#Electronic Supplementary Material for Dalton Transactions #This Journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Montserrat Rodriguez Pizarro' _publ_contact_author_email MONTSE.RODRIGUEZ@UDG.EDU _publ_section_title ; Mn(II) Complexes Containing the polypyridylic chiral ligand (-)-pinene[5,6]bipyridine. Catalysts for oxidation reactions ; loop_ _publ_author_name 'Montserrat Rodriguez Pizarro' 'Marie-Noelle Collomb' 'Montserrat Corbella' 'Xavier Fontrodona' 'Antoni Llobet' ; J.Rich ; 'Isabel Romero' 'Xavier Sala' 'Lydia Vaquer' data_720645 _database_code_depnum_ccdc_archive 'CCDC 720645' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H36 Cl2 Mn N4' _chemical_formula_sum 'C34 H36 Cl2 Mn N4' _chemical_formula_weight 626.51 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.115(6) _cell_length_b 15.739(11) _cell_length_c 25.528(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3662(4) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.532 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 57464 _diffrn_reflns_av_R_equivalents 0.2317 _diffrn_reflns_av_sigmaI/netI 0.2685 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.48 _reflns_number_total 9018 _reflns_number_gt 2878 _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 'BRUKER Shelxtl' _computing_publication_material 'BRUKER Shelxtl' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystal was of poor quality, and so was the data, with ugly large and unsymetric reflections. High Rint was obtained. No better crystals could be obtained. The space group was checked with the PlaTON tool ADDSYM wich didn't suggest any other symmetry. The New Symmetry tool of the same program suggested to try space groups Pmc21, P2cm and Pmcm. The Data was processed in all those three space groups, but no better Rint index were optained, and the crystal couldn't be satisfactory resolved in any of the three space groups. A considerable amount of electron density attibutable to partially disordered solvent molecules was removed with the SQUEEZE option of PLATON (Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, THe Netherlands.). This electron density couldn't be related to any chemical species. Displacement Parameters for atoms c2, c3, c4, c7, c9, c10, c21, c22, c23, c26, c16, c19, c27 and c36 were restrained to approximate to isotropic behavoir with the ISOR instruction, with e.s.d equal to 0.001 C(sp3)-C(sp3) bond distance were restrained to 1.54(1)A for the bonds c15-c16 c15-c20 c15-c21 c16-c17 c16-c18 c31-c34 C(sp3)-C(sp2) bond distance were restrained to 1.51(1)A for the bonds c10-c11 c18-c19 c30-c31 c35-c36 ; _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^)+(0.0886P)^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' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 9018 _refine_ls_number_parameters 374 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.2524 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.2396 _refine_ls_wR_factor_gt 0.1897 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.890 _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 0.25088(15) 0.61924(6) 0.76673(5) 0.0524(3) Uani 1 1 d . . . Cl1 Cl 0.3556(3) 0.50781(12) 0.82444(10) 0.0779(8) Uani 1 1 d . . . N1 N 0.0293(7) 0.5504(4) 0.7705(3) 0.064(2) Uani 1 1 d . . . Cl2 Cl 0.1487(3) 0.73285(13) 0.82393(10) 0.0801(8) Uani 1 1 d . . . N2 N 0.2374(8) 0.5173(3) 0.6992(3) 0.0569(17) Uani 1 1 d . . . C2 C -0.0628(11) 0.5612(6) 0.8125(4) 0.075(3) Uani 1 1 d U . . H2A H -0.0400 0.6014 0.8379 0.090 Uiso 1 1 calc R . . N3 N 0.4711(6) 0.6891(4) 0.7643(3) 0.0531(17) Uani 1 1 d . . . C3 C -0.1870(10) 0.5138(6) 0.8175(4) 0.082(3) Uani 1 1 d U . . H3A H -0.2442 0.5184 0.8476 0.099 Uiso 1 1 calc R . . N4 N 0.2500(8) 0.7194(3) 0.6965(2) 0.0518(15) Uani 1 1 d . . . C4 C -0.2262(12) 0.4612(5) 0.7796(4) 0.077(3) Uani 1 1 d U . . H4A H -0.3167 0.4341 0.7812 0.093 Uiso 1 1 calc R . . C5 C -0.1350(9) 0.4464(4) 0.7380(4) 0.077(3) Uani 1 1 d . . . H5A H -0.1598 0.4057 0.7131 0.092 Uiso 1 1 calc R . . C6 C -0.0022(8) 0.4932(4) 0.7329(4) 0.057(2) Uani 1 1 d . . . C7 C 0.1051(9) 0.4803(5) 0.6916(3) 0.0452(19) Uani 1 1 d U . . C8 C 0.0774(10) 0.4279(5) 0.6505(3) 0.063(3) Uani 1 1 d . . . H8A H -0.0151 0.4038 0.6465 0.075 Uiso 1 1 calc R . . C9 C 0.1896(10) 0.4101(6) 0.6137(4) 0.082(3) Uani 1 1 d U . . H9A H 0.1706 0.3766 0.5845 0.099 Uiso 1 1 calc R . . C10 C 0.3261(9) 0.4430(5) 0.6220(3) 0.062(2) Uani 1 1 d DU . . C11 C 0.4573(9) 0.4217(5) 0.5897(4) 0.066(3) Uani 1 1 d D . . H11A H 0.4425 0.3805 0.5614 0.079 Uiso 1 1 calc R . . C15 C 0.5395(8) 0.5046(5) 0.5751(3) 0.066(3) Uani 1 1 d D . . C16 C 0.5990(9) 0.4989(5) 0.6311(3) 0.069(3) Uani 1 1 d DU . . H16A H 0.7011 0.5177 0.6345 0.082 Uiso 1 1 calc R . . C17 C 0.5814(11) 0.4028(4) 0.6278(4) 0.076(3) Uani 1 1 d D . . H17A H 0.6644 0.3734 0.6125 0.091 Uiso 1 1 calc R . . H17B H 0.5504 0.3762 0.6603 0.091 Uiso 1 1 calc R . . C18 C 0.4962(7) 0.5353(5) 0.6730(4) 0.073(3) Uani 1 1 d D . . H18A H 0.5316 0.5205 0.7077 0.088 Uiso 1 1 calc R . . H18B H 0.4926 0.5968 0.6703 0.088 Uiso 1 1 calc R . . C19 C 0.3440(8) 0.4980(5) 0.6643(3) 0.054(2) Uani 1 1 d DU . . C20 C 0.6609(10) 0.4892(6) 0.5343(4) 0.116(4) Uani 1 1 d D . . H20A H 0.7205 0.4421 0.5451 0.174 Uiso 1 1 calc R . . H20B H 0.7208 0.5391 0.5313 0.174 Uiso 1 1 calc R . . H20C H 0.6171 0.4768 0.5010 0.174 Uiso 1 1 calc R . . C22 C 0.5604(10) 0.6785(5) 0.8038(4) 0.073(3) Uani 1 1 d U . . H22A H 0.5380 0.6388 0.8296 0.088 Uiso 1 1 calc R . . C23 C 0.6959(10) 0.7286(6) 0.8078(4) 0.074(3) Uani 1 1 d U . . H23A H 0.7624 0.7194 0.8349 0.088 Uiso 1 1 calc R . . C24 C 0.7194(8) 0.7858(5) 0.7724(4) 0.066(2) Uani 1 1 d . . . H24A H 0.8033 0.8194 0.7739 0.079 Uiso 1 1 calc R . . C25 C 0.6220(8) 0.7965(4) 0.7336(4) 0.063(2) Uani 1 1 d . . . H25A H 0.6393 0.8386 0.7088 0.076 Uiso 1 1 calc R . . C26 C 0.4991(8) 0.7483(5) 0.7291(3) 0.054(2) Uani 1 1 d U . . C28 C 0.4126(11) 0.8102(5) 0.6419(4) 0.072(3) Uani 1 1 d . . . H28A H 0.5064 0.8302 0.6346 0.087 Uiso 1 1 calc R . . C36 C 0.1426(8) 0.7387(5) 0.6633(3) 0.051(2) Uani 1 1 d DU . . C35 C -0.0027(7) 0.6989(5) 0.6750(3) 0.061(2) Uani 1 1 d D . . H35A H -0.0325 0.7126 0.7105 0.073 Uiso 1 1 calc R . . H35B H 0.0044 0.6377 0.6719 0.073 Uiso 1 1 calc R . . C29 C 0.3002(10) 0.8284(5) 0.6093(4) 0.065(3) Uani 1 1 d . . . H29A H 0.3136 0.8643 0.5807 0.077 Uiso 1 1 calc R . . C27 C 0.3853(9) 0.7586(5) 0.6891(3) 0.059(2) Uani 1 1 d U . . C31 C 0.0233(9) 0.8117(5) 0.5886(3) 0.069(3) Uani 1 1 d D . . H31A H 0.0313 0.8528 0.5599 0.082 Uiso 1 1 calc R . . C33 C -0.1184(8) 0.7337(5) 0.6352(4) 0.066(3) Uani 1 1 d . . . H33A H -0.2199 0.7160 0.6416 0.079 Uiso 1 1 calc R . . C30 C 0.1639(9) 0.7921(4) 0.6193(3) 0.060(2) Uani 1 1 d D . . C32 C -0.0661(11) 0.7277(6) 0.5771(4) 0.077(3) Uani 1 1 d . . . C34 C -0.0928(11) 0.8315(5) 0.6326(4) 0.092(3) Uani 1 1 d D . . H34A H -0.0514 0.8557 0.6643 0.110 Uiso 1 1 calc R . . H34B H -0.1771 0.8637 0.6207 0.110 Uiso 1 1 calc R . . C37 C -0.1875(10) 0.7488(6) 0.5364(3) 0.094(4) Uani 1 1 d . . . H37A H -0.1445 0.7531 0.5022 0.142 Uiso 1 1 calc R . . H37B H -0.2331 0.8018 0.5455 0.142 Uiso 1 1 calc R . . H37C H -0.2599 0.7045 0.5365 0.142 Uiso 1 1 calc R . . C21 C 0.4515(11) 0.5819(5) 0.5576(4) 0.099(3) Uani 1 1 d DU . . H21A H 0.4292 0.6168 0.5874 0.149 Uiso 1 1 calc R . . H21B H 0.3619 0.5635 0.5414 0.149 Uiso 1 1 calc R . . H21C H 0.5080 0.6142 0.5328 0.149 Uiso 1 1 calc R . . C38 C 0.0202(10) 0.6508(6) 0.5595(4) 0.088(3) Uani 1 1 d . . . H38A H 0.0550 0.6597 0.5244 0.132 Uiso 1 1 calc R . . H38B H -0.0418 0.6015 0.5603 0.132 Uiso 1 1 calc R . . H38C H 0.1022 0.6424 0.5825 0.132 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0483(6) 0.0341(5) 0.0750(8) 0.0015(6) -0.0096(11) -0.0042(6) Cl1 0.0815(17) 0.0449(12) 0.107(2) 0.0145(13) -0.0285(16) -0.0040(11) N1 0.057(4) 0.037(3) 0.097(6) 0.023(4) -0.015(5) -0.004(3) Cl2 0.0841(18) 0.0533(13) 0.103(2) -0.0090(13) 0.0081(16) 0.0004(12) N2 0.044(4) 0.035(3) 0.092(5) 0.018(3) -0.001(4) 0.008(4) C2 0.075(3) 0.075(3) 0.076(3) 0.0001(10) 0.0008(10) -0.0008(10) N3 0.044(3) 0.054(4) 0.061(4) -0.002(4) -0.032(4) 0.003(3) C3 0.082(3) 0.083(3) 0.083(3) 0.0009(10) 0.0009(10) -0.0002(10) N4 0.046(3) 0.049(3) 0.060(4) 0.001(3) 0.015(4) -0.011(4) C4 0.077(3) 0.077(3) 0.078(3) 0.0009(10) 0.0006(10) -0.0002(10) C5 0.081(7) 0.035(4) 0.115(8) -0.005(5) -0.035(7) -0.006(4) C6 0.049(5) 0.029(4) 0.092(7) 0.017(5) -0.021(5) -0.006(4) C7 0.045(2) 0.045(2) 0.046(2) 0.0003(10) -0.0009(10) -0.0011(10) C8 0.066(6) 0.040(4) 0.082(7) 0.015(5) -0.035(5) -0.014(4) C9 0.083(3) 0.081(3) 0.082(3) -0.0005(10) -0.0003(10) -0.0003(10) C10 0.062(3) 0.061(3) 0.062(3) -0.0001(10) -0.0003(10) -0.0007(10) C11 0.057(6) 0.041(5) 0.099(8) -0.014(5) 0.020(6) -0.007(4) C15 0.054(5) 0.065(6) 0.080(7) -0.003(5) 0.016(5) 0.020(5) C16 0.068(3) 0.069(3) 0.069(3) 0.0001(10) 0.0007(10) 0.0004(10) C17 0.077(7) 0.055(6) 0.097(8) -0.013(5) 0.027(6) 0.009(5) C18 0.049(6) 0.048(5) 0.122(8) -0.013(5) -0.005(6) -0.015(4) C19 0.054(2) 0.054(2) 0.054(2) 0.0002(10) -0.0012(10) -0.0007(10) C20 0.097(8) 0.093(8) 0.157(11) -0.006(8) 0.043(9) 0.009(7) C22 0.073(3) 0.072(3) 0.074(3) 0.0003(10) -0.0002(10) -0.0004(10) C23 0.073(3) 0.073(3) 0.074(3) -0.0007(10) -0.0012(10) -0.0002(10) C24 0.044(6) 0.059(5) 0.093(7) -0.013(5) -0.008(5) -0.018(4) C25 0.055(5) 0.047(4) 0.087(7) -0.007(5) 0.000(6) -0.029(4) C26 0.054(2) 0.053(2) 0.054(2) 0.0000(10) 0.0001(10) -0.0006(10) C28 0.063(6) 0.056(6) 0.099(8) -0.026(5) 0.021(6) -0.011(5) C36 0.051(2) 0.050(2) 0.051(2) 0.0002(10) 0.0004(10) -0.0003(10) C35 0.039(5) 0.051(5) 0.093(7) 0.016(5) -0.028(5) 0.008(4) C29 0.059(6) 0.052(5) 0.083(7) 0.002(5) -0.005(5) -0.009(4) C27 0.060(2) 0.058(2) 0.060(2) -0.0008(10) 0.0008(10) 0.0005(10) C31 0.074(6) 0.073(6) 0.058(6) 0.015(5) -0.009(5) -0.008(5) C33 0.030(4) 0.052(5) 0.114(8) 0.030(5) 0.008(5) -0.004(4) C30 0.065(6) 0.034(4) 0.081(7) -0.004(4) -0.014(5) 0.009(4) C32 0.081(7) 0.065(6) 0.086(8) -0.017(6) 0.002(6) -0.030(6) C34 0.098(8) 0.059(6) 0.118(9) 0.009(6) 0.010(7) 0.026(6) C37 0.096(8) 0.117(8) 0.071(7) 0.031(6) -0.042(6) -0.045(6) C21 0.099(3) 0.099(3) 0.099(3) 0.0000(10) 0.0001(10) -0.0002(10) C38 0.088(8) 0.080(7) 0.096(8) -0.051(6) -0.017(6) -0.018(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N3 2.290(6) . ? Mn1 N1 2.294(7) . ? Mn1 N2 2.358(6) . ? Mn1 N4 2.387(6) . ? Mn1 Cl1 2.481(3) . ? Mn1 Cl2 2.489(3) . ? N1 C6 1.347(10) . ? N1 C2 1.372(11) . ? N2 C19 1.353(9) . ? N2 C7 1.354(10) . ? C2 C3 1.362(12) . ? N3 C22 1.307(10) . ? N3 C26 1.318(9) . ? C3 C4 1.323(11) . ? N4 C36 1.330(9) . ? N4 C27 1.392(10) . ? C4 C5 1.369(11) . ? C5 C6 1.423(10) . ? C6 C7 1.454(11) . ? C7 C8 1.357(10) . ? C8 C9 1.416(12) . ? C9 C10 1.363(11) . ? C10 C19 1.394(10) . ? C10 C11 1.491(7) . ? C11 C17 1.522(12) . ? C11 C15 1.551(11) . ? C15 C21 1.525(8) . ? C15 C16 1.529(8) . ? C15 C20 1.540(6) . ? C16 C17 1.523(7) . ? C16 C18 1.534(8) . ? C18 C19 1.523(7) . ? C22 C23 1.469(12) . ? C23 C24 1.294(11) . ? C24 C25 1.341(10) . ? C25 C26 1.358(10) . ? C26 C27 1.465(10) . ? C28 C29 1.351(11) . ? C28 C27 1.475(11) . ? C36 C30 1.417(10) . ? C36 C35 1.495(7) . ? C35 C33 1.563(10) . ? C29 C30 1.391(10) . ? C31 C30 1.533(8) . ? C31 C34 1.575(8) . ? C31 C32 1.580(11) . ? C33 C34 1.558(11) . ? C33 C32 1.560(12) . ? C32 C38 1.512(11) . ? C32 C37 1.554(12) . ? 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 N3 Mn1 N1 179.0(3) . . ? N3 Mn1 N2 110.6(2) . . ? N1 Mn1 N2 70.3(3) . . ? N3 Mn1 N4 70.4(2) . . ? N1 Mn1 N4 109.9(2) . . ? N2 Mn1 N4 84.25(19) . . ? N3 Mn1 Cl1 91.07(17) . . ? N1 Mn1 Cl1 88.86(16) . . ? N2 Mn1 Cl1 88.48(16) . . ? N4 Mn1 Cl1 156.05(19) . . ? N3 Mn1 Cl2 89.93(17) . . ? N1 Mn1 Cl2 89.2(2) . . ? N2 Mn1 Cl2 153.91(18) . . ? N4 Mn1 Cl2 88.00(16) . . ? Cl1 Mn1 Cl2 107.65(10) . . ? C6 N1 C2 120.6(7) . . ? C6 N1 Mn1 118.3(6) . . ? C2 N1 Mn1 120.9(6) . . ? C19 N2 C7 116.6(7) . . ? C19 N2 Mn1 126.7(5) . . ? C7 N2 Mn1 116.4(5) . . ? C3 C2 N1 121.0(9) . . ? C22 N3 C26 119.7(7) . . ? C22 N3 Mn1 117.6(6) . . ? C26 N3 Mn1 121.8(5) . . ? C4 C3 C2 119.8(10) . . ? C36 N4 C27 117.7(6) . . ? C36 N4 Mn1 129.2(5) . . ? C27 N4 Mn1 113.0(5) . . ? C3 C4 C5 120.8(10) . . ? C4 C5 C6 119.9(9) . . ? N1 C6 C5 117.6(8) . . ? N1 C6 C7 117.8(7) . . ? C5 C6 C7 124.5(8) . . ? N2 C7 C8 122.6(8) . . ? N2 C7 C6 115.8(7) . . ? C8 C7 C6 121.4(8) . . ? C7 C8 C9 119.8(8) . . ? C10 C9 C8 118.8(9) . . ? C9 C10 C19 117.5(8) . . ? C9 C10 C11 124.1(8) . . ? C19 C10 C11 118.3(8) . . ? C10 C11 C17 106.7(7) . . ? C10 C11 C15 109.3(6) . . ? C17 C11 C15 87.6(6) . . ? C21 C15 C16 120.5(7) . . ? C21 C15 C20 107.7(7) . . ? C16 C15 C20 111.6(7) . . ? C21 C15 C11 119.2(7) . . ? C16 C15 C11 84.2(6) . . ? C20 C15 C11 112.1(7) . . ? C17 C16 C15 88.3(6) . . ? C17 C16 C18 110.1(7) . . ? C15 C16 C18 114.4(7) . . ? C11 C17 C16 85.4(6) . . ? C19 C18 C16 108.0(7) . . ? N2 C19 C10 124.5(7) . . ? N2 C19 C18 118.1(7) . . ? C10 C19 C18 117.4(7) . . ? N3 C22 C23 120.6(9) . . ? C24 C23 C22 117.6(9) . . ? C23 C24 C25 119.5(8) . . ? C24 C25 C26 122.6(8) . . ? N3 C26 C25 119.8(8) . . ? N3 C26 C27 114.6(7) . . ? C25 C26 C27 125.6(8) . . ? C29 C28 C27 119.5(9) . . ? N4 C36 C30 122.7(7) . . ? N4 C36 C35 115.5(7) . . ? C30 C36 C35 121.8(8) . . ? C36 C35 C33 108.8(6) . . ? C28 C29 C30 118.5(9) . . ? N4 C27 C26 118.9(8) . . ? N4 C27 C28 120.3(8) . . ? C26 C27 C28 120.8(8) . . ? C30 C31 C34 103.7(7) . . ? C30 C31 C32 111.0(7) . . ? C34 C31 C32 87.2(7) . . ? C34 C33 C32 88.5(6) . . ? C34 C33 C35 105.8(7) . . ? C32 C33 C35 113.0(7) . . ? C29 C30 C36 120.8(8) . . ? C29 C30 C31 124.8(8) . . ? C36 C30 C31 114.2(8) . . ? C38 C32 C37 110.0(8) . . ? C38 C32 C33 119.4(8) . . ? C37 C32 C33 113.9(8) . . ? C38 C32 C31 117.1(8) . . ? C37 C32 C31 108.2(7) . . ? C33 C32 C31 86.0(6) . . ? C33 C34 C31 86.2(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 N3 Mn1 N1 C6 -178(100) . . . . ? N2 Mn1 N1 C6 -3.9(5) . . . . ? N4 Mn1 N1 C6 72.0(5) . . . . ? Cl1 Mn1 N1 C6 -92.7(5) . . . . ? Cl2 Mn1 N1 C6 159.6(5) . . . . ? N3 Mn1 N1 C2 -5(14) . . . . ? N2 Mn1 N1 C2 170.0(6) . . . . ? N4 Mn1 N1 C2 -114.1(6) . . . . ? Cl1 Mn1 N1 C2 81.2(6) . . . . ? Cl2 Mn1 N1 C2 -26.5(6) . . . . ? N3 Mn1 N2 C19 2.6(6) . . . . ? N1 Mn1 N2 C19 -177.3(6) . . . . ? N4 Mn1 N2 C19 69.1(6) . . . . ? Cl1 Mn1 N2 C19 -88.0(6) . . . . ? Cl2 Mn1 N2 C19 142.6(5) . . . . ? N3 Mn1 N2 C7 -170.8(5) . . . . ? N1 Mn1 N2 C7 9.3(5) . . . . ? N4 Mn1 N2 C7 -104.2(5) . . . . ? Cl1 Mn1 N2 C7 98.7(5) . . . . ? Cl2 Mn1 N2 C7 -30.8(7) . . . . ? C6 N1 C2 C3 0.7(12) . . . . ? Mn1 N1 C2 C3 -173.0(6) . . . . ? N1 Mn1 N3 C22 60(14) . . . . ? N2 Mn1 N3 C22 -114.7(6) . . . . ? N4 Mn1 N3 C22 169.7(6) . . . . ? Cl1 Mn1 N3 C22 -25.9(6) . . . . ? Cl2 Mn1 N3 C22 81.8(6) . . . . ? N1 Mn1 N3 C26 -110(14) . . . . ? N2 Mn1 N3 C26 75.9(6) . . . . ? N4 Mn1 N3 C26 0.2(5) . . . . ? Cl1 Mn1 N3 C26 164.7(6) . . . . ? Cl2 Mn1 N3 C26 -87.7(6) . . . . ? N1 C2 C3 C4 -5.3(14) . . . . ? N3 Mn1 N4 C36 -177.4(7) . . . . ? N1 Mn1 N4 C36 1.6(7) . . . . ? N2 Mn1 N4 C36 68.3(6) . . . . ? Cl1 Mn1 N4 C36 141.3(6) . . . . ? Cl2 Mn1 N4 C36 -86.8(6) . . . . ? N3 Mn1 N4 C27 6.0(5) . . . . ? N1 Mn1 N4 C27 -174.9(5) . . . . ? N2 Mn1 N4 C27 -108.3(5) . . . . ? Cl1 Mn1 N4 C27 -35.3(7) . . . . ? Cl2 Mn1 N4 C27 96.7(5) . . . . ? C2 C3 C4 C5 7.6(14) . . . . ? C3 C4 C5 C6 -5.5(13) . . . . ? C2 N1 C6 C5 1.4(10) . . . . ? Mn1 N1 C6 C5 175.3(5) . . . . ? C2 N1 C6 C7 -175.4(7) . . . . ? Mn1 N1 C6 C7 -1.5(8) . . . . ? C4 C5 C6 N1 0.9(11) . . . . ? C4 C5 C6 C7 177.4(7) . . . . ? C19 N2 C7 C8 -1.7(11) . . . . ? Mn1 N2 C7 C8 172.3(5) . . . . ? C19 N2 C7 C6 172.6(6) . . . . ? Mn1 N2 C7 C6 -13.4(8) . . . . ? N1 C6 C7 N2 10.1(10) . . . . ? C5 C6 C7 N2 -166.4(7) . . . . ? N1 C6 C7 C8 -175.6(6) . . . . ? C5 C6 C7 C8 7.9(12) . . . . ? N2 C7 C8 C9 0.3(11) . . . . ? C6 C7 C8 C9 -173.7(7) . . . . ? C7 C8 C9 C10 3.1(13) . . . . ? C8 C9 C10 C19 -4.9(13) . . . . ? C8 C9 C10 C11 173.1(8) . . . . ? C9 C10 C11 C17 -133.1(9) . . . . ? C19 C10 C11 C17 44.8(10) . . . . ? C9 C10 C11 C15 133.6(9) . . . . ? C19 C10 C11 C15 -48.5(10) . . . . ? C10 C11 C15 C21 -43.2(11) . . . . ? C17 C11 C15 C21 -150.0(8) . . . . ? C10 C11 C15 C16 78.7(8) . . . . ? C17 C11 C15 C16 -28.1(6) . . . . ? C10 C11 C15 C20 -170.4(8) . . . . ? C17 C11 C15 C20 82.8(8) . . . . ? C21 C15 C16 C17 148.7(8) . . . . ? C20 C15 C16 C17 -83.4(8) . . . . ? C11 C15 C16 C17 28.1(6) . . . . ? C21 C15 C16 C18 37.3(11) . . . . ? C20 C15 C16 C18 165.2(7) . . . . ? C11 C15 C16 C18 -83.3(7) . . . . ? C10 C11 C17 C16 -81.2(7) . . . . ? C15 C11 C17 C16 28.2(6) . . . . ? C15 C16 C17 C11 -28.6(6) . . . . ? C18 C16 C17 C11 86.8(7) . . . . ? C17 C16 C18 C19 -48.3(10) . . . . ? C15 C16 C18 C19 49.3(9) . . . . ? C7 N2 C19 C10 -0.3(11) . . . . ? Mn1 N2 C19 C10 -173.6(6) . . . . ? C7 N2 C19 C18 -177.3(7) . . . . ? Mn1 N2 C19 C18 9.4(10) . . . . ? C9 C10 C19 N2 3.6(13) . . . . ? C11 C10 C19 N2 -174.4(7) . . . . ? C9 C10 C19 C18 -179.4(8) . . . . ? C11 C10 C19 C18 2.5(11) . . . . ? C16 C18 C19 N2 175.8(7) . . . . ? C16 C18 C19 C10 -1.4(10) . . . . ? C26 N3 C22 C23 -3.4(12) . . . . ? Mn1 N3 C22 C23 -173.0(6) . . . . ? N3 C22 C23 C24 3.2(13) . . . . ? C22 C23 C24 C25 -0.9(12) . . . . ? C23 C24 C25 C26 -1.2(13) . . . . ? C22 N3 C26 C25 1.3(12) . . . . ? Mn1 N3 C26 C25 170.5(6) . . . . ? C22 N3 C26 C27 -175.4(7) . . . . ? Mn1 N3 C26 C27 -6.2(9) . . . . ? C24 C25 C26 N3 1.1(13) . . . . ? C24 C25 C26 C27 177.4(8) . . . . ? C27 N4 C36 C30 4.6(11) . . . . ? Mn1 N4 C36 C30 -171.8(5) . . . . ? C27 N4 C36 C35 -176.5(6) . . . . ? Mn1 N4 C36 C35 7.1(10) . . . . ? N4 C36 C35 C33 175.6(7) . . . . ? C30 C36 C35 C33 -5.5(11) . . . . ? C27 C28 C29 C30 -4.8(13) . . . . ? C36 N4 C27 C26 171.3(7) . . . . ? Mn1 N4 C27 C26 -11.7(9) . . . . ? C36 N4 C27 C28 -8.1(11) . . . . ? Mn1 N4 C27 C28 168.9(5) . . . . ? N3 C26 C27 N4 12.1(11) . . . . ? C25 C26 C27 N4 -164.4(7) . . . . ? N3 C26 C27 C28 -168.5(7) . . . . ? C25 C26 C27 C28 15.0(12) . . . . ? C29 C28 C27 N4 8.5(12) . . . . ? C29 C28 C27 C26 -170.9(8) . . . . ? C36 C35 C33 C34 -45.2(9) . . . . ? C36 C35 C33 C32 50.0(9) . . . . ? C28 C29 C30 C36 1.3(13) . . . . ? C28 C29 C30 C31 175.0(8) . . . . ? N4 C36 C30 C29 -1.2(12) . . . . ? C35 C36 C30 C29 180.0(8) . . . . ? N4 C36 C30 C31 -175.5(7) . . . . ? C35 C36 C30 C31 5.6(11) . . . . ? C34 C31 C30 C29 -130.1(9) . . . . ? C32 C31 C30 C29 137.5(9) . . . . ? C34 C31 C30 C36 43.9(9) . . . . ? C32 C31 C30 C36 -48.4(10) . . . . ? C34 C33 C32 C38 144.9(8) . . . . ? C35 C33 C32 C38 38.3(10) . . . . ? C34 C33 C32 C37 -82.3(8) . . . . ? C35 C33 C32 C37 171.1(7) . . . . ? C34 C33 C32 C31 25.9(6) . . . . ? C35 C33 C32 C31 -80.7(7) . . . . ? C30 C31 C32 C38 -43.1(11) . . . . ? C34 C31 C32 C38 -146.7(9) . . . . ? C30 C31 C32 C37 -168.1(8) . . . . ? C34 C31 C32 C37 88.3(8) . . . . ? C30 C31 C32 C33 78.1(8) . . . . ? C34 C31 C32 C33 -25.6(6) . . . . ? C32 C33 C34 C31 -26.0(6) . . . . ? C35 C33 C34 C31 87.5(7) . . . . ? C30 C31 C34 C33 -85.3(7) . . . . ? C32 C31 C34 C33 25.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.273 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.066 #END data_720646 _database_code_depnum_ccdc_archive 'CCDC 720646' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H45 Mn2 N4 O6, 2(C H2 Cl2), F6 P' _chemical_formula_sum 'C42 H49 Cl4 F6 Mn2 N4 O6 P' _chemical_formula_weight 1102.50 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 12.63(2) _cell_length_b 18.08(3) _cell_length_c 10.392(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2372(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9105 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 33075 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.45 _reflns_number_total 5860 _reflns_number_gt 4579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER Shelxtl' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. The displacement parameters for carbon atoms of the CH2Cl2 disordered molecules are restrained with ISOR instruction, esd 0.001 ; _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^)+(0.1280P)^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' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 5860 _refine_ls_number_parameters 326 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1826 _refine_ls_wR_factor_gt 0.1691 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.003 _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 0.50964(4) 0.90529(3) 0.67488(5) 0.04354(17) Uani 1 1 d . . . N1 N 0.6394(2) 0.82611(17) 0.6549(3) 0.0467(7) Uani 1 1 d . . . C1 C 0.7394(3) 0.8442(2) 0.6319(5) 0.0557(10) Uani 1 1 d . . . H1A H 0.7560 0.8943 0.6274 0.067 Uiso 1 1 calc R . . O1 O 0.4312(2) 0.91511(16) 0.4911(3) 0.0601(7) Uani 1 1 d . . . O2 O 0.3859(2) 1.00577(18) 0.6135(3) 0.0552(6) Uani 1 1 d . . . N2 N 0.4379(2) 0.79382(15) 0.7069(3) 0.0418(6) Uani 1 1 d . . . C2 C 0.8194(4) 0.7949(3) 0.6146(5) 0.0658(11) Uani 1 1 d . . . H2A H 0.8883 0.8104 0.5980 0.079 Uiso 1 1 calc R . . O3 O 0.5030(3) 0.93971(16) 0.8610(3) 0.0691(8) Uani 1 1 d . . . C3 C 0.7945(3) 0.7225(3) 0.6224(5) 0.0612(11) Uani 1 1 d . . . H3A H 0.8466 0.6868 0.6110 0.073 Uiso 1 1 calc R . . C4 C 0.6922(4) 0.7017(2) 0.6472(4) 0.0573(10) Uani 1 1 d . . . H4A H 0.6748 0.6518 0.6524 0.069 Uiso 1 1 calc R . . C5 C 0.6155(3) 0.75424(18) 0.6643(3) 0.0430(7) Uani 1 1 d . . . C6 C 0.5048(3) 0.73701(18) 0.6943(3) 0.0430(7) Uani 1 1 d . . . C7 C 0.4716(3) 0.6655(2) 0.7121(4) 0.0531(9) Uani 1 1 d . . . H7A H 0.5186 0.6262 0.7027 0.064 Uiso 1 1 calc R . . C8 C 0.3672(3) 0.6530(2) 0.7442(5) 0.0563(9) Uani 1 1 d . . . H8A H 0.3437 0.6048 0.7569 0.068 Uiso 1 1 calc R . . C9 C 0.2979(3) 0.7105(2) 0.7577(4) 0.0494(8) Uani 1 1 d . . . C10 C 0.1844(4) 0.7039(3) 0.7920(4) 0.0597(10) Uani 1 1 d . . . H10A H 0.1569 0.6536 0.8029 0.072 Uiso 1 1 calc R . . C11 C 0.1227(4) 0.7546(3) 0.6998(5) 0.0725(14) Uani 1 1 d . . . H11A H 0.1527 0.7579 0.6141 0.087 Uiso 1 1 calc R . . H11B H 0.0472 0.7449 0.6967 0.087 Uiso 1 1 calc R . . C12 C 0.1529(3) 0.8160(3) 0.7859(5) 0.0655(12) Uani 1 1 d . . . H12A H 0.0992 0.8548 0.7951 0.079 Uiso 1 1 calc R . . C13 C 0.2612(3) 0.8432(2) 0.7524(5) 0.0627(11) Uani 1 1 d . . . H13A H 0.2579 0.8712 0.6729 0.075 Uiso 1 1 calc R . . H13B H 0.2862 0.8760 0.8197 0.075 Uiso 1 1 calc R . . C14 C 0.3367(3) 0.7811(2) 0.7371(4) 0.0445(7) Uani 1 1 d . . . C15 C 0.1559(4) 0.7595(3) 0.8967(5) 0.0638(11) Uani 1 1 d . . . C16 C 0.0454(5) 0.7446(4) 0.9518(6) 0.0877(17) Uani 1 1 d . . . H16A H -0.0037 0.7370 0.8825 0.132 Uiso 1 1 calc R . . H16B H 0.0231 0.7863 1.0023 0.132 Uiso 1 1 calc R . . H16C H 0.0475 0.7012 1.0051 0.132 Uiso 1 1 calc R . . C17 C 0.2338(5) 0.7715(4) 1.0057(5) 0.0845(17) Uani 1 1 d . . . H17A H 0.2307 0.7303 1.0639 0.127 Uiso 1 1 calc R . . H17B H 0.2159 0.8161 1.0509 0.127 Uiso 1 1 calc R . . H17C H 0.3041 0.7757 0.9714 0.127 Uiso 1 1 calc R . . C18 C 0.3842(3) 0.9745(2) 0.5083(4) 0.0489(8) Uani 1 1 d . . . C19 C 0.3259(5) 1.0058(4) 0.3973(5) 0.0794(14) Uani 1 1 d . . . H19A H 0.3503 0.9829 0.3193 0.119 Uiso 1 1 calc R . . H19B H 0.3380 1.0581 0.3930 0.119 Uiso 1 1 calc R . . H19C H 0.2515 0.9965 0.4076 0.119 Uiso 1 1 calc R . . C20 C 0.5000 1.0000 0.9178(6) 0.0602(14) Uani 1 2 d S . . C21 C 0.5000 1.0000 1.0601(7) 0.106(3) Uani 1 2 d S . . H21A H 0.4960 1.0500 1.0909 0.159 Uiso 0.50 1 calc PR . . H21B H 0.5640 0.9774 1.0909 0.159 Uiso 0.50 1 calc PR . . H21C H 0.4400 0.9726 1.0909 0.159 Uiso 0.50 1 calc PR . . P1 P 1.0000 1.0000 0.55405(18) 0.0711(5) Uani 1 2 d S . . F1 F 1.0491(10) 0.9261(4) 0.5498(8) 0.250(5) Uani 1 1 d . . . F2 F 1.0724(7) 1.0266(7) 0.4610(10) 0.358(10) Uani 1 1 d D . . F3 F 1.0707(10) 1.0147(8) 0.6524(9) 0.327(7) Uani 1 1 d D . . Cl1Z Cl 0.8676(7) 0.8988(2) 0.9232(5) 0.148(3) Uani 0.473(9) 1 d PD A -1 C1Z C 0.799(2) 0.9827(8) 0.8863(10) 0.143(8) Uani 0.473(9) 1 d PDU A -1 H1ZA H 0.7290 0.9730 0.8512 0.172 Uiso 0.473(9) 1 calc PR A -1 H1ZB H 0.8385 1.0132 0.8265 0.172 Uiso 0.473(9) 1 calc PR A -1 Cl2Z Cl 0.7913(14) 1.0245(6) 1.0422(8) 0.219(6) Uani 0.473(9) 1 d PD A -1 Cl1Y Cl 0.7622(9) 0.9359(6) 0.9332(7) 0.216(6) Uani 0.527(9) 1 d PD A -2 C1Y C 0.8843(14) 0.9857(14) 0.9447(16) 0.203(11) Uani 0.527(9) 1 d PDU A -2 H1YA H 0.9447 0.9525 0.9443 0.243 Uiso 0.527(9) 1 calc PR A -2 H1YB H 0.8917 1.0212 0.8752 0.243 Uiso 0.527(9) 1 calc PR A -2 Cl2Y Cl 0.8702(11) 1.0310(4) 1.0969(8) 0.206(5) Uani 0.527(9) 1 d PD A -2 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 0.0441(3) 0.0364(2) 0.0501(3) 0.0013(2) 0.0007(2) 0.0018(2) N1 0.0397(14) 0.0429(15) 0.0576(18) 0.0016(14) 0.0031(13) 0.0050(11) C1 0.0415(18) 0.050(2) 0.075(3) 0.0017(19) 0.0034(17) 0.0024(15) O1 0.0649(17) 0.0508(15) 0.0647(17) -0.0044(14) -0.0172(14) -0.0015(13) O2 0.0494(14) 0.0565(15) 0.0598(15) -0.0088(14) -0.0009(12) -0.0078(12) N2 0.0418(14) 0.0371(14) 0.0464(15) 0.0013(11) 0.0045(12) -0.0007(11) C2 0.044(2) 0.075(3) 0.078(3) 0.003(2) 0.002(2) 0.0075(19) O3 0.106(3) 0.0520(15) 0.0490(14) -0.0003(12) 0.0043(17) 0.0069(17) C3 0.050(2) 0.067(3) 0.067(3) -0.007(2) -0.0005(19) 0.0223(19) C4 0.062(2) 0.050(2) 0.060(2) -0.0066(18) 0.0055(18) 0.0140(18) C5 0.0452(16) 0.0461(18) 0.0377(16) 0.0003(14) -0.0006(14) 0.0083(13) C6 0.0506(18) 0.0391(14) 0.0394(15) 0.0001(11) -0.0003(16) 0.0036(14) C7 0.059(2) 0.0361(16) 0.064(2) -0.0051(15) 0.0022(17) -0.0014(15) C8 0.061(2) 0.0415(18) 0.066(2) -0.0007(18) 0.0079(19) -0.0073(16) C9 0.054(2) 0.0515(19) 0.0431(19) 0.0005(16) 0.0060(16) -0.0089(16) C10 0.055(2) 0.069(3) 0.055(2) 0.0015(19) 0.0068(18) -0.0123(19) C11 0.051(2) 0.110(4) 0.057(3) 0.014(2) 0.0012(19) -0.013(2) C12 0.044(2) 0.084(3) 0.069(3) 0.021(2) 0.0101(18) 0.0062(19) C13 0.050(2) 0.053(2) 0.085(3) 0.015(2) 0.014(2) 0.0096(17) C14 0.0421(17) 0.0456(18) 0.0457(18) 0.0025(15) 0.0061(14) 0.0017(13) C15 0.057(2) 0.075(3) 0.059(2) 0.011(2) 0.008(2) -0.004(2) C16 0.076(3) 0.109(4) 0.078(3) 0.019(3) 0.034(3) 0.006(3) C17 0.102(4) 0.104(4) 0.048(2) -0.002(3) 0.002(3) 0.016(3) C18 0.0478(19) 0.0460(18) 0.053(2) 0.0068(16) -0.0104(16) -0.0104(15) C19 0.090(4) 0.082(3) 0.066(3) 0.010(3) -0.016(3) 0.020(3) C20 0.077(4) 0.052(3) 0.051(3) 0.000 0.000 0.013(3) C21 0.176(10) 0.090(5) 0.053(4) 0.000 0.000 0.009(7) P1 0.0728(11) 0.0677(9) 0.0728(10) 0.000 0.000 -0.0221(9) F1 0.435(14) 0.145(5) 0.168(6) 0.013(4) -0.094(8) 0.105(7) F2 0.184(7) 0.441(16) 0.450(17) 0.354(16) 0.152(8) 0.103(9) F3 0.336(16) 0.335(15) 0.309(12) -0.071(12) -0.183(12) -0.061(13) Cl1Z 0.251(9) 0.086(3) 0.108(3) 0.017(2) -0.009(4) 0.023(3) C1Z 0.143(8) 0.143(8) 0.144(8) 0.0003(10) 0.0002(10) 0.0004(10) Cl2Z 0.379(18) 0.148(7) 0.130(6) -0.002(5) -0.010(7) 0.105(9) Cl1Y 0.253(11) 0.252(11) 0.142(5) -0.024(6) -0.002(6) -0.077(10) C1Y 0.203(11) 0.203(11) 0.203(11) 0.0001(10) 0.0000(10) 0.0000(10) Cl2Y 0.360(15) 0.122(4) 0.136(5) -0.015(4) 0.008(7) -0.074(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.034(4) . ? Mn1 O1 2.159(4) . ? Mn1 O2 2.175(4) 2_675 ? Mn1 N1 2.186(4) . ? Mn1 N2 2.234(4) . ? Mn1 O2 2.479(4) . ? N1 C1 1.326(5) . ? N1 C5 1.337(5) . ? C1 C2 1.360(6) . ? O1 C18 1.239(5) . ? O2 C18 1.231(5) . ? O2 Mn1 2.175(4) 2_675 ? N2 C14 1.336(5) . ? N2 C6 1.336(5) . ? C2 C3 1.348(8) . ? O3 C20 1.240(4) . ? C3 C4 1.370(7) . ? C4 C5 1.368(5) . ? C5 C6 1.465(6) . ? C6 C7 1.372(5) . ? C7 C8 1.379(6) . ? C8 C9 1.365(6) . ? C9 C14 1.384(6) . ? C9 C10 1.482(6) . ? C10 C15 1.526(7) . ? C10 C11 1.538(7) . ? C11 C12 1.475(8) . ? C12 C13 1.495(6) . ? C12 C15 1.539(7) . ? C13 C14 1.481(6) . ? C15 C17 1.516(8) . ? C15 C16 1.532(7) . ? C18 C19 1.481(6) . ? C20 O3 1.240(4) 2_675 ? C20 C21 1.479(9) . ? P1 F3 1.383(8) . ? P1 F3 1.383(8) 2_775 ? P1 F2 1.415(7) 2_775 ? P1 F2 1.415(7) . ? P1 F1 1.473(7) . ? P1 F1 1.473(7) 2_775 ? Cl1Z C1Z 1.790(2) . ? C1Z Cl2Z 1.790(3) . ? Cl1Y C1Y 1.790(3) . ? C1Y Cl2Y 1.790(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O1 142.87(15) . . ? O3 Mn1 O2 94.45(14) . 2_675 ? O1 Mn1 O2 87.62(13) . 2_675 ? O3 Mn1 N1 108.76(14) . . ? O1 Mn1 N1 108.30(14) . . ? O2 Mn1 N1 90.08(17) 2_675 . ? O3 Mn1 N2 96.74(13) . . ? O1 Mn1 N2 91.14(12) . . ? O2 Mn1 N2 162.97(11) 2_675 . ? N1 Mn1 N2 74.19(16) . . ? O3 Mn1 O2 89.67(13) . . ? O1 Mn1 O2 54.77(11) . . ? O2 Mn1 O2 76.45(17) 2_675 . ? N1 Mn1 O2 158.12(12) . . ? N2 Mn1 O2 116.32(15) . . ? C1 N1 C5 117.9(3) . . ? C1 N1 Mn1 124.7(3) . . ? C5 N1 Mn1 117.4(2) . . ? N1 C1 C2 124.7(4) . . ? C18 O1 Mn1 99.4(3) . . ? C18 O2 Mn1 127.6(3) . 2_675 ? C18 O2 Mn1 84.4(3) . . ? Mn1 O2 Mn1 94.80(16) 2_675 . ? C14 N2 C6 119.7(3) . . ? C14 N2 Mn1 125.3(2) . . ? C6 N2 Mn1 115.0(3) . . ? C3 C2 C1 117.1(4) . . ? C20 O3 Mn1 136.3(3) . . ? C2 C3 C4 119.9(4) . . ? C5 C4 C3 120.1(4) . . ? N1 C5 C4 120.3(4) . . ? N1 C5 C6 116.0(3) . . ? C4 C5 C6 123.7(4) . . ? N2 C6 C7 121.2(4) . . ? N2 C6 C5 117.4(3) . . ? C7 C6 C5 121.4(3) . . ? C6 C7 C8 118.6(4) . . ? C9 C8 C7 120.9(4) . . ? C8 C9 C14 117.4(4) . . ? C8 C9 C10 125.7(4) . . ? C14 C9 C10 117.0(4) . . ? C9 C10 C15 110.3(4) . . ? C9 C10 C11 107.0(4) . . ? C15 C10 C11 86.1(4) . . ? C12 C11 C10 86.5(4) . . ? C11 C12 C13 110.0(4) . . ? C11 C12 C15 87.8(4) . . ? C13 C12 C15 111.7(4) . . ? C14 C13 C12 111.4(4) . . ? N2 C14 C9 122.2(3) . . ? N2 C14 C13 120.7(3) . . ? C9 C14 C13 117.0(4) . . ? C17 C15 C16 109.7(5) . . ? C17 C15 C10 118.3(4) . . ? C16 C15 C10 111.4(4) . . ? C17 C15 C12 118.7(4) . . ? C16 C15 C12 111.9(4) . . ? C10 C15 C12 84.8(4) . . ? O2 C18 O1 121.3(4) . . ? O2 C18 C19 121.6(4) . . ? O1 C18 C19 117.1(4) . . ? O3 C20 O3 123.2(6) . 2_675 ? O3 C20 C21 118.4(3) . . ? O3 C20 C21 118.4(3) 2_675 . ? F3 P1 F3 84.7(11) . 2_775 ? F3 P1 F2 171.0(10) . 2_775 ? F3 P1 F2 91.3(4) 2_775 2_775 ? F3 P1 F2 91.3(4) . . ? F3 P1 F2 171.0(10) 2_775 . ? F2 P1 F2 93.8(12) 2_775 . ? F3 P1 F1 85.7(7) . . ? F3 P1 F1 96.9(7) 2_775 . ? F2 P1 F1 86.7(5) 2_775 . ? F2 P1 F1 90.9(7) . . ? F3 P1 F1 96.9(7) . 2_775 ? F3 P1 F1 85.7(7) 2_775 2_775 ? F2 P1 F1 90.9(7) 2_775 2_775 ? F2 P1 F1 86.7(6) . 2_775 ? F1 P1 F1 176.5(6) . 2_775 ? Cl1Z C1Z Cl2Z 100.9(5) . . ? Cl2Y C1Y Cl1Y 101.8(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 O3 Mn1 N1 C1 -86.5(4) . . . . ? O1 Mn1 N1 C1 95.8(4) . . . . ? O2 Mn1 N1 C1 8.3(4) 2_675 . . . ? N2 Mn1 N1 C1 -178.4(4) . . . . ? O2 Mn1 N1 C1 59.5(5) . . . . ? O3 Mn1 N1 C5 94.9(3) . . . . ? O1 Mn1 N1 C5 -82.9(3) . . . . ? O2 Mn1 N1 C5 -170.4(3) 2_675 . . . ? N2 Mn1 N1 C5 3.0(3) . . . . ? O2 Mn1 N1 C5 -119.1(3) . . . . ? C5 N1 C1 C2 1.4(7) . . . . ? Mn1 N1 C1 C2 -177.3(4) . . . . ? O3 Mn1 O1 C18 22.0(4) . . . . ? O2 Mn1 O1 C18 -72.2(3) 2_675 . . . ? N1 Mn1 O1 C18 -161.5(2) . . . . ? N2 Mn1 O1 C18 124.8(3) . . . . ? O2 Mn1 O1 C18 2.8(2) . . . . ? O3 Mn1 O2 C18 -171.4(2) . . . . ? O1 Mn1 O2 C18 -2.8(2) . . . . ? O2 Mn1 O2 C18 93.9(2) 2_675 . . . ? N1 Mn1 O2 C18 40.6(4) . . . . ? N2 Mn1 O2 C18 -74.0(2) . . . . ? O3 Mn1 O2 Mn1 61.26(14) . . . 2_675 ? O1 Mn1 O2 Mn1 -130.18(16) . . . 2_675 ? O2 Mn1 O2 Mn1 -33.40(16) 2_675 . . 2_675 ? N1 Mn1 O2 Mn1 -86.8(3) . . . 2_675 ? N2 Mn1 O2 Mn1 158.62(11) . . . 2_675 ? O3 Mn1 N2 C14 69.9(3) . . . . ? O1 Mn1 N2 C14 -73.7(3) . . . . ? O2 Mn1 N2 C14 -159.3(3) 2_675 . . . ? N1 Mn1 N2 C14 177.6(3) . . . . ? O2 Mn1 N2 C14 -23.1(3) . . . . ? O3 Mn1 N2 C6 -109.8(3) . . . . ? O1 Mn1 N2 C6 106.5(3) . . . . ? O2 Mn1 N2 C6 21.0(5) 2_675 . . . ? N1 Mn1 N2 C6 -2.2(2) . . . . ? O2 Mn1 N2 C6 157.2(2) . . . . ? N1 C1 C2 C3 -0.5(8) . . . . ? O1 Mn1 O3 C20 -54.6(5) . . . . ? O2 Mn1 O3 C20 37.3(4) 2_675 . . . ? N1 Mn1 O3 C20 128.9(4) . . . . ? N2 Mn1 O3 C20 -155.5(4) . . . . ? O2 Mn1 O3 C20 -39.1(4) . . . . ? C1 C2 C3 C4 -0.1(8) . . . . ? C2 C3 C4 C5 -0.2(7) . . . . ? C1 N1 C5 C4 -1.6(6) . . . . ? Mn1 N1 C5 C4 177.2(3) . . . . ? C1 N1 C5 C6 177.9(3) . . . . ? Mn1 N1 C5 C6 -3.4(4) . . . . ? C3 C4 C5 N1 1.0(7) . . . . ? C3 C4 C5 C6 -178.4(4) . . . . ? C14 N2 C6 C7 -0.1(5) . . . . ? Mn1 N2 C6 C7 179.6(3) . . . . ? C14 N2 C6 C5 -178.5(3) . . . . ? Mn1 N2 C6 C5 1.2(4) . . . . ? N1 C5 C6 N2 1.4(5) . . . . ? C4 C5 C6 N2 -179.2(4) . . . . ? N1 C5 C6 C7 -177.0(3) . . . . ? C4 C5 C6 C7 2.5(6) . . . . ? N2 C6 C7 C8 -0.4(6) . . . . ? C5 C6 C7 C8 177.9(4) . . . . ? C6 C7 C8 C9 0.3(7) . . . . ? C7 C8 C9 C14 0.3(6) . . . . ? C7 C8 C9 C10 -179.9(4) . . . . ? C8 C9 C10 C15 133.4(5) . . . . ? C14 C9 C10 C15 -46.8(5) . . . . ? C8 C9 C10 C11 -134.5(5) . . . . ? C14 C9 C10 C11 45.3(5) . . . . ? C9 C10 C11 C12 -81.2(4) . . . . ? C15 C10 C11 C12 28.9(3) . . . . ? C10 C11 C12 C13 83.8(4) . . . . ? C10 C11 C12 C15 -28.6(3) . . . . ? C11 C12 C13 C14 -47.3(6) . . . . ? C15 C12 C13 C14 48.5(6) . . . . ? C6 N2 C14 C9 0.8(5) . . . . ? Mn1 N2 C14 C9 -178.9(3) . . . . ? C6 N2 C14 C13 179.6(4) . . . . ? Mn1 N2 C14 C13 -0.1(5) . . . . ? C8 C9 C14 N2 -0.9(6) . . . . ? C10 C9 C14 N2 179.4(4) . . . . ? C8 C9 C14 C13 -179.7(4) . . . . ? C10 C9 C14 C13 0.5(6) . . . . ? C12 C13 C14 N2 179.9(4) . . . . ? C12 C13 C14 C9 -1.2(6) . . . . ? C9 C10 C15 C17 -40.9(6) . . . . ? C11 C10 C15 C17 -147.6(5) . . . . ? C9 C10 C15 C16 -169.4(4) . . . . ? C11 C10 C15 C16 83.9(4) . . . . ? C9 C10 C15 C12 79.0(4) . . . . ? C11 C10 C15 C12 -27.7(3) . . . . ? C11 C12 C15 C17 148.4(5) . . . . ? C13 C12 C15 C17 37.7(6) . . . . ? C11 C12 C15 C16 -82.1(5) . . . . ? C13 C12 C15 C16 167.1(5) . . . . ? C11 C12 C15 C10 28.9(3) . . . . ? C13 C12 C15 C10 -81.8(5) . . . . ? Mn1 O2 C18 O1 96.4(4) 2_675 . . . ? Mn1 O2 C18 O1 4.7(4) . . . . ? Mn1 O2 C18 C19 -83.9(5) 2_675 . . . ? Mn1 O2 C18 C19 -175.6(4) . . . . ? Mn1 O1 C18 O2 -5.4(4) . . . . ? Mn1 O1 C18 C19 174.9(4) . . . . ? Mn1 O3 C20 O3 2.6(3) . . . 2_675 ? Mn1 O3 C20 C21 -177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.217 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.077 #END data_720647 _database_code_depnum_ccdc_archive 'CCDC 720647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H38 Mn N5 O4, N O3, 2(OH2)' _chemical_formula_sum 'C34 H42 Mn N6 O9' _chemical_formula_weight 733.68 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 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 8.953(7) _cell_length_b 12.691(10) _cell_length_c 31.31(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3558(5) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 55797 _diffrn_reflns_av_R_equivalents 0.3152 _diffrn_reflns_av_sigmaI/netI 0.4210 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.81 _reflns_number_total 8934 _reflns_number_gt 2416 _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 ? _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. The hydrogen atoms associated with the solvent waters could not be located and so are omitted from the final refinement and structure factor calculations. They are, however, included in the reported chemical formula and derived values (e.g. formula weight, F_000, etc). The crystal is very weakly diffracting, and few reflections were collected although a large adquisition time was used. That made the Ratio Observed / Unique Reflections being too Low. The Rint is very large and the L.S. GooF smaller than 0.8. This would suggest problems with the crystal system or space group. The space group P212121 used to resolve the structure was checked with the ADDSYM and NEWSYM tools of PLATON to be the correct one. This software didn't suggest any other space group. The Bravais Lattice determination with SMART V.5631(BRUKER 2002) software ranked the Orthorhombic P as the highest symmetry solution (for a Goodness-of fit treshold of 20), and flagged it as the best one. The space group was determined with XPREP V6.14(BRUKER 2003). Looking for higher METRIC symmetry with XPREP also suggested the orthorhombic P as the highest symmetry. The Systematic absence exceptions showed that the 21 glide planes were present, but I/sigma for the reflections violating the exceptions for other planes were higher. The Mean [E*E-1] value also suggested a non-centrosymmetric space group. ; _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^)+(0.0520P)^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' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 8934 _refine_ls_number_parameters 456 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2931 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 0.761 _refine_ls_restrained_S_all 0.761 _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 0.66663(10) 0.69638(7) 0.13529(3) 0.0490(3) Uani 1 1 d . . . O1 O 0.7836(4) 0.7422(3) 0.19361(12) 0.0617(13) Uani 1 1 d . . . H1B H 0.7823 0.8066 0.1959 0.074 Uiso 1 1 calc R . . H1C H 0.7717 0.6996 0.2236 0.074 Uiso 1 1 d R . . N1 N 0.5527(7) 0.8903(6) 0.0912(2) 0.0682(18) Uani 1 1 d . . . C1 C 0.9725(8) 0.8121(6) 0.1138(2) 0.0660(19) Uani 1 1 d . . . H1A H 0.9475 0.8501 0.1381 0.079 Uiso 1 1 calc R . . O2 O 0.6231(5) 0.8699(4) 0.12465(16) 0.0762(15) Uani 1 1 d . . . N2 N 0.8804(5) 0.7341(4) 0.10059(17) 0.0547(15) Uani 1 1 d . . . C2 C 1.1052(8) 0.8379(6) 0.0917(2) 0.070(2) Uani 1 1 d . . . H2A H 1.1689 0.8902 0.1017 0.084 Uiso 1 1 calc R . . N3 N 0.6682(6) 0.6061(4) 0.06988(14) 0.0479(12) Uani 1 1 d . . . O3 O 0.5258(6) 0.9825(4) 0.08135(16) 0.101(2) Uani 1 1 d . . . C3 C 1.1369(8) 0.7834(6) 0.0551(2) 0.068(2) Uani 1 1 d . . . H3A H 1.2247 0.7976 0.0403 0.082 Uiso 1 1 calc R . . N4 N 0.4496(5) 0.6883(4) 0.17106(15) 0.0480(13) Uani 1 1 d . . . O4 O 0.5109(6) 0.8165(5) 0.06852(19) 0.112(2) Uani 1 1 d . . . C4 C 1.0406(7) 0.7081(6) 0.0400(2) 0.0624(19) Uani 1 1 d . . . H4A H 1.0599 0.6737 0.0144 0.075 Uiso 1 1 calc R . . N5 N 0.6489(6) 0.5316(3) 0.16700(15) 0.0474(13) Uani 1 1 d . . . C5 C 0.9135(7) 0.6836(5) 0.0637(2) 0.0509(17) Uani 1 1 d . . . C6 C 0.7990(7) 0.6048(5) 0.0478(2) 0.0486(17) Uani 1 1 d . . . C7 C 0.8243(7) 0.5424(5) 0.0130(2) 0.0519(17) Uani 1 1 d . . . H7A H 0.9185 0.5403 0.0004 0.062 Uiso 1 1 calc R . . C8 C 0.7084(8) 0.4824(5) -0.0036(2) 0.062(2) Uani 1 1 d . . . H8A H 0.7241 0.4392 -0.0272 0.075 Uiso 1 1 calc R . . C9 C 0.5677(8) 0.4877(5) 0.0157(2) 0.0521(17) Uani 1 1 d . . . C10 C 0.4274(8) 0.4423(5) -0.0022(2) 0.0645(19) Uani 1 1 d . . . H10A H 0.4377 0.4050 -0.0295 0.077 Uiso 1 1 calc R . . C11 C 0.3071(7) 0.5296(5) -0.0009(2) 0.0660(19) Uani 1 1 d . . . H11A H 0.2217 0.5167 -0.0192 0.079 Uiso 1 1 calc R . . H11B H 0.3457 0.6004 -0.0047 0.079 Uiso 1 1 calc R . . C12 C 0.2836(7) 0.4967(5) 0.0466(2) 0.0583(19) Uani 1 1 d . . . H12A H 0.1805 0.5014 0.0569 0.070 Uiso 1 1 calc R . . C13 C 0.3360(9) 0.3834(5) 0.0333(2) 0.0634(18) Uani 1 1 d . . . C14 C 0.4016(6) 0.5507(5) 0.07513(19) 0.0531(18) Uani 1 1 d . . . H14A H 0.3725 0.6232 0.0804 0.064 Uiso 1 1 calc R . . H14B H 0.4074 0.5146 0.1024 0.064 Uiso 1 1 calc R . . C15 C 0.5543(8) 0.5482(5) 0.0532(2) 0.0506(17) Uani 1 1 d . . . C16 C 0.2032(8) 0.3200(5) 0.0135(2) 0.096(3) Uani 1 1 d . . . H16A H 0.2380 0.2522 0.0042 0.145 Uiso 1 1 calc R . . H16B H 0.1637 0.3580 -0.0105 0.145 Uiso 1 1 calc R . . H16C H 0.1263 0.3111 0.0345 0.145 Uiso 1 1 calc R . . C17 C 0.4167(7) 0.3150(6) 0.0658(2) 0.087(2) Uani 1 1 d . . . H17A H 0.4513 0.2518 0.0522 0.130 Uiso 1 1 calc R . . H17B H 0.3494 0.2971 0.0885 0.130 Uiso 1 1 calc R . . H17C H 0.5003 0.3530 0.0772 0.130 Uiso 1 1 calc R . . C18 C 0.3591(8) 0.7703(5) 0.1764(2) 0.0624(19) Uani 1 1 d . . . H18A H 0.3886 0.8351 0.1653 0.075 Uiso 1 1 calc R . . C19 C 0.2214(7) 0.7646(6) 0.1978(2) 0.069(2) Uani 1 1 d . . . H19A H 0.1624 0.8240 0.2020 0.083 Uiso 1 1 calc R . . C20 C 0.1780(9) 0.6671(7) 0.2122(2) 0.070(2) Uani 1 1 d . . . H20A H 0.0844 0.6588 0.2246 0.084 Uiso 1 1 calc R . . C21 C 0.2700(7) 0.5831(6) 0.2085(2) 0.062(2) Uani 1 1 d . . . H21A H 0.2418 0.5180 0.2195 0.075 Uiso 1 1 calc R . . C22 C 0.4064(8) 0.5947(5) 0.1883(2) 0.0500(18) Uani 1 1 d . . . C23 C 0.5165(7) 0.5088(5) 0.18529(19) 0.0443(16) Uani 1 1 d . . . C24 C 0.4875(7) 0.4111(6) 0.2017(2) 0.069(2) Uani 1 1 d . . . H24A H 0.3950 0.3974 0.2140 0.082 Uiso 1 1 calc R . . C25 C 0.5954(8) 0.3314(5) 0.2003(2) 0.063(2) Uani 1 1 d . . . H25A H 0.5748 0.2641 0.2105 0.076 Uiso 1 1 calc R . . C26 C 0.7334(8) 0.3558(5) 0.1833(2) 0.0535(19) Uani 1 1 d . . . C27 C 0.8616(8) 0.2799(5) 0.18183(19) 0.0617(19) Uani 1 1 d . . . H27A H 0.8448 0.2106 0.1948 0.074 Uiso 1 1 calc R . . C28 C 1.0030(7) 0.3425(5) 0.1976(2) 0.066(2) Uani 1 1 d . . . H28A H 0.9820 0.3955 0.2191 0.079 Uiso 1 1 calc R . . H28B H 1.0867 0.2984 0.2059 0.079 Uiso 1 1 calc R . . C29 C 1.0119(7) 0.3860(5) 0.1512(2) 0.063(2) Uani 1 1 d . . . H29A H 1.1131 0.3976 0.1402 0.075 Uiso 1 1 calc R . . C30 C 0.9344(7) 0.2803(5) 0.1360(2) 0.0596(17) Uani 1 1 d . . . C31 C 0.9069(7) 0.4795(5) 0.1472(2) 0.0579(19) Uani 1 1 d . . . H31A H 0.9503 0.5399 0.1616 0.069 Uiso 1 1 calc R . . H31B H 0.8947 0.4975 0.1173 0.069 Uiso 1 1 calc R . . C32 C 0.7560(7) 0.4557(6) 0.16644(19) 0.0510(18) Uani 1 1 d . . . C33 C 0.8313(8) 0.2847(5) 0.09728(19) 0.086(2) Uani 1 1 d . . . H33A H 0.8891 0.2985 0.0721 0.129 Uiso 1 1 calc R . . H33B H 0.7592 0.3399 0.1011 0.129 Uiso 1 1 calc R . . H33C H 0.7805 0.2185 0.0942 0.129 Uiso 1 1 calc R . . C34 C 1.0454(7) 0.1886(5) 0.1294(2) 0.078(2) Uani 1 1 d . . . H34A H 1.0936 0.1961 0.1022 0.117 Uiso 1 1 calc R . . H34B H 0.9924 0.1228 0.1303 0.117 Uiso 1 1 calc R . . H34C H 1.1191 0.1898 0.1516 0.117 Uiso 1 1 calc R . . O2S O 0.3274(6) 0.1396(4) 0.23230(16) 0.0960(17) Uani 1 1 d . . . N1S N 0.2370(9) 0.0710(6) 0.2185(2) 0.076(2) Uani 1 1 d . . . O1S O 0.2740(6) 0.0158(4) 0.1882(2) 0.115(2) Uani 1 1 d . . . O3S O 0.1126(6) 0.0652(4) 0.23492(17) 0.0902(18) Uani 1 1 d . . . O1W O 0.8573(5) 0.9517(3) 0.20456(13) 0.0810(14) Uani 1 1 d . . . O2W O 0.6097(5) 1.0662(4) 0.17601(19) 0.116(2) 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 0.0455(5) 0.0515(6) 0.0500(5) -0.0026(5) 0.0034(6) -0.0043(6) O1 0.069(3) 0.056(3) 0.061(3) -0.001(2) -0.004(2) -0.008(2) N1 0.069(5) 0.079(6) 0.057(5) -0.003(5) 0.008(4) 0.000(5) C1 0.063(5) 0.072(5) 0.063(5) 0.000(4) 0.003(4) -0.014(5) O2 0.069(4) 0.086(4) 0.074(4) 0.005(3) -0.008(3) 0.008(3) N2 0.047(4) 0.062(4) 0.055(4) -0.001(3) 0.000(3) -0.014(3) C2 0.052(5) 0.077(6) 0.081(6) -0.009(5) -0.005(4) -0.022(4) N3 0.040(3) 0.052(3) 0.052(3) 0.011(3) 0.002(3) 0.002(3) O3 0.140(5) 0.064(4) 0.100(5) 0.018(3) -0.005(4) 0.027(4) C3 0.055(5) 0.062(5) 0.088(6) 0.016(4) 0.012(5) -0.010(5) N4 0.047(3) 0.044(3) 0.053(3) -0.008(3) 0.010(3) 0.004(3) O4 0.112(5) 0.103(5) 0.121(5) -0.041(4) -0.023(4) -0.004(4) C4 0.056(5) 0.074(5) 0.057(4) 0.007(4) 0.019(4) -0.001(5) N5 0.051(4) 0.041(3) 0.049(3) 0.001(3) -0.002(3) 0.003(3) C5 0.050(4) 0.051(4) 0.052(5) 0.015(4) -0.002(4) 0.011(4) C6 0.055(5) 0.047(4) 0.044(4) 0.008(4) 0.004(4) 0.006(4) C7 0.045(4) 0.054(4) 0.057(5) -0.002(4) 0.017(4) 0.000(4) C8 0.080(6) 0.044(4) 0.062(5) 0.002(4) 0.005(5) 0.007(4) C9 0.059(5) 0.049(4) 0.049(5) -0.010(4) 0.007(4) 0.000(4) C10 0.080(5) 0.066(5) 0.048(5) -0.011(4) -0.001(4) -0.007(5) C11 0.057(5) 0.065(5) 0.075(5) 0.006(4) -0.006(4) -0.001(4) C12 0.049(5) 0.070(5) 0.056(5) -0.007(4) 0.002(4) 0.001(4) C13 0.069(5) 0.062(5) 0.059(5) 0.000(4) 0.006(5) -0.010(5) C14 0.040(4) 0.063(5) 0.056(4) -0.008(4) 0.012(4) -0.005(4) C15 0.052(5) 0.048(4) 0.052(5) 0.007(4) 0.004(4) 0.003(4) C16 0.094(6) 0.086(6) 0.109(6) -0.030(5) -0.002(5) -0.036(5) C17 0.074(5) 0.084(6) 0.103(6) 0.012(5) 0.007(5) -0.002(5) C18 0.060(5) 0.063(5) 0.064(5) 0.005(4) 0.007(4) -0.009(4) C19 0.047(5) 0.081(6) 0.079(6) -0.021(5) -0.002(4) 0.014(4) C20 0.055(5) 0.086(6) 0.070(5) -0.004(4) 0.003(5) -0.015(6) C21 0.047(4) 0.077(6) 0.063(5) -0.006(4) 0.015(4) 0.004(4) C22 0.053(4) 0.037(4) 0.060(5) 0.001(4) 0.008(4) -0.008(4) C23 0.048(5) 0.038(4) 0.047(4) 0.006(3) 0.006(4) -0.004(4) C24 0.051(4) 0.062(5) 0.093(6) 0.009(5) 0.012(4) 0.007(4) C25 0.071(5) 0.045(5) 0.073(5) 0.006(4) 0.009(4) -0.015(4) C26 0.055(5) 0.056(5) 0.049(5) 0.005(4) 0.002(4) -0.005(4) C27 0.077(5) 0.047(4) 0.060(5) 0.006(3) 0.011(4) 0.015(4) C28 0.070(5) 0.059(5) 0.069(5) 0.008(4) -0.008(4) 0.006(4) C29 0.055(5) 0.073(5) 0.061(5) 0.008(4) 0.005(4) 0.013(4) C30 0.067(4) 0.055(5) 0.057(4) 0.000(4) -0.009(4) 0.011(4) C31 0.049(4) 0.056(4) 0.069(5) 0.004(4) 0.009(4) 0.003(4) C32 0.059(5) 0.045(5) 0.049(4) 0.004(4) 0.000(4) -0.008(4) C33 0.094(6) 0.090(6) 0.074(5) -0.017(4) -0.018(5) 0.026(6) C34 0.086(5) 0.074(5) 0.073(5) -0.003(5) 0.006(4) 0.021(4) O2S 0.083(4) 0.110(4) 0.095(4) -0.003(3) 0.006(4) -0.015(4) N1S 0.099(6) 0.061(5) 0.069(6) 0.010(4) 0.001(5) 0.014(5) O1S 0.145(6) 0.085(4) 0.114(5) -0.033(4) 0.019(4) 0.033(4) O3S 0.072(4) 0.105(4) 0.094(4) -0.003(3) 0.018(3) -0.001(4) O1W 0.099(4) 0.065(3) 0.079(3) -0.008(2) -0.008(3) -0.005(3) O2W 0.079(4) 0.096(4) 0.172(5) -0.049(4) -0.011(4) 0.004(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 2.184(4) . ? Mn1 N4 2.246(5) . ? Mn1 N2 2.252(5) . ? Mn1 O2 2.261(5) . ? Mn1 N5 2.321(5) . ? Mn1 N3 2.347(5) . ? N1 O4 1.233(7) . ? N1 O3 1.234(7) . ? N1 O2 1.251(7) . ? C1 N2 1.353(7) . ? C1 C2 1.413(8) . ? N2 C5 1.353(7) . ? C2 C3 1.368(8) . ? N3 C6 1.359(7) . ? N3 C15 1.361(7) . ? C3 C4 1.371(8) . ? N4 C18 1.330(7) . ? N4 C22 1.360(7) . ? C4 C5 1.393(8) . ? N5 C23 1.348(7) . ? N5 C32 1.359(7) . ? C5 C6 1.516(8) . ? C6 C7 1.368(8) . ? C7 C8 1.388(8) . ? C8 C9 1.399(8) . ? C9 C15 1.407(8) . ? C9 C10 1.492(8) . ? C10 C11 1.545(8) . ? C10 C13 1.570(8) . ? C11 C12 1.558(8) . ? C12 C14 1.545(7) . ? C12 C13 1.568(8) . ? C13 C17 1.520(8) . ? C13 C16 1.564(9) . ? C14 C15 1.530(8) . ? C18 C19 1.405(8) . ? C19 C20 1.374(8) . ? C20 C21 1.352(8) . ? C21 C22 1.385(8) . ? C22 C23 1.471(8) . ? C23 C24 1.368(8) . ? C24 C25 1.399(8) . ? C25 C26 1.381(8) . ? C26 C32 1.388(8) . ? C26 C27 1.500(8) . ? C27 C28 1.575(8) . ? C27 C30 1.576(8) . ? C28 C29 1.559(8) . ? C29 C31 1.519(8) . ? C29 C30 1.583(8) . ? C30 C33 1.525(8) . ? C30 C34 1.545(8) . ? C31 C32 1.510(7) . ? O2S N1S 1.265(8) . ? N1S O1S 1.225(7) . ? N1S O3S 1.229(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 N4 90.57(16) . . ? O1 Mn1 N2 86.53(18) . . ? N4 Mn1 N2 170.4(2) . . ? O1 Mn1 O2 86.93(17) . . ? N4 Mn1 O2 88.23(18) . . ? N2 Mn1 O2 82.45(17) . . ? O1 Mn1 N5 85.12(16) . . ? N4 Mn1 N5 71.7(2) . . ? N2 Mn1 N5 117.12(19) . . ? O2 Mn1 N5 158.28(18) . . ? O1 Mn1 N3 148.99(17) . . ? N4 Mn1 N3 114.71(19) . . ? N2 Mn1 N3 71.2(2) . . ? O2 Mn1 N3 110.35(17) . . ? N5 Mn1 N3 86.22(16) . . ? O4 N1 O3 121.2(8) . . ? O4 N1 O2 118.6(8) . . ? O3 N1 O2 120.2(7) . . ? N2 C1 C2 122.2(6) . . ? N1 O2 Mn1 114.3(5) . . ? C5 N2 C1 118.2(5) . . ? C5 N2 Mn1 119.8(4) . . ? C1 N2 Mn1 121.7(4) . . ? C3 C2 C1 117.9(7) . . ? C6 N3 C15 116.4(5) . . ? C6 N3 Mn1 117.0(4) . . ? C15 N3 Mn1 126.4(4) . . ? C2 C3 C4 120.7(6) . . ? C18 N4 C22 117.5(5) . . ? C18 N4 Mn1 123.6(4) . . ? C22 N4 Mn1 118.9(4) . . ? C3 C4 C5 119.1(6) . . ? C23 N5 C32 118.4(5) . . ? C23 N5 Mn1 115.8(4) . . ? C32 N5 Mn1 125.8(5) . . ? N2 C5 C4 121.8(6) . . ? N2 C5 C6 116.4(6) . . ? C4 C5 C6 121.7(7) . . ? N3 C6 C7 123.8(6) . . ? N3 C6 C5 114.1(6) . . ? C7 C6 C5 122.1(6) . . ? C6 C7 C8 119.4(6) . . ? C7 C8 C9 119.1(6) . . ? C8 C9 C15 117.6(7) . . ? C8 C9 C10 125.2(6) . . ? C15 C9 C10 116.9(6) . . ? C9 C10 C11 107.5(5) . . ? C9 C10 C13 110.9(5) . . ? C11 C10 C13 87.7(5) . . ? C10 C11 C12 85.8(5) . . ? C14 C12 C11 109.9(5) . . ? C14 C12 C13 110.8(5) . . ? C11 C12 C13 87.3(5) . . ? C17 C13 C16 109.5(6) . . ? C17 C13 C12 119.2(6) . . ? C16 C13 C12 110.4(6) . . ? C17 C13 C10 119.9(6) . . ? C16 C13 C10 111.1(6) . . ? C12 C13 C10 84.6(5) . . ? C15 C14 C12 110.0(5) . . ? N3 C15 C9 123.4(6) . . ? N3 C15 C14 119.1(6) . . ? C9 C15 C14 117.5(6) . . ? N4 C18 C19 123.6(6) . . ? C20 C19 C18 116.9(7) . . ? C21 C20 C19 120.7(7) . . ? C20 C21 C22 119.5(7) . . ? N4 C22 C21 121.7(6) . . ? N4 C22 C23 115.6(6) . . ? C21 C22 C23 122.7(7) . . ? N5 C23 C24 121.4(6) . . ? N5 C23 C22 117.2(6) . . ? C24 C23 C22 121.4(6) . . ? C23 C24 C25 120.9(6) . . ? C26 C25 C24 117.9(6) . . ? C25 C26 C32 118.8(6) . . ? C25 C26 C27 123.6(6) . . ? C32 C26 C27 117.6(6) . . ? C26 C27 C28 106.4(5) . . ? C26 C27 C30 109.9(5) . . ? C28 C27 C30 87.3(5) . . ? C29 C28 C27 85.8(5) . . ? C31 C29 C28 108.7(5) . . ? C31 C29 C30 111.5(5) . . ? C28 C29 C30 87.6(5) . . ? C33 C30 C34 108.1(6) . . ? C33 C30 C27 118.3(5) . . ? C34 C30 C27 112.6(5) . . ? C33 C30 C29 118.2(5) . . ? C34 C30 C29 113.4(5) . . ? C27 C30 C29 84.9(5) . . ? C32 C31 C29 111.4(5) . . ? N5 C32 C26 122.6(6) . . ? N5 C32 C31 119.7(6) . . ? C26 C32 C31 117.7(6) . . ? O1S N1S O3S 122.3(9) . . ? O1S N1S O2S 119.0(8) . . ? O3S N1S O2S 118.6(8) . . ? 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 O4 N1 O2 Mn1 2.2(8) . . . . ? O3 N1 O2 Mn1 -178.1(5) . . . . ? O1 Mn1 O2 N1 179.1(4) . . . . ? N4 Mn1 O2 N1 -90.3(4) . . . . ? N2 Mn1 O2 N1 92.2(4) . . . . ? N5 Mn1 O2 N1 -112.3(6) . . . . ? N3 Mn1 O2 N1 25.5(5) . . . . ? C2 C1 N2 C5 -3.8(9) . . . . ? C2 C1 N2 Mn1 -178.6(5) . . . . ? O1 Mn1 N2 C5 152.1(4) . . . . ? N4 Mn1 N2 C5 -135.3(10) . . . . ? O2 Mn1 N2 C5 -120.6(5) . . . . ? N5 Mn1 N2 C5 69.3(5) . . . . ? N3 Mn1 N2 C5 -6.0(4) . . . . ? O1 Mn1 N2 C1 -33.3(5) . . . . ? N4 Mn1 N2 C1 39.4(13) . . . . ? O2 Mn1 N2 C1 54.1(5) . . . . ? N5 Mn1 N2 C1 -116.0(5) . . . . ? N3 Mn1 N2 C1 168.7(5) . . . . ? N2 C1 C2 C3 2.2(10) . . . . ? O1 Mn1 N3 C6 -35.4(5) . . . . ? N4 Mn1 N3 C6 -177.2(4) . . . . ? N2 Mn1 N3 C6 11.0(4) . . . . ? O2 Mn1 N3 C6 85.0(4) . . . . ? N5 Mn1 N3 C6 -109.4(4) . . . . ? O1 Mn1 N3 C15 139.4(4) . . . . ? N4 Mn1 N3 C15 -2.5(5) . . . . ? N2 Mn1 N3 C15 -174.3(5) . . . . ? O2 Mn1 N3 C15 -100.2(5) . . . . ? N5 Mn1 N3 C15 65.3(5) . . . . ? C1 C2 C3 C4 1.5(10) . . . . ? O1 Mn1 N4 C18 88.2(5) . . . . ? N2 Mn1 N4 C18 15.8(14) . . . . ? O2 Mn1 N4 C18 1.3(5) . . . . ? N5 Mn1 N4 C18 172.8(5) . . . . ? N3 Mn1 N4 C18 -110.4(5) . . . . ? O1 Mn1 N4 C22 -92.2(4) . . . . ? N2 Mn1 N4 C22 -164.5(10) . . . . ? O2 Mn1 N4 C22 -179.1(5) . . . . ? N5 Mn1 N4 C22 -7.5(4) . . . . ? N3 Mn1 N4 C22 69.3(5) . . . . ? C2 C3 C4 C5 -3.4(10) . . . . ? O1 Mn1 N5 C23 100.3(4) . . . . ? N4 Mn1 N5 C23 8.1(4) . . . . ? N2 Mn1 N5 C23 -176.1(4) . . . . ? O2 Mn1 N5 C23 31.4(7) . . . . ? N3 Mn1 N5 C23 -109.5(4) . . . . ? O1 Mn1 N5 C32 -83.7(5) . . . . ? N4 Mn1 N5 C32 -175.9(5) . . . . ? N2 Mn1 N5 C32 -0.1(5) . . . . ? O2 Mn1 N5 C32 -152.6(5) . . . . ? N3 Mn1 N5 C32 66.5(5) . . . . ? C1 N2 C5 C4 1.9(9) . . . . ? Mn1 N2 C5 C4 176.8(4) . . . . ? C1 N2 C5 C6 -173.8(5) . . . . ? Mn1 N2 C5 C6 1.1(7) . . . . ? C3 C4 C5 N2 1.7(9) . . . . ? C3 C4 C5 C6 177.1(5) . . . . ? C15 N3 C6 C7 -5.9(8) . . . . ? Mn1 N3 C6 C7 169.3(5) . . . . ? C15 N3 C6 C5 170.8(5) . . . . ? Mn1 N3 C6 C5 -14.0(6) . . . . ? N2 C5 C6 N3 8.8(7) . . . . ? C4 C5 C6 N3 -167.0(5) . . . . ? N2 C5 C6 C7 -174.5(5) . . . . ? C4 C5 C6 C7 9.8(9) . . . . ? N3 C6 C7 C8 5.2(9) . . . . ? C5 C6 C7 C8 -171.2(5) . . . . ? C6 C7 C8 C9 0.5(9) . . . . ? C7 C8 C9 C15 -4.8(9) . . . . ? C7 C8 C9 C10 169.5(6) . . . . ? C8 C9 C10 C11 -130.0(7) . . . . ? C15 C9 C10 C11 44.4(7) . . . . ? C8 C9 C10 C13 135.7(7) . . . . ? C15 C9 C10 C13 -49.9(8) . . . . ? C9 C10 C11 C12 -82.8(6) . . . . ? C13 C10 C11 C12 28.4(4) . . . . ? C10 C11 C12 C14 82.8(5) . . . . ? C10 C11 C12 C13 -28.4(5) . . . . ? C14 C12 C13 C17 39.1(8) . . . . ? C11 C12 C13 C17 149.4(6) . . . . ? C14 C12 C13 C16 167.2(5) . . . . ? C11 C12 C13 C16 -82.5(5) . . . . ? C14 C12 C13 C10 -82.3(6) . . . . ? C11 C12 C13 C10 28.0(5) . . . . ? C9 C10 C13 C17 -41.2(8) . . . . ? C11 C10 C13 C17 -149.0(6) . . . . ? C9 C10 C13 C16 -170.6(6) . . . . ? C11 C10 C13 C16 81.6(6) . . . . ? C9 C10 C13 C12 79.6(6) . . . . ? C11 C10 C13 C12 -28.2(5) . . . . ? C11 C12 C14 C15 -41.7(7) . . . . ? C13 C12 C14 C15 53.1(7) . . . . ? C6 N3 C15 C9 1.1(8) . . . . ? Mn1 N3 C15 C9 -173.6(4) . . . . ? C6 N3 C15 C14 -176.9(5) . . . . ? Mn1 N3 C15 C14 8.4(7) . . . . ? C8 C9 C15 N3 4.1(9) . . . . ? C10 C9 C15 N3 -170.7(6) . . . . ? C8 C9 C15 C14 -177.9(6) . . . . ? C10 C9 C15 C14 7.3(8) . . . . ? C12 C14 C15 N3 169.6(5) . . . . ? C12 C14 C15 C9 -8.5(8) . . . . ? C22 N4 C18 C19 -1.5(9) . . . . ? Mn1 N4 C18 C19 178.2(5) . . . . ? N4 C18 C19 C20 -2.6(10) . . . . ? C18 C19 C20 C21 4.8(10) . . . . ? C19 C20 C21 C22 -3.0(10) . . . . ? C18 N4 C22 C21 3.5(9) . . . . ? Mn1 N4 C22 C21 -176.2(5) . . . . ? C18 N4 C22 C23 -174.2(5) . . . . ? Mn1 N4 C22 C23 6.1(7) . . . . ? C20 C21 C22 N4 -1.3(10) . . . . ? C20 C21 C22 C23 176.2(6) . . . . ? C32 N5 C23 C24 -2.1(9) . . . . ? Mn1 N5 C23 C24 174.2(5) . . . . ? C32 N5 C23 C22 175.7(5) . . . . ? Mn1 N5 C23 C22 -8.0(7) . . . . ? N4 C22 C23 N5 1.5(8) . . . . ? C21 C22 C23 N5 -176.1(6) . . . . ? N4 C22 C23 C24 179.3(6) . . . . ? C21 C22 C23 C24 1.7(10) . . . . ? N5 C23 C24 C25 0.4(10) . . . . ? C22 C23 C24 C25 -177.3(6) . . . . ? C23 C24 C25 C26 2.3(10) . . . . ? C24 C25 C26 C32 -3.3(10) . . . . ? C24 C25 C26 C27 176.7(6) . . . . ? C25 C26 C27 C28 -133.9(6) . . . . ? C32 C26 C27 C28 46.0(7) . . . . ? C25 C26 C27 C30 133.0(7) . . . . ? C32 C26 C27 C30 -47.0(8) . . . . ? C26 C27 C28 C29 -81.6(5) . . . . ? C30 C27 C28 C29 28.4(4) . . . . ? C27 C28 C29 C31 83.6(6) . . . . ? C27 C28 C29 C30 -28.3(4) . . . . ? C26 C27 C30 C33 -41.0(8) . . . . ? C28 C27 C30 C33 -147.4(6) . . . . ? C26 C27 C30 C34 -168.3(5) . . . . ? C28 C27 C30 C34 85.3(6) . . . . ? C26 C27 C30 C29 78.5(5) . . . . ? C28 C27 C30 C29 -28.0(4) . . . . ? C31 C29 C30 C33 38.6(8) . . . . ? C28 C29 C30 C33 147.8(6) . . . . ? C31 C29 C30 C34 166.6(5) . . . . ? C28 C29 C30 C34 -84.2(6) . . . . ? C31 C29 C30 C27 -80.9(6) . . . . ? C28 C29 C30 C27 28.3(4) . . . . ? C28 C29 C31 C32 -46.6(7) . . . . ? C30 C29 C31 C32 48.3(7) . . . . ? C23 N5 C32 C26 1.1(9) . . . . ? Mn1 N5 C32 C26 -174.8(4) . . . . ? C23 N5 C32 C31 -178.4(5) . . . . ? Mn1 N5 C32 C31 5.6(8) . . . . ? C25 C26 C32 N5 1.6(10) . . . . ? C27 C26 C32 N5 -178.3(5) . . . . ? C25 C26 C32 C31 -178.8(6) . . . . ? C27 C26 C32 C31 1.2(9) . . . . ? C29 C31 C32 N5 178.0(5) . . . . ? C29 C31 C32 C26 -1.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 'ACTA 50' _diffrn_measured_fraction_theta_full 'ACTA 50' _refine_diff_density_max 0.218 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.054 # Attachment 'Mn-pinenes_revised_CIF.cif' data_720648 _database_code_depnum_ccdc_archive 'CCDC 720648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H36 Cl4 Mn2 N4' _chemical_formula_sum 'C34 H36 Cl4 Mn2 N4' _chemical_formula_weight 752.35 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6452(13) _cell_length_b 8.4060(15) _cell_length_c 25.468(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.982(3) _cell_angle_gamma 90.00 _cell_volume 1635.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.130 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 25595 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 28.30 _reflns_number_total 7938 _reflns_number_gt 6732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Shelxtl' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0332P)^2^+3.7017P] 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' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 7938 _refine_ls_number_parameters 401 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.13307(9) 0.22437(7) 0.77597(3) 0.01529(16) Uani 1 1 d . . . Cl1 Cl 0.16404(15) 0.07204(13) 0.68897(5) 0.0189(2) Uani 1 1 d . . . N1 N 0.0445(5) 0.4357(5) 0.73233(15) 0.0148(8) Uani 1 1 d . . . C1 C -0.0372(6) 0.4295(5) 0.68497(18) 0.0165(10) Uani 1 1 d . . . H1A H -0.0459 0.3315 0.6681 0.020 Uiso 1 1 calc R . . Mn2 Mn 0.45735(9) -0.03320(7) 0.70988(3) 0.01521(16) Uani 1 1 d . . . N2 N 0.1700(5) 0.4355(4) 0.83248(15) 0.0146(8) Uani 1 1 d . . . Cl2 Cl 0.42367(15) 0.11709(13) 0.79603(4) 0.0194(2) Uani 1 1 d . . . C2 C -0.1086(6) 0.5596(6) 0.65998(19) 0.0197(10) Uani 1 1 d . . . H2A H -0.1662 0.5490 0.6274 0.024 Uiso 1 1 calc R . . N3 N 0.5352(5) -0.2442(5) 0.75666(15) 0.0153(8) Uani 1 1 d . . . Cl3 Cl -0.08384(15) 0.08847(13) 0.81974(5) 0.0206(2) Uani 1 1 d . . . C3 C -0.0938(6) 0.7066(6) 0.68381(19) 0.0193(10) Uani 1 1 d . . . H3A H -0.1378 0.7971 0.6670 0.023 Uiso 1 1 calc R . . Cl4 Cl 0.66714(15) 0.11107(14) 0.66509(5) 0.0208(2) Uani 1 1 d . . . N4 N 0.4302(5) -0.2468(5) 0.65406(15) 0.0157(8) Uani 1 1 d . . . C4 C -0.0123(6) 0.7174(6) 0.73329(18) 0.0191(10) Uani 1 1 d . . . H4A H -0.0030 0.8148 0.7505 0.023 Uiso 1 1 calc R . . C5 C 0.0553(6) 0.5796(6) 0.75667(18) 0.0167(10) Uani 1 1 d . . . C6 C 0.1358(6) 0.5805(6) 0.81079(18) 0.0157(9) Uani 1 1 d . . . C7 C 0.1655(6) 0.7208(6) 0.83788(18) 0.0192(10) Uani 1 1 d . . . H7A H 0.1460 0.8185 0.8215 0.023 Uiso 1 1 calc R . . C8 C 0.2253(6) 0.7135(6) 0.89013(18) 0.0188(10) Uani 1 1 d . . . H8A H 0.2439 0.8065 0.9093 0.023 Uiso 1 1 calc R . . C9 C 0.2568(6) 0.5674(6) 0.91327(19) 0.0168(10) Uani 1 1 d . . . C10 C 0.3131(7) 0.5437(6) 0.96967(19) 0.0202(10) Uani 1 1 d . . . H10A H 0.3358 0.6401 0.9904 0.024 Uiso 1 1 calc R . . C12 C 0.4611(6) 0.4154(6) 0.9709(2) 0.0210(11) Uani 1 1 d . . . H12A H 0.5346 0.4172 0.9406 0.025 Uiso 1 1 calc R . . H12B H 0.5304 0.4118 1.0035 0.025 Uiso 1 1 calc R . . C13 C 0.3116(7) 0.2923(6) 0.96727(19) 0.0196(10) Uani 1 1 d . . . H13A H 0.3331 0.1936 0.9869 0.024 Uiso 1 1 calc R . . C14 C 0.2514(7) 0.2705(6) 0.90962(19) 0.0199(10) Uani 1 1 d . . . H14A H 0.3379 0.2090 0.8914 0.024 Uiso 1 1 calc R . . H14B H 0.1419 0.2120 0.9079 0.024 Uiso 1 1 calc R . . C15 C 0.2266(6) 0.4296(6) 0.88300(18) 0.0175(10) Uani 1 1 d . . . C16 C 0.1934(7) 0.4158(7) 0.9946(2) 0.0241(12) Uani 1 1 d . . . C17 C -0.0028(7) 0.4223(6) 0.9817(2) 0.0274(11) Uani 1 1 d . . . H17A H -0.0583 0.3304 0.9961 0.041 Uiso 1 1 calc R . . H17B H -0.0226 0.4239 0.9443 0.041 Uiso 1 1 calc R . . H17C H -0.0512 0.5167 0.9967 0.041 Uiso 1 1 calc R . . C18 C 0.2178(9) 0.4134(7) 1.0548(2) 0.0375(14) Uani 1 1 d . . . H18A H 0.1418 0.3348 1.0691 0.056 Uiso 1 1 calc R . . H18B H 0.1897 0.5161 1.0687 0.056 Uiso 1 1 calc R . . H18C H 0.3371 0.3877 1.0643 0.056 Uiso 1 1 calc R . . C19 C 0.6078(6) -0.2374(6) 0.80585(19) 0.0188(10) Uani 1 1 d . . . H19A H 0.6168 -0.1393 0.8226 0.023 Uiso 1 1 calc R . . C20 C 0.6691(6) -0.3712(6) 0.83195(19) 0.0197(10) Uani 1 1 d . . . H20A H 0.7173 -0.3627 0.8659 0.024 Uiso 1 1 calc R . . C21 C 0.6584(6) -0.5174(6) 0.80762(19) 0.0195(10) Uani 1 1 d . . . H21A H 0.6999 -0.6084 0.8247 0.023 Uiso 1 1 calc R . . C22 C 0.5840(6) -0.5264(6) 0.75681(19) 0.0173(10) Uani 1 1 d . . . H22A H 0.5756 -0.6234 0.7394 0.021 Uiso 1 1 calc R . . C23 C 0.5232(6) -0.3887(6) 0.73294(17) 0.0138(9) Uani 1 1 d . . . C24 C 0.4474(6) -0.3887(6) 0.67808(18) 0.0153(9) Uani 1 1 d . . . C25 C 0.4032(5) -0.5306(6) 0.65312(18) 0.0144(9) Uani 1 1 d . . . H25A H 0.4104 -0.6266 0.6712 0.017 Uiso 1 1 calc R . . C26 C 0.3474(6) -0.5264(6) 0.60012(18) 0.0163(9) Uani 1 1 d . . . H26A H 0.3153 -0.6194 0.5825 0.020 Uiso 1 1 calc R . . C27 C 0.3411(6) -0.3821(6) 0.57468(18) 0.0146(9) Uani 1 1 d . . . C28 C 0.2917(6) -0.3609(5) 0.51687(18) 0.0166(10) Uani 1 1 d . . . H28A H 0.2684 -0.4584 0.4968 0.020 Uiso 1 1 calc R . . C29 C 0.4269(6) -0.2440(5) 0.49387(19) 0.0186(10) Uani 1 1 d . . . H29A H 0.4304 -0.2451 0.4558 0.022 Uiso 1 1 calc R . . H29B H 0.5434 -0.2517 0.5100 0.022 Uiso 1 1 calc R . . C30 C 0.3125(6) -0.1091(5) 0.51648(18) 0.0157(9) Uani 1 1 d . . . H30A H 0.3045 -0.0120 0.4952 0.019 Uiso 1 1 calc R . . C31 C 0.3644(7) -0.0839(6) 0.57485(18) 0.0178(10) Uani 1 1 d . . . H31A H 0.4755 -0.0282 0.5777 0.021 Uiso 1 1 calc R . . H31B H 0.2769 -0.0187 0.5912 0.021 Uiso 1 1 calc R . . C32 C 0.3798(6) -0.2425(5) 0.60322(18) 0.0155(9) Uani 1 1 d . . . C33 C 0.1545(7) -0.2252(6) 0.5098(2) 0.0182(10) Uani 1 1 d . . . C34 C 0.0721(6) -0.2219(6) 0.45398(18) 0.0210(10) Uani 1 1 d . . . H34A H -0.0116 -0.3066 0.4501 0.032 Uiso 1 1 calc R . . H34B H 0.1619 -0.2354 0.4289 0.032 Uiso 1 1 calc R . . H34C H 0.0144 -0.1217 0.4480 0.032 Uiso 1 1 calc R . . C35 C 0.0075(6) -0.2132(6) 0.5482(2) 0.0220(11) Uani 1 1 d . . . H35A H -0.0754 -0.2970 0.5414 0.033 Uiso 1 1 calc R . . H35B H -0.0498 -0.1121 0.5440 0.033 Uiso 1 1 calc R . . H35C H 0.0549 -0.2228 0.5834 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0171(3) 0.0098(3) 0.0192(4) -0.0001(3) 0.0040(3) 0.0013(3) Cl1 0.0178(5) 0.0156(5) 0.0233(6) -0.0048(4) 0.0019(5) 0.0020(4) N1 0.0125(19) 0.013(2) 0.019(2) -0.0012(15) 0.0036(16) -0.0038(15) C1 0.022(2) 0.010(2) 0.017(2) -0.0037(17) 0.0061(19) 0.0025(18) Mn2 0.0170(3) 0.0092(3) 0.0196(4) -0.0006(3) 0.0032(3) 0.0004(3) N2 0.0140(18) 0.008(2) 0.022(2) -0.0008(15) 0.0059(16) 0.0015(15) Cl2 0.0186(5) 0.0165(5) 0.0231(6) -0.0050(5) 0.0002(5) 0.0030(5) C2 0.019(2) 0.021(2) 0.019(2) -0.0025(19) 0.004(2) -0.002(2) N3 0.0140(19) 0.013(2) 0.019(2) -0.0020(15) 0.0013(16) 0.0000(15) Cl3 0.0209(6) 0.0162(6) 0.0252(6) 0.0023(5) 0.0056(5) -0.0011(5) C3 0.024(3) 0.016(2) 0.018(2) 0.0047(19) 0.002(2) 0.002(2) Cl4 0.0200(6) 0.0157(5) 0.0269(6) 0.0015(5) 0.0048(5) -0.0024(5) N4 0.0180(19) 0.012(2) 0.0169(19) -0.0020(15) 0.0031(16) 0.0009(16) C4 0.024(2) 0.015(2) 0.019(2) 0.002(2) 0.0068(19) 0.002(2) C5 0.018(2) 0.015(2) 0.017(2) 0.0017(18) 0.0059(19) -0.0013(19) C6 0.015(2) 0.015(2) 0.017(2) 0.0028(18) 0.0031(18) 0.0014(19) C7 0.023(2) 0.013(2) 0.021(2) 0.003(2) -0.0007(19) -0.002(2) C8 0.023(2) 0.013(2) 0.021(2) -0.0030(19) -0.001(2) 0.000(2) C9 0.014(2) 0.016(2) 0.020(2) 0.0013(19) -0.0008(19) -0.0046(19) C10 0.027(3) 0.016(2) 0.017(2) -0.0024(19) -0.005(2) 0.003(2) C12 0.015(2) 0.018(3) 0.029(3) 0.001(2) -0.007(2) 0.0059(19) C13 0.025(3) 0.019(2) 0.015(2) 0.0006(18) -0.001(2) 0.002(2) C14 0.024(3) 0.015(2) 0.020(2) 0.0021(19) 0.004(2) 0.0052(19) C15 0.015(2) 0.020(3) 0.017(2) -0.0001(18) 0.0034(19) 0.0001(19) C16 0.032(3) 0.025(3) 0.015(2) 0.002(2) -0.005(2) 0.006(2) C17 0.029(3) 0.024(3) 0.030(3) 0.004(2) 0.015(2) 0.002(2) C18 0.062(4) 0.031(3) 0.019(3) 0.002(2) 0.002(3) 0.009(3) C19 0.022(2) 0.015(2) 0.020(2) -0.0039(18) 0.003(2) -0.0038(19) C20 0.022(2) 0.023(3) 0.014(2) 0.0010(19) 0.0016(19) 0.004(2) C21 0.022(2) 0.016(2) 0.021(2) 0.0029(19) 0.002(2) 0.005(2) C22 0.016(2) 0.012(2) 0.024(2) -0.0024(19) 0.0077(19) 0.002(2) C23 0.014(2) 0.014(2) 0.014(2) -0.0050(18) 0.0035(17) -0.0016(19) C24 0.012(2) 0.014(2) 0.020(2) -0.0009(19) 0.0029(18) -0.0012(19) C25 0.012(2) 0.008(2) 0.023(2) -0.0002(19) 0.0016(18) 0.0026(18) C26 0.015(2) 0.009(2) 0.024(2) -0.0008(19) -0.0004(18) -0.0052(19) C27 0.014(2) 0.013(2) 0.017(2) 0.0001(18) 0.0053(18) 0.0047(18) C28 0.020(2) 0.011(2) 0.018(2) -0.0005(18) 0.0019(19) -0.0051(18) C29 0.023(2) 0.013(2) 0.021(2) 0.0027(18) 0.006(2) -0.0028(19) C30 0.017(2) 0.011(2) 0.019(2) 0.0029(17) 0.0014(19) -0.0026(17) C31 0.024(2) 0.010(2) 0.020(2) 0.0002(17) 0.002(2) -0.0029(18) C32 0.017(2) 0.009(2) 0.021(2) 0.0045(17) 0.0050(19) 0.0000(17) C33 0.024(3) 0.015(2) 0.015(2) 0.0005(18) 0.0019(19) -0.0016(19) C34 0.022(2) 0.018(2) 0.023(2) 0.0063(18) -0.004(2) 0.0013(19) C35 0.017(2) 0.023(2) 0.026(3) 0.007(2) -0.001(2) 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 N1 2.190(4) . ? Mn1 N2 2.296(4) . ? Mn1 Cl3 2.3293(13) . ? Mn1 Cl2 2.4356(14) . ? Mn1 Cl1 2.5772(14) . ? Cl1 Mn2 2.4519(14) . ? N1 C1 1.340(6) . ? N1 C5 1.360(6) . ? C1 C2 1.369(7) . ? Mn2 N3 2.207(4) . ? Mn2 N4 2.295(4) . ? Mn2 Cl4 2.3390(13) . ? Mn2 Cl2 2.5526(13) . ? N2 C15 1.344(6) . ? N2 C6 1.359(6) . ? C2 C3 1.380(7) . ? N3 C19 1.354(6) . ? N3 C23 1.358(6) . ? C3 C4 1.389(7) . ? N4 C32 1.339(6) . ? N4 C24 1.345(6) . ? C4 C5 1.394(7) . ? C5 C6 1.490(7) . ? C6 C7 1.382(7) . ? C7 C8 1.393(7) . ? C8 C9 1.380(7) . ? C9 C15 1.406(7) . ? C9 C10 1.499(7) . ? C10 C16 1.560(8) . ? C10 C12 1.562(7) . ? C12 C13 1.542(7) . ? C13 C14 1.534(7) . ? C13 C16 1.556(7) . ? C14 C15 1.509(7) . ? C16 C17 1.526(8) . ? C16 C18 1.540(7) . ? C19 C20 1.380(7) . ? C20 C21 1.377(7) . ? C21 C22 1.397(7) . ? C22 C23 1.381(7) . ? C23 C24 1.494(6) . ? C24 C25 1.388(7) . ? C25 C26 1.402(6) . ? C26 C27 1.375(7) . ? C27 C32 1.407(7) . ? C27 C28 1.518(6) . ? C28 C29 1.555(6) . ? C28 C33 1.556(7) . ? C29 C30 1.555(6) . ? C30 C31 1.540(7) . ? C30 C33 1.558(7) . ? C31 C32 1.519(6) . ? C33 C35 1.518(7) . ? C33 C34 1.535(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Mn1 N2 73.76(15) . . ? N1 Mn1 Cl3 115.34(10) . . ? N2 Mn1 Cl3 98.82(10) . . ? N1 Mn1 Cl2 132.10(10) . . ? N2 Mn1 Cl2 93.62(10) . . ? Cl3 Mn1 Cl2 112.17(5) . . ? N1 Mn1 Cl1 90.15(10) . . ? N2 Mn1 Cl1 155.50(10) . . ? Cl3 Mn1 Cl1 104.83(5) . . ? Cl2 Mn1 Cl1 83.46(4) . . ? Mn2 Cl1 Mn1 95.91(5) . . ? C1 N1 C5 117.6(4) . . ? C1 N1 Mn1 123.5(3) . . ? C5 N1 Mn1 118.5(3) . . ? N1 C1 C2 123.6(4) . . ? N3 Mn2 N4 73.90(15) . . ? N3 Mn2 Cl4 120.22(11) . . ? N4 Mn2 Cl4 98.76(10) . . ? N3 Mn2 Cl1 129.40(11) . . ? N4 Mn2 Cl1 94.90(11) . . ? Cl4 Mn2 Cl1 110.15(5) . . ? N3 Mn2 Cl2 88.11(10) . . ? N4 Mn2 Cl2 155.51(11) . . ? Cl4 Mn2 Cl2 104.71(5) . . ? Cl1 Mn2 Cl2 83.65(4) . . ? C15 N2 C6 118.3(4) . . ? C15 N2 Mn1 126.9(3) . . ? C6 N2 Mn1 114.8(3) . . ? Mn1 Cl2 Mn2 96.97(5) . . ? C1 C2 C3 119.1(5) . . ? C19 N3 C23 117.9(4) . . ? C19 N3 Mn2 124.1(3) . . ? C23 N3 Mn2 117.7(3) . . ? C2 C3 C4 119.0(5) . . ? C32 N4 C24 119.0(4) . . ? C32 N4 Mn2 126.5(3) . . ? C24 N4 Mn2 114.0(3) . . ? C3 C4 C5 118.8(5) . . ? N1 C5 C4 121.9(4) . . ? N1 C5 C6 116.3(4) . . ? C4 C5 C6 121.8(4) . . ? N2 C6 C7 122.4(4) . . ? N2 C6 C5 116.0(4) . . ? C7 C6 C5 121.5(4) . . ? C6 C7 C8 118.8(5) . . ? C9 C8 C7 119.6(5) . . ? C8 C9 C15 118.4(4) . . ? C8 C9 C10 124.6(4) . . ? C15 C9 C10 116.9(4) . . ? C9 C10 C16 109.1(4) . . ? C9 C10 C12 107.1(4) . . ? C16 C10 C12 87.2(4) . . ? C13 C12 C10 85.8(4) . . ? C14 C13 C12 109.5(4) . . ? C14 C13 C16 110.3(4) . . ? C12 C13 C16 88.1(4) . . ? C15 C14 C13 110.7(4) . . ? N2 C15 C9 122.4(4) . . ? N2 C15 C14 119.6(4) . . ? C9 C15 C14 117.9(4) . . ? C17 C16 C18 107.4(5) . . ? C17 C16 C13 120.6(4) . . ? C18 C16 C13 112.6(4) . . ? C17 C16 C10 118.3(4) . . ? C18 C16 C10 111.2(5) . . ? C13 C16 C10 85.4(4) . . ? N3 C19 C20 122.2(4) . . ? C21 C20 C19 119.8(4) . . ? C20 C21 C22 118.7(5) . . ? C23 C22 C21 118.8(4) . . ? N3 C23 C22 122.5(4) . . ? N3 C23 C24 115.7(4) . . ? C22 C23 C24 121.7(4) . . ? N4 C24 C25 122.4(4) . . ? N4 C24 C23 117.0(4) . . ? C25 C24 C23 120.6(4) . . ? C24 C25 C26 118.7(4) . . ? C27 C26 C25 118.7(4) . . ? C26 C27 C32 119.3(4) . . ? C26 C27 C28 124.4(4) . . ? C32 C27 C28 116.3(4) . . ? C27 C28 C29 107.1(4) . . ? C27 C28 C33 110.0(4) . . ? C29 C28 C33 87.0(3) . . ? C28 C29 C30 86.1(3) . . ? C31 C30 C29 109.2(4) . . ? C31 C30 C33 111.4(4) . . ? C29 C30 C33 86.9(3) . . ? C32 C31 C30 110.6(4) . . ? N4 C32 C27 121.7(4) . . ? N4 C32 C31 119.9(4) . . ? C27 C32 C31 118.4(4) . . ? C35 C33 C34 107.8(4) . . ? C35 C33 C28 119.0(4) . . ? C34 C33 C28 112.0(4) . . ? C35 C33 C30 118.4(4) . . ? C34 C33 C30 112.5(4) . . ? C28 C33 C30 85.9(4) . . ? 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 N1 Mn1 Cl1 Mn2 132.10(10) . . . . ? N2 Mn1 Cl1 Mn2 84.0(3) . . . . ? Cl3 Mn1 Cl1 Mn2 -111.58(5) . . . . ? Cl2 Mn1 Cl1 Mn2 -0.32(5) . . . . ? N2 Mn1 N1 C1 -171.4(4) . . . . ? Cl3 Mn1 N1 C1 -79.2(4) . . . . ? Cl2 Mn1 N1 C1 108.7(3) . . . . ? Cl1 Mn1 N1 C1 27.4(3) . . . . ? N2 Mn1 N1 C5 1.2(3) . . . . ? Cl3 Mn1 N1 C5 93.4(3) . . . . ? Cl2 Mn1 N1 C5 -78.8(3) . . . . ? Cl1 Mn1 N1 C5 -160.1(3) . . . . ? C5 N1 C1 C2 0.4(7) . . . . ? Mn1 N1 C1 C2 173.0(4) . . . . ? Mn1 Cl1 Mn2 N3 82.58(14) . . . . ? Mn1 Cl1 Mn2 N4 155.73(10) . . . . ? Mn1 Cl1 Mn2 Cl4 -103.07(5) . . . . ? Mn1 Cl1 Mn2 Cl2 0.30(5) . . . . ? N1 Mn1 N2 C15 177.1(4) . . . . ? Cl3 Mn1 N2 C15 63.1(4) . . . . ? Cl2 Mn1 N2 C15 -50.0(4) . . . . ? Cl1 Mn1 N2 C15 -132.1(3) . . . . ? N1 Mn1 N2 C6 -5.4(3) . . . . ? Cl3 Mn1 N2 C6 -119.3(3) . . . . ? Cl2 Mn1 N2 C6 127.5(3) . . . . ? Cl1 Mn1 N2 C6 45.4(5) . . . . ? N1 Mn1 Cl2 Mn2 -83.95(15) . . . . ? N2 Mn1 Cl2 Mn2 -155.26(10) . . . . ? Cl3 Mn1 Cl2 Mn2 103.69(5) . . . . ? Cl1 Mn1 Cl2 Mn2 0.31(5) . . . . ? N3 Mn2 Cl2 Mn1 -130.31(11) . . . . ? N4 Mn2 Cl2 Mn1 -88.2(3) . . . . ? Cl4 Mn2 Cl2 Mn1 108.89(5) . . . . ? Cl1 Mn2 Cl2 Mn1 -0.32(5) . . . . ? N1 C1 C2 C3 1.3(7) . . . . ? N4 Mn2 N3 C19 171.3(4) . . . . ? Cl4 Mn2 N3 C19 80.4(4) . . . . ? Cl1 Mn2 N3 C19 -105.7(4) . . . . ? Cl2 Mn2 N3 C19 -25.5(4) . . . . ? N4 Mn2 N3 C23 -2.8(3) . . . . ? Cl4 Mn2 N3 C23 -93.7(3) . . . . ? Cl1 Mn2 N3 C23 80.2(3) . . . . ? Cl2 Mn2 N3 C23 160.4(3) . . . . ? C1 C2 C3 C4 -2.2(7) . . . . ? N3 Mn2 N4 C32 -179.1(4) . . . . ? Cl4 Mn2 N4 C32 -60.0(4) . . . . ? Cl1 Mn2 N4 C32 51.3(4) . . . . ? Cl2 Mn2 N4 C32 136.7(3) . . . . ? N3 Mn2 N4 C24 9.5(3) . . . . ? Cl4 Mn2 N4 C24 128.5(3) . . . . ? Cl1 Mn2 N4 C24 -120.2(3) . . . . ? Cl2 Mn2 N4 C24 -34.8(5) . . . . ? C2 C3 C4 C5 1.4(7) . . . . ? C1 N1 C5 C4 -1.3(7) . . . . ? Mn1 N1 C5 C4 -174.3(3) . . . . ? C1 N1 C5 C6 175.9(4) . . . . ? Mn1 N1 C5 C6 2.9(5) . . . . ? C3 C4 C5 N1 0.4(7) . . . . ? C3 C4 C5 C6 -176.6(4) . . . . ? C15 N2 C6 C7 3.4(7) . . . . ? Mn1 N2 C6 C7 -174.4(4) . . . . ? C15 N2 C6 C5 -173.6(4) . . . . ? Mn1 N2 C6 C5 8.6(5) . . . . ? N1 C5 C6 N2 -7.8(6) . . . . ? C4 C5 C6 N2 169.4(4) . . . . ? N1 C5 C6 C7 175.2(4) . . . . ? C4 C5 C6 C7 -7.7(7) . . . . ? N2 C6 C7 C8 -3.0(7) . . . . ? C5 C6 C7 C8 173.9(4) . . . . ? C6 C7 C8 C9 1.3(7) . . . . ? C7 C8 C9 C15 -0.2(7) . . . . ? C7 C8 C9 C10 -177.0(4) . . . . ? C8 C9 C10 C16 130.4(5) . . . . ? C15 C9 C10 C16 -46.5(6) . . . . ? C8 C9 C10 C12 -136.6(5) . . . . ? C15 C9 C10 C12 46.5(6) . . . . ? C9 C10 C12 C13 -81.9(4) . . . . ? C16 C10 C12 C13 27.3(4) . . . . ? C10 C12 C13 C14 83.6(4) . . . . ? C10 C12 C13 C16 -27.3(4) . . . . ? C12 C13 C14 C15 -46.7(5) . . . . ? C16 C13 C14 C15 48.7(6) . . . . ? C6 N2 C15 C9 -2.2(7) . . . . ? Mn1 N2 C15 C9 175.3(3) . . . . ? C6 N2 C15 C14 174.9(4) . . . . ? Mn1 N2 C15 C14 -7.7(6) . . . . ? C8 C9 C15 N2 0.6(7) . . . . ? C10 C9 C15 N2 177.7(4) . . . . ? C8 C9 C15 C14 -176.5(4) . . . . ? C10 C9 C15 C14 0.6(6) . . . . ? C13 C14 C15 N2 -178.4(4) . . . . ? C13 C14 C15 C9 -1.3(6) . . . . ? C14 C13 C16 C17 37.7(6) . . . . ? C12 C13 C16 C17 147.8(5) . . . . ? C14 C13 C16 C18 166.2(5) . . . . ? C12 C13 C16 C18 -83.7(5) . . . . ? C14 C13 C16 C10 -82.8(4) . . . . ? C12 C13 C16 C10 27.4(4) . . . . ? C9 C10 C16 C17 -42.4(6) . . . . ? C12 C10 C16 C17 -149.6(5) . . . . ? C9 C10 C16 C18 -167.4(4) . . . . ? C12 C10 C16 C18 85.5(5) . . . . ? C9 C10 C16 C13 80.1(4) . . . . ? C12 C10 C16 C13 -27.0(4) . . . . ? C23 N3 C19 C20 0.1(7) . . . . ? Mn2 N3 C19 C20 -174.1(3) . . . . ? N3 C19 C20 C21 0.6(7) . . . . ? C19 C20 C21 C22 -0.4(7) . . . . ? C20 C21 C22 C23 -0.3(7) . . . . ? C19 N3 C23 C22 -0.9(6) . . . . ? Mn2 N3 C23 C22 173.6(3) . . . . ? C19 N3 C23 C24 -178.1(4) . . . . ? Mn2 N3 C23 C24 -3.6(5) . . . . ? C21 C22 C23 N3 1.0(7) . . . . ? C21 C22 C23 C24 178.0(4) . . . . ? C32 N4 C24 C25 -4.5(7) . . . . ? Mn2 N4 C24 C25 167.6(3) . . . . ? C32 N4 C24 C23 173.2(4) . . . . ? Mn2 N4 C24 C23 -14.6(5) . . . . ? N3 C23 C24 N4 12.5(6) . . . . ? C22 C23 C24 N4 -164.8(4) . . . . ? N3 C23 C24 C25 -169.7(4) . . . . ? C22 C23 C24 C25 13.1(6) . . . . ? N4 C24 C25 C26 3.4(7) . . . . ? C23 C24 C25 C26 -174.3(4) . . . . ? C24 C25 C26 C27 0.9(6) . . . . ? C25 C26 C27 C32 -4.0(6) . . . . ? C25 C26 C27 C28 177.0(4) . . . . ? C26 C27 C28 C29 -134.8(5) . . . . ? C32 C27 C28 C29 46.1(5) . . . . ? C26 C27 C28 C33 132.1(5) . . . . ? C32 C27 C28 C33 -47.0(5) . . . . ? C27 C28 C29 C30 -82.2(4) . . . . ? C33 C28 C29 C30 27.8(3) . . . . ? C28 C29 C30 C31 83.8(4) . . . . ? C28 C29 C30 C33 -27.8(3) . . . . ? C29 C30 C31 C32 -45.9(5) . . . . ? C33 C30 C31 C32 48.4(5) . . . . ? C24 N4 C32 C27 1.3(7) . . . . ? Mn2 N4 C32 C27 -169.8(3) . . . . ? C24 N4 C32 C31 -178.3(4) . . . . ? Mn2 N4 C32 C31 10.6(6) . . . . ? C26 C27 C32 N4 3.0(7) . . . . ? C28 C27 C32 N4 -177.9(4) . . . . ? C26 C27 C32 C31 -177.4(4) . . . . ? C28 C27 C32 C31 1.7(6) . . . . ? C30 C31 C32 N4 177.5(4) . . . . ? C30 C31 C32 C27 -2.1(6) . . . . ? C27 C28 C33 C35 -41.1(6) . . . . ? C29 C28 C33 C35 -148.2(5) . . . . ? C27 C28 C33 C34 -168.1(4) . . . . ? C29 C28 C33 C34 84.8(4) . . . . ? C27 C28 C33 C30 79.3(4) . . . . ? C29 C28 C33 C30 -27.8(3) . . . . ? C31 C30 C33 C35 39.4(6) . . . . ? C29 C30 C33 C35 148.8(4) . . . . ? C31 C30 C33 C34 166.3(4) . . . . ? C29 C30 C33 C34 -84.3(4) . . . . ? C31 C30 C33 C28 -81.6(4) . . . . ? C29 C30 C33 C28 27.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.027 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.103 #END data_720649 _database_code_depnum_ccdc_archive 'CCDC 720649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H36 F6 Mn N4 O6 S2' _chemical_formula_sum 'C36 H36 F6 Mn N4 O6 S2' _chemical_formula_weight 853.75 _chemical_absolute_configuration ad 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 9.340(5) _cell_length_b 18.511(9) _cell_length_c 21.713(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3754(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1756 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 54593 _diffrn_reflns_av_R_equivalents 0.1081 _diffrn_reflns_av_sigmaI/netI 0.1057 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.45 _reflns_number_total 9293 _reflns_number_gt 6203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Shelxtl' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0586P)^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 SHELXL _refine_ls_extinction_coef 0.0061(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_number_reflns 9293 _refine_ls_number_parameters 501 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.23400(6) 0.37640(3) 0.20666(3) 0.02310(15) Uani 1 1 d . . . S1 S 0.11956(10) 0.23441(5) 0.11720(5) 0.0279(2) Uani 1 1 d . . . N1 N 0.0234(3) 0.43591(16) 0.19635(15) 0.0245(7) Uani 1 1 d . . . O1 O 0.1566(3) 0.30909(14) 0.13202(12) 0.0321(7) Uani 1 1 d . . . F1 F 0.3541(3) 0.22965(18) 0.05201(13) 0.0588(8) Uani 1 1 d . . . C1 C -0.0697(4) 0.4230(2) 0.15079(19) 0.0302(9) Uani 1 1 d . . . H1A H -0.0476 0.3878 0.1217 0.036 Uiso 1 1 calc R . . S2 S 0.33353(10) 0.51563(5) 0.11029(5) 0.0257(2) Uani 1 1 d . . . N2 N 0.2281(3) 0.46367(16) 0.28074(14) 0.0245(7) Uani 1 1 d . . . F2 F 0.1700(3) 0.27082(15) 0.00195(12) 0.0531(7) Uani 1 1 d . . . O2 O 0.1819(3) 0.18167(14) 0.15810(13) 0.0362(7) Uani 1 1 d . . . C2 C -0.1986(4) 0.4603(2) 0.1455(2) 0.0333(10) Uani 1 1 d . . . H2A H -0.2613 0.4504 0.1133 0.040 Uiso 1 1 calc R . . N3 N 0.4387(3) 0.31244(16) 0.20152(15) 0.0263(7) Uani 1 1 d . . . F3 F 0.1902(3) 0.15675(14) 0.02096(13) 0.0600(8) Uani 1 1 d . . . O3 O -0.0297(3) 0.22459(16) 0.10258(14) 0.0421(8) Uani 1 1 d . . . C3 C -0.2318(4) 0.5126(2) 0.18916(19) 0.0361(10) Uani 1 1 d . . . H3A H -0.3183 0.5374 0.1871 0.043 Uiso 1 1 calc R . . N4 N 0.2186(3) 0.28596(16) 0.27901(14) 0.0249(7) Uani 1 1 d . . . O4 O 0.3547(3) 0.45430(14) 0.15166(12) 0.0284(6) Uani 1 1 d . . . F4 F 0.5344(3) 0.45996(16) 0.04053(11) 0.0507(7) Uani 1 1 d . . . C4 C -0.1355(4) 0.5275(2) 0.23564(19) 0.0320(9) Uani 1 1 d . . . H4A H -0.1553 0.5628 0.2649 0.038 Uiso 1 1 calc R . . F5 F 0.3215(3) 0.41921(14) 0.02246(12) 0.0542(8) Uani 1 1 d . . . O5 O 0.4304(3) 0.57409(14) 0.12190(14) 0.0386(7) Uani 1 1 d . . . C5 C -0.0066(4) 0.4881(2) 0.23793(18) 0.0249(8) Uani 1 1 d . . . F6 F 0.3829(3) 0.52538(14) -0.00893(11) 0.0447(7) Uani 1 1 d . . . C6 C 0.1053(4) 0.5025(2) 0.28557(17) 0.0247(8) Uani 1 1 d . . . O6 O 0.1872(3) 0.53377(15) 0.09882(14) 0.0348(7) Uani 1 1 d . . . C7 C 0.0886(4) 0.5548(2) 0.33128(17) 0.0272(9) Uani 1 1 d . . . H7A H 0.0037 0.5808 0.3339 0.033 Uiso 1 1 calc R . . C8 C 0.1984(4) 0.5679(2) 0.37297(18) 0.0287(9) Uani 1 1 d . . . H8A H 0.1869 0.6017 0.4043 0.034 Uiso 1 1 calc R . . C9 C 0.3253(4) 0.5298(2) 0.36711(18) 0.0272(9) Uani 1 1 d . . . C10 C 0.4564(4) 0.5415(2) 0.40662(19) 0.0329(10) Uani 1 1 d . . . H10A H 0.4492 0.5786 0.4387 0.039 Uiso 1 1 calc R . . C11 C 0.5872(5) 0.5470(2) 0.3621(2) 0.0360(10) Uani 1 1 d . . . H11A H 0.5655 0.5692 0.3228 0.043 Uiso 1 1 calc R . . H11B H 0.6721 0.5680 0.3806 0.043 Uiso 1 1 calc R . . C12 C 0.5862(4) 0.4636(2) 0.36113(18) 0.0307(9) Uani 1 1 d . . . H12A H 0.6808 0.4408 0.3586 0.037 Uiso 1 1 calc R . . C13 C 0.4768(4) 0.4367(2) 0.31409(18) 0.0248(8) Uani 1 1 d . . . H13A H 0.5144 0.4433 0.2728 0.030 Uiso 1 1 calc R . . H13B H 0.4599 0.3855 0.3203 0.030 Uiso 1 1 calc R . . C14 C 0.3362(4) 0.4776(2) 0.32040(17) 0.0246(8) Uani 1 1 d . . . C15 C 0.5179(4) 0.4655(2) 0.42718(18) 0.0316(10) Uani 1 1 d . . . C16 C 0.6302(5) 0.4746(3) 0.4788(2) 0.0423(11) Uani 1 1 d . . . H16A H 0.6784 0.4294 0.4855 0.063 Uiso 1 1 calc R . . H16B H 0.5833 0.4893 0.5161 0.063 Uiso 1 1 calc R . . H16C H 0.6987 0.5106 0.4670 0.063 Uiso 1 1 calc R . . C17 C 0.4164(4) 0.4054(2) 0.4460(2) 0.0331(10) Uani 1 1 d . . . H17A H 0.4672 0.3603 0.4471 0.050 Uiso 1 1 calc R . . H17B H 0.3395 0.4022 0.4168 0.050 Uiso 1 1 calc R . . H17C H 0.3781 0.4155 0.4862 0.050 Uiso 1 1 calc R . . C18 C 0.5380(4) 0.3210(2) 0.15638(19) 0.0298(9) Uani 1 1 d . . . H18A H 0.5237 0.3572 0.1273 0.036 Uiso 1 1 calc R . . C19 C 0.6603(4) 0.2782(2) 0.1515(2) 0.0321(9) Uani 1 1 d . . . H19A H 0.7272 0.2861 0.1205 0.038 Uiso 1 1 calc R . . C20 C 0.6788(4) 0.2238(2) 0.19412(18) 0.0308(9) Uani 1 1 d . . . H20A H 0.7597 0.1946 0.1925 0.037 Uiso 1 1 calc R . . C21 C 0.5758(4) 0.2127(2) 0.23968(19) 0.0299(9) Uani 1 1 d . . . H21A H 0.5865 0.1755 0.2680 0.036 Uiso 1 1 calc R . . C22 C 0.4568(4) 0.25801(19) 0.24231(18) 0.0244(8) Uani 1 1 d . . . C23 C 0.3416(4) 0.24761(19) 0.28880(18) 0.0257(8) Uani 1 1 d . . . C24 C 0.3550(4) 0.2000(2) 0.33723(18) 0.0299(9) Uani 1 1 d . . . H24A H 0.4426 0.1780 0.3451 0.036 Uiso 1 1 calc R . . C25 C 0.2376(5) 0.1849(2) 0.37435(18) 0.0308(9) Uani 1 1 d . . . H25A H 0.2458 0.1530 0.4072 0.037 Uiso 1 1 calc R . . C26 C 0.1080(4) 0.2183(2) 0.36154(18) 0.0279(9) Uani 1 1 d . . . C27 C -0.0321(4) 0.2003(2) 0.39213(19) 0.0319(9) Uani 1 1 d . . . H27A H -0.0303 0.1613 0.4227 0.038 Uiso 1 1 calc R . . C28 C -0.1432(4) 0.1929(2) 0.33917(19) 0.0323(9) Uani 1 1 d . . . H28A H -0.1038 0.1744 0.3010 0.039 Uiso 1 1 calc R . . H28B H -0.2299 0.1675 0.3506 0.039 Uiso 1 1 calc R . . C29 C -0.1560(4) 0.2758(2) 0.34157(19) 0.0317(9) Uani 1 1 d . . . H29A H -0.2521 0.2949 0.3337 0.038 Uiso 1 1 calc R . . C30 C -0.0358(4) 0.3099(2) 0.30284(18) 0.0278(9) Uani 1 1 d . . . H30A H -0.0597 0.3066 0.2595 0.033 Uiso 1 1 calc R . . H30B H -0.0257 0.3605 0.3134 0.033 Uiso 1 1 calc R . . C31 C 0.1042(4) 0.2706(2) 0.31499(18) 0.0262(8) Uani 1 1 d . . . C32 C -0.1125(4) 0.2713(2) 0.41105(19) 0.0319(9) Uani 1 1 d . . . C33 C -0.2410(5) 0.2544(2) 0.4530(2) 0.0419(11) Uani 1 1 d . . . H33A H -0.3026 0.2959 0.4550 0.063 Uiso 1 1 calc R . . H33B H -0.2074 0.2427 0.4935 0.063 Uiso 1 1 calc R . . H33C H -0.2933 0.2142 0.4364 0.063 Uiso 1 1 calc R . . C34 C -0.0271(5) 0.3334(2) 0.4395(2) 0.0371(10) Uani 1 1 d . . . H34A H -0.0843 0.3765 0.4394 0.056 Uiso 1 1 calc R . . H34B H 0.0583 0.3414 0.4159 0.056 Uiso 1 1 calc R . . H34C H -0.0018 0.3213 0.4811 0.056 Uiso 1 1 calc R . . C35 C 0.2137(5) 0.2223(2) 0.0448(2) 0.0391(11) Uani 1 1 d . . . C36 C 0.3959(4) 0.4784(2) 0.03711(19) 0.0317(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 0.0175(3) 0.0227(3) 0.0291(3) 0.0007(3) -0.0005(2) 0.0027(2) S1 0.0193(5) 0.0268(5) 0.0376(6) -0.0034(5) 0.0013(4) -0.0002(4) N1 0.0164(15) 0.0244(17) 0.0327(18) 0.0014(14) 0.0008(14) 0.0014(13) O1 0.0347(16) 0.0240(14) 0.0375(16) -0.0006(12) -0.0048(13) -0.0005(12) F1 0.0231(14) 0.089(2) 0.0647(19) -0.0095(17) 0.0166(13) -0.0006(14) C1 0.022(2) 0.032(2) 0.037(2) 0.0078(18) -0.0025(18) 0.0005(17) S2 0.0203(5) 0.0214(5) 0.0355(5) 0.0002(4) -0.0011(4) -0.0014(4) N2 0.0171(15) 0.0251(16) 0.0314(17) 0.0018(13) 0.0022(13) 0.0029(13) F2 0.0662(19) 0.0581(18) 0.0351(14) 0.0006(14) 0.0026(14) -0.0009(15) O2 0.0374(17) 0.0251(14) 0.0460(17) 0.0051(13) 0.0008(14) 0.0020(13) C2 0.018(2) 0.032(2) 0.049(3) 0.009(2) -0.0092(18) -0.0039(16) N3 0.0172(15) 0.0254(17) 0.0362(18) -0.0036(15) 0.0016(14) 0.0004(13) F3 0.073(2) 0.0461(16) 0.0607(18) -0.0268(15) 0.0107(16) -0.0008(15) O3 0.0175(14) 0.0475(19) 0.061(2) -0.0014(16) 0.0019(14) -0.0050(13) C3 0.021(2) 0.034(2) 0.053(3) 0.014(2) -0.001(2) 0.0018(18) N4 0.0214(17) 0.0224(16) 0.0310(18) 0.0014(13) -0.0005(13) 0.0006(13) O4 0.0269(15) 0.0285(15) 0.0297(14) 0.0036(12) 0.0017(12) 0.0037(12) F4 0.0308(14) 0.077(2) 0.0443(15) 0.0095(14) 0.0080(12) 0.0216(14) C4 0.021(2) 0.031(2) 0.043(2) -0.0010(19) 0.0026(19) 0.0040(17) F5 0.074(2) 0.0481(16) 0.0408(15) -0.0119(13) -0.0001(14) -0.0184(15) O5 0.0300(16) 0.0271(15) 0.059(2) -0.0058(14) -0.0053(14) -0.0112(12) C5 0.0169(18) 0.024(2) 0.033(2) 0.0042(17) 0.0027(16) 0.0007(15) F6 0.0412(15) 0.0532(16) 0.0397(14) 0.0167(13) 0.0014(12) 0.0024(13) C6 0.0207(18) 0.027(2) 0.027(2) 0.0050(16) 0.0034(16) 0.0023(15) O6 0.0174(14) 0.0359(16) 0.0511(18) 0.0050(14) 0.0019(13) 0.0064(12) C7 0.025(2) 0.026(2) 0.030(2) 0.0011(17) 0.0074(17) 0.0066(17) C8 0.035(2) 0.025(2) 0.026(2) -0.0020(16) -0.0004(17) 0.0067(17) C9 0.028(2) 0.024(2) 0.030(2) 0.0040(16) 0.0030(17) 0.0046(17) C10 0.033(2) 0.029(2) 0.037(2) -0.0062(19) -0.0058(19) -0.0023(18) C11 0.034(2) 0.029(2) 0.046(3) -0.0026(19) 0.000(2) -0.0085(18) C12 0.024(2) 0.028(2) 0.039(2) -0.0042(18) -0.0048(18) 0.0051(17) C13 0.0183(19) 0.025(2) 0.031(2) -0.0015(16) -0.0003(16) 0.0024(16) C14 0.0194(19) 0.024(2) 0.030(2) 0.0017(16) 0.0014(16) 0.0016(16) C15 0.028(2) 0.032(2) 0.036(2) -0.0040(19) -0.0040(18) 0.0025(18) C16 0.042(3) 0.046(3) 0.039(2) -0.005(2) -0.009(2) 0.007(2) C17 0.025(2) 0.035(2) 0.038(2) 0.0030(19) 0.0024(19) 0.0068(18) C18 0.020(2) 0.033(2) 0.036(2) 0.0025(19) 0.0051(17) 0.0029(17) C19 0.0151(19) 0.040(2) 0.041(2) -0.005(2) -0.0001(17) 0.0039(17) C20 0.0223(19) 0.031(2) 0.039(2) -0.0108(19) -0.0045(18) 0.0048(17) C21 0.025(2) 0.028(2) 0.036(2) -0.0002(18) -0.0025(18) 0.0038(17) C22 0.0189(19) 0.023(2) 0.031(2) -0.0019(17) -0.0067(16) 0.0026(15) C23 0.0210(19) 0.0241(19) 0.032(2) -0.0022(17) 0.0000(17) 0.0028(15) C24 0.026(2) 0.029(2) 0.035(2) 0.0028(18) -0.0022(18) 0.0054(17) C25 0.035(2) 0.026(2) 0.031(2) 0.0049(17) -0.0020(18) 0.0061(18) C26 0.026(2) 0.025(2) 0.033(2) 0.0006(17) 0.0002(17) 0.0002(16) C27 0.030(2) 0.028(2) 0.037(2) 0.0101(19) 0.0067(19) -0.0003(17) C28 0.029(2) 0.029(2) 0.039(2) 0.0067(19) -0.0018(18) -0.0070(18) C29 0.023(2) 0.030(2) 0.042(2) 0.0034(19) 0.0032(18) -0.0020(17) C30 0.0170(18) 0.032(2) 0.034(2) 0.0040(18) -0.0025(17) 0.0004(16) C31 0.0224(19) 0.025(2) 0.031(2) -0.0003(17) 0.0014(16) 0.0017(16) C32 0.024(2) 0.033(2) 0.039(2) 0.0076(19) 0.0057(18) 0.0013(18) C33 0.029(2) 0.050(3) 0.047(3) 0.013(2) 0.012(2) 0.003(2) C34 0.025(2) 0.043(3) 0.043(2) -0.005(2) 0.0033(19) 0.000(2) C35 0.033(3) 0.039(3) 0.046(3) -0.009(2) -0.001(2) -0.003(2) C36 0.024(2) 0.037(2) 0.034(2) 0.012(2) 0.0009(18) 0.0004(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 O1 2.168(3) . ? Mn1 O4 2.186(3) . ? Mn1 N3 2.252(3) . ? Mn1 N1 2.265(3) . ? Mn1 N2 2.280(3) . ? Mn1 N4 2.300(3) . ? S1 O3 1.441(3) . ? S1 O2 1.443(3) . ? S1 O1 1.461(3) . ? S1 C35 1.815(5) . ? N1 C1 1.339(5) . ? N1 C5 1.352(5) . ? F1 C35 1.328(5) . ? C1 C2 1.392(5) . ? S2 O6 1.429(3) . ? S2 O5 1.433(3) . ? S2 O4 1.461(3) . ? S2 C36 1.828(4) . ? N2 C14 1.352(5) . ? N2 C6 1.357(5) . ? F2 C35 1.356(5) . ? C2 C3 1.392(6) . ? N3 C22 1.352(5) . ? N3 C18 1.358(5) . ? F3 C35 1.337(5) . ? C3 C4 1.380(6) . ? N4 C31 1.353(5) . ? N4 C23 1.367(5) . ? F4 C36 1.340(5) . ? C4 C5 1.408(5) . ? F5 C36 1.336(5) . ? C5 C6 1.495(5) . ? F6 C36 1.331(4) . ? C6 C7 1.394(5) . ? C7 C8 1.389(5) . ? C8 C9 1.385(5) . ? C9 C14 1.404(5) . ? C9 C10 1.511(5) . ? C10 C11 1.560(6) . ? C10 C15 1.584(6) . ? C11 C12 1.545(6) . ? C12 C13 1.528(5) . ? C12 C15 1.570(6) . ? C13 C14 1.522(5) . ? C15 C17 1.519(6) . ? C15 C16 1.545(6) . ? C18 C19 1.394(5) . ? C19 C20 1.380(6) . ? C20 C21 1.395(6) . ? C21 C22 1.393(5) . ? C22 C23 1.488(5) . ? C23 C24 1.378(5) . ? C24 C25 1.389(6) . ? C25 C26 1.387(6) . ? C26 C31 1.401(6) . ? C26 C27 1.505(5) . ? C27 C28 1.555(6) . ? C27 C32 1.569(6) . ? C28 C29 1.539(5) . ? C29 C30 1.538(5) . ? C29 C32 1.565(6) . ? C30 C31 1.518(5) . ? C32 C34 1.529(6) . ? C32 C33 1.538(6) . ? 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 O4 98.20(11) . . ? O1 Mn1 N3 86.78(11) . . ? O4 Mn1 N3 83.21(11) . . ? O1 Mn1 N1 85.19(11) . . ? O4 Mn1 N1 94.19(11) . . ? N3 Mn1 N1 171.12(12) . . ? O1 Mn1 N2 157.86(11) . . ? O4 Mn1 N2 86.01(11) . . ? N3 Mn1 N2 115.34(11) . . ? N1 Mn1 N2 72.80(11) . . ? O1 Mn1 N4 94.09(11) . . ? O4 Mn1 N4 152.34(11) . . ? N3 Mn1 N4 72.81(12) . . ? N1 Mn1 N4 111.53(11) . . ? N2 Mn1 N4 91.86(11) . . ? O3 S1 O2 116.15(18) . . ? O3 S1 O1 113.40(17) . . ? O2 S1 O1 114.14(17) . . ? O3 S1 C35 105.2(2) . . ? O2 S1 C35 104.7(2) . . ? O1 S1 C35 101.13(19) . . ? C1 N1 C5 119.1(3) . . ? C1 N1 Mn1 123.4(3) . . ? C5 N1 Mn1 117.5(2) . . ? S1 O1 Mn1 141.94(17) . . ? N1 C1 C2 122.3(4) . . ? O6 S2 O5 117.20(18) . . ? O6 S2 O4 114.78(17) . . ? O5 S2 O4 113.15(17) . . ? O6 S2 C36 104.00(18) . . ? O5 S2 C36 103.68(19) . . ? O4 S2 C36 101.44(17) . . ? C14 N2 C6 118.7(3) . . ? C14 N2 Mn1 124.5(2) . . ? C6 N2 Mn1 116.8(2) . . ? C3 C2 C1 118.8(4) . . ? C22 N3 C18 118.3(3) . . ? C22 N3 Mn1 117.7(2) . . ? C18 N3 Mn1 123.6(3) . . ? C4 C3 C2 119.5(4) . . ? C31 N4 C23 117.7(3) . . ? C31 N4 Mn1 126.6(3) . . ? C23 N4 Mn1 115.5(2) . . ? S2 O4 Mn1 141.14(17) . . ? C3 C4 C5 118.7(4) . . ? N1 C5 C4 121.6(4) . . ? N1 C5 C6 116.4(3) . . ? C4 C5 C6 122.0(4) . . ? N2 C6 C7 121.1(3) . . ? N2 C6 C5 116.3(3) . . ? C7 C6 C5 122.5(3) . . ? C8 C7 C6 120.2(4) . . ? C9 C8 C7 118.8(4) . . ? C8 C9 C14 118.6(4) . . ? C8 C9 C10 124.7(4) . . ? C14 C9 C10 116.7(3) . . ? C9 C10 C11 107.0(3) . . ? C9 C10 C15 109.1(3) . . ? C11 C10 C15 87.1(3) . . ? C12 C11 C10 86.5(3) . . ? C13 C12 C11 109.8(3) . . ? C13 C12 C15 110.2(3) . . ? C11 C12 C15 88.1(3) . . ? C14 C13 C12 110.8(3) . . ? N2 C14 C9 122.5(3) . . ? N2 C14 C13 119.5(3) . . ? C9 C14 C13 118.0(3) . . ? C17 C15 C16 107.9(3) . . ? C17 C15 C12 118.9(3) . . ? C16 C15 C12 113.0(3) . . ? C17 C15 C10 120.0(3) . . ? C16 C15 C10 110.7(3) . . ? C12 C15 C10 84.8(3) . . ? N3 C18 C19 123.3(4) . . ? C20 C19 C18 117.8(4) . . ? C19 C20 C21 119.8(4) . . ? C22 C21 C20 119.4(4) . . ? N3 C22 C21 121.4(4) . . ? N3 C22 C23 116.8(3) . . ? C21 C22 C23 121.8(3) . . ? N4 C23 C24 121.8(4) . . ? N4 C23 C22 115.8(3) . . ? C24 C23 C22 122.3(3) . . ? C23 C24 C25 120.0(4) . . ? C26 C25 C24 118.9(4) . . ? C25 C26 C31 118.3(4) . . ? C25 C26 C27 124.9(4) . . ? C31 C26 C27 116.8(3) . . ? C26 C27 C28 105.8(3) . . ? C26 C27 C32 110.2(3) . . ? C28 C27 C32 87.0(3) . . ? C29 C28 C27 86.6(3) . . ? C30 C29 C28 109.5(3) . . ? C30 C29 C32 111.1(3) . . ? C28 C29 C32 87.7(3) . . ? C31 C30 C29 109.7(3) . . ? N4 C31 C26 122.8(3) . . ? N4 C31 C30 118.6(3) . . ? C26 C31 C30 118.5(3) . . ? C34 C32 C33 108.7(4) . . ? C34 C32 C29 119.0(3) . . ? C33 C32 C29 112.2(3) . . ? C34 C32 C27 119.1(4) . . ? C33 C32 C27 111.0(3) . . ? C29 C32 C27 85.2(3) . . ? F1 C35 F3 107.5(4) . . ? F1 C35 F2 108.1(4) . . ? F3 C35 F2 106.6(3) . . ? F1 C35 S1 111.3(3) . . ? F3 C35 S1 111.6(3) . . ? F2 C35 S1 111.5(3) . . ? F6 C36 F5 108.0(3) . . ? F6 C36 F4 107.2(3) . . ? F5 C36 F4 107.8(4) . . ? F6 C36 S2 112.2(3) . . ? F5 C36 S2 110.5(3) . . ? F4 C36 S2 110.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 N1 C1 -7.2(3) . . . . ? O4 Mn1 N1 C1 90.6(3) . . . . ? N3 Mn1 N1 C1 18.1(9) . . . . ? N2 Mn1 N1 C1 175.2(3) . . . . ? N4 Mn1 N1 C1 -99.8(3) . . . . ? O1 Mn1 N1 C5 174.3(3) . . . . ? O4 Mn1 N1 C5 -87.9(3) . . . . ? N3 Mn1 N1 C5 -160.4(6) . . . . ? N2 Mn1 N1 C5 -3.3(2) . . . . ? N4 Mn1 N1 C5 81.7(3) . . . . ? O3 S1 O1 Mn1 115.9(3) . . . . ? O2 S1 O1 Mn1 -20.2(3) . . . . ? C35 S1 O1 Mn1 -132.1(3) . . . . ? O4 Mn1 O1 S1 147.4(3) . . . . ? N3 Mn1 O1 S1 64.7(3) . . . . ? N1 Mn1 O1 S1 -119.1(3) . . . . ? N2 Mn1 O1 S1 -113.0(3) . . . . ? N4 Mn1 O1 S1 -7.8(3) . . . . ? C5 N1 C1 C2 -1.6(6) . . . . ? Mn1 N1 C1 C2 180.0(3) . . . . ? O1 Mn1 N2 C14 176.6(3) . . . . ? O4 Mn1 N2 C14 -81.3(3) . . . . ? N3 Mn1 N2 C14 -0.8(3) . . . . ? N1 Mn1 N2 C14 -177.0(3) . . . . ? N4 Mn1 N2 C14 71.0(3) . . . . ? O1 Mn1 N2 C6 -1.7(4) . . . . ? O4 Mn1 N2 C6 100.3(3) . . . . ? N3 Mn1 N2 C6 -179.1(2) . . . . ? N1 Mn1 N2 C6 4.7(2) . . . . ? N4 Mn1 N2 C6 -107.3(3) . . . . ? N1 C1 C2 C3 -0.2(6) . . . . ? O1 Mn1 N3 C22 -98.4(3) . . . . ? O4 Mn1 N3 C22 162.9(3) . . . . ? N1 Mn1 N3 C22 -123.7(7) . . . . ? N2 Mn1 N3 C22 80.6(3) . . . . ? N4 Mn1 N3 C22 -3.1(2) . . . . ? O1 Mn1 N3 C18 75.1(3) . . . . ? O4 Mn1 N3 C18 -23.6(3) . . . . ? N1 Mn1 N3 C18 49.8(8) . . . . ? N2 Mn1 N3 C18 -105.9(3) . . . . ? N4 Mn1 N3 C18 170.4(3) . . . . ? C1 C2 C3 C4 1.5(6) . . . . ? O1 Mn1 N4 C31 -90.4(3) . . . . ? O4 Mn1 N4 C31 153.2(3) . . . . ? N3 Mn1 N4 C31 -175.7(3) . . . . ? N1 Mn1 N4 C31 -4.0(3) . . . . ? N2 Mn1 N4 C31 68.3(3) . . . . ? O1 Mn1 N4 C23 94.3(3) . . . . ? O4 Mn1 N4 C23 -22.1(4) . . . . ? N3 Mn1 N4 C23 8.9(3) . . . . ? N1 Mn1 N4 C23 -179.3(2) . . . . ? N2 Mn1 N4 C23 -107.1(3) . . . . ? O6 S2 O4 Mn1 -1.2(3) . . . . ? O5 S2 O4 Mn1 137.0(3) . . . . ? C36 S2 O4 Mn1 -112.6(3) . . . . ? O1 Mn1 O4 S2 74.2(3) . . . . ? N3 Mn1 O4 S2 159.9(3) . . . . ? N1 Mn1 O4 S2 -11.6(3) . . . . ? N2 Mn1 O4 S2 -84.0(3) . . . . ? N4 Mn1 O4 S2 -170.3(2) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C1 N1 C5 C4 2.1(5) . . . . ? Mn1 N1 C5 C4 -179.3(3) . . . . ? C1 N1 C5 C6 -176.8(3) . . . . ? Mn1 N1 C5 C6 1.8(4) . . . . ? C3 C4 C5 N1 -0.8(6) . . . . ? C3 C4 C5 C6 178.0(4) . . . . ? C14 N2 C6 C7 -1.5(5) . . . . ? Mn1 N2 C6 C7 176.9(3) . . . . ? C14 N2 C6 C5 176.1(3) . . . . ? Mn1 N2 C6 C5 -5.4(4) . . . . ? N1 C5 C6 N2 2.5(5) . . . . ? C4 C5 C6 N2 -176.4(3) . . . . ? N1 C5 C6 C7 -179.9(3) . . . . ? C4 C5 C6 C7 1.2(6) . . . . ? N2 C6 C7 C8 0.0(6) . . . . ? C5 C6 C7 C8 -177.5(4) . . . . ? C6 C7 C8 C9 1.8(6) . . . . ? C7 C8 C9 C14 -2.0(6) . . . . ? C7 C8 C9 C10 176.3(4) . . . . ? C8 C9 C10 C11 -132.0(4) . . . . ? C14 C9 C10 C11 46.3(4) . . . . ? C8 C9 C10 C15 135.1(4) . . . . ? C14 C9 C10 C15 -46.5(5) . . . . ? C9 C10 C11 C12 -81.7(3) . . . . ? C15 C10 C11 C12 27.4(3) . . . . ? C10 C11 C12 C13 83.3(4) . . . . ? C10 C11 C12 C15 -27.6(3) . . . . ? C11 C12 C13 C14 -45.7(4) . . . . ? C15 C12 C13 C14 49.7(4) . . . . ? C6 N2 C14 C9 1.2(5) . . . . ? Mn1 N2 C14 C9 -177.1(3) . . . . ? C6 N2 C14 C13 -177.6(3) . . . . ? Mn1 N2 C14 C13 4.1(5) . . . . ? C8 C9 C14 N2 0.6(6) . . . . ? C10 C9 C14 N2 -177.9(3) . . . . ? C8 C9 C14 C13 179.4(3) . . . . ? C10 C9 C14 C13 0.9(5) . . . . ? C12 C13 C14 N2 177.0(3) . . . . ? C12 C13 C14 C9 -1.9(5) . . . . ? C13 C12 C15 C17 38.4(5) . . . . ? C11 C12 C15 C17 148.8(4) . . . . ? C13 C12 C15 C16 166.5(3) . . . . ? C11 C12 C15 C16 -83.1(4) . . . . ? C13 C12 C15 C10 -83.2(3) . . . . ? C11 C12 C15 C10 27.2(3) . . . . ? C9 C10 C15 C17 -40.5(5) . . . . ? C11 C10 C15 C17 -147.5(4) . . . . ? C9 C10 C15 C16 -167.4(3) . . . . ? C11 C10 C15 C16 85.7(4) . . . . ? C9 C10 C15 C12 80.0(3) . . . . ? C11 C10 C15 C12 -26.9(3) . . . . ? C22 N3 C18 C19 -2.6(6) . . . . ? Mn1 N3 C18 C19 -176.0(3) . . . . ? N3 C18 C19 C20 1.3(6) . . . . ? C18 C19 C20 C21 0.7(6) . . . . ? C19 C20 C21 C22 -1.4(6) . . . . ? C18 N3 C22 C21 1.8(5) . . . . ? Mn1 N3 C22 C21 175.7(3) . . . . ? C18 N3 C22 C23 -176.5(3) . . . . ? Mn1 N3 C22 C23 -2.6(4) . . . . ? C20 C21 C22 N3 0.1(6) . . . . ? C20 C21 C22 C23 178.3(4) . . . . ? C31 N4 C23 C24 -6.3(5) . . . . ? Mn1 N4 C23 C24 169.5(3) . . . . ? C31 N4 C23 C22 170.9(3) . . . . ? Mn1 N4 C23 C22 -13.3(4) . . . . ? N3 C22 C23 N4 10.8(5) . . . . ? C21 C22 C23 N4 -167.5(3) . . . . ? N3 C22 C23 C24 -172.0(3) . . . . ? C21 C22 C23 C24 9.7(6) . . . . ? N4 C23 C24 C25 5.9(6) . . . . ? C22 C23 C24 C25 -171.2(4) . . . . ? C23 C24 C25 C26 0.3(6) . . . . ? C24 C25 C26 C31 -5.5(6) . . . . ? C24 C25 C26 C27 171.6(4) . . . . ? C25 C26 C27 C28 -132.8(4) . . . . ? C31 C26 C27 C28 44.4(4) . . . . ? C25 C26 C27 C32 134.6(4) . . . . ? C31 C26 C27 C32 -48.2(5) . . . . ? C26 C27 C28 C29 -82.7(3) . . . . ? C32 C27 C28 C29 27.5(3) . . . . ? C27 C28 C29 C30 84.0(3) . . . . ? C27 C28 C29 C32 -27.6(3) . . . . ? C28 C29 C30 C31 -42.9(4) . . . . ? C32 C29 C30 C31 52.3(4) . . . . ? C23 N4 C31 C26 0.7(6) . . . . ? Mn1 N4 C31 C26 -174.5(3) . . . . ? C23 N4 C31 C30 -177.0(3) . . . . ? Mn1 N4 C31 C30 7.8(5) . . . . ? C25 C26 C31 N4 5.2(6) . . . . ? C27 C26 C31 N4 -172.2(3) . . . . ? C25 C26 C31 C30 -177.1(3) . . . . ? C27 C26 C31 C30 5.5(5) . . . . ? C29 C30 C31 N4 170.9(3) . . . . ? C29 C30 C31 C26 -6.8(5) . . . . ? C30 C29 C32 C34 38.1(5) . . . . ? C28 C29 C32 C34 148.1(4) . . . . ? C30 C29 C32 C33 166.6(3) . . . . ? C28 C29 C32 C33 -83.4(4) . . . . ? C30 C29 C32 C27 -82.7(3) . . . . ? C28 C29 C32 C27 27.3(3) . . . . ? C26 C27 C32 C34 -41.9(5) . . . . ? C28 C27 C32 C34 -147.7(4) . . . . ? C26 C27 C32 C33 -169.3(3) . . . . ? C28 C27 C32 C33 85.0(4) . . . . ? C26 C27 C32 C29 78.7(4) . . . . ? C28 C27 C32 C29 -27.0(3) . . . . ? O3 S1 C35 F1 -179.7(3) . . . . ? O2 S1 C35 F1 -56.7(4) . . . . ? O1 S1 C35 F1 62.1(4) . . . . ? O3 S1 C35 F3 -59.5(4) . . . . ? O2 S1 C35 F3 63.4(3) . . . . ? O1 S1 C35 F3 -177.8(3) . . . . ? O3 S1 C35 F2 59.6(3) . . . . ? O2 S1 C35 F2 -177.5(3) . . . . ? O1 S1 C35 F2 -58.6(3) . . . . ? O6 S2 C36 F6 59.0(3) . . . . ? O5 S2 C36 F6 -64.1(3) . . . . ? O4 S2 C36 F6 178.4(3) . . . . ? O6 S2 C36 F5 -61.7(3) . . . . ? O5 S2 C36 F5 175.3(3) . . . . ? O4 S2 C36 F5 57.7(3) . . . . ? O6 S2 C36 F4 178.8(3) . . . . ? O5 S2 C36 F4 55.7(3) . . . . ? O4 S2 C36 F4 -61.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.660 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.114 #END data_720650 _database_code_depnum_ccdc_archive 'CCDC 720650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Cl2 Mn N2 O' _chemical_formula_sum 'C17 H20 Cl2 Mn N2 O' _chemical_formula_weight 394.19 _chemical_absolute_configuration ad 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 8.189(5) _cell_length_b 8.755(5) _cell_length_c 26.303(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1885.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.988 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS V2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 29245 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4602 _reflns_number_gt 3454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER Shelxtl' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0433P)^2^+0.0114P] 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 -0.03(2) _refine_ls_number_reflns 4602 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.67988(5) 1.08590(4) 0.054206(13) 0.04356(11) Uani 1 1 d . . . Cl1 Cl 0.43971(10) 1.19552(10) 0.09000(3) 0.0697(2) Uani 1 1 d . . . N1 N 0.6832(3) 0.9092(2) -0.00654(7) 0.0607(5) Uani 1 1 d . . . C1 C 0.6867(5) 0.9373(3) -0.05654(11) 0.0827(10) Uani 1 1 d . . . H1A H 0.6824 1.0385 -0.0672 0.099 Uiso 1 1 calc R . . Cl2 Cl 0.92879(10) 1.17989(11) 0.08788(3) 0.0752(2) Uani 1 1 d . . . C6 C 0.6820(4) 0.7348(3) 0.06431(10) 0.0552(6) Uani 1 1 d . . . O1 O 0.6835(4) 1.2620(2) -0.00487(8) 0.0576(5) Uani 1 1 d . . . H1B H 0.602(5) 1.282(5) -0.0258(17) 0.111(16) Uiso 1 1 d . . . H1C H 0.760(5) 1.264(5) -0.0198(17) 0.11(2) Uiso 1 1 d . . . N3 N 0.6769(3) 0.85967(19) 0.09511(7) 0.0499(5) Uani 1 1 d . . . C5 C 0.6852(4) 0.7627(3) 0.00881(10) 0.0565(6) Uani 1 1 d . . . C7 C 0.6878(5) 0.5891(3) 0.08513(12) 0.0786(9) Uani 1 1 d . . . H7A H 0.6919 0.5038 0.0641 0.094 Uiso 1 1 calc R . . C8 C 0.6874(5) 0.5720(3) 0.13738(11) 0.0782(9) Uani 1 1 d . . . H8A H 0.6892 0.4745 0.1514 0.094 Uiso 1 1 calc R . . C9 C 0.6846(4) 0.6968(3) 0.16866(11) 0.0606(7) Uani 1 1 d . . . C10 C 0.6879(4) 0.6961(3) 0.22639(11) 0.0678(8) Uani 1 1 d . . . H10A H 0.6901 0.5953 0.2425 0.081 Uiso 1 1 calc R . . C11 C 0.8186(5) 0.8124(3) 0.24538(10) 0.0654(7) Uani 1 1 d . . . C12 C 0.6814(4) 0.9333(3) 0.23600(9) 0.0621(7) Uani 1 1 d . . . H12A H 0.6789 1.0183 0.2602 0.075 Uiso 1 1 calc R . . C13 C 0.6743(5) 0.9795(3) 0.17941(9) 0.0586(7) Uani 1 1 d . . . H13A H 0.5752 1.0372 0.1731 0.070 Uiso 1 1 calc R . . H13B H 0.7666 1.0447 0.1715 0.070 Uiso 1 1 calc R . . C14 C 0.6774(4) 0.8416(3) 0.14548(9) 0.0529(6) Uani 1 1 d . . . C15 C 0.5549(5) 0.8067(4) 0.24552(14) 0.0787(10) Uani 1 1 d . . . H15A H 0.4591 0.8124 0.2239 0.094 Uiso 1 1 calc R . . H15B H 0.5254 0.7932 0.2809 0.094 Uiso 1 1 calc R . . C3 C 0.6996(7) 0.6785(4) -0.07807(13) 0.1012(14) Uani 1 1 d . . . H3A H 0.7064 0.6001 -0.1018 0.121 Uiso 1 1 calc R . . C4 C 0.6928(6) 0.6454(3) -0.02666(13) 0.0928(12) Uani 1 1 d . . . H4A H 0.6933 0.5443 -0.0158 0.111 Uiso 1 1 calc R . . C2 C 0.6962(6) 0.8245(3) -0.09329(12) 0.0885(12) Uani 1 1 d . . . H2A H 0.7002 0.8494 -0.1276 0.106 Uiso 1 1 calc R . . C17 C 0.8564(6) 0.7954(4) 0.30288(12) 0.0990(13) Uani 1 1 d . . . H17A H 0.7560 0.7837 0.3214 0.149 Uiso 1 1 calc R . . H17B H 0.9125 0.8849 0.3147 0.149 Uiso 1 1 calc R . . H17C H 0.9239 0.7072 0.3082 0.149 Uiso 1 1 calc R . . C16 C 0.9812(4) 0.8252(5) 0.21690(13) 0.0870(10) Uani 1 1 d . . . H16A H 0.9605 0.8413 0.1814 0.131 Uiso 1 1 calc R . . H16B H 1.0424 0.7327 0.2213 0.131 Uiso 1 1 calc R . . H16C H 1.0425 0.9097 0.2302 0.131 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0587(2) 0.03095(16) 0.04107(18) -0.00051(15) -0.0043(2) -0.0006(2) Cl1 0.0663(5) 0.0817(5) 0.0612(5) 0.0038(4) 0.0020(4) 0.0213(4) N1 0.0985(16) 0.0363(10) 0.0474(12) -0.0048(9) -0.0068(14) -0.0036(17) C1 0.155(3) 0.0439(15) 0.0489(15) -0.0041(12) -0.012(2) -0.006(2) Cl2 0.0665(5) 0.1071(6) 0.0520(4) 0.0052(4) -0.0073(4) -0.0289(5) C6 0.0752(17) 0.0339(12) 0.0565(16) -0.0020(10) -0.0053(16) 0.0015(14) O1 0.0767(14) 0.0479(10) 0.0482(11) 0.0093(8) -0.0031(15) 0.0002(12) N3 0.0724(13) 0.0325(9) 0.0448(11) 0.0027(8) -0.0080(12) -0.0030(11) C5 0.0784(17) 0.0375(12) 0.0535(16) -0.0067(10) -0.0148(16) -0.0018(14) C7 0.130(3) 0.0345(12) 0.0714(18) 0.0023(13) -0.012(2) -0.003(2) C8 0.131(3) 0.0327(13) 0.0709(19) 0.0125(12) -0.008(2) -0.005(2) C9 0.0780(18) 0.0432(13) 0.0606(16) 0.0128(11) 0.0005(17) -0.0014(17) C10 0.094(2) 0.0507(15) 0.0584(17) 0.0206(12) 0.0106(18) 0.0023(18) C11 0.085(2) 0.0674(17) 0.0435(15) 0.0114(12) 0.0029(17) 0.008(2) C12 0.0883(19) 0.0572(16) 0.0409(13) 0.0065(11) 0.0093(15) 0.0117(18) C13 0.0906(19) 0.0429(12) 0.0423(14) 0.0038(10) -0.0023(17) 0.0033(16) C14 0.0718(16) 0.0374(12) 0.0496(14) 0.0060(10) -0.0050(15) -0.0015(14) C15 0.089(3) 0.081(2) 0.066(2) 0.0148(17) 0.0237(19) 0.004(2) C3 0.186(4) 0.0562(19) 0.062(2) -0.0206(15) -0.021(3) 0.017(3) C4 0.171(4) 0.0375(14) 0.069(2) -0.0129(13) -0.016(3) 0.005(2) C2 0.155(4) 0.0603(19) 0.0505(18) -0.0147(14) -0.010(2) 0.003(2) C17 0.144(4) 0.103(3) 0.0508(19) 0.0180(18) -0.008(2) 0.024(3) C16 0.080(2) 0.111(3) 0.069(2) -0.005(2) 0.0011(18) 0.007(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 2.189(2) . ? Mn1 N1 2.224(2) . ? Mn1 N3 2.254(2) . ? Mn1 Cl2 2.3698(13) . ? Mn1 Cl1 2.3822(13) . ? N1 C1 1.338(4) . ? N1 C5 1.344(3) . ? C1 C2 1.384(4) . ? C6 N3 1.362(3) . ? C6 C7 1.389(4) . ? C6 C5 1.481(4) . ? N3 C14 1.334(3) . ? C5 C4 1.389(4) . ? C7 C8 1.382(4) . ? C8 C9 1.368(4) . ? C9 C14 1.408(3) . ? C9 C10 1.519(4) . ? C10 C15 1.542(4) . ? C10 C11 1.559(5) . ? C11 C16 1.531(5) . ? C11 C17 1.551(4) . ? C11 C12 1.563(4) . ? C12 C15 1.537(5) . ? C12 C13 1.544(3) . ? C13 C14 1.502(3) . ? C3 C2 1.339(4) . ? C3 C4 1.384(5) . ? 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 N1 88.84(8) . . ? O1 Mn1 N3 163.28(7) . . ? N1 Mn1 N3 74.44(8) . . ? O1 Mn1 Cl2 90.52(9) . . ? N1 Mn1 Cl2 119.96(8) . . ? N3 Mn1 Cl2 97.81(7) . . ? O1 Mn1 Cl1 90.46(9) . . ? N1 Mn1 Cl1 125.05(8) . . ? N3 Mn1 Cl1 99.00(7) . . ? Cl2 Mn1 Cl1 114.99(5) . . ? C1 N1 C5 118.1(2) . . ? C1 N1 Mn1 125.30(18) . . ? C5 N1 Mn1 116.61(16) . . ? N1 C1 C2 123.8(3) . . ? N3 C6 C7 120.3(2) . . ? N3 C6 C5 117.0(2) . . ? C7 C6 C5 122.7(2) . . ? C14 N3 C6 119.69(19) . . ? C14 N3 Mn1 125.33(14) . . ? C6 N3 Mn1 114.93(16) . . ? N1 C5 C4 120.3(2) . . ? N1 C5 C6 117.0(2) . . ? C4 C5 C6 122.8(2) . . ? C8 C7 C6 119.4(3) . . ? C9 C8 C7 120.8(2) . . ? C8 C9 C14 117.4(2) . . ? C8 C9 C10 126.7(2) . . ? C14 C9 C10 115.9(2) . . ? C9 C10 C15 108.1(3) . . ? C9 C10 C11 109.3(2) . . ? C15 C10 C11 88.3(2) . . ? C16 C11 C17 108.1(3) . . ? C16 C11 C10 119.2(3) . . ? C17 C11 C10 112.7(3) . . ? C16 C11 C12 119.9(3) . . ? C17 C11 C12 111.2(3) . . ? C10 C11 C12 84.2(2) . . ? C15 C12 C13 108.7(3) . . ? C15 C12 C11 88.3(2) . . ? C13 C12 C11 110.9(2) . . ? C14 C13 C12 111.2(2) . . ? N3 C14 C9 122.5(2) . . ? N3 C14 C13 119.63(19) . . ? C9 C14 C13 117.9(2) . . ? C12 C15 C10 85.6(2) . . ? C2 C3 C4 119.4(3) . . ? C3 C4 C5 120.2(3) . . ? C3 C2 C1 118.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mn1 N1 C1 0.2(3) . . . . ? N3 Mn1 N1 C1 -179.9(3) . . . . ? Cl2 Mn1 N1 C1 -89.7(3) . . . . ? Cl1 Mn1 N1 C1 90.0(3) . . . . ? O1 Mn1 N1 C5 178.8(3) . . . . ? N3 Mn1 N1 C5 -1.2(2) . . . . ? Cl2 Mn1 N1 C5 88.9(3) . . . . ? Cl1 Mn1 N1 C5 -91.4(3) . . . . ? C5 N1 C1 C2 -1.7(6) . . . . ? Mn1 N1 C1 C2 176.9(3) . . . . ? C7 C6 N3 C14 0.0(5) . . . . ? C5 C6 N3 C14 -178.6(3) . . . . ? C7 C6 N3 Mn1 177.3(3) . . . . ? C5 C6 N3 Mn1 -1.3(4) . . . . ? O1 Mn1 N3 C14 178.7(4) . . . . ? N1 Mn1 N3 C14 178.4(3) . . . . ? Cl2 Mn1 N3 C14 59.4(3) . . . . ? Cl1 Mn1 N3 C14 -57.5(3) . . . . ? O1 Mn1 N3 C6 1.6(5) . . . . ? N1 Mn1 N3 C6 1.3(2) . . . . ? Cl2 Mn1 N3 C6 -117.7(2) . . . . ? Cl1 Mn1 N3 C6 125.3(2) . . . . ? C1 N1 C5 C4 0.9(6) . . . . ? Mn1 N1 C5 C4 -177.9(3) . . . . ? C1 N1 C5 C6 179.7(3) . . . . ? Mn1 N1 C5 C6 1.0(4) . . . . ? N3 C6 C5 N1 0.2(5) . . . . ? C7 C6 C5 N1 -178.3(4) . . . . ? N3 C6 C5 C4 179.1(4) . . . . ? C7 C6 C5 C4 0.5(6) . . . . ? N3 C6 C7 C8 0.3(6) . . . . ? C5 C6 C7 C8 178.8(3) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C7 C8 C9 C14 1.7(6) . . . . ? C7 C8 C9 C10 -178.4(3) . . . . ? C8 C9 C10 C15 -133.5(4) . . . . ? C14 C9 C10 C15 46.4(4) . . . . ? C8 C9 C10 C11 131.9(4) . . . . ? C14 C9 C10 C11 -48.3(4) . . . . ? C9 C10 C11 C16 -39.6(4) . . . . ? C15 C10 C11 C16 -148.3(3) . . . . ? C9 C10 C11 C17 -168.0(3) . . . . ? C15 C10 C11 C17 83.4(3) . . . . ? C9 C10 C11 C12 81.4(2) . . . . ? C15 C10 C11 C12 -27.19(19) . . . . ? C16 C11 C12 C15 147.7(3) . . . . ? C17 C11 C12 C15 -84.9(3) . . . . ? C10 C11 C12 C15 27.3(2) . . . . ? C16 C11 C12 C13 38.3(4) . . . . ? C17 C11 C12 C13 165.7(3) . . . . ? C10 C11 C12 C13 -82.1(3) . . . . ? C15 C12 C13 C14 -48.3(4) . . . . ? C11 C12 C13 C14 47.2(4) . . . . ? C6 N3 C14 C9 0.6(5) . . . . ? Mn1 N3 C14 C9 -176.4(2) . . . . ? C6 N3 C14 C13 179.1(3) . . . . ? Mn1 N3 C14 C13 2.1(4) . . . . ? C8 C9 C14 N3 -1.4(5) . . . . ? C10 C9 C14 N3 178.7(3) . . . . ? C8 C9 C14 C13 -180.0(4) . . . . ? C10 C9 C14 C13 0.1(5) . . . . ? C12 C13 C14 N3 -178.1(3) . . . . ? C12 C13 C14 C9 0.5(4) . . . . ? C13 C12 C15 C10 84.0(3) . . . . ? C11 C12 C15 C10 -27.5(2) . . . . ? C9 C10 C15 C12 -82.1(3) . . . . ? C11 C10 C15 C12 27.61(19) . . . . ? C2 C3 C4 C5 -1.0(8) . . . . ? N1 C5 C4 C3 0.5(7) . . . . ? C6 C5 C4 C3 -178.4(4) . . . . ? C4 C3 C2 C1 0.3(8) . . . . ? N1 C1 C2 C3 1.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.328 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.044