# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_2b_rg999cm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 N6 O7 Re2' _chemical_formula_weight 900.88 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 13.196(4) _cell_length_b 13.787(5) _cell_length_c 15.404(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2802.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 825 _cell_measurement_theta_min 2.512 _cell_measurement_theta_max 22.925 _exptl_crystal_description PRISM _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 8.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.476968 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_% ? _diffrn_reflns_number 11627 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2024 _reflns_number_gt 1401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0260P)^2^+25.5840P] 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 2024 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 Re1 Re 0.12658(4) 0.16722(3) 0.16514(3) 0.0462(2) Uani 1 1 d . . . C1 C 0.1428(10) 0.2438(9) 0.0611(8) 0.059(3) Uani 1 1 d . . . O1 O 0.1427(8) 0.2905(6) -0.0005(5) 0.082(3) Uani 1 1 d . . . C2 C -0.0104(15) 0.1757(9) 0.1343(8) 0.074(4) Uani 1 1 d . . . O2 O -0.0985(8) 0.1807(8) 0.1158(7) 0.090(3) Uani 1 1 d . . . C3 C 0.1346(11) 0.0489(8) 0.1001(7) 0.057(3) Uani 1 1 d . . . O3 O 0.1343(9) -0.0178(6) 0.0562(5) 0.097(4) Uani 1 1 d . . . N1 N 0.0969(8) 0.0777(6) 0.2828(6) 0.046(2) Uani 1 1 d . . . N2 N 0.2724(7) 0.1495(5) 0.2348(5) 0.043(2) Uani 1 1 d . . . N3 N 0.3604(7) 0.1992(6) 0.2362(6) 0.043(2) Uani 1 1 d . . . C11 C 0.0042(11) 0.0457(9) 0.3055(8) 0.059(3) Uani 1 1 d . . . H11 H -0.0518 0.0706 0.2764 0.071 Uiso 1 1 calc R . . C12 C -0.0117(13) -0.0218(10) 0.3696(9) 0.076(4) Uani 1 1 d . . . H12 H -0.0769 -0.0412 0.3847 0.092 Uiso 1 1 calc R . . C13 C 0.0713(14) -0.0597(9) 0.4107(9) 0.073(4) Uani 1 1 d . . . H13 H 0.0628 -0.1073 0.4528 0.087 Uiso 1 1 calc R . . C14 C 0.1665(11) -0.0281(8) 0.3905(7) 0.057(3) Uani 1 1 d . . . H14 H 0.2228 -0.0526 0.4195 0.068 Uiso 1 1 calc R . . C15 C 0.1779(10) 0.0422(8) 0.3248(7) 0.049(3) Uani 1 1 d . . . C16 C 0.2730(10) 0.0872(7) 0.3024(7) 0.045(3) Uani 1 1 d . . . C17 C 0.3635(10) 0.0931(8) 0.3459(7) 0.053(3) Uani 1 1 d . . . H17 H 0.3848 0.0567 0.3934 0.064 Uiso 1 1 calc R . . C18 C 0.4152(10) 0.1644(8) 0.3037(7) 0.056(3) Uani 1 1 d . . . H18 H 0.4794 0.1862 0.3191 0.067 Uiso 1 1 calc R . . O90 O 0.7500 0.2500 0.286(2) 0.34(3) Uani 1 2 d S . . C90 C 0.675(2) 0.278(3) 0.331(2) 0.240(19) Uani 1 1 d . . . H90A H 0.6161 0.2385 0.3174 0.288 Uiso 1 1 calc R . . H90B H 0.6592 0.3450 0.3171 0.288 Uiso 1 1 calc R . . C91 C 0.700(3) 0.269(3) 0.4150(16) 0.25(3) Uani 1 1 d . . . H91A H 0.6538 0.2251 0.4444 0.298 Uiso 1 1 calc R . . H91B H 0.6979 0.3315 0.4439 0.298 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.0697(3) 0.0335(3) 0.0352(3) -0.0010(2) -0.0059(3) 0.0015(3) C1 0.072(9) 0.047(7) 0.058(7) 0.002(6) -0.007(7) -0.002(7) O1 0.137(9) 0.064(5) 0.047(5) 0.024(5) -0.007(6) 0.004(6) C2 0.143(15) 0.038(7) 0.041(7) 0.005(6) 0.004(10) 0.008(9) O2 0.082(8) 0.100(8) 0.089(8) 0.005(6) -0.031(6) -0.001(7) C3 0.085(10) 0.040(7) 0.047(7) 0.008(6) -0.005(8) 0.007(8) O3 0.185(11) 0.046(5) 0.059(5) -0.017(4) -0.005(7) 0.002(7) N1 0.060(7) 0.041(5) 0.037(5) 0.002(4) -0.003(5) -0.006(5) N2 0.063(7) 0.019(4) 0.046(5) 0.004(4) 0.005(5) 0.007(5) N3 0.063(7) 0.022(4) 0.044(5) 0.000(4) 0.002(5) 0.003(5) C11 0.070(9) 0.052(8) 0.055(7) -0.005(7) -0.002(8) -0.011(7) C12 0.101(12) 0.064(10) 0.065(9) -0.006(8) 0.013(9) -0.025(9) C13 0.116(13) 0.045(8) 0.057(8) 0.001(7) 0.010(10) -0.011(9) C14 0.067(9) 0.052(8) 0.052(7) 0.018(6) -0.007(7) -0.008(7) C15 0.077(9) 0.040(6) 0.030(6) 0.002(5) -0.005(7) 0.007(7) C16 0.061(8) 0.032(6) 0.041(6) 0.005(5) 0.002(7) 0.001(6) C17 0.068(8) 0.045(7) 0.047(7) 0.014(5) -0.007(7) 0.004(7) C18 0.069(8) 0.048(7) 0.050(7) 0.003(6) 0.003(7) 0.018(7) O90 0.21(4) 0.62(8) 0.19(3) 0.000 0.000 0.18(5) C90 0.17(3) 0.36(5) 0.19(3) 0.09(4) 0.05(3) 0.14(3) C91 0.39(8) 0.17(4) 0.18(2) -0.07(3) 0.17(4) -0.05(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C2 1.87(2) . ? Re1 C3 1.917(12) . ? Re1 C1 1.931(13) . ? Re1 N3 2.149(8) 2 ? Re1 N2 2.217(9) . ? Re1 N1 2.227(9) . ? C1 O1 1.147(13) . ? C2 O2 1.198(18) . ? C3 O3 1.143(13) . ? N1 C15 1.343(14) . ? N1 C11 1.347(14) . ? N2 N3 1.349(12) . ? N2 C16 1.349(12) . ? N3 C18 1.355(14) . ? N3 Re1 2.149(8) 2 ? C11 C12 1.374(17) . ? C12 C13 1.369(19) . ? C13 C14 1.365(18) . ? C14 C15 1.409(15) . ? C15 C16 1.441(16) . ? C16 C17 1.373(15) . ? C17 C18 1.361(16) . ? O90 C90 1.26(3) 2_655 ? O90 C90 1.26(3) . ? C90 C91 1.35(3) . ? C91 C91 1.42(6) 2_655 ? 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 C2 Re1 C3 88.5(6) . . ? C2 Re1 C1 82.1(5) . . ? C3 Re1 C1 91.4(5) . . ? C2 Re1 N3 98.8(5) . 2 ? C3 Re1 N3 172.2(5) . 2 ? C1 Re1 N3 86.9(4) . 2 ? C2 Re1 N2 165.3(4) . . ? C3 Re1 N2 96.4(4) . . ? C1 Re1 N2 111.5(4) . . ? N3 Re1 N2 77.2(3) 2 . ? C2 Re1 N1 94.1(5) . . ? C3 Re1 N1 87.9(4) . . ? C1 Re1 N1 176.1(5) . . ? N3 Re1 N1 94.3(3) 2 . ? N2 Re1 N1 72.4(3) . . ? O1 C1 Re1 173.5(12) . . ? O2 C2 Re1 179.0(12) . . ? O3 C3 Re1 174.1(11) . . ? C15 N1 C11 118.6(10) . . ? C15 N1 Re1 117.0(8) . . ? C11 N1 Re1 123.6(8) . . ? N3 N2 C16 107.9(9) . . ? N3 N2 Re1 134.3(6) . . ? C16 N2 Re1 116.6(8) . . ? N2 N3 C18 106.9(9) . . ? N2 N3 Re1 119.8(6) . 2 ? C18 N3 Re1 130.7(8) . 2 ? N1 C11 C12 123.2(14) . . ? C13 C12 C11 118.0(14) . . ? C14 C13 C12 120.6(13) . . ? C13 C14 C15 118.8(12) . . ? N1 C15 C14 120.8(12) . . ? N1 C15 C16 114.9(9) . . ? C14 C15 C16 124.2(12) . . ? N2 C16 C17 110.1(10) . . ? N2 C16 C15 117.0(11) . . ? C17 C16 C15 131.7(10) . . ? C18 C17 C16 104.2(10) . . ? N3 C18 C17 110.8(12) . . ? C90 O90 C90 115(4) 2_655 . ? O90 C90 C91 108(3) . . ? C90 C91 C91 105.1(19) . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.338 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.131 _database_code_depnum_ccdc_archive 'CCDC 873520' ####################################################################### # # 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_compound_Li3a_fv6b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 Li Mn N6 O5' _chemical_formula_weight 524.35 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' Li Li -0.0003 0.0001 '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 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4703(11) _cell_length_b 10.3819(9) _cell_length_c 20.924(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.452(9) _cell_angle_gamma 90.00 _cell_volume 2475.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2615 _cell_measurement_theta_min 2.1277 _cell_measurement_theta_max 28.7239 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3502 _exptl_crystal_size_mid 0.1088 _exptl_crystal_size_min 0.0645 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.870 _exptl_absorpt_correction_T_max 0.965 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -16 1 -2 0.0413 -16.0000 1.0000 -2.0000 -0.4406 0.4134 -0.8035 16 -1 2 0.0232 16.0000 -1.0000 2.0000 0.4406 -0.4134 0.8035 4 13 9 0.1320 4.0000 13.0000 9.0000 -0.4948 0.3628 0.7628 8 -13 -5 0.1167 8.0000 -13.0000 -5.0000 0.7422 -0.6908 -0.1087 3 0 -29 0.0601 3.0000 0.0000 -29.0000 0.7882 0.5769 -0.1282 -1 0 29 0.0418 -1.0000 0.0000 29.0000 -0.7308 -0.6170 0.230 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _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 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4757 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10303 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.79 _reflns_number_total 5576 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'Tue Jun 04 15:20:07 2013' ; _computing_cell_refinement ; 'Tue Jun 04 15:20:07 2013' ; _computing_data_reduction ; 'Tue Jun 04 15:20:07 2013' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.2474P] 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 5576 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 -0.08218(4) 0.25552(5) 0.14918(3) 0.04511(18) Uani 1 1 d . . . C1 C -0.0210(3) 0.4143(4) 0.14669(18) 0.0538(9) Uani 1 1 d . . . O1 O 0.0176(3) 0.5156(3) 0.14609(15) 0.0852(9) Uani 1 1 d . . . C2 C -0.0837(3) 0.2641(3) 0.2352(2) 0.0533(9) Uani 1 1 d . . . O2 O -0.0906(3) 0.2722(3) 0.28870(14) 0.0809(9) Uani 1 1 d . . . C3 C -0.2255(4) 0.3257(4) 0.1404(2) 0.0695(12) Uani 1 1 d . . . O3 O -0.3132(3) 0.3778(4) 0.1385(2) 0.1241(15) Uani 1 1 d . . . Li1 Li 0.2320(5) 0.3657(6) 0.0764(4) 0.0680(19) Uani 1 1 d . . . N1 N -0.1390(2) 0.0652(3) 0.14136(16) 0.0512(8) Uani 1 1 d . . . N2 N -0.0903(2) 0.2256(3) 0.05426(14) 0.0466(7) Uani 1 1 d . . . N3 N -0.0756(3) 0.3011(3) 0.00349(15) 0.0561(8) Uani 1 1 d . . . N4 N 0.3698(3) 0.2383(3) 0.06615(18) 0.0686(9) Uani 1 1 d . . . N5 N 0.1708(2) 0.2144(3) 0.12426(15) 0.0491(7) Uani 1 1 d . . . N6 N 0.0840(2) 0.1798(2) 0.15985(14) 0.0455(7) Uani 1 1 d . . . C11 C -0.1638(3) -0.0120(4) 0.1887(2) 0.0653(11) Uani 1 1 d . . . H11 H -0.1618 0.0219 0.2299 0.078 Uiso 1 1 calc R . . C12 C -0.1922(3) -0.1403(4) 0.1793(3) 0.0783(14) Uani 1 1 d . . . H12 H -0.2092 -0.1918 0.2134 0.094 Uiso 1 1 calc R . . C13 C -0.1947(4) -0.1901(4) 0.1183(3) 0.0839(16) Uani 1 1 d . . . H13 H -0.2123 -0.2766 0.1108 0.101 Uiso 1 1 calc R . . C14 C -0.1713(3) -0.1122(4) 0.0691(3) 0.0681(12) Uani 1 1 d . . . H14 H -0.1737 -0.1446 0.0276 0.082 Uiso 1 1 calc R . . C15 C -0.1438(3) 0.0157(3) 0.0815(2) 0.0517(9) Uani 1 1 d . . . C16 C -0.1204(3) 0.1068(3) 0.03314(19) 0.0496(9) Uani 1 1 d . . . C17 C -0.1254(3) 0.1039(4) -0.0333(2) 0.0661(11) Uani 1 1 d . . . H17 H -0.1437 0.0347 -0.0608 0.079 Uiso 1 1 calc R . . C18 C -0.0968(4) 0.2274(4) -0.0489(2) 0.0698(12) Uani 1 1 d . . . H18 H -0.0927 0.2562 -0.0907 0.084 Uiso 1 1 calc R . . C19 C 0.4617(4) 0.2451(5) 0.0320(2) 0.0851(14) Uani 1 1 d . . . H19 H 0.4633 0.3104 0.0017 0.102 Uiso 1 1 calc R . . C20 C 0.5535(4) 0.1598(5) 0.0400(3) 0.0876(15) Uani 1 1 d . . . H20 H 0.6161 0.1671 0.0156 0.105 Uiso 1 1 calc R . . C21 C 0.5510(4) 0.0649(5) 0.0841(3) 0.0907(16) Uani 1 1 d . . . H21 H 0.6119 0.0055 0.0904 0.109 Uiso 1 1 calc R . . C22 C 0.4578(3) 0.0573(4) 0.1194(2) 0.0755(13) Uani 1 1 d . . . H22 H 0.4554 -0.0067 0.1503 0.091 Uiso 1 1 calc R . . C23 C 0.3677(3) 0.1450(4) 0.1089(2) 0.0569(10) Uani 1 1 d . . . C24 C 0.2639(3) 0.1375(3) 0.14304(19) 0.0490(9) Uani 1 1 d . . . C25 C 0.2377(3) 0.0551(4) 0.1910(2) 0.0621(11) Uani 1 1 d . . . H25 H 0.2858 -0.0072 0.2123 0.074 Uiso 1 1 calc R . . C26 C 0.1245(3) 0.0859(3) 0.20030(19) 0.0575(10) Uani 1 1 d . . . H26 H 0.0820 0.0471 0.2304 0.069 Uiso 1 1 calc R . . O40 O 0.3219(3) 0.5011(3) 0.12732(19) 0.0942(10) Uani 1 1 d . . . C41 C 0.3703(7) 0.5998(7) 0.0963(4) 0.201(4) Uani 1 1 d . . . H41A H 0.3090 0.6494 0.0718 0.242 Uiso 1 1 calc R . . H41B H 0.4218 0.5657 0.0667 0.242 Uiso 1 1 calc R . . C42 C 0.4357(9) 0.6808(9) 0.1429(5) 0.215(5) Uani 1 1 d . . . H42A H 0.5126 0.6990 0.1301 0.258 Uiso 1 1 calc R . . H42B H 0.3949 0.7617 0.1470 0.258 Uiso 1 1 calc R . . C43 C 0.4459(10) 0.6163(11) 0.1995(5) 0.229(5) Uani 1 1 d . . . H43A H 0.4070 0.6630 0.2312 0.274 Uiso 1 1 calc R . . H43B H 0.5279 0.6056 0.2157 0.274 Uiso 1 1 calc R . . C44 C 0.3897(2) 0.4893(2) 0.18640(13) 0.172(3) Uani 1 1 d . . . H44A H 0.4486 0.4227 0.1846 0.207 Uiso 1 1 calc R . . H44B H 0.3409 0.4673 0.2198 0.207 Uiso 1 1 calc R . . O50 O 0.1428(2) 0.4349(2) 0.00460(13) 0.0721(8) Uani 1 1 d R . . H50A H 0.1338 0.5102 0.0011 0.087 Uiso 1 1 d R . . H50B H 0.0793 0.3943 0.0056 0.087 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0502(3) 0.0426(3) 0.0430(3) -0.0045(3) 0.0071(2) 0.0028(2) C1 0.069(2) 0.055(2) 0.037(2) -0.0062(18) 0.0048(18) 0.0053(19) O1 0.128(3) 0.0511(16) 0.077(2) -0.0065(16) 0.0136(19) -0.0174(17) C2 0.066(2) 0.047(2) 0.048(2) 0.000(2) 0.0107(18) 0.0005(17) O2 0.127(3) 0.0736(19) 0.0462(19) -0.0012(16) 0.0283(17) 0.0011(17) C3 0.066(3) 0.066(3) 0.076(3) -0.022(2) 0.002(2) 0.004(2) O3 0.069(2) 0.126(3) 0.173(4) -0.050(3) -0.006(2) 0.041(2) Li1 0.061(4) 0.064(4) 0.080(6) 0.010(4) 0.015(3) 0.006(3) N1 0.0408(15) 0.0468(16) 0.066(2) 0.0001(17) 0.0080(15) -0.0007(13) N2 0.0510(16) 0.0466(16) 0.0420(18) -0.0046(14) 0.0042(13) 0.0036(13) N3 0.0701(19) 0.0588(18) 0.039(2) -0.0018(16) 0.0063(15) 0.0018(15) N4 0.0541(19) 0.076(2) 0.078(3) 0.004(2) 0.0173(17) 0.0066(16) N5 0.0447(16) 0.0464(16) 0.056(2) 0.0010(14) 0.0061(14) 0.0005(13) N6 0.0480(16) 0.0418(15) 0.0468(19) -0.0003(14) 0.0054(14) 0.0018(13) C11 0.059(2) 0.058(2) 0.078(3) 0.006(2) 0.007(2) -0.0027(19) C12 0.064(3) 0.058(3) 0.113(5) 0.023(3) 0.011(3) -0.003(2) C13 0.067(3) 0.048(2) 0.137(5) -0.003(3) 0.013(3) 0.001(2) C14 0.055(2) 0.049(2) 0.102(4) -0.019(2) 0.012(2) 0.0008(18) C15 0.0390(18) 0.0439(19) 0.072(3) -0.013(2) 0.0059(18) 0.0052(15) C16 0.0453(19) 0.048(2) 0.056(3) -0.0174(19) 0.0059(17) 0.0060(15) C17 0.064(2) 0.073(3) 0.061(3) -0.028(2) 0.008(2) -0.002(2) C18 0.081(3) 0.088(3) 0.041(2) -0.013(2) 0.009(2) 0.002(2) C19 0.064(3) 0.106(4) 0.089(4) 0.001(3) 0.025(2) 0.002(3) C20 0.050(3) 0.112(4) 0.104(5) -0.022(4) 0.022(3) 0.003(3) C21 0.056(3) 0.091(4) 0.125(5) -0.017(3) 0.010(3) 0.020(3) C22 0.054(2) 0.069(3) 0.102(4) 0.001(3) 0.006(2) 0.010(2) C23 0.045(2) 0.053(2) 0.072(3) -0.010(2) 0.0024(19) 0.0026(17) C24 0.0439(19) 0.0439(18) 0.057(3) -0.0011(18) -0.0020(17) 0.0030(15) C25 0.061(2) 0.054(2) 0.070(3) 0.009(2) 0.000(2) 0.0081(18) C26 0.062(2) 0.057(2) 0.054(3) 0.010(2) 0.0068(19) -0.0037(18) O40 0.079(2) 0.084(2) 0.119(3) 0.016(2) 0.0070(19) -0.0142(17) C41 0.213(8) 0.145(6) 0.221(10) 0.078(7) -0.085(7) -0.099(6) C42 0.252(10) 0.162(8) 0.210(12) 0.022(8) -0.068(9) -0.113(7) C43 0.306(12) 0.230(12) 0.136(9) -0.029(8) -0.041(9) -0.117(10) C44 0.242(9) 0.181(8) 0.093(6) 0.025(6) 0.012(6) -0.055(7) O50 0.0710(16) 0.0616(16) 0.084(2) 0.0085(16) 0.0079(15) 0.0067(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 C3 1.788(4) . ? Mn1 C1 1.795(4) . ? Mn1 C2 1.805(4) . ? Mn1 N2 2.002(3) . ? Mn1 N6 2.051(3) . ? Mn1 N1 2.082(3) . ? C1 O1 1.141(4) . ? C2 O2 1.133(4) . ? C3 O3 1.140(4) . ? Li1 O50 1.864(8) . ? Li1 O40 1.982(8) . ? Li1 N5 2.030(7) . ? Li1 N4 2.090(7) . ? N1 C11 1.329(5) . ? N1 C15 1.348(5) . ? N2 C16 1.343(4) . ? N2 N3 1.346(4) . ? N3 C18 1.337(5) . ? N4 C23 1.320(5) . ? N4 C19 1.340(5) . ? N5 C24 1.355(4) . ? N5 N6 1.357(4) . ? N6 C26 1.339(4) . ? C11 C12 1.380(5) . ? C12 C13 1.374(7) . ? C13 C14 1.360(6) . ? C14 C15 1.383(5) . ? C15 C16 1.432(5) . ? C16 C17 1.386(5) . ? C17 C18 1.372(5) . ? C19 C20 1.371(6) . ? C20 C21 1.353(6) . ? C21 C22 1.368(6) . ? C22 C23 1.377(5) . ? C23 C24 1.458(5) . ? C24 C25 1.378(5) . ? C25 C26 1.372(5) . ? O40 C41 1.364(7) . ? O40 C44 1.390(4) . ? C41 C42 1.435(10) . ? C42 C43 1.353(10) . ? C43 C44 1.479(9) . ? 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 C3 Mn1 C1 88.90(17) . . ? C3 Mn1 C2 88.26(19) . . ? C1 Mn1 C2 91.78(16) . . ? C3 Mn1 N2 91.26(16) . . ? C1 Mn1 N2 95.08(14) . . ? C2 Mn1 N2 173.11(14) . . ? C3 Mn1 N6 178.48(14) . . ? C1 Mn1 N6 89.64(13) . . ? C2 Mn1 N6 91.35(14) . . ? N2 Mn1 N6 89.30(11) . . ? C3 Mn1 N1 95.88(14) . . ? C1 Mn1 N1 171.81(15) . . ? C2 Mn1 N1 95.01(15) . . ? N2 Mn1 N1 78.20(12) . . ? N6 Mn1 N1 85.62(10) . . ? O1 C1 Mn1 178.9(4) . . ? O2 C2 Mn1 176.3(4) . . ? O3 C3 Mn1 174.4(4) . . ? O50 Li1 O40 111.4(3) . . ? O50 Li1 N5 120.4(3) . . ? O40 Li1 N5 118.1(4) . . ? O50 Li1 N4 120.9(4) . . ? O40 Li1 N4 98.6(3) . . ? N5 Li1 N4 82.4(3) . . ? C11 N1 C15 118.2(3) . . ? C11 N1 Mn1 127.2(3) . . ? C15 N1 Mn1 114.5(2) . . ? C16 N2 N3 109.0(3) . . ? C16 N2 Mn1 116.8(3) . . ? N3 N2 Mn1 134.1(2) . . ? C18 N3 N2 106.6(3) . . ? C23 N4 C19 118.3(4) . . ? C23 N4 Li1 108.9(3) . . ? C19 N4 Li1 132.1(4) . . ? C24 N5 N6 106.8(3) . . ? C24 N5 Li1 107.1(3) . . ? N6 N5 Li1 142.3(3) . . ? C26 N6 N5 108.4(3) . . ? C26 N6 Mn1 126.9(2) . . ? N5 N6 Mn1 124.7(2) . . ? N1 C11 C12 122.9(5) . . ? C13 C12 C11 118.3(5) . . ? C14 C13 C12 119.6(4) . . ? C13 C14 C15 119.3(5) . . ? N1 C15 C14 121.6(4) . . ? N1 C15 C16 114.4(3) . . ? C14 C15 C16 123.9(4) . . ? N2 C16 C17 109.3(4) . . ? N2 C16 C15 115.8(3) . . ? C17 C16 C15 134.9(4) . . ? C18 C17 C16 103.6(3) . . ? N3 C18 C17 111.5(4) . . ? N4 C19 C20 122.7(5) . . ? C21 C20 C19 118.6(4) . . ? C20 C21 C22 119.2(4) . . ? C21 C22 C23 119.6(5) . . ? N4 C23 C22 121.6(4) . . ? N4 C23 C24 116.7(3) . . ? C22 C23 C24 121.7(4) . . ? N5 C24 C25 110.3(3) . . ? N5 C24 C23 119.1(3) . . ? C25 C24 C23 130.3(3) . . ? C26 C25 C24 104.2(3) . . ? N6 C26 C25 110.3(3) . . ? C41 O40 C44 105.8(4) . . ? C41 O40 Li1 119.5(5) . . ? C44 O40 Li1 128.4(3) . . ? O40 C41 C42 109.0(7) . . ? C43 C42 C41 107.0(8) . . ? C42 C43 C44 106.7(7) . . ? O40 C44 C43 105.9(5) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.357 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 974910' ####################################################################### # # 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_Compound_Na3a_ma2591am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H24 Mn2 N12 Na2 O6' _chemical_formula_weight 900.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.639(6) _cell_length_b 12.712(5) _cell_length_c 19.580(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.759(7) _cell_angle_gamma 90.00 _cell_volume 3888(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 909 _cell_measurement_theta_min 2.285 _cell_measurement_theta_max 23.085 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.712015 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _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_% ? _diffrn_reflns_number 8447 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2779 _reflns_number_gt 2252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0478P)^2^+1.0867P] 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 2779 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.67919(2) 0.86077(3) 0.822739(18) 0.04298(16) Uani 1 1 d . . . C1 C 0.70535(16) 0.7303(2) 0.84832(12) 0.0476(6) Uani 1 1 d . . . O1 O 0.71517(14) 0.64469(16) 0.86710(11) 0.0690(6) Uani 1 1 d . . . C2 C 0.69009(17) 0.8273(2) 0.73365(15) 0.0559(7) Uani 1 1 d . . . O2 O 0.69673(14) 0.8051(2) 0.67769(11) 0.0882(7) Uani 1 1 d . . . C3 C 0.56935(19) 0.8200(3) 0.82132(14) 0.0716(9) Uani 1 1 d . . . O3 O 0.50066(15) 0.7912(3) 0.82469(13) 0.1381(14) Uani 1 1 d . . . N1 N 0.64289(12) 1.01596(17) 0.80593(11) 0.0508(6) Uani 1 1 d . . . N2 N 0.66615(11) 0.91196(17) 0.91879(9) 0.0427(5) Uani 1 1 d . . . N3 N 0.66940(12) 0.86277(16) 0.98015(10) 0.0460(5) Uani 1 1 d . . . C11 C 0.63594(17) 1.0665(2) 0.74606(15) 0.0634(8) Uani 1 1 d . . . H11 H 0.6470 1.0294 0.7065 0.076 Uiso 1 1 calc R . . C12 C 0.61334(18) 1.1704(3) 0.74013(17) 0.0712(9) Uani 1 1 d . . . H12 H 0.6098 1.2030 0.6976 0.085 Uiso 1 1 calc R . . C13 C 0.5962(2) 1.2247(3) 0.79760(19) 0.0758(9) Uani 1 1 d . . . H13 H 0.5801 1.2951 0.7948 0.091 Uiso 1 1 calc R . . C14 C 0.60274(19) 1.1752(2) 0.85974(17) 0.0668(8) Uani 1 1 d . . . H14 H 0.5914 1.2119 0.8994 0.080 Uiso 1 1 calc R . . C15 C 0.62623(14) 1.0708(2) 0.86313(14) 0.0501(7) Uani 1 1 d . . . C16 C 0.63513(14) 1.0096(2) 0.92567(13) 0.0461(6) Uani 1 1 d . . . C17 C 0.61695(16) 1.0263(2) 0.99294(14) 0.0562(7) Uani 1 1 d . . . H17 H 0.5950 1.0867 1.0124 0.067 Uiso 1 1 calc R . . C18 C 0.63881(16) 0.9334(2) 1.02436(13) 0.0556(7) Uani 1 1 d . . . H18 H 0.6333 0.9203 1.0707 0.067 Uiso 1 1 calc R . . Na Na 0.83640(6) 0.82486(8) 0.99454(5) 0.0535(3) Uani 1 1 d . . . N4 N 0.98991(13) 0.85773(16) 0.98210(11) 0.0474(5) Uani 1 1 d . . . N5 N 0.85700(11) 0.87897(14) 0.88288(10) 0.0390(5) Uani 1 1 d . . . N6 N 0.80227(11) 0.91355(15) 0.83172(9) 0.0397(5) Uani 1 1 d . . . C19 C 1.05625(18) 0.8393(2) 1.02658(15) 0.0605(8) Uani 1 1 d . . . H19 H 1.0459 0.8038 1.0669 0.073 Uiso 1 1 calc R . . C20 C 1.13862(18) 0.8703(2) 1.01570(17) 0.0691(9) Uani 1 1 d . . . H20 H 1.1829 0.8555 1.0476 0.083 Uiso 1 1 calc R . . C21 C 1.15381(18) 0.9232(2) 0.95696(18) 0.0695(9) Uani 1 1 d . . . H21 H 1.2089 0.9453 0.9483 0.083 Uiso 1 1 calc R . . C22 C 1.08672(16) 0.9436(2) 0.91046(15) 0.0574(7) Uani 1 1 d . . . H22 H 1.0961 0.9799 0.8703 0.069 Uiso 1 1 calc R . . C23 C 1.00478(14) 0.90920(19) 0.92432(13) 0.0435(6) Uani 1 1 d . . . C24 C 0.93227(14) 0.92773(18) 0.87580(12) 0.0401(6) Uani 1 1 d . . . C25 C 0.92616(17) 0.9944(2) 0.81991(14) 0.0586(8) Uani 1 1 d . . . H25 H 0.9686 1.0376 0.8035 0.070 Uiso 1 1 calc R . . C26 C 0.84400(17) 0.9828(2) 0.79417(13) 0.0540(7) Uani 1 1 d . . . H26 H 0.8205 1.0180 0.7561 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0397(2) 0.0507(3) 0.0384(2) 0.00589(17) 0.00070(16) -0.00230(18) C1 0.0489(14) 0.0556(18) 0.0381(14) -0.0021(13) 0.0001(11) -0.0119(13) O1 0.0867(15) 0.0477(13) 0.0719(14) 0.0098(10) -0.0020(11) -0.0101(11) C2 0.0496(15) 0.0681(19) 0.0496(18) 0.0058(14) -0.0026(13) -0.0045(14) O2 0.0895(16) 0.128(2) 0.0468(13) -0.0127(13) 0.0010(11) -0.0028(14) C3 0.0558(19) 0.112(3) 0.0465(17) 0.0276(17) -0.0083(13) -0.0115(18) O3 0.0561(15) 0.258(4) 0.097(2) 0.074(2) -0.0215(13) -0.0620(19) N1 0.0424(11) 0.0574(14) 0.0530(14) 0.0169(11) 0.0077(10) 0.0104(10) N2 0.0361(10) 0.0517(13) 0.0405(12) 0.0092(10) 0.0030(9) 0.0024(10) N3 0.0398(11) 0.0581(14) 0.0404(12) 0.0096(10) 0.0041(9) -0.0006(10) C11 0.0573(17) 0.075(2) 0.0588(19) 0.0233(16) 0.0118(13) 0.0181(16) C12 0.0603(18) 0.080(2) 0.074(2) 0.0361(19) 0.0105(16) 0.0151(17) C13 0.073(2) 0.057(2) 0.098(3) 0.0227(19) 0.0026(18) 0.0132(16) C14 0.0673(19) 0.0573(19) 0.076(2) 0.0071(16) 0.0052(15) 0.0136(16) C15 0.0357(13) 0.0578(18) 0.0572(17) 0.0101(14) 0.0057(12) 0.0084(12) C16 0.0334(12) 0.0532(17) 0.0518(17) 0.0070(12) 0.0040(11) 0.0057(12) C17 0.0512(15) 0.0659(19) 0.0520(17) -0.0042(14) 0.0062(12) 0.0129(14) C18 0.0468(15) 0.082(2) 0.0385(15) 0.0043(15) 0.0073(12) 0.0035(14) Na 0.0439(5) 0.0649(7) 0.0523(6) 0.0133(5) 0.0062(4) -0.0094(5) N4 0.0445(12) 0.0492(13) 0.0487(13) -0.0003(10) 0.0035(10) -0.0042(10) N5 0.0375(10) 0.0360(12) 0.0438(12) 0.0014(9) 0.0058(9) -0.0029(9) N6 0.0409(11) 0.0390(12) 0.0396(11) 0.0025(9) 0.0060(9) -0.0006(9) C19 0.0586(18) 0.0645(19) 0.0580(18) -0.0007(14) -0.0017(14) -0.0009(15) C20 0.0463(17) 0.078(2) 0.081(2) -0.0077(18) -0.0111(15) -0.0026(15) C21 0.0400(15) 0.068(2) 0.100(3) -0.0073(19) 0.0052(16) -0.0128(14) C22 0.0443(15) 0.0542(18) 0.074(2) 0.0007(14) 0.0114(13) -0.0111(13) C23 0.0385(13) 0.0372(14) 0.0556(16) -0.0082(12) 0.0101(11) -0.0066(11) C24 0.0403(13) 0.0360(14) 0.0449(14) -0.0044(11) 0.0114(11) -0.0055(11) C25 0.0526(16) 0.065(2) 0.0587(17) 0.0129(14) 0.0139(13) -0.0192(14) C26 0.0569(16) 0.0601(18) 0.0460(16) 0.0160(13) 0.0108(12) -0.0038(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 Mn1 C1 1.774(3) . ? Mn1 C3 1.793(3) . ? Mn1 C2 1.811(3) . ? Mn1 N2 2.010(2) . ? Mn1 N6 2.038(2) . ? Mn1 N1 2.075(2) . ? C1 O1 1.157(3) . ? O1 Na 2.890(3) 7_667 ? C2 O2 1.141(3) . ? C3 O3 1.140(3) . ? N1 C11 1.337(3) . ? N1 C15 1.355(3) . ? N2 C16 1.341(3) . ? N2 N3 1.353(3) . ? N3 C18 1.351(3) . ? N3 Na 2.439(2) 7_667 ? N3 Na 2.657(2) . ? C11 C12 1.371(4) . ? C12 C13 1.358(4) . ? C13 C14 1.369(4) . ? C14 C15 1.378(4) . ? C15 C16 1.452(3) . ? C16 C17 1.377(3) . ? C17 C18 1.368(4) . ? Na N5 2.329(2) . ? Na N3 2.439(2) 7_667 ? Na N4 2.461(2) . ? Na O1 2.890(3) 7_667 ? Na Na 3.321(2) 7_667 ? N4 C23 1.337(3) . ? N4 C19 1.343(3) . ? N5 C24 1.343(3) . ? N5 N6 1.359(3) . ? N6 C26 1.337(3) . ? C19 C20 1.373(4) . ? C20 C21 1.363(4) . ? C21 C22 1.380(4) . ? C22 C23 1.393(3) . ? C23 C24 1.463(3) . ? C24 C25 1.384(3) . ? C25 C26 1.365(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Mn1 C3 86.66(13) . . ? C1 Mn1 C2 91.22(12) . . ? C3 Mn1 C2 92.96(13) . . ? C1 Mn1 N2 94.06(10) . . ? C3 Mn1 N2 88.16(11) . . ? C2 Mn1 N2 174.65(11) . . ? C1 Mn1 N6 94.55(10) . . ? C3 Mn1 N6 175.25(12) . . ? C2 Mn1 N6 91.61(10) . . ? N2 Mn1 N6 87.17(8) . . ? C1 Mn1 N1 172.32(10) . . ? C3 Mn1 N1 91.03(13) . . ? C2 Mn1 N1 96.21(11) . . ? N2 Mn1 N1 78.53(8) . . ? N6 Mn1 N1 87.18(8) . . ? O1 C1 Mn1 173.9(2) . . ? C1 O1 Na 97.65(17) . 7_667 ? O2 C2 Mn1 179.3(3) . . ? O3 C3 Mn1 175.4(2) . . ? C11 N1 C15 117.8(2) . . ? C11 N1 Mn1 127.3(2) . . ? C15 N1 Mn1 114.85(16) . . ? C16 N2 N3 109.67(19) . . ? C16 N2 Mn1 116.56(16) . . ? N3 N2 Mn1 132.84(17) . . ? C18 N3 N2 105.2(2) . . ? C18 N3 Na 120.12(17) . 7_667 ? N2 N3 Na 129.22(16) . 7_667 ? C18 N3 Na 115.42(16) . . ? N2 N3 Na 99.95(13) . . ? Na N3 Na 81.20(7) 7_667 . ? N1 C11 C12 123.2(3) . . ? C13 C12 C11 118.7(3) . . ? C12 C13 C14 119.6(3) . . ? C13 C14 C15 119.6(3) . . ? N1 C15 C14 121.2(2) . . ? N1 C15 C16 114.0(2) . . ? C14 C15 C16 124.9(3) . . ? N2 C16 C17 109.4(2) . . ? N2 C16 C15 115.6(2) . . ? C17 C16 C15 135.0(3) . . ? C18 C17 C16 103.8(2) . . ? N3 C18 C17 112.0(2) . . ? N5 Na N3 119.20(8) . 7_667 ? N5 Na N4 71.17(7) . . ? N3 Na N4 103.43(8) 7_667 . ? N5 Na N3 91.52(7) . . ? N3 Na N3 98.80(7) 7_667 . ? N4 Na N3 156.54(8) . . ? N5 Na O1 153.89(8) . 7_667 ? N3 Na O1 85.74(7) 7_667 7_667 ? N4 Na O1 112.81(7) . 7_667 ? N3 Na O1 75.99(7) . 7_667 ? N5 Na Na 112.31(7) . 7_667 ? N3 Na Na 52.26(6) 7_667 7_667 ? N4 Na Na 154.78(8) . 7_667 ? N3 Na Na 46.53(5) . 7_667 ? O1 Na Na 75.62(5) 7_667 7_667 ? C23 N4 C19 118.3(2) . . ? C23 N4 Na 112.16(16) . . ? C19 N4 Na 129.30(18) . . ? C24 N5 N6 107.37(18) . . ? C24 N5 Na 113.25(15) . . ? N6 N5 Na 132.59(14) . . ? C26 N6 N5 108.15(19) . . ? C26 N6 Mn1 130.79(17) . . ? N5 N6 Mn1 121.05(14) . . ? N4 C19 C20 123.4(3) . . ? C21 C20 C19 118.4(3) . . ? C20 C21 C22 119.4(3) . . ? C21 C22 C23 119.3(3) . . ? N4 C23 C22 121.2(2) . . ? N4 C23 C24 117.9(2) . . ? C22 C23 C24 121.0(2) . . ? N5 C24 C25 109.7(2) . . ? N5 C24 C23 120.9(2) . . ? C25 C24 C23 129.3(2) . . ? C26 C25 C24 104.7(2) . . ? N6 C26 C25 110.1(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.247 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 873521' ####################################################################### # # 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_Compound_K3a_data_fv51a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H44 K2 Mn2 N12 O9' _chemical_formula_weight 1109.02 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' K K 0.2009 0.2494 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6794(9) _cell_length_b 11.8606(10) _cell_length_c 13.2110(8) _cell_angle_alpha 89.590(6) _cell_angle_beta 80.340(6) _cell_angle_gamma 77.518(7) _cell_volume 1459.2(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1729 _cell_measurement_theta_min 2.1830 _cell_measurement_theta_max 28.6695 _exptl_crystal_description BLOCK _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.3357 _exptl_crystal_size_mid 0.1507 _exptl_crystal_size_min 0.1087 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 0.633 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.943 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -13 0 -1 0.0436 -12.9952 0.0000 -0.9990 0.5784 0.7612 -0.2187 0 16 0 0.0743 0.0016 15.9945 0.0006 -0.6463 0.7012 -0.2240 13 0 0 0.0570 12.9951 -0.0000 -0.0008 -0.5828 -0.7507 0.2720 -1 2 18 0.1507 -0.9983 1.9988 17.9954 0.0435 -0.0441 -1.0074 1 -2 -18 0.1470 0.9983 -1.9988 -17.9954 -0.0435 0.0441 1.0074 -5 -16 -4 0.0661 -5.0000 -15.9944 -3.9992 0.8528 -0.3704 0.3324 -11 -2 -13 0.1093 -10.9969 -1.9989 -12.9960 0.5166 0.6844 0.4901 -5 -16 2 0.0666 -4.9996 -15.9945 1.9992 0.8793 -0.4335 0.0129 -9 8 -9 0.0921 -8.9964 7.9975 -8.9968 0.0406 0.9651 0.1789 1 -16 -1 0.0483 0.9980 -15.9944 -1.0004 0.5970 -0.7484 0.2982 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _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 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4757 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9407 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.1442 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.72 _reflns_number_total 6477 _reflns_number_gt 1705 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'Sun Jul 14 21:16:13 2013' ; _computing_cell_refinement ; 'Sun Jul 14 21:16:13 2013' ; _computing_data_reduction ; 'Sun Jul 14 21:16:13 2013' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1416P)^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 6477 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1152 _refine_ls_R_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.2303 _refine_ls_wR_factor_gt 0.2215 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 1.28875(14) -0.11552(13) 0.73458(10) 0.0716(6) Uani 1 1 d . . . C1 C 1.3359(10) -0.0818(8) 0.8558(8) 0.076(3) Uani 1 1 d . . . O1 O 1.3597(9) -0.0622(8) 0.9347(6) 0.121(3) Uani 1 1 d . . . C2 C 1.4690(10) -0.1229(9) 0.6729(7) 0.087(3) Uani 1 1 d . . . O2 O 1.5883(8) -0.1296(8) 0.6354(6) 0.135(3) Uani 1 1 d . . . C3 C 1.3320(12) -0.2642(11) 0.7602(9) 0.097(3) Uani 1 1 d . . . O3 O 1.3607(10) -0.3582(8) 0.7821(8) 0.150(4) Uani 1 1 d . . . N1 N 1.2018(8) -0.1362(6) 0.6058(5) 0.070(2) Uani 1 1 d . . . N2 N 1.0828(7) -0.1126(6) 0.7938(5) 0.069(2) Uani 1 1 d . . . N3 N 1.0132(9) -0.1135(7) 0.8927(6) 0.090(3) Uani 1 1 d . . . N4 N 0.9662(12) 0.3476(9) 0.8683(9) 0.115(3) Uani 1 1 d . . . N5 N 1.1466(8) 0.1368(7) 0.7745(6) 0.073(2) Uani 1 1 d . . . N6 N 1.2370(8) 0.0566(7) 0.7080(5) 0.071(2) Uani 1 1 d . . . K1 K 0.9062(2) 0.1309(2) 0.91114(17) 0.0928(9) Uani 1 1 d . . . C11 C 1.2677(11) -0.1423(9) 0.5063(8) 0.086(3) Uani 1 1 d . . . H11 H 1.3646 -0.1404 0.4932 0.103 Uiso 1 1 calc R . . C12 C 1.2023(13) -0.1510(10) 0.4244(9) 0.104(4) Uani 1 1 d . . . H12 H 1.2530 -0.1551 0.3577 0.125 Uiso 1 1 calc R . . C13 C 1.0618(14) -0.1534(10) 0.4425(8) 0.102(4) Uani 1 1 d . . . H13 H 1.0158 -0.1614 0.3874 0.123 Uiso 1 1 calc R . . C14 C 0.9849(12) -0.1443(9) 0.5408(9) 0.095(3) Uani 1 1 d . . . H14 H 0.8875 -0.1446 0.5531 0.114 Uiso 1 1 calc R . . C15 C 1.0591(10) -0.1346(8) 0.6215(7) 0.071(2) Uani 1 1 d . . . C16 C 0.9962(9) -0.1259(7) 0.7297(7) 0.066(2) Uani 1 1 d . . . C17 C 0.8623(11) -0.1326(9) 0.7848(9) 0.090(3) Uani 1 1 d . . . H17 H 0.7817 -0.1422 0.7592 0.108 Uiso 1 1 calc R . . C18 C 0.8765(11) -0.1219(9) 0.8828(9) 0.092(3) Uani 1 1 d . . . H18 H 0.8186 -0.1572 0.9367 0.110 Uiso 1 1 calc R . . C19 C 0.8884(17) 0.4497(15) 0.9171(14) 0.156(6) Uani 1 1 d . . . H19 H 0.8184 0.4474 0.9742 0.188 Uiso 1 1 calc R . . C20 C 0.911(2) 0.5505(15) 0.8846(19) 0.182(9) Uani 1 1 d . . . H20 H 0.8497 0.6186 0.9122 0.218 Uiso 1 1 calc R . . C21 C 1.027(3) 0.5540(15) 0.8095(18) 0.177(8) Uani 1 1 d . . . H21 H 1.0510 0.6243 0.7922 0.213 Uiso 1 1 calc R . . C22 C 1.1062(15) 0.4548(14) 0.7605(13) 0.136(5) Uani 1 1 d . . . H22 H 1.1822 0.4562 0.7074 0.163 Uiso 1 1 calc R . . C23 C 1.0708(15) 0.3524(11) 0.7914(11) 0.112(4) Uani 1 1 d . . . C24 C 1.1562(11) 0.2447(10) 0.7364(8) 0.082(3) Uani 1 1 d . . . C25 C 1.2545(13) 0.2291(12) 0.6447(9) 0.110(4) Uani 1 1 d . . . H25 H 1.2831 0.2861 0.6027 0.132 Uiso 1 1 calc R . . C26 C 1.3003(11) 0.1107(11) 0.6294(8) 0.092(3) Uani 1 1 d . . . H26 H 1.3652 0.0739 0.5732 0.110 Uiso 1 1 calc R . . O40 O 0.6502(9) 0.2148(11) 0.8382(7) 0.135(3) Uani 1 1 d . . . C41 C 0.5391(17) 0.1561(14) 0.8504(11) 0.149(6) Uani 1 1 d . . . H41A H 0.5653 0.0841 0.8850 0.179 Uiso 1 1 calc R . . H41B H 0.5157 0.1393 0.7844 0.179 Uiso 1 1 calc R . . C42 C 0.4173(15) 0.2348(16) 0.9133(13) 0.160(7) Uani 1 1 d . . . H42A H 0.4113 0.2157 0.9852 0.191 Uiso 1 1 calc R . . H42B H 0.3279 0.2300 0.8915 0.191 Uiso 1 1 calc R . . C43 C 0.446(2) 0.3529(16) 0.897(2) 0.241(12) Uani 1 1 d . . . H43A H 0.3774 0.3986 0.8591 0.289 Uiso 1 1 calc R . . H43B H 0.4390 0.3921 0.9627 0.289 Uiso 1 1 calc R . . C44 C 0.584(2) 0.3367(16) 0.842(2) 0.258(14) Uani 1 1 d . . . H44A H 0.6394 0.3799 0.8751 0.310 Uiso 1 1 calc R . . H44B H 0.5810 0.3643 0.7731 0.310 Uiso 1 1 calc R . . C90 C 0.612(3) 0.527(2) 0.540(3) 0.53(9) Uani 0.50 1 d P . . H90A H 0.5637 0.5700 0.6024 0.802 Uiso 0.50 1 calc PR . . H90B H 0.5677 0.4639 0.5311 0.802 Uiso 0.50 1 calc PR . . H90C H 0.6057 0.5769 0.4830 0.802 Uiso 0.50 1 calc PR . . O90 O 0.752(3) 0.486(2) 0.547(3) 0.43(3) Uani 0.50 1 d PR . . H90 H 0.8005 0.5343 0.5343 0.650 Uiso 0.50 1 d PR . . 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 0.0710(10) 0.0834(12) 0.0610(9) 0.0046(8) -0.0040(7) -0.0235(8) C1 0.086(7) 0.062(7) 0.076(7) 0.021(6) -0.011(5) -0.009(5) O1 0.157(8) 0.154(8) 0.070(5) 0.016(5) -0.049(5) -0.051(6) C2 0.066(6) 0.125(9) 0.074(6) 0.013(6) -0.007(5) -0.034(6) O2 0.065(5) 0.210(10) 0.125(7) 0.007(6) 0.007(4) -0.038(5) C3 0.109(9) 0.093(9) 0.090(8) 0.026(7) -0.023(6) -0.021(7) O3 0.152(8) 0.090(7) 0.191(10) 0.040(7) -0.005(7) -0.009(6) N1 0.082(5) 0.060(5) 0.063(5) 0.000(4) 0.002(4) -0.013(4) N2 0.072(5) 0.083(6) 0.053(4) 0.004(4) 0.004(4) -0.027(4) N3 0.104(6) 0.088(6) 0.074(5) 0.004(4) 0.020(4) -0.040(5) N4 0.134(9) 0.100(9) 0.118(8) -0.007(7) 0.001(7) -0.055(7) N5 0.083(5) 0.081(6) 0.061(5) 0.000(4) -0.019(4) -0.023(4) N6 0.070(5) 0.091(6) 0.056(4) 0.008(4) -0.001(4) -0.034(4) K1 0.0998(17) 0.0923(19) 0.0804(16) 0.0170(13) 0.0059(12) -0.0245(14) C11 0.088(7) 0.104(9) 0.065(6) -0.002(6) -0.012(6) -0.020(6) C12 0.103(9) 0.129(11) 0.084(8) -0.012(7) -0.003(7) -0.043(8) C13 0.123(10) 0.125(10) 0.067(7) -0.009(7) -0.027(7) -0.037(8) C14 0.091(8) 0.100(9) 0.103(9) 0.001(7) -0.039(7) -0.025(6) C15 0.066(6) 0.076(7) 0.072(6) -0.004(5) -0.015(5) -0.018(5) C16 0.060(6) 0.060(6) 0.077(6) -0.003(5) -0.005(5) -0.017(5) C17 0.083(7) 0.087(8) 0.104(9) -0.021(7) -0.006(6) -0.035(6) C18 0.083(7) 0.094(8) 0.103(9) -0.001(7) 0.013(6) -0.052(6) C19 0.171(15) 0.094(12) 0.184(17) -0.050(12) 0.003(12) -0.010(11) C20 0.174(18) 0.063(12) 0.30(3) 0.002(14) -0.035(17) -0.010(12) C21 0.194(19) 0.068(12) 0.27(3) 0.004(13) -0.004(16) -0.056(12) C22 0.135(12) 0.083(10) 0.184(15) 0.030(10) -0.004(10) -0.030(9) C23 0.130(11) 0.079(10) 0.136(11) 0.001(9) -0.020(9) -0.044(9) C24 0.089(7) 0.078(8) 0.085(7) 0.013(6) 0.000(6) -0.043(6) C25 0.118(10) 0.118(11) 0.101(9) 0.017(8) 0.004(7) -0.059(8) C26 0.097(8) 0.116(10) 0.066(6) 0.007(6) 0.001(5) -0.041(7) O40 0.095(6) 0.180(10) 0.132(8) 0.020(7) -0.004(5) -0.046(7) C41 0.125(12) 0.230(19) 0.099(10) -0.025(11) 0.001(8) -0.069(13) C42 0.105(11) 0.213(19) 0.175(16) 0.066(14) -0.032(11) -0.061(12) C43 0.158(17) 0.140(18) 0.39(4) 0.009(18) 0.058(19) -0.034(14) C44 0.175(19) 0.110(16) 0.44(4) 0.077(18) 0.06(2) -0.014(14) C90 0.50(10) 0.18(4) 0.58(11) 0.27(6) 0.45(10) 0.25(6) O90 0.60(7) 0.11(2) 0.47(6) 0.19(3) 0.00(5) 0.11(3) _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 C3 1.766(13) . ? Mn1 C2 1.782(10) . ? Mn1 C1 1.807(12) . ? Mn1 N2 2.009(7) . ? Mn1 N6 2.037(8) . ? Mn1 N1 2.059(8) . ? C1 O1 1.141(11) . ? O1 K1 3.249(9) 2_757 ? C2 O2 1.163(10) . ? C3 O3 1.138(11) . ? N1 C15 1.357(10) . ? N1 C11 1.357(11) . ? N2 C16 1.320(11) . ? N2 N3 1.366(9) . ? N3 C18 1.376(12) . ? N3 K1 2.823(9) 2_757 ? N3 K1 2.857(8) . ? N4 C23 1.319(14) . ? N4 C19 1.379(15) . ? N4 K1 2.789(10) . ? N5 N6 1.356(9) . ? N5 C24 1.388(11) . ? N5 K1 2.709(8) . ? N6 C26 1.346(11) . ? K1 O40 2.789(9) . ? K1 N3 2.823(9) 2_757 ? K1 C18 3.105(10) . ? K1 O1 3.249(9) 2_757 ? K1 C24 3.535(9) . ? K1 K1 4.165(5) 2_757 ? C11 C12 1.356(13) . ? C12 C13 1.347(14) . ? C13 C14 1.377(14) . ? C14 C15 1.400(13) . ? C15 C16 1.451(12) . ? C16 C17 1.394(12) . ? C17 C18 1.334(14) . ? C19 C20 1.32(2) . ? C20 C21 1.37(2) . ? C21 C22 1.359(19) . ? C22 C23 1.372(16) . ? C23 C24 1.483(15) . ? C24 C25 1.396(13) . ? C25 C26 1.383(14) . ? O40 C41 1.389(15) . ? O40 C44 1.447(17) . ? C41 C42 1.469(18) . ? C42 C43 1.492(19) . ? C43 C44 1.38(2) . ? C90 O90 1.3517 . ? 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 C3 Mn1 C2 90.2(5) . . ? C3 Mn1 C1 89.9(5) . . ? C2 Mn1 C1 90.0(4) . . ? C3 Mn1 N2 89.0(4) . . ? C2 Mn1 N2 175.5(4) . . ? C1 Mn1 N2 94.5(4) . . ? C3 Mn1 N6 178.9(4) . . ? C2 Mn1 N6 90.5(4) . . ? C1 Mn1 N6 89.3(3) . . ? N2 Mn1 N6 90.4(3) . . ? C3 Mn1 N1 95.4(4) . . ? C2 Mn1 N1 98.1(4) . . ? C1 Mn1 N1 170.3(3) . . ? N2 Mn1 N1 77.5(3) . . ? N6 Mn1 N1 85.3(3) . . ? O1 C1 Mn1 176.5(9) . . ? C1 O1 K1 102.4(7) . 2_757 ? O2 C2 Mn1 177.7(9) . . ? O3 C3 Mn1 176.1(12) . . ? C15 N1 C11 115.9(8) . . ? C15 N1 Mn1 116.3(6) . . ? C11 N1 Mn1 127.6(7) . . ? C16 N2 N3 109.6(7) . . ? C16 N2 Mn1 117.8(6) . . ? N3 N2 Mn1 132.1(7) . . ? N2 N3 C18 104.3(8) . . ? N2 N3 K1 135.8(6) . 2_757 ? C18 N3 K1 119.3(6) . 2_757 ? N2 N3 K1 95.0(5) . . ? C18 N3 K1 87.0(6) . . ? K1 N3 K1 94.3(2) 2_757 . ? C23 N4 C19 118.4(12) . . ? C23 N4 K1 116.9(9) . . ? C19 N4 K1 124.6(10) . . ? N6 N5 C24 107.4(8) . . ? N6 N5 K1 132.8(6) . . ? C24 N5 K1 115.5(6) . . ? C26 N6 N5 109.0(8) . . ? C26 N6 Mn1 125.8(8) . . ? N5 N6 Mn1 124.7(5) . . ? N5 K1 N4 63.0(3) . . ? N5 K1 O40 114.5(3) . . ? N4 K1 O40 86.1(3) . . ? N5 K1 N3 106.6(2) . 2_757 ? N4 K1 N3 96.6(3) . 2_757 ? O40 K1 N3 134.7(3) . 2_757 ? N5 K1 N3 83.8(2) . . ? N4 K1 N3 146.1(3) . . ? O40 K1 N3 115.9(3) . . ? N3 K1 N3 85.7(2) 2_757 . ? N5 K1 C18 101.9(3) . . ? N4 K1 C18 161.3(3) . . ? O40 K1 C18 91.0(3) . . ? N3 K1 C18 98.5(3) 2_757 . ? N3 K1 C18 26.3(2) . . ? N5 K1 O1 167.2(3) . 2_757 ? N4 K1 O1 129.7(3) . 2_757 ? O40 K1 O1 70.2(2) . 2_757 ? N3 K1 O1 73.9(2) 2_757 2_757 ? N3 K1 O1 83.5(2) . 2_757 ? C18 K1 O1 65.6(2) . 2_757 ? N5 K1 C24 20.7(2) . . ? N4 K1 C24 43.2(3) . . ? O40 K1 C24 102.2(3) . . ? N3 K1 C24 110.4(2) 2_757 . ? N3 K1 C24 104.4(2) . . ? C18 K1 C24 120.2(3) . . ? O1 K1 C24 171.1(2) 2_757 . ? N5 K1 K1 96.90(19) . 2_757 ? N4 K1 K1 130.4(3) . 2_757 ? O40 K1 K1 141.0(2) . 2_757 ? N3 K1 K1 43.16(17) 2_757 2_757 ? N3 K1 K1 42.53(18) . 2_757 ? C18 K1 K1 59.0(2) . 2_757 ? O1 K1 K1 74.60(15) 2_757 2_757 ? C24 K1 K1 114.0(2) . 2_757 ? C12 C11 N1 124.7(10) . . ? C13 C12 C11 118.1(10) . . ? C12 C13 C14 121.3(11) . . ? C13 C14 C15 117.4(10) . . ? N1 C15 C14 122.5(9) . . ? N1 C15 C16 112.5(8) . . ? C14 C15 C16 125.0(9) . . ? N2 C16 C17 109.8(9) . . ? N2 C16 C15 115.7(8) . . ? C17 C16 C15 134.5(10) . . ? C18 C17 C16 104.1(9) . . ? C17 C18 N3 112.2(9) . . ? C17 C18 K1 105.4(7) . . ? N3 C18 K1 66.8(5) . . ? C20 C19 N4 121.4(17) . . ? C19 C20 C21 119.4(17) . . ? C22 C21 C20 120.0(15) . . ? C21 C22 C23 118.1(14) . . ? N4 C23 C22 122.2(13) . . ? N4 C23 C24 120.0(11) . . ? C22 C23 C24 117.8(13) . . ? N5 C24 C25 108.4(10) . . ? N5 C24 C23 121.4(9) . . ? C25 C24 C23 130.2(11) . . ? N5 C24 K1 43.7(4) . . ? C25 C24 K1 147.5(8) . . ? C23 C24 K1 79.8(6) . . ? C26 C25 C24 105.3(10) . . ? N6 C26 C25 109.8(10) . . ? C41 O40 C44 106.5(12) . . ? C41 O40 K1 122.3(10) . . ? C44 O40 K1 122.0(12) . . ? O40 C41 C42 105.0(13) . . ? C41 C42 C43 105.6(13) . . ? C44 C43 C42 105.7(16) . . ? C43 C44 O40 108.8(15) . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.541 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 974911' ####################################################################### # # 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_Compound_4a_ma297am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H47 Mn3 N12 O8' _chemical_formula_weight 1096.81 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.466(4) _cell_length_b 11.453(2) _cell_length_c 23.586(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.795(5) _cell_angle_gamma 90.00 _cell_volume 5147.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 948 _cell_measurement_theta_min 2.338 _cell_measurement_theta_max 22.522 _exptl_crystal_description NEEDDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.784342 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_% ? _diffrn_reflns_number 23566 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 23.32 _reflns_number_total 7420 _reflns_number_gt 4958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0705P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00058(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7420 _refine_ls_number_parameters 651 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.30322(3) 0.74654(5) 0.20308(2) 0.04833(18) Uani 1 1 d . . . C1 C 0.3545(2) 0.6856(4) 0.15491(17) 0.0561(10) Uani 1 1 d . . . O1 O 0.38991(17) 0.6442(3) 0.12712(13) 0.0874(10) Uani 1 1 d . . . C2 C 0.3796(2) 0.8247(4) 0.23984(17) 0.0627(11) Uani 1 1 d . . . O2 O 0.43013(17) 0.8721(3) 0.26142(14) 0.0930(11) Uani 1 1 d . . . C3 C 0.3320(2) 0.6253(4) 0.25149(17) 0.0591(11) Uani 1 1 d . . . O3 O 0.35523(17) 0.5531(3) 0.28341(13) 0.0826(9) Uani 1 1 d . . . N1 N 0.23582(16) 0.7991(3) 0.25663(12) 0.0513(8) Uani 1 1 d . . . N2 N 0.21058(15) 0.6758(2) 0.16295(12) 0.0475(7) Uani 1 1 d . . . N3 N 0.18934(16) 0.6160(3) 0.11243(12) 0.0525(8) Uani 1 1 d . . . C11 C 0.2516(2) 0.8671(3) 0.30418(16) 0.0592(10) Uani 1 1 d . . . H11 H 0.2961 0.9003 0.3134 0.071 Uiso 1 1 calc R . . C12 C 0.2057(3) 0.8898(4) 0.33958(17) 0.0679(12) Uani 1 1 d . . . H12 H 0.2189 0.9370 0.3721 0.081 Uiso 1 1 calc R . . C13 C 0.1398(3) 0.8415(4) 0.32620(19) 0.0750(13) Uani 1 1 d . . . H13 H 0.1074 0.8564 0.3493 0.090 Uiso 1 1 calc R . . C14 C 0.1224(2) 0.7711(4) 0.27837(19) 0.0679(12) Uani 1 1 d . . . H14 H 0.0781 0.7374 0.2690 0.082 Uiso 1 1 calc R . . C15 C 0.1709(2) 0.7503(3) 0.24415(16) 0.0507(9) Uani 1 1 d . . . C16 C 0.1581(2) 0.6792(3) 0.19202(16) 0.0507(9) Uani 1 1 d . . . C17 C 0.1009(2) 0.6172(3) 0.16144(18) 0.0600(11) Uani 1 1 d . . . H17 H 0.0578 0.6041 0.1716 0.072 Uiso 1 1 calc R . . C18 C 0.1229(2) 0.5798(3) 0.11270(17) 0.0598(11) Uani 1 1 d . . . H18 H 0.0957 0.5352 0.0835 0.072 Uiso 1 1 calc R . . Mn2 Mn 0.19700(3) 0.49744(5) -0.09185(3) 0.0580(2) Uani 1 1 d . . . C4 C 0.1902(2) 0.4287(4) -0.0242(2) 0.0683(12) Uani 1 1 d . . . O4 O 0.1861(2) 0.3801(3) 0.01750(16) 0.1013(12) Uani 1 1 d . . . C5 C 0.1373(3) 0.3916(4) -0.1312(2) 0.0791(13) Uani 1 1 d . . . O5 O 0.0995(2) 0.3228(3) -0.15667(17) 0.1171(13) Uani 1 1 d . . . C6 C 0.2687(3) 0.4024(4) -0.0969(2) 0.0748(13) Uani 1 1 d . . . O6 O 0.3135(2) 0.3391(3) -0.10067(19) 0.1149(13) Uani 1 1 d . . . N4 N 0.21519(18) 0.5867(3) -0.16492(13) 0.0651(9) Uani 1 1 d . . . N5 N 0.26199(15) 0.6270(3) -0.05664(13) 0.0505(8) Uani 1 1 d . . . N6 N 0.28853(16) 0.6604(3) -0.00144(13) 0.0542(8) Uani 1 1 d . . . C19 C 0.1857(3) 0.5656(5) -0.2210(2) 0.0890(15) Uani 1 1 d . . . H19 H 0.1501 0.5102 -0.2297 0.107 Uiso 1 1 calc R . . C20 C 0.2067(3) 0.6241(6) -0.2661(2) 0.111(2) Uani 1 1 d . . . H20 H 0.1860 0.6069 -0.3043 0.133 Uiso 1 1 calc R . . C21 C 0.2581(4) 0.7069(6) -0.2541(3) 0.118(2) Uani 1 1 d . . . H21 H 0.2722 0.7477 -0.2839 0.141 Uiso 1 1 calc R . . C22 C 0.2884(3) 0.7290(5) -0.1975(2) 0.0903(15) Uani 1 1 d . . . H22 H 0.3235 0.7850 -0.1885 0.108 Uiso 1 1 calc R . . C23 C 0.2669(2) 0.6684(4) -0.15375(18) 0.0634(11) Uani 1 1 d . . . C24 C 0.2941(2) 0.6867(3) -0.09300(17) 0.0561(10) Uani 1 1 d . . . C25 C 0.3443(2) 0.7594(4) -0.0612(2) 0.0693(12) Uani 1 1 d . . . H25 H 0.3749 0.8095 -0.0747 0.083 Uiso 1 1 calc R . . C26 C 0.3386(2) 0.7405(4) -0.0051(2) 0.0658(11) Uani 1 1 d . . . H26 H 0.3659 0.7780 0.0267 0.079 Uiso 1 1 calc R . . Mn3 Mn 0.19894(3) 0.73091(4) 0.03670(2) 0.04468(18) Uani 1 1 d . . . N7 N 0.20259(15) 0.8932(3) -0.02415(12) 0.0502(8) Uani 1 1 d . . . N8 N 0.25510(15) 0.8726(2) 0.09108(12) 0.0463(7) Uani 1 1 d . . . N9 N 0.27517(15) 0.8872(3) 0.14956(12) 0.0490(8) Uani 1 1 d . . . C27 C 0.1847(2) 0.8967(4) -0.08183(17) 0.0584(10) Uani 1 1 d . . . H27 H 0.1632 0.8313 -0.1011 0.070 Uiso 1 1 calc R . . C28 C 0.1960(2) 0.9904(4) -0.11397(19) 0.0691(12) Uani 1 1 d . . . H28 H 0.1828 0.9886 -0.1542 0.083 Uiso 1 1 calc R . . C29 C 0.2268(3) 1.0868(4) -0.0864(2) 0.0833(14) Uani 1 1 d . . . H29 H 0.2355 1.1516 -0.1076 0.100 Uiso 1 1 calc R . . C30 C 0.2450(2) 1.0879(4) -0.02696(19) 0.0720(12) Uani 1 1 d . . . H30 H 0.2654 1.1538 -0.0075 0.086 Uiso 1 1 calc R . . C31 C 0.23248(19) 0.9887(3) 0.00369(16) 0.0514(9) Uani 1 1 d . . . C32 C 0.25258(19) 0.9797(3) 0.06670(16) 0.0489(9) Uani 1 1 d . . . C33 C 0.2701(2) 1.0637(3) 0.10912(17) 0.0635(11) Uani 1 1 d . . . H33 H 0.2722 1.1442 0.1043 0.076 Uiso 1 1 calc R . . C34 C 0.2839(2) 1.0018(3) 0.15989(17) 0.0597(10) Uani 1 1 d . . . H34 H 0.2973 1.0348 0.1965 0.072 Uiso 1 1 calc R . . N10 N 0.09476(15) 0.8198(3) 0.04781(13) 0.0504(8) Uani 1 1 d . . . N11 N 0.11523(15) 0.6652(2) -0.03438(12) 0.0470(7) Uani 1 1 d . . . N12 N 0.11610(16) 0.6063(3) -0.08449(13) 0.0546(8) Uani 1 1 d . . . C35 C 0.0858(2) 0.8908(4) 0.09105(17) 0.0623(11) Uani 1 1 d . . . H35 H 0.1247 0.9104 0.1195 0.075 Uiso 1 1 calc R . . C36 C 0.0220(3) 0.9352(4) 0.0948(2) 0.0851(14) Uani 1 1 d . . . H36 H 0.0177 0.9855 0.1248 0.102 Uiso 1 1 calc R . . C37 C -0.0358(3) 0.9048(5) 0.0538(2) 0.0984(17) Uani 1 1 d . . . H37 H -0.0799 0.9328 0.0564 0.118 Uiso 1 1 calc R . . C38 C -0.0283(2) 0.8331(4) 0.0092(2) 0.0813(14) Uani 1 1 d . . . H38 H -0.0670 0.8121 -0.0191 0.098 Uiso 1 1 calc R . . C39 C 0.0382(2) 0.7921(3) 0.00680(16) 0.0530(10) Uani 1 1 d . . . C40 C 0.05196(19) 0.7172(3) -0.04018(16) 0.0521(10) Uani 1 1 d . . . C41 C 0.0110(2) 0.6912(4) -0.09389(19) 0.0724(12) Uani 1 1 d . . . H41 H -0.0348 0.7148 -0.1089 0.087 Uiso 1 1 calc R . . C42 C 0.0535(2) 0.6224(4) -0.12007(18) 0.0698(12) Uani 1 1 d . . . H42 H 0.0407 0.5913 -0.1572 0.084 Uiso 1 1 calc R . . C85 C 0.0230(9) 0.956(2) 0.5155(9) 0.310(10) Uani 1 1 d . . . H85A H -0.0002 0.8982 0.5349 0.372 Uiso 1 1 calc R . . H85B H 0.0646 0.9872 0.5409 0.372 Uiso 1 1 calc R . . C86 C 0.0343(14) 0.919(2) 0.4542(13) 0.445(19) Uani 1 1 d . . . H86A H -0.0092 0.8968 0.4284 0.534 Uiso 1 1 calc R . . H86B H 0.0581 0.9784 0.4362 0.534 Uiso 1 1 calc R . . C87 C 0.0783(14) 0.821(2) 0.4734(8) 0.466(19) Uani 1 1 d . . . H87A H 0.0620 0.7820 0.5043 0.699 Uiso 1 1 calc R . . H87B H 0.1257 0.8465 0.4869 0.699 Uiso 1 1 calc R . . H87C H 0.0766 0.7671 0.4417 0.699 Uiso 1 1 calc R . . O90 O 0.0358(5) 1.0254(14) 0.7569(6) 0.296(5) Uani 1 1 d . . . C91 C 0.0686(10) 1.0560(16) 0.7201(8) 0.333(12) Uani 1 1 d . . . H91A H 0.1070 1.1066 0.7377 0.399 Uiso 1 1 calc R . . H91B H 0.0378 1.1001 0.6900 0.399 Uiso 1 1 calc R . . C92 C 0.0927(14) 0.968(2) 0.6976(9) 0.386(16) Uani 1 1 d . . . H92A H 0.1425 0.9796 0.6995 0.463 Uiso 1 1 calc R . . H92B H 0.0699 0.9630 0.6571 0.463 Uiso 1 1 calc R . . C93 C 0.0833(10) 0.8697(16) 0.7236(12) 0.366(15) Uani 1 1 d . . . H93A H 0.1281 0.8358 0.7417 0.439 Uiso 1 1 calc R . . H93B H 0.0580 0.8141 0.6960 0.439 Uiso 1 1 calc R . . C94 C 0.0443(7) 0.8979(16) 0.7655(6) 0.224(6) Uani 1 1 d . . . H94A H 0.0698 0.8793 0.8042 0.269 Uiso 1 1 calc R . . H94B H -0.0006 0.8582 0.7583 0.269 Uiso 1 1 calc R . . O95 O 0.0756(3) 0.4722(7) 0.6437(3) 0.185(2) Uani 1 1 d . . . C96 C 0.0164(8) 0.4383(17) 0.6578(6) 0.307(10) Uani 1 1 d . . . H96A H 0.0092 0.4802 0.6919 0.368 Uiso 1 1 calc R . . H96B H 0.0181 0.3554 0.6663 0.368 Uiso 1 1 calc R . . C97 C -0.0358(10) 0.461(3) 0.6129(14) 0.47(2) Uani 1 1 d . . . H97A H -0.0802 0.4687 0.6254 0.563 Uiso 1 1 calc R . . H97B H -0.0400 0.4002 0.5840 0.563 Uiso 1 1 calc R . . C98 C -0.0165(10) 0.5683(17) 0.5908(11) 0.364(14) Uani 1 1 d . . . H98A H -0.0371 0.5769 0.5500 0.437 Uiso 1 1 calc R . . H98B H -0.0298 0.6343 0.6120 0.437 Uiso 1 1 calc R . . C99 C 0.0576(8) 0.5562(12) 0.6002(7) 0.290(8) Uani 1 1 d . . . H99A H 0.0716 0.5310 0.5650 0.348 Uiso 1 1 calc R . . H99B H 0.0804 0.6300 0.6124 0.348 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0496(3) 0.0500(4) 0.0415(3) -0.0018(2) 0.0001(3) -0.0009(3) C1 0.056(2) 0.056(3) 0.051(3) 0.003(2) -0.003(2) -0.001(2) O1 0.083(2) 0.109(3) 0.072(2) -0.0045(18) 0.0212(18) 0.024(2) C2 0.062(3) 0.070(3) 0.051(2) -0.005(2) -0.001(2) 0.001(2) O2 0.069(2) 0.105(3) 0.091(2) -0.0231(19) -0.0162(18) -0.0148(19) C3 0.058(2) 0.065(3) 0.053(3) -0.007(2) 0.005(2) 0.001(2) O3 0.095(2) 0.078(2) 0.069(2) 0.0234(17) 0.0044(17) 0.0137(19) N1 0.063(2) 0.0437(18) 0.0462(19) 0.0038(15) 0.0080(16) 0.0032(16) N2 0.0542(19) 0.0411(18) 0.0435(18) 0.0008(14) 0.0015(15) -0.0036(15) N3 0.060(2) 0.0439(18) 0.0488(19) -0.0026(15) 0.0006(15) -0.0054(16) C11 0.076(3) 0.050(2) 0.050(2) 0.001(2) 0.009(2) 0.001(2) C12 0.096(3) 0.058(3) 0.050(3) 0.002(2) 0.016(3) 0.009(3) C13 0.094(4) 0.072(3) 0.067(3) 0.003(2) 0.036(3) 0.012(3) C14 0.069(3) 0.065(3) 0.074(3) 0.009(2) 0.023(2) 0.004(2) C15 0.055(2) 0.044(2) 0.053(2) 0.0084(18) 0.013(2) 0.004(2) C16 0.054(2) 0.048(2) 0.049(2) 0.0101(18) 0.008(2) -0.004(2) C17 0.055(2) 0.060(3) 0.063(3) 0.012(2) 0.007(2) -0.010(2) C18 0.062(3) 0.053(3) 0.057(3) 0.004(2) -0.005(2) -0.015(2) Mn2 0.0670(4) 0.0477(4) 0.0575(4) -0.0119(3) 0.0085(3) -0.0033(3) C4 0.078(3) 0.047(3) 0.077(3) -0.012(2) 0.008(3) -0.006(2) O4 0.148(3) 0.072(2) 0.084(3) 0.0089(19) 0.027(2) -0.009(2) C5 0.089(3) 0.073(3) 0.076(3) -0.018(3) 0.017(3) -0.006(3) O5 0.119(3) 0.095(3) 0.129(3) -0.052(2) 0.007(2) -0.035(2) C6 0.078(3) 0.057(3) 0.091(3) -0.012(2) 0.020(3) -0.006(3) O6 0.102(3) 0.076(2) 0.177(4) -0.014(2) 0.051(3) 0.016(2) N4 0.076(2) 0.071(2) 0.048(2) -0.0114(17) 0.0116(18) 0.009(2) N5 0.0536(19) 0.0481(19) 0.0492(19) -0.0057(15) 0.0087(16) -0.0020(16) N6 0.0509(18) 0.056(2) 0.053(2) -0.0044(16) 0.0043(15) -0.0035(17) C19 0.095(4) 0.105(4) 0.063(3) -0.020(3) 0.009(3) 0.001(3) C20 0.127(5) 0.158(6) 0.046(3) -0.004(3) 0.015(3) -0.006(5) C21 0.132(5) 0.148(6) 0.076(4) 0.014(4) 0.029(4) -0.015(5) C22 0.109(4) 0.103(4) 0.061(3) 0.011(3) 0.024(3) -0.010(3) C23 0.066(3) 0.067(3) 0.059(3) -0.005(2) 0.017(2) 0.000(2) C24 0.057(2) 0.056(3) 0.056(3) -0.002(2) 0.013(2) -0.001(2) C25 0.061(3) 0.071(3) 0.079(3) -0.003(2) 0.022(2) -0.012(2) C26 0.052(2) 0.072(3) 0.071(3) -0.012(2) 0.008(2) -0.009(2) Mn3 0.0498(3) 0.0396(3) 0.0411(3) -0.0027(2) 0.0009(2) -0.0026(3) N7 0.0602(19) 0.0455(19) 0.0425(19) -0.0004(14) 0.0051(15) 0.0011(16) N8 0.0543(18) 0.0426(18) 0.0384(18) -0.0011(13) 0.0009(14) -0.0053(15) N9 0.0558(19) 0.0462(19) 0.0425(18) -0.0042(14) 0.0038(14) -0.0060(15) C27 0.067(3) 0.051(2) 0.054(3) -0.001(2) 0.008(2) 0.000(2) C28 0.086(3) 0.066(3) 0.054(3) 0.011(2) 0.010(2) -0.002(3) C29 0.117(4) 0.063(3) 0.068(3) 0.027(3) 0.015(3) -0.007(3) C30 0.096(3) 0.048(3) 0.067(3) 0.004(2) 0.004(3) -0.012(2) C31 0.058(2) 0.042(2) 0.052(2) 0.0048(19) 0.0088(19) 0.0008(19) C32 0.055(2) 0.037(2) 0.054(2) -0.0003(18) 0.0082(18) -0.0047(18) C33 0.086(3) 0.034(2) 0.065(3) -0.005(2) 0.003(2) -0.008(2) C34 0.075(3) 0.045(2) 0.055(3) -0.014(2) 0.004(2) -0.006(2) N10 0.0556(19) 0.0475(18) 0.0473(19) -0.0015(15) 0.0089(16) 0.0027(16) N11 0.0469(18) 0.0445(18) 0.0465(18) -0.0071(14) 0.0021(14) -0.0033(15) N12 0.061(2) 0.0508(19) 0.0475(19) -0.0122(15) 0.0010(16) -0.0053(16) C35 0.075(3) 0.059(3) 0.055(3) -0.003(2) 0.016(2) 0.007(2) C36 0.085(4) 0.094(4) 0.081(3) -0.020(3) 0.029(3) 0.016(3) C37 0.072(3) 0.122(5) 0.106(4) -0.020(4) 0.032(3) 0.024(3) C38 0.057(3) 0.093(4) 0.091(4) -0.010(3) 0.010(2) 0.009(3) C39 0.049(2) 0.053(2) 0.057(3) 0.0027(19) 0.013(2) 0.002(2) C40 0.047(2) 0.053(2) 0.053(2) -0.0010(19) 0.0016(19) -0.0036(19) C41 0.053(2) 0.083(3) 0.070(3) -0.011(2) -0.013(2) 0.006(2) C42 0.066(3) 0.077(3) 0.055(3) -0.017(2) -0.014(2) -0.001(2) C85 0.23(2) 0.46(4) 0.25(2) -0.01(2) 0.049(14) 0.023(17) C86 0.46(4) 0.45(4) 0.49(5) 0.19(3) 0.26(4) 0.06(3) C87 0.52(4) 0.63(5) 0.204(17) -0.07(2) -0.03(2) 0.06(3) O90 0.243(9) 0.350(16) 0.318(13) 0.051(11) 0.110(8) 0.068(10) C91 0.45(3) 0.33(2) 0.302(19) -0.032(16) 0.272(18) -0.16(2) C92 0.55(3) 0.37(3) 0.34(2) -0.18(2) 0.34(2) -0.13(3) C93 0.273(18) 0.199(16) 0.67(4) -0.13(2) 0.20(2) 0.058(14) C94 0.162(10) 0.233(14) 0.264(14) 0.102(13) 0.016(9) -0.029(10) O95 0.134(5) 0.183(6) 0.233(7) -0.016(5) 0.026(5) 0.026(4) C96 0.141(10) 0.54(3) 0.253(16) 0.042(17) 0.078(10) -0.049(16) C97 0.130(12) 0.81(7) 0.45(4) 0.04(4) 0.023(15) -0.10(3) C98 0.231(19) 0.35(2) 0.44(3) 0.01(2) -0.11(2) 0.179(19) C99 0.257(16) 0.195(12) 0.37(2) 0.100(13) -0.050(14) 0.019(11) _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 C2 1.800(4) . ? Mn1 C1 1.800(5) . ? Mn1 C3 1.813(5) . ? Mn1 N2 2.027(3) . ? Mn1 N9 2.051(3) . ? Mn1 N1 2.087(3) . ? C1 O1 1.146(4) . ? C2 O2 1.147(4) . ? C3 O3 1.147(4) . ? N1 C11 1.349(5) . ? N1 C15 1.358(5) . ? N2 C16 1.342(4) . ? N2 N3 1.363(4) . ? N3 C18 1.359(5) . ? N3 Mn3 2.257(3) . ? C11 C12 1.367(5) . ? C12 C13 1.373(6) . ? C13 C14 1.372(6) . ? C14 C15 1.382(5) . ? C15 C16 1.453(5) . ? C16 C17 1.393(5) . ? C17 C18 1.375(5) . ? Mn2 C6 1.793(5) . ? Mn2 C5 1.800(5) . ? Mn2 C4 1.808(5) . ? Mn2 N5 2.016(3) . ? Mn2 N12 2.044(3) . ? Mn2 N4 2.095(3) . ? C4 O4 1.148(5) . ? C5 O5 1.159(5) . ? C6 O6 1.152(5) . ? N4 C19 1.352(5) . ? N4 C23 1.360(5) . ? N5 C24 1.347(5) . ? N5 N6 1.354(4) . ? N6 C26 1.354(5) . ? N6 Mn3 2.268(3) . ? C19 C20 1.389(7) . ? C20 C21 1.365(8) . ? C21 C22 1.369(7) . ? C22 C23 1.377(6) . ? C23 C24 1.438(5) . ? C24 C25 1.383(5) . ? C25 C26 1.366(6) . ? Mn3 N8 2.214(3) . ? Mn3 N11 2.217(3) . ? Mn3 N10 2.331(3) . ? Mn3 N7 2.358(3) . ? N7 C27 1.334(4) . ? N7 C31 1.345(4) . ? N8 C32 1.351(4) . ? N8 N9 1.365(4) . ? N9 C34 1.339(4) . ? C27 C28 1.358(5) . ? C28 C29 1.356(6) . ? C29 C30 1.375(6) . ? C30 C31 1.395(5) . ? C31 C32 1.461(5) . ? C32 C33 1.380(5) . ? C33 C34 1.370(5) . ? N10 C35 1.343(5) . ? N10 C39 1.346(4) . ? N11 C40 1.350(4) . ? N11 N12 1.364(4) . ? N12 C42 1.343(5) . ? C35 C36 1.362(6) . ? C36 C37 1.370(6) . ? C37 C38 1.367(6) . ? C38 C39 1.389(5) . ? C39 C40 1.468(5) . ? C40 C41 1.384(5) . ? C41 C42 1.377(6) . ? C85 C85 1.44(3) 3_576 ? C85 C86 1.57(3) . ? C85 C86 2.03(4) 3_576 ? C86 C87 1.43(3) . ? C86 C85 2.03(4) 3_576 ? O90 C91 1.230(12) . ? O90 C94 1.479(14) . ? C91 C92 1.27(2) . ? C92 C93 1.32(3) . ? C93 C94 1.401(19) . ? O95 C96 1.323(12) . ? O95 C99 1.398(12) . ? C96 C97 1.34(2) . ? C97 C98 1.41(3) . ? C98 C99 1.419(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 C2 Mn1 C1 89.25(18) . . ? C2 Mn1 C3 87.65(18) . . ? C1 Mn1 C3 87.72(17) . . ? C2 Mn1 N2 173.18(16) . . ? C1 Mn1 N2 96.05(15) . . ? C3 Mn1 N2 96.83(14) . . ? C2 Mn1 N9 89.74(15) . . ? C1 Mn1 N9 91.64(15) . . ? C3 Mn1 N9 177.31(15) . . ? N2 Mn1 N9 85.83(11) . . ? C2 Mn1 N1 97.17(16) . . ? C1 Mn1 N1 172.90(15) . . ? C3 Mn1 N1 89.52(15) . . ? N2 Mn1 N1 77.79(12) . . ? N9 Mn1 N1 91.42(11) . . ? O1 C1 Mn1 175.9(3) . . ? O2 C2 Mn1 176.6(4) . . ? O3 C3 Mn1 174.6(4) . . ? C11 N1 C15 117.5(3) . . ? C11 N1 Mn1 127.2(3) . . ? C15 N1 Mn1 115.0(2) . . ? C16 N2 N3 109.6(3) . . ? C16 N2 Mn1 116.5(2) . . ? N3 N2 Mn1 133.7(2) . . ? C18 N3 N2 105.5(3) . . ? C18 N3 Mn3 114.5(2) . . ? N2 N3 Mn3 109.8(2) . . ? N1 C11 C12 123.4(4) . . ? C11 C12 C13 118.7(4) . . ? C14 C13 C12 119.2(4) . . ? C13 C14 C15 119.9(4) . . ? N1 C15 C14 121.3(4) . . ? N1 C15 C16 113.8(3) . . ? C14 C15 C16 124.9(4) . . ? N2 C16 C17 109.4(3) . . ? N2 C16 C15 115.7(3) . . ? C17 C16 C15 134.8(4) . . ? C18 C17 C16 103.8(4) . . ? N3 C18 C17 111.6(3) . . ? C6 Mn2 C5 89.2(2) . . ? C6 Mn2 C4 89.6(2) . . ? C5 Mn2 C4 90.3(2) . . ? C6 Mn2 N5 92.46(16) . . ? C5 Mn2 N5 173.15(18) . . ? C4 Mn2 N5 96.32(16) . . ? C6 Mn2 N12 178.93(18) . . ? C5 Mn2 N12 91.58(17) . . ? C4 Mn2 N12 89.65(17) . . ? N5 Mn2 N12 86.87(12) . . ? C6 Mn2 N4 88.67(18) . . ? C5 Mn2 N4 95.96(18) . . ? C4 Mn2 N4 173.43(17) . . ? N5 Mn2 N4 77.43(13) . . ? N12 Mn2 N4 92.00(13) . . ? O4 C4 Mn2 176.8(4) . . ? O5 C5 Mn2 179.3(5) . . ? O6 C6 Mn2 178.2(4) . . ? C19 N4 C23 117.5(4) . . ? C19 N4 Mn2 127.4(3) . . ? C23 N4 Mn2 114.8(3) . . ? C24 N5 N6 109.5(3) . . ? C24 N5 Mn2 116.5(2) . . ? N6 N5 Mn2 133.5(2) . . ? N5 N6 C26 105.6(3) . . ? N5 N6 Mn3 108.0(2) . . ? C26 N6 Mn3 114.0(3) . . ? N4 C19 C20 122.0(5) . . ? C21 C20 C19 119.7(5) . . ? C20 C21 C22 118.8(6) . . ? C21 C22 C23 120.1(5) . . ? N4 C23 C22 121.8(4) . . ? N4 C23 C24 113.6(4) . . ? C22 C23 C24 124.5(4) . . ? N5 C24 C25 109.2(4) . . ? N5 C24 C23 115.9(4) . . ? C25 C24 C23 134.8(4) . . ? C26 C25 C24 104.0(4) . . ? N6 C26 C25 111.8(4) . . ? N8 Mn3 N11 152.43(11) . . ? N8 Mn3 N3 94.59(11) . . ? N11 Mn3 N3 103.51(11) . . ? N8 Mn3 N6 99.32(11) . . ? N11 Mn3 N6 94.89(11) . . ? N3 Mn3 N6 107.52(11) . . ? N8 Mn3 N10 87.28(11) . . ? N11 Mn3 N10 73.23(11) . . ? N3 Mn3 N10 87.20(11) . . ? N6 Mn3 N10 163.16(11) . . ? N8 Mn3 N7 72.66(10) . . ? N11 Mn3 N7 85.20(10) . . ? N3 Mn3 N7 163.52(11) . . ? N6 Mn3 N7 85.29(11) . . ? N10 Mn3 N7 81.91(10) . . ? C27 N7 C31 118.0(3) . . ? C27 N7 Mn3 127.6(2) . . ? C31 N7 Mn3 114.0(2) . . ? C32 N8 N9 107.3(3) . . ? C32 N8 Mn3 116.6(2) . . ? N9 N8 Mn3 132.9(2) . . ? C34 N9 N8 107.7(3) . . ? C34 N9 Mn1 130.5(3) . . ? N8 N9 Mn1 120.7(2) . . ? N7 C27 C28 123.7(4) . . ? C29 C28 C27 118.8(4) . . ? C28 C29 C30 119.5(4) . . ? C29 C30 C31 119.0(4) . . ? N7 C31 C30 120.9(3) . . ? N7 C31 C32 116.0(3) . . ? C30 C31 C32 123.0(3) . . ? N8 C32 C33 110.0(3) . . ? N8 C32 C31 118.4(3) . . ? C33 C32 C31 131.6(3) . . ? C34 C33 C32 104.4(3) . . ? N9 C34 C33 110.7(3) . . ? C35 N10 C39 118.4(3) . . ? C35 N10 Mn3 126.9(3) . . ? C39 N10 Mn3 114.7(2) . . ? C40 N11 N12 107.6(3) . . ? C40 N11 Mn3 116.2(2) . . ? N12 N11 Mn3 133.3(2) . . ? C42 N12 N11 107.7(3) . . ? C42 N12 Mn2 130.3(3) . . ? N11 N12 Mn2 121.4(2) . . ? N10 C35 C36 122.4(4) . . ? C35 C36 C37 119.3(4) . . ? C38 C37 C36 119.6(4) . . ? C37 C38 C39 118.8(4) . . ? N10 C39 C38 121.5(4) . . ? N10 C39 C40 115.6(3) . . ? C38 C39 C40 122.9(4) . . ? N11 C40 C41 109.9(3) . . ? N11 C40 C39 119.0(3) . . ? C41 C40 C39 131.1(4) . . ? C42 C41 C40 104.3(3) . . ? N12 C42 C41 110.5(4) . . ? C85 C85 C86 85(2) 3_576 . ? C85 C85 C86 50.2(14) 3_576 3_576 ? C86 C85 C86 135.1(14) . 3_576 ? C87 C86 C85 96(2) . . ? C87 C86 C85 141(3) . 3_576 ? C85 C86 C85 44.9(14) . 3_576 ? C91 O90 C94 108.5(14) . . ? O90 C91 C92 111.0(18) . . ? C91 C92 C93 112.7(17) . . ? C92 C93 C94 106.1(14) . . ? C93 C94 O90 101.2(13) . . ? C96 O95 C99 106.6(10) . . ? O95 C96 C97 107.6(15) . . ? C96 C97 C98 104(2) . . ? C99 C98 C97 101.4(14) . . ? O95 C99 C98 106.0(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.32 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.396 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 873522' ####################################################################### # # 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_Compound_5a_na7am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Cl2 Mn N6 O0.50' _chemical_formula_weight 425.18 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' Cl Cl 0.1484 0.1585 '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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.794(2) _cell_length_b 16.680(5) _cell_length_c 17.504(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.509(6) _cell_angle_gamma 90.00 _cell_volume 1974.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 897 _cell_measurement_theta_min 2.637 _cell_measurement_theta_max 23.083 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.953 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.831493 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_% ? _diffrn_reflns_number 8651 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2838 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0722P)^2^+0.7622P] 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 2838 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 0.26267(8) 0.77923(3) 0.13815(3) 0.0322(2) Uani 1 1 d . . . Cl1 Cl 0.03451(14) 0.66690(6) 0.15365(7) 0.0470(3) Uani 1 1 d . . . Cl2 Cl 0.52930(14) 0.73854(6) 0.23584(6) 0.0428(3) Uani 1 1 d . . . N1 N 0.3923(4) 0.90969(18) 0.1459(2) 0.0394(8) Uani 1 1 d . . . N2 N 0.0766(4) 0.85660(18) 0.20771(19) 0.0365(8) Uani 1 1 d . . . N3 N -0.0828(5) 0.84482(19) 0.2459(2) 0.0425(8) Uani 1 1 d . . . H3 H -0.1612 0.8044 0.2390 0.051 Uiso 1 1 calc R . . C11 C 0.5459(6) 0.9356(3) 0.1104(3) 0.0555(13) Uani 1 1 d . . . H11 H 0.5850 0.9059 0.0695 0.067 Uiso 1 1 calc R . . C12 C 0.6483(7) 1.0041(3) 0.1315(3) 0.0645(14) Uani 1 1 d . . . H12 H 0.7534 1.0207 0.1051 0.077 Uiso 1 1 calc R . . C13 C 0.5935(7) 1.0475(3) 0.1921(3) 0.0593(13) Uani 1 1 d . . . H13 H 0.6647 1.0927 0.2092 0.071 Uiso 1 1 calc R . . C14 C 0.4318(6) 1.0233(2) 0.2274(3) 0.0489(11) Uani 1 1 d . . . H14 H 0.3884 1.0533 0.2673 0.059 Uiso 1 1 calc R . . C15 C 0.3347(5) 0.9544(2) 0.2031(2) 0.0364(9) Uani 1 1 d . . . C16 C 0.1574(5) 0.9245(2) 0.2362(2) 0.0354(9) Uani 1 1 d . . . C17 C 0.0470(7) 0.9551(3) 0.2915(3) 0.0578(13) Uani 1 1 d . . . H17 H 0.0712 1.0017 0.3201 0.069 Uiso 1 1 calc R . . C18 C -0.1039(7) 0.9030(3) 0.2954(3) 0.0562(12) Uani 1 1 d . . . H18 H -0.2050 0.9074 0.3274 0.067 Uiso 1 1 calc R . . N4 N 0.1195(5) 0.8135(2) 0.01664(19) 0.0412(8) Uani 1 1 d . . . N5 N 0.4539(5) 0.73579(19) 0.05000(19) 0.0376(8) Uani 1 1 d . . . N6 N 0.6237(5) 0.6956(2) 0.0529(2) 0.0511(9) Uani 1 1 d . . . H6 H 0.6965 0.6848 0.0945 0.061 Uiso 1 1 calc R . . C21 C -0.0433(7) 0.8571(3) 0.0024(3) 0.0602(13) Uani 1 1 d . . . H21 H -0.1009 0.8791 0.0438 0.072 Uiso 1 1 calc R . . C23 C -0.0494(6) 0.8380(3) -0.1313(3) 0.0551(12) Uani 1 1 d . . . H23 H -0.1082 0.8455 -0.1809 0.066 Uiso 1 1 calc R . . C24 C 0.1209(6) 0.7931(2) -0.1182(2) 0.0432(10) Uani 1 1 d . . . H24 H 0.1800 0.7705 -0.1588 0.052 Uiso 1 1 calc R . . C25 C 0.2019(5) 0.7823(2) -0.0436(2) 0.0337(9) Uani 1 1 d . . . C26 C 0.3867(6) 0.7392(2) -0.0235(2) 0.0374(9) Uani 1 1 d . . . C27 C -0.1309(7) 0.8715(3) -0.0700(3) 0.0659(14) Uani 1 1 d . . . H27 H -0.2435 0.9033 -0.0775 0.079 Uiso 1 1 calc R . . C28 C 0.5163(8) 0.7007(4) -0.0674(3) 0.0742(16) Uani 1 1 d . . . H28 H 0.5034 0.6942 -0.1204 0.089 Uiso 1 1 calc R . . C29 C 0.6665(7) 0.6744(3) -0.0168(3) 0.0760(17) Uani 1 1 d . . . H29 H 0.7783 0.6467 -0.0287 0.091 Uiso 1 1 calc R . . O91 O 0.1923(7) 0.5259(3) 0.0459(3) 0.188(7) Uani 0.50 1 d PR . . H91A H 0.1534 0.5482 -0.0053 0.282 Uiso 0.50 1 d PR . . H91B H 0.1649 0.5679 0.0824 0.282 Uiso 0.50 1 d PR . . 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 0.0318(4) 0.0367(3) 0.0282(4) -0.0014(2) 0.0040(2) 0.0012(2) Cl1 0.0408(6) 0.0400(5) 0.0588(8) 0.0033(5) -0.0025(5) -0.0050(4) Cl2 0.0351(5) 0.0568(6) 0.0353(6) 0.0065(4) -0.0026(4) -0.0046(4) N1 0.0351(17) 0.0375(17) 0.047(2) -0.0007(16) 0.0103(16) -0.0034(14) N2 0.0332(17) 0.0387(17) 0.039(2) -0.0019(15) 0.0112(15) -0.0009(14) N3 0.0374(18) 0.0452(19) 0.047(2) 0.0027(16) 0.0134(16) -0.0039(15) C11 0.048(3) 0.047(2) 0.076(4) -0.006(2) 0.025(2) -0.001(2) C12 0.046(3) 0.054(3) 0.098(4) 0.002(3) 0.026(3) -0.012(2) C13 0.049(3) 0.040(2) 0.089(4) -0.006(2) 0.007(3) -0.013(2) C14 0.053(3) 0.039(2) 0.056(3) -0.005(2) 0.007(2) -0.005(2) C15 0.035(2) 0.0302(19) 0.043(3) 0.0015(18) 0.0021(18) 0.0018(16) C16 0.036(2) 0.033(2) 0.038(3) -0.0030(17) 0.0056(18) 0.0018(16) C17 0.070(3) 0.049(2) 0.058(3) -0.012(2) 0.026(3) -0.005(2) C18 0.057(3) 0.061(3) 0.055(3) -0.003(2) 0.028(2) 0.003(2) N4 0.0359(18) 0.054(2) 0.033(2) 0.0015(16) 0.0023(15) 0.0084(16) N5 0.0348(18) 0.0483(19) 0.030(2) -0.0023(15) 0.0017(15) 0.0079(15) N6 0.042(2) 0.067(2) 0.043(2) -0.0001(18) -0.0001(17) 0.0202(18) C21 0.048(3) 0.087(3) 0.046(3) 0.002(3) 0.006(2) 0.022(3) C23 0.050(3) 0.075(3) 0.037(3) 0.010(2) -0.012(2) -0.003(2) C24 0.043(2) 0.053(2) 0.033(3) 0.0000(19) -0.0018(19) -0.0049(19) C25 0.032(2) 0.039(2) 0.030(2) -0.0005(17) 0.0008(17) -0.0046(16) C26 0.040(2) 0.044(2) 0.030(3) -0.0014(17) 0.0051(18) 0.0025(18) C27 0.048(3) 0.090(4) 0.059(4) 0.014(3) -0.003(3) 0.022(3) C28 0.079(4) 0.110(4) 0.036(3) -0.006(3) 0.011(3) 0.041(3) C29 0.068(3) 0.115(5) 0.047(3) -0.009(3) 0.013(3) 0.049(3) O91 0.300(17) 0.079(6) 0.214(15) -0.063(8) 0.174(14) -0.016(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N5 2.231(3) . ? Mn1 N2 2.245(3) . ? Mn1 N4 2.324(3) . ? Mn1 N1 2.347(3) . ? Mn1 Cl1 2.4634(12) . ? Mn1 Cl2 2.4640(12) . ? N1 C11 1.336(5) . ? N1 C15 1.336(5) . ? N2 C16 1.334(5) . ? N2 N3 1.341(4) . ? N3 C18 1.318(6) . ? C11 C12 1.369(6) . ? C12 C13 1.366(7) . ? C13 C14 1.371(6) . ? C14 C15 1.373(6) . ? C15 C16 1.473(5) . ? C16 C17 1.378(6) . ? C17 C18 1.350(6) . ? N4 C21 1.327(5) . ? N4 C25 1.345(5) . ? N5 C26 1.324(5) . ? N5 N6 1.331(4) . ? N6 C29 1.329(6) . ? C21 C27 1.369(7) . ? C23 C27 1.372(7) . ? C23 C24 1.379(6) . ? C24 C25 1.379(6) . ? C25 C26 1.460(5) . ? C26 C28 1.382(6) . ? C28 C29 1.358(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Mn1 N2 163.16(12) . . ? N5 Mn1 N4 70.57(12) . . ? N2 Mn1 N4 98.44(12) . . ? N5 Mn1 N1 95.78(12) . . ? N2 Mn1 N1 70.33(11) . . ? N4 Mn1 N1 86.91(12) . . ? N5 Mn1 Cl1 104.09(9) . . ? N2 Mn1 Cl1 89.12(8) . . ? N4 Mn1 Cl1 94.34(9) . . ? N1 Mn1 Cl1 159.34(8) . . ? N5 Mn1 Cl2 87.27(9) . . ? N2 Mn1 Cl2 101.33(9) . . ? N4 Mn1 Cl2 156.67(9) . . ? N1 Mn1 Cl2 88.21(9) . . ? Cl1 Mn1 Cl2 98.19(4) . . ? C11 N1 C15 117.7(3) . . ? C11 N1 Mn1 125.4(3) . . ? C15 N1 Mn1 115.1(2) . . ? C16 N2 N3 105.1(3) . . ? C16 N2 Mn1 117.3(2) . . ? N3 N2 Mn1 135.2(2) . . ? C18 N3 N2 111.4(3) . . ? N1 C11 C12 122.9(4) . . ? C13 C12 C11 118.9(4) . . ? C12 C13 C14 118.9(4) . . ? C13 C14 C15 119.3(4) . . ? N1 C15 C14 122.2(4) . . ? N1 C15 C16 114.6(3) . . ? C14 C15 C16 123.2(4) . . ? N2 C16 C17 110.2(3) . . ? N2 C16 C15 117.5(3) . . ? C17 C16 C15 132.3(4) . . ? C18 C17 C16 105.3(4) . . ? N3 C18 C17 108.0(4) . . ? C21 N4 C25 117.9(4) . . ? C21 N4 Mn1 125.1(3) . . ? C25 N4 Mn1 116.9(2) . . ? C26 N5 N6 106.0(3) . . ? C26 N5 Mn1 119.2(2) . . ? N6 N5 Mn1 134.2(3) . . ? C29 N6 N5 111.4(4) . . ? N4 C21 C27 123.4(4) . . ? C27 C23 C24 119.1(4) . . ? C23 C24 C25 118.7(4) . . ? N4 C25 C24 122.2(4) . . ? N4 C25 C26 114.5(3) . . ? C24 C25 C26 123.2(4) . . ? N5 C26 C28 110.0(4) . . ? N5 C26 C25 117.6(3) . . ? C28 C26 C25 132.4(4) . . ? C21 C27 C23 118.7(4) . . ? C29 C28 C26 105.5(4) . . ? N6 C29 C28 107.2(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.664 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.079 #===END _database_code_depnum_ccdc_archive 'CCDC 873523'