# 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_1R _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Mn2 N12 Nb O8' _chemical_formula_weight 975.62 _chemical_absolute_configuration rmad 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.946(2) _cell_length_b 13.280(2) _cell_length_c 13.803(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.237(2) _cell_angle_gamma 90.00 _cell_volume 2196.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9840 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 0.884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18511 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10029 _reflns_number_gt 9096 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^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 SHELXL _refine_ls_extinction_coef 0.0268(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.008(15) _refine_ls_number_reflns 10029 _refine_ls_number_parameters 537 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Nb1 Nb 0.988162(17) 0.860084(19) 0.739651(17) 0.02269(8) Uani 1 1 d . . . Mn2 Mn 1.18340(4) 0.67181(3) 1.11725(4) 0.02920(12) Uani 1 1 d . . . Mn1 Mn 1.19438(4) 1.16624(3) 0.63272(4) 0.03071(13) Uani 1 1 d . . . C16 C 1.0522(3) 0.7536(2) 0.8773(3) 0.0318(7) Uani 1 1 d . . . N16 N 1.0891(2) 0.7079(2) 0.9532(2) 0.0401(7) Uani 1 1 d . . . C12 C 1.1276(3) 0.7814(3) 0.7081(3) 0.0345(7) Uani 1 1 d . . . N12 N 1.1950(3) 0.7387(3) 0.6893(3) 0.0526(8) Uani 1 1 d . . . C13 C 0.9152(3) 0.7534(2) 0.6045(3) 0.0326(7) Uani 1 1 d . . . N13 N 0.8773(3) 0.7044(2) 0.5312(2) 0.0429(7) Uani 1 1 d . . . C17 C 0.8386(3) 0.7928(2) 0.7621(3) 0.0337(7) Uani 1 1 d . . . N17 N 0.7618(3) 0.7558(3) 0.7710(3) 0.0525(8) Uani 1 1 d . . . C18 C 0.9498(2) 0.9818(2) 0.8343(2) 0.0287(6) Uani 1 1 d . . . N18 N 0.9236(2) 1.0488(2) 0.8734(2) 0.0378(6) Uani 1 1 d . . . C15 C 1.1512(3) 0.9271(2) 0.8483(2) 0.0310(6) Uani 1 1 d . . . N15 N 1.2318(2) 0.9675(2) 0.9001(2) 0.0435(7) Uani 1 1 d . . . C11 C 1.0397(2) 0.9804(2) 0.6523(2) 0.0291(6) Uani 1 1 d . . . N11 N 1.0747(2) 1.0470(2) 0.6215(2) 0.0372(6) Uani 1 1 d . . . C14 C 0.8332(3) 0.9400(2) 0.6295(3) 0.0322(7) Uani 1 1 d . . . N14 N 0.7570(2) 0.9869(2) 0.5774(3) 0.0460(7) Uani 1 1 d . . . N4 N 1.3137(2) 0.5589(2) 1.1113(2) 0.0352(6) Uani 1 1 d . . . C36 C 1.3070(3) 0.4595(3) 1.1221(3) 0.0426(8) Uani 1 1 d . . . H36 H 1.2426 0.4339 1.1278 0.051 Uiso 1 1 calc R . . C35 C 1.3892(4) 0.3927(3) 1.1253(4) 0.0588(11) Uani 1 1 d . . . H35 H 1.3807 0.3239 1.1320 0.071 Uiso 1 1 calc R . . C34 C 1.4860(4) 0.4319(4) 1.1181(5) 0.0676(13) Uani 1 1 d . . . H34 H 1.5444 0.3896 1.1214 0.081 Uiso 1 1 calc R . . C33 C 1.4938(4) 0.5343(4) 1.1060(4) 0.0571(11) Uani 1 1 d . . . H33 H 1.5576 0.5619 1.1008 0.069 Uiso 1 1 calc R . . C32 C 1.4057(3) 0.5957(3) 1.1017(3) 0.0383(7) Uani 1 1 d . . . C4 C 1.4096(3) 0.7062(3) 1.0831(4) 0.0494(9) Uani 1 1 d . . . H4 H 1.4856 0.7315 1.1202 0.059 Uiso 1 1 calc R . . O4 O 1.3343(2) 0.7552(2) 1.1216(3) 0.0472(7) Uani 1 1 d . . . C8 C 1.3735(5) 0.7248(4) 0.9635(5) 0.0835(18) Uani 1 1 d . . . H8A H 1.2999 0.6983 0.9274 0.125 Uiso 1 1 calc R . . H8B H 1.4249 0.6917 0.9388 0.125 Uiso 1 1 calc R . . H8C H 1.3736 0.7958 0.9505 0.125 Uiso 1 1 calc R . . N3 N 1.1476(3) 0.8232(2) 1.1752(2) 0.0379(6) Uani 1 1 d . . . C31 C 1.1091(4) 0.9019(3) 1.1104(3) 0.0494(9) Uani 1 1 d . . . H31 H 1.0803 0.8903 1.0386 0.059 Uiso 1 1 calc R . . C30 C 1.1105(5) 0.9987(3) 1.1455(4) 0.0626(12) Uani 1 1 d . . . H30 H 1.0815 1.0512 1.0984 0.075 Uiso 1 1 calc R . . C29 C 1.1555(5) 1.0172(3) 1.2518(4) 0.0698(14) Uani 1 1 d . . . H29 H 1.1586 1.0823 1.2775 0.084 Uiso 1 1 calc R . . C28 C 1.1955(5) 0.9372(3) 1.3185(4) 0.0625(13) Uani 1 1 d . . . H28 H 1.2266 0.9475 1.3905 0.075 Uiso 1 1 calc R . . C27 C 1.1892(3) 0.8408(3) 1.2779(3) 0.0405(8) Uani 1 1 d . . . C3 C 1.2247(3) 0.7519(3) 1.3517(3) 0.0394(8) Uani 1 1 d . . . H3 H 1.2942 0.7690 1.4100 0.047 Uiso 1 1 calc R . . O3 O 1.2447(2) 0.66757(19) 1.29619(19) 0.0403(5) Uani 1 1 d . . . C7 C 1.1359(4) 0.7279(4) 1.3949(4) 0.0607(12) Uani 1 1 d . . . H7A H 1.0669 0.7129 1.3382 0.091 Uiso 1 1 calc R . . H7B H 1.1257 0.7848 1.4332 0.091 Uiso 1 1 calc R . . H7C H 1.1588 0.6707 1.4407 0.091 Uiso 1 1 calc R . . N2 N 1.3223(2) 1.0519(2) 0.6276(2) 0.0368(6) Uani 1 1 d . . . C26 C 1.3080(3) 0.9516(3) 0.6242(3) 0.0472(9) Uani 1 1 d . . . H26 H 1.2406 0.9267 0.6234 0.057 Uiso 1 1 calc R . . C25 C 1.3867(4) 0.8836(3) 0.6218(4) 0.0617(12) Uani 1 1 d . . . H25 H 1.3743 0.8146 0.6218 0.074 Uiso 1 1 calc R . . C24 C 1.4863(4) 0.9222(4) 0.6192(4) 0.0674(13) Uani 1 1 d . . . H24 H 1.5418 0.8789 0.6169 0.081 Uiso 1 1 calc R . . C23 C 1.5010(3) 1.0235(4) 0.6200(4) 0.0584(12) Uani 1 1 d . . . H23 H 1.5663 1.0498 0.6170 0.070 Uiso 1 1 calc R . . C22 C 1.4191(3) 1.0875(3) 0.6254(3) 0.0416(8) Uani 1 1 d . . . C2 C 1.4343(3) 1.2004(3) 0.6277(3) 0.0532(10) Uani 1 1 d . . . H2 H 1.5086 1.2165 0.6794 0.064 Uiso 1 1 calc R . . O2 O 1.3533(2) 1.2444(2) 0.6611(3) 0.0556(8) Uani 1 1 d . . . C6 C 1.4253(6) 1.2424(6) 0.5237(5) 0.107(3) Uani 1 1 d . . . H6A H 1.3514 1.2312 0.4730 0.160 Uiso 1 1 calc R . . H6B H 1.4785 1.2095 0.5013 0.160 Uiso 1 1 calc R . . H6C H 1.4404 1.3134 0.5304 0.160 Uiso 1 1 calc R . . N1 N 1.1469(3) 1.3147(2) 0.6862(2) 0.0385(6) Uani 1 1 d . . . C21 C 1.1037(4) 1.3926(3) 0.6198(3) 0.0488(9) Uani 1 1 d . . . H21 H 1.0824 1.3811 0.5485 0.059 Uiso 1 1 calc R . . C20 C 1.0895(4) 1.4871(3) 0.6517(4) 0.0604(11) Uani 1 1 d . . . H20 H 1.0598 1.5385 0.6034 0.072 Uiso 1 1 calc R . . C19 C 1.1203(5) 1.5042(3) 0.7578(4) 0.0691(14) Uani 1 1 d . . . H19 H 1.1114 1.5674 0.7827 0.083 Uiso 1 1 calc R . . C10 C 1.1645(5) 1.4252(3) 0.8257(4) 0.0637(13) Uani 1 1 d . . . H10 H 1.1862 1.4351 0.8974 0.076 Uiso 1 1 calc R . . C9 C 1.1768(3) 1.3319(3) 0.7882(3) 0.0424(8) Uani 1 1 d . . . C1 C 1.2264(3) 1.2459(3) 0.8637(3) 0.0430(8) Uani 1 1 d . . . H1 H 1.3002 1.2667 0.9129 0.052 Uiso 1 1 calc R . . O1 O 1.2403(2) 1.1605(2) 0.8068(2) 0.0470(6) Uani 1 1 d . . . C5 C 1.1553(5) 1.2196(4) 0.9265(4) 0.0651(13) Uani 1 1 d . . . H5A H 1.0849 1.1929 0.8805 0.098 Uiso 1 1 calc R . . H5B H 1.1428 1.2792 0.9601 0.098 Uiso 1 1 calc R . . H5C H 1.1933 1.1703 0.9786 0.098 Uiso 1 1 calc R . . O5 O 1.3757(2) 0.9529(2) 1.1129(2) 0.0616(8) Uani 1 1 d . . . O7 O 1.3461(3) 0.6033(3) 0.6344(3) 0.0807(11) Uani 1 1 d . . . O6 O 1.4143(3) 1.1227(3) 1.2297(4) 0.1191(19) Uani 1 1 d . . . O8 O 1.3999(3) 0.4210(3) 0.7515(4) 0.1116(16) 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 Nb1 0.02771(12) 0.01782(12) 0.02367(13) -0.00016(18) 0.01100(9) -0.00024(19) Mn2 0.0316(2) 0.0242(2) 0.0330(3) 0.0058(2) 0.0137(2) 0.00106(19) Mn1 0.0328(2) 0.0267(3) 0.0320(3) 0.0056(2) 0.0115(2) -0.0021(2) C16 0.0350(15) 0.0290(16) 0.0342(17) 0.0040(13) 0.0161(14) -0.0009(12) N16 0.0457(16) 0.0359(15) 0.0354(15) 0.0106(12) 0.0118(13) -0.0020(13) C12 0.0381(16) 0.0286(16) 0.0396(18) -0.0001(14) 0.0179(15) 0.0031(13) N12 0.0508(19) 0.051(2) 0.066(2) 0.0010(16) 0.0337(18) 0.0108(15) C13 0.0378(16) 0.0311(16) 0.0308(16) -0.0037(13) 0.0151(13) 0.0022(13) N13 0.0461(16) 0.0405(16) 0.0391(16) -0.0111(13) 0.0128(14) 0.0026(13) C17 0.0401(17) 0.0264(15) 0.0395(18) -0.0020(13) 0.0206(15) -0.0027(13) N17 0.0520(19) 0.0409(18) 0.076(2) -0.0049(16) 0.0376(19) -0.0108(14) C18 0.0293(14) 0.0272(15) 0.0296(15) -0.0066(12) 0.0113(12) -0.0020(12) N18 0.0368(14) 0.0352(15) 0.0416(16) -0.0111(13) 0.0153(13) -0.0002(12) C15 0.0337(15) 0.0256(14) 0.0312(15) 0.0027(12) 0.0094(13) 0.0004(12) N15 0.0374(15) 0.0410(16) 0.0431(17) 0.0045(14) 0.0052(13) -0.0040(13) C11 0.0266(13) 0.0299(15) 0.0285(14) 0.0051(12) 0.0079(12) 0.0005(11) N11 0.0371(14) 0.0352(15) 0.0389(15) 0.0089(12) 0.0140(12) -0.0025(12) C14 0.0337(15) 0.0277(16) 0.0356(16) -0.0019(13) 0.0135(14) -0.0016(12) N14 0.0367(15) 0.0435(18) 0.0493(18) 0.0002(14) 0.0067(14) 0.0053(13) N4 0.0352(13) 0.0333(14) 0.0380(15) 0.0022(12) 0.0148(12) 0.0021(11) C36 0.051(2) 0.0317(18) 0.051(2) 0.0034(15) 0.0259(18) 0.0043(15) C35 0.072(3) 0.037(2) 0.076(3) 0.0019(19) 0.038(3) 0.0149(18) C34 0.067(3) 0.057(3) 0.093(4) 0.000(3) 0.046(3) 0.024(2) C33 0.046(2) 0.062(3) 0.074(3) 0.001(2) 0.034(2) 0.0110(19) C32 0.0331(16) 0.0429(19) 0.0391(18) 0.0003(15) 0.0139(15) 0.0031(14) C4 0.0398(19) 0.042(2) 0.074(3) 0.0025(19) 0.030(2) -0.0051(15) O4 0.0417(14) 0.0359(14) 0.073(2) -0.0048(13) 0.0314(14) -0.0065(11) C8 0.110(4) 0.074(3) 0.100(4) 0.038(3) 0.077(4) 0.023(3) N3 0.0472(16) 0.0278(13) 0.0427(16) 0.0034(12) 0.0218(14) 0.0042(12) C31 0.068(3) 0.0346(18) 0.051(2) 0.0121(17) 0.028(2) 0.0139(17) C30 0.095(3) 0.031(2) 0.075(3) 0.0155(19) 0.048(3) 0.017(2) C29 0.112(4) 0.030(2) 0.076(3) -0.003(2) 0.046(3) 0.003(2) C28 0.098(4) 0.034(2) 0.052(3) -0.0066(19) 0.026(3) -0.005(2) C27 0.0481(18) 0.032(2) 0.0418(18) -0.0007(14) 0.0174(15) -0.0048(14) C3 0.0452(19) 0.0334(18) 0.0371(19) 0.0009(14) 0.0129(15) 0.0030(14) O3 0.0542(14) 0.0317(12) 0.0359(13) 0.0056(10) 0.0180(11) 0.0062(11) C7 0.080(3) 0.052(3) 0.065(3) 0.015(2) 0.044(3) 0.014(2) N2 0.0328(13) 0.0404(16) 0.0368(14) 0.0010(13) 0.0127(12) -0.0020(12) C26 0.0463(19) 0.041(2) 0.055(2) -0.0078(17) 0.0193(18) 0.0003(16) C25 0.062(2) 0.051(3) 0.071(3) -0.018(2) 0.024(2) 0.0061(19) C24 0.050(2) 0.083(4) 0.071(3) -0.025(3) 0.024(2) 0.014(2) C23 0.0386(19) 0.086(4) 0.057(3) -0.014(2) 0.0258(19) 0.000(2) C22 0.0328(16) 0.060(2) 0.0319(17) 0.0003(16) 0.0123(14) -0.0043(15) C2 0.0344(18) 0.065(3) 0.059(2) 0.008(2) 0.0161(17) -0.0124(17) O2 0.0414(14) 0.0426(15) 0.082(2) -0.0042(14) 0.0220(15) -0.0128(12) C6 0.092(4) 0.137(6) 0.110(5) 0.064(5) 0.060(4) 0.004(4) N1 0.0476(17) 0.0286(14) 0.0396(16) -0.0001(12) 0.0170(14) -0.0022(12) C21 0.066(2) 0.0364(19) 0.045(2) 0.0074(15) 0.0223(19) 0.0052(17) C20 0.088(3) 0.036(2) 0.059(3) 0.0071(18) 0.030(2) 0.010(2) C19 0.105(4) 0.036(2) 0.070(3) -0.006(2) 0.037(3) 0.010(2) C10 0.099(4) 0.040(2) 0.051(3) -0.0056(19) 0.027(3) -0.005(2) C9 0.053(2) 0.0334(19) 0.0398(19) -0.0002(13) 0.0166(16) -0.0075(14) C1 0.052(2) 0.0377(19) 0.0373(19) -0.0038(15) 0.0151(16) -0.0051(16) O1 0.0701(17) 0.0341(13) 0.0353(13) 0.0050(11) 0.0182(12) 0.0032(12) C5 0.100(4) 0.052(3) 0.061(3) 0.006(2) 0.050(3) -0.002(2) O5 0.0560(17) 0.0474(17) 0.0620(19) 0.0003(14) 0.0005(15) 0.0009(14) O7 0.0565(19) 0.085(3) 0.091(3) -0.011(2) 0.0166(19) 0.0138(17) O6 0.066(2) 0.106(3) 0.160(5) -0.065(3) 0.014(3) 0.021(2) O8 0.071(2) 0.065(2) 0.163(4) -0.017(3) 0.004(3) -0.0154(19) _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 Nb1 C13 2.246(3) . ? Nb1 C18 2.249(3) . ? Nb1 C11 2.250(3) . ? Nb1 C17 2.257(3) . ? Nb1 C15 2.259(3) . ? Nb1 C16 2.260(3) . ? Nb1 C12 2.266(3) . ? Nb1 C14 2.270(3) . ? Mn2 N18 2.177(3) 2_747 ? Mn2 N16 2.180(3) . ? Mn2 O4 2.226(3) . ? Mn2 N3 2.276(3) . ? Mn2 N4 2.282(3) . ? Mn2 O3 2.291(3) . ? Mn1 N13 2.156(3) 2_756 ? Mn1 N11 2.179(3) . ? Mn1 O2 2.204(3) . ? Mn1 O1 2.247(3) . ? Mn1 N2 2.268(3) . ? Mn1 N1 2.270(3) . ? C16 N16 1.146(4) . ? C12 N12 1.150(5) . ? C13 N13 1.145(4) . ? N13 Mn1 2.156(3) 2_746 ? C17 N17 1.157(5) . ? C18 N18 1.156(4) . ? N18 Mn2 2.177(3) 2_757 ? C15 N15 1.151(4) . ? C11 N11 1.146(4) . ? C14 N14 1.158(4) . ? N4 C36 1.335(5) . ? N4 C32 1.339(4) . ? C36 C35 1.374(6) . ? C36 H36 0.9300 . ? C35 C34 1.394(7) . ? C35 H35 0.9300 . ? C34 C33 1.379(7) . ? C34 H34 0.9300 . ? C33 C32 1.385(5) . ? C33 H33 0.9300 . ? C32 C4 1.495(5) . ? C4 O4 1.432(5) . ? C4 C8 1.556(7) . ? C4 H4 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N3 C27 1.333(5) . ? N3 C31 1.343(5) . ? C31 C30 1.371(6) . ? C31 H31 0.9300 . ? C30 C29 1.379(7) . ? C30 H30 0.9300 . ? C29 C28 1.373(7) . ? C29 H29 0.9300 . ? C28 C27 1.387(6) . ? C28 H28 0.9300 . ? C27 C3 1.513(5) . ? C3 O3 1.435(4) . ? C3 C7 1.516(6) . ? C3 H3 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? N2 C26 1.344(5) . ? N2 C22 1.350(4) . ? C26 C25 1.370(6) . ? C26 H26 0.9300 . ? C25 C24 1.401(7) . ? C25 H25 0.9300 . ? C24 C23 1.358(7) . ? C24 H24 0.9300 . ? C23 C22 1.383(6) . ? C23 H23 0.9300 . ? C22 C2 1.511(6) . ? C2 O2 1.421(5) . ? C2 C6 1.503(7) . ? C2 H2 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N1 C9 1.332(5) . ? N1 C21 1.354(5) . ? C21 C20 1.365(6) . ? C21 H21 0.9300 . ? C20 C19 1.383(7) . ? C20 H20 0.9300 . ? C19 C10 1.379(7) . ? C19 H19 0.9300 . ? C10 C9 1.375(6) . ? C10 H10 0.9300 . ? C9 C1 1.515(5) . ? C1 O1 1.430(5) . ? C1 C5 1.525(6) . ? C1 H1 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C13 Nb1 C18 145.10(11) . . ? C13 Nb1 C11 96.89(12) . . ? C18 Nb1 C11 88.62(13) . . ? C13 Nb1 C17 75.63(12) . . ? C18 Nb1 C17 79.36(11) . . ? C11 Nb1 C17 142.97(11) . . ? C13 Nb1 C15 142.53(12) . . ? C18 Nb1 C15 71.76(11) . . ? C11 Nb1 C15 71.57(11) . . ? C17 Nb1 C15 134.34(12) . . ? C13 Nb1 C16 102.04(13) . . ? C18 Nb1 C16 93.03(12) . . ? C11 Nb1 C16 143.76(11) . . ? C17 Nb1 C16 72.38(12) . . ? C15 Nb1 C16 74.63(11) . . ? C13 Nb1 C12 70.42(12) . . ? C18 Nb1 C12 144.09(12) . . ? C11 Nb1 C12 78.77(12) . . ? C17 Nb1 C12 129.13(13) . . ? C15 Nb1 C12 72.36(12) . . ? C16 Nb1 C12 78.91(12) . . ? C13 Nb1 C14 75.63(12) . . ? C18 Nb1 C14 73.71(11) . . ? C11 Nb1 C14 71.05(11) . . ? C17 Nb1 C14 71.97(12) . . ? C15 Nb1 C14 128.87(13) . . ? C16 Nb1 C14 143.67(11) . . ? C12 Nb1 C14 130.80(12) . . ? N18 Mn2 N16 96.21(11) 2_747 . ? N18 Mn2 O4 160.55(11) 2_747 . ? N16 Mn2 O4 93.42(12) . . ? N18 Mn2 N3 115.05(11) 2_747 . ? N16 Mn2 N3 93.57(12) . . ? O4 Mn2 N3 81.05(11) . . ? N18 Mn2 N4 90.26(11) 2_747 . ? N16 Mn2 N4 103.80(11) . . ? O4 Mn2 N4 71.00(10) . . ? N3 Mn2 N4 147.67(11) . . ? N18 Mn2 O3 83.46(10) 2_747 . ? N16 Mn2 O3 162.58(11) . . ? O4 Mn2 O3 92.32(11) . . ? N3 Mn2 O3 71.11(10) . . ? N4 Mn2 O3 93.62(10) . . ? N13 Mn1 N11 94.85(11) 2_756 . ? N13 Mn1 O2 94.45(12) 2_756 . ? N11 Mn1 O2 161.07(11) . . ? N13 Mn1 O1 164.71(12) 2_756 . ? N11 Mn1 O1 86.79(11) . . ? O2 Mn1 O1 88.56(12) . . ? N13 Mn1 N2 98.84(12) 2_756 . ? N11 Mn1 N2 91.14(11) . . ? O2 Mn1 N2 71.15(11) . . ? O1 Mn1 N2 96.32(10) . . ? N13 Mn1 N1 94.30(12) 2_756 . ? N11 Mn1 N1 112.40(11) . . ? O2 Mn1 N1 83.25(11) . . ? O1 Mn1 N1 71.14(10) . . ? N2 Mn1 N1 151.95(11) . . ? N16 C16 Nb1 173.1(3) . . ? C16 N16 Mn2 160.2(3) . . ? N12 C12 Nb1 177.1(3) . . ? N13 C13 Nb1 175.4(3) . . ? C13 N13 Mn1 158.6(3) . 2_746 ? N17 C17 Nb1 177.6(3) . . ? N18 C18 Nb1 173.1(3) . . ? C18 N18 Mn2 155.7(3) . 2_757 ? N15 C15 Nb1 175.2(3) . . ? N11 C11 Nb1 170.3(3) . . ? C11 N11 Mn1 154.7(3) . . ? N14 C14 Nb1 175.1(3) . . ? C36 N4 C32 118.0(3) . . ? C36 N4 Mn2 124.4(2) . . ? C32 N4 Mn2 117.5(2) . . ? N4 C36 C35 124.0(4) . . ? N4 C36 H36 118.0 . . ? C35 C36 H36 118.0 . . ? C36 C35 C34 117.6(4) . . ? C36 C35 H35 121.2 . . ? C34 C35 H35 121.2 . . ? C33 C34 C35 119.1(4) . . ? C33 C34 H34 120.4 . . ? C35 C34 H34 120.4 . . ? C34 C33 C32 119.2(4) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? N4 C32 C33 122.0(4) . . ? N4 C32 C4 117.7(3) . . ? C33 C32 C4 120.3(4) . . ? O4 C4 C32 108.0(3) . . ? O4 C4 C8 110.4(4) . . ? C32 C4 C8 108.8(4) . . ? O4 C4 H4 109.9 . . ? C32 C4 H4 109.9 . . ? C8 C4 H4 109.9 . . ? C4 O4 Mn2 118.6(2) . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C27 N3 C31 118.1(3) . . ? C27 N3 Mn2 118.3(2) . . ? C31 N3 Mn2 121.8(3) . . ? N3 C31 C30 122.8(4) . . ? N3 C31 H31 118.6 . . ? C30 C31 H31 118.6 . . ? C31 C30 C29 119.1(4) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C28 C29 C30 118.4(4) . . ? C28 C29 H29 120.8 . . ? C30 C29 H29 120.8 . . ? C29 C28 C27 119.6(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? N3 C27 C28 122.0(4) . . ? N3 C27 C3 118.5(3) . . ? C28 C27 C3 119.4(3) . . ? O3 C3 C27 108.6(3) . . ? O3 C3 C7 111.3(3) . . ? C27 C3 C7 110.3(3) . . ? O3 C3 H3 108.9 . . ? C27 C3 H3 108.9 . . ? C7 C3 H3 108.9 . . ? C3 O3 Mn2 119.8(2) . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C26 N2 C22 117.6(3) . . ? C26 N2 Mn1 124.9(2) . . ? C22 N2 Mn1 117.5(3) . . ? N2 C26 C25 124.1(4) . . ? N2 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? C26 C25 C24 117.3(4) . . ? C26 C25 H25 121.3 . . ? C24 C25 H25 121.3 . . ? C23 C24 C25 119.3(4) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C23 C22 120.1(4) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? N2 C22 C23 121.5(4) . . ? N2 C22 C2 117.5(3) . . ? C23 C22 C2 121.0(4) . . ? O2 C2 C6 110.9(4) . . ? O2 C2 C22 108.0(3) . . ? C6 C2 C22 112.7(5) . . ? O2 C2 H2 108.4 . . ? C6 C2 H2 108.4 . . ? C22 C2 H2 108.4 . . ? C2 O2 Mn1 120.2(2) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 N1 C21 117.7(3) . . ? C9 N1 Mn1 119.1(2) . . ? C21 N1 Mn1 122.5(2) . . ? N1 C21 C20 123.8(4) . . ? N1 C21 H21 118.1 . . ? C20 C21 H21 118.1 . . ? C21 C20 C19 118.2(4) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C10 C19 C20 118.3(4) . . ? C10 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? C9 C10 C19 120.5(4) . . ? C9 C10 H10 119.8 . . ? C19 C10 H10 119.8 . . ? N1 C9 C10 121.6(4) . . ? N1 C9 C1 118.5(3) . . ? C10 C9 C1 120.0(4) . . ? O1 C1 C9 109.2(3) . . ? O1 C1 C5 111.1(3) . . ? C9 C1 C5 111.9(4) . . ? O1 C1 H1 108.2 . . ? C9 C1 H1 108.2 . . ? C5 C1 H1 108.2 . . ? C1 O1 Mn1 121.6(2) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.084 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.237 _database_code_depnum_ccdc_archive 'CCDC 934232' ####################################################################### # # 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_1S _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Mn2 N12 Nb O8' _chemical_formula_weight 975.62 _chemical_absolute_configuration rmad 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.950(5) _cell_length_b 13.276(5) _cell_length_c 13.810(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 112.258(5) _cell_angle_gamma 90.000(5) _cell_volume 2197.4(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39243 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57363 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.48 _reflns_number_total 10047 _reflns_number_gt 9046 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.2576P] 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 SHELXL _refine_ls_extinction_coef 0.0008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.022(13) _refine_ls_number_reflns 10047 _refine_ls_number_parameters 537 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0749 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Nb1 Nb -0.011149(15) 0.484284(15) 0.240274(14) 0.02216(6) Uani 1 1 d . . . Mn1 Mn 0.19399(3) 0.17798(3) 0.13221(3) 0.03012(10) Uani 1 1 d . . . Mn2 Mn 0.18364(3) 0.67283(3) 0.61758(3) 0.02866(10) Uani 1 1 d . . . N18 N -0.07580(19) 0.29572(18) 0.37391(18) 0.0361(5) Uani 1 1 d . . . C12 C 0.1286(2) 0.5627(2) 0.2096(2) 0.0345(6) Uani 1 1 d . . . N13 N -0.1213(2) 0.63966(19) 0.03229(19) 0.0430(6) Uani 1 1 d . . . C11 C 0.0397(2) 0.3636(2) 0.15295(19) 0.0289(5) Uani 1 1 d . . . N11 N 0.07421(19) 0.29713(18) 0.12133(18) 0.0362(5) Uani 1 1 d . . . N16 N 0.0901(2) 0.63654(18) 0.45367(18) 0.0385(5) Uani 1 1 d . . . C17 C -0.1600(2) 0.5520(2) 0.2630(2) 0.0339(6) Uani 1 1 d . . . C18 C -0.0501(2) 0.36247(19) 0.33457(19) 0.0291(5) Uani 1 1 d . . . N15 N 0.2322(2) 0.3762(2) 0.40050(19) 0.0442(6) Uani 1 1 d . . . C13 C -0.0840(2) 0.5908(2) 0.1053(2) 0.0317(5) Uani 1 1 d . . . C16 C 0.0529(2) 0.59079(19) 0.3778(2) 0.0313(5) Uani 1 1 d . . . N12 N 0.1961(2) 0.6047(2) 0.1910(2) 0.0532(7) Uani 1 1 d . . . C15 C 0.1518(2) 0.41669(19) 0.3490(2) 0.0312(5) Uani 1 1 d . . . N14 N -0.2424(2) 0.3577(2) 0.0784(2) 0.0465(6) Uani 1 1 d . . . C14 C -0.1665(2) 0.40457(19) 0.1304(2) 0.0311(5) Uani 1 1 d . . . N17 N -0.2368(2) 0.5891(2) 0.2724(2) 0.0525(7) Uani 1 1 d . . . O3 O 0.24424(18) 0.67738(15) 0.79599(16) 0.0409(5) Uani 1 1 d . . . O1 O 0.2399(2) 0.18378(16) 0.30634(16) 0.0469(5) Uani 1 1 d . . . N4 N 0.31353(19) 0.78577(18) 0.61149(18) 0.0346(5) Uani 1 1 d . . . N2 N 0.32177(19) 0.29246(19) 0.12706(18) 0.0363(5) Uani 1 1 d . . . N3 N 0.1472(2) 0.52153(17) 0.6750(2) 0.0371(5) Uani 1 1 d . . . O4 O 0.33482(19) 0.58961(16) 0.6227(2) 0.0489(6) Uani 1 1 d . . . N1 N 0.1470(2) 0.02949(18) 0.18617(19) 0.0379(5) Uani 1 1 d . . . O2 O 0.35259(19) 0.09991(17) 0.1600(2) 0.0571(6) Uani 1 1 d . . . C3 C 0.2247(3) 0.5930(2) 0.8513(2) 0.0400(7) Uani 1 1 d . . . H3 H 0.2945 0.5761 0.9093 0.048 Uiso 1 1 calc R . . C1 C 0.2265(3) 0.0983(2) 0.3634(2) 0.0426(7) Uani 1 1 d . . . H1 H 0.3004 0.0776 0.4127 0.051 Uiso 1 1 calc R . . C22 C 0.4188(2) 0.2563(3) 0.1252(2) 0.0415(7) Uani 1 1 d . . . C32 C 0.4057(2) 0.7492(2) 0.6021(2) 0.0379(6) Uani 1 1 d . . . C27 C 0.1891(3) 0.5039(2) 0.7781(2) 0.0397(7) Uani 1 1 d . . . C23 C 0.5008(3) 0.3205(3) 0.1203(3) 0.0587(10) Uani 1 1 d . . . H23 H 0.5659 0.2941 0.1171 0.070 Uiso 1 1 calc R . . C21 C 0.1035(3) -0.0482(2) 0.1197(3) 0.0491(8) Uani 1 1 d . . . H21 H 0.0820 -0.0367 0.0483 0.059 Uiso 1 1 calc R . . C4 C 0.4104(3) 0.6389(2) 0.5843(3) 0.0503(8) Uani 1 1 d . . . H4 H 0.4863 0.6141 0.6223 0.060 Uiso 1 1 calc R . . C31 C 0.1087(3) 0.4425(2) 0.6104(3) 0.0500(8) Uani 1 1 d . . . H31 H 0.0802 0.4542 0.5387 0.060 Uiso 1 1 calc R . . C7 C 0.1361(3) 0.6171(3) 0.8955(3) 0.0595(9) Uani 1 1 d . . . H7A H 0.1590 0.6746 0.9407 0.089 Uiso 1 1 calc R . . H7B H 0.1269 0.5603 0.9345 0.089 Uiso 1 1 calc R . . H7C H 0.0666 0.6314 0.8391 0.089 Uiso 1 1 calc R . . C20 C 0.0895(4) -0.1429(3) 0.1520(3) 0.0608(9) Uani 1 1 d . . . H20 H 0.0596 -0.1945 0.1039 0.073 Uiso 1 1 calc R . . C25 C 0.3872(3) 0.4600(3) 0.1221(3) 0.0614(10) Uani 1 1 d . . . H25 H 0.3747 0.5290 0.1218 0.074 Uiso 1 1 calc R . . C35 C 0.3886(3) 0.9516(3) 0.6243(3) 0.0593(9) Uani 1 1 d . . . H35 H 0.3801 1.0206 0.6305 0.071 Uiso 1 1 calc R . . C30 C 0.1091(4) 0.3463(2) 0.6444(3) 0.0616(10) Uani 1 1 d . . . H30 H 0.0797 0.2939 0.5972 0.074 Uiso 1 1 calc R . . C2 C 0.4336(3) 0.1443(3) 0.1267(3) 0.0530(8) Uani 1 1 d . . . H2 H 0.5079 0.1279 0.1780 0.064 Uiso 1 1 calc R . . C24 C 0.4866(3) 0.4225(4) 0.1203(3) 0.0684(11) Uani 1 1 d . . . H24 H 0.5424 0.4659 0.1190 0.082 Uiso 1 1 calc R . . C19 C 0.1210(4) -0.1597(3) 0.2577(3) 0.0690(12) Uani 1 1 d . . . H19 H 0.1123 -0.2230 0.2824 0.083 Uiso 1 1 calc R . . C26 C 0.3080(3) 0.3924(2) 0.1244(3) 0.0460(7) Uani 1 1 d . . . H26 H 0.2408 0.4176 0.1240 0.055 Uiso 1 1 calc R . . C10 C 0.1655(4) -0.0816(3) 0.3259(3) 0.0639(10) Uani 1 1 d . . . H10 H 0.1879 -0.0920 0.3976 0.077 Uiso 1 1 calc R . . C28 C 0.1940(4) 0.4073(3) 0.8184(3) 0.0634(11) Uani 1 1 d . . . H28 H 0.2239 0.3967 0.8903 0.076 Uiso 1 1 calc R . . C36 C 0.3062(3) 0.8853(2) 0.6218(2) 0.0419(7) Uani 1 1 d . . . H36 H 0.2419 0.9111 0.6275 0.050 Uiso 1 1 calc R . . C34 C 0.4853(3) 0.9126(3) 0.6173(4) 0.0674(11) Uani 1 1 d . . . H34 H 0.5436 0.9551 0.6203 0.081 Uiso 1 1 calc R . . C5 C 0.1553(4) 0.1249(3) 0.4256(3) 0.0658(11) Uani 1 1 d . . . H5B H 0.1925 0.1754 0.4766 0.099 Uiso 1 1 calc R . . H5C H 0.1441 0.0658 0.4605 0.099 Uiso 1 1 calc R . . H5A H 0.0845 0.1501 0.3791 0.099 Uiso 1 1 calc R . . C29 C 0.1544(4) 0.3282(3) 0.7514(4) 0.0739(13) Uani 1 1 d . . . H29 H 0.1578 0.2630 0.7770 0.089 Uiso 1 1 calc R . . C9 C 0.1769(3) 0.0124(2) 0.2883(2) 0.0417(7) Uani 1 1 d . . . C6 C 0.4236(4) 0.1032(5) 0.0222(4) 0.109(2) Uani 1 1 d . . . H6A H 0.4304 0.0311 0.0263 0.164 Uiso 1 1 calc R . . H6B H 0.4819 0.1308 0.0032 0.164 Uiso 1 1 calc R . . H6C H 0.3524 0.1213 -0.0296 0.164 Uiso 1 1 calc R . . C33 C 0.4936(3) 0.8105(3) 0.6059(3) 0.0575(9) Uani 1 1 d . . . H33 H 0.5573 0.7829 0.6009 0.069 Uiso 1 1 calc R . . C8 C 0.3762(4) 0.6193(4) 0.4666(4) 0.0868(15) Uani 1 1 d . . . H8A H 0.3715 0.5481 0.4538 0.130 Uiso 1 1 calc R . . H8B H 0.4310 0.6481 0.4434 0.130 Uiso 1 1 calc R . . H8C H 0.3049 0.6497 0.4290 0.130 Uiso 1 1 calc R . . O5 O 0.3754(2) 0.39188(19) 0.6126(2) 0.0644(7) Uani 1 1 d . . . O7 O 0.3462(2) 0.7405(3) 0.1353(3) 0.0890(10) Uani 1 1 d . . . O8 O 0.4002(3) -0.0761(2) 0.2534(3) 0.1186(14) Uani 1 1 d . . . O6 O 0.4127(3) 0.2217(3) 0.7287(4) 0.1248(16) 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 Nb1 0.02719(10) 0.01687(9) 0.02399(10) -0.00006(16) 0.01147(7) 0.00011(17) Mn1 0.0318(2) 0.0264(2) 0.0316(2) -0.00567(19) 0.01144(16) 0.00194(17) Mn2 0.0310(2) 0.0233(2) 0.0331(2) -0.00608(19) 0.01376(16) -0.00116(16) N18 0.0362(12) 0.0318(12) 0.0401(12) 0.0098(10) 0.0142(10) -0.0019(10) C12 0.0385(15) 0.0287(13) 0.0407(15) -0.0028(11) 0.0201(12) -0.0058(11) N13 0.0454(14) 0.0405(13) 0.0392(13) 0.0104(11) 0.0116(11) -0.0042(11) C11 0.0269(12) 0.0295(13) 0.0286(12) -0.0034(10) 0.0087(10) -0.0008(10) N11 0.0367(12) 0.0341(12) 0.0371(12) -0.0096(10) 0.0131(10) 0.0045(10) N16 0.0433(13) 0.0358(13) 0.0350(12) -0.0102(10) 0.0133(10) 0.0022(10) C17 0.0400(15) 0.0242(13) 0.0443(15) 0.0021(11) 0.0234(13) 0.0029(11) C18 0.0295(12) 0.0262(12) 0.0322(12) 0.0060(10) 0.0124(10) 0.0029(10) N15 0.0367(13) 0.0428(14) 0.0428(13) -0.0065(12) 0.0034(11) 0.0051(11) C13 0.0368(14) 0.0297(13) 0.0304(13) 0.0052(10) 0.0146(11) -0.0018(11) C16 0.0339(13) 0.0268(13) 0.0343(13) -0.0032(10) 0.0141(11) 0.0029(10) N12 0.0512(16) 0.0507(16) 0.0667(18) -0.0015(14) 0.0323(15) -0.0119(13) C15 0.0341(13) 0.0267(12) 0.0313(13) -0.0048(10) 0.0106(11) -0.0012(10) N14 0.0367(13) 0.0411(14) 0.0526(15) 0.0023(12) 0.0067(11) -0.0054(11) C14 0.0329(13) 0.0251(13) 0.0346(13) 0.0038(10) 0.0118(11) 0.0010(10) N17 0.0523(16) 0.0424(15) 0.076(2) 0.0035(14) 0.0391(15) 0.0106(12) O3 0.0540(12) 0.0305(10) 0.0386(11) -0.0049(8) 0.0180(9) -0.0056(9) O1 0.0699(14) 0.0326(11) 0.0377(11) -0.0042(9) 0.0200(10) -0.0025(10) N4 0.0355(12) 0.0318(12) 0.0379(12) -0.0023(10) 0.0153(10) -0.0036(10) N2 0.0331(11) 0.0401(13) 0.0362(12) 0.0003(10) 0.0136(10) 0.0025(10) N3 0.0444(13) 0.0272(11) 0.0441(13) -0.0051(10) 0.0219(11) -0.0043(9) O4 0.0440(13) 0.0359(12) 0.0752(16) 0.0046(11) 0.0321(12) 0.0057(9) N1 0.0465(14) 0.0282(11) 0.0390(13) -0.0002(10) 0.0162(11) 0.0027(10) O2 0.0408(12) 0.0438(13) 0.0858(18) 0.0046(12) 0.0229(12) 0.0119(10) C3 0.0444(16) 0.0351(16) 0.0374(15) -0.0006(12) 0.0120(13) -0.0040(13) C1 0.0529(18) 0.0349(15) 0.0369(15) 0.0025(12) 0.0136(13) 0.0058(13) C22 0.0317(14) 0.061(2) 0.0321(14) -0.0002(13) 0.0124(12) 0.0044(13) C32 0.0320(13) 0.0417(16) 0.0409(15) 0.0006(12) 0.0148(12) -0.0025(12) C27 0.0472(15) 0.0293(17) 0.0422(14) 0.0023(11) 0.0164(12) 0.0044(11) C23 0.0402(17) 0.086(3) 0.059(2) 0.0161(19) 0.0287(16) 0.0029(17) C21 0.067(2) 0.0353(16) 0.0459(17) -0.0066(13) 0.0225(16) -0.0052(14) C4 0.0389(16) 0.0433(18) 0.077(2) -0.0028(16) 0.0316(16) 0.0044(13) C31 0.065(2) 0.0365(15) 0.0517(19) -0.0109(14) 0.0255(17) -0.0104(15) C7 0.078(3) 0.054(2) 0.060(2) -0.0139(17) 0.041(2) -0.0136(18) C20 0.087(3) 0.0358(18) 0.061(2) -0.0058(16) 0.029(2) -0.0109(18) C25 0.060(2) 0.050(2) 0.073(2) 0.0181(17) 0.0243(18) -0.0068(16) C35 0.077(2) 0.0360(17) 0.076(3) -0.0041(16) 0.041(2) -0.0153(16) C30 0.098(3) 0.0297(16) 0.068(2) -0.0153(15) 0.044(2) -0.0160(17) C2 0.0327(15) 0.061(2) 0.063(2) -0.0099(17) 0.0157(14) 0.0113(14) C24 0.050(2) 0.088(3) 0.070(3) 0.028(2) 0.0258(19) -0.014(2) C19 0.109(3) 0.0308(18) 0.073(3) 0.0041(17) 0.040(2) -0.0086(19) C26 0.0472(17) 0.0387(17) 0.0542(18) 0.0071(14) 0.0215(15) 0.0006(13) C10 0.099(3) 0.0401(19) 0.050(2) 0.0074(15) 0.026(2) 0.0045(19) C28 0.097(3) 0.0328(17) 0.056(2) 0.0070(16) 0.025(2) 0.0063(18) C36 0.0489(17) 0.0319(15) 0.0501(17) -0.0029(13) 0.0246(14) -0.0031(13) C34 0.065(2) 0.058(2) 0.095(3) -0.001(2) 0.048(2) -0.0243(19) C5 0.099(3) 0.053(2) 0.063(2) -0.0077(18) 0.050(2) 0.001(2) C29 0.120(4) 0.0263(17) 0.088(3) 0.0044(18) 0.054(3) -0.002(2) C9 0.0508(17) 0.0343(16) 0.0375(15) 0.0003(11) 0.0137(13) 0.0081(12) C6 0.084(3) 0.145(5) 0.112(4) -0.070(4) 0.053(3) -0.005(3) C33 0.0489(19) 0.060(2) 0.076(2) -0.0013(18) 0.0371(18) -0.0080(16) C8 0.111(4) 0.078(3) 0.106(4) -0.037(3) 0.079(3) -0.019(3) O5 0.0575(15) 0.0523(15) 0.0630(16) 0.0005(12) -0.0004(12) 0.0000(12) O7 0.0587(17) 0.091(2) 0.105(3) 0.008(2) 0.0182(17) -0.0170(16) O8 0.071(2) 0.0665(19) 0.179(4) 0.016(2) 0.003(2) 0.0166(16) O6 0.068(2) 0.107(3) 0.178(4) 0.065(3) 0.022(2) -0.0176(19) _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 Nb1 C13 2.243(3) . ? Nb1 C11 2.249(3) . ? Nb1 C18 2.250(3) . ? Nb1 C17 2.254(3) . ? Nb1 C16 2.258(3) . ? Nb1 C15 2.261(3) . ? Nb1 C12 2.262(3) . ? Nb1 C14 2.270(3) . ? Mn1 N13 2.165(3) 2_545 ? Mn1 N11 2.180(2) . ? Mn1 O2 2.201(2) . ? Mn1 O1 2.249(2) . ? Mn1 N2 2.268(3) . ? Mn1 N1 2.271(3) . ? Mn2 N16 2.179(2) . ? Mn2 N18 2.179(2) 2_556 ? Mn2 O4 2.226(2) . ? Mn2 N3 2.274(2) . ? Mn2 N4 2.279(2) . ? Mn2 O3 2.286(2) . ? N18 C18 1.152(3) . ? N18 Mn2 2.179(2) 2_546 ? C12 N12 1.146(4) . ? N13 C13 1.141(3) . ? N13 Mn1 2.165(3) 2 ? C11 N11 1.148(3) . ? N16 C16 1.148(3) . ? C17 N17 1.161(4) . ? N15 C15 1.148(4) . ? N14 C14 1.155(4) . ? O3 C3 1.431(4) . ? O1 C1 1.430(4) . ? N4 C36 1.337(4) . ? N4 C32 1.340(4) . ? N2 C26 1.338(4) . ? N2 C22 1.354(4) . ? N3 C27 1.338(4) . ? N3 C31 1.346(4) . ? O4 C4 1.435(4) . ? N1 C9 1.333(4) . ? N1 C21 1.354(4) . ? O2 C2 1.423(4) . ? C3 C27 1.509(4) . ? C3 C7 1.523(5) . ? C3 H3 0.9800 . ? C1 C9 1.511(4) . ? C1 C5 1.520(5) . ? C1 H1 0.9800 . ? C22 C23 1.383(5) . ? C22 C2 1.498(5) . ? C32 C33 1.383(4) . ? C32 C4 1.490(4) . ? C27 C28 1.390(4) . ? C23 C24 1.366(6) . ? C23 H23 0.9300 . ? C21 C20 1.368(5) . ? C21 H21 0.9300 . ? C4 C8 1.537(6) . ? C4 H4 0.9800 . ? C31 C30 1.360(5) . ? C31 H31 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C20 C19 1.377(6) . ? C20 H20 0.9300 . ? C25 C26 1.373(5) . ? C25 C24 1.389(6) . ? C25 H25 0.9300 . ? C35 C36 1.374(5) . ? C35 C34 1.392(6) . ? C35 H35 0.9300 . ? C30 C29 1.388(6) . ? C30 H30 0.9300 . ? C2 C6 1.502(6) . ? C2 H2 0.9800 . ? C24 H24 0.9300 . ? C19 C10 1.373(5) . ? C19 H19 0.9300 . ? C26 H26 0.9300 . ? C10 C9 1.381(5) . ? C10 H10 0.9300 . ? C28 C29 1.366(5) . ? C28 H28 0.9300 . ? C36 H36 0.9300 . ? C34 C33 1.374(5) . ? C34 H34 0.9300 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C5 H5A 0.9600 . ? C29 H29 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C33 H33 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 C13 Nb1 C11 96.89(10) . . ? C13 Nb1 C18 144.89(9) . . ? C11 Nb1 C18 88.50(11) . . ? C13 Nb1 C17 75.63(10) . . ? C11 Nb1 C17 142.99(10) . . ? C18 Nb1 C17 79.32(10) . . ? C13 Nb1 C16 102.05(11) . . ? C11 Nb1 C16 143.90(9) . . ? C18 Nb1 C16 93.15(10) . . ? C17 Nb1 C16 72.21(10) . . ? C13 Nb1 C15 142.67(10) . . ? C11 Nb1 C15 71.60(9) . . ? C18 Nb1 C15 71.80(9) . . ? C17 Nb1 C15 134.23(10) . . ? C16 Nb1 C15 74.73(9) . . ? C13 Nb1 C12 70.66(10) . . ? C11 Nb1 C12 79.03(10) . . ? C18 Nb1 C12 144.06(10) . . ? C17 Nb1 C12 129.03(11) . . ? C16 Nb1 C12 78.71(10) . . ? C15 Nb1 C12 72.29(10) . . ? C13 Nb1 C14 75.61(10) . . ? C11 Nb1 C14 71.03(9) . . ? C18 Nb1 C14 73.47(10) . . ? C17 Nb1 C14 72.00(10) . . ? C16 Nb1 C14 143.51(10) . . ? C15 Nb1 C14 128.78(10) . . ? C12 Nb1 C14 131.17(10) . . ? N13 Mn1 N11 94.75(9) 2_545 . ? N13 Mn1 O2 94.53(10) 2_545 . ? N11 Mn1 O2 161.13(9) . . ? N13 Mn1 O1 164.54(9) 2_545 . ? N11 Mn1 O1 86.67(8) . . ? O2 Mn1 O1 88.74(10) . . ? N13 Mn1 N2 99.05(9) 2_545 . ? N11 Mn1 N2 91.15(10) . . ? O2 Mn1 N2 71.17(9) . . ? O1 Mn1 N2 96.31(8) . . ? N13 Mn1 N1 94.37(10) 2_545 . ? N11 Mn1 N1 112.36(9) . . ? O2 Mn1 N1 83.24(9) . . ? O1 Mn1 N1 70.98(8) . . ? N2 Mn1 N1 151.85(9) . . ? N16 Mn2 N18 96.10(9) . 2_556 ? N16 Mn2 O4 93.40(10) . . ? N18 Mn2 O4 160.69(9) 2_556 . ? N16 Mn2 N3 93.45(10) . . ? N18 Mn2 N3 114.88(9) 2_556 . ? O4 Mn2 N3 81.17(9) . . ? N16 Mn2 N4 103.57(9) . . ? N18 Mn2 N4 90.37(9) 2_556 . ? O4 Mn2 N4 71.04(9) . . ? N3 Mn2 N4 147.97(9) . . ? N16 Mn2 O3 162.67(9) . . ? N18 Mn2 O3 83.54(8) 2_556 . ? O4 Mn2 O3 92.29(9) . . ? N3 Mn2 O3 71.28(8) . . ? N4 Mn2 O3 93.76(8) . . ? C18 N18 Mn2 155.0(2) . 2_546 ? N12 C12 Nb1 177.2(3) . . ? C13 N13 Mn1 158.7(2) . 2 ? N11 C11 Nb1 170.9(2) . . ? C11 N11 Mn1 154.3(2) . . ? C16 N16 Mn2 160.4(2) . . ? N17 C17 Nb1 177.9(3) . . ? N18 C18 Nb1 173.5(2) . . ? N13 C13 Nb1 175.4(2) . . ? N16 C16 Nb1 173.1(2) . . ? N15 C15 Nb1 175.2(2) . . ? N14 C14 Nb1 175.1(2) . . ? C3 O3 Mn2 119.77(16) . . ? C1 O1 Mn1 121.61(17) . . ? C36 N4 C32 118.0(3) . . ? C36 N4 Mn2 124.31(19) . . ? C32 N4 Mn2 117.56(19) . . ? C26 N2 C22 117.8(3) . . ? C26 N2 Mn1 125.1(2) . . ? C22 N2 Mn1 117.1(2) . . ? C27 N3 C31 117.9(3) . . ? C27 N3 Mn2 118.12(19) . . ? C31 N3 Mn2 122.1(2) . . ? C4 O4 Mn2 118.46(18) . . ? C9 N1 C21 117.9(3) . . ? C9 N1 Mn1 119.2(2) . . ? C21 N1 Mn1 122.2(2) . . ? C2 O2 Mn1 120.11(19) . . ? O3 C3 C27 109.1(2) . . ? O3 C3 C7 111.2(3) . . ? C27 C3 C7 110.3(3) . . ? O3 C3 H3 108.7 . . ? C27 C3 H3 108.7 . . ? C7 C3 H3 108.7 . . ? O1 C1 C9 109.2(2) . . ? O1 C1 C5 110.7(3) . . ? C9 C1 C5 111.8(3) . . ? O1 C1 H1 108.3 . . ? C9 C1 H1 108.3 . . ? C5 C1 H1 108.3 . . ? N2 C22 C23 121.2(3) . . ? N2 C22 C2 117.8(3) . . ? C23 C22 C2 121.1(3) . . ? N4 C32 C33 122.2(3) . . ? N4 C32 C4 117.7(3) . . ? C33 C32 C4 120.1(3) . . ? N3 C27 C28 121.7(3) . . ? N3 C27 C3 118.2(2) . . ? C28 C27 C3 120.0(3) . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? N1 C21 C20 123.5(3) . . ? N1 C21 H21 118.3 . . ? C20 C21 H21 118.3 . . ? O4 C4 C32 108.2(2) . . ? O4 C4 C8 110.6(3) . . ? C32 C4 C8 109.1(3) . . ? O4 C4 H4 109.7 . . ? C32 C4 H4 109.7 . . ? C8 C4 H4 109.7 . . ? N3 C31 C30 123.5(3) . . ? N3 C31 H31 118.3 . . ? C30 C31 H31 118.3 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C21 C20 C19 118.1(4) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C26 C25 C24 118.1(4) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? C36 C35 C34 118.1(3) . . ? C36 C35 H35 120.9 . . ? C34 C35 H35 120.9 . . ? C31 C30 C29 118.4(3) . . ? C31 C30 H30 120.8 . . ? C29 C30 H30 120.8 . . ? O2 C2 C22 108.1(2) . . ? O2 C2 C6 110.8(3) . . ? C22 C2 C6 112.6(4) . . ? O2 C2 H2 108.5 . . ? C22 C2 H2 108.5 . . ? C6 C2 H2 108.5 . . ? C23 C24 C25 118.7(3) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C10 C19 C20 119.0(3) . . ? C10 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? N2 C26 C25 123.8(3) . . ? N2 C26 H26 118.1 . . ? C25 C26 H26 118.1 . . ? C19 C10 C9 120.1(3) . . ? C19 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C29 C28 C27 119.4(4) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? N4 C36 C35 123.4(3) . . ? N4 C36 H36 118.3 . . ? C35 C36 H36 118.3 . . ? C33 C34 C35 119.0(3) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C1 C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? C28 C29 C30 119.1(3) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? N1 C9 C10 121.5(3) . . ? N1 C9 C1 118.4(3) . . ? C10 C9 C1 120.1(3) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C34 C33 C32 119.1(3) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N16 Mn2 O3 C3 25.4(4) . . . . ? N18 Mn2 O3 C3 115.2(2) 2_556 . . . ? O4 Mn2 O3 C3 -83.8(2) . . . . ? N3 Mn2 O3 C3 -3.9(2) . . . . ? N4 Mn2 O3 C3 -154.9(2) . . . . ? N13 Mn1 O1 C1 23.3(5) 2_545 . . . ? N11 Mn1 O1 C1 119.0(2) . . . . ? O2 Mn1 O1 C1 -79.3(2) . . . . ? N2 Mn1 O1 C1 -150.2(2) . . . . ? N1 Mn1 O1 C1 4.0(2) . . . . ? N16 Mn2 N4 C36 101.7(2) . . . . ? N18 Mn2 N4 C36 5.3(2) 2_556 . . . ? O4 Mn2 N4 C36 -169.4(3) . . . . ? N3 Mn2 N4 C36 -138.1(2) . . . . ? O3 Mn2 N4 C36 -78.2(2) . . . . ? N16 Mn2 N4 C32 -81.7(2) . . . . ? N18 Mn2 N4 C32 -178.1(2) 2_556 . . . ? O4 Mn2 N4 C32 7.2(2) . . . . ? N3 Mn2 N4 C32 38.4(3) . . . . ? O3 Mn2 N4 C32 98.4(2) . . . . ? N13 Mn1 N2 C26 98.1(2) 2_545 . . . ? N11 Mn1 N2 C26 3.1(2) . . . . ? O2 Mn1 N2 C26 -170.2(3) . . . . ? O1 Mn1 N2 C26 -83.7(2) . . . . ? N1 Mn1 N2 C26 -144.5(2) . . . . ? N13 Mn1 N2 C22 -81.0(2) 2_545 . . . ? N11 Mn1 N2 C22 -176.0(2) . . . . ? O2 Mn1 N2 C22 10.7(2) . . . . ? O1 Mn1 N2 C22 97.2(2) . . . . ? N1 Mn1 N2 C22 36.4(3) . . . . ? N16 Mn2 N3 C27 179.9(2) . . . . ? N18 Mn2 N3 C27 -81.7(2) 2_556 . . . ? O4 Mn2 N3 C27 87.0(2) . . . . ? N4 Mn2 N3 C27 57.3(3) . . . . ? O3 Mn2 N3 C27 -8.4(2) . . . . ? N16 Mn2 N3 C31 15.6(3) . . . . ? N18 Mn2 N3 C31 113.9(3) 2_556 . . . ? O4 Mn2 N3 C31 -77.3(3) . . . . ? N4 Mn2 N3 C31 -107.1(3) . . . . ? O3 Mn2 N3 C31 -172.8(3) . . . . ? N16 Mn2 O4 C4 81.9(2) . . . . ? N18 Mn2 O4 C4 -37.5(4) 2_556 . . . ? N3 Mn2 O4 C4 174.9(2) . . . . ? N4 Mn2 O4 C4 -21.2(2) . . . . ? O3 Mn2 O4 C4 -114.4(2) . . . . ? N13 Mn1 N1 C9 178.4(2) 2_545 . . . ? N11 Mn1 N1 C9 -84.7(2) . . . . ? O2 Mn1 N1 C9 84.3(2) . . . . ? O1 Mn1 N1 C9 -6.7(2) . . . . ? N2 Mn1 N1 C9 59.9(3) . . . . ? N13 Mn1 N1 C21 7.9(3) 2_545 . . . ? N11 Mn1 N1 C21 104.9(2) . . . . ? O2 Mn1 N1 C21 -86.1(3) . . . . ? O1 Mn1 N1 C21 -177.1(3) . . . . ? N2 Mn1 N1 C21 -110.6(3) . . . . ? N13 Mn1 O2 C2 76.5(2) 2_545 . . . ? N11 Mn1 O2 C2 -42.7(4) . . . . ? O1 Mn1 O2 C2 -118.6(2) . . . . ? N2 Mn1 O2 C2 -21.5(2) . . . . ? N1 Mn1 O2 C2 170.4(2) . . . . ? Mn2 O3 C3 C27 13.5(3) . . . . ? Mn2 O3 C3 C7 -108.3(2) . . . . ? Mn1 O1 C1 C9 -1.3(3) . . . . ? Mn1 O1 C1 C5 -124.9(3) . . . . ? C26 N2 C22 C23 -0.2(4) . . . . ? Mn1 N2 C22 C23 179.0(2) . . . . ? C26 N2 C22 C2 -179.2(3) . . . . ? Mn1 N2 C22 C2 0.0(3) . . . . ? C36 N4 C32 C33 2.0(4) . . . . ? Mn2 N4 C32 C33 -174.8(3) . . . . ? C36 N4 C32 C4 -176.4(3) . . . . ? Mn2 N4 C32 C4 6.8(4) . . . . ? C31 N3 C27 C28 0.5(5) . . . . ? Mn2 N3 C27 C28 -164.5(3) . . . . ? C31 N3 C27 C3 -175.6(3) . . . . ? Mn2 N3 C27 C3 19.4(4) . . . . ? O3 C3 C27 N3 -21.1(4) . . . . ? C7 C3 C27 N3 101.4(3) . . . . ? O3 C3 C27 C28 162.8(3) . . . . ? C7 C3 C27 C28 -74.8(4) . . . . ? N2 C22 C23 C24 1.8(5) . . . . ? C2 C22 C23 C24 -179.2(4) . . . . ? C9 N1 C21 C20 -0.4(5) . . . . ? Mn1 N1 C21 C20 170.2(3) . . . . ? Mn2 O4 C4 C32 30.3(3) . . . . ? Mn2 O4 C4 C8 -89.0(3) . . . . ? N4 C32 C4 O4 -23.3(4) . . . . ? C33 C32 C4 O4 158.2(3) . . . . ? N4 C32 C4 C8 97.0(3) . . . . ? C33 C32 C4 C8 -81.5(4) . . . . ? C27 N3 C31 C30 0.7(5) . . . . ? Mn2 N3 C31 C30 165.1(3) . . . . ? N1 C21 C20 C19 0.3(6) . . . . ? N3 C31 C30 C29 -1.8(6) . . . . ? Mn1 O2 C2 C22 27.2(3) . . . . ? Mn1 O2 C2 C6 -96.5(4) . . . . ? N2 C22 C2 O2 -16.6(4) . . . . ? C23 C22 C2 O2 164.5(3) . . . . ? N2 C22 C2 C6 106.1(4) . . . . ? C23 C22 C2 C6 -72.9(4) . . . . ? C22 C23 C24 C25 -1.8(6) . . . . ? C26 C25 C24 C23 0.3(6) . . . . ? C21 C20 C19 C10 -0.4(7) . . . . ? C22 N2 C26 C25 -1.4(5) . . . . ? Mn1 N2 C26 C25 179.5(3) . . . . ? C24 C25 C26 N2 1.4(6) . . . . ? C20 C19 C10 C9 0.7(7) . . . . ? N3 C27 C28 C29 -0.5(6) . . . . ? C3 C27 C28 C29 175.6(4) . . . . ? C32 N4 C36 C35 -0.7(5) . . . . ? Mn2 N4 C36 C35 175.8(3) . . . . ? C34 C35 C36 N4 -1.0(6) . . . . ? C36 C35 C34 C33 1.4(6) . . . . ? C27 C28 C29 C30 -0.7(7) . . . . ? C31 C30 C29 C28 1.8(7) . . . . ? C21 N1 C9 C10 0.7(5) . . . . ? Mn1 N1 C9 C10 -170.1(3) . . . . ? C21 N1 C9 C1 179.5(3) . . . . ? Mn1 N1 C9 C1 8.6(4) . . . . ? C19 C10 C9 N1 -0.9(6) . . . . ? C19 C10 C9 C1 -179.6(4) . . . . ? O1 C1 C9 N1 -4.7(4) . . . . ? C5 C1 C9 N1 118.2(3) . . . . ? O1 C1 C9 C10 174.1(3) . . . . ? C5 C1 C9 C10 -63.1(4) . . . . ? C35 C34 C33 C32 -0.2(7) . . . . ? N4 C32 C33 C34 -1.5(6) . . . . ? C4 C32 C33 C34 176.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.663 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 934233'