani 1 1 d . . . H11 H 0.9380 0.1254 0.9030 0.078 Uiso 1 1 calc R . . C12 C 0.9335(7) 0.2216(2) 0.9286(2) 0.0612(12) Uani 1 1 d . . . H12 H 0.9394 0.2401 0.8902 0.073 Uiso 1 1 calc R . . C13 C 0.9296(6) 0.2624(2) 0.97569(19) 0.0539(11) Uani 1 1 d . . . H13 H 0.9361 0.3097 0.9698 0.065 Uiso 1 1 calc R . . C14 C 0.9101(8) 0.2839(3) 1.0829(2) 0.0845(17) Uani 1 1 d . . . H14A H 0.8081 0.3154 1.0778 0.127 Uiso 1 1 calc R . . H14B H 1.0245 0.3092 1.0862 0.127 Uiso 1 1 calc R . . H14C H 0.8930 0.2574 1.1187 0.127 Uiso 1 1 calc R . . C15 C 0.3850(7) 0.4597(3) 0.9932(3) 0.0437(19) Uiso 0.50 1 d PG A -1 C16 C 0.5562(8) 0.4337(3) 1.0074(3) 0.0452(19) Uiso 0.50 1 d PG A -1 H16 H 0.5725 0.3865 1.0111 0.054 Uiso 0.50 1 calc PR A -1 C17 C 0.7034(7) 0.4769(4) 1.0160(3) 0.070(3) Uiso 0.50 1 d PG A -1 H17 H 0.8204 0.4591 1.0257 0.084 Uiso 0.50 1 calc PR A -1 C18 C 0.6795(8) 0.5461(3) 1.0105(3) 0.065(3) Uiso 0.50 1 d PG A -1 H18 H 0.7802 0.5756 1.0163 0.078 Uiso 0.50 1 calc PR A -1 C19 C 0.5084(9) 0.5721(3) 0.9963(3) 0.073(3) Uiso 0.50 1 d PG A -1 H19 H 0.4921 0.6193 0.9925 0.087 Uiso 0.50 1 calc PR A -1 C20 C 0.3611(7) 0.5289(3) 0.9877(3) 0.049(2) Uiso 0.50 1 d PG A -1 H20 H 0.2442 0.5467 0.9780 0.059 Uiso 0.50 1 calc PR A -1 C29 C 0.2305(13) 0.4113(4) 0.9846(4) 0.059(2) Uiso 0.50 1 d P A -1 H29C H 0.2615 0.3683 1.0034 0.088 Uiso 0.50 1 calc PR A -1 H29D H 0.2085 0.4041 0.9425 0.088 Uiso 0.50 1 calc PR A -1 H29A H 0.1203 0.4298 1.0022 0.088 Uiso 0.50 1 calc PR A -1 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 Ge 0.01721(16) 0.01987(15) 0.01769(15) -0.00110(12) 0.00003(11) 0.00063(12) Cl1 0.0214(4) 0.0273(4) 0.0237(4) -0.0039(3) 0.0023(3) 0.0038(3) Cl2 0.0202(4) 0.0252(4) 0.0479(5) 0.0000(3) 0.0032(3) -0.0016(3) N1 0.0220(13) 0.0209(12) 0.0187(12) -0.0007(10) -0.0006(10) -0.0002(10) C1 0.0246(16) 0.0221(14) 0.0230(15) 0.0005(12) -0.0014(12) -0.0029(12) C2 0.0262(16) 0.0190(14) 0.0263(15) 0.0031(12) 0.0025(13) 0.0002(12) C3 0.0300(17) 0.0247(15) 0.0279(16) 0.0027(13) -0.0004(13) -0.0014(13) C4 0.0287(18) 0.0277(16) 0.0422(19) 0.0050(14) 0.0000(15) 0.0021(13) C5 0.0338(19) 0.0268(16) 0.044(2) -0.0009(15) 0.0098(15) 0.0054(14) C6 0.043(2) 0.0236(16) 0.0319(17) -0.0050(13) 0.0009(15) 0.0032(14) C7 0.0332(18) 0.0244(15) 0.0257(16) 0.0015(12) -0.0008(13) 0.0018(13) N2 0.0147(12) 0.0312(13) 0.0194(12) -0.0068(10) -0.0006(9) 0.0015(10) C21 0.0205(15) 0.0207(14) 0.0243(15) -0.0007(11) 0.0058(12) -0.0007(11) C22 0.0172(15) 0.0270(15) 0.0260(15) -0.0057(12) 0.0001(12) 0.0011(12) C23 0.0164(14) 0.0266(15) 0.0185(14) -0.0018(11) -0.0011(11) 0.0007(11) C24 0.0259(16) 0.0219(15) 0.0278(16) -0.0014(12) 0.0016(13) 0.0004(12) C25 0.0306(17) 0.0371(17) 0.0205(15) 0.0044(13) 0.0021(13) 0.0006(14) C26 0.0288(17) 0.0429(19) 0.0162(15) -0.0080(13) -0.0013(12) 0.0045(14) C27 0.0296(17) 0.0267(16) 0.0331(17) -0.0085(13) -0.0057(14) -0.0014(13) C28 0.0207(15) 0.0279(15) 0.0212(14) 0.0023(12) -0.0037(12) -0.0042(12) N3 0.0351(15) 0.0183(12) 0.0194(12) -0.0010(10) 0.0009(11) 0.0059(10) C31 0.0354(18) 0.0253(15) 0.0167(14) -0.0043(12) -0.0006(12) 0.0071(13) C32 0.0403(19) 0.0287(16) 0.0180(14) -0.0018(12) 0.0023(13) 0.0107(14) C33 0.0305(17) 0.0215(14) 0.0163(14) 0.0009(11) 0.0014(12) 0.0031(12) C34 0.0301(17) 0.0238(15) 0.0226(15) -0.0015(12) -0.0016(13) -0.0010(12) C35 0.0319(18) 0.0311(17) 0.0274(16) 0.0012(13) -0.0040(14) 0.0105(14) C36 0.047(2) 0.0184(14) 0.0251(16) 0.0008(12) 0.0025(14) 0.0036(14) C37 0.0361(19) 0.0269(16) 0.0276(16) -0.0029(13) 0.0035(14) -0.0076(14) C38 0.0276(17) 0.0279(16) 0.0244(15) -0.0014(12) 0.0029(13) 0.0022(13) F24 0.0521(13) 0.0221(9) 0.0365(10) 0.0019(8) 0.0040(9) -0.0002(8) F25 0.0687(16) 0.0508(12) 0.0256(10) 0.0130(9) 0.0051(10) -0.0010(11) F26 0.0556(14) 0.0587(13) 0.0229(10) -0.0155(9) -0.0025(9) 0.0074(11) F27 0.0552(13) 0.0245(9) 0.0453(12) -0.0129(8) -0.0101(10) -0.0021(9) F28 0.0456(12) 0.0284(9) 0.0297(10) 0.0048(8) -0.0010(8) -0.0104(8) F34 0.0300(10) 0.0278(9) 0.0479(12) 0.0000(8) -0.0044(9) -0.0006(8) F35 0.0375(12) 0.0327(10) 0.0643(14) 0.0056(10) -0.0128(10) 0.0111(9) F36 0.0639(14) 0.0198(9) 0.0403(11) 0.0034(8) 0.0010(10) 0.0054(9) F37 0.0438(13) 0.0297(10) 0.0603(14) -0.0049(9) 0.0070(10) -0.0119(9) F38 0.0278(11) 0.0375(11) 0.0527(12) -0.0019(9) -0.0007(9) 0.0007(8) C8 0.030(2) 0.077(3) 0.054(3) -0.022(2) -0.0091(18) 0.011(2) C9 0.045(3) 0.095(4) 0.058(3) 0.030(3) 0.000(2) 0.011(2) C10 0.064(3) 0.049(3) 0.081(4) 0.011(2) -0.002(3) 0.010(2) C11 0.064(3) 0.060(3) 0.072(3) -0.008(2) 0.009(3) 0.019(2) C12 0.063(3) 0.063(3) 0.058(3) 0.002(2) 0.022(2) 0.012(2) C13 0.050(3) 0.061(3) 0.050(2) 0.011(2) 0.002(2) -0.007(2) C14 0.065(3) 0.127(5) 0.062(3) -0.014(3) -0.011(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge N2 1.832(2) . ? Ge N3 1.836(2) . ? Ge N1 2.157(2) . ? Ge Cl2 2.1798(8) . ? Ge Cl1 2.2269(7) . ? N1 C31 1.483(3) . ? N1 C21 1.487(4) . ? N1 C1 1.509(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.389(4) . ? C2 C7 1.396(4) . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.386(5) . ? C4 H4 0.9500 . ? C5 C6 1.380(5) . ? C5 H5 0.9500 . ? C6 C7 1.382(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? N2 C23 1.412(3) . ? N2 C22 1.469(4) . ? C21 C22 1.510(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.387(4) . ? C23 C24 1.388(4) . ? C24 F24 1.335(3) . ? C24 C25 1.375(4) . ? C25 F25 1.344(3) . ? C25 C26 1.369(4) . ? C26 F26 1.338(3) . ? C26 C27 1.373(4) . ? C27 F27 1.346(3) . ? C27 C28 1.373(4) . ? C28 F28 1.345(3) . ? N3 C33 1.414(3) . ? N3 C32 1.475(4) . ? C31 C32 1.522(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.383(4) . ? C33 C38 1.389(4) . ? C34 F34 1.351(3) . ? C34 C35 1.378(4) . ? C35 F35 1.340(4) . ? C35 C36 1.378(5) . ? C36 F36 1.343(3) . ? C36 C37 1.376(5) . ? C37 F37 1.342(4) . ? C37 C38 1.372(4) . ? C38 F38 1.345(4) . ? C8 C13 1.367(6) . ? C8 C9 1.427(7) . ? C8 C14 1.479(6) . ? C9 C10 1.400(7) . ? C9 H9 0.9500 . ? C10 C11 1.354(6) . ? C10 H10 0.9500 . ? C11 C12 1.356(6) . ? C11 H11 0.9500 . ? C12 C13 1.346(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C15 C29 1.497(10) . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C29 H29C 0.9800 . ? C29 H29D 0.9800 . ? C29 H29A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ge N3 123.47(11) . . ? N2 Ge N1 82.41(9) . . ? N3 Ge N1 82.76(10) . . ? N2 Ge Cl2 120.30(8) . . ? N3 Ge Cl2 113.90(8) . . ? N1 Ge Cl2 90.01(7) . . ? N2 Ge Cl1 95.85(7) . . ? N3 Ge Cl1 96.16(8) . . ? N1 Ge Cl1 176.91(7) . . ? Cl2 Ge Cl1 93.07(3) . . ? C31 N1 C21 112.4(2) . . ? C31 N1 C1 111.6(2) . . ? C21 N1 C1 111.0(2) . . ? C31 N1 Ge 104.87(17) . . ? C21 N1 Ge 100.59(16) . . ? C1 N1 Ge 115.76(17) . . ? C2 C1 N1 115.9(2) . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1B 108.3 . . ? N1 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C3 C2 C7 118.8(3) . . ? C3 C2 C1 121.7(3) . . ? C7 C2 C1 119.4(3) . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C2 120.2(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C23 N2 C22 115.6(2) . . ? C23 N2 Ge 124.19(18) . . ? C22 N2 Ge 119.12(18) . . ? N1 C21 C22 108.5(2) . . ? N1 C21 H21A 110.0 . . ? C22 C21 H21A 110.0 . . ? N1 C21 H21B 110.0 . . ? C22 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? N2 C22 C21 106.8(2) . . ? N2 C22 H22A 110.4 . . ? C21 C22 H22A 110.4 . . ? N2 C22 H22B 110.4 . . ? C21 C22 H22B 110.4 . . ? H22A C22 H22B 108.6 . . ? C28 C23 C24 116.5(3) . . ? C28 C23 N2 122.0(3) . . ? C24 C23 N2 121.4(2) . . ? F24 C24 C25 118.7(3) . . ? F24 C24 C23 119.4(3) . . ? C25 C24 C23 121.9(3) . . ? F25 C25 C26 120.0(3) . . ? F25 C25 C24 120.0(3) . . ? C26 C25 C24 120.1(3) . . ? F26 C26 C25 120.1(3) . . ? F26 C26 C27 120.3(3) . . ? C25 C26 C27 119.6(3) . . ? F27 C27 C26 119.1(3) . . ? F27 C27 C28 120.9(3) . . ? C26 C27 C28 120.0(3) . . ? F28 C28 C27 118.4(3) . . ? F28 C28 C23 119.7(2) . . ? C27 C28 C23 122.0(3) . . ? C33 N3 C32 114.1(2) . . ? C33 N3 Ge 121.59(18) . . ? C32 N3 Ge 119.35(18) . . ? N1 C31 C32 108.7(2) . . ? N1 C31 H31A 109.9 . . ? C32 C31 H31A 109.9 . . ? N1 C31 H31B 109.9 . . ? C32 C31 H31B 109.9 . . ? H31A C31 H31B 108.3 . . ? N3 C32 C31 108.3(2) . . ? N3 C32 H32A 110.0 . . ? C31 C32 H32A 110.0 . . ? N3 C32 H32B 110.0 . . ? C31 C32 H32B 110.0 . . ? H32A C32 H32B 108.4 . . ? C34 C33 C38 116.6(3) . . ? C34 C33 N3 121.5(3) . . ? C38 C33 N3 121.8(3) . . ? F34 C34 C35 117.9(3) . . ? F34 C34 C33 119.9(3) . . ? C35 C34 C33 122.2(3) . . ? F35 C35 C34 121.1(3) . . ? F35 C35 C36 119.6(3) . . ? C34 C35 C36 119.3(3) . . ? F36 C36 C37 120.2(3) . . ? F36 C36 C35 119.6(3) . . ? C37 C36 C35 120.2(3) . . ? F37 C37 C38 120.8(3) . . ? F37 C37 C36 119.9(3) . . ? C38 C37 C36 119.3(3) . . ? F38 C38 C37 118.5(3) . . ? F38 C38 C33 119.1(3) . . ? C37 C38 C33 122.4(3) . . ? C13 C8 C9 118.2(4) . . ? C13 C8 C14 121.7(5) . . ? C9 C8 C14 120.1(5) . . ? C10 C9 C8 118.3(4) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C11 C10 C9 119.6(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 121.9(5) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 122.3(4) . . ? C12 C13 H13 118.8 . . ? C8 C13 H13 118.8 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 120.0 . . ? C16 C15 C29 118.0(5) . . ? C20 C15 C29 122.0(5) . . ? C17 C16 C15 120.0 . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 120.0 . . ? C19 C20 H20 120.0 . . ? C15 C20 H20 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ge N1 C1 32.94(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.854 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.080 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 718436' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Br2 F10 Ge N3, 0.25 (C7 H8)' _chemical_formula_sum 'C24.75 H17 Br2 F10 Ge N3' _chemical_formula_weight 778.82 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' F F 0.0171 0.0103 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7668(5) _cell_length_b 16.6310(10) _cell_length_c 20.6711(12) _cell_angle_alpha 83.2410(10) _cell_angle_beta 80.1600(10) _cell_angle_gamma 87.9790(10) _cell_volume 2612.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3172 _cell_measurement_theta_min 2.560 _cell_measurement_theta_max 24.720 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.980 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1514 _exptl_absorpt_coefficient_mu 4.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4783 _exptl_absorpt_correction_T_max 0.8128 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15498 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.50 _reflns_number_total 9391 _reflns_number_gt 7238 _reflns_threshold_expression I>2\s(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^)+(0.0405P)^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 9391 _refine_ls_number_parameters 720 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.012 _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 0.60242(7) 0.73312(3) 0.26222(2) 0.01844(13) Uani 1 1 d . . . Br11 Br 0.47418(7) 0.82335(3) 0.18287(2) 0.02469(13) Uani 1 1 d . . . Br12 Br 0.43166(7) 0.62516(3) 0.24797(2) 0.02604(13) Uani 1 1 d . . . N11 N 0.7212(5) 0.6577(2) 0.33549(18) 0.0203(9) Uani 1 1 d . . . N12 N 0.5412(5) 0.7949(2) 0.33088(19) 0.0225(9) Uani 1 1 d . . . N13 N 0.8251(5) 0.7325(2) 0.21516(18) 0.0220(9) Uani 1 1 d . . . C1 C 0.6051(7) 0.5972(3) 0.3811(2) 0.0275(12) Uani 1 1 d . . . H1A H 0.5700 0.5568 0.3544 0.033 Uiso 1 1 calc R . . H1B H 0.4976 0.6259 0.3998 0.033 Uiso 1 1 calc R . . C2 C 0.6823(7) 0.5522(3) 0.4376(3) 0.0315(13) Uani 1 1 d . . . C3 C 0.6542(7) 0.5819(3) 0.4994(2) 0.0331(13) Uani 1 1 d . . . H3 H 0.5944 0.6322 0.5046 0.040 Uiso 1 1 calc R . . C4 C 0.7129(8) 0.5383(4) 0.5528(3) 0.0451(16) Uani 1 1 d . . . H4 H 0.6938 0.5589 0.5945 0.054 Uiso 1 1 calc R . . C5 C 0.7993(8) 0.4650(4) 0.5458(3) 0.0475(17) Uani 1 1 d . . . H5 H 0.8382 0.4350 0.5827 0.057 Uiso 1 1 calc R . . C6 C 0.8291(8) 0.4353(4) 0.4851(3) 0.0451(16) Uani 1 1 d . . . H6 H 0.8898 0.3852 0.4801 0.054 Uiso 1 1 calc R . . C7 C 0.7701(7) 0.4789(3) 0.4315(3) 0.0367(14) Uani 1 1 d . . . H7 H 0.7902 0.4581 0.3899 0.044 Uiso 1 1 calc R . . C11 C 0.7763(7) 0.7203(3) 0.3730(2) 0.0237(11) Uani 1 1 d . . . H11A H 0.8750 0.7513 0.3459 0.028 Uiso 1 1 calc R . . H11B H 0.8149 0.6944 0.4138 0.028 Uiso 1 1 calc R . . C12 C 0.6218(7) 0.7762(3) 0.3901(2) 0.0251(12) Uani 1 1 d . . . H12A H 0.5366 0.7496 0.4268 0.030 Uiso 1 1 calc R . . H12B H 0.6608 0.8266 0.4040 0.030 Uiso 1 1 calc R . . C13 C 0.4224(7) 0.8604(3) 0.3330(2) 0.0232(11) Uani 1 1 d . . . C14 C 0.4754(7) 0.9401(3) 0.3131(3) 0.0292(12) Uani 1 1 d . . . C15 C 0.3622(8) 1.0044(3) 0.3153(3) 0.0384(15) Uani 1 1 d . . . C16 C 0.1875(8) 0.9913(3) 0.3386(3) 0.0343(14) Uani 1 1 d . . . C17 C 0.1284(7) 0.9147(3) 0.3595(2) 0.0263(12) Uani 1 1 d . . . C18 C 0.2457(7) 0.8507(3) 0.3561(2) 0.0238(11) Uani 1 1 d . . . C21 C 0.8719(7) 0.6187(3) 0.2964(2) 0.0242(11) Uani 1 1 d . . . H21A H 0.8315 0.5731 0.2763 0.029 Uiso 1 1 calc R . . H21B H 0.9557 0.5970 0.3255 0.029 Uiso 1 1 calc R . . C22 C 0.9597(6) 0.6809(3) 0.2430(2) 0.0218(11) Uani 1 1 d . . . H22A H 1.0369 0.7148 0.2617 0.026 Uiso 1 1 calc R . . H22B H 1.0324 0.6534 0.2077 0.026 Uiso 1 1 calc R . . C23 C 0.8969(6) 0.7989(3) 0.1712(2) 0.0204(11) Uani 1 1 d . . . C24 C 0.9692(7) 0.8645(3) 0.1924(2) 0.0241(11) Uani 1 1 d . . . C25 C 1.0494(7) 0.9269(3) 0.1501(2) 0.0251(12) Uani 1 1 d . . . C26 C 1.0615(7) 0.9268(3) 0.0835(2) 0.0251(12) Uani 1 1 d . . . C27 C 0.9896(7) 0.8629(3) 0.0599(2) 0.0241(12) Uani 1 1 d . . . C28 C 0.9089(6) 0.8008(3) 0.1032(2) 0.0209(11) Uani 1 1 d . . . F14 F 0.6452(4) 0.95423(17) 0.29133(16) 0.0444(9) Uani 1 1 d . . . F15 F 0.4173(5) 1.08066(18) 0.29678(19) 0.0593(11) Uani 1 1 d . . . F16 F 0.0737(5) 1.05487(19) 0.34140(16) 0.0517(10) Uani 1 1 d . . . F17 F -0.0412(4) 0.90216(18) 0.38307(15) 0.0373(8) Uani 1 1 d . . . F18 F 0.1849(4) 0.77555(16) 0.37592(14) 0.0337(7) Uani 1 1 d . . . F24 F 0.9627(4) 0.86627(16) 0.25800(13) 0.0318(7) Uani 1 1 d . . . F25 F 1.1154(4) 0.98924(16) 0.17417(14) 0.0370(8) Uani 1 1 d . . . F26 F 1.1428(4) 0.98641(17) 0.04121(15) 0.0384(8) Uani 1 1 d . . . F27 F 1.0034(4) 0.86140(17) -0.00559(13) 0.0355(8) Uani 1 1 d . . . F28 F 0.8454(4) 0.74054(15) 0.07733(13) 0.0280(7) Uani 1 1 d . . . Ge2 Ge 0.99467(7) 0.36283(3) 0.19593(2) 0.01846(13) Uani 1 1 d . . . Br21 Br 1.14264(7) 0.44701(3) 0.25654(2) 0.02402(13) Uani 1 1 d . . . Br22 Br 0.71760(7) 0.41556(3) 0.23269(3) 0.02870(13) Uani 1 1 d . . . N21 N 0.8985(5) 0.2788(2) 0.13824(18) 0.0167(8) Uani 1 1 d . . . N22 N 1.0742(6) 0.2680(2) 0.23726(18) 0.0222(9) Uani 1 1 d . . . N23 N 1.0929(5) 0.4090(2) 0.11365(18) 0.0217(9) Uani 1 1 d . . . C31 C 0.7213(6) 0.2451(3) 0.1678(2) 0.0219(11) Uani 1 1 d . . . H31A H 0.6341 0.2899 0.1672 0.026 Uiso 1 1 calc R . . H31B H 0.7227 0.2245 0.2147 0.026 Uiso 1 1 calc R . . C32 C 0.6614(7) 0.1777(3) 0.1338(2) 0.0262(12) Uani 1 1 d . . . C33 C 0.6847(7) 0.0980(3) 0.1586(3) 0.0311(13) Uani 1 1 d . . . H33 H 0.7433 0.0857 0.1954 0.037 Uiso 1 1 calc R . . C34 C 0.6231(8) 0.0360(3) 0.1301(3) 0.0402(15) Uani 1 1 d . . . H34 H 0.6393 -0.0186 0.1477 0.048 Uiso 1 1 calc R . . C35 C 0.5389(8) 0.0523(3) 0.0768(3) 0.0402(15) Uani 1 1 d . . . H35 H 0.4965 0.0094 0.0576 0.048 Uiso 1 1 calc R . . C36 C 0.5166(7) 0.1318(4) 0.0514(3) 0.0397(15) Uani 1 1 d . . . H36 H 0.4594 0.1437 0.0142 0.048 Uiso 1 1 calc R . . C37 C 0.5773(7) 0.1944(3) 0.0799(3) 0.0332(13) Uani 1 1 d . . . H37 H 0.5610 0.2489 0.0622 0.040 Uiso 1 1 calc R . . C41 C 1.0377(7) 0.2150(3) 0.1377(2) 0.0210(11) Uani 1 1 d . . . H41A H 1.1468 0.2356 0.1096 0.025 Uiso 1 1 calc R . . H41B H 1.0013 0.1670 0.1197 0.025 Uiso 1 1 calc R . . C42 C 1.0680(7) 0.1922(3) 0.2079(2) 0.0247(12) Uani 1 1 d . . . H42A H 0.9719 0.1581 0.2332 0.030 Uiso 1 1 calc R . . H42B H 1.1795 0.1616 0.2083 0.030 Uiso 1 1 calc R . . C43 C 1.0907(7) 0.2583(3) 0.3047(2) 0.0222(11) Uani 1 1 d . . . C44 C 1.2510(7) 0.2596(3) 0.3249(2) 0.0254(12) Uani 1 1 d . . . C45 C 1.2657(8) 0.2504(3) 0.3909(3) 0.0322(13) Uani 1 1 d . . . C46 C 1.1190(9) 0.2395(3) 0.4380(2) 0.0352(14) Uani 1 1 d . . . C47 C 0.9572(8) 0.2378(3) 0.4202(3) 0.0375(14) Uani 1 1 d . . . C48 C 0.9447(8) 0.2456(3) 0.3538(3) 0.0308(13) Uani 1 1 d . . . C51 C 0.8980(6) 0.3239(3) 0.0722(2) 0.0199(11) Uani 1 1 d . . . H51A H 0.7922 0.3590 0.0729 0.024 Uiso 1 1 calc R . . H51B H 0.8974 0.2857 0.0390 0.024 Uiso 1 1 calc R . . C52 C 1.0607(7) 0.3752(3) 0.0545(2) 0.0243(11) Uani 1 1 d . . . H52A H 1.1622 0.3416 0.0373 0.029 Uiso 1 1 calc R . . H52B H 1.0443 0.4196 0.0196 0.029 Uiso 1 1 calc R . . C53 C 1.2125(6) 0.4731(3) 0.1013(2) 0.0177(10) Uani 1 1 d . . . C54 C 1.3922(7) 0.4601(3) 0.0907(2) 0.0228(11) Uani 1 1 d . . . C55 C 1.5101(6) 0.5214(3) 0.0771(2) 0.0217(11) Uani 1 1 d . . . C56 C 1.4494(7) 0.6003(3) 0.0731(2) 0.0230(11) Uani 1 1 d . . . C57 C 1.2732(7) 0.6170(3) 0.0835(2) 0.0202(11) Uani 1 1 d . . . C58 C 1.1569(6) 0.5545(3) 0.0976(2) 0.0192(11) Uani 1 1 d . . . F44 F 1.3954(4) 0.26929(18) 0.27946(14) 0.0353(7) Uani 1 1 d . . . F45 F 1.4232(5) 0.2534(2) 0.40879(16) 0.0513(9) Uani 1 1 d . . . F46 F 1.1336(5) 0.2291(2) 0.50216(14) 0.0543(10) Uani 1 1 d . . . F47 F 0.8155(5) 0.2255(2) 0.46683(16) 0.0606(11) Uani 1 1 d . . . F48 F 0.7853(4) 0.2419(2) 0.33715(15) 0.0472(9) Uani 1 1 d . . . F54 F 1.4538(4) 0.38299(15) 0.09302(14) 0.0309(7) Uani 1 1 d . . . F55 F 1.6818(4) 0.50583(17) 0.06548(14) 0.0328(7) Uani 1 1 d . . . F56 F 1.5622(4) 0.66157(16) 0.05880(14) 0.0312(7) Uani 1 1 d . . . F57 F 1.2152(4) 0.69367(15) 0.08027(13) 0.0293(7) Uani 1 1 d . . . F58 F 0.9847(4) 0.57129(16) 0.10827(14) 0.0280(7) Uani 1 1 d . . . C62 C 0.6127(12) 0.9521(5) 0.5297(4) 0.082(2) Uiso 1 1 d . . . H62 H 0.6928 0.9182 0.5506 0.098 Uiso 1 1 calc R . . C63 C 0.4467(14) 0.9360(6) 0.5439(5) 0.102(3) Uiso 1 1 d . A . H63 H 0.4075 0.8910 0.5750 0.123 Uiso 1 1 calc R . . C64 C 0.1405(14) 0.9621(10) 0.5212(8) 0.090(5) Uiso 0.50 1 d PD A 1 H64A H 0.0702 1.0103 0.5104 0.135 Uiso 0.50 1 calc PR A 1 H64B H 0.0994 0.9393 0.5669 0.135 Uiso 0.50 1 calc PR A 1 H64C H 0.1289 0.9218 0.4913 0.135 Uiso 0.50 1 calc PR A 1 C61 C 0.3264(12) 0.9846(5) 0.5137(4) 0.089(3) Uiso 1 1 d D . . H61 H 0.2050 0.9732 0.5234 0.107 Uiso 0.50 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ge1 0.0193(3) 0.0163(3) 0.0209(3) -0.0039(2) -0.0047(2) -0.0042(2) Br11 0.0265(3) 0.0222(3) 0.0266(3) -0.0009(2) -0.0087(2) -0.0021(2) Br12 0.0279(3) 0.0207(3) 0.0322(3) -0.0037(2) -0.0108(2) -0.0082(2) N11 0.025(2) 0.016(2) 0.020(2) -0.0025(16) -0.0061(19) -0.0037(17) N12 0.025(3) 0.020(2) 0.024(2) -0.0063(17) -0.0063(19) 0.0009(18) N13 0.025(3) 0.020(2) 0.021(2) -0.0030(17) -0.0039(19) 0.0000(18) C1 0.028(3) 0.027(3) 0.025(3) 0.001(2) 0.000(2) -0.008(2) C2 0.030(3) 0.027(3) 0.037(3) 0.003(2) -0.006(3) -0.014(2) C3 0.037(4) 0.034(3) 0.027(3) 0.008(2) -0.005(3) -0.015(3) C4 0.045(4) 0.052(4) 0.037(4) 0.006(3) -0.006(3) -0.016(3) C5 0.030(4) 0.059(4) 0.050(4) 0.028(3) -0.017(3) -0.014(3) C6 0.032(4) 0.039(3) 0.059(4) 0.011(3) -0.004(3) -0.005(3) C7 0.028(3) 0.032(3) 0.048(4) 0.001(3) -0.001(3) -0.007(3) C11 0.031(3) 0.022(3) 0.020(3) -0.001(2) -0.008(2) -0.008(2) C12 0.031(3) 0.025(3) 0.020(3) -0.004(2) -0.006(2) 0.000(2) C13 0.029(3) 0.020(3) 0.021(3) -0.007(2) -0.002(2) 0.001(2) C14 0.026(3) 0.026(3) 0.032(3) -0.003(2) 0.004(3) -0.004(2) C15 0.051(4) 0.017(3) 0.041(3) 0.000(2) 0.009(3) 0.001(3) C16 0.047(4) 0.025(3) 0.030(3) -0.005(2) -0.003(3) 0.012(3) C17 0.026(3) 0.031(3) 0.023(3) -0.013(2) -0.003(2) 0.002(2) C18 0.033(3) 0.023(3) 0.017(3) -0.007(2) -0.004(2) 0.000(2) C21 0.028(3) 0.021(3) 0.022(3) 0.000(2) -0.003(2) -0.001(2) C22 0.020(3) 0.025(3) 0.021(3) -0.005(2) -0.004(2) -0.001(2) C23 0.014(3) 0.018(2) 0.029(3) -0.002(2) -0.002(2) -0.005(2) C24 0.026(3) 0.029(3) 0.017(3) -0.005(2) -0.002(2) -0.002(2) C25 0.021(3) 0.023(3) 0.033(3) -0.008(2) -0.006(2) -0.005(2) C26 0.025(3) 0.020(3) 0.027(3) 0.003(2) 0.001(2) -0.005(2) C27 0.030(3) 0.025(3) 0.016(3) -0.002(2) -0.002(2) 0.000(2) C28 0.020(3) 0.019(2) 0.025(3) -0.005(2) -0.004(2) -0.003(2) F14 0.036(2) 0.0268(17) 0.063(2) -0.0019(15) 0.0109(17) -0.0076(14) F15 0.066(3) 0.0179(17) 0.083(3) 0.0016(16) 0.015(2) -0.0011(16) F16 0.060(3) 0.0348(19) 0.054(2) 0.0001(16) 0.0027(19) 0.0209(17) F17 0.0261(19) 0.0450(19) 0.0428(19) -0.0172(15) -0.0047(15) 0.0046(15) F18 0.0319(19) 0.0263(16) 0.0417(18) -0.0055(13) -0.0002(15) -0.0088(13) F24 0.040(2) 0.0340(17) 0.0239(16) -0.0093(12) -0.0052(14) -0.0120(14) F25 0.043(2) 0.0291(17) 0.0432(19) -0.0096(14) -0.0103(16) -0.0195(14) F26 0.044(2) 0.0291(17) 0.0401(19) 0.0051(14) -0.0060(16) -0.0156(15) F27 0.053(2) 0.0339(17) 0.0194(15) -0.0013(12) -0.0048(15) -0.0038(15) F28 0.0394(19) 0.0201(14) 0.0279(16) -0.0093(12) -0.0093(14) -0.0082(13) Ge2 0.0235(3) 0.0144(2) 0.0180(3) -0.00216(19) -0.0036(2) -0.0052(2) Br21 0.0330(3) 0.0180(2) 0.0232(3) -0.00461(19) -0.0078(2) -0.0069(2) Br22 0.0257(3) 0.0262(3) 0.0346(3) -0.0121(2) 0.0005(2) -0.0042(2) N21 0.018(2) 0.0142(19) 0.019(2) -0.0030(15) -0.0032(17) -0.0051(16) N22 0.038(3) 0.0121(19) 0.017(2) 0.0006(15) -0.0076(19) -0.0066(18) N23 0.029(3) 0.018(2) 0.020(2) -0.0019(16) -0.0063(19) -0.0106(18) C31 0.015(3) 0.028(3) 0.022(3) -0.003(2) 0.001(2) -0.008(2) C32 0.026(3) 0.026(3) 0.026(3) -0.006(2) 0.001(2) -0.009(2) C33 0.033(3) 0.029(3) 0.032(3) -0.001(2) -0.007(3) -0.013(2) C34 0.046(4) 0.026(3) 0.048(4) -0.004(3) 0.000(3) -0.020(3) C35 0.035(4) 0.037(3) 0.055(4) -0.020(3) -0.012(3) -0.013(3) C36 0.031(4) 0.053(4) 0.041(4) -0.018(3) -0.013(3) -0.010(3) C37 0.034(4) 0.031(3) 0.037(3) -0.009(2) -0.009(3) -0.002(3) C41 0.028(3) 0.014(2) 0.023(3) -0.0072(19) -0.004(2) -0.003(2) C42 0.033(3) 0.016(2) 0.027(3) -0.003(2) -0.010(2) -0.001(2) C43 0.039(3) 0.011(2) 0.016(2) 0.0022(18) -0.004(2) -0.007(2) C44 0.032(3) 0.021(3) 0.022(3) 0.001(2) -0.003(2) -0.005(2) C45 0.040(4) 0.028(3) 0.033(3) -0.001(2) -0.021(3) -0.005(3) C46 0.060(4) 0.031(3) 0.015(3) -0.001(2) -0.008(3) -0.013(3) C47 0.042(4) 0.042(3) 0.026(3) 0.000(2) 0.001(3) -0.013(3) C48 0.037(4) 0.029(3) 0.028(3) -0.002(2) -0.009(3) -0.011(2) C51 0.024(3) 0.018(2) 0.020(3) -0.0015(19) -0.008(2) -0.006(2) C52 0.030(3) 0.026(3) 0.017(3) 0.001(2) -0.006(2) -0.005(2) C53 0.020(3) 0.020(2) 0.014(2) 0.0013(19) -0.004(2) -0.009(2) C54 0.030(3) 0.018(2) 0.021(3) -0.002(2) -0.006(2) -0.001(2) C55 0.017(3) 0.027(3) 0.022(3) -0.006(2) -0.003(2) -0.003(2) C56 0.025(3) 0.024(3) 0.021(3) -0.003(2) -0.001(2) -0.010(2) C57 0.028(3) 0.016(2) 0.017(2) -0.0019(19) -0.004(2) -0.004(2) C58 0.020(3) 0.021(2) 0.016(2) -0.0016(19) -0.004(2) -0.003(2) F44 0.0259(19) 0.0410(18) 0.0378(19) -0.0023(14) -0.0028(15) -0.0017(14) F45 0.049(2) 0.061(2) 0.052(2) -0.0023(17) -0.0307(19) -0.0032(18) F46 0.091(3) 0.054(2) 0.0230(18) -0.0036(15) -0.0202(19) -0.017(2) F47 0.065(3) 0.078(3) 0.032(2) -0.0012(18) 0.0106(19) -0.026(2) F48 0.034(2) 0.068(2) 0.039(2) 0.0045(16) -0.0062(16) -0.0226(18) F54 0.0281(18) 0.0195(15) 0.0452(19) -0.0023(13) -0.0073(15) 0.0000(13) F55 0.0222(18) 0.0351(17) 0.0405(18) -0.0010(13) -0.0045(14) -0.0061(13) F56 0.0279(18) 0.0250(16) 0.0402(18) -0.0039(13) -0.0016(14) -0.0146(13) F57 0.0353(19) 0.0157(14) 0.0355(17) -0.0014(12) -0.0033(14) -0.0015(13) F58 0.0220(17) 0.0249(15) 0.0372(17) -0.0029(12) -0.0056(14) -0.0035(12) _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 N13 1.834(4) . ? Ge1 N12 1.837(4) . ? Ge1 N11 2.161(4) . ? Ge1 Br12 2.3442(7) . ? Ge1 Br11 2.4100(7) . ? N11 C21 1.479(6) . ? N11 C11 1.484(6) . ? N11 C1 1.505(6) . ? N12 C13 1.403(6) . ? N12 C12 1.464(6) . ? N13 C23 1.412(6) . ? N13 C22 1.479(6) . ? C1 C2 1.512(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C7 1.385(7) . ? C2 C3 1.402(7) . ? C3 C4 1.384(7) . ? C3 H3 0.9500 . ? C4 C5 1.381(8) . ? C4 H4 0.9500 . ? C5 C6 1.382(9) . ? C5 H5 0.9500 . ? C6 C7 1.388(8) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C11 C12 1.511(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.382(7) . ? C13 C14 1.395(7) . ? C14 F14 1.338(6) . ? C14 C15 1.360(7) . ? C15 F15 1.344(6) . ? C15 C16 1.376(8) . ? C16 F16 1.354(6) . ? C16 C17 1.365(7) . ? C17 F17 1.339(6) . ? C17 C18 1.377(7) . ? C18 F18 1.345(5) . ? C21 C22 1.509(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.389(6) . ? C23 C24 1.391(7) . ? C24 F24 1.351(5) . ? C24 C25 1.371(7) . ? C25 F25 1.353(5) . ? C25 C26 1.363(7) . ? C26 F26 1.340(5) . ? C26 C27 1.392(7) . ? C27 F27 1.344(5) . ? C27 C28 1.376(7) . ? C28 F28 1.337(5) . ? Ge2 N23 1.831(4) . ? Ge2 N22 1.842(4) . ? Ge2 N21 2.169(3) . ? Ge2 Br22 2.3328(7) . ? Ge2 Br21 2.4226(7) . ? N21 C51 1.479(5) . ? N21 C41 1.487(6) . ? N21 C31 1.506(6) . ? N22 C43 1.412(6) . ? N22 C42 1.467(5) . ? N23 C53 1.411(6) . ? N23 C52 1.466(6) . ? C31 C32 1.517(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.381(7) . ? C32 C37 1.381(7) . ? C33 C34 1.384(7) . ? C33 H33 0.9500 . ? C34 C35 1.370(8) . ? C34 H34 0.9500 . ? C35 C36 1.380(8) . ? C35 H35 0.9500 . ? C36 C37 1.388(7) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C41 C42 1.512(6) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.381(7) . ? C43 C48 1.391(7) . ? C44 F44 1.335(6) . ? C44 C45 1.379(7) . ? C45 F45 1.341(6) . ? C45 C46 1.368(8) . ? C46 F46 1.341(5) . ? C46 C47 1.371(8) . ? C47 F47 1.338(6) . ? C47 C48 1.382(7) . ? C48 F48 1.346(6) . ? C51 C52 1.517(7) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.389(7) . ? C53 C58 1.403(6) . ? C54 F54 1.351(5) . ? C54 C55 1.366(7) . ? C55 F55 1.336(5) . ? C55 C56 1.378(6) . ? C56 F56 1.340(5) . ? C56 C57 1.372(7) . ? C57 F57 1.336(5) . ? C57 C58 1.373(6) . ? C58 F58 1.343(5) . ? C62 C63 1.302(12) . ? C62 C61 1.343(10) 2_676 ? C62 H62 0.9500 . ? C63 C61 1.395(11) . ? C63 H63 0.9500 . ? C64 C61 1.482(5) . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C61 C62 1.343(10) 2_676 ? C61 H61 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 N13 Ge1 N12 121.75(18) . . ? N13 Ge1 N11 82.82(16) . . ? N12 Ge1 N11 82.01(15) . . ? N13 Ge1 Br12 114.13(12) . . ? N12 Ge1 Br12 122.01(13) . . ? N11 Ge1 Br12 90.95(10) . . ? N13 Ge1 Br11 97.02(12) . . ? N12 Ge1 Br11 95.58(12) . . ? N11 Ge1 Br11 177.01(10) . . ? Br12 Ge1 Br11 91.83(2) . . ? C21 N11 C11 112.2(4) . . ? C21 N11 C1 112.4(4) . . ? C11 N11 C1 110.4(4) . . ? C21 N11 Ge1 104.1(3) . . ? C11 N11 Ge1 100.5(3) . . ? C1 N11 Ge1 116.7(3) . . ? C13 N12 C12 114.7(4) . . ? C13 N12 Ge1 126.4(3) . . ? C12 N12 Ge1 118.8(3) . . ? C23 N13 C22 112.7(4) . . ? C23 N13 Ge1 123.2(3) . . ? C22 N13 Ge1 118.6(3) . . ? N11 C1 C2 116.3(4) . . ? N11 C1 H1A 108.2 . . ? C2 C1 H1A 108.2 . . ? N11 C1 H1B 108.2 . . ? C2 C1 H1B 108.2 . . ? H1A C1 H1B 107.4 . . ? C7 C2 C3 118.5(5) . . ? C7 C2 C1 121.5(5) . . ? C3 C2 C1 119.8(5) . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.2(6) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.1(5) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 119.7(6) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 121.1(6) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? N11 C11 C12 108.0(4) . . ? N11 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? N11 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? N12 C12 C11 107.5(4) . . ? N12 C12 H12A 110.2 . . ? C11 C12 H12A 110.2 . . ? N12 C12 H12B 110.2 . . ? C11 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C18 C13 C14 115.5(4) . . ? C18 C13 N12 122.4(4) . . ? C14 C13 N12 122.1(5) . . ? F14 C14 C15 118.3(5) . . ? F14 C14 C13 118.8(4) . . ? C15 C14 C13 122.9(5) . . ? F15 C15 C14 121.7(5) . . ? F15 C15 C16 119.1(5) . . ? C14 C15 C16 119.2(5) . . ? F16 C16 C17 119.8(5) . . ? F16 C16 C15 119.8(5) . . ? C17 C16 C15 120.4(5) . . ? F17 C17 C16 120.4(5) . . ? F17 C17 C18 120.6(5) . . ? C16 C17 C18 119.0(5) . . ? F18 C18 C17 118.3(5) . . ? F18 C18 C13 118.8(4) . . ? C17 C18 C13 122.9(5) . . ? N11 C21 C22 108.7(4) . . ? N11 C21 H21A 109.9 . . ? C22 C21 H21A 109.9 . . ? N11 C21 H21B 109.9 . . ? C22 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? N13 C22 C21 109.4(4) . . ? N13 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? N13 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? C28 C23 C24 115.5(4) . . ? C28 C23 N13 121.8(4) . . ? C24 C23 N13 122.6(4) . . ? F24 C24 C25 118.2(4) . . ? F24 C24 C23 118.6(4) . . ? C25 C24 C23 123.2(4) . . ? F25 C25 C26 119.7(4) . . ? F25 C25 C24 120.2(4) . . ? C26 C25 C24 120.1(4) . . ? F26 C26 C25 121.0(4) . . ? F26 C26 C27 120.2(4) . . ? C25 C26 C27 118.7(4) . . ? F27 C27 C28 120.3(4) . . ? F27 C27 C26 119.3(4) . . ? C28 C27 C26 120.4(4) . . ? F28 C28 C27 117.4(4) . . ? F28 C28 C23 120.6(4) . . ? C27 C28 C23 122.0(4) . . ? N23 Ge2 N22 124.13(18) . . ? N23 Ge2 N21 81.87(15) . . ? N22 Ge2 N21 81.62(15) . . ? N23 Ge2 Br22 113.14(13) . . ? N22 Ge2 Br22 120.96(13) . . ? N21 Ge2 Br22 93.95(10) . . ? N23 Ge2 Br21 95.81(12) . . ? N22 Ge2 Br21 93.25(12) . . ? N21 Ge2 Br21 171.72(10) . . ? Br22 Ge2 Br21 94.27(2) . . ? C51 N21 C41 112.5(4) . . ? C51 N21 C31 111.7(4) . . ? C41 N21 C31 111.8(3) . . ? C51 N21 Ge2 105.4(2) . . ? C41 N21 Ge2 100.6(3) . . ? C31 N21 Ge2 114.3(3) . . ? C43 N22 C42 115.0(3) . . ? C43 N22 Ge2 122.7(3) . . ? C42 N22 Ge2 119.5(3) . . ? C53 N23 C52 114.8(4) . . ? C53 N23 Ge2 124.8(3) . . ? C52 N23 Ge2 120.2(3) . . ? N21 C31 C32 115.5(4) . . ? N21 C31 H31A 108.4 . . ? C32 C31 H31A 108.4 . . ? N21 C31 H31B 108.4 . . ? C32 C31 H31B 108.4 . . ? H31A C31 H31B 107.5 . . ? C33 C32 C37 119.0(5) . . ? C33 C32 C31 119.6(4) . . ? C37 C32 C31 121.3(4) . . ? C32 C33 C34 120.3(5) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 120.8(5) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C36 119.2(5) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C35 C36 C37 120.3(5) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C32 C37 C36 120.3(5) . . ? C32 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? N21 C41 C42 108.3(4) . . ? N21 C41 H41A 110.0 . . ? C42 C41 H41A 110.0 . . ? N21 C41 H41B 110.0 . . ? C42 C41 H41B 110.0 . . ? H41A C41 H41B 108.4 . . ? N22 C42 C41 107.0(3) . . ? N22 C42 H42A 110.3 . . ? C41 C42 H42A 110.3 . . ? N22 C42 H42B 110.3 . . ? C41 C42 H42B 110.3 . . ? H42A C42 H42B 108.6 . . ? C44 C43 C48 117.1(4) . . ? C44 C43 N22 122.0(5) . . ? C48 C43 N22 120.9(5) . . ? F44 C44 C45 119.2(5) . . ? F44 C44 C43 119.3(4) . . ? C45 C44 C43 121.5(5) . . ? F45 C45 C46 120.2(5) . . ? F45 C45 C44 120.0(5) . . ? C46 C45 C44 119.8(5) . . ? F46 C46 C45 119.8(5) . . ? F46 C46 C47 119.6(5) . . ? C45 C46 C47 120.6(5) . . ? F47 C47 C46 119.8(5) . . ? F47 C47 C48 121.1(5) . . ? C46 C47 C48 119.0(5) . . ? F48 C48 C47 118.3(5) . . ? F48 C48 C43 119.9(4) . . ? C47 C48 C43 121.9(5) . . ? N21 C51 C52 108.4(4) . . ? N21 C51 H51A 110.0 . . ? C52 C51 H51A 110.0 . . ? N21 C51 H51B 110.0 . . ? C52 C51 H51B 110.0 . . ? H51A C51 H51B 108.4 . . ? N23 C52 C51 109.0(4) . . ? N23 C52 H52A 109.9 . . ? C51 C52 H52A 109.9 . . ? N23 C52 H52B 109.9 . . ? C51 C52 H52B 109.9 . . ? H52A C52 H52B 108.3 . . ? C54 C53 C58 115.7(4) . . ? C54 C53 N23 122.4(4) . . ? C58 C53 N23 121.9(4) . . ? F54 C54 C55 118.3(4) . . ? F54 C54 C53 118.5(4) . . ? C55 C54 C53 123.3(4) . . ? F55 C55 C54 121.1(4) . . ? F55 C55 C56 119.8(4) . . ? C54 C55 C56 119.0(5) . . ? F56 C56 C57 119.5(4) . . ? F56 C56 C55 120.2(5) . . ? C57 C56 C55 120.3(4) . . ? F57 C57 C56 120.1(4) . . ? F57 C57 C58 120.2(4) . . ? C56 C57 C58 119.8(4) . . ? F58 C58 C57 119.4(4) . . ? F58 C58 C53 118.7(4) . . ? C57 C58 C53 121.9(4) . . ? C63 C62 C61 121.8(9) . 2_676 ? C63 C62 H62 119.1 . . ? C61 C62 H62 119.1 2_676 . ? C62 C63 C61 120.3(10) . . ? C62 C63 H63 119.9 . . ? C61 C63 H63 119.9 . . ? C61 C64 H64A 109.5 . . ? C61 C64 H64B 109.5 . . ? C61 C64 H64C 109.5 . . ? C62 C61 C63 117.9(9) 2_676 . ? C62 C61 C64 119.7(11) 2_676 . ? C63 C61 C64 121.9(11) . . ? C62 C61 H61 121.0 2_676 . ? C63 C61 H61 121.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N11 Ge1 Br12 -36.8(3) . . . . ? C31 N21 Ge2 Br22 -34.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.887 _refine_diff_density_min -0.629 _refine_diff_density_rms 0.108 #===END data_12 _database_code_depnum_ccdc_archive 'CCDC 718437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H52 Cl2 Ge2 N6 Si4' _chemical_formula_sum 'C20 H52 Cl2 Ge2 N6 Si4' _chemical_formula_weight 705.12 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' Si Si 0.0817 0.0704 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.744(3) _cell_length_b 14.569(2) _cell_length_c 13.503(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.501(4) _cell_angle_gamma 90.00 _cell_volume 3293.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3108 _cell_measurement_theta_min 2.384 _cell_measurement_theta_max 22.857 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 2.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6726 _exptl_absorpt_correction_T_max 0.9188 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _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 18868 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7896 _reflns_number_gt 5494 _reflns_threshold_expression I>2\s(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. The structure contains two crystallographycally independent pseudo-symmetric molecules. However, the refinement in higher symmetry space group Pbca was found to be unsatisfactory. ; _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^)+(0.0524P)^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 7896 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 0.476214(19) 0.55135(2) 0.40304(2) 0.01959(10) Uani 1 1 d . . . Ge2 Ge 0.026671(19) 0.43880(2) 0.08866(2) 0.01959(10) Uani 1 1 d . . . Cl1 Cl 0.48638(5) 0.70075(5) 0.35267(6) 0.02911(19) Uani 1 1 d . . . Cl2 Cl 0.00497(5) 0.28840(6) 0.12776(6) 0.0304(2) Uani 1 1 d . . . Si11 Si 0.57631(5) 0.54212(6) 0.20001(7) 0.0238(2) Uani 1 1 d . . . Si12 Si 0.29421(6) 0.62297(8) 0.36737(8) 0.0357(3) Uani 1 1 d . . . Si21 Si -0.07129(6) 0.44807(6) 0.29742(7) 0.0274(2) Uani 1 1 d . . . Si22 Si 0.20096(5) 0.34463(6) 0.10782(7) 0.0250(2) Uani 1 1 d . . . N11 N 0.54601(17) 0.50066(19) 0.3143(2) 0.0292(6) Uani 1 1 d . . . N12 N 0.36751(16) 0.5397(2) 0.3931(2) 0.0312(7) Uani 1 1 d . . . N13 N 0.47421(15) 0.41976(18) 0.46962(19) 0.0218(6) Uani 1 1 d . . . N21 N -0.01902(17) 0.49179(19) 0.19748(19) 0.0274(6) Uani 1 1 d . . . N22 N 0.13527(16) 0.43136(19) 0.0706(2) 0.0263(6) Uani 1 1 d . . . N23 N 0.03661(15) 0.57348(17) 0.03210(19) 0.0216(6) Uani 1 1 d . . . C11 C 0.5189(2) 0.3583(2) 0.4038(2) 0.0313(8) Uani 1 1 d . . . H11A H 0.4828 0.3321 0.3526 0.038 Uiso 1 1 calc R . . H11B H 0.5429 0.3072 0.4422 0.038 Uiso 1 1 calc R . . C12 C 0.5843(2) 0.4160(3) 0.3553(3) 0.0381(9) Uani 1 1 d . . . H12A H 0.6256 0.4326 0.4050 0.046 Uiso 1 1 calc R . . H12B H 0.6099 0.3807 0.3017 0.046 Uiso 1 1 calc R . . C13 C 0.38950(19) 0.3936(2) 0.4768(3) 0.0302(8) Uani 1 1 d . . . H13A H 0.3674 0.4143 0.5408 0.036 Uiso 1 1 calc R . . H13B H 0.3838 0.3261 0.4725 0.036 Uiso 1 1 calc R . . C14 C 0.3457(2) 0.4394(2) 0.3914(3) 0.0421(10) Uani 1 1 d . . . H14A H 0.3616 0.4114 0.3278 0.051 Uiso 1 1 calc R . . H14B H 0.2873 0.4319 0.3989 0.051 Uiso 1 1 calc R . . C15 C 0.1946(2) 0.5679(3) 0.3801(4) 0.0592(14) Uani 1 1 d . . . H15A H 0.1904 0.5402 0.4460 0.089 Uiso 1 1 calc R . . H15B H 0.1882 0.5202 0.3295 0.089 Uiso 1 1 calc R . . H15C H 0.1527 0.6143 0.3716 0.089 Uiso 1 1 calc R . . C16 C 0.2981(2) 0.6682(3) 0.2389(3) 0.0431(10) Uani 1 1 d . . . H16A H 0.3436 0.7100 0.2327 0.065 Uiso 1 1 calc R . . H16B H 0.2485 0.7015 0.2238 0.065 Uiso 1 1 calc R . . H16C H 0.3040 0.6171 0.1924 0.065 Uiso 1 1 calc R . . C17 C 0.2955(2) 0.7182(3) 0.4573(3) 0.0450(11) Uani 1 1 d . . . H17A H 0.3477 0.7486 0.4560 0.067 Uiso 1 1 calc R . . H17B H 0.2857 0.6941 0.5239 0.067 Uiso 1 1 calc R . . H17C H 0.2536 0.7626 0.4398 0.067 Uiso 1 1 calc R . . C18 C 0.6536(2) 0.6341(3) 0.2128(3) 0.0444(10) Uani 1 1 d . . . H18A H 0.6297 0.6884 0.2435 0.067 Uiso 1 1 calc R . . H18B H 0.6738 0.6503 0.1472 0.067 Uiso 1 1 calc R . . H18C H 0.6977 0.6118 0.2545 0.067 Uiso 1 1 calc R . . C19 C 0.4915(2) 0.5845(3) 0.1231(3) 0.0384(9) Uani 1 1 d . . . H19A H 0.4647 0.6348 0.1577 0.058 Uiso 1 1 calc R . . H19B H 0.4535 0.5344 0.1116 0.058 Uiso 1 1 calc R . . H19C H 0.5115 0.6067 0.0595 0.058 Uiso 1 1 calc R . . C20 C 0.6224(2) 0.4444(2) 0.1308(3) 0.0342(8) Uani 1 1 d . . . H20A H 0.5858 0.3920 0.1304 0.051 Uiso 1 1 calc R . . H20B H 0.6727 0.4267 0.1632 0.051 Uiso 1 1 calc R . . H20C H 0.6330 0.4634 0.0625 0.051 Uiso 1 1 calc R . . C21 C -0.0011(2) 0.6344(2) 0.1059(2) 0.0300(8) Uani 1 1 d . . . H21A H -0.0586 0.6425 0.0903 0.036 Uiso 1 1 calc R . . H21B H 0.0249 0.6954 0.1060 0.036 Uiso 1 1 calc R . . C22 C 0.0095(2) 0.5884(2) 0.2055(3) 0.0391(9) Uani 1 1 d . . . H22A H 0.0665 0.5895 0.2255 0.047 Uiso 1 1 calc R . . H22B H -0.0216 0.6216 0.2563 0.047 Uiso 1 1 calc R . . C23 C 0.12226(19) 0.5921(2) 0.0208(3) 0.0286(8) Uani 1 1 d . . . H23A H 0.1441 0.6199 0.0822 0.034 Uiso 1 1 calc R . . H23B H 0.1308 0.6353 -0.0346 0.034 Uiso 1 1 calc R . . C24 C 0.1637(2) 0.5021(2) 0.0002(3) 0.0346(9) Uani 1 1 d . . . H24A H 0.1520 0.4824 -0.0686 0.041 Uiso 1 1 calc R . . H24B H 0.2222 0.5099 0.0074 0.041 Uiso 1 1 calc R . . C25 C -0.1473(2) 0.3602(3) 0.2644(3) 0.0510(11) Uani 1 1 d . . . H25A H -0.1820 0.3838 0.2114 0.076 Uiso 1 1 calc R . . H25B H -0.1795 0.3461 0.3227 0.076 Uiso 1 1 calc R . . H25C H -0.1205 0.3043 0.2417 0.076 Uiso 1 1 calc R . . C26 C -0.1278(3) 0.5448(3) 0.3523(3) 0.0577(13) Uani 1 1 d . . . H26A H -0.0907 0.5863 0.3866 0.086 Uiso 1 1 calc R . . H26B H -0.1667 0.5209 0.3996 0.086 Uiso 1 1 calc R . . H26C H -0.1559 0.5785 0.2997 0.086 Uiso 1 1 calc R . . C27 C -0.0020(2) 0.4016(3) 0.3932(3) 0.0354(9) Uani 1 1 d . . . H27A H 0.0345 0.4502 0.4154 0.053 Uiso 1 1 calc R . . H27B H 0.0289 0.3510 0.3651 0.053 Uiso 1 1 calc R . . H27C H -0.0328 0.3792 0.4497 0.053 Uiso 1 1 calc R . . C28 C 0.30459(19) 0.3915(3) 0.1058(3) 0.0355(9) Uani 1 1 d . . . H28A H 0.3068 0.4485 0.1442 0.053 Uiso 1 1 calc R . . H28B H 0.3199 0.4041 0.0372 0.053 Uiso 1 1 calc R . . H28C H 0.3415 0.3466 0.1348 0.053 Uiso 1 1 calc R . . C29 C 0.1990(2) 0.2457(3) 0.0200(3) 0.0353(9) Uani 1 1 d . . . H29A H 0.1449 0.2201 0.0169 0.053 Uiso 1 1 calc R . . H29B H 0.2364 0.1984 0.0431 0.053 Uiso 1 1 calc R . . H29C H 0.2146 0.2667 -0.0460 0.053 Uiso 1 1 calc R . . C30 C 0.1825(2) 0.3080(2) 0.2373(2) 0.0304(8) Uani 1 1 d . . . H30A H 0.1655 0.3611 0.2765 0.046 Uiso 1 1 calc R . . H30B H 0.2317 0.2826 0.2659 0.046 Uiso 1 1 calc R . . H30C H 0.1405 0.2611 0.2379 0.046 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 0.02136(18) 0.01852(18) 0.01885(19) 0.00344(13) -0.00320(13) -0.00033(13) Ge2 0.02128(18) 0.01856(18) 0.01884(19) 0.00428(13) -0.00450(13) -0.00062(13) Cl1 0.0372(5) 0.0216(4) 0.0286(5) 0.0070(3) 0.0017(3) 0.0025(3) Cl2 0.0323(4) 0.0223(4) 0.0366(5) 0.0112(3) -0.0019(4) 0.0005(3) Si11 0.0246(5) 0.0250(5) 0.0218(5) 0.0030(4) -0.0004(4) -0.0029(4) Si12 0.0247(5) 0.0476(7) 0.0349(6) 0.0141(5) -0.0022(4) 0.0076(5) Si21 0.0305(5) 0.0300(5) 0.0216(5) 0.0021(4) 0.0005(4) 0.0031(4) Si22 0.0241(5) 0.0277(5) 0.0232(5) 0.0068(4) -0.0009(4) 0.0044(4) N11 0.0413(17) 0.0224(15) 0.0240(16) 0.0035(12) 0.0060(12) 0.0068(13) N12 0.0235(14) 0.0307(16) 0.0392(18) 0.0150(13) -0.0099(13) -0.0042(12) N13 0.0252(14) 0.0207(13) 0.0195(14) 0.0035(11) -0.0044(11) -0.0037(11) N21 0.0384(16) 0.0228(15) 0.0209(15) 0.0000(11) -0.0005(12) 0.0001(12) N22 0.0225(14) 0.0265(15) 0.0299(16) 0.0128(12) -0.0035(11) 0.0008(12) N23 0.0240(14) 0.0185(13) 0.0221(14) 0.0010(11) -0.0058(11) -0.0010(11) C11 0.050(2) 0.0204(17) 0.0236(19) -0.0005(14) -0.0026(16) 0.0006(16) C12 0.049(2) 0.033(2) 0.032(2) 0.0036(16) 0.0044(17) 0.0120(18) C13 0.0282(18) 0.0270(18) 0.035(2) 0.0095(15) -0.0081(15) -0.0120(15) C14 0.041(2) 0.035(2) 0.049(3) 0.0078(18) -0.0156(19) -0.0123(18) C15 0.024(2) 0.090(4) 0.063(3) 0.023(3) -0.0062(19) 0.001(2) C16 0.041(2) 0.055(3) 0.034(2) 0.0119(18) -0.0023(17) 0.0185(19) C17 0.036(2) 0.054(3) 0.045(3) 0.015(2) 0.0010(18) 0.0167(19) C18 0.039(2) 0.043(2) 0.052(3) -0.0085(19) 0.0052(19) -0.0158(19) C19 0.040(2) 0.046(2) 0.029(2) 0.0017(17) -0.0051(16) 0.0040(18) C20 0.039(2) 0.036(2) 0.028(2) 0.0042(15) 0.0064(15) 0.0024(16) C21 0.045(2) 0.0187(17) 0.0263(19) -0.0025(14) -0.0069(15) -0.0024(15) C22 0.061(3) 0.0270(19) 0.029(2) -0.0042(15) -0.0064(18) -0.0052(18) C23 0.0239(16) 0.0248(18) 0.037(2) 0.0084(15) -0.0095(14) -0.0073(14) C24 0.0241(17) 0.039(2) 0.040(2) 0.0182(17) -0.0028(15) -0.0013(16) C25 0.042(2) 0.073(3) 0.038(2) 0.001(2) 0.0082(18) -0.018(2) C26 0.066(3) 0.052(3) 0.055(3) 0.012(2) 0.025(2) 0.024(2) C27 0.045(2) 0.035(2) 0.026(2) 0.0075(15) -0.0036(16) -0.0031(17) C28 0.0273(18) 0.045(2) 0.034(2) 0.0076(17) -0.0030(15) 0.0053(16) C29 0.036(2) 0.042(2) 0.028(2) 0.0008(16) 0.0095(16) 0.0049(17) C30 0.0332(19) 0.0323(19) 0.0257(19) 0.0045(15) -0.0042(14) 0.0078(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 N12 1.832(3) . ? Ge1 N11 1.836(3) . ? Ge1 N13 1.949(3) 3_666 ? Ge1 N13 2.118(3) . ? Ge1 Cl1 2.2872(9) . ? Ge2 N21 1.833(3) . ? Ge2 N22 1.840(3) . ? Ge2 N23 1.945(3) 3_565 ? Ge2 N23 2.113(3) . ? Ge2 Cl2 2.2837(9) . ? Si11 N11 1.737(3) . ? Si11 C19 1.858(4) . ? Si11 C18 1.870(4) . ? Si11 C20 1.873(4) . ? Si12 N12 1.759(3) . ? Si12 C17 1.844(4) . ? Si12 C16 1.857(4) . ? Si12 C15 1.860(4) . ? Si21 N21 1.736(3) . ? Si21 C25 1.857(4) . ? Si21 C26 1.857(4) . ? Si21 C27 1.858(4) . ? Si22 N22 1.746(3) . ? Si22 C30 1.856(3) . ? Si22 C28 1.865(4) . ? Si22 C29 1.866(4) . ? N11 C12 1.494(4) . ? N12 C14 1.506(4) . ? N13 C11 1.471(4) . ? N13 C13 1.473(4) . ? N13 Ge1 1.949(3) 3_666 ? N21 C22 1.490(4) . ? N22 C24 1.484(4) . ? N23 C23 1.469(4) . ? N23 C21 1.480(4) . ? N23 Ge2 1.945(3) 3_565 ? C11 C12 1.532(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.517(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.511(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.510(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? 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 N12 Ge1 N11 123.55(13) . . ? N12 Ge1 N13 119.99(13) . 3_666 ? N11 Ge1 N13 113.21(12) . 3_666 ? N12 Ge1 N13 85.85(11) . . ? N11 Ge1 N13 85.73(11) . . ? N13 Ge1 N13 80.16(11) 3_666 . ? N12 Ge1 Cl1 98.22(9) . . ? N11 Ge1 Cl1 98.00(9) . . ? N13 Ge1 Cl1 91.41(8) 3_666 . ? N13 Ge1 Cl1 171.57(7) . . ? N21 Ge2 N22 123.43(12) . . ? N21 Ge2 N23 118.86(12) . 3_565 ? N22 Ge2 N23 114.54(12) . 3_565 ? N21 Ge2 N23 86.18(11) . . ? N22 Ge2 N23 85.74(11) . . ? N23 Ge2 N23 80.00(11) 3_565 . ? N21 Ge2 Cl2 98.65(9) . . ? N22 Ge2 Cl2 97.67(9) . . ? N23 Ge2 Cl2 91.08(8) 3_565 . ? N23 Ge2 Cl2 171.08(7) . . ? N11 Si11 C19 112.60(16) . . ? N11 Si11 C18 111.98(17) . . ? C19 Si11 C18 109.79(19) . . ? N11 Si11 C20 107.70(15) . . ? C19 Si11 C20 106.88(17) . . ? C18 Si11 C20 107.62(18) . . ? N12 Si12 C17 112.66(16) . . ? N12 Si12 C16 113.56(16) . . ? C17 Si12 C16 110.33(19) . . ? N12 Si12 C15 108.00(18) . . ? C17 Si12 C15 105.6(2) . . ? C16 Si12 C15 106.15(19) . . ? N21 Si21 C25 114.56(16) . . ? N21 Si21 C26 107.11(17) . . ? C25 Si21 C26 105.6(2) . . ? N21 Si21 C27 111.02(15) . . ? C25 Si21 C27 109.80(19) . . ? C26 Si21 C27 108.4(2) . . ? N22 Si22 C30 111.66(15) . . ? N22 Si22 C28 108.34(15) . . ? C30 Si22 C28 106.37(16) . . ? N22 Si22 C29 111.61(15) . . ? C30 Si22 C29 111.97(17) . . ? C28 Si22 C29 106.55(17) . . ? C12 N11 Si11 119.3(2) . . ? C12 N11 Ge1 111.3(2) . . ? Si11 N11 Ge1 129.23(16) . . ? C14 N12 Si12 119.8(2) . . ? C14 N12 Ge1 109.4(2) . . ? Si12 N12 Ge1 129.93(17) . . ? C11 N13 C13 112.2(3) . . ? C11 N13 Ge1 116.7(2) . 3_666 ? C13 N13 Ge1 113.6(2) . 3_666 ? C11 N13 Ge1 106.54(19) . . ? C13 N13 Ge1 106.35(19) . . ? Ge1 N13 Ge1 99.84(11) 3_666 . ? C22 N21 Si21 117.0(2) . . ? C22 N21 Ge2 108.7(2) . . ? Si21 N21 Ge2 133.27(17) . . ? C24 N22 Si22 118.8(2) . . ? C24 N22 Ge2 111.5(2) . . ? Si22 N22 Ge2 128.71(15) . . ? C23 N23 C21 112.5(3) . . ? C23 N23 Ge2 117.1(2) . 3_565 ? C21 N23 Ge2 112.8(2) . 3_565 ? C23 N23 Ge2 106.78(18) . . ? C21 N23 Ge2 106.13(19) . . ? Ge2 N23 Ge2 99.99(11) 3_565 . ? N13 C11 C12 107.0(3) . . ? N13 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? N13 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.6 . . ? N11 C12 C11 107.8(3) . . ? N11 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? N11 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.5 . . ? N13 C13 C14 107.2(3) . . ? N13 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? N13 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.5 . . ? N12 C14 C13 107.4(3) . . ? N12 C14 H14A 110.2 . . ? C13 C14 H14A 110.2 . . ? N12 C14 H14B 110.2 . . ? C13 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? Si12 C15 H15A 109.5 . . ? Si12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Si12 C16 H16A 109.5 . . ? Si12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Si12 C17 H17A 109.5 . . ? Si12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si11 C18 H18A 109.5 . . ? Si11 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si11 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Si11 C19 H19A 109.5 . . ? Si11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? Si11 C20 H20A 109.5 . . ? Si11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N23 C21 C22 106.6(3) . . ? N23 C21 H21A 110.4 . . ? C22 C21 H21A 110.4 . . ? N23 C21 H21B 110.4 . . ? C22 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? N21 C22 C21 108.6(3) . . ? N21 C22 H22A 110.0 . . ? C21 C22 H22A 110.0 . . ? N21 C22 H22B 110.0 . . ? C21 C22 H22B 110.0 . . ? H22A C22 H22B 108.4 . . ? N23 C23 C24 108.0(3) . . ? N23 C23 H23A 110.1 . . ? C24 C23 H23A 110.1 . . ? N23 C23 H23B 110.1 . . ? C24 C23 H23B 110.1 . . ? H23A C23 H23B 108.4 . . ? N22 C24 C23 109.5(3) . . ? N22 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? N22 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? Si21 C25 H25A 109.5 . . ? Si21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? Si21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Si21 C26 H26A 109.5 . . ? Si21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? Si21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? Si21 C27 H27A 109.5 . . ? Si21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? Si21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Si22 C28 H28A 109.5 . . ? Si22 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? Si22 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Si22 C29 H29A 109.5 . . ? Si22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? Si22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? Si22 C30 H30A 109.5 . . ? Si22 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? Si22 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.971 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.112