# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_submission _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- 825564.cif' _publ_contact_author_name 'En-Qing Gao' _publ_contact_author_address ; Department of Chemistry, East China Normal University, Shanghai 200062, China. ; _publ_contact_author_email eqgao@chem.ecnu.edu.cn _publ_contact_author_phone 86-21-62233404 _publ_contact_author_fax 86-21-62233404 _publ_author_name 'En-Qing Gao' data_1 _database_code_depnum_ccdc_archive 'CCDC 825564' #TrackingRef '- 825564.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 Mn N4 O7' _chemical_formula_weight 384.24 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 Orthorhombic _symmetry_space_group_name_H-M Pmna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x+1/2, y, -z+1/2' 'x, -y, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x-1/2, -y, z-1/2' '-x, y, z' _cell_length_a 7.2233(3) _cell_length_b 11.4170(4) _cell_length_c 20.3946(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1681.91(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8012 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9368 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 21730 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2234 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0578P)^2^+1.4684P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2234 _refine_ls_number_parameters 145 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.161 _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 Mn1 Mn 0.2500 -0.24286(4) 0.2500 0.02345(16) Uani 1 2 d S . . C1 C 0.0000 -0.0660(3) 0.16870(15) 0.0289(6) Uani 1 2 d S . . C2 C 0.0000 0.0266(3) 0.11479(16) 0.0321(7) Uani 1 2 d S . . C3 C 0.1625(4) 0.0670(3) 0.08899(15) 0.0546(8) Uani 1 1 d . . . H3A H 0.2749 0.0425 0.1065 0.066 Uiso 1 1 calc R . . C4 C 0.1596(4) 0.1441(3) 0.03691(16) 0.0582(8) Uani 1 1 d . . . H4A H 0.2703 0.1714 0.0194 0.070 Uiso 1 1 calc R . . C5 C 0.0000 0.2606(3) -0.04559(18) 0.0439(9) Uani 1 2 d S . . H5A H -0.1087 0.2463 -0.0723 0.053 Uiso 0.50 1 calc PR . . H5B H 0.1087 0.2463 -0.0723 0.053 Uiso 0.50 1 calc PR . . C6 C 0.0000 0.3854(3) -0.02250(16) 0.0387(8) Uani 1 2 d S . . C7 C -0.1653(4) 0.4426(2) -0.01141(14) 0.0472(6) Uani 1 1 d . . . H7A H -0.2769 0.4044 -0.0192 0.057 Uiso 1 1 calc R . . C8 C 0.0000 -0.4329(3) 0.18187(15) 0.0303(7) Uani 1 2 d S . . C9 C 0.0000 -0.5622(4) 0.1686(2) 0.0564(11) Uani 1 2 d S . . H9A H 0.1253 -0.5898 0.1657 0.085 Uiso 0.50 1 calc PR . . H9B H -0.0628 -0.5775 0.1280 0.085 Uiso 0.50 1 calc PR . . H9C H -0.0625 -0.6022 0.2037 0.085 Uiso 0.50 1 calc PR . . O1 O 0.1533(2) -0.10140(18) 0.18649(9) 0.0488(5) Uani 1 1 d . . . O2 O 0.1530(2) -0.38274(16) 0.18721(8) 0.0412(4) Uani 1 1 d . . . N1 N 0.0000 -0.2375(3) 0.31195(13) 0.0314(6) Uani 1 2 d S . . N2 N 0.0000 -0.2136(3) 0.36858(14) 0.0398(7) Uani 1 2 d S . . N3 N 0.0000 -0.1908(5) 0.42375(17) 0.0755(14) Uani 1 2 d S . . N4 N 0.0000 0.1794(2) 0.01177(13) 0.0368(7) Uani 1 2 d S . . O3 O 0.0000 0.2673(11) 0.3933(8) 0.122(5) Uani 0.50 2 d SP . . O3' O 0.0000 0.2451(9) 0.3418(11) 0.137(6) Uani 0.50 2 d SP . . O5 O 0.0000 -0.5062(4) 0.3520(2) 0.0850(12) Uani 1 2 d SD . . H5W2 H 0.0000 -0.440(3) 0.333(3) 0.127 Uiso 1 2 d SD . . H5W1 H 0.0000 -0.560(4) 0.323(3) 0.127 Uiso 1 2 d SD . . O4 O 0.2500 0.1489(6) 0.2500 0.173(5) Uani 0.837(12) 2 d SP . . O4' O 0.0000 0.061(3) 0.3038(16) 0.116(15) Uani 0.163(12) 2 d SP . . 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 Mn1 0.0153(2) 0.0304(3) 0.0246(2) 0.000 0.00013(16) 0.000 C1 0.0275(15) 0.0260(15) 0.0331(15) 0.0033(12) 0.000 0.000 C2 0.0312(16) 0.0289(16) 0.0360(16) 0.0052(13) 0.000 0.000 C3 0.0324(14) 0.0651(18) 0.0664(18) 0.0331(15) 0.0006(13) 0.0015(13) C4 0.0392(15) 0.0666(19) 0.0688(19) 0.0339(16) 0.0108(14) 0.0006(14) C5 0.072(3) 0.0339(19) 0.0257(16) 0.0043(13) 0.000 0.000 C6 0.054(2) 0.0324(17) 0.0295(16) 0.0049(13) 0.000 0.000 C7 0.0450(15) 0.0402(14) 0.0562(16) 0.0047(12) -0.0042(13) -0.0053(12) C8 0.0295(16) 0.0336(16) 0.0278(15) -0.0043(12) 0.000 0.000 C9 0.066(3) 0.039(2) 0.065(3) -0.0035(19) 0.000 0.000 O1 0.0289(9) 0.0581(12) 0.0592(11) 0.0297(9) 0.0031(8) 0.0076(8) O2 0.0275(9) 0.0505(10) 0.0454(9) -0.0157(8) 0.0000(7) -0.0044(8) N1 0.0172(12) 0.0500(17) 0.0269(13) -0.0036(11) 0.000 0.000 N2 0.0199(13) 0.066(2) 0.0329(15) -0.0043(14) 0.000 0.000 N3 0.047(2) 0.147(4) 0.0324(18) -0.023(2) 0.000 0.000 N4 0.0499(18) 0.0284(14) 0.0320(14) 0.0031(11) 0.000 0.000 O3 0.147(12) 0.090(8) 0.129(10) 0.021(7) 0.000 0.000 O3' 0.122(11) 0.058(6) 0.230(18) 0.028(9) 0.000 0.000 O5 0.065(2) 0.065(2) 0.125(4) 0.035(2) 0.000 0.000 O4 0.285(13) 0.086(5) 0.147(7) 0.000 -0.041(7) 0.000 O4' 0.067(17) 0.15(3) 0.13(3) -0.09(2) 0.000 0.000 _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 Mn1 O2 2.1637(17) . ? Mn1 O2 2.1637(17) 3 ? Mn1 O1 2.1849(17) 3 ? Mn1 O1 2.1849(17) . ? Mn1 N1 2.2048(15) 6_656 ? Mn1 N1 2.2048(15) . ? C1 O1 1.234(2) . ? C1 O1 1.234(2) 8 ? C1 C2 1.525(4) . ? C2 C3 1.366(3) 8 ? C2 C3 1.366(3) . ? C3 C4 1.380(4) . ? C3 H3A 0.9300 . ? C4 N4 1.325(3) . ? C4 H4A 0.9300 . ? C5 N4 1.493(4) . ? C5 C6 1.500(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.380(3) 8 ? C6 C7 1.380(3) . ? C7 C7 1.391(5) 4_565 ? C7 H7A 0.9300 . ? C8 O2 1.249(2) . ? C8 O2 1.249(2) 8 ? C8 C9 1.501(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N1 N2 1.187(4) . ? N1 Mn1 2.2048(15) 6_556 ? N2 N3 1.155(4) . ? N4 C4 1.325(3) 8 ? O3 O3' 1.080(19) . ? O5 H5W2 0.85(2) . ? O5 H5W1 0.845(19) . ? 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 Mn1 O2 84.86(10) . 3 ? O2 Mn1 O1 179.74(6) . 3 ? O2 Mn1 O1 95.23(8) 3 3 ? O2 Mn1 O1 95.23(8) . . ? O2 Mn1 O1 179.74(6) 3 . ? O1 Mn1 O1 84.68(12) 3 . ? O2 Mn1 N1 86.95(8) . 6_656 ? O2 Mn1 N1 95.43(8) 3 6_656 ? O1 Mn1 N1 93.28(8) 3 6_656 ? O1 Mn1 N1 84.34(8) . 6_656 ? O2 Mn1 N1 95.43(8) . . ? O2 Mn1 N1 86.95(8) 3 . ? O1 Mn1 N1 84.34(8) 3 . ? O1 Mn1 N1 93.28(8) . . ? N1 Mn1 N1 176.79(15) 6_656 . ? O1 C1 O1 127.7(3) . 8 ? O1 C1 C2 116.06(15) . . ? O1 C1 C2 116.06(15) 8 . ? C3 C2 C3 118.4(3) 8 . ? C3 C2 C1 120.74(16) 8 . ? C3 C2 C1 120.74(16) . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? N4 C4 C3 120.4(3) . . ? N4 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N4 C5 C6 110.1(3) . . ? N4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C7 119.9(3) 8 . ? C7 C6 C5 120.06(17) 8 . ? C7 C6 C5 120.06(17) . . ? C6 C7 C7 120.07(17) . 4_565 ? C6 C7 H7A 120.0 . . ? C7 C7 H7A 120.0 4_565 . ? O2 C8 O2 124.4(3) . 8 ? O2 C8 C9 117.80(16) . . ? O2 C8 C9 117.80(16) 8 . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 O1 Mn1 134.73(17) . . ? C8 O2 Mn1 132.55(17) . . ? N2 N1 Mn1 124.34(7) . 6_556 ? N2 N1 Mn1 124.34(7) . . ? Mn1 N1 Mn1 109.98(11) 6_556 . ? N3 N2 N1 179.7(5) . . ? C4 N4 C4 121.0(3) . 8 ? C4 N4 C5 119.51(15) . . ? C4 N4 C5 119.51(15) 8 . ? H5W2 O5 H5W1 110(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.458 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.074 # Attachment '- 825565.cif' #TrackingRef '- 825565.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 825565' #TrackingRef '- 825565.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Mn2 N14 O7' _chemical_formula_weight 694.42 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7321(2) _cell_length_b 12.8829(3) _cell_length_c 13.4251(3) _cell_angle_alpha 117.7680(10) _cell_angle_beta 93.6470(10) _cell_angle_gamma 104.5730(10) _cell_volume 1408.95(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7396 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.04 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9268 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 18238 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.51 _reflns_number_total 5733 _reflns_number_gt 4756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0443P)^2^+1.3514P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5733 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _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 Mn1 Mn 0.07590(3) 0.16051(3) 0.07926(3) 0.02952(10) Uani 1 1 d . . . Mn2 Mn 0.41108(3) 0.35212(3) 0.13069(3) 0.03049(10) Uani 1 1 d . . . C1 C 0.1232(2) 0.41615(19) 0.10165(18) 0.0290(4) Uani 1 1 d . . . C2 C 0.0670(2) 0.52612(19) 0.13806(17) 0.0271(4) Uani 1 1 d . . . C3 C -0.0796(2) 0.5119(2) 0.12649(18) 0.0298(5) Uani 1 1 d . . . H3A H -0.1475 0.4334 0.0940 0.036 Uiso 1 1 calc R . . C4 C -0.1248(2) 0.6145(2) 0.16334(19) 0.0308(5) Uani 1 1 d . . . H4A H -0.2235 0.6049 0.1549 0.037 Uiso 1 1 calc R . . C5 C 0.1163(3) 0.7440(2) 0.2232(2) 0.0391(5) Uani 1 1 d . . . H5A H 0.1823 0.8234 0.2566 0.047 Uiso 1 1 calc R . . C6 C 0.1656(2) 0.6444(2) 0.1866(2) 0.0356(5) Uani 1 1 d . . . H6A H 0.2647 0.6559 0.1941 0.043 Uiso 1 1 calc R . . C7 C -0.0775(3) 0.8395(2) 0.2510(2) 0.0368(5) Uani 1 1 d . . . H7A H -0.1822 0.8126 0.2262 0.044 Uiso 1 1 calc R . . H7B H -0.0347 0.8865 0.2152 0.044 Uiso 1 1 calc R . . C8 C -0.0362(2) 0.9222(2) 0.3804(2) 0.0341(5) Uani 1 1 d . . . C9 C -0.1204(3) 0.8960(2) 0.4495(2) 0.0441(6) Uani 1 1 d . . . H9A H -0.202(4) 0.823(3) 0.417(3) 0.064(9) Uiso 1 1 d . . . C10 C 0.0847(3) 1.0277(2) 0.4318(2) 0.0441(6) Uani 1 1 d . . . H10A H 0.147(3) 1.045(3) 0.389(2) 0.048(8) Uiso 1 1 d . . . C11 C -0.1312(2) 0.4987(2) 0.35609(19) 0.0346(5) Uani 1 1 d . . . C12 C 0.0235(2) 0.5792(2) 0.42074(18) 0.0290(4) Uani 1 1 d . . . C13 C 0.0474(3) 0.7032(2) 0.4985(2) 0.0371(5) Uani 1 1 d . . . H13A H -0.0307 0.7334 0.5139 0.044 Uiso 1 1 calc R . . C14 C 0.1857(3) 0.7809(2) 0.5525(2) 0.0401(6) Uani 1 1 d . . . H14A H 0.2015 0.8640 0.6043 0.048 Uiso 1 1 calc R . . C15 C 0.2798(3) 0.6189(2) 0.4581(2) 0.0393(5) Uani 1 1 d . . . H15A H 0.3596 0.5908 0.4446 0.047 Uiso 1 1 calc R . . C16 C 0.1417(3) 0.5373(2) 0.4022(2) 0.0362(5) Uani 1 1 d . . . H16A H 0.1283 0.4541 0.3520 0.043 Uiso 1 1 calc R . . C17 C 0.4486(3) 0.8301(2) 0.5891(2) 0.0444(6) Uani 1 1 d . . . H17A H 0.5204 0.7874 0.5741 0.053 Uiso 1 1 calc R . . H17B H 0.4561 0.8752 0.6717 0.053 Uiso 1 1 calc R . . C18 C 0.4775(2) 0.9194(2) 0.5436(2) 0.0365(5) Uani 1 1 d . . . C19 C 0.4857(3) 1.0419(2) 0.6131(2) 0.0434(6) Uani 1 1 d . . . H19A H 0.475(3) 1.069(3) 0.689(3) 0.053(8) Uiso 1 1 d . . . C20 C 0.4923(3) 0.8790(2) 0.4309(2) 0.0432(6) Uani 1 1 d . . . H20A H 0.493(3) 0.799(3) 0.386(2) 0.043(7) Uiso 1 1 d . . . C21 C 0.5823(5) 0.1639(3) 0.0867(4) 0.114(2) Uani 1 1 d . . . H21A H 0.6546 0.1425 0.1184 0.170 Uiso 1 1 calc R . . H21B H 0.6111 0.1743 0.0240 0.170 Uiso 1 1 calc R . . H21C H 0.4909 0.0991 0.0593 0.170 Uiso 1 1 calc R . . N1 N 0.0907(2) -0.01370(17) 0.07459(18) 0.0401(5) Uani 1 1 d . . . N2 N 0.1861(2) -0.01808(17) 0.13072(18) 0.0376(5) Uani 1 1 d . . . N3 N 0.2769(3) -0.0224(3) 0.1862(3) 0.0704(8) Uani 1 1 d . . . N4 N 0.2582(2) 0.17205(18) -0.01604(17) 0.0372(4) Uani 1 1 d . . . N5 N 0.2703(2) 0.09332(16) -0.10331(16) 0.0305(4) Uani 1 1 d . . . N6 N 0.2794(3) 0.01611(19) -0.19030(19) 0.0483(5) Uani 1 1 d . . . N7 N 0.2636(2) 0.28889(19) 0.22422(17) 0.0388(5) Uani 1 1 d . . . N8 N 0.2868(3) 0.2957(2) 0.3149(2) 0.0541(6) Uani 1 1 d . . . N9 N 0.3064(5) 0.3028(5) 0.4029(3) 0.1253(18) Uani 1 1 d . . . N10 N 0.5401(2) 0.3830(2) 0.0139(2) 0.0470(5) Uani 1 1 d . . . N11 N 0.4929(2) 0.34754(17) -0.08323(19) 0.0371(5) Uani 1 1 d . . . N12 N 0.4476(3) 0.3121(2) -0.1802(2) 0.0470(5) Uani 1 1 d . . . N13 N -0.0278(2) 0.72804(16) 0.21130(15) 0.0304(4) Uani 1 1 d . . . N14 N 0.2996(2) 0.73806(17) 0.53145(16) 0.0343(4) Uani 1 1 d . . . O1 O -0.0569(2) 0.19157(19) 0.20798(18) 0.0494(5) Uani 1 1 d . . . H1W1 H -0.085(4) 0.256(4) 0.234(3) 0.074(11) Uiso 1 1 d . . . H1W2 H -0.120(4) 0.134(4) 0.210(3) 0.078(12) Uiso 1 1 d . . . O2 O 0.51702(18) 0.53444(15) 0.28003(15) 0.0404(4) Uani 1 1 d . . . H2W2 H 0.5819 0.5304 0.3023 0.061 Uiso 1 1 d R . . H2W1 H 0.532(4) 0.590(3) 0.255(3) 0.071(11) Uiso 1 1 d . . . O3 O 0.5681(2) 0.27510(16) 0.17239(18) 0.0555(5) Uani 1 1 d . . . H3B H 0.6476 0.3105 0.2071 0.083 Uiso 1 1 d R . . O4 O 0.03117(17) 0.31406(14) 0.07076(15) 0.0391(4) Uani 1 1 d . . . O5 O 0.25666(17) 0.44007(15) 0.10780(16) 0.0394(4) Uani 1 1 d . . . O6 O -0.15913(19) 0.38400(16) 0.30555(16) 0.0490(5) Uani 1 1 d . . . O7 O -0.2162(2) 0.55609(18) 0.35869(18) 0.0600(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.02673(17) 0.02163(16) 0.03545(19) 0.01164(14) 0.00521(13) 0.00584(12) Mn2 0.02431(17) 0.02592(17) 0.03595(19) 0.01216(14) 0.00439(13) 0.00676(13) C1 0.0317(11) 0.0277(11) 0.0294(11) 0.0148(9) 0.0059(9) 0.0115(9) C2 0.0297(11) 0.0283(10) 0.0259(10) 0.0138(9) 0.0082(8) 0.0121(8) C3 0.0297(11) 0.0271(10) 0.0318(11) 0.0144(9) 0.0071(9) 0.0081(9) C4 0.0265(11) 0.0319(11) 0.0341(11) 0.0160(10) 0.0074(9) 0.0101(9) C5 0.0319(12) 0.0261(11) 0.0520(14) 0.0149(11) 0.0052(11) 0.0079(9) C6 0.0259(11) 0.0318(11) 0.0453(13) 0.0159(10) 0.0075(10) 0.0102(9) C7 0.0416(13) 0.0304(11) 0.0415(13) 0.0163(10) 0.0064(10) 0.0200(10) C8 0.0339(12) 0.0284(11) 0.0419(13) 0.0155(10) 0.0088(10) 0.0171(9) C9 0.0374(13) 0.0301(12) 0.0487(15) 0.0100(11) 0.0121(11) 0.0044(10) C10 0.0447(14) 0.0366(13) 0.0475(15) 0.0191(12) 0.0180(12) 0.0093(11) C11 0.0326(12) 0.0369(12) 0.0266(11) 0.0113(10) 0.0056(9) 0.0082(10) C12 0.0314(11) 0.0302(11) 0.0255(10) 0.0142(9) 0.0070(9) 0.0093(9) C13 0.0332(12) 0.0348(12) 0.0395(13) 0.0140(10) 0.0082(10) 0.0141(10) C14 0.0401(13) 0.0298(12) 0.0404(13) 0.0101(10) 0.0081(11) 0.0105(10) C15 0.0325(12) 0.0384(13) 0.0484(14) 0.0204(11) 0.0113(10) 0.0155(10) C16 0.0361(12) 0.0282(11) 0.0389(12) 0.0113(10) 0.0093(10) 0.0121(9) C17 0.0306(12) 0.0451(14) 0.0469(14) 0.0221(12) -0.0034(10) 0.0001(10) C18 0.0256(11) 0.0371(12) 0.0396(13) 0.0169(10) 0.0028(9) 0.0037(9) C19 0.0413(14) 0.0393(13) 0.0356(13) 0.0113(11) 0.0117(11) 0.0047(11) C20 0.0425(14) 0.0308(12) 0.0423(14) 0.0091(11) 0.0129(11) 0.0074(10) C21 0.116(3) 0.051(2) 0.109(3) -0.012(2) -0.054(3) 0.051(2) N1 0.0366(11) 0.0263(9) 0.0484(12) 0.0154(9) -0.0060(9) 0.0059(8) N2 0.0363(11) 0.0308(10) 0.0450(11) 0.0205(9) 0.0043(9) 0.0074(8) N3 0.0585(16) 0.0725(18) 0.0831(19) 0.0458(16) -0.0119(14) 0.0181(14) N4 0.0317(10) 0.0313(10) 0.0341(10) 0.0071(9) 0.0075(8) 0.0057(8) N5 0.0311(10) 0.0260(9) 0.0353(11) 0.0168(9) 0.0072(8) 0.0073(7) N6 0.0641(15) 0.0323(11) 0.0435(12) 0.0137(10) 0.0234(11) 0.0155(10) N7 0.0368(11) 0.0390(11) 0.0345(11) 0.0192(9) 0.0020(8) 0.0019(9) N8 0.0668(16) 0.0683(16) 0.0416(13) 0.0261(12) 0.0164(11) 0.0458(13) N9 0.174(4) 0.215(5) 0.061(2) 0.082(3) 0.050(2) 0.144(4) N10 0.0357(11) 0.0538(13) 0.0476(13) 0.0244(11) 0.0118(10) 0.0094(10) N11 0.0304(10) 0.0293(10) 0.0511(14) 0.0186(10) 0.0168(10) 0.0097(8) N12 0.0503(13) 0.0373(11) 0.0453(13) 0.0166(10) 0.0098(10) 0.0095(10) N13 0.0331(10) 0.0282(9) 0.0308(9) 0.0129(8) 0.0063(8) 0.0147(8) N14 0.0298(10) 0.0340(10) 0.0359(10) 0.0181(9) 0.0031(8) 0.0046(8) O1 0.0501(11) 0.0343(10) 0.0646(13) 0.0227(10) 0.0305(10) 0.0141(9) O2 0.0310(9) 0.0339(9) 0.0469(10) 0.0147(8) 0.0001(7) 0.0086(7) O3 0.0395(10) 0.0363(9) 0.0703(13) 0.0135(9) -0.0130(9) 0.0124(8) O4 0.0319(8) 0.0264(8) 0.0575(10) 0.0200(8) 0.0063(7) 0.0094(7) O5 0.0282(8) 0.0352(9) 0.0617(11) 0.0275(8) 0.0116(7) 0.0138(7) O6 0.0396(10) 0.0338(9) 0.0519(11) 0.0093(8) 0.0002(8) 0.0041(8) O7 0.0370(10) 0.0524(12) 0.0700(13) 0.0141(10) -0.0047(9) 0.0189(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.172(2) . ? Mn1 O4 2.1802(16) . ? Mn1 N1 2.2053(19) 2 ? Mn1 N7 2.2108(19) . ? Mn1 N1 2.2572(19) . ? Mn1 N4 2.267(2) . ? Mn2 O2 2.1748(16) . ? Mn2 O5 2.1816(15) . ? Mn2 N10 2.185(2) . ? Mn2 O3 2.1921(18) . ? Mn2 N7 2.212(2) . ? Mn2 N4 2.2600(19) . ? C1 O5 1.245(3) . ? C1 O4 1.247(3) . ? C1 C2 1.525(3) . ? C2 C3 1.381(3) . ? C2 C6 1.388(3) . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 N13 1.340(3) . ? C4 H4A 0.9300 . ? C5 N13 1.353(3) . ? C5 C6 1.367(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 N13 1.499(3) . ? C7 C8 1.512(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.375(4) . ? C8 C10 1.387(3) . ? C9 C10 1.388(4) 2_576 ? C9 H9A 0.95(3) . ? C10 C9 1.388(4) 2_576 ? C10 H10A 0.92(3) . ? C11 O7 1.232(3) . ? C11 O6 1.249(3) . ? C11 C12 1.518(3) . ? C12 C16 1.379(3) . ? C12 C13 1.387(3) . ? C13 C14 1.363(3) . ? C13 H13A 0.9300 . ? C14 N14 1.348(3) . ? C14 H14A 0.9300 . ? C15 N14 1.335(3) . ? C15 C16 1.378(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 N14 1.498(3) . ? C17 C18 1.512(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C20 1.383(4) . ? C18 C19 1.386(4) . ? C19 C20 1.379(4) 2_676 ? C19 H19A 0.94(3) . ? C20 C19 1.379(4) 2_676 ? C20 H20A 0.92(3) . ? C21 O3 1.407(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 N2 1.187(3) . ? N1 Mn1 2.2053(19) 2 ? N2 N3 1.148(3) . ? N4 N5 1.177(3) . ? N5 N6 1.156(3) . ? N7 N8 1.182(3) . ? N8 N9 1.141(4) . ? N10 N11 1.176(3) . ? N11 N12 1.170(3) . ? O1 H1W1 0.86(4) . ? O1 H1W2 0.84(4) . ? O2 H2W2 0.7059 . ? O2 H2W1 0.91(4) . ? O3 H3B 0.7758 . ? 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 Mn1 O4 86.23(8) . . ? O1 Mn1 N1 99.20(8) . 2 ? O4 Mn1 N1 95.56(7) . 2 ? O1 Mn1 N7 86.63(8) . . ? O4 Mn1 N7 91.33(7) . . ? N1 Mn1 N7 171.24(8) 2 . ? O1 Mn1 N1 91.64(8) . . ? O4 Mn1 N1 172.18(7) . . ? N1 Mn1 N1 77.34(8) 2 . ? N7 Mn1 N1 96.06(7) . . ? O1 Mn1 N4 165.00(7) . . ? O4 Mn1 N4 90.40(7) . . ? N1 Mn1 N4 95.67(8) 2 . ? N7 Mn1 N4 78.84(7) . . ? N1 Mn1 N4 93.53(8) . . ? O2 Mn2 O5 82.98(6) . . ? O2 Mn2 N10 95.72(8) . . ? O5 Mn2 N10 94.86(8) . . ? O2 Mn2 O3 92.35(7) . . ? O5 Mn2 O3 174.23(7) . . ? N10 Mn2 O3 88.96(9) . . ? O2 Mn2 N7 93.92(7) . . ? O5 Mn2 N7 86.89(7) . . ? N10 Mn2 N7 170.35(8) . . ? O3 Mn2 N7 90.06(8) . . ? O2 Mn2 N4 168.11(7) . . ? O5 Mn2 N4 87.10(7) . . ? N10 Mn2 N4 91.63(8) . . ? O3 Mn2 N4 97.13(7) . . ? N7 Mn2 N4 78.96(7) . . ? O5 C1 O4 127.9(2) . . ? O5 C1 C2 115.48(19) . . ? O4 C1 C2 116.58(19) . . ? C3 C2 C6 118.8(2) . . ? C3 C2 C1 121.86(19) . . ? C6 C2 C1 119.33(19) . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? N13 C4 C3 120.6(2) . . ? N13 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? N13 C5 C6 120.5(2) . . ? N13 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C2 119.7(2) . . ? C5 C6 H6A 120.1 . . ? C2 C6 H6A 120.1 . . ? N13 C7 C8 112.28(18) . . ? N13 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? N13 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C10 118.6(2) . . ? C9 C8 C7 120.5(2) . . ? C10 C8 C7 120.9(2) . . ? C8 C9 C10 121.0(2) . 2_576 ? C8 C9 H9A 120.9(19) . . ? C10 C9 H9A 118.0(19) 2_576 . ? C8 C10 C9 120.4(3) . 2_576 ? C8 C10 H10A 121.3(18) . . ? C9 C10 H10A 118.1(18) 2_576 . ? O7 C11 O6 127.0(2) . . ? O7 C11 C12 114.9(2) . . ? O6 C11 C12 118.1(2) . . ? C16 C12 C13 118.4(2) . . ? C16 C12 C11 123.6(2) . . ? C13 C12 C11 117.9(2) . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? N14 C14 C13 120.6(2) . . ? N14 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? N14 C15 C16 120.4(2) . . ? N14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C12 C16 C15 119.9(2) . . ? C12 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? N14 C17 C18 109.65(19) . . ? N14 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? N14 C17 H17B 109.7 . . ? C18 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C20 C18 C19 119.0(2) . . ? C20 C18 C17 120.3(2) . . ? C19 C18 C17 120.7(2) . . ? C20 C19 C18 119.8(2) 2_676 . ? C20 C19 H19A 121.0(18) 2_676 . ? C18 C19 H19A 119.2(18) . . ? C19 C20 C18 121.1(2) 2_676 . ? C19 C20 H20A 119.8(17) 2_676 . ? C18 C20 H20A 119.0(17) . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 N1 Mn1 131.27(16) . 2 ? N2 N1 Mn1 124.62(15) . . ? Mn1 N1 Mn1 102.66(8) 2 . ? N3 N2 N1 178.9(3) . . ? N5 N4 Mn2 135.02(16) . . ? N5 N4 Mn1 127.47(16) . . ? Mn2 N4 Mn1 95.80(7) . . ? N6 N5 N4 178.4(2) . . ? N8 N7 Mn1 127.92(19) . . ? N8 N7 Mn2 130.99(19) . . ? Mn1 N7 Mn2 98.83(8) . . ? N9 N8 N7 178.5(3) . . ? N11 N10 Mn2 124.14(17) . . ? N12 N11 N10 179.1(3) . . ? C4 N13 C5 120.66(19) . . ? C4 N13 C7 120.46(19) . . ? C5 N13 C7 118.87(19) . . ? C15 N14 C14 120.9(2) . . ? C15 N14 C17 121.6(2) . . ? C14 N14 C17 117.5(2) . . ? Mn1 O1 H1W1 120(2) . . ? Mn1 O1 H1W2 124(3) . . ? H1W1 O1 H1W2 109(3) . . ? Mn2 O2 H2W2 104.7 . . ? Mn2 O2 H2W1 107(2) . . ? H2W2 O2 H2W1 113.2 . . ? C21 O3 Mn2 119.58(18) . . ? C21 O3 H3B 101.2 . . ? Mn2 O3 H3B 127.3 . . ? C1 O4 Mn1 125.22(14) . . ? C1 O5 Mn2 132.88(14) . . ? 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 O5 C1 C2 C3 174.4(2) . . . . ? O4 C1 C2 C3 -6.4(3) . . . . ? O5 C1 C2 C6 -7.0(3) . . . . ? O4 C1 C2 C6 172.2(2) . . . . ? C6 C2 C3 C4 -0.2(3) . . . . ? C1 C2 C3 C4 178.4(2) . . . . ? C2 C3 C4 N13 -0.7(3) . . . . ? N13 C5 C6 C2 -0.8(4) . . . . ? C3 C2 C6 C5 0.9(3) . . . . ? C1 C2 C6 C5 -177.7(2) . . . . ? N13 C7 C8 C9 -82.4(3) . . . . ? N13 C7 C8 C10 99.3(3) . . . . ? C10 C8 C9 C10 -0.7(4) . . . 2_576 ? C7 C8 C9 C10 -179.0(2) . . . 2_576 ? C9 C8 C10 C9 0.7(4) . . . 2_576 ? C7 C8 C10 C9 179.0(2) . . . 2_576 ? O7 C11 C12 C16 -160.6(2) . . . . ? O6 C11 C12 C16 18.5(3) . . . . ? O7 C11 C12 C13 16.0(3) . . . . ? O6 C11 C12 C13 -164.8(2) . . . . ? C16 C12 C13 C14 1.4(4) . . . . ? C11 C12 C13 C14 -175.4(2) . . . . ? C12 C13 C14 N14 -0.4(4) . . . . ? C13 C12 C16 C15 -1.7(3) . . . . ? C11 C12 C16 C15 174.9(2) . . . . ? N14 C15 C16 C12 0.9(4) . . . . ? N14 C17 C18 C20 -68.1(3) . . . . ? N14 C17 C18 C19 110.1(3) . . . . ? C20 C18 C19 C20 0.3(4) . . . 2_676 ? C17 C18 C19 C20 -178.0(2) . . . 2_676 ? C19 C18 C20 C19 -0.3(4) . . . 2_676 ? C17 C18 C20 C19 178.0(2) . . . 2_676 ? O1 Mn1 N1 N2 -93.4(2) . . . . ? O4 Mn1 N1 N2 -167.4(5) . . . . ? N1 Mn1 N1 N2 167.5(3) 2 . . . ? N7 Mn1 N1 N2 -6.6(2) . . . . ? N4 Mn1 N1 N2 72.5(2) . . . . ? O1 Mn1 N1 Mn1 99.06(9) . . . 2 ? O4 Mn1 N1 Mn1 25.1(6) . . . 2 ? N1 Mn1 N1 Mn1 0.0 2 . . 2 ? N7 Mn1 N1 Mn1 -174.16(9) . . . 2 ? N4 Mn1 N1 Mn1 -95.03(9) . . . 2 ? Mn1 N1 N2 N3 -95(13) 2 . . . ? Mn1 N1 N2 N3 101(13) . . . . ? O2 Mn2 N4 N5 161.3(3) . . . . ? O5 Mn2 N4 N5 127.8(2) . . . . ? N10 Mn2 N4 N5 33.0(2) . . . . ? O3 Mn2 N4 N5 -56.1(3) . . . . ? N7 Mn2 N4 N5 -144.8(3) . . . . ? O2 Mn2 N4 Mn1 -33.5(4) . . . . ? O5 Mn2 N4 Mn1 -67.00(8) . . . . ? N10 Mn2 N4 Mn1 -161.79(9) . . . . ? O3 Mn2 N4 Mn1 109.06(8) . . . . ? N7 Mn2 N4 Mn1 20.39(8) . . . . ? O1 Mn1 N4 N5 160.9(3) . . . . ? O4 Mn1 N4 N5 -122.3(2) . . . . ? N1 Mn1 N4 N5 -26.7(2) 2 . . . ? N7 Mn1 N4 N5 146.4(2) . . . . ? N1 Mn1 N4 N5 50.9(2) . . . . ? O1 Mn1 N4 Mn2 -6.0(3) . . . . ? O4 Mn1 N4 Mn2 70.86(7) . . . . ? N1 Mn1 N4 Mn2 166.49(8) 2 . . . ? N7 Mn1 N4 Mn2 -20.42(8) . . . . ? N1 Mn1 N4 Mn2 -115.90(8) . . . . ? Mn2 N4 N5 N6 -132(9) . . . . ? Mn1 N4 N5 N6 67(9) . . . . ? O1 Mn1 N7 N8 40.5(2) . . . . ? O4 Mn1 N7 N8 126.6(2) . . . . ? N1 Mn1 N7 N8 -91.5(6) 2 . . . ? N1 Mn1 N7 N8 -50.8(2) . . . . ? N4 Mn1 N7 N8 -143.2(2) . . . . ? O1 Mn1 N7 Mn2 -155.27(9) . . . . ? O4 Mn1 N7 Mn2 -69.12(8) . . . . ? N1 Mn1 N7 Mn2 72.8(5) 2 . . . ? N1 Mn1 N7 Mn2 113.44(9) . . . . ? N4 Mn1 N7 Mn2 21.03(8) . . . . ? O2 Mn2 N7 N8 -47.2(2) . . . . ? O5 Mn2 N7 N8 -129.9(2) . . . . ? N10 Mn2 N7 N8 129.3(5) . . . . ? O3 Mn2 N7 N8 45.2(2) . . . . ? N4 Mn2 N7 N8 142.5(3) . . . . ? O2 Mn2 N7 Mn1 149.30(8) . . . . ? O5 Mn2 N7 Mn1 66.56(8) . . . . ? N10 Mn2 N7 Mn1 -34.2(5) . . . . ? O3 Mn2 N7 Mn1 -118.34(8) . . . . ? N4 Mn2 N7 Mn1 -21.09(8) . . . . ? Mn1 N7 N8 N9 -58(16) . . . . ? Mn2 N7 N8 N9 143(16) . . . . ? O2 Mn2 N10 N11 -140.7(2) . . . . ? O5 Mn2 N10 N11 -57.3(2) . . . . ? O3 Mn2 N10 N11 127.1(2) . . . . ? N7 Mn2 N10 N11 42.8(6) . . . . ? N4 Mn2 N10 N11 30.0(2) . . . . ? Mn2 N10 N11 N12 -146(17) . . . . ? C3 C4 N13 C5 0.8(3) . . . . ? C3 C4 N13 C7 179.8(2) . . . . ? C6 C5 N13 C4 0.0(4) . . . . ? C6 C5 N13 C7 -179.1(2) . . . . ? C8 C7 N13 C4 113.4(2) . . . . ? C8 C7 N13 C5 -67.5(3) . . . . ? C16 C15 N14 C14 0.2(4) . . . . ? C16 C15 N14 C17 -176.9(2) . . . . ? C13 C14 N14 C15 -0.4(4) . . . . ? C13 C14 N14 C17 176.8(2) . . . . ? C18 C17 N14 C15 111.7(3) . . . . ? C18 C17 N14 C14 -65.5(3) . . . . ? O2 Mn2 O3 C21 -161.6(3) . . . . ? O5 Mn2 O3 C21 162.5(7) . . . . ? N10 Mn2 O3 C21 -65.9(3) . . . . ? N7 Mn2 O3 C21 104.5(3) . . . . ? N4 Mn2 O3 C21 25.6(3) . . . . ? O5 C1 O4 Mn1 24.7(3) . . . . ? C2 C1 O4 Mn1 -154.36(14) . . . . ? O1 Mn1 O4 C1 113.50(19) . . . . ? N1 Mn1 O4 C1 -147.61(19) 2 . . . ? N7 Mn1 O4 C1 26.97(19) . . . . ? N1 Mn1 O4 C1 -172.1(5) . . . . ? N4 Mn1 O4 C1 -51.87(19) . . . . ? O4 C1 O5 Mn2 -25.2(4) . . . . ? C2 C1 O5 Mn2 153.93(15) . . . . ? O2 Mn2 O5 C1 -122.5(2) . . . . ? N10 Mn2 O5 C1 142.4(2) . . . . ? O3 Mn2 O5 C1 -86.3(7) . . . . ? N7 Mn2 O5 C1 -28.1(2) . . . . ? N4 Mn2 O5 C1 51.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.359 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.055 # Attachment '- 825566.cif' #TrackingRef '- 825566.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 825566' #TrackingRef '- 825566.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 Mn3 N10 O20' _chemical_formula_weight 1221.73 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5483(4) _cell_length_b 11.1328(4) _cell_length_c 13.1810(5) _cell_angle_alpha 70.2760(10) _cell_angle_beta 72.4020(10) _cell_angle_gamma 74.0820(10) _cell_volume 1233.83(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5728 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.79 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 625 _exptl_absorpt_coefficient_mu 0.848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9750 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 15937 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.51 _reflns_number_total 5007 _reflns_number_gt 3966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0593P)^2^+0.5373P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5007 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Mn1 Mn 0.84565(4) 0.33703(3) 0.42295(3) 0.03080(12) Uani 1 1 d . . . Mn2 Mn 0.5000 0.5000 0.5000 0.02913(14) Uani 1 2 d S . . C1 C 0.5644(3) 0.2286(2) 0.44667(19) 0.0308(5) Uani 1 1 d . . . C2 C 0.5253(3) 0.1439(2) 0.39302(18) 0.0284(5) Uani 1 1 d . . . C3 C 0.6383(3) 0.0541(2) 0.3496(2) 0.0375(6) Uani 1 1 d . . . H3 H 0.7363 0.0459 0.3534 0.045 Uiso 1 1 calc R . . C4 C 0.6060(3) -0.0226(3) 0.3010(2) 0.0404(6) Uani 1 1 d . . . H4 H 0.6823 -0.0831 0.2722 0.048 Uiso 1 1 calc R . . C5 C 0.3538(3) 0.0742(2) 0.3363(2) 0.0358(5) Uani 1 1 d . . . H5 H 0.2566 0.0800 0.3320 0.043 Uiso 1 1 calc R . . C6 C 0.3816(3) 0.1534(2) 0.3855(2) 0.0339(5) Uani 1 1 d . . . H6 H 0.3036 0.2133 0.4137 0.041 Uiso 1 1 calc R . . C7 C 0.4344(3) -0.0967(3) 0.2399(2) 0.0425(6) Uani 1 1 d . . . H7B H 0.3297 -0.1035 0.2665 0.051 Uiso 1 1 calc R . . H7A H 0.4938 -0.1832 0.2608 0.051 Uiso 1 1 calc R . . C8 C 0.4699(3) -0.0451(2) 0.1153(2) 0.0358(5) Uani 1 1 d . . . C9 C 0.6138(3) -0.0706(3) 0.0519(2) 0.0451(6) Uani 1 1 d . . . H9 H 0.6913 -0.1185 0.0866 0.054 Uiso 1 1 calc R . . C10 C 0.3570(3) 0.0254(3) 0.0622(2) 0.0434(6) Uani 1 1 d . . . H10 H 0.2597 0.0428 0.1037 0.052 Uiso 1 1 calc R . . C11 C 0.7076(3) 0.5721(3) 0.2556(2) 0.0500(7) Uani 1 1 d . . . C12 C 0.7369(3) 0.3475(3) 0.6538(2) 0.0394(6) Uani 1 1 d . . . C13 C 0.9780(3) 0.0863(3) 0.5917(2) 0.0365(6) Uani 1 1 d . . . C14 C 0.2892(3) 0.3836(3) 0.1693(2) 0.0462(7) Uani 1 1 d . . . C15 C 0.4550(3) 0.3604(2) 0.1141(2) 0.0360(6) Uani 1 1 d . . . C16 C 0.5059(3) 0.3102(3) 0.0239(2) 0.0407(6) Uani 1 1 d . . . H16 H 0.4387 0.2915 -0.0044 0.049 Uiso 1 1 calc R . . C17 C 0.6558(3) 0.2883(3) -0.0234(2) 0.0428(6) Uani 1 1 d . . . H17 H 0.6899 0.2556 -0.0847 0.051 Uiso 1 1 calc R . . C18 C 0.5590(3) 0.3875(3) 0.1534(2) 0.0425(6) Uani 1 1 d . . . H18 H 0.5274 0.4232 0.2129 0.051 Uiso 1 1 calc R . . C19 C 0.7088(3) 0.3615(3) 0.1040(2) 0.0442(6) Uani 1 1 d . . . H19 H 0.7790 0.3776 0.1312 0.053 Uiso 1 1 calc R . . C20 C 0.9170(3) 0.2796(3) -0.0355(3) 0.0518(7) Uani 1 1 d . . . H20B H 0.9756 0.3080 -0.0025 0.062 Uiso 1 1 calc R . . H20A H 0.9357 0.3237 -0.1142 0.062 Uiso 1 1 calc R . . C21 C 0.9621(3) 0.1349(3) -0.0181(2) 0.0416(6) Uani 1 1 d . . . C22 C 1.0045(3) 0.0815(3) -0.1060(2) 0.0467(7) Uani 1 1 d . . . H22 H 1.0077 0.1356 -0.1777 0.056 Uiso 1 1 calc R . . C23 C 0.9579(3) 0.0513(3) 0.0881(2) 0.0469(7) Uani 1 1 d . . . H23 H 0.9264 0.0906 0.1454 0.056 Uiso 1 1 d R . . N1 N 0.6708(2) 0.5052(2) 0.34318(17) 0.0388(5) Uani 1 1 d . . . N2 N 0.6944(2) 0.3991(2) 0.57312(17) 0.0371(5) Uani 1 1 d . . . N3 N 0.9926(2) 0.1767(2) 0.5139(2) 0.0444(5) Uani 1 1 d . . . N4 N 0.4656(2) -0.01126(19) 0.29445(16) 0.0340(4) Uani 1 1 d . . . N5 N 0.7536(2) 0.3130(2) 0.01683(17) 0.0388(5) Uani 1 1 d . . . O1 O 0.9938(3) 0.4668(2) 0.3803(2) 0.0590(6) Uani 1 1 d . . . H1W2 H 0.959(4) 0.545(4) 0.383(3) 0.069(11) Uiso 1 1 d . . . H1W1 H 1.064(5) 0.467(4) 0.336(3) 0.078(13) Uiso 1 1 d . . . O2 O 0.9511(2) 0.2812(2) 0.26635(17) 0.0426(5) Uani 1 1 d . . . H2W2 H 1.039(4) 0.304(3) 0.226(3) 0.062(10) Uiso 1 1 d . . . H2W1 H 0.980(4) 0.213(4) 0.280(3) 0.065(13) Uiso 1 1 d . . . O3 O 0.7488(4) 0.6370(3) 0.1637(2) 0.1227(13) Uani 1 1 d . . . O4 O 0.7842(3) 0.2891(2) 0.73463(18) 0.0714(7) Uani 1 1 d . . . O5 O 0.9648(2) -0.00472(19) 0.67314(17) 0.0538(5) Uani 1 1 d . . . O6 O 0.46173(19) 0.30970(17) 0.48509(15) 0.0390(4) Uani 1 1 d . . . O7 O 0.6997(2) 0.20747(18) 0.44601(17) 0.0448(4) Uani 1 1 d . . . O8 O 0.2526(3) 0.4434(3) 0.2381(3) 0.0904(9) Uani 1 1 d . . . O9 O 0.2098(3) 0.3374(3) 0.1406(2) 0.0862(9) Uani 1 1 d . . . O10 O 0.1590(3) 0.2871(2) 0.6111(2) 0.0566(6) Uani 1 1 d . . . H10B H 0.255(5) 0.308(4) 0.563(3) 0.095(14) Uiso 1 1 d . . . H10A H 0.101(7) 0.262(6) 0.579(5) 0.14(2) Uiso 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 Mn1 0.02325(19) 0.0334(2) 0.0370(2) -0.01206(15) -0.00653(14) -0.00488(14) Mn2 0.0216(3) 0.0330(3) 0.0339(3) -0.0131(2) -0.00450(19) -0.00438(19) C1 0.0305(12) 0.0305(12) 0.0331(12) -0.0082(9) -0.0051(9) -0.0122(9) C2 0.0300(12) 0.0265(11) 0.0273(10) -0.0045(9) -0.0040(9) -0.0098(9) C3 0.0289(12) 0.0442(14) 0.0418(13) -0.0159(11) -0.0073(10) -0.0066(10) C4 0.0377(14) 0.0399(14) 0.0449(14) -0.0204(11) -0.0071(11) -0.0016(11) C5 0.0316(13) 0.0391(13) 0.0399(13) -0.0128(11) -0.0092(10) -0.0085(10) C6 0.0303(12) 0.0338(12) 0.0384(12) -0.0141(10) -0.0058(10) -0.0049(10) C7 0.0498(16) 0.0400(14) 0.0462(14) -0.0199(12) -0.0071(12) -0.0168(12) C8 0.0377(13) 0.0353(13) 0.0436(13) -0.0191(11) -0.0086(11) -0.0120(10) C9 0.0351(14) 0.0548(17) 0.0531(16) -0.0250(13) -0.0140(12) -0.0038(12) C10 0.0314(13) 0.0538(16) 0.0511(15) -0.0276(13) -0.0044(11) -0.0072(11) C11 0.0488(17) 0.0434(16) 0.0484(17) -0.0084(13) -0.0107(13) -0.0001(13) C12 0.0455(15) 0.0402(14) 0.0385(14) -0.0162(12) -0.0084(12) -0.0125(11) C13 0.0268(12) 0.0401(15) 0.0507(15) -0.0231(13) -0.0133(11) -0.0012(10) C14 0.0390(15) 0.0364(14) 0.0500(16) -0.0049(12) 0.0017(12) -0.0086(12) C15 0.0353(13) 0.0250(11) 0.0375(12) -0.0022(9) -0.0031(10) -0.0039(10) C16 0.0387(14) 0.0406(14) 0.0440(14) -0.0128(11) -0.0086(11) -0.0094(11) C17 0.0383(14) 0.0467(15) 0.0435(14) -0.0196(12) -0.0032(11) -0.0066(11) C18 0.0436(15) 0.0394(14) 0.0415(14) -0.0147(11) -0.0054(11) -0.0041(11) C19 0.0402(15) 0.0449(15) 0.0501(15) -0.0149(12) -0.0138(12) -0.0063(12) C20 0.0298(14) 0.0541(17) 0.0622(18) -0.0173(14) 0.0011(12) -0.0050(12) C21 0.0229(12) 0.0484(15) 0.0455(14) -0.0116(12) -0.0051(10) 0.0009(11) C22 0.0351(14) 0.0564(17) 0.0356(13) -0.0070(12) -0.0068(11) 0.0030(12) C23 0.0366(14) 0.0588(18) 0.0415(14) -0.0198(13) -0.0078(11) 0.0027(12) N1 0.0321(11) 0.0466(12) 0.0340(11) -0.0110(10) -0.0029(9) -0.0076(9) N2 0.0314(11) 0.0435(12) 0.0395(11) -0.0158(9) -0.0116(9) -0.0028(9) N3 0.0380(13) 0.0411(13) 0.0529(14) -0.0109(11) -0.0167(10) -0.0016(10) N4 0.0403(12) 0.0310(10) 0.0343(10) -0.0107(8) -0.0079(9) -0.0112(9) N5 0.0308(11) 0.0345(11) 0.0444(12) -0.0098(9) -0.0032(9) -0.0034(9) O1 0.0351(11) 0.0498(13) 0.0925(18) -0.0339(12) 0.0079(12) -0.0163(10) O2 0.0344(11) 0.0450(12) 0.0475(11) -0.0180(9) -0.0043(9) -0.0054(9) O3 0.144(3) 0.109(2) 0.0639(18) 0.0345(17) -0.0108(18) -0.032(2) O4 0.105(2) 0.0647(14) 0.0491(12) -0.0129(11) -0.0392(13) -0.0026(13) O5 0.0650(14) 0.0381(11) 0.0552(12) -0.0097(9) -0.0132(10) -0.0098(9) O6 0.0313(9) 0.0402(10) 0.0526(10) -0.0246(8) -0.0050(8) -0.0088(7) O7 0.0310(10) 0.0416(10) 0.0720(13) -0.0266(9) -0.0141(9) -0.0071(8) O8 0.0506(14) 0.096(2) 0.134(2) -0.0818(19) 0.0294(15) -0.0222(13) O9 0.0409(13) 0.153(3) 0.0788(17) -0.0574(18) 0.0119(12) -0.0374(15) O10 0.0433(12) 0.0591(13) 0.0756(15) -0.0326(11) -0.0047(11) -0.0151(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.120(2) . ? Mn1 O7 2.1599(18) . ? Mn1 N3 2.189(2) . ? Mn1 O2 2.219(2) . ? Mn1 N2 2.265(2) . ? Mn1 N1 2.327(2) . ? Mn2 N2 2.201(2) . ? Mn2 N2 2.201(2) 2_666 ? Mn2 N1 2.207(2) . ? Mn2 N1 2.207(2) 2_666 ? Mn2 O6 2.3259(16) 2_666 ? Mn2 O6 2.3259(16) . ? C1 O7 1.246(3) . ? C1 O6 1.247(3) . ? C1 C2 1.527(3) . ? C2 C6 1.378(3) . ? C2 C3 1.383(3) . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 N4 1.338(3) . ? C4 H4 0.9300 . ? C5 N4 1.338(3) . ? C5 C6 1.374(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N4 1.502(3) . ? C7 C8 1.509(4) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 C10 1.374(4) . ? C8 C9 1.385(4) . ? C9 C10 1.381(4) 2_655 ? C9 H9 0.9300 . ? C10 C9 1.381(4) 2_655 ? C10 H10 0.9300 . ? C11 N1 1.153(3) . ? C11 O3 1.192(4) . ? C12 N2 1.160(3) . ? C12 O4 1.194(3) . ? C13 N3 1.174(3) . ? C13 O5 1.204(3) . ? C14 O8 1.216(4) . ? C14 O9 1.224(4) . ? C14 C15 1.520(4) . ? C15 C16 1.384(4) . ? C15 C18 1.387(4) . ? C16 C17 1.366(4) . ? C16 H16 0.9300 . ? C17 N5 1.330(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(4) . ? C18 H18 0.9300 . ? C19 N5 1.338(3) . ? C19 H19 0.9300 . ? C20 N5 1.501(3) . ? C20 C21 1.504(4) . ? C20 H20B 0.9700 . ? C20 H20A 0.9700 . ? C21 C22 1.382(4) . ? C21 C23 1.391(4) . ? C22 C23 1.377(4) 2_755 ? C22 H22 0.9300 . ? C23 C22 1.377(4) 2_755 ? C23 H23 0.9303 . ? O1 H1W2 0.85(4) . ? O1 H1W1 0.74(4) . ? O2 H2W2 0.90(4) . ? O2 H2W1 0.72(4) . ? O10 H10B 0.98(5) . ? O10 H10A 0.94(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O7 173.34(9) . . ? O1 Mn1 N3 92.58(10) . . ? O7 Mn1 N3 90.38(8) . . ? O1 Mn1 O2 91.19(9) . . ? O7 Mn1 O2 82.72(8) . . ? N3 Mn1 O2 92.41(9) . . ? O1 Mn1 N2 96.38(9) . . ? O7 Mn1 N2 89.24(8) . . ? N3 Mn1 N2 95.91(8) . . ? O2 Mn1 N2 168.47(8) . . ? O1 Mn1 N1 90.38(9) . . ? O7 Mn1 N1 87.22(7) . . ? N3 Mn1 N1 174.13(8) . . ? O2 Mn1 N1 92.60(8) . . ? N2 Mn1 N1 78.71(7) . . ? N2 Mn2 N2 180.0 . 2_666 ? N2 Mn2 N1 82.72(8) . . ? N2 Mn2 N1 97.28(8) 2_666 . ? N2 Mn2 N1 97.28(8) . 2_666 ? N2 Mn2 N1 82.72(8) 2_666 2_666 ? N1 Mn2 N1 180.0 . 2_666 ? N2 Mn2 O6 86.79(7) . 2_666 ? N2 Mn2 O6 93.21(7) 2_666 2_666 ? N1 Mn2 O6 93.79(7) . 2_666 ? N1 Mn2 O6 86.21(7) 2_666 2_666 ? N2 Mn2 O6 93.21(7) . . ? N2 Mn2 O6 86.79(7) 2_666 . ? N1 Mn2 O6 86.21(7) . . ? N1 Mn2 O6 93.79(7) 2_666 . ? O6 Mn2 O6 180.00(9) 2_666 . ? O7 C1 O6 127.4(2) . . ? O7 C1 C2 114.2(2) . . ? O6 C1 C2 118.4(2) . . ? C6 C2 C3 118.3(2) . . ? C6 C2 C1 122.7(2) . . ? C3 C2 C1 119.0(2) . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? N4 C4 C3 120.6(2) . . ? N4 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N4 C5 C6 120.5(2) . . ? N4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C2 119.9(2) . . ? C5 C6 H6 120.1 . . ? C2 C6 H6 120.1 . . ? N4 C7 C8 112.3(2) . . ? N4 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? N4 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? H7B C7 H7A 107.9 . . ? C10 C8 C9 118.7(2) . . ? C10 C8 C7 119.8(2) . . ? C9 C8 C7 121.5(2) . . ? C10 C9 C8 120.6(3) 2_655 . ? C10 C9 H9 119.7 2_655 . ? C8 C9 H9 119.7 . . ? C8 C10 C9 120.8(2) . 2_655 ? C8 C10 H10 119.6 . . ? C9 C10 H10 119.6 2_655 . ? N1 C11 O3 177.4(4) . . ? N2 C12 O4 176.6(3) . . ? N3 C13 O5 178.0(3) . . ? O8 C14 O9 128.2(3) . . ? O8 C14 C15 115.7(3) . . ? O9 C14 C15 116.1(3) . . ? C16 C15 C18 118.4(2) . . ? C16 C15 C14 120.5(2) . . ? C18 C15 C14 121.1(2) . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? N5 C17 C16 121.0(2) . . ? N5 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C15 119.7(2) . . ? C19 C18 H18 120.1 . . ? C15 C18 H18 120.1 . . ? N5 C19 C18 120.0(3) . . ? N5 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? N5 C20 C21 109.2(2) . . ? N5 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? N5 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? H20B C20 H20A 108.3 . . ? C22 C21 C23 118.4(3) . . ? C22 C21 C20 121.2(3) . . ? C23 C21 C20 120.4(3) . . ? C23 C22 C21 120.4(3) 2_755 . ? C23 C22 H22 119.8 2_755 . ? C21 C22 H22 119.8 . . ? C22 C23 C21 121.2(3) 2_755 . ? C22 C23 H23 122.8 2_755 . ? C21 C23 H23 116.0 . . ? C11 N1 Mn2 142.2(2) . . ? C11 N1 Mn1 119.9(2) . . ? Mn2 N1 Mn1 94.82(8) . . ? C12 N2 Mn2 146.6(2) . . ? C12 N2 Mn1 114.01(18) . . ? Mn2 N2 Mn1 96.77(8) . . ? C13 N3 Mn1 136.7(2) . . ? C5 N4 C4 120.8(2) . . ? C5 N4 C7 120.1(2) . . ? C4 N4 C7 119.1(2) . . ? C17 N5 C19 121.3(2) . . ? C17 N5 C20 118.0(2) . . ? C19 N5 C20 120.7(2) . . ? Mn1 O1 H1W2 120(3) . . ? Mn1 O1 H1W1 125(3) . . ? H1W2 O1 H1W1 108(4) . . ? Mn1 O2 H2W2 119(2) . . ? Mn1 O2 H2W1 108(3) . . ? H2W2 O2 H2W1 96(4) . . ? C1 O6 Mn2 123.33(15) . . ? C1 O7 Mn1 131.47(16) . . ? H10B O10 H10A 115(4) . . ? 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 O7 C1 C2 C6 -179.8(2) . . . . ? O6 C1 C2 C6 -0.1(3) . . . . ? O7 C1 C2 C3 0.0(3) . . . . ? O6 C1 C2 C3 179.7(2) . . . . ? C6 C2 C3 C4 -0.1(4) . . . . ? C1 C2 C3 C4 -179.9(2) . . . . ? C2 C3 C4 N4 0.3(4) . . . . ? N4 C5 C6 C2 -0.7(4) . . . . ? C3 C2 C6 C5 0.3(3) . . . . ? C1 C2 C6 C5 -179.9(2) . . . . ? N4 C7 C8 C10 -98.2(3) . . . . ? N4 C7 C8 C9 83.9(3) . . . . ? C10 C8 C9 C10 0.4(4) . . . 2_655 ? C7 C8 C9 C10 178.2(2) . . . 2_655 ? C9 C8 C10 C9 -0.4(4) . . . 2_655 ? C7 C8 C10 C9 -178.2(2) . . . 2_655 ? O8 C14 C15 C16 -170.7(3) . . . . ? O9 C14 C15 C16 10.8(4) . . . . ? O8 C14 C15 C18 10.0(4) . . . . ? O9 C14 C15 C18 -168.5(3) . . . . ? C18 C15 C16 C17 0.3(4) . . . . ? C14 C15 C16 C17 -179.0(2) . . . . ? C15 C16 C17 N5 0.9(4) . . . . ? C16 C15 C18 C19 -1.4(4) . . . . ? C14 C15 C18 C19 177.9(2) . . . . ? C15 C18 C19 N5 1.5(4) . . . . ? N5 C20 C21 C22 113.0(3) . . . . ? N5 C20 C21 C23 -65.1(3) . . . . ? C23 C21 C22 C23 -0.3(5) . . . 2_755 ? C20 C21 C22 C23 -178.5(3) . . . 2_755 ? C22 C21 C23 C22 0.3(5) . . . 2_755 ? C20 C21 C23 C22 178.5(3) . . . 2_755 ? O3 C11 N1 Mn2 -162(9) . . . . ? O3 C11 N1 Mn1 44(9) . . . . ? N2 Mn2 N1 C11 -138.0(4) . . . . ? N2 Mn2 N1 C11 42.0(4) 2_666 . . . ? N1 Mn2 N1 C11 -102(100) 2_666 . . . ? O6 Mn2 N1 C11 -51.8(4) 2_666 . . . ? O6 Mn2 N1 C11 128.2(4) . . . . ? N2 Mn2 N1 Mn1 19.85(8) . . . . ? N2 Mn2 N1 Mn1 -160.15(8) 2_666 . . . ? N1 Mn2 N1 Mn1 56(100) 2_666 . . . ? O6 Mn2 N1 Mn1 106.13(7) 2_666 . . . ? O6 Mn2 N1 Mn1 -73.87(7) . . . . ? O1 Mn1 N1 C11 48.6(3) . . . . ? O7 Mn1 N1 C11 -125.1(3) . . . . ? N3 Mn1 N1 C11 169.0(7) . . . . ? O2 Mn1 N1 C11 -42.6(3) . . . . ? N2 Mn1 N1 C11 145.1(3) . . . . ? O1 Mn1 N1 Mn2 -115.93(10) . . . . ? O7 Mn1 N1 Mn2 70.29(8) . . . . ? N3 Mn1 N1 Mn2 4.4(8) . . . . ? O2 Mn1 N1 Mn2 152.86(9) . . . . ? N2 Mn1 N1 Mn2 -19.50(8) . . . . ? O4 C12 N2 Mn2 128(5) . . . . ? O4 C12 N2 Mn1 -28(5) . . . . ? N2 Mn2 N2 C12 3(100) 2_666 . . . ? N1 Mn2 N2 C12 -177.9(4) . . . . ? N1 Mn2 N2 C12 2.1(4) 2_666 . . . ? O6 Mn2 N2 C12 87.8(4) 2_666 . . . ? O6 Mn2 N2 C12 -92.2(4) . . . . ? N2 Mn2 N2 Mn1 160(100) 2_666 . . . ? N1 Mn2 N2 Mn1 -20.50(8) . . . . ? N1 Mn2 N2 Mn1 159.50(8) 2_666 . . . ? O6 Mn2 N2 Mn1 -114.73(8) 2_666 . . . ? O6 Mn2 N2 Mn1 65.27(8) . . . . ? O1 Mn1 N2 C12 -84.6(2) . . . . ? O7 Mn1 N2 C12 98.9(2) . . . . ? N3 Mn1 N2 C12 8.6(2) . . . . ? O2 Mn1 N2 C12 144.6(4) . . . . ? N1 Mn1 N2 C12 -173.8(2) . . . . ? O1 Mn1 N2 Mn2 108.74(10) . . . . ? O7 Mn1 N2 Mn2 -67.69(8) . . . . ? N3 Mn1 N2 Mn2 -157.99(9) . . . . ? O2 Mn1 N2 Mn2 -22.0(5) . . . . ? N1 Mn1 N2 Mn2 19.62(8) . . . . ? O5 C13 N3 Mn1 -115(8) . . . . ? O1 Mn1 N3 C13 147.6(3) . . . . ? O7 Mn1 N3 C13 -38.4(3) . . . . ? O2 Mn1 N3 C13 -121.1(3) . . . . ? N2 Mn1 N3 C13 50.9(3) . . . . ? N1 Mn1 N3 C13 27.3(10) . . . . ? C6 C5 N4 C4 0.9(4) . . . . ? C6 C5 N4 C7 -179.5(2) . . . . ? C3 C4 N4 C5 -0.7(4) . . . . ? C3 C4 N4 C7 179.7(2) . . . . ? C8 C7 N4 C5 98.9(3) . . . . ? C8 C7 N4 C4 -81.5(3) . . . . ? C16 C17 N5 C19 -0.8(4) . . . . ? C16 C17 N5 C20 176.7(2) . . . . ? C18 C19 N5 C17 -0.4(4) . . . . ? C18 C19 N5 C20 -177.8(2) . . . . ? C21 C20 N5 C17 -63.7(3) . . . . ? C21 C20 N5 C19 113.9(3) . . . . ? O7 C1 O6 Mn2 26.7(3) . . . . ? C2 C1 O6 Mn2 -152.96(15) . . . . ? N2 Mn2 O6 C1 -46.77(19) . . . . ? N2 Mn2 O6 C1 133.23(19) 2_666 . . . ? N1 Mn2 O6 C1 35.71(19) . . . . ? N1 Mn2 O6 C1 -144.29(19) 2_666 . . . ? O6 Mn2 O6 C1 -145(100) 2_666 . . . ? O6 C1 O7 Mn1 -37.1(4) . . . . ? C2 C1 O7 Mn1 142.52(17) . . . . ? O1 Mn1 O7 C1 -88.0(7) . . . . ? N3 Mn1 O7 C1 155.7(2) . . . . ? O2 Mn1 O7 C1 -112.0(2) . . . . ? N2 Mn1 O7 C1 59.7(2) . . . . ? N1 Mn1 O7 C1 -19.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.523 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.059