# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_925289 #TrackingRef '19319_web_deposit_cif_file_0_En-QingGao_1365557359.925289.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Mn N8 O2' _chemical_formula_weight 279.14 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)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.828(8) _cell_length_b 6.521(4) _cell_length_c 15.217(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.498(8) _cell_angle_gamma 90.00 _cell_volume 1092.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1186 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max ?23.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8388 _exptl_absorpt_correction_T_max 0.9418 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4278 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1826 _reflns_number_gt 1496 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0327P)^2^+0.1282P] 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 1826 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 0.98665(3) 0.04266(6) 0.24898(3) 0.02411(15) Uani 1 1 d . . . C1 C 0.9382(2) -0.2252(4) 0.39731(19) 0.0267(6) Uani 1 1 d . . . C2 C 0.8652(3) -0.2724(4) 0.4583(2) 0.0358(7) Uani 1 1 d . . . H2A H 0.8336 -0.4109 0.4450 0.043 Uiso 1 1 calc R . . H2B H 0.9186 -0.2670 0.5241 0.043 Uiso 1 1 calc R . . C3 C 0.7672(2) 0.0348(4) 0.4934(2) 0.0321(7) Uani 1 1 d . . . H3A H 0.8342 0.0821 0.5438 0.039 Uiso 1 1 calc R . . C4 C 0.6507(3) -0.1492(5) 0.3755(2) 0.0438(8) Uani 1 1 d . . . H4A H 0.6239 -0.2525 0.3304 0.053 Uiso 1 1 calc R . . C5 C 0.5854(3) 0.0094(5) 0.3859(2) 0.0466(9) Uani 1 1 d . . . H5A H 0.5046 0.0373 0.3495 0.056 Uiso 1 1 calc R . . C6 C 0.6281(3) 0.3107(5) 0.4980(3) 0.0576(10) Uani 1 1 d . . . H6A H 0.6971 0.3574 0.5506 0.086 Uiso 1 1 calc R . . H6B H 0.5617 0.2842 0.5184 0.086 Uiso 1 1 calc R . . H6C H 0.6048 0.4142 0.4497 0.086 Uiso 1 1 calc R . . O1 O 0.94139(17) -0.0454(3) 0.37020(13) 0.0324(5) Uani 1 1 d . . . O2 O 0.99351(18) -0.3759(3) 0.38162(13) 0.0352(5) Uani 1 1 d . . . N1 N 0.8619(2) 0.3059(3) 0.22481(17) 0.0302(6) Uani 1 1 d . . . N2 N 0.7854(2) 0.3325(3) 0.25818(18) 0.0359(6) Uani 1 1 d . . . N3 N 0.7102(3) 0.3613(5) 0.2876(2) 0.0676(9) Uani 1 1 d . . . N4 N 0.87305(19) -0.2203(3) 0.17678(16) 0.0271(5) Uani 1 1 d . . . N5 N 0.7659(2) -0.2305(3) 0.15507(18) 0.0348(6) Uani 1 1 d . . . N6 N 0.6628(2) -0.2422(5) 0.1320(3) 0.0755(11) Uani 1 1 d . . . N7 N 0.7643(2) -0.1314(4) 0.44334(17) 0.0321(6) Uani 1 1 d . . . N8 N 0.6596(2) 0.1230(4) 0.46023(17) 0.0349(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0273(2) 0.0178(2) 0.0300(3) -0.00026(18) 0.01374(18) -0.00111(17) C1 0.0276(14) 0.0316(16) 0.0221(15) -0.0014(12) 0.0105(12) 0.0014(12) C2 0.0453(17) 0.0342(17) 0.0380(19) 0.0086(14) 0.0274(15) 0.0108(14) C3 0.0296(14) 0.0350(16) 0.0338(18) -0.0023(14) 0.0139(13) 0.0024(13) C4 0.0403(17) 0.048(2) 0.040(2) -0.0101(16) 0.0109(15) -0.0019(15) C5 0.0331(16) 0.056(2) 0.046(2) -0.0035(17) 0.0081(15) 0.0017(15) C6 0.053(2) 0.047(2) 0.076(3) -0.0118(19) 0.027(2) 0.0120(17) O1 0.0426(11) 0.0249(11) 0.0360(12) 0.0032(9) 0.0218(10) -0.0004(9) O2 0.0488(12) 0.0297(10) 0.0347(12) 0.0044(9) 0.0244(10) 0.0130(10) N1 0.0259(12) 0.0271(13) 0.0413(15) 0.0025(11) 0.0167(11) 0.0001(10) N2 0.0352(14) 0.0275(14) 0.0465(17) 0.0046(11) 0.0169(13) -0.0021(11) N3 0.062(2) 0.067(2) 0.100(3) -0.0002(19) 0.060(2) 0.0019(17) N4 0.0245(12) 0.0235(12) 0.0322(14) 0.0014(10) 0.0090(10) -0.0012(9) N5 0.0325(14) 0.0285(13) 0.0426(16) 0.0042(11) 0.0130(12) -0.0018(11) N6 0.0294(16) 0.077(2) 0.113(3) 0.015(2) 0.0189(17) -0.0050(15) N7 0.0330(12) 0.0346(13) 0.0341(15) 0.0031(12) 0.0189(11) 0.0044(11) N8 0.0321(13) 0.0350(13) 0.0415(15) 0.0007(12) 0.0180(12) 0.0057(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 O2 2.151(2) 2_755 ? Mn1 O1 2.178(2) . ? Mn1 N1 2.205(2) . ? Mn1 N4 2.207(2) . ? Mn1 N4 2.246(2) 2_755 ? Mn1 N1 2.286(2) 2_745 ? C1 O1 1.248(3) . ? C1 O2 1.251(3) . ? C1 C2 1.513(4) . ? C2 N7 1.457(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N7 1.318(3) . ? C3 N8 1.317(3) . ? C3 H3A 0.9300 . ? C4 C5 1.334(4) . ? C4 N7 1.367(4) . ? C4 H4A 0.9300 . ? C5 N8 1.368(4) . ? C5 H5A 0.9300 . ? C6 N8 1.457(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? O2 Mn1 2.151(2) 2_745 ? N1 N2 1.201(3) . ? N1 Mn1 2.286(2) 2_755 ? N2 N3 1.149(3) . ? N4 N5 1.188(3) . ? N4 Mn1 2.246(2) 2_745 ? N5 N6 1.141(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1 172.49(7) 2_755 . ? O2 Mn1 N1 86.93(8) 2_755 . ? O1 Mn1 N1 89.40(8) . . ? O2 Mn1 N4 89.12(9) 2_755 . ? O1 Mn1 N4 85.58(9) . . ? N1 Mn1 N4 105.90(9) . . ? O2 Mn1 N4 89.09(9) 2_755 2_755 ? O1 Mn1 N4 96.95(9) . 2_755 ? N1 Mn1 N4 82.76(10) . 2_755 ? N4 Mn1 N4 171.05(6) . 2_755 ? O2 Mn1 N1 89.10(8) 2_755 2_745 ? O1 Mn1 N1 95.40(8) . 2_745 ? N1 Mn1 N1 171.26(8) . 2_745 ? N4 Mn1 N1 81.79(9) . 2_745 ? N4 Mn1 N1 89.41(9) 2_755 2_745 ? O1 C1 O2 126.4(3) . . ? O1 C1 C2 119.1(2) . . ? O2 C1 C2 114.4(2) . . ? N7 C2 C1 113.2(2) . . ? N7 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N7 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? N7 C3 N8 108.7(3) . . ? N7 C3 H3A 125.6 . . ? N8 C3 H3A 125.6 . . ? C5 C4 N7 107.2(3) . . ? C5 C4 H4A 126.4 . . ? N7 C4 H4A 126.4 . . ? C4 C5 N8 107.1(3) . . ? C4 C5 H5A 126.4 . . ? N8 C5 H5A 126.4 . . ? N8 C6 H6A 109.5 . . ? N8 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N8 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 O1 Mn1 125.04(18) . . ? C1 O2 Mn1 127.73(17) . 2_745 ? N2 N1 Mn1 127.10(19) . . ? N2 N1 Mn1 119.48(19) . 2_755 ? Mn1 N1 Mn1 93.62(10) . 2_755 ? N3 N2 N1 177.8(3) . . ? N5 N4 Mn1 125.03(19) . . ? N5 N4 Mn1 128.14(19) . 2_745 ? Mn1 N4 Mn1 94.67(9) . 2_745 ? N6 N5 N4 178.2(4) . . ? C3 N7 C4 108.4(2) . . ? C3 N7 C2 125.7(2) . . ? C4 N7 C2 125.9(3) . . ? C3 N8 C5 108.5(3) . . ? C3 N8 C6 124.5(3) . . ? C5 N8 C6 127.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N7 27.0(4) . . . . ? O2 C1 C2 N7 -155.1(2) . . . . ? N7 C4 C5 N8 -0.1(4) . . . . ? O2 C1 O1 Mn1 23.6(4) . . . . ? C2 C1 O1 Mn1 -158.70(19) . . . . ? O2 Mn1 O1 C1 87.2(6) 2_755 . . . ? N1 Mn1 O1 C1 147.9(2) . . . . ? N4 Mn1 O1 C1 41.9(2) . . . . ? N4 Mn1 O1 C1 -129.5(2) 2_755 . . . ? N1 Mn1 O1 C1 -39.4(2) 2_745 . . . ? O1 C1 O2 Mn1 -43.3(4) . . . 2_745 ? C2 C1 O2 Mn1 139.0(2) . . . 2_745 ? O2 Mn1 N1 N2 158.5(2) 2_755 . . . ? O1 Mn1 N1 N2 -14.9(2) . . . . ? N4 Mn1 N1 N2 70.3(2) . . . . ? N4 Mn1 N1 N2 -112.0(2) 2_755 . . . ? N1 Mn1 N1 N2 -138.4(2) 2_745 . . . ? O2 Mn1 N1 Mn1 -69.69(8) 2_755 . . 2_755 ? O1 Mn1 N1 Mn1 116.87(9) . . . 2_755 ? N4 Mn1 N1 Mn1 -157.90(8) . . . 2_755 ? N4 Mn1 N1 Mn1 19.78(8) 2_755 . . 2_755 ? N1 Mn1 N1 Mn1 -6.63(16) 2_745 . . 2_755 ? Mn1 N1 N2 N3 -150(8) . . . . ? Mn1 N1 N2 N3 89(9) 2_755 . . . ? O2 Mn1 N4 N5 -106.4(2) 2_755 . . . ? O1 Mn1 N4 N5 68.2(2) . . . . ? N1 Mn1 N4 N5 -19.9(3) . . . . ? N4 Mn1 N4 N5 175.0(3) 2_755 . . . ? N1 Mn1 N4 N5 164.3(2) 2_745 . . . ? O2 Mn1 N4 Mn1 109.05(9) 2_755 . . 2_745 ? O1 Mn1 N4 Mn1 -76.29(9) . . . 2_745 ? N1 Mn1 N4 Mn1 -164.40(8) . . . 2_745 ? N4 Mn1 N4 Mn1 30.5(3) 2_755 . . 2_745 ? N1 Mn1 N4 Mn1 19.83(8) 2_745 . . 2_745 ? Mn1 N4 N5 N6 136(10) . . . . ? Mn1 N4 N5 N6 -92(10) 2_745 . . . ? N8 C3 N7 C4 0.3(3) . . . . ? N8 C3 N7 C2 -179.5(2) . . . . ? C5 C4 N7 C3 -0.1(4) . . . . ? C5 C4 N7 C2 179.6(3) . . . . ? C1 C2 N7 C3 -94.4(3) . . . . ? C1 C2 N7 C4 85.9(4) . . . . ? N7 C3 N8 C5 -0.3(3) . . . . ? N7 C3 N8 C6 179.9(3) . . . . ? C4 C5 N8 C3 0.2(4) . . . . ? C4 C5 N8 C6 -180.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.269 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 925289' ####################################################################### # # 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_925290 #TrackingRef '19320_web_deposit_cif_file_1_En-QingGao_1365557359.925290.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 Mn N5 O4' _chemical_formula_weight 280.12 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 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 7.854(2) _cell_length_b 17.806(5) _cell_length_c 7.879(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.267(3) _cell_angle_gamma 90.00 _cell_volume 1012.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3138 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9020 _exptl_absorpt_correction_T_max 0.9492 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3138 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_unetI/netI 0.0261 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1159 _reflns_number_gt 1019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0232P)^2^+1.4073P] 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 1159 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0655 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2322(3) 0.41151(12) 0.6528(3) 0.0296(5) Uani 1 1 d . . . C2 C 0.0635(3) 0.35969(12) 0.5796(3) 0.0295(5) Uani 1 1 d . . . H2A H 0.0840 0.3175 0.6631 0.035 Uiso 1 1 calc R . . H2B H -0.0442 0.3869 0.5779 0.035 Uiso 1 1 calc R . . C3 C 0.0161(3) 0.25784(12) 0.3406(3) 0.0342(5) Uani 1 1 d . . . H3A H 0.0294 0.2159 0.4150 0.041 Uiso 1 1 calc R . . C4 C 0.0000 0.37487(17) 0.2500 0.0305(6) Uani 1 2 d S . . H4A H 0.0000 0.4271 0.2500 0.037 Uiso 1 2 calc SR . . N4 N 0.0255(2) 0.33143(9) 0.3944(2) 0.0273(4) Uani 1 1 d . . . O1 O 0.3191(2) 0.42168(9) 0.5527(2) 0.0387(4) Uani 1 1 d . . . O2 O 0.2641(2) 0.43753(10) 0.8099(2) 0.0416(4) Uani 1 1 d . . . Mn1 Mn 0.5000 0.5000 0.5000 0.02191(14) Uani 1 2 d S . . N1 N 0.5000 0.56657(14) 0.7500 0.0350(6) Uani 1 2 d S . . N2 N 0.470(2) 0.63254(19) 0.733(3) 0.035(3) Uani 0.50 1 d P A -1 N3 N 0.4413(9) 0.6960(2) 0.7197(14) 0.068(3) Uani 0.50 1 d P A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0333(12) 0.0323(11) 0.0220(10) -0.0022(8) 0.0098(9) -0.0055(9) C2 0.0343(11) 0.0359(11) 0.0197(9) -0.0029(8) 0.0123(9) -0.0071(9) C3 0.0452(13) 0.0266(11) 0.0285(11) 0.0014(9) 0.0119(10) -0.0018(9) C4 0.0410(18) 0.0269(15) 0.0210(14) 0.000 0.0093(13) 0.000 N4 0.0326(10) 0.0288(9) 0.0194(8) -0.0018(7) 0.0090(7) -0.0037(7) O1 0.0474(10) 0.0440(9) 0.0315(8) -0.0068(7) 0.0229(7) -0.0179(8) O2 0.0420(10) 0.0608(11) 0.0247(8) -0.0151(7) 0.0160(7) -0.0227(8) Mn1 0.0258(2) 0.0235(2) 0.0172(2) 0.00140(15) 0.00936(17) 0.00019(16) N1 0.0603(19) 0.0250(13) 0.0263(13) 0.000 0.0241(13) 0.000 N2 0.056(9) 0.0296(16) 0.025(7) -0.002(2) 0.022(7) -0.001(2) N3 0.120(8) 0.0250(19) 0.084(7) 0.003(3) 0.067(7) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.243(2) . ? C1 O2 1.251(2) . ? C1 C2 1.528(3) . ? C2 N4 1.458(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C3 1.348(4) 2 ? C3 N4 1.370(3) . ? C3 H3A 0.9300 . ? C4 N4 1.324(2) 2 ? C4 N4 1.324(2) . ? C4 H4A 0.9300 . ? O1 Mn1 2.1448(15) . ? O2 Mn1 2.1726(15) 2_656 ? Mn1 O1 2.1448(15) 5_666 ? Mn1 O2 2.1726(15) 6_565 ? Mn1 O2 2.1726(15) 2_656 ? Mn1 N1 2.2990(14) . ? Mn1 N1 2.2990(14) 5_666 ? N1 N2 1.195(5) 2_656 ? N1 N2 1.195(5) . ? N1 Mn1 2.2990(14) 2_656 ? N2 N3 1.149(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 128.9(2) . . ? O1 C1 C2 117.38(18) . . ? O2 C1 C2 113.68(18) . . ? N4 C2 C1 112.99(16) . . ? N4 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N4 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C3 C3 N4 107.00(11) 2 . ? C3 C3 H3A 126.5 2 . ? N4 C3 H3A 126.5 . . ? N4 C4 N4 108.5(3) 2 . ? N4 C4 H4A 125.7 2 . ? N4 C4 H4A 125.7 . . ? C4 N4 C3 108.75(18) . . ? C4 N4 C2 124.05(18) . . ? C3 N4 C2 127.17(17) . . ? C1 O1 Mn1 142.08(14) . . ? C1 O2 Mn1 130.88(14) . 2_656 ? O1 Mn1 O1 180.0 5_666 . ? O1 Mn1 O2 89.04(7) 5_666 6_565 ? O1 Mn1 O2 90.96(7) . 6_565 ? O1 Mn1 O2 90.96(7) 5_666 2_656 ? O1 Mn1 O2 89.04(7) . 2_656 ? O2 Mn1 O2 180.0 6_565 2_656 ? O1 Mn1 N1 93.13(6) 5_666 . ? O1 Mn1 N1 86.87(6) . . ? O2 Mn1 N1 92.18(5) 6_565 . ? O2 Mn1 N1 87.82(5) 2_656 . ? O1 Mn1 N1 86.87(6) 5_666 5_666 ? O1 Mn1 N1 93.13(6) . 5_666 ? O2 Mn1 N1 87.82(5) 6_565 5_666 ? O2 Mn1 N1 92.18(5) 2_656 5_666 ? N1 Mn1 N1 180.0 . 5_666 ? N2 N1 Mn1 122.5(13) 2_656 . ? N2 N1 Mn1 118.4(12) . . ? N2 N1 Mn1 118.4(12) 2_656 2_656 ? N2 N1 Mn1 122.5(13) . 2_656 ? Mn1 N1 Mn1 117.92(11) . 2_656 ? N3 N2 N1 179(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N4 -2.2(3) . . . . ? O2 C1 C2 N4 178.49(19) . . . . ? N4 C4 N4 C3 0.03(12) 2 . . . ? N4 C4 N4 C2 178.0(2) 2 . . . ? C3 C3 N4 C4 -0.1(3) 2 . . . ? C3 C3 N4 C2 -178.0(2) 2 . . . ? C1 C2 N4 C4 -55.4(2) . . . . ? C1 C2 N4 C3 122.2(2) . . . . ? O2 C1 O1 Mn1 -24.8(4) . . . . ? C2 C1 O1 Mn1 155.97(18) . . . . ? O1 C1 O2 Mn1 -9.0(4) . . . 2_656 ? C2 C1 O2 Mn1 170.24(14) . . . 2_656 ? C1 O1 Mn1 O1 139(100) . . . 5_666 ? C1 O1 Mn1 O2 -86.9(3) . . . 6_565 ? C1 O1 Mn1 O2 93.1(3) . . . 2_656 ? C1 O1 Mn1 N1 5.3(3) . . . . ? C1 O1 Mn1 N1 -174.7(3) . . . 5_666 ? O1 Mn1 N1 N2 25.1(7) 5_666 . . 2_656 ? O1 Mn1 N1 N2 -154.9(7) . . . 2_656 ? O2 Mn1 N1 N2 -64.1(7) 6_565 . . 2_656 ? O2 Mn1 N1 N2 115.9(7) 2_656 . . 2_656 ? N1 Mn1 N1 N2 168(100) 5_666 . . 2_656 ? O1 Mn1 N1 N2 49.5(8) 5_666 . . . ? O1 Mn1 N1 N2 -130.5(8) . . . . ? O2 Mn1 N1 N2 -39.7(8) 6_565 . . . ? O2 Mn1 N1 N2 140.3(8) 2_656 . . . ? N1 Mn1 N1 N2 -168(100) 5_666 . . . ? O1 Mn1 N1 Mn1 -142.46(5) 5_666 . . 2_656 ? O1 Mn1 N1 Mn1 37.54(5) . . . 2_656 ? O2 Mn1 N1 Mn1 128.38(5) 6_565 . . 2_656 ? O2 Mn1 N1 Mn1 -51.62(5) 2_656 . . 2_656 ? N1 Mn1 N1 Mn1 0(9) 5_666 . . 2_656 ? Mn1 N1 N2 N3 179(100) . . . . ? Mn1 N1 N2 N3 11(63) 2_656 . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.251 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 925290' ####################################################################### # # 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_925291 #TrackingRef '19321_web_deposit_cif_file_2_En-QingGao_1365557359.925291.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9.50 H13 Mn N5 O4.50' _chemical_formula_weight 324.19 _chemical_absolute_configuration syn 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.3176(8) _cell_length_b 7.6287(4) _cell_length_c 10.7629(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.4000(10) _cell_angle_gamma 90.00 _cell_volume 1271.29(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7436 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_T_min 0.8700 _exptl_absorpt_correction_T_max 0.9158 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7816 _diffrn_reflns_av_R_equivalents 0.0839 _diffrn_reflns_av_unetI/netI 0.0809 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2202 _reflns_number_gt 2102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1101P)^2^+1.1732P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_number_reflns 2202 _refine_ls_number_parameters 187 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.021 _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 0.24823(4) 0.14780(12) 0.48486(6) 0.0231(2) Uani 1 1 d . . . C4 C 0.0592(4) 0.2609(8) 0.8715(5) 0.0345(13) Uani 1 1 d . . . H4A H 0.0529 0.3533 0.9242 0.041 Uiso 1 1 calc R . . C6 C 0.1130(3) 0.0905(7) 0.7547(5) 0.0256(11) Uani 1 1 d . . . H6A H 0.1494 0.0436 0.7119 0.031 Uiso 1 1 calc R . . C5 C 0.0048(3) 0.1298(12) 0.8312(5) 0.0403(15) Uani 1 1 d . . . H5A H -0.0469 0.1139 0.8489 0.048 Uiso 1 1 calc R . . C2 C 0.1974(3) 0.3654(7) 0.8431(5) 0.0254(11) Uani 1 1 d . . . H2A H 0.1772 0.4783 0.8657 0.030 Uiso 1 1 calc R . . C1 C 0.2236(3) 0.3917(8) 0.7186(5) 0.0254(10) Uani 1 1 d . . . C3 C 0.2766(4) 0.3096(10) 0.9573(5) 0.0379(14) Uani 1 1 d . . . H3A H 0.2601 0.2935 1.0346 0.057 Uiso 1 1 calc R . . H3B H 0.3202 0.3989 0.9730 0.057 Uiso 1 1 calc R . . H3C H 0.2991 0.2016 0.9357 0.057 Uiso 1 1 calc R . . C7 C -0.0051(5) -0.2802(11) 0.7957(8) 0.0567(19) Uani 1 1 d . . . H7A H 0.0509 -0.2978 0.8585 0.085 Uiso 1 1 calc R . . H7B H -0.0262 -0.3893 0.7531 0.085 Uiso 1 1 calc R . . H7C H -0.0442 -0.2377 0.8395 0.085 Uiso 1 1 calc R . . C8 C 0.0013(4) -0.1452(7) 0.6930(6) 0.0299(11) Uani 1 1 d . . . H8A H 0.0398 -0.1929 0.6475 0.036 Uiso 1 1 calc R . . C9 C -0.0884(3) -0.1144(8) 0.5905(5) 0.0290(11) Uani 1 1 d . . . N5 N 0.0390(3) 0.0189(7) 0.7568(4) 0.0282(9) Uani 1 1 d . . . N4 N 0.1270(3) 0.2384(6) 0.8225(4) 0.0252(9) Uani 1 1 d . . . N3 N 0.1488(4) 0.4225(9) 0.1586(5) 0.0500(14) Uani 1 1 d . . . N1 N 0.2013(3) 0.4061(7) 0.3888(4) 0.0322(10) Uani 1 1 d . . . N2 N 0.1744(3) 0.4155(6) 0.2708(4) 0.0274(9) Uani 1 1 d . . . O1 O 0.2334(3) 0.2564(5) 0.6608(4) 0.0348(9) Uani 1 1 d . . . O2 O 0.2365(3) 0.5454(6) 0.6932(4) 0.0430(11) Uani 1 1 d . . . O3 O -0.1181(3) 0.0363(6) 0.5776(5) 0.0439(11) Uani 1 1 d . . . O4 O -0.1211(2) -0.2499(6) 0.5313(4) 0.0368(9) Uani 1 1 d . . . C10 C 0.0000 0.388(2) 0.5000 0.067(3) Uani 1 2 d S . . O5 O 0.0527(8) 0.4815(17) 0.5898(13) 0.070(3) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0311(4) 0.0198(4) 0.0160(3) -0.0008(4) 0.0040(3) -0.0007(3) C4 0.044(3) 0.040(4) 0.025(2) -0.010(2) 0.019(2) -0.006(3) C6 0.025(2) 0.027(3) 0.024(2) -0.001(2) 0.006(2) -0.003(2) C5 0.035(3) 0.057(4) 0.033(2) -0.011(4) 0.017(2) -0.005(3) C2 0.032(3) 0.026(3) 0.019(2) -0.0042(19) 0.009(2) -0.004(2) C1 0.031(2) 0.024(3) 0.019(2) 0.000(2) 0.006(2) -0.006(2) C3 0.037(3) 0.055(4) 0.016(2) 0.001(3) 0.000(2) -0.006(3) C7 0.060(4) 0.033(4) 0.061(4) 0.021(3) -0.004(4) -0.003(3) C8 0.029(3) 0.025(3) 0.031(3) 0.001(2) 0.003(2) -0.004(2) C9 0.025(2) 0.033(3) 0.026(2) 0.005(2) 0.004(2) 0.002(3) N5 0.027(2) 0.030(2) 0.026(2) -0.0012(18) 0.0059(18) -0.0001(19) N4 0.032(2) 0.027(2) 0.0177(19) 0.0016(18) 0.0086(18) -0.003(2) N3 0.073(4) 0.052(4) 0.022(2) -0.002(2) 0.010(2) -0.007(3) N1 0.043(2) 0.030(3) 0.018(2) -0.0019(18) 0.0020(19) -0.001(2) N2 0.036(2) 0.019(2) 0.025(2) -0.0027(17) 0.0066(19) -0.0024(19) O1 0.055(3) 0.030(2) 0.0245(17) -0.0018(16) 0.0202(18) 0.0004(19) O2 0.081(3) 0.026(2) 0.0235(18) 0.0009(16) 0.018(2) -0.012(2) O3 0.034(2) 0.030(2) 0.052(3) 0.003(2) -0.0085(19) -0.0014(18) O4 0.0275(19) 0.033(2) 0.044(2) -0.0099(19) 0.0029(17) -0.0037(18) C10 0.063(7) 0.063(8) 0.065(7) 0.000 0.003(6) 0.000 O5 0.067(7) 0.070(9) 0.064(7) 0.008(6) 0.010(6) 0.005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.149(4) . ? Mn1 O2 2.156(4) 4_546 ? Mn1 O4 2.175(4) 3 ? Mn1 O3 2.187(4) 2_556 ? Mn1 N1 2.245(5) . ? Mn1 N1 2.284(5) 4_546 ? C4 C5 1.317(9) . ? C4 N4 1.379(6) . ? C4 H4A 0.9300 . ? C6 N4 1.324(7) . ? C6 N5 1.332(7) . ? C6 H6A 0.9300 . ? C5 N5 1.397(8) . ? C5 H5A 0.9300 . ? C2 N4 1.466(7) . ? C2 C3 1.536(8) . ? C2 C1 1.543(6) . ? C2 H2A 0.9800 . ? C1 O2 1.236(7) . ? C1 O1 1.241(7) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C7 C8 1.538(9) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N5 1.466(8) . ? C8 C9 1.547(7) . ? C8 H8A 0.9800 . ? C9 O3 1.239(8) . ? C9 O4 1.243(8) . ? N3 N2 1.147(7) . ? N1 N2 1.208(6) . ? N1 Mn1 2.284(5) 4_556 ? O2 Mn1 2.156(4) 4_556 ? O3 Mn1 2.187(4) 2_556 ? O4 Mn1 2.175(4) 3_445 ? C10 O5 1.289(16) . ? C10 O5 1.289(16) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 178.56(18) . 4_546 ? O1 Mn1 O4 91.92(16) . 3 ? O2 Mn1 O4 87.37(17) 4_546 3 ? O1 Mn1 O3 93.01(17) . 2_556 ? O2 Mn1 O3 87.7(2) 4_546 2_556 ? O4 Mn1 O3 175.06(17) 3 2_556 ? O1 Mn1 N1 87.16(16) . . ? O2 Mn1 N1 91.55(16) 4_546 . ? O4 Mn1 N1 87.60(17) 3 . ? O3 Mn1 N1 92.45(18) 2_556 . ? O1 Mn1 N1 84.63(16) . 4_546 ? O2 Mn1 N1 96.63(16) 4_546 4_546 ? O4 Mn1 N1 90.55(17) 3 4_546 ? O3 Mn1 N1 90.10(18) 2_556 4_546 ? N1 Mn1 N1 171.52(14) . 4_546 ? C5 C4 N4 108.6(5) . . ? C5 C4 H4A 125.7 . . ? N4 C4 H4A 125.7 . . ? N4 C6 N5 109.9(4) . . ? N4 C6 H6A 125.1 . . ? N5 C6 H6A 125.1 . . ? C4 C5 N5 107.4(4) . . ? C4 C5 H5A 126.3 . . ? N5 C5 H5A 126.3 . . ? N4 C2 C3 111.0(4) . . ? N4 C2 C1 111.9(4) . . ? C3 C2 C1 109.7(4) . . ? N4 C2 H2A 108.0 . . ? C3 C2 H2A 108.0 . . ? C1 C2 H2A 108.0 . . ? O2 C1 O1 128.3(4) . . ? O2 C1 C2 115.3(5) . . ? O1 C1 C2 116.2(5) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N5 C8 C7 110.4(5) . . ? N5 C8 C9 111.6(5) . . ? C7 C8 C9 110.5(5) . . ? N5 C8 H8A 108.1 . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? O3 C9 O4 128.7(5) . . ? O3 C9 C8 118.0(5) . . ? O4 C9 C8 113.3(5) . . ? C6 N5 C5 106.9(5) . . ? C6 N5 C8 126.2(5) . . ? C5 N5 C8 126.9(5) . . ? C6 N4 C4 107.3(4) . . ? C6 N4 C2 129.6(4) . . ? C4 N4 C2 123.1(5) . . ? N2 N1 Mn1 119.6(4) . . ? N2 N1 Mn1 121.4(4) . 4_556 ? Mn1 N1 Mn1 115.34(18) . 4_556 ? N3 N2 N1 179.3(7) . . ? C1 O1 Mn1 146.1(3) . . ? C1 O2 Mn1 127.9(3) . 4_556 ? C9 O3 Mn1 134.7(4) . 2_556 ? C9 O4 Mn1 130.4(4) . 3_445 ? O5 C10 O5 112.5(17) . 2_556 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C4 C5 N5 1.1(7) . . . . ? N4 C2 C1 O2 137.0(5) . . . . ? C3 C2 C1 O2 -99.3(6) . . . . ? N4 C2 C1 O1 -46.6(6) . . . . ? C3 C2 C1 O1 77.2(6) . . . . ? N5 C8 C9 O3 -2.3(6) . . . . ? C7 C8 C9 O3 120.9(6) . . . . ? N5 C8 C9 O4 177.8(4) . . . . ? C7 C8 C9 O4 -59.0(7) . . . . ? N4 C6 N5 C5 0.0(6) . . . . ? N4 C6 N5 C8 180.0(5) . . . . ? C4 C5 N5 C6 -0.7(7) . . . . ? C4 C5 N5 C8 179.3(5) . . . . ? C7 C8 N5 C6 117.5(6) . . . . ? C9 C8 N5 C6 -119.2(5) . . . . ? C7 C8 N5 C5 -62.5(8) . . . . ? C9 C8 N5 C5 60.8(7) . . . . ? N5 C6 N4 C4 0.7(6) . . . . ? N5 C6 N4 C2 -177.2(5) . . . . ? C5 C4 N4 C6 -1.2(6) . . . . ? C5 C4 N4 C2 176.9(5) . . . . ? C3 C2 N4 C6 -84.5(6) . . . . ? C1 C2 N4 C6 38.5(7) . . . . ? C3 C2 N4 C4 97.9(6) . . . . ? C1 C2 N4 C4 -139.1(5) . . . . ? O1 Mn1 N1 N2 -161.5(4) . . . . ? O2 Mn1 N1 N2 19.2(4) 4_546 . . . ? O4 Mn1 N1 N2 106.5(4) 3 . . . ? O3 Mn1 N1 N2 -68.6(4) 2_556 . . . ? N1 Mn1 N1 N2 -176.0(6) 4_546 . . . ? O1 Mn1 N1 Mn1 39.7(2) . . . 4_556 ? O2 Mn1 N1 Mn1 -139.7(2) 4_546 . . 4_556 ? O4 Mn1 N1 Mn1 -52.4(2) 3 . . 4_556 ? O3 Mn1 N1 Mn1 132.6(2) 2_556 . . 4_556 ? N1 Mn1 N1 Mn1 25.2(5) 4_546 . . 4_556 ? Mn1 N1 N2 N3 11(45) . . . . ? Mn1 N1 N2 N3 168(100) 4_556 . . . ? O2 C1 O1 Mn1 -17.2(10) . . . . ? C2 C1 O1 Mn1 166.9(5) . . . . ? O2 Mn1 O1 C1 12(8) 4_546 . . . ? O4 Mn1 O1 C1 72.3(7) 3 . . . ? O3 Mn1 O1 C1 -107.5(7) 2_556 . . . ? N1 Mn1 O1 C1 -15.2(7) . . . . ? N1 Mn1 O1 C1 162.7(7) 4_546 . . . ? O1 C1 O2 Mn1 15.8(9) . . . 4_556 ? C2 C1 O2 Mn1 -168.3(4) . . . 4_556 ? O4 C9 O3 Mn1 27.5(9) . . . 2_556 ? C8 C9 O3 Mn1 -152.3(4) . . . 2_556 ? O3 C9 O4 Mn1 -45.3(8) . . . 3_445 ? C8 C9 O4 Mn1 134.5(4) . . . 3_445 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.858 _refine_diff_density_min -0.984 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 925291' ####################################################################### # # 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_925292 #TrackingRef '19322_web_deposit_cif_file_3_En-QingGao_1365557359.925292.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 Mn3 N16 O10' _chemical_formula_weight 791.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.243(4) _cell_length_b 18.103(8) _cell_length_c 9.337(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.91(4) _cell_angle_gamma 90.00 _cell_volume 1509.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7436 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 802 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8700 _exptl_absorpt_correction_T_max 0.9158 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8224 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2930 _reflns_number_gt 2614 _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^)+(0.0595P)^2^+2.4912P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2930 _refine_ls_number_parameters 222 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.156 _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 -0.25411(6) 0.16001(3) 0.85472(6) 0.02980(18) Uani 1 1 d . . . Mn2 Mn 0.0000 0.0000 1.0000 0.0315(2) Uani 1 2 d S . . C1 C 0.0122(4) 0.1066(2) 0.7329(4) 0.0367(8) Uani 1 1 d . . . C2 C 0.1330(5) 0.1279(3) 0.6564(7) 0.0625(14) Uani 1 1 d . . . H2A H 0.0808 0.1432 0.5557 0.075 Uiso 1 1 calc R . . C3 C 0.3374(5) 0.0360(3) 0.7468(5) 0.0526(11) Uani 1 1 d . . . H3A H 0.3705 0.0540 0.8430 0.063 Uiso 1 1 calc R . . C4 C 0.2107(6) 0.0227(3) 0.5161(6) 0.0617(12) Uani 1 1 d . . . H4A H 0.1408 0.0299 0.4258 0.074 Uiso 1 1 calc R . . C5 C 0.3142(5) -0.0301(3) 0.5476(5) 0.0535(11) Uani 1 1 d . . . H5A H 0.3302 -0.0663 0.4826 0.064 Uiso 1 1 calc R . . C6 C 0.5253(4) -0.0633(2) 0.7781(5) 0.0481(10) Uani 1 1 d . . . H6A H 0.5012 -0.0797 0.8694 0.058 Uiso 1 1 calc R . . C7 C 0.6614(4) -0.01078(19) 0.8262(4) 0.0365(8) Uani 1 1 d . . . C8 C 0.2218(8) 0.1902(4) 0.7241(10) 0.105(2) Uani 1 1 d U . . H8A H 0.2951 0.2013 0.6707 0.157 Uiso 1 1 calc R . . H8B H 0.2714 0.1786 0.8251 0.157 Uiso 1 1 calc R . . H8C H 0.1579 0.2323 0.7216 0.157 Uiso 1 1 calc R . . C9 C 0.5562(7) -0.1302(3) 0.7028(8) 0.0793(17) Uani 1 1 d . . . H9A H 0.4679 -0.1604 0.6769 0.119 Uiso 1 1 calc R . . H9B H 0.6360 -0.1573 0.7676 0.119 Uiso 1 1 calc R . . H9C H 0.5850 -0.1167 0.6146 0.119 Uiso 1 1 calc R . . N1 N -0.0958(4) 0.10612(19) 1.0484(4) 0.0460(8) Uani 1 1 d . . . N2 N -0.0556(5) 0.1281(2) 1.1669(4) 0.0606(11) Uani 1 1 d . . . N3 N -0.0037(9) 0.1508(4) 1.2849(6) 0.122(3) Uani 1 1 d . . . N4 N -0.4148(5) 0.1864(2) 0.9950(5) 0.0585(10) Uani 1 1 d . . . N5 N -0.4048(4) 0.2390(2) 1.0730(4) 0.0464(8) Uani 1 1 d . . . N6 N -0.4009(4) 0.2910(2) 1.1496(4) 0.0484(8) Uani 1 1 d . . . N7 N 0.2261(4) 0.0639(2) 0.6408(4) 0.0501(9) Uani 1 1 d . . . N8 N 0.3930(3) -0.02172(18) 0.6923(4) 0.0414(7) Uani 1 1 d . . . O1 O -0.0881(3) 0.15442(16) 0.7242(3) 0.0456(7) Uani 1 1 d . . . O2 O 0.0187(3) 0.04483(15) 0.7909(3) 0.0471(7) Uani 1 1 d . . . O3 O 0.6439(3) 0.05560(13) 0.7925(3) 0.0428(6) Uani 1 1 d . . . O4 O 0.7761(3) -0.04177(15) 0.9004(4) 0.0546(8) Uani 1 1 d . . . O5 O -0.1588(5) 0.2669(2) 0.9427(4) 0.0723(11) Uani 1 1 d D . . H5C H -0.159(8) 0.286(3) 1.027(4) 0.108 Uiso 1 1 d D . . H5B H -0.131(8) 0.299(3) 0.888(6) 0.108 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0291(3) 0.0250(3) 0.0331(3) -0.00084(19) 0.0039(2) 0.00130(19) Mn2 0.0253(4) 0.0308(4) 0.0348(4) 0.0066(3) 0.0016(3) 0.0047(3) C1 0.0296(18) 0.042(2) 0.0368(19) 0.0041(16) 0.0056(15) 0.0064(15) C2 0.045(2) 0.052(3) 0.098(4) 0.026(3) 0.034(3) 0.017(2) C3 0.044(2) 0.058(3) 0.052(3) -0.008(2) 0.0057(19) 0.016(2) C4 0.051(3) 0.073(3) 0.050(3) 0.008(2) -0.007(2) 0.004(2) C5 0.053(3) 0.055(3) 0.046(2) -0.007(2) 0.002(2) -0.001(2) C6 0.034(2) 0.032(2) 0.070(3) 0.0009(18) -0.0013(19) 0.0011(16) C7 0.0299(18) 0.0309(18) 0.043(2) -0.0036(15) -0.0002(15) 0.0014(14) C8 0.076(3) 0.082(4) 0.163(5) -0.019(4) 0.043(3) -0.006(3) C9 0.067(3) 0.047(3) 0.113(5) -0.014(3) 0.004(3) -0.002(2) N1 0.050(2) 0.0446(19) 0.0356(19) -0.0025(15) -0.0043(15) 0.0159(15) N2 0.090(3) 0.047(2) 0.039(2) -0.0002(17) 0.005(2) 0.028(2) N3 0.186(7) 0.110(5) 0.046(3) -0.026(3) -0.011(3) 0.071(5) N4 0.059(2) 0.059(2) 0.063(2) -0.017(2) 0.026(2) -0.0073(19) N5 0.0379(18) 0.059(2) 0.0407(18) -0.0068(17) 0.0071(14) 0.0054(16) N6 0.0417(19) 0.056(2) 0.0446(19) -0.0171(17) 0.0064(15) -0.0030(16) N7 0.0292(16) 0.056(2) 0.068(2) 0.0192(18) 0.0174(16) 0.0126(15) N8 0.0264(15) 0.0407(17) 0.0513(19) -0.0073(15) -0.0008(14) 0.0009(13) O1 0.0362(14) 0.0504(16) 0.0532(17) 0.0112(13) 0.0169(13) 0.0127(12) O2 0.0572(18) 0.0424(15) 0.0470(16) 0.0104(13) 0.0228(14) 0.0093(13) O3 0.0399(14) 0.0269(13) 0.0532(16) -0.0010(11) -0.0035(12) -0.0015(11) O4 0.0307(14) 0.0377(15) 0.082(2) 0.0072(15) -0.0096(14) 0.0008(12) O5 0.093(3) 0.063(2) 0.071(2) -0.0245(18) 0.038(2) -0.038(2) _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 O3 2.125(3) 1_455 ? Mn1 O1 2.194(3) . ? Mn1 O5 2.196(3) . ? Mn1 N6 2.226(3) 4_565 ? Mn1 N1 2.236(3) . ? Mn1 N4 2.270(4) . ? Mn2 O2 2.162(3) . ? Mn2 O2 2.162(3) 3_557 ? Mn2 O4 2.175(3) 3_657 ? Mn2 O4 2.175(3) 1_455 ? Mn2 N1 2.210(3) 3_557 ? Mn2 N1 2.210(3) . ? C1 O2 1.238(5) . ? C1 O1 1.255(4) . ? C1 C2 1.522(6) . ? C2 C8 1.443(9) . ? C2 N7 1.472(6) . ? C2 H2A 0.9800 . ? C3 N8 1.322(5) . ? C3 N7 1.331(5) . ? C3 H3A 0.9300 . ? C4 C5 1.330(7) . ? C4 N7 1.359(7) . ? C4 H4A 0.9300 . ? C5 N8 1.369(6) . ? C5 H5A 0.9300 . ? C6 C9 1.465(7) . ? C6 N8 1.484(5) . ? C6 C7 1.548(5) . ? C6 H6A 0.9800 . ? C7 O4 1.241(4) . ? C7 O3 1.242(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N1 N2 1.145(5) . ? N2 N3 1.158(6) . ? N4 N5 1.188(5) . ? N5 N6 1.178(5) . ? N6 Mn1 2.226(3) 4_566 ? O3 Mn1 2.125(3) 1_655 ? O4 Mn2 2.175(3) 1_655 ? O5 H5C 0.86(2) . ? O5 H5B 0.86(2) . ? 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 O3 Mn1 O1 97.58(12) 1_455 . ? O3 Mn1 O5 173.16(13) 1_455 . ? O1 Mn1 O5 88.72(13) . . ? O3 Mn1 N6 89.40(12) 1_455 4_565 ? O1 Mn1 N6 84.21(12) . 4_565 ? O5 Mn1 N6 93.90(16) . 4_565 ? O3 Mn1 N1 89.15(12) 1_455 . ? O1 Mn1 N1 91.33(13) . . ? O5 Mn1 N1 88.05(16) . . ? N6 Mn1 N1 175.09(13) 4_565 . ? O3 Mn1 N4 91.98(13) 1_455 . ? O1 Mn1 N4 170.23(13) . . ? O5 Mn1 N4 81.83(14) . . ? N6 Mn1 N4 93.92(15) 4_565 . ? N1 Mn1 N4 90.82(15) . . ? O2 Mn2 O2 180.0 . 3_557 ? O2 Mn2 O4 88.13(13) . 3_657 ? O2 Mn2 O4 91.87(13) 3_557 3_657 ? O2 Mn2 O4 91.87(13) . 1_455 ? O2 Mn2 O4 88.13(13) 3_557 1_455 ? O4 Mn2 O4 180.0 3_657 1_455 ? O2 Mn2 N1 90.71(12) . 3_557 ? O2 Mn2 N1 89.29(12) 3_557 3_557 ? O4 Mn2 N1 90.13(12) 3_657 3_557 ? O4 Mn2 N1 89.87(12) 1_455 3_557 ? O2 Mn2 N1 89.29(12) . . ? O2 Mn2 N1 90.71(12) 3_557 . ? O4 Mn2 N1 89.87(12) 3_657 . ? O4 Mn2 N1 90.13(12) 1_455 . ? N1 Mn2 N1 180.0 3_557 . ? O2 C1 O1 127.1(4) . . ? O2 C1 C2 118.3(3) . . ? O1 C1 C2 114.5(3) . . ? C8 C2 N7 112.2(5) . . ? C8 C2 C1 113.3(5) . . ? N7 C2 C1 111.5(4) . . ? C8 C2 H2A 106.5 . . ? N7 C2 H2A 106.5 . . ? C1 C2 H2A 106.5 . . ? N8 C3 N7 108.4(4) . . ? N8 C3 H3A 125.8 . . ? N7 C3 H3A 125.8 . . ? C5 C4 N7 107.1(4) . . ? C5 C4 H4A 126.4 . . ? N7 C4 H4A 126.4 . . ? C4 C5 N8 108.0(4) . . ? C4 C5 H5A 126.0 . . ? N8 C5 H5A 126.0 . . ? C9 C6 N8 113.3(4) . . ? C9 C6 C7 113.8(4) . . ? N8 C6 C7 109.9(3) . . ? C9 C6 H6A 106.4 . . ? N8 C6 H6A 106.4 . . ? C7 C6 H6A 106.4 . . ? O4 C7 O3 128.0(3) . . ? O4 C7 C6 113.4(3) . . ? O3 C7 C6 118.5(3) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 N1 Mn2 116.9(3) . . ? N2 N1 Mn1 127.7(3) . . ? Mn2 N1 Mn1 115.30(15) . . ? N1 N2 N3 174.5(7) . . ? N5 N4 Mn1 124.3(3) . . ? N6 N5 N4 177.4(4) . . ? N5 N6 Mn1 139.3(3) . 4_566 ? C3 N7 C4 108.6(4) . . ? C3 N7 C2 125.8(4) . . ? C4 N7 C2 125.6(4) . . ? C3 N8 C5 107.9(4) . . ? C3 N8 C6 122.7(4) . . ? C5 N8 C6 129.3(4) . . ? C1 O1 Mn1 127.3(2) . . ? C1 O2 Mn2 136.7(3) . . ? C7 O3 Mn1 140.5(2) . 1_655 ? C7 O4 Mn2 131.6(3) . 1_655 ? Mn1 O5 H5C 127(4) . . ? Mn1 O5 H5B 122(4) . . ? H5C O5 H5B 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C8 -117.2(5) . . . . ? O1 C1 C2 C8 65.5(6) . . . . ? O2 C1 C2 N7 10.4(6) . . . . ? O1 C1 C2 N7 -166.9(4) . . . . ? N7 C4 C5 N8 0.4(6) . . . . ? C9 C6 C7 O4 -52.6(6) . . . . ? N8 C6 C7 O4 179.2(4) . . . . ? C9 C6 C7 O3 129.8(5) . . . . ? N8 C6 C7 O3 1.5(6) . . . . ? O2 Mn2 N1 N2 -138.4(4) . . . . ? O2 Mn2 N1 N2 41.6(4) 3_557 . . . ? O4 Mn2 N1 N2 -50.3(4) 3_657 . . . ? O4 Mn2 N1 N2 129.7(4) 1_455 . . . ? N1 Mn2 N1 N2 130.1(6) 3_557 . . . ? O2 Mn2 N1 Mn1 39.18(18) . . . . ? O2 Mn2 N1 Mn1 -140.82(18) 3_557 . . . ? O4 Mn2 N1 Mn1 127.31(19) 3_657 . . . ? O4 Mn2 N1 Mn1 -52.69(19) 1_455 . . . ? N1 Mn2 N1 Mn1 -52.3(7) 3_557 . . . ? O3 Mn1 N1 N2 -138.6(5) 1_455 . . . ? O1 Mn1 N1 N2 123.8(5) . . . . ? O5 Mn1 N1 N2 35.1(5) . . . . ? N6 Mn1 N1 N2 148.5(15) 4_565 . . . ? N4 Mn1 N1 N2 -46.7(5) . . . . ? O3 Mn1 N1 Mn2 44.07(18) 1_455 . . . ? O1 Mn1 N1 Mn2 -53.49(18) . . . . ? O5 Mn1 N1 Mn2 -142.16(19) . . . . ? N6 Mn1 N1 Mn2 -28.8(17) 4_565 . . . ? N4 Mn1 N1 Mn2 136.04(19) . . . . ? Mn2 N1 N2 N3 64(5) . . . . ? Mn1 N1 N2 N3 -114(5) . . . . ? O3 Mn1 N4 N5 173.3(4) 1_455 . . . ? O1 Mn1 N4 N5 -18.6(11) . . . . ? O5 Mn1 N4 N5 -3.8(4) . . . . ? N6 Mn1 N4 N5 -97.2(4) 4_565 . . . ? N1 Mn1 N4 N5 84.1(4) . . . . ? Mn1 N4 N5 N6 154(10) . . . . ? N4 N5 N6 Mn1 142(10) . . . 4_566 ? N8 C3 N7 C4 0.2(5) . . . . ? N8 C3 N7 C2 179.0(4) . . . . ? C5 C4 N7 C3 -0.4(6) . . . . ? C5 C4 N7 C2 -179.2(4) . . . . ? C8 C2 N7 C3 48.9(7) . . . . ? C1 C2 N7 C3 -79.3(6) . . . . ? C8 C2 N7 C4 -132.4(6) . . . . ? C1 C2 N7 C4 99.3(6) . . . . ? N7 C3 N8 C5 0.1(5) . . . . ? N7 C3 N8 C6 176.0(4) . . . . ? C4 C5 N8 C3 -0.3(6) . . . . ? C4 C5 N8 C6 -175.9(4) . . . . ? C9 C6 N8 C3 173.0(5) . . . . ? C7 C6 N8 C3 -58.5(6) . . . . ? C9 C6 N8 C5 -11.9(7) . . . . ? C7 C6 N8 C5 116.6(5) . . . . ? O2 C1 O1 Mn1 17.5(6) . . . . ? C2 C1 O1 Mn1 -165.5(3) . . . . ? O3 Mn1 O1 C1 -58.9(3) 1_455 . . . ? O5 Mn1 O1 C1 118.4(4) . . . . ? N6 Mn1 O1 C1 -147.6(4) 4_565 . . . ? N1 Mn1 O1 C1 30.4(3) . . . . ? N4 Mn1 O1 C1 133.1(8) . . . . ? O1 C1 O2 Mn2 -50.0(6) . . . . ? C2 C1 O2 Mn2 133.1(4) . . . . ? O2 Mn2 O2 C1 32(62) 3_557 . . . ? O4 Mn2 O2 C1 -75.7(4) 3_657 . . . ? O4 Mn2 O2 C1 104.3(4) 1_455 . . . ? N1 Mn2 O2 C1 -165.8(4) 3_557 . . . ? N1 Mn2 O2 C1 14.2(4) . . . . ? O4 C7 O3 Mn1 -16.7(8) . . . 1_655 ? C6 C7 O3 Mn1 160.6(3) . . . 1_655 ? O3 C7 O4 Mn2 -2.4(7) . . . 1_655 ? C6 C7 O4 Mn2 -179.8(3) . . . 1_655 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.814 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 925292'