# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef 'Complex 2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 Mn N2 O4' _chemical_formula_weight 451.33 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 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 25.655(8) _cell_length_b 11.570(4) _cell_length_c 7.024(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.927(4) _cell_angle_gamma 90.00 _cell_volume 2053.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6438 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 26.05 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.740 _exptl_absorpt_correction_T_max 0.768 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6438 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.05 _reflns_number_total 2042 _reflns_number_gt 1895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0900P)^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 2042 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.5000 -0.12030(2) 0.7500 0.02785(16) Uani 1 2 d S . . O2 O 0.56871(4) -0.02426(9) 0.72485(14) 0.0389(3) Uani 1 1 d . . . N1 N 0.55113(5) -0.28498(10) 0.72527(16) 0.0342(3) Uani 1 1 d . . . C12 C 0.52738(6) -0.38832(11) 0.7388(2) 0.0340(4) Uani 1 1 d . . . C10 C 0.55387(7) -0.49443(12) 0.7302(2) 0.0437(4) Uani 1 1 d . . . C1 C 0.56935(5) 0.07609(11) 0.65537(18) 0.0300(3) Uani 1 1 d . . . C8 C 0.63138(8) -0.38538(16) 0.6999(3) 0.0572(5) Uani 1 1 d . . . H8A H 0.6669 -0.3814 0.6883 0.069 Uiso 1 1 calc R . . C7 C 0.60150(6) -0.28378(14) 0.7056(2) 0.0437(4) Uani 1 1 d . . . H7A H 0.6178 -0.2129 0.6950 0.052 Uiso 1 1 calc R . . C9 C 0.60753(8) -0.48923(15) 0.7118(3) 0.0569(5) Uani 1 1 d . . . H9A H 0.6267 -0.5571 0.7076 0.068 Uiso 1 1 calc R . . C3 C 0.65686(6) 0.11691(12) 0.8497(2) 0.0396(4) Uani 1 1 d . . . C2 C 0.62033(6) 0.14144(13) 0.7010(2) 0.0364(3) Uani 1 1 d . . . C6 C 0.72292(6) 0.27322(15) 0.8160(2) 0.0472(4) Uani 1 1 d . . . H6A H 0.7052 0.2893 0.6918 0.057 Uiso 1 1 calc R . . C4 C 0.70516(5) 0.18396(13) 0.9217(2) 0.0401(3) Uani 1 1 d . . . C11 C 0.52521(8) -0.60116(14) 0.7403(3) 0.0563(5) Uani 1 1 d . . . H11A H 0.5425 -0.6712 0.7330 0.068 Uiso 1 1 calc R . . C5 C 0.73313(6) 0.16161(15) 1.1054(3) 0.0479(4) Uani 1 1 d . . . H5A H 0.7222 0.1017 1.1775 0.057 Uiso 1 1 calc R . . O1 O 0.53103(4) 0.12754(7) 0.55657(15) 0.0356(3) Uani 1 1 d . . . H2 H 0.6513(7) 0.0541(16) 0.919(3) 0.057(5) Uiso 1 1 d . . . H1 H 0.6231(6) 0.2089(15) 0.628(2) 0.049(5) 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 0.0211(2) 0.0205(2) 0.0385(2) 0.000 -0.00486(14) 0.000 O2 0.0289(5) 0.0293(5) 0.0539(6) 0.0051(4) -0.0061(4) -0.0079(4) N1 0.0350(6) 0.0284(6) 0.0377(6) -0.0003(5) 0.0019(5) 0.0022(5) C12 0.0475(9) 0.0251(7) 0.0276(7) 0.0005(4) 0.0016(6) 0.0053(5) C10 0.0655(11) 0.0292(7) 0.0357(7) 0.0011(5) 0.0071(7) 0.0115(7) C1 0.0257(6) 0.0288(6) 0.0331(7) -0.0039(5) -0.0014(5) -0.0048(5) C8 0.0446(11) 0.0624(12) 0.0649(12) 0.0005(8) 0.0107(9) 0.0192(8) C7 0.0395(8) 0.0408(8) 0.0507(8) -0.0003(7) 0.0073(7) 0.0064(6) C9 0.0707(12) 0.0436(9) 0.0567(9) 0.0021(7) 0.0118(9) 0.0293(9) C3 0.0276(8) 0.0384(8) 0.0495(9) 0.0001(6) -0.0026(7) -0.0105(5) C2 0.0278(7) 0.0307(6) 0.0490(9) 0.0007(6) 0.0021(6) -0.0074(6) C6 0.0318(7) 0.0559(9) 0.0486(8) 0.0062(7) -0.0077(6) -0.0116(7) C4 0.0242(7) 0.0407(7) 0.0523(8) -0.0013(6) -0.0022(6) -0.0076(5) C11 0.0985(16) 0.0239(7) 0.0457(9) 0.0002(6) 0.0101(10) 0.0126(8) C5 0.0322(8) 0.0503(9) 0.0573(9) 0.0095(8) -0.0034(7) -0.0148(7) O1 0.0298(6) 0.0342(5) 0.0384(6) -0.0020(4) -0.0065(4) 0.0009(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 2.1167(11) . ? Mn1 O2 2.1167(11) 2_656 ? Mn1 O1 2.1649(12) 5_656 ? Mn1 O1 2.1649(12) 6_556 ? Mn1 N1 2.3365(13) 2_656 ? Mn1 N1 2.3365(13) . ? O2 C1 1.2605(16) . ? N1 C7 1.3233(19) . ? N1 C12 1.3527(17) . ? C12 C10 1.4096(19) . ? C12 C12 1.440(3) 2_656 ? C10 C9 1.406(3) . ? C10 C11 1.445(2) . ? C1 O1 1.2518(16) . ? C1 C2 1.4968(18) . ? C8 C9 1.357(3) . ? C8 C7 1.407(2) . ? C3 C2 1.309(2) . ? C3 C4 1.4756(19) . ? C6 C5 1.389(2) 7_657 ? C6 C4 1.394(2) . ? C4 C5 1.388(2) . ? C11 C11 1.324(4) 2_656 ? C5 C6 1.389(2) 7_657 ? O1 Mn1 2.1649(12) 5_656 ? 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 O2 116.67(6) . 2_656 ? O2 Mn1 O1 96.08(4) . 5_656 ? O2 Mn1 O1 86.25(4) 2_656 5_656 ? O2 Mn1 O1 86.25(4) . 6_556 ? O2 Mn1 O1 96.08(4) 2_656 6_556 ? O1 Mn1 O1 175.57(5) 5_656 6_556 ? O2 Mn1 N1 157.00(4) . 2_656 ? O2 Mn1 N1 86.31(5) 2_656 2_656 ? O1 Mn1 N1 85.84(4) 5_656 2_656 ? O1 Mn1 N1 90.54(4) 6_556 2_656 ? O2 Mn1 N1 86.31(5) . . ? O2 Mn1 N1 157.00(4) 2_656 . ? O1 Mn1 N1 90.54(4) 5_656 . ? O1 Mn1 N1 85.84(4) 6_556 . ? N1 Mn1 N1 70.74(7) 2_656 . ? C1 O2 Mn1 125.62(9) . . ? C7 N1 C12 118.46(12) . . ? C7 N1 Mn1 124.76(10) . . ? C12 N1 Mn1 116.74(10) . . ? N1 C12 C10 122.70(16) . . ? N1 C12 C12 117.86(8) . 2_656 ? C10 C12 C12 119.43(10) . 2_656 ? C12 C10 C9 116.98(15) . . ? C12 C10 C11 119.26(16) . . ? C9 C10 C11 123.76(16) . . ? O1 C1 O2 126.24(12) . . ? O1 C1 C2 116.87(12) . . ? O2 C1 C2 116.85(12) . . ? C9 C8 C7 118.96(18) . . ? N1 C7 C8 122.72(16) . . ? C8 C9 C10 120.16(15) . . ? C2 C3 C4 127.10(14) . . ? C3 C2 C1 122.70(14) . . ? C5 C6 C4 120.52(15) 7_657 . ? C5 C4 C6 117.99(13) . . ? C5 C4 C3 119.31(14) . . ? C6 C4 C3 122.63(14) . . ? C11 C11 C10 121.30(10) 2_656 . ? C6 C5 C4 121.48(15) 7_657 . ? C1 O1 Mn1 130.69(9) . 5_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.262 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 842660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CP2 #TrackingRef 'CP2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Mn N2 O4' _chemical_formula_weight 425.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 21.9137(15) _cell_length_b 11.7028(8) _cell_length_c 7.3134(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.4230(10) _cell_angle_gamma 90.00 _cell_volume 1844.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5149 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.861 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5149 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1576 _reflns_number_gt 1491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.1300P)^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 1576 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1429 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.0000 0.38259(4) 0.7500 0.0197(3) Uani 1 2 d S . . O1 O 0.07688(8) 0.48041(16) 0.8718(3) 0.0322(5) Uani 1 1 d . . . O3 O 0.04712(8) 0.63622(14) 1.0100(2) 0.0268(4) Uani 1 1 d . . . N1 N 0.05535(9) 0.22218(18) 0.8669(3) 0.0217(5) Uani 1 1 d . . . C7 C 0.11024(11) 0.2232(2) 0.9794(3) 0.0269(6) Uani 1 1 d . . . H7A H 0.1277 0.2933 1.0195 0.032 Uiso 1 1 calc R . . C8 C 0.14280(14) 0.1235(2) 1.0400(4) 0.0347(7) Uani 1 1 d . . . H8A H 0.1812 0.1275 1.1182 0.042 Uiso 1 1 calc R . . C9 C 0.11719(12) 0.0197(2) 0.9825(4) 0.0316(6) Uani 1 1 d . . . H9A H 0.1387 -0.0474 1.0195 0.038 Uiso 1 1 calc R . . C10 C 0.05874(12) 0.0150(2) 0.8680(3) 0.0259(6) Uani 1 1 d . . . C11 C 0.02796(13) -0.0907(2) 0.8065(4) 0.0298(6) Uani 1 1 d . . . H11A H 0.0469 -0.1598 0.8454 0.036 Uiso 1 1 calc R . . C12 C 0.02997(12) 0.11964(17) 0.8109(3) 0.0205(6) Uani 1 1 d . . . C2 C 0.14907(12) 0.6276(2) 0.9442(4) 0.0259(6) Uiso 1 1 d . . . C1 C 0.08545(10) 0.5785(2) 0.9438(3) 0.0217(5) Uiso 1 1 d . . . C5 C 0.17092(12) 0.7171(2) 1.0553(3) 0.0298(6) Uiso 1 1 d . . . H5A H 0.1456 0.7469 1.1329 0.036 Uiso 1 1 calc R . . C3 C 0.1887(2) 0.5917(4) 0.8352(6) 0.0233(9) Uiso 0.50 1 d P . . H3A H 0.1778 0.5295 0.7570 0.028 Uiso 1 1 calc R . . C4 C 0.2463(2) 0.6462(4) 0.8366(6) 0.0222(9) Uiso 0.50 1 d P . . H4A H 0.2704 0.6175 0.7545 0.027 Uiso 1 1 calc R . . C6 C 0.23035(13) 0.7681(2) 1.0602(4) 0.0347(6) 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 0.0148(4) 0.0141(4) 0.0305(4) 0.000 0.0052(2) 0.000 O1 0.0237(9) 0.0233(9) 0.0503(11) -0.0095(8) 0.0084(8) -0.0095(7) O3 0.0214(9) 0.0253(8) 0.0351(10) 0.0001(7) 0.0093(7) -0.0014(6) N1 0.0214(10) 0.0217(10) 0.0232(10) -0.0008(7) 0.0069(8) -0.0004(8) C7 0.0267(13) 0.0275(13) 0.0273(13) -0.0023(10) 0.0071(10) -0.0009(10) C8 0.0247(14) 0.0438(17) 0.0342(15) 0.0047(11) 0.0015(12) 0.0077(10) C9 0.0359(14) 0.0297(13) 0.0316(14) 0.0076(10) 0.0126(11) 0.0134(11) C10 0.0376(14) 0.0224(12) 0.0211(12) 0.0027(9) 0.0147(10) 0.0078(10) C11 0.0493(16) 0.0160(11) 0.0299(13) 0.0042(10) 0.0223(11) 0.0054(11) C12 0.0269(14) 0.0182(12) 0.0186(12) -0.0005(8) 0.0106(11) 0.0005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.0975(16) 2_556 ? Mn1 O1 2.0976(16) . ? Mn1 O3 2.2027(17) 5_567 ? Mn1 O3 2.2027(17) 6_565 ? Mn1 N1 2.313(2) 2_556 ? Mn1 N1 2.313(2) . ? O1 C1 1.262(3) . ? O3 C1 1.243(3) . ? O3 Mn1 2.2027(17) 5_567 ? N1 C7 1.329(3) . ? N1 C12 1.355(3) . ? C7 C8 1.397(4) . ? C7 H7A 0.9300 . ? C8 C9 1.373(4) . ? C8 H8A 0.9300 . ? C9 C10 1.399(4) . ? C9 H9A 0.9300 . ? C10 C12 1.406(3) . ? C10 C11 1.442(4) . ? C11 C11 1.349(6) 2_556 ? C11 H11A 0.9300 . ? C12 C12 1.447(5) 2_556 ? C2 C3 1.347(6) . ? C2 C5 1.358(4) . ? C2 C1 1.508(3) . ? C5 C6 1.427(4) . ? C5 H5A 0.9300 . ? C3 C4 1.413(6) . ? C3 H3A 0.9300 . ? C4 C6 1.303(5) 7_567 ? C4 H4A 0.9300 . ? C6 C4 1.303(5) 7_567 ? C6 C6 1.404(6) 7_567 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O1 113.85(11) 2_556 . ? O1 Mn1 O3 86.38(7) 2_556 5_567 ? O1 Mn1 O3 99.92(7) . 5_567 ? O1 Mn1 O3 99.92(7) 2_556 6_565 ? O1 Mn1 O3 86.38(7) . 6_565 ? O3 Mn1 O3 168.53(9) 5_567 6_565 ? O1 Mn1 N1 87.64(7) 2_556 2_556 ? O1 Mn1 N1 157.98(8) . 2_556 ? O3 Mn1 N1 85.61(7) 5_567 2_556 ? O3 Mn1 N1 85.08(6) 6_565 2_556 ? O1 Mn1 N1 157.98(8) 2_556 . ? O1 Mn1 N1 87.64(7) . . ? O3 Mn1 N1 85.08(6) 5_567 . ? O3 Mn1 N1 85.61(7) 6_565 . ? N1 Mn1 N1 71.51(10) 2_556 . ? C1 O1 Mn1 136.11(16) . . ? C1 O3 Mn1 134.72(16) . 5_567 ? C7 N1 C12 118.1(2) . . ? C7 N1 Mn1 125.24(16) . . ? C12 N1 Mn1 116.61(15) . . ? N1 C7 C8 122.8(2) . . ? N1 C7 H7A 118.6 . . ? C8 C7 H7A 118.6 . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C12 C10 C9 117.2(2) . . ? C12 C10 C11 119.7(2) . . ? C9 C10 C11 123.1(2) . . ? C11 C11 C10 120.88(15) 2_556 . ? C11 C11 H11A 119.6 2_556 . ? C10 C11 H11A 119.6 . . ? N1 C12 C10 123.0(2) . . ? N1 C12 C12 117.61(13) . 2_556 ? C10 C12 C12 119.42(15) . 2_556 ? C3 C2 C5 113.5(3) . . ? C3 C2 C1 125.1(3) . . ? C5 C2 C1 121.4(2) . . ? O3 C1 O1 126.6(2) . . ? O3 C1 C2 118.8(2) . . ? O1 C1 C2 114.5(2) . . ? C2 C5 C6 124.0(3) . . ? C2 C5 H5A 118.0 . . ? C6 C5 H5A 118.0 . . ? C2 C3 C4 121.7(4) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C6 C4 C3 127.4(4) 7_567 . ? C6 C4 H4A 116.3 7_567 . ? C3 C4 H4A 116.3 . . ? C4 C6 C6 112.0(4) 7_567 7_567 ? C4 C6 C5 126.7(3) 7_567 . ? C6 C6 C5 121.2(3) 7_567 . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.168 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 921240'