# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kil Sik Min ' _publ_contact_author_email minks@knu.ac.kr _publ_author_name 'Kil Sik Min' # Attachment 'Fe4.cif' data_Fe4 _database_code_depnum_ccdc_archive 'CCDC 749014' #TrackingRef 'Fe4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Fe2 N15 O2' _chemical_formula_weight 553.15 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.780(4) _cell_length_b 13.921(4) _cell_length_c 22.471(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4311(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4184 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 23.99 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 1.396 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 30470 _diffrn_reflns_av_R_equivalents 0.1362 _diffrn_reflns_av_sigmaI/netI 0.1487 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.37 _reflns_number_total 5362 _reflns_number_gt 2317 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5362 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1369 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _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 Fe1 Fe 0.49505(4) 0.20528(4) 0.36485(3) 0.02293(17) Uani 1 1 d . . . Fe2 Fe 0.51578(4) 0.12153(5) 0.49612(3) 0.02597(18) Uani 1 1 d . . . N1 N 0.5642(2) 0.0993(3) 0.31036(16) 0.0249(9) Uani 1 1 d . . . N2 N 0.6230(2) 0.2789(2) 0.32644(15) 0.0241(9) Uani 1 1 d . . . N3 N 0.4707(2) 0.3489(2) 0.39162(16) 0.0253(9) Uani 1 1 d . . . C1 C 0.5474(3) 0.0047(3) 0.3136(2) 0.0292(12) Uani 1 1 d . . . H1 H 0.5064 -0.0190 0.3443 0.035 Uiso 1 1 calc R . . C2 C 0.5877(3) -0.0598(3) 0.2739(2) 0.0359(12) Uani 1 1 d . . . H2 H 0.5756 -0.1267 0.2776 0.043 Uiso 1 1 calc R . . C3 C 0.6446(3) -0.0258(4) 0.2296(2) 0.0423(14) Uani 1 1 d . . . H3 H 0.6732 -0.0688 0.2018 0.051 Uiso 1 1 calc R . . C4 C 0.6611(3) 0.0723(4) 0.2249(2) 0.0388(13) Uani 1 1 d . . . H4 H 0.6993 0.0973 0.1933 0.047 Uiso 1 1 calc R . . C5 C 0.6216(3) 0.1325(3) 0.2664(2) 0.0277(11) Uani 1 1 d . . . C6 C 0.6369(3) 0.2386(3) 0.2658(2) 0.0311(12) Uani 1 1 d . . . H6A H 0.7034 0.2530 0.2517 0.037 Uiso 1 1 calc R . . H6B H 0.5904 0.2688 0.2379 0.037 Uiso 1 1 calc R . . C7 C 0.6070(3) 0.3838(3) 0.3254(2) 0.0284(11) Uani 1 1 d . . . H7A H 0.5837 0.4029 0.2855 0.034 Uiso 1 1 calc R . . H7B H 0.6694 0.4169 0.3328 0.034 Uiso 1 1 calc R . . C8 C 0.5341(3) 0.4153(3) 0.3715(2) 0.0266(11) Uani 1 1 d . . . C9 C 0.5267(3) 0.5092(3) 0.3905(2) 0.0347(12) Uani 1 1 d . . . H9 H 0.5716 0.5561 0.3768 0.042 Uiso 1 1 calc R . . C10 C 0.4536(3) 0.5349(4) 0.4297(2) 0.0415(13) Uani 1 1 d . . . H10 H 0.4477 0.5996 0.4426 0.050 Uiso 1 1 calc R . . C11 C 0.3888(3) 0.4659(4) 0.4501(2) 0.0367(13) Uani 1 1 d . . . H11 H 0.3383 0.4819 0.4771 0.044 Uiso 1 1 calc R . . C12 C 0.4005(3) 0.3744(3) 0.4298(2) 0.0308(11) Uani 1 1 d . . . H12 H 0.3568 0.3263 0.4434 0.037 Uiso 1 1 calc R . . C13 C 0.7055(3) 0.2513(3) 0.3665(2) 0.0287(11) Uani 1 1 d . . . H13A H 0.7584 0.2990 0.3624 0.034 Uiso 1 1 calc R . . H13B H 0.7312 0.1879 0.3542 0.034 Uiso 1 1 calc R . . C14 C 0.6728(3) 0.2467(3) 0.43118(19) 0.0286(11) Uani 1 1 d . . . H14A H 0.7241 0.2173 0.4561 0.034 Uiso 1 1 calc R . . H14B H 0.6594 0.3121 0.4464 0.034 Uiso 1 1 calc R . . C15 C 0.3191(3) 0.1229(3) 0.4265(2) 0.0349(12) Uani 1 1 d . . . H15A H 0.2885 0.1608 0.3949 0.052 Uiso 1 1 calc R . . H15B H 0.2951 0.1446 0.4653 0.052 Uiso 1 1 calc R . . H15C H 0.3033 0.0549 0.4211 0.052 Uiso 1 1 calc R . . O1 O 0.58761(18) 0.1903(2) 0.43286(13) 0.0252(7) Uani 1 1 d . . . O2 O 0.42135(18) 0.13524(19) 0.42401(12) 0.0243(7) Uani 1 1 d . . . N4 N 0.4337(2) 0.0141(2) 0.53821(16) 0.0252(9) Uani 1 1 d . . . N5 N 0.3522(3) 0.0192(3) 0.55839(17) 0.0324(10) Uani 1 1 d . . . N6 N 0.2761(3) 0.0208(3) 0.5777(2) 0.0549(13) Uani 1 1 d . . . N7 N 0.6319(3) 0.1301(3) 0.54904(18) 0.0417(11) Uani 1 1 d . . . N8 N 0.6490(3) 0.1224(3) 0.5995(2) 0.0472(12) Uani 1 1 d . . . N9 N 0.6690(3) 0.1098(4) 0.6503(2) 0.0829(19) Uani 1 1 d . . . N10 N 0.4406(3) 0.2246(3) 0.53925(19) 0.0360(10) Uani 1 1 d . . . N11 N 0.4558(3) 0.2377(3) 0.5910(2) 0.0398(11) Uani 1 1 d . . . N12 N 0.4692(4) 0.2520(4) 0.6421(2) 0.0600(14) Uani 1 1 d . . . N13 N 0.3973(2) 0.2201(3) 0.29944(17) 0.0270(9) Uani 1 1 d . . . N14 N 0.3823(2) 0.1615(3) 0.26172(19) 0.0329(10) Uani 1 1 d . . . N15 N 0.3654(3) 0.1046(3) 0.2259(2) 0.0512(13) 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 Fe1 0.0210(3) 0.0216(3) 0.0262(4) 0.0012(3) 0.0002(3) -0.0003(3) Fe2 0.0271(3) 0.0240(4) 0.0269(4) 0.0013(3) 0.0002(3) 0.0004(3) N1 0.0224(19) 0.025(2) 0.027(2) -0.0024(18) -0.0023(17) 0.0010(16) N2 0.0192(19) 0.024(2) 0.029(2) 0.0017(18) 0.0027(16) -0.0012(15) N3 0.024(2) 0.019(2) 0.033(2) -0.0006(18) 0.0002(18) 0.0006(16) C1 0.029(3) 0.026(3) 0.033(3) 0.000(2) -0.006(2) -0.004(2) C2 0.041(3) 0.029(3) 0.038(3) -0.011(3) -0.009(3) 0.003(2) C3 0.031(3) 0.054(4) 0.042(3) -0.026(3) -0.001(3) 0.008(3) C4 0.033(3) 0.054(4) 0.030(3) -0.008(3) 0.005(2) -0.003(3) C5 0.022(2) 0.035(3) 0.026(3) 0.001(2) 0.000(2) 0.002(2) C6 0.028(3) 0.040(3) 0.026(3) 0.001(2) 0.007(2) 0.001(2) C7 0.028(2) 0.019(3) 0.039(3) 0.007(2) 0.001(2) -0.006(2) C8 0.027(2) 0.023(3) 0.030(3) 0.005(2) -0.004(2) 0.0011(19) C9 0.039(3) 0.020(3) 0.046(3) 0.004(2) -0.002(3) -0.004(2) C10 0.045(3) 0.027(3) 0.053(4) -0.006(3) -0.007(3) 0.006(2) C11 0.033(3) 0.035(3) 0.042(3) -0.005(3) 0.003(2) 0.009(2) C12 0.026(3) 0.028(3) 0.038(3) 0.000(3) 0.002(2) 0.003(2) C13 0.016(2) 0.028(3) 0.042(3) 0.004(2) -0.004(2) -0.0041(19) C14 0.019(2) 0.031(3) 0.036(3) 0.006(2) -0.005(2) -0.004(2) C15 0.024(3) 0.041(3) 0.039(3) 0.005(3) 0.001(2) -0.007(2) O1 0.0191(15) 0.0250(17) 0.0316(19) 0.0026(15) -0.0031(13) -0.0052(13) O2 0.0200(15) 0.0239(17) 0.0292(19) 0.0008(14) 0.0008(13) -0.0015(13) N4 0.025(2) 0.021(2) 0.030(2) 0.0050(17) 0.0125(18) 0.0052(16) N5 0.039(3) 0.029(2) 0.029(3) 0.0034(19) 0.005(2) 0.002(2) N6 0.043(3) 0.057(3) 0.065(4) 0.002(3) 0.015(3) 0.004(2) N7 0.042(2) 0.058(3) 0.025(3) 0.004(2) -0.006(2) 0.001(2) N8 0.029(2) 0.067(3) 0.045(3) -0.014(3) -0.001(2) 0.000(2) N9 0.058(3) 0.142(6) 0.049(4) -0.017(4) -0.011(3) 0.022(3) N10 0.045(2) 0.036(3) 0.028(3) -0.004(2) -0.004(2) 0.0029(19) N11 0.039(3) 0.021(2) 0.059(3) 0.004(3) 0.010(3) 0.0050(18) N12 0.087(4) 0.058(3) 0.035(3) -0.009(3) -0.001(3) 0.013(3) N13 0.031(2) 0.026(2) 0.024(2) -0.0028(18) -0.0045(18) 0.0027(17) N14 0.024(2) 0.046(3) 0.029(3) 0.001(2) -0.0018(19) 0.0037(19) N15 0.049(3) 0.060(3) 0.044(3) -0.011(3) -0.005(2) -0.003(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 Fe1 O2 1.936(3) . ? Fe1 O1 2.001(3) . ? Fe1 N13 2.005(4) . ? Fe1 N3 2.115(3) . ? Fe1 N1 2.141(3) . ? Fe1 N2 2.215(3) . ? Fe2 O1 1.979(3) . ? Fe2 N7 1.997(4) . ? Fe2 N10 2.018(4) . ? Fe2 O2 2.087(3) . ? Fe2 N4 2.100(3) . ? Fe2 N4 2.155(3) 5_656 ? N1 C1 1.339(5) . ? N1 C5 1.348(5) . ? N2 C7 1.476(5) . ? N2 C6 1.487(5) . ? N2 C13 1.500(5) . ? N3 C12 1.341(5) . ? N3 C8 1.350(5) . ? C1 C2 1.383(6) . ? C1 H1 0.9500 . ? C2 C3 1.354(6) . ? C2 H2 0.9500 . ? C3 C4 1.388(7) . ? C3 H3 0.9500 . ? C4 C5 1.367(6) . ? C4 H4 0.9500 . ? C5 C6 1.492(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.507(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.379(6) . ? C9 C10 1.385(6) . ? C9 H9 0.9500 . ? C10 C11 1.389(6) . ? C10 H10 0.9500 . ? C11 C12 1.363(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.524(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O1 1.414(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O2 1.420(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N4 N5 1.214(5) . ? N4 Fe2 2.155(3) 5_656 ? N5 N6 1.134(5) . ? N7 N8 1.164(6) . ? N8 N9 1.186(6) . ? N10 N11 1.196(6) . ? N11 N12 1.179(6) . ? N13 N14 1.194(5) . ? N14 N15 1.153(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 O2 Fe1 O1 75.97(11) . . ? O2 Fe1 N13 101.68(13) . . ? O1 Fe1 N13 177.34(13) . . ? O2 Fe1 N3 101.40(13) . . ? O1 Fe1 N3 88.99(12) . . ? N13 Fe1 N3 90.28(14) . . ? O2 Fe1 N1 106.19(13) . . ? O1 Fe1 N1 94.67(12) . . ? N13 Fe1 N1 87.17(14) . . ? N3 Fe1 N1 152.25(14) . . ? O2 Fe1 N2 156.67(12) . . ? O1 Fe1 N2 80.70(12) . . ? N13 Fe1 N2 101.65(14) . . ? N3 Fe1 N2 78.43(13) . . ? N1 Fe1 N2 75.06(13) . . ? O1 Fe2 N7 89.91(14) . . ? O1 Fe2 N10 104.94(15) . . ? N7 Fe2 N10 94.76(17) . . ? O1 Fe2 O2 73.13(11) . . ? N7 Fe2 O2 163.03(14) . . ? N10 Fe2 O2 89.31(14) . . ? O1 Fe2 N4 159.59(13) . . ? N7 Fe2 N4 101.87(16) . . ? N10 Fe2 N4 90.79(15) . . ? O2 Fe2 N4 94.52(13) . . ? O1 Fe2 N4 90.28(12) . 5_656 ? N7 Fe2 N4 90.36(16) . 5_656 ? N10 Fe2 N4 163.91(15) . 5_656 ? O2 Fe2 N4 90.21(13) . 5_656 ? N4 Fe2 N4 73.22(15) . 5_656 ? C1 N1 C5 118.6(4) . . ? C1 N1 Fe1 124.7(3) . . ? C5 N1 Fe1 116.3(3) . . ? C7 N2 C6 112.3(3) . . ? C7 N2 C13 112.1(3) . . ? C6 N2 C13 110.8(3) . . ? C7 N2 Fe1 110.2(2) . . ? C6 N2 Fe1 106.6(2) . . ? C13 N2 Fe1 104.6(2) . . ? C12 N3 C8 120.0(4) . . ? C12 N3 Fe1 123.1(3) . . ? C8 N3 Fe1 116.7(3) . . ? N1 C1 C2 122.2(5) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 118.8(5) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.7(5) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.1(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 121.6(5) . . ? N1 C5 C6 115.4(4) . . ? C4 C5 C6 123.0(4) . . ? N2 C6 C5 110.3(4) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 112.2(3) . . ? N2 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N2 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N3 C8 C9 119.8(4) . . ? N3 C8 C7 117.5(4) . . ? C9 C8 C7 122.6(4) . . ? C8 C9 C10 119.7(4) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C11 120.0(5) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 117.4(4) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? N3 C12 C11 123.1(4) . . ? N3 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? N2 C13 C14 111.0(3) . . ? N2 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N2 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O1 C14 C13 107.1(3) . . ? O1 C14 H14A 110.3 . . ? C13 C14 H14A 110.3 . . ? O1 C14 H14B 110.3 . . ? C13 C14 H14B 110.3 . . ? H14A C14 H14B 108.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 O1 Fe2 134.7(3) . . ? C14 O1 Fe1 116.8(2) . . ? Fe2 O1 Fe1 106.27(12) . . ? C15 O2 Fe1 127.5(3) . . ? C15 O2 Fe2 125.2(3) . . ? Fe1 O2 Fe2 104.60(12) . . ? N5 N4 Fe2 128.7(3) . . ? N5 N4 Fe2 119.0(3) . 5_656 ? Fe2 N4 Fe2 106.78(15) . 5_656 ? N6 N5 N4 177.7(5) . . ? N8 N7 Fe2 137.5(4) . . ? N7 N8 N9 176.3(6) . . ? N11 N10 Fe2 119.1(3) . . ? N12 N11 N10 178.6(5) . . ? N14 N13 Fe1 124.5(3) . . ? N15 N14 N13 178.1(5) . . ? 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 Fe1 N1 C1 7.6(4) . . . . ? O1 Fe1 N1 C1 84.3(3) . . . . ? N13 Fe1 N1 C1 -93.7(3) . . . . ? N3 Fe1 N1 C1 -178.9(3) . . . . ? N2 Fe1 N1 C1 163.4(4) . . . . ? O2 Fe1 N1 C5 -178.7(3) . . . . ? O1 Fe1 N1 C5 -101.9(3) . . . . ? N13 Fe1 N1 C5 80.0(3) . . . . ? N3 Fe1 N1 C5 -5.2(5) . . . . ? N2 Fe1 N1 C5 -22.9(3) . . . . ? O2 Fe1 N2 C7 -107.8(4) . . . . ? O1 Fe1 N2 C7 -106.7(3) . . . . ? N13 Fe1 N2 C7 72.1(3) . . . . ? N3 Fe1 N2 C7 -15.8(3) . . . . ? N1 Fe1 N2 C7 155.9(3) . . . . ? O2 Fe1 N2 C6 130.2(3) . . . . ? O1 Fe1 N2 C6 131.3(3) . . . . ? N13 Fe1 N2 C6 -49.9(3) . . . . ? N3 Fe1 N2 C6 -137.8(3) . . . . ? N1 Fe1 N2 C6 33.9(3) . . . . ? O2 Fe1 N2 C13 12.8(5) . . . . ? O1 Fe1 N2 C13 13.9(2) . . . . ? N13 Fe1 N2 C13 -167.3(3) . . . . ? N3 Fe1 N2 C13 104.8(3) . . . . ? N1 Fe1 N2 C13 -83.5(3) . . . . ? O2 Fe1 N3 C12 -15.1(3) . . . . ? O1 Fe1 N3 C12 -90.6(3) . . . . ? N13 Fe1 N3 C12 86.9(3) . . . . ? N1 Fe1 N3 C12 171.3(3) . . . . ? N2 Fe1 N3 C12 -171.3(3) . . . . ? O2 Fe1 N3 C8 160.5(3) . . . . ? O1 Fe1 N3 C8 85.0(3) . . . . ? N13 Fe1 N3 C8 -97.5(3) . . . . ? N1 Fe1 N3 C8 -13.1(5) . . . . ? N2 Fe1 N3 C8 4.3(3) . . . . ? C5 N1 C1 C2 0.6(6) . . . . ? Fe1 N1 C1 C2 174.2(3) . . . . ? N1 C1 C2 C3 -1.1(7) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? C2 C3 C4 C5 2.0(7) . . . . ? C1 N1 C5 C4 1.3(6) . . . . ? Fe1 N1 C5 C4 -172.8(3) . . . . ? C1 N1 C5 C6 -179.9(4) . . . . ? Fe1 N1 C5 C6 6.0(5) . . . . ? C3 C4 C5 N1 -2.6(7) . . . . ? C3 C4 C5 C6 178.7(4) . . . . ? C7 N2 C6 C5 -162.2(3) . . . . ? C13 N2 C6 C5 71.7(4) . . . . ? Fe1 N2 C6 C5 -41.5(4) . . . . ? N1 C5 C6 N2 25.1(5) . . . . ? C4 C5 C6 N2 -156.2(4) . . . . ? C6 N2 C7 C8 142.8(4) . . . . ? C13 N2 C7 C8 -91.8(4) . . . . ? Fe1 N2 C7 C8 24.2(4) . . . . ? C12 N3 C8 C9 0.3(6) . . . . ? Fe1 N3 C8 C9 -175.5(3) . . . . ? C12 N3 C8 C7 -175.8(4) . . . . ? Fe1 N3 C8 C7 8.4(5) . . . . ? N2 C7 C8 N3 -22.4(5) . . . . ? N2 C7 C8 C9 161.6(4) . . . . ? N3 C8 C9 C10 -0.7(7) . . . . ? C7 C8 C9 C10 175.3(4) . . . . ? C8 C9 C10 C11 0.7(7) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C8 N3 C12 C11 0.1(7) . . . . ? Fe1 N3 C12 C11 175.6(3) . . . . ? C10 C11 C12 N3 -0.1(7) . . . . ? C7 N2 C13 C14 81.8(4) . . . . ? C6 N2 C13 C14 -151.9(3) . . . . ? Fe1 N2 C13 C14 -37.5(4) . . . . ? N2 C13 C14 O1 49.7(4) . . . . ? C13 C14 O1 Fe2 162.2(3) . . . . ? C13 C14 O1 Fe1 -37.4(4) . . . . ? N7 Fe2 O1 C14 -16.4(4) . . . . ? N10 Fe2 O1 C14 78.5(4) . . . . ? O2 Fe2 O1 C14 163.1(4) . . . . ? N4 Fe2 O1 C14 -142.3(4) . . . . ? N4 Fe2 O1 C14 -106.8(4) 5_656 . . . ? N7 Fe2 O1 Fe1 -178.29(17) . . . . ? N10 Fe2 O1 Fe1 -83.39(16) . . . . ? O2 Fe2 O1 Fe1 1.22(12) . . . . ? N4 Fe2 O1 Fe1 55.9(4) . . . . ? N4 Fe2 O1 Fe1 91.35(15) 5_656 . . . ? O2 Fe1 O1 C14 -166.9(3) . . . . ? N13 Fe1 O1 C14 -139(3) . . . . ? N3 Fe1 O1 C14 -64.9(3) . . . . ? N1 Fe1 O1 C14 87.5(3) . . . . ? N2 Fe1 O1 C14 13.5(3) . . . . ? O2 Fe1 O1 Fe2 -1.29(12) . . . . ? N13 Fe1 O1 Fe2 27(3) . . . . ? N3 Fe1 O1 Fe2 100.72(14) . . . . ? N1 Fe1 O1 Fe2 -106.83(15) . . . . ? N2 Fe1 O1 Fe2 179.16(15) . . . . ? O1 Fe1 O2 C15 163.1(3) . . . . ? N13 Fe1 O2 C15 -15.6(3) . . . . ? N3 Fe1 O2 C15 77.0(3) . . . . ? N1 Fe1 O2 C15 -106.1(3) . . . . ? N2 Fe1 O2 C15 164.2(3) . . . . ? O1 Fe1 O2 Fe2 1.22(12) . . . . ? N13 Fe1 O2 Fe2 -177.51(14) . . . . ? N3 Fe1 O2 Fe2 -84.83(14) . . . . ? N1 Fe1 O2 Fe2 92.06(14) . . . . ? N2 Fe1 O2 Fe2 2.3(4) . . . . ? O1 Fe2 O2 C15 -163.6(3) . . . . ? N7 Fe2 O2 C15 -162.0(5) . . . . ? N10 Fe2 O2 C15 -57.8(3) . . . . ? N4 Fe2 O2 C15 32.9(3) . . . . ? N4 Fe2 O2 C15 106.1(3) 5_656 . . . ? O1 Fe2 O2 Fe1 -1.25(12) . . . . ? N7 Fe2 O2 Fe1 0.4(6) . . . . ? N10 Fe2 O2 Fe1 104.60(16) . . . . ? N4 Fe2 O2 Fe1 -164.66(14) . . . . ? N4 Fe2 O2 Fe1 -91.48(14) 5_656 . . . ? O1 Fe2 N4 N5 -115.5(4) . . . . ? N7 Fe2 N4 N5 120.4(4) . . . . ? N10 Fe2 N4 N5 25.4(4) . . . . ? O2 Fe2 N4 N5 -64.0(4) . . . . ? N4 Fe2 N4 N5 -152.8(5) 5_656 . . . ? O1 Fe2 N4 Fe2 37.3(4) . . . 5_656 ? N7 Fe2 N4 Fe2 -86.75(19) . . . 5_656 ? N10 Fe2 N4 Fe2 178.22(18) . . . 5_656 ? O2 Fe2 N4 Fe2 88.85(15) . . . 5_656 ? N4 Fe2 N4 Fe2 0.0 5_656 . . 5_656 ? Fe2 N4 N5 N6 177(100) . . . . ? Fe2 N4 N5 N6 27(13) 5_656 . . . ? O1 Fe2 N7 N8 162.7(6) . . . . ? N10 Fe2 N7 N8 57.7(6) . . . . ? O2 Fe2 N7 N8 161.0(5) . . . . ? N4 Fe2 N7 N8 -34.1(6) . . . . ? N4 Fe2 N7 N8 -107.1(6) 5_656 . . . ? Fe2 N7 N8 N9 109(9) . . . . ? O1 Fe2 N10 N11 -119.2(4) . . . . ? N7 Fe2 N10 N11 -28.0(4) . . . . ? O2 Fe2 N10 N11 168.5(4) . . . . ? N4 Fe2 N10 N11 73.9(4) . . . . ? N4 Fe2 N10 N11 80.1(7) 5_656 . . . ? Fe2 N10 N11 N12 -174(100) . . . . ? O2 Fe1 N13 N14 -85.6(4) . . . . ? O1 Fe1 N13 N14 -113(3) . . . . ? N3 Fe1 N13 N14 172.7(4) . . . . ? N1 Fe1 N13 N14 20.3(4) . . . . ? N2 Fe1 N13 N14 94.4(4) . . . . ? Fe1 N13 N14 N15 116(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.817 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.129 #===END data_mksco-ma1 _database_code_depnum_ccdc_archive 'CCDC 806664' #TrackingRef '- cif files (1-6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Co3 N20 O8' _chemical_formula_weight 953.52 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' Co Co 0.3494 0.9721 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.544(3) _cell_length_b 18.177(7) _cell_length_c 12.538(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.358(8) _cell_angle_gamma 90.00 _cell_volume 1908.9(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 970 _exptl_absorpt_coefficient_mu 1.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 0.448 0.750 38 29 2 0.250 0.107 0.750 12 2 3 0.250 0.182 0.250 8 1 4 0.750 0.552 0.250 38 30 5 0.750 0.893 0.250 12 2 6 0.750 0.818 0.750 8 1 _platon_squeeze_details ; SQUEEZE (PLATON, A.Spek) was used to treat diffuse anion contributions. Total electron count found = 65/unit cell. calculated for two NO3- = 64/unit cell. The intensive properties (density, F(000), and Mol. Wght., etc.) reflect these contributions. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13681 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.1180 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.12 _diffrn_reflns_theta_max 28.33 _reflns_number_total 4737 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.9790P] 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 4737 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.009 _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 Co1 Co 0.73453(8) 0.24717(4) 0.52002(6) 0.0285(2) Uani 1 1 d . . . Co2 Co 0.7500 0.18062(7) 0.7500 0.0338(3) Uani 1 2 d S . . N1 N 0.7973(5) 0.1546(3) 0.4627(3) 0.0305(11) Uani 1 1 d . . . N2 N 0.9183(5) 0.2882(3) 0.4697(4) 0.0355(11) Uani 1 1 d . . . N3 N 0.7003(6) 0.3480(3) 0.5577(4) 0.0447(13) Uani 1 1 d . . . N4 N 0.5785(6) 0.2052(3) 0.5976(4) 0.0415(13) Uani 1 1 d . . . N5 N 0.4485(6) 0.1794(3) 0.5567(4) 0.0370(12) Uani 1 1 d . . . N6 N 0.3275(7) 0.1552(3) 0.5205(5) 0.0599(17) Uani 1 1 d . . . N7 N 0.5920(6) 0.2612(3) 0.3802(4) 0.0372(12) Uani 1 1 d . . . N8 N 0.4606(7) 0.2888(3) 0.3819(4) 0.0374(12) Uani 1 1 d . . . N9 N 0.3358(7) 0.3143(3) 0.3799(5) 0.0537(15) Uani 1 1 d . . . N10 N 0.7500 0.0364(9) 0.7500 0.094(4) Uani 1 2 d S . . O1 O 0.8726(4) 0.2323(2) 0.6555(3) 0.0347(9) Uani 1 1 d . . . O2 O 0.6356(10) 0.0770(4) 0.7545(5) 0.116(3) Uani 1 1 d . . . O3 O 0.7500 -0.0253(7) 0.7500 0.289(15) Uani 1 2 d S . . C1 C 0.7399(7) 0.0880(3) 0.4783(5) 0.0399(15) Uani 1 1 d . . . H1 H 0.6638 0.0832 0.5238 0.048 Uiso 1 1 calc R . . C2 C 0.7884(9) 0.0253(4) 0.4296(6) 0.058(2) Uani 1 1 d . . . H2 H 0.7459 -0.0217 0.4409 0.070 Uiso 1 1 calc R . . C3 C 0.9006(10) 0.0337(4) 0.3644(6) 0.065(2) Uani 1 1 d . . . H3 H 0.9363 -0.0080 0.3303 0.079 Uiso 1 1 calc R . . C4 C 0.9605(8) 0.1025(4) 0.3487(6) 0.0545(19) Uani 1 1 d . . . H4 H 1.0374 0.1085 0.3040 0.065 Uiso 1 1 calc R . . C5 C 0.9071(7) 0.1620(3) 0.3989(4) 0.0359(14) Uani 1 1 d . . . C6 C 0.9564(7) 0.2396(3) 0.3821(4) 0.0371(15) Uani 1 1 d . . . H6A H 1.0725 0.2413 0.3830 0.045 Uiso 1 1 calc R . . H6B H 0.8996 0.2575 0.3102 0.045 Uiso 1 1 calc R . . C7 C 0.8729(8) 0.3639(3) 0.4296(6) 0.0493(18) Uani 1 1 d . . . H7A H 0.9695 0.3935 0.4275 0.059 Uiso 1 1 calc R . . H7B H 0.8067 0.3620 0.3554 0.059 Uiso 1 1 calc R . . C8 C 0.7818(8) 0.3966(4) 0.5061(6) 0.0524(18) Uani 1 1 d . . . C9 C 0.7657(11) 0.4716(4) 0.5248(9) 0.081(3) Uani 1 1 d . . . H9 H 0.8202 0.5059 0.4882 0.097 Uiso 1 1 calc R . . C10 C 0.6742(14) 0.4968(5) 0.5940(10) 0.101(4) Uani 1 1 d . . . H10 H 0.6642 0.5481 0.6055 0.121 Uiso 1 1 calc R . . C11 C 0.5970(11) 0.4473(5) 0.6467(8) 0.085(3) Uani 1 1 d . . . H11 H 0.5338 0.4638 0.6964 0.102 Uiso 1 1 calc R . . C12 C 0.6112(8) 0.3715(4) 0.6272(5) 0.0554(19) Uani 1 1 d . . . H12 H 0.5570 0.3369 0.6637 0.067 Uiso 1 1 calc R . . C13 C 1.0530(7) 0.2922(3) 0.5671(5) 0.0375(14) Uani 1 1 d . . . H13A H 1.1566 0.2881 0.5434 0.045 Uiso 1 1 calc R . . H13B H 1.0503 0.3401 0.6042 0.045 Uiso 1 1 calc R . . C14 C 1.0370(6) 0.2307(3) 0.6443(4) 0.0376(15) Uani 1 1 d . . . H14A H 1.0633 0.1829 0.6144 0.045 Uiso 1 1 calc R . . H14B H 1.1090 0.2387 0.7155 0.045 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 Co1 0.0255(4) 0.0399(4) 0.0199(4) -0.0006(3) 0.0044(3) -0.0029(4) Co2 0.0308(6) 0.0516(7) 0.0204(5) 0.000 0.0085(4) 0.000 N1 0.034(3) 0.036(3) 0.021(2) 0.003(2) 0.0054(19) -0.001(2) N2 0.027(3) 0.043(3) 0.033(3) 0.001(2) -0.004(2) -0.001(2) N3 0.036(3) 0.061(3) 0.034(3) -0.011(3) -0.002(2) 0.008(3) N4 0.040(3) 0.064(3) 0.019(2) 0.006(2) 0.001(2) -0.010(3) N5 0.023(3) 0.053(3) 0.035(3) 0.004(3) 0.003(2) 0.000(2) N6 0.038(3) 0.069(4) 0.071(4) 0.005(3) 0.005(3) -0.015(3) N7 0.035(3) 0.055(3) 0.022(2) -0.001(2) 0.005(2) 0.006(2) N8 0.049(3) 0.046(3) 0.017(2) 0.003(2) 0.007(2) -0.010(3) N9 0.036(3) 0.070(4) 0.053(4) 0.005(3) 0.005(3) 0.009(3) N10 0.072(8) 0.110(11) 0.131(10) 0.000 0.096(8) 0.000 O1 0.027(2) 0.049(2) 0.027(2) 0.0006(18) 0.0014(16) -0.0035(18) O2 0.170(8) 0.108(5) 0.073(5) 0.006(4) 0.026(5) -0.033(5) O3 0.44(3) 0.054(7) 0.50(3) 0.000 0.41(3) 0.000 C1 0.043(4) 0.042(4) 0.032(3) 0.006(3) 0.001(3) 0.001(3) C2 0.063(5) 0.044(4) 0.060(5) -0.004(4) -0.006(4) -0.003(4) C3 0.067(5) 0.060(5) 0.062(5) -0.026(4) -0.004(4) 0.019(4) C4 0.042(4) 0.077(5) 0.043(4) -0.021(4) 0.005(3) 0.008(4) C5 0.032(3) 0.053(4) 0.022(3) 0.000(3) 0.004(2) 0.004(3) C6 0.032(3) 0.066(4) 0.017(3) 0.008(3) 0.014(2) -0.006(3) C7 0.045(4) 0.045(4) 0.055(4) 0.021(3) 0.004(3) -0.007(3) C8 0.035(4) 0.045(4) 0.070(5) 0.003(4) -0.008(3) 0.000(3) C9 0.068(6) 0.041(4) 0.120(8) -0.002(5) -0.019(6) 0.004(4) C10 0.103(8) 0.051(5) 0.119(9) -0.024(6) -0.053(7) 0.034(6) C11 0.079(6) 0.083(6) 0.074(6) -0.045(5) -0.028(5) 0.044(5) C12 0.043(4) 0.079(5) 0.039(4) -0.015(4) -0.007(3) 0.023(4) C13 0.032(3) 0.052(4) 0.028(3) -0.008(3) 0.006(2) -0.010(3) C14 0.026(3) 0.062(4) 0.023(3) 0.004(3) 0.000(2) -0.008(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 Co1 O1 1.887(4) . ? Co1 N3 1.929(5) . ? Co1 N7 1.944(5) . ? Co1 N1 1.947(5) . ? Co1 N2 1.952(5) . ? Co1 N4 1.953(5) . ? Co2 O1 1.968(4) . ? Co2 O1 1.968(4) 2_656 ? Co2 O2 2.128(7) 2_656 ? Co2 O2 2.128(7) . ? Co2 N4 2.212(5) . ? Co2 N4 2.212(5) 2_656 ? N1 C1 1.335(7) . ? N1 C5 1.354(7) . ? N2 C7 1.489(7) . ? N2 C6 1.494(7) . ? N2 C13 1.506(7) . ? N3 C12 1.335(8) . ? N3 C8 1.365(9) . ? N4 N5 1.222(6) . ? N5 N6 1.132(6) . ? N7 N8 1.233(7) . ? N8 N9 1.159(7) . ? N10 O3 1.123(14) . ? N10 O2 1.235(10) . ? N10 O2 1.235(10) 2_656 ? O1 C14 1.440(7) . ? C1 C2 1.393(9) . ? C1 H1 0.9500 . ? C2 C3 1.386(11) . ? C2 H2 0.9500 . ? C3 C4 1.379(10) . ? C3 H3 0.9500 . ? C4 C5 1.375(8) . ? C4 H4 0.9500 . ? C5 C6 1.499(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.474(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.394(10) . ? C9 C10 1.357(14) . ? C9 H9 0.9500 . ? C10 C11 1.361(14) . ? C10 H10 0.9500 . ? C11 C12 1.409(10) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.501(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 Co1 N3 90.75(19) . . ? O1 Co1 N7 179.30(19) . . ? N3 Co1 N7 89.9(2) . . ? O1 Co1 N1 92.31(18) . . ? N3 Co1 N1 167.9(2) . . ? N7 Co1 N1 87.08(19) . . ? O1 Co1 N2 86.90(18) . . ? N3 Co1 N2 83.5(2) . . ? N7 Co1 N2 93.4(2) . . ? N1 Co1 N2 85.0(2) . . ? O1 Co1 N4 82.10(18) . . ? N3 Co1 N4 95.6(2) . . ? N7 Co1 N4 97.6(2) . . ? N1 Co1 N4 96.4(2) . . ? N2 Co1 N4 168.95(19) . . ? O1 Co2 O1 122.9(2) . 2_656 ? O1 Co2 O2 96.0(3) . 2_656 ? O1 Co2 O2 137.8(2) 2_656 2_656 ? O1 Co2 O2 137.8(2) . . ? O1 Co2 O2 96.0(3) 2_656 . ? O2 Co2 O2 55.5(5) 2_656 . ? O1 Co2 N4 73.98(17) . . ? O1 Co2 N4 94.76(17) 2_656 . ? O2 Co2 N4 112.7(2) 2_656 . ? O2 Co2 N4 88.4(2) . . ? O1 Co2 N4 94.76(17) . 2_656 ? O1 Co2 N4 73.98(17) 2_656 2_656 ? O2 Co2 N4 88.4(2) 2_656 2_656 ? O2 Co2 N4 112.7(2) . 2_656 ? N4 Co2 N4 156.7(3) . 2_656 ? C1 N1 C5 119.7(5) . . ? C1 N1 Co1 126.4(4) . . ? C5 N1 Co1 113.9(4) . . ? C7 N2 C6 112.2(5) . . ? C7 N2 C13 109.6(5) . . ? C6 N2 C13 112.5(4) . . ? C7 N2 Co1 106.8(4) . . ? C6 N2 Co1 108.5(3) . . ? C13 N2 Co1 106.9(3) . . ? C12 N3 C8 120.7(6) . . ? C12 N3 Co1 126.7(5) . . ? C8 N3 Co1 112.5(5) . . ? N5 N4 Co1 126.5(4) . . ? N5 N4 Co2 132.6(4) . . ? Co1 N4 Co2 96.2(2) . . ? N6 N5 N4 178.9(6) . . ? N8 N7 Co1 116.6(4) . . ? N9 N8 N7 177.8(6) . . ? O3 N10 O2 126.7(7) . . ? O3 N10 O2 126.7(7) . 2_656 ? O2 N10 O2 106.7(14) . 2_656 ? C14 O1 Co1 111.3(3) . . ? C14 O1 Co2 134.0(3) . . ? Co1 O1 Co2 107.32(18) . . ? N10 O2 Co2 98.9(9) . . ? N1 C1 C2 121.8(6) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 117.9(7) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C4 C3 C2 120.2(7) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 118.8(7) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.5(6) . . ? N1 C5 C6 115.1(5) . . ? C4 C5 C6 123.3(6) . . ? N2 C6 C5 110.1(4) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 N2 106.8(5) . . ? C8 C7 H7A 110.4 . . ? N2 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? N2 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? N3 C8 C9 118.5(8) . . ? N3 C8 C7 115.5(6) . . ? C9 C8 C7 125.9(8) . . ? C10 C9 C8 121.8(10) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 118.8(8) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C12 119.7(9) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N3 C12 C11 120.5(8) . . ? N3 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 N2 109.6(4) . . ? C14 C13 H13A 109.8 . . ? N2 C13 H13A 109.8 . . ? C14 C13 H13B 109.8 . . ? N2 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O1 C14 C13 105.2(5) . . ? O1 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? O1 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? 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 Co1 N1 C1 82.6(5) . . . . ? N3 Co1 N1 C1 -172.8(8) . . . . ? N7 Co1 N1 C1 -97.0(5) . . . . ? N2 Co1 N1 C1 169.3(5) . . . . ? N4 Co1 N1 C1 0.3(5) . . . . ? O1 Co1 N1 C5 -99.2(4) . . . . ? N3 Co1 N1 C5 5.3(11) . . . . ? N7 Co1 N1 C5 81.1(4) . . . . ? N2 Co1 N1 C5 -12.6(4) . . . . ? N4 Co1 N1 C5 178.4(4) . . . . ? O1 Co1 N2 C7 -123.4(4) . . . . ? N3 Co1 N2 C7 -32.3(4) . . . . ? N7 Co1 N2 C7 57.2(4) . . . . ? N1 Co1 N2 C7 144.0(4) . . . . ? N4 Co1 N2 C7 -118.2(11) . . . . ? O1 Co1 N2 C6 115.4(3) . . . . ? N3 Co1 N2 C6 -153.5(4) . . . . ? N7 Co1 N2 C6 -63.9(4) . . . . ? N1 Co1 N2 C6 22.8(3) . . . . ? N4 Co1 N2 C6 120.6(11) . . . . ? O1 Co1 N2 C13 -6.1(4) . . . . ? N3 Co1 N2 C13 85.0(4) . . . . ? N7 Co1 N2 C13 174.5(4) . . . . ? N1 Co1 N2 C13 -98.7(4) . . . . ? N4 Co1 N2 C13 -0.9(13) . . . . ? O1 Co1 N3 C12 -74.5(5) . . . . ? N7 Co1 N3 C12 105.2(5) . . . . ? N1 Co1 N3 C12 -179.3(7) . . . . ? N2 Co1 N3 C12 -161.3(5) . . . . ? N4 Co1 N3 C12 7.6(5) . . . . ? O1 Co1 N3 C8 104.3(4) . . . . ? N7 Co1 N3 C8 -75.9(4) . . . . ? N1 Co1 N3 C8 -0.4(12) . . . . ? N2 Co1 N3 C8 17.5(4) . . . . ? N4 Co1 N3 C8 -173.6(4) . . . . ? O1 Co1 N4 N5 -162.5(6) . . . . ? N3 Co1 N4 N5 107.5(5) . . . . ? N7 Co1 N4 N5 16.9(6) . . . . ? N1 Co1 N4 N5 -71.0(5) . . . . ? N2 Co1 N4 N5 -167.7(9) . . . . ? O1 Co1 N4 Co2 -4.43(18) . . . . ? N3 Co1 N4 Co2 -94.4(2) . . . . ? N7 Co1 N4 Co2 174.9(2) . . . . ? N1 Co1 N4 Co2 87.0(2) . . . . ? N2 Co1 N4 Co2 -9.6(12) . . . . ? O1 Co2 N4 N5 160.3(6) . . . . ? O1 Co2 N4 N5 -76.8(6) 2_656 . . . ? O2 Co2 N4 N5 70.4(6) 2_656 . . . ? O2 Co2 N4 N5 19.1(6) . . . . ? N4 Co2 N4 N5 -136.3(6) 2_656 . . . ? O1 Co2 N4 Co1 4.38(18) . . . . ? O1 Co2 N4 Co1 127.3(2) 2_656 . . . ? O2 Co2 N4 Co1 -85.5(3) 2_656 . . . ? O2 Co2 N4 Co1 -136.8(3) . . . . ? N4 Co2 N4 Co1 67.75(17) 2_656 . . . ? N3 Co1 N7 N8 -50.2(5) . . . . ? N1 Co1 N7 N8 141.5(4) . . . . ? N2 Co1 N7 N8 -133.7(4) . . . . ? N4 Co1 N7 N8 45.4(5) . . . . ? N3 Co1 O1 C14 -104.7(4) . . . . ? N1 Co1 O1 C14 63.6(4) . . . . ? N2 Co1 O1 C14 -21.3(4) . . . . ? N4 Co1 O1 C14 159.7(4) . . . . ? N3 Co1 O1 Co2 100.7(2) . . . . ? N1 Co1 O1 Co2 -90.9(2) . . . . ? N2 Co1 O1 Co2 -175.8(2) . . . . ? N4 Co1 O1 Co2 5.2(2) . . . . ? O1 Co2 O1 C14 123.9(5) 2_656 . . . ? O2 Co2 O1 C14 -39.0(5) 2_656 . . . ? O2 Co2 O1 C14 -82.0(6) . . . . ? N4 Co2 O1 C14 -150.9(5) . . . . ? N4 Co2 O1 C14 49.9(5) 2_656 . . . ? O1 Co2 O1 Co1 -89.95(17) 2_656 . . . ? O2 Co2 O1 Co1 107.2(3) 2_656 . . . ? O2 Co2 O1 Co1 64.2(4) . . . . ? N4 Co2 O1 Co1 -163.9(2) 2_656 . . . ? O3 N10 O2 Co2 180.0 . . . . ? O2 N10 O2 Co2 0.000(1) 2_656 . . . ? O1 Co2 O2 N10 55.3(5) . . . . ? O1 Co2 O2 N10 -146.2(3) 2_656 . . . ? O2 Co2 O2 N10 0.0 2_656 . . . ? N4 Co2 O2 N10 119.1(4) . . . . ? N4 Co2 O2 N10 -71.1(4) 2_656 . . . ? C5 N1 C1 C2 -0.7(8) . . . . ? Co1 N1 C1 C2 177.3(4) . . . . ? N1 C1 C2 C3 0.6(10) . . . . ? C1 C2 C3 C4 -0.2(11) . . . . ? C2 C3 C4 C5 0.0(11) . . . . ? C1 N1 C5 C4 0.5(8) . . . . ? Co1 N1 C5 C4 -177.7(4) . . . . ? C1 N1 C5 C6 176.8(5) . . . . ? Co1 N1 C5 C6 -1.5(6) . . . . ? C3 C4 C5 N1 -0.2(9) . . . . ? C3 C4 C5 C6 -176.1(6) . . . . ? C7 N2 C6 C5 -146.5(5) . . . . ? C13 N2 C6 C5 89.4(5) . . . . ? Co1 N2 C6 C5 -28.7(5) . . . . ? N1 C5 C6 N2 20.2(6) . . . . ? C4 C5 C6 N2 -163.6(5) . . . . ? C6 N2 C7 C8 158.9(5) . . . . ? C13 N2 C7 C8 -75.4(6) . . . . ? Co1 N2 C7 C8 40.1(5) . . . . ? C12 N3 C8 C9 -2.0(9) . . . . ? Co1 N3 C8 C9 179.1(5) . . . . ? C12 N3 C8 C7 -178.7(5) . . . . ? Co1 N3 C8 C7 2.4(7) . . . . ? N2 C7 C8 N3 -28.4(7) . . . . ? N2 C7 C8 C9 155.2(6) . . . . ? N3 C8 C9 C10 1.2(11) . . . . ? C7 C8 C9 C10 177.5(7) . . . . ? C8 C9 C10 C11 0.3(13) . . . . ? C9 C10 C11 C12 -1.1(13) . . . . ? C8 N3 C12 C11 1.3(9) . . . . ? Co1 N3 C12 C11 -179.9(5) . . . . ? C10 C11 C12 N3 0.3(11) . . . . ? C7 N2 C13 C14 146.6(5) . . . . ? C6 N2 C13 C14 -87.8(5) . . . . ? Co1 N2 C13 C14 31.2(5) . . . . ? Co1 O1 C14 C13 42.6(5) . . . . ? Co2 O1 C14 C13 -172.2(3) . . . . ? N2 C13 C14 O1 -47.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.862 _refine_diff_density_min -0.860 _refine_diff_density_rms 0.135 #===END #===END data_jw008-ma _database_code_depnum_ccdc_archive 'CCDC 806665' #TrackingRef '- cif files (1-6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Co N5 O S2' _chemical_formula_weight 418.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4373(7) _cell_length_b 11.4202(9) _cell_length_c 19.3899(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.095(2) _cell_angle_gamma 90.00 _cell_volume 1863.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.159 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13476 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.0894 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4616 _reflns_number_gt 2546 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+1.5906P] 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 4616 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.007 _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 Co1 Co 0.52210(8) 0.41332(6) 0.21779(3) 0.0342(2) Uani 1 1 d . . . S1 S 1.01241(17) 0.38932(14) 0.11230(7) 0.0524(4) Uani 1 1 d . . . S2 S 0.47122(18) 0.07466(13) 0.07442(7) 0.0508(4) Uani 1 1 d . . . N1 N 0.4532(5) 0.5376(4) 0.1388(2) 0.0384(10) Uani 1 1 d . . . N2 N 0.5141(5) 0.5725(3) 0.2765(2) 0.0341(9) Uani 1 1 d . . . N3 N 0.5797(5) 0.3526(4) 0.3204(2) 0.0384(10) Uani 1 1 d . . . N4 N 0.7596(5) 0.4329(4) 0.1955(2) 0.0490(12) Uani 1 1 d . . . N5 N 0.4895(5) 0.2633(4) 0.1641(2) 0.0468(11) Uani 1 1 d . . . O1 O 0.2699(4) 0.4114(3) 0.24074(19) 0.0446(9) Uani 1 1 d . . . H1 H 0.206(8) 0.393(6) 0.196(4) 0.10(3) Uiso 1 1 d . . . C1 C 0.3868(6) 0.5155(6) 0.0756(3) 0.0503(14) Uani 1 1 d . . . H1A H 0.3712 0.4363 0.0617 0.060 Uiso 1 1 calc R . . C2 C 0.3398(7) 0.6035(7) 0.0295(3) 0.068(2) Uani 1 1 d . . . H2 H 0.2931 0.5857 -0.0153 0.082 Uiso 1 1 calc R . . C3 C 0.3627(8) 0.7169(7) 0.0506(4) 0.078(2) Uani 1 1 d . . . H3 H 0.3315 0.7791 0.0200 0.093 Uiso 1 1 calc R . . C4 C 0.4297(8) 0.7414(6) 0.1149(3) 0.0641(17) Uani 1 1 d . . . H4 H 0.4456 0.8202 0.1295 0.077 Uiso 1 1 calc R . . C5 C 0.4741(6) 0.6500(5) 0.1582(3) 0.0487(14) Uani 1 1 d . . . C6 C 0.5493(6) 0.6698(5) 0.2302(3) 0.0469(14) Uani 1 1 d . . . H6A H 0.6658 0.6774 0.2283 0.056 Uiso 1 1 calc R . . H6B H 0.5086 0.7438 0.2488 0.056 Uiso 1 1 calc R . . C7 C 0.6347(6) 0.5584(5) 0.3350(3) 0.0447(13) Uani 1 1 d . . . H7A H 0.6182 0.6185 0.3707 0.054 Uiso 1 1 calc R . . H7B H 0.7422 0.5694 0.3187 0.054 Uiso 1 1 calc R . . C8 C 0.6216(6) 0.4380(5) 0.3659(3) 0.0419(13) Uani 1 1 d . . . C9 C 0.6520(7) 0.4157(6) 0.4354(3) 0.0577(16) Uani 1 1 d . . . H9 H 0.6823 0.4775 0.4664 0.069 Uiso 1 1 calc R . . C10 C 0.6381(8) 0.3030(6) 0.4595(3) 0.0656(18) Uani 1 1 d . . . H10 H 0.6594 0.2860 0.5072 0.079 Uiso 1 1 calc R . . C11 C 0.5933(7) 0.2161(6) 0.4138(3) 0.0612(17) Uani 1 1 d . . . H11 H 0.5813 0.1379 0.4294 0.073 Uiso 1 1 calc R . . C12 C 0.5658(6) 0.2435(5) 0.3451(3) 0.0451(13) Uani 1 1 d . . . H12 H 0.5355 0.1825 0.3136 0.054 Uiso 1 1 calc R . . C13 C 0.3530(6) 0.5833(5) 0.3027(3) 0.0546(16) Uani 1 1 d . . . H13A H 0.3552 0.5474 0.3493 0.066 Uiso 1 1 calc R . . H13B H 0.3283 0.6675 0.3078 0.066 Uiso 1 1 calc R . . C14 C 0.2279(7) 0.5302(6) 0.2599(4) 0.080(2) Uani 1 1 d . . . H14A H 0.2063 0.5777 0.2176 0.096 Uiso 1 1 calc R . . H14B H 0.1298 0.5282 0.2851 0.096 Uiso 1 1 calc R . . C15 C 0.8640(6) 0.4146(4) 0.1612(3) 0.0411(12) Uani 1 1 d . . . C16 C 0.4817(6) 0.1859(4) 0.1268(2) 0.0342(11) 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 Co1 0.0366(4) 0.0275(4) 0.0381(4) -0.0038(3) 0.0003(3) -0.0004(3) S1 0.0440(8) 0.0684(11) 0.0454(8) 0.0022(7) 0.0069(6) 0.0099(7) S2 0.0616(9) 0.0465(9) 0.0444(8) -0.0149(7) 0.0029(7) -0.0025(7) N1 0.036(2) 0.040(3) 0.039(2) 0.004(2) 0.0035(19) 0.0024(19) N2 0.039(2) 0.023(2) 0.040(2) -0.0034(18) 0.0022(18) -0.0032(17) N3 0.040(2) 0.032(2) 0.042(2) -0.005(2) -0.0022(19) 0.0000(19) N4 0.038(3) 0.049(3) 0.061(3) 0.002(2) 0.008(2) 0.008(2) N5 0.052(3) 0.033(3) 0.056(3) -0.015(2) 0.006(2) -0.003(2) O1 0.042(2) 0.048(2) 0.045(2) -0.0130(19) 0.0065(17) -0.0082(17) C1 0.043(3) 0.066(4) 0.042(3) -0.003(3) 0.006(2) -0.002(3) C2 0.056(4) 0.106(6) 0.043(3) 0.020(4) 0.005(3) 0.008(4) C3 0.074(5) 0.086(6) 0.073(5) 0.038(5) 0.008(4) 0.015(4) C4 0.071(4) 0.052(4) 0.069(4) 0.018(3) 0.006(4) 0.006(3) C5 0.047(3) 0.051(4) 0.049(3) 0.013(3) 0.005(3) 0.000(3) C6 0.049(3) 0.026(3) 0.065(4) 0.005(3) -0.001(3) -0.007(2) C7 0.048(3) 0.041(3) 0.044(3) -0.010(2) -0.006(2) -0.006(2) C8 0.041(3) 0.039(3) 0.046(3) 0.001(2) 0.001(2) -0.003(2) C9 0.070(4) 0.055(4) 0.046(3) 0.002(3) -0.007(3) -0.018(3) C10 0.082(5) 0.068(5) 0.045(3) 0.016(3) -0.006(3) -0.020(4) C11 0.075(4) 0.049(4) 0.058(4) 0.021(3) -0.007(3) -0.011(3) C12 0.047(3) 0.029(3) 0.060(4) 0.003(3) 0.000(3) 0.000(2) C13 0.041(3) 0.042(3) 0.083(4) -0.022(3) 0.019(3) -0.003(3) C14 0.043(4) 0.085(5) 0.114(6) -0.054(5) 0.025(4) -0.004(3) C15 0.043(3) 0.034(3) 0.044(3) 0.005(2) -0.012(2) -0.002(2) C16 0.035(3) 0.030(3) 0.037(3) 0.003(2) 0.003(2) 0.002(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 Co1 N5 2.013(4) . ? Co1 N4 2.092(4) . ? Co1 N3 2.129(4) . ? Co1 N1 2.138(4) . ? Co1 N2 2.149(4) . ? Co1 O1 2.205(3) . ? S1 C15 1.649(6) . ? S2 C16 1.625(5) . ? N1 C1 1.335(6) . ? N1 C5 1.345(7) . ? N2 C6 1.473(6) . ? N2 C7 1.477(6) . ? N2 C13 1.490(6) . ? N3 C12 1.344(6) . ? N3 C8 1.345(6) . ? N4 C15 1.160(6) . ? N5 C16 1.141(6) . ? O1 C14 1.457(7) . ? O1 H1 1.01(7) . ? C1 C2 1.384(8) . ? C1 H1A 0.9500 . ? C2 C3 1.367(10) . ? C2 H2 0.9500 . ? C3 C4 1.361(9) . ? C3 H3 0.9500 . ? C4 C5 1.375(8) . ? C4 H4 0.9500 . ? C5 C6 1.510(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.507(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.378(7) . ? C9 C10 1.376(8) . ? C9 H9 0.9500 . ? C10 C11 1.366(8) . ? C10 H10 0.9500 . ? C11 C12 1.372(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.430(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Co1 N4 94.69(18) . . ? N5 Co1 N3 102.66(17) . . ? N4 Co1 N3 94.01(17) . . ? N5 Co1 N1 100.06(18) . . ? N4 Co1 N1 89.79(17) . . ? N3 Co1 N1 156.56(16) . . ? N5 Co1 N2 170.28(16) . . ? N4 Co1 N2 94.93(17) . . ? N3 Co1 N2 78.11(15) . . ? N1 Co1 N2 78.52(16) . . ? N5 Co1 O1 89.88(16) . . ? N4 Co1 O1 174.40(17) . . ? N3 Co1 O1 88.15(15) . . ? N1 Co1 O1 86.21(15) . . ? N2 Co1 O1 80.44(14) . . ? C1 N1 C5 118.3(5) . . ? C1 N1 Co1 127.4(4) . . ? C5 N1 Co1 114.2(3) . . ? C6 N2 C7 113.1(4) . . ? C6 N2 C13 111.9(4) . . ? C7 N2 C13 110.0(4) . . ? C6 N2 Co1 107.4(3) . . ? C7 N2 Co1 105.6(3) . . ? C13 N2 Co1 108.4(3) . . ? C12 N3 C8 117.6(5) . . ? C12 N3 Co1 128.0(4) . . ? C8 N3 Co1 114.1(3) . . ? C15 N4 Co1 151.3(4) . . ? C16 N5 Co1 170.5(4) . . ? C14 O1 Co1 107.4(3) . . ? C14 O1 H1 107(4) . . ? Co1 O1 H1 107(4) . . ? N1 C1 C2 122.6(6) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C3 C2 C1 117.8(6) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C3 C2 120.6(7) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.7(7) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 122.0(5) . . ? N1 C5 C6 116.0(5) . . ? C4 C5 C6 121.9(6) . . ? N2 C6 C5 111.2(4) . . ? N2 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 109.7(4) . . ? N2 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N2 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N3 C8 C9 122.0(5) . . ? N3 C8 C7 115.1(4) . . ? C9 C8 C7 122.9(5) . . ? C10 C9 C8 119.3(6) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 119.1(6) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 118.9(6) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? N3 C12 C11 123.1(5) . . ? N3 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C14 C13 N2 114.9(5) . . ? C14 C13 H13A 108.6 . . ? N2 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? N2 C13 H13B 108.6 . . ? H13A C13 H13B 107.5 . . ? C13 C14 O1 111.1(5) . . ? C13 C14 H14A 109.4 . . ? O1 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? O1 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N4 C15 S1 179.6(5) . . ? N5 C16 S2 179.3(5) . . ? 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 N5 Co1 N1 C1 8.2(4) . . . . ? N4 Co1 N1 C1 102.9(4) . . . . ? N3 Co1 N1 C1 -157.4(4) . . . . ? N2 Co1 N1 C1 -162.0(4) . . . . ? O1 Co1 N1 C1 -81.0(4) . . . . ? N5 Co1 N1 C5 -175.2(3) . . . . ? N4 Co1 N1 C5 -80.4(4) . . . . ? N3 Co1 N1 C5 19.2(6) . . . . ? N2 Co1 N1 C5 14.6(3) . . . . ? O1 Co1 N1 C5 95.6(4) . . . . ? N4 Co1 N2 C6 60.3(3) . . . . ? N3 Co1 N2 C6 153.4(3) . . . . ? N1 Co1 N2 C6 -28.4(3) . . . . ? O1 Co1 N2 C6 -116.5(3) . . . . ? N4 Co1 N2 C7 -60.7(3) . . . . ? N3 Co1 N2 C7 32.4(3) . . . . ? N1 Co1 N2 C7 -149.5(3) . . . . ? O1 Co1 N2 C7 122.5(3) . . . . ? N4 Co1 N2 C13 -178.5(4) . . . . ? N3 Co1 N2 C13 -85.5(4) . . . . ? N1 Co1 N2 C13 92.7(4) . . . . ? O1 Co1 N2 C13 4.7(3) . . . . ? N5 Co1 N3 C12 -12.0(5) . . . . ? N4 Co1 N3 C12 -107.8(4) . . . . ? N1 Co1 N3 C12 153.5(4) . . . . ? N2 Co1 N3 C12 158.0(4) . . . . ? O1 Co1 N3 C12 77.4(4) . . . . ? N5 Co1 N3 C8 174.3(3) . . . . ? N4 Co1 N3 C8 78.5(4) . . . . ? N1 Co1 N3 C8 -20.2(6) . . . . ? O1 Co1 N3 C8 -96.3(3) . . . . ? N5 Co1 N4 C15 23.1(9) . . . . ? N3 Co1 N4 C15 126.2(9) . . . . ? N1 Co1 N4 C15 -77.0(9) . . . . ? N2 Co1 N4 C15 -155.4(9) . . . . ? N5 Co1 O1 C14 -160.3(4) . . . . ? N3 Co1 O1 C14 97.1(4) . . . . ? N1 Co1 O1 C14 -60.2(4) . . . . ? N2 Co1 O1 C14 18.8(4) . . . . ? C5 N1 C1 C2 0.3(8) . . . . ? Co1 N1 C1 C2 176.8(4) . . . . ? N1 C1 C2 C3 -0.2(9) . . . . ? C1 C2 C3 C4 0.0(10) . . . . ? C2 C3 C4 C5 0.1(10) . . . . ? C1 N1 C5 C4 -0.2(8) . . . . ? Co1 N1 C5 C4 -177.2(4) . . . . ? C1 N1 C5 C6 179.9(5) . . . . ? Co1 N1 C5 C6 2.9(6) . . . . ? C3 C4 C5 N1 0.0(9) . . . . ? C3 C4 C5 C6 180.0(6) . . . . ? C7 N2 C6 C5 154.4(4) . . . . ? C13 N2 C6 C5 -80.7(5) . . . . ? Co1 N2 C6 C5 38.2(5) . . . . ? N1 C5 C6 N2 -28.3(7) . . . . ? C4 C5 C6 N2 151.7(5) . . . . ? C6 N2 C7 C8 -161.7(4) . . . . ? C13 N2 C7 C8 72.3(5) . . . . ? Co1 N2 C7 C8 -44.5(5) . . . . ? C12 N3 C8 C9 1.0(8) . . . . ? Co1 N3 C8 C9 175.4(4) . . . . ? C12 N3 C8 C7 -179.8(4) . . . . ? Co1 N3 C8 C7 -5.4(6) . . . . ? N2 C7 C8 N3 34.5(6) . . . . ? N2 C7 C8 C9 -146.4(5) . . . . ? N3 C8 C9 C10 -0.6(9) . . . . ? C7 C8 C9 C10 -179.7(5) . . . . ? C8 C9 C10 C11 -0.5(10) . . . . ? C9 C10 C11 C12 1.0(10) . . . . ? C8 N3 C12 C11 -0.5(8) . . . . ? Co1 N3 C12 C11 -174.0(4) . . . . ? C10 C11 C12 N3 -0.5(9) . . . . ? C6 N2 C13 C14 88.7(6) . . . . ? C7 N2 C13 C14 -144.6(6) . . . . ? Co1 N2 C13 C14 -29.6(7) . . . . ? N2 C13 C14 O1 48.5(8) . . . . ? Co1 O1 C14 C13 -40.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.860 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.117 #===END data_jw025-ma _database_code_depnum_ccdc_archive 'CCDC 806666' #TrackingRef '- cif files (1-6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Fe N5 O S2' _chemical_formula_weight 415.32 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' Fe Fe 0.3463 0.8444 '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 monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4629(9) _cell_length_b 11.5128(12) _cell_length_c 19.611(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.807(3) _cell_angle_gamma 90.00 _cell_volume 1904.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 195(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 195(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13975 _diffrn_reflns_av_R_equivalents 0.0813 _diffrn_reflns_av_sigmaI/netI 0.1040 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4719 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4719 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1677 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.006 _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 Fe1 Fe 0.52657(8) 0.09213(6) 0.21531(4) 0.0472(2) Uani 1 1 d . . . S1 S 1.01334(18) 0.11119(14) 0.11156(8) 0.0766(5) Uani 1 1 d . . . S2 S 0.4690(2) 0.42800(12) 0.07463(8) 0.0732(5) Uani 1 1 d . . . O1 O 0.2706(4) 0.0916(3) 0.2395(2) 0.0601(10) Uani 1 1 d . . . H1A H 0.238(9) 0.099(6) 0.200(4) 0.13(3) Uiso 1 1 d . . . N1 N 0.4554(5) -0.0404(4) 0.1389(2) 0.0552(11) Uani 1 1 d . . . N2 N 0.5126(5) -0.0696(3) 0.2760(2) 0.0507(11) Uani 1 1 d . . . N3 N 0.5820(5) 0.1487(3) 0.3206(2) 0.0533(11) Uani 1 1 d . . . N4 N 0.7655(5) 0.0715(4) 0.1922(3) 0.0669(13) Uani 1 1 d . . . N5 N 0.4884(5) 0.2419(4) 0.1633(2) 0.0701(13) Uani 1 1 d . . . C1 C 0.3907(7) -0.0203(6) 0.0756(3) 0.0715(16) Uani 1 1 d . . . H1 H 0.3756 0.0576 0.0605 0.086 Uiso 1 1 calc R . . C2 C 0.3451(9) -0.1105(8) 0.0313(4) 0.099(2) Uani 1 1 d . . . H2 H 0.2971 -0.0947 -0.0132 0.119 Uiso 1 1 calc R . . C3 C 0.3703(9) -0.2221(8) 0.0530(4) 0.109(3) Uani 1 1 d . . . H3 H 0.3423 -0.2850 0.0229 0.130 Uiso 1 1 calc R . . C4 C 0.4354(8) -0.2433(6) 0.1175(4) 0.093(2) Uani 1 1 d . . . H4 H 0.4524 -0.3207 0.1331 0.111 Uiso 1 1 calc R . . C5 C 0.4766(6) -0.1507(5) 0.1601(3) 0.0621(15) Uani 1 1 d . . . C6 C 0.5513(7) -0.1656(4) 0.2319(3) 0.0648(16) Uani 1 1 d . . . H6A H 0.5139 -0.2393 0.2510 0.078 Uiso 1 1 calc R . . H6B H 0.6678 -0.1705 0.2309 0.078 Uiso 1 1 calc R . . C7 C 0.6316(7) -0.0559(4) 0.3350(3) 0.0646(16) Uani 1 1 d . . . H7A H 0.7392 -0.0678 0.3199 0.077 Uiso 1 1 calc R . . H7B H 0.6136 -0.1152 0.3701 0.077 Uiso 1 1 calc R . . C8 C 0.6206(6) 0.0634(4) 0.3655(3) 0.0608(15) Uani 1 1 d . . . C9 C 0.6471(8) 0.0851(6) 0.4343(3) 0.085(2) Uani 1 1 d . . . H9 H 0.6746 0.0232 0.4651 0.102 Uiso 1 1 calc R . . C10 C 0.6338(9) 0.1956(7) 0.4586(4) 0.100(2) Uani 1 1 d . . . H10 H 0.6518 0.2113 0.5061 0.119 Uiso 1 1 calc R . . C11 C 0.5942(8) 0.2831(6) 0.4133(4) 0.090(2) Uani 1 1 d . . . H11 H 0.5840 0.3607 0.4288 0.108 Uiso 1 1 calc R . . C12 C 0.5695(6) 0.2569(5) 0.3452(3) 0.0648(16) Uani 1 1 d . . . H12 H 0.5422 0.3180 0.3139 0.078 Uiso 1 1 calc R . . C13 C 0.3526(6) -0.0804(5) 0.2988(3) 0.0769(18) Uani 1 1 d . . . H13A H 0.3244 -0.1639 0.2976 0.092 Uiso 1 1 calc R . . H13B H 0.3575 -0.0556 0.3472 0.092 Uiso 1 1 calc R . . C14 C 0.2300(8) -0.0208(8) 0.2640(5) 0.154(4) Uani 1 1 d . . . H14A H 0.1435 -0.0116 0.2946 0.185 Uiso 1 1 calc R . . H14B H 0.1883 -0.0683 0.2244 0.185 Uiso 1 1 calc R . . C15 C 0.8682(6) 0.0872(4) 0.1590(3) 0.0517(12) Uani 1 1 d . . . C16 C 0.4808(6) 0.3187(4) 0.1260(3) 0.0484(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0468(4) 0.0387(4) 0.0562(5) 0.0067(3) 0.0036(3) -0.0003(3) S1 0.0587(9) 0.1024(13) 0.0698(11) -0.0031(9) 0.0123(8) -0.0125(8) S2 0.0957(12) 0.0633(9) 0.0608(10) 0.0220(7) 0.0076(9) 0.0068(8) O1 0.054(2) 0.064(2) 0.063(3) 0.015(2) 0.011(2) 0.0072(18) N1 0.049(3) 0.060(3) 0.057(3) -0.005(2) 0.007(2) -0.004(2) N2 0.050(2) 0.033(2) 0.069(3) 0.0072(18) 0.003(2) 0.0018(16) N3 0.053(3) 0.047(2) 0.058(3) 0.000(2) -0.006(2) 0.0079(19) N4 0.050(3) 0.070(3) 0.081(3) -0.009(2) 0.010(3) -0.006(2) N5 0.072(3) 0.058(3) 0.083(4) 0.023(3) 0.015(3) 0.009(2) C1 0.069(4) 0.092(5) 0.055(4) 0.000(4) 0.009(3) -0.002(3) C2 0.095(5) 0.139(7) 0.062(5) -0.026(5) -0.004(4) -0.009(5) C3 0.119(7) 0.112(7) 0.095(6) -0.059(5) 0.008(5) -0.018(5) C4 0.107(5) 0.062(4) 0.109(6) -0.033(4) 0.011(5) -0.014(4) C5 0.057(3) 0.050(3) 0.081(4) -0.010(3) 0.014(3) -0.002(3) C6 0.074(4) 0.034(3) 0.086(4) -0.001(3) 0.001(3) 0.013(2) C7 0.068(4) 0.057(3) 0.066(4) 0.013(3) -0.007(3) 0.012(3) C8 0.065(4) 0.058(4) 0.058(4) -0.001(3) -0.007(3) 0.011(3) C9 0.113(5) 0.076(4) 0.064(4) -0.001(3) -0.007(4) 0.029(4) C10 0.125(6) 0.100(6) 0.070(5) -0.020(4) -0.010(4) 0.028(5) C11 0.102(5) 0.080(5) 0.085(5) -0.028(4) -0.017(4) 0.016(4) C12 0.061(3) 0.048(3) 0.083(5) -0.005(3) -0.008(3) 0.003(3) C13 0.065(4) 0.056(3) 0.114(5) 0.030(3) 0.034(4) 0.000(3) C14 0.059(4) 0.180(8) 0.229(10) 0.157(8) 0.043(5) 0.028(5) C15 0.045(3) 0.051(3) 0.057(3) -0.011(3) -0.007(3) 0.000(2) C16 0.051(3) 0.045(3) 0.050(3) -0.002(2) 0.005(3) 0.004(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 Fe1 N5 2.016(4) . ? Fe1 N4 2.122(5) . ? Fe1 N3 2.178(4) . ? Fe1 N1 2.187(4) . ? Fe1 N2 2.219(4) . ? Fe1 O1 2.256(4) . ? S1 C15 1.626(6) . ? S2 C16 1.609(5) . ? O1 C14 1.431(8) . ? O1 H1A 0.80(7) . ? N1 C1 1.335(6) . ? N1 C5 1.343(6) . ? N2 C6 1.457(6) . ? N2 C13 1.466(6) . ? N2 C7 1.477(6) . ? N3 C8 1.341(6) . ? N3 C12 1.343(6) . ? N4 C15 1.144(6) . ? N5 C16 1.146(6) . ? C1 C2 1.387(9) . ? C1 H1 0.9500 . ? C2 C3 1.365(9) . ? C2 H2 0.9500 . ? C3 C4 1.359(9) . ? C3 H3 0.9500 . ? C4 C5 1.381(7) . ? C4 H4 0.9500 . ? C5 C6 1.503(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.504(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.373(8) . ? C9 C10 1.366(8) . ? C9 H9 0.9500 . ? C10 C11 1.366(8) . ? C10 H10 0.9500 . ? C11 C12 1.368(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.376(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Fe1 N4 95.90(19) . . ? N5 Fe1 N3 103.70(18) . . ? N4 Fe1 N3 95.86(17) . . ? N5 Fe1 N1 103.09(18) . . ? N4 Fe1 N1 89.34(16) . . ? N3 Fe1 N1 152.00(17) . . ? N5 Fe1 N2 167.43(17) . . ? N4 Fe1 N2 96.62(17) . . ? N3 Fe1 N2 76.08(15) . . ? N1 Fe1 N2 75.99(16) . . ? N5 Fe1 O1 89.61(16) . . ? N4 Fe1 O1 173.40(16) . . ? N3 Fe1 O1 86.31(15) . . ? N1 Fe1 O1 85.87(15) . . ? N2 Fe1 O1 77.83(14) . . ? C14 O1 Fe1 109.6(3) . . ? C14 O1 H1A 110(5) . . ? Fe1 O1 H1A 93(6) . . ? C1 N1 C5 119.0(5) . . ? C1 N1 Fe1 125.8(4) . . ? C5 N1 Fe1 115.2(4) . . ? C6 N2 C13 112.1(4) . . ? C6 N2 C7 112.0(4) . . ? C13 N2 C7 111.0(4) . . ? C6 N2 Fe1 107.0(3) . . ? C13 N2 Fe1 109.0(3) . . ? C7 N2 Fe1 105.4(3) . . ? C8 N3 C12 117.8(5) . . ? C8 N3 Fe1 115.1(3) . . ? C12 N3 Fe1 126.9(4) . . ? C15 N4 Fe1 152.5(4) . . ? C16 N5 Fe1 168.9(5) . . ? N1 C1 C2 121.6(6) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C3 C2 C1 118.8(7) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 119.9(7) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.2(7) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.4(6) . . ? N1 C5 C6 115.6(4) . . ? C4 C5 C6 122.9(6) . . ? N2 C6 C5 111.8(4) . . ? N2 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? N2 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N2 C7 C8 110.4(4) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 121.6(5) . . ? N3 C8 C7 115.3(5) . . ? C9 C8 C7 123.1(5) . . ? C10 C9 C8 120.0(6) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 118.9(6) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C12 118.8(6) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? N3 C12 C11 123.0(6) . . ? N3 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C14 C13 N2 119.0(5) . . ? C14 C13 H13A 107.6 . . ? N2 C13 H13A 107.6 . . ? C14 C13 H13B 107.6 . . ? N2 C13 H13B 107.6 . . ? H13A C13 H13B 107.0 . . ? C13 C14 O1 115.1(6) . . ? C13 C14 H14A 108.5 . . ? O1 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? O1 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? N4 C15 S1 179.2(5) . . ? N5 C16 S2 179.0(5) . . ? 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 N5 Fe1 O1 C14 165.4(5) . . . . ? N3 Fe1 O1 C14 -90.8(5) . . . . ? N1 Fe1 O1 C14 62.3(5) . . . . ? N2 Fe1 O1 C14 -14.3(5) . . . . ? N5 Fe1 N1 C1 -4.9(5) . . . . ? N4 Fe1 N1 C1 -100.8(4) . . . . ? N3 Fe1 N1 C1 157.9(4) . . . . ? N2 Fe1 N1 C1 162.2(4) . . . . ? O1 Fe1 N1 C1 83.8(4) . . . . ? N5 Fe1 N1 C5 177.0(3) . . . . ? N4 Fe1 N1 C5 81.1(4) . . . . ? N3 Fe1 N1 C5 -20.2(5) . . . . ? N2 Fe1 N1 C5 -15.9(3) . . . . ? O1 Fe1 N1 C5 -94.3(4) . . . . ? N5 Fe1 N2 C6 117.5(8) . . . . ? N4 Fe1 N2 C6 -57.5(3) . . . . ? N3 Fe1 N2 C6 -151.9(3) . . . . ? N1 Fe1 N2 C6 30.2(3) . . . . ? O1 Fe1 N2 C6 118.9(3) . . . . ? N5 Fe1 N2 C13 -3.9(10) . . . . ? N4 Fe1 N2 C13 -178.9(4) . . . . ? N3 Fe1 N2 C13 86.6(4) . . . . ? N1 Fe1 N2 C13 -91.3(4) . . . . ? O1 Fe1 N2 C13 -2.5(4) . . . . ? N5 Fe1 N2 C7 -123.1(8) . . . . ? N4 Fe1 N2 C7 61.9(3) . . . . ? N3 Fe1 N2 C7 -32.6(3) . . . . ? N1 Fe1 N2 C7 149.5(3) . . . . ? O1 Fe1 N2 C7 -121.7(3) . . . . ? N5 Fe1 N3 C8 -176.7(4) . . . . ? N4 Fe1 N3 C8 -79.1(4) . . . . ? N1 Fe1 N3 C8 20.6(5) . . . . ? N2 Fe1 N3 C8 16.2(4) . . . . ? O1 Fe1 N3 C8 94.6(4) . . . . ? N5 Fe1 N3 C12 8.8(5) . . . . ? N4 Fe1 N3 C12 106.4(4) . . . . ? N1 Fe1 N3 C12 -153.9(4) . . . . ? N2 Fe1 N3 C12 -158.2(5) . . . . ? O1 Fe1 N3 C12 -79.9(4) . . . . ? N5 Fe1 N4 C15 -24.4(9) . . . . ? N3 Fe1 N4 C15 -128.9(9) . . . . ? N1 Fe1 N4 C15 78.7(9) . . . . ? N2 Fe1 N4 C15 154.5(9) . . . . ? N4 Fe1 N5 C16 40(2) . . . . ? N3 Fe1 N5 C16 137(2) . . . . ? N1 Fe1 N5 C16 -51(2) . . . . ? N2 Fe1 N5 C16 -135(2) . . . . ? O1 Fe1 N5 C16 -137(2) . . . . ? C5 N1 C1 C2 0.0(8) . . . . ? Fe1 N1 C1 C2 -178.1(4) . . . . ? N1 C1 C2 C3 -1.4(10) . . . . ? C1 C2 C3 C4 1.6(11) . . . . ? C2 C3 C4 C5 -0.6(11) . . . . ? C1 N1 C5 C4 1.1(8) . . . . ? Fe1 N1 C5 C4 179.4(4) . . . . ? C1 N1 C5 C6 179.5(5) . . . . ? Fe1 N1 C5 C6 -2.2(6) . . . . ? C3 C4 C5 N1 -0.8(9) . . . . ? C3 C4 C5 C6 -179.1(6) . . . . ? C13 N2 C6 C5 78.5(5) . . . . ? C7 N2 C6 C5 -156.1(4) . . . . ? Fe1 N2 C6 C5 -41.0(5) . . . . ? N1 C5 C6 N2 30.2(7) . . . . ? C4 C5 C6 N2 -151.4(5) . . . . ? C6 N2 C7 C8 161.1(5) . . . . ? C13 N2 C7 C8 -72.8(5) . . . . ? Fe1 N2 C7 C8 45.1(5) . . . . ? C12 N3 C8 C9 -0.2(8) . . . . ? Fe1 N3 C8 C9 -175.2(5) . . . . ? C12 N3 C8 C7 179.5(5) . . . . ? Fe1 N3 C8 C7 4.5(6) . . . . ? N2 C7 C8 N3 -34.7(7) . . . . ? N2 C7 C8 C9 145.0(6) . . . . ? C7 C8 C9 C10 -179.5(6) . . . . ? Fe1 N3 C12 C11 174.3(4) . . . . ? C10 C11 C12 N3 0.1(10) . . . . ? C6 N2 C13 C14 -97.0(8) . . . . ? C7 N2 C13 C14 137.0(7) . . . . ? Fe1 N2 C13 C14 21.3(8) . . . . ? N2 C13 C14 O1 -36.4(11) . . . . ? Fe1 O1 C14 C13 30.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.506 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.077 #===END data_mnn37-ma _database_code_depnum_ccdc_archive 'CCDC 806667' #TrackingRef '- cif files (1-6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Mn N9 O' _chemical_formula_weight 381.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6742(8) _cell_length_b 13.3698(13) _cell_length_c 13.6701(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.150(2) _cell_angle_gamma 90.00 _cell_volume 1569.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11303 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3870 _reflns_number_gt 2614 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+3.3584P] 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 3870 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 0.35081(6) 0.61305(4) 0.21034(4) 0.01704(16) Uani 1 1 d . . . C1 C 0.0202(5) 0.5535(3) 0.2749(3) 0.0237(8) Uani 1 1 d . . . H1 H 0.0063 0.5168 0.2165 0.028 Uiso 1 1 calc R . . C2 C -0.0970(4) 0.5530(3) 0.3337(3) 0.0256(9) Uani 1 1 d . . . H2 H -0.1873 0.5160 0.3157 0.031 Uiso 1 1 calc R . . C3 C -0.0768(4) 0.6091(3) 0.4203(3) 0.0257(8) Uani 1 1 d . . . H3 H -0.1528 0.6093 0.4620 0.031 Uiso 1 1 calc R . . C4 C 0.0578(4) 0.6644(3) 0.4435(3) 0.0224(8) Uani 1 1 d . . . H4 H 0.0715 0.7051 0.4992 0.027 Uiso 1 1 calc R . . C5 C 0.1726(4) 0.6586(3) 0.3825(3) 0.0173(7) Uani 1 1 d . . . C6 C 0.3286(4) 0.7081(3) 0.4094(3) 0.0212(8) Uani 1 1 d . . . H6A H 0.3168 0.7683 0.4472 0.025 Uiso 1 1 calc R . . H6B H 0.3985 0.6632 0.4501 0.025 Uiso 1 1 calc R . . C7 C 0.5665(4) 0.7514(3) 0.3426(2) 0.0201(8) Uani 1 1 d . . . H7A H 0.6086 0.7062 0.3952 0.024 Uiso 1 1 calc R . . H7B H 0.5844 0.8192 0.3666 0.024 Uiso 1 1 calc R . . C8 C 0.6516(4) 0.7355(3) 0.2545(3) 0.0191(7) Uani 1 1 d . . . C9 C 0.7864(4) 0.7855(3) 0.2440(3) 0.0233(8) Uani 1 1 d . . . H9 H 0.8252 0.8345 0.2891 0.028 Uiso 1 1 calc R . . C10 C 0.8641(5) 0.7614(3) 0.1648(3) 0.0288(9) Uani 1 1 d . . . H10 H 0.9567 0.7934 0.1570 0.035 Uiso 1 1 calc R . . C11 C 0.8022(4) 0.6896(3) 0.0977(3) 0.0253(9) Uani 1 1 d . . . H11 H 0.8528 0.6719 0.0447 0.030 Uiso 1 1 calc R . . C12 C 0.6633(5) 0.6448(3) 0.1114(3) 0.0239(8) Uani 1 1 d . . . H12 H 0.6200 0.5976 0.0656 0.029 Uiso 1 1 calc R . . C13 C 0.3157(4) 0.8224(3) 0.2692(3) 0.0209(8) Uani 1 1 d . . . H13A H 0.3695 0.8833 0.2927 0.025 Uiso 1 1 calc R . . H13B H 0.2098 0.8259 0.2841 0.025 Uiso 1 1 calc R . . C14 C 0.3150(5) 0.8118(3) 0.1591(3) 0.0235(8) Uani 1 1 d . . . H14A H 0.2474 0.8619 0.1244 0.028 Uiso 1 1 calc R . . H14B H 0.4194 0.8218 0.1432 0.028 Uiso 1 1 calc R . . O1 O 0.2615(3) 0.71489(18) 0.12901(17) 0.0201(5) Uani 1 1 d . . . N1 N 0.1538(3) 0.6048(2) 0.2988(2) 0.0185(6) Uani 1 1 d . . . N2 N 0.3964(3) 0.7341(2) 0.3182(2) 0.0173(6) Uani 1 1 d . . . N3 N 0.5882(3) 0.6663(2) 0.1881(2) 0.0200(7) Uani 1 1 d . . . N4 N 0.4588(4) 0.5118(2) 0.3030(2) 0.0271(8) Uani 1 1 d . . . N5 N 0.4080(4) 0.4756(2) 0.3727(2) 0.0216(7) Uani 1 1 d . . . N6 N 0.3660(4) 0.4390(3) 0.4402(3) 0.0307(8) Uani 1 1 d . . . N7 N 0.2859(4) 0.5128(2) 0.1028(2) 0.0289(8) Uani 1 1 d . . . N8 N 0.2063(4) 0.5418(2) 0.0275(3) 0.0264(7) Uani 1 1 d . . . N9 N 0.1313(5) 0.5660(3) -0.0450(3) 0.0391(9) 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 0.0207(3) 0.0147(3) 0.0163(3) -0.0005(2) 0.0045(2) 0.0008(2) C1 0.028(2) 0.0157(18) 0.025(2) 0.0008(15) -0.0052(16) -0.0018(15) C2 0.0164(18) 0.022(2) 0.038(2) 0.0082(17) 0.0024(16) -0.0036(15) C3 0.0206(19) 0.032(2) 0.025(2) 0.0113(17) 0.0053(15) 0.0043(17) C4 0.0220(19) 0.027(2) 0.0182(18) 0.0036(15) 0.0030(15) 0.0043(16) C5 0.0174(18) 0.0169(17) 0.0174(18) 0.0023(14) 0.0020(14) 0.0039(14) C6 0.026(2) 0.0202(19) 0.0183(18) 0.0001(14) 0.0074(15) 0.0002(15) C7 0.0169(18) 0.028(2) 0.0139(17) -0.0065(15) -0.0026(14) -0.0078(15) C8 0.0179(18) 0.0200(18) 0.0188(18) 0.0023(14) 0.0010(14) 0.0000(15) C9 0.0185(19) 0.0227(19) 0.028(2) 0.0009(16) 0.0019(16) -0.0016(15) C10 0.024(2) 0.031(2) 0.034(2) 0.0081(18) 0.0096(17) -0.0006(17) C11 0.021(2) 0.031(2) 0.025(2) 0.0051(16) 0.0093(16) 0.0061(16) C12 0.027(2) 0.0209(19) 0.024(2) 0.0020(15) 0.0054(16) 0.0043(16) C13 0.0214(19) 0.0163(18) 0.025(2) -0.0028(14) 0.0023(15) -0.0015(15) C14 0.035(2) 0.0124(17) 0.023(2) -0.0011(14) 0.0036(17) -0.0022(16) O1 0.0271(14) 0.0186(13) 0.0144(12) -0.0007(10) 0.0019(10) -0.0019(11) N1 0.0192(15) 0.0168(15) 0.0197(16) 0.0013(12) 0.0037(12) 0.0029(13) N2 0.0168(15) 0.0190(15) 0.0163(15) 0.0029(12) 0.0026(12) 0.0017(12) N3 0.0178(16) 0.0224(16) 0.0209(16) 0.0007(12) 0.0063(12) 0.0018(13) N4 0.036(2) 0.0230(17) 0.0247(18) 0.0073(14) 0.0117(15) 0.0090(15) N5 0.0231(17) 0.0170(16) 0.0236(17) -0.0001(13) -0.0006(14) 0.0029(13) N6 0.032(2) 0.0297(19) 0.031(2) 0.0071(15) 0.0054(16) -0.0029(16) N7 0.044(2) 0.0180(16) 0.0250(18) -0.0026(14) 0.0041(16) 0.0010(15) N8 0.036(2) 0.0188(16) 0.0256(19) -0.0061(14) 0.0082(16) -0.0061(14) N9 0.054(3) 0.035(2) 0.026(2) -0.0002(16) -0.0018(18) -0.0119(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 1.856(2) . ? Mn1 N4 1.994(3) . ? Mn1 N7 2.010(3) . ? Mn1 N2 2.188(3) . ? Mn1 N1 2.232(3) . ? Mn1 N3 2.240(3) . ? C1 N1 1.346(5) . ? C1 C2 1.382(5) . ? C1 H1 0.9300 . ? C2 C3 1.392(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(5) . ? C3 H3 0.9300 . ? C4 C5 1.388(5) . ? C4 H4 0.9300 . ? C5 N1 1.341(4) . ? C5 C6 1.504(5) . ? C6 N2 1.492(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N2 1.484(4) . ? C7 C8 1.515(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N3 1.356(5) . ? C8 C9 1.371(5) . ? C9 C10 1.392(5) . ? C9 H9 0.9300 . ? C10 C11 1.382(6) . ? C10 H10 0.9300 . ? C11 C12 1.382(5) . ? C11 H11 0.9300 . ? C12 N3 1.342(5) . ? C12 H12 0.9300 . ? C13 N2 1.484(4) . ? C13 C14 1.510(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O1 1.417(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N4 N5 1.207(4) . ? N5 N6 1.148(4) . ? N7 N8 1.219(5) . ? N8 N9 1.152(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 Mn1 N4 175.37(13) . . ? O1 Mn1 N7 90.09(12) . . ? N4 Mn1 N7 93.98(14) . . ? O1 Mn1 N2 83.19(11) . . ? N4 Mn1 N2 92.86(12) . . ? N7 Mn1 N2 172.57(13) . . ? O1 Mn1 N1 94.24(11) . . ? N4 Mn1 N1 87.07(12) . . ? N7 Mn1 N1 101.92(13) . . ? N2 Mn1 N1 75.55(11) . . ? O1 Mn1 N3 89.97(11) . . ? N4 Mn1 N3 86.79(13) . . ? N7 Mn1 N3 106.30(13) . . ? N2 Mn1 N3 76.95(11) . . ? N1 Mn1 N3 151.45(11) . . ? N1 C1 C2 122.7(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 118.6(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.1(3) . . ? N1 C5 C6 116.2(3) . . ? C4 C5 C6 121.7(3) . . ? N2 C6 C5 110.2(3) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 112.4(3) . . ? N2 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? N2 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? N3 C8 C9 122.3(3) . . ? N3 C8 C7 115.5(3) . . ? C9 C8 C7 122.2(3) . . ? C8 C9 C10 118.8(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.4(4) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 118.4(4) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? N3 C12 C11 122.8(4) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N2 C13 C14 108.1(3) . . ? N2 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N2 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? O1 C14 C13 109.3(3) . . ? O1 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? O1 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C14 O1 Mn1 113.9(2) . . ? C5 N1 C1 118.5(3) . . ? C5 N1 Mn1 115.2(2) . . ? C1 N1 Mn1 126.3(2) . . ? C7 N2 C13 111.6(3) . . ? C7 N2 C6 110.2(3) . . ? C13 N2 C6 110.3(3) . . ? C7 N2 Mn1 110.2(2) . . ? C13 N2 Mn1 104.8(2) . . ? C6 N2 Mn1 109.6(2) . . ? C12 N3 C8 118.3(3) . . ? C12 N3 Mn1 126.5(3) . . ? C8 N3 Mn1 114.8(2) . . ? N5 N4 Mn1 125.7(3) . . ? N6 N5 N4 176.9(4) . . ? N8 N7 Mn1 118.1(3) . . ? N9 N8 N7 177.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.9(6) . . . . ? C1 C2 C3 C4 1.2(5) . . . . ? C2 C3 C4 C5 -3.3(5) . . . . ? C3 C4 C5 N1 3.5(5) . . . . ? C3 C4 C5 C6 -173.3(3) . . . . ? N1 C5 C6 N2 30.7(4) . . . . ? C4 C5 C6 N2 -152.4(3) . . . . ? N2 C7 C8 N3 -30.9(4) . . . . ? N2 C7 C8 C9 151.0(3) . . . . ? N3 C8 C9 C10 -2.7(6) . . . . ? C7 C8 C9 C10 175.3(3) . . . . ? C8 C9 C10 C11 1.3(6) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C10 C11 C12 N3 -1.6(6) . . . . ? N2 C13 C14 O1 49.4(4) . . . . ? C13 C14 O1 Mn1 -45.7(4) . . . . ? N7 Mn1 O1 C14 -161.6(2) . . . . ? N2 Mn1 O1 C14 21.6(2) . . . . ? N1 Mn1 O1 C14 96.5(2) . . . . ? N3 Mn1 O1 C14 -55.3(2) . . . . ? C4 C5 N1 C1 -1.4(5) . . . . ? C6 C5 N1 C1 175.5(3) . . . . ? C4 C5 N1 Mn1 177.4(3) . . . . ? C6 C5 N1 Mn1 -5.7(4) . . . . ? C2 C1 N1 C5 -0.8(5) . . . . ? C2 C1 N1 Mn1 -179.4(3) . . . . ? O1 Mn1 N1 C5 -94.8(2) . . . . ? N4 Mn1 N1 C5 80.7(3) . . . . ? N7 Mn1 N1 C5 174.2(2) . . . . ? N2 Mn1 N1 C5 -13.0(2) . . . . ? N3 Mn1 N1 C5 2.9(4) . . . . ? O1 Mn1 N1 C1 83.8(3) . . . . ? N4 Mn1 N1 C1 -100.6(3) . . . . ? N7 Mn1 N1 C1 -7.2(3) . . . . ? N2 Mn1 N1 C1 165.6(3) . . . . ? N3 Mn1 N1 C1 -178.4(3) . . . . ? C8 C7 N2 C13 -80.9(4) . . . . ? C8 C7 N2 C6 156.2(3) . . . . ? C8 C7 N2 Mn1 35.1(3) . . . . ? C14 C13 N2 C7 89.2(3) . . . . ? C14 C13 N2 C6 -147.9(3) . . . . ? C14 C13 N2 Mn1 -30.1(3) . . . . ? C5 C6 N2 C7 -161.5(3) . . . . ? C5 C6 N2 C13 74.8(4) . . . . ? C5 C6 N2 Mn1 -40.1(3) . . . . ? O1 Mn1 N2 C7 -114.0(2) . . . . ? N4 Mn1 N2 C7 63.6(2) . . . . ? N1 Mn1 N2 C7 149.8(2) . . . . ? N3 Mn1 N2 C7 -22.4(2) . . . . ? O1 Mn1 N2 C13 6.2(2) . . . . ? N4 Mn1 N2 C13 -176.2(2) . . . . ? N1 Mn1 N2 C13 -90.0(2) . . . . ? N3 Mn1 N2 C13 97.8(2) . . . . ? N4 Mn1 N2 C6 -57.9(2) . . . . ? N1 Mn1 N2 C6 28.4(2) . . . . ? N3 Mn1 N2 C6 -143.9(2) . . . . ? C11 C12 N3 C8 0.3(5) . . . . ? C11 C12 N3 Mn1 172.5(3) . . . . ? C9 C8 N3 C12 1.9(5) . . . . ? C7 C8 N3 C12 -176.2(3) . . . . ? C9 C8 N3 Mn1 -171.2(3) . . . . ? C7 C8 N3 Mn1 10.7(4) . . . . ? O1 Mn1 N3 C12 -82.7(3) . . . . ? N4 Mn1 N3 C12 100.6(3) . . . . ? N7 Mn1 N3 C12 7.4(3) . . . . ? N2 Mn1 N3 C12 -165.7(3) . . . . ? N1 Mn1 N3 C12 178.5(3) . . . . ? O1 Mn1 N3 C8 89.8(3) . . . . ? N4 Mn1 N3 C8 -86.9(3) . . . . ? N7 Mn1 N3 C8 179.8(2) . . . . ? N2 Mn1 N3 C8 6.7(2) . . . . ? N1 Mn1 N3 C8 -9.1(4) . . . . ? N7 Mn1 N4 N5 -102.3(3) . . . . ? N2 Mn1 N4 N5 74.8(3) . . . . ? N1 Mn1 N4 N5 -0.5(3) . . . . ? N3 Mn1 N4 N5 151.6(3) . . . . ? O1 Mn1 N7 N8 -5.0(3) . . . . ? N4 Mn1 N7 N8 177.2(3) . . . . ? N1 Mn1 N7 N8 89.3(3) . . . . ? N3 Mn1 N7 N8 -95.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.022 _refine_diff_density_min -1.029 _refine_diff_density_rms 0.149 data_ks1 _database_code_depnum_ccdc_archive 'CCDC 806668' #TrackingRef '- cif files (1-6).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Mn N5 O S2' _chemical_formula_weight 414.41 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' Mn Mn 0.3368 0.7283 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.3632(12) _cell_length_b 11.6074(17) _cell_length_c 9.7721(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.997(3) _cell_angle_gamma 90.00 _cell_volume 946.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5965 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4078 _reflns_number_gt 3412 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+1.8783P] 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 (1983), 1616 Friedel pairs' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 4078 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.21100(9) 0.55767(7) 0.06714(8) 0.01853(19) Uani 1 1 d . . . N1 N 0.1544(6) 0.4956(4) -0.1508(5) 0.0259(11) Uani 1 1 d . . . N2 N 0.2346(5) 0.7162(4) -0.0711(4) 0.0178(9) Uani 1 1 d . . . N3 N 0.2697(6) 0.7059(4) 0.2135(5) 0.0225(11) Uani 1 1 d . . . O1 O 0.4795(4) 0.5668(4) 0.0319(4) 0.0277(8) Uani 1 1 d . . . H1A H 0.5356 0.5493 0.1035 0.033 Uiso 1 1 calc R . . C1 C 0.1607(8) 0.3862(5) -0.1947(7) 0.0302(15) Uani 1 1 d . . . H1 H 0.1857 0.3272 -0.1292 0.036 Uiso 1 1 calc R . . C2 C 0.1323(8) 0.3557(6) -0.3308(7) 0.0361(16) Uani 1 1 d . . . H2 H 0.1401 0.2777 -0.3589 0.043 Uiso 1 1 calc R . . C3 C 0.0925(8) 0.4409(6) -0.4245(7) 0.0358(15) Uani 1 1 d . . . H3 H 0.0704 0.4225 -0.5187 0.043 Uiso 1 1 calc R . . C4 C 0.0849(7) 0.5543(7) -0.3798(5) 0.0327(12) Uani 1 1 d . . . H4 H 0.0570 0.6144 -0.4429 0.039 Uiso 1 1 calc R . . C5 C 0.1185(6) 0.5785(4) -0.2425(6) 0.0225(13) Uani 1 1 d . . . C6 C 0.1130(7) 0.6999(5) -0.1861(6) 0.0255(13) Uani 1 1 d . . . H6A H 0.1322 0.7556 -0.2598 0.031 Uiso 1 1 calc R . . H6B H 0.0052 0.7151 -0.1543 0.031 Uiso 1 1 calc R . . C7 C 0.2013(7) 0.8195(5) 0.0086(6) 0.0258(13) Uani 1 1 d . . . H7A H 0.0842 0.8332 0.0027 0.031 Uiso 1 1 calc R . . H7B H 0.2526 0.8867 -0.0327 0.031 Uiso 1 1 calc R . . C8 C 0.2604(6) 0.8107(5) 0.1570(6) 0.0249(13) Uani 1 1 d . . . C9 C 0.2942(8) 0.9091(5) 0.2339(7) 0.0339(15) Uani 1 1 d . . . H9 H 0.2824 0.9831 0.1930 0.041 Uiso 1 1 calc R . . C10 C 0.3452(9) 0.8981(7) 0.3703(9) 0.046(2) Uani 1 1 d . . . H10 H 0.3761 0.9640 0.4233 0.056 Uiso 1 1 calc R . . C11 C 0.3508(9) 0.7899(6) 0.4288(7) 0.0417(17) Uani 1 1 d . . . H11 H 0.3780 0.7805 0.5242 0.050 Uiso 1 1 calc R . . C12 C 0.3163(8) 0.6959(6) 0.3465(7) 0.0357(15) Uani 1 1 d . . . H12 H 0.3261 0.6211 0.3856 0.043 Uiso 1 1 calc R . . C13 C 0.3979(6) 0.7165(6) -0.1227(6) 0.0291(13) Uani 1 1 d . . . H13A H 0.4225 0.7949 -0.1552 0.035 Uiso 1 1 calc R . . H13B H 0.3998 0.6634 -0.2018 0.035 Uiso 1 1 calc R . . C14 C 0.5254(7) 0.6806(5) -0.0142(7) 0.0269(13) Uani 1 1 d . . . H14A H 0.6316 0.6776 -0.0530 0.032 Uiso 1 1 calc R . . H14B H 0.5308 0.7358 0.0632 0.032 Uiso 1 1 calc R . . N4 N 0.2543(7) 0.4071(4) 0.1827(6) 0.0291(13) Uani 1 1 d . . . C15 C 0.2664(6) 0.3306(5) 0.2553(6) 0.0208(12) Uani 1 1 d . . . S1 S 0.28148(19) 0.21919(14) 0.35834(17) 0.0286(4) Uani 1 1 d . . . N5 N -0.0402(6) 0.5858(4) 0.1057(6) 0.0331(13) Uani 1 1 d . . . C16 C -0.1352(6) 0.5651(6) 0.1846(5) 0.0262(12) Uani 1 1 d . . . S2 S -0.2706(2) 0.53472(14) 0.29329(16) 0.0368(4) 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 0.0163(4) 0.0137(3) 0.0256(4) 0.0030(4) 0.0017(3) 0.0001(4) N1 0.021(3) 0.024(3) 0.032(3) 0.000(2) 0.002(2) 0.004(2) N2 0.017(2) 0.018(2) 0.019(2) 0.002(2) 0.0016(17) 0.0009(19) N3 0.019(2) 0.021(3) 0.028(3) 0.000(2) 0.001(2) -0.001(2) O1 0.0234(19) 0.028(2) 0.031(2) 0.008(2) 0.0007(15) 0.005(2) C1 0.032(4) 0.020(3) 0.038(4) 0.003(3) 0.004(3) 0.006(3) C2 0.038(4) 0.028(3) 0.043(4) -0.007(3) 0.004(3) -0.002(3) C3 0.043(4) 0.034(4) 0.031(3) -0.012(3) 0.001(3) 0.004(3) C4 0.038(3) 0.033(3) 0.027(3) 0.008(4) 0.000(2) 0.010(4) C5 0.015(3) 0.019(3) 0.033(3) -0.002(2) 0.001(2) 0.003(2) C6 0.030(3) 0.024(3) 0.023(3) 0.004(2) 0.001(2) 0.003(3) C7 0.027(3) 0.019(3) 0.031(3) -0.002(2) -0.005(3) 0.006(2) C8 0.016(3) 0.027(3) 0.032(3) 0.000(3) 0.003(3) 0.003(2) C9 0.049(4) 0.020(3) 0.033(4) -0.003(3) 0.001(3) -0.001(3) C10 0.043(4) 0.045(5) 0.049(5) -0.019(4) -0.008(4) -0.011(4) C11 0.058(5) 0.046(4) 0.020(3) -0.010(3) -0.006(3) -0.002(3) C12 0.034(4) 0.036(4) 0.036(4) 0.006(3) -0.002(3) 0.004(3) C13 0.022(3) 0.030(3) 0.036(3) 0.008(3) 0.006(2) -0.002(3) C14 0.017(3) 0.022(3) 0.042(4) 0.003(3) 0.003(3) 0.000(2) N4 0.033(3) 0.020(3) 0.034(3) 0.010(2) 0.002(2) 0.008(2) C15 0.014(3) 0.024(3) 0.025(3) -0.004(3) 0.000(2) 0.002(2) S1 0.0297(8) 0.0271(8) 0.0288(8) 0.0101(7) 0.0004(7) 0.0034(7) N5 0.023(3) 0.023(3) 0.054(3) -0.009(2) 0.008(2) -0.0061(19) C16 0.022(3) 0.022(3) 0.033(3) -0.015(3) -0.012(2) -0.003(3) S2 0.0399(9) 0.0430(12) 0.0281(8) 0.0007(7) 0.0061(7) -0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N4 2.099(5) . ? Mn1 N5 2.184(5) . ? Mn1 N1 2.267(5) . ? Mn1 N3 2.269(5) . ? Mn1 O1 2.298(4) . ? Mn1 N2 2.300(4) . ? N1 C5 1.334(7) . ? N1 C1 1.343(8) . ? N2 C7 1.467(7) . ? N2 C6 1.474(7) . ? N2 C13 1.488(7) . ? N3 C12 1.335(8) . ? N3 C8 1.336(7) . ? O1 C14 1.456(7) . ? O1 H1A 0.8400 . ? C1 C2 1.381(10) . ? C1 H1 0.9500 . ? C2 C3 1.372(9) . ? C2 H2 0.9500 . ? C3 C4 1.390(10) . ? C3 H3 0.9500 . ? C4 C5 1.380(8) . ? C4 H4 0.9500 . ? C5 C6 1.515(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.503(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.385(8) . ? C9 C10 1.377(10) . ? C9 H9 0.9500 . ? C10 C11 1.379(11) . ? C10 H10 0.9500 . ? C11 C12 1.374(9) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.509(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N4 C15 1.136(8) . ? C15 S1 1.639(6) . ? N5 C16 1.170(7) . ? C16 S2 1.644(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Mn1 N5 99.4(2) . . ? N4 Mn1 N1 105.0(2) . . ? N5 Mn1 N1 93.96(19) . . ? N4 Mn1 N3 105.69(18) . . ? N5 Mn1 N3 86.92(18) . . ? N1 Mn1 N3 148.76(18) . . ? N4 Mn1 O1 89.2(2) . . ? N5 Mn1 O1 168.69(17) . . ? N1 Mn1 O1 90.92(16) . . ? N3 Mn1 O1 83.63(17) . . ? N4 Mn1 N2 164.59(19) . . ? N5 Mn1 N2 96.01(17) . . ? N1 Mn1 N2 73.91(17) . . ? N3 Mn1 N2 74.94(17) . . ? O1 Mn1 N2 75.54(15) . . ? C5 N1 C1 118.6(5) . . ? C5 N1 Mn1 115.1(4) . . ? C1 N1 Mn1 126.2(4) . . ? C7 N2 C6 111.3(4) . . ? C7 N2 C13 113.0(5) . . ? C6 N2 C13 110.1(4) . . ? C7 N2 Mn1 108.3(3) . . ? C6 N2 Mn1 105.2(3) . . ? C13 N2 Mn1 108.6(3) . . ? C12 N3 C8 119.1(5) . . ? C12 N3 Mn1 125.7(4) . . ? C8 N3 Mn1 115.2(4) . . ? C14 O1 Mn1 111.7(3) . . ? C14 O1 H1A 109.5 . . ? Mn1 O1 H1A 111.0 . . ? N1 C1 C2 122.8(6) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.4(6) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.1(6) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.2(6) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 121.8(6) . . ? N1 C5 C6 115.9(5) . . ? C4 C5 C6 122.3(6) . . ? N2 C6 C5 111.1(5) . . ? N2 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 113.3(5) . . ? N2 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N3 C8 C9 121.5(6) . . ? N3 C8 C7 117.8(5) . . ? C9 C8 C7 120.6(5) . . ? C10 C9 C8 119.1(6) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 119.0(7) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C12 C11 C10 118.7(6) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N3 C12 C11 122.4(6) . . ? N3 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? N2 C13 C14 112.5(5) . . ? N2 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? O1 C14 C13 106.3(4) . . ? O1 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? O1 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C15 N4 Mn1 172.3(5) . . ? N4 C15 S1 179.0(6) . . ? C16 N5 Mn1 142.0(5) . . ? N5 C16 S2 179.0(5) . . ? 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 Mn1 N1 C5 178.4(4) . . . . ? N5 Mn1 N1 C5 77.5(4) . . . . ? N3 Mn1 N1 C5 -13.1(6) . . . . ? O1 Mn1 N1 C5 -92.3(4) . . . . ? N2 Mn1 N1 C5 -17.6(4) . . . . ? N4 Mn1 N1 C1 -4.6(5) . . . . ? N5 Mn1 N1 C1 -105.5(5) . . . . ? N3 Mn1 N1 C1 163.9(4) . . . . ? O1 Mn1 N1 C1 84.7(5) . . . . ? N2 Mn1 N1 C1 159.4(5) . . . . ? N4 Mn1 N2 C7 -119.3(8) . . . . ? N5 Mn1 N2 C7 60.4(4) . . . . ? N1 Mn1 N2 C7 152.8(4) . . . . ? N3 Mn1 N2 C7 -24.8(3) . . . . ? O1 Mn1 N2 C7 -112.0(4) . . . . ? N4 Mn1 N2 C6 121.6(7) . . . . ? N5 Mn1 N2 C6 -58.8(4) . . . . ? N1 Mn1 N2 C6 33.6(3) . . . . ? N3 Mn1 N2 C6 -144.0(3) . . . . ? O1 Mn1 N2 C6 128.9(4) . . . . ? N4 Mn1 N2 C13 3.8(9) . . . . ? N5 Mn1 N2 C13 -176.6(4) . . . . ? N1 Mn1 N2 C13 -84.2(4) . . . . ? N3 Mn1 N2 C13 98.2(4) . . . . ? O1 Mn1 N2 C13 11.1(3) . . . . ? N4 Mn1 N3 C12 -2.1(5) . . . . ? N5 Mn1 N3 C12 96.8(5) . . . . ? N1 Mn1 N3 C12 -170.6(5) . . . . ? O1 Mn1 N3 C12 -89.4(5) . . . . ? N2 Mn1 N3 C12 -166.1(5) . . . . ? N4 Mn1 N3 C8 175.6(4) . . . . ? N5 Mn1 N3 C8 -85.5(4) . . . . ? N1 Mn1 N3 C8 7.1(6) . . . . ? O1 Mn1 N3 C8 88.3(4) . . . . ? N2 Mn1 N3 C8 11.6(4) . . . . ? N4 Mn1 O1 C14 -163.0(4) . . . . ? N5 Mn1 O1 C14 -23.5(11) . . . . ? N1 Mn1 O1 C14 92.1(4) . . . . ? N3 Mn1 O1 C14 -57.1(4) . . . . ? N2 Mn1 O1 C14 19.0(3) . . . . ? C5 N1 C1 C2 0.3(9) . . . . ? Mn1 N1 C1 C2 -176.6(5) . . . . ? N1 C1 C2 C3 -1.5(10) . . . . ? C1 C2 C3 C4 1.1(10) . . . . ? C2 C3 C4 C5 0.4(9) . . . . ? C1 N1 C5 C4 1.3(8) . . . . ? Mn1 N1 C5 C4 178.5(4) . . . . ? C1 N1 C5 C6 179.8(5) . . . . ? Mn1 N1 C5 C6 -2.9(6) . . . . ? C3 C4 C5 N1 -1.6(8) . . . . ? C3 C4 C5 C6 179.9(6) . . . . ? C7 N2 C6 C5 -163.7(5) . . . . ? C13 N2 C6 C5 70.2(6) . . . . ? Mn1 N2 C6 C5 -46.6(5) . . . . ? N1 C5 C6 N2 35.0(7) . . . . ? C4 C5 C6 N2 -146.5(5) . . . . ? C6 N2 C7 C8 150.7(5) . . . . ? C13 N2 C7 C8 -84.9(6) . . . . ? Mn1 N2 C7 C8 35.5(6) . . . . ? C12 N3 C8 C9 -1.6(9) . . . . ? Mn1 N3 C8 C9 -179.5(5) . . . . ? C12 N3 C8 C7 -177.7(5) . . . . ? Mn1 N3 C8 C7 4.5(6) . . . . ? N2 C7 C8 N3 -28.1(7) . . . . ? N2 C7 C8 C9 155.8(5) . . . . ? N3 C8 C9 C10 2.8(10) . . . . ? C7 C8 C9 C10 178.8(6) . . . . ? C8 C9 C10 C11 -4.3(11) . . . . ? C9 C10 C11 C12 4.6(12) . . . . ? C8 N3 C12 C11 2.0(10) . . . . ? Mn1 N3 C12 C11 179.6(5) . . . . ? C10 C11 C12 N3 -3.5(11) . . . . ? C7 N2 C13 C14 80.2(6) . . . . ? C6 N2 C13 C14 -154.7(5) . . . . ? Mn1 N2 C13 C14 -40.0(6) . . . . ? Mn1 O1 C14 C13 -44.6(5) . . . . ? N2 C13 C14 O1 57.1(6) . . . . ? N4 Mn1 N5 C16 23.8(8) . . . . ? N1 Mn1 N5 C16 129.7(7) . . . . ? N3 Mn1 N5 C16 -81.6(7) . . . . ? O1 Mn1 N5 C16 -114.9(10) . . . . ? N2 Mn1 N5 C16 -156.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.657 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.100