# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1102w99 _database_code_depnum_ccdc_archive 'CCDC 906265' #TrackingRef 'complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Br2 F Mn N2 O5 P, H O0.50, 1.3(H0.40 O0.20)' _chemical_formula_sum 'C26 H25 Br2 F Mn N2 O6 P' _chemical_formula_weight 726.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9205(7) _cell_length_b 15.7116(16) _cell_length_c 13.5636(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.2480(10) _cell_angle_gamma 90.00 _cell_volume 1459.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 7209 _cell_measurement_theta_min 2.591 _cell_measurement_theta_max 27.497 _exptl_crystal_description rod _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 3.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.387 _exptl_absorpt_correction_T_max 0.454 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 11193 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5595 _reflns_number_gt 4711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.034(13) _refine_ls_number_reflns 5595 _refine_ls_number_parameters 371 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.71187(15) 0.66779(7) 0.09331(8) 0.0334(2) Uani 1 1 d . . . P1 P 1.2166(3) 0.63050(12) 0.13257(14) 0.0350(4) Uani 1 1 d . . . O1 O 0.7404(7) 0.5572(3) 0.1515(3) 0.0349(11) Uani 1 1 d . . . O2 O 0.6836(7) 0.6259(3) -0.0397(4) 0.0390(11) Uani 1 1 d . . . O3 O 1.0399(7) 0.6783(3) 0.0892(4) 0.0394(11) Uani 1 1 d . . . O4 O 1.2096(7) 0.5410(3) 0.1013(4) 0.0408(12) Uani 1 1 d . . . H4A H 1.2048 0.5321 0.0391 0.049 Uiso 1 1 d R . . O5 O 1.4038(7) 0.6676(3) 0.1082(3) 0.0354(10) Uani 1 1 d . . . O1W O 0.9051(12) 0.4658(6) 0.9864(6) 0.035(2) Uani 0.50 1 d P . . H1X H 0.8655 0.4811 1.0402 0.042 Uiso 0.50 1 d PR . . H1Y H 0.8797 0.5047 0.9428 0.042 Uiso 0.50 1 d PR . . O2W O 0.155(2) 0.8568(11) 0.9535(12) 0.039(4) Uani 0.30 1 d P . . H2X H 0.2220 0.8192 0.9886 0.047 Uiso 0.30 1 d PR . . H2Y H 0.1245 0.8384 0.8942 0.047 Uiso 0.30 1 d PR . . O3W O 0.207(4) 0.7414(15) 0.8778(18) 0.038(6) Uani 0.20 1 d P . . H3X H 0.2678 0.7552 0.8300 0.046 Uiso 0.20 1 d PR . . H3Y H 0.2890 0.7302 0.9291 0.046 Uiso 0.20 1 d PR . . N1 N 0.6820(9) 0.7880(4) 0.0466(4) 0.0370(13) Uani 1 1 d . . . N2 N 0.7630(8) 0.7259(4) 0.2274(5) 0.0366(13) Uani 1 1 d . . . C1 C 0.7155(10) 0.5381(5) 0.2412(6) 0.0367(16) Uani 1 1 d . . . C2 C 0.6903(11) 0.4473(6) 0.2642(5) 0.0430(16) Uani 1 1 d . . . H2 H 0.6810 0.4071 0.2134 0.052 Uiso 1 1 calc R . . C3 C 0.6806(10) 0.4216(4) 0.3610(5) 0.0326(14) Uani 1 1 d . . . H3 H 0.6711 0.3642 0.3759 0.039 Uiso 1 1 calc R . . C4 C 0.6853(10) 0.4845(5) 0.4383(6) 0.0388(16) Uani 1 1 d . . . C5 C 0.7104(12) 0.5668(5) 0.4182(6) 0.0446(18) Uani 1 1 d . . . H5 H 0.7182 0.6055 0.4705 0.054 Uiso 1 1 calc R . . C6 C 0.7256(10) 0.5976(5) 0.3239(5) 0.0366(16) Uani 1 1 d . . . C7 C 0.7574(10) 0.6889(4) 0.3098(6) 0.0392(17) Uani 1 1 d . . . H7 H 0.7750 0.7227 0.3667 0.047 Uiso 1 1 calc R . . C8 C 0.8006(10) 0.8159(5) 0.2161(5) 0.0408(16) Uani 1 1 d . . . H8 H 0.9290 0.8234 0.1948 0.049 Uiso 1 1 calc R . . C9 C 0.7896(11) 0.8696(4) 0.3109(5) 0.0370(15) Uani 1 1 d . . . H9A H 0.8939 0.8530 0.3629 0.044 Uiso 1 1 calc R . . H9B H 0.6661 0.8593 0.3348 0.044 Uiso 1 1 calc R . . C10 C 0.8085(12) 0.9659(4) 0.2871(5) 0.0415(17) Uani 1 1 d . . . H10A H 0.7901 0.9993 0.3452 0.050 Uiso 1 1 calc R . . H10B H 0.9388 0.9773 0.2718 0.050 Uiso 1 1 calc R . . C11 C 0.6630(10) 0.9918(4) 0.2019(5) 0.0334(14) Uani 1 1 d . . . H11A H 0.6898 1.0493 0.1816 0.040 Uiso 1 1 calc R . . H11B H 0.5331 0.9906 0.2208 0.040 Uiso 1 1 calc R . . C12 C 0.6746(9) 0.9299(4) 0.1156(6) 0.0349(16) Uani 1 1 d . . . H12A H 0.5797 0.9485 0.0601 0.042 Uiso 1 1 calc R . . H12B H 0.8025 0.9366 0.0952 0.042 Uiso 1 1 calc R . . C13 C 0.6426(11) 0.8346(5) 0.1296(5) 0.0394(16) Uani 1 1 d . . . H13 H 0.5120 0.8225 0.1461 0.047 Uiso 1 1 calc R . . C14 C 0.6861(9) 0.8131(5) -0.0446(5) 0.0394(16) Uani 1 1 d . . . H14 H 0.6684 0.8708 -0.0583 0.047 Uiso 1 1 calc R . . C15 C 0.7157(10) 0.7587(5) -0.1247(5) 0.0371(16) Uani 1 1 d . . . C16 C 0.7411(11) 0.7991(5) -0.2159(5) 0.0410(16) Uani 1 1 d . . . H16 H 0.7363 0.8582 -0.2208 0.049 Uiso 1 1 calc R . . C17 C 0.7733(10) 0.7505(5) -0.2981(6) 0.0369(16) Uani 1 1 d . . . C18 C 0.7863(9) 0.6634(5) -0.2913(5) 0.0328(14) Uani 1 1 d . . . H18 H 0.8113 0.6318 -0.3460 0.039 Uiso 1 1 calc R . . C19 C 0.7621(10) 0.6219(5) -0.2027(5) 0.0341(14) Uani 1 1 d . . . H19 H 0.7768 0.5631 -0.1983 0.041 Uiso 1 1 calc R . . C20 C 0.7155(11) 0.6682(5) -0.1197(5) 0.0416(16) Uani 1 1 d . . . C21 C 1.2279(12) 0.6280(5) 0.2686(5) 0.0425(17) Uani 1 1 d . . . C22 C 1.2052(10) 0.5552(4) 0.3246(5) 0.0306(13) Uani 1 1 d . . . H22 H 1.1847 0.5036 0.2911 0.037 Uiso 1 1 calc R . . C23 C 1.2109(10) 0.5548(4) 0.4232(5) 0.0335(15) Uani 1 1 d . . . H23 H 1.1930 0.5045 0.4569 0.040 Uiso 1 1 calc R . . C24 C 1.2449(12) 0.6325(4) 0.4759(6) 0.0427(17) Uani 1 1 d . . . H24 H 1.2499 0.6330 0.5448 0.051 Uiso 1 1 calc R . . C25 C 1.2711(11) 0.7090(5) 0.4255(6) 0.0387(16) Uani 1 1 d . . . H25 H 1.2942 0.7604 0.4592 0.046 Uiso 1 1 calc R . . C26 C 1.2605(10) 0.7034(5) 0.3230(5) 0.0365(15) Uani 1 1 d . . . Br1 Br 0.65926(10) 0.44751(4) 0.56863(5) 0.03838(17) Uani 1 1 d . . . Br2 Br 0.81062(11) 0.80521(5) -0.41797(5) 0.04057(19) Uani 1 1 d . . . F1 F 1.2866(6) 0.7769(2) 0.2739(3) 0.0404(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0284(5) 0.0329(5) 0.0388(5) 0.0010(4) 0.0037(4) 0.0009(4) P1 0.0344(9) 0.0376(9) 0.0324(9) -0.0050(7) 0.0028(7) -0.0021(7) O1 0.038(2) 0.042(3) 0.028(2) 0.002(2) 0.0132(19) 0.004(2) O2 0.031(2) 0.039(3) 0.046(3) -0.003(2) 0.001(2) 0.0011(19) O3 0.039(3) 0.043(3) 0.035(2) -0.009(2) 0.001(2) -0.001(2) O4 0.030(2) 0.051(3) 0.041(3) -0.007(2) 0.002(2) 0.007(2) O5 0.045(3) 0.040(2) 0.022(2) -0.010(2) 0.0069(18) -0.011(2) O1W 0.024(4) 0.064(7) 0.015(4) -0.005(4) -0.001(3) 0.019(4) O2W 0.032(8) 0.046(9) 0.043(9) -0.017(8) 0.012(7) -0.013(7) O3W 0.038(13) 0.036(13) 0.035(13) -0.004(10) -0.014(10) 0.019(11) N1 0.042(3) 0.030(3) 0.039(3) 0.006(2) 0.007(2) 0.008(2) N2 0.030(3) 0.039(3) 0.039(3) -0.003(3) 0.001(2) -0.005(2) C1 0.034(4) 0.036(4) 0.044(4) 0.000(3) 0.019(3) 0.001(3) C2 0.048(4) 0.044(4) 0.037(4) 0.005(4) 0.007(3) 0.006(4) C3 0.035(3) 0.031(3) 0.033(3) -0.001(3) 0.011(3) 0.006(3) C4 0.035(4) 0.042(4) 0.040(4) 0.012(3) 0.010(3) 0.008(3) C5 0.050(4) 0.043(4) 0.037(4) 0.000(3) -0.009(3) 0.014(4) C6 0.041(4) 0.037(4) 0.029(3) 0.002(3) -0.002(3) 0.011(3) C7 0.037(4) 0.035(4) 0.042(4) 0.007(3) -0.008(3) 0.009(3) C8 0.028(3) 0.061(5) 0.034(3) 0.000(3) 0.006(3) -0.004(4) C9 0.032(4) 0.037(4) 0.045(4) -0.001(3) 0.013(3) -0.008(3) C10 0.059(5) 0.034(4) 0.036(4) -0.003(3) 0.019(3) -0.012(3) C11 0.038(4) 0.034(3) 0.032(3) 0.005(3) 0.018(3) 0.013(3) C12 0.024(3) 0.031(4) 0.055(4) -0.003(3) 0.024(3) 0.004(3) C13 0.038(4) 0.042(4) 0.037(4) -0.001(3) 0.000(3) 0.012(3) C14 0.031(3) 0.040(4) 0.045(4) 0.002(3) -0.002(3) 0.025(3) C15 0.030(4) 0.046(4) 0.035(4) 0.006(3) 0.002(3) -0.004(3) C16 0.048(4) 0.032(4) 0.042(4) 0.013(3) 0.002(3) 0.004(3) C17 0.030(4) 0.034(4) 0.049(4) 0.007(3) 0.012(3) -0.014(3) C18 0.030(3) 0.034(3) 0.037(3) -0.002(3) 0.010(3) 0.004(3) C19 0.038(3) 0.033(3) 0.031(3) -0.008(3) 0.006(3) -0.009(3) C20 0.045(4) 0.045(4) 0.034(4) -0.005(3) 0.004(3) 0.007(4) C21 0.045(4) 0.045(4) 0.036(4) 0.001(3) -0.001(3) 0.007(3) C22 0.034(3) 0.028(3) 0.031(3) 0.003(2) 0.006(3) 0.001(3) C23 0.041(4) 0.026(3) 0.036(4) 0.011(3) 0.013(3) 0.012(3) C24 0.056(5) 0.032(4) 0.039(4) 0.000(3) 0.007(4) 0.003(3) C25 0.038(4) 0.033(4) 0.047(4) 0.002(3) 0.013(3) 0.012(3) C26 0.030(3) 0.041(4) 0.035(3) -0.001(3) -0.004(3) 0.002(3) Br1 0.0489(4) 0.0279(3) 0.0382(4) 0.0096(3) 0.0056(3) -0.0070(3) Br2 0.0433(4) 0.0407(4) 0.0409(4) 0.0034(3) 0.0168(3) -0.0062(3) F1 0.048(2) 0.034(2) 0.038(2) 0.0013(17) 0.0019(18) -0.0017(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 Mn1 O2 1.904(5) . ? Mn1 O1 1.907(5) . ? Mn1 N1 1.994(6) . ? Mn1 N2 2.020(6) . ? Mn1 O5 2.170(5) 1_455 ? Mn1 O3 2.285(5) . ? P1 O4 1.468(5) . ? P1 O3 1.482(5) . ? P1 O5 1.500(5) . ? P1 C21 1.836(8) . ? O1 C1 1.288(9) . ? O2 C20 1.319(9) . ? O4 H4A 0.8510 . ? O5 Mn1 2.170(5) 1_655 ? O1W H1X 0.8504 . ? O1W H1Y 0.8517 . ? O2W H2X 0.8524 . ? O2W H2Y 0.8518 . ? O3W H3X 0.8500 . ? O3W H3Y 0.8500 . ? N1 C14 1.302(9) . ? N1 C13 1.403(9) . ? N2 C7 1.266(9) . ? N2 C8 1.449(10) . ? C1 C6 1.454(10) . ? C1 C2 1.477(11) . ? C2 C3 1.385(10) . ? C2 H2 0.9300 . ? C3 C4 1.437(10) . ? C3 H3 0.9300 . ? C4 C5 1.338(11) . ? C4 Br1 1.894(7) . ? C5 C6 1.386(10) . ? C5 H5 0.9300 . ? C6 C7 1.467(10) . ? C7 H7 0.9300 . ? C8 C13 1.514(10) . ? C8 C9 1.549(10) . ? C8 H8 0.9800 . ? C9 C10 1.557(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.477(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.533(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.529(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9800 . ? C14 C15 1.420(11) . ? C14 H14 0.9300 . ? C15 C16 1.424(10) . ? C15 C20 1.424(12) . ? C16 C17 1.395(11) . ? C16 H16 0.9300 . ? C17 C18 1.373(10) . ? C17 Br2 1.889(7) . ? C18 C19 1.398(9) . ? C18 H18 0.9300 . ? C19 C20 1.416(10) . ? C19 H19 0.9300 . ? C21 C22 1.395(10) . ? C21 C26 1.397(11) . ? C22 C23 1.332(9) . ? C22 H22 0.9300 . ? C23 C24 1.417(10) . ? C23 H23 0.9300 . ? C24 C25 1.406(10) . ? C24 H24 0.9300 . ? C25 C26 1.385(10) . ? C25 H25 0.9300 . ? C26 F1 1.357(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 Mn1 O1 93.9(2) . . ? O2 Mn1 N1 92.0(2) . . ? O1 Mn1 N1 174.1(2) . . ? O2 Mn1 N2 172.0(2) . . ? O1 Mn1 N2 92.6(2) . . ? N1 Mn1 N2 81.7(2) . . ? O2 Mn1 O5 96.83(18) . 1_455 ? O1 Mn1 O5 90.3(2) . 1_455 ? N1 Mn1 O5 88.4(2) . 1_455 ? N2 Mn1 O5 88.0(2) . 1_455 ? O2 Mn1 O3 88.25(19) . . ? O1 Mn1 O3 91.8(2) . . ? N1 Mn1 O3 89.0(2) . . ? N2 Mn1 O3 86.7(2) . . ? O5 Mn1 O3 174.36(18) 1_455 . ? O4 P1 O3 112.3(3) . . ? O4 P1 O5 107.6(3) . . ? O3 P1 O5 113.9(3) . . ? O4 P1 C21 105.3(3) . . ? O3 P1 C21 108.9(3) . . ? O5 P1 C21 108.4(3) . . ? C1 O1 Mn1 125.7(4) . . ? C20 O2 Mn1 126.8(5) . . ? P1 O3 Mn1 136.0(3) . . ? P1 O4 H4A 116.0 . . ? P1 O5 Mn1 155.8(3) . 1_655 ? H1X O1W H1Y 109.4 . . ? H2X O2W H2Y 109.5 . . ? H3X O3W H3Y 109.5 . . ? C14 N1 C13 129.7(6) . . ? C14 N1 Mn1 125.0(5) . . ? C13 N1 Mn1 105.2(4) . . ? C7 N2 C8 124.7(6) . . ? C7 N2 Mn1 124.3(5) . . ? C8 N2 Mn1 110.9(5) . . ? O1 C1 C6 125.5(7) . . ? O1 C1 C2 117.4(6) . . ? C6 C1 C2 116.9(6) . . ? C3 C2 C1 120.3(7) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.5(7) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.4(7) . . ? C5 C4 Br1 121.3(6) . . ? C3 C4 Br1 118.4(5) . . ? C4 C5 C6 123.7(8) . . ? C4 C5 H5 118.1 . . ? C6 C5 H5 118.1 . . ? C5 C6 C1 119.0(7) . . ? C5 C6 C7 119.6(7) . . ? C1 C6 C7 121.3(6) . . ? N2 C7 C6 126.0(7) . . ? N2 C7 H7 117.0 . . ? C6 C7 H7 117.0 . . ? N2 C8 C13 98.7(6) . . ? N2 C8 C9 114.4(6) . . ? C13 C8 C9 114.9(6) . . ? N2 C8 H8 109.5 . . ? C13 C8 H8 109.5 . . ? C9 C8 H8 109.5 . . ? C8 C9 C10 110.0(6) . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C9 111.2(6) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 108.5(5) . . ? C10 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? C10 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C13 C12 C11 120.1(6) . . ? C13 C12 H12A 107.3 . . ? C11 C12 H12A 107.3 . . ? C13 C12 H12B 107.3 . . ? C11 C12 H12B 107.3 . . ? H12A C12 H12B 106.9 . . ? N1 C13 C8 108.6(6) . . ? N1 C13 C12 111.2(6) . . ? C8 C13 C12 100.7(6) . . ? N1 C13 H13 111.9 . . ? C8 C13 H13 111.9 . . ? C12 C13 H13 111.9 . . ? N1 C14 C15 124.8(7) . . ? N1 C14 H14 117.6 . . ? C15 C14 H14 117.6 . . ? C14 C15 C16 116.5(7) . . ? C14 C15 C20 124.3(7) . . ? C16 C15 C20 119.2(7) . . ? C17 C16 C15 120.3(7) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.5(7) . . ? C18 C17 Br2 119.7(6) . . ? C16 C17 Br2 119.7(5) . . ? C17 C18 C19 120.5(7) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C20 120.8(7) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? O2 C20 C19 118.6(7) . . ? O2 C20 C15 123.0(6) . . ? C19 C20 C15 118.3(7) . . ? C22 C21 C26 115.5(6) . . ? C22 C21 P1 125.0(6) . . ? C26 C21 P1 119.5(6) . . ? C23 C22 C21 124.1(7) . . ? C23 C22 H22 118.0 . . ? C21 C22 H22 118.0 . . ? C22 C23 C24 118.8(6) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 121.0(7) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 116.2(7) . . ? C26 C25 H25 121.9 . . ? C24 C25 H25 121.9 . . ? F1 C26 C25 116.5(6) . . ? F1 C26 C21 119.0(6) . . ? C25 C26 C21 124.4(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 O2 Mn1 O1 C1 -160.7(6) . . . . ? N1 Mn1 O1 C1 13(3) . . . . ? N2 Mn1 O1 C1 24.1(6) . . . . ? O5 Mn1 O1 C1 -63.9(6) 1_455 . . . ? O3 Mn1 O1 C1 110.9(6) . . . . ? O1 Mn1 O2 C20 -157.9(6) . . . . ? N1 Mn1 O2 C20 22.7(6) . . . . ? N2 Mn1 O2 C20 -15(2) . . . . ? O5 Mn1 O2 C20 111.3(6) 1_455 . . . ? O3 Mn1 O2 C20 -66.2(6) . . . . ? O4 P1 O3 Mn1 59.4(5) . . . . ? O5 P1 O3 Mn1 -178.0(3) . . . . ? C21 P1 O3 Mn1 -56.9(5) . . . . ? O2 Mn1 O3 P1 -105.8(4) . . . . ? O1 Mn1 O3 P1 -12.0(4) . . . . ? N1 Mn1 O3 P1 162.2(4) . . . . ? N2 Mn1 O3 P1 80.5(4) . . . . ? O5 Mn1 O3 P1 100(2) 1_455 . . . ? O4 P1 O5 Mn1 -37.7(7) . . . 1_655 ? O3 P1 O5 Mn1 -162.9(6) . . . 1_655 ? C21 P1 O5 Mn1 75.8(7) . . . 1_655 ? O2 Mn1 N1 C14 -11.8(6) . . . . ? O1 Mn1 N1 C14 174(2) . . . . ? N2 Mn1 N1 C14 163.3(6) . . . . ? O5 Mn1 N1 C14 -108.5(6) 1_455 . . . ? O3 Mn1 N1 C14 76.5(6) . . . . ? O2 Mn1 N1 C13 164.0(5) . . . . ? O1 Mn1 N1 C13 -10(3) . . . . ? N2 Mn1 N1 C13 -20.9(4) . . . . ? O5 Mn1 N1 C13 67.2(4) 1_455 . . . ? O3 Mn1 N1 C13 -107.8(5) . . . . ? O2 Mn1 N2 C7 -158.6(14) . . . . ? O1 Mn1 N2 C7 -15.5(6) . . . . ? N1 Mn1 N2 C7 163.4(6) . . . . ? O5 Mn1 N2 C7 74.7(6) 1_455 . . . ? O3 Mn1 N2 C7 -107.2(6) . . . . ? O2 Mn1 N2 C8 23.2(19) . . . . ? O1 Mn1 N2 C8 166.3(5) . . . . ? N1 Mn1 N2 C8 -14.8(4) . . . . ? O5 Mn1 N2 C8 -103.5(5) 1_455 . . . ? O3 Mn1 N2 C8 74.7(4) . . . . ? Mn1 O1 C1 C6 -21.8(10) . . . . ? Mn1 O1 C1 C2 163.5(5) . . . . ? O1 C1 C2 C3 174.2(7) . . . . ? C6 C1 C2 C3 -1.1(11) . . . . ? C1 C2 C3 C4 3.1(11) . . . . ? C2 C3 C4 C5 -3.9(11) . . . . ? C2 C3 C4 Br1 177.1(5) . . . . ? C3 C4 C5 C6 2.6(12) . . . . ? Br1 C4 C5 C6 -178.4(6) . . . . ? C4 C5 C6 C1 -0.5(12) . . . . ? C4 C5 C6 C7 -178.6(7) . . . . ? O1 C1 C6 C5 -175.1(7) . . . . ? C2 C1 C6 C5 -0.3(10) . . . . ? O1 C1 C6 C7 3.0(11) . . . . ? C2 C1 C6 C7 177.8(7) . . . . ? C8 N2 C7 C6 -178.0(7) . . . . ? Mn1 N2 C7 C6 4.1(11) . . . . ? C5 C6 C7 N2 -175.8(7) . . . . ? C1 C6 C7 N2 6.1(12) . . . . ? C7 N2 C8 C13 -135.3(7) . . . . ? Mn1 N2 C8 C13 42.9(6) . . . . ? C7 N2 C8 C9 -12.9(10) . . . . ? Mn1 N2 C8 C9 165.3(5) . . . . ? N2 C8 C9 C10 -173.5(6) . . . . ? C13 C8 C9 C10 -60.4(8) . . . . ? C8 C9 C10 C11 54.1(8) . . . . ? C9 C10 C11 C12 -50.8(7) . . . . ? C10 C11 C12 C13 58.2(8) . . . . ? C14 N1 C13 C8 -131.1(8) . . . . ? Mn1 N1 C13 C8 53.4(7) . . . . ? C14 N1 C13 C12 -21.2(11) . . . . ? Mn1 N1 C13 C12 163.4(5) . . . . ? N2 C8 C13 N1 -63.8(7) . . . . ? C9 C8 C13 N1 174.1(6) . . . . ? N2 C8 C13 C12 179.3(5) . . . . ? C9 C8 C13 C12 57.2(7) . . . . ? C11 C12 C13 N1 -173.0(6) . . . . ? C11 C12 C13 C8 -58.0(8) . . . . ? C13 N1 C14 C15 -175.7(7) . . . . ? Mn1 N1 C14 C15 -1.0(10) . . . . ? N1 C14 C15 C16 -172.0(7) . . . . ? N1 C14 C15 C20 9.9(12) . . . . ? C14 C15 C16 C17 179.2(7) . . . . ? C20 C15 C16 C17 -2.5(11) . . . . ? C15 C16 C17 C18 -1.8(11) . . . . ? C15 C16 C17 Br2 -179.1(5) . . . . ? C16 C17 C18 C19 1.8(11) . . . . ? Br2 C17 C18 C19 179.0(5) . . . . ? C17 C18 C19 C20 2.7(10) . . . . ? Mn1 O2 C20 C19 155.6(5) . . . . ? Mn1 O2 C20 C15 -21.0(10) . . . . ? C18 C19 C20 O2 176.3(6) . . . . ? C18 C19 C20 C15 -7.0(11) . . . . ? C14 C15 C20 O2 1.4(12) . . . . ? C16 C15 C20 O2 -176.7(7) . . . . ? C14 C15 C20 C19 -175.1(7) . . . . ? C16 C15 C20 C19 6.8(11) . . . . ? O4 P1 C21 C22 -8.3(8) . . . . ? O3 P1 C21 C22 112.4(7) . . . . ? O5 P1 C21 C22 -123.2(7) . . . . ? O4 P1 C21 C26 172.1(6) . . . . ? O3 P1 C21 C26 -67.3(7) . . . . ? O5 P1 C21 C26 57.1(7) . . . . ? C26 C21 C22 C23 0.7(11) . . . . ? P1 C21 C22 C23 -178.9(6) . . . . ? C21 C22 C23 C24 -0.9(11) . . . . ? C22 C23 C24 C25 0.4(12) . . . . ? C23 C24 C25 C26 0.4(12) . . . . ? C24 C25 C26 F1 -179.7(6) . . . . ? C24 C25 C26 C21 -0.6(12) . . . . ? C22 C21 C26 F1 179.2(6) . . . . ? P1 C21 C26 F1 -1.2(10) . . . . ? C22 C21 C26 C25 0.1(12) . . . . ? P1 C21 C26 C25 179.8(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.427 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.100 data_1205w875 _database_code_depnum_ccdc_archive 'CCDC 906266' #TrackingRef 'complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Br2 F Mn N2 O5 P, H O0.50, 1.3(H0.40 O0.20)' _chemical_formula_sum 'C26 H25 Br2 F Mn N2 O6 P' _chemical_formula_weight 726.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9095(17) _cell_length_b 15.6772(13) _cell_length_c 13.5492(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.441(3) _cell_angle_gamma 90.00 _cell_volume 1451.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 3026 _cell_measurement_theta_min 2.601 _cell_measurement_theta_max 26.570 _exptl_crystal_description rod _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 3.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.483 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 11331 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5417 _reflns_number_gt 4511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0699P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.025(13) _refine_ls_number_reflns 5417 _refine_ls_number_parameters 371 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.28763(14) 0.33252(7) 0.90648(8) 0.0249(2) Uani 1 1 d . . . P1 P -0.2178(3) 0.36936(12) 0.86731(12) 0.0267(4) Uani 1 1 d . . . O1 O 0.2596(7) 0.4412(3) 0.8482(3) 0.0232(10) Uani 1 1 d . . . O2 O 0.3180(7) 0.3755(3) 1.0388(4) 0.0329(11) Uani 1 1 d . . . O3 O -0.0411(7) 0.3232(3) 0.9096(4) 0.0339(11) Uani 1 1 d . . . O4 O -0.2079(8) 0.4659(4) 0.8922(4) 0.0366(12) Uani 1 1 d . . . H4A H -0.1041 0.4763 0.8677 0.055 Uiso 1 1 d R . . O5 O -0.4038(6) 0.3327(3) 0.8915(3) 0.0247(9) Uani 1 1 d . . . O1W O 0.0958(14) 0.5353(8) 0.0129(6) 0.037(3) Uani 0.50 1 d P . . H1X H 0.1454 0.5320 -0.0409 0.045 Uiso 0.50 1 d PR . . H1Y H 0.1212 0.4964 0.0565 0.045 Uiso 0.50 1 d PR . . O2W O 0.842(3) 0.1486(17) 0.0490(16) 0.059(6) Uani 0.30 1 d P . . H2X H 0.7755 0.1862 0.0138 0.071 Uiso 0.30 1 d PR . . H2Y H 0.8730 0.1670 0.1082 0.071 Uiso 0.30 1 d PR . . O3W O 0.790(3) 0.2580(14) 0.1229(18) 0.028(5) Uani 0.20 1 d P . . H3X H 0.7291 0.2442 0.1707 0.034 Uiso 0.20 1 d PR . . H3Y H 0.7078 0.2692 0.0716 0.034 Uiso 0.20 1 d PR . . N1 N 0.3162(9) 0.2129(4) 0.9536(4) 0.0303(13) Uani 1 1 d . . . N2 N 0.2355(8) 0.2749(4) 0.7725(4) 0.0277(13) Uani 1 1 d . . . C1 C 0.2829(11) 0.4627(5) 0.7571(6) 0.0331(16) Uani 1 1 d . . . C2 C 0.3104(12) 0.5497(6) 0.7349(5) 0.0394(18) Uani 1 1 d . . . H2 H 0.3253 0.5892 0.7867 0.047 Uiso 1 1 calc R . . C3 C 0.3160(12) 0.5778(5) 0.6380(5) 0.0332(17) Uani 1 1 d . . . H3 H 0.3215 0.6358 0.6241 0.040 Uiso 1 1 calc R . . C4 C 0.3131(10) 0.5181(5) 0.5626(6) 0.0325(17) Uani 1 1 d . . . C5 C 0.2870(11) 0.4343(5) 0.5830(5) 0.0333(16) Uani 1 1 d . . . H5 H 0.2776 0.3961 0.5299 0.040 Uiso 1 1 calc R . . C6 C 0.2736(10) 0.4017(5) 0.6753(5) 0.0291(15) Uani 1 1 d . . . C7 C 0.2406(11) 0.3129(5) 0.6896(5) 0.0360(18) Uani 1 1 d . . . H7 H 0.2208 0.2792 0.6325 0.043 Uiso 1 1 calc R . . C8 C 0.1977(9) 0.1835(5) 0.7823(5) 0.0331(16) Uani 1 1 d . . . H8 H 0.0669 0.1762 0.8009 0.040 Uiso 1 1 calc R . . C9 C 0.2115(11) 0.1299(4) 0.6888(5) 0.0298(15) Uani 1 1 d . . . H9A H 0.3368 0.1395 0.6665 0.036 Uiso 1 1 calc R . . H9B H 0.1090 0.1467 0.6356 0.036 Uiso 1 1 calc R . . C10 C 0.1894(12) 0.0346(4) 0.7138(5) 0.0357(18) Uani 1 1 d . . . H10A H 0.0601 0.0249 0.7314 0.043 Uiso 1 1 calc R . . H10B H 0.2014 0.0006 0.6552 0.043 Uiso 1 1 calc R . . C11 C 0.3382(11) 0.0067(4) 0.7970(5) 0.0288(15) Uani 1 1 d . . . H11A H 0.4671 0.0113 0.7772 0.035 Uiso 1 1 calc R . . H11B H 0.3161 -0.0527 0.8120 0.035 Uiso 1 1 calc R . . C12 C 0.3309(11) 0.0593(5) 0.8884(6) 0.0346(16) Uani 1 1 d . . . H12A H 0.4353 0.0413 0.9400 0.042 Uiso 1 1 calc R . . H12B H 0.2076 0.0489 0.9125 0.042 Uiso 1 1 calc R . . C13 C 0.3510(10) 0.1537(5) 0.8706(5) 0.0297(15) Uani 1 1 d . . . H13 H 0.4820 0.1647 0.8539 0.036 Uiso 1 1 calc R . . C14 C 0.3131(10) 0.1865(6) 1.0460(6) 0.0346(16) Uani 1 1 d . . . H14 H 0.3292 0.1285 1.0593 0.042 Uiso 1 1 calc R . . C15 C 0.2870(11) 0.2411(6) 1.1255(6) 0.0359(18) Uani 1 1 d . . . C16 C 0.2523(10) 0.2015(5) 1.2146(6) 0.0350(16) Uani 1 1 d . . . H16 H 0.2461 0.1424 1.2180 0.042 Uiso 1 1 calc R . . C17 C 0.2273(10) 0.2500(4) 1.2973(5) 0.0221(14) Uani 1 1 d . . . C18 C 0.2173(10) 0.3390(5) 1.2934(5) 0.0300(15) Uani 1 1 d . . . H18 H 0.1991 0.3711 1.3490 0.036 Uiso 1 1 calc R . . C19 C 0.2357(10) 0.3772(4) 1.2039(4) 0.0238(13) Uani 1 1 d . . . H19 H 0.2158 0.4358 1.1979 0.029 Uiso 1 1 calc R . . C20 C 0.2835(11) 0.3316(5) 1.1195(5) 0.0337(15) Uani 1 1 d . . . C21 C -0.2264(13) 0.3721(5) 0.7328(5) 0.0383(19) Uani 1 1 d . . . C22 C -0.2028(10) 0.4461(4) 0.6751(5) 0.0264(14) Uani 1 1 d . . . H22 H -0.1754 0.4971 0.7094 0.032 Uiso 1 1 calc R . . C23 C -0.2169(10) 0.4487(5) 0.5742(6) 0.0291(16) Uani 1 1 d . . . H23 H -0.2083 0.4996 0.5398 0.035 Uiso 1 1 calc R . . C24 C -0.2461(12) 0.3677(5) 0.5233(6) 0.0385(19) Uani 1 1 d . . . H24 H -0.2496 0.3658 0.4545 0.046 Uiso 1 1 calc R . . C25 C -0.2692(14) 0.2923(5) 0.5752(6) 0.0385(19) Uani 1 1 d . . . H25 H -0.2897 0.2404 0.5421 0.046 Uiso 1 1 calc R . . C26 C -0.2607(11) 0.2975(5) 0.6746(5) 0.0311(15) Uani 1 1 d . . . Br1 Br 0.34115(11) 0.55241(4) 0.43139(5) 0.03203(18) Uani 1 1 d . . . Br2 Br 0.18952(12) 0.19448(5) 1.41786(5) 0.0368(2) Uani 1 1 d . . . F1 F -0.2893(7) 0.2231(3) 0.7259(3) 0.0385(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0201(5) 0.0255(5) 0.0289(5) -0.0004(4) 0.0033(4) 0.0004(4) P1 0.0255(9) 0.0308(9) 0.0237(8) 0.0045(7) 0.0031(7) 0.0030(7) O1 0.032(3) 0.020(2) 0.019(2) 0.0044(17) 0.0076(18) 0.0033(19) O2 0.025(2) 0.036(3) 0.037(3) 0.005(2) 0.005(2) 0.006(2) O3 0.034(3) 0.037(3) 0.030(2) 0.005(2) 0.004(2) -0.006(2) O4 0.028(3) 0.042(3) 0.038(3) 0.003(2) -0.003(2) 0.005(2) O5 0.027(2) 0.035(3) 0.0142(19) 0.0112(19) 0.0092(16) 0.006(2) O1W 0.028(5) 0.067(8) 0.016(4) -0.009(4) 0.004(4) 0.019(5) O2W 0.024(10) 0.101(18) 0.054(12) -0.030(12) 0.013(8) -0.027(11) O3W 0.029(13) 0.020(12) 0.029(12) -0.003(9) -0.020(10) 0.012(10) N1 0.038(3) 0.026(3) 0.030(3) -0.005(2) 0.014(2) 0.009(3) N2 0.021(3) 0.031(3) 0.026(3) -0.006(2) -0.013(2) -0.002(2) C1 0.035(4) 0.029(4) 0.035(4) 0.006(3) 0.005(3) -0.002(3) C2 0.052(5) 0.032(4) 0.033(4) -0.009(4) 0.003(3) -0.011(4) C3 0.044(4) 0.026(4) 0.033(4) -0.010(3) 0.017(3) 0.000(3) C4 0.021(4) 0.030(4) 0.049(4) -0.006(3) 0.015(3) -0.011(3) C5 0.028(4) 0.037(4) 0.031(4) -0.001(3) -0.007(3) 0.000(3) C6 0.029(4) 0.029(4) 0.027(3) 0.000(3) -0.003(3) -0.003(3) C7 0.041(4) 0.036(4) 0.028(4) 0.000(3) -0.005(3) -0.018(3) C8 0.017(3) 0.045(5) 0.039(4) 0.003(3) 0.012(3) 0.009(3) C9 0.033(4) 0.030(4) 0.029(4) 0.001(3) 0.017(3) -0.004(3) C10 0.055(5) 0.025(4) 0.028(4) 0.006(3) 0.011(3) 0.008(3) C11 0.046(4) 0.016(3) 0.031(3) -0.002(3) 0.027(3) -0.005(3) C12 0.027(3) 0.028(4) 0.054(4) -0.002(4) 0.022(3) -0.013(3) C13 0.029(4) 0.030(4) 0.028(3) 0.009(3) -0.003(3) 0.000(3) C14 0.025(3) 0.030(4) 0.047(4) -0.001(3) -0.003(3) -0.006(3) C15 0.022(4) 0.049(5) 0.033(4) -0.012(3) -0.007(3) 0.004(3) C16 0.033(4) 0.026(4) 0.045(4) 0.000(3) 0.001(3) 0.005(3) C17 0.031(4) 0.012(3) 0.027(3) 0.003(2) 0.015(3) 0.001(2) C18 0.031(4) 0.028(4) 0.033(4) 0.001(3) 0.010(3) 0.000(3) C19 0.029(3) 0.022(3) 0.020(3) 0.000(3) 0.000(3) 0.008(3) C20 0.037(4) 0.028(4) 0.035(4) 0.001(3) 0.003(3) -0.006(3) C21 0.058(5) 0.030(4) 0.020(3) -0.004(3) -0.016(3) -0.012(3) C22 0.034(4) 0.024(3) 0.022(3) 0.003(2) 0.011(3) 0.016(3) C23 0.024(3) 0.022(4) 0.043(4) 0.005(3) 0.011(3) 0.008(3) C24 0.053(5) 0.030(4) 0.040(4) -0.012(3) 0.032(4) -0.021(3) C25 0.066(6) 0.019(4) 0.033(4) 0.007(3) 0.018(4) -0.004(4) C26 0.030(4) 0.028(4) 0.031(4) 0.009(3) -0.010(3) -0.002(3) Br1 0.0437(4) 0.0228(3) 0.0295(3) -0.0049(3) 0.0050(3) 0.0033(3) Br2 0.0433(4) 0.0372(4) 0.0334(4) -0.0015(3) 0.0168(3) 0.0054(4) F1 0.047(3) 0.038(3) 0.030(2) 0.0112(18) 0.0038(18) 0.002(2) _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 1.876(4) . ? Mn1 O2 1.898(5) . ? Mn1 N1 1.981(6) . ? Mn1 N2 2.013(6) . ? Mn1 O5 2.171(4) 1_655 ? Mn1 O3 2.283(5) . ? P1 O3 1.462(5) . ? P1 O5 1.487(5) . ? P1 O4 1.549(6) . ? P1 C21 1.815(7) . ? P1 H4A 1.8508 . ? O1 C1 1.312(9) . ? O2 C20 1.342(9) . ? O4 H4A 0.8495 . ? O5 Mn1 2.171(4) 1_455 ? O1W H1X 0.8514 . ? O1W H1Y 0.8499 . ? O2W H2X 0.8500 . ? O2W H2Y 0.8501 . ? O3W H3X 0.8499 . ? O3W H3Y 0.8474 . ? N1 C14 1.322(10) . ? N1 C13 1.505(9) . ? N2 C7 1.277(9) . ? N2 C8 1.466(10) . ? C1 C2 1.415(12) . ? C1 C6 1.459(11) . ? C2 C3 1.392(11) . ? C2 H2 0.9300 . ? C3 C4 1.383(10) . ? C3 H3 0.9300 . ? C4 C5 1.360(11) . ? C4 Br1 1.895(8) . ? C5 C6 1.367(10) . ? C5 H5 0.9300 . ? C6 C7 1.428(10) . ? C7 H7 0.9300 . ? C8 C9 1.534(10) . ? C8 C13 1.548(10) . ? C8 H8 0.9800 . ? C9 C10 1.545(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.476(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.495(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.509(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9800 . ? C14 C15 1.408(11) . ? C14 H14 0.9300 . ? C15 C16 1.409(12) . ? C15 C20 1.421(12) . ? C16 C17 1.385(10) . ? C16 H16 0.9300 . ? C17 C18 1.397(10) . ? C17 Br2 1.902(6) . ? C18 C19 1.376(10) . ? C18 H18 0.9300 . ? C19 C20 1.428(10) . ? C19 H19 0.9300 . ? C21 C26 1.412(10) . ? C21 C22 1.421(10) . ? C22 C23 1.357(10) . ? C22 H22 0.9300 . ? C23 C24 1.444(10) . ? C23 H23 0.9300 . ? C24 C25 1.397(10) . ? C24 H24 0.9300 . ? C25 C26 1.341(11) . ? C25 H25 0.9300 . ? C26 F1 1.386(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 O1 Mn1 O2 93.8(2) . . ? O1 Mn1 N1 174.0(2) . . ? O2 Mn1 N1 92.3(2) . . ? O1 Mn1 N2 92.0(2) . . ? O2 Mn1 N2 172.7(3) . . ? N1 Mn1 N2 82.1(2) . . ? O1 Mn1 O5 90.07(19) . 1_655 ? O2 Mn1 O5 96.54(19) . 1_655 ? N1 Mn1 O5 88.8(2) . 1_655 ? N2 Mn1 O5 88.0(2) . 1_655 ? O1 Mn1 O3 91.4(2) . . ? O2 Mn1 O3 88.7(2) . . ? N1 Mn1 O3 89.2(2) . . ? N2 Mn1 O3 86.6(2) . . ? O5 Mn1 O3 174.45(19) 1_655 . ? O3 P1 O5 114.9(3) . . ? O3 P1 O4 113.0(3) . . ? O5 P1 O4 109.9(3) . . ? O3 P1 C21 108.0(4) . . ? O5 P1 C21 109.2(3) . . ? O4 P1 C21 100.9(3) . . ? O3 P1 H4A 96.8 . . ? O5 P1 H4A 136.8 . . ? O4 P1 H4A 27.1 . . ? C21 P1 H4A 86.1 . . ? C1 O1 Mn1 127.6(4) . . ? C20 O2 Mn1 125.4(5) . . ? P1 O3 Mn1 137.5(3) . . ? P1 O4 H4A 96.6 . . ? P1 O5 Mn1 156.0(3) . 1_455 ? H1X O1W H1Y 118.9 . . ? H2X O2W H2Y 109.5 . . ? H3X O3W H3Y 109.5 . . ? C14 N1 C13 122.8(6) . . ? C14 N1 Mn1 126.0(5) . . ? C13 N1 Mn1 111.2(4) . . ? C7 N2 C8 124.4(6) . . ? C7 N2 Mn1 124.0(5) . . ? C8 N2 Mn1 111.6(4) . . ? O1 C1 C2 119.1(7) . . ? O1 C1 C6 123.2(7) . . ? C2 C1 C6 117.6(7) . . ? C3 C2 C1 121.9(7) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C4 C3 C2 118.8(7) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 119.5(7) . . ? C5 C4 Br1 119.9(6) . . ? C3 C4 Br1 120.5(6) . . ? C4 C5 C6 125.1(7) . . ? C4 C5 H5 117.4 . . ? C6 C5 H5 117.4 . . ? C5 C6 C7 121.5(7) . . ? C5 C6 C1 116.6(7) . . ? C7 C6 C1 121.8(7) . . ? N2 C7 C6 126.9(7) . . ? N2 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N2 C8 C9 115.2(6) . . ? N2 C8 C13 104.7(6) . . ? C9 C8 C13 110.8(6) . . ? N2 C8 H8 108.6 . . ? C9 C8 H8 108.6 . . ? C13 C8 H8 108.6 . . ? C8 C9 C10 109.2(5) . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? C11 C10 C9 112.0(6) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 111.4(6) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 113.2(6) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N1 C13 C12 117.2(6) . . ? N1 C13 C8 103.0(6) . . ? C12 C13 C8 110.5(6) . . ? N1 C13 H13 108.6 . . ? C12 C13 H13 108.6 . . ? C8 C13 H13 108.6 . . ? N1 C14 C15 123.7(8) . . ? N1 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C14 C15 C16 116.4(8) . . ? C14 C15 C20 124.5(8) . . ? C16 C15 C20 119.0(7) . . ? C17 C16 C15 120.6(7) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 121.9(7) . . ? C16 C17 Br2 119.5(5) . . ? C18 C17 Br2 118.5(5) . . ? C19 C18 C17 117.3(6) . . ? C19 C18 H18 121.4 . . ? C17 C18 H18 121.4 . . ? C18 C19 C20 123.3(7) . . ? C18 C19 H19 118.3 . . ? C20 C19 H19 118.3 . . ? O2 C20 C15 123.7(7) . . ? O2 C20 C19 119.0(7) . . ? C15 C20 C19 117.3(7) . . ? C26 C21 C22 113.1(6) . . ? C26 C21 P1 121.3(6) . . ? C22 C21 P1 125.6(6) . . ? C23 C22 C21 125.6(7) . . ? C23 C22 H22 117.2 . . ? C21 C22 H22 117.2 . . ? C22 C23 C24 116.0(7) . . ? C22 C23 H23 122.0 . . ? C24 C23 H23 122.0 . . ? C25 C24 C23 121.5(7) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C24 117.6(7) . . ? C26 C25 H25 121.2 . . ? C24 C25 H25 121.2 . . ? C25 C26 F1 117.6(6) . . ? C25 C26 C21 126.1(7) . . ? F1 C26 C21 116.2(6) . . ? 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 O2 Mn1 O1 C1 160.6(6) . . . . ? N1 Mn1 O1 C1 -15(3) . . . . ? N2 Mn1 O1 C1 -24.0(6) . . . . ? O5 Mn1 O1 C1 64.0(6) 1_655 . . . ? O3 Mn1 O1 C1 -110.6(6) . . . . ? O1 Mn1 O2 C20 157.4(6) . . . . ? N1 Mn1 O2 C20 -23.0(6) . . . . ? N2 Mn1 O2 C20 16(2) . . . . ? O5 Mn1 O2 C20 -112.1(6) 1_655 . . . ? O3 Mn1 O2 C20 66.1(6) . . . . ? O5 P1 O3 Mn1 177.9(4) . . . . ? O4 P1 O3 Mn1 -54.9(5) . . . . ? C21 P1 O3 Mn1 55.8(6) . . . . ? O1 Mn1 O3 P1 11.8(5) . . . . ? O2 Mn1 O3 P1 105.6(5) . . . . ? N1 Mn1 O3 P1 -162.1(5) . . . . ? N2 Mn1 O3 P1 -80.0(5) . . . . ? O5 Mn1 O3 P1 -93(2) 1_655 . . . ? O3 P1 O5 Mn1 162.8(6) . . . 1_455 ? O4 P1 O5 Mn1 34.0(7) . . . 1_455 ? C21 P1 O5 Mn1 -75.8(7) . . . 1_455 ? O1 Mn1 N1 C14 -172.4(19) . . . . ? O2 Mn1 N1 C14 11.8(6) . . . . ? N2 Mn1 N1 C14 -163.6(6) . . . . ? O5 Mn1 N1 C14 108.3(6) 1_655 . . . ? O3 Mn1 N1 C14 -76.9(6) . . . . ? O1 Mn1 N1 C13 10(3) . . . . ? O2 Mn1 N1 C13 -165.9(5) . . . . ? N2 Mn1 N1 C13 18.7(5) . . . . ? O5 Mn1 N1 C13 -69.4(5) 1_655 . . . ? O3 Mn1 N1 C13 105.5(5) . . . . ? O1 Mn1 N2 C7 15.2(6) . . . . ? O2 Mn1 N2 C7 156.9(16) . . . . ? N1 Mn1 N2 C7 -163.9(7) . . . . ? O5 Mn1 N2 C7 -74.8(6) 1_655 . . . ? O3 Mn1 N2 C7 106.5(6) . . . . ? O1 Mn1 N2 C8 -166.7(4) . . . . ? O2 Mn1 N2 C8 -25(2) . . . . ? N1 Mn1 N2 C8 14.2(4) . . . . ? O5 Mn1 N2 C8 103.3(4) 1_655 . . . ? O3 Mn1 N2 C8 -75.4(4) . . . . ? Mn1 O1 C1 C2 -162.2(6) . . . . ? Mn1 O1 C1 C6 20.6(10) . . . . ? O1 C1 C2 C3 -173.3(7) . . . . ? C6 C1 C2 C3 4.1(12) . . . . ? C1 C2 C3 C4 -6.2(12) . . . . ? C2 C3 C4 C5 6.0(11) . . . . ? C2 C3 C4 Br1 -175.0(6) . . . . ? C3 C4 C5 C6 -3.9(12) . . . . ? Br1 C4 C5 C6 177.0(6) . . . . ? C4 C5 C6 C7 178.2(7) . . . . ? C4 C5 C6 C1 1.7(11) . . . . ? O1 C1 C6 C5 175.6(7) . . . . ? C2 C1 C6 C5 -1.7(10) . . . . ? O1 C1 C6 C7 -0.9(11) . . . . ? C2 C1 C6 C7 -178.2(8) . . . . ? C8 N2 C7 C6 178.9(7) . . . . ? Mn1 N2 C7 C6 -3.2(12) . . . . ? C5 C6 C7 N2 176.1(8) . . . . ? C1 C6 C7 N2 -7.6(13) . . . . ? C7 N2 C8 C9 13.9(10) . . . . ? Mn1 N2 C8 C9 -164.2(5) . . . . ? C7 N2 C8 C13 135.9(7) . . . . ? Mn1 N2 C8 C13 -42.2(6) . . . . ? N2 C8 C9 C10 174.2(6) . . . . ? C13 C8 C9 C10 55.6(8) . . . . ? C8 C9 C10 C11 -57.5(8) . . . . ? C9 C10 C11 C12 56.8(7) . . . . ? C10 C11 C12 C13 -55.4(8) . . . . ? C14 N1 C13 C12 15.6(10) . . . . ? Mn1 N1 C13 C12 -166.7(5) . . . . ? C14 N1 C13 C8 137.1(7) . . . . ? Mn1 N1 C13 C8 -45.2(6) . . . . ? C11 C12 C13 N1 171.3(6) . . . . ? C11 C12 C13 C8 53.7(8) . . . . ? N2 C8 C13 N1 54.9(6) . . . . ? C9 C8 C13 N1 179.7(5) . . . . ? N2 C8 C13 C12 -179.1(5) . . . . ? C9 C8 C13 C12 -54.3(8) . . . . ? C13 N1 C14 C15 177.9(7) . . . . ? Mn1 N1 C14 C15 0.5(10) . . . . ? N1 C14 C15 C16 169.0(7) . . . . ? N1 C14 C15 C20 -7.7(12) . . . . ? C14 C15 C16 C17 179.2(7) . . . . ? C20 C15 C16 C17 -4.0(11) . . . . ? C15 C16 C17 C18 6.0(11) . . . . ? C15 C16 C17 Br2 -177.9(5) . . . . ? C16 C17 C18 C19 -0.7(10) . . . . ? Br2 C17 C18 C19 -176.9(5) . . . . ? C17 C18 C19 C20 -6.6(11) . . . . ? Mn1 O2 C20 C15 23.2(10) . . . . ? Mn1 O2 C20 C19 -155.1(5) . . . . ? C14 C15 C20 O2 -4.6(12) . . . . ? C16 C15 C20 O2 178.8(7) . . . . ? C14 C15 C20 C19 173.7(7) . . . . ? C16 C15 C20 C19 -2.8(10) . . . . ? C18 C19 C20 O2 -173.2(7) . . . . ? C18 C19 C20 C15 8.3(11) . . . . ? O3 P1 C21 C26 69.2(8) . . . . ? O5 P1 C21 C26 -56.4(8) . . . . ? O4 P1 C21 C26 -172.1(7) . . . . ? O3 P1 C21 C22 -111.5(7) . . . . ? O5 P1 C21 C22 123.0(7) . . . . ? O4 P1 C21 C22 7.2(8) . . . . ? C26 C21 C22 C23 2.1(12) . . . . ? P1 C21 C22 C23 -177.3(6) . . . . ? C21 C22 C23 C24 -4.1(11) . . . . ? C22 C23 C24 C25 3.4(12) . . . . ? C23 C24 C25 C26 -0.9(13) . . . . ? C24 C25 C26 F1 178.2(7) . . . . ? C24 C25 C26 C21 -1.4(14) . . . . ? C22 C21 C26 C25 0.9(13) . . . . ? P1 C21 C26 C25 -179.7(7) . . . . ? C22 C21 C26 F1 -178.7(6) . . . . ? P1 C21 C26 F1 0.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.545 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.110 data_102 _database_code_depnum_ccdc_archive 'CCDC 906267' #TrackingRef 'complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H26 Br2 Mn N2 O5 P, C H4 O, H2 O' _chemical_formula_sum 'C28 H31 Br2 Mn N2 O7 P' _chemical_formula_weight 753.28 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9258(8) _cell_length_b 15.9043(19) _cell_length_c 13.5363(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.125(2) _cell_angle_gamma 90.00 _cell_volume 1476.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4597 _cell_measurement_theta_min 2.563 _cell_measurement_theta_max 26.584 _exptl_crystal_description rod _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 758 _exptl_absorpt_coefficient_mu 3.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.446 _exptl_absorpt_correction_T_max 0.521 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 11555 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.99 _reflns_number_total 5164 _reflns_number_gt 4354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0616P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.034(12) _refine_ls_number_reflns 5164 _refine_ls_number_parameters 372 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.30076(17) 0.32728(8) 0.91222(8) 0.0305(3) Uani 1 1 d . . . P1 P -0.2065(3) 0.29321(12) 0.87432(15) 0.0289(4) Uani 1 1 d . . . O1 O 0.2859(8) 0.2184(3) 0.8532(4) 0.0335(12) Uani 1 1 d . . . O2 O 0.3372(8) 0.2885(3) 1.0437(4) 0.0321(12) Uani 1 1 d . . . O3 O -0.0204(7) 0.3315(4) 0.9189(4) 0.0355(12) Uani 1 1 d . . . O5 O -0.3827(7) 0.3372(4) 0.9048(4) 0.0327(12) Uani 1 1 d . . . O4 O -0.2123(8) 0.1969(3) 0.9006(4) 0.0320(12) Uani 1 1 d . . . H4B H -0.3393 0.1826 0.9162 0.048 Uiso 1 1 d R . . O6 O 0.2332(9) 0.9572(5) 0.9399(5) 0.0530(16) Uani 1 1 d . . . H6A H 0.3311 0.9372 0.9920 0.064 Uiso 1 1 d R . . O1W O 0.8996(7) 0.6133(4) 0.0102(4) 0.0356(12) Uani 1 1 d . . . H1X H 0.8757 0.6648 0.0199 0.053 Uiso 1 1 d R . . H1Y H 0.8018 0.5910 -0.0252 0.053 Uiso 1 1 d R . . N2 N 0.2429(9) 0.3815(4) 0.7781(4) 0.0304(13) Uani 1 1 d . . . N1 N 0.3198(9) 0.4457(4) 0.9561(5) 0.0329(15) Uani 1 1 d . . . C1 C 0.3014(11) 0.1985(5) 0.7630(6) 0.0313(16) Uani 1 1 d . . . C2 C 0.3338(10) 0.1108(6) 0.7398(6) 0.0321(16) Uani 1 1 d . . . H2 H 0.3441 0.0711 0.7907 0.038 Uiso 1 1 calc R . . C3 C 0.3494(11) 0.0854(5) 0.6441(5) 0.0331(18) Uani 1 1 d . . . H3 H 0.3702 0.0290 0.6306 0.040 Uiso 1 1 calc R . . C4 C 0.3338(12) 0.1450(5) 0.5668(6) 0.0350(18) Uani 1 1 d . . . C5 C 0.3054(13) 0.2288(5) 0.5862(6) 0.0385(19) Uani 1 1 d . . . H5 H 0.2995 0.2680 0.5348 0.046 Uiso 1 1 calc R . . C6 C 0.2854(11) 0.2552(5) 0.6822(6) 0.0305(16) Uani 1 1 d . . . C7 C 0.2475(11) 0.3450(5) 0.6931(5) 0.0319(17) Uani 1 1 d . . . H7 H 0.2254 0.3777 0.6356 0.038 Uiso 1 1 calc R . . C8 C 0.2007(11) 0.4716(6) 0.7874(5) 0.0328(16) Uani 1 1 d . . . H8 H 0.0701 0.4760 0.8069 0.039 Uiso 1 1 calc R . . C9 C 0.1984(12) 0.5214(5) 0.6920(6) 0.0329(17) Uani 1 1 d . . . H9A H 0.0971 0.5003 0.6412 0.040 Uiso 1 1 calc R . . H9B H 0.3228 0.5160 0.6675 0.040 Uiso 1 1 calc R . . C10 C 0.1583(11) 0.6166(5) 0.7156(5) 0.0326(15) Uani 1 1 d . . . H10A H 0.1603 0.6502 0.6559 0.039 Uiso 1 1 calc R . . H10B H 0.0302 0.6220 0.7360 0.039 Uiso 1 1 calc R . . C11 C 0.3089(11) 0.6482(5) 0.7963(5) 0.0321(17) Uani 1 1 d . . . H11A H 0.2844 0.7068 0.8098 0.038 Uiso 1 1 calc R . . H11B H 0.4371 0.6438 0.7757 0.038 Uiso 1 1 calc R . . C12 C 0.3016(12) 0.5970(5) 0.8880(6) 0.0334(18) Uani 1 1 d . . . H12A H 0.3960 0.6188 0.9416 0.040 Uiso 1 1 calc R . . H12B H 0.1731 0.6020 0.9081 0.040 Uiso 1 1 calc R . . C13 C 0.3430(13) 0.5086(5) 0.8722(6) 0.0351(18) Uani 1 1 d . . . H13 H 0.4755 0.5037 0.8552 0.042 Uiso 1 1 calc R . . C14 C 0.3117(9) 0.4743(6) 1.0478(5) 0.0284(15) Uani 1 1 d . . . H14 H 0.3202 0.5319 1.0595 0.034 Uiso 1 1 calc R . . C15 C 0.2904(10) 0.4192(5) 1.1286(5) 0.0293(17) Uani 1 1 d . . . C16 C 0.2597(11) 0.4619(6) 1.2195(5) 0.0351(17) Uani 1 1 d . . . H16 H 0.2594 0.5203 1.2237 0.042 Uiso 1 1 calc R . . C17 C 0.2307(11) 0.4118(5) 1.3003(6) 0.0345(18) Uani 1 1 d . . . C18 C 0.2316(11) 0.3238(5) 1.2954(5) 0.0298(16) Uani 1 1 d . . . H18 H 0.2092 0.2918 1.3502 0.036 Uiso 1 1 calc R . . C19 C 0.2658(10) 0.2854(5) 1.2088(5) 0.0263(15) Uani 1 1 d . . . H19 H 0.2689 0.2269 1.2062 0.032 Uiso 1 1 calc R . . C20 C 0.2959(11) 0.3311(6) 1.1249(5) 0.0341(17) Uani 1 1 d . . . C21 C -0.2245(11) 0.2952(5) 0.7403(6) 0.0301(16) Uani 1 1 d . . . C22 C -0.1881(11) 0.2272(5) 0.6811(6) 0.0341(17) Uani 1 1 d . . . H22 H -0.1530 0.1763 0.7124 0.041 Uiso 1 1 calc R . . C23 C -0.2011(12) 0.2309(5) 0.5791(6) 0.0324(17) Uani 1 1 d . . . H23 H -0.1823 0.1831 0.5422 0.039 Uiso 1 1 calc R . . C24 C -0.2441(10) 0.3098(5) 0.5311(5) 0.0286(15) Uani 1 1 d . . . C25 C -0.2785(11) 0.3796(5) 0.5885(5) 0.0293(16) Uani 1 1 d . . . H25 H -0.3110 0.4307 0.5572 0.035 Uiso 1 1 calc R . . C26 C -0.2651(11) 0.3740(6) 0.6914(6) 0.0376(19) Uani 1 1 d . . . H26 H -0.2825 0.4218 0.7287 0.045 Uiso 1 1 calc R . . C27 C -0.2558(12) 0.3166(5) 0.4154(5) 0.0318(17) Uani 1 1 d . . . H27A H -0.3272 0.3663 0.3924 0.048 Uiso 1 1 calc R . . H27B H -0.3210 0.2680 0.3846 0.048 Uiso 1 1 calc R . . H27C H -0.1264 0.3197 0.3979 0.048 Uiso 1 1 calc R . . C28 C 0.2087(13) 0.8977(6) 0.8625(6) 0.0415(19) Uani 1 1 d . . . H28A H 0.1723 0.9258 0.7999 0.062 Uiso 1 1 calc R . . H28B H 0.1083 0.8586 0.8735 0.062 Uiso 1 1 calc R . . H28C H 0.3289 0.8679 0.8611 0.062 Uiso 1 1 calc R . . Br1 Br 0.36514(11) 0.11265(5) 0.43448(5) 0.03198(18) Uani 1 1 d . . . Br2 Br 0.19163(11) 0.46799(5) 1.42067(5) 0.03134(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0309(6) 0.0296(7) 0.0306(6) 0.0006(5) 0.0032(5) -0.0005(5) P1 0.0280(9) 0.0272(11) 0.0323(10) 0.0053(7) 0.0065(8) -0.0013(8) O1 0.029(3) 0.032(3) 0.042(3) 0.000(2) 0.015(2) -0.002(2) O2 0.033(3) 0.031(3) 0.034(3) -0.004(2) 0.010(2) 0.004(2) O3 0.027(3) 0.039(3) 0.042(3) 0.000(3) 0.011(2) -0.003(3) O5 0.030(3) 0.035(3) 0.036(3) 0.001(2) 0.012(2) 0.011(2) O4 0.037(3) 0.028(3) 0.031(3) 0.008(2) 0.007(2) -0.012(2) O6 0.053(4) 0.053(5) 0.053(4) 0.000(3) 0.008(3) 0.000(3) O1W 0.035(3) 0.035(3) 0.039(3) -0.002(3) 0.012(2) 0.008(3) N2 0.027(3) 0.037(4) 0.027(3) 0.000(3) 0.002(2) -0.007(3) N1 0.035(3) 0.031(4) 0.035(3) -0.003(3) 0.012(3) -0.011(3) C1 0.030(4) 0.028(4) 0.035(4) 0.009(3) 0.004(3) 0.007(3) C2 0.025(3) 0.033(4) 0.039(4) 0.003(4) 0.008(3) 0.006(4) C3 0.034(4) 0.036(5) 0.028(4) -0.016(3) 0.000(3) 0.012(3) C4 0.038(4) 0.035(4) 0.031(4) -0.007(3) 0.004(3) 0.007(3) C5 0.045(5) 0.035(5) 0.034(4) 0.010(3) 0.003(3) 0.009(4) C6 0.034(4) 0.023(4) 0.034(4) -0.004(3) 0.003(3) -0.003(3) C7 0.033(4) 0.034(4) 0.028(4) -0.004(3) 0.004(3) 0.005(3) C8 0.040(4) 0.032(4) 0.028(3) 0.005(3) 0.009(3) 0.007(4) C9 0.036(4) 0.028(4) 0.036(4) 0.004(3) 0.009(3) 0.003(3) C10 0.037(4) 0.028(4) 0.031(3) 0.000(3) 0.003(3) -0.001(4) C11 0.033(4) 0.031(4) 0.031(4) 0.009(3) 0.003(3) 0.001(3) C12 0.039(4) 0.031(5) 0.032(4) 0.006(3) 0.014(3) -0.007(3) C13 0.045(5) 0.028(4) 0.032(4) -0.005(3) 0.007(3) 0.002(4) C14 0.026(3) 0.040(4) 0.020(3) -0.003(3) 0.005(2) -0.011(4) C15 0.020(3) 0.046(5) 0.023(3) -0.005(3) 0.004(3) -0.008(3) C16 0.034(4) 0.037(5) 0.036(4) -0.006(4) 0.011(3) -0.023(4) C17 0.028(4) 0.031(4) 0.043(4) 0.001(3) 0.000(3) 0.009(3) C18 0.032(4) 0.031(4) 0.027(3) 0.004(3) 0.007(3) 0.007(3) C19 0.024(3) 0.024(4) 0.032(4) 0.009(3) 0.008(3) 0.005(3) C20 0.038(4) 0.036(4) 0.026(3) -0.002(3) -0.005(3) 0.001(4) C21 0.026(4) 0.029(4) 0.034(4) -0.004(3) 0.002(3) -0.006(3) C22 0.035(4) 0.038(5) 0.032(4) 0.006(3) 0.013(3) -0.002(3) C23 0.034(4) 0.023(4) 0.039(4) -0.008(3) -0.001(3) -0.006(3) C24 0.029(4) 0.023(4) 0.036(4) -0.009(3) 0.012(3) -0.003(3) C25 0.031(4) 0.025(4) 0.029(4) -0.005(3) -0.006(3) -0.004(3) C26 0.032(4) 0.046(5) 0.032(4) 0.013(3) -0.008(3) 0.003(4) C27 0.041(4) 0.022(4) 0.032(4) 0.002(3) 0.000(3) 0.003(3) C28 0.041(5) 0.041(5) 0.041(4) 0.000(4) 0.006(4) 0.000(4) Br1 0.0359(4) 0.0278(4) 0.0335(4) -0.0084(3) 0.0093(3) 0.0055(3) Br2 0.0340(4) 0.0364(4) 0.0265(3) -0.0066(3) 0.0142(3) -0.0025(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 1.867(5) . ? Mn1 O1 1.904(6) . ? Mn1 N1 1.974(6) . ? Mn1 N2 1.999(6) . ? Mn1 O5 2.214(5) 1_655 ? Mn1 O3 2.240(5) . ? P1 O3 1.476(6) . ? P1 O5 1.514(5) . ? P1 O4 1.575(6) . ? P1 C21 1.801(8) . ? O1 C1 1.280(9) . ? O2 C20 1.355(9) . ? O5 Mn1 2.214(5) 1_455 ? O4 H4B 0.9600 . ? O6 C28 1.405(11) . ? O6 H6A 0.9600 . ? O1W H1X 0.8500 . ? O1W H1Y 0.8500 . ? N2 C7 1.293(9) . ? N2 C8 1.472(11) . ? N1 C14 1.330(9) . ? N1 C13 1.539(10) . ? C1 C6 1.410(10) . ? C1 C2 1.453(12) . ? C2 C3 1.376(10) . ? C2 H2 0.9300 . ? C3 C4 1.404(12) . ? C3 H3 0.9300 . ? C4 C5 1.378(12) . ? C4 Br1 1.906(8) . ? C5 C6 1.391(11) . ? C5 H5 0.9300 . ? C6 C7 1.464(11) . ? C7 H7 0.9300 . ? C8 C9 1.513(10) . ? C8 C13 1.521(11) . ? C8 H8 0.9800 . ? C9 C10 1.581(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.487(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.491(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.457(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13 0.9800 . ? C14 C15 1.425(11) . ? C14 H14 0.9300 . ? C15 C20 1.403(12) . ? C15 C16 1.446(10) . ? C16 C17 1.391(11) . ? C16 H16 0.9300 . ? C17 C18 1.401(11) . ? C17 Br2 1.911(8) . ? C18 C19 1.373(10) . ? C18 H18 0.9300 . ? C19 C20 1.389(10) . ? C19 H19 0.9300 . ? C21 C22 1.390(11) . ? C21 C26 1.427(11) . ? C22 C23 1.372(11) . ? C22 H22 0.9300 . ? C23 C24 1.424(11) . ? C23 H23 0.9300 . ? C24 C25 1.395(10) . ? C24 C27 1.561(10) . ? C25 C26 1.386(10) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 95.3(2) . . ? O2 Mn1 N1 91.9(3) . . ? O1 Mn1 N1 172.6(3) . . ? O2 Mn1 N2 172.4(3) . . ? O1 Mn1 N2 91.1(3) . . ? N1 Mn1 N2 81.8(3) . . ? O2 Mn1 O5 93.7(2) . 1_655 ? O1 Mn1 O5 92.4(2) . 1_655 ? N1 Mn1 O5 85.5(2) . 1_655 ? N2 Mn1 O5 90.1(2) . 1_655 ? O2 Mn1 O3 88.4(2) . . ? O1 Mn1 O3 92.8(2) . . ? N1 Mn1 O3 89.0(3) . . ? N2 Mn1 O3 87.2(2) . . ? O5 Mn1 O3 174.2(2) 1_655 . ? O3 P1 O5 112.9(3) . . ? O3 P1 O4 111.0(3) . . ? O5 P1 O4 110.0(3) . . ? O3 P1 C21 109.7(3) . . ? O5 P1 C21 108.9(3) . . ? O4 P1 C21 104.1(3) . . ? C1 O1 Mn1 128.3(5) . . ? C20 O2 Mn1 126.3(5) . . ? P1 O3 Mn1 141.8(4) . . ? P1 O5 Mn1 145.1(4) . 1_455 ? P1 O4 H4B 109.5 . . ? C28 O6 H6A 108.9 . . ? H1X O1W H1Y 109.5 . . ? C7 N2 C8 123.0(6) . . ? C7 N2 Mn1 126.0(6) . . ? C8 N2 Mn1 111.0(4) . . ? C14 N1 C13 119.3(7) . . ? C14 N1 Mn1 126.7(6) . . ? C13 N1 Mn1 114.0(5) . . ? O1 C1 C6 125.0(7) . . ? O1 C1 C2 118.7(7) . . ? C6 C1 C2 116.3(7) . . ? C3 C2 C1 121.4(7) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 119.6(8) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.7(7) . . ? C5 C4 Br1 118.6(6) . . ? C3 C4 Br1 120.7(6) . . ? C4 C5 C6 120.3(8) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 121.7(7) . . ? C5 C6 C7 115.5(7) . . ? C1 C6 C7 122.8(7) . . ? N2 C7 C6 123.7(7) . . ? N2 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? N2 C8 C9 114.5(6) . . ? N2 C8 C13 109.0(6) . . ? C9 C8 C13 111.7(7) . . ? N2 C8 H8 107.1 . . ? C9 C8 H8 107.1 . . ? C13 C8 H8 107.1 . . ? C8 C9 C10 108.0(6) . . ? C8 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? C8 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C11 C10 C9 110.3(7) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 108.9(7) . . ? C10 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? C10 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? C13 C12 C11 112.0(7) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C8 111.3(7) . . ? C12 C13 N1 118.4(6) . . ? C8 C13 N1 100.5(6) . . ? C12 C13 H13 108.7 . . ? C8 C13 H13 108.7 . . ? N1 C13 H13 108.7 . . ? N1 C14 C15 121.9(8) . . ? N1 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C20 C15 C14 125.4(7) . . ? C20 C15 C16 120.5(7) . . ? C14 C15 C16 114.1(8) . . ? C17 C16 C15 117.1(8) . . ? C17 C16 H16 121.5 . . ? C15 C16 H16 121.5 . . ? C16 C17 C18 122.2(8) . . ? C16 C17 Br2 117.1(6) . . ? C18 C17 Br2 120.6(6) . . ? C19 C18 C17 119.2(7) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 122.0(7) . . ? C18 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? O2 C20 C19 118.3(7) . . ? O2 C20 C15 122.6(7) . . ? C19 C20 C15 119.1(7) . . ? C22 C21 C26 117.1(7) . . ? C22 C21 P1 125.1(6) . . ? C26 C21 P1 117.6(6) . . ? C23 C22 C21 123.8(8) . . ? C23 C22 H22 118.1 . . ? C21 C22 H22 118.1 . . ? C22 C23 C24 118.5(7) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C25 C24 C23 119.2(7) . . ? C25 C24 C27 121.0(7) . . ? C23 C24 C27 119.8(6) . . ? C26 C25 C24 121.1(8) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C21 120.2(8) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Mn1 O1 C1 -164.0(6) . . . . ? N1 Mn1 O1 C1 3(2) . . . . ? N2 Mn1 O1 C1 20.0(7) . . . . ? O5 Mn1 O1 C1 -70.1(6) 1_655 . . . ? O3 Mn1 O1 C1 107.3(6) . . . . ? O1 Mn1 O2 C20 -156.4(6) . . . . ? N1 Mn1 O2 C20 25.3(6) . . . . ? N2 Mn1 O2 C20 -9(2) . . . . ? O5 Mn1 O2 C20 110.8(6) 1_655 . . . ? O3 Mn1 O2 C20 -63.7(6) . . . . ? O5 P1 O3 Mn1 -171.2(5) . . . . ? O4 P1 O3 Mn1 64.9(6) . . . . ? C21 P1 O3 Mn1 -49.6(7) . . . . ? O2 Mn1 O3 P1 -115.7(6) . . . . ? O1 Mn1 O3 P1 -20.4(6) . . . . ? N1 Mn1 O3 P1 152.4(6) . . . . ? N2 Mn1 O3 P1 70.5(6) . . . . ? O5 Mn1 O3 P1 132.2(18) 1_655 . . . ? O3 P1 O5 Mn1 -163.7(5) . . . 1_455 ? O4 P1 O5 Mn1 -39.2(6) . . . 1_455 ? C21 P1 O5 Mn1 74.3(6) . . . 1_455 ? O2 Mn1 N2 C7 -161.0(17) . . . . ? O1 Mn1 N2 C7 -13.6(7) . . . . ? N1 Mn1 N2 C7 164.2(7) . . . . ? O5 Mn1 N2 C7 78.8(6) 1_655 . . . ? O3 Mn1 N2 C7 -106.4(7) . . . . ? O2 Mn1 N2 C8 21(2) . . . . ? O1 Mn1 N2 C8 168.8(5) . . . . ? N1 Mn1 N2 C8 -13.4(5) . . . . ? O5 Mn1 N2 C8 -98.8(5) 1_655 . . . ? O3 Mn1 N2 C8 76.0(5) . . . . ? O2 Mn1 N1 C14 -13.7(6) . . . . ? O1 Mn1 N1 C14 179.5(17) . . . . ? N2 Mn1 N1 C14 162.0(7) . . . . ? O5 Mn1 N1 C14 -107.3(6) 1_655 . . . ? O3 Mn1 N1 C14 74.8(6) . . . . ? O2 Mn1 N1 C13 167.3(5) . . . . ? O1 Mn1 N1 C13 0(2) . . . . ? N2 Mn1 N1 C13 -17.0(5) . . . . ? O5 Mn1 N1 C13 73.7(5) 1_655 . . . ? O3 Mn1 N1 C13 -104.3(5) . . . . ? Mn1 O1 C1 C6 -16.5(11) . . . . ? Mn1 O1 C1 C2 164.9(5) . . . . ? O1 C1 C2 C3 179.3(7) . . . . ? C6 C1 C2 C3 0.5(11) . . . . ? C1 C2 C3 C4 0.0(11) . . . . ? C2 C3 C4 C5 0.8(12) . . . . ? C2 C3 C4 Br1 177.5(6) . . . . ? C3 C4 C5 C6 -2.1(13) . . . . ? Br1 C4 C5 C6 -178.8(6) . . . . ? C4 C5 C6 C1 2.7(13) . . . . ? C4 C5 C6 C7 -177.5(8) . . . . ? O1 C1 C6 C5 179.5(8) . . . . ? C2 C1 C6 C5 -1.8(11) . . . . ? O1 C1 C6 C7 -0.3(13) . . . . ? C2 C1 C6 C7 178.3(7) . . . . ? C8 N2 C7 C6 -178.8(7) . . . . ? Mn1 N2 C7 C6 3.9(11) . . . . ? C5 C6 C7 N2 -173.4(8) . . . . ? C1 C6 C7 N2 6.5(12) . . . . ? C7 N2 C8 C9 -10.3(10) . . . . ? Mn1 N2 C8 C9 167.4(5) . . . . ? C7 N2 C8 C13 -136.2(7) . . . . ? Mn1 N2 C8 C13 41.5(7) . . . . ? N2 C8 C9 C10 -178.2(6) . . . . ? C13 C8 C9 C10 -53.7(8) . . . . ? C8 C9 C10 C11 57.4(8) . . . . ? C9 C10 C11 C12 -60.2(8) . . . . ? C10 C11 C12 C13 61.2(9) . . . . ? C11 C12 C13 C8 -58.0(9) . . . . ? C11 C12 C13 N1 -173.6(7) . . . . ? N2 C8 C13 C12 -177.2(6) . . . . ? C9 C8 C13 C12 55.4(9) . . . . ? N2 C8 C13 N1 -51.0(7) . . . . ? C9 C8 C13 N1 -178.4(6) . . . . ? C14 N1 C13 C12 -16.8(10) . . . . ? Mn1 N1 C13 C12 162.3(6) . . . . ? C14 N1 C13 C8 -138.1(7) . . . . ? Mn1 N1 C13 C8 41.0(7) . . . . ? C13 N1 C14 C15 -180.0(7) . . . . ? Mn1 N1 C14 C15 1.1(10) . . . . ? N1 C14 C15 C20 7.0(11) . . . . ? N1 C14 C15 C16 -172.6(7) . . . . ? C20 C15 C16 C17 -1.8(10) . . . . ? C14 C15 C16 C17 177.7(6) . . . . ? C15 C16 C17 C18 0.3(11) . . . . ? C15 C16 C17 Br2 179.7(5) . . . . ? C16 C17 C18 C19 1.3(11) . . . . ? Br2 C17 C18 C19 -178.1(6) . . . . ? C17 C18 C19 C20 -1.3(11) . . . . ? Mn1 O2 C20 C19 157.6(5) . . . . ? Mn1 O2 C20 C15 -25.1(10) . . . . ? C18 C19 C20 O2 177.1(7) . . . . ? C18 C19 C20 C15 -0.3(11) . . . . ? C14 C15 C20 O2 5.0(12) . . . . ? C16 C15 C20 O2 -175.4(7) . . . . ? C14 C15 C20 C19 -177.7(7) . . . . ? C16 C15 C20 C19 1.9(11) . . . . ? O3 P1 C21 C22 100.8(7) . . . . ? O5 P1 C21 C22 -135.3(7) . . . . ? O4 P1 C21 C22 -18.0(8) . . . . ? O3 P1 C21 C26 -74.3(7) . . . . ? O5 P1 C21 C26 49.6(7) . . . . ? O4 P1 C21 C26 166.9(6) . . . . ? C26 C21 C22 C23 -4.2(12) . . . . ? P1 C21 C22 C23 -179.3(6) . . . . ? C21 C22 C23 C24 3.5(12) . . . . ? C22 C23 C24 C25 -2.3(11) . . . . ? C22 C23 C24 C27 178.8(7) . . . . ? C23 C24 C25 C26 2.2(11) . . . . ? C27 C24 C25 C26 -178.9(7) . . . . ? C24 C25 C26 C21 -3.0(12) . . . . ? C22 C21 C26 C25 3.8(11) . . . . ? P1 C21 C26 C25 179.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.456 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.113