# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '2.CIF' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H49 Ge N13' _chemical_formula_weight 748.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.2975(12) _cell_length_b 15.6680(6) _cell_length_c 15.2402(11) _cell_angle_alpha 90.00 _cell_angle_beta 114.497(9) _cell_angle_gamma 90.00 _cell_volume 3975.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5421 _cell_measurement_theta_min 3.6360 _cell_measurement_theta_max 31.7010 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_T_min 0.56494 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16291 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6881 _reflns_number_gt 5588 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.8315P] 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 6881 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.012 _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 0.745134(14) 0.847192(14) 0.320867(18) 0.01971(8) Uani 1 1 d . . . N1 N 0.81753(10) 1.00306(11) 0.26607(13) 0.0172(4) Uani 1 1 d . . . C1 C 0.81728(12) 0.91801(14) 0.27556(16) 0.0180(5) Uani 1 1 d . . . C2 C 0.77822(12) 0.74721(13) 0.25894(16) 0.0181(5) Uani 1 1 d . . . N3 N 0.74121(10) 0.67124(11) 0.23333(13) 0.0175(4) Uani 1 1 d . . . C3 C 0.87729(13) 1.02809(15) 0.23883(17) 0.0236(5) Uani 1 1 d . . . H3 H 0.8894 1.0849 0.2277 0.028 Uiso 1 1 calc R . . N4 N 0.84386(10) 0.74049(11) 0.24094(13) 0.0181(4) Uani 1 1 d . . . C4 C 0.91501(13) 0.95703(15) 0.23111(17) 0.0249(5) Uani 1 1 d . . . H4 H 0.9592 0.9536 0.2138 0.030 Uiso 1 1 calc R . . N5 N 0.65064(11) 0.86991(13) 0.19219(16) 0.0285(5) Uani 1 1 d . . . C5 C 0.78466(13) 0.61690(15) 0.20181(17) 0.0224(5) Uani 1 1 d . . . H5 H 0.7714 0.5596 0.1810 0.027 Uiso 1 1 calc R . . N6 N 0.58694(13) 0.87489(15) 0.19676(17) 0.0391(6) Uani 1 1 d . . . C6 C 0.84921(13) 0.66065(14) 0.20629(17) 0.0232(5) Uani 1 1 d . . . H6 H 0.8904 0.6405 0.1890 0.028 Uiso 1 1 calc R . . N7 N 0.52445(15) 0.8805(2) 0.1969(2) 0.0767(10) Uani 1 1 d . . . C7 C 0.90775(13) 0.80316(14) 0.26496(18) 0.0233(5) Uani 1 1 d . . . H7A H 0.9363 0.7945 0.2229 0.028 Uiso 1 1 calc R . . H7B H 0.9468 0.7946 0.3326 0.028 Uiso 1 1 calc R . . N8 N 0.89391(13) 0.80396(15) 0.45081(19) 0.0424(6) Uani 1 1 d . . . C8 C 0.76693(12) 1.06169(13) 0.28842(16) 0.0178(5) Uani 1 1 d . . . N9 N 0.92568(12) 0.79212(14) 0.52854(16) 0.0258(5) Uani 1 1 d . . . C9 C 0.78655(13) 1.07841(13) 0.38546(17) 0.0199(5) Uani 1 1 d . . . N10 N 0.96512(16) 0.7865(2) 0.6126(2) 0.0639(8) Uani 1 1 d . . . C10 C 0.73832(14) 1.13673(15) 0.40598(19) 0.0283(6) Uani 1 1 d . . . H10 H 0.7491 1.1492 0.4712 0.034 Uiso 1 1 calc R . . N11 N 0.68882(19) 1.3901(2) 0.1228(3) 0.0804(10) Uani 1 1 d . . . C11 C 0.67523(15) 1.17650(15) 0.3329(2) 0.0309(6) Uani 1 1 d . . . H11 H 0.6433 1.2166 0.3482 0.037 Uiso 1 1 calc R . . N12 N 0.90998(15) 1.43052(17) 0.30306(19) 0.0526(7) Uani 1 1 d . . . C12 C 0.65790(14) 1.15885(15) 0.23811(19) 0.0281(6) Uani 1 1 d . . . H12 H 0.6144 1.1875 0.1888 0.034 Uiso 1 1 calc R . . N13 N 1.0795(2) 0.6699(3) 0.3976(3) 0.1062(16) Uani 1 1 d . . . C13 C 0.70256(13) 1.10008(14) 0.21286(17) 0.0222(5) Uani 1 1 d . . . C14 C 0.68139(15) 1.08017(16) 0.10795(18) 0.0307(6) Uani 1 1 d . . . H14 H 0.7144 1.0301 0.1056 0.037 Uiso 1 1 calc R . . C15 C 0.59318(16) 1.05591(18) 0.0544(2) 0.0456(8) Uani 1 1 d . . . H15A H 0.5811 1.0075 0.0869 0.068 Uiso 1 1 calc R . . H15B H 0.5823 1.0400 -0.0121 0.068 Uiso 1 1 calc R . . H15C H 0.5595 1.1046 0.0540 0.068 Uiso 1 1 calc R . . C16 C 0.70194(18) 1.15497(18) 0.0577(2) 0.0466(8) Uani 1 1 d . . . H16A H 0.6748 1.2066 0.0651 0.070 Uiso 1 1 calc R . . H16B H 0.6840 1.1420 -0.0110 0.070 Uiso 1 1 calc R . . H16C H 0.7601 1.1642 0.0868 0.070 Uiso 1 1 calc R . . C17 C 0.85859(13) 1.03897(15) 0.46671(17) 0.0250(5) Uani 1 1 d . . . H17 H 0.8774 0.9902 0.4390 0.030 Uiso 1 1 calc R . . C18 C 0.92661(16) 1.1029(2) 0.5059(2) 0.0552(9) Uani 1 1 d . . . H18A H 0.9104 1.1510 0.5349 0.083 Uiso 1 1 calc R . . H18B H 0.9394 1.1237 0.4532 0.083 Uiso 1 1 calc R . . H18C H 0.9741 1.0754 0.5549 0.083 Uiso 1 1 calc R . . C19 C 0.83876(18) 1.00390(19) 0.5464(2) 0.0463(8) Uani 1 1 d . . . H19A H 0.8209 1.0505 0.5757 0.069 Uiso 1 1 calc R . . H19B H 0.8866 0.9771 0.5954 0.069 Uiso 1 1 calc R . . H19C H 0.7959 0.9614 0.5198 0.069 Uiso 1 1 calc R . . C20 C 0.66665(13) 0.64857(13) 0.23887(17) 0.0200(5) Uani 1 1 d . . . C21 C 0.66891(14) 0.62870(14) 0.32883(18) 0.0257(6) Uani 1 1 d . . . C22 C 0.59643(16) 0.60493(16) 0.3313(2) 0.0369(7) Uani 1 1 d . . . H22 H 0.5948 0.5914 0.3913 0.044 Uiso 1 1 calc R . . C23 C 0.52704(16) 0.60092(17) 0.2476(2) 0.0417(8) Uani 1 1 d . . . H23 H 0.4783 0.5836 0.2505 0.050 Uiso 1 1 calc R . . C24 C 0.52722(15) 0.62149(16) 0.1606(2) 0.0367(7) Uani 1 1 d . . . H24 H 0.4784 0.6187 0.1041 0.044 Uiso 1 1 calc R . . C25 C 0.59718(13) 0.64636(14) 0.15304(18) 0.0252(5) Uani 1 1 d . . . C26 C 0.59722(15) 0.66810(15) 0.05637(19) 0.0314(6) Uani 1 1 d . . . H26 H 0.6502 0.6952 0.0691 0.038 Uiso 1 1 calc R . . C27 C 0.58994(18) 0.58854(18) -0.0041(2) 0.0448(7) Uani 1 1 d . . . H27A H 0.6338 0.5491 0.0316 0.067 Uiso 1 1 calc R . . H27B H 0.5929 0.6047 -0.0647 0.067 Uiso 1 1 calc R . . H27C H 0.5384 0.5606 -0.0183 0.067 Uiso 1 1 calc R . . C28 C 0.53201(17) 0.73200(18) -0.0006(2) 0.0487(8) Uani 1 1 d . . . H28A H 0.4791 0.7070 -0.0152 0.073 Uiso 1 1 calc R . . H28B H 0.5364 0.7461 -0.0609 0.073 Uiso 1 1 calc R . . H28C H 0.5386 0.7840 0.0376 0.073 Uiso 1 1 calc R . . C29 C 0.74626(16) 0.62707(16) 0.41946(18) 0.0330(6) Uani 1 1 d . . . H29 H 0.7871 0.6604 0.4061 0.040 Uiso 1 1 calc R . . C30 C 0.7382(2) 0.6684(2) 0.5054(2) 0.0560(9) Uani 1 1 d . . . H30A H 0.7146 0.7253 0.4873 0.084 Uiso 1 1 calc R . . H30B H 0.7914 0.6732 0.5590 0.084 Uiso 1 1 calc R . . H30C H 0.7035 0.6331 0.5253 0.084 Uiso 1 1 calc R . . C31 C 0.77709(18) 0.53546(18) 0.4423(2) 0.0479(8) Uani 1 1 d . . . H31A H 0.7366 0.5001 0.4515 0.072 Uiso 1 1 calc R . . H31B H 0.8269 0.5348 0.5013 0.072 Uiso 1 1 calc R . . H31C H 0.7875 0.5127 0.3886 0.072 Uiso 1 1 calc R . . C32 C 0.65758(17) 1.39358(17) 0.1723(2) 0.0405(7) Uani 1 1 d . . . C33 C 0.6168(2) 1.3970(2) 0.2343(2) 0.0584(9) Uani 1 1 d . . . H33A H 0.5973 1.4551 0.2350 0.088 Uiso 1 1 calc R . . H33B H 0.6539 1.3807 0.2998 0.088 Uiso 1 1 calc R . . H33C H 0.5712 1.3574 0.2108 0.088 Uiso 1 1 calc R . . C34 C 0.88360(16) 1.36473(19) 0.2945(2) 0.0420(7) Uani 1 1 d . . . C35 C 0.8516(2) 1.2791(2) 0.2834(4) 0.0940(16) Uani 1 1 d . . . H35A H 0.8206 1.2670 0.2147 0.141 Uiso 1 1 calc R . . H35B H 0.8166 1.2742 0.3174 0.141 Uiso 1 1 calc R . . H35C H 0.8959 1.2382 0.3104 0.141 Uiso 1 1 calc R . . C36 C 1.0336(3) 0.6427(3) 0.4213(3) 0.0687(12) Uani 1 1 d . . . C37 C 0.9725(2) 0.6099(2) 0.4495(3) 0.0694(11) Uani 1 1 d . . . H37A H 0.9342 0.6554 0.4443 0.104 Uiso 1 1 calc R . . H37B H 0.9978 0.5896 0.5162 0.104 Uiso 1 1 calc R . . H37C H 0.9442 0.5626 0.4069 0.104 Uiso 1 1 calc R . . N2 N 0.87709(10) 0.89005(11) 0.25326(13) 0.0188(4) Uani 1 1 d . . . 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 0.02116(13) 0.01589(12) 0.02568(15) -0.00337(11) 0.01330(11) -0.00064(10) N1 0.0170(9) 0.0154(10) 0.0197(11) 0.0018(8) 0.0080(8) 0.0020(7) C1 0.0169(11) 0.0211(12) 0.0147(12) -0.0014(9) 0.0053(10) 0.0022(9) C2 0.0186(11) 0.0168(11) 0.0167(12) 0.0003(9) 0.0052(10) 0.0003(9) N3 0.0184(9) 0.0166(10) 0.0187(10) -0.0004(8) 0.0088(8) 0.0007(7) C3 0.0237(12) 0.0206(12) 0.0301(14) 0.0027(10) 0.0146(11) -0.0003(10) N4 0.0153(9) 0.0165(10) 0.0216(11) -0.0032(8) 0.0066(9) 0.0002(7) C4 0.0231(12) 0.0269(13) 0.0305(14) 0.0006(11) 0.0170(11) -0.0031(10) N5 0.0196(11) 0.0301(12) 0.0366(13) 0.0006(10) 0.0124(10) 0.0050(8) C5 0.0273(13) 0.0174(11) 0.0242(13) -0.0050(10) 0.0123(11) 0.0020(10) N6 0.0264(13) 0.0513(15) 0.0356(14) -0.0028(11) 0.0087(11) 0.0105(10) C6 0.0237(12) 0.0197(12) 0.0293(14) -0.0059(11) 0.0143(11) 0.0026(10) N7 0.0277(14) 0.141(3) 0.062(2) 0.000(2) 0.0193(14) 0.0221(16) C7 0.0171(11) 0.0186(12) 0.0347(15) -0.0050(11) 0.0112(11) -0.0004(9) N8 0.0298(13) 0.0460(15) 0.0496(18) -0.0067(13) 0.0146(13) -0.0004(11) C8 0.0192(11) 0.0133(11) 0.0237(13) 0.0013(9) 0.0117(10) -0.0008(9) N9 0.0252(11) 0.0447(13) 0.0147(12) 0.0174(10) 0.0155(10) 0.0192(10) C9 0.0220(12) 0.0159(11) 0.0239(13) -0.0001(10) 0.0116(11) -0.0052(9) N10 0.0516(16) 0.100(2) 0.0533(19) 0.0221(17) 0.0348(15) 0.0255(16) C10 0.0349(14) 0.0267(14) 0.0290(14) -0.0045(11) 0.0191(12) -0.0019(11) N11 0.078(2) 0.082(2) 0.104(3) 0.036(2) 0.060(2) 0.0213(18) C11 0.0299(14) 0.0253(14) 0.0435(17) -0.0047(12) 0.0213(13) 0.0041(11) N12 0.0601(17) 0.0432(16) 0.0515(17) -0.0028(13) 0.0203(14) -0.0094(13) C12 0.0204(12) 0.0255(13) 0.0344(15) 0.0023(12) 0.0074(11) 0.0060(10) N13 0.083(3) 0.113(3) 0.127(4) -0.040(3) 0.049(3) 0.029(2) C13 0.0220(12) 0.0177(12) 0.0250(14) -0.0005(10) 0.0079(11) -0.0015(10) C14 0.0335(14) 0.0274(14) 0.0231(14) 0.0007(11) 0.0037(12) 0.0110(11) C15 0.0439(17) 0.0359(16) 0.0340(17) -0.0010(13) -0.0069(14) 0.0044(13) C16 0.064(2) 0.0451(18) 0.0327(17) 0.0057(14) 0.0214(16) 0.0041(15) C17 0.0287(13) 0.0227(13) 0.0220(13) -0.0002(10) 0.0088(11) -0.0019(10) C18 0.0343(16) 0.055(2) 0.053(2) 0.0195(16) -0.0057(15) -0.0165(14) C19 0.0589(19) 0.0484(18) 0.0337(17) 0.0137(14) 0.0214(15) -0.0001(15) C20 0.0208(11) 0.0124(11) 0.0294(14) -0.0024(10) 0.0131(11) 0.0001(9) C21 0.0350(14) 0.0170(12) 0.0310(15) -0.0019(10) 0.0195(12) 0.0007(10) C22 0.0487(17) 0.0276(14) 0.0525(19) 0.0030(13) 0.0391(16) 0.0022(12) C23 0.0320(15) 0.0337(16) 0.072(2) 0.0013(15) 0.0347(17) -0.0009(12) C24 0.0234(13) 0.0311(14) 0.0536(19) 0.0009(13) 0.0141(14) 0.0002(11) C25 0.0236(12) 0.0160(12) 0.0342(15) 0.0013(11) 0.0102(12) 0.0005(10) C26 0.0250(13) 0.0295(14) 0.0313(15) 0.0039(12) 0.0032(12) -0.0055(11) C27 0.0573(19) 0.0412(17) 0.0374(17) 0.0021(14) 0.0211(15) 0.0055(14) C28 0.0541(18) 0.0327(16) 0.0377(18) 0.0027(13) -0.0025(15) 0.0057(14) C29 0.0465(16) 0.0318(14) 0.0240(14) 0.0012(11) 0.0178(13) -0.0008(12) C30 0.080(2) 0.059(2) 0.0325(17) -0.0040(15) 0.0274(18) 0.0077(18) C31 0.0600(19) 0.0440(18) 0.0373(18) 0.0090(14) 0.0178(16) 0.0119(15) C32 0.0345(16) 0.0299(15) 0.053(2) 0.0082(14) 0.0138(15) 0.0026(12) C33 0.083(2) 0.0416(19) 0.056(2) -0.0052(16) 0.034(2) 0.0073(17) C34 0.0337(15) 0.0384(18) 0.0470(19) 0.0033(14) 0.0099(14) 0.0013(13) C35 0.046(2) 0.037(2) 0.163(5) 0.017(2) 0.007(2) -0.0049(16) C36 0.065(3) 0.058(3) 0.061(3) -0.022(2) 0.004(2) 0.034(2) C37 0.094(3) 0.044(2) 0.046(2) -0.0012(17) 0.006(2) 0.013(2) N2 0.0160(9) 0.0184(10) 0.0218(11) -0.0036(8) 0.0077(9) -0.0003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 N5 2.037(2) . ? Ge1 C2 2.046(2) . ? Ge1 C1 2.051(2) . ? N1 C1 1.341(3) . ? N1 C3 1.378(3) . ? N1 C8 1.442(3) . ? C1 N2 1.347(3) . ? C2 N4 1.342(3) . ? C2 N3 1.345(3) . ? N3 C5 1.380(3) . ? N3 C20 1.446(3) . ? C3 C4 1.341(3) . ? N4 C6 1.377(3) . ? N4 C7 1.453(3) . ? C4 N2 1.375(3) . ? N5 N6 1.199(3) . ? C5 C6 1.343(3) . ? N6 N7 1.148(3) . ? C7 N2 1.455(3) . ? N8 N9 1.098(3) . ? C8 C9 1.394(3) . ? C8 C13 1.397(3) . ? N9 N10 1.185(3) . ? C9 C10 1.393(3) . ? C9 C17 1.516(3) . ? C10 C11 1.377(4) . ? N11 C32 1.121(4) . ? C11 C12 1.373(4) . ? N12 C34 1.123(3) . ? C12 C13 1.387(3) . ? N13 C36 1.126(6) . ? C13 C14 1.513(3) . ? C14 C15 1.524(3) . ? C14 C16 1.530(4) . ? C17 C19 1.508(3) . ? C17 C18 1.514(3) . ? C20 C21 1.390(3) . ? C20 C25 1.396(3) . ? C21 C22 1.393(3) . ? C21 C29 1.513(4) . ? C22 C23 1.379(4) . ? C23 C24 1.366(4) . ? C24 C25 1.388(3) . ? C25 C26 1.513(4) . ? C26 C27 1.523(4) . ? C26 C28 1.523(3) . ? C29 C30 1.522(4) . ? C29 C31 1.529(4) . ? C32 C33 1.427(4) . ? C34 C35 1.445(4) . ? C36 C37 1.448(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Ge1 C2 89.14(8) . . ? N5 Ge1 C1 89.38(8) . . ? C2 Ge1 C1 84.49(9) . . ? C1 N1 C3 110.74(18) . . ? C1 N1 C8 125.20(18) . . ? C3 N1 C8 123.88(18) . . ? N1 C1 N2 104.87(19) . . ? N1 C1 Ge1 127.28(16) . . ? N2 C1 Ge1 127.79(16) . . ? N4 C2 N3 104.88(18) . . ? N4 C2 Ge1 127.97(15) . . ? N3 C2 Ge1 127.01(16) . . ? C2 N3 C5 110.71(18) . . ? C2 N3 C20 125.05(18) . . ? C5 N3 C20 124.23(18) . . ? C4 C3 N1 107.0(2) . . ? C2 N4 C6 111.20(18) . . ? C2 N4 C7 126.18(18) . . ? C6 N4 C7 122.20(18) . . ? C3 C4 N2 106.4(2) . . ? N6 N5 Ge1 114.40(18) . . ? C6 C5 N3 106.8(2) . . ? N7 N6 N5 177.0(3) . . ? C5 C6 N4 106.40(19) . . ? N4 C7 N2 111.87(17) . . ? C9 C8 C13 123.5(2) . . ? C9 C8 N1 117.53(19) . . ? C13 C8 N1 119.0(2) . . ? N8 N9 N10 173.0(3) . . ? C10 C9 C8 116.9(2) . . ? C10 C9 C17 120.1(2) . . ? C8 C9 C17 122.9(2) . . ? C11 C10 C9 120.8(2) . . ? C12 C11 C10 120.7(2) . . ? C11 C12 C13 121.3(2) . . ? C12 C13 C8 116.7(2) . . ? C12 C13 C14 120.5(2) . . ? C8 C13 C14 122.8(2) . . ? C13 C14 C15 111.5(2) . . ? C13 C14 C16 111.3(2) . . ? C15 C14 C16 110.4(2) . . ? C19 C17 C18 110.9(2) . . ? C19 C17 C9 112.8(2) . . ? C18 C17 C9 110.3(2) . . ? C21 C20 C25 124.2(2) . . ? C21 C20 N3 118.0(2) . . ? C25 C20 N3 117.8(2) . . ? C20 C21 C22 116.6(2) . . ? C20 C21 C29 122.6(2) . . ? C22 C21 C29 120.7(2) . . ? C23 C22 C21 120.6(3) . . ? C24 C23 C22 121.1(2) . . ? C23 C24 C25 121.3(3) . . ? C24 C25 C20 116.3(2) . . ? C24 C25 C26 121.1(2) . . ? C20 C25 C26 122.6(2) . . ? C25 C26 C27 111.7(2) . . ? C25 C26 C28 112.7(2) . . ? C27 C26 C28 110.0(2) . . ? C21 C29 C30 113.0(2) . . ? C21 C29 C31 109.9(2) . . ? C30 C29 C31 111.2(2) . . ? N11 C32 C33 179.0(4) . . ? N12 C34 C35 178.5(4) . . ? N13 C36 C37 177.9(5) . . ? C1 N2 C4 111.06(18) . . ? C1 N2 C7 125.86(19) . . ? C4 N2 C7 122.41(18) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.359 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 935359' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef '3.CIF' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H64.50 B Cl Ge N5.50' _chemical_formula_weight 957.50 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1255(12) _cell_length_b 12.1448(9) _cell_length_c 31.202(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.799(8) _cell_angle_gamma 90.00 _cell_volume 5350.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3162 _cell_measurement_theta_min 3.3771 _cell_measurement_theta_max 32.4884 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2020 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_T_min 0.15401 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22821 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.1501 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9398 _reflns_number_gt 6048 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^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 9398 _refine_ls_number_parameters 627 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1337 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1360 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.80327(3) 0.36776(4) 0.562303(16) 0.02461(16) Uani 1 1 d . . . Cl1 Cl 0.70504(10) 0.51843(10) 0.55345(4) 0.0418(4) Uani 1 1 d . . . N1 N 0.7211(2) 0.3582(3) 0.65218(11) 0.0184(9) Uani 1 1 d . . . C1 C 0.7971(3) 0.3762(4) 0.62761(14) 0.0186(10) Uani 1 1 d . . . B1 B 0.4169(3) 0.0337(4) 0.69891(18) 0.0192(12) Uani 1 1 d . . . C18B C 1.072(2) 0.176(2) 0.6870(9) 0.049(8) Uani 0.261(13) 1 d PU A 2 H18A H 1.1374 0.1795 0.6774 0.074 Uiso 0.261(13) 1 calc PR A 2 H18B H 1.0553 0.0998 0.6933 0.074 Uiso 0.261(13) 1 calc PR A 2 H18C H 1.0664 0.2210 0.7129 0.074 Uiso 0.261(13) 1 calc PR A 2 C19B C 0.973(2) 0.1544(19) 0.6213(8) 0.058(9) Uani 0.261(13) 1 d PU A 2 H19A H 0.9122 0.1791 0.6089 0.087 Uiso 0.261(13) 1 calc PR A 2 H19B H 0.9657 0.0816 0.6342 0.087 Uiso 0.261(13) 1 calc PR A 2 H19C H 1.0197 0.1503 0.5986 0.087 Uiso 0.261(13) 1 calc PR A 2 N2 N 0.6303(2) 0.2567(3) 0.59934(11) 0.0160(8) Uani 1 1 d . . . C2 C 0.6900(3) 0.2635(3) 0.56645(13) 0.0153(10) Uani 1 1 d . . . N3 N 0.8672(2) 0.4011(3) 0.65610(12) 0.0196(9) Uani 1 1 d . . . C3 C 0.6260(3) 0.3344(4) 0.63481(15) 0.0213(11) Uani 1 1 d . . . H3A H 0.5870 0.3030 0.6576 0.026 Uiso 1 1 calc R . . H3B H 0.5956 0.4035 0.6247 0.026 Uiso 1 1 calc R . . N4 N 0.6625(2) 0.1853(3) 0.53847(11) 0.0170(9) Uani 1 1 d . . . C4 C 0.7442(3) 0.3742(4) 0.69491(14) 0.0235(11) Uani 1 1 d . . . H4A H 0.7031 0.3668 0.7182 0.028 Uiso 1 1 calc R . . N5 N 0.0573(4) 0.4530(4) 0.75330(19) 0.0664(17) Uani 1 1 d . . . C5 C 0.8360(3) 0.4022(4) 0.69722(15) 0.0245(11) Uani 1 1 d . . . H5A H 0.8724 0.4195 0.7225 0.029 Uiso 1 1 calc R . . N6 N 1.0560(10) 0.2404(12) 0.5204(4) 0.097(4) Uiso 0.50 1 d P B -1 C6 C 0.5646(3) 0.1750(4) 0.59172(15) 0.0213(11) Uani 1 1 d . . . H6A H 0.5147 0.1546 0.6098 0.026 Uiso 1 1 calc R . . C7 C 0.5846(3) 0.1295(4) 0.55385(15) 0.0254(11) Uani 1 1 d . . . H7A H 0.5517 0.0704 0.5401 0.030 Uiso 1 1 calc R . . C8 C 0.9629(3) 0.4278(4) 0.64342(15) 0.0216(11) Uani 1 1 d . . . C9 C 0.9841(3) 0.5378(4) 0.63558(15) 0.0259(12) Uani 1 1 d . . . C10 C 1.0758(3) 0.5593(5) 0.62302(17) 0.0390(14) Uani 1 1 d . . . H10A H 1.0940 0.6331 0.6175 0.047 Uiso 1 1 calc R . . C11 C 1.1403(4) 0.4765(5) 0.61839(19) 0.0492(17) Uani 1 1 d . . . H11A H 1.2024 0.4934 0.6095 0.059 Uiso 1 1 calc R . . C12 C 1.1160(3) 0.3695(5) 0.62649(19) 0.0468(16) Uani 1 1 d . . . H12A H 1.1620 0.3133 0.6232 0.056 Uiso 1 1 calc R . . C13 C 1.0260(3) 0.3404(4) 0.63943(17) 0.0335(13) Uani 1 1 d . A . C14 C 0.9146(4) 0.6299(4) 0.6434(2) 0.0457(16) Uani 1 1 d . . . H14A H 0.8503 0.5963 0.6454 0.055 Uiso 1 1 calc R . . C15 C 0.9099(5) 0.7130(5) 0.6084(3) 0.101(3) Uani 1 1 d . . . H15A H 0.8975 0.6759 0.5809 0.152 Uiso 1 1 calc R . . H15B H 0.9704 0.7525 0.6076 0.152 Uiso 1 1 calc R . . H15C H 0.8589 0.7654 0.6137 0.152 Uiso 1 1 calc R . . C16 C 0.9398(4) 0.6851(5) 0.6871(2) 0.073(2) Uani 1 1 d . . . H16A H 0.8945 0.7443 0.6925 0.110 Uiso 1 1 calc R . . H16B H 1.0039 0.7158 0.6865 0.110 Uiso 1 1 calc R . . H16C H 0.9370 0.6302 0.7100 0.110 Uiso 1 1 calc R . . C17 C 1.0020(4) 0.2231(4) 0.6501(3) 0.0556(19) Uani 1 1 d . . . H17A H 0.9327 0.2125 0.6441 0.067 Uiso 1 1 calc R A 1 C20 C 0.7078(3) 0.1632(4) 0.49855(14) 0.0197(11) Uani 1 1 d . . . C21 C 0.6816(3) 0.2272(4) 0.46289(16) 0.0277(12) Uani 1 1 d . . . C22 C 0.7290(4) 0.2064(4) 0.42498(16) 0.0374(14) Uani 1 1 d . . . H22A H 0.7137 0.2478 0.3999 0.045 Uiso 1 1 calc R . . C23 C 0.7979(4) 0.1261(5) 0.42395(18) 0.0471(16) Uani 1 1 d . . . H23A H 0.8307 0.1138 0.3983 0.056 Uiso 1 1 calc R . . C24 C 0.8196(4) 0.0640(5) 0.45941(17) 0.0439(15) Uani 1 1 d . . . H24A H 0.8667 0.0086 0.4576 0.053 Uiso 1 1 calc R . . C25 C 0.7752(3) 0.0793(4) 0.49775(16) 0.0305(12) Uani 1 1 d . . . C26 C 0.6027(4) 0.3108(4) 0.46422(17) 0.0364(13) Uani 1 1 d . . . H26A H 0.5949 0.3318 0.4949 0.044 Uiso 1 1 calc R . . C27 C 0.5101(4) 0.2584(5) 0.4482(2) 0.067(2) Uani 1 1 d . . . H27A H 0.4997 0.1896 0.4638 0.100 Uiso 1 1 calc R . . H27B H 0.5135 0.2428 0.4175 0.100 Uiso 1 1 calc R . . H27C H 0.4575 0.3092 0.4531 0.100 Uiso 1 1 calc R . . C28 C 0.6209(5) 0.4169(5) 0.4390(2) 0.076(2) Uani 1 1 d . . . H28A H 0.6802 0.4506 0.4495 0.114 Uiso 1 1 calc R . . H28B H 0.5685 0.4684 0.4428 0.114 Uiso 1 1 calc R . . H28C H 0.6257 0.3993 0.4085 0.114 Uiso 1 1 calc R . . C29 C 0.7975(4) 0.0063(5) 0.53607(17) 0.0443(16) Uani 1 1 d . . . H29A H 0.7702 0.0422 0.5617 0.053 Uiso 1 1 calc R . . C30 C 0.7500(4) -0.1064(5) 0.53062(18) 0.0505(17) Uani 1 1 d . . . H30A H 0.6817 -0.0965 0.5256 0.076 Uiso 1 1 calc R . . H30B H 0.7613 -0.1502 0.5567 0.076 Uiso 1 1 calc R . . H30C H 0.7767 -0.1447 0.5061 0.076 Uiso 1 1 calc R . . C31 C 0.9030(5) -0.0072(5) 0.5450(2) 0.090(3) Uani 1 1 d . . . H31A H 0.9336 0.0652 0.5447 0.135 Uiso 1 1 calc R . . H31B H 0.9298 -0.0542 0.5229 0.135 Uiso 1 1 calc R . . H31C H 0.9136 -0.0413 0.5732 0.135 Uiso 1 1 calc R . . C32 C 0.3800(3) 0.1268(4) 0.66461(14) 0.0171(10) Uani 1 1 d . . . C33 C 0.3435(3) 0.0966(4) 0.62389(15) 0.0226(11) Uani 1 1 d . . . H33A H 0.3313 0.0209 0.6184 0.027 Uiso 1 1 calc R . . C34 C 0.3242(3) 0.1715(4) 0.59149(16) 0.0312(13) Uani 1 1 d . . . H34A H 0.2996 0.1467 0.5645 0.037 Uiso 1 1 calc R . . C35 C 0.3407(3) 0.2818(5) 0.59806(19) 0.0374(14) Uani 1 1 d . . . H35A H 0.3287 0.3331 0.5756 0.045 Uiso 1 1 calc R . . C36 C 0.3748(3) 0.3173(4) 0.63774(18) 0.0300(13) Uani 1 1 d . . . H36A H 0.3852 0.3935 0.6429 0.036 Uiso 1 1 calc R . . C37 C 0.3938(3) 0.2408(4) 0.66999(15) 0.0224(11) Uani 1 1 d . . . H37A H 0.4172 0.2667 0.6970 0.027 Uiso 1 1 calc R . . C38 C 0.5276(3) 0.0143(3) 0.68559(14) 0.0166(10) Uani 1 1 d . . . C39 C 0.5542(3) -0.0642(4) 0.65505(15) 0.0242(11) Uani 1 1 d . . . H39A H 0.5078 -0.1140 0.6439 0.029 Uiso 1 1 calc R . . C40 C 0.6468(3) -0.0714(4) 0.64059(16) 0.0309(13) Uani 1 1 d . . . H40A H 0.6624 -0.1266 0.6204 0.037 Uiso 1 1 calc R . . C41 C 0.7151(3) 0.0005(4) 0.65536(16) 0.0309(13) Uani 1 1 d . . . H41A H 0.7779 -0.0044 0.6455 0.037 Uiso 1 1 calc R . . C42 C 0.6915(3) 0.0805(4) 0.68488(16) 0.0280(12) Uani 1 1 d . . . H42A H 0.7379 0.1314 0.6952 0.034 Uiso 1 1 calc R . . C43 C 0.5991(3) 0.0856(4) 0.69937(14) 0.0217(11) Uani 1 1 d . . . H43A H 0.5843 0.1408 0.7197 0.026 Uiso 1 1 calc R . . C44 C 0.4107(3) 0.0743(3) 0.74895(14) 0.0157(10) Uani 1 1 d . . . C45 C 0.4732(3) 0.0385(4) 0.78160(14) 0.0206(11) Uani 1 1 d . . . H45A H 0.5242 -0.0082 0.7743 0.025 Uiso 1 1 calc R . . C46 C 0.4641(3) 0.0684(4) 0.82434(15) 0.0264(12) Uani 1 1 d . . . H46A H 0.5094 0.0437 0.8453 0.032 Uiso 1 1 calc R . . C47 C 0.3895(4) 0.1339(4) 0.83645(16) 0.0310(12) Uani 1 1 d . . . H47A H 0.3824 0.1539 0.8656 0.037 Uiso 1 1 calc R . . C48 C 0.3248(3) 0.1699(4) 0.80476(16) 0.0285(12) Uani 1 1 d . . . H48A H 0.2730 0.2150 0.8123 0.034 Uiso 1 1 calc R . . C49 C 0.3357(3) 0.1404(4) 0.76269(15) 0.0250(11) Uani 1 1 d . . . H49A H 0.2904 0.1659 0.7419 0.030 Uiso 1 1 calc R . . C50 C 0.3505(3) -0.0767(4) 0.69678(14) 0.0172(10) Uani 1 1 d . . . C51 C 0.3811(3) -0.1855(4) 0.70135(14) 0.0208(11) Uani 1 1 d . . . H51A H 0.4473 -0.1991 0.7039 0.025 Uiso 1 1 calc R . . C52 C 0.3202(3) -0.2745(4) 0.70234(14) 0.0260(12) Uani 1 1 d . . . H52A H 0.3449 -0.3469 0.7056 0.031 Uiso 1 1 calc R . . C53 C 0.2222(3) -0.2582(4) 0.69855(14) 0.0232(11) Uani 1 1 d . . . H53A H 0.1798 -0.3188 0.6988 0.028 Uiso 1 1 calc R . . C54 C 0.1890(3) -0.1527(4) 0.69452(14) 0.0216(11) Uani 1 1 d . . . H54A H 0.1227 -0.1400 0.6928 0.026 Uiso 1 1 calc R . . C55 C 0.2506(3) -0.0645(4) 0.69299(14) 0.0191(10) Uani 1 1 d . . . H55A H 0.2251 0.0073 0.6892 0.023 Uiso 1 1 calc R . . C56 C 0.1320(4) 0.4388(4) 0.74353(19) 0.0425(15) Uani 1 1 d . . . C57 C 0.2293(4) 0.4187(4) 0.73119(18) 0.0430(15) Uani 1 1 d . . . H57A H 0.2677 0.3972 0.7565 0.064 Uiso 1 1 calc R . . H57B H 0.2554 0.4860 0.7189 0.064 Uiso 1 1 calc R . . H57C H 0.2302 0.3594 0.7099 0.064 Uiso 1 1 calc R . . C58 C 1.0469(9) 0.3296(12) 0.5128(4) 0.064(4) Uiso 0.50 1 d P B -1 C59 C 1.0325(10) 0.4419(10) 0.5035(5) 0.080(5) Uiso 0.50 1 d P B -1 H59A H 1.0904 0.4732 0.4920 0.121 Uiso 0.50 1 calc PR B -1 H59B H 1.0166 0.4811 0.5297 0.121 Uiso 0.50 1 calc PR B -1 H59C H 0.9804 0.4497 0.4822 0.121 Uiso 0.50 1 calc PR B -1 C18A C 1.0214(9) 0.1946(9) 0.6939(4) 0.072(4) Uani 0.739(13) 1 d PU A 1 H18D H 1.0886 0.2073 0.7010 0.108 Uiso 0.739(13) 1 calc PR A 1 H18E H 1.0063 0.1168 0.6984 0.108 Uiso 0.739(13) 1 calc PR A 1 H18F H 0.9827 0.2403 0.7124 0.108 Uiso 0.739(13) 1 calc PR A 1 C19A C 1.0591(7) 0.1402(7) 0.6188(3) 0.064(3) Uani 0.739(13) 1 d PU A 1 H19D H 1.0520 0.1658 0.5891 0.096 Uiso 0.739(13) 1 calc PR A 1 H19E H 1.0331 0.0657 0.6211 0.096 Uiso 0.739(13) 1 calc PR A 1 H19F H 1.1263 0.1394 0.6275 0.096 Uiso 0.739(13) 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 0.0206(3) 0.0378(3) 0.0154(3) 0.0014(3) 0.00061(19) -0.0094(2) Cl1 0.0627(9) 0.0260(7) 0.0357(9) 0.0083(7) -0.0137(7) 0.0043(7) N1 0.020(2) 0.020(2) 0.015(2) -0.0038(19) -0.0015(16) -0.0011(17) C1 0.019(2) 0.025(3) 0.012(2) 0.000(2) 0.0005(19) -0.004(2) B1 0.016(3) 0.017(3) 0.025(3) -0.006(3) -0.002(2) -0.005(2) C18B 0.054(11) 0.039(10) 0.053(11) 0.012(8) -0.011(8) -0.012(8) C19B 0.067(12) 0.048(11) 0.060(12) 0.001(8) 0.007(8) -0.014(8) N2 0.0129(18) 0.021(2) 0.014(2) -0.0008(18) -0.0027(15) -0.0030(16) C2 0.023(2) 0.019(2) 0.004(2) -0.004(2) -0.0060(18) 0.003(2) N3 0.016(2) 0.025(2) 0.018(2) 0.0026(19) -0.0043(16) -0.0063(17) C3 0.014(2) 0.025(3) 0.025(3) -0.006(2) -0.0013(19) -0.002(2) N4 0.024(2) 0.017(2) 0.010(2) 0.0014(18) -0.0014(16) -0.0021(17) C4 0.030(3) 0.027(3) 0.014(3) -0.005(3) 0.005(2) -0.001(2) N5 0.051(4) 0.065(4) 0.083(5) -0.010(3) -0.005(3) 0.009(3) C5 0.031(3) 0.031(3) 0.011(3) -0.008(2) -0.003(2) -0.004(2) C6 0.019(2) 0.024(3) 0.020(3) 0.005(2) -0.002(2) -0.008(2) C7 0.028(3) 0.027(3) 0.022(3) 0.000(3) -0.002(2) -0.013(2) C8 0.011(2) 0.032(3) 0.021(3) -0.002(2) -0.0055(19) -0.007(2) C9 0.020(3) 0.032(3) 0.024(3) -0.002(2) -0.009(2) -0.008(2) C10 0.024(3) 0.044(3) 0.049(4) 0.012(3) -0.006(2) -0.013(3) C11 0.022(3) 0.066(4) 0.060(5) -0.004(4) 0.006(3) -0.012(3) C12 0.014(3) 0.053(4) 0.073(5) -0.022(4) -0.003(3) 0.001(3) C13 0.022(3) 0.032(3) 0.045(4) -0.009(3) -0.013(2) -0.005(2) C14 0.027(3) 0.032(3) 0.077(5) 0.003(3) -0.016(3) -0.001(3) C15 0.088(6) 0.056(5) 0.158(9) 0.063(5) -0.021(5) 0.017(4) C16 0.046(4) 0.061(4) 0.111(7) -0.044(5) -0.027(4) 0.005(3) C17 0.027(3) 0.031(3) 0.107(6) -0.005(4) -0.027(3) 0.004(3) C20 0.026(3) 0.026(3) 0.006(2) -0.003(2) -0.0059(19) -0.008(2) C21 0.033(3) 0.029(3) 0.021(3) 0.004(3) -0.009(2) -0.015(2) C22 0.049(4) 0.051(4) 0.012(3) 0.005(3) -0.005(2) -0.031(3) C23 0.038(3) 0.079(5) 0.025(3) -0.020(4) 0.008(3) -0.014(3) C24 0.033(3) 0.072(4) 0.026(3) -0.019(3) -0.007(2) 0.011(3) C25 0.029(3) 0.041(3) 0.021(3) -0.009(3) -0.009(2) 0.009(2) C26 0.050(4) 0.032(3) 0.027(3) 0.006(3) -0.015(3) -0.003(3) C27 0.042(4) 0.064(4) 0.093(6) -0.007(4) -0.028(3) 0.002(3) C28 0.112(6) 0.045(4) 0.069(5) 0.029(4) -0.024(4) -0.001(4) C29 0.061(4) 0.052(4) 0.018(3) -0.009(3) -0.018(3) 0.024(3) C30 0.046(4) 0.069(4) 0.036(4) 0.011(3) 0.002(3) 0.005(3) C31 0.078(5) 0.064(5) 0.124(7) 0.016(5) -0.077(5) -0.007(4) C32 0.009(2) 0.023(3) 0.019(3) 0.002(2) 0.0036(18) -0.0017(19) C33 0.022(3) 0.025(3) 0.020(3) 0.003(2) -0.007(2) -0.008(2) C34 0.023(3) 0.049(4) 0.021(3) 0.011(3) -0.009(2) -0.003(2) C35 0.019(3) 0.047(4) 0.046(4) 0.024(3) -0.002(2) 0.001(2) C36 0.020(3) 0.022(3) 0.048(4) 0.008(3) 0.007(2) -0.001(2) C37 0.016(2) 0.026(3) 0.025(3) -0.001(2) -0.001(2) -0.002(2) C38 0.017(2) 0.018(2) 0.015(3) 0.007(2) -0.0043(18) 0.0024(19) C39 0.025(3) 0.022(3) 0.026(3) 0.003(2) 0.001(2) -0.002(2) C40 0.036(3) 0.028(3) 0.029(3) 0.002(3) 0.012(2) 0.008(2) C41 0.024(3) 0.037(3) 0.031(3) 0.015(3) 0.006(2) 0.008(2) C42 0.017(3) 0.034(3) 0.033(3) 0.014(3) -0.006(2) -0.004(2) C43 0.018(2) 0.026(3) 0.020(3) 0.004(2) -0.008(2) 0.004(2) C44 0.020(2) 0.011(2) 0.015(3) 0.000(2) -0.0012(19) -0.0042(19) C45 0.023(3) 0.020(3) 0.018(3) 0.006(2) -0.003(2) -0.005(2) C46 0.032(3) 0.026(3) 0.021(3) 0.005(2) -0.011(2) -0.008(2) C47 0.052(3) 0.027(3) 0.014(3) -0.007(3) 0.000(2) -0.015(3) C48 0.033(3) 0.025(3) 0.028(3) -0.007(3) 0.005(2) -0.002(2) C49 0.026(3) 0.028(3) 0.021(3) -0.001(3) -0.003(2) -0.001(2) C50 0.022(2) 0.021(3) 0.009(2) 0.001(2) -0.0007(18) -0.002(2) C51 0.020(2) 0.027(3) 0.016(3) 0.003(2) -0.001(2) -0.002(2) C52 0.040(3) 0.021(3) 0.016(3) 0.001(2) -0.007(2) -0.003(2) C53 0.027(3) 0.022(3) 0.019(3) 0.007(2) -0.007(2) -0.011(2) C54 0.020(2) 0.030(3) 0.015(3) 0.000(2) -0.0050(19) -0.006(2) C55 0.024(3) 0.020(2) 0.013(3) 0.000(2) -0.0014(19) 0.000(2) C56 0.049(4) 0.035(3) 0.043(4) -0.007(3) -0.009(3) 0.003(3) C57 0.047(4) 0.036(3) 0.045(4) -0.011(3) -0.009(3) 0.002(3) C18A 0.088(7) 0.053(6) 0.076(7) 0.005(5) 0.011(6) -0.012(6) C19A 0.065(6) 0.046(5) 0.080(6) -0.020(5) -0.015(5) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 C1 2.045(4) . ? Ge1 C2 2.048(4) . ? Ge1 Cl1 2.3078(14) . ? N1 C1 1.357(5) . ? N1 C4 1.376(5) . ? N1 C3 1.462(5) . ? C1 N3 1.344(5) . ? B1 C32 1.631(7) . ? B1 C50 1.636(6) . ? B1 C44 1.642(7) . ? B1 C38 1.647(6) . ? C18B C17 1.60(3) . ? C19B C17 1.28(2) . ? N2 C2 1.351(5) . ? N2 C6 1.374(5) . ? N2 C3 1.457(5) . ? C2 N4 1.339(5) . ? N3 C5 1.370(5) . ? N3 C8 1.456(5) . ? N4 C7 1.391(5) . ? N4 C20 1.443(5) . ? C4 C5 1.340(6) . ? N5 C56 1.122(7) . ? N6 C58 1.116(15) . ? C6 C7 1.342(6) . ? C8 C9 1.392(6) . ? C8 C13 1.395(6) . ? C9 C10 1.389(6) . ? C9 C14 1.513(7) . ? C10 C11 1.367(7) . ? C11 C12 1.371(7) . ? C12 C13 1.391(6) . ? C13 C17 1.504(7) . ? C14 C15 1.487(8) . ? C14 C16 1.552(8) . ? C17 C18A 1.427(12) . ? C17 C19A 1.632(10) . ? C20 C25 1.396(6) . ? C20 C21 1.397(6) . ? C21 C22 1.401(7) . ? C21 C26 1.509(7) . ? C22 C23 1.378(7) . ? C23 C24 1.366(7) . ? C24 C25 1.380(7) . ? C25 C29 1.514(7) . ? C26 C27 1.524(7) . ? C26 C28 1.536(7) . ? C29 C31 1.516(7) . ? C29 C30 1.531(7) . ? C32 C33 1.405(6) . ? C32 C37 1.407(6) . ? C33 C34 1.381(6) . ? C34 C35 1.373(7) . ? C35 C36 1.384(7) . ? C36 C37 1.389(6) . ? C38 C43 1.388(6) . ? C38 C39 1.408(6) . ? C39 C40 1.399(6) . ? C40 C41 1.370(7) . ? C41 C42 1.386(6) . ? C42 C43 1.396(6) . ? C44 C45 1.397(6) . ? C44 C49 1.407(6) . ? C45 C46 1.392(6) . ? C46 C47 1.383(6) . ? C47 C48 1.395(7) . ? C48 C49 1.374(6) . ? C50 C51 1.397(6) . ? C50 C55 1.419(6) . ? C51 C52 1.383(6) . ? C52 C53 1.399(6) . ? C53 C54 1.368(6) . ? C54 C55 1.382(6) . ? C56 C57 1.460(7) . ? C58 C59 1.408(16) . ? 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 C1 Ge1 C2 84.86(16) . . ? C1 Ge1 Cl1 92.02(13) . . ? C2 Ge1 Cl1 91.71(12) . . ? C1 N1 C4 110.9(4) . . ? C1 N1 C3 123.8(4) . . ? C4 N1 C3 125.1(3) . . ? N3 C1 N1 104.0(4) . . ? N3 C1 Ge1 128.1(3) . . ? N1 C1 Ge1 127.9(3) . . ? C32 B1 C50 111.7(4) . . ? C32 B1 C44 113.0(4) . . ? C50 B1 C44 103.7(3) . . ? C32 B1 C38 102.7(3) . . ? C50 B1 C38 114.9(4) . . ? C44 B1 C38 111.2(4) . . ? C2 N2 C6 110.3(4) . . ? C2 N2 C3 125.4(4) . . ? C6 N2 C3 123.7(3) . . ? N4 C2 N2 106.1(4) . . ? N4 C2 Ge1 127.5(3) . . ? N2 C2 Ge1 126.4(3) . . ? C1 N3 C5 111.7(4) . . ? C1 N3 C8 122.7(4) . . ? C5 N3 C8 125.5(4) . . ? N2 C3 N1 110.5(3) . . ? C2 N4 C7 109.7(4) . . ? C2 N4 C20 124.6(4) . . ? C7 N4 C20 125.7(4) . . ? C5 C4 N1 106.7(4) . . ? C4 C5 N3 106.6(4) . . ? C7 C6 N2 106.9(4) . . ? C6 C7 N4 107.1(4) . . ? C9 C8 C13 124.9(4) . . ? C9 C8 N3 118.0(4) . . ? C13 C8 N3 117.1(4) . . ? C10 C9 C8 116.0(4) . . ? C10 C9 C14 121.5(5) . . ? C8 C9 C14 122.4(4) . . ? C11 C10 C9 121.5(5) . . ? C10 C11 C12 120.4(5) . . ? C11 C12 C13 122.1(5) . . ? C12 C13 C8 115.2(5) . . ? C12 C13 C17 121.3(5) . . ? C8 C13 C17 123.5(4) . . ? C15 C14 C9 113.4(5) . . ? C15 C14 C16 110.8(6) . . ? C9 C14 C16 109.2(5) . . ? C19B C17 C18A 124.1(13) . . ? C19B C17 C13 121.9(13) . . ? C18A C17 C13 113.8(7) . . ? C19B C17 C18B 116.7(16) . . ? C18A C17 C18B 29.4(10) . . ? C13 C17 C18B 110.9(11) . . ? C19B C17 C19A 48.1(13) . . ? C18A C17 C19A 109.8(7) . . ? C13 C17 C19A 109.4(6) . . ? C18B C17 C19A 84.6(11) . . ? C25 C20 C21 123.8(4) . . ? C25 C20 N4 118.2(4) . . ? C21 C20 N4 118.0(4) . . ? C20 C21 C22 116.8(5) . . ? C20 C21 C26 122.0(4) . . ? C22 C21 C26 121.2(5) . . ? C23 C22 C21 120.3(5) . . ? C24 C23 C22 120.8(5) . . ? C23 C24 C25 122.1(5) . . ? C24 C25 C20 116.2(5) . . ? C24 C25 C29 121.2(5) . . ? C20 C25 C29 122.6(4) . . ? C21 C26 C27 109.7(4) . . ? C21 C26 C28 114.5(5) . . ? C27 C26 C28 109.7(5) . . ? C25 C29 C31 112.8(5) . . ? C25 C29 C30 110.9(5) . . ? C31 C29 C30 110.4(5) . . ? C33 C32 C37 114.2(4) . . ? C33 C32 B1 120.9(4) . . ? C37 C32 B1 124.3(4) . . ? C34 C33 C32 123.2(5) . . ? C35 C34 C33 120.3(5) . . ? C34 C35 C36 119.4(5) . . ? C35 C36 C37 119.6(5) . . ? C36 C37 C32 123.3(5) . . ? C43 C38 C39 115.2(4) . . ? C43 C38 B1 121.3(4) . . ? C39 C38 B1 122.9(4) . . ? C40 C39 C38 122.2(4) . . ? C41 C40 C39 120.4(5) . . ? C40 C41 C42 119.3(4) . . ? C41 C42 C43 119.5(5) . . ? C38 C43 C42 123.3(4) . . ? C45 C44 C49 114.8(4) . . ? C45 C44 B1 123.3(4) . . ? C49 C44 B1 121.6(4) . . ? C46 C45 C44 122.9(4) . . ? C47 C46 C45 120.4(5) . . ? C46 C47 C48 118.3(5) . . ? C49 C48 C47 120.3(5) . . ? C48 C49 C44 123.2(5) . . ? C51 C50 C55 114.3(4) . . ? C51 C50 B1 126.5(4) . . ? C55 C50 B1 119.0(4) . . ? C52 C51 C50 123.4(4) . . ? C51 C52 C53 120.1(4) . . ? C54 C53 C52 118.4(4) . . ? C53 C54 C55 120.9(4) . . ? C54 C55 C50 122.8(4) . . ? N5 C56 C57 179.1(7) . . ? N6 C58 C59 178.2(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.850 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 935360' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 #TrackingRef '4.CIF' _audit_creation_method ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H63 B Ge N8' _chemical_formula_weight 943.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1299(3) _cell_length_b 12.3150(2) _cell_length_c 30.9315(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.667(2) _cell_angle_gamma 90.00 _cell_volume 5380.10(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18497 _cell_measurement_theta_min 2.8530 _cell_measurement_theta_max 73.4480 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 1.099 _exptl_absorpt_correction_T_min 0.52801 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset, Atlas' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36892 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 67.50 _reflns_number_total 9652 _reflns_number_gt 8822 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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^)+(0.0647P)^2^+6.8861P] 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 9652 _refine_ls_number_parameters 650 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.083 _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 N1 N 0.16571(14) 0.82287(18) 0.03861(6) 0.0287(5) Uani 1 1 d . B . C1 C 0.19252(16) 0.7448(2) 0.06661(8) 0.0273(5) Uani 1 1 d . . . B1 B 0.91855(19) -0.0291(2) 0.20062(9) 0.0262(6) Uani 1 1 d . . . N6B N 0.1763(12) 0.517(3) 0.0479(10) 0.121(8) Uani 0.25 1 d PDU A 2 N2 N 0.13182(13) 0.75141(18) 0.09934(6) 0.0268(4) Uani 1 1 d . B . C2 C 0.29715(17) 0.6306(2) 0.12795(8) 0.0296(5) Uani 1 1 d . . . N3 N 0.22203(14) 0.64880(18) 0.15233(7) 0.0278(5) Uani 1 1 d . B . C3 C 0.08797(19) 0.8778(2) 0.05379(9) 0.0339(6) Uani 1 1 d . . . H16 H 0.0557 0.9363 0.0399 0.041 Uiso 1 1 calc R B . N4 N 0.36813(15) 0.60466(19) 0.15587(7) 0.0299(5) Uani 1 1 d . B . C4 C 0.06659(17) 0.8328(2) 0.09196(8) 0.0311(6) Uani 1 1 d . B . H46 H 0.0165 0.8531 0.1101 0.037 Uiso 1 1 calc R . . C5 C 0.24445(19) 0.6317(2) 0.19562(8) 0.0323(6) Uani 1 1 d . . . H10 H 0.2031 0.6382 0.2191 0.039 Uiso 1 1 calc R B . C6 C 0.33641(19) 0.6041(2) 0.19773(8) 0.0339(6) Uani 1 1 d . B . H39 H 0.3728 0.5873 0.2232 0.041 Uiso 1 1 calc R . . C7 C 0.12708(17) 0.6745(2) 0.13501(8) 0.0308(5) Uani 1 1 d . . . H7A H 0.0956 0.6070 0.1248 0.037 Uiso 1 1 calc R B . H7B H 0.0888 0.7059 0.1582 0.037 Uiso 1 1 calc R . . N8 N 0.5583(2) 0.5511(3) 0.25355(12) 0.0722(9) Uani 1 1 d . . . C8 C 0.21340(19) 0.8458(2) -0.00142(8) 0.0344(6) Uani 1 1 d . . . C9 C 0.2793(2) 0.9293(3) -0.00122(9) 0.0453(7) Uani 1 1 d . B . C10 C 0.3268(2) 0.9479(4) -0.03952(11) 0.0637(11) Uani 1 1 d . . . H52 H 0.3730 1.0037 -0.0407 0.076 Uiso 1 1 calc R B . C11 C 0.3068(3) 0.8855(4) -0.07568(11) 0.0711(13) Uani 1 1 d . B . H54 H 0.3402 0.8984 -0.1014 0.085 Uiso 1 1 calc R . . C12 C 0.2393(3) 0.8051(4) -0.07519(10) 0.0620(11) Uani 1 1 d . . . H48 H 0.2261 0.7643 -0.1007 0.074 Uiso 1 1 calc R B . C13 C 0.1897(2) 0.7823(3) -0.03777(9) 0.0455(8) Uani 1 1 d . B . C14 C 0.1117(3) 0.6994(3) -0.03731(11) 0.0582(10) Uani 1 1 d . . . H29 H 0.1016 0.6789 -0.0065 0.070 Uiso 1 1 calc R B . C15 C 0.1363(5) 0.5953(4) -0.06212(17) 0.111(2) Uani 1 1 d . B . H60A H 0.1394 0.6116 -0.0931 0.167 Uiso 1 1 calc R . . H60B H 0.0874 0.5403 -0.0576 0.167 Uiso 1 1 calc R . . H60C H 0.1977 0.5676 -0.0515 0.167 Uiso 1 1 calc R . . C16 C 0.0187(4) 0.7496(5) -0.0556(2) 0.107(2) Uani 1 1 d . B . H63A H 0.0060 0.8176 -0.0404 0.161 Uiso 1 1 calc R . . H63B H -0.0336 0.6987 -0.0514 0.161 Uiso 1 1 calc R . . H63C H 0.0248 0.7642 -0.0865 0.161 Uiso 1 1 calc R . . C17 C 0.2979(3) 1.0020(3) 0.03785(11) 0.0584(10) Uani 1 1 d . . . H18 H 0.2701 0.9659 0.0635 0.070 Uiso 1 1 calc R B . C18 C 0.2491(3) 1.1111(3) 0.03158(12) 0.0615(10) Uani 1 1 d . B . H43A H 0.2576 1.1547 0.0579 0.092 Uiso 1 1 calc R . . H43B H 0.1814 1.0997 0.0255 0.092 Uiso 1 1 calc R . . H43C H 0.2769 1.1494 0.0072 0.092 Uiso 1 1 calc R . . C19 C 0.4035(3) 1.0194(4) 0.0477(2) 0.1031(19) Uani 1 1 d . B . H61A H 0.4309 1.0620 0.0244 0.155 Uiso 1 1 calc R . . H61B H 0.4354 0.9488 0.0498 0.155 Uiso 1 1 calc R . . H61C H 0.4119 1.0585 0.0751 0.155 Uiso 1 1 calc R . . C20 C 0.46333(17) 0.5797(2) 0.14323(8) 0.0304(5) Uani 1 1 d . . . C21 C 0.48566(19) 0.4716(2) 0.13497(9) 0.0368(6) Uani 1 1 d . B . C22 C 0.5777(2) 0.4503(3) 0.12201(10) 0.0488(8) Uani 1 1 d . . . H58 H 0.5961 0.3779 0.1157 0.059 Uiso 1 1 calc R B . C23 C 0.6423(2) 0.5339(3) 0.11825(12) 0.0587(9) Uani 1 1 d . B . H53 H 0.7045 0.5181 0.1093 0.070 Uiso 1 1 calc R . . C24 C 0.6179(2) 0.6399(3) 0.12730(13) 0.0540(9) Uani 1 1 d . . . H44 H 0.6637 0.6958 0.1246 0.065 Uiso 1 1 calc R B . C25 C 0.5276(2) 0.6658(3) 0.14020(10) 0.0417(7) Uani 1 1 d . B . C26 C 0.5022(2) 0.7823(3) 0.15173(14) 0.0580(9) Uani 1 1 d . . . H55 H 0.4324 0.7931 0.1476 0.070 Uiso 1 1 calc R B . C27 C 0.5565(4) 0.8653(4) 0.1224(2) 0.1048(19) Uani 1 1 d . B . H3A H 0.5291 0.9378 0.1255 0.157 Uiso 1 1 calc R . . H3B H 0.5505 0.8424 0.0921 0.157 Uiso 1 1 calc R . . H3C H 0.6236 0.8671 0.1314 0.157 Uiso 1 1 calc R . . C28 C 0.5307(5) 0.8094(4) 0.19635(18) 0.115(2) Uani 1 1 d . B . H62A H 0.5054 0.7549 0.2160 0.173 Uiso 1 1 calc R . . H62B H 0.5058 0.8812 0.2037 0.173 Uiso 1 1 calc R . . H62C H 0.5999 0.8104 0.1992 0.173 Uiso 1 1 calc R . . C29 C 0.4157(2) 0.3806(3) 0.14163(12) 0.0497(8) Uani 1 1 d . . . H47 H 0.3531 0.4141 0.1478 0.060 Uiso 1 1 calc R B . C30 C 0.4456(3) 0.3130(4) 0.1804(2) 0.107(2) Uani 1 1 d . B . H64A H 0.5061 0.2774 0.1749 0.161 Uiso 1 1 calc R . . H64B H 0.3973 0.2577 0.1856 0.161 Uiso 1 1 calc R . . H64C H 0.4527 0.3599 0.2059 0.161 Uiso 1 1 calc R . . C31 C 0.4029(5) 0.3108(5) 0.1018(2) 0.133(3) Uani 1 1 d . B . H1A H 0.3887 0.3571 0.0767 0.199 Uiso 1 1 calc R . . H1B H 0.3505 0.2600 0.1058 0.199 Uiso 1 1 calc R . . H1C H 0.4612 0.2700 0.0971 0.199 Uiso 1 1 calc R . . C32 C 0.88201(16) -0.1221(2) 0.16602(8) 0.0265(5) Uani 1 1 d . . . C33 C 0.89744(17) -0.2343(2) 0.17282(8) 0.0310(6) Uani 1 1 d . . . H9 H 0.9213 -0.2579 0.2003 0.037 Uiso 1 1 calc R . . C34 C 0.87899(18) -0.3117(2) 0.14073(10) 0.0375(6) Uani 1 1 d . . . H35 H 0.8904 -0.3863 0.1466 0.045 Uiso 1 1 calc R . . C35 C 0.84425(19) -0.2803(3) 0.10038(10) 0.0432(7) Uani 1 1 d . . . H34 H 0.8329 -0.3326 0.0782 0.052 Uiso 1 1 calc R . . C36 C 0.82634(19) -0.1714(3) 0.09283(9) 0.0413(7) Uani 1 1 d . . . H49 H 0.8011 -0.1489 0.0655 0.050 Uiso 1 1 calc R . . C37 C 0.84493(17) -0.0947(2) 0.12487(8) 0.0322(6) Uani 1 1 d . . . H13 H 0.8320 -0.0205 0.1187 0.039 Uiso 1 1 calc R . . C38 C 0.85125(17) 0.0797(2) 0.19713(7) 0.0259(5) Uani 1 1 d . . . C39 C 0.75228(17) 0.0679(2) 0.19339(8) 0.0283(5) Uani 1 1 d . . . H12 H 0.7268 -0.0032 0.1905 0.034 Uiso 1 1 calc R . . C40 C 0.69014(18) 0.1549(2) 0.19376(8) 0.0322(6) Uani 1 1 d . . . H20 H 0.6238 0.1427 0.1916 0.039 Uiso 1 1 calc R . . C41 C 0.72514(19) 0.2602(2) 0.19735(8) 0.0343(6) Uani 1 1 d . . . H25 H 0.6833 0.3205 0.1972 0.041 Uiso 1 1 calc R . . C42 C 0.82143(19) 0.2753(2) 0.20115(8) 0.0332(6) Uani 1 1 d . . . H21 H 0.8461 0.3469 0.2035 0.040 Uiso 1 1 calc R . . C43 C 0.88342(18) 0.1870(2) 0.20155(8) 0.0293(5) Uani 1 1 d . . . H4 H 0.9495 0.2000 0.2049 0.035 Uiso 1 1 calc R . . C44 C 1.02952(17) -0.0113(2) 0.18740(8) 0.0269(5) Uani 1 1 d . . . C45 C 1.05866(19) 0.0662(2) 0.15747(8) 0.0338(6) Uani 1 1 d . . . H38 H 1.0136 0.1170 0.1463 0.041 Uiso 1 1 calc R . . C46 C 1.1513(2) 0.0718(3) 0.14336(9) 0.0415(7) Uani 1 1 d . . . H33 H 1.1681 0.1263 0.1232 0.050 Uiso 1 1 calc R . . C47 C 1.21872(19) -0.0007(3) 0.15824(10) 0.0416(7) Uani 1 1 d . . . H31 H 1.2819 0.0031 0.1486 0.050 Uiso 1 1 calc R . . C48 C 1.19246(19) -0.0798(2) 0.18774(9) 0.0371(6) Uani 1 1 d . . . H27 H 1.2379 -0.1308 0.1983 0.044 Uiso 1 1 calc R . . C49 C 1.10032(17) -0.0841(2) 0.20163(8) 0.0299(5) Uani 1 1 d . . . H36 H 1.0842 -0.1389 0.2217 0.036 Uiso 1 1 calc R . . C50 C 0.90958(17) -0.0694(2) 0.25103(8) 0.0268(5) Uani 1 1 d . . . C51 C 0.83425(18) -0.1336(2) 0.26433(9) 0.0323(6) Uani 1 1 d . . . H5 H 0.7893 -0.1582 0.2431 0.039 Uiso 1 1 calc R . . C52 C 0.8220(2) -0.1631(2) 0.30702(9) 0.0375(6) Uani 1 1 d . . . H23 H 0.7696 -0.2071 0.3144 0.045 Uiso 1 1 calc R . . C53 C 0.8858(2) -0.1286(2) 0.33899(9) 0.0390(7) Uani 1 1 d . . . H8 H 0.8782 -0.1490 0.3683 0.047 Uiso 1 1 calc R . . C54 C 0.9606(2) -0.0642(2) 0.32743(8) 0.0348(6) Uani 1 1 d . . . H22 H 1.0048 -0.0398 0.3490 0.042 Uiso 1 1 calc R . . C55 C 0.97200(18) -0.0345(2) 0.28449(8) 0.0298(5) Uani 1 1 d . . . H19 H 1.0238 0.0109 0.2775 0.036 Uiso 1 1 calc R . . C56 C 0.7308(2) 0.5884(3) 0.23151(12) 0.0536(8) Uani 1 1 d . . . H59A H 0.7305 0.6463 0.2098 0.080 Uiso 1 1 calc R . . H59B H 0.7583 0.5225 0.2194 0.080 Uiso 1 1 calc R . . H59C H 0.7687 0.6113 0.2569 0.080 Uiso 1 1 calc R . . C57 C 0.6340(3) 0.5663(3) 0.24411(11) 0.0503(8) Uani 1 1 d . . . Ge1A Ge 0.29801(10) 0.63157(11) 0.06155(5) 0.0282(2) Uani 0.75 1 d PU B 1 N5A N 0.2013(3) 0.5127(5) 0.05879(16) 0.0537(11) Uani 0.75 1 d PDU B 1 N6A N 0.2100(4) 0.4443(3) 0.03255(14) 0.0707(12) Uani 0.75 1 d PDU B 1 N7A N 0.2128(6) 0.3751(5) 0.0074(2) 0.120(3) Uani 0.75 1 d PDU B 1 Ge1B Ge 0.3168(3) 0.6626(4) 0.06270(16) 0.0488(10) Uani 0.25 1 d PU A 2 N5B N 0.2599(12) 0.5329(15) 0.0443(6) 0.091(4) Uani 0.25 1 d PDU A 2 N7B N 0.0922(12) 0.5016(16) 0.0463(6) 0.104(5) Uani 0.25 1 d PDU 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 N1 0.0265(10) 0.0361(12) 0.0232(10) -0.0013(9) -0.0037(8) 0.0052(9) C1 0.0211(11) 0.0361(14) 0.0243(12) -0.0031(10) -0.0044(9) 0.0011(10) B1 0.0243(13) 0.0288(14) 0.0251(13) 0.0004(11) -0.0044(10) 0.0018(11) N6B 0.101(6) 0.129(12) 0.133(13) -0.010(9) -0.003(8) -0.008(9) N2 0.0188(9) 0.0350(11) 0.0264(10) -0.0021(9) -0.0021(8) 0.0005(8) C2 0.0241(12) 0.0374(14) 0.0270(13) 0.0006(10) -0.0034(9) 0.0031(10) N3 0.0221(10) 0.0378(12) 0.0236(10) 0.0018(8) 0.0010(8) 0.0032(8) C3 0.0292(13) 0.0374(15) 0.0349(14) -0.0008(11) -0.0027(11) 0.0106(11) N4 0.0250(10) 0.0405(12) 0.0240(10) 0.0000(9) -0.0041(8) 0.0040(9) C4 0.0211(12) 0.0389(15) 0.0332(13) -0.0041(11) -0.0014(10) 0.0055(10) C5 0.0334(14) 0.0392(15) 0.0243(12) 0.0029(10) 0.0031(10) 0.0023(11) C6 0.0354(14) 0.0416(15) 0.0243(13) 0.0033(11) -0.0038(10) 0.0022(12) C7 0.0212(12) 0.0415(15) 0.0298(13) 0.0027(11) 0.0011(10) 0.0001(10) N8 0.055(2) 0.077(2) 0.084(2) 0.0183(19) -0.0006(17) -0.0064(17) C8 0.0326(13) 0.0494(17) 0.0210(12) 0.0036(11) -0.0024(10) 0.0134(12) C9 0.0359(15) 0.068(2) 0.0319(15) 0.0169(14) -0.0056(12) -0.0007(14) C10 0.0435(18) 0.105(3) 0.0424(19) 0.032(2) 0.0009(14) 0.0031(19) C11 0.061(2) 0.119(4) 0.0341(19) 0.027(2) 0.0127(16) 0.037(2) C12 0.080(3) 0.083(3) 0.0227(15) -0.0017(16) -0.0033(15) 0.043(2) C13 0.0552(18) 0.0545(19) 0.0261(14) -0.0044(12) -0.0105(12) 0.0286(15) C14 0.076(2) 0.053(2) 0.0442(18) -0.0119(15) -0.0304(17) 0.0127(18) C15 0.194(6) 0.066(3) 0.071(3) -0.031(2) -0.037(4) 0.029(4) C16 0.083(3) 0.088(4) 0.146(5) 0.008(3) -0.066(3) -0.002(3) C17 0.064(2) 0.073(2) 0.0370(17) 0.0181(16) -0.0168(15) -0.0299(19) C18 0.061(2) 0.080(3) 0.0427(19) -0.0037(18) -0.0043(16) -0.0137(19) C19 0.081(3) 0.087(3) 0.137(5) 0.016(3) -0.070(3) -0.012(3) C20 0.0229(12) 0.0427(15) 0.0251(12) 0.0016(11) -0.0055(9) 0.0064(11) C21 0.0288(13) 0.0485(17) 0.0326(14) -0.0036(12) -0.0087(11) 0.0067(12) C22 0.0368(16) 0.060(2) 0.0496(18) -0.0085(15) -0.0047(13) 0.0194(15) C23 0.0258(15) 0.084(3) 0.067(2) 0.0065(19) 0.0072(14) 0.0130(16) C24 0.0262(15) 0.061(2) 0.075(2) 0.0152(18) 0.0004(14) 0.0016(14) C25 0.0292(14) 0.0474(17) 0.0479(17) 0.0059(13) -0.0088(12) 0.0037(12) C26 0.0329(16) 0.0436(18) 0.097(3) 0.0019(18) -0.0159(17) 0.0008(13) C27 0.109(4) 0.076(3) 0.128(5) 0.032(3) -0.021(4) -0.010(3) C28 0.191(7) 0.064(3) 0.089(4) -0.023(3) -0.035(4) 0.047(4) C29 0.0353(16) 0.0384(17) 0.075(2) -0.0019(15) -0.0131(15) 0.0068(13) C30 0.054(2) 0.094(4) 0.173(6) 0.077(4) -0.031(3) -0.013(2) C31 0.136(5) 0.105(5) 0.156(6) -0.069(4) -0.011(5) -0.045(4) C32 0.0164(11) 0.0374(14) 0.0257(12) -0.0030(10) -0.0007(9) 0.0020(9) C33 0.0207(11) 0.0403(15) 0.0321(13) -0.0035(11) 0.0008(10) 0.0001(10) C34 0.0245(12) 0.0374(15) 0.0506(17) -0.0111(13) 0.0036(11) -0.0017(11) C35 0.0261(13) 0.058(2) 0.0452(16) -0.0247(14) -0.0026(12) -0.0021(13) C36 0.0267(13) 0.066(2) 0.0308(14) -0.0125(13) -0.0082(11) 0.0074(13) C37 0.0237(12) 0.0430(15) 0.0296(13) -0.0043(11) -0.0044(10) 0.0073(11) C38 0.0265(12) 0.0328(13) 0.0182(11) -0.0004(9) -0.0035(9) 0.0029(10) C39 0.0271(12) 0.0329(13) 0.0247(12) -0.0023(10) -0.0045(9) 0.0019(10) C40 0.0252(12) 0.0441(16) 0.0268(13) -0.0034(11) -0.0057(10) 0.0055(11) C41 0.0351(14) 0.0379(15) 0.0293(13) -0.0031(11) -0.0075(10) 0.0120(12) C42 0.0391(14) 0.0304(14) 0.0296(13) -0.0017(10) -0.0057(11) 0.0020(11) C43 0.0268(12) 0.0368(14) 0.0241(12) -0.0013(10) -0.0044(9) 0.0015(10) C44 0.0253(12) 0.0324(13) 0.0228(11) -0.0053(10) -0.0042(9) 0.0002(10) C45 0.0355(14) 0.0349(14) 0.0312(13) -0.0006(11) 0.0033(11) 0.0016(11) C46 0.0456(16) 0.0426(17) 0.0367(15) -0.0049(12) 0.0103(12) -0.0093(13) C47 0.0272(13) 0.0543(18) 0.0435(16) -0.0166(14) 0.0067(11) -0.0086(13) C48 0.0265(13) 0.0453(16) 0.0390(15) -0.0110(12) -0.0067(11) 0.0025(11) C49 0.0257(12) 0.0349(14) 0.0289(13) -0.0038(10) -0.0052(10) -0.0003(10) C50 0.0241(12) 0.0306(13) 0.0255(12) -0.0015(10) -0.0042(9) 0.0073(10) C51 0.0280(13) 0.0400(15) 0.0287(13) -0.0010(11) -0.0026(10) 0.0008(11) C52 0.0394(15) 0.0378(15) 0.0354(15) 0.0049(12) 0.0038(11) 0.0018(12) C53 0.0508(17) 0.0414(16) 0.0250(13) 0.0026(11) 0.0008(12) 0.0105(13) C54 0.0392(15) 0.0381(15) 0.0267(13) -0.0041(11) -0.0092(11) 0.0085(12) C55 0.0284(12) 0.0317(14) 0.0289(13) -0.0011(10) -0.0053(10) 0.0046(10) C56 0.0529(19) 0.053(2) 0.054(2) 0.0109(16) -0.0037(15) -0.0011(16) C57 0.055(2) 0.0424(18) 0.0525(19) 0.0081(14) -0.0086(15) -0.0010(15) Ge1A 0.0233(4) 0.0383(5) 0.0229(3) -0.0026(3) -0.0002(2) 0.0057(3) N5A 0.055(3) 0.053(2) 0.053(3) -0.0069(17) 0.003(2) -0.014(2) N6A 0.093(3) 0.054(2) 0.064(3) -0.0136(17) -0.020(2) 0.006(2) N7A 0.209(8) 0.069(3) 0.080(4) -0.034(3) -0.037(4) 0.003(4) Ge1B 0.043(2) 0.078(3) 0.0262(11) 0.0109(18) 0.0055(13) 0.0331(17) N5B 0.090(6) 0.087(8) 0.095(8) -0.024(7) -0.019(7) 0.014(7) N7B 0.111(6) 0.110(9) 0.091(8) 0.045(7) -0.001(7) -0.044(7) _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 N1 C1 1.341(3) . ? N1 C3 1.383(3) . ? N1 C8 1.454(3) . ? C1 N2 1.348(3) . ? C1 Ge1B 2.034(6) . ? C1 Ge1A 2.050(3) . ? B1 C32 1.640(4) . ? B1 C50 1.644(4) . ? B1 C38 1.645(4) . ? B1 C44 1.647(4) . ? N6B N7B 1.203(9) . ? N6B N5B 1.206(9) . ? N2 C4 1.376(3) . ? N2 C7 1.457(3) . ? C2 N3 1.339(3) . ? C2 N4 1.343(3) . ? C2 Ge1A 2.054(3) . ? C2 Ge1B 2.083(6) . ? N3 C5 1.383(3) . ? N3 C7 1.465(3) . ? C3 C4 1.346(4) . ? N4 C6 1.383(3) . ? N4 C20 1.445(3) . ? C5 C6 1.343(4) . ? N8 C57 1.132(5) . ? C8 C9 1.387(4) . ? C8 C13 1.402(4) . ? C9 C10 1.397(4) . ? C9 C17 1.521(5) . ? C10 C11 1.380(6) . ? C11 C12 1.375(6) . ? C12 C13 1.399(5) . ? C13 C14 1.503(5) . ? C14 C15 1.539(5) . ? C14 C16 1.544(5) . ? C17 C18 1.520(6) . ? C17 C19 1.530(5) . ? C20 C21 1.393(4) . ? C20 C25 1.401(4) . ? C21 C22 1.397(4) . ? C21 C29 1.513(4) . ? C22 C23 1.382(5) . ? C23 C24 1.381(5) . ? C24 C25 1.384(4) . ? C25 C26 1.525(5) . ? C26 C28 1.465(6) . ? C26 C27 1.580(6) . ? C29 C31 1.508(6) . ? C29 C30 1.510(6) . ? C32 C37 1.403(3) . ? C32 C33 1.414(4) . ? C33 C34 1.395(4) . ? C34 C35 1.383(4) . ? C35 C36 1.383(5) . ? C36 C37 1.389(4) . ? C38 C43 1.403(4) . ? C38 C39 1.407(3) . ? C39 C40 1.385(4) . ? C40 C41 1.391(4) . ? C41 C42 1.375(4) . ? C42 C43 1.396(4) . ? C44 C45 1.400(4) . ? C44 C49 1.405(3) . ? C45 C46 1.394(4) . ? C46 C47 1.375(4) . ? C47 C48 1.392(4) . ? C48 C49 1.384(4) . ? C50 C51 1.398(4) . ? C50 C55 1.407(3) . ? C51 C52 1.385(4) . ? C52 C53 1.386(4) . ? C53 C54 1.376(4) . ? C54 C55 1.392(4) . ? C56 C57 1.459(5) . ? Ge1A N5A 2.003(5) . ? N5A N6A 1.179(6) . ? N6A N7A 1.155(5) . ? Ge1B N5B 1.870(18) . ? 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 C1 N1 C3 110.1(2) . . ? C1 N1 C8 124.0(2) . . ? C3 N1 C8 125.9(2) . . ? N1 C1 N2 105.5(2) . . ? N1 C1 Ge1B 123.1(2) . . ? N2 C1 Ge1B 130.1(2) . . ? N1 C1 Ge1A 129.09(19) . . ? N2 C1 Ge1A 125.34(19) . . ? Ge1B C1 Ge1A 13.10(11) . . ? C32 B1 C50 112.2(2) . . ? C32 B1 C38 110.82(19) . . ? C50 B1 C38 104.31(19) . . ? C32 B1 C44 102.42(19) . . ? C50 B1 C44 112.08(19) . . ? C38 B1 C44 115.3(2) . . ? N7B N6B N5B 172(3) . . ? C1 N2 C4 110.9(2) . . ? C1 N2 C7 125.0(2) . . ? C4 N2 C7 123.6(2) . . ? N3 C2 N4 105.5(2) . . ? N3 C2 Ge1A 126.16(18) . . ? N4 C2 Ge1A 128.18(19) . . ? N3 C2 Ge1B 130.1(2) . . ? N4 C2 Ge1B 123.3(2) . . ? Ge1A C2 Ge1B 12.92(11) . . ? C2 N3 C5 110.9(2) . . ? C2 N3 C7 124.3(2) . . ? C5 N3 C7 124.6(2) . . ? C4 C3 N1 107.3(2) . . ? C2 N4 C6 110.3(2) . . ? C2 N4 C20 124.1(2) . . ? C6 N4 C20 125.6(2) . . ? C3 C4 N2 106.2(2) . . ? C6 C5 N3 106.2(2) . . ? C5 C6 N4 107.0(2) . . ? N2 C7 N3 110.83(19) . . ? C9 C8 C13 124.2(3) . . ? C9 C8 N1 117.9(2) . . ? C13 C8 N1 118.0(3) . . ? C8 C9 C10 117.2(3) . . ? C8 C9 C17 122.7(3) . . ? C10 C9 C17 120.1(3) . . ? C11 C10 C9 120.3(4) . . ? C12 C11 C10 121.2(3) . . ? C11 C12 C13 121.2(3) . . ? C12 C13 C8 116.0(3) . . ? C12 C13 C14 121.9(3) . . ? C8 C13 C14 122.0(3) . . ? C13 C14 C15 112.6(4) . . ? C13 C14 C16 109.9(3) . . ? C15 C14 C16 110.7(4) . . ? C18 C17 C9 110.6(3) . . ? C18 C17 C19 109.7(3) . . ? C9 C17 C19 112.7(4) . . ? C21 C20 C25 124.0(2) . . ? C21 C20 N4 118.1(2) . . ? C25 C20 N4 117.9(2) . . ? C20 C21 C22 116.7(3) . . ? C20 C21 C29 122.1(3) . . ? C22 C21 C29 121.2(3) . . ? C23 C22 C21 120.4(3) . . ? C24 C23 C22 121.2(3) . . ? C23 C24 C25 120.9(3) . . ? C24 C25 C20 116.7(3) . . ? C24 C25 C26 120.6(3) . . ? C20 C25 C26 122.6(3) . . ? C28 C26 C25 112.0(3) . . ? C28 C26 C27 105.6(4) . . ? C25 C26 C27 110.7(4) . . ? C31 C29 C30 111.0(5) . . ? C31 C29 C21 112.0(4) . . ? C30 C29 C21 110.4(3) . . ? C37 C32 C33 114.9(2) . . ? C37 C32 B1 121.8(2) . . ? C33 C32 B1 122.7(2) . . ? C34 C33 C32 122.5(3) . . ? C35 C34 C33 120.4(3) . . ? C34 C35 C36 118.8(3) . . ? C35 C36 C37 120.6(3) . . ? C36 C37 C32 122.8(3) . . ? C43 C38 C39 115.1(2) . . ? C43 C38 B1 125.2(2) . . ? C39 C38 B1 119.5(2) . . ? C40 C39 C38 123.2(2) . . ? C39 C40 C41 119.8(2) . . ? C42 C41 C40 118.8(2) . . ? C41 C42 C43 120.9(3) . . ? C42 C43 C38 122.1(2) . . ? C45 C44 C49 115.0(2) . . ? C45 C44 B1 123.8(2) . . ? C49 C44 B1 120.8(2) . . ? C46 C45 C44 122.5(3) . . ? C47 C46 C45 120.7(3) . . ? C46 C47 C48 118.6(3) . . ? C49 C48 C47 120.1(3) . . ? C48 C49 C44 123.1(3) . . ? C51 C50 C55 115.0(2) . . ? C51 C50 B1 122.0(2) . . ? C55 C50 B1 122.8(2) . . ? C52 C51 C50 123.1(2) . . ? C51 C52 C53 120.2(3) . . ? C54 C53 C52 118.7(3) . . ? C53 C54 C55 120.7(2) . . ? C54 C55 C50 122.3(3) . . ? N8 C57 C56 178.6(4) . . ? N5A Ge1A C1 90.20(18) . . ? N5A Ge1A C2 90.84(17) . . ? C1 Ge1A C2 84.38(11) . . ? N6A N5A Ge1A 117.9(4) . . ? N7A N6A N5A 175.7(8) . . ? N5B Ge1B C1 94.5(5) . . ? N5B Ge1B C2 93.8(6) . . ? C1 Ge1B C2 84.1(2) . . ? N6B N5B Ge1B 122(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.521 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.060 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.000 0.500 143.8 17.0 2 0.500 0.500 0.000 143.7 16.4 _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 935361'