# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1835 data_dc06m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18.79 Cl Mn N2 O4.39' _chemical_formula_weight 447.87 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' 'Cl' 'Cl' 0.1484 0.1585 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.004(2) _cell_length_b 14.6410(9) _cell_length_c 13.6091(9) _cell_angle_alpha 90.00 _cell_angle_beta 117.987(2) _cell_angle_gamma 90.00 _cell_volume 4575.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3397 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Equant _exptl_crystal_colour Black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.721 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8296 _exptl_absorpt_correction_T_max 0.9630 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14554 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5553 _reflns_number_gt 2862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5553 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1201 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.2342 _refine_ls_wR_factor_gt 0.2032 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.23909(2) 0.25167(4) 0.84670(5) 0.0504(3) Uani 1 1 d . . . Cl1 Cl 0.24196(6) 0.31100(8) 0.68739(11) 0.0757(4) Uani 1 1 d . . . O1 O 0.22528(12) 0.3598(2) 0.9048(3) 0.0628(8) Uani 1 1 d . . . O2 O 0.16073(12) 0.2166(2) 0.7881(3) 0.0613(8) Uani 1 1 d . . . O3 O 0.1457(2) 0.5982(4) 0.8633(5) 0.149(2) Uani 1 1 d . . . O4 O -0.01304(15) 0.2176(3) 0.6236(4) 0.1052(14) Uani 1 1 d . . . O5 O 0.3851(7) -0.0968(11) 0.884(2) 0.220(14) Uani 0.395(17) 1 d P . . N1 N 0.32385(14) 0.2646(2) 0.9488(3) 0.0516(8) Uani 1 1 d . . . N2 N 0.26248(14) 0.1253(2) 0.8378(3) 0.0524(8) Uani 1 1 d . . . C1 C 0.26014(18) 0.4333(3) 0.9345(4) 0.0535(10) Uani 1 1 d . . . C2 C 0.2353(2) 0.5209(3) 0.9270(4) 0.0582(11) Uani 1 1 d . . . C3 C 0.2715(2) 0.5968(3) 0.9619(4) 0.0620(12) Uani 1 1 d . . . C4 C 0.3312(2) 0.5923(3) 1.0045(4) 0.0601(11) Uani 1 1 d . . . C5 C 0.35469(19) 0.5067(3) 1.0118(3) 0.0574(11) Uani 1 1 d . . . C6 C 0.32033(17) 0.4266(3) 0.9767(3) 0.0502(10) Uani 1 1 d . . . C7 C 0.34956(17) 0.3406(3) 0.9902(3) 0.0523(10) Uani 1 1 d . . . C8 C 0.35691(18) 0.1778(3) 0.9745(4) 0.0650(12) Uani 1 1 d . . . C9 C 0.32523(19) 0.1172(3) 0.8736(4) 0.0672(13) Uani 1 1 d . . . C10 C 0.22914(18) 0.0543(3) 0.8055(4) 0.0524(10) Uani 1 1 d . . . C11 C 0.16696(18) 0.0552(3) 0.7617(3) 0.0513(10) Uani 1 1 d . . . C12 C 0.1375(2) -0.0276(3) 0.7286(4) 0.0592(11) Uani 1 1 d . . . C13 C 0.0777(2) -0.0346(3) 0.6813(4) 0.0636(12) Uani 1 1 d . . . C14 C 0.04794(19) 0.0467(4) 0.6657(4) 0.0695(13) Uani 1 1 d . . . C15 C 0.07438(18) 0.1308(3) 0.6988(4) 0.0625(12) Uani 1 1 d . . . C16 C 0.13576(18) 0.1368(3) 0.7503(3) 0.0540(10) Uani 1 1 d . . . C17 C 0.1691(3) 0.5264(4) 0.8777(5) 0.0917(19) Uani 1 1 d . . . C18 C 0.3677(2) 0.6759(3) 1.0416(5) 0.0814(16) Uani 1 1 d . . . C19 C 0.0482(2) -0.1262(4) 0.6462(5) 0.0902(18) Uani 1 1 d . . . C20 C 0.0396(2) 0.2156(4) 0.6765(5) 0.0827(15) Uani 1 1 d . . . H3A H 0.2593 0.6584 0.9594 0.080 Uiso 1 1 d . . . H5A H 0.4025 0.4886 1.0532 0.080 Uiso 1 1 d . . . H7A H 0.3888 0.3407 1.0396 0.080 Uiso 1 1 d . . . H8A H 0.3442 0.1425 1.0269 0.080 Uiso 1 1 d . . . H8B H 0.3988 0.1864 0.9913 0.080 Uiso 1 1 d . . . H9A H 0.3429 0.0481 0.8954 0.080 Uiso 1 1 d . . . H9B H 0.3401 0.1358 0.8173 0.080 Uiso 1 1 d . . . H10A H 0.2524 0.0006 0.8135 0.080 Uiso 1 1 d . . . H12A H 0.1550 -0.0850 0.7416 0.080 Uiso 1 1 d . . . H14A H 0.0076 0.0484 0.6365 0.080 Uiso 1 1 d . . . H17A H 0.1349 0.4793 0.8577 0.080 Uiso 1 1 d . . . H18A H 0.3559 0.7218 1.0691 0.080 Uiso 1 1 d . . . H18B H 0.4107 0.6633 1.0928 0.080 Uiso 1 1 d . . . H18C H 0.3802 0.6995 0.9860 0.080 Uiso 1 1 d . . . H19A H 0.0071 -0.1284 0.6332 0.080 Uiso 1 1 d . . . H19B H 0.0588 -0.1677 0.7011 0.080 Uiso 1 1 d . . . H19C H 0.0327 -0.1412 0.5767 0.080 Uiso 1 1 d . . . H20A H 0.0636 0.2726 0.7208 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0403(4) 0.0475(4) 0.0595(4) -0.0066(3) 0.0202(3) -0.0012(3) Cl1 0.0932(9) 0.0636(7) 0.0655(8) -0.0013(6) 0.0333(7) -0.0144(6) O1 0.0499(17) 0.0554(18) 0.085(2) -0.0167(16) 0.0331(16) -0.0041(13) O2 0.0419(15) 0.0562(16) 0.076(2) -0.0079(16) 0.0194(15) -0.0008(13) O3 0.107(4) 0.121(4) 0.214(6) -0.023(4) 0.071(4) 0.006(3) O4 0.045(2) 0.121(3) 0.115(3) -0.009(3) 0.008(2) 0.008(2) O5 0.148(15) 0.127(14) 0.36(3) -0.074(16) 0.101(17) -0.041(10) N1 0.0423(18) 0.050(2) 0.057(2) -0.0031(16) 0.0193(16) 0.0007(15) N2 0.0471(19) 0.0477(18) 0.062(2) -0.0043(16) 0.0255(17) -0.0020(15) C1 0.057(2) 0.055(2) 0.051(2) -0.005(2) 0.028(2) -0.001(2) C2 0.065(3) 0.055(3) 0.059(3) 0.003(2) 0.032(2) 0.006(2) C3 0.080(3) 0.050(2) 0.055(3) -0.001(2) 0.030(2) 0.002(2) C4 0.070(3) 0.052(2) 0.051(3) -0.002(2) 0.022(2) -0.002(2) C5 0.059(3) 0.063(3) 0.045(2) -0.002(2) 0.020(2) -0.002(2) C6 0.053(2) 0.051(2) 0.044(2) -0.0042(18) 0.0209(19) -0.0038(19) C7 0.042(2) 0.063(3) 0.047(2) -0.005(2) 0.0159(18) -0.0024(19) C8 0.043(2) 0.055(3) 0.089(3) -0.003(2) 0.023(2) 0.003(2) C9 0.046(2) 0.055(3) 0.096(4) -0.014(3) 0.030(2) 0.002(2) C10 0.053(2) 0.052(2) 0.055(2) -0.0026(19) 0.028(2) -0.0004(19) C11 0.054(2) 0.056(2) 0.045(2) -0.0050(19) 0.0245(19) -0.0089(19) C12 0.069(3) 0.061(3) 0.050(2) -0.009(2) 0.030(2) -0.013(2) C13 0.059(3) 0.073(3) 0.052(3) -0.011(2) 0.021(2) -0.022(2) C14 0.047(2) 0.090(4) 0.064(3) -0.015(3) 0.020(2) -0.018(2) C15 0.044(2) 0.078(3) 0.055(3) -0.005(2) 0.015(2) -0.004(2) C16 0.049(2) 0.064(3) 0.046(2) -0.003(2) 0.0192(19) -0.006(2) C17 0.109(5) 0.078(4) 0.106(4) 0.032(3) 0.066(4) 0.059(3) C18 0.078(3) 0.057(3) 0.086(4) -0.002(3) 0.019(3) -0.013(3) C19 0.081(4) 0.092(4) 0.080(4) -0.008(3) 0.023(3) -0.041(3) C20 0.054(3) 0.091(4) 0.085(4) -0.014(3) 0.017(3) -0.002(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 O2 1.878(3) . ? Mn1 O1 1.878(3) . ? Mn1 N2 1.969(3) . ? Mn1 N1 1.987(3) . ? Mn1 Cl1 2.3691(14) . ? O1 C1 1.341(5) . ? O2 C16 1.318(5) . ? O3 C17 1.183(6) . ? O4 C20 1.213(6) . ? N1 C7 1.284(5) . ? N1 C8 1.481(5) . ? N2 C10 1.291(5) . ? N2 C9 1.472(5) . ? C1 C6 1.395(6) . ? C1 C2 1.418(6) . ? C2 C3 1.389(6) . ? C2 C17 1.528(7) . ? C3 C4 1.380(6) . ? C4 C5 1.377(6) . ? C4 C18 1.484(6) . ? C5 C6 1.415(6) . ? C6 C7 1.437(6) . ? C8 C9 1.513(7) . ? C10 C11 1.437(6) . ? C11 C12 1.391(6) . ? C11 C16 1.411(6) . ? C12 C13 1.381(6) . ? C13 C14 1.381(7) . ? C13 C19 1.507(7) . ? C14 C15 1.378(7) . ? C15 C16 1.413(6) . ? C15 C20 1.481(7) . ? 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 91.47(13) . . ? O2 Mn1 N2 91.26(14) . . ? O1 Mn1 N2 160.70(15) . . ? O2 Mn1 N1 161.70(15) . . ? O1 Mn1 N1 89.65(13) . . ? N2 Mn1 N1 81.92(14) . . ? O2 Mn1 Cl1 101.84(11) . . ? O1 Mn1 Cl1 99.81(11) . . ? N2 Mn1 Cl1 98.32(11) . . ? N1 Mn1 Cl1 95.96(11) . . ? C1 O1 Mn1 124.6(3) . . ? C16 O2 Mn1 130.2(3) . . ? C7 N1 C8 121.0(4) . . ? C7 N1 Mn1 124.6(3) . . ? C8 N1 Mn1 114.4(3) . . ? C10 N2 C9 120.7(3) . . ? C10 N2 Mn1 126.9(3) . . ? C9 N2 Mn1 112.5(3) . . ? O1 C1 C6 122.4(4) . . ? O1 C1 C2 118.9(4) . . ? C6 C1 C2 118.6(4) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 C17 123.5(4) . . ? C1 C2 C17 117.5(4) . . ? C4 C3 C2 123.7(4) . . ? C5 C4 C3 116.6(4) . . ? C5 C4 C18 122.3(4) . . ? C3 C4 C18 121.1(4) . . ? C4 C5 C6 122.8(4) . . ? C1 C6 C5 119.3(4) . . ? C1 C6 C7 122.6(4) . . ? C5 C6 C7 118.1(4) . . ? N1 C7 C6 124.6(4) . . ? N1 C8 C9 106.3(4) . . ? N2 C9 C8 107.5(4) . . ? N2 C10 C11 125.4(4) . . ? C12 C11 C16 120.1(4) . . ? C12 C11 C10 117.9(4) . . ? C16 C11 C10 122.0(4) . . ? C13 C12 C11 123.0(4) . . ? C14 C13 C12 115.7(4) . . ? C14 C13 C19 123.6(4) . . ? C12 C13 C19 120.6(5) . . ? C15 C14 C13 124.2(4) . . ? C14 C15 C16 119.5(4) . . ? C14 C15 C20 121.3(4) . . ? C16 C15 C20 119.2(4) . . ? O2 C16 C11 123.7(4) . . ? O2 C16 C15 119.0(4) . . ? C11 C16 C15 117.3(4) . . ? O3 C17 C2 120.4(6) . . ? O4 C20 C15 123.5(5) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.937 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.140