data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 Mn N4 O8' _chemical_formula_weight 625.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5296(14) _cell_length_b 8.8986(14) _cell_length_c 10.5757(15) _cell_angle_alpha 71.300(4) _cell_angle_beta 78.698(4) _cell_angle_gamma 74.264(5) _cell_volume 726.59(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2628 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.61 _exptl_crystal_description plan _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 323 _exptl_absorpt_coefficient_mu 0.512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8784 _exptl_absorpt_correction_T_max 0.9506 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6072 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.75 _reflns_number_total 2748 _reflns_number_gt 2121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0960P)^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 2748 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.5000 1.0000 0.0000 0.0316(2) Uani 1 2 d S . . N2 N 0.3433(3) 0.1983(3) 0.8469(2) 0.0393(6) Uani 1 1 d . . . N1 N -0.0143(3) 0.7059(3) 0.5757(2) 0.0333(6) Uani 1 1 d . . . O1 O 0.2857(3) 0.9460(2) 0.1339(2) 0.0432(5) Uani 1 1 d . . . O2 O 0.2778(4) 0.7074(3) 0.1143(2) 0.0650(8) Uani 1 1 d . . . O3 O 0.5056(3) 1.1802(3) 0.0964(2) 0.0440(5) Uani 1 1 d . . . O4 O 0.2664(4) 0.3844(3) 0.2029(3) 0.0984(12) Uani 1 1 d . . . C13 C 0.3795(4) 0.2039(4) 0.7181(3) 0.0423(8) Uani 1 1 d . . . H13 H 0.4550 0.1168 0.6949 0.051 Uiso 1 1 calc R . . C12 C 0.3105(4) 0.3333(4) 0.6161(3) 0.0396(7) Uani 1 1 d . . . H12 H 0.3414 0.3325 0.5270 0.047 Uiso 1 1 calc R . . C11 C 0.1951(3) 0.4641(3) 0.6471(3) 0.0331(7) Uani 1 1 d . . . C15 C 0.1552(4) 0.4557(4) 0.7821(3) 0.0456(8) Uani 1 1 d . . . H15 H 0.0780 0.5397 0.8086 0.055 Uiso 1 1 calc R . . C14 C 0.2299(4) 0.3228(4) 0.8773(3) 0.0508(9) Uani 1 1 d . . . H14 H 0.1999 0.3194 0.9674 0.061 Uiso 1 1 calc R . . C9 C 0.1242(3) 0.6087(3) 0.5406(3) 0.0323(6) Uani 1 1 d . . . C8 C 0.2047(3) 0.6416(3) 0.4085(3) 0.0353(7) Uani 1 1 d . . . H7 H 0.2999 0.5691 0.3869 0.042 Uiso 1 1 calc R . . C7 C 0.1452(3) 0.7782(3) 0.3118(3) 0.0325(7) Uani 1 1 d . . . C10 C 0.2431(4) 0.8143(4) 0.1732(3) 0.0366(7) Uani 1 1 d . . . C6 C -0.0011(3) 0.8863(3) 0.3462(3) 0.0330(7) Uani 1 1 d . . . C5 C -0.0775(3) 0.8443(3) 0.4804(3) 0.0336(7) Uani 1 1 d . . . C4 C -0.2241(4) 0.9486(4) 0.5192(3) 0.0421(8) Uani 1 1 d . . . H4 H -0.2741 0.9229 0.6075 0.051 Uiso 1 1 calc R . . C3 C -0.2914(4) 1.0856(4) 0.4278(3) 0.0480(8) Uani 1 1 d . . . H3 H -0.3877 1.1534 0.4542 0.058 Uiso 1 1 calc R . . C2 C -0.2190(4) 1.1270(4) 0.2950(3) 0.0458(8) Uani 1 1 d . . . H2 H -0.2682 1.2211 0.2338 0.055 Uiso 1 1 calc R . . C1 C -0.0766(4) 1.0308(4) 0.2537(3) 0.0418(8) Uani 1 1 d . . . H1 H -0.0291 1.0601 0.1649 0.050 Uiso 1 1 calc R . . H4A H 0.2667 0.4841 0.1866 0.063 Uiso 1 1 d R . . H4B H 0.1963 0.3552 0.2686 0.063 Uiso 1 1 d R . . H3A H 0.4297 1.2464 0.1286 0.063 Uiso 1 1 d R . . H3B H 0.5695 1.2335 0.0364 0.063 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0289(4) 0.0311(4) 0.0288(4) -0.0045(3) 0.0050(2) -0.0076(3) N2 0.0368(15) 0.0409(15) 0.0321(14) -0.0051(11) 0.0023(10) -0.0062(12) N1 0.0268(13) 0.0355(14) 0.0341(13) -0.0095(10) 0.0059(10) -0.0082(11) O1 0.0392(12) 0.0381(12) 0.0444(12) -0.0083(9) 0.0142(9) -0.0134(10) O2 0.084(2) 0.0546(15) 0.0580(16) -0.0261(13) 0.0347(13) -0.0362(14) O3 0.0393(13) 0.0467(13) 0.0454(12) -0.0181(10) 0.0090(9) -0.0127(10) O4 0.100(2) 0.0447(15) 0.119(2) -0.0294(15) 0.0791(19) -0.0232(15) C13 0.0400(18) 0.0392(18) 0.0409(18) -0.0108(14) -0.0001(14) -0.0021(14) C12 0.0418(18) 0.0410(18) 0.0310(16) -0.0108(13) 0.0010(13) -0.0044(14) C11 0.0263(15) 0.0334(16) 0.0365(16) -0.0073(12) 0.0040(12) -0.0104(12) C15 0.0426(19) 0.0450(19) 0.0373(18) -0.0111(14) 0.0036(14) 0.0027(15) C14 0.049(2) 0.056(2) 0.0335(17) -0.0093(15) 0.0036(14) 0.0021(17) C9 0.0282(15) 0.0317(15) 0.0354(16) -0.0086(12) 0.0027(11) -0.0100(12) C8 0.0258(15) 0.0343(16) 0.0398(16) -0.0088(13) 0.0044(12) -0.0050(12) C7 0.0258(15) 0.0343(16) 0.0346(16) -0.0081(12) 0.0057(11) -0.0107(12) C10 0.0317(16) 0.0347(17) 0.0362(17) -0.0052(13) 0.0072(12) -0.0095(14) C6 0.0256(15) 0.0349(16) 0.0369(16) -0.0081(12) -0.0006(12) -0.0088(13) C5 0.0256(15) 0.0369(16) 0.0377(16) -0.0114(13) 0.0030(12) -0.0098(13) C4 0.0299(17) 0.0463(19) 0.0447(18) -0.0160(14) 0.0058(13) -0.0033(14) C3 0.0292(17) 0.047(2) 0.063(2) -0.0218(17) 0.0009(15) 0.0025(15) C2 0.0368(19) 0.0397(18) 0.056(2) -0.0087(15) -0.0137(15) -0.0009(15) C1 0.0356(18) 0.0428(18) 0.0418(17) -0.0072(14) -0.0022(13) -0.0080(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.146(2) 2_675 ? Mn1 O1 2.146(2) . ? Mn1 O3 2.173(2) 2_675 ? Mn1 O3 2.173(2) . ? Mn1 N2 2.293(2) 2_666 ? Mn1 N2 2.293(2) 1_564 ? N2 C13 1.325(4) . ? N2 C14 1.339(4) . ? N2 Mn1 2.293(2) 1_546 ? N1 C9 1.327(4) . ? N1 C5 1.371(3) . ? O1 C10 1.240(3) . ? O2 C10 1.239(4) . ? O3 H3A 0.8468 . ? O3 H3B 0.8585 . ? O4 H4A 0.8486 . ? O4 H4B 0.8449 . ? C13 C12 1.385(4) . ? C13 H13 0.9300 . ? C12 C11 1.388(4) . ? C12 H12 0.9300 . ? C11 C15 1.385(4) . ? C11 C9 1.485(4) . ? C15 C14 1.377(4) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? C9 C8 1.408(4) . ? C8 C7 1.361(4) . ? C8 H7 0.9300 . ? C7 C6 1.417(4) . ? C7 C10 1.521(4) . ? C6 C5 1.417(4) . ? C6 C1 1.420(4) . ? C5 C4 1.417(4) . ? C4 C3 1.354(4) . ? C4 H4 0.9300 . ? C3 C2 1.393(5) . ? C3 H3 0.9300 . ? C2 C1 1.366(4) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O1 180.0 2_675 . ? O1 Mn1 O3 89.93(8) 2_675 2_675 ? O1 Mn1 O3 90.07(8) . 2_675 ? O1 Mn1 O3 90.07(8) 2_675 . ? O1 Mn1 O3 89.93(8) . . ? O3 Mn1 O3 180.00(8) 2_675 . ? O1 Mn1 N2 91.61(9) 2_675 2_666 ? O1 Mn1 N2 88.39(8) . 2_666 ? O3 Mn1 N2 89.79(8) 2_675 2_666 ? O3 Mn1 N2 90.21(8) . 2_666 ? O1 Mn1 N2 88.39(8) 2_675 1_564 ? O1 Mn1 N2 91.61(9) . 1_564 ? O3 Mn1 N2 90.21(8) 2_675 1_564 ? O3 Mn1 N2 89.79(8) . 1_564 ? N2 Mn1 N2 180.0 2_666 1_564 ? C13 N2 C14 116.9(2) . . ? C13 N2 Mn1 119.02(19) . 1_546 ? C14 N2 Mn1 123.48(19) . 1_546 ? C9 N1 C5 118.5(2) . . ? C10 O1 Mn1 126.91(18) . . ? Mn1 O3 H3A 131.9 . . ? Mn1 O3 H3B 99.7 . . ? H3A O3 H3B 109.0 . . ? H4A O4 H4B 111.5 . . ? N2 C13 C12 123.2(3) . . ? N2 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C15 C11 C12 116.4(3) . . ? C15 C11 C9 121.8(3) . . ? C12 C11 C9 121.7(2) . . ? C14 C15 C11 119.9(3) . . ? C14 C15 H15 120.0 . . ? C11 C15 H15 120.0 . . ? N2 C14 C15 123.5(3) . . ? N2 C14 H14 118.3 . . ? C15 C14 H14 118.3 . . ? N1 C9 C8 121.9(3) . . ? N1 C9 C11 117.6(2) . . ? C8 C9 C11 120.4(2) . . ? C7 C8 C9 120.9(3) . . ? C7 C8 H7 119.6 . . ? C9 C8 H7 119.6 . . ? C8 C7 C6 118.7(2) . . ? C8 C7 C10 118.8(2) . . ? C6 C7 C10 122.4(2) . . ? O2 C10 O1 127.0(3) . . ? O2 C10 C7 117.2(3) . . ? O1 C10 C7 115.8(3) . . ? C5 C6 C7 117.5(2) . . ? C5 C6 C1 118.6(3) . . ? C7 C6 C1 123.9(3) . . ? N1 C5 C6 122.4(3) . . ? N1 C5 C4 118.1(3) . . ? C6 C5 C4 119.4(3) . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C1 C6 120.1(3) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 O1 C10 49(100) 2_675 . . . ? O3 Mn1 O1 C10 28.9(2) 2_675 . . . ? O3 Mn1 O1 C10 -151.1(2) . . . . ? N2 Mn1 O1 C10 -60.9(3) 2_666 . . . ? N2 Mn1 O1 C10 119.1(3) 1_564 . . . ? C14 N2 C13 C12 2.3(5) . . . . ? Mn1 N2 C13 C12 -169.1(2) 1_546 . . . ? N2 C13 C12 C11 -1.2(5) . . . . ? C13 C12 C11 C15 -0.3(5) . . . . ? C13 C12 C11 C9 177.0(3) . . . . ? C12 C11 C15 C14 0.5(5) . . . . ? C9 C11 C15 C14 -176.8(3) . . . . ? C13 N2 C14 C15 -2.2(5) . . . . ? Mn1 N2 C14 C15 168.8(3) 1_546 . . . ? C11 C15 C14 N2 0.8(6) . . . . ? C5 N1 C9 C8 -1.8(4) . . . . ? C5 N1 C9 C11 176.8(2) . . . . ? C15 C11 C9 N1 -21.1(4) . . . . ? C12 C11 C9 N1 161.8(3) . . . . ? C15 C11 C9 C8 157.6(3) . . . . ? C12 C11 C9 C8 -19.5(4) . . . . ? N1 C9 C8 C7 1.9(5) . . . . ? C11 C9 C8 C7 -176.6(3) . . . . ? C9 C8 C7 C6 -0.8(4) . . . . ? C9 C8 C7 C10 175.7(3) . . . . ? Mn1 O1 C10 O2 -26.2(5) . . . . ? Mn1 O1 C10 C7 150.5(2) . . . . ? C8 C7 C10 O2 55.7(4) . . . . ? C6 C7 C10 O2 -127.9(3) . . . . ? C8 C7 C10 O1 -121.3(3) . . . . ? C6 C7 C10 O1 55.0(4) . . . . ? C8 C7 C6 C5 -0.4(4) . . . . ? C10 C7 C6 C5 -176.7(3) . . . . ? C8 C7 C6 C1 -178.8(3) . . . . ? C10 C7 C6 C1 4.8(5) . . . . ? C9 N1 C5 C6 0.5(4) . . . . ? C9 N1 C5 C4 -179.0(3) . . . . ? C7 C6 C5 N1 0.5(4) . . . . ? C1 C6 C5 N1 179.1(3) . . . . ? C7 C6 C5 C4 -179.9(3) . . . . ? C1 C6 C5 C4 -1.4(4) . . . . ? N1 C5 C4 C3 -179.3(3) . . . . ? C6 C5 C4 C3 1.1(5) . . . . ? C5 C4 C3 C2 0.0(5) . . . . ? C4 C3 C2 C1 -0.7(5) . . . . ? C3 C2 C1 C6 0.4(5) . . . . ? C5 C6 C1 C2 0.6(4) . . . . ? C7 C6 C1 C2 179.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.973 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.099