# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Michael Watkinson' _publ_contact_author_email M.WATKINSON@QMUL.AC.UK _publ_section_title ; Is there a diagnostically useful relationship between the carbon-oxygen stretching frequencies in metal carboxylate complexes and their coordination mode? ; loop_ _publ_author_name 'Michael Watkinson' 'David Martinez' 'Majid Motevalli' # Attachment '12.cif' data_mwmn1 _database_code_depnum_ccdc_archive 'CCDC 739761' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 Mn N2 O5' _chemical_formula_weight 452.38 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 17.354(2) _cell_length_b 13.042(2) _cell_length_c 9.360(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.17(2) _cell_angle_gamma 90.00 _cell_volume 2109.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.19 _cell_measurement_theta_max 12.46 _exptl_crystal_description Block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.7777 _exptl_absorpt_correction_T_max 0.8790 _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _diffrn_ambient_temperature 120(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 '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3918 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.96 _reflns_number_total 3687 _reflns_number_gt 3072 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.2000P)^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 3687 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.3270 _refine_ls_wR_factor_gt 0.3106 _refine_ls_goodness_of_fit_ref 1.510 _refine_ls_restrained_S_all 1.510 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.09817(17) 0.1770(2) 0.2375(3) 0.0402(11) Uani 1 1 d G . . C2 C 0.10555(18) 0.2690(2) 0.1650(4) 0.0508(13) Uani 1 1 d G . . H2 H 0.1438 0.3174 0.1993 0.061 Uiso 1 1 calc R . . C3 C 0.0570(2) 0.2904(2) 0.0423(4) 0.0556(15) Uani 1 1 d G . . H3 H 0.0620 0.3532 -0.0072 0.067 Uiso 1 1 calc R . . C4 C 0.00098(19) 0.2197(3) -0.0079(3) 0.0530(14) Uani 1 1 d G . . H4 H -0.0322 0.2342 -0.0917 0.064 Uiso 1 1 calc R . . C5 C -0.00640(17) 0.1277(3) 0.0646(3) 0.0494(13) Uani 1 1 d G . . H5 H -0.0447 0.0793 0.0303 0.059 Uiso 1 1 calc R . . C6 C 0.04219(19) 0.1063(2) 0.1873(3) 0.0414(12) Uani 1 1 d G . . C7 C 0.0318(3) 0.0081(4) 0.2572(5) 0.0409(11) Uani 1 1 d . . . H7 H -0.0133 -0.0299 0.2264 0.049 Uiso 1 1 calc R . . C8 C 0.0502(3) -0.1246(4) 0.4261(6) 0.0430(12) Uani 1 1 d . . . H8A H 0.0067 -0.1542 0.3638 0.052 Uiso 1 1 calc R . . H8B H 0.0299 -0.1043 0.5175 0.052 Uiso 1 1 calc R . . C9 C 0.1104(3) -0.2063(4) 0.4572(5) 0.0419(12) Uani 1 1 d . . . H9 H 0.0851 -0.2657 0.5021 0.050 Uiso 1 1 calc R . . C10 C 0.1792(3) -0.1716(4) 0.5610(6) 0.0418(11) Uani 1 1 d . . . H10A H 0.1596 -0.1407 0.6473 0.050 Uiso 1 1 calc R . . H10B H 0.2110 -0.2319 0.5919 0.050 Uiso 1 1 calc R . . C11 C 0.33960(15) 0.0198(2) 0.3296(4) 0.0423(12) Uani 1 1 d G . . C12 C 0.3979(2) 0.0682(2) 0.2624(4) 0.0522(14) Uani 1 1 d G . . H12 H 0.3881 0.1322 0.2158 0.063 Uiso 1 1 calc R . . C13 C 0.47044(18) 0.0230(3) 0.2633(4) 0.0586(16) Uani 1 1 d G . . H13 H 0.5103 0.0561 0.2173 0.070 Uiso 1 1 calc R . . C14 C 0.48474(15) -0.0707(3) 0.3314(5) 0.0618(16) Uani 1 1 d G . . H14 H 0.5343 -0.1016 0.3320 0.074 Uiso 1 1 calc R . . C15 C 0.4265(2) -0.1192(2) 0.3986(4) 0.0562(15) Uani 1 1 d G . . H15 H 0.4362 -0.1832 0.4451 0.067 Uiso 1 1 calc R . . C16 C 0.35390(16) -0.0739(2) 0.3977(4) 0.0433(12) Uani 1 1 d G . . C17 C 0.2968(3) -0.1278(3) 0.4700(5) 0.0377(11) Uani 1 1 d . . . H17 H 0.3108 -0.1941 0.5054 0.045 Uiso 1 1 calc R . . C18 C 0.1923(3) 0.1047(4) 0.6925(5) 0.0413(12) Uani 1 1 d . . . C19 C 0.1940(4) 0.1426(5) 0.8456(6) 0.0540(14) Uani 1 1 d . . . H19A H 0.1887 0.2182 0.8447 0.065 Uiso 1 1 calc R . . H19B H 0.1490 0.1139 0.8897 0.065 Uiso 1 1 calc R . . C20 C 0.2667(4) 0.1142(6) 0.9372(7) 0.0658(18) Uani 1 1 d . . . H20A H 0.2606 0.1338 1.0378 0.079 Uiso 1 1 calc R . . H20B H 0.3104 0.1543 0.9050 0.079 Uiso 1 1 calc R . . C21 C 0.2869(5) 0.0007(6) 0.9328(8) 0.074(2) Uani 1 1 d . . . H21A H 0.2949 -0.0175 0.8326 0.088 Uiso 1 1 calc R . . H21B H 0.3368 -0.0097 0.9910 0.088 Uiso 1 1 calc R . . C22 C 0.2295(6) -0.0723(9) 0.9846(10) 0.100(3) Uani 1 1 d . . . H22A H 0.2127 -0.0477 1.0758 0.151 Uiso 1 1 calc R . . H22B H 0.2533 -0.1401 0.9987 0.151 Uiso 1 1 calc R . . H22C H 0.1846 -0.0772 0.9134 0.151 Uiso 1 1 calc R . . Mn1 Mn 0.18365(4) 0.03901(5) 0.43035(7) 0.0358(4) Uani 1 1 d . . . N1 N 0.0778(2) -0.0314(3) 0.3559(5) 0.0377(10) Uani 1 1 d . . . N2 N 0.2279(2) -0.0955(3) 0.4926(4) 0.0370(9) Uani 1 1 d . . . O1 O 0.1412(2) 0.1635(3) 0.3637(4) 0.0446(9) Uani 1 1 d . . . O2 O 0.2689(2) 0.0636(3) 0.3189(4) 0.0484(10) Uani 1 1 d . . . O3 O 0.1370(2) 0.0525(3) 0.6383(4) 0.0448(9) Uani 1 1 d . . . O4 O 0.2479(2) 0.1248(3) 0.6182(4) 0.0475(9) Uani 1 1 d . . . O5 O 0.1341(2) -0.2394(3) 0.3240(4) 0.0450(9) Uani 1 1 d . . . H5A H 0.1742 -0.2754 0.3383 0.068 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 C1 0.030(2) 0.060(2) 0.031(3) -0.004(2) 0.005(2) 0.007(2) C2 0.040(3) 0.072(3) 0.041(3) 0.000(3) 0.005(2) 0.001(3) C3 0.058(4) 0.072(3) 0.037(3) 0.000(3) 0.006(3) 0.013(3) C4 0.047(3) 0.078(3) 0.033(3) 0.004(3) -0.001(2) 0.018(3) C5 0.032(3) 0.081(3) 0.035(3) -0.006(3) 0.000(2) 0.006(3) C6 0.026(2) 0.071(3) 0.028(2) -0.004(2) 0.005(2) 0.009(2) C7 0.021(2) 0.072(3) 0.031(3) -0.010(2) 0.0074(19) 0.000(2) C8 0.023(3) 0.067(3) 0.040(3) 0.002(2) 0.010(2) 0.001(2) C9 0.033(3) 0.060(3) 0.034(3) 0.003(2) 0.010(2) 0.002(2) C10 0.035(3) 0.060(2) 0.031(3) 0.009(2) 0.005(2) 0.001(2) C11 0.033(3) 0.067(2) 0.027(3) -0.007(2) 0.008(2) 0.002(2) C12 0.048(4) 0.075(3) 0.035(3) 0.000(3) 0.012(3) -0.006(3) C13 0.037(3) 0.088(4) 0.053(4) 0.004(3) 0.016(3) -0.005(3) C14 0.028(3) 0.093(4) 0.066(4) 0.003(4) 0.012(3) 0.005(3) C15 0.036(3) 0.080(3) 0.053(4) -0.004(3) 0.006(3) 0.006(3) C16 0.029(3) 0.066(3) 0.034(3) -0.004(2) 0.003(2) -0.002(2) C17 0.030(2) 0.053(2) 0.029(3) -0.001(2) -0.004(2) 0.004(2) C18 0.031(3) 0.062(2) 0.032(3) 0.006(2) 0.007(2) 0.005(2) C19 0.047(3) 0.082(3) 0.034(3) -0.009(3) 0.006(2) 0.006(3) C20 0.054(4) 0.102(5) 0.041(3) -0.008(4) 0.002(3) 0.001(4) C21 0.083(5) 0.091(4) 0.046(4) 0.000(4) -0.002(4) 0.024(4) C22 0.101(8) 0.125(7) 0.074(6) -0.004(6) 0.001(5) 0.003(6) Mn1 0.0255(6) 0.0540(6) 0.0277(6) -0.0002(3) 0.0017(4) 0.0019(3) N1 0.024(2) 0.059(2) 0.031(2) 0.0006(18) 0.0061(18) 0.0061(17) N2 0.032(2) 0.0549(19) 0.023(2) -0.0043(18) -0.0005(17) -0.0001(18) O1 0.041(2) 0.0525(17) 0.038(2) -0.0078(15) -0.0115(16) 0.0004(15) O2 0.042(2) 0.0691(19) 0.035(2) 0.0084(18) 0.0126(17) 0.0051(18) O3 0.0282(19) 0.0709(19) 0.036(2) -0.0058(17) 0.0048(16) -0.0013(16) O4 0.037(2) 0.070(2) 0.036(2) 0.0007(17) 0.0035(16) -0.0084(16) O5 0.0330(19) 0.068(2) 0.0348(19) -0.0078(17) 0.0049(15) 0.0036(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.351(4) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.457(6) . ? C7 N1 1.273(7) . ? C7 H7 0.9500 . ? C8 N1 1.481(6) . ? C8 C9 1.502(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O5 1.415(6) . ? C9 C10 1.538(7) . ? C9 H9 1.0000 . ? C10 N2 1.486(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.349(5) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.433(6) . ? C17 N2 1.302(6) . ? C17 H17 0.9500 . ? C18 O3 1.247(6) . ? C18 O4 1.267(6) . ? C18 C19 1.514(8) . ? C18 Mn1 2.590(5) . ? C19 C20 1.507(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.522(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.491(14) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Mn1 O1 1.868(4) . ? Mn1 O2 1.912(4) . ? Mn1 N2 1.982(4) . ? Mn1 N1 2.116(4) . ? Mn1 O3 2.182(4) . ? Mn1 O4 2.288(4) . ? O5 H5A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 118.1(3) . . ? O1 C1 C6 121.6(3) . . ? C2 C1 C6 120.0 . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 117.2(3) . . ? C1 C6 C7 122.8(3) . . ? N1 C7 C6 126.0(4) . . ? N1 C7 H7 117.0 . . ? C6 C7 H7 117.0 . . ? N1 C8 C9 114.9(4) . . ? N1 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? N1 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? O5 C9 C8 107.4(4) . . ? O5 C9 C10 112.0(4) . . ? C8 C9 C10 113.6(4) . . ? O5 C9 H9 107.9 . . ? C8 C9 H9 107.9 . . ? C10 C9 H9 107.9 . . ? N2 C10 C9 111.4(4) . . ? N2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O2 C11 C12 117.9(3) . . ? O2 C11 C16 122.0(3) . . ? C12 C11 C16 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 C17 117.0(3) . . ? C11 C16 C17 123.0(3) . . ? N2 C17 C16 127.0(4) . . ? N2 C17 H17 116.5 . . ? C16 C17 H17 116.5 . . ? O3 C18 O4 119.1(5) . . ? O3 C18 C19 120.8(5) . . ? O4 C18 C19 120.1(5) . . ? O3 C18 Mn1 57.1(3) . . ? O4 C18 Mn1 62.0(3) . . ? C19 C18 Mn1 177.8(4) . . ? C20 C19 C18 113.8(5) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 114.0(6) . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 116.8(8) . . ? C22 C21 H21A 108.1 . . ? C20 C21 H21A 108.1 . . ? C22 C21 H21B 108.1 . . ? C20 C21 H21B 108.1 . . ? H21A C21 H21B 107.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O1 Mn1 O2 88.46(17) . . ? O1 Mn1 N2 177.52(15) . . ? O2 Mn1 N2 90.59(17) . . ? O1 Mn1 N1 87.85(15) . . ? O2 Mn1 N1 125.79(18) . . ? N2 Mn1 N1 90.84(16) . . ? O1 Mn1 O3 93.49(16) . . ? O2 Mn1 O3 147.21(17) . . ? N2 Mn1 O3 88.56(15) . . ? N1 Mn1 O3 87.00(15) . . ? O1 Mn1 O4 88.98(14) . . ? O2 Mn1 O4 89.40(16) . . ? N2 Mn1 O4 93.31(15) . . ? N1 Mn1 O4 144.53(15) . . ? O3 Mn1 O4 57.95(14) . . ? O1 Mn1 C18 90.93(16) . . ? O2 Mn1 C18 118.65(17) . . ? N2 Mn1 C18 91.54(16) . . ? N1 Mn1 C18 115.48(17) . . ? O3 Mn1 C18 28.69(15) . . ? O4 Mn1 C18 29.27(15) . . ? C7 N1 C8 116.6(4) . . ? C7 N1 Mn1 122.1(4) . . ? C8 N1 Mn1 121.0(3) . . ? C17 N2 C10 114.9(4) . . ? C17 N2 Mn1 125.2(3) . . ? C10 N2 Mn1 119.8(3) . . ? C1 O1 Mn1 125.2(3) . . ? C11 O2 Mn1 129.2(3) . . ? C18 O3 Mn1 94.2(3) . . ? C18 O4 Mn1 88.7(3) . . ? C9 O5 H5A 109.5 . . ? 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 O1 C1 C2 C3 -173.6(3) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -179.4(4) . . . . ? O1 C1 C6 C5 173.4(3) . . . . ? C2 C1 C6 C5 0.0 . . . . ? O1 C1 C6 C7 -7.2(4) . . . . ? C2 C1 C6 C7 179.4(4) . . . . ? C5 C6 C7 N1 168.4(4) . . . . ? C1 C6 C7 N1 -11.0(6) . . . . ? N1 C8 C9 O5 -62.7(6) . . . . ? N1 C8 C9 C10 61.8(6) . . . . ? O5 C9 C10 N2 51.7(6) . . . . ? C8 C9 C10 N2 -70.2(5) . . . . ? O2 C11 C12 C13 -176.3(4) . . . . ? C16 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C14 C15 C16 C17 -179.5(4) . . . . ? O2 C11 C16 C15 176.1(4) . . . . ? C12 C11 C16 C15 0.0 . . . . ? O2 C11 C16 C17 -4.4(4) . . . . ? C12 C11 C16 C17 179.5(4) . . . . ? C15 C16 C17 N2 173.8(4) . . . . ? C11 C16 C17 N2 -5.7(6) . . . . ? O3 C18 C19 C20 126.3(6) . . . . ? O4 C18 C19 C20 -52.7(7) . . . . ? Mn1 C18 C19 C20 146(10) . . . . ? C18 C19 C20 C21 -51.4(8) . . . . ? C19 C20 C21 C22 -61.3(9) . . . . ? O3 C18 Mn1 O1 95.6(3) . . . . ? O4 C18 Mn1 O1 -86.3(3) . . . . ? C19 C18 Mn1 O1 75(10) . . . . ? O3 C18 Mn1 O2 -175.7(3) . . . . ? O4 C18 Mn1 O2 2.5(3) . . . . ? C19 C18 Mn1 O2 164(10) . . . . ? O3 C18 Mn1 N2 -84.2(3) . . . . ? O4 C18 Mn1 N2 94.0(3) . . . . ? C19 C18 Mn1 N2 -105(10) . . . . ? O3 C18 Mn1 N1 7.5(3) . . . . ? O4 C18 Mn1 N1 -174.3(3) . . . . ? C19 C18 Mn1 N1 -13(10) . . . . ? O4 C18 Mn1 O3 178.2(5) . . . . ? C19 C18 Mn1 O3 -20(10) . . . . ? O3 C18 Mn1 O4 -178.2(5) . . . . ? C19 C18 Mn1 O4 161(10) . . . . ? C6 C7 N1 C8 171.3(4) . . . . ? C6 C7 N1 Mn1 -3.1(7) . . . . ? C9 C8 N1 C7 139.6(5) . . . . ? C9 C8 N1 Mn1 -45.9(6) . . . . ? O1 Mn1 N1 C7 23.4(4) . . . . ? O2 Mn1 N1 C7 -63.2(4) . . . . ? N2 Mn1 N1 C7 -154.5(4) . . . . ? O3 Mn1 N1 C7 117.0(4) . . . . ? O4 Mn1 N1 C7 108.6(4) . . . . ? C18 Mn1 N1 C7 113.4(4) . . . . ? O1 Mn1 N1 C8 -150.8(4) . . . . ? O2 Mn1 N1 C8 122.6(4) . . . . ? N2 Mn1 N1 C8 31.3(4) . . . . ? O3 Mn1 N1 C8 -57.2(4) . . . . ? O4 Mn1 N1 C8 -65.6(4) . . . . ? C18 Mn1 N1 C8 -60.8(4) . . . . ? C16 C17 N2 C10 175.5(4) . . . . ? C16 C17 N2 Mn1 0.2(7) . . . . ? C9 C10 N2 C17 -112.3(5) . . . . ? C9 C10 N2 Mn1 63.2(5) . . . . ? O1 Mn1 N2 C17 77(4) . . . . ? O2 Mn1 N2 C17 9.5(4) . . . . ? N1 Mn1 N2 C17 135.3(4) . . . . ? O3 Mn1 N2 C17 -137.8(4) . . . . ? O4 Mn1 N2 C17 -80.0(4) . . . . ? C18 Mn1 N2 C17 -109.2(4) . . . . ? O1 Mn1 N2 C10 -98(4) . . . . ? O2 Mn1 N2 C10 -165.6(4) . . . . ? N1 Mn1 N2 C10 -39.8(4) . . . . ? O3 Mn1 N2 C10 47.2(4) . . . . ? O4 Mn1 N2 C10 105.0(4) . . . . ? C18 Mn1 N2 C10 75.7(4) . . . . ? C2 C1 O1 Mn1 -145.1(2) . . . . ? C6 C1 O1 Mn1 41.4(4) . . . . ? O2 Mn1 O1 C1 83.7(3) . . . . ? N2 Mn1 O1 C1 16(4) . . . . ? N1 Mn1 O1 C1 -42.2(3) . . . . ? O3 Mn1 O1 C1 -129.1(3) . . . . ? O4 Mn1 O1 C1 173.1(3) . . . . ? C18 Mn1 O1 C1 -157.7(3) . . . . ? C12 C11 O2 Mn1 -163.7(3) . . . . ? C16 C11 O2 Mn1 20.1(5) . . . . ? O1 Mn1 O2 C11 162.5(4) . . . . ? N2 Mn1 O2 C11 -19.8(4) . . . . ? N1 Mn1 O2 C11 -111.2(4) . . . . ? O3 Mn1 O2 C11 68.5(5) . . . . ? O4 Mn1 O2 C11 73.5(4) . . . . ? C18 Mn1 O2 C11 72.3(4) . . . . ? O4 C18 O3 Mn1 -1.8(5) . . . . ? C19 C18 O3 Mn1 179.1(4) . . . . ? O1 Mn1 O3 C18 -85.6(3) . . . . ? O2 Mn1 O3 C18 7.0(5) . . . . ? N2 Mn1 O3 C18 95.9(3) . . . . ? N1 Mn1 O3 C18 -173.2(3) . . . . ? O4 Mn1 O3 C18 1.1(3) . . . . ? O3 C18 O4 Mn1 1.8(5) . . . . ? C19 C18 O4 Mn1 -179.2(4) . . . . ? O1 Mn1 O4 C18 93.7(3) . . . . ? O2 Mn1 O4 C18 -177.8(3) . . . . ? N2 Mn1 O4 C18 -87.3(3) . . . . ? N1 Mn1 O4 C18 8.9(4) . . . . ? O3 Mn1 O4 C18 -1.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O4 0.84 1.89 2.723(5) 169.4 2_546 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.135 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.166 # Attachment '739762.cif' data_mwmn2 _database_code_depnum_ccdc_archive 'CCDC 739762' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H34 Br4 Mn1 N4 O8' _chemical_formula_sum 'C38 H34 Br4 Mn2 N4 O8' _chemical_formula_weight 1104.21 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.449(3) _cell_length_b 26.229(5) _cell_length_c 10.973(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3870.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 4.840 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.3246 _exptl_absorpt_correction_T_max 0.7600 _exptl_absorpt_process_details ; ? ; _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7200 _diffrn_reflns_av_R_equivalents 0.1222 _diffrn_reflns_av_sigmaI/netI 0.1740 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.12 _reflns_number_total 3607 _reflns_number_gt 1994 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0392P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _refine_ls_number_reflns 3607 _refine_ls_number_parameters 417 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.924 _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 C1 C 0.7769(3) 0.32704(16) 0.1536(5) 0.023(2) Uani 1 1 d G . . C2 C 0.6955(4) 0.33369(18) 0.0772(6) 0.020(3) Uani 1 1 d GU . . H2 H 0.6613 0.3048 0.0459 0.024 Uiso 1 1 calc R . . C3 C 0.6642(4) 0.3825(2) 0.0466(7) 0.022(3) Uani 1 1 d G . . H3 H 0.6086 0.3871 -0.0056 0.027 Uiso 1 1 calc R . . C4 C 0.7143(4) 0.42475(18) 0.0925(6) 0.036(3) Uani 1 1 d G . . C5 C 0.7957(5) 0.41810(16) 0.1689(7) 0.027(3) Uani 1 1 d G . . H5 H 0.8299 0.4469 0.2002 0.032 Uiso 1 1 calc R . . C6 C 0.8270(4) 0.36925(16) 0.1995(6) 0.022(2) Uani 1 1 d G . . C7 C 0.9089(10) 0.3677(5) 0.2871(12) 0.025(3) Uani 1 1 d . . . H7 H 0.9329 0.3989 0.3203 0.030 Uiso 1 1 calc R . . C8 C 1.0291(9) 0.3245(5) 0.4113(13) 0.026(2) Uani 1 1 d . . . H8A H 1.0015 0.3154 0.4921 0.032 Uiso 1 1 calc R . . H8B H 1.0598 0.3587 0.4174 0.032 Uiso 1 1 calc R . . C9 C 1.1061(9) 0.2860(4) 0.3744(15) 0.026(2) Uani 1 1 d . . . H9A H 1.1490 0.3001 0.3093 0.032 Uiso 1 1 calc R . . H9B H 1.1484 0.2769 0.4450 0.032 Uiso 1 1 calc R . . C10 C 0.9656(4) 0.14944(16) 0.2285(5) 0.023(2) Uani 1 1 d G . . C11 C 0.9274(5) 0.10355(16) 0.1858(6) 0.024(3) Uani 1 1 d G . . H11 H 0.8759 0.1036 0.1266 0.029 Uiso 1 1 calc R . . C12 C 0.9646(5) 0.05766(16) 0.2298(7) 0.032(4) Uani 1 1 d G . . H12 H 0.9385 0.0263 0.2006 0.038 Uiso 1 1 calc R . . C13 C 1.0400(5) 0.05766(19) 0.3164(7) 0.036(3) Uani 1 1 d G . . C14 C 1.0782(5) 0.1035(2) 0.3591(7) 0.026(3) Uani 1 1 d GU . . H14 H 1.1298 0.1033 0.4183 0.031 Uiso 1 1 calc R . . C15 C 1.0418(8) 0.1499(5) 0.3160(13) 0.022(2) Uani 1 1 d G . . C16 C 1.0826(9) 0.1968(4) 0.3562(12) 0.018(3) Uani 1 1 d . . . H16 H 1.1387 0.1947 0.4085 0.021 Uiso 1 1 calc R . . C17 C 1.0409(4) 0.36083(17) -0.2467(5) 0.024(3) Uani 1 1 d G . . C18 C 1.1027(5) 0.40284(16) -0.2622(7) 0.033(3) Uani 1 1 d G . . H18 H 1.1609 0.4001 -0.3107 0.039 Uiso 1 1 calc R . . C19 C 1.0791(5) 0.44893(16) -0.2067(8) 0.044(5) Uani 1 1 d G . . H19 H 1.1213 0.4776 -0.2173 0.052 Uiso 1 1 calc R . . C20 C 0.9939(5) 0.45301(18) -0.1357(7) 0.039(4) Uani 1 1 d G . . C21 C 0.9322(4) 0.41100(19) -0.1202(7) 0.024(3) Uani 1 1 d G . . H21 H 0.8739 0.4138 -0.0717 0.029 Uiso 1 1 calc R . . C22 C 0.9557(4) 0.36491(18) -0.1757(7) 0.030(4) Uani 1 1 d G . . C23 C 0.8906(9) 0.3228(5) -0.1510(13) 0.026(4) Uani 1 1 d . . . H23 H 0.8294 0.3300 -0.1113 0.031 Uiso 1 1 calc R . . C24 C 0.8396(9) 0.2363(5) -0.1513(14) 0.029(4) Uani 1 1 d U . . H24A H 0.8001 0.2278 -0.2247 0.035 Uiso 1 1 calc R . . H24B H 0.7935 0.2471 -0.0859 0.035 Uiso 1 1 calc R . . C25 C 0.8984(9) 0.1913(5) -0.1112(15) 0.026(3) Uani 1 1 d . . . H25A H 0.8571 0.1601 -0.1156 0.031 Uiso 1 1 calc R . . H25B H 0.9207 0.1959 -0.0259 0.031 Uiso 1 1 calc R . . C26 C 1.1719(4) 0.17365(18) -0.3374(5) 0.022(3) Uani 1 1 d GU . . C27 C 1.2596(5) 0.1626(2) -0.3989(7) 0.033(3) Uani 1 1 d G . . H27 H 1.2966 0.1893 -0.4362 0.039 Uiso 1 1 calc R . . C28 C 1.2934(5) 0.1126(2) -0.4057(7) 0.030(4) Uani 1 1 d G . . H28 H 1.3534 0.1051 -0.4477 0.036 Uiso 1 1 calc R . . C29 C 1.2394(5) 0.07364(19) -0.3511(7) 0.035(4) Uani 1 1 d G . . C30 C 1.1516(6) 0.08467(17) -0.2896(8) 0.035(4) Uani 1 1 d GU . . H30 H 1.1147 0.0580 -0.2526 0.042 Uiso 1 1 calc R . . C31 C 1.1172(10) 0.1350(5) -0.2821(15) 0.033(4) Uani 1 1 d G . . C32 C 1.0271(9) 0.1428(5) -0.2132(11) 0.018(3) Uani 1 1 d . . . H32 H 0.9954 0.1137 -0.1794 0.022 Uiso 1 1 calc R . . C33 C 1.0826(10) 0.2908(5) 0.0176(13) 0.026(3) Uani 1 1 d . . . C34 C 1.1623(9) 0.3315(5) 0.0403(16) 0.031(3) Uani 1 1 d U . . H34A H 1.2174 0.3154 0.0862 0.037 Uiso 1 1 calc R . . H34B H 1.1894 0.3421 -0.0397 0.037 Uiso 1 1 calc R . . C35 C 1.1314(11) 0.3782(5) 0.1071(15) 0.040(4) Uani 1 1 d . . . H35A H 1.0785 0.3955 0.0617 0.061 Uiso 1 1 calc R . . H35B H 1.1885 0.4011 0.1156 0.061 Uiso 1 1 calc R . . H35C H 1.1069 0.3687 0.1881 0.061 Uiso 1 1 calc R . . C36 C 0.8790(11) 0.2147(5) 0.5194(14) 0.026(3) Uani 1 1 d . . . C37 C 0.8212(10) 0.1681(5) 0.5641(14) 0.030(4) Uani 1 1 d . . . H37A H 0.8591 0.1522 0.6314 0.036 Uiso 1 1 calc R . . H37B H 0.7570 0.1799 0.5980 0.036 Uiso 1 1 calc R . . C38 C 0.8008(10) 0.1286(5) 0.4701(14) 0.031(4) Uani 1 1 d . . . H38A H 0.7773 0.1450 0.3953 0.046 Uiso 1 1 calc R . . H38B H 0.7498 0.1051 0.5003 0.046 Uiso 1 1 calc R . . H38C H 0.8620 0.1096 0.4530 0.046 Uiso 1 1 calc R . . N1 N 0.9500(7) 0.3253(4) 0.3210(10) 0.018(2) Uani 1 1 d U . . N2 N 1.0526(7) 0.2412(4) 0.3304(11) 0.0219(19) Uani 1 1 d . . . N3 N 0.9091(7) 0.2766(4) -0.1783(11) 0.024(3) Uani 1 1 d U . . N4 N 0.9874(7) 0.1863(4) -0.1947(10) 0.0219(19) Uani 1 1 d . . . O1 O 0.8039(5) 0.2800(3) 0.1754(8) 0.023(2) Uani 1 1 d U . . O2 O 0.9194(6) 0.1902(3) 0.1847(8) 0.024(2) Uani 1 1 d U . . O3 O 1.0689(6) 0.3178(4) -0.3030(8) 0.027(2) Uani 1 1 d . . . O4 O 1.1470(6) 0.2222(3) -0.3277(9) 0.025(2) Uani 1 1 d . . . O5 O 1.0107(6) 0.2869(3) 0.0901(8) 0.026(2) Uani 1 1 d . . . O6 O 1.0988(6) 0.2638(4) -0.0737(9) 0.034(3) Uani 1 1 d . . . O7 O 0.8498(6) 0.2308(3) 0.4141(9) 0.027(2) Uani 1 1 d . . . O8 O 0.9423(6) 0.2366(4) 0.5799(9) 0.033(3) Uani 1 1 d . . . Mn1 Mn 0.92478(12) 0.25657(7) 0.2470(2) 0.0200(5) Uani 1 1 d . . . Mn2 Mn 1.03361(12) 0.25204(8) -0.2557(2) 0.0210(4) Uani 1 1 d . . . Br1 Br 0.67704(11) 0.49107(6) 0.03709(17) 0.0470(5) Uani 1 1 d . . . Br2 Br 1.09757(12) -0.00254(6) 0.37693(17) 0.0512(5) Uani 1 1 d . . . Br3 Br 0.96236(13) 0.51476(6) -0.05831(19) 0.0533(5) Uani 1 1 d . . . Br4 Br 1.28762(11) 0.00585(6) -0.35583(19) 0.0462(5) 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 C1 0.026(5) 0.030(5) 0.013(5) 0.000(5) 0.013(5) -0.001(4) C2 0.020(5) 0.023(5) 0.016(5) -0.005(4) 0.000(4) -0.008(4) C3 0.014(7) 0.036(8) 0.017(8) 0.005(7) -0.007(7) 0.000(6) C4 0.024(6) 0.047(7) 0.038(7) 0.006(6) 0.017(6) 0.012(5) C5 0.015(7) 0.040(8) 0.027(9) -0.012(7) 0.000(7) -0.007(6) C6 0.013(5) 0.020(5) 0.033(6) 0.004(5) 0.001(4) -0.007(4) C7 0.030(8) 0.034(8) 0.010(8) 0.002(6) -0.010(6) 0.005(7) C8 0.023(6) 0.027(5) 0.029(7) 0.005(5) -0.016(5) -0.005(4) C9 0.023(6) 0.027(5) 0.029(7) 0.005(5) -0.016(5) -0.005(4) C10 0.026(5) 0.030(5) 0.013(5) 0.000(5) 0.013(5) -0.001(4) C11 0.023(7) 0.038(8) 0.012(8) -0.005(7) -0.010(7) -0.001(6) C12 0.035(8) 0.018(7) 0.042(10) -0.002(8) 0.001(9) -0.016(6) C13 0.024(6) 0.047(7) 0.038(7) 0.006(6) 0.017(6) 0.012(5) C14 0.022(5) 0.030(5) 0.027(5) -0.003(4) 0.002(4) 0.007(4) C15 0.013(5) 0.020(5) 0.033(6) 0.004(5) 0.001(4) -0.007(4) C16 0.010(7) 0.021(7) 0.022(9) 0.007(6) -0.004(6) -0.005(5) C17 0.024(7) 0.027(7) 0.021(8) 0.015(8) 0.010(8) 0.003(6) C18 0.025(5) 0.035(6) 0.039(7) 0.005(6) 0.011(6) 0.002(4) C19 0.039(9) 0.015(7) 0.077(15) 0.000(8) 0.025(9) -0.008(6) C20 0.023(8) 0.055(10) 0.039(11) 0.018(9) 0.003(8) 0.008(7) C21 0.022(7) 0.022(7) 0.029(8) 0.002(7) -0.004(7) 0.007(6) C22 0.014(8) 0.031(8) 0.045(10) 0.006(8) 0.005(7) 0.009(6) C23 0.007(7) 0.044(9) 0.026(10) 0.011(7) 0.008(6) -0.001(6) C24 0.023(5) 0.031(5) 0.034(6) -0.005(4) -0.002(4) -0.002(4) C25 0.018(7) 0.030(7) 0.030(9) -0.001(8) -0.001(7) -0.008(6) C26 0.018(4) 0.026(5) 0.021(5) -0.002(4) -0.001(4) 0.007(4) C27 0.025(5) 0.035(6) 0.039(7) 0.005(6) 0.011(6) 0.002(4) C28 0.014(7) 0.049(9) 0.026(9) -0.019(7) 0.003(7) 0.005(7) C29 0.043(9) 0.037(9) 0.025(9) -0.022(8) -0.005(8) 0.010(7) C30 0.030(5) 0.039(5) 0.036(6) -0.004(4) -0.008(4) 0.003(4) C31 0.033(9) 0.019(7) 0.046(12) -0.009(7) 0.007(8) -0.001(6) C32 0.019(7) 0.023(7) 0.012(8) -0.001(5) 0.003(6) -0.009(6) C33 0.024(5) 0.028(5) 0.025(7) 0.007(5) -0.001(6) 0.011(4) C34 0.028(5) 0.030(5) 0.035(5) -0.007(4) -0.001(4) -0.005(4) C35 0.038(9) 0.036(9) 0.046(12) 0.001(8) 0.012(9) 0.012(7) C36 0.024(5) 0.028(5) 0.025(7) 0.007(5) -0.001(6) 0.011(4) C37 0.033(8) 0.035(8) 0.021(9) 0.015(7) 0.002(7) -0.009(7) C38 0.035(9) 0.034(8) 0.023(9) -0.004(7) 0.011(7) -0.007(6) N1 0.018(4) 0.026(4) 0.011(4) -0.002(4) 0.002(4) -0.006(3) N2 0.016(4) 0.030(5) 0.020(5) -0.006(4) -0.001(4) -0.001(3) N3 0.018(4) 0.034(4) 0.020(5) -0.001(4) 0.008(4) 0.003(4) N4 0.016(4) 0.030(5) 0.020(5) -0.006(4) -0.001(4) -0.001(3) O1 0.017(4) 0.033(4) 0.021(4) -0.006(3) -0.004(3) -0.002(3) O2 0.019(4) 0.035(4) 0.018(4) -0.001(3) -0.004(3) 0.000(3) O3 0.026(6) 0.041(6) 0.014(5) 0.007(4) 0.005(4) -0.004(4) O4 0.020(5) 0.032(5) 0.023(6) 0.005(5) 0.006(4) 0.001(4) O5 0.017(5) 0.042(5) 0.018(5) 0.001(5) 0.000(4) -0.001(4) O6 0.017(5) 0.063(7) 0.020(6) -0.022(5) 0.000(5) 0.002(5) O7 0.008(5) 0.043(6) 0.031(6) -0.003(5) -0.006(4) 0.002(4) O8 0.020(5) 0.064(7) 0.016(6) -0.005(5) 0.000(4) -0.011(5) Mn1 0.0127(9) 0.0334(11) 0.0140(11) -0.0028(11) -0.0055(11) -0.0018(8) Mn2 0.0138(9) 0.0327(10) 0.0165(10) 0.0017(11) 0.0032(12) 0.0019(9) Br1 0.0419(9) 0.0421(10) 0.0571(12) 0.0128(10) -0.0060(10) 0.0063(7) Br2 0.0512(10) 0.0429(9) 0.0593(11) 0.0105(11) -0.0128(9) 0.0050(8) Br3 0.0525(10) 0.0390(9) 0.0685(13) -0.0136(10) 0.0168(10) 0.0002(8) Br4 0.0342(8) 0.0350(9) 0.0693(12) -0.0063(10) 0.0010(10) 0.0088(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.307(9) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 Br1 1.909(5) . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.463(13) . ? C7 N1 1.297(15) . ? C7 H7 0.9500 . ? C8 N1 1.454(15) . ? C8 C9 1.501(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.460(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O2 1.327(10) . ? C10 C11 1.3900 . ? C10 C15 1.405(14) . ? C11 C12 1.3900 . ? C11 H11 0.9500 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 Br2 1.879(5) . ? C14 C15 1.393(13) . ? C14 H14 0.9500 . ? C15 C16 1.418(16) . ? C16 N2 1.265(15) . ? C16 H16 0.9500 . ? C17 O3 1.341(10) . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 C21 1.3900 . ? C20 Br3 1.877(5) . ? C21 C22 1.3900 . ? C21 H21 0.9500 . ? C22 C23 1.434(13) . ? C23 N3 1.275(16) . ? C23 H23 0.9500 . ? C24 N3 1.440(16) . ? C24 C25 1.487(17) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N4 1.512(16) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O4 1.320(9) . ? C26 C27 1.3900 . ? C26 C31 1.391(14) . ? C27 C28 1.3900 . ? C27 H27 0.9500 . ? C28 C29 1.3900 . ? C28 H28 0.9500 . ? C29 C30 1.3900 . ? C29 Br4 1.893(5) . ? C30 C31 1.402(13) . ? C30 H30 0.9500 . ? C31 C32 1.442(17) . ? C32 N4 1.278(15) . ? C32 H32 0.9500 . ? C33 O6 1.246(16) . ? C33 O5 1.257(15) . ? C33 C34 1.534(18) . ? C34 C35 1.487(18) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 O8 1.222(16) . ? C36 O7 1.292(16) . ? C36 C37 1.528(18) . ? C37 C38 1.488(19) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? N1 Mn1 2.005(10) . ? N2 Mn1 1.988(10) . ? N3 Mn2 1.984(11) . ? N4 Mn2 1.951(10) . ? O1 Mn1 1.908(8) . ? O2 Mn1 1.871(9) . ? O3 Mn2 1.863(9) . ? O4 Mn2 1.888(8) . ? O5 Mn1 2.221(9) . ? O6 Mn2 2.203(10) . ? O7 Mn1 2.199(10) . ? O8 Mn2 2.220(10) 1_556 ? Mn2 O8 2.220(10) 1_554 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 116.5(4) . . ? O1 C1 C6 123.4(4) . . ? C2 C1 C6 120.0 . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 Br1 118.9(3) . . ? C5 C4 Br1 120.9(3) . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 114.3(6) . . ? C1 C6 C7 125.5(6) . . ? N1 C7 C6 122.1(11) . . ? N1 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? N1 C8 C9 109.3(11) . . ? N1 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N1 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? N2 C9 C8 106.9(10) . . ? N2 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? N2 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? O2 C10 C11 113.8(4) . . ? O2 C10 C15 125.6(7) . . ? C11 C10 C15 120.5(5) . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 Br2 117.1(3) . . ? C12 C13 Br2 122.8(3) . . ? C13 C14 C15 120.8(6) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 118.7(9) . . ? C14 C15 C16 121.1(11) . . ? C10 C15 C16 120.1(10) . . ? N2 C16 C15 127.4(12) . . ? N2 C16 H16 116.3 . . ? C15 C16 H16 116.3 . . ? O3 C17 C18 116.3(4) . . ? O3 C17 C22 123.7(4) . . ? C18 C17 C22 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.0 . . ? C21 C20 Br3 119.6(3) . . ? C19 C20 Br3 120.4(3) . . ? C20 C21 C22 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 120.0 . . ? C21 C22 C23 116.6(6) . . ? C17 C22 C23 123.4(6) . . ? N3 C23 C22 124.7(11) . . ? N3 C23 H23 117.7 . . ? C22 C23 H23 117.7 . . ? N3 C24 C25 107.3(10) . . ? N3 C24 H24A 110.3 . . ? C25 C24 H24A 110.3 . . ? N3 C24 H24B 110.3 . . ? C25 C24 H24B 110.3 . . ? H24A C24 H24B 108.5 . . ? C24 C25 N4 108.1(12) . . ? C24 C25 H25A 110.1 . . ? N4 C25 H25A 110.1 . . ? C24 C25 H25B 110.1 . . ? N4 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? O4 C26 C27 117.0(4) . . ? O4 C26 C31 122.2(8) . . ? C27 C26 C31 120.6(6) . . ? C28 C27 C26 120.0 . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C29 C28 C27 120.0 . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.0 . . ? C28 C29 Br4 120.0(3) . . ? C30 C29 Br4 120.0(3) . . ? C31 C30 C29 120.3(6) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C26 119.1(11) . . ? C30 C31 C32 116.1(11) . . ? C26 C31 C32 124.8(11) . . ? N4 C32 C31 124.1(11) . . ? N4 C32 H32 117.9 . . ? C31 C32 H32 117.9 . . ? O6 C33 O5 126.8(13) . . ? O6 C33 C34 113.8(12) . . ? O5 C33 C34 119.4(13) . . ? C35 C34 C33 117.2(12) . . ? C35 C34 H34A 108.0 . . ? C33 C34 H34A 108.0 . . ? C35 C34 H34B 108.0 . . ? C33 C34 H34B 108.0 . . ? H34A C34 H34B 107.2 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O8 C36 O7 122.9(12) . . ? O8 C36 C37 123.7(13) . . ? O7 C36 C37 113.2(13) . . ? C38 C37 C36 115.4(12) . . ? C38 C37 H37A 108.4 . . ? C36 C37 H37A 108.4 . . ? C38 C37 H37B 108.4 . . ? C36 C37 H37B 108.4 . . ? H37A C37 H37B 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C7 N1 C8 121.2(11) . . ? C7 N1 Mn1 125.7(9) . . ? C8 N1 Mn1 112.7(8) . . ? C16 N2 C9 120.7(11) . . ? C16 N2 Mn1 124.4(8) . . ? C9 N2 Mn1 114.6(8) . . ? C23 N3 C24 121.5(11) . . ? C23 N3 Mn2 125.0(9) . . ? C24 N3 Mn2 113.5(8) . . ? C32 N4 C25 120.3(10) . . ? C32 N4 Mn2 127.0(9) . . ? C25 N4 Mn2 112.6(7) . . ? C1 O1 Mn1 128.0(6) . . ? C10 O2 Mn1 126.8(6) . . ? C17 O3 Mn2 125.4(6) . . ? C26 O4 Mn2 129.6(6) . . ? C33 O5 Mn1 157.0(8) . . ? C33 O6 Mn2 137.6(8) . . ? C36 O7 Mn1 135.0(8) . . ? C36 O8 Mn2 155.8(10) . 1_556 ? O2 Mn1 O1 96.7(4) . . ? O2 Mn1 N2 90.8(4) . . ? O1 Mn1 N2 172.5(4) . . ? O2 Mn1 N1 172.0(4) . . ? O1 Mn1 N1 91.2(4) . . ? N2 Mn1 N1 81.3(4) . . ? O2 Mn1 O7 90.1(4) . . ? O1 Mn1 O7 93.0(4) . . ? N2 Mn1 O7 87.1(4) . . ? N1 Mn1 O7 90.9(4) . . ? O2 Mn1 O5 94.0(4) . . ? O1 Mn1 O5 90.5(4) . . ? N2 Mn1 O5 88.8(4) . . ? N1 Mn1 O5 84.5(4) . . ? O7 Mn1 O5 174.3(3) . . ? O3 Mn2 O4 93.5(4) . . ? O3 Mn2 N4 174.3(5) . . ? O4 Mn2 N4 92.0(4) . . ? O3 Mn2 N3 92.0(4) . . ? O4 Mn2 N3 174.4(4) . . ? N4 Mn2 N3 82.6(4) . . ? O3 Mn2 O6 91.3(4) . . ? O4 Mn2 O6 96.7(4) . . ? N4 Mn2 O6 86.5(4) . . ? N3 Mn2 O6 84.4(4) . . ? O3 Mn2 O8 94.8(4) . 1_554 ? O4 Mn2 O8 91.8(4) . 1_554 ? N4 Mn2 O8 86.6(4) . 1_554 ? N3 Mn2 O8 86.6(4) . 1_554 ? O6 Mn2 O8 169.3(3) . 1_554 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.0(5) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C2 C3 C4 Br1 174.4(3) . . . . ? C3 C4 C5 C6 0.0 . . . . ? Br1 C4 C5 C6 -174.3(3) . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -175.9(7) . . . . ? O1 C1 C6 C5 177.9(5) . . . . ? C2 C1 C6 C5 0.0 . . . . ? O1 C1 C6 C7 -6.7(9) . . . . ? C2 C1 C6 C7 175.4(8) . . . . ? C5 C6 C7 N1 -176.8(10) . . . . ? C1 C6 C7 N1 7.6(16) . . . . ? N1 C8 C9 N2 -42.1(15) . . . . ? O2 C10 C11 C12 -176.0(5) . . . . ? C15 C10 C11 C12 0.0(7) . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C11 C12 C13 Br2 -177.9(3) . . . . ? C12 C13 C14 C15 0.0(7) . . . . ? Br2 C13 C14 C15 178.0(9) . . . . ? C13 C14 C15 C10 0.0(14) . . . . ? C13 C14 C15 C16 -178.0(9) . . . . ? O2 C10 C15 C14 175.5(8) . . . . ? C11 C10 C15 C14 0.0(14) . . . . ? O2 C10 C15 C16 -6.5(16) . . . . ? C11 C10 C15 C16 178.0(9) . . . . ? C14 C15 C16 N2 -175.3(12) . . . . ? C10 C15 C16 N2 7(2) . . . . ? O3 C17 C18 C19 -179.9(5) . . . . ? C22 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C18 C19 C20 Br3 179.0(3) . . . . ? C19 C20 C21 C22 0.0 . . . . ? Br3 C20 C21 C22 -179.0(3) . . . . ? C20 C21 C22 C17 0.0 . . . . ? C20 C21 C22 C23 177.4(8) . . . . ? O3 C17 C22 C21 179.9(5) . . . . ? C18 C17 C22 C21 0.0 . . . . ? O3 C17 C22 C23 2.7(10) . . . . ? C18 C17 C22 C23 -177.2(8) . . . . ? C21 C22 C23 N3 -168.6(11) . . . . ? C17 C22 C23 N3 8.6(17) . . . . ? N3 C24 C25 N4 -42.7(15) . . . . ? O4 C26 C27 C28 176.0(5) . . . . ? C31 C26 C27 C28 0.2(9) . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C27 C28 C29 Br4 -177.9(3) . . . . ? C28 C29 C30 C31 -0.2(8) . . . . ? Br4 C29 C30 C31 177.8(10) . . . . ? C29 C30 C31 C26 0.3(17) . . . . ? C29 C30 C31 C32 -178.1(9) . . . . ? O4 C26 C31 C30 -175.9(9) . . . . ? C27 C26 C31 C30 -0.3(17) . . . . ? O4 C26 C31 C32 2.4(19) . . . . ? C27 C26 C31 C32 178.0(10) . . . . ? C30 C31 C32 N4 178.1(12) . . . . ? C26 C31 C32 N4 0(2) . . . . ? O6 C33 C34 C35 153.7(13) . . . . ? O5 C33 C34 C35 -28(2) . . . . ? O8 C36 C37 C38 -142.2(13) . . . . ? O7 C36 C37 C38 42.1(16) . . . . ? C6 C7 N1 C8 -177.9(10) . . . . ? C6 C7 N1 Mn1 8.8(17) . . . . ? C9 C8 N1 C7 -140.4(12) . . . . ? C9 C8 N1 Mn1 33.7(12) . . . . ? C15 C16 N2 C9 -176.8(13) . . . . ? C15 C16 N2 Mn1 11(2) . . . . ? C8 C9 N2 C16 -140.0(13) . . . . ? C8 C9 N2 Mn1 33.2(14) . . . . ? C22 C23 N3 C24 -179.5(12) . . . . ? C22 C23 N3 Mn2 2(2) . . . . ? C25 C24 N3 C23 -141.2(14) . . . . ? C25 C24 N3 Mn2 37.2(14) . . . . ? C31 C32 N4 C25 -174.1(13) . . . . ? C31 C32 N4 Mn2 1.7(19) . . . . ? C24 C25 N4 C32 -152.6(12) . . . . ? C24 C25 N4 Mn2 31.0(13) . . . . ? C2 C1 O1 Mn1 166.3(5) . . . . ? C6 C1 O1 Mn1 -11.6(10) . . . . ? C11 C10 O2 Mn1 163.2(5) . . . . ? C15 C10 O2 Mn1 -12.6(12) . . . . ? C18 C17 O3 Mn2 155.2(5) . . . . ? C22 C17 O3 Mn2 -24.7(9) . . . . ? C27 C26 O4 Mn2 178.2(6) . . . . ? C31 C26 O4 Mn2 -6.0(14) . . . . ? O6 C33 O5 Mn1 83(3) . . . . ? C34 C33 O5 Mn1 -96(2) . . . . ? O5 C33 O6 Mn2 69.9(19) . . . . ? C34 C33 O6 Mn2 -111.4(13) . . . . ? O8 C36 O7 Mn1 48.2(19) . . . . ? C37 C36 O7 Mn1 -136.0(11) . . . . ? O7 C36 O8 Mn2 170.9(14) . . . 1_556 ? C37 C36 O8 Mn2 -4(3) . . . 1_556 ? C10 O2 Mn1 O1 -158.3(7) . . . . ? C10 O2 Mn1 N2 21.9(8) . . . . ? C10 O2 Mn1 N1 32(4) . . . . ? C10 O2 Mn1 O7 -65.3(7) . . . . ? C10 O2 Mn1 O5 110.8(7) . . . . ? C1 O1 Mn1 O2 -158.5(8) . . . . ? C1 O1 Mn1 N2 20(4) . . . . ? C1 O1 Mn1 N1 20.1(8) . . . . ? C1 O1 Mn1 O7 111.1(8) . . . . ? C1 O1 Mn1 O5 -64.4(8) . . . . ? C16 N2 Mn1 O2 -21.0(12) . . . . ? C9 N2 Mn1 O2 166.1(10) . . . . ? C16 N2 Mn1 O1 160(3) . . . . ? C9 N2 Mn1 O1 -13(4) . . . . ? C16 N2 Mn1 N1 160.3(12) . . . . ? C9 N2 Mn1 N1 -12.5(10) . . . . ? C16 N2 Mn1 O7 69.0(11) . . . . ? C9 N2 Mn1 O7 -103.9(10) . . . . ? C16 N2 Mn1 O5 -115.1(11) . . . . ? C9 N2 Mn1 O5 72.1(10) . . . . ? C7 N1 Mn1 O2 152(3) . . . . ? C8 N1 Mn1 O2 -22(4) . . . . ? C7 N1 Mn1 O1 -18.6(11) . . . . ? C8 N1 Mn1 O1 167.7(8) . . . . ? C7 N1 Mn1 N2 161.5(12) . . . . ? C8 N1 Mn1 N2 -12.3(8) . . . . ? C7 N1 Mn1 O7 -111.6(11) . . . . ? C8 N1 Mn1 O7 74.7(8) . . . . ? C7 N1 Mn1 O5 71.8(11) . . . . ? C8 N1 Mn1 O5 -101.9(8) . . . . ? C36 O7 Mn1 O2 92.7(12) . . . . ? C36 O7 Mn1 O1 -170.6(12) . . . . ? C36 O7 Mn1 N2 1.9(12) . . . . ? C36 O7 Mn1 N1 -79.4(12) . . . . ? C36 O7 Mn1 O5 -43(4) . . . . ? C33 O5 Mn1 O2 -61(2) . . . . ? C33 O5 Mn1 O1 -157(2) . . . . ? C33 O5 Mn1 N2 30(2) . . . . ? C33 O5 Mn1 N1 111(2) . . . . ? C33 O5 Mn1 O7 75(4) . . . . ? C17 O3 Mn2 O4 -154.3(7) . . . . ? C17 O3 Mn2 N4 10(5) . . . . ? C17 O3 Mn2 N3 26.9(8) . . . . ? C17 O3 Mn2 O6 -57.6(7) . . . . ? C17 O3 Mn2 O8 113.6(7) . . . 1_554 ? C26 O4 Mn2 O3 -175.8(9) . . . . ? C26 O4 Mn2 N4 5.7(9) . . . . ? C26 O4 Mn2 N3 -8(5) . . . . ? C26 O4 Mn2 O6 92.5(9) . . . . ? C26 O4 Mn2 O8 -80.9(9) . . . 1_554 ? C32 N4 Mn2 O3 -167(4) . . . . ? C25 N4 Mn2 O3 9(5) . . . . ? C32 N4 Mn2 O4 -3.5(11) . . . . ? C25 N4 Mn2 O4 172.6(9) . . . . ? C32 N4 Mn2 N3 175.1(12) . . . . ? C25 N4 Mn2 N3 -8.8(9) . . . . ? C32 N4 Mn2 O6 -100.0(11) . . . . ? C25 N4 Mn2 O6 76.0(9) . . . . ? C32 N4 Mn2 O8 88.2(11) . . . 1_554 ? C25 N4 Mn2 O8 -95.8(9) . . . 1_554 ? C23 N3 Mn2 O3 -16.3(12) . . . . ? C24 N3 Mn2 O3 165.5(9) . . . . ? C23 N3 Mn2 O4 176(4) . . . . ? C24 N3 Mn2 O4 -2(5) . . . . ? C23 N3 Mn2 N4 162.0(12) . . . . ? C24 N3 Mn2 N4 -16.3(9) . . . . ? C23 N3 Mn2 O6 74.8(12) . . . . ? C24 N3 Mn2 O6 -103.5(10) . . . . ? C23 N3 Mn2 O8 -110.9(12) . . . 1_554 ? C24 N3 Mn2 O8 70.8(10) . . . 1_554 ? C33 O6 Mn2 O3 66.1(14) . . . . ? C33 O6 Mn2 O4 159.8(14) . . . . ? C33 O6 Mn2 N4 -108.6(14) . . . . ? C33 O6 Mn2 N3 -25.8(14) . . . . ? C33 O6 Mn2 O8 -59(3) . . . 1_554 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.664 _refine_diff_density_min -0.906 _refine_diff_density_rms 0.153 # Attachment '10.cif' data_mwmn3 _database_code_depnum_ccdc_archive 'CCDC 739763' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 Mn N2 O4' _chemical_formula_weight 436.38 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 monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 18.843(8) _cell_length_b 11.738(6) _cell_length_c 20.626(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.16(7) _cell_angle_gamma 90.00 _cell_volume 4162.4(38) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.4 _cell_measurement_theta_max 13.55 _exptl_crystal_description prism _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 0.665 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9338 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 160(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 '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3829 _diffrn_reflns_av_R_equivalents 0.0105 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3631 _reflns_number_gt 2746 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'DIRDIF-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0489P)^2^+5.8931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00013(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3631 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.39393(11) 0.42031(15) 0.88360(8) 0.0211(6) Uani 1 1 d G . . C2 C 0.41224(11) 0.52181(14) 0.92162(10) 0.0281(7) Uani 1 1 d G . . H2 H 0.4318 0.5844 0.9047 0.034 Uiso 1 1 calc R . . C3 C 0.40192(13) 0.53172(15) 0.98436(10) 0.0363(8) Uani 1 1 d G . . H3 H 0.4144 0.6011 1.0103 0.044 Uiso 1 1 calc R . . C4 C 0.37330(14) 0.44013(19) 1.00908(9) 0.0452(10) Uani 1 1 d G . . H4 H 0.3662 0.4469 1.0520 0.054 Uiso 1 1 calc R . . C5 C 0.35499(14) 0.33862(16) 0.97107(11) 0.0427(9) Uani 1 1 d G . . H5 H 0.3354 0.2760 0.9880 0.051 Uiso 1 1 calc R . . C6 C 0.36531(12) 0.32871(13) 0.90832(10) 0.0276(7) Uani 1 1 d G . . C7 C 0.34014(16) 0.2202(3) 0.86973(16) 0.0262(6) Uani 1 1 d . . . H7 H 0.3122 0.1691 0.8864 0.031 Uiso 1 1 calc R . . C8 C 0.31270(17) 0.0833(3) 0.77867(17) 0.0286(7) Uani 1 1 d . . . H8A H 0.2665 0.1049 0.7355 0.034 Uiso 1 1 calc R . . H8B H 0.2943 0.0406 0.8102 0.034 Uiso 1 1 calc R . . C9 C 0.36399(17) 0.0055(3) 0.75723(16) 0.0257(7) Uani 1 1 d . . . H9A H 0.3345 -0.0643 0.7352 0.031 Uiso 1 1 calc R . . H9B H 0.4097 -0.0175 0.8004 0.031 Uiso 1 1 calc R . . C10 C 0.39219(17) 0.0619(2) 0.70487(15) 0.0238(6) Uani 1 1 d . . . H10A H 0.4128 0.0029 0.6829 0.029 Uiso 1 1 calc R . . H10B H 0.3478 0.0997 0.6665 0.029 Uiso 1 1 calc R . . C11 C 0.59589(8) 0.25906(15) 0.84313(9) 0.0202(6) Uani 1 1 d G . . C12 C 0.66712(9) 0.30257(15) 0.88984(8) 0.0231(6) Uani 1 1 d G . . H12 H 0.6698 0.3504 0.9279 0.028 Uiso 1 1 calc R . . C13 C 0.73440(7) 0.27615(16) 0.88078(9) 0.0269(7) Uani 1 1 d G . . H13 H 0.7831 0.3059 0.9127 0.032 Uiso 1 1 calc R . . C14 C 0.73045(8) 0.20622(17) 0.82501(10) 0.0269(7) Uani 1 1 d G . . H14 H 0.7764 0.1882 0.8188 0.032 Uiso 1 1 calc R . . C15 C 0.65921(10) 0.16271(15) 0.77831(8) 0.0252(7) Uani 1 1 d G . . H15 H 0.6565 0.1149 0.7402 0.030 Uiso 1 1 calc R . . C16 C 0.59193(8) 0.18913(15) 0.78736(8) 0.0207(6) Uani 1 1 d G . . C17 C 0.52200(16) 0.1278(2) 0.74362(14) 0.0201(6) Uani 1 1 d . . . H17 H 0.5269 0.0688 0.7142 0.024 Uiso 1 1 calc R . . C18 C 0.38447(17) 0.3823(2) 0.66289(15) 0.0221(6) Uani 1 1 d . . . C19 C 0.34820(17) 0.4450(3) 0.59250(15) 0.0261(7) Uani 1 1 d . . . H19A H 0.3131 0.3919 0.5563 0.031 Uiso 1 1 calc R . . H19B H 0.3159 0.5080 0.5976 0.031 Uiso 1 1 calc R . . C20 C 0.40545(18) 0.4939(3) 0.56538(16) 0.0303(7) Uani 1 1 d . . . H20A H 0.4333 0.4304 0.5544 0.036 Uiso 1 1 calc R . . H20B H 0.4444 0.5403 0.6034 0.036 Uiso 1 1 calc R . . C21 C 0.36681(19) 0.5675(3) 0.49924(17) 0.0339(8) Uani 1 1 d . . . H21A H 0.3303 0.5196 0.4603 0.041 Uiso 1 1 calc R . . H21B H 0.3360 0.6278 0.5094 0.041 Uiso 1 1 calc R . . C22 C 0.4236(2) 0.6226(4) 0.4745(2) 0.0529(11) Uani 1 1 d . . . H22A H 0.4628 0.6646 0.5141 0.079 Uiso 1 1 calc R . . H22B H 0.3957 0.6753 0.4355 0.079 Uiso 1 1 calc R . . H22C H 0.4491 0.5637 0.4580 0.079 Uiso 1 1 calc R . . Mn1 Mn 0.42770(2) 0.28529(4) 0.78289(2) 0.01788(14) Uani 1 1 d . . . N1 N 0.35242(13) 0.18816(19) 0.81559(12) 0.0213(5) Uani 1 1 d . . . N2 N 0.45362(13) 0.14693(19) 0.74129(12) 0.0194(5) Uani 1 1 d . . . O1 O 0.40307(11) 0.41628(16) 0.82218(10) 0.0232(4) Uani 1 1 d . . . O2 O 0.53248(11) 0.28862(17) 0.85424(10) 0.0234(4) Uani 1 1 d . . . O3 O 0.45508(11) 0.39353(17) 0.70238(10) 0.0253(5) Uani 1 1 d . . . O4 O 0.34046(11) 0.32146(17) 0.68241(10) 0.0261(5) 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 C1 0.0160(13) 0.0274(16) 0.0211(14) 0.0014(12) 0.0088(11) 0.0058(12) C2 0.0243(15) 0.0313(17) 0.0285(16) -0.0015(13) 0.0105(13) 0.0064(13) C3 0.0369(19) 0.040(2) 0.0282(17) -0.0074(15) 0.0098(15) 0.0108(16) C4 0.065(3) 0.052(2) 0.0299(19) -0.0016(17) 0.0312(18) 0.012(2) C5 0.063(2) 0.041(2) 0.0365(19) 0.0034(16) 0.0338(18) 0.0043(18) C6 0.0286(16) 0.0303(17) 0.0278(16) 0.0025(13) 0.0156(13) 0.0059(13) C7 0.0266(15) 0.0256(16) 0.0342(16) 0.0066(14) 0.0202(13) 0.0009(14) C8 0.0248(16) 0.0264(16) 0.0357(17) -0.0018(14) 0.0135(13) -0.0075(13) C9 0.0266(16) 0.0188(15) 0.0319(17) -0.0029(13) 0.0120(13) -0.0060(13) C10 0.0268(15) 0.0204(15) 0.0229(15) -0.0065(12) 0.0087(12) -0.0042(13) C11 0.0239(14) 0.0181(14) 0.0203(14) 0.0065(11) 0.0109(12) 0.0027(11) C12 0.0259(15) 0.0216(15) 0.0211(14) -0.0033(12) 0.0090(12) -0.0006(12) C13 0.0202(14) 0.0276(17) 0.0296(16) 0.0040(14) 0.0068(12) -0.0004(13) C14 0.0215(14) 0.0277(16) 0.0335(16) 0.0030(14) 0.0134(13) 0.0046(13) C15 0.0310(16) 0.0232(15) 0.0262(15) 0.0003(13) 0.0164(13) 0.0027(13) C16 0.0222(14) 0.0190(15) 0.0222(14) 0.0037(12) 0.0104(12) 0.0005(11) C17 0.0289(16) 0.0160(14) 0.0180(13) 0.0014(11) 0.0123(12) 0.0038(12) C18 0.0283(16) 0.0171(14) 0.0234(15) -0.0038(12) 0.0133(13) 0.0018(12) C19 0.0265(16) 0.0271(16) 0.0235(15) 0.0014(13) 0.0088(13) 0.0028(13) C20 0.0308(17) 0.0339(18) 0.0305(17) 0.0092(14) 0.0171(14) 0.0100(14) C21 0.0364(18) 0.0386(19) 0.0293(17) 0.0070(15) 0.0161(15) 0.0073(15) C22 0.042(2) 0.066(3) 0.060(2) 0.037(2) 0.0304(19) 0.021(2) Mn1 0.0188(2) 0.0176(2) 0.0196(2) -0.00183(18) 0.01027(17) -0.00033(19) N1 0.0186(12) 0.0219(13) 0.0244(12) 0.0014(10) 0.0098(10) 0.0000(10) N2 0.0237(13) 0.0165(12) 0.0201(12) -0.0015(10) 0.0113(10) -0.0006(10) O1 0.0296(11) 0.0212(10) 0.0249(10) -0.0010(8) 0.0174(9) 0.0019(9) O2 0.0204(10) 0.0297(11) 0.0208(10) -0.0050(9) 0.0091(8) 0.0017(9) O3 0.0225(11) 0.0255(11) 0.0251(10) -0.0003(9) 0.0070(9) 0.0000(9) O4 0.0234(10) 0.0278(11) 0.0284(11) 0.0026(9) 0.0120(9) -0.0004(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.347(2) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.474(3) . ? C7 N1 1.286(4) . ? C7 H7 0.9500 . ? C8 N1 1.480(4) . ? C8 C9 1.521(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.535(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.479(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.351(2) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.447(3) . ? C17 N2 1.289(3) . ? C17 H17 0.9500 . ? C18 O3 1.251(4) . ? C18 O4 1.278(3) . ? C18 C19 1.518(4) . ? C18 Mn1 2.537(3) . ? C19 C20 1.516(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.525(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.506(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Mn1 O1 1.883(2) . ? Mn1 O2 1.920(3) . ? Mn1 N2 1.989(2) . ? Mn1 O4 2.095(3) . ? Mn1 N1 2.133(2) . ? Mn1 O3 2.311(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 117.57(15) . . ? O1 C1 C6 122.41(15) . . ? C2 C1 C6 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 116.01(16) . . ? C1 C6 C7 123.90(16) . . ? N1 C7 C6 126.1(2) . . ? N1 C7 H7 116.9 . . ? C6 C7 H7 116.9 . . ? N1 C8 C9 113.7(2) . . ? N1 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N1 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 113.0(3) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N2 C10 C9 111.0(2) . . ? N2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O2 C11 C12 117.28(13) . . ? O2 C11 C16 122.72(14) . . ? C12 C11 C16 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 C17 116.94(15) . . ? C11 C16 C17 122.42(15) . . ? N2 C17 C16 125.3(2) . . ? N2 C17 H17 117.3 . . ? C16 C17 H17 117.3 . . ? O3 C18 O4 120.5(3) . . ? O3 C18 C19 121.0(3) . . ? O4 C18 C19 118.4(3) . . ? O3 C18 Mn1 65.20(16) . . ? O4 C18 Mn1 55.41(15) . . ? C19 C18 Mn1 171.8(2) . . ? C20 C19 C18 115.2(3) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C21 113.1(3) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 113.6(3) . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O1 Mn1 O2 90.62(9) . . ? O1 Mn1 N2 179.93(13) . . ? O2 Mn1 N2 89.44(9) . . ? O1 Mn1 O4 91.63(8) . . ? O2 Mn1 O4 153.95(9) . . ? N2 Mn1 O4 88.31(9) . . ? O1 Mn1 N1 89.28(9) . . ? O2 Mn1 N1 112.14(9) . . ? N2 Mn1 N1 90.71(10) . . ? O4 Mn1 N1 93.84(9) . . ? O1 Mn1 O3 91.56(8) . . ? O2 Mn1 O3 94.45(9) . . ? N2 Mn1 O3 88.42(9) . . ? O4 Mn1 O3 59.55(7) . . ? N1 Mn1 O3 153.39(9) . . ? O1 Mn1 C18 90.91(9) . . ? O2 Mn1 C18 123.88(10) . . ? N2 Mn1 C18 89.04(9) . . ? O4 Mn1 C18 30.15(9) . . ? N1 Mn1 C18 123.98(10) . . ? O3 Mn1 C18 29.43(8) . . ? C7 N1 C8 117.2(2) . . ? C7 N1 Mn1 119.8(2) . . ? C8 N1 Mn1 122.94(18) . . ? C17 N2 C10 117.7(2) . . ? C17 N2 Mn1 123.0(2) . . ? C10 N2 Mn1 119.38(17) . . ? C1 O1 Mn1 125.61(15) . . ? C11 O2 Mn1 124.63(14) . . ? C18 O3 Mn1 85.37(17) . . ? C18 O4 Mn1 94.44(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.26(19) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -176.7(2) . . . . ? O1 C1 C6 C5 -178.2(2) . . . . ? C2 C1 C6 C5 0.0 . . . . ? O1 C1 C6 C7 -1.8(2) . . . . ? C2 C1 C6 C7 176.4(2) . . . . ? C5 C6 C7 N1 -171.5(2) . . . . ? C1 C6 C7 N1 12.0(4) . . . . ? N1 C8 C9 C10 -61.6(3) . . . . ? C8 C9 C10 N2 74.2(3) . . . . ? O2 C11 C12 C13 -179.37(18) . . . . ? C16 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C14 C15 C16 C17 -171.07(19) . . . . ? O2 C11 C16 C15 179.34(19) . . . . ? C12 C11 C16 C15 0.0 . . . . ? O2 C11 C16 C17 -10.1(2) . . . . ? C12 C11 C16 C17 170.6(2) . . . . ? C15 C16 C17 N2 -174.8(2) . . . . ? C11 C16 C17 N2 14.4(3) . . . . ? O3 C18 C19 C20 15.7(4) . . . . ? O4 C18 C19 C20 -167.3(3) . . . . ? Mn1 C18 C19 C20 153.2(13) . . . . ? C18 C19 C20 C21 -173.3(3) . . . . ? C19 C20 C21 C22 176.3(3) . . . . ? O3 C18 Mn1 O1 91.55(16) . . . . ? O4 C18 Mn1 O1 -91.68(17) . . . . ? C19 C18 Mn1 O1 -48.8(15) . . . . ? O3 C18 Mn1 O2 0.2(2) . . . . ? O4 C18 Mn1 O2 176.96(15) . . . . ? C19 C18 Mn1 O2 -140.1(14) . . . . ? O3 C18 Mn1 N2 -88.49(17) . . . . ? O4 C18 Mn1 N2 88.28(17) . . . . ? C19 C18 Mn1 N2 131.2(15) . . . . ? O3 C18 Mn1 O4 -176.8(3) . . . . ? C19 C18 Mn1 O4 42.9(14) . . . . ? O3 C18 Mn1 N1 -178.70(14) . . . . ? O4 C18 Mn1 N1 -1.9(2) . . . . ? C19 C18 Mn1 N1 41.0(15) . . . . ? O4 C18 Mn1 O3 176.8(3) . . . . ? C19 C18 Mn1 O3 -140.3(15) . . . . ? C6 C7 N1 C8 -171.6(2) . . . . ? C6 C7 N1 Mn1 8.5(4) . . . . ? C9 C8 N1 C7 -138.1(3) . . . . ? C9 C8 N1 Mn1 41.8(3) . . . . ? O1 Mn1 N1 C7 -27.4(2) . . . . ? O2 Mn1 N1 C7 63.0(2) . . . . ? N2 Mn1 N1 C7 152.7(2) . . . . ? O4 Mn1 N1 C7 -119.0(2) . . . . ? O3 Mn1 N1 C7 -119.4(2) . . . . ? C18 Mn1 N1 C7 -118.0(2) . . . . ? O1 Mn1 N1 C8 152.8(2) . . . . ? O2 Mn1 N1 C8 -116.9(2) . . . . ? N2 Mn1 N1 C8 -27.2(2) . . . . ? O4 Mn1 N1 C8 61.2(2) . . . . ? O3 Mn1 N1 C8 60.7(3) . . . . ? C18 Mn1 N1 C8 62.1(2) . . . . ? C16 C17 N2 C10 -168.0(2) . . . . ? C16 C17 N2 Mn1 12.9(4) . . . . ? C9 C10 N2 C17 115.9(3) . . . . ? C9 C10 N2 Mn1 -65.0(3) . . . . ? O1 Mn1 N2 C17 133(100) . . . . ? O2 Mn1 N2 C17 -31.1(2) . . . . ? O4 Mn1 N2 C17 122.9(2) . . . . ? N1 Mn1 N2 C17 -143.3(2) . . . . ? O3 Mn1 N2 C17 63.3(2) . . . . ? C18 Mn1 N2 C17 92.8(2) . . . . ? O1 Mn1 N2 C10 -46(81) . . . . ? O2 Mn1 N2 C10 149.8(2) . . . . ? O4 Mn1 N2 C10 -56.1(2) . . . . ? N1 Mn1 N2 C10 37.7(2) . . . . ? O3 Mn1 N2 C10 -115.7(2) . . . . ? C18 Mn1 N2 C10 -86.3(2) . . . . ? C2 C1 O1 Mn1 150.21(13) . . . . ? C6 C1 O1 Mn1 -31.6(2) . . . . ? O2 Mn1 O1 C1 -72.78(19) . . . . ? N2 Mn1 O1 C1 123(100) . . . . ? O4 Mn1 O1 C1 133.17(18) . . . . ? N1 Mn1 O1 C1 39.35(19) . . . . ? O3 Mn1 O1 C1 -167.25(18) . . . . ? C18 Mn1 O1 C1 163.32(19) . . . . ? C12 C11 O2 Mn1 157.68(12) . . . . ? C16 C11 O2 Mn1 -21.7(2) . . . . ? O1 Mn1 O2 C11 -144.24(19) . . . . ? N2 Mn1 O2 C11 35.74(19) . . . . ? O4 Mn1 O2 C11 -49.3(3) . . . . ? N1 Mn1 O2 C11 126.28(18) . . . . ? O3 Mn1 O2 C11 -52.63(19) . . . . ? C18 Mn1 O2 C11 -52.7(2) . . . . ? O4 C18 O3 Mn1 -3.1(2) . . . . ? C19 C18 O3 Mn1 173.9(2) . . . . ? O1 Mn1 O3 C18 -89.09(17) . . . . ? O2 Mn1 O3 C18 -179.84(16) . . . . ? N2 Mn1 O3 C18 90.84(17) . . . . ? O4 Mn1 O3 C18 1.88(15) . . . . ? N1 Mn1 O3 C18 2.4(3) . . . . ? O3 C18 O4 Mn1 3.4(3) . . . . ? C19 C18 O4 Mn1 -173.7(2) . . . . ? O1 Mn1 O4 C18 89.01(17) . . . . ? O2 Mn1 O4 C18 -5.7(3) . . . . ? N2 Mn1 O4 C18 -91.00(17) . . . . ? N1 Mn1 O4 C18 178.40(16) . . . . ? O3 Mn1 O4 C18 -1.84(15) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.488 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.065 # Attachment '739764.cif' data_mwmn4 _database_code_depnum_ccdc_archive 'CCDC 739764' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 Mn1 N2 O5' _chemical_formula_sum 'C21 H23 Mn N2 O5' _chemical_formula_weight 438.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5430(10) _cell_length_b 12.336(2) _cell_length_c 17.840(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.42(2) _cell_angle_gamma 90.00 _cell_volume 2082.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.91 _cell_measurement_theta_max 11.68 _exptl_crystal_description prism _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.668 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8780 _exptl_absorpt_correction_T_max 0.9362 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 180(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 '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_reflns_number 3878 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3644 _reflns_number_gt 2390 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0532P)^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 3644 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1852(2) 0.02510(18) 0.19006(10) 0.0276(8) Uani 1 1 d G . . C2 C 0.2589(2) 0.07883(16) 0.13893(14) 0.0372(9) Uani 1 1 d G . . H2 H 0.3111 0.1425 0.1540 0.045 Uiso 1 1 calc R . . C3 C 0.2562(3) 0.0394(2) 0.06576(12) 0.0463(11) Uani 1 1 d G . . H3 H 0.3066 0.0762 0.0308 0.056 Uiso 1 1 calc R . . C4 C 0.1798(3) -0.0537(2) 0.04372(10) 0.0490(11) Uani 1 1 d G . . H4 H 0.1779 -0.0806 -0.0063 0.059 Uiso 1 1 calc R . . C5 C 0.1060(3) -0.10741(17) 0.09484(13) 0.0410(10) Uani 1 1 d G . . H5 H 0.0538 -0.1711 0.0798 0.049 Uiso 1 1 calc R . . C6 C 0.1087(2) -0.06802(18) 0.16801(11) 0.0288(8) Uani 1 1 d G . . C7 C 0.0358(4) -0.1306(3) 0.21872(19) 0.0271(8) Uani 1 1 d . . . H7 H 0.0014 -0.1995 0.2011 0.033 Uiso 1 1 calc R . . C8 C -0.0522(4) -0.1841(3) 0.33097(19) 0.0269(8) Uani 1 1 d . . . H8A H -0.0820 -0.2477 0.2990 0.032 Uiso 1 1 calc R . . H8B H -0.1374 -0.1527 0.3488 0.032 Uiso 1 1 calc R . . C9 C 0.0509(4) -0.2209(3) 0.39912(19) 0.0266(8) Uani 1 1 d . . . H9 H 0.0073 -0.2845 0.4221 0.032 Uiso 1 1 calc R . . C10 C 0.0801(4) -0.1358(3) 0.46009(19) 0.0294(8) Uani 1 1 d . . . H10A H -0.0092 -0.1186 0.4802 0.035 Uiso 1 1 calc R . . H10B H 0.1466 -0.1661 0.5021 0.035 Uiso 1 1 calc R . . C11 C 0.24628(19) 0.18791(17) 0.41130(12) 0.0266(8) Uani 1 1 d G . . C12 C 0.3168(2) 0.28323(16) 0.39808(12) 0.0346(9) Uani 1 1 d G . . H12 H 0.2757 0.3330 0.3610 0.041 Uiso 1 1 calc R . . C13 C 0.4474(2) 0.30570(16) 0.43918(14) 0.0398(10) Uani 1 1 d G . . H13 H 0.4956 0.3708 0.4301 0.048 Uiso 1 1 calc R . . C14 C 0.50752(19) 0.2328(2) 0.49350(13) 0.0399(10) Uani 1 1 d G . . H14 H 0.5968 0.2482 0.5216 0.048 Uiso 1 1 calc R . . C15 C 0.4370(2) 0.13752(18) 0.50672(12) 0.0339(9) Uani 1 1 d G . . H15 H 0.4781 0.0877 0.5438 0.041 Uiso 1 1 calc R . . C16 C 0.3064(2) 0.11505(15) 0.46562(12) 0.0269(8) Uani 1 1 d G . . C17 C 0.2424(4) 0.0096(3) 0.47764(18) 0.0251(8) Uani 1 1 d . . . H17 H 0.2796 -0.0296 0.5216 0.030 Uiso 1 1 calc R . . C18 C -0.1993(4) 0.1001(3) 0.2962(2) 0.0311(9) Uani 1 1 d . . . C19 C -0.3515(4) 0.1361(4) 0.2829(3) 0.0503(12) Uani 1 1 d . . . H19A H -0.3594 0.2065 0.3085 0.060 Uiso 1 1 calc R . . H19B H -0.3777 0.1481 0.2280 0.060 Uiso 1 1 calc R . . C20 C -0.4555(4) 0.0595(4) 0.3094(2) 0.0528(13) Uani 1 1 d . . . H20A H -0.5505 0.0930 0.3008 0.063 Uiso 1 1 calc R . . H20B H -0.4313 0.0488 0.3646 0.063 Uiso 1 1 calc R . . C21 C -0.4621(5) -0.0494(5) 0.2715(3) 0.0839(18) Uani 1 1 d . . . H21A H -0.4789 -0.0397 0.2166 0.126 Uiso 1 1 calc R . . H21B H -0.5392 -0.0920 0.2880 0.126 Uiso 1 1 calc R . . H21C H -0.3724 -0.0876 0.2853 0.126 Uiso 1 1 calc R . . Mn1 Mn 0.06061(5) 0.04049(4) 0.33058(3) 0.02236(16) Uani 1 1 d . . . N1 N 0.0121(3) -0.1032(2) 0.28567(15) 0.0236(6) Uani 1 1 d . . . N2 N 0.1401(3) -0.0348(2) 0.43390(15) 0.0243(6) Uani 1 1 d . . . O1 O 0.1923(2) 0.06505(19) 0.26023(13) 0.0306(6) Uani 1 1 d . . . O2 O 0.1130(2) 0.17341(19) 0.37571(13) 0.0283(6) Uani 1 1 d . . . O3 O -0.1502(2) 0.0533(2) 0.35799(13) 0.0321(6) Uani 1 1 d . . . O4 O -0.1182(3) 0.1168(2) 0.24729(14) 0.0336(6) Uani 1 1 d . . . O5 O 0.1821(2) -0.2552(2) 0.37897(13) 0.0316(6) Uani 1 1 d . . . H5A H 0.1683 -0.2982 0.3422 0.047 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 C1 0.0197(17) 0.029(2) 0.034(2) 0.0029(17) 0.0040(15) 0.0044(16) C2 0.031(2) 0.031(2) 0.050(3) 0.0041(19) 0.0099(18) 0.0008(17) C3 0.046(2) 0.054(3) 0.042(2) 0.018(2) 0.0173(19) 0.003(2) C4 0.063(3) 0.056(3) 0.030(2) -0.002(2) 0.014(2) 0.002(3) C5 0.052(3) 0.040(2) 0.031(2) -0.0051(19) 0.0066(19) -0.004(2) C6 0.0304(19) 0.028(2) 0.0279(19) 0.0000(16) 0.0037(15) 0.0041(16) C7 0.0284(19) 0.0223(19) 0.028(2) -0.0043(15) -0.0052(15) 0.0002(16) C8 0.0265(18) 0.0231(19) 0.031(2) 0.0003(15) 0.0029(15) -0.0040(16) C9 0.0285(19) 0.024(2) 0.0276(19) 0.0028(15) 0.0037(15) -0.0019(16) C10 0.034(2) 0.027(2) 0.0277(19) 0.0011(16) 0.0075(16) 0.0014(17) C11 0.032(2) 0.0227(19) 0.0250(18) -0.0111(15) 0.0034(15) 0.0010(16) C12 0.041(2) 0.027(2) 0.035(2) -0.0027(17) 0.0044(17) -0.0030(18) C13 0.039(2) 0.031(2) 0.051(3) -0.014(2) 0.0106(19) -0.0109(19) C14 0.027(2) 0.040(2) 0.050(3) -0.013(2) -0.0004(18) 0.0004(19) C15 0.030(2) 0.035(2) 0.036(2) -0.0053(18) 0.0003(17) 0.0076(18) C16 0.0288(19) 0.029(2) 0.0228(18) -0.0071(16) 0.0043(15) 0.0002(16) C17 0.0265(18) 0.0261(19) 0.0227(18) -0.0021(15) 0.0032(15) 0.0065(15) C18 0.029(2) 0.025(2) 0.039(2) 0.0004(17) 0.0036(17) 0.0025(17) C19 0.030(2) 0.061(3) 0.061(3) 0.014(2) 0.007(2) 0.016(2) C20 0.028(2) 0.084(4) 0.046(3) -0.002(2) 0.0010(19) 0.003(2) C21 0.051(3) 0.082(4) 0.109(5) -0.016(4) -0.024(3) 0.004(3) Mn1 0.0247(3) 0.0187(3) 0.0230(3) -0.0006(2) 0.00084(19) -0.0003(2) N1 0.0252(15) 0.0222(16) 0.0223(15) 0.0013(12) -0.0008(12) 0.0003(13) N2 0.0274(15) 0.0230(15) 0.0227(14) -0.0020(13) 0.0037(12) 0.0046(14) O1 0.0276(13) 0.0312(15) 0.0338(14) -0.0066(11) 0.0066(11) -0.0066(11) O2 0.0309(14) 0.0189(13) 0.0332(14) -0.0032(11) -0.0028(11) 0.0020(11) O3 0.0328(14) 0.0356(15) 0.0275(13) 0.0040(12) 0.0021(11) 0.0051(12) O4 0.0315(14) 0.0333(15) 0.0368(14) 0.0091(12) 0.0082(11) 0.0010(12) O5 0.0324(14) 0.0322(15) 0.0295(14) -0.0053(12) 0.0020(11) 0.0044(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.339(3) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.436(4) . ? C7 N1 1.289(4) . ? C7 H7 0.9500 . ? C8 N1 1.467(4) . ? C8 C9 1.531(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O5 1.411(4) . ? C9 C10 1.512(5) . ? C9 H9 1.0000 . ? C10 N2 1.472(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.358(3) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 C17 1.464(4) . ? C17 N2 1.290(4) . ? C17 H17 0.9500 . ? C18 O4 1.255(4) . ? C18 O3 1.279(4) . ? C18 C19 1.508(5) . ? C18 Mn1 2.584(4) . ? C19 C20 1.492(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.502(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Mn1 O2 1.866(2) . ? Mn1 O1 1.912(2) . ? Mn1 N1 1.976(3) . ? Mn1 N2 2.115(3) . ? Mn1 O3 2.136(2) . ? Mn1 O4 2.313(3) . ? O5 H5A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 117.97(18) . . ? O1 C1 C6 122.03(18) . . ? C2 C1 C6 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 116.9(2) . . ? C1 C6 C7 123.1(2) . . ? N1 C7 C6 126.9(3) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N1 C8 C9 111.5(3) . . ? N1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O5 C9 C10 107.7(3) . . ? O5 C9 C8 112.8(3) . . ? C10 C9 C8 113.9(3) . . ? O5 C9 H9 107.4 . . ? C10 C9 H9 107.4 . . ? C8 C9 H9 107.4 . . ? N2 C10 C9 113.7(3) . . ? N2 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? N2 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? O2 C11 C12 118.48(17) . . ? O2 C11 C16 121.20(18) . . ? C12 C11 C16 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 C17 117.54(19) . . ? C11 C16 C17 122.28(19) . . ? N2 C17 C16 125.8(3) . . ? N2 C17 H17 117.1 . . ? C16 C17 H17 117.1 . . ? O4 C18 O3 118.9(3) . . ? O4 C18 C19 120.7(3) . . ? O3 C18 C19 120.4(3) . . ? O4 C18 Mn1 63.44(18) . . ? O3 C18 Mn1 55.46(17) . . ? C19 C18 Mn1 175.3(3) . . ? C20 C19 C18 115.5(4) . . ? C20 C19 H19A 108.4 . . ? C18 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? C18 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C21 114.5(4) . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 Mn1 O1 88.95(11) . . ? O2 Mn1 N1 177.47(11) . . ? O1 Mn1 N1 90.88(11) . . ? O2 Mn1 N2 87.91(11) . . ? O1 Mn1 N2 116.70(10) . . ? N1 Mn1 N2 89.91(11) . . ? O2 Mn1 O3 92.54(10) . . ? O1 Mn1 O3 148.98(10) . . ? N1 Mn1 O3 88.90(11) . . ? N2 Mn1 O3 94.32(10) . . ? O2 Mn1 O4 93.09(10) . . ? O1 Mn1 O4 90.38(10) . . ? N1 Mn1 O4 89.43(10) . . ? N2 Mn1 O4 152.91(10) . . ? O3 Mn1 O4 58.60(9) . . ? O2 Mn1 C18 92.75(11) . . ? O1 Mn1 C18 119.42(11) . . ? N1 Mn1 C18 89.53(11) . . ? N2 Mn1 C18 123.88(11) . . ? O3 Mn1 C18 29.56(10) . . ? O4 Mn1 C18 29.04(10) . . ? C7 N1 C8 117.9(3) . . ? C7 N1 Mn1 123.4(2) . . ? C8 N1 Mn1 118.6(2) . . ? C17 N2 C10 117.5(3) . . ? C17 N2 Mn1 119.9(2) . . ? C10 N2 Mn1 122.5(2) . . ? C1 O1 Mn1 126.65(17) . . ? C11 O2 Mn1 120.01(17) . . ? C18 O3 Mn1 95.0(2) . . ? C18 O4 Mn1 87.5(2) . . ? C9 O5 H5A 109.5 . . ? 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 O1 C1 C2 C3 179.1(2) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -177.1(3) . . . . ? O1 C1 C6 C5 -179.0(2) . . . . ? C2 C1 C6 C5 0.0 . . . . ? O1 C1 C6 C7 -2.2(3) . . . . ? C2 C1 C6 C7 176.9(3) . . . . ? C5 C6 C7 N1 -171.9(3) . . . . ? C1 C6 C7 N1 11.2(5) . . . . ? N1 C8 C9 O5 -52.2(4) . . . . ? N1 C8 C9 C10 71.0(4) . . . . ? O5 C9 C10 N2 66.8(4) . . . . ? C8 C9 C10 N2 -59.1(4) . . . . ? O2 C11 C12 C13 173.5(2) . . . . ? C16 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C14 C15 C16 C17 175.2(2) . . . . ? O2 C11 C16 C15 -173.4(2) . . . . ? C12 C11 C16 C15 0.0 . . . . ? O2 C11 C16 C17 11.7(3) . . . . ? C12 C11 C16 C17 -175.0(2) . . . . ? C15 C16 C17 N2 -163.7(3) . . . . ? C11 C16 C17 N2 11.4(4) . . . . ? O4 C18 C19 C20 140.7(4) . . . . ? O3 C18 C19 C20 -40.3(6) . . . . ? Mn1 C18 C19 C20 -68(4) . . . . ? C18 C19 C20 C21 -61.8(5) . . . . ? O4 C18 Mn1 O2 91.4(2) . . . . ? O3 C18 Mn1 O2 -90.3(2) . . . . ? C19 C18 Mn1 O2 -61(4) . . . . ? O4 C18 Mn1 O1 1.1(2) . . . . ? O3 C18 Mn1 O1 179.36(19) . . . . ? C19 C18 Mn1 O1 -151(4) . . . . ? O4 C18 Mn1 N1 -89.7(2) . . . . ? O3 C18 Mn1 N1 88.6(2) . . . . ? C19 C18 Mn1 N1 118(4) . . . . ? O4 C18 Mn1 N2 -179.26(19) . . . . ? O3 C18 Mn1 N2 -1.0(3) . . . . ? C19 C18 Mn1 N2 28(4) . . . . ? O4 C18 Mn1 O3 -178.3(4) . . . . ? C19 C18 Mn1 O3 29(3) . . . . ? O3 C18 Mn1 O4 178.3(4) . . . . ? C19 C18 Mn1 O4 -153(4) . . . . ? C6 C7 N1 C8 -174.0(3) . . . . ? C6 C7 N1 Mn1 5.0(5) . . . . ? C9 C8 N1 C7 112.5(3) . . . . ? C9 C8 N1 Mn1 -66.5(3) . . . . ? O2 Mn1 N1 C7 -106(3) . . . . ? O1 Mn1 N1 C7 -20.0(3) . . . . ? N2 Mn1 N1 C7 -136.7(3) . . . . ? O3 Mn1 N1 C7 129.0(3) . . . . ? O4 Mn1 N1 C7 70.4(3) . . . . ? C18 Mn1 N1 C7 99.4(3) . . . . ? O2 Mn1 N1 C8 73(3) . . . . ? O1 Mn1 N1 C8 159.0(2) . . . . ? N2 Mn1 N1 C8 42.3(2) . . . . ? O3 Mn1 N1 C8 -52.0(2) . . . . ? O4 Mn1 N1 C8 -110.6(2) . . . . ? C18 Mn1 N1 C8 -81.6(2) . . . . ? C16 C17 N2 C10 -173.4(3) . . . . ? C16 C17 N2 Mn1 4.6(4) . . . . ? C9 C10 N2 C17 -137.5(3) . . . . ? C9 C10 N2 Mn1 44.5(4) . . . . ? O2 Mn1 N2 C17 -29.3(3) . . . . ? O1 Mn1 N2 C17 58.5(3) . . . . ? N1 Mn1 N2 C17 149.4(3) . . . . ? O3 Mn1 N2 C17 -121.7(3) . . . . ? O4 Mn1 N2 C17 -122.0(3) . . . . ? C18 Mn1 N2 C17 -121.2(3) . . . . ? O2 Mn1 N2 C10 148.7(2) . . . . ? O1 Mn1 N2 C10 -123.6(2) . . . . ? N1 Mn1 N2 C10 -32.6(2) . . . . ? O3 Mn1 N2 C10 56.3(2) . . . . ? O4 Mn1 N2 C10 56.0(4) . . . . ? C18 Mn1 N2 C10 56.7(3) . . . . ? C2 C1 O1 Mn1 158.20(16) . . . . ? C6 C1 O1 Mn1 -22.7(3) . . . . ? O2 Mn1 O1 C1 -153.2(2) . . . . ? N1 Mn1 O1 C1 29.3(2) . . . . ? N2 Mn1 O1 C1 119.6(2) . . . . ? O3 Mn1 O1 C1 -60.0(3) . . . . ? O4 Mn1 O1 C1 -60.1(2) . . . . ? C18 Mn1 O1 C1 -60.7(3) . . . . ? C12 C11 O2 Mn1 135.22(15) . . . . ? C16 C11 O2 Mn1 -51.3(3) . . . . ? O1 Mn1 O2 C11 -65.4(2) . . . . ? N1 Mn1 O2 C11 21(3) . . . . ? N2 Mn1 O2 C11 51.4(2) . . . . ? O3 Mn1 O2 C11 145.6(2) . . . . ? O4 Mn1 O2 C11 -155.7(2) . . . . ? C18 Mn1 O2 C11 175.2(2) . . . . ? O4 C18 O3 Mn1 1.7(4) . . . . ? C19 C18 O3 Mn1 -177.4(3) . . . . ? O2 Mn1 O3 C18 91.1(2) . . . . ? O1 Mn1 O3 C18 -1.1(3) . . . . ? N1 Mn1 O3 C18 -91.0(2) . . . . ? N2 Mn1 O3 C18 179.2(2) . . . . ? O4 Mn1 O3 C18 -1.0(2) . . . . ? O3 C18 O4 Mn1 -1.6(3) . . . . ? C19 C18 O4 Mn1 177.5(4) . . . . ? O2 Mn1 O4 C18 -90.1(2) . . . . ? O1 Mn1 O4 C18 -179.1(2) . . . . ? N1 Mn1 O4 C18 90.0(2) . . . . ? N2 Mn1 O4 C18 1.3(3) . . . . ? O3 Mn1 O4 C18 1.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O4 0.84 1.92 2.754(3) 172.5 2_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.462 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.072 # Attachment '739765.cif' data_mw-016a _database_code_depnum_ccdc_archive 'CCDC 739765' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C68 H62 Mn4 N8 O12, 2(C2 H3 O2), 4(H2 O) ; _chemical_formula_sum 'C72 H76 Mn4 N8 O20' _chemical_formula_weight 1593.17 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8025(2) _cell_length_b 13.2412(3) _cell_length_c 13.5735(3) _cell_angle_alpha 100.1700(10) _cell_angle_beta 94.6520(10) _cell_angle_gamma 102.2140(10) _cell_volume 1681.96(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7593 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Brown _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.818 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7408 _exptl_absorpt_correction_T_max 0.9602 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33488 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.65 _reflns_number_total 7743 _reflns_number_gt 6058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; ? ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. H atoms on solvent molecules not located, due to extensive disorder. Disorder on acetate and water molecules found to be corellated and in final refinement tied to single variable. ; _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^)+(0.0584P)^2^+3.0332P] 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 7743 _refine_ls_number_parameters 458 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.31145(18) 1.11458(14) 0.48317(14) 0.0188(6) Uani 1 1 d G . . C2 C 0.32206(19) 1.21828(14) 0.47226(15) 0.0232(7) Uani 1 1 d G . . H2 H 0.3923 1.2503 0.4359 0.028 Uiso 1 1 calc R . . C3 C 0.2299(2) 1.27518(12) 0.51457(17) 0.0293(8) Uani 1 1 d G . . H3 H 0.2372 1.3461 0.5071 0.035 Uiso 1 1 calc R . . C4 C 0.1272(2) 1.22837(15) 0.56778(17) 0.0313(8) Uani 1 1 d G . . H4 H 0.0642 1.2673 0.5967 0.038 Uiso 1 1 calc R . . C5 C 0.11658(18) 1.12467(15) 0.57869(15) 0.0244(7) Uani 1 1 d G . . H5 H 0.0464 1.0927 0.6151 0.029 Uiso 1 1 calc R . . C6 C 0.20870(19) 1.06777(11) 0.53639(15) 0.0193(6) Uani 1 1 d G . . C7 C 0.1972(3) 0.9616(2) 0.5552(2) 0.0190(6) Uani 1 1 d . . . H7 H 0.1373 0.9398 0.6029 0.023 Uiso 1 1 calc R . . C8 C 0.2560(3) 0.7921(2) 0.5400(2) 0.0235(7) Uani 1 1 d . . . H8A H 0.1674 0.7695 0.5685 0.028 Uiso 1 1 calc R . . H8B H 0.3359 0.7966 0.5913 0.028 Uiso 1 1 calc R . . C9 C 0.2624(3) 0.7136(2) 0.4450(2) 0.0229(7) Uani 1 1 d . . . H9A H 0.2882 0.6502 0.4629 0.028 Uiso 1 1 calc R . . H9B H 0.1696 0.6915 0.4032 0.028 Uiso 1 1 calc R . . C10 C 0.5705(2) 0.85781(14) 0.25847(15) 0.0219(6) Uani 1 1 d G . . C11 C 0.6635(2) 0.89028(13) 0.19207(16) 0.0301(8) Uani 1 1 d G . . H11 H 0.6779 0.9602 0.1804 0.036 Uiso 1 1 calc R . . C12 C 0.7353(2) 0.82044(17) 0.14276(16) 0.0351(9) Uani 1 1 d G . . H12 H 0.7988 0.8426 0.0974 0.042 Uiso 1 1 calc R . . C13 C 0.7141(2) 0.71813(16) 0.15986(17) 0.0345(9) Uani 1 1 d G . . H13 H 0.7632 0.6704 0.1262 0.041 Uiso 1 1 calc R . . C14 C 0.6212(2) 0.68566(13) 0.22627(16) 0.0270(7) Uani 1 1 d G . . H14 H 0.6067 0.6157 0.2380 0.032 Uiso 1 1 calc R . . C15 C 0.54934(19) 0.75549(15) 0.27557(14) 0.0215(6) Uani 1 1 d G . . C16 C 0.4482(3) 0.7141(2) 0.3391(2) 0.0195(6) Uani 1 1 d . . . H16 H 0.4389 0.6426 0.3449 0.023 Uiso 1 1 calc R . . C17 C -0.04615(19) 0.73606(15) -0.09215(13) 0.0191(6) Uani 1 1 d G . . C18 C -0.16988(16) 0.75788(16) -0.13109(15) 0.0219(6) Uani 1 1 d G . . H18 H -0.2542 0.7378 -0.1024 0.026 Uiso 1 1 calc R . . C19 C -0.17016(17) 0.80916(17) -0.21204(15) 0.0256(7) Uani 1 1 d G . . H19 H -0.2547 0.8241 -0.2387 0.031 Uiso 1 1 calc R . . C20 C -0.0467(2) 0.83861(17) -0.25405(14) 0.0277(7) Uani 1 1 d G . . H20 H -0.0469 0.8737 -0.3094 0.033 Uiso 1 1 calc R . . C21 C 0.07700(17) 0.81678(17) -0.21511(15) 0.0260(7) Uani 1 1 d G . . H21 H 0.1614 0.8369 -0.2438 0.031 Uiso 1 1 calc R . . C22 C 0.07729(16) 0.76551(16) -0.13416(14) 0.0214(6) Uani 1 1 d G . . C23 C 0.2099(3) 0.7445(3) -0.0980(2) 0.0230(7) Uani 1 1 d . . . H23 H 0.2887 0.7668 -0.1317 0.028 Uiso 1 1 calc R . . C24 C 0.3707(3) 0.6821(3) 0.0080(3) 0.0291(8) Uani 1 1 d . . . H24A H 0.4172 0.7360 0.0682 0.035 Uiso 1 1 calc R . . H24B H 0.4308 0.6876 -0.0469 0.035 Uiso 1 1 calc R . . C25 C 0.3479(3) 0.5730(3) 0.0322(3) 0.0271(7) Uani 1 1 d . . . H25A H 0.3231 0.5185 -0.0306 0.033 Uiso 1 1 calc R . . H25B H 0.4343 0.5640 0.0694 0.033 Uiso 1 1 calc R . . C26 C -0.01875(19) 0.51411(16) 0.19801(12) 0.0187(6) Uani 1 1 d G . . C27 C -0.12728(15) 0.49516(17) 0.25699(15) 0.0236(7) Uani 1 1 d G . . H27 H -0.2163 0.5080 0.2372 0.028 Uiso 1 1 calc R . . C28 C -0.10562(18) 0.45745(17) 0.34489(14) 0.0263(7) Uani 1 1 d G . . H28 H -0.1798 0.4445 0.3852 0.032 Uiso 1 1 calc R . . C29 C 0.0246(2) 0.43868(17) 0.37380(12) 0.0249(7) Uani 1 1 d G . . H29 H 0.0394 0.4129 0.4339 0.030 Uiso 1 1 calc R . . C30 C 0.13312(16) 0.45762(16) 0.31482(14) 0.0229(7) Uani 1 1 d G . . H30 H 0.2221 0.4448 0.3346 0.027 Uiso 1 1 calc R . . C31 C 0.11146(16) 0.49534(16) 0.22692(13) 0.0207(6) Uani 1 1 d G . . C32 C 0.2287(3) 0.5123(2) 0.1674(2) 0.0217(6) Uani 1 1 d . . . H32 H 0.3073 0.4840 0.1829 0.026 Uiso 1 1 calc R . . C33 C 0.1579(3) 0.8504(3) 0.2123(2) 0.0231(7) Uani 1 1 d . . . C34 C 0.1237(5) 0.9117(3) 0.1336(3) 0.0473(11) Uani 1 1 d . . . H34A H 0.0780 0.8625 0.0713 0.071 Uiso 1 1 calc R . . H34B H 0.2106 0.9565 0.1202 0.071 Uiso 1 1 calc R . . H34C H 0.0601 0.9559 0.1582 0.071 Uiso 1 1 calc R . . C35 C 0.5195(4) 0.3781(4) 0.2754(3) 0.0384(10) Uani 1 1 d D . . C36 C 0.4864(7) 0.4648(4) 0.3345(4) 0.0343(11) Uani 0.640(4) 1 d P A 1 O7 O 0.5499(6) 0.3159(5) 0.3113(7) 0.070(2) Uani 0.640(4) 1 d PD A 1 O8 O 0.5025(7) 0.3891(6) 0.1900(5) 0.0562(18) Uani 0.640(4) 1 d PD A 1 O9 O 0.4716(7) 0.8949(4) 0.7954(5) 0.076(2) Uani 0.640(4) 1 d P A 1 O11 O 0.4279(9) 0.9682(8) 0.0087(9) 0.134(3) Uani 0.640(4) 1 d P . 1 C36' C 0.5195(12) 0.2705(8) 0.2180(8) 0.0343(11) Uani 0.360(4) 1 d P A 2 O7' O 0.5644(8) 0.3768(8) 0.3653(6) 0.041(2) Uani 0.360(4) 1 d PD A 2 O8' O 0.5097(11) 0.4407(8) 0.2298(11) 0.059(4) Uani 0.360(4) 1 d PD A 2 O10 O 0.4271(7) 0.5246(5) 0.4628(5) 0.0293(17) Uani 0.360(4) 1 d P A 2 O12 O 0.4274(17) 0.0656(15) 0.0549(15) 0.134(3) Uani 0.360(4) 1 d P A 2 Mn1 Mn 0.37824(4) 0.91828(3) 0.40067(3) 0.01716(12) Uani 1 1 d . . . Mn2 Mn 0.08444(4) 0.63622(4) 0.05482(3) 0.01799(13) Uani 1 1 d . . . O1 O 0.4126(2) 1.06574(16) 0.44801(16) 0.0195(4) Uani 1 1 d . . . O2 O 0.5088(2) 0.93170(17) 0.30738(16) 0.0223(5) Uani 1 1 d . . . O3 O -0.0546(2) 0.68349(17) -0.01485(15) 0.0193(4) Uani 1 1 d . . . O4 O -0.0488(2) 0.54356(18) 0.10904(16) 0.0222(5) Uani 1 1 d . . . O5 O 0.1478(2) 0.75301(18) 0.18845(16) 0.0246(5) Uani 1 1 d . . . O6 O 0.1984(2) 0.90360(19) 0.30077(17) 0.0278(5) Uani 1 1 d . . . N1 N 0.2630(2) 0.8954(2) 0.51157(19) 0.0180(5) Uani 1 1 d . . . N2 N 0.3701(3) 0.7664(2) 0.38832(19) 0.0187(5) Uani 1 1 d . . . N3 N 0.2295(3) 0.6981(2) -0.02378(19) 0.0204(5) Uani 1 1 d . . . N4 N 0.2312(3) 0.5634(2) 0.09514(19) 0.0200(5) 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 C1 0.0163(13) 0.0200(15) 0.0165(14) -0.0040(12) -0.0036(11) 0.0049(11) C2 0.0220(15) 0.0227(16) 0.0227(16) 0.0031(13) -0.0037(12) 0.0040(12) C3 0.0268(17) 0.0251(18) 0.0351(19) 0.0019(15) -0.0060(14) 0.0108(14) C4 0.0212(16) 0.0308(19) 0.040(2) -0.0040(16) -0.0035(14) 0.0130(14) C5 0.0148(14) 0.0277(17) 0.0266(17) -0.0042(13) 0.0015(12) 0.0044(12) C6 0.0151(13) 0.0206(15) 0.0176(15) -0.0040(12) -0.0019(11) 0.0016(11) C7 0.0131(13) 0.0215(15) 0.0181(15) -0.0027(12) 0.0020(11) -0.0002(11) C8 0.0267(16) 0.0194(16) 0.0243(16) 0.0051(13) 0.0088(13) 0.0026(13) C9 0.0202(15) 0.0173(15) 0.0295(17) 0.0013(13) 0.0081(13) 0.0014(12) C10 0.0168(14) 0.0260(17) 0.0175(15) -0.0058(12) 0.0002(12) 0.0025(12) C11 0.0282(17) 0.0322(19) 0.0247(17) -0.0032(14) 0.0096(14) 0.0007(14) C12 0.0289(18) 0.042(2) 0.0286(19) -0.0033(16) 0.0146(15) 0.0001(16) C13 0.0250(17) 0.043(2) 0.0313(19) -0.0083(16) 0.0067(15) 0.0100(16) C14 0.0211(15) 0.0291(18) 0.0272(17) -0.0051(14) 0.0009(13) 0.0073(13) C15 0.0163(14) 0.0262(17) 0.0175(15) -0.0041(12) -0.0012(11) 0.0030(12) C16 0.0168(14) 0.0187(15) 0.0196(15) -0.0032(12) -0.0028(11) 0.0042(11) C17 0.0214(14) 0.0163(15) 0.0167(14) -0.0026(11) 0.0026(12) 0.0023(12) C18 0.0227(15) 0.0187(15) 0.0234(16) 0.0023(12) 0.0069(13) 0.0026(12) C19 0.0278(16) 0.0216(17) 0.0269(17) 0.0034(13) 0.0014(13) 0.0066(13) C20 0.0347(18) 0.0232(17) 0.0267(17) 0.0088(14) 0.0066(14) 0.0056(14) C21 0.0280(16) 0.0248(17) 0.0225(16) 0.0031(13) 0.0079(13) -0.0007(13) C22 0.0246(15) 0.0197(16) 0.0167(15) -0.0011(12) 0.0039(12) 0.0011(12) C23 0.0197(15) 0.0263(17) 0.0180(15) -0.0015(13) 0.0058(12) -0.0019(12) C24 0.0137(14) 0.046(2) 0.0262(17) 0.0085(15) 0.0029(13) 0.0021(14) C25 0.0185(15) 0.039(2) 0.0232(16) 0.0000(14) 0.0049(13) 0.0106(14) C26 0.0212(14) 0.0131(14) 0.0193(15) -0.0003(11) 0.0013(12) 0.0014(11) C27 0.0224(15) 0.0211(16) 0.0274(17) 0.0051(13) 0.0029(13) 0.0052(12) C28 0.0318(17) 0.0231(17) 0.0234(16) 0.0029(13) 0.0066(14) 0.0050(14) C29 0.0342(17) 0.0185(16) 0.0196(16) 0.0016(12) -0.0028(13) 0.0047(13) C30 0.0267(16) 0.0150(15) 0.0231(16) -0.0031(12) -0.0051(13) 0.0049(12) C31 0.0213(15) 0.0145(14) 0.0225(16) -0.0035(12) -0.0006(12) 0.0027(12) C32 0.0183(14) 0.0176(15) 0.0237(16) -0.0052(12) -0.0050(12) 0.0024(12) C33 0.0176(14) 0.0282(18) 0.0214(16) -0.0014(13) 0.0029(12) 0.0056(13) C34 0.082(3) 0.025(2) 0.030(2) -0.0012(16) -0.007(2) 0.013(2) C35 0.0197(17) 0.061(3) 0.024(2) 0.0065(19) 0.0087(14) -0.0136(18) C36 0.051(3) 0.025(2) 0.027(2) -0.008(2) 0.012(2) 0.016(2) O7 0.035(3) 0.047(4) 0.139(7) 0.046(5) 0.008(4) 0.012(3) O8 0.031(3) 0.052(4) 0.088(5) 0.021(4) 0.012(3) 0.010(3) O9 0.101(5) 0.054(3) 0.093(5) 0.037(3) 0.066(4) 0.022(3) O11 0.102(5) 0.122(7) 0.179(9) 0.043(7) 0.026(6) 0.012(6) C36' 0.051(3) 0.025(2) 0.027(2) -0.008(2) 0.012(2) 0.016(2) O7' 0.032(4) 0.040(5) 0.060(6) 0.024(4) 0.010(4) 0.015(4) O8' 0.022(4) 0.039(6) 0.121(11) 0.041(7) -0.003(6) 0.006(5) O10 0.035(4) 0.019(3) 0.029(4) 0.000(3) -0.016(3) 0.008(3) O12 0.102(5) 0.122(7) 0.179(9) 0.043(7) 0.026(6) 0.012(6) Mn1 0.0162(2) 0.0146(2) 0.0177(2) -0.00231(17) 0.00499(17) 0.00062(17) Mn2 0.0138(2) 0.0208(3) 0.0174(2) 0.00150(18) 0.00232(17) 0.00148(17) O1 0.0168(10) 0.0158(10) 0.0235(11) -0.0022(9) 0.0061(8) 0.0020(8) O2 0.0230(11) 0.0205(11) 0.0213(11) -0.0009(9) 0.0084(9) 0.0022(9) O3 0.0181(10) 0.0224(11) 0.0178(10) 0.0044(9) 0.0047(8) 0.0042(8) O4 0.0159(10) 0.0279(12) 0.0224(11) 0.0083(9) 0.0011(9) 0.0016(9) O5 0.0303(12) 0.0230(12) 0.0180(11) -0.0020(9) 0.0014(9) 0.0060(9) O6 0.0228(11) 0.0336(14) 0.0221(12) -0.0091(10) -0.0007(9) 0.0093(10) N1 0.0158(11) 0.0175(13) 0.0173(12) -0.0013(10) 0.0023(10) 0.0001(10) N2 0.0164(12) 0.0178(13) 0.0190(13) -0.0015(10) 0.0022(10) 0.0019(10) N3 0.0138(11) 0.0253(14) 0.0187(13) -0.0001(11) 0.0029(10) 0.0003(10) N4 0.0150(12) 0.0211(13) 0.0200(13) -0.0032(10) 0.0003(10) 0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.367(2) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.456(3) . ? C7 N1 1.286(4) . ? C7 H7 0.9500 . ? C8 N1 1.475(4) . ? C8 C9 1.521(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.484(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O2 1.360(3) . ? C10 C11 1.3900 . ? C10 C15 1.3900 . ? C11 C12 1.3900 . ? C11 H11 0.9500 . ? C12 C13 1.3900 . ? C12 H12 0.9500 . ? C13 C14 1.3900 . ? C13 H13 0.9500 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.450(3) . ? C16 N2 1.287(4) . ? C16 H16 0.9500 . ? C17 O3 1.356(2) . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 C19 1.3900 . ? C18 H18 0.9500 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 C21 1.3900 . ? C20 H20 0.9500 . ? C21 C22 1.3900 . ? C21 H21 0.9500 . ? C22 C23 1.450(4) . ? C23 N3 1.292(4) . ? C23 H23 0.9500 . ? C24 N3 1.486(4) . ? C24 C25 1.513(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N4 1.480(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 O4 1.362(2) . ? C26 C27 1.3900 . ? C26 C31 1.3900 . ? C27 C28 1.3900 . ? C27 H27 0.9500 . ? C28 C29 1.3900 . ? C28 H28 0.9500 . ? C29 C30 1.3900 . ? C29 H29 0.9500 . ? C30 C31 1.3900 . ? C30 H30 0.9500 . ? C31 C32 1.459(3) . ? C32 N4 1.286(4) . ? C32 H32 0.9500 . ? C33 O5 1.253(4) . ? C33 O6 1.266(4) . ? C33 C34 1.508(5) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 O7 1.107(6) . ? C35 O8' 1.134(8) . ? C35 O8 1.197(6) . ? C35 O7' 1.268(7) . ? C35 C36 1.393(7) . ? C35 C36' 1.498(11) . ? O11 O11 1.545(16) 2_675 ? Mn1 O2 1.876(2) . ? Mn1 O1 1.893(2) . ? Mn1 N2 1.972(3) . ? Mn1 N1 1.982(2) . ? Mn1 O6 2.088(2) . ? Mn2 O3 1.872(2) . ? Mn2 O4 1.884(2) . ? Mn2 N3 1.973(2) . ? Mn2 N4 1.986(3) . ? Mn2 O5 2.118(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 117.36(15) . . ? O1 C1 C6 122.37(15) . . ? C2 C1 C6 120.0 . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 117.33(16) . . ? C1 C6 C7 122.58(16) . . ? N1 C7 C6 124.3(3) . . ? N1 C7 H7 117.9 . . ? C6 C7 H7 117.9 . . ? N1 C8 C9 107.5(2) . . ? N1 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? N1 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? N2 C9 C8 107.7(2) . . ? N2 C9 H9A 110.2 . . ? C8 C9 H9A 110.2 . . ? N2 C9 H9B 110.2 . . ? C8 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O2 C10 C11 116.73(16) . . ? O2 C10 C15 123.20(16) . . ? C11 C10 C15 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 120.0 . . ? C14 C15 C16 116.78(17) . . ? C10 C15 C16 123.12(17) . . ? N2 C16 C15 125.3(3) . . ? N2 C16 H16 117.3 . . ? C15 C16 H16 117.3 . . ? O3 C17 C18 116.72(15) . . ? O3 C17 C22 123.26(15) . . ? C18 C17 C22 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 120.0 . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 120.0 . . ? C21 C22 C23 116.98(17) . . ? C17 C22 C23 123.02(17) . . ? N3 C23 C22 125.4(3) . . ? N3 C23 H23 117.3 . . ? C22 C23 H23 117.3 . . ? N3 C24 C25 106.7(3) . . ? N3 C24 H24A 110.4 . . ? C25 C24 H24A 110.4 . . ? N3 C24 H24B 110.4 . . ? C25 C24 H24B 110.4 . . ? H24A C24 H24B 108.6 . . ? N4 C25 C24 106.5(3) . . ? N4 C25 H25A 110.4 . . ? C24 C25 H25A 110.4 . . ? N4 C25 H25B 110.4 . . ? C24 C25 H25B 110.4 . . ? H25A C25 H25B 108.6 . . ? O4 C26 C27 117.45(15) . . ? O4 C26 C31 122.38(15) . . ? C27 C26 C31 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.0 . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 120.0 . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C31 C30 C29 120.0 . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C26 120.0 . . ? C30 C31 C32 117.49(17) . . ? C26 C31 C32 122.51(17) . . ? N4 C32 C31 123.5(3) . . ? N4 C32 H32 118.2 . . ? C31 C32 H32 118.2 . . ? O5 C33 O6 123.7(3) . . ? O5 C33 C34 120.4(3) . . ? O6 C33 C34 115.9(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O7 C35 O8' 167.3(9) . . ? O7 C35 O8 134.0(8) . . ? O8' C35 O8 38.9(7) . . ? O7 C35 O7' 47.4(5) . . ? O8' C35 O7' 136.2(10) . . ? O8 C35 O7' 167.7(6) . . ? O7 C35 C36 119.8(6) . . ? O8' C35 C36 69.0(9) . . ? O8 C35 C36 106.1(6) . . ? O7' C35 C36 74.6(5) . . ? O7 C35 C36' 56.7(7) . . ? O8' C35 C36' 117.2(9) . . ? O8 C35 C36' 78.4(6) . . ? O7' C35 C36' 104.1(7) . . ? C36 C35 C36' 165.3(6) . . ? O2 Mn1 O1 93.12(9) . . ? O2 Mn1 N2 92.10(10) . . ? O1 Mn1 N2 164.12(10) . . ? O2 Mn1 N1 170.73(10) . . ? O1 Mn1 N1 89.75(10) . . ? N2 Mn1 N1 82.91(10) . . ? O2 Mn1 O6 97.27(9) . . ? O1 Mn1 O6 97.03(9) . . ? N2 Mn1 O6 97.17(10) . . ? N1 Mn1 O6 91.11(10) . . ? O3 Mn2 O4 92.75(9) . . ? O3 Mn2 N3 91.90(10) . . ? O4 Mn2 N3 164.80(11) . . ? O3 Mn2 N4 165.59(10) . . ? O4 Mn2 N4 89.56(10) . . ? N3 Mn2 N4 82.46(11) . . ? O3 Mn2 O5 103.47(9) . . ? O4 Mn2 O5 96.30(9) . . ? N3 Mn2 O5 96.67(10) . . ? N4 Mn2 O5 90.39(10) . . ? C1 O1 Mn1 122.76(15) . . ? C10 O2 Mn1 129.30(16) . . ? C17 O3 Mn2 129.86(15) . . ? C26 O4 Mn2 122.36(15) . . ? C33 O5 Mn2 136.0(2) . . ? C33 O6 Mn1 131.8(2) . . ? C7 N1 C8 121.6(3) . . ? C7 N1 Mn1 124.8(2) . . ? C8 N1 Mn1 113.57(19) . . ? C16 N2 C9 120.6(3) . . ? C16 N2 Mn1 126.4(2) . . ? C9 N2 Mn1 113.01(19) . . ? C23 N3 C24 120.9(3) . . ? C23 N3 Mn2 126.5(2) . . ? C24 N3 Mn2 112.6(2) . . ? C32 N4 C25 121.9(3) . . ? C32 N4 Mn2 125.2(2) . . ? C25 N4 Mn2 112.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -174.2(2) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 176.7(2) . . . . ? O1 C1 C6 C5 173.9(2) . . . . ? C2 C1 C6 C5 0.0 . . . . ? O1 C1 C6 C7 -2.6(2) . . . . ? C2 C1 C6 C7 -176.5(2) . . . . ? C5 C6 C7 N1 171.3(2) . . . . ? C1 C6 C7 N1 -12.2(4) . . . . ? N1 C8 C9 N2 41.9(3) . . . . ? O2 C10 C11 C12 177.1(2) . . . . ? C15 C10 C11 C12 0.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C10 0.0 . . . . ? C13 C14 C15 C16 176.5(2) . . . . ? O2 C10 C15 C14 -176.9(2) . . . . ? C11 C10 C15 C14 0.0 . . . . ? O2 C10 C15 C16 6.7(3) . . . . ? C11 C10 C15 C16 -176.3(2) . . . . ? C14 C15 C16 N2 -178.2(2) . . . . ? C10 C15 C16 N2 -1.8(4) . . . . ? O3 C17 C18 C19 -178.4(2) . . . . ? C22 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C17 0.0 . . . . ? C20 C21 C22 C23 179.5(2) . . . . ? O3 C17 C22 C21 178.3(2) . . . . ? C18 C17 C22 C21 0.0 . . . . ? O3 C17 C22 C23 -1.2(3) . . . . ? C18 C17 C22 C23 -179.5(2) . . . . ? C21 C22 C23 N3 179.9(3) . . . . ? C17 C22 C23 N3 -0.6(4) . . . . ? N3 C24 C25 N4 -46.3(3) . . . . ? O4 C26 C27 C28 175.3(2) . . . . ? C31 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C28 C29 C30 C31 0.0 . . . . ? C29 C30 C31 C26 0.0 . . . . ? C29 C30 C31 C32 -179.2(2) . . . . ? O4 C26 C31 C30 -175.0(2) . . . . ? C27 C26 C31 C30 0.0 . . . . ? O4 C26 C31 C32 4.1(3) . . . . ? C27 C26 C31 C32 179.1(2) . . . . ? C30 C31 C32 N4 -167.5(2) . . . . ? C26 C31 C32 N4 13.4(4) . . . . ? C2 C1 O1 Mn1 -151.07(13) . . . . ? C6 C1 O1 Mn1 34.9(2) . . . . ? O2 Mn1 O1 C1 148.85(19) . . . . ? N2 Mn1 O1 C1 -102.2(4) . . . . ? N1 Mn1 O1 C1 -39.97(19) . . . . ? O6 Mn1 O1 C1 51.1(2) . . . . ? C11 C10 O2 Mn1 179.45(14) . . . . ? C15 C10 O2 Mn1 -3.5(3) . . . . ? O1 Mn1 O2 C10 162.6(2) . . . . ? N2 Mn1 O2 C10 -2.4(2) . . . . ? N1 Mn1 O2 C10 54.8(7) . . . . ? O6 Mn1 O2 C10 -99.9(2) . . . . ? C18 C17 O3 Mn2 177.94(14) . . . . ? C22 C17 O3 Mn2 -0.4(3) . . . . ? O4 Mn2 O3 C17 -163.2(2) . . . . ? N3 Mn2 O3 C17 2.4(2) . . . . ? N4 Mn2 O3 C17 -64.2(5) . . . . ? O5 Mn2 O3 C17 99.7(2) . . . . ? C27 C26 O4 Mn2 147.17(13) . . . . ? C31 C26 O4 Mn2 -37.7(3) . . . . ? O3 Mn2 O4 C26 -153.0(2) . . . . ? N3 Mn2 O4 C26 99.3(4) . . . . ? N4 Mn2 O4 C26 41.2(2) . . . . ? O5 Mn2 O4 C26 -49.1(2) . . . . ? O6 C33 O5 Mn2 179.1(2) . . . . ? C34 C33 O5 Mn2 -2.1(5) . . . . ? O3 Mn2 O5 C33 -32.3(3) . . . . ? O4 Mn2 O5 C33 -126.6(3) . . . . ? N3 Mn2 O5 C33 61.3(3) . . . . ? N4 Mn2 O5 C33 143.8(3) . . . . ? O5 C33 O6 Mn1 53.5(4) . . . . ? C34 C33 O6 Mn1 -125.3(3) . . . . ? O2 Mn1 O6 C33 44.2(3) . . . . ? O1 Mn1 O6 C33 138.3(3) . . . . ? N2 Mn1 O6 C33 -48.8(3) . . . . ? N1 Mn1 O6 C33 -131.8(3) . . . . ? C6 C7 N1 C8 174.9(3) . . . . ? C6 C7 N1 Mn1 -6.3(4) . . . . ? C9 C8 N1 C7 146.4(3) . . . . ? C9 C8 N1 Mn1 -32.5(3) . . . . ? O2 Mn1 N1 C7 134.7(6) . . . . ? O1 Mn1 N1 C7 26.6(2) . . . . ? N2 Mn1 N1 C7 -167.5(3) . . . . ? O6 Mn1 N1 C7 -70.5(2) . . . . ? O2 Mn1 N1 C8 -46.4(7) . . . . ? O1 Mn1 N1 C8 -154.5(2) . . . . ? N2 Mn1 N1 C8 11.3(2) . . . . ? O6 Mn1 N1 C8 108.4(2) . . . . ? C15 C16 N2 C9 175.4(3) . . . . ? C15 C16 N2 Mn1 -5.9(4) . . . . ? C8 C9 N2 C16 144.5(3) . . . . ? C8 C9 N2 Mn1 -34.4(3) . . . . ? O2 Mn1 N2 C16 6.9(3) . . . . ? O1 Mn1 N2 C16 -102.2(4) . . . . ? N1 Mn1 N2 C16 -165.2(3) . . . . ? O6 Mn1 N2 C16 104.5(3) . . . . ? O2 Mn1 N2 C9 -174.3(2) . . . . ? O1 Mn1 N2 C9 76.6(4) . . . . ? N1 Mn1 N2 C9 13.6(2) . . . . ? O6 Mn1 N2 C9 -76.7(2) . . . . ? C22 C23 N3 C24 -179.0(3) . . . . ? C22 C23 N3 Mn2 3.8(5) . . . . ? C25 C24 N3 C23 -139.7(3) . . . . ? C25 C24 N3 Mn2 37.9(3) . . . . ? O3 Mn2 N3 C23 -4.0(3) . . . . ? O4 Mn2 N3 C23 103.8(4) . . . . ? N4 Mn2 N3 C23 162.7(3) . . . . ? O5 Mn2 N3 C23 -107.8(3) . . . . ? O3 Mn2 N3 C24 178.6(2) . . . . ? O4 Mn2 N3 C24 -73.6(4) . . . . ? N4 Mn2 N3 C24 -14.7(2) . . . . ? O5 Mn2 N3 C24 74.8(2) . . . . ? C31 C32 N4 C25 -175.9(3) . . . . ? C31 C32 N4 Mn2 3.8(4) . . . . ? C24 C25 N4 C32 -144.1(3) . . . . ? C24 C25 N4 Mn2 36.1(3) . . . . ? O3 Mn2 N4 C32 -124.8(4) . . . . ? O4 Mn2 N4 C32 -25.4(3) . . . . ? N3 Mn2 N4 C32 167.6(3) . . . . ? O5 Mn2 N4 C32 70.9(3) . . . . ? O3 Mn2 N4 C25 54.9(5) . . . . ? O4 Mn2 N4 C25 154.3(2) . . . . ? N3 Mn2 N4 C25 -12.7(2) . . . . ? O5 Mn2 N4 C25 -109.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.051 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.098