# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1890 data_global _publ_contact_author ; Dra. Miren Karmele Urtiaga Dpto. de Mineralog\'ia y Petrolog\'ia Universidad del Pa\'is Vasco Apartado 644 48080 Bilbao Spain ; _publ_contact_author_phone '34 4 6012555' _publ_contact_author_fax '34 4 4648500' _publ_contact_author_email nppurgrm@lg.ehu.es _publ_requested_journal 'J.Chem.Soc.Dalton Trans.' loop_ _publ_author_name _publ_author_address 'Barandika, M.G.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Hernandez, M.L.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Urtiaga, M.K.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Cortes, R.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Lezama, L.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Ciencia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Arriortua, M.I.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Rojo, T.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Ciencia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; data_mnmar _audit_creation_method SHELXL _chemical_formula_sum 'C26 H24 Mn N6 O2 S2' _chemical_formula_weight 571.57 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' '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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.432(4) _cell_length_b 12.851(5) _cell_length_c 21.164(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.86(2) _cell_angle_gamma 90.00 _cell_volume 2817.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 0.650 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w-2\q' _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_reflns_number 8593 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 29.97 _reflns_number_total 8184 _reflns_number_observed 5892 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4' _computing_cell_refinement 'Enraf-Nonius CAD-4' _computing_data_reduction 'Xtal 3.2 (Hall, Flack & Stewart, 1992)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 28 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.3049P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_number_reflns 8156 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_obs 0.0429 _refine_ls_wR_factor_all 0.1403 _refine_ls_wR_factor_obs 0.1144 _refine_ls_goodness_of_fit_all 1.087 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_restrained_S_all 1.166 _refine_ls_restrained_S_obs 1.126 _refine_ls_shift/esd_max 1.186 _refine_ls_shift/esd_mean 0.161 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.10474(2) 0.06797(2) 0.202246(11) 0.04182(9) Uani 1 d . . O1 O -0.02897(13) -0.00693(13) 0.26222(7) 0.0572(4) Uani 1 d . . O2 O -0.0061(2) 0.20570(14) 0.22647(8) 0.0660(4) Uani 1 d . . N5 N 0.2115(2) 0.1760(2) 0.15094(9) 0.0635(4) Uani 1 d . . C25 C 0.2528(2) 0.2458(2) 0.12620(8) 0.0494(4) Uani 1 d . . S1 S 0.30936(7) 0.34439(7) 0.09056(4) 0.0931(3) Uani 1 d . . N6 N 0.1953(2) -0.08130(15) 0.19089(9) 0.0595(4) Uani 1 d . . C26 C 0.1922(2) -0.1678(2) 0.17677(9) 0.0481(4) Uani 1 d . . S2 S 0.18594(8) -0.29055(5) 0.15788(4) 0.0899(2) Uani 1 d . . N1 N 0.24424(14) 0.09452(12) 0.29202(7) 0.0450(3) Uani 1 d . . C1 C 0.2090(2) 0.12530(15) 0.34768(9) 0.0469(4) Uani 1 d . . C2 C 0.2946(2) 0.13644(15) 0.40201(9) 0.0473(4) Uani 1 d . . C3 C 0.4248(2) 0.11612(14) 0.40007(8) 0.0438(4) Uani 1 d . . C4 C 0.4621(2) 0.0851(2) 0.34188(9) 0.0512(4) Uani 1 d . . C5 C 0.3701(2) 0.0751(2) 0.29009(9) 0.0513(4) Uani 1 d . . C6 C 0.5141(2) 0.1277(2) 0.45866(9) 0.0501(4) Uani 1 d . . C7 C 0.6389(2) 0.1076(2) 0.46488(8) 0.0481(4) Uani 1 d . . C8 C 0.7742(2) 0.1446(2) 0.63622(9) 0.0523(4) Uani 1 d . . C9 C 0.6849(2) 0.1403(2) 0.58283(9) 0.0485(4) Uani 1 d . . C10 C 0.7262(2) 0.11789(14) 0.52372(8) 0.0448(4) Uani 1 d . . C11 C 0.8573(2) 0.1023(2) 0.52307(10) 0.0563(5) Uani 1 d . . C12 C 0.9393(2) 0.1093(2) 0.57879(11) 0.0611(5) Uani 1 d . . N2 N 0.9001(2) 0.12956(15) 0.63504(8) 0.0569(4) Uani 1 d . . N3 N -0.0355(2) 0.03334(14) 0.11334(7) 0.0506(4) Uani 1 d . . C13 C -0.0643(2) 0.1054(2) 0.06833(10) 0.0576(5) Uani 1 d . . C14 C -0.1584(2) 0.0927(2) 0.01752(9) 0.0566(5) Uani 1 d . . C15 C -0.2289(2) 0.00027(15) 0.01139(8) 0.0468(4) Uani 1 d . . C16 C -0.1950(2) -0.0757(2) 0.05663(10) 0.0558(5) Uani 1 d . . C17 C -0.1003(2) -0.0566(2) 0.10637(10) 0.0560(5) Uani 1 d . . C18 C -0.3359(2) -0.0181(2) -0.03872(8) 0.0506(4) Uani 1 d . . C19 C -0.3895(2) 0.0527(2) -0.07863(9) 0.0488(4) Uani 1 d . . C20 C -0.6451(2) 0.1022(2) -0.21349(11) 0.0625(5) Uani 1 d . . C21 C -0.5402(2) 0.1168(2) -0.16803(10) 0.0553(5) Uani 1 d . . C22 C -0.4972(2) 0.0351(2) -0.12840(8) 0.0461(4) Uani 1 d . . C23 C -0.5608(2) -0.0593(2) -0.13847(11) 0.0585(5) Uani 1 d . . C24 C -0.6647(2) -0.0666(2) -0.18490(12) 0.0652(6) Uani 1 d . . N4 N -0.7088(2) 0.0125(2) -0.22167(9) 0.0627(5) Uani 1 d . . H1 H 0.1183(25) 0.1383(19) 0.3471(12) 0.069(2) Uiso 1 d . . H2 H 0.2643(24) 0.1580(20) 0.4386(13) 0.069(2) Uiso 1 d . . H4 H 0.5470(26) 0.0693(19) 0.3364(12) 0.069(2) Uiso 1 d . . H5 H 0.3927(24) 0.0523(20) 0.2515(13) 0.069(2) Uiso 1 d . . H6 H 0.4796(24) 0.1548(20) 0.4965(13) 0.069(2) Uiso 1 d . . H7 H 0.6750(25) 0.0826(19) 0.4265(13) 0.069(2) Uiso 1 d . . H8 H 0.7454(24) 0.1566(20) 0.6772(12) 0.069(2) Uiso 1 d . . H9 H 0.5984(26) 0.1527(20) 0.5892(12) 0.069(2) Uiso 1 d . . H11 H 0.8933(24) 0.0857(19) 0.4822(13) 0.069(2) Uiso 1 d . . H12 H 1.0343(25) 0.0971(20) 0.5759(12) 0.069(2) Uiso 1 d . . H13 H -0.0165(24) 0.1761(20) 0.0731(12) 0.069(2) Uiso 1 d . . H14 H -0.1704(23) 0.1452(20) -0.0136(13) 0.069(2) Uiso 1 d . . H16 H -0.2395(25) -0.1371(21) 0.0576(12) 0.069(2) Uiso 1 d . . H17 H -0.0811(24) -0.1117(19) 0.1374(13) 0.069(2) Uiso 1 d . . H18 H -0.3789(25) -0.0883(21) -0.0382(12) 0.069(2) Uiso 1 d . . H19 H -0.3557(26) 0.1237(20) -0.0751(13) 0.069(2) Uiso 1 d . . H20 H -0.6749(24) 0.1571(21) -0.2391(13) 0.069(2) Uiso 1 d . . H21 H -0.4968(24) 0.1841(20) -0.1632(12) 0.069(2) Uiso 1 d . . H23 H -0.5385(25) -0.1141(21) -0.1158(12) 0.069(2) Uiso 1 d . . H24 H -0.7132(25) -0.1282(20) -0.1892(12) 0.069(2) Uiso 1 d . . H1W H -0.1030(28) -0.0081(20) 0.2578(13) 0.069(2) Uiso 1 d . . H2W H -0.0045(27) -0.0480(22) 0.2876(13) 0.069(2) Uiso 1 d . . H3W H -0.0198(26) 0.2572(22) 0.2083(13) 0.069(2) Uiso 1 d . . H4W H -0.0555(26) 0.2052(22) 0.2494(14) 0.069(2) Uiso 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 0.04004(14) 0.0483(2) 0.03447(13) 0.00190(10) -0.00627(9) -0.00207(10) O1 0.0368(6) 0.0761(10) 0.0552(8) 0.0222(7) -0.0082(6) -0.0020(6) O2 0.0789(11) 0.0657(9) 0.0550(8) 0.0155(7) 0.0144(7) 0.0245(8) N5 0.0668(11) 0.0696(11) 0.0540(9) 0.0059(8) 0.0065(8) -0.0128(9) C25 0.0416(8) 0.0661(11) 0.0407(8) 0.0015(8) 0.0058(7) -0.0050(8) S1 0.0738(4) 0.1028(5) 0.1070(6) 0.0407(5) 0.0281(4) -0.0167(4) N6 0.0581(10) 0.0620(11) 0.0568(10) -0.0031(8) 0.0003(8) 0.0055(8) C26 0.0447(9) 0.0580(11) 0.0425(9) 0.0033(8) 0.0091(7) 0.0070(8) S2 0.1084(6) 0.0594(4) 0.1108(6) -0.0169(3) 0.0501(5) 0.0019(3) N1 0.0379(7) 0.0563(8) 0.0383(7) -0.0009(6) -0.0061(5) -0.0028(6) C1 0.0397(8) 0.0542(10) 0.0441(9) -0.0029(7) -0.0058(7) 0.0021(7) C2 0.0467(9) 0.0536(10) 0.0394(8) -0.0060(7) -0.0032(7) 0.0008(7) C3 0.0409(8) 0.0479(9) 0.0395(8) 0.0000(7) -0.0076(6) -0.0062(7) C4 0.0340(8) 0.0734(12) 0.0444(9) -0.0007(8) -0.0025(7) -0.0043(8) C5 0.0414(9) 0.0722(13) 0.0387(8) -0.0044(8) -0.0019(7) -0.0041(8) C6 0.0455(9) 0.0641(11) 0.0380(8) -0.0050(8) -0.0059(7) -0.0033(8) C7 0.0445(9) 0.0605(11) 0.0367(8) 0.0009(7) -0.0055(7) -0.0064(8) C8 0.0521(10) 0.0618(11) 0.0398(8) 0.0013(8) -0.0077(7) -0.0068(8) C9 0.0421(9) 0.0580(10) 0.0429(9) 0.0012(7) -0.0057(7) -0.0033(8) C10 0.0425(8) 0.0492(9) 0.0395(8) 0.0049(7) -0.0078(7) -0.0078(7) C11 0.0462(10) 0.0773(13) 0.0436(9) 0.0014(9) -0.0019(8) -0.0050(9) C12 0.0406(9) 0.0808(14) 0.0583(11) 0.0063(10) -0.0093(8) -0.0059(9) N2 0.0479(8) 0.0754(11) 0.0431(8) 0.0079(7) -0.0129(6) -0.0109(8) N3 0.0531(8) 0.0568(9) 0.0383(7) 0.0015(6) -0.0099(6) -0.0033(7) C13 0.0634(12) 0.0567(11) 0.0473(10) 0.0032(8) -0.0156(9) -0.0106(9) C14 0.0644(12) 0.0590(11) 0.0418(9) 0.0087(8) -0.0126(8) -0.0072(9) C15 0.0453(9) 0.0570(10) 0.0361(8) -0.0054(7) -0.0039(6) -0.0007(7) C16 0.0576(11) 0.0530(11) 0.0529(10) 0.0003(8) -0.0096(9) -0.0077(9) C17 0.0610(11) 0.0566(11) 0.0459(9) 0.0064(8) -0.0127(8) -0.0041(9) C18 0.0503(9) 0.0584(11) 0.0404(8) -0.0047(8) -0.0054(7) -0.0039(8) C19 0.0442(9) 0.0603(11) 0.0401(8) -0.0041(8) -0.0026(7) -0.0046(8) C20 0.0544(11) 0.0683(13) 0.0605(12) 0.0114(10) -0.0109(9) 0.0021(10) C21 0.0487(10) 0.0584(11) 0.0560(11) 0.0026(9) -0.0056(8) -0.0050(9) C22 0.0356(7) 0.0607(10) 0.0405(8) -0.0019(7) -0.0016(6) -0.0004(7) C23 0.0516(10) 0.0597(12) 0.0595(11) 0.0070(9) -0.0133(9) -0.0059(9) C24 0.0535(11) 0.0657(13) 0.0702(13) 0.0032(10) -0.0180(10) -0.0135(10) N4 0.0464(8) 0.0794(12) 0.0573(10) 0.0047(9) -0.0139(7) -0.0059(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N5 2.153(2) . ? Mn1 N6 2.164(2) . ? Mn1 O2 2.208(2) . ? Mn1 O1 2.215(2) . ? Mn1 N1 2.277(2) . ? Mn1 N3 2.285(2) . ? N5 C25 1.148(3) . ? C25 S1 1.621(2) . ? N6 C26 1.151(3) . ? C26 S2 1.627(2) . ? N1 C1 1.335(2) . ? N1 C5 1.342(2) . ? C1 C2 1.376(2) . ? C2 C3 1.389(3) . ? C3 C4 1.393(3) . ? C3 C6 1.467(2) . ? C4 C5 1.374(2) . ? C6 C7 1.318(3) . ? C7 C10 1.458(2) . ? C8 N2 1.332(3) . ? C8 C9 1.377(2) . ? C9 C10 1.401(3) . ? C10 C11 1.384(3) . ? C11 C12 1.375(3) . ? C12 N2 1.330(3) . ? N3 C13 1.336(3) . ? N3 C17 1.339(3) . ? C13 C14 1.376(3) . ? C14 C15 1.395(3) . ? C15 C16 1.383(3) . ? C15 C18 1.464(2) . ? C16 C17 1.377(3) . ? C18 C19 1.320(3) . ? C19 C22 1.463(2) . ? C20 N4 1.332(3) . ? C20 C21 1.381(3) . ? C21 C22 1.385(3) . ? C22 C23 1.386(3) . ? C23 C24 1.377(3) . ? C24 N4 1.329(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 N5 Mn1 N6 104.85(8) . . ? N5 Mn1 O2 85.25(8) . . ? N6 Mn1 O2 169.74(7) . . ? N5 Mn1 O1 165.54(7) . . ? N6 Mn1 O1 89.52(7) . . ? O2 Mn1 O1 80.33(7) . . ? N5 Mn1 N1 90.38(7) . . ? N6 Mn1 N1 88.94(6) . . ? O2 Mn1 N1 89.22(6) . . ? O1 Mn1 N1 88.31(6) . . ? N5 Mn1 N3 91.67(7) . . ? N6 Mn1 N3 88.91(7) . . ? O2 Mn1 N3 92.62(7) . . ? O1 Mn1 N3 90.12(6) . . ? N1 Mn1 N3 177.35(6) . . ? C25 N5 Mn1 168.1(2) . . ? N5 C25 S1 179.3(2) . . ? C26 N6 Mn1 152.4(2) . . ? N6 C26 S2 178.9(2) . . ? C1 N1 C5 117.09(15) . . ? C1 N1 Mn1 124.39(12) . . ? C5 N1 Mn1 118.49(12) . . ? N1 C1 C2 123.3(2) . . ? C1 C2 C3 119.7(2) . . ? C2 C3 C4 117.2(2) . . ? C2 C3 C6 118.7(2) . . ? C4 C3 C6 124.1(2) . . ? C5 C4 C3 119.3(2) . . ? N1 C5 C4 123.5(2) . . ? C7 C6 C3 125.8(2) . . ? C6 C7 C10 125.2(2) . . ? N2 C8 C9 123.4(2) . . ? C8 C9 C10 119.5(2) . . ? C11 C10 C9 116.6(2) . . ? C11 C10 C7 119.7(2) . . ? C9 C10 C7 123.7(2) . . ? C12 C11 C10 119.8(2) . . ? N2 C12 C11 123.7(2) . . ? C12 N2 C8 117.0(2) . . ? C13 N3 C17 116.9(2) . . ? C13 N3 Mn1 121.29(13) . . ? C17 N3 Mn1 121.61(12) . . ? N3 C13 C14 123.6(2) . . ? C13 C14 C15 119.5(2) . . ? C16 C15 C14 116.6(2) . . ? C16 C15 C18 119.8(2) . . ? C14 C15 C18 123.6(2) . . ? C17 C16 C15 120.3(2) . . ? N3 C17 C16 123.0(2) . . ? C19 C18 C15 125.5(2) . . ? C18 C19 C22 125.8(2) . . ? N4 C20 C21 123.4(2) . . ? C20 C21 C22 119.4(2) . . ? C21 C22 C23 117.1(2) . . ? C21 C22 C19 118.9(2) . . ? C23 C22 C19 124.0(2) . . ? C24 C23 C22 119.4(2) . . ? N4 C24 C23 123.6(2) . . ? C24 N4 C20 117.0(2) . . ? _refine_diff_density_max 0.498 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.056 data_mnncs _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_formula_sum 'C21 H18 Mn N5 O S2' _chemical_formula_weight 475.46 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' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.807(2) _cell_length_b 11.130(2) _cell_length_c 12.9720(10) _cell_angle_alpha 114.500(10) _cell_angle_beta 92.070(10) _cell_angle_gamma 93.870(10) _cell_volume 1151.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.371 _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.776 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w-2\q' _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6709 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 29.97 _reflns_number_total 6709 _reflns_number_observed 4341 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4' _computing_cell_refinement 'Enraf-Nonius CAD-4' _computing_data_reduction 'Xtal 3.2 (Hall, Flack & Stewart, 1992)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.2478P)^2^+1.6471P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6709 _refine_ls_number_parameters 305 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_obs 0.0481 _refine_ls_wR_factor_all 0.2361 _refine_ls_wR_factor_obs 0.1594 _refine_ls_goodness_of_fit_all 0.663 _refine_ls_goodness_of_fit_obs 0.548 _refine_ls_restrained_S_all 0.663 _refine_ls_restrained_S_obs 0.548 _refine_ls_shift/esd_max -1.468 _refine_ls_shift/esd_mean 0.081 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn -0.06913(5) 0.42880(4) 0.18844(4) 0.0354(2) Uani 1 d . . N4 N -0.1882(4) 0.2829(3) 0.2329(3) 0.0533(8) Uani 1 d . . C19 C -0.2779(5) 0.2333(4) 0.2685(3) 0.0517(8) Uani 1 d . . S1A S -0.4201(12) 0.1812(13) 0.3208(8) 0.091(3) Uani 0.50 d P . S1B S -0.3872(12) 0.1510(13) 0.3181(10) 0.099(3) Uani 0.50 d P . N5 N 0.0395(4) 0.5795(3) 0.1418(3) 0.0499(7) Uani 1 d . . C20 C 0.1021(4) 0.6362(3) 0.0960(3) 0.0375(6) Uani 1 d . . S2 S 0.19327(12) 0.71391(10) 0.03046(8) 0.0499(2) Uani 1 d . . N1 N 0.1347(3) 0.3075(3) 0.1370(3) 0.0419(6) Uani 1 d . . C1 C 0.1156(4) 0.1757(4) 0.1062(4) 0.0514(9) Uani 1 d . . H1 H 0.0201(4) 0.1388(4) 0.1120(4) 0.096(5) Uiso 1 calc R . C2 C 0.2293(4) 0.0930(3) 0.0668(4) 0.0517(9) Uani 1 d . . H2 H 0.2098(4) 0.0025(3) 0.0462(4) 0.096(5) Uiso 1 calc R . C3 C 0.3741(4) 0.1450(3) 0.0577(3) 0.0400(6) Uani 1 d . . C4 C 0.3947(4) 0.2811(3) 0.0918(4) 0.0499(8) Uani 1 d . . H4 H 0.4896(4) 0.3211(3) 0.0888(4) 0.096(5) Uiso 1 calc R . C5 C 0.2731(4) 0.3574(3) 0.1302(4) 0.0506(8) Uani 1 d . . H5 H 0.2895(4) 0.4484(3) 0.1523(4) 0.096(5) Uiso 1 calc R . C6 C 0.5024(4) 0.0645(3) 0.0176(3) 0.0442(7) Uani 1 d D . H6 H 0.6071(31) 0.1113(55) 0.0240(53) 0.096(5) Uiso 1 d D . N2 N -0.2787(3) 0.5465(3) 0.2303(3) 0.0464(6) Uani 1 d . . C7 C -0.3235(5) 0.6129(4) 0.1702(4) 0.0627(11) Uani 1 d . . H7 H -0.2783(5) 0.5987(4) 0.1029(4) 0.096(5) Uiso 1 calc R . C8 C -0.4333(6) 0.7009(5) 0.2040(6) 0.089(2) Uani 1 d . . H8 H -0.4627(6) 0.7420(5) 0.1579(6) 0.096(5) Uiso 1 calc R . C9 C -0.5001(5) 0.7292(5) 0.3043(6) 0.088(2) Uani 1 d . . C10 C -0.4554(5) 0.6584(5) 0.3652(5) 0.077(2) Uani 1 d . . H10 H -0.4991(5) 0.6715(5) 0.4329(5) 0.096(5) Uiso 1 calc R . C11 C -0.3469(4) 0.5690(4) 0.3265(4) 0.0554(9) Uani 1 d . . H11 H -0.3201(4) 0.5226(4) 0.3688(4) 0.096(5) Uiso 1 calc R . C12A C -0.5995(8) 0.8408(7) 0.3163(6) 0.0441(14) Uani 0.50 d P . C13A C -0.6618(8) 0.8933(7) 0.4173(7) 0.0451(15) Uani 0.50 d P . C13B C -0.6604(9) 0.9037(8) 0.3438(7) 0.049(2) Uani 0.50 d P . C12B C -0.6118(9) 0.8212(9) 0.3839(8) 0.052(2) Uani 0.50 d P . C14 C -0.9094(6) 1.1694(5) 0.4145(5) 0.0705(12) Uani 1 d . . H14 H -0.9485(6) 1.2089(5) 0.3698(5) 0.096(5) Uiso 1 calc R . C15 C -0.8184(7) 1.0684(5) 0.3661(6) 0.089(2) Uani 1 d . . H15 H -0.7957(7) 1.0420(5) 0.2908(6) 0.096(5) Uiso 1 calc R . C16 C -0.7600(5) 1.0052(4) 0.4293(6) 0.088(2) Uani 1 d . . C17 C -0.7996(5) 1.0504(4) 0.5399(6) 0.080(2) Uani 1 d . . H17 H -0.7646(5) 1.0110(4) 0.5859(6) 0.096(5) Uiso 1 calc R . C18 C -0.8904(5) 1.1529(4) 0.5829(4) 0.0593(10) Uani 1 d . . H18 H -0.9150(5) 1.1810(4) 0.6579(4) 0.096(5) Uiso 1 calc R . N3 N -0.9449(4) 1.2144(3) 0.5228(3) 0.0582(8) Uani 1 d . . O1 O 0.0354(4) 0.5426(3) 0.3605(2) 0.0564(7) Uani 1 d D . H100 H 0.0046(70) 0.6351(25) 0.4018(45) 0.096(5) Uiso 1 d D . C21 C 0.1610(6) 0.5211(5) 0.4179(4) 0.0664(11) Uani 1 d . . H211 H 0.1765(6) 0.5910(5) 0.4930(4) 0.096(5) Uiso 1 calc R . H212 H 0.2504(6) 0.5198(5) 0.3773(4) 0.096(5) Uiso 1 calc R . H213 H 0.1424(6) 0.4376(5) 0.4226(4) 0.096(5) Uiso 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 0.0354(2) 0.0365(3) 0.0362(3) 0.0162(2) 0.0054(2) 0.0079(2) N4 0.053(2) 0.055(2) 0.063(2) 0.035(2) 0.0127(15) 0.0056(14) C19 0.056(2) 0.061(2) 0.045(2) 0.030(2) -0.001(2) -0.004(2) S1A 0.075(3) 0.151(7) 0.057(2) 0.061(3) -0.003(2) -0.038(3) S1B 0.096(6) 0.138(6) 0.088(3) 0.085(4) -0.028(3) -0.056(4) N5 0.060(2) 0.046(2) 0.0430(15) 0.0191(12) 0.0024(13) -0.0049(13) C20 0.0409(15) 0.0332(13) 0.0339(14) 0.0098(11) -0.0007(11) 0.0034(11) S2 0.0558(5) 0.0508(5) 0.0422(4) 0.0218(4) -0.0049(4) -0.0141(4) N1 0.0378(13) 0.0355(12) 0.048(2) 0.0123(11) 0.0050(11) 0.0084(10) C1 0.038(2) 0.040(2) 0.071(2) 0.018(2) 0.009(2) 0.0059(13) C2 0.040(2) 0.0331(14) 0.075(3) 0.015(2) 0.009(2) 0.0059(12) C3 0.0354(14) 0.0385(14) 0.042(2) 0.0117(12) 0.0028(12) 0.0068(11) C4 0.039(2) 0.037(2) 0.066(2) 0.014(2) 0.009(2) 0.0024(12) C5 0.042(2) 0.0345(15) 0.067(2) 0.0127(15) 0.008(2) 0.0050(13) C6 0.0316(14) 0.039(2) 0.055(2) 0.0122(14) 0.0052(13) 0.0066(11) N2 0.0409(14) 0.0456(15) 0.045(2) 0.0110(12) 0.0000(12) 0.0094(11) C7 0.065(2) 0.060(2) 0.060(2) 0.022(2) -0.012(2) 0.021(2) C8 0.079(3) 0.065(3) 0.103(4) 0.016(3) -0.038(3) 0.033(3) C9 0.039(2) 0.051(2) 0.122(5) -0.016(3) -0.013(2) 0.016(2) C10 0.041(2) 0.063(3) 0.088(3) -0.009(2) 0.018(2) 0.001(2) C11 0.044(2) 0.053(2) 0.057(2) 0.011(2) 0.011(2) 0.003(2) C12A 0.044(3) 0.041(3) 0.041(3) 0.010(3) -0.003(3) 0.016(3) C13A 0.042(3) 0.038(3) 0.049(4) 0.011(3) 0.003(3) 0.014(3) C13B 0.044(4) 0.046(4) 0.056(4) 0.020(3) -0.002(3) 0.009(3) C12B 0.047(4) 0.055(4) 0.059(5) 0.027(4) -0.003(3) 0.013(3) C14 0.077(3) 0.055(2) 0.071(3) 0.017(2) 0.004(2) 0.012(2) C15 0.079(3) 0.060(3) 0.096(4) 0.000(3) 0.024(3) 0.011(3) C16 0.044(2) 0.034(2) 0.145(5) -0.004(3) 0.004(3) 0.009(2) C17 0.050(2) 0.041(2) 0.134(5) 0.027(3) -0.030(3) -0.001(2) C18 0.053(2) 0.045(2) 0.068(3) 0.014(2) -0.009(2) -0.004(2) N3 0.054(2) 0.0396(15) 0.069(2) 0.0111(15) -0.002(2) 0.0111(13) O1 0.077(2) 0.0475(13) 0.0375(12) 0.0098(11) -0.0107(12) 0.0193(13) C21 0.064(3) 0.074(3) 0.055(2) 0.020(2) -0.008(2) 0.015(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 N4 2.159(3) . ? Mn1 N5 2.182(3) . ? Mn1 O1 2.186(3) . ? Mn1 N1 2.271(3) . ? Mn1 N2 2.286(3) . ? Mn1 S2 2.7535(11) 2_565 ? N4 C19 1.149(5) . ? C19 S1A 1.630(10) . ? C19 S1B 1.610(10) . ? N5 C20 1.158(4) . ? C20 S2 1.637(3) . ? S2 Mn1 2.7536(11) 2_565 ? N1 C5 1.326(4) . ? N1 C1 1.347(4) . ? C1 C2 1.373(5) . ? C2 C3 1.394(5) . ? C3 C4 1.388(5) . ? C3 C6 1.463(4) . ? C4 C5 1.388(5) . ? C6 C6 1.312(7) 2_655 ? N2 C7 1.343(5) . ? N2 C11 1.340(5) . ? C7 C8 1.374(6) . ? C8 C9 1.371(10) . ? C9 C10 1.393(9) . ? C9 C12A 1.526(8) . ? C9 C12B 1.554(10) . ? C10 C11 1.380(6) . ? C12A C13B 0.873(9) . ? C12A C12B 0.996(11) . ? C12A C13A 1.349(10) . ? C13A C13B 1.006(11) . ? C13A C12B 0.894(10) . ? C13A C16 1.522(8) . ? C13B C12B 1.315(10) . ? C13B C16 1.562(10) . ? C14 N3 1.338(6) . ? C14 C15 1.368(7) . ? C15 C16 1.388(10) . ? C16 C17 1.377(9) . ? C17 C18 1.371(6) . ? C18 N3 1.329(6) . ? O1 C21 1.400(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 N4 Mn1 N5 176.97(13) . . ? N4 Mn1 O1 93.38(13) . . ? N5 Mn1 O1 87.88(12) . . ? N4 Mn1 N1 91.90(12) . . ? N5 Mn1 N1 90.83(12) . . ? O1 Mn1 N1 91.60(11) . . ? N4 Mn1 N2 88.57(13) . . ? N5 Mn1 N2 88.64(13) . . ? O1 Mn1 N2 91.35(11) . . ? N1 Mn1 N2 176.98(11) . . ? N4 Mn1 S2 87.71(10) . 2_565 ? N5 Mn1 S2 91.09(9) . 2_565 ? O1 Mn1 S2 178.46(9) . 2_565 ? N1 Mn1 S2 87.28(8) . 2_565 ? N2 Mn1 S2 89.76(8) . 2_565 ? C19 N4 Mn1 160.8(3) . . ? N4 C19 S1A 171.4(6) . . ? N4 C19 S1B 172.6(6) . . ? S1A C19 S1B 15.9(7) . . ? C20 N5 Mn1 165.4(3) . . ? N5 C20 S2 178.7(3) . . ? C20 S2 Mn1 100.49(11) . 2_565 ? C5 N1 C1 116.7(3) . . ? C5 N1 Mn1 123.9(2) . . ? C1 N1 Mn1 119.3(2) . . ? N1 C1 C2 123.6(3) . . ? C1 C2 C3 119.8(3) . . ? C4 C3 C2 116.6(3) . . ? C4 C3 C6 119.8(3) . . ? C2 C3 C6 123.6(3) . . ? C5 C4 C3 119.8(3) . . ? N1 C5 C4 123.5(3) . . ? C6 C6 C3 125.8(4) 2_655 . ? C7 N2 C11 116.9(4) . . ? C7 N2 Mn1 121.7(3) . . ? C11 N2 Mn1 120.6(3) . . ? N2 C7 C8 122.8(5) . . ? C9 C8 C7 121.2(5) . . ? C8 C9 C10 115.7(4) . . ? C8 C9 C12A 104.7(6) . . ? C10 C9 C12A 139.4(6) . . ? C8 C9 C12B 142.4(6) . . ? C10 C9 C12B 101.8(6) . . ? C12A C9 C12B 37.7(4) . . ? C11 C10 C9 120.8(5) . . ? N2 C11 C10 122.5(5) . . ? C13B C12A C12B 89.2(10) . . ? C13B C12A C13A 48.2(7) . . ? C12B C12A C13A 41.5(6) . . ? C13B C12A C9 161.7(11) . . ? C12B C12A C9 72.6(8) . . ? C13A C12A C9 113.5(7) . . ? C13B C13A C12B 87.3(9) . . ? C13B C13A C12A 40.3(6) . . ? C12B C13A C12A 47.6(7) . . ? C13B C13A C16 73.1(7) . . ? C12B C13A C16 159.3(11) . . ? C12A C13A C16 113.4(7) . . ? C12A C13B C13A 91.5(9) . . ? C12A C13B C12B 49.2(7) . . ? C13A C13B C12B 42.8(6) . . ? C12A C13B C16 160.3(11) . . ? C13A C13B C16 68.8(7) . . ? C12B C13B C16 111.3(8) . . ? C12A C12B C13A 90.9(9) . . ? C12A C12B C13B 41.6(6) . . ? C13A C12B C13B 49.9(7) . . ? C12A C12B C9 69.7(8) . . ? C13A C12B C9 158.3(11) . . ? C13B C12B C9 111.2(8) . . ? N3 C14 C15 123.4(5) . . ? C14 C15 C16 120.1(6) . . ? C17 C16 C15 116.1(4) . . ? C17 C16 C13A 103.3(6) . . ? C15 C16 C13A 140.6(6) . . ? C17 C16 C13B 141.2(6) . . ? C15 C16 C13B 102.6(6) . . ? C13A C16 C13B 38.1(4) . . ? C16 C17 C18 120.5(5) . . ? N3 C18 C17 123.4(5) . . ? C18 N3 C14 116.5(4) . . ? C21 O1 Mn1 131.1(3) . . ? _refine_diff_density_max 0.565 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.072