# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Shouvik Chattopadhyay' _publ_contact_author_address ; 88 Raja SC Mullik Rd Jadavpur Kolkata 700 032 Kolkta West Bengal India 700032 ; _publ_contact_author_email shouvik.chem@gmail.com loop_ _publ_author_name P.Bhowmik H.P.Nayek M.Corbella N.Aliaga-Alcalde 'Shouvik Chattopadhyay' # Attachment '- 2.txt' data_2 _database_code_depnum_ccdc_archive 'CCDC 794445' #TrackingRef '- 2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Mn N5 O5, 2(H2 O)' _chemical_formula_sum 'C22 H24 Mn N5 O7' _chemical_formula_weight 525.40 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.069(3) _cell_length_b 15.616(3) _cell_length_c 18.099(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4541.7(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20572 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 28.0 _exptl_crystal_description Parallelopiped _exptl_crystal_colour Black _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.636 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8995 _exptl_absorpt_correction_T_max 0.9162 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20572 _diffrn_reflns_av_R_equivalents 0.0997 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5474 _reflns_number_gt 3296 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA, PLATON (A.L.Spek, 2005)' _computing_data_reduction 'STOE X-RED, PLATON (A.L.Spek, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond 2.1e/3' _computing_publication_material 'WINGX V1.80.05' _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^ > 2\s(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^)+(0.0925P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5474 _refine_ls_number_parameters 338 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _refine_ls_shift/su_max 0.025 _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 0.48568(3) 0.56727(3) 0.61718(3) 0.03594(15) Uani 1 1 d . . . O4 O 0.48025(15) 0.28856(15) 0.56951(13) 0.0409(5) Uani 1 1 d . . . O3 O 0.49471(14) 0.44799(15) 0.60641(13) 0.0387(5) Uani 1 1 d . . . O1 O 0.28010(14) 0.53926(17) 0.45820(14) 0.0463(6) Uani 1 1 d . . . O5 O 0.58630(16) 0.58821(18) 0.53213(14) 0.0393(5) Uani 1 1 d . . . O2 O 0.39963(14) 0.57238(15) 0.54724(13) 0.0391(5) Uani 1 1 d . . . C16 C 0.5993(2) 0.4177(2) 0.69897(18) 0.0385(7) Uani 1 1 d . . . N1 N 0.48623(17) 0.69361(18) 0.63141(15) 0.0383(6) Uani 1 1 d . . . N2 N 0.57537(17) 0.57151(18) 0.69262(15) 0.0370(6) Uani 1 1 d . . . C21 C 0.54258(19) 0.3938(2) 0.64231(18) 0.0364(7) Uani 1 1 d . . . O6 O 0.2473(3) 0.4913(2) 0.6313(2) 0.0730(9) Uani 1 1 d . . . C15 C 0.6120(2) 0.5049(2) 0.72036(19) 0.0405(7) Uani 1 1 d . . . H15 H 0.6503 0.5148 0.7579 0.049 Uiso 1 1 calc R . . C17 C 0.6462(2) 0.3542(2) 0.73528(19) 0.0424(8) Uani 1 1 d . . . H17 H 0.6831 0.3701 0.7724 0.051 Uiso 1 1 calc R . . C2 C 0.2878(2) 0.6240(2) 0.47710(19) 0.0408(8) Uani 1 1 d . . . C19 C 0.5831(2) 0.2454(2) 0.6610(2) 0.0413(7) Uani 1 1 d . . . H19 H 0.5777 0.1878 0.6486 0.050 Uiso 1 1 calc R . . N4 N 0.41945(19) 0.5416(2) 0.76969(18) 0.0451(7) Uani 1 1 d . . . N5 N 0.4472(2) 0.5258(2) 0.82771(18) 0.0557(8) Uani 1 1 d . . . C9 C 0.5481(2) 0.7215(2) 0.68246(18) 0.0394(7) Uani 1 1 d . . . C22 C 0.4664(2) 0.1999(2) 0.5518(2) 0.0470(8) Uani 1 1 d . . . H22A H 0.4261 0.1958 0.5128 0.071 Uiso 1 1 calc R . . H22B H 0.4461 0.1705 0.5947 0.071 Uiso 1 1 calc R . . H22C H 0.5178 0.1744 0.5360 0.071 Uiso 1 1 calc R . . C7 C 0.35419(19) 0.6393(2) 0.52787(18) 0.0383(7) Uani 1 1 d . . . C10 C 0.5633(2) 0.8068(2) 0.7011(2) 0.0434(8) Uani 1 1 d . . . H10 H 0.5352 0.8505 0.6768 0.052 Uiso 1 1 calc R . . C14 C 0.5930(2) 0.6562(2) 0.71764(19) 0.0386(7) Uani 1 1 d . . . C6 C 0.3668(2) 0.7229(2) 0.55286(19) 0.0413(8) Uani 1 1 d . . . C20 C 0.5364(2) 0.3058(2) 0.62423(18) 0.0379(7) Uani 1 1 d . . . C11 C 0.6201(2) 0.8258(2) 0.7556(2) 0.0440(8) Uani 1 1 d . . . H11 H 0.6305 0.8827 0.7679 0.053 Uiso 1 1 calc R . . C12 C 0.6619(2) 0.7613(2) 0.7923(2) 0.0464(8) Uani 1 1 d . . . H12 H 0.6984 0.7749 0.8303 0.056 Uiso 1 1 calc R . . C8 C 0.4325(2) 0.7462(2) 0.60284(19) 0.0421(8) Uani 1 1 d . . . H8 H 0.4369 0.8036 0.6158 0.050 Uiso 1 1 calc R . . C18 C 0.6387(2) 0.2700(2) 0.7172(2) 0.0456(8) Uani 1 1 d . . . H18 H 0.6701 0.2289 0.7417 0.055 Uiso 1 1 calc R . . C13 C 0.6498(2) 0.6767(2) 0.7730(2) 0.0435(8) Uani 1 1 d . . . H13 H 0.6794 0.6337 0.7968 0.052 Uiso 1 1 calc R . . N3 N 0.39233(19) 0.5582(2) 0.71083(17) 0.0480(7) Uani 1 1 d . . . C5 C 0.3144(2) 0.7895(2) 0.5272(2) 0.0486(9) Uani 1 1 d . . . H5 H 0.3230 0.8452 0.5437 0.058 Uiso 1 1 calc R . . C3 C 0.2385(2) 0.6895(3) 0.4530(2) 0.0484(9) Uani 1 1 d . . . H3 H 0.1960 0.6785 0.4195 0.058 Uiso 1 1 calc R . . C4 C 0.2514(2) 0.7730(3) 0.4785(2) 0.0514(9) Uani 1 1 d . . . H4 H 0.2171 0.8173 0.4624 0.062 Uiso 1 1 calc R . . O7 O 0.5657(4) 0.4715(4) 0.9335(5) 0.179(4) Uani 1 1 d D . . C1 C 0.2123(2) 0.5172(3) 0.4102(2) 0.0562(10) Uani 1 1 d . . . H1A H 0.2131 0.4566 0.4009 0.084 Uiso 1 1 calc R . . H1B H 0.2179 0.5475 0.3644 0.084 Uiso 1 1 calc R . . H1C H 0.1606 0.5325 0.4333 0.084 Uiso 1 1 calc R . . H5B H 0.605(3) 0.541(3) 0.522(2) 0.049(12) Uiso 1 1 d . . . H5A H 0.557(4) 0.613(4) 0.501(3) 0.090(19) Uiso 1 1 d . . . H6A H 0.191(5) 0.494(4) 0.608(4) 0.13(3) Uiso 1 1 d . . . H6B H 0.300(4) 0.504(4) 0.641(3) 0.11(2) Uiso 1 1 d . . . H7A H 0.523(4) 0.465(5) 0.966(4) 0.175 Uiso 1 1 d D . . H7B H 0.537(3) 0.489(4) 0.892(2) 0.175 Uiso 1 1 d 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 0.0385(3) 0.0340(3) 0.0353(3) -0.0005(2) -0.0016(2) 0.0007(2) O4 0.0467(13) 0.0375(12) 0.0385(12) -0.0002(10) -0.0066(10) -0.0027(10) O3 0.0415(12) 0.0362(12) 0.0383(12) 0.0012(9) -0.0056(9) 0.0006(9) O1 0.0421(13) 0.0473(14) 0.0494(14) 0.0015(11) -0.0116(11) -0.0015(11) O5 0.0415(13) 0.0369(14) 0.0395(13) 0.0015(11) 0.0010(10) 0.0006(11) O2 0.0425(12) 0.0358(12) 0.0389(12) -0.0012(10) -0.0044(9) 0.0031(9) C16 0.0403(17) 0.0388(19) 0.0365(17) -0.0001(14) -0.0022(13) -0.0015(13) N1 0.0425(14) 0.0364(14) 0.0361(14) -0.0012(11) 0.0030(11) 0.0010(12) N2 0.0391(14) 0.0352(14) 0.0369(14) -0.0008(12) 0.0007(11) -0.0001(11) C21 0.0351(15) 0.0374(17) 0.0365(16) 0.0026(14) 0.0025(12) 0.0003(13) O6 0.063(2) 0.083(2) 0.073(2) 0.0045(18) 0.0058(17) -0.0169(18) C15 0.0404(17) 0.044(2) 0.0374(17) 0.0000(14) -0.0019(13) -0.0019(14) C17 0.0421(17) 0.045(2) 0.0405(18) 0.0010(15) -0.0070(14) -0.0010(15) C2 0.0362(17) 0.046(2) 0.0403(18) 0.0019(15) 0.0018(13) 0.0016(14) C19 0.0430(18) 0.0354(18) 0.0455(19) 0.0000(15) -0.0006(14) 0.0012(14) N4 0.0499(17) 0.0419(16) 0.0434(18) -0.0039(13) 0.0126(14) -0.0035(13) N5 0.065(2) 0.060(2) 0.0422(18) -0.0003(15) 0.0060(15) -0.0059(17) C9 0.0399(17) 0.0406(19) 0.0376(17) -0.0021(14) 0.0051(14) 0.0002(14) C22 0.052(2) 0.0385(19) 0.051(2) -0.0020(16) -0.0044(16) -0.0040(15) C7 0.0357(16) 0.0402(19) 0.0391(17) 0.0046(14) 0.0061(13) 0.0036(14) C10 0.0429(18) 0.0393(19) 0.0479(19) -0.0013(15) 0.0055(15) -0.0018(15) C14 0.0384(16) 0.0382(18) 0.0392(17) -0.0036(14) 0.0059(13) -0.0017(13) C6 0.0401(17) 0.044(2) 0.0400(18) 0.0015(15) 0.0054(14) 0.0032(14) C20 0.0389(16) 0.0376(17) 0.0373(17) 0.0014(14) 0.0000(13) -0.0022(13) C11 0.0459(18) 0.0392(19) 0.047(2) -0.0086(16) 0.0055(15) -0.0055(15) C12 0.0452(19) 0.051(2) 0.0430(19) -0.0091(16) 0.0015(15) -0.0087(16) C8 0.0429(18) 0.0395(18) 0.0438(18) -0.0020(14) 0.0050(14) 0.0050(14) C18 0.0437(19) 0.043(2) 0.050(2) 0.0076(16) -0.0082(15) 0.0029(15) C13 0.0448(18) 0.045(2) 0.0412(18) -0.0016(15) -0.0012(14) -0.0031(15) N3 0.0511(17) 0.0510(19) 0.0421(17) 0.0021(14) 0.0083(13) -0.0004(14) C5 0.050(2) 0.045(2) 0.051(2) -0.0003(17) 0.0034(16) 0.0101(16) C3 0.0406(18) 0.053(2) 0.052(2) 0.0066(17) -0.0024(15) 0.0040(16) C4 0.0436(19) 0.051(2) 0.059(2) 0.0092(18) -0.0016(17) 0.0102(17) O7 0.195(7) 0.101(4) 0.242(9) 0.045(5) -0.141(6) 0.000(5) C1 0.048(2) 0.059(3) 0.062(2) 0.001(2) -0.0150(18) -0.0044(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 1.876(2) . ? Mn1 O3 1.879(2) . ? Mn1 N2 1.986(3) . ? Mn1 N1 1.990(3) . ? Mn1 O5 2.256(2) . ? Mn1 N3 2.268(3) . ? O4 C20 1.366(4) . ? O4 C22 1.438(4) . ? O3 C21 1.315(4) . ? O1 C2 1.372(4) . ? O1 C1 1.435(4) . ? O5 H5B 0.81(5) . ? O5 H5A 0.83(6) . ? O2 C7 1.322(4) . ? C16 C17 1.409(5) . ? C16 C21 1.422(5) . ? C16 C15 1.429(5) . ? N1 C8 1.299(4) . ? N1 C9 1.426(4) . ? N2 C15 1.297(4) . ? N2 C14 1.426(4) . ? C21 C20 1.416(5) . ? O6 H6A 0.99(8) . ? O6 H6B 0.89(7) . ? C15 H15 0.9300 . ? C17 C18 1.361(5) . ? C17 H17 0.9300 . ? C2 C3 1.366(5) . ? C2 C7 1.429(5) . ? C19 C20 1.377(5) . ? C19 C18 1.406(5) . ? C19 H19 0.9300 . ? N4 N5 1.167(5) . ? N4 N3 1.180(4) . ? C9 C10 1.396(5) . ? C9 C14 1.402(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C7 C6 1.396(5) . ? C10 C11 1.377(5) . ? C10 H10 0.9300 . ? C14 C13 1.393(5) . ? C6 C5 1.416(5) . ? C6 C8 1.437(5) . ? C11 C12 1.381(5) . ? C11 H11 0.9300 . ? C12 C13 1.379(5) . ? C12 H12 0.9300 . ? C8 H8 0.9300 . ? C18 H18 0.9300 . ? C13 H13 0.9300 . ? C5 C4 1.367(6) . ? C5 H5 0.9300 . ? C3 C4 1.399(6) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? O7 H7A 0.91(7) . ? O7 H7B 0.93(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mn1 O3 91.67(10) . . ? O2 Mn1 N2 175.54(11) . . ? O3 Mn1 N2 92.77(11) . . ? O2 Mn1 N1 92.77(11) . . ? O3 Mn1 N1 175.10(11) . . ? N2 Mn1 N1 82.81(11) . . ? O2 Mn1 O5 93.54(10) . . ? O3 Mn1 O5 91.01(10) . . ? N2 Mn1 O5 86.80(11) . . ? N1 Mn1 O5 86.64(11) . . ? O2 Mn1 N3 91.11(11) . . ? O3 Mn1 N3 93.84(11) . . ? N2 Mn1 N3 88.18(12) . . ? N1 Mn1 N3 88.16(12) . . ? O5 Mn1 N3 173.19(11) . . ? C20 O4 C22 117.0(3) . . ? C21 O3 Mn1 129.2(2) . . ? C2 O1 C1 116.8(3) . . ? Mn1 O5 H5B 107(3) . . ? Mn1 O5 H5A 97(4) . . ? H5B O5 H5A 119(5) . . ? C7 O2 Mn1 128.3(2) . . ? C17 C16 C21 119.6(3) . . ? C17 C16 C15 117.9(3) . . ? C21 C16 C15 122.5(3) . . ? C8 N1 C9 121.9(3) . . ? C8 N1 Mn1 124.9(2) . . ? C9 N1 Mn1 112.9(2) . . ? C15 N2 C14 122.1(3) . . ? C15 N2 Mn1 124.7(2) . . ? C14 N2 Mn1 113.2(2) . . ? O3 C21 C20 118.0(3) . . ? O3 C21 C16 124.2(3) . . ? C20 C21 C16 117.8(3) . . ? H6A O6 H6B 159(6) . . ? N2 C15 C16 126.4(3) . . ? N2 C15 H15 116.8 . . ? C16 C15 H15 116.8 . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C3 C2 O1 126.2(3) . . ? C3 C2 C7 120.9(3) . . ? O1 C2 C7 112.9(3) . . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? N5 N4 N3 179.0(4) . . ? C10 C9 C14 119.6(3) . . ? C10 C9 N1 124.7(3) . . ? C14 C9 N1 115.6(3) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C7 C6 125.0(3) . . ? O2 C7 C2 116.8(3) . . ? C6 C7 C2 118.2(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C13 C14 C9 119.7(3) . . ? C13 C14 N2 124.9(3) . . ? C9 C14 N2 115.3(3) . . ? C7 C6 C5 119.6(3) . . ? C7 C6 C8 123.2(3) . . ? C5 C6 C8 117.2(3) . . ? O4 C20 C19 125.1(3) . . ? O4 C20 C21 113.9(3) . . ? C19 C20 C21 121.0(3) . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N1 C8 C6 125.4(3) . . ? N1 C8 H8 117.3 . . ? C6 C8 H8 117.3 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? N4 N3 Mn1 116.4(2) . . ? C4 C5 C6 120.9(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? H7A O7 H7B 101(6) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.035 _refine_diff_density_min -0.984 _refine_diff_density_rms 0.119 # Attachment '- 3.txt' data_3 _database_code_depnum_ccdc_archive 'CCDC 794446' #TrackingRef '- 3.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Mn N5 O2' _chemical_formula_sum 'C20 H14 Mn N5 O2' _chemical_formula_weight 411.30 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 ? _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.760 _cell_length_b 13.356 _cell_length_c 6.616 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1657.696 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Parallelopiped _exptl_crystal_colour black _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.848 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7096 _diffrn_reflns_av_R_equivalents 0.1069 _diffrn_reflns_av_sigmaI/netI 0.0901 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2075 _reflns_number_gt 3131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1401P)^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 riding _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 0.48(4) _refine_ls_number_reflns 3781 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.1954 _refine_ls_wR_factor_gt 0.1904 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.39431(4) 0.22521(4) 0.94592(14) 0.0372(2) Uani 1 1 d . . . N3 N 0.4317(3) 0.2175(4) 1.2758(8) 0.0487(11) Uani 1 1 d . . . N1 N 0.4892(2) 0.2853(3) 0.8854(7) 0.0385(9) Uani 1 1 d . . . N2 N 0.4476(2) 0.0983(3) 0.8919(6) 0.0354(8) Uani 1 1 d . . . N4 N 0.4017(2) 0.2181(3) 1.4336(10) 0.0402(9) Uani 1 1 d . . . N5 N 0.3727(3) 0.2175(4) 1.5910(8) 0.0496(11) Uani 1 1 d . . . O2 O 0.35097(19) 0.3511(2) 0.9716(7) 0.0434(8) Uani 1 1 d . . . O3 O 0.3091(2) 0.1570(2) 0.9968(5) 0.0415(8) Uani 1 1 d . . . C1 C 0.3781(3) 0.4405(3) 0.9463(9) 0.0381(9) Uani 1 1 d . . . C2 C 0.3337(3) 0.5238(4) 0.9820(9) 0.0417(11) Uani 1 1 d . . . H2 H 0.2874 0.5136 1.0282 0.050 Uiso 1 1 calc R . . C3 C 0.3574(3) 0.6196(3) 0.9496(11) 0.0468(11) Uani 1 1 d . . . H3 H 0.3268 0.6733 0.9709 0.056 Uiso 1 1 calc R . . C4 C 0.4273(3) 0.6375(4) 0.8850(9) 0.0450(12) Uani 1 1 d . . . H4 H 0.4430 0.7027 0.8637 0.054 Uiso 1 1 calc R . . C5 C 0.4723(3) 0.5590(4) 0.8535(8) 0.0412(11) Uani 1 1 d . . . H5 H 0.5188 0.5710 0.8108 0.049 Uiso 1 1 calc R . . C6 C 0.4490(3) 0.4587(4) 0.8852(8) 0.0398(10) Uani 1 1 d . . . C7 C 0.5010(3) 0.3814(4) 0.8575(7) 0.0395(10) Uani 1 1 d . . . H7 H 0.5464 0.4005 0.8167 0.047 Uiso 1 1 calc R . . C8 C 0.5456(3) 0.2127(4) 0.8721(8) 0.0385(10) Uani 1 1 d . . . C9 C 0.6174(3) 0.2347(4) 0.8608(9) 0.0460(12) Uani 1 1 d . . . H9 H 0.6325 0.3010 0.8592 0.055 Uiso 1 1 calc R . . C10 C 0.6674(3) 0.1573(4) 0.8516(8) 0.0454(12) Uani 1 1 d . . . H10 H 0.7158 0.1715 0.8434 0.054 Uiso 1 1 calc R . . C11 C 0.6433(3) 0.0574(4) 0.8551(8) 0.0465(12) Uani 1 1 d . . . H11 H 0.6760 0.0052 0.8485 0.056 Uiso 1 1 calc R . . C12 C 0.5719(3) 0.0367(4) 0.8681(8) 0.0427(11) Uani 1 1 d . . . H12 H 0.5568 -0.0296 0.8721 0.051 Uiso 1 1 calc R . . C13 C 0.5216(3) 0.1127(3) 0.8754(7) 0.0380(10) Uani 1 1 d . . . C14 C 0.4175(3) 0.0128(4) 0.8607(8) 0.0419(11) Uani 1 1 d . . . H14 H 0.4469 -0.0399 0.8217 0.050 Uiso 1 1 calc R . . C15 C 0.3431(3) -0.0082(3) 0.8806(8) 0.0378(10) Uani 1 1 d . . . C16 C 0.3196(3) -0.1071(4) 0.8380(7) 0.0422(11) Uani 1 1 d . . . H16 H 0.3523 -0.1533 0.7884 0.051 Uiso 1 1 calc R . . C17 C 0.2515(3) -0.1362(4) 0.8672(9) 0.0437(11) Uani 1 1 d . . . H17 H 0.2370 -0.2004 0.8316 0.052 Uiso 1 1 calc R . . C18 C 0.2022(3) -0.0670(4) 0.9534(10) 0.0444(10) Uani 1 1 d . . . H18 H 0.1560 -0.0875 0.9829 0.053 Uiso 1 1 calc R . . C19 C 0.2231(3) 0.0310(4) 0.9936(7) 0.0410(11) Uani 1 1 d . . . H19 H 0.1901 0.0762 1.0454 0.049 Uiso 1 1 calc R . . C20 C 0.2931(2) 0.0624(3) 0.9571(9) 0.0364(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 0.0516(4) 0.0248(3) 0.0352(4) -0.0009(3) 0.0036(4) 0.0007(3) N3 0.064(3) 0.046(3) 0.037(2) -0.0018(18) -0.002(2) -0.006(2) N1 0.052(2) 0.0272(18) 0.036(2) 0.0001(15) 0.0016(16) -0.0003(16) N2 0.060(2) 0.0233(16) 0.0224(16) -0.0020(13) 0.0030(15) 0.0063(16) N4 0.060(2) 0.0288(17) 0.032(2) 0.0023(18) 0.001(2) 0.0026(15) N5 0.061(3) 0.051(3) 0.037(2) 0.0042(19) 0.001(2) 0.010(2) O2 0.061(2) 0.0229(14) 0.046(2) 0.0000(16) 0.0077(18) -0.0012(13) O3 0.059(2) 0.0266(15) 0.0387(19) -0.0033(12) 0.0074(14) -0.0016(14) C1 0.061(3) 0.0293(18) 0.0241(16) -0.002(2) 0.003(2) -0.0008(17) C2 0.050(2) 0.032(2) 0.043(3) -0.003(2) -0.001(2) 0.0037(18) C3 0.069(3) 0.029(2) 0.042(2) -0.007(2) -0.002(3) 0.004(2) C4 0.073(3) 0.0177(19) 0.045(3) 0.0004(18) -0.006(2) -0.001(2) C5 0.059(3) 0.029(2) 0.035(2) 0.0033(18) 0.004(2) -0.007(2) C6 0.052(3) 0.028(2) 0.040(2) 0.0028(19) 0.006(2) -0.0003(19) C7 0.053(3) 0.039(3) 0.027(2) 0.001(2) 0.005(2) -0.005(2) C8 0.052(3) 0.033(2) 0.0303(19) -0.0019(18) 0.0029(19) 0.0092(19) C9 0.066(3) 0.037(3) 0.035(2) 0.001(2) 0.003(2) 0.000(2) C10 0.057(3) 0.051(3) 0.028(2) -0.001(2) 0.002(2) 0.002(2) C11 0.059(3) 0.048(3) 0.032(2) -0.003(2) -0.006(2) 0.014(2) C12 0.061(3) 0.030(2) 0.038(2) -0.001(2) 0.004(2) 0.007(2) C13 0.062(3) 0.029(2) 0.0229(17) -0.0001(18) -0.0010(19) 0.009(2) C14 0.061(3) 0.033(2) 0.031(2) -0.002(2) -0.003(2) 0.004(2) C15 0.061(3) 0.027(2) 0.0254(19) -0.0038(16) -0.0020(19) 0.003(2) C16 0.074(3) 0.027(2) 0.025(2) -0.0034(17) -0.001(2) 0.002(2) C17 0.062(3) 0.031(2) 0.038(2) -0.002(2) -0.005(2) 0.001(2) C18 0.061(3) 0.035(2) 0.037(2) 0.001(3) -0.002(3) -0.0053(19) C19 0.062(3) 0.031(2) 0.031(2) -0.0020(17) -0.0013(19) 0.001(2) C20 0.059(2) 0.0270(18) 0.0235(18) -0.001(2) 0.000(2) 0.0025(17) _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 1.871(4) . ? Mn1 O2 1.876(3) . ? Mn1 N1 1.993(5) . ? Mn1 N2 2.000(4) . ? Mn1 N3 2.295(5) . ? Mn1 N5 2.385(5) 1_554 ? N3 N4 1.186(8) . ? N1 C7 1.316(7) . ? N1 C8 1.439(6) . ? N2 C14 1.290(7) . ? N2 C13 1.407(7) . ? N4 N5 1.175(9) . ? N5 Mn1 2.385(5) 1_556 ? O2 C1 1.309(5) . ? O3 C20 1.326(5) . ? C1 C2 1.410(7) . ? C1 C6 1.412(7) . ? C2 C3 1.371(7) . ? C2 H2 0.9300 . ? C3 C4 1.400(8) . ? C3 H3 0.9300 . ? C4 C5 1.362(8) . ? C4 H4 0.9300 . ? C5 C6 1.424(7) . ? C5 H5 0.9300 . ? C6 C7 1.432(8) . ? C7 H7 0.9300 . ? C8 C9 1.379(8) . ? C8 C13 1.410(7) . ? C9 C10 1.396(8) . ? C9 H9 0.9300 . ? C10 C11 1.410(9) . ? C10 H10 0.9300 . ? C11 C12 1.370(8) . ? C11 H11 0.9300 . ? C12 C13 1.386(7) . ? C12 H12 0.9300 . ? C14 C15 1.430(8) . ? C14 H14 0.9300 . ? C15 C16 1.420(7) . ? C15 C20 1.423(7) . ? C16 C17 1.349(8) . ? C16 H16 0.9300 . ? C17 C18 1.426(8) . ? C17 H17 0.9300 . ? C18 C19 1.392(7) . ? C18 H18 0.9300 . ? C19 C20 1.399(8) . ? C19 H19 0.9300 . ? 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 O2 92.85(15) . . ? O3 Mn1 N1 174.56(16) . . ? O2 Mn1 N1 92.54(16) . . ? O3 Mn1 N2 92.66(17) . . ? O2 Mn1 N2 173.10(17) . . ? N1 Mn1 N2 81.91(17) . . ? O3 Mn1 N3 93.92(17) . . ? O2 Mn1 N3 94.97(19) . . ? N1 Mn1 N3 86.34(19) . . ? N2 Mn1 N3 88.80(17) . . ? O3 Mn1 N5 90.63(18) . 1_554 ? O2 Mn1 N5 93.10(19) . 1_554 ? N1 Mn1 N5 88.4(2) . 1_554 ? N2 Mn1 N5 82.68(16) . 1_554 ? N3 Mn1 N5 170.53(19) . 1_554 ? N4 N3 Mn1 133.8(5) . . ? C7 N1 C8 121.6(5) . . ? C7 N1 Mn1 124.8(4) . . ? C8 N1 Mn1 113.5(3) . . ? C14 N2 C13 122.7(4) . . ? C14 N2 Mn1 124.1(4) . . ? C13 N2 Mn1 113.0(3) . . ? N5 N4 N3 178.9(6) . . ? N4 N5 Mn1 142.6(5) . 1_556 ? C1 O2 Mn1 129.6(3) . . ? C20 O3 Mn1 128.5(3) . . ? O2 C1 C2 117.9(4) . . ? O2 C1 C6 124.1(4) . . ? C2 C1 C6 118.0(4) . . ? C3 C2 C1 121.2(5) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 120.7(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.7(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 119.6(5) . . ? C1 C6 C7 123.6(4) . . ? C5 C6 C7 116.8(5) . . ? N1 C7 C6 124.8(5) . . ? N1 C7 H7 117.6 . . ? C6 C7 H7 117.6 . . ? C9 C8 C13 121.0(5) . . ? C9 C8 N1 125.4(5) . . ? C13 C8 N1 113.7(5) . . ? C8 C9 C10 120.0(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 119.0(6) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C12 C11 C10 120.4(5) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.3(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 N2 125.0(5) . . ? C12 C13 C8 118.4(5) . . ? N2 C13 C8 116.5(4) . . ? N2 C14 C15 125.8(5) . . ? N2 C14 H14 117.1 . . ? C15 C14 H14 117.1 . . ? C16 C15 C20 118.8(5) . . ? C16 C15 C14 117.8(5) . . ? C20 C15 C14 123.2(5) . . ? C17 C16 C15 122.2(5) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 119.0(5) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 120.2(5) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.8(5) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? O3 C20 C19 117.6(4) . . ? O3 C20 C15 123.6(4) . . ? C19 C20 C15 118.8(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.062 _refine_diff_density_min -0.881 _refine_diff_density_rms 0.115 data_1 _database_code_depnum_ccdc_archive 'CCDC 801737' #TrackingRef '- 1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 Mn N3 O6, Cl O4' _chemical_formula_sum 'C25 H27 Cl Mn N3 O10' _chemical_formula_weight 619.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1430(2) _cell_length_b 16.3594(3) _cell_length_c 15.4001(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.4170(10) _cell_angle_gamma 90.00 _cell_volume 2663.54(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour Black _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.877 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45311 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.42 _reflns_number_total 6701 _reflns_number_gt 4769 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0935P)^2^+1.0785P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6689 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 0.10949(3) 0.07168(2) 0.90429(2) 0.03987(14) Uani 1 1 d . . . Cl1 Cl 0.26255(9) 0.00217(5) 0.55801(6) 0.0717(3) Uani 1 1 d . . . O3 O 0.11216(16) -0.04266(11) 0.91359(11) 0.0463(4) Uani 1 1 d . . . O5 O -0.0987(2) 0.07603(15) 0.89679(17) 0.0496(5) Uani 1 1 d . . . O2 O 0.15630(17) 0.08456(10) 1.03172(12) 0.0474(4) Uani 1 1 d . . . O1 O 0.2133(2) 0.06726(13) 1.20700(13) 0.0609(5) Uani 1 1 d . . . O6 O 0.31284(18) 0.08018(14) 0.91066(15) 0.0615(5) Uani 1 1 d . . . O4 O 0.1523(2) -0.19217(12) 0.96828(13) 0.0632(5) Uani 1 1 d . . . N2 N 0.06087(19) 0.06760(12) 0.76854(14) 0.0421(4) Uani 1 1 d . . . N3 N 0.4867(2) 0.06222(15) 0.86871(18) 0.0566(6) Uani 1 1 d . . . N1 N 0.10144(19) 0.19118(13) 0.88167(15) 0.0461(5) Uani 1 1 d . . . C21 C 0.1050(2) -0.09806(15) 0.84994(17) 0.0436(5) Uani 1 1 d . . . C15 C 0.0535(2) 0.00159(16) 0.72094(17) 0.0487(6) Uani 1 1 d . . . H15 H 0.0313 0.0076 0.6578 0.058 Uiso 1 1 calc R . . C14 C 0.0434(2) 0.14642(17) 0.72664(18) 0.0501(6) Uani 1 1 d . . . C16 C 0.0761(3) -0.07939(16) 0.75605(18) 0.0498(6) Uani 1 1 d . . . C20 C 0.1275(3) -0.18019(16) 0.87721(19) 0.0504(6) Uani 1 1 d . . . O10 O 0.2606(4) 0.0558(2) 0.6284(2) 0.1229(12) Uani 1 1 d . . . C7 C 0.1723(2) 0.15277(17) 1.07969(18) 0.0475(6) Uani 1 1 d . . . C2 C 0.2048(3) 0.14554(18) 1.17566(19) 0.0545(7) Uani 1 1 d . . . C6 C 0.1591(3) 0.23163(17) 1.0414(2) 0.0590(7) Uani 1 1 d . . . C9 C 0.0682(3) 0.21232(16) 0.78728(19) 0.0511(6) Uani 1 1 d . . . C23 C 0.3648(3) 0.05832(18) 0.8556(2) 0.0537(7) Uani 1 1 d . . . H23 H 0.3139 0.0373 0.8001 0.064 Uiso 1 1 calc R . . C13 C 0.0054(3) 0.1597(2) 0.6329(2) 0.0685(8) Uani 1 1 d . . . H13 H -0.0118 0.1157 0.5926 0.082 Uiso 1 1 calc R . . C8 C 0.1254(3) 0.24662(17) 0.9461(2) 0.0579(7) Uani 1 1 d . . . H8 H 0.1197 0.3010 0.9275 0.070 Uiso 1 1 calc R . . C17 C 0.0707(4) -0.1440(2) 0.6930(2) 0.0705(9) Uani 1 1 d . . . H17 H 0.0497 -0.1323 0.6309 0.085 Uiso 1 1 calc R . . C19 C 0.1242(3) -0.24071(18) 0.8140(2) 0.0690(8) Uani 1 1 d . . . H19 H 0.1412 -0.2946 0.8333 0.083 Uiso 1 1 calc R . . C10 C 0.0579(4) 0.2918(2) 0.7534(2) 0.0714(9) Uani 1 1 d . . . H10 H 0.0762 0.3361 0.7933 0.086 Uiso 1 1 calc R . . C18 C 0.0956(4) -0.2217(2) 0.7218(2) 0.0793(10) Uani 1 1 d . . . H18 H 0.0935 -0.2629 0.6797 0.095 Uiso 1 1 calc R . . C3 C 0.2277(3) 0.2146(2) 1.2298(2) 0.0747(9) Uani 1 1 d . . . H3 H 0.2514 0.2091 1.2930 0.090 Uiso 1 1 calc R . . C12 C -0.0066(4) 0.2386(2) 0.6002(3) 0.0867(12) Uani 1 1 d . . . H12 H -0.0329 0.2480 0.5374 0.104 Uiso 1 1 calc R . . C5 C 0.1818(4) 0.3013(2) 1.0998(3) 0.0813(11) Uani 1 1 d . . . H5 H 0.1730 0.3535 1.0746 0.098 Uiso 1 1 calc R . . C11 C 0.0204(4) 0.3042(2) 0.6603(3) 0.0918(12) Uani 1 1 d . . . H11 H 0.0131 0.3572 0.6375 0.110 Uiso 1 1 calc R . . C1 C 0.2589(4) 0.0549(2) 1.3039(2) 0.0730(9) Uani 1 1 d . . . H1A H 0.2606 -0.0026 1.3168 0.109 Uiso 1 1 calc R . . H1B H 0.2038 0.0820 1.3316 0.109 Uiso 1 1 calc R . . H1C H 0.3427 0.0769 1.3281 0.109 Uiso 1 1 calc R . . O7 O 0.3575(5) 0.0202(4) 0.5251(4) 0.210(3) Uani 1 1 d . . . C4 C 0.2161(4) 0.2920(2) 1.1916(3) 0.0882(12) Uani 1 1 d . . . H4 H 0.2320 0.3378 1.2293 0.106 Uiso 1 1 calc R . . C22 C 0.1812(5) -0.2736(2) 1.0011(3) 0.1027(15) Uani 1 1 d . . . H22A H 0.1966 -0.2747 1.0661 0.154 Uiso 1 1 calc R . . H22B H 0.2552 -0.2922 0.9878 0.154 Uiso 1 1 calc R . . H22C H 0.1112 -0.3088 0.9716 0.154 Uiso 1 1 calc R . . C24 C 0.5714(3) 0.0946(3) 0.9513(3) 0.0972(13) Uani 1 1 d . . . H24A H 0.6563 0.0925 0.9487 0.146 Uiso 1 1 calc R . . H24B H 0.5658 0.0629 1.0023 0.146 Uiso 1 1 calc R . . H24C H 0.5491 0.1503 0.9584 0.146 Uiso 1 1 calc R . . O9 O 0.2663(9) -0.0737(3) 0.5847(5) 0.278(4) Uani 1 1 d . . . C25 C 0.5405(4) 0.0363(4) 0.7990(3) 0.1138(17) Uani 1 1 d . . . H25A H 0.6306 0.0437 0.8209 0.171 Uiso 1 1 calc R . . H25B H 0.5052 0.0684 0.7447 0.171 Uiso 1 1 calc R . . H25C H 0.5214 -0.0204 0.7851 0.171 Uiso 1 1 calc R . . O8 O 0.1557(6) 0.0163(4) 0.4888(3) 0.243(3) Uani 1 1 d . . . H5A H -0.105(3) 0.088(2) 0.936(2) 0.055(12) Uiso 1 1 d . . . H5B H -0.128(4) 0.036(3) 0.881(3) 0.086(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0397(2) 0.0409(2) 0.0382(2) -0.00240(14) 0.01102(15) -0.00024(14) Cl1 0.1017(7) 0.0626(5) 0.0576(4) -0.0003(3) 0.0347(4) 0.0046(4) O3 0.0556(11) 0.0427(9) 0.0395(9) -0.0014(7) 0.0137(8) 0.0025(7) O5 0.0457(11) 0.0564(13) 0.0484(12) -0.0031(10) 0.0173(9) -0.0017(9) O2 0.0530(10) 0.0467(9) 0.0410(9) -0.0070(7) 0.0128(8) -0.0026(7) O1 0.0675(13) 0.0687(13) 0.0420(10) -0.0074(9) 0.0108(9) 0.0038(10) O6 0.0414(10) 0.0853(15) 0.0594(12) -0.0062(10) 0.0185(9) 0.0023(9) O4 0.0827(14) 0.0470(10) 0.0531(11) 0.0032(8) 0.0116(10) 0.0024(9) N2 0.0383(10) 0.0474(11) 0.0387(10) 0.0019(8) 0.0095(8) 0.0011(8) N3 0.0414(12) 0.0642(15) 0.0647(15) 0.0029(11) 0.0175(11) 0.0029(10) N1 0.0429(11) 0.0434(11) 0.0539(12) 0.0009(9) 0.0180(9) -0.0019(8) C21 0.0392(12) 0.0434(12) 0.0473(13) -0.0046(10) 0.0123(10) -0.0016(10) C15 0.0506(15) 0.0548(15) 0.0380(12) -0.0036(10) 0.0102(11) -0.0024(11) C14 0.0465(14) 0.0524(14) 0.0513(14) 0.0077(11) 0.0154(12) 0.0033(11) C16 0.0528(15) 0.0511(14) 0.0436(13) -0.0066(11) 0.0127(11) -0.0039(11) C20 0.0506(15) 0.0461(13) 0.0507(14) -0.0035(11) 0.0107(12) -0.0029(11) O10 0.137(3) 0.145(3) 0.094(2) -0.041(2) 0.048(2) 0.001(2) C7 0.0391(13) 0.0551(14) 0.0481(13) -0.0130(11) 0.0135(11) -0.0087(10) C2 0.0492(15) 0.0628(17) 0.0506(14) -0.0133(12) 0.0143(12) -0.0040(12) C6 0.0663(18) 0.0473(15) 0.0647(17) -0.0137(13) 0.0224(14) -0.0138(13) C9 0.0473(14) 0.0491(14) 0.0596(16) 0.0064(12) 0.0210(12) 0.0031(11) C23 0.0399(13) 0.0637(17) 0.0553(16) -0.0008(13) 0.0118(12) 0.0002(11) C13 0.081(2) 0.071(2) 0.0510(16) 0.0100(14) 0.0167(15) 0.0073(16) C8 0.0662(18) 0.0418(14) 0.0681(18) -0.0046(13) 0.0246(14) -0.0118(12) C17 0.100(3) 0.0609(18) 0.0490(16) -0.0104(14) 0.0207(16) -0.0051(17) C19 0.087(2) 0.0436(15) 0.0714(19) -0.0079(13) 0.0185(17) 0.0009(14) C10 0.091(2) 0.0528(17) 0.075(2) 0.0110(15) 0.0329(18) 0.0048(16) C18 0.120(3) 0.0531(18) 0.0618(19) -0.0172(15) 0.025(2) -0.0026(18) C3 0.087(2) 0.083(2) 0.0517(17) -0.0254(16) 0.0192(16) -0.0149(19) C12 0.118(3) 0.078(2) 0.061(2) 0.0242(18) 0.024(2) 0.015(2) C5 0.111(3) 0.0526(18) 0.081(2) -0.0203(16) 0.031(2) -0.0230(18) C11 0.132(4) 0.067(2) 0.085(3) 0.031(2) 0.046(3) 0.022(2) C1 0.083(2) 0.093(2) 0.0414(15) -0.0052(15) 0.0174(15) 0.0072(19) O7 0.203(5) 0.270(7) 0.224(6) -0.075(5) 0.162(5) -0.053(4) C4 0.119(3) 0.068(2) 0.080(2) -0.0373(19) 0.035(2) -0.026(2) C22 0.168(4) 0.0543(19) 0.070(2) 0.0147(17) 0.015(3) 0.009(2) C24 0.051(2) 0.131(4) 0.097(3) -0.021(3) 0.0046(19) -0.009(2) O9 0.541(13) 0.091(3) 0.303(8) 0.080(4) 0.275(9) 0.105(5) C25 0.068(2) 0.177(5) 0.110(3) -0.022(3) 0.047(2) 0.004(3) O8 0.212(6) 0.301(8) 0.130(4) -0.050(4) -0.067(4) 0.034(5) _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 1.8754(19) . ? Mn1 O2 1.8763(18) . ? Mn1 N1 1.983(2) . ? Mn1 N2 1.988(2) . ? Mn1 O6 2.2413(19) . ? Mn1 O5 2.287(2) . ? Cl1 O9 1.304(4) . ? Cl1 O7 1.343(4) . ? Cl1 O8 1.344(5) . ? Cl1 O10 1.400(3) . ? O3 C21 1.319(3) . ? O2 C7 1.319(3) . ? O1 C2 1.361(4) . ? O1 C1 1.430(3) . ? O6 C23 1.222(3) . ? O4 C20 1.355(3) . ? O4 C22 1.425(4) . ? N2 C15 1.293(3) . ? N2 C14 1.427(3) . ? N3 C23 1.310(4) . ? N3 C24 1.425(4) . ? N3 C25 1.449(5) . ? N1 C8 1.308(4) . ? N1 C9 1.425(4) . ? C21 C20 1.406(4) . ? C21 C16 1.412(4) . ? C15 C16 1.423(4) . ? C14 C13 1.387(4) . ? C14 C9 1.396(4) . ? C16 C17 1.424(4) . ? C20 C19 1.381(4) . ? C7 C6 1.407(4) . ? C7 C2 1.411(4) . ? C2 C3 1.379(4) . ? C6 C8 1.418(4) . ? C6 C5 1.424(4) . ? C9 C10 1.393(4) . ? C13 C12 1.377(5) . ? C17 C18 1.347(5) . ? C19 C18 1.388(5) . ? C10 C11 1.375(5) . ? C3 C4 1.385(5) . ? C12 C11 1.388(6) . ? C5 C4 1.352(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 O3 Mn1 O2 92.28(7) . . ? O3 Mn1 N1 174.55(8) . . ? O2 Mn1 N1 93.17(8) . . ? O3 Mn1 N2 92.25(8) . . ? O2 Mn1 N2 175.45(8) . . ? N1 Mn1 N2 82.30(9) . . ? O3 Mn1 O6 93.85(8) . . ? O2 Mn1 O6 90.24(8) . . ? N1 Mn1 O6 86.30(8) . . ? N2 Mn1 O6 89.08(8) . . ? O3 Mn1 O5 91.51(8) . . ? O2 Mn1 O5 89.53(9) . . ? N1 Mn1 O5 88.37(8) . . ? N2 Mn1 O5 90.74(9) . . ? O6 Mn1 O5 174.65(9) . . ? O9 Cl1 O7 112.1(4) . . ? O9 Cl1 O8 110.3(5) . . ? O7 Cl1 O8 105.6(4) . . ? O9 Cl1 O10 111.1(3) . . ? O7 Cl1 O10 111.2(3) . . ? O8 Cl1 O10 106.2(3) . . ? C21 O3 Mn1 129.27(16) . . ? C7 O2 Mn1 128.65(17) . . ? C2 O1 C1 117.7(2) . . ? C23 O6 Mn1 130.23(19) . . ? C20 O4 C22 116.9(2) . . ? C15 N2 C14 121.5(2) . . ? C15 N2 Mn1 124.85(18) . . ? C14 N2 Mn1 113.45(16) . . ? C23 N3 C24 121.2(3) . . ? C23 N3 C25 121.5(3) . . ? C24 N3 C25 117.3(3) . . ? C8 N1 C9 122.0(2) . . ? C8 N1 Mn1 124.3(2) . . ? C9 N1 Mn1 113.66(17) . . ? O3 C21 C20 118.1(2) . . ? O3 C21 C16 123.6(2) . . ? C20 C21 C16 118.3(2) . . ? N2 C15 C16 126.2(2) . . ? C13 C14 C9 120.4(3) . . ? C13 C14 N2 124.4(3) . . ? C9 C14 N2 115.2(2) . . ? C21 C16 C15 123.1(2) . . ? C21 C16 C17 119.0(3) . . ? C15 C16 C17 117.9(3) . . ? O4 C20 C19 125.3(3) . . ? O4 C20 C21 113.9(2) . . ? C19 C20 C21 120.8(3) . . ? O2 C7 C6 124.3(2) . . ? O2 C7 C2 117.4(3) . . ? C6 C7 C2 118.3(2) . . ? O1 C2 C3 125.3(3) . . ? O1 C2 C7 114.6(2) . . ? C3 C2 C7 120.1(3) . . ? C7 C6 C8 123.4(2) . . ? C7 C6 C5 119.7(3) . . ? C8 C6 C5 116.8(3) . . ? C10 C9 C14 119.7(3) . . ? C10 C9 N1 124.9(3) . . ? C14 C9 N1 115.3(2) . . ? O6 C23 N3 125.1(3) . . ? C12 C13 C14 119.3(3) . . ? N1 C8 C6 126.1(3) . . ? C18 C17 C16 121.1(3) . . ? C20 C19 C18 120.5(3) . . ? C11 C10 C9 119.3(3) . . ? C17 C18 C19 120.3(3) . . ? C2 C3 C4 121.2(3) . . ? C13 C12 C11 120.4(3) . . ? C4 C5 C6 120.3(3) . . ? C10 C11 C12 120.8(3) . . ? C5 C4 C3 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.810 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.065