# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_p1 _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 H48 Ge N2' _chemical_formula_weight 593.36 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.0288(5) _cell_length_b 9.0787(4) _cell_length_c 11.5349(6) _cell_angle_alpha 71.459(4) _cell_angle_beta 80.307(4) _cell_angle_gamma 65.603(5) _cell_volume 815.64(7) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5055 _cell_measurement_theta_min 3.5565 _cell_measurement_theta_max 32.4657 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8296 _exptl_absorpt_correction_T_max 0.9479 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 16.3031 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6052 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3868 _reflns_number_gt 3863 _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 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0398P)^2^+0.1110P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(6) _refine_ls_number_reflns 3868 _refine_ls_number_parameters 369 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ge1 Ge 0.7853 0.8041 0.1792 0.02042(7) Uani 1 1 d . . . N1 N 0.8142(2) 0.9835(2) 0.06486(18) 0.0183(4) Uani 1 1 d . . . N2 N 0.8506(2) 0.8363(2) 0.31141(18) 0.0181(4) Uani 1 1 d . . . C19 C 0.8950(3) 1.0887(3) 0.0801(2) 0.0183(5) Uani 1 1 d . . . H19 H 0.8363 1.2053 0.0281 0.022 Uiso 1 1 calc R . . C14 C 0.8818(3) 1.1014(3) 0.2093(2) 0.0187(5) Uani 1 1 d . . . C13 C 0.8679(3) 0.9844(3) 0.3122(2) 0.0170(5) Uani 1 1 d . . . C18 C 0.8676(3) 1.0036(3) 0.4375(2) 0.0231(5) Uani 1 1 d . . . H18A H 0.9421 0.8961 0.4888 0.028 Uiso 1 1 calc R . . H18B H 0.7568 1.0258 0.4760 0.028 Uiso 1 1 calc R . . C2 C 0.9753(3) 0.5779(3) 0.4761(2) 0.0217(5) Uani 1 1 d . . . C20 C 1.0712(3) 1.0317(3) 0.0281(2) 0.0198(5) Uani 1 1 d . . . C27 C 0.8171(3) 0.9455(3) -0.1398(2) 0.0205(5) Uani 1 1 d . . . C17 C 0.9190(4) 1.1443(4) 0.4367(3) 0.0315(6) Uani 1 1 d . . . H17A H 0.8905 1.1686 0.5173 0.038 Uiso 1 1 calc R . . H17B H 1.0383 1.1085 0.4220 0.038 Uiso 1 1 calc R . . C31 C 0.6062(3) 1.1883(3) -0.0801(2) 0.0202(5) Uani 1 1 d . . . C30 C 0.5436(3) 1.2465(3) -0.1962(2) 0.0252(6) Uani 1 1 d . . . H30 H 0.4513 1.3491 -0.2164 0.030 Uiso 1 1 calc R . . C1 C 0.8353(3) 0.7156(3) 0.4265(2) 0.0191(5) Uani 1 1 d . . . C26 C 0.7469(3) 1.0379(3) -0.0538(2) 0.0181(5) Uani 1 1 d . . . C28 C 0.7453(3) 1.0077(3) -0.2527(2) 0.0234(5) Uani 1 1 d . . . H28 H 0.7888 0.9447 -0.3109 0.028 Uiso 1 1 calc R . . C15 C 0.8872(4) 1.2650(3) 0.2132(2) 0.0282(6) Uani 1 1 d . . . H15A H 0.8154 1.3593 0.1506 0.034 Uiso 1 1 calc R . . H15B H 0.9996 1.2605 0.1917 0.034 Uiso 1 1 calc R . . C6 C 0.6804(4) 0.7321(4) 0.4820(2) 0.0217(6) Uani 1 1 d . . . C32 C 0.5178(3) 1.2830(3) 0.0152(3) 0.0284(6) Uani 1 1 d . . . H32 H 0.5820 1.2256 0.0908 0.034 Uiso 1 1 calc R . . C21 C 1.1973(3) 0.9023(3) 0.0973(2) 0.0246(5) Uani 1 1 d . . . H21 H 1.1756 0.8489 0.1798 0.030 Uiso 1 1 calc R . . C10 C 1.1442(3) 0.5638(3) 0.4179(2) 0.0262(6) Uani 1 1 d . . . H10 H 1.1396 0.6808 0.3782 0.031 Uiso 1 1 calc R . . C7 C 0.5260(3) 0.8832(4) 0.4356(3) 0.0277(6) Uani 1 1 d . . . H7 H 0.5591 0.9686 0.3705 0.033 Uiso 1 1 calc R . . C29 C 0.6131(3) 1.1580(4) -0.2820(3) 0.0265(6) Uani 1 1 d . . . H29 H 0.5700 1.2005 -0.3610 0.032 Uiso 1 1 calc R . . C4 C 0.8051(4) 0.4660(4) 0.6325(3) 0.0342(7) Uani 1 1 d . . . H4 H 0.7947 0.3791 0.7015 0.041 Uiso 1 1 calc R . . C16 C 0.8341(4) 1.3002(4) 0.3379(3) 0.0358(7) Uani 1 1 d . . . H16A H 0.8620 1.3936 0.3407 0.043 Uiso 1 1 calc R . . H16B H 0.7148 1.3341 0.3511 0.043 Uiso 1 1 calc R . . C5 C 0.6681(3) 0.6037(3) 0.5850(3) 0.0300(6) Uani 1 1 d . . . H5 H 0.5642 0.6115 0.6228 0.036 Uiso 1 1 calc R . . C22 C 1.3557(3) 0.8494(3) 0.0471(3) 0.0302(6) Uani 1 1 d . . . H22 H 1.4416 0.7620 0.0959 0.036 Uiso 1 1 calc R . . C35 C 0.9620(3) 0.7772(4) -0.1153(3) 0.0272(6) Uani 1 1 d . . . H35 H 1.0106 0.7605 -0.0380 0.033 Uiso 1 1 calc R . . C25 C 1.1046(3) 1.1086(4) -0.0931(2) 0.0299(6) Uani 1 1 d . . . H25 H 1.0195 1.1978 -0.1416 0.036 Uiso 1 1 calc R . . C3 C 0.9578(4) 0.4544(4) 0.5794(3) 0.0288(7) Uani 1 1 d . . . H3 H 1.0516 0.3608 0.6141 0.035 Uiso 1 1 calc R . . C24 C 1.2639(4) 1.0542(4) -0.1433(3) 0.0363(7) Uani 1 1 d . . . H24 H 1.2865 1.1072 -0.2257 0.044 Uiso 1 1 calc R . . C9 C 0.4297(4) 0.9659(4) 0.5378(3) 0.0415(7) Uani 1 1 d . . . H9A H 0.3881 0.8881 0.5999 0.062 Uiso 1 1 calc R . . H9B H 0.3384 1.0698 0.5027 0.062 Uiso 1 1 calc R . . H9C H 0.5016 0.9924 0.5756 0.062 Uiso 1 1 calc R . . C23 C 1.3877(3) 0.9246(4) -0.0739(3) 0.0336(6) Uani 1 1 d . . . H23 H 1.4950 0.8866 -0.1089 0.040 Uiso 1 1 calc R . . C8 C 0.4142(4) 0.8393(4) 0.3789(3) 0.0420(7) Uani 1 1 d . . . H8A H 0.4763 0.7812 0.3171 0.063 Uiso 1 1 calc R . . H8B H 0.3249 0.9428 0.3402 0.063 Uiso 1 1 calc R . . H8C H 0.3697 0.7658 0.4428 0.063 Uiso 1 1 calc R . . C11 C 1.2765(4) 0.4776(4) 0.5116(3) 0.0369(7) Uani 1 1 d . . . H11A H 1.2447 0.5344 0.5765 0.055 Uiso 1 1 calc R . . H11B H 1.3792 0.4837 0.4712 0.055 Uiso 1 1 calc R . . H11C H 1.2907 0.3594 0.5471 0.055 Uiso 1 1 calc R . . C12 C 1.1897(4) 0.4736(4) 0.3181(3) 0.0398(7) Uani 1 1 d . . . H12A H 1.1856 0.3618 0.3527 0.060 Uiso 1 1 calc R . . H12B H 1.3001 0.4621 0.2850 0.060 Uiso 1 1 calc R . . H12C H 1.1128 0.5391 0.2524 0.060 Uiso 1 1 calc R . . C33 C 0.3491(4) 1.2743(5) 0.0480(4) 0.0493(9) Uani 1 1 d . . . H33A H 0.2854 1.3257 -0.0256 0.074 Uiso 1 1 calc R . . H33B H 0.2928 1.3352 0.1094 0.074 Uiso 1 1 calc R . . H33C H 0.3613 1.1564 0.0812 0.074 Uiso 1 1 calc R . . C36 C 1.0940(4) 0.7737(5) -0.2183(3) 0.0439(8) Uani 1 1 d . . . H36A H 1.0525 0.7789 -0.2933 0.066 Uiso 1 1 calc R . . H36B H 1.1901 0.6694 -0.1948 0.066 Uiso 1 1 calc R . . H36C H 1.1239 0.8705 -0.2326 0.066 Uiso 1 1 calc R . . C34 C 0.5039(5) 1.4658(4) -0.0283(4) 0.0508(9) Uani 1 1 d . . . H34A H 0.6131 1.4682 -0.0414 0.076 Uiso 1 1 calc R . . H34B H 0.4427 1.5236 0.0338 0.076 Uiso 1 1 calc R . . H34C H 0.4471 1.5227 -0.1053 0.076 Uiso 1 1 calc R . . C37 C 0.9056(4) 0.6334(4) -0.0959(3) 0.0428(8) Uani 1 1 d . . . H37A H 0.8211 0.6379 -0.0300 0.064 Uiso 1 1 calc R . . H37B H 0.9982 0.5254 -0.0737 0.064 Uiso 1 1 calc R . . H37C H 0.8613 0.6446 -0.1716 0.064 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 0.03288(12) 0.02069(12) 0.01261(11) -0.00239(8) -0.00366(8) -0.01567(9) N1 0.0243(9) 0.0221(10) 0.0112(10) -0.0032(8) -0.0037(8) -0.0114(8) N2 0.0279(10) 0.0168(9) 0.0120(10) -0.0026(8) -0.0020(8) -0.0116(8) C19 0.0227(11) 0.0188(11) 0.0145(11) -0.0022(9) -0.0026(9) -0.0101(9) C14 0.0208(10) 0.0217(12) 0.0169(12) -0.0062(10) -0.0012(9) -0.0107(9) C13 0.0171(10) 0.0188(11) 0.0174(11) -0.0064(9) -0.0014(9) -0.0080(9) C18 0.0324(13) 0.0259(13) 0.0168(12) -0.0072(10) 0.0011(10) -0.0168(11) C2 0.0303(12) 0.0199(12) 0.0178(12) -0.0035(10) -0.0041(10) -0.0126(10) C20 0.0253(12) 0.0232(12) 0.0169(12) -0.0063(10) -0.0006(10) -0.0146(10) C27 0.0201(12) 0.0249(14) 0.0166(13) -0.0043(11) 0.0006(11) -0.0103(10) C17 0.0483(16) 0.0372(15) 0.0210(14) -0.0127(12) 0.0022(12) -0.0261(13) C31 0.0209(11) 0.0209(12) 0.0203(12) -0.0036(10) -0.0012(10) -0.0112(9) C30 0.0214(12) 0.0237(13) 0.0258(14) 0.0036(11) -0.0085(11) -0.0089(10) C1 0.0288(12) 0.0214(12) 0.0117(11) -0.0046(9) -0.0026(10) -0.0134(10) C26 0.0214(11) 0.0229(12) 0.0124(11) -0.0007(9) -0.0017(9) -0.0137(9) C28 0.0253(12) 0.0344(14) 0.0132(12) -0.0068(10) -0.0001(10) -0.0142(10) C15 0.0467(15) 0.0240(13) 0.0198(13) -0.0036(11) -0.0012(12) -0.0214(12) C6 0.0321(15) 0.0237(15) 0.0156(13) -0.0057(12) -0.0015(12) -0.0166(12) C32 0.0242(12) 0.0270(14) 0.0355(15) -0.0160(12) -0.0030(11) -0.0053(10) C21 0.0288(12) 0.0242(13) 0.0233(13) -0.0048(11) -0.0011(11) -0.0139(11) C10 0.0286(12) 0.0210(12) 0.0255(14) -0.0031(11) -0.0025(11) -0.0081(10) C7 0.0305(14) 0.0298(14) 0.0238(14) -0.0046(12) 0.0002(12) -0.0152(12) C29 0.0299(13) 0.0359(15) 0.0144(14) 0.0009(12) -0.0070(12) -0.0168(11) C4 0.0475(17) 0.0339(15) 0.0211(14) 0.0067(12) -0.0063(13) -0.0242(13) C16 0.0558(18) 0.0276(14) 0.0313(15) -0.0112(12) -0.0010(14) -0.0211(13) C5 0.0334(14) 0.0352(15) 0.0233(13) -0.0026(12) 0.0016(12) -0.0203(12) C22 0.0270(13) 0.0282(14) 0.0383(16) -0.0125(12) -0.0017(12) -0.0108(11) C35 0.0257(13) 0.0313(16) 0.0209(14) -0.0106(12) -0.0059(12) -0.0032(12) C25 0.0311(13) 0.0420(16) 0.0191(13) -0.0024(12) -0.0020(11) -0.0204(12) C3 0.0357(15) 0.0246(15) 0.0237(17) 0.0010(13) -0.0094(14) -0.0120(12) C24 0.0367(15) 0.058(2) 0.0218(14) -0.0093(14) 0.0057(12) -0.0297(15) C9 0.0359(15) 0.0426(18) 0.0508(19) -0.0246(15) 0.0044(14) -0.0135(13) C23 0.0276(13) 0.0446(17) 0.0394(17) -0.0213(14) 0.0088(13) -0.0209(12) C8 0.0324(14) 0.0528(19) 0.0449(19) -0.0190(16) -0.0047(14) -0.0152(14) C11 0.0302(14) 0.0338(16) 0.0409(18) -0.0015(14) -0.0106(13) -0.0100(12) C12 0.0379(15) 0.0423(17) 0.0370(17) -0.0161(14) 0.0011(14) -0.0104(13) C33 0.0339(16) 0.069(2) 0.063(2) -0.051(2) 0.0160(16) -0.0199(15) C36 0.0246(13) 0.062(2) 0.0422(19) -0.0296(17) 0.0059(13) -0.0056(14) C34 0.061(2) 0.0283(16) 0.065(2) -0.0201(16) -0.0171(19) -0.0091(15) C37 0.0485(17) 0.0293(15) 0.0454(19) -0.0143(14) -0.0062(15) -0.0054(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ge1 N1 1.8250(19) . ? Ge1 N2 1.867(2) . ? N1 C26 1.445(3) . ? N1 C19 1.482(3) . ? N2 C13 1.419(3) . ? N2 C1 1.456(3) . ? C19 C14 1.513(3) . ? C19 C20 1.534(3) . ? C19 H19 1.0000 . ? C14 C13 1.346(3) . ? C14 C15 1.521(3) . ? C13 C18 1.510(3) . ? C18 C17 1.525(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C2 C3 1.392(4) . ? C2 C1 1.404(3) . ? C2 C10 1.530(3) . ? C20 C21 1.385(3) . ? C20 C25 1.394(3) . ? C27 C28 1.397(4) . ? C27 C26 1.402(4) . ? C27 C35 1.525(4) . ? C17 C16 1.504(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C31 C30 1.396(4) . ? C31 C26 1.416(3) . ? C31 C32 1.523(4) . ? C30 C29 1.378(4) . ? C30 H30 0.9500 . ? C1 C6 1.406(4) . ? C28 C29 1.377(4) . ? C28 H28 0.9500 . ? C15 C16 1.529(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C6 C5 1.402(4) . ? C6 C7 1.522(4) . ? C32 C34 1.531(4) . ? C32 C33 1.535(4) . ? C32 H32 1.0000 . ? C21 C22 1.393(4) . ? C21 H21 0.9500 . ? C10 C12 1.526(4) . ? C10 C11 1.527(4) . ? C10 H10 1.0000 . ? C7 C8 1.525(4) . ? C7 C9 1.545(4) . ? C7 H7 1.0000 . ? C29 H29 0.9500 . ? C4 C5 1.381(4) . ? C4 C3 1.386(4) . ? C4 H4 0.9500 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C5 H5 0.9500 . ? C22 C23 1.385(4) . ? C22 H22 0.9500 . ? C35 C37 1.530(5) . ? C35 C36 1.533(4) . ? C35 H35 1.0000 . ? C25 C24 1.400(4) . ? C25 H25 0.9500 . ? C3 H3 0.9500 . ? C24 C23 1.375(5) . ? C24 H24 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C23 H23 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 Ge1 N2 95.89(9) . . ? C26 N1 C19 114.16(18) . . ? C26 N1 Ge1 118.37(16) . . ? C19 N1 Ge1 127.42(15) . . ? C13 N2 C1 119.9(2) . . ? C13 N2 Ge1 125.49(16) . . ? C1 N2 Ge1 112.21(15) . . ? N1 C19 C14 113.99(19) . . ? N1 C19 C20 110.46(19) . . ? C14 C19 C20 112.7(2) . . ? N1 C19 H19 106.4 . . ? C14 C19 H19 106.4 . . ? C20 C19 H19 106.4 . . ? C13 C14 C19 125.8(2) . . ? C13 C14 C15 121.7(2) . . ? C19 C14 C15 112.5(2) . . ? C14 C13 N2 123.0(2) . . ? C14 C13 C18 121.7(2) . . ? N2 C13 C18 115.2(2) . . ? C13 C18 C17 114.1(2) . . ? C13 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? C13 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C3 C2 C1 118.8(2) . . ? C3 C2 C10 120.5(2) . . ? C1 C2 C10 120.7(2) . . ? C21 C20 C25 119.0(2) . . ? C21 C20 C19 121.7(2) . . ? C25 C20 C19 119.2(2) . . ? C28 C27 C26 118.0(2) . . ? C28 C27 C35 118.0(2) . . ? C26 C27 C35 124.0(2) . . ? C16 C17 C18 109.8(2) . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? C16 C17 H17B 109.7 . . ? C18 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C30 C31 C26 118.1(2) . . ? C30 C31 C32 119.5(2) . . ? C26 C31 C32 122.3(2) . . ? C29 C30 C31 121.3(2) . . ? C29 C30 H30 119.3 . . ? C31 C30 H30 119.3 . . ? C2 C1 C6 120.9(2) . . ? C2 C1 N2 119.2(2) . . ? C6 C1 N2 119.8(2) . . ? C27 C26 C31 121.0(2) . . ? C27 C26 N1 121.6(2) . . ? C31 C26 N1 117.4(2) . . ? C29 C28 C27 121.8(3) . . ? C29 C28 H28 119.1 . . ? C27 C28 H28 119.1 . . ? C14 C15 C16 113.3(2) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C5 C6 C1 118.4(3) . . ? C5 C6 C7 118.7(2) . . ? C1 C6 C7 122.9(2) . . ? C31 C32 C34 111.9(2) . . ? C31 C32 C33 109.8(2) . . ? C34 C32 C33 110.9(3) . . ? C31 C32 H32 108.0 . . ? C34 C32 H32 108.0 . . ? C33 C32 H32 108.0 . . ? C20 C21 C22 120.7(2) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C12 C10 C11 110.1(2) . . ? C12 C10 C2 111.3(2) . . ? C11 C10 C2 112.8(2) . . ? C12 C10 H10 107.5 . . ? C11 C10 H10 107.5 . . ? C2 C10 H10 107.5 . . ? C6 C7 C8 112.7(2) . . ? C6 C7 C9 111.8(2) . . ? C8 C7 C9 109.2(2) . . ? C6 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? C9 C7 H7 107.7 . . ? C28 C29 C30 119.7(3) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C17 C16 C15 109.4(2) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C27 C35 C37 110.2(2) . . ? C27 C35 C36 111.9(2) . . ? C37 C35 C36 110.7(3) . . ? C27 C35 H35 107.9 . . ? C37 C35 H35 107.9 . . ? C36 C35 H35 107.9 . . ? C20 C25 C24 120.0(3) . . ? C20 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C23 C24 C25 120.4(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C24 C23 C22 119.9(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.306 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 967657' ####################################################################### # # 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_p21c _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 'C38 H48 Ge N2 O2' _chemical_formula_weight 637.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8770(11) _cell_length_b 18.4080(17) _cell_length_c 16.0265(15) _cell_angle_alpha 90.00 _cell_angle_beta 105.434(9) _cell_angle_gamma 90.00 _cell_volume 3377.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3147 _cell_measurement_theta_min 3.4364 _cell_measurement_theta_max 32.5634 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7334 _exptl_absorpt_correction_T_max 0.9159 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14941 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5913 _reflns_number_gt 4881 _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^)+(0.0388P)^2^+2.1497P] 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 5913 _refine_ls_number_parameters 414 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ge1 Ge 0.44672(2) 0.296876(16) 0.828932(18) 0.02127(10) Uani 1 1 d . . . C2 C 0.5913(2) 0.32511(16) 0.70785(18) 0.0250(6) Uani 1 1 d U C . C3 C 0.4936(2) 0.35095(16) 0.64384(18) 0.0269(6) Uani 1 1 d . C . C4 C 0.3776(2) 0.33635(15) 0.64309(17) 0.0217(6) Uani 1 1 d . C . C5 C 0.2872(2) 0.34876(16) 0.55859(17) 0.0227(6) Uani 1 1 d . . . C6 C 0.2736(3) 0.29979(18) 0.49082(19) 0.0335(7) Uani 1 1 d . . . H6 H 0.3200 0.2570 0.4984 0.040 Uiso 1 1 calc R . . C7 C 0.1930(3) 0.3127(2) 0.4122(2) 0.0430(9) Uani 1 1 d . . . H7 H 0.1827 0.2782 0.3668 0.052 Uiso 1 1 calc R . . C8 C 0.1275(3) 0.3759(2) 0.3998(2) 0.0410(8) Uani 1 1 d . . . H8 H 0.0727 0.3850 0.3457 0.049 Uiso 1 1 calc R . . C9 C 0.1418(3) 0.42547(19) 0.4657(2) 0.0378(8) Uani 1 1 d . . . H9 H 0.0975 0.4691 0.4569 0.045 Uiso 1 1 calc R . . C10 C 0.2214(2) 0.41212(17) 0.54549(19) 0.0296(7) Uani 1 1 d . . . H10A H 0.2305 0.4465 0.5910 0.036 Uiso 1 1 calc R . . C11 C 0.2227(2) 0.28738(15) 0.69996(16) 0.0211(6) Uani 1 1 d . . . C12 C 0.1900(2) 0.21559(16) 0.67608(17) 0.0258(6) Uani 1 1 d . . . C13 C 0.0765(2) 0.19339(17) 0.67201(18) 0.0302(7) Uani 1 1 d . . . H13A H 0.0531 0.1451 0.6551 0.036 Uiso 1 1 calc R . . C14 C -0.0026(2) 0.24083(18) 0.6923(2) 0.0332(7) Uani 1 1 d . . . H14A H -0.0796 0.2250 0.6898 0.040 Uiso 1 1 calc R . . C15 C 0.0309(2) 0.31085(17) 0.71619(19) 0.0304(7) Uani 1 1 d . . . H15A H -0.0241 0.3430 0.7300 0.036 Uiso 1 1 calc R . . C16 C 0.1425(2) 0.33629(15) 0.72078(17) 0.0222(6) Uani 1 1 d . . . C17 C 0.1732(2) 0.41348(15) 0.75174(19) 0.0266(6) Uani 1 1 d . . . H17A H 0.2505 0.4258 0.7417 0.032 Uiso 1 1 calc R . . C18 C 0.1849(3) 0.41856(18) 0.8484(2) 0.0367(8) Uani 1 1 d . . . H18A H 0.1091 0.4087 0.8595 0.055 Uiso 1 1 calc R . . H18B H 0.2110 0.4675 0.8690 0.055 Uiso 1 1 calc R . . H18C H 0.2422 0.3828 0.8792 0.055 Uiso 1 1 calc R . . C19 C 0.0833(3) 0.46932(18) 0.7031(2) 0.0428(8) Uani 1 1 d . . . H19A H 0.0711 0.4631 0.6406 0.064 Uiso 1 1 calc R . . H19B H 0.1122 0.5185 0.7198 0.064 Uiso 1 1 calc R . . H19C H 0.0092 0.4620 0.7179 0.064 Uiso 1 1 calc R . . C20 C 0.2717(3) 0.15917(17) 0.6554(2) 0.0336(7) Uani 1 1 d . . . H20 H 0.3471 0.1835 0.6558 0.040 Uiso 1 1 calc R . . C21 C 0.2206(3) 0.12557(19) 0.5656(2) 0.0479(9) Uani 1 1 d . . . H21A H 0.1529 0.0955 0.5665 0.072 Uiso 1 1 calc R . . H21B H 0.2801 0.0954 0.5501 0.072 Uiso 1 1 calc R . . H21C H 0.1964 0.1644 0.5227 0.072 Uiso 1 1 calc R . . C22 C 0.2966(3) 0.09994(19) 0.7244(2) 0.0477(9) Uani 1 1 d . . . H22A H 0.3358 0.1213 0.7806 0.072 Uiso 1 1 calc R . . H22B H 0.3471 0.0629 0.7093 0.072 Uiso 1 1 calc R . . H22C H 0.2229 0.0776 0.7274 0.072 Uiso 1 1 calc R . . C23 C 0.6862(2) 0.25943(16) 0.83958(18) 0.0261(6) Uani 1 1 d . . . C24 C 0.6954(2) 0.18340(17) 0.83726(19) 0.0321(7) Uani 1 1 d . . . C25 C 0.7911(3) 0.15071(19) 0.8943(2) 0.0467(9) Uani 1 1 d . . . H25 H 0.7990 0.0994 0.8933 0.056 Uiso 1 1 calc R . . C26 C 0.8740(3) 0.1906(2) 0.9518(2) 0.0497(10) Uani 1 1 d . . . H26 H 0.9387 0.1670 0.9900 0.060 Uiso 1 1 calc R . . C27 C 0.8633(3) 0.2650(2) 0.9539(2) 0.0397(8) Uani 1 1 d . . . H27 H 0.9214 0.2922 0.9939 0.048 Uiso 1 1 calc R . . C28 C 0.7695(2) 0.30136(17) 0.89902(18) 0.0285(7) Uani 1 1 d . . . C29 C 0.7629(2) 0.38329(17) 0.90725(19) 0.0311(7) Uani 1 1 d . . . H29 H 0.6938 0.4012 0.8615 0.037 Uiso 1 1 calc R . . C30 C 0.8729(3) 0.4209(2) 0.8946(2) 0.0502(9) Uani 1 1 d . . . H30A H 0.9408 0.4067 0.9416 0.075 Uiso 1 1 calc R . . H30B H 0.8628 0.4737 0.8953 0.075 Uiso 1 1 calc R . . H30C H 0.8853 0.4061 0.8390 0.075 Uiso 1 1 calc R . . C31 C 0.7459(3) 0.4032(2) 0.9958(2) 0.0459(9) Uani 1 1 d . . . H31A H 0.6799 0.3756 1.0056 0.069 Uiso 1 1 calc R . . H31B H 0.7299 0.4553 0.9974 0.069 Uiso 1 1 calc R . . H31C H 0.8169 0.3913 1.0411 0.069 Uiso 1 1 calc R . . C32 C 0.6068(3) 0.13766(17) 0.7725(2) 0.0394(8) Uani 1 1 d . . . H32 H 0.5288 0.1613 0.7643 0.047 Uiso 1 1 calc R . . C33 C 0.6336(4) 0.1366(2) 0.6846(2) 0.0647(12) Uani 1 1 d . . . H33A H 0.6342 0.1864 0.6632 0.097 Uiso 1 1 calc R . . H33B H 0.5736 0.1084 0.6436 0.097 Uiso 1 1 calc R . . H33C H 0.7102 0.1142 0.6905 0.097 Uiso 1 1 calc R . . C34 C 0.5963(3) 0.06014(19) 0.8026(3) 0.0571(10) Uani 1 1 d . . . H34A H 0.6708 0.0349 0.8095 0.086 Uiso 1 1 calc R . . H34B H 0.5349 0.0347 0.7595 0.086 Uiso 1 1 calc R . . H34C H 0.5763 0.0609 0.8581 0.086 Uiso 1 1 calc R . . C35 C 0.5170(3) 0.3900(2) 0.5661(2) 0.0474(9) Uani 1 1 d U . . H35A H 0.4986 0.3560 0.5165 0.057 Uiso 1 1 calc R A 1 H35B H 0.4615 0.4311 0.5509 0.057 Uiso 1 1 calc R A 1 C1 C 0.7090(2) 0.3316(2) 0.6895(2) 0.0393(8) Uani 1 1 d U . . H1A H 0.7711 0.3233 0.7436 0.047 Uiso 1 1 calc R B 1 H1B H 0.7162 0.2937 0.6474 0.047 Uiso 1 1 calc R B 1 C36A C 0.6255(17) 0.4163(10) 0.5744(13) 0.079(4) Uani 0.50 1 d PU C 1 H36C H 0.6172 0.4694 0.5654 0.095 Uiso 0.50 1 calc PR C 1 H36D H 0.6515 0.3967 0.5250 0.095 Uiso 0.50 1 calc PR C 1 C36 C 0.6282(16) 0.4352(8) 0.5875(12) 0.053(3) Uani 0.50 1 d PU C 2 H36A H 0.6398 0.4644 0.6409 0.063 Uiso 0.50 1 calc PR C 2 H36B H 0.6379 0.4653 0.5387 0.063 Uiso 0.50 1 calc PR C 2 C38 C 0.7252(6) 0.4050(5) 0.6539(6) 0.063(2) Uani 0.50 1 d PU C 1 H38A H 0.8007 0.4072 0.6388 0.075 Uiso 0.50 1 calc PR C 1 H38B H 0.7246 0.4431 0.6973 0.075 Uiso 0.50 1 calc PR C 1 C38A C 0.7127(6) 0.3499(5) 0.6024(4) 0.058(2) Uani 0.50 1 d PU C 2 H38C H 0.6745 0.3123 0.5601 0.069 Uiso 0.50 1 calc PR C 2 H38D H 0.7936 0.3577 0.5986 0.069 Uiso 0.50 1 calc PR C 2 C37 C 0.4668(2) 0.43154(19) 0.9160(2) 0.0362(8) Uani 1 1 d . C . H37A H 0.4791 0.4826 0.9202 0.043 Uiso 1 1 calc R . . N1 N 0.58444(17) 0.29416(12) 0.78186(14) 0.0213(5) Uani 1 1 d . . . N2 N 0.34290(17) 0.31029(12) 0.71018(14) 0.0204(5) Uani 1 1 d . . . O1 O 0.46508(15) 0.40220(11) 0.84269(12) 0.0271(4) Uani 1 1 d . . . O2 O 0.45442(19) 0.40126(14) 0.98016(14) 0.0468(6) 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 0.01919(15) 0.02669(17) 0.01706(16) 0.00286(13) 0.00332(10) 0.00468(12) C2 0.0213(14) 0.0314(16) 0.0221(15) -0.0003(13) 0.0052(11) 0.0039(12) C3 0.0208(14) 0.0345(17) 0.0246(16) 0.0036(13) 0.0043(11) 0.0025(12) C4 0.0232(14) 0.0224(15) 0.0188(14) 0.0013(12) 0.0041(11) 0.0054(11) C5 0.0151(13) 0.0340(16) 0.0193(14) 0.0055(13) 0.0051(10) 0.0011(11) C6 0.0343(16) 0.0397(19) 0.0254(16) 0.0027(15) 0.0061(12) 0.0095(14) C7 0.0448(19) 0.059(2) 0.0206(16) -0.0064(16) 0.0013(13) 0.0068(17) C8 0.0274(16) 0.066(2) 0.0238(17) 0.0085(17) -0.0029(12) 0.0118(16) C9 0.0328(17) 0.045(2) 0.0307(18) 0.0092(16) 0.0002(13) 0.0153(14) C10 0.0257(15) 0.0366(18) 0.0244(16) 0.0031(14) 0.0027(12) 0.0051(13) C11 0.0177(13) 0.0269(16) 0.0174(13) 0.0028(12) 0.0025(10) 0.0012(11) C12 0.0256(15) 0.0308(17) 0.0194(14) -0.0013(13) 0.0034(11) 0.0015(12) C13 0.0273(15) 0.0332(17) 0.0277(16) -0.0065(14) 0.0033(12) -0.0069(13) C14 0.0171(14) 0.044(2) 0.0359(18) -0.0014(15) 0.0023(12) -0.0052(13) C15 0.0187(14) 0.0380(19) 0.0344(17) -0.0013(14) 0.0068(12) 0.0055(12) C16 0.0188(13) 0.0280(16) 0.0179(14) 0.0034(12) 0.0013(10) 0.0045(11) C17 0.0164(13) 0.0280(16) 0.0360(17) 0.0021(14) 0.0078(11) 0.0063(11) C18 0.0282(16) 0.044(2) 0.0393(19) -0.0137(16) 0.0120(13) -0.0022(14) C19 0.0278(17) 0.0368(19) 0.063(2) 0.0118(18) 0.0108(15) 0.0111(14) C20 0.0310(16) 0.0317(18) 0.0395(19) -0.0067(15) 0.0116(13) -0.0006(13) C21 0.060(2) 0.041(2) 0.049(2) -0.0196(18) 0.0240(17) -0.0072(17) C22 0.043(2) 0.038(2) 0.061(2) -0.0004(18) 0.0127(17) 0.0100(16) C23 0.0227(14) 0.0334(17) 0.0208(15) 0.0026(13) 0.0035(11) 0.0116(12) C24 0.0299(16) 0.0341(18) 0.0283(17) -0.0031(14) 0.0007(12) 0.0122(13) C25 0.046(2) 0.039(2) 0.044(2) -0.0034(17) -0.0069(16) 0.0218(16) C26 0.0375(19) 0.053(2) 0.045(2) 0.0029(18) -0.0117(15) 0.0234(17) C27 0.0288(17) 0.052(2) 0.0306(18) -0.0041(16) -0.0058(13) 0.0104(15) C28 0.0234(14) 0.0396(18) 0.0217(15) -0.0039(14) 0.0048(11) 0.0065(13) C29 0.0216(15) 0.0375(18) 0.0310(17) -0.0042(14) 0.0014(12) 0.0035(13) C30 0.0279(17) 0.056(2) 0.062(2) -0.003(2) 0.0047(15) -0.0048(16) C31 0.0402(19) 0.055(2) 0.0378(19) -0.0157(18) 0.0021(14) 0.0087(16) C32 0.0388(18) 0.0300(18) 0.041(2) -0.0062(16) -0.0041(14) 0.0143(14) C33 0.086(3) 0.061(3) 0.039(2) -0.019(2) 0.003(2) 0.000(2) C34 0.056(2) 0.035(2) 0.069(3) -0.0020(19) -0.0034(19) 0.0103(17) C35 0.0272(17) 0.074(3) 0.0400(19) 0.0254(19) 0.0068(14) -0.0055(16) C1 0.0215(15) 0.062(2) 0.0367(18) 0.0061(17) 0.0123(13) 0.0093(15) C36A 0.048(6) 0.122(10) 0.072(7) 0.053(7) 0.021(5) 0.008(7) C36 0.044(5) 0.052(6) 0.048(6) 0.025(4) -0.011(5) -0.030(4) C38 0.034(4) 0.084(6) 0.070(5) 0.029(5) 0.012(3) -0.001(4) C38A 0.031(3) 0.123(7) 0.024(3) 0.021(4) 0.015(3) 0.036(4) C37 0.0245(16) 0.0384(19) 0.041(2) -0.0095(17) 0.0012(13) 0.0076(13) N1 0.0185(11) 0.0244(12) 0.0190(12) 0.0013(10) 0.0018(9) 0.0074(10) N2 0.0166(11) 0.0242(13) 0.0199(12) 0.0012(10) 0.0038(9) 0.0032(9) O1 0.0246(10) 0.0305(11) 0.0252(11) -0.0035(9) 0.0047(8) 0.0061(8) O2 0.0452(14) 0.0664(17) 0.0284(13) -0.0087(13) 0.0091(10) 0.0037(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 O1 1.957(2) . ? Ge1 N1 1.976(2) . ? Ge1 N2 1.989(2) . ? C2 N1 1.338(3) . ? C2 C3 1.411(4) . ? C2 C1 1.507(4) . ? C3 C4 1.400(4) . ? C3 C35 1.527(4) . ? C4 N2 1.339(3) . ? C4 C5 1.505(4) . ? C5 C6 1.388(4) . ? C5 C10 1.388(4) . ? C6 C7 1.385(4) . ? C7 C8 1.385(5) . ? C8 C9 1.371(5) . ? C9 C10 1.395(4) . ? C11 C12 1.402(4) . ? C11 C16 1.414(4) . ? C11 N2 1.456(3) . ? C12 C13 1.393(4) . ? C12 C20 1.517(4) . ? C13 C14 1.383(4) . ? C14 C15 1.373(4) . ? C15 C16 1.389(4) . ? C16 C17 1.517(4) . ? C17 C18 1.522(4) . ? C17 C19 1.536(4) . ? C20 C22 1.524(5) . ? C20 C21 1.537(4) . ? C23 C24 1.405(4) . ? C23 C28 1.407(4) . ? C23 N1 1.459(3) . ? C24 C25 1.391(4) . ? C24 C32 1.521(4) . ? C25 C26 1.369(5) . ? C26 C27 1.377(5) . ? C27 C28 1.394(4) . ? C28 C29 1.518(4) . ? C29 C31 1.530(4) . ? C29 C30 1.538(4) . ? C32 C34 1.522(5) . ? C32 C33 1.525(5) . ? C35 C36A 1.349(19) . ? C35 C36 1.520(15) . ? C1 C38A 1.449(7) . ? C1 C38 1.499(9) . ? C36A C38 1.51(2) . ? C36 C38A 1.844(19) . ? C37 O2 1.213(4) . ? C37 O1 1.288(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ge1 N1 89.38(8) . . ? O1 Ge1 N2 90.40(8) . . ? N1 Ge1 N2 90.18(8) . . ? N1 C2 C3 123.8(2) . . ? N1 C2 C1 119.0(2) . . ? C3 C2 C1 117.2(3) . . ? C4 C3 C2 123.9(3) . . ? C4 C3 C35 118.4(2) . . ? C2 C3 C35 117.3(2) . . ? N2 C4 C3 125.1(2) . . ? N2 C4 C5 118.6(2) . . ? C3 C4 C5 116.3(2) . . ? C6 C5 C10 118.9(3) . . ? C6 C5 C4 120.8(2) . . ? C10 C5 C4 120.1(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 C8 120.1(3) . . ? C9 C8 C7 119.9(3) . . ? C8 C9 C10 120.3(3) . . ? C5 C10 C9 120.2(3) . . ? C12 C11 C16 120.6(2) . . ? C12 C11 N2 119.7(2) . . ? C16 C11 N2 119.4(2) . . ? C13 C12 C11 118.9(3) . . ? C13 C12 C20 117.2(3) . . ? C11 C12 C20 123.9(2) . . ? C14 C13 C12 120.8(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C16 122.2(3) . . ? C15 C16 C11 117.8(3) . . ? C15 C16 C17 118.4(2) . . ? C11 C16 C17 123.7(2) . . ? C16 C17 C18 109.9(2) . . ? C16 C17 C19 112.7(2) . . ? C18 C17 C19 109.8(2) . . ? C12 C20 C22 110.1(2) . . ? C12 C20 C21 111.3(3) . . ? C22 C20 C21 110.1(3) . . ? C24 C23 C28 121.2(3) . . ? C24 C23 N1 118.5(3) . . ? C28 C23 N1 120.2(3) . . ? C25 C24 C23 118.0(3) . . ? C25 C24 C32 120.3(3) . . ? C23 C24 C32 121.6(3) . . ? C26 C25 C24 121.7(3) . . ? C25 C26 C27 119.7(3) . . ? C26 C27 C28 121.8(3) . . ? C27 C28 C23 117.6(3) . . ? C27 C28 C29 118.3(3) . . ? C23 C28 C29 124.1(2) . . ? C28 C29 C31 109.9(3) . . ? C28 C29 C30 111.7(2) . . ? C31 C29 C30 110.0(3) . . ? C24 C32 C34 113.8(3) . . ? C24 C32 C33 111.2(3) . . ? C34 C32 C33 109.6(3) . . ? C36A C35 C36 14.7(15) . . ? C36A C35 C3 117.7(9) . . ? C36 C35 C3 114.2(7) . . ? C38A C1 C38 51.9(5) . . ? C38A C1 C2 118.3(3) . . ? C38 C1 C2 111.4(4) . . ? C35 C36A C38 123.3(15) . . ? C35 C36 C38A 88.5(7) . . ? C1 C38 C36A 107.2(9) . . ? C1 C38A C36 99.7(8) . . ? O2 C37 O1 127.2(3) . . ? C2 N1 C23 120.9(2) . . ? C2 N1 Ge1 125.42(17) . . ? C23 N1 Ge1 113.52(17) . . ? C4 N2 C11 121.1(2) . . ? C4 N2 Ge1 124.62(17) . . ? C11 N2 Ge1 114.30(16) . . ? C37 O1 Ge1 119.5(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.633 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 967658' ####################################################################### # # 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_c2c _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 'C59 H84 Al Ge N4 O2' _chemical_formula_weight 980.87 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.2130 0.2455 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.8625(3) _cell_length_b 15.1844(2) _cell_length_c 14.7693(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.2710(10) _cell_angle_gamma 90.00 _cell_volume 5560.25(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6570 _cell_measurement_theta_min 4.4720 _cell_measurement_theta_max 73.4740 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2108 _exptl_absorpt_coefficient_mu 1.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8666 _exptl_absorpt_correction_T_max 0.9092 _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 1.54178 _diffrn_radiation_type CuK\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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10763 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 73.62 _reflns_number_total 5448 _reflns_number_gt 5030 _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 'Bruker SHELXTL' _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^)+(0.0718P)^2^+6.8210P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00014(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5448 _refine_ls_number_parameters 340 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Al1 Al 0.32457(5) 0.28268(9) 1.07708(8) 0.0222(3) Uani 0.50 1 d PD . . H1 H 0.2824(17) 0.333(3) 1.098(3) 0.027 Uiso 1 1 d D . . Ge1 Ge 0.172831(18) 0.24889(4) 0.95382(4) 0.02525(15) Uani 0.50 1 d P . . N1 N 0.14301(5) 0.29210(9) 0.83088(9) 0.0218(3) Uani 1 1 d . . . N2 N 0.10957(5) 0.16432(8) 0.95574(9) 0.0200(3) Uani 1 1 d . . . C1 C 0.08739(9) 0.29663(15) 0.68543(12) 0.0414(5) Uani 1 1 d . . . H1A H 0.0841 0.3606 0.6917 0.062 Uiso 1 1 calc R . . H1B H 0.0527 0.2721 0.6618 0.062 Uiso 1 1 calc R . . H1C H 0.1149 0.2832 0.6433 0.062 Uiso 1 1 calc R . . C2 C 0.10353(7) 0.25646(11) 0.77709(11) 0.0265(4) Uani 1 1 d . . . C3 C 0.07404(6) 0.18287(12) 0.80163(11) 0.0270(4) Uani 1 1 d . . . H3A H 0.0519 0.1557 0.7544 0.032 Uiso 1 1 calc R . . C4 C 0.07347(6) 0.14476(10) 0.88777(11) 0.0223(3) Uani 1 1 d . . . C5 C 0.02766(7) 0.08243(12) 0.90309(12) 0.0297(4) Uani 1 1 d . . . H5A H 0.0418 0.0306 0.9365 0.045 Uiso 1 1 calc R . . H5B H 0.0103 0.0640 0.8444 0.045 Uiso 1 1 calc R . . H5C H 0.0012 0.1123 0.9383 0.045 Uiso 1 1 calc R . . C6 C 0.16699(6) 0.37380(10) 0.80241(10) 0.0233(3) Uani 1 1 d . . . C7 C 0.14798(7) 0.45387(11) 0.83580(12) 0.0275(4) Uani 1 1 d . . . C8 C 0.16796(8) 0.53159(11) 0.80158(13) 0.0335(4) Uani 1 1 d . . . H8A H 0.1548 0.5863 0.8219 0.040 Uiso 1 1 calc R . . C9 C 0.20649(8) 0.53121(12) 0.73871(13) 0.0349(4) Uani 1 1 d . . . H9A H 0.2186 0.5850 0.7145 0.042 Uiso 1 1 calc R . . C10 C 0.22718(8) 0.45206(12) 0.71139(12) 0.0319(4) Uani 1 1 d . . . H10A H 0.2549 0.4522 0.6705 0.038 Uiso 1 1 calc R . . C11 C 0.20827(7) 0.37160(11) 0.74251(11) 0.0262(3) Uani 1 1 d . . . C12 C 0.23406(8) 0.28672(11) 0.71288(12) 0.0313(4) Uani 1 1 d . . . H12A H 0.2140 0.2362 0.7377 0.038 Uiso 1 1 calc R . . C13 C 0.29245(9) 0.28195(13) 0.75201(15) 0.0406(5) Uani 1 1 d . . . H13A H 0.2935 0.2809 0.8185 0.061 Uiso 1 1 calc R . . H13B H 0.3122 0.3336 0.7324 0.061 Uiso 1 1 calc R . . H13C H 0.3093 0.2283 0.7304 0.061 Uiso 1 1 calc R . . C14 C 0.23168(10) 0.27755(15) 0.60917(13) 0.0459(5) Uani 1 1 d . . . H14A H 0.1943 0.2847 0.5840 0.069 Uiso 1 1 calc R . . H14B H 0.2449 0.2192 0.5932 0.069 Uiso 1 1 calc R . . H14C H 0.2543 0.3230 0.5841 0.069 Uiso 1 1 calc R . . C15 C 0.10654(8) 0.45637(12) 0.90669(14) 0.0350(4) Uani 1 1 d . . . H15A H 0.1086 0.3986 0.9393 0.042 Uiso 1 1 calc R . . C16 C 0.11848(9) 0.52821(16) 0.97755(16) 0.0488(5) Uani 1 1 d . . . H16A H 0.1554 0.5213 1.0047 0.073 Uiso 1 1 calc R . . H16B H 0.0931 0.5233 1.0250 0.073 Uiso 1 1 calc R . . H16C H 0.1146 0.5861 0.9485 0.073 Uiso 1 1 calc R . . C17 C 0.04947(9) 0.4654(2) 0.8635(2) 0.0643(7) Uani 1 1 d . . . H17A H 0.0412 0.4153 0.8230 0.096 Uiso 1 1 calc R . . H17B H 0.0464 0.5202 0.8284 0.096 Uiso 1 1 calc R . . H17C H 0.0240 0.4666 0.9110 0.096 Uiso 1 1 calc R . . C18 C 0.10161(6) 0.13081(10) 1.04555(10) 0.0220(3) Uani 1 1 d . . . C19 C 0.12264(6) 0.04835(11) 1.07228(11) 0.0254(3) Uani 1 1 d . . . C20 C 0.11382(8) 0.01821(13) 1.15936(12) 0.0341(4) Uani 1 1 d . . . H20A H 0.1274 -0.0378 1.1787 0.041 Uiso 1 1 calc R . . C21 C 0.08569(8) 0.06864(14) 1.21775(13) 0.0386(4) Uani 1 1 d . . . H21A H 0.0797 0.0471 1.2766 0.046 Uiso 1 1 calc R . . C22 C 0.06626(8) 0.15031(13) 1.19063(12) 0.0353(4) Uani 1 1 d . . . H22A H 0.0474 0.1847 1.2316 0.042 Uiso 1 1 calc R . . C23 C 0.07367(6) 0.18351(12) 1.10461(12) 0.0277(4) Uani 1 1 d . . . C24 C 0.05171(7) 0.27372(12) 1.07707(13) 0.0335(4) Uani 1 1 d . . . H24A H 0.0637 0.2868 1.0154 0.040 Uiso 1 1 calc R . . C25 C -0.01011(9) 0.27505(17) 1.06955(18) 0.0518(6) Uani 1 1 d . . . H25A H -0.0229 0.3318 1.0447 0.078 Uiso 1 1 calc R . . H25B H -0.0233 0.2667 1.1299 0.078 Uiso 1 1 calc R . . H25C H -0.0237 0.2275 1.0292 0.078 Uiso 1 1 calc R . . C26 C 0.07424(10) 0.34522(15) 1.14032(19) 0.0537(6) Uani 1 1 d . . . H26A H 0.1137 0.3445 1.1422 0.081 Uiso 1 1 calc R . . H26B H 0.0627 0.3349 1.2014 0.081 Uiso 1 1 calc R . . H26C H 0.0609 0.4027 1.1183 0.081 Uiso 1 1 calc R . . C27 C 0.15483(7) -0.00834(11) 1.01124(12) 0.0300(4) Uani 1 1 d . . . H27A H 0.1580 0.0239 0.9528 0.036 Uiso 1 1 calc R . . C28 C 0.12781(10) -0.09688(14) 0.98977(17) 0.0494(5) Uani 1 1 d . . . H28A H 0.0913 -0.0871 0.9617 0.074 Uiso 1 1 calc R . . H28B H 0.1258 -0.1306 1.0460 0.074 Uiso 1 1 calc R . . H28C H 0.1489 -0.1299 0.9478 0.074 Uiso 1 1 calc R . . C29 C 0.21128(10) -0.0238(2) 1.0550(2) 0.0707(9) Uani 1 1 d . . . H29A H 0.2291 0.0330 1.0672 0.106 Uiso 1 1 calc R . . H29B H 0.2321 -0.0585 1.0139 0.106 Uiso 1 1 calc R . . H29C H 0.2090 -0.0559 1.1122 0.106 Uiso 1 1 calc R . . C50 C 0.26549(13) 0.1504(2) 0.9748(2) 0.0251(6) Uani 0.50 1 d P . . O1 O 0.22286(17) 0.1738(3) 0.9124(3) 0.0249(6) Uani 0.50 1 d P . . O2A O 0.30754(9) 0.21102(17) 0.97922(15) 0.0289(5) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al1 0.0283(6) 0.0214(6) 0.0163(6) -0.0029(4) -0.0017(4) -0.0077(5) Ge1 0.0191(2) 0.0285(3) 0.0279(3) 0.0072(2) -0.0002(2) -0.00081(19) N1 0.0231(6) 0.0207(6) 0.0214(6) 0.0007(5) 0.0001(5) -0.0016(5) N2 0.0186(6) 0.0198(6) 0.0214(6) 0.0003(5) 0.0014(5) -0.0010(5) C1 0.0499(11) 0.0460(11) 0.0261(9) 0.0077(8) -0.0113(8) -0.0131(9) C2 0.0285(8) 0.0293(9) 0.0213(7) -0.0018(6) -0.0018(6) -0.0013(6) C3 0.0269(8) 0.0297(8) 0.0234(8) -0.0041(6) -0.0036(6) -0.0048(6) C4 0.0200(7) 0.0200(7) 0.0268(8) -0.0035(6) 0.0010(6) -0.0006(6) C5 0.0239(8) 0.0318(9) 0.0329(9) -0.0005(7) -0.0007(6) -0.0086(7) C6 0.0281(8) 0.0198(7) 0.0212(7) 0.0035(6) -0.0042(6) -0.0008(6) C7 0.0275(8) 0.0239(8) 0.0304(8) 0.0031(6) -0.0029(6) 0.0047(6) C8 0.0392(10) 0.0192(8) 0.0412(10) 0.0041(7) -0.0025(8) 0.0034(7) C9 0.0462(11) 0.0220(8) 0.0361(9) 0.0077(7) -0.0003(8) -0.0041(7) C10 0.0414(10) 0.0268(9) 0.0279(8) 0.0030(7) 0.0050(7) -0.0059(7) C11 0.0349(9) 0.0229(8) 0.0206(7) 0.0010(6) 0.0011(6) -0.0039(7) C12 0.0461(10) 0.0211(8) 0.0286(8) -0.0023(6) 0.0148(7) -0.0082(7) C13 0.0452(11) 0.0303(9) 0.0476(11) -0.0005(8) 0.0129(9) 0.0050(8) C14 0.0683(14) 0.0401(11) 0.0315(10) -0.0115(8) 0.0175(9) -0.0162(10) C15 0.0347(9) 0.0251(9) 0.0462(10) 0.0016(8) 0.0094(8) 0.0076(7) C16 0.0479(12) 0.0514(13) 0.0479(12) -0.0090(10) 0.0093(10) 0.0094(10) C17 0.0310(11) 0.0779(18) 0.0842(19) -0.0265(15) 0.0053(11) 0.0021(11) C18 0.0179(7) 0.0250(8) 0.0234(7) -0.0001(6) 0.0028(6) -0.0042(6) C19 0.0243(8) 0.0246(8) 0.0272(8) 0.0011(6) 0.0002(6) -0.0038(6) C20 0.0379(9) 0.0326(9) 0.0314(9) 0.0080(7) 0.0009(7) -0.0052(8) C21 0.0425(10) 0.0465(11) 0.0278(9) 0.0062(8) 0.0083(8) -0.0122(9) C22 0.0328(9) 0.0438(11) 0.0308(9) -0.0033(8) 0.0130(7) -0.0055(8) C23 0.0212(7) 0.0314(9) 0.0310(8) -0.0030(7) 0.0059(6) -0.0027(6) C24 0.0325(9) 0.0316(9) 0.0380(9) -0.0034(8) 0.0125(7) 0.0051(7) C25 0.0371(11) 0.0498(13) 0.0677(15) -0.0024(11) -0.0006(10) 0.0091(10) C26 0.0539(13) 0.0357(11) 0.0700(15) -0.0140(11) -0.0059(11) 0.0021(10) C27 0.0320(9) 0.0235(8) 0.0345(9) 0.0005(7) 0.0020(7) 0.0032(7) C28 0.0612(14) 0.0334(11) 0.0543(13) -0.0109(9) 0.0077(11) -0.0059(10) C29 0.0374(12) 0.0839(19) 0.0880(19) -0.0473(16) -0.0150(12) 0.0235(12) C50 0.0227(15) 0.0229(15) 0.0288(16) 0.0040(12) -0.0050(12) -0.0019(12) O1 0.0201(13) 0.0297(14) 0.0245(14) -0.0022(10) -0.0025(10) 0.0027(10) O2A 0.0271(12) 0.0411(14) 0.0175(10) -0.0032(10) -0.0054(9) -0.0173(10) _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 Al1 Ge1 0.6683(11) 7_557 ? Al1 O1 1.371(5) 7_557 ? Al1 O2A 1.833(3) . ? Al1 N1 1.9037(17) 7_557 ? Al1 N2 1.9191(17) 7_557 ? Ge1 Al1 0.6683(11) 7_557 ? Ge1 O2A 1.231(2) 7_557 ? Ge1 O1 1.826(5) . ? Ge1 N1 2.0191(14) . ? Ge1 N2 2.0324(14) . ? Ge1 C50 2.358(3) 7_557 ? N1 C2 1.331(2) . ? N1 C6 1.452(2) . ? N1 Al1 1.9037(17) 7_557 ? N2 C4 1.329(2) . ? N2 C18 1.4479(19) . ? N2 Al1 1.9191(17) 7_557 ? C1 C2 1.512(2) . ? C2 C3 1.399(2) . ? C3 C4 1.399(2) . ? C4 C5 1.511(2) . ? C6 C11 1.405(2) . ? C6 C7 1.407(2) . ? C7 C8 1.390(2) . ? C7 C15 1.523(3) . ? C8 C9 1.383(3) . ? C9 C10 1.380(3) . ? C10 C11 1.399(2) . ? C11 C12 1.518(2) . ? C12 C13 1.524(3) . ? C12 C14 1.535(2) . ? C15 C17 1.518(3) . ? C15 C16 1.525(3) . ? C18 C19 1.402(2) . ? C18 C23 1.405(2) . ? C19 C20 1.398(2) . ? C19 C27 1.517(2) . ? C20 C21 1.382(3) . ? C21 C22 1.379(3) . ? C22 C23 1.392(2) . ? C23 C24 1.519(3) . ? C24 C26 1.512(3) . ? C24 C25 1.533(3) . ? C27 C29 1.519(3) . ? C27 C28 1.526(3) . ? C50 O2A 1.391(4) . ? C50 O1 1.398(5) . ? C50 Ge1 2.358(3) 7_557 ? O1 Al1 1.371(5) 7_557 ? O2A Ge1 1.231(2) 7_557 ? 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 Ge1 Al1 O1 123.4(2) 7_557 7_557 ? Ge1 Al1 O2A 20.67(12) 7_557 . ? O1 Al1 O2A 103.03(18) 7_557 . ? Ge1 Al1 N1 90.14(14) 7_557 7_557 ? O1 Al1 N1 121.9(2) 7_557 7_557 ? O2A Al1 N1 105.64(11) . 7_557 ? Ge1 Al1 N2 90.03(14) 7_557 7_557 ? O1 Al1 N2 125.7(2) 7_557 7_557 ? O2A Al1 N2 101.60(10) . 7_557 ? N1 Al1 N2 96.11(8) 7_557 7_557 ? Al1 Ge1 O2A 148.29(19) 7_557 7_557 ? Al1 Ge1 O1 38.77(16) 7_557 . ? O2A Ge1 O1 109.80(16) 7_557 . ? Al1 Ge1 N1 70.53(13) 7_557 . ? O2A Ge1 N1 131.22(13) 7_557 . ? O1 Ge1 N1 96.62(14) . . ? Al1 Ge1 N2 70.78(13) 7_557 . ? O2A Ge1 N2 124.22(12) 7_557 . ? O1 Ge1 N2 99.05(14) . . ? N1 Ge1 N2 89.14(6) . . ? Al1 Ge1 C50 132.65(15) 7_557 7_557 ? O2A Ge1 C50 27.67(14) 7_557 7_557 ? O1 Ge1 C50 96.78(14) . 7_557 ? N1 Ge1 C50 111.98(9) . 7_557 ? N2 Ge1 C50 151.86(9) . 7_557 ? C2 N1 C6 118.36(13) . . ? C2 N1 Al1 115.98(12) . 7_557 ? C6 N1 Al1 123.72(11) . 7_557 ? C2 N1 Ge1 127.58(11) . . ? C6 N1 Ge1 114.00(10) . . ? Al1 N1 Ge1 19.33(4) 7_557 . ? C4 N2 C18 118.86(13) . . ? C4 N2 Al1 116.35(11) . 7_557 ? C18 N2 Al1 123.79(10) . 7_557 ? C4 N2 Ge1 127.61(11) . . ? C18 N2 Ge1 113.17(9) . . ? Al1 N2 Ge1 19.20(4) 7_557 . ? N1 C2 C3 123.20(15) . . ? N1 C2 C1 120.35(15) . . ? C3 C2 C1 116.43(15) . . ? C4 C3 C2 127.38(15) . . ? N2 C4 C3 122.85(14) . . ? N2 C4 C5 120.06(14) . . ? C3 C4 C5 117.02(14) . . ? C11 C6 C7 121.45(15) . . ? C11 C6 N1 119.81(14) . . ? C7 C6 N1 118.74(14) . . ? C8 C7 C6 117.88(16) . . ? C8 C7 C15 120.47(16) . . ? C6 C7 C15 121.64(15) . . ? C9 C8 C7 121.66(17) . . ? C10 C9 C8 119.48(16) . . ? C9 C10 C11 121.53(17) . . ? C10 C11 C6 117.74(16) . . ? C10 C11 C12 119.16(15) . . ? C6 C11 C12 123.08(14) . . ? C11 C12 C13 109.99(15) . . ? C11 C12 C14 112.27(16) . . ? C13 C12 C14 109.82(16) . . ? C17 C15 C7 111.84(18) . . ? C17 C15 C16 110.60(17) . . ? C7 C15 C16 112.48(16) . . ? C19 C18 C23 121.67(15) . . ? C19 C18 N2 119.88(14) . . ? C23 C18 N2 118.44(14) . . ? C20 C19 C18 118.08(16) . . ? C20 C19 C27 119.13(16) . . ? C18 C19 C27 122.78(15) . . ? C21 C20 C19 120.94(18) . . ? C22 C21 C20 119.97(17) . . ? C21 C22 C23 121.56(17) . . ? C22 C23 C18 117.75(17) . . ? C22 C23 C24 120.11(16) . . ? C18 C23 C24 122.14(15) . . ? C26 C24 C23 111.89(17) . . ? C26 C24 C25 111.01(17) . . ? C23 C24 C25 111.70(17) . . ? C19 C27 C29 110.27(16) . . ? C19 C27 C28 112.32(16) . . ? C29 C27 C28 109.31(19) . . ? O2A C50 O1 113.1(3) . . ? O2A C50 Ge1 24.27(12) . 7_557 ? O1 C50 Ge1 124.5(3) . 7_557 ? Al1 O1 C50 131.6(4) 7_557 . ? Al1 O1 Ge1 17.78(9) 7_557 . ? C50 O1 Ge1 116.1(3) . . ? Ge1 O2A C50 128.1(2) 7_557 . ? Ge1 O2A Al1 11.05(7) 7_557 . ? C50 O2A Al1 123.9(2) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 73.62 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.469 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 967659' ####################################################################### # # 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_c2c _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 'C60 H86 Al2 N4 O4' _chemical_formula_weight 981.29 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.8530(10) _cell_length_b 15.1491(6) _cell_length_c 14.8791(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.999(4) _cell_angle_gamma 90.00 _cell_volume 5588.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10503 _cell_measurement_theta_min 4.4290 _cell_measurement_theta_max 73.6870 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8697 _exptl_absorpt_correction_T_max 0.9355 _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 1.54178 _diffrn_radiation_type CuK\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 \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17256 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 67.50 _reflns_number_total 5037 _reflns_number_gt 4426 _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 'Bruker SHELXTL' _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^)+(0.0992P)^2^+2.6555P] 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 5037 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1409 _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 Al1 Al 0.326588(16) 0.23057(3) 0.56372(3) 0.01971(16) Uani 1 1 d . . . N1 N 0.38902(5) 0.16344(8) 0.54312(8) 0.0216(3) Uani 1 1 d . . . N2 N 0.35483(5) 0.29132(9) 0.66802(8) 0.0227(3) Uani 1 1 d . . . O1 O 0.31201(4) 0.29734(8) 0.47240(7) 0.0262(3) Uani 1 1 d . . . O2 O 0.27315(4) 0.16692(7) 0.59351(7) 0.0259(3) Uani 1 1 d . . . C1 C 0.47341(7) 0.08630(12) 0.59448(12) 0.0317(4) Uani 1 1 d . . . H1A H 0.4610 0.0366 0.5563 0.048 Uiso 1 1 calc R . . H1B H 0.4890 0.0640 0.6524 0.048 Uiso 1 1 calc R . . H1C H 0.5008 0.1197 0.5645 0.048 Uiso 1 1 calc R . . C2 C 0.42626(6) 0.14596(11) 0.61024(11) 0.0247(3) Uani 1 1 d . . . C3 C 0.42566(6) 0.18473(11) 0.69561(11) 0.0278(4) Uani 1 1 d . . . H3 H 0.4487 0.1588 0.7419 0.033 Uiso 1 1 calc R . . C4 C 0.39523(7) 0.25702(11) 0.72092(10) 0.0264(3) Uani 1 1 d . . . C5 C 0.41099(8) 0.29779(13) 0.81180(12) 0.0378(4) Uani 1 1 d . . . H5A H 0.4122 0.3622 0.8059 0.057 Uiso 1 1 calc R . . H5B H 0.4466 0.2759 0.8339 0.057 Uiso 1 1 calc R . . H5C H 0.3843 0.2817 0.8545 0.057 Uiso 1 1 calc R . . C6 C 0.39809(6) 0.13005(10) 0.45405(10) 0.0236(3) Uani 1 1 d . . . C7 C 0.42605(6) 0.18419(12) 0.39608(11) 0.0286(4) Uani 1 1 d . . . C8 C 0.43563(7) 0.15046(13) 0.31108(12) 0.0355(4) Uani 1 1 d . . . H8 H 0.4545 0.1856 0.2707 0.043 Uiso 1 1 calc R . . C9 C 0.41827(8) 0.06735(13) 0.28478(12) 0.0375(4) Uani 1 1 d . . . H9 H 0.4257 0.0455 0.2271 0.045 Uiso 1 1 calc R . . C10 C 0.39024(7) 0.01597(12) 0.34185(12) 0.0339(4) Uani 1 1 d . . . H10 H 0.3782 -0.0410 0.3228 0.041 Uiso 1 1 calc R . . C11 C 0.37925(7) 0.04638(11) 0.42740(11) 0.0277(4) Uani 1 1 d . . . C12 C 0.34684(7) -0.01213(11) 0.48682(12) 0.0316(4) Uani 1 1 d . . . H12 H 0.3390 0.0220 0.5419 0.038 Uiso 1 1 calc R . . C13 C 0.29306(8) -0.03758(12) 0.43659(14) 0.0384(4) Uani 1 1 d . . . H13A H 0.2757 0.0154 0.4101 0.058 Uiso 1 1 calc R . . H13B H 0.2694 -0.0646 0.4789 0.058 Uiso 1 1 calc R . . H13C H 0.2997 -0.0798 0.3887 0.058 Uiso 1 1 calc R . . C14 C 0.37773(9) -0.09636(13) 0.51644(14) 0.0437(5) Uani 1 1 d . . . H14A H 0.3852 -0.1311 0.4632 0.066 Uiso 1 1 calc R . . H14B H 0.3558 -0.1314 0.5555 0.066 Uiso 1 1 calc R . . H14C H 0.4118 -0.0802 0.5495 0.066 Uiso 1 1 calc R . . C15 C 0.44622(7) 0.27560(12) 0.42236(12) 0.0347(4) Uani 1 1 d . . . H15 H 0.4329 0.2895 0.4827 0.042 Uiso 1 1 calc R . . C16 C 0.50824(9) 0.27894(16) 0.43215(18) 0.0527(6) Uani 1 1 d . . . H16A H 0.5225 0.2692 0.3732 0.079 Uiso 1 1 calc R . . H16B H 0.5218 0.2328 0.4741 0.079 Uiso 1 1 calc R . . H16C H 0.5199 0.3369 0.4554 0.079 Uiso 1 1 calc R . . C17 C 0.42418(9) 0.34565(14) 0.35730(17) 0.0510(5) Uani 1 1 d . . . H17A H 0.4369 0.3344 0.2975 0.076 Uiso 1 1 calc R . . H17B H 0.4367 0.4039 0.3785 0.076 Uiso 1 1 calc R . . H17C H 0.3847 0.3440 0.3538 0.076 Uiso 1 1 calc R . . C18 C 0.33125(6) 0.37378(10) 0.69559(10) 0.0249(3) Uani 1 1 d . . . C19 C 0.35113(7) 0.45336(11) 0.66199(11) 0.0299(4) Uani 1 1 d . . . C20 C 0.33158(8) 0.53227(12) 0.69508(13) 0.0356(4) Uani 1 1 d . . . H20 H 0.3454 0.5867 0.6747 0.043 Uiso 1 1 calc R . . C21 C 0.29255(8) 0.53309(12) 0.75688(12) 0.0365(4) Uani 1 1 d . . . H21 H 0.2804 0.5876 0.7798 0.044 Uiso 1 1 calc R . . C22 C 0.27136(7) 0.45458(11) 0.78520(12) 0.0327(4) Uani 1 1 d . . . H22 H 0.2436 0.4557 0.8259 0.039 Uiso 1 1 calc R . . C23 C 0.28992(7) 0.37323(11) 0.75524(10) 0.0266(4) Uani 1 1 d . . . C24 C 0.26363(7) 0.28912(11) 0.78661(11) 0.0298(4) Uani 1 1 d . . . H24 H 0.2829 0.2376 0.7618 0.036 Uiso 1 1 calc R . . C25 C 0.20473(8) 0.28532(12) 0.75024(13) 0.0379(4) Uani 1 1 d . . . H25A H 0.1858 0.3379 0.7699 0.057 Uiso 1 1 calc R . . H25B H 0.1877 0.2323 0.7732 0.057 Uiso 1 1 calc R . . H25C H 0.2029 0.2834 0.6843 0.057 Uiso 1 1 calc R . . C26 C 0.26718(10) 0.28134(14) 0.88962(12) 0.0439(5) Uani 1 1 d . . . H26A H 0.2473 0.3301 0.9151 0.066 Uiso 1 1 calc R . . H26B H 0.3051 0.2839 0.9126 0.066 Uiso 1 1 calc R . . H26C H 0.2515 0.2251 0.9069 0.066 Uiso 1 1 calc R . . C27 C 0.39321(8) 0.45491(12) 0.59247(13) 0.0382(4) Uani 1 1 d . . . H27 H 0.3899 0.3981 0.5583 0.046 Uiso 1 1 calc R . . C28 C 0.45034(9) 0.45920(17) 0.63636(18) 0.0586(6) Uani 1 1 d . . . H28A H 0.4543 0.5122 0.6740 0.088 Uiso 1 1 calc R . . H28B H 0.4761 0.4615 0.5895 0.088 Uiso 1 1 calc R . . H28C H 0.4574 0.4067 0.6738 0.088 Uiso 1 1 calc R . . C29 C 0.38400(9) 0.52985(15) 0.52412(14) 0.0481(5) Uani 1 1 d . . . H29A H 0.3903 0.5867 0.5545 0.072 Uiso 1 1 calc R . . H29B H 0.3468 0.5275 0.4977 0.072 Uiso 1 1 calc R . . H29C H 0.4090 0.5233 0.4764 0.072 Uiso 1 1 calc R . . C30 C 0.23008(7) 0.14130(11) 0.53375(11) 0.0283(4) Uani 1 1 d . . . H30A H 0.2434 0.1327 0.4732 0.034 Uiso 1 1 calc R . . H30B H 0.2160 0.0839 0.5537 0.034 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 Al1 0.0224(3) 0.0211(3) 0.0162(3) -0.00104(16) 0.00523(18) 0.00135(15) N1 0.0240(6) 0.0233(7) 0.0181(6) -0.0010(5) 0.0062(5) 0.0009(5) N2 0.0276(7) 0.0216(7) 0.0194(6) -0.0016(5) 0.0052(5) 0.0003(5) O1 0.0271(6) 0.0305(6) 0.0218(5) 0.0045(5) 0.0066(4) 0.0031(4) O2 0.0260(5) 0.0315(6) 0.0206(5) 0.0029(4) 0.0040(4) -0.0018(4) C1 0.0297(8) 0.0355(9) 0.0303(8) 0.0004(7) 0.0042(7) 0.0078(7) C2 0.0250(7) 0.0242(8) 0.0256(8) 0.0041(6) 0.0062(6) 0.0010(6) C3 0.0289(8) 0.0329(8) 0.0212(8) 0.0028(7) 0.0002(6) 0.0033(6) C4 0.0302(8) 0.0296(8) 0.0197(7) -0.0006(6) 0.0027(6) -0.0020(6) C5 0.0429(10) 0.0440(11) 0.0257(9) -0.0072(8) -0.0034(7) 0.0067(8) C6 0.0246(7) 0.0273(8) 0.0198(7) 0.0002(6) 0.0079(6) 0.0054(6) C7 0.0277(8) 0.0333(9) 0.0262(8) 0.0029(7) 0.0119(6) 0.0042(6) C8 0.0380(9) 0.0431(10) 0.0277(9) 0.0056(8) 0.0187(7) 0.0064(8) C9 0.0454(10) 0.0452(11) 0.0235(8) -0.0051(8) 0.0133(7) 0.0127(8) C10 0.0427(9) 0.0327(9) 0.0271(8) -0.0056(7) 0.0079(7) 0.0053(7) C11 0.0314(8) 0.0285(8) 0.0241(8) -0.0011(7) 0.0079(6) 0.0047(6) C12 0.0422(9) 0.0257(8) 0.0284(8) -0.0030(7) 0.0124(7) -0.0018(7) C13 0.0410(10) 0.0297(9) 0.0454(11) -0.0020(8) 0.0105(8) -0.0034(7) C14 0.0532(11) 0.0352(10) 0.0430(11) 0.0088(8) 0.0059(9) -0.0001(9) C15 0.0389(10) 0.0332(9) 0.0342(9) 0.0029(7) 0.0176(8) -0.0033(7) C16 0.0457(12) 0.0480(12) 0.0643(14) 0.0040(11) 0.0025(10) -0.0088(9) C17 0.0545(12) 0.0356(11) 0.0633(14) 0.0090(10) 0.0078(11) -0.0016(9) C18 0.0321(8) 0.0237(8) 0.0189(7) -0.0037(6) 0.0009(6) 0.0012(6) C19 0.0349(9) 0.0271(8) 0.0278(8) -0.0031(7) 0.0035(7) -0.0044(7) C20 0.0466(10) 0.0234(8) 0.0372(10) -0.0039(7) 0.0060(8) -0.0050(7) C21 0.0498(11) 0.0252(9) 0.0349(9) -0.0065(7) 0.0058(8) 0.0041(7) C22 0.0438(10) 0.0290(9) 0.0262(8) -0.0048(7) 0.0095(7) 0.0049(7) C23 0.0367(8) 0.0248(8) 0.0185(7) -0.0022(6) 0.0034(6) 0.0027(6) C24 0.0435(9) 0.0252(8) 0.0224(8) -0.0008(6) 0.0143(7) 0.0053(7) C25 0.0446(10) 0.0312(9) 0.0396(10) -0.0005(8) 0.0146(8) -0.0022(8) C26 0.0669(13) 0.0402(11) 0.0265(9) 0.0071(8) 0.0167(9) 0.0112(9) C27 0.0449(10) 0.0296(9) 0.0421(10) -0.0052(8) 0.0177(8) -0.0091(7) C28 0.0395(11) 0.0641(15) 0.0739(16) 0.0165(13) 0.0161(11) 0.0001(10) C29 0.0546(12) 0.0481(12) 0.0433(11) 0.0047(9) 0.0151(9) -0.0157(9) C30 0.0302(8) 0.0263(8) 0.0282(8) -0.0022(7) 0.0002(7) 0.0013(6) _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 Al1 O1 1.7123(11) . ? Al1 O2 1.7239(11) . ? Al1 N2 1.8963(13) . ? Al1 N1 1.8979(13) . ? N1 C2 1.340(2) . ? N1 C6 1.4507(19) . ? N2 C4 1.337(2) . ? N2 C18 1.451(2) . ? O1 C30 1.397(2) 7_556 ? O2 C30 1.3981(19) . ? C1 C2 1.511(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.400(2) . ? C3 C4 1.397(2) . ? C3 H3 0.9500 . ? C4 C5 1.513(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.399(2) . ? C6 C7 1.408(2) . ? C7 C8 1.400(2) . ? C7 C15 1.515(3) . ? C8 C9 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? C10 C11 1.398(2) . ? C10 H10 0.9500 . ? C11 C12 1.522(2) . ? C12 C13 1.534(3) . ? C12 C14 1.538(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.513(3) . ? C15 C16 1.539(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.403(2) . ? C18 C19 1.408(2) . ? C19 C20 1.393(3) . ? C19 C27 1.522(2) . ? C20 C21 1.382(3) . ? C20 H20 0.9500 . ? C21 C22 1.379(3) . ? C21 H21 0.9500 . ? C22 C23 1.400(2) . ? C22 H22 0.9500 . ? C23 C24 1.520(2) . ? C24 C25 1.526(3) . ? C24 C26 1.534(2) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.522(3) . ? C27 C29 1.531(3) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O1 1.397(2) 7_556 ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Al1 O2 114.22(6) . . ? O1 Al1 N2 114.11(6) . . ? O2 Al1 N2 107.98(6) . . ? O1 Al1 N1 108.58(6) . . ? O2 Al1 N1 113.27(6) . . ? N2 Al1 N1 97.59(6) . . ? C2 N1 C6 117.96(13) . . ? C2 N1 Al1 121.03(11) . . ? C6 N1 Al1 121.01(10) . . ? C4 N2 C18 118.01(13) . . ? C4 N2 Al1 120.87(11) . . ? C18 N2 Al1 121.03(10) . . ? C30 O1 Al1 124.12(10) 7_556 . ? C30 O2 Al1 124.14(10) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.88(14) . . ? N1 C2 C1 120.35(14) . . ? C3 C2 C1 116.67(14) . . ? C4 C3 C2 127.82(14) . . ? C4 C3 H3 116.1 . . ? C2 C3 H3 116.1 . . ? N2 C4 C3 122.98(14) . . ? N2 C4 C5 120.29(15) . . ? C3 C4 C5 116.71(14) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 121.59(15) . . ? C11 C6 N1 120.30(14) . . ? C7 C6 N1 118.11(14) . . ? C8 C7 C6 117.58(16) . . ? C8 C7 C15 119.53(15) . . ? C6 C7 C15 122.89(15) . . ? C9 C8 C7 121.35(16) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 120.20(16) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.97(17) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C6 118.28(16) . . ? C10 C11 C12 118.81(16) . . ? C6 C11 C12 122.91(14) . . ? C11 C12 C13 109.99(14) . . ? C11 C12 C14 112.08(15) . . ? C13 C12 C14 109.37(15) . . ? C11 C12 H12 108.4 . . ? C13 C12 H12 108.4 . . ? C14 C12 H12 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C15 C7 112.18(17) . . ? C17 C15 C16 110.68(16) . . ? C7 C15 C16 111.46(16) . . ? C17 C15 H15 107.4 . . ? C7 C15 H15 107.4 . . ? C16 C15 H15 107.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 121.34(15) . . ? C23 C18 N2 120.09(14) . . ? C19 C18 N2 118.56(14) . . ? C20 C19 C18 118.00(16) . . ? C20 C19 C27 120.01(16) . . ? C18 C19 C27 121.98(15) . . ? C21 C20 C19 121.40(17) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C22 C21 C20 119.76(16) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 121.39(16) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 117.91(15) . . ? C22 C23 C24 118.81(15) . . ? C18 C23 C24 123.26(14) . . ? C23 C24 C25 110.18(14) . . ? C23 C24 C26 112.04(15) . . ? C25 C24 C26 109.78(16) . . ? C23 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? C26 C24 H24 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 C28 111.95(17) . . ? C19 C27 C29 112.65(16) . . ? C28 C27 C29 110.19(16) . . ? C19 C27 H27 107.2 . . ? C28 C27 H27 107.2 . . ? C29 C27 H27 107.2 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O1 C30 O2 113.16(13) 7_556 . ? O1 C30 H30A 108.9 7_556 . ? O2 C30 H30A 108.9 . . ? O1 C30 H30B 108.9 7_556 . ? O2 C30 H30B 108.9 . . ? H30A C30 H30B 107.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.619 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 967660'