# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 Mn2 N2 O11' _chemical_formula_weight 728.46 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' Mn Mn 0.3368 0.7283 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6283(13) _cell_length_b 14.9622(17) _cell_length_c 18.9869(16) _cell_angle_alpha 90.00 _cell_angle_beta 123.236(5) _cell_angle_gamma 90.00 _cell_volume 3000.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7784 _exptl_absorpt_correction_T_max 0.8113 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16519 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.56 _reflns_number_total 6157 _reflns_number_gt 3703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6157 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1039 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.2031 _refine_ls_wR_factor_gt 0.1682 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.002 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 C1 C 0.1272(4) 0.6100(3) 0.9242(3) 0.0265(11) Uani 1 1 d . . . C2 C 0.2035(4) 0.6086(3) 0.8851(3) 0.0267(11) Uani 1 1 d . . . C3 C 0.3100(5) 0.5544(4) 0.9161(3) 0.0389(13) Uani 1 1 d . . . H3 H 0.3336 0.5151 0.9603 0.047 Uiso 1 1 calc R . . C4 C 0.3800(5) 0.5596(4) 0.8804(3) 0.0383(13) Uani 1 1 d . . . H4 H 0.4534 0.5258 0.9025 0.046 Uiso 1 1 calc R . . C5 C 0.3418(4) 0.6149(3) 0.8118(3) 0.0172(9) Uani 1 1 d . . . C6 C 0.2368(5) 0.6654(3) 0.7796(3) 0.0333(12) Uani 1 1 d . . . H6 H 0.2109 0.7015 0.7330 0.040 Uiso 1 1 calc R . . C7 C 0.1682(5) 0.6633(3) 0.8161(3) 0.0356(12) Uani 1 1 d . . . H7 H 0.0966 0.6991 0.7942 0.043 Uiso 1 1 calc R . . C8 C 0.4238(4) 0.6201(3) 0.7752(3) 0.0197(9) Uani 1 1 d . . . C9 C 0.5570(4) 0.6204(3) 0.8292(3) 0.0224(10) Uani 1 1 d . . . H9 H 0.5930 0.6150 0.8868 0.027 Uiso 1 1 calc R . . C10 C 0.6368(4) 0.6282(3) 0.8008(3) 0.0184(9) Uani 1 1 d . . . C11 C 0.7760(4) 0.6335(3) 0.8666(3) 0.0218(10) Uani 1 1 d . . . C12 C 0.5854(4) 0.6362(3) 0.7142(3) 0.0197(9) Uani 1 1 d . . . C13 C 0.4519(4) 0.6346(3) 0.6597(3) 0.0222(10) Uani 1 1 d . . . H13 H 0.4162 0.6390 0.6021 0.027 Uiso 1 1 calc R . . C14 C 0.3717(4) 0.6267(3) 0.6878(3) 0.0195(9) Uani 1 1 d . . . C15 C 0.2316(4) 0.6223(3) 0.6214(3) 0.0207(9) Uani 1 1 d . . . C16 C 0.6654(4) 0.6426(3) 0.6762(3) 0.0197(9) Uani 1 1 d . . . C17 C 0.7701(5) 0.5914(3) 0.7078(3) 0.0302(11) Uani 1 1 d . . . H17 H 0.7963 0.5550 0.7543 0.036 Uiso 1 1 calc R . . C18 C 0.8382(5) 0.5937(3) 0.6705(3) 0.0320(12) Uani 1 1 d . . . H18 H 0.9091 0.5573 0.6913 0.038 Uiso 1 1 calc R . . C19 C 0.8025(4) 0.6494(3) 0.6023(3) 0.0258(11) Uani 1 1 d . . . C20 C 0.6972(5) 0.7043(3) 0.5724(3) 0.0339(12) Uani 1 1 d . . . H20 H 0.6740 0.7441 0.5286 0.041 Uiso 1 1 calc R . . C21 C 0.6269(5) 0.6990(3) 0.6088(3) 0.0332(12) Uani 1 1 d . . . H21 H 0.5543 0.7334 0.5877 0.040 Uiso 1 1 calc R . . C22 C 0.8774(4) 0.6479(3) 0.5621(3) 0.0276(11) Uani 1 1 d . . . C23 C 0.0316(7) 0.8811(4) 0.7521(4) 0.0547(18) Uani 1 1 d . . . H23A H 0.0686 0.8311 0.7404 0.066 Uiso 1 1 calc R . . H23B H 0.0563 0.9362 0.7379 0.066 Uiso 1 1 calc R . . C24 C -0.1071(8) 0.8730(5) 0.7044(5) 0.082(3) Uani 1 1 d . . . H24A H -0.1335 0.8149 0.6774 0.098 Uiso 1 1 calc R . . H24B H -0.1465 0.9188 0.6613 0.098 Uiso 1 1 calc R . . C25 C -0.1450(6) 0.8839(4) 0.7664(3) 0.0545(17) Uani 1 1 d . . . H25A H -0.1889 0.9401 0.7575 0.065 Uiso 1 1 calc R . . H25B H -0.1999 0.8354 0.7612 0.065 Uiso 1 1 calc R . . C26 C -0.0243(5) 0.8822(3) 0.8504(3) 0.0305(11) Uani 1 1 d . . . C27 C 0.2048(6) 0.8795(4) 0.9109(4) 0.0579(18) Uani 1 1 d . . . H27A H 0.2241 0.9328 0.9439 0.087 Uiso 1 1 calc R . . H27B H 0.2578 0.8763 0.8893 0.087 Uiso 1 1 calc R . . H27C H 0.2197 0.8282 0.9456 0.087 Uiso 1 1 calc R . . C28 C 0.5720(7) 0.8784(4) 0.7748(7) 0.082(3) Uani 1 1 d . . . H28A H 0.6101 0.8278 0.7649 0.098 Uiso 1 1 calc R . . H28B H 0.6073 0.9329 0.7681 0.098 Uiso 1 1 calc R . . C29 C 0.5959(11) 0.8740(6) 0.8560(9) 0.134(5) Uani 1 1 d . . . H29A H 0.6545 0.9211 0.8904 0.161 Uiso 1 1 calc R . . H29B H 0.6354 0.8171 0.8814 0.161 Uiso 1 1 calc R . . C30 C 0.4752(6) 0.8837(5) 0.8546(7) 0.131(5) Uani 1 1 d . . . H30A H 0.4722 0.9400 0.8789 0.157 Uiso 1 1 calc R . . H30B H 0.4634 0.8345 0.8829 0.157 Uiso 1 1 calc R . . C31 C 0.3713(7) 0.8807(4) 0.7506(6) 0.065(2) Uani 1 1 d . . . C32 C 0.3727(8) 0.8789(5) 0.6352(5) 0.066(2) Uani 1 1 d . . . H32A H 0.3279 0.8236 0.6127 0.099 Uiso 1 1 calc R . . H32B H 0.4315 0.8869 0.6187 0.099 Uiso 1 1 calc R . . H32C H 0.3134 0.9276 0.6140 0.099 Uiso 1 1 calc R . . Mn1 Mn 0.00429(6) 0.75184(4) 0.98574(4) 0.0207(2) Uani 1 1 d . . . Mn2 Mn 0.0000 0.5000 0.5000 0.0188(2) Uani 1 2 d S . . Mn3 Mn 0.0000 0.5000 1.0000 0.0205(3) Uani 1 2 d S . . N1 N 0.0718(4) 0.8812(3) 0.8408(3) 0.0403(11) Uani 1 1 d . . . N2 N 0.4321(9) 0.8772(4) 0.7146(8) 0.113(3) Uani 1 1 d . . . O1 O 0.1015(3) 0.5376(2) 0.9435(2) 0.0395(9) Uani 1 1 d . . . O2 O 0.0981(3) 0.6861(2) 0.9363(2) 0.0401(9) Uani 1 1 d . . . O3 O 0.8274(3) 0.5645(2) 0.9085(2) 0.0394(9) Uani 1 1 d . . . O4 O 0.8285(3) 0.7074(2) 0.8759(2) 0.0359(8) Uani 1 1 d . . . O5 O 0.1821(3) 0.5462(2) 0.6030(2) 0.0310(8) Uani 1 1 d . . . O6 O 0.1788(3) 0.6952(2) 0.5880(2) 0.0327(8) Uani 1 1 d . . . O7 O 0.9146(3) 0.5735(2) 0.5541(2) 0.0409(9) Uani 1 1 d . . . O8 O 0.8959(3) 0.7219(2) 0.5387(2) 0.0404(9) Uani 1 1 d . . . O9 O -0.0125(3) 0.88171(18) 0.9216(2) 0.0290(8) Uani 1 1 d . . . O10 O 0.0511(3) 0.62674(18) 1.07604(19) 0.0273(7) Uani 1 1 d . . . H10A H 0.1405 0.6264 1.1203 0.033 Uiso 1 1 calc R . . H10B H 0.0033 0.6308 1.1021 0.033 Uiso 1 1 calc R . . O11 O 0.2594(4) 0.8809(2) 0.7244(2) 0.0473(10) 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 C1 0.019(2) 0.040(3) 0.025(3) -0.002(2) 0.015(2) 0.000(2) C2 0.021(3) 0.034(3) 0.029(3) 0.000(2) 0.016(2) 0.003(2) C3 0.035(3) 0.058(4) 0.034(3) 0.013(3) 0.025(3) 0.011(3) C4 0.030(3) 0.055(3) 0.040(3) 0.018(3) 0.025(3) 0.017(3) C5 0.014(2) 0.023(2) 0.015(2) 0.0008(17) 0.0084(18) -0.0015(18) C6 0.038(3) 0.037(3) 0.032(3) 0.008(2) 0.024(3) 0.002(2) C7 0.032(3) 0.040(3) 0.043(3) 0.010(3) 0.026(3) 0.012(2) C8 0.014(2) 0.027(2) 0.017(2) -0.0024(18) 0.0082(19) -0.0029(19) C9 0.014(2) 0.029(2) 0.025(2) 0.000(2) 0.011(2) 0.0012(19) C10 0.014(2) 0.019(2) 0.024(2) -0.0024(18) 0.012(2) -0.0011(18) C11 0.014(2) 0.037(3) 0.016(2) -0.004(2) 0.0088(19) -0.003(2) C12 0.008(2) 0.028(3) 0.022(2) -0.0001(18) 0.0076(19) 0.0003(18) C13 0.012(2) 0.035(3) 0.013(2) 0.0019(19) 0.0028(19) 0.0045(19) C14 0.015(2) 0.020(2) 0.021(2) 0.0011(18) 0.0086(19) 0.0003(18) C15 0.016(2) 0.031(3) 0.014(2) 0.0003(19) 0.0075(19) 0.002(2) C16 0.015(2) 0.025(2) 0.016(2) -0.0004(17) 0.0065(19) -0.0073(18) C17 0.027(3) 0.043(3) 0.028(3) 0.003(2) 0.020(2) 0.002(2) C18 0.028(3) 0.042(3) 0.035(3) 0.005(2) 0.023(2) 0.009(2) C19 0.023(3) 0.032(3) 0.031(3) -0.004(2) 0.020(2) -0.002(2) C20 0.031(3) 0.045(3) 0.034(3) 0.009(2) 0.023(3) 0.004(2) C21 0.028(3) 0.043(3) 0.036(3) 0.006(2) 0.023(2) 0.006(2) C22 0.020(3) 0.040(3) 0.024(2) 0.000(2) 0.014(2) 0.000(2) C23 0.093(6) 0.046(4) 0.047(4) 0.001(3) 0.053(4) -0.001(4) C24 0.070(6) 0.124(7) 0.041(4) -0.005(4) 0.023(4) -0.004(5) C25 0.042(4) 0.080(5) 0.028(3) -0.004(3) 0.011(3) -0.005(3) C26 0.034(3) 0.026(3) 0.040(3) 0.001(2) 0.025(3) -0.001(2) C27 0.032(3) 0.078(5) 0.062(4) 0.009(3) 0.025(3) 0.001(3) C28 0.035(4) 0.035(4) 0.173(10) 0.014(5) 0.057(6) 0.008(3) C29 0.081(8) 0.093(8) 0.165(13) 0.003(7) 0.028(9) -0.018(6) C30 0.015(4) 0.080(6) 0.205(12) 0.013(6) 0.001(5) 0.002(4) C31 0.066(5) 0.040(4) 0.118(7) 0.000(4) 0.069(5) 0.005(3) C32 0.054(5) 0.064(5) 0.072(5) 0.002(4) 0.029(4) 0.005(4) Mn1 0.0156(4) 0.0247(4) 0.0222(4) -0.0031(3) 0.0107(3) -0.0013(3) Mn2 0.0144(5) 0.0218(5) 0.0201(5) -0.0020(4) 0.0094(4) -0.0019(4) Mn3 0.0150(5) 0.0236(5) 0.0214(5) 0.0053(4) 0.0089(4) 0.0009(4) N1 0.038(3) 0.047(3) 0.039(3) -0.001(2) 0.024(2) -0.001(2) N2 0.101(7) 0.047(4) 0.192(11) 0.019(5) 0.080(8) 0.006(4) O1 0.051(2) 0.036(2) 0.057(2) 0.0063(18) 0.046(2) 0.0019(18) O2 0.044(2) 0.042(2) 0.054(2) -0.0035(18) 0.039(2) 0.0027(18) O3 0.0175(18) 0.042(2) 0.042(2) 0.0158(18) 0.0055(17) 0.0047(16) O4 0.0204(18) 0.041(2) 0.0326(19) -0.0044(17) 0.0059(16) -0.0112(16) O5 0.0156(17) 0.030(2) 0.0318(19) 0.0005(15) 0.0031(16) -0.0048(14) O6 0.0188(18) 0.034(2) 0.0290(18) 0.0028(15) 0.0025(15) 0.0046(15) O7 0.047(2) 0.044(2) 0.055(2) -0.0050(19) 0.042(2) 0.0040(18) O8 0.046(2) 0.046(2) 0.052(2) 0.0093(18) 0.041(2) 0.0035(18) O9 0.039(2) 0.0236(17) 0.0265(18) 0.0003(14) 0.0191(17) 0.0009(15) O10 0.0254(18) 0.0332(19) 0.0237(17) -0.0004(14) 0.0136(15) -0.0014(14) O11 0.025(2) 0.071(3) 0.042(2) 0.0019(19) 0.0158(19) 0.0037(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 C1 O1 1.242(5) . ? C1 O2 1.256(5) . ? C1 C2 1.504(6) . ? C2 C7 1.394(7) . ? C2 C3 1.396(6) . ? C3 C4 1.378(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C6 1.346(6) . ? C5 C8 1.535(6) . ? C6 C7 1.375(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.410(6) . ? C8 C14 1.414(6) . ? C9 C10 1.384(6) . ? C9 H9 0.9300 . ? C10 C12 1.403(6) . ? C10 C11 1.500(6) . ? C11 O3 1.248(5) . ? C11 O4 1.251(5) . ? C12 C13 1.415(6) . ? C12 C16 1.533(6) . ? C13 C14 1.384(6) . ? C13 H13 0.9300 . ? C14 C15 1.509(6) . ? C15 O5 1.253(5) . ? C15 O6 1.255(5) . ? C16 C17 1.351(6) . ? C16 C21 1.381(6) . ? C17 C18 1.382(6) . ? C17 H17 0.9300 . ? C18 C19 1.390(7) . ? C18 H18 0.9300 . ? C19 C20 1.392(6) . ? C19 C22 1.507(6) . ? C20 C21 1.394(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 O7 1.249(6) . ? C22 O8 1.262(5) . ? C23 N1 1.469(7) . ? C23 C24 1.472(10) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.503(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.483(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 O9 1.278(6) . ? C26 N1 1.322(6) . ? C27 N1 1.464(7) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.400(15) . ? C28 N2 1.489(13) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.517(14) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.669(13) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 O11 1.214(8) . ? C31 N2 1.278(11) . ? C32 N2 1.263(12) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? Mn1 O2 2.114(3) . ? Mn1 O8 2.132(3) 4_476 ? Mn1 O6 2.136(3) 4_576 ? Mn1 O4 2.155(3) 1_455 ? Mn1 O9 2.240(3) . ? Mn1 O10 2.383(3) . ? Mn2 O7 2.155(3) 1_455 ? Mn2 O7 2.155(3) 3_666 ? Mn2 O5 2.159(3) 3_566 ? Mn2 O5 2.159(3) . ? Mn2 O9 2.261(3) 2_546 ? Mn2 O9 2.261(3) 4_575 ? Mn3 O3 2.133(3) 1_455 ? Mn3 O3 2.133(3) 3_667 ? Mn3 O1 2.149(3) 3_567 ? Mn3 O1 2.149(3) . ? Mn3 O10 2.253(3) . ? Mn3 O10 2.253(3) 3_567 ? O3 Mn3 2.133(3) 1_655 ? O4 Mn1 2.155(3) 1_655 ? O6 Mn1 2.136(3) 4_575 ? O7 Mn2 2.155(3) 1_655 ? O8 Mn1 2.132(3) 4_675 ? O9 Mn2 2.261(3) 2_556 ? O10 H10A 0.9700 . ? O10 H10B 0.9700 . ? 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 C1 O2 125.9(4) . . ? O1 C1 C2 118.4(4) . . ? O2 C1 C2 115.7(4) . . ? C7 C2 C3 118.4(4) . . ? C7 C2 C1 119.6(4) . . ? C3 C2 C1 122.0(4) . . ? C4 C3 C2 119.3(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.6(4) . . ? C6 C5 C8 120.5(4) . . ? C4 C5 C8 118.8(4) . . ? C5 C6 C7 119.6(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 121.4(4) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? C9 C8 C14 117.1(4) . . ? C9 C8 C5 120.2(4) . . ? C14 C8 C5 122.7(4) . . ? C10 C9 C8 123.4(4) . . ? C10 C9 H9 118.3 . . ? C8 C9 H9 118.3 . . ? C9 C10 C12 119.7(4) . . ? C9 C10 C11 116.9(4) . . ? C12 C10 C11 123.4(4) . . ? O3 C11 O4 126.3(4) . . ? O3 C11 C10 116.7(4) . . ? O4 C11 C10 116.9(4) . . ? C10 C12 C13 117.2(4) . . ? C10 C12 C16 123.7(4) . . ? C13 C12 C16 119.1(4) . . ? C14 C13 C12 123.4(4) . . ? C14 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? C13 C14 C8 119.3(4) . . ? C13 C14 C15 116.9(4) . . ? C8 C14 C15 123.8(4) . . ? O5 C15 O6 127.1(4) . . ? O5 C15 C14 116.7(4) . . ? O6 C15 C14 116.0(4) . . ? C17 C16 C21 121.2(4) . . ? C17 C16 C12 119.6(4) . . ? C21 C16 C12 119.2(4) . . ? C16 C17 C18 119.5(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 121.1(4) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C20 118.9(4) . . ? C18 C19 C22 119.3(4) . . ? C20 C19 C22 121.8(4) . . ? C19 C20 C21 119.3(4) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C16 C21 C20 119.9(4) . . ? C16 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? O7 C22 O8 125.8(4) . . ? O7 C22 C19 117.2(4) . . ? O8 C22 C19 117.0(4) . . ? N1 C23 C24 104.6(6) . . ? N1 C23 H23A 110.8 . . ? C24 C23 H23A 110.8 . . ? N1 C23 H23B 110.8 . . ? C24 C23 H23B 110.8 . . ? H23A C23 H23B 108.9 . . ? C23 C24 C25 106.9(6) . . ? C23 C24 H24A 110.3 . . ? C25 C24 H24A 110.3 . . ? C23 C24 H24B 110.3 . . ? C25 C24 H24B 110.3 . . ? H24A C24 H24B 108.6 . . ? C26 C25 C24 105.0(5) . . ? C26 C25 H25A 110.7 . . ? C24 C25 H25A 110.7 . . ? C26 C25 H25B 110.7 . . ? C24 C25 H25B 110.7 . . ? H25A C25 H25B 108.8 . . ? O9 C26 N1 124.2(5) . . ? O9 C26 C25 126.3(5) . . ? N1 C26 C25 109.4(5) . . ? N1 C27 H27A 109.5 . . ? N1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 N2 107.1(10) . . ? C29 C28 H28A 110.3 . . ? N2 C28 H28A 110.3 . . ? C29 C28 H28B 110.3 . . ? N2 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? C28 C29 C30 111.6(10) . . ? C28 C29 H29A 109.3 . . ? C30 C29 H29A 109.3 . . ? C28 C29 H29B 109.3 . . ? C30 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? C29 C30 C31 98.6(9) . . ? C29 C30 H30A 112.1 . . ? C31 C30 H30A 112.1 . . ? C29 C30 H30B 112.1 . . ? C31 C30 H30B 112.1 . . ? H30A C30 H30B 109.7 . . ? O11 C31 N2 133.3(9) . . ? O11 C31 C30 118.0(7) . . ? N2 C31 C30 108.7(8) . . ? N2 C32 H32A 109.5 . . ? N2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O2 Mn1 O8 162.87(14) . 4_476 ? O2 Mn1 O6 91.49(14) . 4_576 ? O8 Mn1 O6 96.44(14) 4_476 4_576 ? O2 Mn1 O4 87.59(14) . 1_455 ? O8 Mn1 O4 85.75(14) 4_476 1_455 ? O6 Mn1 O4 175.04(13) 4_576 1_455 ? O2 Mn1 O9 94.10(12) . . ? O8 Mn1 O9 101.67(13) 4_476 . ? O6 Mn1 O9 85.14(13) 4_576 . ? O4 Mn1 O9 90.07(13) 1_455 . ? O2 Mn1 O10 88.60(12) . . ? O8 Mn1 O10 77.05(13) 4_476 . ? O6 Mn1 O10 84.95(12) 4_576 . ? O4 Mn1 O10 99.89(12) 1_455 . ? O9 Mn1 O10 169.79(11) . . ? O7 Mn2 O7 180.00(15) 1_455 3_666 ? O7 Mn2 O5 91.85(13) 1_455 3_566 ? O7 Mn2 O5 88.15(13) 3_666 3_566 ? O7 Mn2 O5 88.15(13) 1_455 . ? O7 Mn2 O5 91.85(13) 3_666 . ? O5 Mn2 O5 180.0 3_566 . ? O7 Mn2 O9 87.63(12) 1_455 2_546 ? O7 Mn2 O9 92.37(12) 3_666 2_546 ? O5 Mn2 O9 90.07(12) 3_566 2_546 ? O5 Mn2 O9 89.93(12) . 2_546 ? O7 Mn2 O9 92.37(12) 1_455 4_575 ? O7 Mn2 O9 87.63(12) 3_666 4_575 ? O5 Mn2 O9 89.93(12) 3_566 4_575 ? O5 Mn2 O9 90.07(12) . 4_575 ? O9 Mn2 O9 180.000(1) 2_546 4_575 ? O3 Mn3 O3 180.000(1) 1_455 3_667 ? O3 Mn3 O1 84.39(14) 1_455 3_567 ? O3 Mn3 O1 95.61(13) 3_667 3_567 ? O3 Mn3 O1 95.61(13) 1_455 . ? O3 Mn3 O1 84.39(14) 3_667 . ? O1 Mn3 O1 180.000(1) 3_567 . ? O3 Mn3 O10 86.98(13) 1_455 . ? O3 Mn3 O10 93.02(13) 3_667 . ? O1 Mn3 O10 86.58(12) 3_567 . ? O1 Mn3 O10 93.42(12) . . ? O3 Mn3 O10 93.02(13) 1_455 3_567 ? O3 Mn3 O10 86.98(13) 3_667 3_567 ? O1 Mn3 O10 93.42(12) 3_567 3_567 ? O1 Mn3 O10 86.58(12) . 3_567 ? O10 Mn3 O10 180.000(1) . 3_567 ? C26 N1 C27 123.9(5) . . ? C26 N1 C23 113.0(5) . . ? C27 N1 C23 123.1(5) . . ? C32 N2 C31 119.9(10) . . ? C32 N2 C28 126.5(11) . . ? C31 N2 C28 113.4(12) . . ? C1 O1 Mn3 134.4(3) . . ? C1 O2 Mn1 142.6(3) . . ? C11 O3 Mn3 146.8(3) . 1_655 ? C11 O4 Mn1 126.5(3) . 1_655 ? C15 O5 Mn2 131.6(3) . . ? C15 O6 Mn1 141.2(3) . 4_575 ? C22 O7 Mn2 146.3(3) . 1_655 ? C22 O8 Mn1 128.2(3) . 4_675 ? C26 O9 Mn1 120.1(3) . . ? C26 O9 Mn2 128.1(3) . 2_556 ? Mn1 O9 Mn2 111.70(13) . 2_556 ? Mn3 O10 Mn1 109.22(12) . . ? Mn3 O10 H10A 109.8 . . ? Mn1 O10 H10A 109.8 . . ? Mn3 O10 H10B 109.8 . . ? Mn1 O10 H10B 109.8 . . ? H10A O10 H10B 108.3 . . ? 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 O1 C1 C2 C7 136.3(5) . . . . ? O2 C1 C2 C7 -45.5(7) . . . . ? O1 C1 C2 C3 -44.1(7) . . . . ? O2 C1 C2 C3 134.1(5) . . . . ? C7 C2 C3 C4 3.1(8) . . . . ? C1 C2 C3 C4 -176.5(5) . . . . ? C2 C3 C4 C5 -3.1(8) . . . . ? C3 C4 C5 C6 1.0(8) . . . . ? C3 C4 C5 C8 178.8(4) . . . . ? C4 C5 C6 C7 1.2(8) . . . . ? C8 C5 C6 C7 -176.6(4) . . . . ? C5 C6 C7 C2 -1.1(8) . . . . ? C3 C2 C7 C6 -1.0(8) . . . . ? C1 C2 C7 C6 178.6(5) . . . . ? C6 C5 C8 C9 138.5(5) . . . . ? C4 C5 C8 C9 -39.3(6) . . . . ? C6 C5 C8 C14 -40.1(6) . . . . ? C4 C5 C8 C14 142.1(5) . . . . ? C14 C8 C9 C10 1.1(6) . . . . ? C5 C8 C9 C10 -177.5(4) . . . . ? C8 C9 C10 C12 -0.2(6) . . . . ? C8 C9 C10 C11 176.0(4) . . . . ? C9 C10 C11 O3 68.9(5) . . . . ? C12 C10 C11 O3 -115.0(5) . . . . ? C9 C10 C11 O4 -108.9(4) . . . . ? C12 C10 C11 O4 67.2(6) . . . . ? C9 C10 C12 C13 -0.8(6) . . . . ? C11 C10 C12 C13 -176.7(4) . . . . ? C9 C10 C12 C16 -178.2(4) . . . . ? C11 C10 C12 C16 5.8(6) . . . . ? C10 C12 C13 C14 0.8(6) . . . . ? C16 C12 C13 C14 178.4(4) . . . . ? C12 C13 C14 C8 0.2(6) . . . . ? C12 C13 C14 C15 -177.6(4) . . . . ? C9 C8 C14 C13 -1.1(6) . . . . ? C5 C8 C14 C13 177.5(4) . . . . ? C9 C8 C14 C15 176.5(4) . . . . ? C5 C8 C14 C15 -4.9(6) . . . . ? C13 C14 C15 O5 99.0(5) . . . . ? C8 C14 C15 O5 -78.6(5) . . . . ? C13 C14 C15 O6 -77.9(5) . . . . ? C8 C14 C15 O6 104.5(5) . . . . ? C10 C12 C16 C17 40.0(6) . . . . ? C13 C12 C16 C17 -137.4(5) . . . . ? C10 C12 C16 C21 -141.7(4) . . . . ? C13 C12 C16 C21 40.9(6) . . . . ? C21 C16 C17 C18 -1.8(7) . . . . ? C12 C16 C17 C18 176.4(4) . . . . ? C16 C17 C18 C19 1.7(8) . . . . ? C17 C18 C19 C20 0.8(8) . . . . ? C17 C18 C19 C22 -178.4(4) . . . . ? C18 C19 C20 C21 -3.0(7) . . . . ? C22 C19 C20 C21 176.1(4) . . . . ? C17 C16 C21 C20 -0.4(7) . . . . ? C12 C16 C21 C20 -178.7(4) . . . . ? C19 C20 C21 C16 2.9(7) . . . . ? C18 C19 C22 O7 39.7(7) . . . . ? C20 C19 C22 O7 -139.4(5) . . . . ? C18 C19 C22 O8 -140.9(5) . . . . ? C20 C19 C22 O8 39.9(7) . . . . ? N1 C23 C24 C25 9.2(7) . . . . ? C23 C24 C25 C26 -9.6(7) . . . . ? C24 C25 C26 O9 -173.5(5) . . . . ? C24 C25 C26 N1 6.4(6) . . . . ? N2 C28 C29 C30 -8.6(10) . . . . ? C28 C29 C30 C31 7.6(9) . . . . ? C29 C30 C31 O11 175.2(6) . . . . ? C29 C30 C31 N2 -3.9(7) . . . . ? O9 C26 N1 C27 -0.1(7) . . . . ? C25 C26 N1 C27 -180.0(5) . . . . ? O9 C26 N1 C23 179.3(4) . . . . ? C25 C26 N1 C23 -0.6(6) . . . . ? C24 C23 N1 C26 -5.6(7) . . . . ? C24 C23 N1 C27 173.8(5) . . . . ? O11 C31 N2 C32 4.7(12) . . . . ? C30 C31 N2 C32 -176.5(7) . . . . ? O11 C31 N2 C28 -179.8(6) . . . . ? C30 C31 N2 C28 -0.9(7) . . . . ? C29 C28 N2 C32 -178.9(8) . . . . ? C29 C28 N2 C31 6.0(9) . . . . ? O2 C1 O1 Mn3 1.6(8) . . . . ? C2 C1 O1 Mn3 179.6(3) . . . . ? O3 Mn3 O1 C1 57.0(5) 1_455 . . . ? O3 Mn3 O1 C1 -123.0(5) 3_667 . . . ? O1 Mn3 O1 C1 94(100) 3_567 . . . ? O10 Mn3 O1 C1 -30.3(5) . . . . ? O10 Mn3 O1 C1 149.7(5) 3_567 . . . ? O1 C1 O2 Mn1 -0.3(9) . . . . ? C2 C1 O2 Mn1 -178.3(4) . . . . ? O8 Mn1 O2 C1 -6.2(9) 4_476 . . . ? O6 Mn1 O2 C1 111.5(6) 4_576 . . . ? O4 Mn1 O2 C1 -73.4(6) 1_455 . . . ? O9 Mn1 O2 C1 -163.3(6) . . . . ? O10 Mn1 O2 C1 26.6(6) . . . . ? O4 C11 O3 Mn3 -9.2(9) . . . 1_655 ? C10 C11 O3 Mn3 173.3(4) . . . 1_655 ? O3 C11 O4 Mn1 -18.7(6) . . . 1_655 ? C10 C11 O4 Mn1 158.8(3) . . . 1_655 ? O6 C15 O5 Mn2 9.4(7) . . . . ? C14 C15 O5 Mn2 -167.1(3) . . . . ? O7 Mn2 O5 C15 -68.7(4) 1_455 . . . ? O7 Mn2 O5 C15 111.3(4) 3_666 . . . ? O5 Mn2 O5 C15 134(100) 3_566 . . . ? O9 Mn2 O5 C15 -156.3(4) 2_546 . . . ? O9 Mn2 O5 C15 23.7(4) 4_575 . . . ? O5 C15 O6 Mn1 -6.8(8) . . . 4_575 ? C14 C15 O6 Mn1 169.7(3) . . . 4_575 ? O8 C22 O7 Mn2 -8.8(10) . . . 1_655 ? C19 C22 O7 Mn2 170.4(4) . . . 1_655 ? O7 C22 O8 Mn1 -4.2(8) . . . 4_675 ? C19 C22 O8 Mn1 176.5(3) . . . 4_675 ? N1 C26 O9 Mn1 -86.9(5) . . . . ? C25 C26 O9 Mn1 93.0(5) . . . . ? N1 C26 O9 Mn2 91.2(5) . . . 2_556 ? C25 C26 O9 Mn2 -88.9(6) . . . 2_556 ? O2 Mn1 O9 C26 31.6(4) . . . . ? O8 Mn1 O9 C26 -141.7(4) 4_476 . . . ? O6 Mn1 O9 C26 122.7(4) 4_576 . . . ? O4 Mn1 O9 C26 -56.0(4) 1_455 . . . ? O10 Mn1 O9 C26 136.6(6) . . . . ? O2 Mn1 O9 Mn2 -146.81(16) . . . 2_556 ? O8 Mn1 O9 Mn2 39.93(18) 4_476 . . 2_556 ? O6 Mn1 O9 Mn2 -55.66(15) 4_576 . . 2_556 ? O4 Mn1 O9 Mn2 125.60(15) 1_455 . . 2_556 ? O10 Mn1 O9 Mn2 -41.8(7) . . . 2_556 ? O3 Mn3 O10 Mn1 -45.27(14) 1_455 . . . ? O3 Mn3 O10 Mn1 134.73(14) 3_667 . . . ? O1 Mn3 O10 Mn1 -129.82(15) 3_567 . . . ? O1 Mn3 O10 Mn1 50.18(15) . . . . ? O10 Mn3 O10 Mn1 -13(100) 3_567 . . . ? O2 Mn1 O10 Mn3 -47.78(15) . . . . ? O8 Mn1 O10 Mn3 122.80(16) 4_476 . . . ? O6 Mn1 O10 Mn3 -139.39(15) 4_576 . . . ? O4 Mn1 O10 Mn3 39.53(15) 1_455 . . . ? O9 Mn1 O10 Mn3 -153.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.56 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.659 _refine_diff_density_min -1.117 _refine_diff_density_rms 0.191 _database_code_depnum_ccdc_archive 'CCDC 929833' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Mn2 N2 O11' _chemical_formula_weight 704.44 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' Mn Mn 0.3368 0.7283 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.646(3) _cell_length_b 14.834(4) _cell_length_c 18.979(3) _cell_angle_alpha 90.00 _cell_angle_beta 123.145(11) _cell_angle_gamma 90.00 _cell_volume 2981.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7778 _exptl_absorpt_correction_T_max 0.8245 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13793 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.37 _reflns_number_total 4826 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4826 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.2621 _refine_ls_wR_factor_gt 0.1839 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.109 _refine_ls_shift/su_mean 0.012 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 C1 C 0.1156(5) 0.8499(4) 0.9356(3) 0.0222(12) Uani 1 1 d . . . C2 C 0.1875(5) 0.8463(3) 0.8926(3) 0.0178(11) Uani 1 1 d . . . C3 C 0.1578(5) 0.9061(4) 0.8278(3) 0.0240(12) Uani 1 1 d . . . H3 H 0.0900 0.9453 0.8087 0.029 Uiso 1 1 calc R . . C4 C 0.2258(5) 0.9087(4) 0.7912(3) 0.0225(12) Uani 1 1 d . . . H4 H 0.2014 0.9471 0.7461 0.027 Uiso 1 1 calc R . . C5 C 0.3321(5) 0.8534(3) 0.8216(3) 0.0174(11) Uani 1 1 d . . . C6 C 0.3634(5) 0.7921(4) 0.8852(4) 0.0275(13) Uani 1 1 d . . . H6 H 0.4326 0.7541 0.9049 0.033 Uiso 1 1 calc R . . C7 C 0.2894(5) 0.7880(4) 0.9197(3) 0.0235(12) Uani 1 1 d . . . H7 H 0.3087 0.7458 0.9613 0.028 Uiso 1 1 calc R . . C8 C 0.4141(5) 0.8613(3) 0.7860(3) 0.0170(11) Uani 1 1 d . . . C9 C 0.3632(5) 0.8707(3) 0.6995(3) 0.0141(11) Uani 1 1 d . . . C10 C 0.2233(5) 0.8663(3) 0.6326(3) 0.0167(12) Uani 1 1 d . . . C11 C 0.4422(5) 0.8817(3) 0.6720(3) 0.0168(12) Uani 1 1 d . . . H11 H 0.4071 0.8889 0.6146 0.020 Uiso 1 1 calc R . . C12 C 0.5746(5) 0.8824(3) 0.7271(3) 0.0143(11) Uani 1 1 d . . . C13 C 0.6256(5) 0.8734(3) 0.8139(3) 0.0152(12) Uani 1 1 d . . . C14 C 0.7665(5) 0.8773(3) 0.8804(3) 0.0133(11) Uani 1 1 d . . . C15 C 0.5428(5) 0.8642(3) 0.8401(3) 0.0179(12) Uani 1 1 d . . . H15 H 0.5766 0.8599 0.8975 0.021 Uiso 1 1 calc R . . C16 C 0.6564(5) 0.8876(3) 0.6910(3) 0.0131(11) Uani 1 1 d . . . C17 C 0.6225(5) 0.9464(4) 0.6236(3) 0.0269(13) Uani 1 1 d . . . H17 H 0.5519 0.9831 0.6028 0.032 Uiso 1 1 calc R . . C18 C 0.6915(5) 0.9502(4) 0.5883(3) 0.0254(13) Uani 1 1 d . . . H18 H 0.6680 0.9895 0.5438 0.030 Uiso 1 1 calc R . . C19 C 0.7984(5) 0.8949(3) 0.6190(3) 0.0194(12) Uani 1 1 d . . . C20 C 0.8296(5) 0.8356(4) 0.6851(3) 0.0259(13) Uani 1 1 d . . . H20 H 0.8972 0.7962 0.7046 0.031 Uiso 1 1 calc R . . C21 C 0.7609(5) 0.8355(4) 0.7210(3) 0.0238(12) Uani 1 1 d . . . H21 H 0.7865 0.7987 0.7674 0.029 Uiso 1 1 calc R . . C22 C 0.8744(5) 0.8922(4) 0.5782(3) 0.0196(12) Uani 1 1 d . . . C23 C 0.8164(6) 0.8807(4) 1.0891(5) 0.0442(18) Uani 1 1 d . . . H23A H 0.8006 0.8811 1.1331 0.066 Uiso 1 1 calc R . . H23B H 0.7814 0.8270 1.0560 0.066 Uiso 1 1 calc R . . H23C H 0.7776 0.9326 1.0538 0.066 Uiso 1 1 calc R . . C24 C 0.9846(14) 0.8837(4) 1.1347(7) 0.095(5) Uani 1 1 d . . . C25 C 0.9943(10) 0.8808(4) 1.2646(5) 0.071(3) Uani 1 1 d . . . H25A H 1.0323 0.9339 1.2982 0.107 Uiso 1 1 calc R . . H25B H 1.0369 0.8283 1.2976 0.107 Uiso 1 1 calc R . . H25C H 0.9068 0.8784 1.2457 0.107 Uiso 1 1 calc R . . C26 C 1.1722(7) 0.8858(5) 1.2356(5) 0.053(2) Uani 1 1 d . . . H26A H 1.1961 0.8311 1.2208 0.080 Uiso 1 1 calc R . . H26B H 1.2180 0.8908 1.2958 0.080 Uiso 1 1 calc R . . H26C H 1.1915 0.9364 1.2131 0.080 Uiso 1 1 calc R . . C27 C 0.6159(11) 0.6206(4) 0.8433(7) 0.066(3) Uani 1 1 d . . . H27A H 0.6248 0.5603 0.8642 0.098 Uiso 1 1 calc R . . H27B H 0.5341 0.6436 0.8260 0.098 Uiso 1 1 calc R . . H27C H 0.6801 0.6583 0.8869 0.098 Uiso 1 1 calc R . . C28 C 0.6296(7) 0.6202(4) 0.7681(5) 0.0400(18) Uani 1 1 d . . . C29 C 0.4009(9) 0.6256(5) 0.6718(9) 0.095(5) Uani 1 1 d . . . H29A H 0.4015 0.6225 0.7225 0.142 Uiso 1 1 calc R . . H29B H 0.3507 0.5771 0.6350 0.142 Uiso 1 1 calc R . . H29C H 0.3655 0.6822 0.6443 0.142 Uiso 1 1 calc R . . C30 C 0.5423(10) 0.6144(7) 0.6207(6) 0.099(4) Uani 1 1 d . . . H30A H 0.5482 0.6746 0.6045 0.149 Uiso 1 1 calc R . . H30B H 0.4717 0.5842 0.5738 0.149 Uiso 1 1 calc R . . H30C H 0.6185 0.5821 0.6380 0.149 Uiso 1 1 calc R . . Mn1 Mn 0.99281(7) 0.75129(4) 1.01530(5) 0.0136(3) Uani 1 1 d . . . Mn2 Mn 1.0000 1.0000 1.0000 0.0138(4) Uani 1 2 d S . . Mn3 Mn 1.0000 0.5000 1.0000 0.0153(4) Uani 1 2 d S . . N1 N 1.0049(15) 0.8838(4) 1.1928(8) 0.131(6) Uani 1 1 d . . . N2 N 0.5243(6) 0.6183(4) 0.6914(5) 0.066(2) Uani 1 1 d . . . O1 O 0.0981(4) 0.7757(3) 0.9588(3) 0.0329(10) Uani 1 1 d . . . O2 O 0.0850(4) 0.9247(3) 0.9455(3) 0.0335(10) Uani 1 1 d . . . O3 O 0.1690(4) 0.7919(3) 0.6234(2) 0.0330(10) Uani 1 1 d . . . O4 O 0.1714(3) 0.9355(3) 0.5901(3) 0.0366(11) Uani 1 1 d . . . O5 O 0.8177(3) 0.8041(2) 0.9139(2) 0.0257(9) Uani 1 1 d . . . O6 O 0.8178(3) 0.9532(2) 0.8987(2) 0.0272(9) Uani 1 1 d . . . O7 O 0.8993(4) 0.9649(3) 0.5593(3) 0.0322(10) Uani 1 1 d . . . O8 O 0.9017(4) 0.8148(3) 0.5667(3) 0.0339(10) Uani 1 1 d . . . O9 O 1.0075(4) 0.8822(2) 1.0795(2) 0.0221(9) Uani 1 1 d . . . O10 O 0.9451(4) 0.6268(2) 0.9241(2) 0.0226(9) Uani 1 1 d . . . H10A H 0.8555 0.6259 0.8808 0.027 Uiso 1 1 calc R . . H10B H 0.9912 0.6318 0.8969 0.027 Uiso 1 1 calc R . . O11 O 0.7353(4) 0.6184(3) 0.7790(3) 0.0409(12) 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 C1 0.019(3) 0.027(3) 0.020(3) -0.003(2) 0.011(2) -0.004(2) C2 0.017(3) 0.021(3) 0.021(3) -0.005(2) 0.013(2) -0.006(2) C3 0.023(3) 0.026(3) 0.024(3) 0.002(2) 0.014(3) 0.008(2) C4 0.024(3) 0.029(3) 0.021(3) 0.006(2) 0.017(2) 0.010(2) C5 0.017(3) 0.021(3) 0.010(3) -0.003(2) 0.004(2) -0.005(2) C6 0.027(3) 0.033(3) 0.029(3) 0.012(3) 0.020(3) 0.010(3) C7 0.023(3) 0.029(3) 0.026(3) 0.009(2) 0.019(3) 0.010(2) C8 0.017(3) 0.018(3) 0.018(3) 0.001(2) 0.010(2) 0.002(2) C9 0.016(3) 0.010(2) 0.017(3) 0.0011(18) 0.010(2) 0.0012(18) C10 0.013(3) 0.025(3) 0.012(3) -0.003(2) 0.007(2) -0.001(2) C11 0.016(3) 0.023(3) 0.010(3) -0.0023(19) 0.006(2) 0.000(2) C12 0.015(3) 0.015(3) 0.014(3) -0.0012(19) 0.009(2) -0.0010(19) C13 0.014(3) 0.014(3) 0.017(3) 0.0009(19) 0.008(2) -0.0001(18) C14 0.013(3) 0.015(3) 0.013(3) 0.0010(19) 0.007(2) -0.0004(19) C15 0.017(3) 0.024(3) 0.011(3) 0.003(2) 0.007(2) 0.005(2) C16 0.013(3) 0.016(2) 0.009(2) -0.0001(19) 0.005(2) -0.0057(19) C17 0.030(3) 0.031(3) 0.021(3) 0.007(2) 0.014(3) 0.007(2) C18 0.028(3) 0.034(3) 0.027(3) 0.010(2) 0.023(3) 0.010(2) C19 0.018(3) 0.019(3) 0.025(3) -0.004(2) 0.015(3) -0.002(2) C20 0.028(3) 0.030(3) 0.023(3) 0.004(2) 0.016(3) 0.003(2) C21 0.029(3) 0.026(3) 0.020(3) 0.009(2) 0.016(3) 0.010(2) C22 0.018(3) 0.028(3) 0.018(3) -0.005(2) 0.013(2) 0.004(2) C23 0.026(4) 0.054(5) 0.047(5) -0.005(3) 0.016(3) 0.005(3) C24 0.251(15) 0.014(4) 0.098(8) -0.001(4) 0.145(10) 0.000(5) C25 0.163(11) 0.039(5) 0.063(6) 0.000(4) 0.095(8) -0.001(5) C26 0.051(5) 0.058(5) 0.033(4) -0.009(3) 0.012(4) 0.008(4) C27 0.106(8) 0.031(4) 0.089(7) -0.007(4) 0.072(7) -0.004(4) C28 0.042(5) 0.024(3) 0.046(4) 0.005(3) 0.019(4) 0.008(3) C29 0.041(6) 0.055(6) 0.151(12) -0.006(5) 0.028(7) 0.002(4) C30 0.065(7) 0.130(10) 0.041(5) 0.006(5) -0.010(5) 0.030(6) Mn1 0.0114(5) 0.0154(5) 0.0141(5) 0.0028(3) 0.0071(4) 0.0017(3) Mn2 0.0114(6) 0.0151(6) 0.0147(6) -0.0012(4) 0.0070(5) -0.0001(4) Mn3 0.0135(7) 0.0151(6) 0.0156(6) -0.0051(4) 0.0069(5) -0.0017(4) N1 0.342(18) 0.028(4) 0.157(10) 0.013(4) 0.221(12) 0.023(6) N2 0.041(4) 0.045(4) 0.070(5) 0.010(3) 0.003(4) 0.006(3) O1 0.038(2) 0.030(2) 0.053(3) 0.007(2) 0.039(2) 0.0016(19) O2 0.043(3) 0.031(2) 0.045(3) -0.0023(19) 0.036(2) 0.0084(19) O3 0.026(2) 0.030(2) 0.027(2) -0.0028(18) 0.0046(19) -0.0138(18) O4 0.018(2) 0.034(2) 0.037(2) 0.014(2) 0.0017(19) 0.0022(18) O5 0.016(2) 0.024(2) 0.023(2) 0.0020(16) 0.0023(17) 0.0022(16) O6 0.019(2) 0.028(2) 0.024(2) 0.0009(16) 0.0049(17) -0.0063(16) O7 0.045(3) 0.025(2) 0.051(3) 0.0064(18) 0.042(2) 0.0010(18) O8 0.045(3) 0.030(2) 0.046(3) -0.0024(19) 0.038(2) 0.0030(19) O9 0.034(2) 0.0164(19) 0.019(2) 0.0005(14) 0.0168(19) -0.0012(15) O10 0.025(2) 0.025(2) 0.017(2) 0.0017(14) 0.0106(17) 0.0024(15) O11 0.019(2) 0.055(3) 0.040(3) 0.005(2) 0.011(2) 0.0073(18) _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 C1 O2 1.224(7) . ? C1 O1 1.249(7) . ? C1 C2 1.517(7) . ? C2 C3 1.392(8) . ? C2 C7 1.396(7) . ? C3 C4 1.370(8) . ? C3 H3 0.9300 . ? C4 C5 1.402(7) . ? C4 H4 0.9300 . ? C5 C6 1.385(7) . ? C5 C8 1.519(7) . ? C6 C7 1.406(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C15 1.370(8) . ? C8 C9 1.405(7) . ? C9 C11 1.367(8) . ? C9 C10 1.513(8) . ? C10 O4 1.247(6) . ? C10 O3 1.260(6) . ? C11 C12 1.409(8) . ? C11 H11 0.9300 . ? C12 C13 1.410(8) . ? C12 C16 1.522(7) . ? C13 C15 1.389(8) . ? C13 C14 1.521(7) . ? C14 O5 1.247(6) . ? C14 O6 1.250(6) . ? C15 H15 0.9300 . ? C16 C21 1.358(7) . ? C16 C17 1.408(7) . ? C17 C18 1.361(8) . ? C17 H17 0.9300 . ? C18 C19 1.407(7) . ? C18 H18 0.9300 . ? C19 C20 1.401(8) . ? C19 C22 1.528(7) . ? C20 C21 1.366(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 O7 1.230(6) . ? C22 O8 1.253(6) . ? C23 C24 1.806(16) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N1 0.987(12) . ? C24 O9 1.230(10) . ? C25 N1 1.439(10) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N1 1.805(16) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.529(12) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O11 1.235(9) . ? C28 N2 1.332(10) . ? C29 N2 1.397(13) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 N2 1.479(15) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? Mn1 O8 2.114(4) 4_576 ? Mn1 O5 2.135(3) . ? Mn1 O3 2.141(4) 4_676 ? Mn1 O1 2.149(4) 1_655 ? Mn1 O9 2.246(3) . ? Mn1 O10 2.373(3) . ? Mn2 O6 2.155(3) 3_777 ? Mn2 O6 2.155(3) . ? Mn2 O2 2.165(4) 3_677 ? Mn2 O2 2.165(4) 1_655 ? Mn2 O9 2.276(3) 3_777 ? Mn2 O9 2.276(3) . ? Mn3 O4 2.118(4) 4_676 ? Mn3 O4 2.118(4) 2_646 ? Mn3 O7 2.175(4) 4_576 ? Mn3 O7 2.175(4) 2_746 ? Mn3 O10 2.236(3) 3_767 ? Mn3 O10 2.236(3) . ? O1 Mn1 2.149(4) 1_455 ? O2 Mn2 2.165(4) 1_455 ? O3 Mn1 2.141(4) 4_475 ? O4 Mn3 2.118(4) 2_656 ? O7 Mn3 2.175(4) 2_756 ? O8 Mn1 2.114(4) 4_575 ? O10 H10A 0.9700 . ? O10 H10B 0.9700 . ? 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 O2 C1 O1 127.8(5) . . ? O2 C1 C2 116.6(5) . . ? O1 C1 C2 115.6(5) . . ? C3 C2 C7 117.9(5) . . ? C3 C2 C1 120.1(5) . . ? C7 C2 C1 121.8(5) . . ? C4 C3 C2 121.7(5) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.7(5) . . ? C6 C5 C8 119.9(5) . . ? C4 C5 C8 120.4(4) . . ? C5 C6 C7 119.2(5) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 121.2(5) . . ? C2 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C15 C8 C9 118.0(5) . . ? C15 C8 C5 119.3(5) . . ? C9 C8 C5 122.6(5) . . ? C11 C9 C8 119.7(5) . . ? C11 C9 C10 116.5(5) . . ? C8 C9 C10 123.7(5) . . ? O4 C10 O3 125.2(5) . . ? O4 C10 C9 117.9(4) . . ? O3 C10 C9 116.9(4) . . ? C9 C11 C12 122.5(5) . . ? C9 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C11 C12 C13 117.7(5) . . ? C11 C12 C16 119.4(5) . . ? C13 C12 C16 122.8(5) . . ? C15 C13 C12 118.4(5) . . ? C15 C13 C14 118.5(5) . . ? C12 C13 C14 123.1(5) . . ? O5 C14 O6 126.6(5) . . ? O5 C14 C13 115.9(4) . . ? O6 C14 C13 117.4(4) . . ? C8 C15 C13 123.7(5) . . ? C8 C15 H15 118.2 . . ? C13 C15 H15 118.2 . . ? C21 C16 C17 118.5(5) . . ? C21 C16 C12 121.8(4) . . ? C17 C16 C12 119.7(4) . . ? C18 C17 C16 121.0(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 118.2(5) . . ? C20 C19 C22 119.4(5) . . ? C18 C19 C22 122.2(5) . . ? C21 C20 C19 120.2(5) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C16 C21 C20 121.9(5) . . ? C16 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? O7 C22 O8 127.9(5) . . ? O7 C22 C19 117.2(4) . . ? O8 C22 C19 114.9(5) . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C24 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N1 C24 O9 156.0(18) . . ? N1 C24 C23 93.1(13) . . ? O9 C24 C23 110.8(9) . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.4 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1 C26 H26A 109.5 . . ? N1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C28 C27 H27C 109.4 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O11 C28 N2 121.8(8) . . ? O11 C28 C27 120.5(7) . . ? N2 C28 C27 117.6(8) . . ? N2 C29 H29A 109.5 . . ? N2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N2 C30 H30A 109.5 . . ? N2 C30 H30B 109.4 . . ? H30A C30 H30B 109.5 . . ? N2 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O8 Mn1 O5 91.58(16) 4_576 . ? O8 Mn1 O3 87.90(17) 4_576 4_676 ? O5 Mn1 O3 175.00(15) . 4_676 ? O8 Mn1 O1 162.04(16) 4_576 1_655 ? O5 Mn1 O1 96.26(16) . 1_655 ? O3 Mn1 O1 85.65(17) 4_676 1_655 ? O8 Mn1 O9 93.14(15) 4_576 . ? O5 Mn1 O9 84.77(14) . . ? O3 Mn1 O9 90.29(15) 4_676 . ? O1 Mn1 O9 103.62(15) 1_655 . ? O8 Mn1 O10 89.44(15) 4_576 . ? O5 Mn1 O10 84.45(14) . . ? O3 Mn1 O10 100.51(14) 4_676 . ? O1 Mn1 O10 75.33(15) 1_655 . ? O9 Mn1 O10 168.98(13) . . ? O6 Mn2 O6 180.000(1) 3_777 . ? O6 Mn2 O2 88.58(16) 3_777 3_677 ? O6 Mn2 O2 91.42(16) . 3_677 ? O6 Mn2 O2 91.42(16) 3_777 1_655 ? O6 Mn2 O2 88.58(16) . 1_655 ? O2 Mn2 O2 180.000(2) 3_677 1_655 ? O6 Mn2 O9 88.90(14) 3_777 3_777 ? O6 Mn2 O9 91.10(14) . 3_777 ? O2 Mn2 O9 93.96(14) 3_677 3_777 ? O2 Mn2 O9 86.04(14) 1_655 3_777 ? O6 Mn2 O9 91.10(14) 3_777 . ? O6 Mn2 O9 88.90(14) . . ? O2 Mn2 O9 86.04(14) 3_677 . ? O2 Mn2 O9 93.96(14) 1_655 . ? O9 Mn2 O9 180.000(1) 3_777 . ? O4 Mn3 O4 180.000(1) 4_676 2_646 ? O4 Mn3 O7 95.99(16) 4_676 4_576 ? O4 Mn3 O7 84.01(17) 2_646 4_576 ? O4 Mn3 O7 84.01(17) 4_676 2_746 ? O4 Mn3 O7 95.99(16) 2_646 2_746 ? O7 Mn3 O7 180.000(2) 4_576 2_746 ? O4 Mn3 O10 92.28(15) 4_676 3_767 ? O4 Mn3 O10 87.72(15) 2_646 3_767 ? O7 Mn3 O10 86.07(14) 4_576 3_767 ? O7 Mn3 O10 93.93(14) 2_746 3_767 ? O4 Mn3 O10 87.72(15) 4_676 . ? O4 Mn3 O10 92.28(15) 2_646 . ? O7 Mn3 O10 93.93(14) 4_576 . ? O7 Mn3 O10 86.07(14) 2_746 . ? O10 Mn3 O10 180.000(1) 3_767 . ? C24 N1 C25 162.8(19) . . ? C24 N1 C26 91.6(12) . . ? C25 N1 C26 105.5(10) . . ? C28 N2 C29 126.4(11) . . ? C28 N2 C30 115.8(8) . . ? C29 N2 C30 117.7(9) . . ? C1 O1 Mn1 127.0(4) . 1_455 ? C1 O2 Mn2 145.5(4) . 1_455 ? C10 O3 Mn1 126.7(3) . 4_475 ? C10 O4 Mn3 147.0(4) . 2_656 ? C14 O5 Mn1 140.6(3) . . ? C14 O6 Mn2 132.7(3) . . ? C22 O7 Mn3 132.6(3) . 2_756 ? C22 O8 Mn1 141.0(4) . 4_575 ? C24 O9 Mn1 119.2(4) . . ? C24 O9 Mn2 127.4(4) . . ? Mn1 O9 Mn2 110.05(15) . . ? Mn3 O10 Mn1 108.61(15) . . ? Mn3 O10 H10A 110.0 . . ? Mn1 O10 H10A 110.0 . . ? Mn3 O10 H10B 110.0 . . ? Mn1 O10 H10B 110.0 . . ? H10A O10 H10B 108.3 . . ? 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 O2 C1 C2 C3 -36.7(7) . . . . ? O1 C1 C2 C3 145.4(5) . . . . ? O2 C1 C2 C7 139.2(5) . . . . ? O1 C1 C2 C7 -38.8(7) . . . . ? C7 C2 C3 C4 -0.2(8) . . . . ? C1 C2 C3 C4 175.8(5) . . . . ? C2 C3 C4 C5 -3.2(9) . . . . ? C3 C4 C5 C6 4.1(8) . . . . ? C3 C4 C5 C8 -175.1(5) . . . . ? C4 C5 C6 C7 -1.6(8) . . . . ? C8 C5 C6 C7 177.6(5) . . . . ? C3 C2 C7 C6 2.8(8) . . . . ? C1 C2 C7 C6 -173.2(5) . . . . ? C5 C6 C7 C2 -1.9(9) . . . . ? C6 C5 C8 C15 -45.2(7) . . . . ? C4 C5 C8 C15 133.9(5) . . . . ? C6 C5 C8 C9 138.3(5) . . . . ? C4 C5 C8 C9 -42.6(7) . . . . ? C15 C8 C9 C11 0.5(7) . . . . ? C5 C8 C9 C11 177.0(5) . . . . ? C15 C8 C9 C10 178.2(4) . . . . ? C5 C8 C9 C10 -5.2(7) . . . . ? C11 C9 C10 O4 -66.4(6) . . . . ? C8 C9 C10 O4 115.9(6) . . . . ? C11 C9 C10 O3 112.5(5) . . . . ? C8 C9 C10 O3 -65.3(6) . . . . ? C8 C9 C11 C12 1.1(7) . . . . ? C10 C9 C11 C12 -176.8(4) . . . . ? C9 C11 C12 C13 -1.4(7) . . . . ? C9 C11 C12 C16 175.3(4) . . . . ? C11 C12 C13 C15 0.0(6) . . . . ? C16 C12 C13 C15 -176.5(4) . . . . ? C11 C12 C13 C14 -177.2(4) . . . . ? C16 C12 C13 C14 6.3(7) . . . . ? C15 C13 C14 O5 75.9(6) . . . . ? C12 C13 C14 O5 -106.9(5) . . . . ? C15 C13 C14 O6 -100.9(5) . . . . ? C12 C13 C14 O6 76.3(6) . . . . ? C9 C8 C15 C13 -1.9(7) . . . . ? C5 C8 C15 C13 -178.6(5) . . . . ? C12 C13 C15 C8 1.6(7) . . . . ? C14 C13 C15 C8 179.0(4) . . . . ? C11 C12 C16 C21 -136.6(5) . . . . ? C13 C12 C16 C21 39.9(7) . . . . ? C11 C12 C16 C17 42.1(6) . . . . ? C13 C12 C16 C17 -141.4(5) . . . . ? C21 C16 C17 C18 0.9(8) . . . . ? C12 C16 C17 C18 -177.8(5) . . . . ? C16 C17 C18 C19 0.1(8) . . . . ? C17 C18 C19 C20 1.0(8) . . . . ? C17 C18 C19 C22 176.1(5) . . . . ? C18 C19 C20 C21 -3.3(8) . . . . ? C22 C19 C20 C21 -178.5(5) . . . . ? C17 C16 C21 C20 -3.2(8) . . . . ? C12 C16 C21 C20 175.5(5) . . . . ? C19 C20 C21 C16 4.5(9) . . . . ? C20 C19 C22 O7 -140.2(6) . . . . ? C18 C19 C22 O7 44.8(8) . . . . ? C20 C19 C22 O8 41.1(7) . . . . ? C18 C19 C22 O8 -133.9(5) . . . . ? O9 C24 N1 C25 -171.7(17) . . . . ? C23 C24 N1 C25 5(3) . . . . ? O9 C24 N1 C26 3(2) . . . . ? C23 C24 N1 C26 179.6(4) . . . . ? O11 C28 N2 C29 -175.8(6) . . . . ? C27 C28 N2 C29 6.8(10) . . . . ? O11 C28 N2 C30 -0.3(9) . . . . ? C27 C28 N2 C30 -177.8(6) . . . . ? O2 C1 O1 Mn1 5.9(9) . . . 1_455 ? C2 C1 O1 Mn1 -176.4(3) . . . 1_455 ? O1 C1 O2 Mn2 2.9(11) . . . 1_455 ? C2 C1 O2 Mn2 -174.8(4) . . . 1_455 ? O4 C10 O3 Mn1 18.4(8) . . . 4_475 ? C9 C10 O3 Mn1 -160.4(3) . . . 4_475 ? O3 C10 O4 Mn3 9.6(11) . . . 2_656 ? C9 C10 O4 Mn3 -171.7(5) . . . 2_656 ? O6 C14 O5 Mn1 5.4(9) . . . . ? C13 C14 O5 Mn1 -171.0(4) . . . . ? O8 Mn1 O5 C14 124.2(6) 4_576 . . . ? O3 Mn1 O5 C14 40(2) 4_676 . . . ? O1 Mn1 O5 C14 -72.0(6) 1_655 . . . ? O9 Mn1 O5 C14 31.2(6) . . . . ? O10 Mn1 O5 C14 -146.5(6) . . . . ? O5 C14 O6 Mn2 -9.0(8) . . . . ? C13 C14 O6 Mn2 167.4(3) . . . . ? O6 Mn2 O6 C14 -42(16) 3_777 . . . ? O2 Mn2 O6 C14 -110.9(5) 3_677 . . . ? O2 Mn2 O6 C14 69.1(5) 1_655 . . . ? O9 Mn2 O6 C14 155.1(5) 3_777 . . . ? O9 Mn2 O6 C14 -24.9(5) . . . . ? O8 C22 O7 Mn3 -0.6(10) . . . 2_756 ? C19 C22 O7 Mn3 -179.2(3) . . . 2_756 ? O7 C22 O8 Mn1 -0.8(11) . . . 4_575 ? C19 C22 O8 Mn1 177.8(4) . . . 4_575 ? N1 C24 O9 Mn1 99(2) . . . . ? C23 C24 O9 Mn1 -77.2(6) . . . . ? N1 C24 O9 Mn2 -103.6(19) . . . . ? C23 C24 O9 Mn2 80.2(7) . . . . ? O8 Mn1 O9 C24 11.6(9) 4_576 . . . ? O5 Mn1 O9 C24 102.9(9) . . . . ? O3 Mn1 O9 C24 -76.3(9) 4_676 . . . ? O1 Mn1 O9 C24 -161.9(8) 1_655 . . . ? O10 Mn1 O9 C24 114.9(10) . . . . ? O8 Mn1 O9 Mn2 -149.42(18) 4_576 . . . ? O5 Mn1 O9 Mn2 -58.12(18) . . . . ? O3 Mn1 O9 Mn2 122.67(18) 4_676 . . . ? O1 Mn1 O9 Mn2 37.1(2) 1_655 . . . ? O10 Mn1 O9 Mn2 -46.1(8) . . . . ? O6 Mn2 O9 C24 79.7(9) 3_777 . . . ? O6 Mn2 O9 C24 -100.3(9) . . . . ? O2 Mn2 O9 C24 -8.8(9) 3_677 . . . ? O2 Mn2 O9 C24 171.2(9) 1_655 . . . ? O9 Mn2 O9 C24 -74(100) 3_777 . . . ? O6 Mn2 O9 Mn1 -121.24(18) 3_777 . . . ? O6 Mn2 O9 Mn1 58.76(18) . . . . ? O2 Mn2 O9 Mn1 150.26(19) 3_677 . . . ? O2 Mn2 O9 Mn1 -29.74(19) 1_655 . . . ? O9 Mn2 O9 Mn1 85(100) 3_777 . . . ? O4 Mn3 O10 Mn1 -45.12(18) 4_676 . . . ? O4 Mn3 O10 Mn1 134.88(18) 2_646 . . . ? O7 Mn3 O10 Mn1 50.73(18) 4_576 . . . ? O7 Mn3 O10 Mn1 -129.27(18) 2_746 . . . ? O10 Mn3 O10 Mn1 -136(100) 3_767 . . . ? O8 Mn1 O10 Mn3 -48.45(18) 4_576 . . . ? O5 Mn1 O10 Mn3 -140.10(18) . . . . ? O3 Mn1 O10 Mn3 39.3(2) 4_676 . . . ? O1 Mn1 O10 Mn3 121.93(19) 1_655 . . . ? O9 Mn1 O10 Mn3 -152.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.072 _refine_diff_density_min -1.205 _refine_diff_density_rms 0.253 _database_code_depnum_ccdc_archive 'CCDC 929834' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Mn2 N2 O10' _chemical_formula_weight 658.37 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.463(2) _cell_length_b 7.4574(13) _cell_length_c 29.451(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.324(3) _cell_angle_gamma 90.00 _cell_volume 2720.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7553 _exptl_absorpt_correction_T_max 0.8114 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16387 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 28.39 _reflns_number_total 6575 _reflns_number_gt 4490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.5157P] 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 6575 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C1 C 0.8092(3) 0.7336(5) 0.46847(12) 0.0178(7) Uani 1 1 d . . . C2 C 0.6967(3) 0.7217(5) 0.44546(12) 0.0180(7) Uani 1 1 d . . . C3 C 0.6207(3) 0.6105(5) 0.46197(13) 0.0240(8) Uani 1 1 d . . . H3 H 0.6408 0.5380 0.4872 0.029 Uiso 1 1 calc R . . C4 C 0.5155(3) 0.6059(5) 0.44155(13) 0.0260(8) Uani 1 1 d . . . H4 H 0.4649 0.5354 0.4542 0.031 Uiso 1 1 calc R . . C5 C 0.4844(3) 0.7039(5) 0.40281(11) 0.0177(7) Uani 1 1 d . . . C6 C 0.5630(3) 0.8087(5) 0.38454(13) 0.0235(8) Uani 1 1 d . . . H6 H 0.5451 0.8707 0.3574 0.028 Uiso 1 1 calc R . . C7 C 0.6656(3) 0.8202(5) 0.40634(12) 0.0228(8) Uani 1 1 d . . . H7 H 0.7153 0.8956 0.3947 0.027 Uiso 1 1 calc R . . C8 C 0.3695(3) 0.7145(5) 0.38226(12) 0.0166(7) Uani 1 1 d . . . C9 C 0.2878(3) 0.7329(5) 0.41118(12) 0.0190(7) Uani 1 1 d . . . H9 H 0.3069 0.7291 0.4426 0.023 Uiso 1 1 calc R . . C10 C 0.1801(3) 0.7563(4) 0.39505(12) 0.0162(7) Uani 1 1 d . . . C11 C 0.1025(3) 0.7692(5) 0.43107(12) 0.0174(7) Uani 1 1 d . . . C12 C 0.1493(3) 0.7672(4) 0.34790(12) 0.0179(7) Uani 1 1 d . . . C13 C 0.2300(3) 0.7509(5) 0.31891(12) 0.0201(7) Uani 1 1 d . . . H13 H 0.2112 0.7590 0.2875 0.024 Uiso 1 1 calc R . . C14 C 0.3378(3) 0.7229(4) 0.33529(12) 0.0169(7) Uani 1 1 d . . . C15 C 0.4149(3) 0.6889(5) 0.30042(12) 0.0166(7) Uani 1 1 d . . . C16 C 0.0339(3) 0.7947(5) 0.32828(12) 0.0177(7) Uani 1 1 d . . . C17 C -0.0287(3) 0.9249(5) 0.34505(13) 0.0245(8) Uani 1 1 d . . . H17 H 0.0013 1.0007 0.3681 0.029 Uiso 1 1 calc R . . C18 C -0.1364(3) 0.9448(5) 0.32799(13) 0.0236(8) Uani 1 1 d . . . H18 H -0.1776 1.0353 0.3392 0.028 Uiso 1 1 calc R . . C19 C -0.1829(3) 0.8301(5) 0.29425(12) 0.0197(7) Uani 1 1 d . . . C20 C -0.1186(3) 0.7024(5) 0.27622(14) 0.0277(9) Uani 1 1 d . . . H20 H -0.1483 0.6265 0.2531 0.033 Uiso 1 1 calc R . . C21 C -0.0103(3) 0.6870(5) 0.29245(13) 0.0263(8) Uani 1 1 d . . . H21 H 0.0330 0.6045 0.2793 0.032 Uiso 1 1 calc R . . C22 C -0.3042(3) 0.8371(5) 0.27977(12) 0.0201(7) Uani 1 1 d . . . C23 C -0.1593(3) 0.2515(5) 0.43806(15) 0.0275(9) Uani 1 1 d . . . H23 H -0.2093 0.1935 0.4541 0.033 Uiso 1 1 calc R . . C24 C -0.1217(4) 0.4175(7) 0.37085(17) 0.0523(14) Uani 1 1 d . . . H24A H -0.0500 0.4177 0.3866 0.078 Uiso 1 1 calc R . . H24B H -0.1461 0.5388 0.3660 0.078 Uiso 1 1 calc R . . H24C H -0.1212 0.3583 0.3419 0.078 Uiso 1 1 calc R . . C25 C -0.3074(4) 0.3106(7) 0.37964(19) 0.0513(14) Uani 1 1 d . . . H25A H -0.3473 0.2466 0.4005 0.077 Uiso 1 1 calc R . . H25B H -0.3127 0.2482 0.3510 0.077 Uiso 1 1 calc R . . H25C H -0.3366 0.4291 0.3750 0.077 Uiso 1 1 calc R . . C26 C 0.6446(5) 0.6972(7) 0.15648(19) 0.0531(14) Uani 1 1 d . . . H26 H 0.6925 0.7305 0.1815 0.064 Uiso 1 1 calc R . . C27 C 0.7851(6) 0.7693(8) 0.1093(3) 0.093(3) Uani 1 1 d . . . H27A H 0.8238 0.7998 0.1383 0.140 Uiso 1 1 calc R . . H27B H 0.7807 0.8727 0.0897 0.140 Uiso 1 1 calc R . . H27C H 0.8224 0.6748 0.0954 0.140 Uiso 1 1 calc R . . C28 C 0.6071(6) 0.6580(9) 0.0748(2) 0.085(2) Uani 1 1 d . . . H28A H 0.5384 0.6210 0.0835 0.127 Uiso 1 1 calc R . . H28B H 0.6393 0.5604 0.0599 0.127 Uiso 1 1 calc R . . H28C H 0.5972 0.7581 0.0543 0.127 Uiso 1 1 calc R . . Mn1 Mn 0.0000 0.5000 0.5000 0.01660(19) Uani 1 2 d S . . Mn2 Mn 0.0000 1.0000 0.5000 0.01617(18) Uani 1 2 d S . . Mn3 Mn 0.51589(4) 0.56814(7) 0.232705(18) 0.01758(16) Uani 1 1 d . . . N1 N -0.1946(3) 0.3224(5) 0.39842(12) 0.0320(8) Uani 1 1 d . . . N2 N 0.6784(4) 0.7107(6) 0.11592(18) 0.0610(14) Uani 1 1 d . . . O1 O 0.8438(2) 0.5993(4) 0.49150(10) 0.0288(6) Uani 1 1 d . . . O2 O 0.8605(2) 0.8752(3) 0.46402(9) 0.0264(6) Uani 1 1 d . . . O3 O 0.0516(2) 0.6304(3) 0.43919(9) 0.0238(6) Uani 1 1 d . . . O4 O 0.1008(2) 0.9177(3) 0.45104(9) 0.0267(6) Uani 1 1 d . . . O5 O 0.41796(19) 0.7995(3) 0.26759(8) 0.0196(5) Uani 1 1 d . . . O6 O 0.4665(2) 0.5466(3) 0.30244(9) 0.0245(6) Uani 1 1 d . . . O7 O -0.35510(19) 0.9707(3) 0.29175(9) 0.0235(6) Uani 1 1 d . . . O8 O -0.3422(2) 0.7054(4) 0.25696(11) 0.0325(7) Uani 1 1 d . . . O9 O -0.0639(2) 0.2558(3) 0.45581(9) 0.0257(6) Uani 1 1 d . . . O10 O 0.5519(2) 0.6426(4) 0.16443(10) 0.0383(7) 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 C1 0.0116(16) 0.0258(18) 0.0155(16) -0.0031(14) 0.0000(13) 0.0046(13) C2 0.0110(16) 0.0216(17) 0.0198(17) -0.0012(14) -0.0056(13) 0.0002(13) C3 0.0142(17) 0.039(2) 0.0186(18) 0.0080(16) 0.0012(14) -0.0005(15) C4 0.0138(17) 0.037(2) 0.027(2) 0.0115(17) 0.0003(15) -0.0047(15) C5 0.0128(16) 0.0273(18) 0.0140(16) -0.0020(14) 0.0052(13) -0.0035(13) C6 0.0164(18) 0.031(2) 0.0223(19) 0.0093(16) 0.0005(14) -0.0028(15) C7 0.0162(18) 0.031(2) 0.0212(18) 0.0093(15) 0.0031(14) -0.0050(14) C8 0.0106(16) 0.0220(17) 0.0172(16) 0.0012(14) 0.0009(13) -0.0003(12) C9 0.0168(17) 0.0303(19) 0.0100(15) 0.0003(14) 0.0015(13) 0.0007(14) C10 0.0092(15) 0.0222(17) 0.0168(16) -0.0017(13) 0.0007(13) -0.0012(12) C11 0.0097(15) 0.0280(19) 0.0145(16) 0.0000(14) 0.0009(12) 0.0019(13) C12 0.0118(16) 0.0228(18) 0.0191(17) -0.0028(14) 0.0010(13) -0.0003(13) C13 0.0125(16) 0.033(2) 0.0141(16) -0.0019(14) -0.0026(13) 0.0009(14) C14 0.0138(16) 0.0185(17) 0.0183(17) -0.0007(13) 0.0020(13) -0.0013(13) C15 0.0079(15) 0.0245(17) 0.0168(17) -0.0024(14) -0.0016(12) -0.0022(12) C16 0.0110(16) 0.0258(18) 0.0159(16) 0.0018(14) -0.0005(13) -0.0005(13) C17 0.0176(18) 0.029(2) 0.0258(19) -0.0073(16) -0.0033(15) -0.0020(15) C18 0.0144(17) 0.0280(19) 0.027(2) -0.0043(16) -0.0034(14) 0.0028(14) C19 0.0096(16) 0.0273(19) 0.0212(18) 0.0020(15) -0.0023(13) 0.0002(13) C20 0.0182(19) 0.034(2) 0.028(2) -0.0108(17) -0.0077(15) 0.0020(15) C21 0.0137(17) 0.038(2) 0.027(2) -0.0085(17) -0.0009(15) 0.0060(15) C22 0.0110(16) 0.0285(19) 0.0205(18) 0.0041(15) 0.0009(13) 0.0002(13) C23 0.024(2) 0.0217(19) 0.035(2) -0.0016(16) -0.0040(17) -0.0009(15) C24 0.069(4) 0.053(3) 0.033(3) 0.012(2) -0.005(2) -0.017(3) C25 0.043(3) 0.040(3) 0.062(3) -0.017(3) -0.030(2) 0.015(2) C26 0.072(4) 0.041(3) 0.049(3) -0.003(2) 0.023(3) -0.008(3) C27 0.096(6) 0.058(4) 0.139(7) 0.008(4) 0.075(6) -0.006(4) C28 0.143(7) 0.067(4) 0.049(4) 0.022(3) 0.034(4) 0.027(4) Mn1 0.0107(3) 0.0178(4) 0.0209(4) 0.0026(3) 0.0001(3) 0.0005(3) Mn2 0.0112(3) 0.0187(4) 0.0185(4) -0.0052(3) 0.0010(3) -0.0005(3) Mn3 0.0115(3) 0.0233(3) 0.0180(3) -0.0053(2) 0.00180(19) -0.0020(2) N1 0.038(2) 0.0258(17) 0.0295(19) -0.0021(14) -0.0083(15) 0.0010(14) N2 0.088(4) 0.034(2) 0.070(3) 0.004(2) 0.050(3) -0.001(2) O1 0.0165(13) 0.0328(15) 0.0361(16) 0.0108(12) -0.0020(11) 0.0045(11) O2 0.0172(13) 0.0238(13) 0.0366(16) -0.0035(12) -0.0041(11) -0.0050(10) O3 0.0229(13) 0.0262(13) 0.0237(14) -0.0005(11) 0.0087(11) -0.0058(11) O4 0.0261(14) 0.0292(14) 0.0279(15) -0.0089(12) 0.0167(12) -0.0062(11) O5 0.0172(12) 0.0236(13) 0.0182(12) 0.0024(10) 0.0033(10) -0.0035(10) O6 0.0262(14) 0.0271(14) 0.0207(13) 0.0022(11) 0.0045(11) 0.0078(11) O7 0.0135(12) 0.0322(14) 0.0247(14) 0.0011(11) 0.0008(10) 0.0040(10) O8 0.0130(13) 0.0367(16) 0.0459(18) -0.0145(14) -0.0049(12) -0.0036(11) O9 0.0261(14) 0.0229(13) 0.0265(14) -0.0007(11) -0.0040(11) -0.0022(10) O10 0.0420(18) 0.0439(18) 0.0305(16) 0.0034(14) 0.0104(14) -0.0130(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.249(4) . ? C1 O1 1.259(4) . ? C1 C2 1.491(4) . ? C2 C7 1.385(5) . ? C2 C3 1.387(5) . ? C3 C4 1.382(5) . ? C4 C5 1.374(5) . ? C5 C6 1.405(5) . ? C5 C8 1.494(5) . ? C6 C7 1.369(5) . ? C8 C14 1.398(5) . ? C8 C9 1.404(5) . ? C9 C10 1.385(5) . ? C10 C12 1.402(5) . ? C10 C11 1.516(5) . ? C11 O3 1.251(4) . ? C11 O4 1.255(4) . ? C12 C13 1.395(5) . ? C12 C16 1.504(5) . ? C13 C14 1.392(5) . ? C14 C15 1.503(5) . ? C15 O6 1.240(4) . ? C15 O5 1.275(4) . ? C16 C17 1.371(5) . ? C16 C21 1.390(5) . ? C17 C18 1.389(5) . ? C18 C19 1.389(5) . ? C19 C20 1.388(5) . ? C19 C22 1.525(4) . ? C20 C21 1.386(5) . ? C22 O7 1.253(4) . ? C22 O8 1.253(4) . ? C23 O9 1.246(4) . ? C23 N1 1.313(5) . ? C24 N1 1.467(6) . ? C25 N1 1.455(6) . ? C26 O10 1.271(6) . ? C26 N2 1.314(7) . ? C27 N2 1.433(7) . ? C28 N2 1.474(9) . ? Mn1 O1 2.071(2) 3_666 ? Mn1 O1 2.071(2) 1_455 ? Mn1 O3 2.195(2) 3_566 ? Mn1 O3 2.195(2) . ? Mn1 O9 2.327(3) 3_566 ? Mn1 O9 2.327(3) . ? Mn2 O4 2.105(2) . ? Mn2 O4 2.105(2) 3_576 ? Mn2 O2 2.146(2) 3_676 ? Mn2 O2 2.146(2) 1_455 ? Mn2 O9 2.396(3) 3_566 ? Mn2 O9 2.396(3) 1_565 ? Mn3 O8 2.099(3) 1_655 ? Mn3 O5 2.166(2) 2_645 ? Mn3 O7 2.178(2) 2_545 ? Mn3 O10 2.180(3) . ? Mn3 O6 2.214(3) . ? Mn3 O5 2.408(2) . ? O1 Mn1 2.071(2) 1_655 ? O2 Mn2 2.146(2) 1_655 ? O5 Mn3 2.166(2) 2_655 ? O7 Mn3 2.178(2) 2 ? O8 Mn3 2.099(3) 1_455 ? O9 Mn2 2.396(3) 1_545 ? 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 O2 C1 O1 125.5(3) . . ? O2 C1 C2 118.0(3) . . ? O1 C1 C2 116.6(3) . . ? C7 C2 C3 118.0(3) . . ? C7 C2 C1 120.7(3) . . ? C3 C2 C1 121.4(3) . . ? C4 C3 C2 121.0(3) . . ? C5 C4 C3 121.0(3) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 C8 122.3(3) . . ? C6 C5 C8 119.5(3) . . ? C7 C6 C5 120.6(3) . . ? C6 C7 C2 121.2(3) . . ? C14 C8 C9 116.8(3) . . ? C14 C8 C5 123.8(3) . . ? C9 C8 C5 119.1(3) . . ? C10 C9 C8 123.0(3) . . ? C9 C10 C12 119.8(3) . . ? C9 C10 C11 115.9(3) . . ? C12 C10 C11 124.3(3) . . ? O3 C11 O4 127.3(3) . . ? O3 C11 C10 117.2(3) . . ? O4 C11 C10 115.4(3) . . ? C13 C12 C10 117.7(3) . . ? C13 C12 C16 120.0(3) . . ? C10 C12 C16 122.3(3) . . ? C14 C13 C12 122.3(3) . . ? C13 C14 C8 120.4(3) . . ? C13 C14 C15 117.0(3) . . ? C8 C14 C15 122.5(3) . . ? O6 C15 O5 122.1(3) . . ? O6 C15 C14 118.6(3) . . ? O5 C15 C14 119.0(3) . . ? C17 C16 C21 119.2(3) . . ? C17 C16 C12 121.1(3) . . ? C21 C16 C12 119.7(3) . . ? C16 C17 C18 120.8(3) . . ? C19 C18 C17 120.2(3) . . ? C20 C19 C18 118.9(3) . . ? C20 C19 C22 120.9(3) . . ? C18 C19 C22 120.1(3) . . ? C21 C20 C19 120.4(3) . . ? C20 C21 C16 120.2(3) . . ? O7 C22 O8 126.9(3) . . ? O7 C22 C19 117.7(3) . . ? O8 C22 C19 115.3(3) . . ? O9 C23 N1 125.0(4) . . ? O10 C26 N2 125.6(6) . . ? O1 Mn1 O1 180.000(1) 3_666 1_455 ? O1 Mn1 O3 95.67(10) 3_666 3_566 ? O1 Mn1 O3 84.33(10) 1_455 3_566 ? O1 Mn1 O3 84.33(10) 3_666 . ? O1 Mn1 O3 95.67(10) 1_455 . ? O3 Mn1 O3 180.0 3_566 . ? O1 Mn1 O9 87.31(10) 3_666 3_566 ? O1 Mn1 O9 92.69(10) 1_455 3_566 ? O3 Mn1 O9 90.18(9) 3_566 3_566 ? O3 Mn1 O9 89.82(10) . 3_566 ? O1 Mn1 O9 92.69(10) 3_666 . ? O1 Mn1 O9 87.31(10) 1_455 . ? O3 Mn1 O9 89.82(10) 3_566 . ? O3 Mn1 O9 90.18(9) . . ? O9 Mn1 O9 180.0 3_566 . ? O4 Mn2 O4 180.000(1) . 3_576 ? O4 Mn2 O2 87.28(10) . 3_676 ? O4 Mn2 O2 92.72(10) 3_576 3_676 ? O4 Mn2 O2 92.72(10) . 1_455 ? O4 Mn2 O2 87.28(10) 3_576 1_455 ? O2 Mn2 O2 180.0 3_676 1_455 ? O4 Mn2 O9 87.26(10) . 3_566 ? O4 Mn2 O9 92.74(10) 3_576 3_566 ? O2 Mn2 O9 82.78(9) 3_676 3_566 ? O2 Mn2 O9 97.22(9) 1_455 3_566 ? O4 Mn2 O9 92.74(10) . 1_565 ? O4 Mn2 O9 87.26(10) 3_576 1_565 ? O2 Mn2 O9 97.22(9) 3_676 1_565 ? O2 Mn2 O9 82.78(9) 1_455 1_565 ? O9 Mn2 O9 180.00(11) 3_566 1_565 ? O8 Mn3 O5 98.36(10) 1_655 2_645 ? O8 Mn3 O7 170.07(10) 1_655 2_545 ? O5 Mn3 O7 91.54(10) 2_645 2_545 ? O8 Mn3 O10 86.47(12) 1_655 . ? O5 Mn3 O10 96.58(11) 2_645 . ? O7 Mn3 O10 93.17(11) 2_545 . ? O8 Mn3 O6 91.70(11) 1_655 . ? O5 Mn3 O6 94.67(9) 2_645 . ? O7 Mn3 O6 86.71(10) 2_545 . ? O10 Mn3 O6 168.75(11) . . ? O8 Mn3 O5 87.30(9) 1_655 . ? O5 Mn3 O5 151.07(6) 2_645 . ? O7 Mn3 O5 83.64(9) 2_545 . ? O10 Mn3 O5 112.12(10) . . ? O6 Mn3 O5 56.67(9) . . ? C23 N1 C25 121.9(4) . . ? C23 N1 C24 121.3(4) . . ? C25 N1 C24 116.8(4) . . ? C26 N2 C27 122.9(7) . . ? C26 N2 C28 120.1(5) . . ? C27 N2 C28 117.0(6) . . ? C1 O1 Mn1 127.7(2) . 1_655 ? C1 O2 Mn2 135.3(2) . 1_655 ? C11 O3 Mn1 136.3(2) . . ? C11 O4 Mn2 128.3(2) . . ? C15 O5 Mn3 130.1(2) . 2_655 ? C15 O5 Mn3 85.35(19) . . ? Mn3 O5 Mn3 116.74(10) 2_655 . ? C15 O6 Mn3 95.1(2) . . ? C22 O7 Mn3 130.4(2) . 2 ? C22 O8 Mn3 145.0(2) . 1_455 ? C23 O9 Mn1 120.5(2) . . ? C23 O9 Mn2 116.9(2) . 1_545 ? Mn1 O9 Mn2 104.28(10) . 1_545 ? C26 O10 Mn3 122.4(3) . . ? 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 O2 C1 C2 C7 27.3(5) . . . . ? O1 C1 C2 C7 -153.7(3) . . . . ? O2 C1 C2 C3 -153.6(3) . . . . ? O1 C1 C2 C3 25.3(5) . . . . ? C7 C2 C3 C4 -3.6(6) . . . . ? C1 C2 C3 C4 177.3(3) . . . . ? C2 C3 C4 C5 3.6(6) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C3 C4 C5 C8 -174.5(3) . . . . ? C4 C5 C6 C7 -3.7(6) . . . . ? C8 C5 C6 C7 171.1(3) . . . . ? C5 C6 C7 C2 3.7(6) . . . . ? C3 C2 C7 C6 0.0(6) . . . . ? C1 C2 C7 C6 179.1(3) . . . . ? C4 C5 C8 C14 -144.4(4) . . . . ? C6 C5 C8 C14 41.0(5) . . . . ? C4 C5 C8 C9 41.3(5) . . . . ? C6 C5 C8 C9 -133.2(4) . . . . ? C14 C8 C9 C10 0.7(5) . . . . ? C5 C8 C9 C10 175.3(3) . . . . ? C8 C9 C10 C12 -1.7(5) . . . . ? C8 C9 C10 C11 178.6(3) . . . . ? C9 C10 C11 O3 -98.8(4) . . . . ? C12 C10 C11 O3 81.4(4) . . . . ? C9 C10 C11 O4 77.8(4) . . . . ? C12 C10 C11 O4 -102.0(4) . . . . ? C9 C10 C12 C13 1.0(5) . . . . ? C11 C10 C12 C13 -179.3(3) . . . . ? C9 C10 C12 C16 -179.3(3) . . . . ? C11 C10 C12 C16 0.5(5) . . . . ? C10 C12 C13 C14 0.7(5) . . . . ? C16 C12 C13 C14 -179.1(3) . . . . ? C12 C13 C14 C8 -1.6(5) . . . . ? C12 C13 C14 C15 173.9(3) . . . . ? C9 C8 C14 C13 0.9(5) . . . . ? C5 C8 C14 C13 -173.4(3) . . . . ? C9 C8 C14 C15 -174.4(3) . . . . ? C5 C8 C14 C15 11.2(5) . . . . ? C13 C14 C15 O6 -121.1(4) . . . . ? C8 C14 C15 O6 54.4(5) . . . . ? C13 C14 C15 O5 52.9(4) . . . . ? C8 C14 C15 O5 -131.7(4) . . . . ? C13 C12 C16 C17 -132.5(4) . . . . ? C10 C12 C16 C17 47.7(5) . . . . ? C13 C12 C16 C21 47.3(5) . . . . ? C10 C12 C16 C21 -132.5(4) . . . . ? C21 C16 C17 C18 2.8(6) . . . . ? C12 C16 C17 C18 -177.4(3) . . . . ? C16 C17 C18 C19 1.4(6) . . . . ? C17 C18 C19 C20 -3.5(6) . . . . ? C17 C18 C19 C22 172.4(3) . . . . ? C18 C19 C20 C21 1.5(6) . . . . ? C22 C19 C20 C21 -174.4(4) . . . . ? C19 C20 C21 C16 2.7(6) . . . . ? C17 C16 C21 C20 -4.8(6) . . . . ? C12 C16 C21 C20 175.4(4) . . . . ? C20 C19 C22 O7 -169.4(4) . . . . ? C18 C19 C22 O7 14.7(5) . . . . ? C20 C19 C22 O8 10.9(5) . . . . ? C18 C19 C22 O8 -165.0(3) . . . . ? O9 C23 N1 C25 179.4(4) . . . . ? O9 C23 N1 C24 -0.4(6) . . . . ? O10 C26 N2 C27 -178.4(5) . . . . ? O10 C26 N2 C28 -0.8(8) . . . . ? O2 C1 O1 Mn1 -35.5(5) . . . 1_655 ? C2 C1 O1 Mn1 145.6(3) . . . 1_655 ? O1 C1 O2 Mn2 -18.0(6) . . . 1_655 ? C2 C1 O2 Mn2 160.9(2) . . . 1_655 ? O4 C11 O3 Mn1 -34.9(6) . . . . ? C10 C11 O3 Mn1 141.2(3) . . . . ? O1 Mn1 O3 C11 -81.7(3) 3_666 . . . ? O1 Mn1 O3 C11 98.3(3) 1_455 . . . ? O3 Mn1 O3 C11 -67(100) 3_566 . . . ? O9 Mn1 O3 C11 5.6(3) 3_566 . . . ? O9 Mn1 O3 C11 -174.4(3) . . . . ? O3 C11 O4 Mn2 -7.8(6) . . . . ? C10 C11 O4 Mn2 176.0(2) . . . . ? O4 Mn2 O4 C11 -33(100) 3_576 . . . ? O2 Mn2 O4 C11 138.7(3) 3_676 . . . ? O2 Mn2 O4 C11 -41.3(3) 1_455 . . . ? O9 Mn2 O4 C11 55.8(3) 3_566 . . . ? O9 Mn2 O4 C11 -124.2(3) 1_565 . . . ? O6 C15 O5 Mn3 -113.1(3) . . . 2_655 ? C14 C15 O5 Mn3 73.2(4) . . . 2_655 ? O6 C15 O5 Mn3 8.4(3) . . . . ? C14 C15 O5 Mn3 -165.3(3) . . . . ? O8 Mn3 O5 C15 -98.6(2) 1_655 . . . ? O5 Mn3 O5 C15 3.9(2) 2_645 . . . ? O7 Mn3 O5 C15 85.50(19) 2_545 . . . ? O10 Mn3 O5 C15 176.35(19) . . . . ? O6 Mn3 O5 C15 -4.75(18) . . . . ? O8 Mn3 O5 Mn3 34.53(13) 1_655 . . 2_655 ? O5 Mn3 O5 Mn3 137.00(17) 2_645 . . 2_655 ? O7 Mn3 O5 Mn3 -141.40(13) 2_545 . . 2_655 ? O10 Mn3 O5 Mn3 -50.55(15) . . . 2_655 ? O6 Mn3 O5 Mn3 128.35(16) . . . 2_655 ? O5 C15 O6 Mn3 -9.1(4) . . . . ? C14 C15 O6 Mn3 164.6(3) . . . . ? O8 Mn3 O6 C15 90.5(2) 1_655 . . . ? O5 Mn3 O6 C15 -170.9(2) 2_645 . . . ? O7 Mn3 O6 C15 -79.7(2) 2_545 . . . ? O10 Mn3 O6 C15 10.1(7) . . . . ? O5 Mn3 O6 C15 4.89(19) . . . . ? O8 C22 O7 Mn3 -15.9(6) . . . 2 ? C19 C22 O7 Mn3 164.4(2) . . . 2 ? O7 C22 O8 Mn3 -15.1(7) . . . 1_455 ? C19 C22 O8 Mn3 164.6(3) . . . 1_455 ? N1 C23 O9 Mn1 86.1(4) . . . . ? N1 C23 O9 Mn2 -145.7(3) . . . 1_545 ? O1 Mn1 O9 C23 -175.6(3) 3_666 . . . ? O1 Mn1 O9 C23 4.4(3) 1_455 . . . ? O3 Mn1 O9 C23 88.7(3) 3_566 . . . ? O3 Mn1 O9 C23 -91.3(3) . . . . ? O9 Mn1 O9 C23 43(100) 3_566 . . . ? O1 Mn1 O9 Mn2 50.69(11) 3_666 . . 1_545 ? O1 Mn1 O9 Mn2 -129.31(11) 1_455 . . 1_545 ? O3 Mn1 O9 Mn2 -44.98(11) 3_566 . . 1_545 ? O3 Mn1 O9 Mn2 135.02(11) . . . 1_545 ? O9 Mn1 O9 Mn2 -91(100) 3_566 . . 1_545 ? N2 C26 O10 Mn3 165.8(4) . . . . ? O8 Mn3 O10 C26 16.2(4) 1_655 . . . ? O5 Mn3 O10 C26 -81.8(4) 2_645 . . . ? O7 Mn3 O10 C26 -173.7(4) 2_545 . . . ? O6 Mn3 O10 C26 97.2(7) . . . . ? O5 Mn3 O10 C26 101.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.690 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.189 _database_code_depnum_ccdc_archive 'CCDC 929835'