# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 186/1217 data_Figure2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H21 Mn N2 O9' _chemical_formula_weight 488.33 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.053(2) _cell_length_b 19.874(4) _cell_length_c 9.312(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.97(2) _cell_angle_gamma 90.00 _cell_volume 2196.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12.5 _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max .34 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method ? _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator beta-filter _diffrn_measurement_device 'Nicolet P3' _diffrn_measurement_method theta/2theta _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 2166 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2166 _reflns_number_observed 2166 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+2.2997P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0058(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2166 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_obs 0.0433 _refine_ls_wR_factor_all 0.1186 _refine_ls_wR_factor_obs 0.1186 _refine_ls_goodness_of_fit_all 1.093 _refine_ls_goodness_of_fit_obs 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_restrained_S_obs 1.093 _refine_ls_shift/esd_max 0.741 _refine_ls_shift/esd_mean 0.216 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn Mn 0.59342(6) 0.60774(3) 0.55498(7) 0.0348(3) Uani 1 d . . O1 O 0.4958(3) 0.5935(2) 0.3755(3) 0.0416(8) Uani 1 d . . O2 O 0.6760(2) 0.52767(15) 0.5477(3) 0.0379(8) Uani 1 d . . O3 O 0.3916(3) 0.5473(2) 0.1301(4) 0.0566(10) Uani 1 d . . O4 O 0.7846(3) 0.4320(2) 0.4454(4) 0.0552(10) Uani 1 d . . O5 O 0.7138(3) 0.6681(2) 0.4716(4) 0.0464(8) Uani 1 d . . O6 O 0.8466(4) 0.6997(3) 0.3514(5) 0.0832(14) Uani 1 d . . O1W O 0.4650(4) 0.5515(2) 0.6732(5) 0.0474(9) Uani 1 d . . O2W O 0.9142(5) 0.7914(3) 0.5783(6) 0.110(2) Uani 1 d . . O3W O 1.0319(11) 0.8077(7) 0.3591(15) 0.267(6) Uani 1 d . . N1 N 0.5113(4) 0.6914(2) 0.5894(5) 0.0434(10) Uani 1 d . . N2 N 0.6763(3) 0.6280(2) 0.7537(4) 0.0413(10) Uani 1 d . . C1 C 0.4013(4) 0.6245(2) 0.3200(5) 0.0383(11) Uani 1 d . . C2 C 0.3417(4) 0.6008(3) 0.1860(5) 0.0452(12) Uani 1 d . . C3 C 0.2419(5) 0.6315(3) 0.1227(7) 0.060(2) Uani 1 d . . C4 C 0.1995(5) 0.6860(3) 0.1902(8) 0.069(2) Uani 1 d . . C5 C 0.2563(5) 0.7108(3) 0.3184(7) 0.0575(15) Uani 1 d . . C6 C 0.3582(4) 0.6810(2) 0.3841(6) 0.0431(12) Uani 1 d . . C7 C 0.4175(5) 0.7116(2) 0.5163(6) 0.0461(13) Uani 1 d . . C8 C 0.5714(6) 0.7303(3) 0.7123(6) 0.0559(15) Uani 1 d . . C9 C 0.6221(5) 0.6806(3) 0.8290(6) 0.0506(14) Uani 1 d . . C10 C 0.7732(5) 0.6040(3) 0.8073(5) 0.0469(12) Uani 1 d . . C11 C 0.8296(4) 0.5505(3) 0.7453(5) 0.0443(12) Uani 1 d . . C12 C 0.9375(5) 0.5321(4) 0.8184(7) 0.066(2) Uani 1 d . . C13 C 0.9930(6) 0.4809(4) 0.7677(8) 0.079(2) Uani 1 d . . C14 C 0.9456(5) 0.4461(4) 0.6441(8) 0.068(2) Uani 1 d . . C15 C 0.8406(4) 0.4627(2) 0.5697(6) 0.0449(12) Uani 1 d . . C16 C 0.7782(4) 0.5156(2) 0.6201(5) 0.0396(11) Uani 1 d . . C17 C 0.3431(8) 0.5229(5) -0.0104(7) 0.073(2) Uani 1 d . . C18 C 0.8420(8) 0.3785(4) 0.3855(10) 0.076(2) Uani 1 d . . C19 C 0.7676(4) 0.6619(3) 0.3678(6) 0.0452(12) Uani 1 d . . C20 C 0.7366(6) 0.6059(3) 0.2588(7) 0.0565(14) Uani 1 d . . H3 H 0.2049(48) 0.6104(27) 0.0353(62) 0.055(16) Uiso 1 d . . H4 H 0.1333(50) 0.7033(29) 0.1504(60) 0.060(17) Uiso 1 d . . H5 H 0.2141(47) 0.7509(30) 0.3718(61) 0.064(17) Uiso 1 d . . H7 H 0.3828(48) 0.7530(30) 0.5379(62) 0.069(17) Uiso 1 d . . H81 H 0.6412(52) 0.7572(30) 0.6818(61) 0.074(18) Uiso 1 d . . H82 H 0.5230(46) 0.7564(28) 0.7509(62) 0.052(16) Uiso 1 d . . H91 H 0.6713(45) 0.7037(28) 0.9030(60) 0.055(15) Uiso 1 d . . H92 H 0.5670(46) 0.6596(29) 0.8699(58) 0.058(17) Uiso 1 d . . H10 H 0.8082(39) 0.6243(24) 0.8907(55) 0.041(14) Uiso 1 d . . H12 H 0.9700(46) 0.5590(30) 0.9043(64) 0.071(18) Uiso 1 d . . H13 H 1.0634(56) 0.4684(31) 0.8246(70) 0.082(19) Uiso 1 d . . H14 H 0.9807(55) 0.4141(32) 0.6113(68) 0.075(20) Uiso 1 d . . H171 H 0.3903(66) 0.4830(41) -0.0318(81) 0.101(27) Uiso 1 d . . H172 H 0.2665(58) 0.5107(31) -0.0128(67) 0.072(20) Uiso 1 d . . H173 H 0.3375(48) 0.5600(31) -0.0820(67) 0.068(19) Uiso 1 d . . H181 H 0.9140(60) 0.3960(32) 0.3507(72) 0.087(21) Uiso 1 d . . H182 H 0.7926(48) 0.3701(29) 0.2960(69) 0.062(19) Uiso 1 d . . H183 H 0.8577(65) 0.3454(43) 0.4521(89) 0.096(30) Uiso 1 d . . H201 H 0.7688(46) 0.6091(26) 0.1761(63) 0.058(15) Uiso 1 d . . H202 H 0.7595(51) 0.5621(32) 0.3039(65) 0.065(18) Uiso 1 d . . H203 H 0.6574(48) 0.6007(24) 0.2326(53) 0.047(14) Uiso 1 d . . H11W H 0.4088(65) 0.5471(38) 0.6366(81) 0.098(31) Uiso 1 d . . H12W H 0.4846(53) 0.5186(34) 0.6969(68) 0.060(23) Uiso 1 d . . H21W H 0.8880 0.7905 0.6425 0.289 Uiso 1 d . . H22W H 0.8784 0.7395 0.5370 0.250 Uiso 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 Mn 0.0377(4) 0.0304(4) 0.0357(4) -0.0041(3) 0.0049(3) 0.0044(3) O1 0.039(2) 0.039(2) 0.044(2) -0.0004(14) 0.0015(15) 0.0064(14) O2 0.035(2) 0.032(2) 0.046(2) -0.0013(14) 0.0038(15) 0.0066(13) O3 0.057(2) 0.063(2) 0.045(2) -0.009(2) -0.005(2) -0.001(2) O4 0.057(2) 0.043(2) 0.069(2) -0.006(2) 0.019(2) 0.012(2) O5 0.055(2) 0.041(2) 0.046(2) -0.004(2) 0.017(2) -0.005(2) O6 0.088(3) 0.096(3) 0.075(3) -0.019(3) 0.041(3) -0.042(3) O1W 0.046(3) 0.042(2) 0.054(2) 0.000(2) 0.008(2) -0.001(2) O2W 0.089(4) 0.155(5) 0.090(4) -0.044(3) 0.025(3) -0.027(4) O3W 0.249(12) 0.264(14) 0.279(15) 0.026(11) 0.018(11) 0.005(11) N1 0.045(2) 0.037(2) 0.049(2) -0.002(2) 0.013(2) 0.006(2) N2 0.046(3) 0.040(2) 0.038(2) -0.003(2) 0.008(2) -0.002(2) C1 0.030(3) 0.041(3) 0.043(3) 0.011(2) 0.005(2) -0.002(2) C2 0.042(3) 0.043(3) 0.050(3) 0.013(2) 0.007(2) -0.004(2) C3 0.048(3) 0.071(4) 0.056(4) 0.019(3) -0.005(3) -0.006(3) C4 0.041(4) 0.076(4) 0.089(5) 0.037(4) 0.013(4) 0.020(3) C5 0.045(3) 0.053(3) 0.075(4) 0.019(3) 0.011(3) 0.012(3) C6 0.036(3) 0.041(3) 0.055(3) 0.014(2) 0.014(2) 0.003(2) C7 0.052(3) 0.034(3) 0.057(3) 0.005(2) 0.022(3) 0.009(2) C8 0.074(4) 0.041(3) 0.057(3) -0.017(3) 0.021(3) 0.006(3) C9 0.065(4) 0.052(3) 0.037(3) -0.012(2) 0.016(3) -0.005(3) C10 0.051(3) 0.056(3) 0.032(3) -0.001(3) 0.003(2) -0.012(3) C11 0.040(3) 0.053(3) 0.040(3) 0.009(2) 0.006(2) 0.002(2) C12 0.044(3) 0.095(5) 0.053(4) 0.001(3) -0.007(3) 0.005(3) C13 0.052(4) 0.109(6) 0.073(5) 0.008(4) -0.002(4) 0.028(4) C14 0.051(4) 0.080(4) 0.074(5) 0.006(4) 0.016(3) 0.025(3) C15 0.041(3) 0.045(3) 0.050(3) 0.009(2) 0.012(2) 0.005(2) C16 0.041(3) 0.039(3) 0.040(3) 0.011(2) 0.010(2) -0.002(2) C17 0.075(5) 0.093(6) 0.045(4) -0.008(4) -0.006(3) -0.015(5) C18 0.092(6) 0.061(5) 0.083(6) -0.003(4) 0.036(5) 0.026(4) C19 0.043(3) 0.049(3) 0.045(3) 0.005(2) 0.011(2) 0.002(2) C20 0.067(4) 0.056(4) 0.051(3) -0.009(3) 0.022(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn O2 1.885(3) . ? Mn O1 1.891(3) . ? Mn N2 1.986(4) . ? Mn N1 1.988(4) . ? Mn O5 2.130(3) . ? Mn O1W 2.334(4) . ? O1 C1 1.320(5) . ? O2 C16 1.320(6) . ? O3 C2 1.367(6) . ? O3 C17 1.422(7) . ? O4 C15 1.378(6) . ? O4 C18 1.432(7) . ? O5 C19 1.259(6) . ? O6 C19 1.243(6) . ? N1 C7 1.279(6) . ? N1 C8 1.465(7) . ? N2 C10 1.281(6) . ? N2 C9 1.472(6) . ? C1 C2 1.409(7) . ? C1 C6 1.412(7) . ? C2 C3 1.386(8) . ? C3 C4 1.393(9) . ? C4 C5 1.361(9) . ? C5 C6 1.405(7) . ? C6 C7 1.446(8) . ? C8 C9 1.517(8) . ? C10 C11 1.436(7) . ? C11 C16 1.404(7) . ? C11 C12 1.407(7) . ? C12 C13 1.348(9) . ? C13 C14 1.379(10) . ? C14 C15 1.373(8) . ? C15 C16 1.420(7) . ? C19 C20 1.509(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn O1 95.36(13) . . ? O2 Mn N2 91.2(2) . . ? O1 Mn N2 171.6(2) . . ? O2 Mn N1 172.9(2) . . ? O1 Mn N1 91.0(2) . . ? N2 Mn N1 82.2(2) . . ? O2 Mn O5 93.69(13) . . ? O1 Mn O5 96.96(14) . . ? N2 Mn O5 87.77(15) . . ? N1 Mn O5 88.73(15) . . ? O2 Mn O1W 90.6(2) . . ? O1 Mn O1W 89.0(2) . . ? N2 Mn O1W 85.7(2) . . ? N1 Mn O1W 86.3(2) . . ? O5 Mn O1W 172.28(14) . . ? C1 O1 Mn 129.7(3) . . ? C16 O2 Mn 125.9(3) . . ? C2 O3 C17 118.5(5) . . ? C15 O4 C18 117.1(5) . . ? C19 O5 Mn 134.3(3) . . ? C7 N1 C8 121.4(4) . . ? C7 N1 Mn 126.6(4) . . ? C8 N1 Mn 112.0(3) . . ? C10 N2 C9 122.0(4) . . ? C10 N2 Mn 124.4(4) . . ? C9 N2 Mn 113.3(3) . . ? O1 C1 C2 117.6(4) . . ? O1 C1 C6 124.2(4) . . ? C2 C1 C6 118.2(4) . . ? O3 C2 C3 125.9(5) . . ? O3 C2 C1 114.0(4) . . ? C3 C2 C1 120.0(5) . . ? C2 C3 C4 120.7(6) . . ? C5 C4 C3 120.6(6) . . ? C4 C5 C6 119.8(6) . . ? C5 C6 C1 120.6(5) . . ? C5 C6 C7 117.4(5) . . ? C1 C6 C7 122.0(4) . . ? N1 C7 C6 125.6(5) . . ? N1 C8 C9 107.4(4) . . ? N2 C9 C8 106.1(4) . . ? N2 C10 C11 125.7(5) . . ? C16 C11 C12 120.8(5) . . ? C16 C11 C10 121.8(5) . . ? C12 C11 C10 117.4(5) . . ? C13 C12 C11 120.0(6) . . ? C12 C13 C14 120.7(7) . . ? C15 C14 C13 121.0(6) . . ? C14 C15 O4 126.4(5) . . ? C14 C15 C16 120.3(5) . . ? O4 C15 C16 113.3(4) . . ? O2 C16 C11 125.0(4) . . ? O2 C16 C15 117.8(4) . . ? C11 C16 C15 117.2(4) . . ? O6 C19 O5 122.8(5) . . ? O6 C19 C20 118.0(5) . . ? O5 C19 C20 119.2(5) . . ? _refine_diff_density_max 0.515 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.061 #=END data_Figure3a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H31 Cl2 Mn N2 O6' _chemical_formula_weight 581.36 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.034(3) _cell_length_b 12.111(4) _cell_length_c 18.446(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.760(10) _cell_angle_gamma 90.00 _cell_volume 2839.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 9.549 _cell_measurement_theta_max 25.179 _exptl_crystal_description blocks _exptl_crystal_colour black _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method ? _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.693 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 71.06 _diffrn_reflns_number 4731 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3679 _reflns_number_observed 2910 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1248P)^2^+7.4759P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3679 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_obs 0.0748 _refine_ls_wR_factor_all 0.2287 _refine_ls_wR_factor_obs 0.2098 _refine_ls_goodness_of_fit_all 1.065 _refine_ls_goodness_of_fit_obs 1.109 _refine_ls_restrained_S_all 1.065 _refine_ls_restrained_S_obs 1.109 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.15681(7) -0.01150(7) 0.17647(5) 0.0417(4) Uani 1 d . . N1 N 0.0453(4) -0.1047(4) 0.0964(3) 0.0472(13) Uani 1 d . . N2 N 0.2268(4) -0.1513(4) 0.2163(3) 0.0448(12) Uani 1 d . . O1 O 0.0851(3) 0.1162(3) 0.1372(2) 0.0501(11) Uani 1 d . . O2 O 0.1075(3) 0.0046(3) 0.2665(2) 0.0515(11) Uani 1 d . . O3 O 0.0072(4) 0.3091(4) 0.1602(3) 0.0708(14) Uani 1 d . . O4 O 0.0609(4) 0.1070(4) 0.3799(3) 0.0776(15) Uani 1 d . . O5 O 0.3166(4) 0.0793(4) 0.2174(2) 0.0582(12) Uani 1 d . . O6 O 0.2625(3) 0.0062(3) 0.1083(2) 0.0543(11) Uani 1 d . . C1 C -0.0192(5) 0.1254(5) 0.1219(3) 0.0459(15) Uani 1 d . . C2 C -0.0641(5) 0.2283(5) 0.1327(3) 0.053(2) Uani 1 d . . C3 C -0.1713(6) 0.2427(6) 0.1147(4) 0.064(2) Uani 1 d . . H3A H -0.2001(6) 0.3135(6) 0.1227(4) 0.080 Uiso 1 d R . C4 C -0.2365(6) 0.1574(7) 0.0856(4) 0.077(2) Uani 1 d . . H4A H -0.3113(6) 0.1680(7) 0.0745(4) 0.080 Uiso 1 d R . C5 C -0.1952(6) 0.0575(7) 0.0731(4) 0.067(2) Uani 1 d . . H5A H -0.2411(6) -0.0014(7) 0.0513(4) 0.080 Uiso 1 d R . C6 C -0.0861(5) 0.0388(5) 0.0913(3) 0.051(2) Uani 1 d . . C7 C -0.0481(6) -0.0671(5) 0.0730(3) 0.054(2) Uani 1 d . . H7A H -0.0973(6) -0.1139(5) 0.0405(3) 0.080 Uiso 1 d R . C8 C 0.0734(6) -0.2089(5) 0.0658(4) 0.061(2) Uani 1 d . . H8A H 0.1139(6) -0.1929(5) 0.0294(4) 0.080 Uiso 1 d R . H8B H 0.0104(6) -0.2461(5) 0.0409(4) 0.080 Uiso 1 d R . C9 C 0.1374(6) -0.2844(5) 0.1229(4) 0.061(2) Uani 1 d . . H9A H 0.1481(6) -0.3535(5) 0.1002(4) 0.080 Uiso 1 d R . H9B H 0.0973(6) -0.2987(5) 0.1597(4) 0.080 Uiso 1 d R . C10 C 0.2417(6) -0.2370(5) 0.1622(3) 0.058(2) Uani 1 d . . H10A H 0.2860(6) -0.2947(5) 0.1876(3) 0.080 Uiso 1 d R . H10B H 0.2754(6) -0.2049(5) 0.1259(3) 0.080 Uiso 1 d R . C11 C 0.2582(5) -0.1718(5) 0.2851(3) 0.050(2) Uani 1 d . . H11A H 0.2998(5) -0.2371(5) 0.2983(3) 0.080 Uiso 1 d R . C12 C 0.2381(5) -0.1057(5) 0.3454(3) 0.052(2) Uani 1 d . . C13 C 0.2915(6) -0.1333(7) 0.4185(4) 0.074(2) Uani 1 d . . H13A H 0.3441(6) -0.1902(7) 0.4261(4) 0.080 Uiso 1 d R . C14 C 0.2692(8) -0.0783(8) 0.4781(4) 0.090(3) Uani 1 d . . H14A H 0.3065(8) -0.0963(8) 0.5276(4) 0.080 Uiso 1 d R . C15 C 0.1932(8) 0.0022(8) 0.4667(4) 0.080(2) Uani 1 d . . H15A H 0.1780(8) 0.0411(8) 0.5085(4) 0.080 Uiso 1 d R . C16 C 0.1367(6) 0.0288(6) 0.3962(4) 0.063(2) Uani 1 d . . C17 C 0.1608(5) -0.0240(5) 0.3330(3) 0.052(2) Uani 1 d . . C18 C 0.3329(5) 0.0578(5) 0.1547(3) 0.050(2) Uani 1 d . . C19 C 0.4353(5) 0.0877(6) 0.1333(4) 0.059(2) Uani 1 d . . C20 C 0.4110(8) 0.1541(9) 0.0626(5) 0.101(3) Uani 1 d . . H20A H 0.3774(8) 0.2220(9) 0.0709(5) 0.080 Uiso 1 d R . H20B H 0.4750(8) 0.1701(9) 0.0469(5) 0.080 Uiso 1 d R . H20C H 0.3649(8) 0.1124(9) 0.0246(5) 0.080 Uiso 1 d R . C21 C 0.5037(7) 0.1574(8) 0.1926(5) 0.091(3) Uani 1 d . . H21A H 0.4682(7) 0.2252(8) 0.1983(5) 0.080 Uiso 1 d R . H21B H 0.5172(7) 0.1174(8) 0.2387(5) 0.080 Uiso 1 d R . H21C H 0.5692(7) 0.1734(8) 0.1791(5) 0.080 Uiso 1 d R . C22 C 0.4887(7) -0.0176(8) 0.1220(6) 0.100(3) Uani 1 d . . H22A H 0.5540(7) -0.0028(8) 0.1080(6) 0.080 Uiso 1 d R . H22B H 0.5020(7) -0.0588(8) 0.1676(6) 0.080 Uiso 1 d R . H22C H 0.4437(7) -0.0597(8) 0.0836(6) 0.080 Uiso 1 d R . C23 C 0.0328(8) 0.1656(8) 0.4404(5) 0.104(3) Uani 1 d . . H23A H -0.0214(8) 0.2181(8) 0.4208(5) 0.080 Uiso 1 d R . H23B H 0.0076(8) 0.1146(8) 0.4723(5) 0.080 Uiso 1 d R . H23C H 0.0934(8) 0.2037(8) 0.4683(5) 0.080 Uiso 1 d R . C24 C -0.0269(8) 0.4180(7) 0.1555(6) 0.111(4) Uani 1 d . . H24A H 0.0301(8) 0.4662(7) 0.1772(6) 0.080 Uiso 1 d R . H24B H -0.0520(8) 0.4366(7) 0.1040(6) 0.080 Uiso 1 d R . H24C H -0.0830(8) 0.4263(7) 0.1812(6) 0.080 Uiso 1 d R . C1X C 0.8478(9) 1.0254(7) 0.2652(6) 0.196(9) Uani 1 d D . H1XA H 0.8288(9) 1.0658(7) 0.2194(6) 0.080 Uiso 1 d R . H1XB H 0.9223(9) 1.0320(7) 0.2840(6) 0.080 Uiso 1 d R . Cl1 Cl 0.8124(7) 0.8894(6) 0.2483(7) 0.452(9) Uani 1 d D . Cl2 Cl 0.7840(4) 1.0810(8) 0.3288(3) 0.283(4) Uani 1 d D . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0433(6) 0.0394(5) 0.0422(6) -0.0006(4) 0.0087(4) 0.0011(4) N1 0.052(4) 0.046(3) 0.042(3) -0.003(2) 0.008(2) -0.005(3) N2 0.046(3) 0.042(3) 0.046(3) 0.000(2) 0.011(2) 0.001(2) O1 0.046(3) 0.042(2) 0.061(3) 0.002(2) 0.007(2) 0.003(2) O2 0.050(3) 0.056(3) 0.052(3) -0.002(2) 0.018(2) 0.006(2) O3 0.064(3) 0.050(3) 0.091(3) -0.010(2) 0.003(3) 0.011(2) O4 0.087(4) 0.074(3) 0.084(3) -0.023(3) 0.046(3) 0.000(3) O5 0.063(3) 0.058(3) 0.057(3) -0.006(2) 0.022(2) -0.001(2) O6 0.050(3) 0.060(3) 0.054(3) -0.002(2) 0.014(2) -0.009(2) C1 0.043(4) 0.055(4) 0.039(3) 0.005(3) 0.009(3) 0.003(3) C2 0.052(4) 0.063(4) 0.045(3) 0.002(3) 0.009(3) 0.009(3) C3 0.054(5) 0.075(5) 0.063(4) -0.003(4) 0.010(3) 0.015(4) C4 0.045(5) 0.103(6) 0.080(5) 0.002(5) 0.009(4) 0.014(5) C5 0.049(5) 0.082(5) 0.066(4) 0.001(4) 0.003(4) -0.005(4) C6 0.043(4) 0.061(4) 0.046(3) 0.002(3) 0.003(3) -0.003(3) C7 0.054(5) 0.056(4) 0.050(4) -0.001(3) 0.004(3) -0.011(3) C8 0.077(5) 0.052(4) 0.053(4) -0.012(3) 0.011(3) 0.003(4) C9 0.087(5) 0.044(3) 0.053(4) -0.011(3) 0.015(4) -0.001(4) C10 0.075(5) 0.046(3) 0.056(4) -0.006(3) 0.020(3) 0.011(3) C11 0.044(4) 0.048(3) 0.053(4) 0.005(3) 0.004(3) -0.001(3) C12 0.061(4) 0.051(4) 0.045(3) -0.002(3) 0.011(3) -0.006(3) C13 0.083(6) 0.084(5) 0.049(4) 0.001(4) 0.003(4) 0.001(4) C14 0.103(7) 0.109(7) 0.049(4) 0.004(4) -0.001(5) -0.015(6) C15 0.096(7) 0.100(6) 0.048(4) -0.020(4) 0.026(4) -0.024(5) C16 0.071(5) 0.063(4) 0.066(5) -0.016(3) 0.037(4) -0.020(4) C17 0.057(4) 0.056(4) 0.045(4) -0.003(3) 0.015(3) -0.019(3) C18 0.055(4) 0.046(3) 0.050(4) 0.002(3) 0.012(3) 0.000(3) C19 0.049(4) 0.068(4) 0.065(4) -0.005(3) 0.020(3) -0.012(3) C20 0.100(7) 0.124(8) 0.087(6) 0.005(5) 0.041(5) -0.037(6) C21 0.081(6) 0.106(7) 0.090(6) -0.010(5) 0.032(5) -0.026(5) C22 0.067(6) 0.104(7) 0.140(9) -0.013(6) 0.048(6) 0.003(5) C23 0.124(8) 0.084(6) 0.121(7) -0.042(6) 0.061(6) -0.007(6) C24 0.094(7) 0.070(6) 0.153(9) -0.029(6) -0.008(6) 0.021(5) C1X 0.124(11) 0.358(26) 0.117(9) 0.123(13) 0.049(8) 0.012(13) Cl1 0.368(10) 0.244(7) 0.879(24) 0.305(11) 0.431(14) 0.134(7) Cl2 0.134(3) 0.569(13) 0.164(4) -0.057(6) 0.068(3) -0.057(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 1.868(4) . ? Mn1 O2 1.918(4) . ? Mn1 N2 1.986(5) . ? Mn1 O6 2.071(4) . ? Mn1 N1 2.150(5) . ? Mn1 O5 2.329(5) . ? Mn1 C18 2.557(7) . ? N1 C7 1.282(8) . ? N1 C8 1.462(8) . ? N2 C11 1.269(7) . ? N2 C10 1.482(7) . ? O1 C1 1.331(7) . ? O2 C17 1.316(7) . ? O3 C2 1.368(8) . ? O3 C24 1.388(9) . ? O4 C16 1.354(9) . ? O4 C23 1.437(9) . ? O5 C18 1.249(7) . ? O6 C18 1.271(7) . ? C1 C6 1.401(9) . ? C1 C2 1.409(9) . ? C2 C3 1.375(10) . ? C3 C4 1.369(11) . ? C4 C5 1.365(11) . ? C5 C6 1.406(10) . ? C6 C7 1.442(9) . ? C8 C9 1.501(9) . ? C9 C10 1.506(9) . ? C11 C12 1.440(9) . ? C12 C17 1.395(9) . ? C12 C13 1.416(9) . ? C13 C14 1.369(11) . ? C14 C15 1.373(12) . ? C15 C16 1.383(12) . ? C16 C17 1.423(9) . ? C18 C19 1.517(9) . ? C19 C22 1.488(11) . ? C19 C20 1.506(11) . ? C19 C21 1.508(10) . ? C1X Cl2 1.719(2) . ? C1X Cl1 1.719(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 Mn1 O2 91.0(2) . . ? O1 Mn1 N2 177.3(2) . . ? O2 Mn1 N2 88.9(2) . . ? O1 Mn1 O6 91.2(2) . . ? O2 Mn1 O6 155.5(2) . . ? N2 Mn1 O6 90.0(2) . . ? O1 Mn1 N1 87.9(2) . . ? O2 Mn1 N1 110.1(2) . . ? N2 Mn1 N1 89.6(2) . . ? O6 Mn1 N1 94.4(2) . . ? O1 Mn1 O5 94.0(2) . . ? O2 Mn1 O5 96.8(2) . . ? N2 Mn1 O5 88.7(2) . . ? O6 Mn1 O5 58.7(2) . . ? N1 Mn1 O5 153.1(2) . . ? O1 Mn1 C18 93.2(2) . . ? O2 Mn1 C18 125.9(2) . . ? N2 Mn1 C18 89.0(2) . . ? O6 Mn1 C18 29.6(2) . . ? N1 Mn1 C18 123.9(2) . . ? O5 Mn1 C18 29.2(2) . . ? C7 N1 C8 118.5(5) . . ? C7 N1 Mn1 119.5(4) . . ? C8 N1 Mn1 122.0(4) . . ? C11 N2 C10 118.4(5) . . ? C11 N2 Mn1 123.8(4) . . ? C10 N2 Mn1 117.8(4) . . ? C1 O1 Mn1 123.5(4) . . ? C17 O2 Mn1 124.9(4) . . ? C2 O3 C24 118.3(6) . . ? C16 O4 C23 118.2(7) . . ? C18 O5 Mn1 85.6(4) . . ? C18 O6 Mn1 96.9(4) . . ? O1 C1 C6 122.6(6) . . ? O1 C1 C2 118.8(6) . . ? C6 C1 C2 118.5(6) . . ? O3 C2 C3 124.7(6) . . ? O3 C2 C1 114.6(6) . . ? C3 C2 C1 120.7(6) . . ? C4 C3 C2 120.5(7) . . ? C5 C4 C3 120.2(7) . . ? C4 C5 C6 121.2(7) . . ? C1 C6 C5 118.9(6) . . ? C1 C6 C7 123.0(6) . . ? C5 C6 C7 118.0(6) . . ? N1 C7 C6 126.0(6) . . ? N1 C8 C9 113.7(5) . . ? C8 C9 C10 114.1(6) . . ? N2 C10 C9 110.7(5) . . ? N2 C11 C12 126.2(6) . . ? C17 C12 C13 120.5(6) . . ? C17 C12 C11 121.1(6) . . ? C13 C12 C11 118.1(6) . . ? C14 C13 C12 120.2(8) . . ? C13 C14 C15 119.8(7) . . ? C14 C15 C16 121.7(7) . . ? O4 C16 C15 125.6(7) . . ? O4 C16 C17 114.5(7) . . ? C15 C16 C17 119.9(8) . . ? O2 C17 C12 123.5(6) . . ? O2 C17 C16 118.7(7) . . ? C12 C17 C16 117.8(6) . . ? O5 C18 O6 118.8(6) . . ? O5 C18 C19 122.0(6) . . ? O6 C18 C19 119.2(6) . . ? O5 C18 Mn1 65.2(4) . . ? O6 C18 Mn1 53.5(3) . . ? C19 C18 Mn1 172.3(5) . . ? C22 C19 C20 110.6(7) . . ? C22 C19 C21 111.2(7) . . ? C20 C19 C21 107.9(7) . . ? C22 C19 C18 107.3(6) . . ? C20 C19 C18 108.9(6) . . ? C21 C19 C18 111.0(6) . . ? Cl2 C1X Cl1 110.4(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 N1 C7 -28.7(5) . . . . ? O2 Mn1 N1 C7 61.6(5) . . . . ? N2 Mn1 N1 C7 150.3(5) . . . . ? O6 Mn1 N1 C7 -119.8(5) . . . . ? O5 Mn1 N1 C7 -123.4(5) . . . . ? C18 Mn1 N1 C7 -121.2(5) . . . . ? O1 Mn1 N1 C8 149.5(5) . . . . ? O2 Mn1 N1 C8 -120.2(4) . . . . ? N2 Mn1 N1 C8 -31.5(5) . . . . ? O6 Mn1 N1 C8 58.4(5) . . . . ? O5 Mn1 N1 C8 54.8(6) . . . . ? C18 Mn1 N1 C8 57.0(5) . . . . ? O1 Mn1 N2 C11 -115.2(39) . . . . ? O2 Mn1 N2 C11 -27.0(5) . . . . ? O6 Mn1 N2 C11 128.5(5) . . . . ? N1 Mn1 N2 C11 -137.1(5) . . . . ? O5 Mn1 N2 C11 69.8(5) . . . . ? C18 Mn1 N2 C11 99.0(5) . . . . ? O1 Mn1 N2 C10 63.8(41) . . . . ? O2 Mn1 N2 C10 152.0(5) . . . . ? O6 Mn1 N2 C10 -52.5(4) . . . . ? N1 Mn1 N2 C10 41.9(4) . . . . ? O5 Mn1 N2 C10 -111.2(4) . . . . ? C18 Mn1 N2 C10 -82.0(5) . . . . ? O2 Mn1 O1 C1 -64.7(4) . . . . ? N2 Mn1 O1 C1 23.5(42) . . . . ? O6 Mn1 O1 C1 139.8(4) . . . . ? N1 Mn1 O1 C1 45.4(4) . . . . ? O5 Mn1 O1 C1 -161.5(4) . . . . ? C18 Mn1 O1 C1 169.3(4) . . . . ? O1 Mn1 O2 C17 -146.7(5) . . . . ? N2 Mn1 O2 C17 36.0(5) . . . . ? O6 Mn1 O2 C17 -51.5(7) . . . . ? N1 Mn1 O2 C17 125.2(5) . . . . ? O5 Mn1 O2 C17 -52.6(5) . . . . ? C18 Mn1 O2 C17 -52.0(5) . . . . ? O1 Mn1 O5 C18 -89.5(4) . . . . ? O2 Mn1 O5 C18 179.0(4) . . . . ? N2 Mn1 O5 C18 90.3(4) . . . . ? O6 Mn1 O5 C18 -0.5(3) . . . . ? N1 Mn1 O5 C18 3.8(6) . . . . ? C18 Mn1 O5 C18 0.0 . . . . ? O1 Mn1 O6 C18 94.4(4) . . . . ? O2 Mn1 O6 C18 -0.7(6) . . . . ? N2 Mn1 O6 C18 -88.1(4) . . . . ? N1 Mn1 O6 C18 -177.6(4) . . . . ? O5 Mn1 O6 C18 0.5(3) . . . . ? C18 Mn1 O6 C18 0.0 . . . . ? Mn1 O1 C1 C6 -39.0(7) . . . . ? Mn1 O1 C1 C2 145.1(4) . . . . ? C24 O3 C2 C3 -14.4(11) . . . . ? C24 O3 C2 C1 164.4(7) . . . . ? O1 C1 C2 O3 -1.6(8) . . . . ? C6 C1 C2 O3 -177.7(5) . . . . ? O1 C1 C2 C3 177.3(6) . . . . ? C6 C1 C2 C3 1.2(9) . . . . ? O3 C2 C3 C4 178.4(6) . . . . ? C1 C2 C3 C4 -0.4(10) . . . . ? C2 C3 C4 C5 -1.1(12) . . . . ? C3 C4 C5 C6 1.7(12) . . . . ? O1 C1 C6 C5 -176.5(6) . . . . ? C2 C1 C6 C5 -0.6(9) . . . . ? O1 C1 C6 C7 -0.5(9) . . . . ? C2 C1 C6 C7 175.4(6) . . . . ? C4 C5 C6 C1 -0.8(10) . . . . ? C4 C5 C6 C7 -177.0(7) . . . . ? C8 N1 C7 C6 -173.4(6) . . . . ? Mn1 N1 C7 C6 4.9(9) . . . . ? C1 C6 C7 N1 16.6(10) . . . . ? C5 C6 C7 N1 -167.4(6) . . . . ? C7 N1 C8 C9 -138.2(7) . . . . ? Mn1 N1 C8 C9 43.6(8) . . . . ? N1 C8 C9 C10 -61.2(8) . . . . ? C11 N2 C10 C9 111.1(6) . . . . ? Mn1 N2 C10 C9 -68.0(6) . . . . ? C8 C9 C10 N2 74.2(7) . . . . ? C10 N2 C11 C12 -171.1(6) . . . . ? Mn1 N2 C11 C12 7.9(9) . . . . ? N2 C11 C12 C17 14.9(10) . . . . ? N2 C11 C12 C13 -171.4(6) . . . . ? C17 C12 C13 C14 -1.3(11) . . . . ? C11 C12 C13 C14 -175.1(7) . . . . ? C12 C13 C14 C15 1.4(13) . . . . ? C13 C14 C15 C16 0.9(13) . . . . ? C23 O4 C16 C15 -2.4(11) . . . . ? C23 O4 C16 C17 -179.1(6) . . . . ? C14 C15 C16 O4 -179.8(7) . . . . ? C14 C15 C16 C17 -3.2(12) . . . . ? Mn1 O2 C17 C12 -25.9(8) . . . . ? Mn1 O2 C17 C16 155.8(4) . . . . ? C13 C12 C17 O2 -179.2(6) . . . . ? C11 C12 C17 O2 -5.7(9) . . . . ? C13 C12 C17 C16 -0.9(9) . . . . ? C11 C12 C17 C16 172.6(6) . . . . ? O4 C16 C17 O2 -1.6(9) . . . . ? C15 C16 C17 O2 -178.5(6) . . . . ? O4 C16 C17 C12 -179.9(6) . . . . ? C15 C16 C17 C12 3.2(10) . . . . ? Mn1 O5 C18 O6 0.7(5) . . . . ? Mn1 O5 C18 C19 -177.0(6) . . . . ? Mn1 O5 C18 Mn1 0.0 . . . . ? Mn1 O6 C18 O5 -0.8(6) . . . . ? Mn1 O6 C18 C19 177.0(5) . . . . ? Mn1 O6 C18 Mn1 0.0 . . . . ? O1 Mn1 C18 O5 92.4(4) . . . . ? O2 Mn1 C18 O5 -1.2(4) . . . . ? N2 Mn1 C18 O5 -89.2(4) . . . . ? O6 Mn1 C18 O5 179.2(6) . . . . ? N1 Mn1 C18 O5 -177.9(3) . . . . ? O5 Mn1 C18 O5 0.0 . . . . ? O1 Mn1 C18 O6 -86.8(4) . . . . ? O2 Mn1 C18 O6 179.6(3) . . . . ? N2 Mn1 C18 O6 91.7(4) . . . . ? O6 Mn1 C18 O6 0.0 . . . . ? N1 Mn1 C18 O6 2.9(4) . . . . ? O5 Mn1 C18 O6 -179.2(6) . . . . ? O1 Mn1 C18 C19 -107.0(34) . . . . ? O2 Mn1 C18 C19 159.5(33) . . . . ? N2 Mn1 C18 C19 71.5(34) . . . . ? O6 Mn1 C18 C19 -20.2(32) . . . . ? N1 Mn1 C18 C19 -17.3(34) . . . . ? O5 Mn1 C18 C19 160.7(36) . . . . ? O5 C18 C19 C22 114.1(8) . . . . ? O6 C18 C19 C22 -63.6(8) . . . . ? Mn1 C18 C19 C22 -45.1(36) . . . . ? O5 C18 C19 C20 -126.1(7) . . . . ? O6 C18 C19 C20 56.1(8) . . . . ? Mn1 C18 C19 C20 74.6(35) . . . . ? O5 C18 C19 C21 -7.5(9) . . . . ? O6 C18 C19 C21 174.7(6) . . . . ? Mn1 C18 C19 C21 -166.8(31) . . . . ? _refine_diff_density_max 1.461 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.087 #=END data_Figure3b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Mn N2 O6' _chemical_formula_weight 482.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.692(2) _cell_length_b 12.088(2) _cell_length_c 20.027(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.55(3) _cell_angle_gamma 90.00 _cell_volume 2313.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 12.5 _exptl_crystal_description rod _exptl_crystal_colour dark-red _exptl_crystal_size_max .52 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator beta-filter _diffrn_measurement_device_type 'Nicolet P3' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 8 _diffrn_reflns_number 1097 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 22.42 _reflns_number_total 1097 _reflns_number_gt 1076 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1097 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.1051 _refine_ls_wR_factor_ref 0.2957 _refine_ls_wR_factor_gt 0.2923 _refine_ls_goodness_of_fit_ref 1.451 _refine_ls_restrained_S_all 1.451 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn 0.4622(3) 0.5205(2) 0.32552(13) 0.0380(12) Uani 1 d . . . O1 O 0.4149(12) 0.3901(10) 0.3662(6) 0.046(4) Uiso 1 d . . . O2 O 0.3027(11) 0.5091(9) 0.2587(6) 0.039(4) Uiso 1 d . . . O3 O 0.2876(14) 0.1995(12) 0.3603(7) 0.065(5) Uiso 1 d . . . O4 O 0.1126(14) 0.4080(12) 0.1675(7) 0.061(4) Uiso 1 d . . . O5 O 0.6181(13) 0.4321(10) 0.2629(6) 0.051(4) Uiso 1 d . . . O6 O 0.6680(13) 0.5029(10) 0.3636(7) 0.058(4) Uiso 1 d . . . N1 N 0.4256(15) 0.6100(12) 0.4137(8) 0.044(4) Uiso 1 d . . . N2 N 0.5082(14) 0.6583(12) 0.2848(8) 0.039(4) Uiso 1 d . . . C1 C 0.3107(18) 0.3790(16) 0.4009(9) 0.037(5) Uiso 1 d . . . C2 C 0.247(2) 0.2761(16) 0.4015(10) 0.045(5) Uiso 1 d . . . C3 C 0.138(2) 0.2573(18) 0.4379(10) 0.057(6) Uiso 1 d . . . C4 C 0.101(2) 0.3423(18) 0.4793(10) 0.056(6) Uiso 1 d . . . C5 C 0.162(2) 0.4401(18) 0.4820(11) 0.064(7) Uiso 1 d . . . C6 C 0.280(2) 0.4649(18) 0.4476(10) 0.049(6) Uiso 1 d . . . C7 C 0.345(2) 0.5661(16) 0.4520(10) 0.047(6) Uiso 1 d . . . C8 C 0.502(2) 0.7131(18) 0.4345(10) 0.056(6) Uiso 1 d . . . C9 C 0.514(2) 0.7930(16) 0.3790(10) 0.054(6) Uiso 1 d . . . C10 C 0.591(2) 0.7435(19) 0.3262(10) 0.060(6) Uiso 1 d . . . C11 C 0.466(2) 0.6825(15) 0.2208(10) 0.040(5) Uiso 1 d . . . C12 C 0.372(2) 0.6266(17) 0.1743(11) 0.056(7) Uiso 1 d . . . C13 C 0.2903(18) 0.5356(16) 0.1945(9) 0.039(5) Uiso 1 d . . . C14 C 0.1891(19) 0.4871(16) 0.1438(10) 0.046(6) Uiso 1 d . . . C15 C 0.174(2) 0.5174(19) 0.0785(11) 0.069(7) Uiso 1 d . . . C16 C 0.355(2) 0.657(2) 0.1052(12) 0.072(7) Uiso 1 d . . . C17 C 0.252(3) 0.090(2) 0.3681(12) 0.087(8) Uiso 1 d . . . C18 C 0.021(3) 0.345(2) 0.1184(14) 0.101(9) Uiso 1 d . . . C19 C 0.259(2) 0.608(2) 0.0589(12) 0.081(8) Uiso 1 d . . . C20 C 0.860(2) 0.4229(19) 0.3218(11) 0.066(7) Uiso 1 d . . . C21 C 0.942(2) 0.521(2) 0.3162(12) 0.085(8) Uiso 1 d . . . C22 C 0.886(3) 0.334(2) 0.2755(13) 0.096(9) Uiso 1 d . . . C23 C 0.706(2) 0.4477(16) 0.3132(11) 0.051(6) Uiso 1 d . . . H3A H 0.0921 0.1848 0.4364 0.080 Uiso 1 d . . . H4A H 0.0273 0.3310 0.5056 0.080 Uiso 1 d . . . H5A H 0.1308 0.5014 0.5099 0.080 Uiso 1 d . . . H7A H 0.3214 0.6143 0.4891 0.080 Uiso 1 d . . . H8A H 0.5988 0.6942 0.4581 0.080 Uiso 1 d . . . H8B H 0.4621 0.7498 0.4721 0.080 Uiso 1 d . . . H9A H 0.5527 0.8644 0.3967 0.080 Uiso 1 d . . . H9B H 0.4172 0.8124 0.3568 0.080 Uiso 1 d . . . H10A H 0.6163 0.8070 0.2955 0.080 Uiso 1 d . . . H10B H 0.6837 0.7190 0.3478 0.080 Uiso 1 d . . . H11A H 0.5065 0.7500 0.2039 0.080 Uiso 1 d . . . H15A H 0.1014 0.4823 0.0449 0.080 Uiso 1 d . . . H16A H 0.4163 0.7149 0.0906 0.080 Uiso 1 d . . . H17A H 0.2857 0.0408 0.3375 0.080 Uiso 1 d . . . H17B H 0.2847 0.0632 0.4146 0.080 Uiso 1 d . . . H17C H 0.1482 0.0810 0.3616 0.080 Uiso 1 d . . . H18A H -0.0298 0.2909 0.1374 0.080 Uiso 1 d . . . H18B H -0.0475 0.3960 0.0909 0.080 Uiso 1 d . . . H18C H 0.0727 0.3111 0.0858 0.080 Uiso 1 d . . . H19A H 0.2517 0.6300 0.0105 0.080 Uiso 1 d . . . H20A H 0.8881 0.3891 0.3671 0.080 Uiso 1 d . . . H21A H 1.0413 0.5068 0.3233 0.080 Uiso 1 d . . . H21B H 0.9144 0.5566 0.2737 0.080 Uiso 1 d . . . H21C H 0.9259 0.5742 0.3519 0.080 Uiso 1 d . . . H22A H 0.9838 0.3113 0.2786 0.080 Uiso 1 d . . . H22B H 0.8331 0.2647 0.2794 0.080 Uiso 1 d . . . H22C H 0.8568 0.3561 0.2269 0.080 Uiso 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 Mn 0.058(2) 0.0313(19) 0.0271(18) -0.0053(17) 0.0144(15) -0.0022(18) _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 Mn O1 1.867(12) . ? Mn O2 1.875(11) . ? Mn N2 1.939(15) . ? Mn O6 2.026(13) . ? Mn N1 2.150(15) . ? Mn O5 2.372(12) . ? Mn C23 2.57(2) . ? O1 C1 1.324(18) . ? O2 C13 1.310(19) . ? O3 C2 1.34(2) . ? O3 C17 1.39(3) . ? O4 C14 1.34(2) . ? O4 C18 1.43(3) . ? O5 C23 1.22(2) . ? O6 C23 1.31(2) . ? N1 C7 1.30(2) . ? N1 C8 1.47(2) . ? N2 C11 1.31(2) . ? N2 C10 1.47(2) . ? C1 C2 1.39(2) . ? C1 C6 1.46(2) . ? C2 C3 1.40(2) . ? C3 C4 1.40(3) . ? C4 C5 1.32(2) . ? C5 C6 1.46(3) . ? C6 C7 1.37(2) . ? C8 C9 1.49(2) . ? C9 C10 1.52(3) . ? C11 C12 1.37(2) . ? C12 C16 1.41(3) . ? C12 C13 1.45(2) . ? C13 C14 1.42(2) . ? C14 C15 1.34(3) . ? C15 C19 1.46(3) . ? C16 C19 1.34(3) . ? C20 C21 1.44(3) . ? C20 C22 1.47(3) . ? C20 C23 1.50(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn O2 91.0(5) . . ? O1 Mn N2 178.4(6) . . ? O2 Mn N2 89.0(6) . . ? O1 Mn O6 92.5(5) . . ? O2 Mn O6 154.8(5) . . ? N2 Mn O6 88.2(6) . . ? O1 Mn N1 88.9(6) . . ? O2 Mn N1 113.3(5) . . ? N2 Mn N1 89.7(6) . . ? O6 Mn N1 91.7(5) . . ? O1 Mn O5 94.2(5) . . ? O2 Mn O5 96.4(5) . . ? N2 Mn O5 87.3(5) . . ? O6 Mn O5 58.5(5) . . ? N1 Mn O5 150.1(5) . . ? O1 Mn C23 92.8(6) . . ? O2 Mn C23 124.6(6) . . ? N2 Mn C23 88.6(6) . . ? O6 Mn C23 30.4(5) . . ? N1 Mn C23 122.1(6) . . ? O5 Mn C23 28.2(5) . . ? C1 O1 Mn 125.3(12) . . ? C13 O2 Mn 127.8(11) . . ? C2 O3 C17 119.3(17) . . ? C14 O4 C18 116.8(17) . . ? C23 O5 Mn 84.8(12) . . ? C23 O6 Mn 98.3(12) . . ? C7 N1 C8 120.2(17) . . ? C7 N1 Mn 118.5(13) . . ? C8 N1 Mn 121.0(12) . . ? C11 N2 C10 116.5(17) . . ? C11 N2 Mn 123.0(13) . . ? C10 N2 Mn 120.4(13) . . ? O1 C1 C2 118.3(17) . . ? O1 C1 C6 121.1(17) . . ? C2 C1 C6 119.6(17) . . ? O3 C2 C1 115.8(17) . . ? O3 C2 C3 122.2(19) . . ? C1 C2 C3 121.7(19) . . ? C2 C3 C4 118(2) . . ? C5 C4 C3 122(2) . . ? C4 C5 C6 123(2) . . ? C7 C6 C1 122.5(18) . . ? C7 C6 C5 123(2) . . ? C1 C6 C5 114.4(18) . . ? N1 C7 C6 129.9(19) . . ? N1 C8 C9 115.7(17) . . ? C8 C9 C10 111.9(17) . . ? N2 C10 C9 112.2(17) . . ? N2 C11 C12 128.3(18) . . ? C11 C12 C16 120(2) . . ? C11 C12 C13 121.2(19) . . ? C16 C12 C13 119(2) . . ? O2 C13 C14 122.8(18) . . ? O2 C13 C12 119.5(17) . . ? C14 C13 C12 117.3(18) . . ? O4 C14 C15 124.3(19) . . ? O4 C14 C13 113.5(17) . . ? C15 C14 C13 122(2) . . ? C14 C15 C19 120(2) . . ? C19 C16 C12 121(2) . . ? C16 C19 C15 120(2) . . ? C21 C20 C22 113(2) . . ? C21 C20 C23 112.3(19) . . ? C22 C20 C23 110(2) . . ? O5 C23 O6 118.2(18) . . ? O5 C23 C20 127(2) . . ? O6 C23 C20 114.2(19) . . ? O5 C23 Mn 67.0(11) . . ? O6 C23 Mn 51.3(9) . . ? C20 C23 Mn 165.3(16) . . ? _diffrn_measured_fraction_theta_max 0.345 _diffrn_reflns_theta_full 22.42 _diffrn_measured_fraction_theta_full 0.345 _refine_diff_density_max 1.263 _refine_diff_density_min -0.881 _refine_diff_density_rms 0.150 #=END data_Figure4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H27 Mn N2 O8' _chemical_formula_weight 550.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.927(2) _cell_length_b 13.495(3) _cell_length_c 18.761(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.88(3) _cell_angle_gamma 90.00 _cell_volume 2500.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 11.8 _cell_measurement_theta_max 12.7 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max .40 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.582 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator beta-filter _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% .5 _diffrn_reflns_number 941 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 22.45 _reflns_number_total 888 _reflns_number_gt 888 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^2^+1.9494P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 888 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1385 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn 0.5183(2) 0.49540(19) 0.37084(11) 0.0448(7) Uani 1 d . . . O1 O 0.3804(9) 0.5696(6) 0.4072(5) 0.048(3) Uani 1 d . . . O2 O 0.4871(9) 0.3829(7) 0.4266(5) 0.052(3) Uani 1 d . . . O3 O 0.3723(10) 0.2482(7) 0.4935(5) 0.060(3) Uani 1 d . . . O4 O 0.1876(9) 0.6347(8) 0.4726(5) 0.069(3) Uani 1 d . . . O5 O 0.4060(10) 0.4401(7) 0.2760(5) 0.060(3) Uani 1 d . . . O6 O 0.2494(11) 0.4123(10) 0.1864(6) 0.093(4) Uani 1 d . . . O1W O 0.6785(9) 0.5474(7) 0.4645(5) 0.053(3) Uiso 1 d . . . O2W O 0.0634(19) 0.4597(15) 0.0698(10) 0.195(8) Uiso 1 d . . . N1 N 0.6796(10) 0.4324(9) 0.3344(5) 0.045(3) Uiso 1 d . . . N2 N 0.5757(10) 0.6095(8) 0.3157(5) 0.046(3) Uiso 1 d . . . C1 C 0.5248(13) 0.2912(11) 0.4127(7) 0.046(4) Uiso 1 d . . . C2 C 0.4612(14) 0.2167(11) 0.4488(7) 0.047(4) Uiso 1 d . . . C3 C 0.4895(16) 0.1173(13) 0.4357(8) 0.066(5) Uiso 1 d . . . C4 C 0.5833(17) 0.0933(13) 0.3891(9) 0.074(5) Uiso 1 d . . . C5 C 0.6498(14) 0.1621(12) 0.3559(8) 0.060(4) Uiso 1 d . . . C6 C 0.6195(14) 0.2662(11) 0.3675(7) 0.051(4) Uiso 1 d . . . C7 C 0.6999(14) 0.3354(12) 0.3350(7) 0.055(4) Uiso 1 d . . . C8 C 0.7664(14) 0.5047(12) 0.3035(7) 0.056(4) Uiso 1 d . . . C9 C 0.6784(14) 0.5819(11) 0.2678(8) 0.059(4) Uiso 1 d . . . C10 C 0.5267(14) 0.6988(11) 0.3147(7) 0.049(4) Uiso 1 d . . . C11 C 0.4196(14) 0.7293(11) 0.3554(8) 0.052(4) Uiso 1 d . . . C12 C 0.3536(13) 0.6650(11) 0.3984(7) 0.043(4) Uiso 1 d . . . C13 C 0.2455(14) 0.7022(11) 0.4323(8) 0.049(4) Uiso 1 d . . . C14 C 0.2074(15) 0.8018(12) 0.4287(8) 0.065(5) Uiso 1 d . . . C15 C 0.2808(16) 0.8629(12) 0.3861(8) 0.067(5) Uiso 1 d . . . C16 C 0.3816(15) 0.8320(12) 0.3498(8) 0.064(4) Uiso 1 d . . . C17 C 0.2885(17) 0.4243(11) 0.2503(8) 0.047(4) Uiso 1 d . . . C18 C 0.1804(15) 0.4169(12) 0.3032(8) 0.068(5) Uiso 1 d . . . C19 C 0.1118(15) 0.3170(12) 0.3017(9) 0.064(4) Uiso 1 d . . . C20 C 0.1315(15) 0.2541(12) 0.3598(8) 0.063(5) Uiso 1 d . . . C21 C 0.0715(15) 0.1624(13) 0.3591(9) 0.070(5) Uiso 1 d . . . C22 C -0.0091(16) 0.1307(12) 0.3021(9) 0.074(5) Uiso 1 d . . . C23 C -0.0296(16) 0.1914(14) 0.2407(9) 0.079(5) Uiso 1 d . . . C24 C 0.0288(15) 0.2814(12) 0.2416(9) 0.063(5) Uiso 1 d . . . C25 C 0.3017(15) 0.1772(13) 0.5319(9) 0.076(5) Uiso 1 d . . . C26 C 0.073(2) 0.6657(15) 0.5038(10) 0.098(6) Uiso 1 d . . . H3 H 0.4436 0.0664 0.4612 0.080 Uiso 1 d . . . H4 H 0.5957 0.0229 0.3739 0.080 Uiso 1 d . . . H5 H 0.7126 0.1475 0.3207 0.080 Uiso 1 d . . . H7 H 0.7743 0.3013 0.3109 0.080 Uiso 1 d . . . H81 H 0.8241 0.4754 0.2712 0.080 Uiso 1 d . . . H82 H 0.8289 0.5361 0.3422 0.080 Uiso 1 d . . . H91 H 0.7295 0.6417 0.2570 0.080 Uiso 1 d . . . H92 H 0.6359 0.5582 0.2224 0.080 Uiso 1 d . . . H10 H 0.5498 0.7565 0.2876 0.080 Uiso 1 d . . . H14 H 0.1325 0.8280 0.4543 0.080 Uiso 1 d . . . H15 H 0.2513 0.9356 0.3818 0.080 Uiso 1 d . . . H16 H 0.4276 0.8777 0.3212 0.080 Uiso 1 d . . . H181 H 0.1123 0.4696 0.2921 0.080 Uiso 1 d . . . H182 H 0.2207 0.4316 0.3514 0.080 Uiso 1 d . . . H20 H 0.1948 0.2743 0.4022 0.080 Uiso 1 d . . . H21 H 0.0823 0.1210 0.4034 0.080 Uiso 1 d . . . H22 H -0.0505 0.0649 0.3039 0.080 Uiso 1 d . . . H23 H -0.0896 0.1692 0.1972 0.080 Uiso 1 d . . . H24 H 0.0162 0.3255 0.2012 0.080 Uiso 1 d . . . H251 H 0.3810 0.1570 0.5628 0.080 Uiso 1 d . . . H252 H 0.2612 0.2146 0.5816 0.080 Uiso 1 d . . . H253 H 0.2209 0.1403 0.5058 0.080 Uiso 1 d . . . H261 H 0.0589 0.6992 0.5477 0.080 Uiso 1 d . . . H262 H -0.0212 0.6909 0.4558 0.080 Uiso 1 d . . . H263 H 0.0300 0.6010 0.5146 0.080 Uiso 1 d . . . H11W H 0.6800 0.5031 0.5103 0.080 Uiso 1 d . . . H12W H 0.6392 0.5963 0.4717 0.080 Uiso 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 Mn 0.0525(12) 0.0322(11) 0.0521(12) 0.0005(14) 0.0168(9) 0.0000(15) O1 0.064(7) 0.026(6) 0.056(6) 0.000(5) 0.024(5) 0.001(5) O2 0.084(7) 0.025(5) 0.054(6) 0.002(5) 0.035(6) 0.001(5) O3 0.081(8) 0.036(6) 0.067(6) 0.023(6) 0.025(6) -0.009(5) O4 0.068(7) 0.067(8) 0.078(8) 0.004(6) 0.040(6) 0.030(6) O5 0.049(7) 0.069(7) 0.064(7) -0.013(6) 0.012(6) 0.002(6) O6 0.083(9) 0.131(12) 0.066(8) -0.010(8) 0.010(7) -0.012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn O1 1.880(9) . ? Mn O2 1.887(9) . ? Mn N2 1.971(11) . ? Mn N1 1.995(11) . ? Mn O5 2.135(10) . ? Mn O1W 2.353(9) . ? O1 C12 1.322(15) . ? O2 C1 1.327(15) . ? O3 C2 1.347(15) . ? O3 C25 1.424(18) . ? O4 C13 1.349(16) . ? O4 C26 1.40(2) . ? O5 C17 1.234(16) . ? O6 C17 1.232(15) . ? N1 C7 1.323(17) . ? N1 C8 1.461(17) . ? N2 C10 1.298(16) . ? N2 C9 1.475(16) . ? C1 C6 1.371(18) . ? C1 C2 1.397(18) . ? C2 C3 1.398(19) . ? C3 C4 1.379(19) . ? C4 C5 1.331(19) . ? C5 C6 1.458(19) . ? C6 C7 1.407(18) . ? C8 C9 1.476(19) . ? C10 C11 1.431(18) . ? C11 C12 1.393(18) . ? C11 C16 1.44(2) . ? C12 C13 1.396(17) . ? C13 C14 1.40(2) . ? C14 C15 1.40(2) . ? C15 C16 1.333(19) . ? C17 C18 1.538(19) . ? C18 C19 1.51(2) . ? C19 C20 1.380(19) . ? C19 C24 1.410(19) . ? C20 C21 1.37(2) . ? C21 C22 1.34(2) . ? C22 C23 1.41(2) . ? C23 C24 1.35(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 Mn O2 93.5(4) . . ? O1 Mn N2 92.0(4) . . ? O2 Mn N2 172.7(4) . . ? O1 Mn N1 172.5(5) . . ? O2 Mn N1 91.7(4) . . ? N2 Mn N1 82.4(5) . . ? O1 Mn O5 98.7(4) . . ? O2 Mn O5 94.5(4) . . ? N2 Mn O5 89.5(4) . . ? N1 Mn O5 86.2(4) . . ? O1 Mn O1W 91.8(4) . . ? O2 Mn O1W 87.9(4) . . ? N2 Mn O1W 87.1(4) . . ? N1 Mn O1W 83.0(4) . . ? O5 Mn O1W 169.1(3) . . ? C12 O1 Mn 128.2(9) . . ? C1 O2 Mn 125.2(8) . . ? C2 O3 C25 119.4(12) . . ? C13 O4 C26 116.5(12) . . ? C17 O5 Mn 141.2(9) . . ? C7 N1 C8 124.7(13) . . ? C7 N1 Mn 123.0(10) . . ? C8 N1 Mn 112.2(9) . . ? C10 N2 C9 120.4(12) . . ? C10 N2 Mn 127.2(9) . . ? C9 N2 Mn 112.2(9) . . ? O2 C1 C6 125.2(13) . . ? O2 C1 C2 115.2(12) . . ? C6 C1 C2 119.7(14) . . ? O3 C2 C1 115.7(13) . . ? O3 C2 C3 124.6(14) . . ? C1 C2 C3 119.7(14) . . ? C4 C3 C2 119.8(15) . . ? C5 C4 C3 122.2(17) . . ? C4 C5 C6 118.8(14) . . ? C1 C6 C7 124.0(14) . . ? C1 C6 C5 119.7(13) . . ? C7 C6 C5 116.1(13) . . ? N1 C7 C6 124.6(14) . . ? N1 C8 C9 107.8(11) . . ? N2 C9 C8 108.4(11) . . ? N2 C10 C11 123.8(13) . . ? C12 C11 C10 123.3(13) . . ? C12 C11 C16 120.4(14) . . ? C10 C11 C16 116.3(13) . . ? O1 C12 C11 125.3(13) . . ? O1 C12 C13 116.6(13) . . ? C11 C12 C13 118.0(13) . . ? O4 C13 C14 123.3(14) . . ? O4 C13 C12 113.9(13) . . ? C14 C13 C12 122.7(15) . . ? C13 C14 C15 116.1(15) . . ? C16 C15 C14 124.5(16) . . ? C15 C16 C11 118.1(15) . . ? O6 C17 O5 126.5(14) . . ? O6 C17 C18 116.6(14) . . ? O5 C17 C18 116.9(13) . . ? C19 C18 C17 112.9(13) . . ? C20 C19 C24 116.5(14) . . ? C20 C19 C18 120.5(14) . . ? C24 C19 C18 123.0(14) . . ? C21 C20 C19 121.3(15) . . ? C22 C21 C20 121.3(16) . . ? C21 C22 C23 119.4(16) . . ? C24 C23 C22 119.2(15) . . ? C23 C24 C19 122.2(15) . . ? _diffrn_measured_fraction_theta_max 0.260 _diffrn_reflns_theta_full 22.45 _diffrn_measured_fraction_theta_full 0.260 _refine_diff_density_max 0.437 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.073 #=END data_Figure4b _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H32 Mn N2 O8' _chemical_formula_weight 579.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.440(6) _cell_length_b 13.647(5) _cell_length_c 19.300(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.33(6) _cell_angle_gamma 90.00 _cell_volume 2713.4(24) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 10.162 _cell_measurement_theta_max 22.102 _exptl_crystal_description blocks _exptl_crystal_colour 'deep red' _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min .21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method ? _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.540 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 37.83 _diffrn_reflns_number 4657 _diffrn_reflns_av_R_equivalents 0.0866 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 22.51 _reflns_number_total 3547 _reflns_number_observed 2169 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1375P)^2^+10.5499P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3544 _refine_ls_number_parameters 343 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1491 _refine_ls_R_factor_obs 0.0961 _refine_ls_wR_factor_all 0.3005 _refine_ls_wR_factor_obs 0.2527 _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.175 _refine_ls_restrained_S_all 1.070 _refine_ls_restrained_S_obs 1.175 _refine_ls_shift/esd_max -0.055 _refine_ls_shift/esd_mean 0.003 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.02490(14) 0.00310(10) 0.36780(7) 0.0525(5) Uani 1 d . . N1 N 0.1776(8) 0.0782(7) 0.3420(4) 0.063(2) Uani 1 d . . N2 N 0.0699(8) -0.1215(7) 0.3178(4) 0.068(2) Uani 1 d . . O1 O -0.0173(6) 0.1126(4) 0.4215(3) 0.057(2) Uani 1 d . . O2 O -0.1113(6) -0.0659(4) 0.4025(3) 0.059(2) Uani 1 d . . O3 O -0.1377(7) 0.2399(5) 0.4891(3) 0.068(2) Uani 1 d . . O4 O -0.3020(7) -0.1189(5) 0.4677(4) 0.079(2) Uani 1 d . . O5 O -0.0784(7) 0.0580(6) 0.2710(4) 0.074(2) Uani 1 d . . O6 O 0.1697(6) -0.0455(5) 0.4656(3) 0.063(2) Uani 1 d . . H6A H 0.1527(6) -0.1042(5) 0.4756(3) 0.080 Uiso 1 d R . O7 O -0.2108(8) 0.0920(7) 0.1732(4) 0.094(3) Uani 1 d . . C1 C 0.0079(9) 0.2074(7) 0.4124(5) 0.055(2) Uani 1 d . . C2 C -0.0550(11) 0.2771(7) 0.4475(5) 0.065(3) Uani 1 d . . C3 C -0.0304(13) 0.3781(8) 0.4389(6) 0.081(3) Uani 1 d . . H3A H -0.0752(13) 0.4249(8) 0.4634(6) 0.080 Uiso 1 d R . C4 C 0.0566(12) 0.4088(8) 0.3982(7) 0.085(4) Uani 1 d . . H4A H 0.0699(12) 0.4776(8) 0.3918(7) 0.080 Uiso 1 d R . C5 C 0.1212(13) 0.3424(8) 0.3653(6) 0.084(4) Uani 1 d . . H5A H 0.1844(13) 0.3651(8) 0.3380(6) 0.080 Uiso 1 d R . C6 C 0.1006(10) 0.2403(7) 0.3707(5) 0.062(3) Uani 1 d . . C7 C 0.1857(11) 0.1738(9) 0.3433(6) 0.077(3) Uani 1 d . . H7A H 0.2547(11) 0.2029(9) 0.3229(6) 0.080 Uiso 1 d R . C8 C 0.2936(11) 0.0314(12) 0.3201(8) 0.111(5) Uani 1 d D . H8A H 0.3623(11) 0.0269(12) 0.3596(8) 0.080 Uiso 1 d R . H8B H 0.3227(11) 0.0741(12) 0.2864(8) 0.080 Uiso 1 d R . C9 C 0.2605(20) -0.0428(13) 0.2599(12) 0.332(24) Uani 1 d D . H9A H 0.3147(20) -0.0841(13) 0.2926(12) 0.080 Uiso 1 d R . H9B H 0.3036(20) -0.0392(13) 0.2196(12) 0.080 Uiso 1 d R . C10 C 0.1734(17) -0.1281(15) 0.2757(8) 0.151(7) Uani 1 d D . H10A H 0.1306(17) -0.1038(15) 0.2313(8) 0.080 Uiso 1 d R . H10B H 0.2036(17) -0.1931(15) 0.2682(8) 0.080 Uiso 1 d R . C11 C 0.0113(11) -0.2043(8) 0.3195(5) 0.065(3) Uani 1 d . . H11A H 0.0391(11) -0.2563(8) 0.2919(5) 0.080 Uiso 1 d R . C12 C -0.0885(11) -0.2288(7) 0.3585(5) 0.066(3) Uani 1 d . . C13 C -0.1286(12) -0.3278(8) 0.3564(6) 0.079(3) Uani 1 d . . H13A H -0.0873(12) -0.3748(8) 0.3303(6) 0.080 Uiso 1 d R . C14 C -0.2267(13) -0.3557(9) 0.3918(7) 0.090(4) Uani 1 d . . H14A H -0.2528(13) -0.4232(9) 0.3911(7) 0.080 Uiso 1 d R . C15 C -0.2833(13) -0.2879(9) 0.4298(6) 0.088(4) Uani 1 d . . H15A H -0.3533(13) -0.3073(9) 0.4535(6) 0.080 Uiso 1 d R . C16 C -0.2472(10) -0.1907(8) 0.4324(5) 0.065(3) Uani 1 d . . C17 C -0.1469(9) -0.1596(7) 0.3974(5) 0.055(2) Uani 1 d . . C18 C -0.1904(12) 0.0663(7) 0.2354(6) 0.062(3) Uani 1 d . . C19 C -0.3092(10) 0.0407(8) 0.2693(6) 0.076(3) Uani 1 d . . H19A H -0.2820(10) 0.0044(8) 0.3118(6) 0.080 Uiso 1 d R . H19B H -0.3670(10) 0.0001(8) 0.2378(6) 0.080 Uiso 1 d R . C20 C -0.3807(9) 0.1330(7) 0.2853(6) 0.060(3) Uani 1 d . . C21 C -0.4648(10) 0.1793(8) 0.2338(5) 0.067(3) Uani 1 d . . H21A H -0.4804(10) 0.1519(8) 0.1874(5) 0.080 Uiso 1 d R . C22 C -0.5303(11) 0.2640(9) 0.2490(7) 0.082(3) Uani 1 d . . H22A H -0.5880(11) 0.2959(9) 0.2120(7) 0.080 Uiso 1 d R . C23 C -0.5060(12) 0.3016(10) 0.3161(7) 0.090(4) Uani 1 d . . H23A H -0.5518(12) 0.3591(10) 0.3271(7) 0.080 Uiso 1 d R . C24 C -0.4234(14) 0.2571(11) 0.3665(7) 0.098(4) Uani 1 d . . H24A H -0.4049(14) 0.2852(11) 0.4126(7) 0.080 Uiso 1 d R . C25 C -0.3591(10) 0.1723(10) 0.3505(6) 0.081(3) Uani 1 d . . H25A H -0.3027(10) 0.1390(10) 0.3873(6) 0.080 Uiso 1 d R . C26 C -0.1998(12) 0.3059(9) 0.5302(6) 0.087(4) Uani 1 d . . H26A H -0.2541(12) 0.2694(9) 0.5566(6) 0.080 Uiso 1 d R . H26B H -0.1349(12) 0.3404(9) 0.5620(6) 0.080 Uiso 1 d R . H26C H -0.2518(12) 0.3520(9) 0.5004(6) 0.080 Uiso 1 d R . C27 C -0.4161(14) -0.1411(12) 0.4948(8) 0.120(5) Uani 1 d . . H27A H -0.4433(14) -0.0839(12) 0.5175(8) 0.080 Uiso 1 d R . H27B H -0.4843(14) -0.1615(12) 0.4582(8) 0.080 Uiso 1 d R . H27C H -0.3969(14) -0.1929(12) 0.5285(8) 0.080 Uiso 1 d R . O1X O 0.5586(18) -0.0164(14) 0.0363(9) 0.224(7) Uiso 1 d . . H1A H 0.4938(18) 0.0012(14) -0.0054(9) 0.080 Uiso 1 d R . C1X C 0.5552(20) 0.0622(15) 0.0772(11) 0.178(8) Uiso 1 d . . H1X1 H 0.6355(30) 0.0670(29) 0.1093(23) 0.080 Uiso 1 calc R . H1X2 H 0.4846(41) 0.0559(25) 0.1031(26) 0.080 Uiso 1 calc R . H1X3 H 0.5432(60) 0.1200(16) 0.0486(11) 0.080 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0627(9) 0.0449(9) 0.0506(8) 0.0022(7) 0.0117(6) -0.0024(7) N1 0.059(5) 0.065(6) 0.067(5) 0.014(5) 0.016(4) 0.000(4) N2 0.065(6) 0.086(7) 0.056(5) -0.012(5) 0.020(4) -0.003(5) O1 0.076(5) 0.040(4) 0.057(4) 0.002(3) 0.018(3) -0.002(3) O2 0.078(5) 0.045(4) 0.055(4) -0.001(3) 0.018(3) -0.014(3) O3 0.087(5) 0.050(4) 0.070(4) -0.011(4) 0.020(4) 0.004(4) O4 0.079(5) 0.077(5) 0.089(5) -0.009(4) 0.035(4) -0.020(4) O5 0.066(5) 0.099(6) 0.057(4) 0.018(4) 0.009(4) 0.000(4) O6 0.080(5) 0.055(4) 0.052(4) 0.009(3) 0.005(3) 0.005(4) O7 0.092(6) 0.121(7) 0.068(5) 0.021(5) 0.008(4) 0.023(5) C1 0.065(6) 0.040(6) 0.056(6) -0.001(5) 0.001(5) 0.003(5) C2 0.081(8) 0.048(6) 0.057(6) 0.000(5) -0.011(6) -0.014(5) C3 0.103(9) 0.044(6) 0.089(9) -0.001(6) -0.009(7) 0.000(6) C4 0.094(9) 0.042(7) 0.117(10) 0.008(7) 0.012(8) -0.011(6) C5 0.104(10) 0.056(7) 0.093(9) 0.006(7) 0.017(7) -0.027(7) C6 0.067(7) 0.060(7) 0.062(6) 0.007(5) 0.014(5) -0.009(6) C7 0.082(8) 0.082(9) 0.065(7) 0.013(6) 0.010(6) -0.013(7) C8 0.058(7) 0.159(14) 0.126(11) 0.002(11) 0.042(8) 0.015(8) C9 0.232(31) 0.213(27) 0.613(67) -0.203(37) 0.257(41) -0.020(24) C10 0.153(15) 0.197(20) 0.119(12) -0.063(13) 0.072(12) -0.031(15) C11 0.075(7) 0.055(7) 0.065(7) -0.018(5) 0.008(6) -0.003(6) C12 0.090(8) 0.046(6) 0.055(6) 0.000(5) -0.010(6) 0.000(6) C13 0.097(9) 0.050(7) 0.086(8) -0.016(6) 0.000(7) 0.006(6) C14 0.104(10) 0.053(7) 0.107(10) -0.001(7) 0.004(8) -0.025(7) C15 0.105(10) 0.075(9) 0.082(8) 0.005(7) 0.014(7) -0.039(8) C16 0.068(7) 0.060(7) 0.065(7) -0.009(6) 0.003(5) -0.009(6) C17 0.060(6) 0.051(6) 0.050(6) -0.001(5) 0.001(5) -0.011(5) C18 0.090(8) 0.040(6) 0.058(7) -0.003(5) 0.013(6) 0.015(5) C19 0.058(6) 0.066(7) 0.110(9) 0.020(7) 0.027(6) -0.003(6) C20 0.046(6) 0.065(7) 0.067(7) 0.015(6) 0.005(5) -0.011(5) C21 0.065(7) 0.079(8) 0.060(6) 0.008(6) 0.013(5) -0.006(6) C22 0.067(8) 0.091(9) 0.086(9) 0.011(8) 0.009(7) 0.008(7) C23 0.090(9) 0.086(9) 0.095(10) -0.012(8) 0.019(8) 0.006(7) C24 0.102(10) 0.117(12) 0.069(8) -0.013(8) -0.004(8) -0.001(9) C25 0.055(7) 0.105(10) 0.079(9) 0.003(8) -0.005(6) -0.009(7) C26 0.109(9) 0.077(8) 0.072(7) -0.019(6) 0.008(7) 0.026(7) C27 0.115(12) 0.127(12) 0.124(12) -0.016(10) 0.035(10) -0.042(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 Mn1 O1 1.911(6) . ? Mn1 O2 1.915(6) . ? Mn1 N1 2.024(8) . ? Mn1 N2 2.047(9) . ? Mn1 O5 2.136(7) . ? Mn1 O6 2.316(6) . ? N1 C7 1.307(14) . ? N1 C8 1.490(14) . ? N2 C11 1.288(13) . ? N2 C10 1.46(2) . ? O1 C1 1.337(10) . ? O2 C17 1.330(11) . ? O3 C2 1.369(12) . ? O3 C26 1.424(11) . ? O4 C16 1.371(12) . ? O4 C27 1.409(14) . ? O5 C18 1.261(12) . ? O7 C18 1.235(11) . ? C1 C2 1.392(13) . ? C1 C6 1.428(13) . ? C2 C3 1.417(14) . ? C3 C4 1.36(2) . ? C4 C5 1.35(2) . ? C5 C6 1.417(14) . ? C6 C7 1.430(15) . ? C8 C9 1.538(2) . ? C9 C10 1.538(2) . ? C11 C12 1.421(15) . ? C12 C17 1.406(14) . ? C12 C13 1.413(15) . ? C13 C14 1.37(2) . ? C14 C15 1.37(2) . ? C15 C16 1.378(15) . ? C16 C17 1.401(13) . ? C18 C19 1.534(14) . ? C19 C20 1.521(14) . ? C20 C25 1.353(14) . ? C20 C21 1.369(14) . ? C21 C22 1.398(15) . ? C22 C23 1.38(2) . ? C23 C24 1.34(2) . ? C24 C25 1.40(2) . ? O1X C1X 1.34(2) . ? O1X O1X 1.76(3) 3_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 86.9(3) . . ? O1 Mn1 N1 89.8(3) . . ? O2 Mn1 N1 173.8(3) . . ? O1 Mn1 N2 175.1(3) . . ? O2 Mn1 N2 89.8(3) . . ? N1 Mn1 N2 93.1(3) . . ? O1 Mn1 O5 94.1(3) . . ? O2 Mn1 O5 100.4(3) . . ? N1 Mn1 O5 85.0(3) . . ? N2 Mn1 O5 90.0(3) . . ? O1 Mn1 O6 87.7(3) . . ? O2 Mn1 O6 89.9(3) . . ? N1 Mn1 O6 84.8(3) . . ? N2 Mn1 O6 88.7(3) . . ? O5 Mn1 O6 169.7(3) . . ? C7 N1 C8 112.3(10) . . ? C7 N1 Mn1 123.5(8) . . ? C8 N1 Mn1 124.1(8) . . ? C11 N2 C10 111.0(11) . . ? C11 N2 Mn1 124.8(7) . . ? C10 N2 Mn1 124.2(9) . . ? C1 O1 Mn1 128.2(6) . . ? C17 O2 Mn1 131.4(6) . . ? C2 O3 C26 118.7(8) . . ? C16 O4 C27 118.5(9) . . ? C18 O5 Mn1 143.1(7) . . ? O1 C1 C2 118.6(9) . . ? O1 C1 C6 122.9(9) . . ? C2 C1 C6 118.4(9) . . ? O3 C2 C1 115.1(8) . . ? O3 C2 C3 124.9(11) . . ? C1 C2 C3 120.0(11) . . ? C4 C3 C2 121.2(12) . . ? C5 C4 C3 119.8(11) . . ? C4 C5 C6 122.2(11) . . ? C5 C6 C7 119.1(10) . . ? C5 C6 C1 118.4(10) . . ? C7 C6 C1 121.9(9) . . ? N1 C7 C6 126.7(11) . . ? N1 C8 C9 113.8(12) . . ? C10 C9 C8 114.5(16) . . ? N2 C10 C9 125.5(15) . . ? N2 C11 C12 127.8(9) . . ? C17 C12 C13 120.4(11) . . ? C17 C12 C11 122.9(9) . . ? C13 C12 C11 116.7(10) . . ? C14 C13 C12 119.5(11) . . ? C13 C14 C15 119.9(11) . . ? C14 C15 C16 122.0(12) . . ? O4 C16 C15 124.9(11) . . ? O4 C16 C17 115.3(9) . . ? C15 C16 C17 119.8(11) . . ? O2 C17 C16 118.5(9) . . ? O2 C17 C12 123.1(9) . . ? C16 C17 C12 118.4(9) . . ? O7 C18 O5 123.6(10) . . ? O7 C18 C19 117.1(11) . . ? O5 C18 C19 119.3(9) . . ? C20 C19 C18 110.8(8) . . ? C25 C20 C21 118.8(11) . . ? C25 C20 C19 120.3(10) . . ? C21 C20 C19 120.9(10) . . ? C20 C21 C22 120.6(11) . . ? C23 C22 C21 118.9(11) . . ? C24 C23 C22 120.9(13) . . ? C23 C24 C25 119.5(12) . . ? C20 C25 C24 121.4(11) . . ? C1X O1X O1X 100.6(19) . 3_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 N1 C7 -22.7(9) . . . . ? O2 Mn1 N1 C7 -80.4(31) . . . . ? N2 Mn1 N1 C7 161.2(9) . . . . ? O5 Mn1 N1 C7 71.5(9) . . . . ? O6 Mn1 N1 C7 -110.4(9) . . . . ? O1 Mn1 N1 C8 156.8(9) . . . . ? O2 Mn1 N1 C8 99.1(30) . . . . ? N2 Mn1 N1 C8 -19.3(9) . . . . ? O5 Mn1 N1 C8 -109.1(9) . . . . ? O6 Mn1 N1 C8 69.1(9) . . . . ? O1 Mn1 N2 C11 47.2(41) . . . . ? O2 Mn1 N2 C11 -0.4(9) . . . . ? N1 Mn1 N2 C11 174.1(9) . . . . ? O5 Mn1 N2 C11 -100.8(9) . . . . ? O6 Mn1 N2 C11 89.4(9) . . . . ? O1 Mn1 N2 C10 -132.6(36) . . . . ? O2 Mn1 N2 C10 179.8(11) . . . . ? N1 Mn1 N2 C10 -5.6(11) . . . . ? O5 Mn1 N2 C10 79.4(11) . . . . ? O6 Mn1 N2 C10 -90.3(11) . . . . ? O2 Mn1 O1 C1 -158.2(8) . . . . ? N1 Mn1 O1 C1 27.0(8) . . . . ? N2 Mn1 O1 C1 154.1(34) . . . . ? O5 Mn1 O1 C1 -58.0(8) . . . . ? O6 Mn1 O1 C1 111.8(8) . . . . ? O1 Mn1 O2 C17 -171.9(8) . . . . ? N1 Mn1 O2 C17 -114.1(29) . . . . ? N2 Mn1 O2 C17 4.4(8) . . . . ? O5 Mn1 O2 C17 94.4(8) . . . . ? O6 Mn1 O2 C17 -84.3(8) . . . . ? O1 Mn1 O5 C18 -79.6(12) . . . . ? O2 Mn1 O5 C18 7.9(12) . . . . ? N1 Mn1 O5 C18 -169.1(12) . . . . ? N2 Mn1 O5 C18 97.8(12) . . . . ? O6 Mn1 O5 C18 -179.3(12) . . . . ? Mn1 O1 C1 C2 166.4(6) . . . . ? Mn1 O1 C1 C6 -16.3(13) . . . . ? C26 O3 C2 C1 176.1(9) . . . . ? C26 O3 C2 C3 -3.5(15) . . . . ? O1 C1 C2 O3 0.5(13) . . . . ? C6 C1 C2 O3 -177.0(8) . . . . ? O1 C1 C2 C3 -180.0(9) . . . . ? C6 C1 C2 C3 2.6(14) . . . . ? O3 C2 C3 C4 177.9(10) . . . . ? C1 C2 C3 C4 -1.6(17) . . . . ? C2 C3 C4 C5 -0.2(19) . . . . ? C3 C4 C5 C6 0.9(20) . . . . ? C4 C5 C6 C7 -170.8(11) . . . . ? C4 C5 C6 C1 0.1(18) . . . . ? O1 C1 C6 C5 -179.2(9) . . . . ? C2 C1 C6 C5 -1.9(14) . . . . ? O1 C1 C6 C7 -8.6(15) . . . . ? C2 C1 C6 C7 168.7(9) . . . . ? C8 N1 C7 C6 -170.9(11) . . . . ? Mn1 N1 C7 C6 8.6(16) . . . . ? C5 C6 C7 N1 -177.6(11) . . . . ? C1 C6 C7 N1 11.8(17) . . . . ? C7 N1 C8 C9 -128.2(15) . . . . ? Mn1 N1 C8 C9 52.3(16) . . . . ? N1 C8 C9 C10 -58.6(22) . . . . ? C11 N2 C10 C9 177.7(17) . . . . ? Mn1 N2 C10 C9 -2.5(24) . . . . ? C8 C9 C10 N2 34.9(28) . . . . ? C10 N2 C11 C12 175.5(12) . . . . ? Mn1 N2 C11 C12 -4.3(16) . . . . ? N2 C11 C12 C17 6.2(17) . . . . ? N2 C11 C12 C13 -174.2(11) . . . . ? C17 C12 C13 C14 1.1(16) . . . . ? C11 C12 C13 C14 -178.6(10) . . . . ? C12 C13 C14 C15 -1.1(18) . . . . ? C13 C14 C15 C16 1.7(20) . . . . ? C27 O4 C16 C15 -10.1(17) . . . . ? C27 O4 C16 C17 170.2(10) . . . . ? C14 C15 C16 O4 178.2(11) . . . . ? C14 C15 C16 C17 -2.2(18) . . . . ? Mn1 O2 C17 C16 176.1(6) . . . . ? Mn1 O2 C17 C12 -3.8(13) . . . . ? O4 C16 C17 O2 1.7(13) . . . . ? C15 C16 C17 O2 -177.9(9) . . . . ? O4 C16 C17 C12 -178.3(8) . . . . ? C15 C16 C17 C12 2.0(15) . . . . ? C13 C12 C17 O2 178.5(9) . . . . ? C11 C12 C17 O2 -1.9(15) . . . . ? C13 C12 C17 C16 -1.5(14) . . . . ? C11 C12 C17 C16 178.2(9) . . . . ? Mn1 O5 C18 O7 -168.6(8) . . . . ? Mn1 O5 C18 C19 9.5(17) . . . . ? O7 C18 C19 C20 -75.2(12) . . . . ? O5 C18 C19 C20 106.6(11) . . . . ? C18 C19 C20 C25 -97.4(12) . . . . ? C18 C19 C20 C21 80.8(12) . . . . ? C25 C20 C21 C22 -2.0(15) . . . . ? C19 C20 C21 C22 179.9(9) . . . . ? C20 C21 C22 C23 1.8(16) . . . . ? C21 C22 C23 C24 -1.4(19) . . . . ? C22 C23 C24 C25 1.2(20) . . . . ? C21 C20 C25 C24 1.8(16) . . . . ? C19 C20 C25 C24 179.9(10) . . . . ? C23 C24 C25 C20 -1.4(19) . . . . ? _refine_diff_density_max 0.603 _refine_diff_density_min -0.895 _refine_diff_density_rms 0.094 #=END data_Figure5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 Cl Mn N3 O2' _chemical_formula_weight 411.76 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' 'Cl' 'Cl' 0.1484 0.1585 '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 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.849(3) _cell_length_b 12.409(3) _cell_length_c 13.610(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.54(3) _cell_angle_gamma 90.00 _cell_volume 1823.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3339 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3161 _reflns_number_gt 1628 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+4.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3161 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1405 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1527 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.005 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.56237(8) 0.52968(7) 0.61640(7) 0.0371(3) Uani 1 d . . . Cl1 Cl 0.61312(15) 0.45931(14) 0.78378(11) 0.0523(4) Uani 1 d . . . O1 O 0.4755(3) 0.4075(3) 0.5574(3) 0.0412(10) Uani 1 d . . . O2 O 0.4068(3) 0.5852(3) 0.6368(3) 0.0463(10) Uani 1 d . . . N1 N 0.7190(4) 0.4639(4) 0.5725(3) 0.0406(11) Uani 1 d . . . N2 N 0.6422(5) 0.6747(4) 0.6533(4) 0.0426(12) Uani 1 d . . . C1 C 0.5161(5) 0.3056(5) 0.5720(4) 0.0375(13) Uani 1 d . . . C2 C 0.4320(6) 0.2219(5) 0.5780(5) 0.0479(16) Uani 1 d . . . H2 H 0.3477 0.2367 0.5748 0.058 Uiso 1 calc R . . C3 C 0.4732(7) 0.1167(5) 0.5889(5) 0.0577(18) Uani 1 d . . . H3 H 0.4163 0.0615 0.5944 0.069 Uiso 1 calc R . . C4 C 0.5963(7) 0.0928(6) 0.5916(5) 0.0562(18) Uani 1 d . . . H4 H 0.6224 0.0216 0.5983 0.067 Uiso 1 calc R . . C5 C 0.6815(6) 0.1732(6) 0.5846(5) 0.0529(17) Uani 1 d . . . H5 H 0.7652 0.1566 0.5856 0.063 Uiso 1 calc R . . C6 C 0.6420(5) 0.2806(5) 0.5759(4) 0.0423(15) Uani 1 d . . . C7 C 0.7351(5) 0.3615(6) 0.5651(5) 0.0490(16) Uani 1 d . . . H7 H 0.8131 0.3378 0.5517 0.059 Uiso 1 calc R . . C8 C 0.8238(5) 0.5326(5) 0.5525(5) 0.0509(16) Uani 1 d . . . H8A H 0.8012 0.5763 0.4945 0.061 Uiso 1 calc R . . H8B H 0.8938 0.4879 0.5395 0.061 Uiso 1 calc R . . C9 C 0.8596(6) 0.6046(6) 0.6399(5) 0.0588(19) Uani 1 d . . . H9A H 0.8582 0.5628 0.7001 0.071 Uiso 1 calc R . . H9B H 0.9436 0.6300 0.6365 0.071 Uiso 1 calc R . . C10 C 0.7759(6) 0.6992(6) 0.6447(6) 0.064(2) Uani 1 d . . . H10A H 0.7813 0.7423 0.5858 0.077 Uiso 1 calc R . . H10B H 0.8065 0.7430 0.7008 0.077 Uiso 1 calc R . . C11 C 0.5830(6) 0.7553(5) 0.6884(5) 0.0499(17) Uani 1 d . . . H11 H 0.6297 0.8157 0.7079 0.060 Uiso 1 calc R . . C12 C 0.4549(6) 0.7602(5) 0.6998(5) 0.0501(16) Uani 1 d . . . C13 C 0.4076(8) 0.8570(6) 0.7364(6) 0.070(2) Uani 1 d . . . H13 H 0.4624 0.9124 0.7558 0.084 Uiso 1 calc R . . C14 C 0.2838(8) 0.8720(6) 0.7440(6) 0.075(2) Uani 1 d . . . H14 H 0.2548 0.9358 0.7692 0.090 Uiso 1 calc R . . C15 C 0.2030(7) 0.7895(6) 0.7133(5) 0.063(2) Uani 1 d . . . H15 H 0.1185 0.7992 0.7168 0.075 Uiso 1 calc R . . C16 C 0.2442(6) 0.6940(5) 0.6779(5) 0.0537(17) Uani 1 d . . . H16 H 0.1880 0.6400 0.6577 0.064 Uiso 1 calc R . . C17 C 0.3698(6) 0.6781(5) 0.6723(5) 0.0476(16) Uani 1 d . . . N3 N 1.4931(7) 0.7410(8) 0.9723(6) 0.104(3) Uani 1 d . . . C18 C 1.3748(7) 0.5663(6) 0.9252(6) 0.077(2) Uani 1 d . . . H18A H 1.4313 0.5145 0.9026 0.116 Uiso 1 calc R . . H18B H 1.3100 0.5805 0.8737 0.116 Uiso 1 calc R . . H18C H 1.3395 0.5384 0.9821 0.116 Uiso 1 calc R . . C19 C 1.4406(7) 0.6654(8) 0.9515(6) 0.063(2) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0336(4) 0.0380(5) 0.0397(5) -0.0027(5) 0.0032(3) -0.0011(4) Cl1 0.0614(10) 0.0550(10) 0.0401(9) 0.0050(8) 0.0030(8) 0.0019(8) O1 0.032(2) 0.041(2) 0.050(3) -0.004(2) 0.0007(18) 0.0004(18) O2 0.035(2) 0.049(3) 0.055(3) -0.006(2) 0.006(2) 0.0024(19) N1 0.035(2) 0.045(3) 0.042(3) -0.007(2) 0.002(2) -0.003(2) N2 0.050(3) 0.037(3) 0.039(3) -0.002(2) -0.003(2) -0.009(2) C1 0.043(3) 0.039(3) 0.031(3) 0.000(3) 0.006(3) 0.004(3) C2 0.043(3) 0.051(4) 0.050(4) 0.003(3) 0.005(3) -0.001(3) C3 0.064(4) 0.048(4) 0.061(5) 0.007(3) 0.003(4) -0.003(3) C4 0.068(5) 0.051(4) 0.048(4) -0.002(3) -0.003(3) 0.014(4) C5 0.048(4) 0.062(4) 0.049(4) 0.006(3) 0.006(3) 0.016(3) C6 0.039(3) 0.055(4) 0.033(3) -0.002(3) 0.002(3) 0.011(3) C7 0.028(3) 0.069(5) 0.050(4) -0.004(3) 0.003(3) 0.011(3) C8 0.046(3) 0.050(4) 0.059(4) 0.007(3) 0.016(3) -0.010(3) C9 0.048(4) 0.066(5) 0.060(5) 0.002(4) -0.004(3) -0.013(3) C10 0.049(4) 0.067(5) 0.076(5) -0.004(4) 0.006(4) -0.023(4) C11 0.068(5) 0.033(3) 0.048(4) -0.002(3) -0.005(3) -0.006(3) C12 0.063(4) 0.047(4) 0.039(4) 0.000(3) 0.000(3) 0.011(3) C13 0.087(6) 0.050(4) 0.073(6) -0.008(4) 0.004(5) 0.012(4) C14 0.106(7) 0.053(5) 0.068(5) -0.009(4) 0.016(5) 0.039(5) C15 0.071(5) 0.069(5) 0.050(4) 0.000(4) 0.011(4) 0.025(4) C16 0.059(4) 0.049(4) 0.055(4) -0.008(3) 0.011(3) 0.019(3) C17 0.051(4) 0.058(4) 0.035(4) 0.005(3) 0.010(3) 0.010(3) N3 0.073(5) 0.126(8) 0.117(7) -0.004(6) 0.029(5) -0.027(5) C18 0.063(5) 0.084(6) 0.084(6) -0.010(5) 0.004(4) 0.005(4) C19 0.045(4) 0.095(7) 0.051(5) 0.005(5) 0.014(4) 0.011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 1.868(4) . ? Mn1 O1 1.919(4) . ? Mn1 N1 2.026(5) . ? Mn1 N2 2.039(5) . ? Mn1 Cl1 2.4521(18) . ? Mn1 O1 2.487(4) 3_666 ? O1 C1 1.348(6) . ? O1 Mn1 2.487(4) 3_666 ? O2 C17 1.327(7) . ? N1 C7 1.288(8) . ? N1 C8 1.468(7) . ? N2 C11 1.303(7) . ? N2 C10 1.498(7) . ? C1 C2 1.390(8) . ? C1 C6 1.396(8) . ? C2 C3 1.383(9) . ? C3 C4 1.364(9) . ? C4 C5 1.370(9) . ? C5 C6 1.401(8) . ? C6 C7 1.442(9) . ? C8 C9 1.508(9) . ? C9 C10 1.489(9) . ? C11 C12 1.414(9) . ? C12 C17 1.402(9) . ? C12 C13 1.416(9) . ? C13 C14 1.369(11) . ? C14 C15 1.386(11) . ? C15 C16 1.370(9) . ? C16 C17 1.386(8) . ? N3 C19 1.120(10) . ? C18 C19 1.448(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1 86.51(17) . . ? O2 Mn1 N1 170.96(19) . . ? O1 Mn1 N1 87.16(18) . . ? O2 Mn1 N2 90.36(19) . . ? O1 Mn1 N2 168.47(18) . . ? N1 Mn1 N2 94.6(2) . . ? O2 Mn1 Cl1 96.78(14) . . ? O1 Mn1 Cl1 99.45(13) . . ? N1 Mn1 Cl1 90.62(14) . . ? N2 Mn1 Cl1 91.92(15) . . ? O2 Mn1 O1 87.56(16) . 3_666 ? O1 Mn1 O1 79.66(17) . 3_666 ? N1 Mn1 O1 84.96(16) . 3_666 ? N2 Mn1 O1 89.14(17) . 3_666 ? Cl1 Mn1 O1 175.52(10) . 3_666 ? C1 O1 Mn1 122.6(3) . . ? C1 O1 Mn1 117.1(3) . 3_666 ? Mn1 O1 Mn1 100.34(17) . 3_666 ? C17 O2 Mn1 133.1(4) . . ? C7 N1 C8 116.4(5) . . ? C7 N1 Mn1 123.0(4) . . ? C8 N1 Mn1 120.5(4) . . ? C11 N2 C10 112.9(5) . . ? C11 N2 Mn1 123.7(4) . . ? C10 N2 Mn1 123.4(4) . . ? O1 C1 C2 120.1(5) . . ? O1 C1 C6 121.3(5) . . ? C2 C1 C6 118.5(6) . . ? C3 C2 C1 120.2(6) . . ? C4 C3 C2 120.9(7) . . ? C3 C4 C5 120.3(6) . . ? C4 C5 C6 119.7(6) . . ? C1 C6 C5 120.3(6) . . ? C1 C6 C7 122.3(6) . . ? C5 C6 C7 117.3(6) . . ? N1 C7 C6 125.2(5) . . ? N1 C8 C9 110.0(5) . . ? C10 C9 C8 112.9(6) . . ? C9 C10 N2 116.3(5) . . ? N2 C11 C12 126.7(6) . . ? C17 C12 C11 124.6(6) . . ? C17 C12 C13 117.3(6) . . ? C11 C12 C13 118.0(7) . . ? C14 C13 C12 122.2(8) . . ? C13 C14 C15 118.3(7) . . ? C16 C15 C14 121.7(7) . . ? C15 C16 C17 119.9(7) . . ? O2 C17 C16 118.5(6) . . ? O2 C17 C12 121.0(6) . . ? C16 C17 C12 120.5(6) . . ? N3 C19 C18 178.9(9) . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.392 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.099 #=END data_Figure8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 Mn N2 O4' _chemical_formula_weight 422.35 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 17.844(3) _cell_length_b 18.881(4) _cell_length_c 12.337(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4156.5(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.663 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8011 _exptl_absorpt_correction_T_max 0.8788 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3643 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0946 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3643 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0906P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3643 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1366 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.003 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.82849(4) 0.46957(4) 0.03763(5) 0.0367(2) Uani 1 d . . . O1 O 0.75270(19) 0.39998(18) 0.0555(3) 0.0514(9) Uani 1 d . . . O2 O 0.87257(19) 0.44032(17) 0.1679(2) 0.0457(8) Uani 1 d . . . O3 O 0.7588(2) 0.55814(18) 0.1173(3) 0.0605(10) Uani 1 d . . . O4 O 0.87039(19) 0.57322(18) 0.0487(3) 0.0538(9) Uani 1 d . . . N1 N 0.7849(2) 0.4952(2) -0.1056(3) 0.0426(9) Uani 1 d . . . N2 N 0.9250(2) 0.4294(2) -0.0431(3) 0.0423(9) Uani 1 d . . . C1 C 0.6822(3) 0.4063(2) 0.0235(4) 0.0452(12) Uani 1 d . . . C2 C 0.6257(3) 0.3695(3) 0.0785(5) 0.0558(14) Uani 1 d . . . C3 C 0.5526(4) 0.3745(4) 0.0465(6) 0.0705(18) Uani 1 d . . . C4 C 0.5314(4) 0.4146(4) -0.0407(7) 0.077(2) Uani 1 d . . . C5 C 0.5854(3) 0.4506(4) -0.0970(5) 0.0615(16) Uani 1 d . . . C6 C 0.6614(3) 0.4485(3) -0.0648(4) 0.0459(12) Uani 1 d . . . C7 C 0.7151(3) 0.4853(3) -0.1303(4) 0.0478(13) Uani 1 d . . . C8 C 0.8340(3) 0.5280(3) -0.1878(4) 0.0546(13) Uani 1 d . . . C9 C 0.8937(3) 0.4759(4) -0.2257(4) 0.0574(15) Uani 1 d . . . C10 C 0.9540(3) 0.4614(4) -0.1433(5) 0.0548(14) Uani 1 d . . . C11 C 0.9599(3) 0.3765(3) -0.0016(5) 0.0521(14) Uani 1 d . . . C12 C 0.9424(3) 0.3418(3) 0.0992(4) 0.0468(12) Uani 1 d . . . C13 C 0.9726(4) 0.2749(3) 0.1215(7) 0.078(2) Uani 1 d . . . C14 C 0.9576(5) 0.2405(4) 0.2163(7) 0.088(3) Uani 1 d . . . C15 C 0.9113(4) 0.2705(4) 0.2919(6) 0.078(2) Uani 1 d . . . C16 C 0.8833(4) 0.3370(3) 0.2745(5) 0.0610(16) Uani 1 d . . . C17 C 0.8982(3) 0.3737(3) 0.1804(4) 0.0463(12) Uani 1 d . . . C18 C 0.8125(3) 0.5982(3) 0.0919(4) 0.0522(13) Uani 1 d . . . C19 C 0.8061(4) 0.6780(3) 0.1109(5) 0.0681(17) Uani 1 d . . . C20 C 0.7475(7) 0.7063(4) 0.0356(10) 0.189(7) Uani 1 d . . . H20A H 0.7671 0.7078 -0.0368 0.283 Uiso 1 calc R . . H20B H 0.7335 0.7532 0.0579 0.283 Uiso 1 calc R . . H20C H 0.7043 0.6760 0.0375 0.283 Uiso 1 calc R . . C21 C 0.7882(7) 0.6947(4) 0.2259(8) 0.144(4) Uani 1 d . . . H21A H 0.8290 0.6800 0.2714 0.216 Uiso 1 calc R . . H21B H 0.7434 0.6700 0.2470 0.216 Uiso 1 calc R . . H21C H 0.7806 0.7447 0.2336 0.216 Uiso 1 calc R . . H2 H 0.640(2) 0.340(2) 0.144(4) 0.033(12) Uiso 1 d . . . H3 H 0.517(3) 0.357(3) 0.094(4) 0.069(18) Uiso 1 d . . . H4 H 0.482(3) 0.421(3) -0.062(4) 0.058(16) Uiso 1 d . . . H5 H 0.572(3) 0.482(3) -0.144(5) 0.061(19) Uiso 1 d . . . H7 H 0.694(2) 0.501(2) -0.204(4) 0.041(12) Uiso 1 d . . . H8A H 0.853(2) 0.569(2) -0.144(4) 0.039(13) Uiso 1 d . . . H8B H 0.805(3) 0.539(3) -0.252(5) 0.067(16) Uiso 1 d . . . H9A H 0.919(3) 0.503(3) -0.292(5) 0.078(18) Uiso 1 d . . . H9B H 0.872(3) 0.433(3) -0.242(4) 0.059(17) Uiso 1 d . . . H10A H 0.985(3) 0.432(3) -0.170(5) 0.08(2) Uiso 1 d . . . H10B H 0.975(4) 0.512(4) -0.115(5) 0.10(2) Uiso 1 d . . . H11 H 0.998(3) 0.364(3) -0.033(4) 0.048(15) Uiso 1 d . . . H13 H 1.002(3) 0.255(3) 0.070(4) 0.048(15) Uiso 1 d . . . H14 H 0.972(5) 0.203(4) 0.237(6) 0.12(3) Uiso 1 d . . . H15 H 0.897(3) 0.251(3) 0.358(4) 0.060(16) Uiso 1 d . . . H16 H 0.862(3) 0.363(3) 0.330(4) 0.054(16) Uiso 1 d . . . H19 H 0.866(4) 0.698(3) 0.117(5) 0.10(2) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0363(4) 0.0390(4) 0.0348(4) 0.0003(3) -0.0005(3) 0.0003(3) O1 0.049(2) 0.0434(19) 0.062(2) 0.0116(16) -0.0072(18) -0.0068(16) O2 0.049(2) 0.0459(19) 0.0420(19) -0.0037(15) -0.0057(16) 0.0096(17) O3 0.063(2) 0.047(2) 0.072(3) -0.0005(18) 0.017(2) -0.0043(19) O4 0.046(2) 0.048(2) 0.068(2) -0.0050(18) 0.0014(19) 0.0041(17) N1 0.047(3) 0.047(2) 0.033(2) 0.0011(18) -0.0001(19) 0.002(2) N2 0.035(2) 0.046(2) 0.045(2) -0.009(2) -0.004(2) -0.0044(19) C1 0.048(3) 0.037(3) 0.051(3) -0.008(2) 0.004(2) -0.002(2) C2 0.063(4) 0.045(3) 0.059(3) -0.003(3) 0.001(3) -0.013(3) C3 0.054(4) 0.066(4) 0.092(5) -0.012(4) 0.015(4) -0.013(3) C4 0.045(4) 0.081(5) 0.105(6) -0.010(4) -0.007(4) -0.006(3) C5 0.046(3) 0.070(4) 0.069(4) -0.003(3) -0.009(3) -0.001(3) C6 0.043(3) 0.049(3) 0.046(3) -0.005(2) -0.002(2) 0.001(2) C7 0.048(3) 0.052(3) 0.043(3) -0.001(2) -0.014(3) 0.006(3) C8 0.057(3) 0.064(3) 0.043(3) 0.010(3) 0.005(3) -0.004(3) C9 0.058(4) 0.066(4) 0.048(3) -0.001(3) 0.011(3) -0.011(3) C10 0.048(3) 0.061(4) 0.055(3) -0.005(3) 0.009(3) -0.003(3) C11 0.033(3) 0.055(4) 0.068(4) -0.018(3) 0.001(3) 0.000(3) C12 0.045(3) 0.041(3) 0.055(3) -0.001(2) -0.010(3) 0.002(2) C13 0.072(5) 0.058(4) 0.105(6) -0.017(4) -0.009(4) 0.015(3) C14 0.111(6) 0.052(4) 0.101(6) 0.020(4) -0.031(5) 0.011(4) C15 0.093(5) 0.064(4) 0.078(5) 0.021(4) -0.017(4) -0.008(4) C16 0.071(4) 0.060(4) 0.052(4) 0.011(3) -0.018(3) -0.002(3) C17 0.039(3) 0.046(3) 0.054(3) -0.004(2) -0.016(2) -0.001(2) C18 0.059(4) 0.043(3) 0.055(3) -0.001(3) -0.001(3) -0.001(3) C19 0.075(4) 0.042(3) 0.087(5) -0.006(3) 0.006(4) 0.003(3) C20 0.247(14) 0.054(5) 0.265(15) -0.009(6) -0.150(12) 0.029(7) C21 0.227(11) 0.069(5) 0.138(8) -0.029(5) 0.049(8) -0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 1.872(3) . ? Mn1 O1 1.899(3) . ? Mn1 N1 1.990(4) . ? Mn1 O4 2.099(4) . ? Mn1 N2 2.128(4) . ? Mn1 O3 2.304(4) . ? Mn1 C18 2.535(5) . ? O1 C1 1.323(6) . ? O2 C17 1.347(6) . ? O3 C18 1.261(6) . ? O4 C18 1.254(6) . ? N1 C7 1.295(6) . ? N1 C8 1.477(6) . ? N2 C11 1.284(7) . ? N2 C10 1.471(7) . ? C1 C2 1.401(7) . ? C1 C6 1.400(7) . ? C2 C3 1.367(8) . ? C3 C4 1.369(10) . ? C4 C5 1.368(9) . ? C5 C6 1.413(7) . ? C6 C7 1.434(7) . ? C8 C9 1.524(8) . ? C9 C10 1.506(8) . ? C11 C12 1.439(8) . ? C12 C13 1.401(8) . ? C12 C17 1.411(7) . ? C13 C14 1.364(10) . ? C14 C15 1.369(10) . ? C15 C16 1.369(9) . ? C16 C17 1.379(7) . ? C18 C19 1.529(7) . ? C19 C21 1.488(10) . ? C19 C20 1.497(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O1 89.73(15) . . ? O2 Mn1 N1 176.21(15) . . ? O1 Mn1 N1 89.59(15) . . ? O2 Mn1 O4 93.98(14) . . ? O1 Mn1 O4 153.03(15) . . ? N1 Mn1 O4 88.32(15) . . ? O2 Mn1 N2 87.51(15) . . ? O1 Mn1 N2 112.59(15) . . ? N1 Mn1 N2 89.31(16) . . ? O4 Mn1 N2 94.28(14) . . ? O2 Mn1 O3 94.30(14) . . ? O1 Mn1 O3 93.90(15) . . ? N1 Mn1 O3 89.47(15) . . ? O4 Mn1 O3 59.21(13) . . ? N2 Mn1 O3 153.48(14) . . ? O2 Mn1 C18 95.93(16) . . ? O1 Mn1 C18 123.51(17) . . ? N1 Mn1 C18 87.56(16) . . ? O4 Mn1 C18 29.53(14) . . ? N2 Mn1 C18 123.76(17) . . ? O3 Mn1 C18 29.72(14) . . ? C1 O1 Mn1 125.4(3) . . ? C17 O2 Mn1 121.1(3) . . ? C18 O3 Mn1 85.3(3) . . ? C18 O4 Mn1 94.8(3) . . ? C7 N1 C8 118.0(4) . . ? C7 N1 Mn1 123.4(3) . . ? C8 N1 Mn1 118.6(3) . . ? C11 N2 C10 118.9(5) . . ? C11 N2 Mn1 118.9(4) . . ? C10 N2 Mn1 122.2(4) . . ? O1 C1 C2 119.6(5) . . ? O1 C1 C6 122.5(4) . . ? C2 C1 C6 117.9(5) . . ? C3 C2 C1 120.9(6) . . ? C2 C3 C4 121.9(6) . . ? C5 C4 C3 118.7(6) . . ? C4 C5 C6 121.3(6) . . ? C1 C6 C5 119.3(5) . . ? C1 C6 C7 122.4(5) . . ? C5 C6 C7 118.0(5) . . ? N1 C7 C6 125.4(5) . . ? N1 C8 C9 110.8(5) . . ? C10 C9 C8 114.2(5) . . ? N2 C10 C9 113.0(4) . . ? N2 C11 C12 126.4(5) . . ? C13 C12 C17 117.4(6) . . ? C13 C12 C11 119.8(6) . . ? C17 C12 C11 122.7(5) . . ? C14 C13 C12 121.5(7) . . ? C13 C14 C15 120.3(7) . . ? C16 C15 C14 119.6(7) . . ? C15 C16 C17 121.5(7) . . ? O2 C17 C16 120.0(5) . . ? O2 C17 C12 120.5(5) . . ? C16 C17 C12 119.5(5) . . ? O4 C18 O3 120.5(5) . . ? O4 C18 C19 119.8(5) . . ? O3 C18 C19 119.7(5) . . ? O4 C18 Mn1 55.6(3) . . ? O3 C18 Mn1 65.0(3) . . ? C19 C18 Mn1 173.1(4) . . ? C21 C19 C20 111.5(8) . . ? C21 C19 C18 111.8(6) . . ? C20 C19 C18 108.0(6) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.639 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.080 #=END data_Figure9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Mn N4 O9' _chemical_formula_weight 488.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.014(2) _cell_length_b 12.086(2) _cell_length_c 13.370(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.71(2) _cell_angle_gamma 90.00 _cell_volume 2040.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7899 _exptl_absorpt_correction_T_max 0.9013 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3742 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.1437 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3573 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3573 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1612 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.009 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.90713(6) 0.06858(6) 0.29329(7) 0.0253(2) Uani 1 d . . . O1 O 0.8674(3) -0.0742(3) 0.3171(3) 0.0309(8) Uani 1 d . . . O2 O 1.0523(3) 0.0307(3) 0.3627(3) 0.0321(9) Uani 1 d . . . O3 O 0.3961(4) -0.2270(6) 0.0907(6) 0.103(2) Uani 1 d . . . O4 O 0.4745(5) -0.3832(5) 0.1492(5) 0.097(2) Uani 1 d . . . O5 O 1.4921(3) 0.2527(4) 0.6003(5) 0.0737(17) Uani 1 d . . . O6 O 1.3951(3) 0.3991(4) 0.5565(4) 0.0592(14) Uani 1 d . . . O7 O 0.9214(4) 0.1316(4) 0.4653(4) 0.0455(12) Uani 1 d . . . O8 O 0.8856(3) 0.0297(3) 0.1300(3) 0.0369(10) Uani 1 d . . . O9 O 0.9525(5) 0.1640(4) 0.0649(5) 0.0775(17) Uani 1 d . . . N1 N 0.7591(3) 0.1208(3) 0.2356(4) 0.0290(11) Uani 1 d . . . N2 N 0.9374(3) 0.2253(3) 0.2786(4) 0.0259(10) Uani 1 d . . . N3 N 0.4754(5) -0.2825(6) 0.1390(5) 0.0687(19) Uani 1 d . . . N4 N 1.4060(4) 0.2979(5) 0.5565(4) 0.0445(13) Uani 1 d . . . C1 C 0.6776(4) 0.0605(5) 0.2077(5) 0.0363(14) Uani 1 d . . . C2 C 0.7505(5) 0.2450(5) 0.2276(6) 0.0417(17) Uani 1 d . . . C3 C 0.8409(4) 0.2867(5) 0.2055(5) 0.0349(15) Uani 1 d . . . C4 C 1.0277(4) 0.2712(4) 0.3252(5) 0.0290(13) Uani 1 d . . . C5 C 0.7734(4) -0.1191(4) 0.2766(4) 0.0273(12) Uani 1 d . . . C6 C 0.6790(4) -0.0586(5) 0.2206(4) 0.0315(12) Uani 1 d . . . C7 C 0.5814(5) -0.1142(5) 0.1771(5) 0.0402(16) Uani 1 d . . . C8 C 0.5783(5) -0.2253(5) 0.1876(5) 0.0424(16) Uani 1 d . . . C9 C 0.6705(5) -0.2867(5) 0.2427(5) 0.0394(16) Uani 1 d . . . C10 C 0.7663(5) -0.2355(4) 0.2882(5) 0.0339(14) Uani 1 d . . . C11 C 1.2166(5) 0.2786(5) 0.4439(5) 0.0295(13) Uani 1 d . . . C12 C 1.1252(4) 0.2148(4) 0.3931(4) 0.0250(12) Uani 1 d . . . C13 C 1.1339(4) 0.0980(4) 0.4073(4) 0.0253(12) Uani 1 d . . . C14 C 1.2356(4) 0.0505(4) 0.4693(5) 0.0328(13) Uani 1 d . . . C15 C 1.3231(4) 0.1153(5) 0.5155(5) 0.0355(15) Uani 1 d . . . C16 C 1.3127(4) 0.2299(5) 0.5041(4) 0.0317(13) Uani 1 d . . . C17 C 0.8992(5) 0.0769(5) 0.0527(5) 0.0442(16) Uani 1 d . . . C18 C 0.8505(9) 0.0233(8) -0.0592(7) 0.075(3) Uani 1 d . . . H1 H 0.606(5) 0.099(6) 0.180(5) 0.07(2) Uiso 1 d . . . H2A H 0.663(5) 0.264(5) 0.159(4) 0.044(16) Uiso 1 d . . . H2B H 0.750(6) 0.270(6) 0.294(6) 0.07(3) Uiso 1 d . . . H3A H 0.850(4) 0.363(4) 0.222(4) 0.030(14) Uiso 1 d . . . H3B H 0.832(4) 0.268(4) 0.130(4) 0.025(15) Uiso 1 d . . . H4 H 1.031(4) 0.342(4) 0.318(4) 0.018(13) Uiso 1 d . . . H7 H 0.528(4) -0.068(5) 0.150(4) 0.030(15) Uiso 1 d . . . H7A H 0.945(6) 0.095(7) 0.519(7) 0.08(3) Uiso 1 d . . . H7B H 0.945(6) 0.175(6) 0.512(6) 0.06(3) Uiso 1 d . . . H9 H 0.671(5) -0.354(5) 0.251(5) 0.05(2) Uiso 1 d . . . H10 H 0.845(5) -0.277(5) 0.333(5) 0.052(18) Uiso 1 d . . . H11 H 1.205(4) 0.339(4) 0.438(4) 0.016(14) Uiso 1 d . . . H14 H 1.252(4) -0.028(5) 0.488(5) 0.046(17) Uiso 1 d . . . H15 H 1.382(5) 0.086(5) 0.553(5) 0.06(2) Uiso 1 d . . . H18B H 0.862(6) 0.055(7) -0.116(6) 0.08(3) Uiso 1 d . . . H18A H 0.772(7) 0.019(7) -0.078(7) 0.10(3) Uiso 1 d . . . H18C H 0.875(7) -0.066(9) -0.044(7) 0.13(3) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0204(4) 0.0124(3) 0.0353(4) 0.0019(4) 0.0048(3) 0.0001(4) O1 0.0258(18) 0.0189(17) 0.040(2) 0.0059(17) 0.0066(16) -0.0008(17) O2 0.0226(19) 0.0128(16) 0.053(3) -0.0006(17) 0.0091(19) 0.0013(15) O3 0.038(3) 0.093(5) 0.146(6) -0.007(4) 0.010(4) -0.029(3) O4 0.082(4) 0.058(3) 0.129(5) -0.008(3) 0.027(4) -0.047(3) O5 0.022(2) 0.063(3) 0.105(4) -0.004(3) -0.002(3) -0.008(2) O6 0.050(3) 0.039(3) 0.071(3) -0.011(2) 0.010(3) -0.021(2) O7 0.064(3) 0.032(2) 0.035(3) 0.000(2) 0.016(2) -0.001(2) O8 0.052(2) 0.0205(19) 0.034(2) 0.0027(17) 0.015(2) -0.0001(18) O9 0.121(5) 0.030(3) 0.098(4) -0.004(3) 0.062(4) -0.025(3) N1 0.027(2) 0.013(2) 0.042(3) 0.002(2) 0.011(2) 0.0002(19) N2 0.023(2) 0.014(2) 0.036(3) 0.0020(19) 0.007(2) 0.0032(17) N3 0.047(4) 0.071(5) 0.076(5) -0.007(4) 0.015(3) -0.032(3) N4 0.032(3) 0.051(3) 0.044(3) -0.006(3) 0.009(3) -0.014(3) C1 0.025(3) 0.031(3) 0.048(4) -0.001(3) 0.010(3) 0.000(3) C2 0.028(3) 0.018(3) 0.070(5) 0.004(3) 0.012(3) 0.009(3) C3 0.028(3) 0.020(3) 0.043(4) 0.004(3) 0.002(3) 0.003(2) C4 0.031(3) 0.011(2) 0.045(4) -0.003(2) 0.016(3) -0.001(2) C5 0.029(3) 0.020(2) 0.035(3) -0.001(2) 0.015(3) -0.005(2) C6 0.030(3) 0.027(3) 0.036(3) -0.002(3) 0.013(2) 0.000(3) C7 0.025(3) 0.042(3) 0.049(4) -0.001(3) 0.011(3) -0.005(3) C8 0.046(4) 0.030(3) 0.049(4) -0.009(3) 0.019(3) -0.026(3) C9 0.050(4) 0.028(3) 0.044(4) -0.005(3) 0.023(3) -0.018(3) C10 0.042(3) 0.020(3) 0.044(4) 0.002(3) 0.022(3) -0.004(3) C11 0.036(3) 0.020(3) 0.034(3) -0.006(3) 0.016(3) -0.002(3) C12 0.025(3) 0.019(3) 0.028(3) -0.002(2) 0.009(2) -0.002(2) C13 0.023(3) 0.022(3) 0.026(3) 0.001(2) 0.006(2) -0.003(2) C14 0.029(3) 0.024(3) 0.041(3) 0.000(3) 0.010(3) 0.004(2) C15 0.018(3) 0.041(3) 0.036(3) 0.003(3) 0.000(3) 0.004(3) C16 0.023(3) 0.037(3) 0.026(3) -0.004(3) 0.003(2) -0.008(2) C17 0.065(4) 0.022(3) 0.048(4) 0.003(3) 0.027(3) 0.009(3) C18 0.114(8) 0.072(6) 0.041(5) 0.005(4) 0.035(5) -0.011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 1.882(4) . ? Mn1 O2 1.890(3) . ? Mn1 N2 1.969(4) . ? Mn1 N1 1.977(4) . ? Mn1 O8 2.123(4) . ? Mn1 O7 2.347(5) . ? O1 C5 1.306(6) . ? O2 C13 1.316(6) . ? O3 N3 1.216(8) . ? O4 N3 1.225(8) . ? O5 N4 1.218(6) . ? O6 N4 1.233(7) . ? O8 C17 1.265(7) . ? O9 C17 1.260(7) . ? N1 C1 1.267(7) . ? N1 C2 1.506(6) . ? N2 C4 1.270(6) . ? N2 C3 1.479(6) . ? N3 C8 1.472(8) . ? N4 C16 1.442(7) . ? C1 C6 1.449(8) . ? C2 C3 1.507(9) . ? C4 C12 1.442(7) . ? C5 C6 1.409(7) . ? C5 C10 1.424(7) . ? C6 C7 1.404(7) . ? C7 C8 1.354(8) . ? C8 C9 1.392(9) . ? C9 C10 1.359(8) . ? C11 C16 1.367(8) . ? C11 C12 1.394(7) . ? C12 C13 1.423(7) . ? C13 C14 1.422(7) . ? C14 C15 1.357(8) . ? C15 C16 1.394(8) . ? C17 C18 1.497(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 91.67(14) . . ? O1 Mn1 N2 172.31(17) . . ? O2 Mn1 N2 92.81(16) . . ? O1 Mn1 N1 91.25(15) . . ? O2 Mn1 N1 173.09(17) . . ? N2 Mn1 N1 83.63(16) . . ? O1 Mn1 O8 92.86(15) . . ? O2 Mn1 O8 95.39(16) . . ? N2 Mn1 O8 92.93(17) . . ? N1 Mn1 O8 90.71(18) . . ? O1 Mn1 O7 92.17(17) . . ? O2 Mn1 O7 88.94(17) . . ? N2 Mn1 O7 81.68(18) . . ? N1 Mn1 O7 84.69(19) . . ? O8 Mn1 O7 173.26(16) . . ? C5 O1 Mn1 129.0(3) . . ? C13 O2 Mn1 127.7(3) . . ? C17 O8 Mn1 137.3(4) . . ? C1 N1 C2 121.2(5) . . ? C1 N1 Mn1 126.2(4) . . ? C2 N1 Mn1 112.6(3) . . ? C4 N2 C3 122.4(4) . . ? C4 N2 Mn1 125.7(3) . . ? C3 N2 Mn1 111.9(3) . . ? O3 N3 O4 123.8(7) . . ? O3 N3 C8 118.0(6) . . ? O4 N3 C8 118.1(7) . . ? O5 N4 O6 122.7(5) . . ? O5 N4 C16 118.6(5) . . ? O6 N4 C16 118.7(5) . . ? N1 C1 C6 124.9(5) . . ? N1 C2 C3 107.3(5) . . ? N2 C3 C2 108.0(5) . . ? N2 C4 C12 124.9(5) . . ? O1 C5 C6 123.4(5) . . ? O1 C5 C10 118.1(5) . . ? C6 C5 C10 118.5(5) . . ? C7 C6 C5 119.6(5) . . ? C7 C6 C1 117.8(5) . . ? C5 C6 C1 122.7(5) . . ? C8 C7 C6 120.1(6) . . ? C7 C8 C9 121.3(5) . . ? C7 C8 N3 119.3(6) . . ? C9 C8 N3 119.4(5) . . ? C10 C9 C8 120.3(5) . . ? C9 C10 C5 120.3(6) . . ? C16 C11 C12 120.8(5) . . ? C11 C12 C13 118.4(5) . . ? C11 C12 C4 117.7(5) . . ? C13 C12 C4 123.8(5) . . ? O2 C13 C14 118.0(4) . . ? O2 C13 C12 123.0(4) . . ? C14 C13 C12 119.0(5) . . ? C15 C14 C13 120.8(5) . . ? C14 C15 C16 119.6(5) . . ? C11 C16 C15 121.4(5) . . ? C11 C16 N4 119.6(5) . . ? C15 C16 N4 118.9(5) . . ? O9 C17 O8 124.2(6) . . ? O9 C17 C18 118.6(7) . . ? O8 C17 C18 117.2(6) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.434 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.095 #=END data_Figure10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H59 Br4 Mn2 N13 O19' _chemical_formula_weight 1563.61 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.592(2) _cell_length_b 12.103(3) _cell_length_c 20.266(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.11(2) _cell_angle_gamma 90.00 _cell_volume 3086.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1572 _exptl_absorpt_coefficient_mu 3.079 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5133 _exptl_absorpt_correction_T_max 0.5780 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5398 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 378.2902 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5398 _reflns_number_gt 1291 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0160P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5398 _refine_ls_number_parameters 418 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.4375 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 0.744 _refine_ls_restrained_S_all 0.744 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.004 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.40050(8) 0.04459(10) 1.00321(6) 0.0359(3) Uani 1 d . . . O1 O 0.2946(4) 0.0427(5) 1.0698(2) 0.0444(15) Uani 1 d . . . O2 O 0.6863(4) -0.1374(4) 1.0563(3) 0.0451(16) Uani 1 d . . . O3 O 0.5097(3) 0.0397(4) 0.9477(2) 0.0363(14) Uani 1 d . . . O4 O 0.0538(4) -0.3044(5) 1.2303(3) 0.074(2) Uani 1 d . . . O5 O 0.0878(5) -0.4012(6) 1.1449(3) 0.084(2) Uani 1 d . . . O6 O 0.5541(5) -0.4970(6) 1.2514(4) 0.100(3) Uani 1 d . . . O7 O 0.4578(6) -0.5489(5) 1.1674(3) 0.089(2) Uani 1 d . . . N1 N 0.3258(4) -0.0831(5) 0.9598(3) 0.0330(17) Uani 1 d . . . N2 N 0.5445(4) -0.1839(5) 0.9557(3) 0.0371(17) Uani 1 d . . . N3 N 0.0951(6) -0.3165(7) 1.1771(4) 0.059(2) Uani 1 d . . . N4 N 0.5246(6) -0.4859(6) 1.1921(5) 0.069(3) Uani 1 d . . . Br1 Br 0.21485(8) 0.09657(8) 1.20321(5) 0.0703(3) Uani 1 d . . . Br2 Br 0.81307(7) -0.17705(9) 1.18225(5) 0.0690(3) Uani 1 d . . . C1 C 0.2521(5) -0.0429(7) 1.0938(4) 0.031(2) Uani 1 d . . . C2 C 0.2060(5) -0.0375(7) 1.1564(4) 0.040(2) Uani 1 d . . . C3 C 0.1582(6) -0.1274(7) 1.1854(4) 0.049(3) Uani 1 d . . . H3 H 0.1341 -0.1236 1.2282 0.059 Uiso 1 calc R . . C4 C 0.1481(6) -0.2189(7) 1.1499(4) 0.043(2) Uani 1 d . . . C5 C 0.1899(5) -0.2348(7) 1.0874(4) 0.047(2) Uani 1 d . . . H5 H 0.1843 -0.3020 1.0653 0.056 Uiso 1 calc R . . C6 C 0.2402(6) -0.1440(8) 1.0605(4) 0.041(2) Uani 1 d . . . C7 C 0.2697(5) -0.1504(6) 0.9931(4) 0.041(2) Uani 1 d . . . H7 H 0.2448 -0.2122 0.9701 0.049 Uiso 1 calc R . . C8 C 0.3326(6) -0.1009(6) 0.8859(3) 0.039(2) Uani 1 d . . . H8A H 0.2614 -0.1104 0.8668 0.047 Uiso 1 calc R . . H8B H 0.3630 -0.0355 0.8663 0.047 Uiso 1 calc R . . C9 C 0.3970(5) -0.1973(6) 0.8693(4) 0.043(2) Uani 1 d . . . H9A H 0.3864 -0.2120 0.8225 0.051 Uiso 1 calc R . . H9B H 0.3705 -0.2607 0.8929 0.051 Uiso 1 calc R . . C10 C 0.5162(6) -0.1875(7) 0.8848(3) 0.043(2) Uani 1 d . . . H10A H 0.5518 -0.2500 0.8653 0.051 Uiso 1 calc R . . H10B H 0.5423 -0.1210 0.8642 0.051 Uiso 1 calc R . . C11 C 0.5302(5) -0.2699(7) 0.9891(4) 0.033(2) Uani 1 d . . . H11 H 0.4940 -0.3276 0.9679 0.039 Uiso 1 calc R . . C12 C 0.5647(6) -0.2880(7) 1.0576(4) 0.047(2) Uani 1 d . . . C13 C 0.6479(6) -0.2215(7) 1.0848(4) 0.043(2) Uani 1 d . . . C14 C 0.6926(5) -0.2557(7) 1.1473(4) 0.035(2) Uani 1 d . . . C15 C 0.6497(7) -0.3420(7) 1.1828(4) 0.055(3) Uani 1 d . . . H15 H 0.6775 -0.3603 1.2245 0.066 Uiso 1 calc R . . C16 C 0.5662(6) -0.3990(7) 1.1554(5) 0.050(3) Uani 1 d . . . C17 C 0.5265(7) -0.3755(7) 1.0926(4) 0.054(3) Uani 1 d . . . H17 H 0.4731 -0.4196 1.0738 0.064 Uiso 1 calc R . . O21 O 0.6358(8) -0.2018(8) 1.3718(5) 0.175(4) Uani 1 d D . . N21 N 0.5485(7) -0.1233(7) 1.2856(4) 0.079(3) Uani 1 d D . . C21 C 0.5593(9) -0.1994(10) 1.3296(6) 0.109(4) Uani 1 d D . . H21 H 0.5085 -0.2551 1.3305 0.131 Uiso 1 calc R . . C22 C 0.6245(8) -0.0310(8) 1.2858(6) 0.115(5) Uani 1 d D . . H22A H 0.6587 -0.0246 1.3288 0.172 Uiso 1 calc R . . H22B H 0.5874 0.0363 1.2752 0.172 Uiso 1 calc R . . H22C H 0.6770 -0.0445 1.2536 0.172 Uiso 1 calc R . . C23 C 0.4591(9) -0.1321(10) 1.2413(6) 0.149(6) Uani 1 d D . . H23A H 0.4759 -0.1002 1.1995 0.224 Uiso 1 calc R . . H23B H 0.4000 -0.0934 1.2590 0.224 Uiso 1 calc R . . H23C H 0.4409 -0.2085 1.2352 0.224 Uiso 1 calc R . . O31 O 0.8245(6) -0.0557(7) 1.4997(4) 0.119(3) Uani 1 d D . . N31 N 0.6970(8) 0.0698(8) 1.5091(6) 0.098(4) Uani 1 d D . . C31 C 0.7462(10) -0.0080(10) 1.4789(6) 0.110(5) Uani 1 d D . . H31 H 0.7187 -0.0290 1.4375 0.132 Uiso 1 calc R . . C32 C 0.7276(10) 0.1062(11) 1.5723(6) 0.150(6) Uani 1 d D . . H32A H 0.6793 0.0775 1.6036 0.225 Uiso 1 calc R . . H32B H 0.7262 0.1855 1.5734 0.225 Uiso 1 calc R . . H32C H 0.7982 0.0806 1.5832 0.225 Uiso 1 calc R . . C33 C 0.6040(10) 0.1138(12) 1.4766(7) 0.208(9) Uani 1 d D . . H33A H 0.6181 0.1875 1.4617 0.313 Uiso 1 calc R . . H33B H 0.5470 0.1153 1.5067 0.313 Uiso 1 calc R . . H33C H 0.5843 0.0682 1.4393 0.313 Uiso 1 calc R . . O41 O 0.978(2) -0.160(2) 0.9614(11) 0.189(12) Uani 0.50 d PD . . N41 N 1.0000 0.0000 1.0000 0.078(4) Uani 1 d SD . . C41 C 0.9558(19) -0.099(2) 1.0119(14) 0.123(12) Uani 0.50 d PD . . H41 H 0.9177 -0.1194 1.0484 0.147 Uiso 0.50 calc PR . . C42 C 1.0505(17) 0.013(3) 0.9383(10) 0.106(11) Uani 0.50 d PD . . H42A H 1.1253 -0.0011 0.9445 0.159 Uiso 0.50 calc PR . . H42B H 1.0394 0.0863 0.9222 0.159 Uiso 0.50 calc PR . . H42C H 1.0206 -0.0393 0.9070 0.159 Uiso 0.50 calc PR . . C43 C 0.975(3) 0.077(2) 1.0538(16) 0.17(2) Uani 0.50 d PD . . H43A H 0.9572 0.0352 1.0923 0.261 Uiso 0.50 calc PR . . H43B H 0.9152 0.1219 1.0402 0.261 Uiso 0.50 calc PR . . H43C H 1.0351 0.1228 1.0640 0.261 Uiso 0.50 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0376(7) 0.0407(8) 0.0295(8) 0.0028(7) 0.0023(6) -0.0034(7) O1 0.043(3) 0.062(4) 0.029(3) -0.007(3) 0.009(3) -0.001(3) O2 0.042(3) 0.045(4) 0.047(4) -0.001(3) -0.004(3) 0.002(3) O3 0.035(3) 0.045(3) 0.029(3) -0.004(3) 0.006(3) 0.004(3) O4 0.075(4) 0.096(5) 0.053(4) 0.019(4) 0.030(3) 0.001(4) O5 0.117(5) 0.064(5) 0.075(5) -0.009(4) 0.046(4) -0.030(5) O6 0.089(5) 0.121(7) 0.090(6) 0.057(5) 0.000(5) -0.010(5) O7 0.129(6) 0.050(5) 0.089(6) 0.009(4) 0.026(5) -0.029(5) N1 0.030(4) 0.035(4) 0.035(4) -0.012(4) 0.006(3) 0.001(3) N2 0.035(4) 0.048(5) 0.027(4) 0.002(4) -0.002(3) 0.003(4) N3 0.070(5) 0.062(6) 0.045(6) -0.007(5) 0.013(5) 0.013(5) N4 0.075(6) 0.034(6) 0.098(8) 0.024(6) 0.012(6) -0.003(5) Br1 0.0787(7) 0.0742(8) 0.0597(7) -0.0266(6) 0.0240(6) -0.0131(6) Br2 0.0603(6) 0.0908(8) 0.0545(6) 0.0116(6) -0.0174(5) -0.0061(6) C1 0.014(4) 0.044(6) 0.035(6) 0.008(5) 0.003(4) -0.016(4) C2 0.022(4) 0.062(6) 0.037(6) -0.003(5) 0.004(4) 0.003(5) C3 0.052(6) 0.067(7) 0.027(5) -0.005(5) 0.009(5) 0.000(5) C4 0.037(5) 0.045(6) 0.048(6) 0.017(5) 0.017(5) -0.012(5) C5 0.032(5) 0.054(6) 0.053(7) -0.009(5) 0.007(5) -0.003(5) C6 0.032(5) 0.067(7) 0.023(5) 0.011(5) -0.003(4) -0.014(5) C7 0.034(5) 0.041(6) 0.047(6) 0.004(5) -0.003(5) -0.018(5) C8 0.044(5) 0.046(6) 0.028(5) 0.003(5) 0.003(4) -0.016(5) C9 0.052(5) 0.057(6) 0.020(5) 0.004(5) 0.009(4) 0.001(5) C10 0.054(5) 0.049(6) 0.024(5) -0.004(5) -0.003(4) 0.000(5) C11 0.037(5) 0.039(6) 0.023(5) 0.005(4) 0.009(4) -0.006(4) C12 0.057(6) 0.028(6) 0.054(7) 0.016(5) 0.005(5) -0.001(5) C13 0.040(5) 0.030(6) 0.057(7) 0.013(5) -0.001(5) 0.006(5) C14 0.024(4) 0.052(6) 0.029(5) -0.015(5) 0.000(4) 0.012(4) C15 0.070(6) 0.057(7) 0.039(6) 0.039(5) 0.025(5) 0.017(6) C16 0.042(6) 0.039(6) 0.070(7) 0.004(6) 0.011(5) -0.020(5) C17 0.054(6) 0.059(7) 0.047(6) -0.018(6) -0.004(5) 0.006(5) O21 0.187(9) 0.174(9) 0.160(9) 0.022(8) -0.047(8) 0.044(8) N21 0.081(6) 0.088(8) 0.069(7) 0.028(6) 0.001(5) 0.025(6) C21 0.104(10) 0.127(12) 0.095(11) 0.006(9) -0.019(8) 0.008(9) C22 0.124(10) 0.092(10) 0.135(12) 0.043(9) 0.081(8) 0.002(8) C23 0.135(11) 0.166(14) 0.143(13) -0.013(10) -0.048(10) 0.067(10) O31 0.113(6) 0.119(7) 0.122(7) 0.017(6) -0.014(6) 0.039(6) N31 0.087(7) 0.066(8) 0.144(11) -0.011(7) 0.033(7) 0.014(6) C31 0.137(12) 0.079(10) 0.110(12) 0.056(9) -0.038(10) -0.022(9) C32 0.159(13) 0.181(15) 0.114(13) -0.027(12) 0.050(11) -0.050(11) C33 0.140(12) 0.28(2) 0.207(19) 0.049(16) 0.000(13) 0.081(15) O41 0.26(3) 0.22(3) 0.097(17) -0.046(19) 0.063(18) -0.06(2) N41 0.048(9) 0.077(11) 0.109(13) -0.008(10) -0.008(8) 0.007(8) C41 0.073(18) 0.20(4) 0.09(3) 0.02(3) 0.000(18) -0.03(2) C42 0.056(14) 0.19(3) 0.071(19) 0.07(2) 0.024(14) 0.07(2) C43 0.19(4) 0.06(2) 0.27(6) 0.00(3) -0.07(4) 0.06(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 1.797(4) 3_657 ? Mn1 O3 1.809(5) . ? Mn1 O1 1.933(5) . ? Mn1 O2 1.952(5) 3_657 ? Mn1 N2 1.993(6) 3_657 ? Mn1 N1 1.997(6) . ? Mn1 Mn1 2.736(2) 3_657 ? O1 C1 1.270(8) . ? O2 C13 1.275(9) . ? O2 Mn1 1.952(5) 3_657 ? O3 Mn1 1.797(4) 3_657 ? O4 N3 1.224(8) . ? O5 N3 1.217(8) . ? O6 N4 1.252(9) . ? O7 N4 1.229(8) . ? N1 C7 1.285(9) . ? N1 C8 1.518(9) . ? N2 C11 1.258(8) . ? N2 C10 1.469(8) . ? N2 Mn1 1.993(6) 3_657 ? N3 C4 1.473(10) . ? N4 C16 1.401(11) . ? Br1 C2 1.882(8) . ? Br2 C14 1.905(7) . ? C1 C6 1.403(11) . ? C1 C2 1.416(10) . ? C2 C3 1.384(10) . ? C3 C4 1.325(10) . ? C4 C5 1.403(10) . ? C5 C6 1.390(10) . ? C6 C7 1.430(10) . ? C8 C9 1.466(9) . ? C9 C10 1.527(8) . ? C11 C12 1.457(10) . ? C12 C17 1.371(10) . ? C12 C13 1.417(10) . ? C13 C14 1.428(10) . ? C14 C15 1.389(10) . ? C15 C16 1.359(10) . ? C16 C17 1.379(11) . ? O21 C21 1.265(10) . ? N21 C21 1.285(11) . ? N21 C23 1.419(10) . ? N21 C22 1.471(11) . ? O31 C31 1.206(11) . ? N31 C31 1.294(13) . ? N31 C32 1.394(12) . ? N31 C33 1.426(12) . ? O41 C41 1.30(2) . ? N41 C41 1.35(2) . ? N41 C42 1.431(19) . ? N41 C43 1.48(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O3 81.3(2) 3_657 . ? O3 Mn1 O1 92.5(2) 3_657 . ? O3 Mn1 O1 173.6(2) . . ? O3 Mn1 O2 174.5(2) 3_657 3_657 ? O3 Mn1 O2 93.2(2) . 3_657 ? O1 Mn1 O2 93.1(2) . 3_657 ? O3 Mn1 N2 92.7(2) 3_657 3_657 ? O3 Mn1 N2 91.6(2) . 3_657 ? O1 Mn1 N2 87.5(2) . 3_657 ? O2 Mn1 N2 87.1(2) 3_657 3_657 ? O3 Mn1 N1 94.7(2) 3_657 . ? O3 Mn1 N1 93.3(2) . . ? O1 Mn1 N1 88.4(2) . . ? O2 Mn1 N1 86.0(2) 3_657 . ? N2 Mn1 N1 171.7(2) 3_657 . ? O3 Mn1 Mn1 40.82(15) 3_657 3_657 ? O3 Mn1 Mn1 40.49(14) . 3_657 ? O1 Mn1 Mn1 133.26(16) . 3_657 ? O2 Mn1 Mn1 133.66(18) 3_657 3_657 ? N2 Mn1 Mn1 92.81(17) 3_657 3_657 ? N1 Mn1 Mn1 95.24(17) . 3_657 ? C1 O1 Mn1 126.0(5) . . ? C13 O2 Mn1 121.8(5) . 3_657 ? Mn1 O3 Mn1 98.7(2) 3_657 . ? C7 N1 C8 118.7(6) . . ? C7 N1 Mn1 121.2(6) . . ? C8 N1 Mn1 120.1(5) . . ? C11 N2 C10 117.8(7) . . ? C11 N2 Mn1 122.0(5) . 3_657 ? C10 N2 Mn1 120.1(5) . 3_657 ? O5 N3 O4 123.1(9) . . ? O5 N3 C4 120.1(8) . . ? O4 N3 C4 116.6(8) . . ? O7 N4 O6 120.0(9) . . ? O7 N4 C16 120.8(9) . . ? O6 N4 C16 119.2(9) . . ? O1 C1 C6 124.5(8) . . ? O1 C1 C2 119.9(8) . . ? C6 C1 C2 115.5(8) . . ? C3 C2 C1 123.0(8) . . ? C3 C2 Br1 118.8(6) . . ? C1 C2 Br1 118.2(7) . . ? C4 C3 C2 117.4(8) . . ? C3 C4 C5 125.0(8) . . ? C3 C4 N3 120.2(8) . . ? C5 C4 N3 114.7(8) . . ? C6 C5 C4 115.9(8) . . ? C5 C6 C1 122.9(8) . . ? C5 C6 C7 118.0(8) . . ? C1 C6 C7 118.6(8) . . ? N1 C7 C6 129.4(8) . . ? C9 C8 N1 113.0(6) . . ? C8 C9 C10 116.0(6) . . ? N2 C10 C9 113.9(6) . . ? N2 C11 C12 126.4(7) . . ? C17 C12 C13 120.4(8) . . ? C17 C12 C11 120.8(8) . . ? C13 C12 C11 118.4(8) . . ? O2 C13 C12 124.4(8) . . ? O2 C13 C14 119.4(8) . . ? C12 C13 C14 116.2(8) . . ? C15 C14 C13 121.9(7) . . ? C15 C14 Br2 120.2(6) . . ? C13 C14 Br2 117.9(6) . . ? C16 C15 C14 118.7(8) . . ? C15 C16 C17 121.3(9) . . ? C15 C16 N4 117.6(9) . . ? C17 C16 N4 121.1(9) . . ? C12 C17 C16 121.0(8) . . ? C21 N21 C23 116.6(10) . . ? C21 N21 C22 119.3(9) . . ? C23 N21 C22 124.0(9) . . ? O21 C21 N21 123.0(12) . . ? C31 N31 C32 122.9(12) . . ? C31 N31 C33 116.8(12) . . ? C32 N31 C33 120.1(11) . . ? O31 C31 N31 125.6(13) . . ? C41 N41 C42 116.8(14) . . ? C41 N41 C43 109.0(16) . . ? C42 N41 C43 133.9(15) . . ? O41 C41 N41 105(2) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.319 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.079