# 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_2 _database_code_depnum_ccdc_archive 'CCDC 890438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Mn N8 O6' _chemical_formula_weight 475.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4755(4) _cell_length_b 9.7344(7) _cell_length_c 10.4118(7) _cell_angle_alpha 66.600(2) _cell_angle_beta 76.852(2) _cell_angle_gamma 83.026(2) _cell_volume 495.66(6) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5207 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 245 _exptl_absorpt_coefficient_mu 0.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8997 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details ? _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 6215 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1919 _reflns_number_gt 1842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.1580P] 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 1919 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 0.5000 0.0000 0.5000 0.02709(13) Uani 1 2 d S . . O1 O 0.7089(2) 0.09175(16) 0.28603(12) 0.0412(3) Uani 1 1 d . . . O2 O 0.4654(2) 0.06270(17) 0.15319(14) 0.0475(4) Uani 1 1 d . . . O3 O 0.2407(2) -0.09509(14) 0.42463(13) 0.0373(3) Uani 1 1 d . . . H1 H 0.2664 -0.0405 0.3322 0.056 Uiso 1 1 d R . . H2 H 0.0792 -0.1199 0.4606 0.056 Uiso 1 1 d R . . N1 N 0.7500(3) -0.20759(18) 0.54345(17) 0.0405(4) Uani 1 1 d . . . N2 N 0.7392(3) -0.30920(18) 0.65557(18) 0.0431(4) Uani 1 1 d . . . N3 N 0.7296(5) -0.4097(2) 0.7641(2) 0.0753(7) Uani 1 1 d . . . N4 N 1.2247(2) 0.30549(14) -0.19153(14) 0.0285(3) Uani 1 1 d . . . C1 C 0.6521(3) 0.10871(18) 0.17040(17) 0.0305(3) Uani 1 1 d . . . C2 C 0.8439(3) 0.18910(17) 0.03782(16) 0.0274(3) Uani 1 1 d . . . C3 C 1.0149(3) 0.28143(19) 0.04033(17) 0.0328(4) Uani 1 1 d . . . H3A H 1.0021 0.3039 0.1205 0.039 Uiso 1 1 calc R . . C4 C 1.2035(3) 0.33950(19) -0.07625(18) 0.0330(4) Uani 1 1 d . . . H4A H 1.3171 0.4027 -0.0754 0.040 Uiso 1 1 calc R . . C5 C 1.0550(3) 0.22123(18) -0.19893(16) 0.0315(3) Uani 1 1 d . . . H5A H 1.0688 0.2027 -0.2813 0.038 Uiso 1 1 calc R . . C6 C 0.8615(3) 0.16245(18) -0.08549(17) 0.0309(3) Uani 1 1 d . . . H6A H 0.7433 0.1052 -0.0912 0.037 Uiso 1 1 calc R . . C7 C 1.4442(3) 0.35429(19) -0.31076(17) 0.0346(4) Uani 1 1 d . . . H7A H 1.5095 0.2705 -0.3380 0.041 Uiso 1 1 calc R . . H7B H 1.5749 0.3826 -0.2777 0.041 Uiso 1 1 calc R . . C8 C 1.3836(3) 0.48402(19) -0.44001(17) 0.0327(4) Uani 1 1 d . . . H8A H 1.3342 0.5719 -0.4168 0.039 Uiso 1 1 calc R . . H8B H 1.2454 0.4599 -0.4705 0.039 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 0.02433(19) 0.0368(2) 0.01762(19) -0.00902(14) 0.00126(12) -0.00702(13) O1 0.0360(6) 0.0631(8) 0.0186(6) -0.0103(5) 0.0032(5) -0.0153(6) O2 0.0385(7) 0.0713(9) 0.0294(7) -0.0148(6) 0.0022(5) -0.0233(6) O3 0.0311(6) 0.0472(7) 0.0323(6) -0.0138(5) -0.0011(5) -0.0119(5) N1 0.0350(8) 0.0427(8) 0.0393(9) -0.0126(7) -0.0038(6) -0.0033(6) N2 0.0478(9) 0.0409(9) 0.0469(10) -0.0173(8) -0.0170(7) -0.0084(7) N3 0.119(2) 0.0478(11) 0.0590(13) 0.0001(10) -0.0459(13) -0.0210(11) N4 0.0298(7) 0.0292(6) 0.0193(6) -0.0040(5) 0.0011(5) -0.0048(5) C1 0.0293(8) 0.0360(8) 0.0210(8) -0.0083(6) 0.0014(6) -0.0040(6) C2 0.0285(7) 0.0288(7) 0.0192(7) -0.0045(6) -0.0021(6) -0.0017(6) C3 0.0381(9) 0.0392(9) 0.0215(8) -0.0124(7) -0.0025(6) -0.0064(7) C4 0.0366(9) 0.0351(8) 0.0266(8) -0.0098(7) -0.0034(7) -0.0104(7) C5 0.0393(9) 0.0346(8) 0.0189(7) -0.0091(6) -0.0016(6) -0.0065(7) C6 0.0343(8) 0.0338(8) 0.0226(8) -0.0076(6) -0.0033(6) -0.0088(6) C7 0.0293(8) 0.0391(9) 0.0243(8) -0.0052(7) 0.0051(6) -0.0048(6) C8 0.0309(8) 0.0373(8) 0.0231(8) -0.0075(7) 0.0033(7) -0.0065(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 2.1394(12) . ? Mn1 O1 2.1394(12) 2_656 ? Mn1 O3 2.2117(12) 2_656 ? Mn1 O3 2.2117(12) . ? Mn1 N1 2.2462(16) 2_656 ? Mn1 N1 2.2462(16) . ? O1 C1 1.254(2) . ? O2 C1 1.239(2) . ? O3 H1 0.8822 . ? O3 H2 0.9002 . ? N1 N2 1.188(2) . ? N2 N3 1.159(3) . ? N4 C4 1.344(2) . ? N4 C5 1.345(2) . ? N4 C7 1.484(2) . ? C1 C2 1.517(2) . ? C2 C3 1.386(2) . ? C2 C6 1.388(2) . ? C3 C4 1.373(2) . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 C6 1.373(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.506(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.531(3) 2_864 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O1 180.0 . 2_656 ? O1 Mn1 O3 90.86(5) . 2_656 ? O1 Mn1 O3 89.14(5) 2_656 2_656 ? O1 Mn1 O3 89.14(5) . . ? O1 Mn1 O3 90.86(5) 2_656 . ? O3 Mn1 O3 180.00(5) 2_656 . ? O1 Mn1 N1 89.92(6) . 2_656 ? O1 Mn1 N1 90.08(6) 2_656 2_656 ? O3 Mn1 N1 91.85(5) 2_656 2_656 ? O3 Mn1 N1 88.15(5) . 2_656 ? O1 Mn1 N1 90.08(6) . . ? O1 Mn1 N1 89.92(6) 2_656 . ? O3 Mn1 N1 88.15(5) 2_656 . ? O3 Mn1 N1 91.85(5) . . ? N1 Mn1 N1 180.000(1) 2_656 . ? C1 O1 Mn1 130.27(11) . . ? Mn1 O3 H1 102.7 . . ? Mn1 O3 H2 130.8 . . ? H1 O3 H2 112.0 . . ? N2 N1 Mn1 125.24(13) . . ? N3 N2 N1 179.1(2) . . ? C4 N4 C5 121.12(13) . . ? C4 N4 C7 120.31(14) . . ? C5 N4 C7 118.51(14) . . ? O2 C1 O1 127.72(15) . . ? O2 C1 C2 117.31(14) . . ? O1 C1 C2 114.90(14) . . ? C3 C2 C6 118.87(14) . . ? C3 C2 C1 120.97(14) . . ? C6 C2 C1 120.00(14) . . ? C4 C3 C2 119.62(15) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? N4 C4 C3 120.35(14) . . ? N4 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N4 C5 C6 120.38(14) . . ? N4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C2 119.49(14) . . ? C5 C6 H6A 120.3 . . ? C2 C6 H6A 120.3 . . ? N4 C7 C8 113.36(14) . . ? N4 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N4 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C8 108.87(17) . 2_864 ? C7 C8 H8A 109.9 . . ? C8 C8 H8A 109.9 2_864 . ? C7 C8 H8B 109.9 . . ? C8 C8 H8B 109.9 2_864 . ? H8A C8 H8B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 O1 C1 -170(100) 2_656 . . . ? O3 Mn1 O1 C1 -165.41(16) 2_656 . . . ? O3 Mn1 O1 C1 14.59(16) . . . . ? N1 Mn1 O1 C1 -73.56(16) 2_656 . . . ? N1 Mn1 O1 C1 106.44(16) . . . . ? O1 Mn1 N1 N2 176.09(15) . . . . ? O1 Mn1 N1 N2 -3.91(15) 2_656 . . . ? O3 Mn1 N1 N2 85.23(15) 2_656 . . . ? O3 Mn1 N1 N2 -94.77(15) . . . . ? N1 Mn1 N1 N2 19(100) 2_656 . . . ? Mn1 N1 N2 N3 145(13) . . . . ? Mn1 O1 C1 O2 -7.3(3) . . . . ? Mn1 O1 C1 C2 175.77(10) . . . . ? O2 C1 C2 C3 160.68(17) . . . . ? O1 C1 C2 C3 -22.1(2) . . . . ? O2 C1 C2 C6 -23.9(2) . . . . ? O1 C1 C2 C6 153.32(16) . . . . ? C6 C2 C3 C4 -2.6(2) . . . . ? C1 C2 C3 C4 172.86(15) . . . . ? C5 N4 C4 C3 3.8(2) . . . . ? C7 N4 C4 C3 -173.19(15) . . . . ? C2 C3 C4 N4 -1.0(3) . . . . ? C4 N4 C5 C6 -2.9(2) . . . . ? C7 N4 C5 C6 174.12(15) . . . . ? N4 C5 C6 C2 -0.8(2) . . . . ? C3 C2 C6 C5 3.5(2) . . . . ? C1 C2 C6 C5 -172.05(15) . . . . ? C4 N4 C7 C8 -104.99(18) . . . . ? C5 N4 C7 C8 77.99(19) . . . . ? N4 C7 C8 C8 -175.20(16) . . . 2_864 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.212 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.053 data_2 _database_code_depnum_ccdc_archive 'CCDC 911378' #TrackingRef 'OCN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Mn N4 O8' _chemical_formula_weight 475.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.453(3) _cell_length_b 9.807(5) _cell_length_c 10.363(5) _cell_angle_alpha 66.809(5) _cell_angle_beta 77.466(5) _cell_angle_gamma 83.677(6) _cell_volume 497.1(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.28 _exptl_crystal_description rectangular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 245 _exptl_absorpt_coefficient_mu 0.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9186 _exptl_absorpt_correction_T_max 0.9649 _exptl_absorpt_process_details 'SADABS (Bruker, 2007)' _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 2574 _diffrn_reflns_av_R_equivalents 0.0088 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1720 _reflns_number_gt 1618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.2065P] 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 1720 _refine_ls_number_parameters 148 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0670 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.5000 0.0000 0.5000 0.02898(13) Uani 1 2 d S . . O1 O 0.7178(2) 0.08743(16) 0.28506(12) 0.0440(3) Uani 1 1 d . . . O2 O 0.4658(3) 0.06548(18) 0.15091(14) 0.0522(4) Uani 1 1 d . . . O3 O 0.2383(2) -0.09601(15) 0.42295(14) 0.0393(3) Uani 1 1 d D . . H1 H 0.252(4) -0.040(2) 0.3365(17) 0.059 Uiso 1 1 d D . . H2 H 0.093(3) -0.118(3) 0.463(2) 0.059 Uiso 1 1 d D . . N1 N 0.7421(3) -0.20587(18) 0.55195(18) 0.0428(4) Uani 1 1 d . . . C9 C 0.7399(4) -0.3093(2) 0.6580(2) 0.0482(5) Uani 1 1 d . . . O4 O 0.7401(5) -0.4174(2) 0.7663(2) 0.0960(8) Uani 1 1 d . . . N4 N 1.2299(3) 0.30409(15) -0.19206(14) 0.0314(3) Uani 1 1 d . . . C1 C 0.6569(3) 0.1073(2) 0.16922(18) 0.0337(4) Uani 1 1 d . . . C2 C 0.8494(3) 0.18770(19) 0.03663(17) 0.0299(4) Uani 1 1 d . . . C3 C 1.0196(3) 0.2804(2) 0.03921(18) 0.0355(4) Uani 1 1 d . . . H3A H 1.0066 0.3032 0.1195 0.043 Uiso 1 1 calc R . . C4 C 1.2081(3) 0.3389(2) -0.07701(18) 0.0361(4) Uani 1 1 d . . . H4A H 1.3211 0.4028 -0.0760 0.043 Uiso 1 1 calc R . . C5 C 1.0608(3) 0.2186(2) -0.19918(18) 0.0347(4) Uani 1 1 d . . . H5A H 1.0755 0.1989 -0.2813 0.042 Uiso 1 1 calc R . . C6 C 0.8674(3) 0.16038(19) -0.08673(17) 0.0333(4) Uani 1 1 d . . . H6A H 0.7489 0.1030 -0.0929 0.040 Uiso 1 1 calc R . . C7 C 1.4490(3) 0.3544(2) -0.31126(18) 0.0372(4) Uani 1 1 d . . . H7A H 1.5146 0.2722 -0.3396 0.045 Uiso 1 1 calc R . . H7B H 1.5802 0.3832 -0.2778 0.045 Uiso 1 1 calc R . . C8 C 1.3846(3) 0.48321(19) -0.43966(17) 0.0335(4) Uani 1 1 d . . . H8A H 1.3357 0.5696 -0.4154 0.040 Uiso 1 1 calc R . . H8B H 1.2449 0.4587 -0.4700 0.040 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 0.0254(2) 0.0378(2) 0.02096(19) -0.00948(15) 0.00103(13) -0.00680(14) O1 0.0388(7) 0.0667(9) 0.0201(6) -0.0103(6) 0.0021(5) -0.0147(6) O2 0.0399(8) 0.0793(11) 0.0340(7) -0.0163(7) 0.0008(6) -0.0236(7) O3 0.0326(7) 0.0479(8) 0.0357(7) -0.0141(6) -0.0019(6) -0.0108(6) N1 0.0370(9) 0.0428(9) 0.0463(10) -0.0151(8) -0.0058(7) -0.0029(7) C9 0.0545(13) 0.0448(12) 0.0521(13) -0.0185(11) -0.0193(10) -0.0107(9) O4 0.160(2) 0.0553(11) 0.0717(13) 0.0051(10) -0.0619(13) -0.0313(12) N4 0.0324(8) 0.0320(7) 0.0226(7) -0.0048(6) -0.0001(6) -0.0042(6) C1 0.0321(9) 0.0380(10) 0.0254(9) -0.0088(7) 0.0005(7) -0.0028(7) C2 0.0299(9) 0.0324(9) 0.0226(8) -0.0063(7) -0.0029(7) -0.0013(7) C3 0.0413(10) 0.0425(10) 0.0239(8) -0.0141(8) -0.0029(7) -0.0065(8) C4 0.0393(10) 0.0385(10) 0.0296(9) -0.0107(8) -0.0040(7) -0.0110(8) C5 0.0427(10) 0.0378(9) 0.0221(8) -0.0103(7) -0.0023(7) -0.0070(8) C6 0.0363(9) 0.0360(9) 0.0251(8) -0.0079(7) -0.0045(7) -0.0083(7) C7 0.0314(9) 0.0419(10) 0.0271(9) -0.0054(8) 0.0041(7) -0.0051(8) C8 0.0319(9) 0.0355(9) 0.0259(8) -0.0071(7) 0.0024(7) -0.0055(7) _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 2.1632(14) . ? Mn1 O1 2.1632(14) 2_656 ? Mn1 O3 2.2232(14) 2_656 ? Mn1 O3 2.2232(14) . ? Mn1 N1 2.2304(19) . ? Mn1 N1 2.2304(19) 2_656 ? O1 C1 1.250(2) . ? O2 C1 1.238(2) . ? O3 H1 0.837(15) . ? O3 H2 0.822(15) . ? N1 C9 1.164(3) . ? C9 O4 1.203(3) . ? N4 C4 1.342(2) . ? N4 C5 1.344(2) . ? N4 C7 1.485(2) . ? C1 C2 1.521(2) . ? C2 C3 1.380(3) . ? C2 C6 1.388(2) . ? C3 C4 1.373(2) . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 C6 1.368(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.507(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.530(3) 2_864 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O1 180.0 . 2_656 ? O1 Mn1 O3 90.70(6) . 2_656 ? O1 Mn1 O3 89.30(6) 2_656 2_656 ? O1 Mn1 O3 89.30(6) . . ? O1 Mn1 O3 90.70(6) 2_656 . ? O3 Mn1 O3 180.00(6) 2_656 . ? O1 Mn1 N1 90.57(6) . . ? O1 Mn1 N1 89.43(6) 2_656 . ? O3 Mn1 N1 87.78(7) 2_656 . ? O3 Mn1 N1 92.22(7) . . ? O1 Mn1 N1 89.43(6) . 2_656 ? O1 Mn1 N1 90.57(6) 2_656 2_656 ? O3 Mn1 N1 92.22(7) 2_656 2_656 ? O3 Mn1 N1 87.78(7) . 2_656 ? N1 Mn1 N1 180.0 . 2_656 ? C1 O1 Mn1 129.36(12) . . ? Mn1 O3 H1 103.4(16) . . ? Mn1 O3 H2 124.5(16) . . ? H1 O3 H2 113(2) . . ? C9 N1 Mn1 131.00(16) . . ? N1 C9 O4 179.0(3) . . ? C4 N4 C5 120.97(14) . . ? C4 N4 C7 120.14(15) . . ? C5 N4 C7 118.83(15) . . ? O2 C1 O1 127.91(16) . . ? O2 C1 C2 117.32(15) . . ? O1 C1 C2 114.72(16) . . ? C3 C2 C6 118.78(15) . . ? C3 C2 C1 121.14(15) . . ? C6 C2 C1 119.93(15) . . ? C4 C3 C2 119.86(16) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? N4 C4 C3 120.18(16) . . ? N4 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? N4 C5 C6 120.61(16) . . ? N4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C2 119.44(16) . . ? C5 C6 H6A 120.3 . . ? C2 C6 H6A 120.3 . . ? N4 C7 C8 112.88(14) . . ? N4 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N4 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C8 108.66(18) . 2_864 ? C7 C8 H8A 110.0 . . ? C8 C8 H8A 110.0 2_864 . ? C7 C8 H8B 110.0 . . ? C8 C8 H8B 110.0 2_864 . ? H8A C8 H8B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 O1 C1 -111(100) 2_656 . . . ? O3 Mn1 O1 C1 -161.99(17) 2_656 . . . ? O3 Mn1 O1 C1 18.01(17) . . . . ? N1 Mn1 O1 C1 110.22(17) . . . . ? N1 Mn1 O1 C1 -69.78(17) 2_656 . . . ? O1 Mn1 N1 C9 177.60(19) . . . . ? O1 Mn1 N1 C9 -2.40(19) 2_656 . . . ? O3 Mn1 N1 C9 86.93(19) 2_656 . . . ? O3 Mn1 N1 C9 -93.07(19) . . . . ? N1 Mn1 N1 C9 46(100) 2_656 . . . ? Mn1 N1 C9 O4 167(13) . . . . ? Mn1 O1 C1 O2 -9.2(3) . . . . ? Mn1 O1 C1 C2 173.35(11) . . . . ? O2 C1 C2 C3 157.81(18) . . . . ? O1 C1 C2 C3 -24.5(2) . . . . ? O2 C1 C2 C6 -26.7(3) . . . . ? O1 C1 C2 C6 151.02(17) . . . . ? C6 C2 C3 C4 -2.6(3) . . . . ? C1 C2 C3 C4 173.01(17) . . . . ? C5 N4 C4 C3 3.7(3) . . . . ? C7 N4 C4 C3 -173.55(17) . . . . ? C2 C3 C4 N4 -1.1(3) . . . . ? C4 N4 C5 C6 -2.5(3) . . . . ? C7 N4 C5 C6 174.82(16) . . . . ? N4 C5 C6 C2 -1.3(3) . . . . ? C3 C2 C6 C5 3.8(3) . . . . ? C1 C2 C6 C5 -171.86(16) . . . . ? C4 N4 C7 C8 -104.0(2) . . . . ? C5 N4 C7 C8 78.7(2) . . . . ? N4 C7 C8 C8 -174.83(17) . . . 2_864 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1 O2 0.837(15) 1.965(16) 2.719(2) 149(2) . O3 H2 N1 0.822(15) 2.054(16) 2.865(2) 169(2) 1_455 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.185 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.048 data_3 _database_code_depnum_ccdc_archive 'CCDC 911379' #TrackingRef 'SCN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Mn N4 O6 S2' _chemical_formula_weight 507.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 5.5469(18) _cell_length_b 10.583(3) _cell_length_c 12.227(3) _cell_angle_alpha 53.692(17) _cell_angle_beta 69.966(11) _cell_angle_gamma 81.833(9) _cell_volume 541.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3821 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 28.28 _exptl_crystal_description rectangular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 261 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8492 _exptl_absorpt_correction_T_max 0.9590 _exptl_absorpt_process_details 'SADABS (Bruker, 2007)' _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 5048 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1904 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.2720P] 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 1904 _refine_ls_number_parameters 148 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.135 _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 0.5000 0.5000 0.5000 0.02782(14) Uani 1 2 d SU . . C1 C 0.3253(4) 0.2601(2) 0.83116(19) 0.0298(4) Uani 1 1 d . . . C2 C 0.3818(3) 0.2034(2) 0.96629(18) 0.0272(4) Uani 1 1 d . . . C3 C 0.5528(4) 0.2901(2) 0.9622(2) 0.0348(4) Uani 1 1 d . . . H3A H 0.6218 0.3891 0.8788 0.042 Uiso 1 1 calc R . . C4 C 0.6212(4) 0.2297(2) 1.0819(2) 0.0354(4) Uani 1 1 d . . . H4A H 0.7343 0.2890 1.0795 0.042 Uiso 1 1 calc R . . C5 C 0.3511(4) 0.0013(2) 1.2103(2) 0.0325(4) Uani 1 1 d . . . H5A H 0.2827 -0.0967 1.2954 0.039 Uiso 1 1 calc R . . C6 C 0.2729(4) 0.0581(2) 1.09468(19) 0.0307(4) Uani 1 1 d . . . H6A H 0.1491 0.0006 1.1019 0.037 Uiso 1 1 calc R . . C7 C 0.6189(4) 0.0161(3) 1.3262(2) 0.0353(4) Uani 1 1 d . . . H7A H 0.7897 0.0641 1.2915 0.042 Uiso 1 1 calc R . . H7B H 0.6326 -0.0955 1.3704 0.042 Uiso 1 1 calc R . . C8 C 0.4453(4) 0.0386(2) 1.43807(19) 0.0335(4) Uani 1 1 d . . . H8B H 0.2736 -0.0089 1.4737 0.040 Uiso 1 1 calc R . . H8C H 0.4339 0.1499 1.3960 0.040 Uiso 1 1 calc R . . C9 C 0.8833(4) 0.3579(2) 0.3426(2) 0.0334(4) Uani 1 1 d U . . O1 O 0.4998(3) 0.35426(16) 0.71602(13) 0.0365(3) Uani 1 1 d . . . O2 O 0.1238(3) 0.20695(19) 0.84511(15) 0.0475(4) Uani 1 1 d . . . O3 O 0.1687(3) 0.34575(19) 0.57021(17) 0.0420(4) Uani 1 1 d . . . H1 H 0.096(6) 0.299(3) 0.656(3) 0.063 Uiso 1 1 d . . . H2 H 0.065(6) 0.369(3) 0.530(3) 0.063 Uiso 1 1 d . . . N1 N 0.7843(4) 0.3525(2) 0.44625(19) 0.0429(4) Uani 1 1 d U . . N4 N 0.5254(3) 0.08554(18) 1.20222(15) 0.0294(3) Uani 1 1 d . . . S1 S 1.02282(13) 0.36578(8) 0.19786(7) 0.0569(2) Uani 1 1 d U . . 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 0.0316(2) 0.0302(2) 0.0176(2) -0.01058(17) -0.00959(16) 0.00016(16) C1 0.0362(10) 0.0290(9) 0.0219(9) -0.0125(8) -0.0120(8) 0.0028(8) C2 0.0315(9) 0.0300(9) 0.0192(8) -0.0143(8) -0.0077(7) 0.0028(7) C3 0.0422(11) 0.0311(10) 0.0220(9) -0.0098(8) -0.0088(8) -0.0063(8) C4 0.0414(11) 0.0378(11) 0.0269(10) -0.0170(9) -0.0106(8) -0.0078(8) C5 0.0417(10) 0.0282(9) 0.0204(9) -0.0106(8) -0.0073(8) -0.0032(8) C6 0.0371(10) 0.0324(10) 0.0205(9) -0.0139(8) -0.0078(8) -0.0040(8) C7 0.0425(11) 0.0434(11) 0.0233(9) -0.0189(9) -0.0173(8) 0.0083(9) C8 0.0395(10) 0.0377(10) 0.0247(10) -0.0170(8) -0.0152(8) 0.0050(8) C9 0.0355(10) 0.0322(10) 0.0330(9) -0.0186(9) -0.0113(8) -0.0005(8) O1 0.0391(7) 0.0426(8) 0.0178(6) -0.0107(6) -0.0095(6) -0.0048(6) O2 0.0483(9) 0.0556(9) 0.0297(8) -0.0151(7) -0.0156(7) -0.0145(7) O3 0.0416(8) 0.0486(9) 0.0341(8) -0.0192(7) -0.0174(7) -0.0046(7) N1 0.0479(10) 0.0446(10) 0.0378(10) -0.0261(8) -0.0126(8) 0.0065(8) N4 0.0362(8) 0.0337(8) 0.0199(7) -0.0161(7) -0.0104(6) 0.0039(7) S1 0.0648(4) 0.0679(4) 0.0425(3) -0.0398(3) 0.0029(3) -0.0196(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 O1 2.1283(14) 2_666 ? Mn1 O1 2.1283(14) . ? Mn1 O3 2.2112(17) . ? Mn1 O3 2.2112(17) 2_666 ? Mn1 N1 2.2721(19) . ? Mn1 N1 2.2721(19) 2_666 ? C1 O2 1.236(2) . ? C1 O1 1.261(2) . ? C1 C2 1.522(2) . ? C2 C3 1.381(3) . ? C2 C6 1.396(3) . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 N4 1.346(3) . ? C4 H4A 0.9300 . ? C5 N4 1.347(3) . ? C5 C6 1.374(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 N4 1.490(2) . ? C7 C8 1.507(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.534(3) 2_658 ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 N1 1.165(3) . ? C9 S1 1.626(2) . ? O3 H1 0.81(3) . ? O3 H2 0.80(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 O1 Mn1 O1 180.000(1) 2_666 . ? O1 Mn1 O3 92.32(6) 2_666 . ? O1 Mn1 O3 87.68(6) . . ? O1 Mn1 O3 87.68(6) 2_666 2_666 ? O1 Mn1 O3 92.32(6) . 2_666 ? O3 Mn1 O3 180.00(10) . 2_666 ? O1 Mn1 N1 88.94(6) 2_666 . ? O1 Mn1 N1 91.06(6) . . ? O3 Mn1 N1 91.73(7) . . ? O3 Mn1 N1 88.27(7) 2_666 . ? O1 Mn1 N1 91.06(6) 2_666 2_666 ? O1 Mn1 N1 88.94(6) . 2_666 ? O3 Mn1 N1 88.27(7) . 2_666 ? O3 Mn1 N1 91.73(7) 2_666 2_666 ? N1 Mn1 N1 180.000(1) . 2_666 ? O2 C1 O1 127.66(17) . . ? O2 C1 C2 118.09(16) . . ? O1 C1 C2 114.21(16) . . ? C3 C2 C6 118.80(17) . . ? C3 C2 C1 120.67(16) . . ? C6 C2 C1 120.42(17) . . ? C4 C3 C2 119.86(18) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? N4 C4 C3 120.45(18) . . ? N4 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N4 C5 C6 120.91(17) . . ? N4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C2 119.14(18) . . ? C5 C6 H6A 120.4 . . ? C2 C6 H6A 120.4 . . ? N4 C7 C8 113.04(15) . . ? N4 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N4 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C8 109.2(2) . 2_658 ? C7 C8 H8B 109.8 . . ? C8 C8 H8B 109.8 2_658 . ? C7 C8 H8C 109.8 . . ? C8 C8 H8C 109.8 2_658 . ? H8B C8 H8C 108.3 . . ? N1 C9 S1 179.7(2) . . ? C1 O1 Mn1 130.64(12) . . ? Mn1 O3 H1 110(2) . . ? Mn1 O3 H2 126(2) . . ? H1 O3 H2 110(3) . . ? C9 N1 Mn1 134.08(16) . . ? C4 N4 C5 120.67(15) . . ? C4 N4 C7 119.77(16) . . ? C5 N4 C7 119.53(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -159.46(19) . . . . ? O1 C1 C2 C3 22.8(3) . . . . ? O2 C1 C2 C6 24.3(3) . . . . ? O1 C1 C2 C6 -153.39(18) . . . . ? C6 C2 C3 C4 2.7(3) . . . . ? C1 C2 C3 C4 -173.55(18) . . . . ? C2 C3 C4 N4 1.0(3) . . . . ? N4 C5 C6 C2 1.7(3) . . . . ? C3 C2 C6 C5 -4.1(3) . . . . ? C1 C2 C6 C5 172.21(17) . . . . ? N4 C7 C8 C8 179.2(2) . . . 2_658 ? O2 C1 O1 Mn1 14.7(3) . . . . ? C2 C1 O1 Mn1 -167.88(12) . . . . ? O1 Mn1 O1 C1 126(100) 2_666 . . . ? O3 Mn1 O1 C1 -20.04(18) . . . . ? O3 Mn1 O1 C1 159.96(18) 2_666 . . . ? N1 Mn1 O1 C1 -111.73(18) . . . . ? N1 Mn1 O1 C1 68.27(18) 2_666 . . . ? S1 C9 N1 Mn1 106(47) . . . . ? O1 Mn1 N1 C9 -0.3(2) 2_666 . . . ? O1 Mn1 N1 C9 179.7(2) . . . . ? O3 Mn1 N1 C9 92.0(2) . . . . ? O3 Mn1 N1 C9 -88.0(2) 2_666 . . . ? N1 Mn1 N1 C9 -85(100) 2_666 . . . ? C3 C4 N4 C5 -3.5(3) . . . . ? C3 C4 N4 C7 174.58(18) . . . . ? C6 C5 N4 C4 2.1(3) . . . . ? C6 C5 N4 C7 -175.99(17) . . . . ? C8 C7 N4 C4 96.9(2) . . . . ? C8 C7 N4 C5 -85.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1 O2 0.81(3) 1.96(3) 2.683(2) 148(3) . O3 H2 N1 0.80(3) 2.21(3) 2.982(2) 162(3) 1_455 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.377 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.058