# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # 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_mnschifm #TrackingRef 'mnschifm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 F6 Mn N4 O7 S2' _chemical_formula_weight 695.56 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.3603(10) _cell_length_b 17.4152(19) _cell_length_c 18.206(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2967.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4225 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.73 _exptl_crystal_description PLATES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9239 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17052 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6419 _reflns_number_gt 5785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+2.9858P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(3) _refine_ls_number_reflns 6419 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1632 _refine_ls_goodness_of_fit_ref 1.294 _refine_ls_restrained_S_all 1.294 _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 O7 O 0.5618(5) 0.7955(2) 0.8496(2) 0.0304(10) Uani 1 1 d . . . O6 O 0.4457(6) 0.6865(3) 0.7931(3) 0.0440(13) Uani 1 1 d . . . O5 O 0.6825(5) 0.6736(2) 0.8441(2) 0.0336(11) Uani 1 1 d . . . S2 S 0.54838(17) 0.71411(8) 0.84424(8) 0.0204(3) Uani 1 1 d . . . F6 F 0.3526(5) 0.7201(3) 0.9463(3) 0.0598(14) Uani 1 1 d . . . F5 F 0.5667(6) 0.7084(3) 0.9865(2) 0.0506(12) Uani 1 1 d . . . F4 F 0.4595(5) 0.6114(2) 0.9380(3) 0.0562(13) Uani 1 1 d . . . C22 C 0.4788(8) 0.6873(4) 0.9338(4) 0.0341(16) Uani 1 1 d . . . Mn1 Mn 0.30550(9) 0.99300(4) 0.82350(4) 0.01415(19) Uani 1 1 d . . . S1 S 0.04128(16) 1.10216(8) 0.90801(8) 0.0205(3) Uani 1 1 d . . . N1 N 0.4203(5) 0.9601(3) 0.9243(2) 0.0178(10) Uani 1 1 d . . . N2 N 0.5361(6) 1.0348(3) 0.8045(2) 0.0196(10) Uani 1 1 d . . . H2D H 0.543(9) 1.082(4) 0.786(4) 0.050 Uiso 1 1 d . . . N3 N 0.3993(5) 0.9035(3) 0.7490(3) 0.0174(10) Uani 1 1 d . . . H3D H 0.429(9) 0.880(5) 0.783(4) 0.050 Uiso 1 1 d . . . N4 N 0.1389(5) 0.8990(3) 0.8133(3) 0.0175(10) Uani 1 1 d . . . O1 O 0.2048(6) 1.0686(3) 0.7466(3) 0.0296(11) Uani 1 1 d . . . O2 O 0.1720(5) 1.0575(2) 0.9066(2) 0.0261(10) Uani 1 1 d . . . O3 O -0.0173(5) 1.1151(3) 0.8367(2) 0.0295(10) Uani 1 1 d . . . O4 O -0.0571(5) 1.0797(3) 0.9633(3) 0.0446(13) Uani 1 1 d . . . F1 F 0.1966(6) 1.2229(3) 0.8870(3) 0.0661(15) Uani 1 1 d . . . F2 F 0.1660(6) 1.1956(2) 1.0004(3) 0.0638(15) Uani 1 1 d . . . F3 F -0.0020(6) 1.2463(3) 0.9390(3) 0.0623(15) Uani 1 1 d . . . C1 C 0.3738(7) 0.9105(4) 0.9737(3) 0.0243(14) Uani 1 1 d . . . H1A H 0.2806 0.8926 0.9690 0.029 Uiso 1 1 calc R . . C2 C 0.4538(8) 0.8835(4) 1.0318(3) 0.0308(15) Uani 1 1 d . . . H2 H 0.4149 0.8505 1.0666 0.037 Uiso 1 1 calc R . . C3 C 0.5927(8) 0.9073(4) 1.0361(3) 0.0305(15) Uani 1 1 d . . . H3 H 0.6511 0.8892 1.0736 0.037 Uiso 1 1 calc R . . C4 C 0.6463(7) 0.9578(4) 0.9853(3) 0.0261(15) Uani 1 1 d . . . H4 H 0.7411 0.9736 0.9878 0.031 Uiso 1 1 calc R . . C5 C 0.5573(6) 0.9853(3) 0.9299(3) 0.0197(12) Uani 1 1 d . . . C6 C 0.6031(7) 1.0475(3) 0.8773(3) 0.0234(14) Uani 1 1 d . . . H6 H 0.7072 1.0456 0.8718 0.028 Uiso 1 1 calc R . . C7 C 0.6176(6) 0.9770(3) 0.7605(3) 0.0190(12) Uani 1 1 d . . . H7 H 0.6533 0.9382 0.7949 0.023 Uiso 1 1 calc R . . C8 C 0.7463(6) 1.0115(4) 0.7223(3) 0.0225(13) Uani 1 1 d . . . H8A H 0.8088 1.0344 0.7587 0.027 Uiso 1 1 calc R . . H8B H 0.7146 1.0520 0.6895 0.027 Uiso 1 1 calc R . . C9 C 0.8296(6) 0.9520(4) 0.6785(4) 0.0278(14) Uani 1 1 d . . . H9A H 0.8701 0.9141 0.7115 0.033 Uiso 1 1 calc R . . H9B H 0.9074 0.9768 0.6524 0.033 Uiso 1 1 calc R . . C10 C 0.7303(7) 0.9127(3) 0.6237(3) 0.0270(15) Uani 1 1 d . . . H10A H 0.7828 0.8734 0.5972 0.032 Uiso 1 1 calc R . . H10B H 0.6962 0.9501 0.5883 0.032 Uiso 1 1 calc R . . C11 C 0.6026(7) 0.8759(3) 0.6628(3) 0.0239(13) Uani 1 1 d . . . H11A H 0.5399 0.8524 0.6269 0.029 Uiso 1 1 calc R . . H11B H 0.6361 0.8361 0.6958 0.029 Uiso 1 1 calc R . . C12 C 0.5204(6) 0.9362(3) 0.7062(3) 0.0178(12) Uani 1 1 d . . . H12 H 0.4824 0.9743 0.6717 0.021 Uiso 1 1 calc R . . C13 C 0.2880(7) 0.8621(3) 0.7082(3) 0.0235(13) Uani 1 1 d . . . H13 H 0.3271 0.8132 0.6909 0.028 Uiso 1 1 calc R . . C14 C 0.1659(6) 0.8461(3) 0.7605(3) 0.0207(13) Uani 1 1 d . . . C15 C 0.0801(8) 0.7823(4) 0.7534(4) 0.0322(16) Uani 1 1 d . . . H15 H 0.1024 0.7451 0.7186 0.039 Uiso 1 1 calc R . . C16 C -0.0387(8) 0.7732(4) 0.7974(4) 0.0358(17) Uani 1 1 d . . . H16 H -0.0990 0.7313 0.7912 0.043 Uiso 1 1 calc R . . C17 C -0.0662(7) 0.8274(4) 0.8507(4) 0.0315(16) Uani 1 1 d . . . H17 H -0.1446 0.8223 0.8817 0.038 Uiso 1 1 calc R . . C18 C 0.0254(6) 0.8895(4) 0.8571(3) 0.0226(13) Uani 1 1 d . . . H18 H 0.0073 0.9261 0.8932 0.027 Uiso 1 1 calc R . . C19 C 0.5608(9) 1.1262(4) 0.9071(4) 0.0385(18) Uani 1 1 d . . . H19A H 0.5898 1.1652 0.8729 0.058 Uiso 1 1 calc R . . H19B H 0.6070 1.1346 0.9534 0.058 Uiso 1 1 calc R . . H19C H 0.4591 1.1282 0.9135 0.058 Uiso 1 1 calc R . . C20 C 0.2318(7) 0.9069(4) 0.6428(3) 0.0243(14) Uani 1 1 d . . . H20A H 0.2014 0.9569 0.6587 0.036 Uiso 1 1 calc R . . H20B H 0.1524 0.8800 0.6216 0.036 Uiso 1 1 calc R . . H20C H 0.3061 0.9122 0.6068 0.036 Uiso 1 1 calc R . . C21 C 0.1053(9) 1.1978(4) 0.9356(4) 0.0390(18) Uani 1 1 d . . . H1C H 0.137(8) 1.084(4) 0.756(4) 0.02(2) Uiso 1 1 d . . . H1D H 0.229(9) 1.100(5) 0.714(4) 0.05(2) 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 O7 0.038(3) 0.024(2) 0.030(2) 0.0029(18) 0.001(2) -0.003(2) O6 0.046(3) 0.049(3) 0.037(3) -0.009(2) -0.016(3) 0.003(3) O5 0.032(3) 0.031(2) 0.037(3) -0.0086(19) 0.007(2) 0.009(2) S2 0.0240(8) 0.0181(7) 0.0190(7) -0.0005(5) 0.0003(6) 0.0006(6) F6 0.036(3) 0.057(3) 0.086(4) -0.011(3) 0.039(3) -0.004(2) F5 0.073(3) 0.055(3) 0.023(2) 0.0035(19) -0.005(2) 0.006(3) F4 0.063(3) 0.032(2) 0.073(3) 0.015(2) 0.024(3) -0.007(2) C22 0.032(4) 0.035(4) 0.036(4) 0.005(3) 0.016(3) -0.005(3) Mn1 0.0125(4) 0.0122(4) 0.0177(4) -0.0012(3) 0.0001(4) -0.0019(3) S1 0.0172(7) 0.0200(7) 0.0243(7) -0.0015(6) 0.0051(6) 0.0019(6) N1 0.012(2) 0.025(3) 0.016(2) -0.0037(19) -0.0010(19) 0.002(2) N2 0.019(3) 0.022(2) 0.018(2) -0.0002(19) 0.000(2) -0.006(2) N3 0.012(2) 0.026(3) 0.014(2) -0.003(2) -0.0042(19) -0.002(2) N4 0.013(2) 0.019(2) 0.021(2) 0.004(2) -0.0054(19) -0.0066(19) O1 0.031(3) 0.027(2) 0.031(3) 0.011(2) 0.008(2) 0.015(2) O2 0.027(3) 0.034(2) 0.017(2) 0.0020(18) -0.0036(19) 0.010(2) O3 0.022(2) 0.037(2) 0.030(2) -0.0030(19) 0.002(2) 0.0004(19) O4 0.031(3) 0.059(3) 0.043(3) 0.007(2) 0.014(2) -0.002(3) F1 0.071(4) 0.039(3) 0.088(4) 0.013(2) 0.001(3) -0.026(3) F2 0.092(4) 0.041(3) 0.058(3) -0.014(2) -0.034(3) 0.008(3) F3 0.076(4) 0.036(2) 0.075(3) -0.018(2) -0.022(3) 0.028(2) C1 0.019(3) 0.032(3) 0.022(3) 0.008(3) 0.003(3) -0.005(3) C2 0.043(4) 0.035(4) 0.014(3) 0.004(2) 0.007(3) -0.004(3) C3 0.045(4) 0.028(3) 0.019(3) 0.002(3) -0.005(3) 0.005(3) C4 0.020(3) 0.035(4) 0.023(3) -0.012(3) -0.007(3) 0.004(3) C5 0.019(3) 0.025(3) 0.015(3) -0.009(2) -0.002(2) 0.002(3) C6 0.017(3) 0.027(3) 0.027(3) -0.005(3) -0.006(3) -0.009(3) C7 0.014(3) 0.023(3) 0.020(3) 0.005(2) -0.001(2) -0.001(2) C8 0.013(3) 0.031(3) 0.023(3) -0.001(3) -0.003(2) -0.001(3) C9 0.013(3) 0.042(4) 0.028(3) 0.015(3) 0.000(3) 0.007(3) C10 0.037(4) 0.021(3) 0.023(3) 0.007(2) 0.009(3) 0.017(3) C11 0.033(4) 0.025(3) 0.014(3) 0.000(2) 0.000(3) 0.007(3) C12 0.016(3) 0.022(3) 0.015(3) 0.002(2) -0.006(2) -0.001(2) C13 0.019(3) 0.018(3) 0.034(3) -0.009(2) -0.002(3) 0.005(3) C14 0.012(3) 0.019(3) 0.031(3) 0.003(2) -0.003(2) -0.004(2) C15 0.040(4) 0.020(3) 0.037(4) -0.007(3) -0.003(3) -0.010(3) C16 0.034(4) 0.025(3) 0.048(4) 0.005(3) -0.009(3) -0.021(3) C17 0.015(3) 0.047(4) 0.033(3) 0.019(3) -0.007(3) -0.019(3) C18 0.018(3) 0.031(3) 0.019(3) 0.008(2) 0.001(2) 0.006(3) C19 0.066(6) 0.023(3) 0.027(3) -0.003(3) 0.000(4) -0.011(4) C20 0.022(3) 0.033(3) 0.018(3) -0.006(3) -0.007(2) -0.004(3) C21 0.048(5) 0.025(4) 0.043(4) -0.011(3) -0.011(4) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7 S2 1.426(4) . ? O6 S2 1.422(5) . ? O5 S2 1.440(5) . ? S2 C22 1.816(7) . ? F6 C22 1.331(8) . ? F5 C22 1.317(9) . ? F4 C22 1.337(8) . ? Mn1 O1 2.141(5) . ? Mn1 N1 2.203(5) . ? Mn1 N3 2.246(5) . ? Mn1 O2 2.261(4) . ? Mn1 N4 2.268(4) . ? Mn1 N2 2.304(5) . ? Mn1 H1C 2.55(7) . ? S1 O4 1.420(5) . ? S1 O3 1.428(5) . ? S1 O2 1.450(5) . ? S1 C21 1.840(7) . ? N1 C1 1.321(7) . ? N1 C5 1.360(7) . ? N2 C6 1.484(7) . ? N2 C7 1.495(7) . ? N2 H2D 0.89(8) . ? N3 C13 1.468(7) . ? N3 C12 1.489(7) . ? N3 H3D 0.78(8) . ? N4 C18 1.339(7) . ? N4 C14 1.355(8) . ? O1 H1C 0.71(7) . ? O1 H1D 0.84(8) . ? F1 C21 1.305(9) . ? F2 C21 1.310(8) . ? F3 C21 1.313(9) . ? C1 C2 1.379(9) . ? C1 H1A 0.9300 . ? C2 C3 1.367(10) . ? C2 H2 0.9300 . ? C3 C4 1.372(9) . ? C3 H3 0.9300 . ? C4 C5 1.392(8) . ? C4 H4 0.9300 . ? C5 C6 1.508(8) . ? C6 C19 1.526(9) . ? C6 H6 0.9800 . ? C7 C8 1.515(8) . ? C7 C12 1.521(8) . ? C7 H7 0.9800 . ? C8 C9 1.523(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.526(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.531(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12 0.9800 . ? C13 C14 1.514(9) . ? C13 C20 1.518(8) . ? C13 H13 0.9800 . ? C14 C15 1.377(8) . ? C15 C16 1.380(10) . ? C15 H15 0.9300 . ? C16 C17 1.377(10) . ? C16 H16 0.9300 . ? C17 C18 1.386(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 O6 S2 O7 116.1(3) . . ? O6 S2 O5 115.0(3) . . ? O7 S2 O5 114.2(3) . . ? O6 S2 C22 105.0(3) . . ? O7 S2 C22 103.0(3) . . ? O5 S2 C22 100.9(3) . . ? F5 C22 F6 108.0(6) . . ? F5 C22 F4 108.5(6) . . ? F6 C22 F4 107.2(6) . . ? F5 C22 S2 111.0(5) . . ? F6 C22 S2 111.2(5) . . ? F4 C22 S2 110.7(5) . . ? O1 Mn1 N1 156.89(19) . . ? O1 Mn1 N3 101.76(19) . . ? N1 Mn1 N3 97.61(17) . . ? O1 Mn1 O2 83.63(17) . . ? N1 Mn1 O2 80.84(16) . . ? N3 Mn1 O2 164.84(17) . . ? O1 Mn1 N4 95.02(19) . . ? N1 Mn1 N4 102.47(17) . . ? N3 Mn1 N4 73.63(17) . . ? O2 Mn1 N4 91.89(17) . . ? O1 Mn1 N2 96.9(2) . . ? N1 Mn1 N2 75.57(18) . . ? N3 Mn1 N2 76.25(17) . . ? O2 Mn1 N2 117.50(17) . . ? N4 Mn1 N2 149.28(18) . . ? O1 Mn1 H1C 14.4(15) . . ? N1 Mn1 H1C 149.7(15) . . ? N3 Mn1 H1C 112.6(15) . . ? O2 Mn1 H1C 70.7(15) . . ? N4 Mn1 H1C 89.1(16) . . ? N2 Mn1 H1C 108.1(16) . . ? O4 S1 O3 116.1(3) . . ? O4 S1 O2 114.3(3) . . ? O3 S1 O2 113.2(3) . . ? O4 S1 C21 105.5(4) . . ? O3 S1 C21 103.3(3) . . ? O2 S1 C21 102.5(3) . . ? C1 N1 C5 118.1(5) . . ? C1 N1 Mn1 125.2(4) . . ? C5 N1 Mn1 116.0(4) . . ? C6 N2 C7 111.2(5) . . ? C6 N2 Mn1 108.0(4) . . ? C7 N2 Mn1 110.3(3) . . ? C6 N2 H2D 100(5) . . ? C7 N2 H2D 112(5) . . ? Mn1 N2 H2D 115(6) . . ? C13 N3 C12 117.6(4) . . ? C13 N3 Mn1 111.6(3) . . ? C12 N3 Mn1 110.4(3) . . ? C13 N3 H3D 113(6) . . ? C12 N3 H3D 110(6) . . ? Mn1 N3 H3D 91(6) . . ? C18 N4 C14 119.1(5) . . ? C18 N4 Mn1 125.9(4) . . ? C14 N4 Mn1 114.9(4) . . ? Mn1 O1 H1C 117(5) . . ? Mn1 O1 H1D 138(6) . . ? H1C O1 H1D 100(7) . . ? S1 O2 Mn1 138.1(3) . . ? N1 C1 C2 124.5(6) . . ? N1 C1 H1A 117.8 . . ? C2 C1 H1A 117.8 . . ? C3 C2 C1 117.3(6) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 119.4(6) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 120.5(6) . . ? N1 C5 C6 116.9(5) . . ? C4 C5 C6 122.5(6) . . ? N2 C6 C5 109.9(5) . . ? N2 C6 C19 110.0(5) . . ? C5 C6 C19 110.2(5) . . ? N2 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? C19 C6 H6 108.9 . . ? N2 C7 C8 112.6(5) . . ? N2 C7 C12 110.9(5) . . ? C8 C7 C12 111.2(5) . . ? N2 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? C12 C7 H7 107.3 . . ? C7 C8 C9 112.2(5) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 109.6(5) . . ? 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 . . ? C9 C10 C11 111.0(5) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 110.4(5) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N3 C12 C7 107.1(4) . . ? N3 C12 C11 113.1(5) . . ? C7 C12 C11 110.9(5) . . ? N3 C12 H12 108.5 . . ? C7 C12 H12 108.5 . . ? C11 C12 H12 108.5 . . ? N3 C13 C14 107.9(5) . . ? N3 C13 C20 113.0(5) . . ? C14 C13 C20 109.1(5) . . ? N3 C13 H13 108.9 . . ? C14 C13 H13 108.9 . . ? C20 C13 H13 108.9 . . ? N4 C14 C15 120.5(6) . . ? N4 C14 C13 117.5(5) . . ? C15 C14 C13 122.0(6) . . ? C14 C15 C16 120.5(6) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 118.8(6) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 118.6(6) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? N4 C18 C17 122.5(6) . . ? N4 C18 H18 118.7 . . ? C17 C18 H18 118.7 . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? F1 C21 F2 109.7(7) . . ? F1 C21 F3 108.6(6) . . ? F2 C21 F3 107.9(6) . . ? F1 C21 S1 109.3(5) . . ? F2 C21 S1 111.1(5) . . ? F3 C21 S1 110.2(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.780 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 933759' ####################################################################### # # 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_mntoffm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 F6 Mn N4 O7 S2' _chemical_formula_weight 695.56 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.3527(19) _cell_length_b 17.384(3) _cell_length_c 18.184(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2956.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4552 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.76 _exptl_crystal_description PLATES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8499 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17075 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6411 _reflns_number_gt 5892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.4417P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(3) _refine_ls_number_reflns 6411 _refine_ls_number_parameters 395 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1728 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _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 0.19446(8) 0.49314(4) 0.82345(4) 0.01718(18) Uani 1 1 d . . . S1 S 0.45888(14) 0.60217(7) 0.90809(7) 0.0230(3) Uani 1 1 d . . . S2 S 0.04837(15) 0.71411(7) 0.65577(7) 0.0229(3) Uani 1 1 d . . . O1 O 0.2958(5) 0.5690(2) 0.7465(2) 0.0307(9) Uani 1 1 d D . . O2 O 0.3286(4) 0.5577(2) 0.9065(2) 0.0276(9) Uani 1 1 d . . . O3 O 0.5178(4) 0.6156(2) 0.8366(2) 0.0308(9) Uani 1 1 d . . . O4 O 0.5571(5) 0.5796(3) 0.9631(3) 0.0466(12) Uani 1 1 d . . . O5 O 0.1827(5) 0.6740(2) 0.6558(2) 0.0360(10) Uani 1 1 d . . . O6 O -0.0548(5) 0.6865(3) 0.7074(2) 0.0445(11) Uani 1 1 d . . . O7 O 0.0616(5) 0.7952(2) 0.6503(2) 0.0336(9) Uani 1 1 d . . . N1 N 0.3604(4) 0.3992(2) 0.8133(2) 0.0208(9) Uani 1 1 d . . . N2 N 0.1010(5) 0.4036(3) 0.7491(2) 0.0195(9) Uani 1 1 d . . . N3 N -0.0365(5) 0.5352(2) 0.8044(2) 0.0214(9) Uani 1 1 d . . . N4 N 0.0797(5) 0.4603(2) 0.9239(2) 0.0204(9) Uani 1 1 d . . . F1 F 0.3031(6) 0.7230(2) 0.8870(3) 0.0664(13) Uani 1 1 d . . . F2 F 0.3343(6) 0.6955(2) 1.0006(2) 0.0655(14) Uani 1 1 d . . . F3 F 0.5025(6) 0.7461(2) 0.9388(2) 0.0662(14) Uani 1 1 d . . . F4 F -0.0409(5) 0.6115(2) 0.5616(2) 0.0588(12) Uani 1 1 d . . . F6 F 0.0673(5) 0.7085(2) 0.51326(19) 0.0537(11) Uani 1 1 d . . . F5 F -0.1478(4) 0.7200(3) 0.5534(3) 0.0606(13) Uani 1 1 d . . . C1 C 0.4743(6) 0.3900(3) 0.8574(3) 0.0244(11) Uani 1 1 d . . . H1A H 0.4917 0.4264 0.8938 0.029 Uiso 1 1 calc R . . C2 C 0.5676(6) 0.3275(4) 0.8505(3) 0.0327(14) Uani 1 1 d . . . H2 H 0.6469 0.3227 0.8810 0.039 Uiso 1 1 calc R . . C3 C 0.5388(7) 0.2736(3) 0.7975(3) 0.0361(14) Uani 1 1 d . . . H3 H 0.5992 0.2316 0.7916 0.043 Uiso 1 1 calc R . . C4 C 0.4198(7) 0.2817(3) 0.7528(3) 0.0352(14) Uani 1 1 d . . . H4 H 0.3974 0.2444 0.7180 0.042 Uiso 1 1 calc R . . C5 C 0.3350(6) 0.3465(3) 0.7610(3) 0.0240(12) Uani 1 1 d . . . C6 C 0.2118(6) 0.3619(3) 0.7083(3) 0.0246(12) Uani 1 1 d . . . H6 H 0.1726 0.3127 0.6915 0.029 Uiso 1 1 calc R . . C7 C -0.0211(6) 0.4361(3) 0.7067(3) 0.0195(10) Uani 1 1 d . . . H7 H 0.0166 0.4746 0.6724 0.023 Uiso 1 1 calc R . . C8 C -0.1031(6) 0.3763(3) 0.6628(3) 0.0275(12) Uani 1 1 d . . . H8A H -0.1366 0.3362 0.6956 0.033 Uiso 1 1 calc R . . H8B H -0.0400 0.3530 0.6268 0.033 Uiso 1 1 calc R . . C9 C -0.2300(6) 0.4126(3) 0.6238(3) 0.0293(13) Uani 1 1 d . . . H9A H -0.2821 0.3732 0.5972 0.035 Uiso 1 1 calc R . . H9B H -0.1959 0.4501 0.5884 0.035 Uiso 1 1 calc R . . C10 C -0.3300(6) 0.4518(3) 0.6783(3) 0.0309(13) Uani 1 1 d . . . H10A H -0.3708 0.4138 0.7112 0.037 Uiso 1 1 calc R . . H10B H -0.4075 0.4767 0.6520 0.037 Uiso 1 1 calc R . . C11 C -0.2468(6) 0.5117(3) 0.7227(3) 0.0265(11) Uani 1 1 d . . . H11A H -0.2146 0.5522 0.6900 0.032 Uiso 1 1 calc R . . H11B H -0.3097 0.5345 0.7590 0.032 Uiso 1 1 calc R . . C12 C -0.1191(5) 0.4767(3) 0.7610(3) 0.0200(10) Uani 1 1 d . . . H12 H -0.1548 0.4380 0.7956 0.024 Uiso 1 1 calc R . . C13 C -0.1027(6) 0.5479(3) 0.8771(3) 0.0251(12) Uani 1 1 d . . . H13 H -0.2069 0.5463 0.8716 0.030 Uiso 1 1 calc R . . C14 C -0.0580(5) 0.4855(3) 0.9302(3) 0.0212(10) Uani 1 1 d . . . C15 C -0.1465(6) 0.4578(3) 0.9851(3) 0.0292(13) Uani 1 1 d . . . H15 H -0.2414 0.4735 0.9875 0.035 Uiso 1 1 calc R . . C16 C -0.0933(7) 0.4070(3) 1.0361(3) 0.0341(14) Uani 1 1 d . . . H16 H -0.1520 0.3884 1.0733 0.041 Uiso 1 1 calc R . . C17 C 0.0480(7) 0.3837(3) 1.0319(3) 0.0317(13) Uani 1 1 d . . . H17 H 0.0881 0.3514 1.0670 0.038 Uiso 1 1 calc R . . C18 C 0.1263(6) 0.4107(3) 0.9733(3) 0.0275(12) Uani 1 1 d . . . H18 H 0.2193 0.3926 0.9681 0.033 Uiso 1 1 calc R . . C19 C 0.2668(6) 0.4067(3) 0.6421(3) 0.0283(13) Uani 1 1 d . . . H19A H 0.1908 0.4134 0.6072 0.042 Uiso 1 1 calc R . . H19B H 0.3438 0.3788 0.6196 0.042 Uiso 1 1 calc R . . H19C H 0.3006 0.4562 0.6579 0.042 Uiso 1 1 calc R . . C20 C -0.0607(9) 0.6260(3) 0.9073(3) 0.0403(16) Uani 1 1 d . . . H20A H 0.0412 0.6282 0.9130 0.060 Uiso 1 1 calc R . . H20B H -0.1057 0.6338 0.9541 0.060 Uiso 1 1 calc R . . H20C H -0.0910 0.6654 0.8737 0.060 Uiso 1 1 calc R . . C21 C 0.3945(8) 0.6973(4) 0.9351(4) 0.0401(15) Uani 1 1 d . . . C22 C -0.0220(7) 0.6865(3) 0.5662(3) 0.0357(14) Uani 1 1 d . . . H1C H 0.265(6) 0.602(3) 0.709(3) 0.06(2) Uiso 1 1 d D . . H1D H 0.388(3) 0.582(3) 0.761(3) 0.025(16) Uiso 1 1 d D . . H2C H 0.077(9) 0.375(4) 0.781(4) 0.050 Uiso 1 1 d . . . H3C H -0.045(8) 0.583(4) 0.779(4) 0.050 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 0.0125(4) 0.0193(3) 0.0197(4) -0.0010(3) 0.0001(3) 0.0016(3) S1 0.0148(6) 0.0279(6) 0.0262(7) -0.0011(5) -0.0048(5) -0.0010(5) S2 0.0226(7) 0.0252(6) 0.0208(6) 0.0004(5) -0.0008(5) -0.0001(5) O1 0.030(2) 0.032(2) 0.030(2) 0.0083(16) -0.0086(19) -0.0070(18) O2 0.023(2) 0.037(2) 0.0221(19) 0.0011(16) 0.0022(16) -0.0095(17) O3 0.021(2) 0.044(2) 0.027(2) -0.0014(17) -0.0021(16) -0.0028(16) O4 0.032(3) 0.063(3) 0.045(3) 0.007(2) -0.016(2) 0.001(2) O5 0.026(2) 0.039(2) 0.042(2) 0.0073(18) -0.006(2) 0.0051(18) O6 0.042(3) 0.051(3) 0.041(3) 0.011(2) 0.015(2) 0.002(2) O7 0.035(3) 0.034(2) 0.032(2) 0.0002(17) -0.0021(18) 0.0030(18) N1 0.012(2) 0.024(2) 0.026(2) 0.0036(19) 0.0068(17) 0.0055(16) N2 0.012(2) 0.030(2) 0.016(2) 0.0023(18) 0.0038(16) 0.0056(18) N3 0.020(2) 0.025(2) 0.019(2) -0.0010(16) -0.0007(18) 0.0034(18) N4 0.019(2) 0.027(2) 0.015(2) -0.0019(17) -0.0006(17) 0.0001(17) F1 0.073(3) 0.044(2) 0.082(3) 0.011(2) 0.000(3) 0.028(2) F2 0.095(4) 0.049(2) 0.053(3) -0.0128(19) 0.037(3) -0.010(2) F3 0.083(4) 0.041(2) 0.074(3) -0.020(2) 0.018(3) -0.028(2) F4 0.068(3) 0.036(2) 0.073(3) -0.0138(19) -0.025(2) -0.004(2) F6 0.076(3) 0.062(2) 0.0229(18) -0.0039(17) 0.004(2) 0.002(2) F5 0.031(2) 0.064(3) 0.086(3) 0.012(2) -0.035(2) -0.0056(19) C1 0.015(3) 0.037(3) 0.021(3) 0.006(2) 0.000(2) -0.002(2) C2 0.014(3) 0.050(3) 0.035(3) 0.016(3) 0.007(2) 0.016(2) C3 0.033(4) 0.032(3) 0.043(3) -0.001(3) 0.007(3) 0.022(3) C4 0.036(4) 0.031(3) 0.038(3) -0.008(3) 0.005(3) 0.008(3) C5 0.017(3) 0.025(3) 0.031(3) 0.004(2) 0.005(2) 0.0043(19) C6 0.017(3) 0.024(2) 0.033(3) -0.011(2) 0.004(2) 0.003(2) C7 0.017(3) 0.027(3) 0.014(2) 0.0012(19) 0.0053(19) 0.004(2) C8 0.028(3) 0.034(3) 0.020(3) 0.002(2) -0.003(2) -0.004(2) C9 0.029(3) 0.032(3) 0.027(3) 0.004(2) -0.011(2) -0.011(2) C10 0.013(3) 0.046(3) 0.033(3) 0.012(3) -0.001(2) -0.003(2) C11 0.011(2) 0.040(3) 0.029(3) 0.000(2) 0.003(2) -0.001(2) C12 0.012(2) 0.028(3) 0.020(3) 0.004(2) 0.003(2) 0.0008(19) C13 0.014(3) 0.037(3) 0.024(3) -0.006(2) 0.001(2) 0.006(2) C14 0.017(2) 0.029(3) 0.017(2) -0.012(2) 0.004(2) -0.003(2) C15 0.023(3) 0.042(3) 0.022(3) -0.010(2) 0.008(2) -0.003(2) C16 0.044(4) 0.037(3) 0.022(3) 0.004(2) 0.007(3) -0.008(3) C17 0.039(4) 0.041(3) 0.015(3) 0.003(2) -0.006(3) 0.001(3) C18 0.016(3) 0.037(3) 0.030(3) 0.007(2) 0.001(2) -0.001(2) C19 0.018(3) 0.044(3) 0.023(3) -0.009(2) 0.005(2) 0.003(2) C20 0.064(5) 0.026(3) 0.031(3) -0.004(2) -0.002(3) 0.010(3) C21 0.042(4) 0.037(3) 0.041(4) -0.008(3) 0.008(3) 0.000(3) C22 0.032(4) 0.037(3) 0.039(3) -0.003(3) -0.016(3) 0.000(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 O1 2.144(4) . ? Mn1 N4 2.195(4) . ? Mn1 N2 2.239(4) . ? Mn1 N1 2.260(4) . ? Mn1 O2 2.262(4) . ? Mn1 N3 2.307(5) . ? S1 O4 1.414(4) . ? S1 O3 1.432(4) . ? S1 O2 1.443(4) . ? S1 C21 1.826(6) . ? S2 O7 1.419(4) . ? S2 O6 1.429(5) . ? S2 O5 1.437(4) . ? S2 C22 1.821(6) . ? O1 H1C 0.940(19) . ? O1 H1D 0.935(19) . ? N1 C5 1.342(7) . ? N1 C1 1.344(7) . ? N2 C6 1.466(6) . ? N2 C7 1.489(6) . ? N2 H2C 0.80(8) . ? N3 C13 1.476(7) . ? N3 C12 1.500(7) . ? N3 H3C 0.96(7) . ? N4 C18 1.318(7) . ? N4 C14 1.365(7) . ? F1 C21 1.302(8) . ? F2 C21 1.319(8) . ? F3 C21 1.321(8) . ? F4 C22 1.318(7) . ? F6 C22 1.330(8) . ? F5 C22 1.334(7) . ? C1 C2 1.399(8) . ? C1 H1A 0.9300 . ? C2 C3 1.370(9) . ? C2 H2 0.9300 . ? C3 C4 1.385(9) . ? C3 H3 0.9300 . ? C4 C5 1.385(7) . ? C4 H4 0.9300 . ? C5 C6 1.522(8) . ? C6 C19 1.523(8) . ? C6 H6 0.9800 . ? C7 C8 1.519(7) . ? C7 C12 1.521(7) . ? C7 H7 0.9800 . ? C8 C9 1.519(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.523(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.529(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12 0.9800 . ? C13 C14 1.511(8) . ? C13 C20 1.515(8) . ? C13 H13 0.9800 . ? C14 C15 1.383(7) . ? C15 C16 1.373(9) . ? C15 H15 0.9300 . ? C16 C17 1.384(9) . ? C16 H16 0.9300 . ? C17 C18 1.375(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 O1 Mn1 N4 156.86(16) . . ? O1 Mn1 N2 101.93(16) . . ? N4 Mn1 N2 97.51(16) . . ? O1 Mn1 N1 95.03(16) . . ? N4 Mn1 N1 102.47(16) . . ? N2 Mn1 N1 73.51(16) . . ? O1 Mn1 O2 83.39(14) . . ? N4 Mn1 O2 81.05(15) . . ? N2 Mn1 O2 164.71(15) . . ? N1 Mn1 O2 91.85(16) . . ? O1 Mn1 N3 96.97(16) . . ? N4 Mn1 N3 75.47(16) . . ? N2 Mn1 N3 76.36(15) . . ? N1 Mn1 N3 149.27(16) . . ? O2 Mn1 N3 117.55(15) . . ? O4 S1 O3 116.0(3) . . ? O4 S1 O2 114.4(3) . . ? O3 S1 O2 113.2(2) . . ? O4 S1 C21 106.0(3) . . ? O3 S1 C21 102.9(3) . . ? O2 S1 C21 102.2(3) . . ? O7 S2 O6 116.0(3) . . ? O7 S2 O5 114.0(3) . . ? O6 S2 O5 115.3(3) . . ? O7 S2 C22 103.3(3) . . ? O6 S2 C22 104.8(3) . . ? O5 S2 C22 100.8(3) . . ? Mn1 O1 H1C 136(4) . . ? Mn1 O1 H1D 112(3) . . ? H1C O1 H1D 110(3) . . ? S1 O2 Mn1 138.4(2) . . ? C5 N1 C1 118.8(4) . . ? C5 N1 Mn1 115.5(3) . . ? C1 N1 Mn1 125.6(4) . . ? C6 N2 C7 117.9(4) . . ? C6 N2 Mn1 111.9(3) . . ? C7 N2 Mn1 110.3(3) . . ? C6 N2 H2C 105(6) . . ? C7 N2 H2C 113(6) . . ? Mn1 N2 H2C 96(5) . . ? C13 N3 C12 110.9(4) . . ? C13 N3 Mn1 107.8(3) . . ? C12 N3 Mn1 110.3(3) . . ? C13 N3 H3C 105(4) . . ? C12 N3 H3C 107(4) . . ? Mn1 N3 H3C 115(5) . . ? C18 N4 C14 117.7(5) . . ? C18 N4 Mn1 125.1(4) . . ? C14 N4 Mn1 116.6(3) . . ? N1 C1 C2 122.3(5) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C3 C2 C1 118.1(5) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 120.1(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 118.6(5) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 122.0(5) . . ? N1 C5 C6 117.3(4) . . ? C4 C5 C6 120.6(5) . . ? N2 C6 C5 107.7(4) . . ? N2 C6 C19 112.7(4) . . ? C5 C6 C19 109.4(4) . . ? N2 C6 H6 109.0 . . ? C5 C6 H6 109.0 . . ? C19 C6 H6 109.0 . . ? N2 C7 C8 113.6(4) . . ? N2 C7 C12 107.6(4) . . ? C8 C7 C12 110.7(4) . . ? N2 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C12 C7 H7 108.3 . . ? C7 C8 C9 110.9(4) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.2(5) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 109.6(4) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 111.9(5) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C11 112.2(4) . . ? N3 C12 C7 110.2(4) . . ? C11 C12 C7 111.3(4) . . ? N3 C12 H12 107.6 . . ? C11 C12 H12 107.6 . . ? C7 C12 H12 107.6 . . ? N3 C13 C14 110.4(4) . . ? N3 C13 C20 110.5(5) . . ? C14 C13 C20 109.9(5) . . ? N3 C13 H13 108.7 . . ? C14 C13 H13 108.7 . . ? C20 C13 H13 108.7 . . ? N4 C14 C15 120.9(5) . . ? N4 C14 C13 115.9(4) . . ? C15 C14 C13 123.1(5) . . ? C16 C15 C14 119.6(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.8(5) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 116.8(5) . . ? C18 C17 H17 121.6 . . ? C16 C17 H17 121.6 . . ? N4 C18 C17 125.1(5) . . ? N4 C18 H18 117.5 . . ? C17 C18 H18 117.5 . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? F1 C21 F2 109.5(6) . . ? F1 C21 F3 108.4(6) . . ? F2 C21 F3 107.1(5) . . ? F1 C21 S1 110.3(5) . . ? F2 C21 S1 111.2(5) . . ? F3 C21 S1 110.1(5) . . ? F4 C22 F6 108.9(5) . . ? F4 C22 F5 107.6(5) . . ? F6 C22 F5 107.6(5) . . ? F4 C22 S2 111.4(4) . . ? F6 C22 S2 110.2(4) . . ? F5 C22 S2 111.1(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.348 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 945142'