# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. #========================================================================== _journal_coden_Cambridge 0182 _publ_contact_author_name 'Alexander Briceno' _publ_contact_author_address ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; _publ_contact_author_phone '(58-212) 504-1320' _publ_contact_author_fax '(58-212) 504-1350' _publ_contact_author_email abriceno@ivic.ve _publ_requested_category ? _publ_requested_coeditor_name ? #========================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Exploiting the use of multivalent interactions to design photoreactive multi-component metal assemblies ; loop_ _publ_author_name _publ_author_address 'Alexander Briceno' ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; 'Yennifer Hill' ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; 'Reinaldo Atencio' ; Centro de Quimica Instituto Venezolano de Investigaciones Cientifica (IVIC) Apartado 21827 Caracas 1020-A Venezuela ; # Attachment 'shelxle_I_rev.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 644639' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Mn N4 O4,2(C12 H10 N2),2(ClO4),2(H2O)' _chemical_formula_sum 'C48 H52 Cl2 Mn N8 O14' _chemical_formula_weight 1090.82 _chemical_compound_source Synthesis 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' 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' N N 0.0061 0.0033 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.821(2) _cell_length_b 10.751(2) _cell_length_c 12.742(3) _cell_angle_alpha 80.17(1) _cell_angle_beta 78.99(1) _cell_angle_gamma 89.31(2) _cell_volume 1300.7(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1630 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 27.860 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 567 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.930 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14710 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.86 _reflns_number_total 4903 _reflns_number_gt 3785 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All H atoms bound to carbon were included in calculated positions (C-H = 0.93\%A) and refined as riding with U~iso~(H) = 1.2Ueq(C). H-atoms on coordinated water molecules were found from the Difference Fourier map. They were refined with isotropic displacement parameters set to 1.2Ueq(O) of the attached atom. The ClO4^-^ anion displayed highly anisotropic thermal motion and was modelled as disordered in two set of positions and these were refined isotropically constraining Cl-O and O...O distances to 1.400(3) \%A and 2.280(3) \%A, respectively, to force tetrahedral symmetry. The occupational parameters were determined to be 0.60 and 0.40. ; _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.1190P)^2^+0.9456P] 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 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4903 _refine_ls_number_parameters 328 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.2126 _refine_ls_wR_factor_gt 0.1936 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.062 _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 0.5000 0.5000 0.0000 0.0450(3) Uani 1 2 d S . . N1 N 0.8924(3) -0.3452(3) 0.0981(3) 0.0571(8) Uani 1 1 d . . . N2 N 0.6049(3) 0.3138(2) 0.0471(2) 0.0476(7) Uani 1 1 d . . . N3 N 0.6453(4) 1.3143(4) 0.4519(3) 0.0704(10) Uani 1 1 d . . . N4 N 0.5200(5) 0.7200(3) 0.2597(3) 0.0747(11) Uani 1 1 d . . . Cl1 Cl 0.82861(11) 0.86808(9) 0.73674(8) 0.0629(3) Uani 1 1 d D . . O1 O 0.7380(5) 0.9207(5) 0.8168(3) 0.105(2) Uiso 0.60 1 d PD A 1 O2 O 0.9473(4) 0.9484(4) 0.7023(4) 0.0833(16) Uiso 0.60 1 d PD A 1 O3 O 0.8657(6) 0.7487(3) 0.7797(4) 0.098(2) Uiso 0.60 1 d PD A 1 O4 O 0.7639(5) 0.8658(5) 0.6490(3) 0.0857(18) Uiso 0.60 1 d PD A 1 O1A O 0.7008(5) 0.8555(9) 0.8083(5) 0.114(3) Uiso 0.40 1 d PD A 2 O2A O 0.8848(9) 0.9884(4) 0.7252(7) 0.138(5) Uiso 0.40 1 d PD A 2 O3A O 0.9192(7) 0.7781(7) 0.7772(6) 0.110(4) Uiso 0.40 1 d PD A 2 O4A O 0.8107(8) 0.8439(8) 0.6352(4) 0.096(3) Uiso 0.40 1 d PD A 2 O2W O 0.4546(3) 0.5201(2) 0.1689(2) 0.0637(7) Uani 1 1 d . . . H1W2 H 0.4767 0.5947 0.1944 0.076 Uiso 1 1 d R . . H2W2 H 0.4356 0.4536 0.2353 0.076 Uiso 1 1 d R . . O1W O 0.6903(3) 0.6164(2) -0.0197(2) 0.0598(7) Uani 1 1 d . . . H1W1 H 0.7654 0.6347 0.0184 0.072 Uiso 1 1 d R . . H2W1 H 0.7327 0.6574 -0.0921 0.072 Uiso 1 1 d R . . O3W O 0.4010(4) 0.3567(3) 0.3581(3) 0.0861(10) Uani 1 1 d . . . H1W3 H 0.4761 0.3258 0.3976 0.103 Uiso 1 1 d R . . H2W3 H 0.3510 0.2799 0.3605 0.103 Uiso 1 1 d R . . C1 C 0.8423(4) -0.1251(3) 0.0844(3) 0.0500(8) Uani 1 1 d . . . H1 H 0.7800 -0.1367 0.0402 0.060 Uiso 1 1 calc R . . C2 C 0.8479(4) -0.0134(3) 0.1139(3) 0.0480(8) Uani 1 1 d . . . H2 H 0.9139 -0.0029 0.1553 0.058 Uiso 1 1 calc R . . C3 C 0.9289(3) -0.2322(3) 0.1174(3) 0.0457(8) Uani 1 1 d . . . C4 C 0.9660(4) -0.4453(4) 0.1295(4) 0.0665(11) Uani 1 1 d . . . H4 H 0.9414 -0.5233 0.1156 0.080 Uiso 1 1 calc R . . C5 C 1.0767(4) -0.4396(4) 0.1816(4) 0.0675(11) Uani 1 1 d . . . H5 H 1.1237 -0.5119 0.2041 0.081 Uiso 1 1 calc R . . C6 C 1.1140(4) -0.3245(4) 0.1984(4) 0.0643(11) Uani 1 1 d . . . H6 H 1.1891 -0.3167 0.2317 0.077 Uiso 1 1 calc R . . C7 C 1.0411(4) -0.2193(4) 0.1664(3) 0.0550(9) Uani 1 1 d . . . H7 H 1.0670 -0.1403 0.1774 0.066 Uiso 1 1 calc R . . C8 C 0.7614(4) 0.0964(3) 0.0884(3) 0.0456(8) Uani 1 1 d . . . C9 C 0.6588(4) 0.0993(3) 0.0269(3) 0.0508(8) Uani 1 1 d . . . H9 H 0.6401 0.0285 -0.0015 0.061 Uiso 1 1 calc R . . C10 C 0.5846(4) 0.2080(3) 0.0081(3) 0.0517(9) Uani 1 1 d . . . H10 H 0.5168 0.2083 -0.0339 0.062 Uiso 1 1 calc R . . C11 C 0.7025(4) 0.3090(3) 0.1076(3) 0.0532(9) Uani 1 1 d . . . H11 H 0.7174 0.3802 0.1367 0.064 Uiso 1 1 calc R . . C12 C 0.7819(4) 0.2057(3) 0.1296(3) 0.0517(9) Uani 1 1 d . . . H12 H 0.8491 0.2082 0.1717 0.062 Uiso 1 1 calc R . . C13 C 0.6941(5) 0.9935(4) 0.4055(3) 0.0660(11) Uani 1 1 d . . . H13 H 0.7700 0.9684 0.4372 0.079 Uiso 1 1 calc R . . C14 C 0.6539(5) 1.1088(4) 0.4063(3) 0.0670(11) Uani 1 1 d . . . H14 H 0.5759 1.1316 0.3765 0.080 Uiso 1 1 calc R . . C15 C 0.7187(5) 1.2088(4) 0.4497(3) 0.0660(11) Uani 1 1 d . . . C16 C 0.6950(6) 1.4078(4) 0.4912(4) 0.0796(14) Uani 1 1 d . . . H16 H 0.6429 1.4803 0.4943 0.096 Uiso 1 1 calc R . . C17 C 0.8177(7) 1.4039(6) 0.5270(5) 0.0977(18) Uani 1 1 d . . . H17 H 0.8488 1.4718 0.5533 0.117 Uiso 1 1 calc R . . C18 C 0.8940(6) 1.2954(7) 0.5230(5) 0.1038(19) Uani 1 1 d . . . H18 H 0.9787 1.2890 0.5458 0.125 Uiso 1 1 calc R . . C19 C 0.8429(6) 1.1973(6) 0.4847(5) 0.0918(16) Uani 1 1 d . . . H19 H 0.8923 1.1231 0.4825 0.110 Uiso 1 1 calc R . . C20 C 0.6295(4) 0.9002(4) 0.3585(3) 0.0568(9) Uani 1 1 d . . . C21 C 0.5146(4) 0.9249(4) 0.3097(3) 0.0604(10) Uani 1 1 d . . . H21 H 0.4717 1.0026 0.3090 0.073 Uiso 1 1 calc R . . C22 C 0.4651(5) 0.8340(4) 0.2626(4) 0.0695(11) Uani 1 1 d . . . H22 H 0.3882 0.8528 0.2305 0.083 Uiso 1 1 calc R . . C23 C 0.6274(6) 0.6964(4) 0.3082(4) 0.0769(14) Uani 1 1 d . . . H24 H 0.6671 0.6174 0.3084 0.092 Uiso 1 1 calc R . . C24 C 0.6840(5) 0.7806(4) 0.3583(3) 0.0691(11) Uani 1 1 d . . . H25 H 0.7588 0.7575 0.3920 0.083 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 0.0530(5) 0.0345(4) 0.0519(5) -0.0081(3) -0.0208(3) 0.0039(3) N1 0.0526(18) 0.0470(17) 0.078(2) -0.0179(15) -0.0226(16) 0.0076(14) N2 0.0553(17) 0.0360(14) 0.0550(17) -0.0055(12) -0.0219(14) 0.0027(12) N3 0.090(3) 0.067(2) 0.057(2) -0.0113(16) -0.0204(19) -0.017(2) N4 0.110(3) 0.057(2) 0.057(2) -0.0161(16) -0.011(2) -0.005(2) Cl1 0.0662(6) 0.0612(6) 0.0644(6) -0.0056(4) -0.0245(5) -0.0012(5) O2W 0.094(2) 0.0466(14) 0.0531(16) -0.0113(11) -0.0198(14) 0.0020(13) O1W 0.0568(16) 0.0545(15) 0.0703(18) -0.0032(12) -0.0236(13) -0.0095(12) O3W 0.124(3) 0.0639(18) 0.076(2) -0.0015(15) -0.044(2) -0.0153(18) C1 0.0453(19) 0.0484(19) 0.057(2) -0.0042(16) -0.0149(16) 0.0031(15) C2 0.0473(19) 0.0442(18) 0.053(2) -0.0030(15) -0.0155(16) 0.0040(15) C3 0.0411(17) 0.0418(17) 0.054(2) -0.0079(14) -0.0076(15) 0.0019(14) C4 0.063(2) 0.046(2) 0.098(3) -0.021(2) -0.025(2) 0.0081(18) C5 0.061(2) 0.053(2) 0.092(3) -0.014(2) -0.026(2) 0.0171(19) C6 0.053(2) 0.063(2) 0.085(3) -0.018(2) -0.030(2) 0.0135(19) C7 0.051(2) 0.0462(19) 0.071(2) -0.0118(17) -0.0199(18) 0.0058(16) C8 0.0462(18) 0.0419(17) 0.0458(19) 0.0015(14) -0.0096(15) -0.0005(14) C9 0.054(2) 0.0397(17) 0.062(2) -0.0104(15) -0.0197(17) 0.0003(15) C10 0.053(2) 0.0445(19) 0.063(2) -0.0091(16) -0.0245(18) 0.0040(15) C11 0.061(2) 0.0396(17) 0.067(2) -0.0118(16) -0.0281(19) 0.0018(16) C12 0.052(2) 0.0493(19) 0.059(2) -0.0074(16) -0.0251(17) 0.0019(16) C13 0.072(3) 0.071(3) 0.055(2) -0.0104(19) -0.013(2) -0.004(2) C14 0.068(3) 0.076(3) 0.057(2) -0.014(2) -0.010(2) -0.003(2) C15 0.073(3) 0.074(3) 0.049(2) -0.0114(19) -0.006(2) -0.017(2) C16 0.112(4) 0.062(3) 0.068(3) -0.008(2) -0.028(3) -0.014(3) C17 0.117(5) 0.095(4) 0.092(4) -0.030(3) -0.032(4) -0.032(4) C18 0.079(4) 0.131(5) 0.115(5) -0.043(4) -0.035(3) -0.010(4) C19 0.083(4) 0.104(4) 0.097(4) -0.037(3) -0.021(3) 0.001(3) C20 0.064(2) 0.062(2) 0.0408(19) -0.0073(16) -0.0040(17) -0.0027(19) C21 0.069(3) 0.054(2) 0.060(2) -0.0164(18) -0.012(2) 0.0039(18) C22 0.081(3) 0.068(3) 0.064(3) -0.020(2) -0.017(2) -0.004(2) C23 0.113(4) 0.053(2) 0.055(3) -0.0057(19) 0.002(3) 0.009(2) C24 0.078(3) 0.071(3) 0.052(2) 0.0000(19) -0.006(2) 0.011(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 O2W 2.161(3) 2_665 ? Mn1 O2W 2.161(3) . ? Mn1 O1W 2.211(3) . ? Mn1 O1W 2.211(3) 2_665 ? Mn1 N2 2.282(3) 2_665 ? Mn1 N2 2.282(3) . ? N1 C4 1.335(5) . ? N1 C3 1.346(4) . ? N2 C11 1.335(4) . ? N2 C10 1.348(4) . ? N3 C16 1.333(6) . ? N3 C15 1.337(6) . ? N4 C23 1.322(6) . ? N4 C22 1.336(6) . ? Cl1 O3 1.379(2) . ? Cl1 O2A 1.385(3) . ? Cl1 O4 1.391(2) . ? Cl1 O1A 1.396(3) . ? Cl1 O4A 1.405(3) . ? Cl1 O3A 1.406(3) . ? Cl1 O1 1.411(2) . ? Cl1 O2 1.413(2) . ? O2W H1W2 0.9563 . ? O2W H2W2 0.9985 . ? O1W H1W1 0.9956 . ? O1W H2W1 0.9692 . ? O3W H1W3 0.9927 . ? O3W H2W3 0.9583 . ? C1 C2 1.322(5) . ? C1 C3 1.474(5) . ? C1 H1 0.9300 . ? C2 C8 1.473(5) . ? C2 H2 0.9300 . ? C3 C7 1.385(5) . ? C4 C5 1.384(6) . ? C4 H4 0.9300 . ? C5 C6 1.358(6) . ? C5 H5 0.9300 . ? C6 C7 1.375(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.387(5) . ? C8 C12 1.398(5) . ? C9 C10 1.380(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.370(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.298(6) . ? C13 C20 1.460(6) . ? C13 H13 0.9300 . ? C14 C15 1.490(6) . ? C14 H14 0.9300 . ? C15 C19 1.374(7) . ? C16 C17 1.366(8) . ? C16 H16 0.9300 . ? C17 C18 1.382(8) . ? C17 H17 0.9300 . ? C18 C19 1.372(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C24 1.387(6) . ? C20 C21 1.391(6) . ? C21 C22 1.369(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.371(7) . ? C23 H24 0.9300 . ? C24 H25 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 O2W Mn1 O2W 180.0 2_665 . ? O2W Mn1 O1W 91.64(11) 2_665 . ? O2W Mn1 O1W 88.36(11) . . ? O2W Mn1 O1W 88.36(11) 2_665 2_665 ? O2W Mn1 O1W 91.64(11) . 2_665 ? O1W Mn1 O1W 180.00(15) . 2_665 ? O2W Mn1 N2 89.15(11) 2_665 2_665 ? O2W Mn1 N2 90.85(11) . 2_665 ? O1W Mn1 N2 85.68(10) . 2_665 ? O1W Mn1 N2 94.32(10) 2_665 2_665 ? O2W Mn1 N2 90.85(11) 2_665 . ? O2W Mn1 N2 89.15(11) . . ? O1W Mn1 N2 94.32(10) . . ? O1W Mn1 N2 85.68(10) 2_665 . ? N2 Mn1 N2 180.00(15) 2_665 . ? C4 N1 C3 118.0(3) . . ? C11 N2 C10 116.2(3) . . ? C11 N2 Mn1 120.0(2) . . ? C10 N2 Mn1 123.4(2) . . ? C16 N3 C15 118.0(4) . . ? C23 N4 C22 115.8(4) . . ? O3 Cl1 O2A 134.6(4) . . ? O3 Cl1 O4 111.5(2) . . ? O2A Cl1 O4 107.4(5) . . ? O2A Cl1 O1A 110.8(3) . . ? O2A Cl1 O4A 109.8(3) . . ? O1A Cl1 O4A 109.3(3) . . ? O2A Cl1 O3A 109.8(3) . . ? O1A Cl1 O3A 108.8(2) . . ? O4A Cl1 O3A 108.3(2) . . ? O3 Cl1 O1 110.1(2) . . ? O4 Cl1 O1 109.0(2) . . ? O3A Cl1 O1 114.7(4) . . ? O3 Cl1 O2 110.1(2) . . ? O4 Cl1 O2 108.9(2) . . ? O4A Cl1 O2 99.0(4) . . ? O1 Cl1 O2 107.2(2) . . ? Mn1 O2W H1W2 123.4 . . ? Mn1 O2W H2W2 129.4 . . ? H1W2 O2W H2W2 104.8 . . ? Mn1 O1W H1W1 142.8 . . ? Mn1 O1W H2W1 118.2 . . ? H1W1 O1W H2W1 98.0 . . ? H1W3 O3W H2W3 101.8 . . ? C2 C1 C3 123.9(3) . . ? C2 C1 H1 118.0 . . ? C3 C1 H1 118.0 . . ? C1 C2 C8 127.3(3) . . ? C1 C2 H2 116.3 . . ? C8 C2 H2 116.3 . . ? N1 C3 C7 121.1(3) . . ? N1 C3 C1 116.2(3) . . ? C7 C3 C1 122.7(3) . . ? N1 C4 C5 123.8(4) . . ? N1 C4 H4 118.1 . . ? C5 C4 H4 118.1 . . ? C6 C5 C4 117.4(4) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C5 C6 C7 120.3(4) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C3 119.3(4) . . ? C6 C7 H7 120.3 . . ? C3 C7 H7 120.3 . . ? C9 C8 C12 116.9(3) . . ? C9 C8 C2 124.7(3) . . ? C12 C8 C2 118.4(3) . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N2 C10 C9 123.7(3) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N2 C11 C12 124.1(3) . . ? N2 C11 H11 118.0 . . ? C12 C11 H11 118.0 . . ? C11 C12 C8 119.7(3) . . ? C11 C12 H12 120.2 . . ? C8 C12 H12 120.2 . . ? C14 C13 C20 125.1(4) . . ? C14 C13 H13 117.5 . . ? C20 C13 H13 117.5 . . ? C13 C14 C15 127.2(5) . . ? C13 C14 H14 116.4 . . ? C15 C14 H14 116.4 . . ? N3 C15 C19 121.4(4) . . ? N3 C15 C14 114.1(4) . . ? C19 C15 C14 124.5(5) . . ? N3 C16 C17 124.2(5) . . ? N3 C16 H16 117.9 . . ? C17 C16 H16 117.9 . . ? C16 C17 C18 117.6(5) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? C19 C18 C17 119.0(5) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C15 119.9(6) . . ? C18 C19 H19 120.0 . . ? C15 C19 H19 120.0 . . ? C24 C20 C21 116.2(4) . . ? C24 C20 C13 120.5(4) . . ? C21 C20 C13 123.4(4) . . ? C22 C21 C20 119.5(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? N4 C22 C21 124.4(5) . . ? N4 C22 H22 117.8 . . ? C21 C22 H22 117.8 . . ? N4 C23 C24 124.3(4) . . ? N4 C23 H24 117.8 . . ? C24 C23 H24 117.8 . . ? C23 C24 C20 119.8(4) . . ? C23 C24 H25 120.1 . . ? C20 C24 H25 120.1 . . ? _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.600 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.071 # Attachment 'shelxle_II_rev.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 644640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 Mn N6 O2 S2' _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' Mn Mn 0.3368 0.7283 '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' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8749(9) _cell_length_b 10.3195(11) _cell_length_c 17.814(2) _cell_angle_alpha 78.178(8) _cell_angle_beta 82.985(9) _cell_angle_gamma 78.844(7) _cell_volume 1385.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2155 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 27.60 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_absorpt_coefficient_mu 0.661 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.930 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16070 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.06 _reflns_number_total 5261 _reflns_number_gt 3467 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All H atoms bound to carbon were included in calculated positions (C-H = 0.93\%A) and refined as riding with U~iso~(H) = 1.2Ueq(C). H-atoms on coordinated water molecules were found from the Difference Fourier map. They were refined with isotropic displacement parameters set to 1.2Ueq(O) of the attached atom. One coordinated 2,4-bpe molecule was found to be disordered and was modelled in two sets of positions and constraining the pyridyl rings to be regular hexagons. ; _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.1024P)^2^+0.1073P] 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_number_reflns 5261 _refine_ls_number_parameters 413 _refine_ls_number_restraints 462 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.1998 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.055 _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 0.19904(8) -0.00135(6) 0.22383(3) 0.0523(2) Uani 1 1 d . . . S1 S -0.37660(16) 0.25312(14) 0.19535(8) 0.0768(4) Uani 1 1 d . A . S2 S 0.68343(19) -0.20354(17) 0.38313(8) 0.0962(5) Uani 1 1 d . A . O1 O 0.0537(4) -0.1148(3) 0.31855(18) 0.0805(9) Uani 1 1 d . A . H1W1 H -0.0529 -0.1226 0.3254 0.097 Uiso 1 1 d R . . H2W1 H 0.0937 -0.1548 0.3610 0.097 Uiso 1 1 d R . . O2 O 0.3564(4) 0.1081(3) 0.13129(15) 0.0697(9) Uani 1 1 d . A . H1W2 H 0.3561 0.1263 0.0826 0.084 Uiso 1 1 d R . . H2W2 H 0.4469 0.1249 0.1463 0.084 Uiso 1 1 d R . . N1 N -0.0485(6) 0.1000(4) 0.1771(2) 0.0746(11) Uani 1 1 d . A . N2 N 0.4236(5) -0.1074(4) 0.2839(2) 0.0647(10) Uani 1 1 d . A . N5 N 0.1884(5) 0.1753(4) 0.28720(18) 0.0586(9) Uani 1 1 d . A . N6 N 0.1733(5) 0.7544(4) 0.4610(2) 0.0715(11) Uani 1 1 d . . . C1 C -0.1856(6) 0.1628(4) 0.1845(2) 0.0544(10) Uani 1 1 d . . . C2 C 0.5309(6) -0.1482(4) 0.3253(2) 0.0543(10) Uani 1 1 d . . . C5 C 0.2297(9) -0.3423(7) 0.0499(4) 0.0449(19) Uani 0.584(8) 1 d PGDU A 1 C6 C 0.1502(12) -0.2098(8) 0.0268(4) 0.053(2) Uani 0.584(8) 1 d PGDU A 1 H6A H 0.1013 -0.1836 -0.0201 0.064 Uiso 0.584(8) 1 calc PR A 1 C7 C 0.1437(18) -0.1164(6) 0.0737(6) 0.068(3) Uani 0.584(8) 1 d PGDU A 1 H7A H 0.0905 -0.0278 0.0582 0.081 Uiso 0.584(8) 1 calc PR A 1 N3 N 0.217(2) -0.1555(8) 0.1438(6) 0.047(2) Uani 0.584(8) 1 d PGDU A 1 C8 C 0.2964(16) -0.2880(8) 0.1669(4) 0.0480(19) Uani 0.584(8) 1 d PGDU A 1 H8A H 0.3453 -0.3141 0.2138 0.058 Uiso 0.584(8) 1 calc PR A 1 C9 C 0.3028(11) -0.3814(6) 0.1200(4) 0.054(2) Uani 0.584(8) 1 d PGDU A 1 H9A H 0.3560 -0.4700 0.1354 0.064 Uiso 0.584(8) 1 calc PR A 1 C3 C 0.2275(10) -0.4346(7) -0.0021(4) 0.053(2) Uani 0.584(8) 1 d PDU A 1 H3A H 0.1865 -0.3950 -0.0498 0.063 Uiso 0.584(8) 1 calc PR A 1 C4 C 0.2755(10) -0.5657(7) 0.0092(5) 0.052(2) Uani 0.584(8) 1 d PDU A 1 H4A H 0.3184 -0.6072 0.0562 0.063 Uiso 0.584(8) 1 calc PR A 1 C10 C 0.2679(12) -0.6519(7) -0.0445(4) 0.043(2) Uani 0.584(8) 1 d PGDU A 1 N4 N 0.3064(13) -0.7898(7) -0.0182(4) 0.049(2) Uani 0.584(8) 1 d PGDU A 1 C11 C 0.3077(17) -0.8780(6) -0.0678(5) 0.061(3) Uani 0.584(8) 1 d PGDU A 1 H11A H 0.3335 -0.9703 -0.0501 0.073 Uiso 0.584(8) 1 calc PR A 1 C12 C 0.270(2) -0.8283(9) -0.1437(5) 0.063(3) Uani 0.584(8) 1 d PGDU A 1 H12A H 0.2714 -0.8873 -0.1768 0.076 Uiso 0.584(8) 1 calc PR A 1 C13 C 0.232(2) -0.6904(9) -0.1700(4) 0.065(3) Uani 0.584(8) 1 d PGDU A 1 H13A H 0.2070 -0.6571 -0.2208 0.079 Uiso 0.584(8) 1 calc PR A 1 C14 C 0.2306(14) -0.6021(6) -0.1204(5) 0.054(2) Uani 0.584(8) 1 d PGDU A 1 H14A H 0.2048 -0.5099 -0.1380 0.065 Uiso 0.584(8) 1 calc PR A 1 C5A C 0.2665(12) -0.3837(8) 0.0778(6) 0.048(3) Uani 0.416(8) 1 d PGDU A 2 C6A C 0.1849(15) -0.2554(9) 0.0466(5) 0.052(3) Uani 0.416(8) 1 d PGDU A 2 H6AA H 0.1420 -0.2392 -0.0015 0.062 Uiso 0.416(8) 1 calc PR A 2 C7A C 0.167(2) -0.1514(8) 0.0872(7) 0.037(2) Uani 0.416(8) 1 d PGDU A 2 H7AA H 0.1127 -0.0655 0.0663 0.044 Uiso 0.416(8) 1 calc PR A 2 N3A N 0.231(3) -0.1756(11) 0.1590(8) 0.048(3) Uani 0.416(8) 1 d PGDU A 2 C8A C 0.313(3) -0.3039(12) 0.1902(7) 0.071(3) Uani 0.416(8) 1 d PGDU A 2 H8AA H 0.3560 -0.3201 0.2382 0.085 Uiso 0.416(8) 1 calc PR A 2 C9A C 0.3307(17) -0.4079(9) 0.1496(6) 0.060(3) Uani 0.416(8) 1 d PGDU A 2 H9AA H 0.3853 -0.4938 0.1705 0.072 Uiso 0.416(8) 1 calc PR A 2 C3A C 0.2790(14) -0.4999(10) 0.0410(6) 0.057(3) Uani 0.416(8) 1 d PDU A 2 H3AA H 0.3379 -0.5808 0.0664 0.069 Uiso 0.416(8) 1 calc PR A 2 C4A C 0.2176(15) -0.5042(13) -0.0234(6) 0.058(3) Uani 0.416(8) 1 d PDU A 2 H4AA H 0.1536 -0.4236 -0.0467 0.069 Uiso 0.416(8) 1 calc PR A 2 C10A C 0.2335(17) -0.6142(10) -0.0639(7) 0.051(3) Uani 0.416(8) 1 d PGDU A 2 N4A N 0.2986(17) -0.7396(12) -0.0222(5) 0.044(3) Uani 0.416(8) 1 d PGDU A 2 C11A C 0.322(2) -0.8531(9) -0.0555(8) 0.046(3) Uani 0.416(8) 1 d PGDU A 2 H11B H 0.3658 -0.9370 -0.0276 0.055 Uiso 0.416(8) 1 calc PR A 2 C12A C 0.281(3) -0.8412(11) -0.1306(8) 0.057(3) Uani 0.416(8) 1 d PGDU A 2 H12B H 0.2968 -0.9171 -0.1529 0.069 Uiso 0.416(8) 1 calc PR A 2 C13A C 0.216(3) -0.7158(14) -0.1723(6) 0.060(3) Uani 0.416(8) 1 d PGDU A 2 H13B H 0.1883 -0.7078 -0.2225 0.072 Uiso 0.416(8) 1 calc PR A 2 C14A C 0.192(2) -0.6023(10) -0.1390(7) 0.060(3) Uani 0.416(8) 1 d PGDU A 2 H14B H 0.1487 -0.5184 -0.1669 0.072 Uiso 0.416(8) 1 calc PR A 2 C15 C 0.1713(7) 0.5139(5) 0.3939(3) 0.0806(15) Uani 1 1 d D . . H15A H 0.1167 0.5961 0.3679 0.097 Uiso 1 1 calc R . . C16 C 0.2366(7) 0.5119(5) 0.4586(2) 0.0814(15) Uani 1 1 d D . . H16A H 0.2912 0.4290 0.4838 0.098 Uiso 1 1 calc R . . C17 C 0.1793(7) 0.3947(5) 0.3602(3) 0.0695(13) Uani 1 1 d . . . C18 C 0.1108(7) 0.4093(5) 0.2912(3) 0.0810(15) Uani 1 1 d . A . H18A H 0.0593 0.4941 0.2672 0.097 Uiso 1 1 calc R . . C19 C 0.1172(7) 0.3012(5) 0.2573(3) 0.0728(13) Uani 1 1 d . . . H19A H 0.0692 0.3159 0.2105 0.087 Uiso 1 1 calc R A . C20 C 0.2589(7) 0.1586(5) 0.3534(2) 0.0719(13) Uani 1 1 d . . . H20A H 0.3129 0.0731 0.3750 0.086 Uiso 1 1 calc R A . C21 C 0.2550(7) 0.2644(6) 0.3915(3) 0.0798(15) Uani 1 1 d . A . H21A H 0.3034 0.2478 0.4384 0.096 Uiso 1 1 calc R . . C22 C 0.2314(6) 0.6291(5) 0.4953(2) 0.0652(12) Uani 1 1 d . . . C23 C 0.1776(8) 0.8524(5) 0.4997(3) 0.0926(17) Uani 1 1 d . . . H23A H 0.1386 0.9408 0.4765 0.111 Uiso 1 1 calc R . . C24 C 0.2367(9) 0.8293(7) 0.5720(3) 0.099(2) Uani 1 1 d . . . H24A H 0.2367 0.9002 0.5969 0.119 Uiso 1 1 calc R . . C25 C 0.2951(8) 0.7000(7) 0.6058(3) 0.0951(18) Uani 1 1 d . . . H25A H 0.3361 0.6805 0.6544 0.114 Uiso 1 1 calc R . . C26 C 0.2922(8) 0.6003(6) 0.5673(3) 0.0874(16) Uani 1 1 d . . . H26A H 0.3317 0.5115 0.5895 0.105 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 0.0579(4) 0.0498(4) 0.0541(4) -0.0205(3) -0.0162(3) -0.0025(3) S1 0.0594(8) 0.0849(10) 0.0927(9) -0.0340(7) -0.0162(6) -0.0043(7) S2 0.0764(10) 0.1235(13) 0.0812(9) 0.0221(8) -0.0346(7) -0.0257(9) O1 0.066(2) 0.099(3) 0.0768(19) -0.0064(17) -0.0126(16) -0.0217(19) O2 0.085(2) 0.079(2) 0.0547(16) -0.0187(14) -0.0145(15) -0.0248(18) N1 0.075(3) 0.071(3) 0.086(3) -0.033(2) -0.031(2) 0.002(2) N2 0.064(2) 0.071(3) 0.061(2) -0.0208(18) -0.0137(19) -0.003(2) N5 0.068(2) 0.056(2) 0.056(2) -0.0212(16) -0.0080(17) -0.0088(19) N6 0.080(3) 0.076(3) 0.062(2) -0.026(2) -0.0005(19) -0.012(2) C1 0.066(3) 0.047(2) 0.055(2) -0.0145(18) -0.024(2) -0.004(2) C2 0.062(3) 0.052(3) 0.052(2) -0.0118(18) -0.011(2) -0.013(2) C5 0.043(4) 0.047(5) 0.043(4) -0.011(4) -0.009(3) 0.001(4) C6 0.062(5) 0.052(5) 0.043(4) -0.014(4) -0.024(3) 0.014(4) C7 0.076(6) 0.056(5) 0.067(6) -0.009(5) -0.020(5) 0.006(5) N3 0.054(5) 0.035(4) 0.052(5) -0.009(3) -0.013(4) 0.001(3) C8 0.063(4) 0.040(4) 0.042(4) -0.006(3) -0.026(4) 0.003(4) C9 0.069(5) 0.039(4) 0.048(6) 0.001(4) -0.018(5) 0.002(4) C3 0.061(4) 0.051(5) 0.048(4) -0.019(3) -0.009(3) -0.004(4) C4 0.064(5) 0.044(4) 0.052(4) -0.016(3) -0.012(3) -0.005(4) C10 0.050(5) 0.034(5) 0.046(4) -0.010(4) -0.006(3) -0.008(4) N4 0.066(4) 0.031(4) 0.058(4) -0.020(3) -0.003(3) -0.016(4) C11 0.082(6) 0.064(5) 0.052(5) -0.036(4) -0.011(4) -0.018(5) C12 0.073(6) 0.066(6) 0.053(5) -0.021(4) -0.007(4) -0.010(5) C13 0.078(6) 0.061(5) 0.066(5) -0.024(4) -0.011(4) -0.017(5) C14 0.069(6) 0.052(4) 0.052(5) -0.026(4) -0.021(4) -0.010(4) C5A 0.051(6) 0.036(5) 0.052(7) 0.003(5) -0.019(5) 0.001(4) C6A 0.057(6) 0.062(8) 0.036(5) -0.008(6) -0.032(4) 0.009(6) C7A 0.049(5) 0.027(5) 0.032(5) -0.004(4) -0.024(4) 0.009(5) N3A 0.056(6) 0.054(7) 0.041(5) -0.016(5) -0.022(4) -0.005(6) C8A 0.083(7) 0.054(6) 0.074(8) -0.013(6) -0.016(7) -0.002(6) C9A 0.075(7) 0.042(6) 0.066(8) -0.016(5) -0.019(6) -0.001(5) C3A 0.059(6) 0.048(6) 0.064(6) -0.016(5) -0.012(5) 0.002(5) C4A 0.057(6) 0.056(7) 0.057(6) -0.015(5) -0.004(5) -0.001(5) C10A 0.055(6) 0.051(6) 0.050(6) -0.012(5) -0.017(5) -0.008(5) N4A 0.057(5) 0.038(6) 0.050(4) -0.027(4) -0.001(4) -0.019(5) C11A 0.058(5) 0.036(5) 0.055(5) -0.026(4) -0.007(5) -0.016(4) C12A 0.071(6) 0.055(6) 0.056(6) -0.027(5) -0.010(6) -0.015(6) C13A 0.077(7) 0.062(6) 0.055(6) -0.033(5) -0.014(5) -0.015(6) C14A 0.073(8) 0.068(6) 0.052(6) -0.029(5) -0.025(5) -0.012(5) C15 0.090(4) 0.073(3) 0.086(3) -0.030(3) -0.012(3) -0.011(3) C16 0.093(4) 0.084(4) 0.076(3) -0.034(3) -0.005(3) -0.018(3) C17 0.075(3) 0.053(3) 0.087(3) -0.032(2) 0.006(3) -0.013(3) C18 0.098(4) 0.056(3) 0.098(4) -0.028(3) -0.033(3) -0.004(3) C19 0.084(4) 0.057(3) 0.082(3) -0.022(2) -0.022(3) -0.004(3) C20 0.098(4) 0.065(3) 0.061(3) -0.028(2) -0.021(2) -0.007(3) C21 0.091(4) 0.103(4) 0.059(3) -0.040(3) -0.012(3) -0.022(3) C22 0.072(3) 0.070(3) 0.062(3) -0.030(2) 0.000(2) -0.018(3) C23 0.115(5) 0.058(3) 0.103(4) -0.025(3) 0.000(3) -0.008(3) C24 0.124(5) 0.103(5) 0.093(4) -0.066(4) 0.013(4) -0.039(4) C25 0.116(5) 0.113(5) 0.074(3) -0.044(3) -0.017(3) -0.030(4) C26 0.120(5) 0.078(4) 0.070(3) -0.022(3) -0.019(3) -0.016(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 N2 2.169(4) . ? Mn1 O1 2.183(3) . ? Mn1 O2 2.193(3) . ? Mn1 N1 2.199(4) . ? Mn1 N3A 2.288(7) . ? Mn1 N5 2.316(3) . ? Mn1 N3 2.319(5) . ? S1 C1 1.621(5) . ? S2 C2 1.620(4) . ? O1 H1W1 0.8499 . ? O1 H2W1 0.8500 . ? O2 H1W2 0.8500 . ? O2 H2W2 0.8500 . ? N1 C1 1.155(5) . ? N2 C2 1.150(5) . ? N5 C20 1.330(5) . ? N5 C19 1.340(5) . ? N6 C22 1.330(6) . ? N6 C23 1.343(6) . ? C5 C6 1.3900 . ? C5 C9 1.3900 . ? C5 C3 1.462(2) . ? C6 C7 1.3900 . ? C6 H6A 0.9300 . ? C7 N3 1.3900 . ? C7 H7A 0.9300 . ? N3 C8 1.3900 . ? C8 C9 1.3900 . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C3 C4 1.313(9) . ? C3 H3A 0.9300 . ? C4 C10 1.447(7) . ? C4 H4A 0.9300 . ? C10 N4 1.3900 . ? C10 C14 1.3900 . ? N4 C11 1.3900 . ? C11 C12 1.3900 . ? C11 H11A 0.9300 . ? C12 C13 1.3900 . ? C12 H12A 0.9300 . ? C13 C14 1.3900 . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C5A C6A 1.3900 . ? C5A C9A 1.3900 . ? C5A C3A 1.462(2) . ? C6A C7A 1.3900 . ? C6A H6AA 0.9300 . ? C7A N3A 1.3900 . ? C7A H7AA 0.9300 . ? N3A C8A 1.3900 . ? C8A C9A 1.3900 . ? C8A H8AA 0.9300 . ? C9A H9AA 0.9300 . ? C3A C4A 1.310(12) . ? C3A H3AA 0.9300 . ? C4A C10A 1.443(10) . ? C4A H4AA 0.9300 . ? C10A N4A 1.3900 . ? C10A C14A 1.3900 . ? N4A C11A 1.3900 . ? C11A C12A 1.3900 . ? C11A H11B 0.9300 . ? C12A C13A 1.3900 . ? C12A H12B 0.9300 . ? C13A C14A 1.3900 . ? C13A H13B 0.9300 . ? C14A H14B 0.9300 . ? C15 C16 1.3133(19) . ? C15 C17 1.464(6) . ? C15 H15A 0.9300 . ? C16 C22 1.480(6) . ? C16 H16A 0.9300 . ? C17 C18 1.370(6) . ? C17 C21 1.392(7) . ? C18 C19 1.363(6) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.393(6) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 C26 1.379(6) . ? C23 C24 1.383(8) . ? C23 H23A 0.9300 . ? C24 C25 1.362(8) . ? C24 H24A 0.9300 . ? C25 C26 1.354(7) . ? C25 H25A 0.9300 . ? C26 H26A 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 N2 Mn1 O1 84.13(13) . . ? N2 Mn1 O2 93.15(13) . . ? O1 Mn1 O2 177.28(11) . . ? N2 Mn1 N1 172.64(15) . . ? O1 Mn1 N1 88.97(15) . . ? O2 Mn1 N1 93.75(14) . . ? N2 Mn1 N3A 88.1(4) . . ? O1 Mn1 N3A 89.2(5) . . ? O2 Mn1 N3A 90.8(6) . . ? N1 Mn1 N3A 94.3(4) . . ? N2 Mn1 N5 89.01(13) . . ? O1 Mn1 N5 93.78(12) . . ? O2 Mn1 N5 86.10(11) . . ? N1 Mn1 N5 88.92(13) . . ? N3A Mn1 N5 175.7(6) . . ? N2 Mn1 N3 94.9(3) . . ? O1 Mn1 N3 94.1(4) . . ? O2 Mn1 N3 86.2(4) . . ? N1 Mn1 N3 88.1(3) . . ? N3A Mn1 N3 8.0(5) . . ? N5 Mn1 N3 171.5(3) . . ? Mn1 O1 H1W1 131.2 . . ? Mn1 O1 H2W1 124.7 . . ? H1W1 O1 H2W1 103.7 . . ? Mn1 O2 H1W2 133.8 . . ? Mn1 O2 H2W2 113.2 . . ? H1W2 O2 H2W2 112.1 . . ? C1 N1 Mn1 150.3(3) . . ? C2 N2 Mn1 167.4(3) . . ? C20 N5 C19 116.3(4) . . ? C20 N5 Mn1 122.1(3) . . ? C19 N5 Mn1 121.6(3) . . ? C22 N6 C23 116.8(4) . . ? N1 C1 S1 179.0(4) . . ? N2 C2 S2 179.0(4) . . ? C6 C5 C9 120.0 . . ? C6 C5 C3 116.5(5) . . ? C9 C5 C3 123.5(5) . . ? C5 C6 C7 120.0 . . ? C5 C6 H6A 120.0 . . ? C7 C6 H6A 120.0 . . ? C6 C7 N3 120.0 . . ? C6 C7 H7A 120.0 . . ? N3 C7 H7A 120.0 . . ? C8 N3 C7 120.0 . . ? C8 N3 Mn1 119.9(4) . . ? C7 N3 Mn1 120.0(4) . . ? C9 C8 N3 120.0 . . ? C9 C8 H8A 120.0 . . ? N3 C8 H8A 120.0 . . ? C8 C9 C5 120.0 . . ? C8 C9 H9A 120.0 . . ? C5 C9 H9A 120.0 . . ? C4 C3 C5 128.8(8) . . ? C4 C3 H3A 115.6 . . ? C5 C3 H3A 115.6 . . ? C3 C4 C10 126.1(8) . . ? C3 C4 H4A 116.9 . . ? C10 C4 H4A 116.9 . . ? N4 C10 C14 120.0 . . ? N4 C10 C4 117.1(6) . . ? C14 C10 C4 122.8(6) . . ? C10 N4 C11 120.0 . . ? C12 C11 N4 120.0 . . ? C12 C11 H11A 120.0 . . ? N4 C11 H11A 120.0 . . ? C13 C12 C11 120.0 . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C14 C10 120.0 . . ? C13 C14 H14A 120.0 . . ? C10 C14 H14A 120.0 . . ? C6A C5A C9A 120.0 . . ? C6A C5A C3A 123.0(7) . . ? C9A C5A C3A 116.8(7) . . ? C5A C6A C7A 120.0 . . ? C5A C6A H6AA 120.0 . . ? C7A C6A H6AA 120.0 . . ? N3A C7A C6A 120.0 . . ? N3A C7A H7AA 120.0 . . ? C6A C7A H7AA 120.0 . . ? C8A N3A C7A 120.0 . . ? C8A N3A Mn1 121.2(5) . . ? C7A N3A Mn1 118.8(5) . . ? N3A C8A C9A 120.0 . . ? N3A C8A H8AA 120.0 . . ? C9A C8A H8AA 120.0 . . ? C8A C9A C5A 120.0 . . ? C8A C9A H9AA 120.0 . . ? C5A C9A H9AA 120.0 . . ? C4A C3A C5A 128.1(11) . . ? C4A C3A H3AA 115.9 . . ? C5A C3A H3AA 115.9 . . ? C3A C4A C10A 130.2(12) . . ? C3A C4A H4AA 114.9 . . ? C10A C4A H4AA 114.9 . . ? N4A C10A C14A 120.0 . . ? N4A C10A C4A 114.7(9) . . ? C14A C10A C4A 125.3(9) . . ? C11A N4A C10A 120.0 . . ? N4A C11A C12A 120.0 . . ? N4A C11A H11B 120.0 . . ? C12A C11A H11B 120.0 . . ? C13A C12A C11A 120.0 . . ? C13A C12A H12B 120.0 . . ? C11A C12A H12B 120.0 . . ? C12A C13A C14A 120.0 . . ? C12A C13A H13B 120.0 . . ? C14A C13A H13B 120.0 . . ? C13A C14A C10A 120.0 . . ? C13A C14A H14B 120.0 . . ? C10A C14A H14B 120.0 . . ? C16 C15 C17 124.0(5) . . ? C16 C15 H15A 118.0 . . ? C17 C15 H15A 118.0 . . ? C15 C16 C22 126.1(5) . . ? C15 C16 H16A 116.9 . . ? C22 C16 H16A 116.9 . . ? C18 C17 C21 115.6(4) . . ? C18 C17 C15 118.9(4) . . ? C21 C17 C15 125.5(4) . . ? C19 C18 C17 120.8(5) . . ? C19 C18 H18A 119.6 . . ? C17 C18 H18A 119.6 . . ? N5 C19 C18 124.1(4) . . ? N5 C19 H19A 117.9 . . ? C18 C19 H19A 117.9 . . ? N5 C20 C21 122.5(4) . . ? N5 C20 H20A 118.7 . . ? C21 C20 H20A 118.7 . . ? C17 C21 C20 120.6(4) . . ? C17 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? N6 C22 C26 122.0(4) . . ? N6 C22 C16 122.4(4) . . ? C26 C22 C16 115.6(5) . . ? N6 C23 C24 123.7(5) . . ? N6 C23 H23A 118.1 . . ? C24 C23 H23A 118.1 . . ? C25 C24 C23 118.2(5) . . ? C25 C24 H24A 120.9 . . ? C23 C24 H24A 120.9 . . ? C26 C25 C24 118.6(5) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? C25 C26 C22 120.7(5) . . ? C25 C26 H26A 119.7 . . ? C22 C26 H26A 119.7 . . ? _diffrn_measured_fraction_theta_max 0.779 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.705 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.064 # Attachment 'SHELXLE_III_rev.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 644641' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 N4' _chemical_formula_sum 'C24 H20 N4' _chemical_formula_weight 364.44 _chemical_compound_source Synthesis 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c _symmetry_space_group_name_Hall -P2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.307(3) _cell_length_b 5.7271(7) _cell_length_c 24.026(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.525(3) _cell_angle_gamma 90.00 _cell_volume 1971.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1216 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.80 _exptl_crystal_description Prism _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21651 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.75 _reflns_number_total 3777 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.0636P)^2^+0.3082P] 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_number_reflns 3777 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 N1 N 0.17392(15) 0.9381(3) 0.36993(10) 0.0609(6) Uani 1 1 d . . . N2 N -0.08417(15) 0.5206(4) 0.38329(11) 0.0710(7) Uani 1 1 d . . . N3 N 0.31680(15) 1.1869(3) 0.60611(10) 0.0618(6) Uani 1 1 d . . . N4 N 0.60321(17) 0.7650(6) 0.65358(13) 0.0856(8) Uani 1 1 d . . . C1 C 0.27185(16) 0.6843(4) 0.45744(11) 0.0502(6) Uani 1 1 d . . . H1A H 0.3119 0.5465 0.4669 0.060 Uiso 1 1 calc R . . C2 C 0.21105(15) 0.6749(4) 0.49194(11) 0.0468(6) Uani 1 1 d . . . H2A H 0.2388 0.5615 0.5266 0.056 Uiso 1 1 calc R . . C3 C 0.24623(15) 0.9210(4) 0.51899(10) 0.0466(6) Uani 1 1 d . . . H3A H 0.2008 1.0364 0.4911 0.056 Uiso 1 1 calc R . . C4 C 0.32585(16) 0.8967(4) 0.50010(11) 0.0501(6) Uani 1 1 d . . . H4A H 0.3263 1.0297 0.4746 0.060 Uiso 1 1 calc R . . C5 C 0.22070(16) 0.7359(4) 0.38760(11) 0.0492(6) Uani 1 1 d . . . C6 C 0.1287(2) 0.9854(5) 0.30798(14) 0.0718(8) Uani 1 1 d . . . H6A H 0.0952 1.1244 0.2951 0.086 Uiso 1 1 calc R . . C7 C 0.1285(2) 0.8416(6) 0.26222(14) 0.0806(9) Uani 1 1 d . . . H7A H 0.0959 0.8824 0.2196 0.097 Uiso 1 1 calc R . . C8 C 0.1772(2) 0.6380(5) 0.28072(14) 0.0757(8) Uani 1 1 d . . . H8A H 0.1791 0.5377 0.2509 0.091 Uiso 1 1 calc R . . C9 C 0.22360(18) 0.5825(4) 0.34420(12) 0.0599(7) Uani 1 1 d . . . H9A H 0.2566 0.4431 0.3577 0.072 Uiso 1 1 calc R . . C10 C 0.10825(16) 0.6257(4) 0.45404(10) 0.0477(6) Uani 1 1 d . . . C11 C 0.07632(18) 0.4297(4) 0.41554(12) 0.0565(7) Uani 1 1 d . . . H11A H 0.1183 0.3287 0.4121 0.068 Uiso 1 1 calc R . . C12 C -0.0183(2) 0.3861(5) 0.38238(13) 0.0684(8) Uani 1 1 d . . . H12A H -0.0376 0.2523 0.3575 0.082 Uiso 1 1 calc R . . C13 C -0.05259(19) 0.7062(5) 0.42038(14) 0.0744(8) Uani 1 1 d . . . H13A H -0.0961 0.8041 0.4230 0.089 Uiso 1 1 calc R . . C14 C 0.04046(17) 0.7645(4) 0.45540(12) 0.0635(7) Uani 1 1 d . . . H14A H 0.0575 0.8989 0.4801 0.076 Uiso 1 1 calc R . . C15 C 0.27310(16) 0.9810(4) 0.58607(11) 0.0475(6) Uani 1 1 d . . . C16 C 0.3439(2) 1.2475(5) 0.66602(14) 0.0782(9) Uani 1 1 d . . . H16A H 0.3743 1.3897 0.6804 0.094 Uiso 1 1 calc R . . C17 C 0.3296(2) 1.1126(5) 0.70765(14) 0.0841(9) Uani 1 1 d . . . H17A H 0.3505 1.1617 0.7492 0.101 Uiso 1 1 calc R . . C18 C 0.2839(2) 0.9047(5) 0.68708(14) 0.0761(8) Uani 1 1 d . . . H18A H 0.2726 0.8098 0.7141 0.091 Uiso 1 1 calc R . . C19 C 0.25510(17) 0.8387(4) 0.62535(12) 0.0596(7) Uani 1 1 d . . . H19A H 0.2235 0.6984 0.6101 0.071 Uiso 1 1 calc R . . C20 C 0.42189(16) 0.8465(4) 0.55333(11) 0.0518(6) Uani 1 1 d . . . C21 C 0.49376(19) 1.0066(5) 0.56982(13) 0.0660(7) Uani 1 1 d . . . H21A H 0.4831 1.1461 0.5476 0.079 Uiso 1 1 calc R . . C22 C 0.5810(2) 0.9579(6) 0.61924(16) 0.0806(9) Uani 1 1 d . . . H22A H 0.6276 1.0688 0.6292 0.097 Uiso 1 1 calc R . . C23 C 0.5344(2) 0.6134(5) 0.63791(15) 0.0837(9) Uani 1 1 d . . . H23A H 0.5474 0.4764 0.6614 0.100 Uiso 1 1 calc R . . C24 C 0.44451(18) 0.6440(4) 0.58900(13) 0.0677(8) Uani 1 1 d . . . H24A H 0.3996 0.5292 0.5802 0.081 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 N1 0.0666(15) 0.0613(13) 0.0462(13) 0.0000(10) 0.0199(11) 0.0059(11) N2 0.0493(14) 0.0842(16) 0.0676(16) 0.0006(13) 0.0184(12) -0.0111(13) N3 0.0773(16) 0.0518(12) 0.0479(13) -0.0032(9) 0.0232(12) -0.0046(10) N4 0.0500(16) 0.111(2) 0.0793(19) -0.0242(16) 0.0177(14) 0.0037(15) C1 0.0440(14) 0.0505(13) 0.0506(15) -0.0021(11) 0.0182(12) 0.0024(10) C2 0.0435(14) 0.0471(13) 0.0445(14) 0.0032(10) 0.0166(11) 0.0007(10) C3 0.0444(14) 0.0460(13) 0.0440(14) 0.0013(10) 0.0169(11) 0.0006(10) C4 0.0506(15) 0.0513(13) 0.0447(14) 0.0001(11) 0.0198(12) -0.0069(11) C5 0.0435(14) 0.0559(15) 0.0494(15) -0.0042(11) 0.0231(12) -0.0045(11) C6 0.082(2) 0.0667(17) 0.0544(18) 0.0061(14) 0.0230(16) 0.0070(14) C7 0.094(2) 0.093(2) 0.0465(17) 0.0032(16) 0.0271(17) -0.0048(18) C8 0.085(2) 0.089(2) 0.0555(19) -0.0186(16) 0.0356(17) -0.0075(17) C9 0.0572(17) 0.0642(16) 0.0570(18) -0.0085(13) 0.0262(14) -0.0006(12) C10 0.0461(15) 0.0503(14) 0.0424(14) 0.0026(11) 0.0177(12) -0.0023(11) C11 0.0513(16) 0.0513(14) 0.0595(16) -0.0021(12) 0.0205(14) -0.0028(12) C12 0.068(2) 0.0596(16) 0.0631(18) -0.0059(13) 0.0194(16) -0.0158(14) C13 0.0505(18) 0.088(2) 0.082(2) -0.0082(17) 0.0297(16) 0.0014(15) C14 0.0515(17) 0.0695(16) 0.0668(18) -0.0138(13) 0.0260(15) -0.0036(13) C15 0.0450(14) 0.0459(13) 0.0470(15) 0.0001(11) 0.0185(12) 0.0020(10) C16 0.103(2) 0.0654(17) 0.0575(19) -0.0119(14) 0.0312(17) -0.0137(15) C17 0.105(3) 0.091(2) 0.0495(18) -0.0124(16) 0.0317(18) -0.0080(18) C18 0.091(2) 0.090(2) 0.0548(19) 0.0059(15) 0.0403(17) -0.0064(17) C19 0.0595(17) 0.0622(15) 0.0555(17) -0.0003(12) 0.0262(14) -0.0064(12) C20 0.0443(15) 0.0634(15) 0.0473(15) -0.0097(12) 0.0215(12) -0.0062(12) C21 0.0591(18) 0.0809(18) 0.0590(18) -0.0117(14) 0.0289(15) -0.0170(15) C22 0.0494(19) 0.115(3) 0.078(2) -0.035(2) 0.0312(18) -0.0284(18) C23 0.058(2) 0.084(2) 0.080(2) -0.0019(17) 0.0094(17) 0.0094(16) C24 0.0460(17) 0.0682(17) 0.0699(19) 0.0027(14) 0.0122(14) -0.0023(12) _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 N1 C6 1.336(3) . ? N1 C5 1.339(3) . ? N2 C13 1.323(3) . ? N2 C12 1.330(3) . ? N3 C16 1.334(3) . ? N3 C15 1.342(3) . ? N4 C22 1.322(4) . ? N4 C23 1.323(4) . ? C1 C5 1.504(3) . ? C1 C4 1.563(3) . ? C1 C2 1.568(3) . ? C1 H1A 0.9800 . ? C2 C10 1.504(3) . ? C2 C3 1.543(3) . ? C2 H2A 0.9800 . ? C3 C15 1.494(3) . ? C3 C4 1.573(3) . ? C3 H3A 0.9800 . ? C4 C20 1.503(3) . ? C4 H4A 0.9800 . ? C5 C9 1.381(3) . ? C6 C7 1.372(4) . ? C6 H6A 0.9300 . ? C7 C8 1.361(4) . ? C7 H7A 0.9300 . ? C8 C9 1.378(4) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 C14 1.375(3) . ? C10 C11 1.388(3) . ? C11 C12 1.380(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.379(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C19 1.380(3) . ? C16 C17 1.370(4) . ? C16 H16A 0.9300 . ? C17 C18 1.365(4) . ? C17 H17A 0.9300 . ? C18 C19 1.377(4) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C24 1.384(3) . ? C20 C21 1.388(3) . ? C21 C22 1.378(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.384(4) . ? C23 H23A 0.9300 . ? C24 H24A 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 C6 N1 C5 117.2(2) . . ? C13 N2 C12 114.8(2) . . ? C16 N3 C15 117.5(2) . . ? C22 N4 C23 115.4(3) . . ? C5 C1 C4 114.66(18) . . ? C5 C1 C2 116.28(19) . . ? C4 C1 C2 88.88(17) . . ? C5 C1 H1A 111.7 . . ? C4 C1 H1A 111.7 . . ? C2 C1 H1A 111.7 . . ? C10 C2 C3 120.59(18) . . ? C10 C2 C1 119.33(19) . . ? C3 C2 C1 89.40(16) . . ? C10 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C15 C3 C2 121.52(19) . . ? C15 C3 C4 118.31(19) . . ? C2 C3 C4 89.40(16) . . ? C15 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C20 C4 C1 116.18(18) . . ? C20 C4 C3 116.09(19) . . ? C1 C4 C3 88.51(16) . . ? C20 C4 H4A 111.4 . . ? C1 C4 H4A 111.4 . . ? C3 C4 H4A 111.4 . . ? N1 C5 C9 122.0(2) . . ? N1 C5 C1 116.9(2) . . ? C9 C5 C1 121.1(2) . . ? N1 C6 C7 124.0(3) . . ? N1 C6 H6A 118.0 . . ? C7 C6 H6A 118.0 . . ? C8 C7 C6 118.4(3) . . ? C8 C7 H7A 120.8 . . ? C6 C7 H7A 120.8 . . ? C7 C8 C9 119.1(3) . . ? C7 C8 H8A 120.5 . . ? C9 C8 H8A 120.5 . . ? C8 C9 C5 119.4(2) . . ? C8 C9 H9A 120.3 . . ? C5 C9 H9A 120.3 . . ? C14 C10 C11 115.7(2) . . ? C14 C10 C2 123.6(2) . . ? C11 C10 C2 120.7(2) . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11A 120.3 . . ? C10 C11 H11A 120.3 . . ? N2 C12 C11 125.1(2) . . ? N2 C12 H12A 117.5 . . ? C11 C12 H12A 117.5 . . ? N2 C13 C14 124.5(3) . . ? N2 C13 H13A 117.8 . . ? C14 C13 H13A 117.8 . . ? C10 C14 C13 120.6(2) . . ? C10 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? N3 C15 C19 121.5(2) . . ? N3 C15 C3 114.9(2) . . ? C19 C15 C3 123.6(2) . . ? N3 C16 C17 123.9(3) . . ? N3 C16 H16A 118.1 . . ? C17 C16 H16A 118.1 . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17A 120.6 . . ? C16 C17 H17A 120.6 . . ? C17 C18 C19 118.4(3) . . ? C17 C18 H18A 120.8 . . ? C19 C18 H18A 120.8 . . ? C18 C19 C15 120.0(2) . . ? C18 C19 H19A 120.0 . . ? C15 C19 H19A 120.0 . . ? C24 C20 C21 116.0(2) . . ? C24 C20 C4 123.3(2) . . ? C21 C20 C4 120.8(2) . . ? C22 C21 C20 119.7(3) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? N4 C22 C21 124.7(3) . . ? N4 C22 H22A 117.6 . . ? C21 C22 H22A 117.6 . . ? N4 C23 C24 124.7(3) . . ? N4 C23 H23A 117.7 . . ? C24 C23 H23A 117.7 . . ? C20 C24 C23 119.5(3) . . ? C20 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? _diffrn_measured_fraction_theta_max 0.810 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.142 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.040 # Attachment 'shelxle_IV_rev.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 644642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H40 Mn N10 S2' _chemical_formula_sum 'C50 H40 Mn N10 S2' _chemical_formula_weight 899.98 _chemical_compound_source Synthesis 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.104(3) _cell_length_b 14.0400(16) _cell_length_c 17.205(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.244(2) _cell_angle_gamma 90.00 _cell_volume 4751.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1360 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.0 _exptl_crystal_description Prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1868 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.930 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Mercury' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27061 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.13 _reflns_number_total 4615 _reflns_number_gt 2714 _reflns_threshold_expression >2sigma(I) _publ_section_exptl_refinement ; All H atoms bound to carbon were included in calculated positions (C-H = 0.93 \%A) and refined as riding with U~iso~(H) = 1.2Ueq(C). The NCS^-^ ligand was found disordered and was modelled in two set of positions. The C25A-S1A distance was restraining to 1.680(2) \%A. The occupational parameters were determined to be 0.70 and 0.30. All non-hydrogen atoms were refined with anisotropic thermal parameters except the atoms of the low ocuppancy site of the disordered NCS^-^ ; _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_structure_refinement 'SHELXLTL-NT V5.1 (Bruker AXS, 1998)' _computing_molecular_graphics ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND (Brandenburg, 1998) ; _computing_publication_material ; SHELXLTL-NT V5.1 (Bruker AXS, 1998) and PLATON (Spek, 2003). ; _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^)+(0.1060P)^2^+4.1272P] 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_number_reflns 4615 _refine_ls_number_parameters 294 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2175 _refine_ls_wR_factor_gt 0.1834 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.5000 0.5000 0.5000 0.0483(3) Uani 1 2 d S . . N1 N 0.59329(15) 0.4264(2) 0.5986(2) 0.0531(8) Uani 1 1 d . . . N2 N 0.8888(2) 0.4573(3) 0.7408(3) 0.0806(12) Uani 1 1 d . . . N3 N 0.95678(15) 0.0591(2) 0.59706(19) 0.0529(8) Uani 1 1 d . . . N4 N 0.74361(18) 0.1817(2) 0.5892(2) 0.0612(9) Uani 1 1 d . . . N5 N 0.44248(17) 0.3700(3) 0.4933(2) 0.0638(10) Uani 1 1 d . . . C1 C 0.77643(18) 0.2801(3) 0.7521(2) 0.0538(10) Uani 1 1 d . . . H1 H 0.7845 0.2914 0.8112 0.065 Uiso 1 1 calc R . . C2 C 0.84303(18) 0.2997(3) 0.7363(2) 0.0531(10) Uani 1 1 d . . . H2 H 0.8309 0.3117 0.6766 0.064 Uiso 1 1 calc R . . C3 C 0.86153(19) 0.1936(3) 0.7524(2) 0.0533(10) Uani 1 1 d . . . H3 H 0.8895 0.1845 0.8113 0.064 Uiso 1 1 calc R . . C4 C 0.78522(19) 0.1712(3) 0.7387(2) 0.0550(10) Uani 1 1 d . . . H4 H 0.7810 0.1325 0.7840 0.066 Uiso 1 1 calc R . . C5 C 0.71307(18) 0.3324(3) 0.6998(2) 0.0523(10) Uani 1 1 d . . . C6 C 0.6494(2) 0.3040(3) 0.6973(3) 0.0687(12) Uani 1 1 d . . . H6 H 0.6452 0.2531 0.7296 0.082 Uiso 1 1 calc R . . C7 C 0.5920(2) 0.3522(3) 0.6461(3) 0.0680(12) Uani 1 1 d . . . H7 H 0.5498 0.3313 0.6450 0.082 Uiso 1 1 calc R . . C8 C 0.65527(19) 0.4540(3) 0.6029(3) 0.0572(10) Uani 1 1 d . . . H8 H 0.6584 0.5062 0.5711 0.069 Uiso 1 1 calc R . . C9 C 0.71454(18) 0.4098(3) 0.6514(2) 0.0562(11) Uani 1 1 d . . . H9 H 0.7560 0.4325 0.6516 0.067 Uiso 1 1 calc R . . C10 C 0.8913(2) 0.3761(3) 0.7829(3) 0.0593(11) Uani 1 1 d . . . C11 C 0.9355(2) 0.3628(4) 0.8638(3) 0.0840(16) Uani 1 1 d . . . H11 H 0.9357 0.3059 0.8916 0.101 Uiso 1 1 calc R . . C12 C 0.9800(3) 0.4362(6) 0.9030(4) 0.116(2) Uani 1 1 d . . . H12 H 1.0105 0.4286 0.9573 0.139 Uiso 1 1 calc R . . C13 C 0.9786(4) 0.5191(6) 0.8617(6) 0.125(3) Uani 1 1 d . . . H13 H 1.0085 0.5683 0.8867 0.150 Uiso 1 1 calc R . . C14 C 0.9308(4) 0.5286(5) 0.7803(5) 0.111(2) Uani 1 1 d . . . H14 H 0.9281 0.5862 0.7526 0.133 Uiso 1 1 calc R . . C15 C 0.89525(18) 0.1459(3) 0.6995(2) 0.0493(9) Uani 1 1 d . . . C16 C 0.8997(2) 0.0489(3) 0.6949(3) 0.0623(11) Uani 1 1 d . . . H16 H 0.8820 0.0100 0.7259 0.075 Uiso 1 1 calc R . . C17 C 0.9305(2) 0.0090(3) 0.6439(3) 0.0633(12) Uani 1 1 d . . . H17 H 0.9331 -0.0571 0.6422 0.076 Uiso 1 1 calc R . . C18 C 0.95337(19) 0.1535(3) 0.6025(3) 0.0552(10) Uani 1 1 d . . . H18 H 0.9717 0.1910 0.5713 0.066 Uiso 1 1 calc R . . C19 C 0.9239(2) 0.1978(3) 0.6524(3) 0.0604(11) Uani 1 1 d . . . H19 H 0.9232 0.2640 0.6544 0.073 Uiso 1 1 calc R . . C20 C 0.74483(18) 0.1309(3) 0.6546(2) 0.0514(10) Uani 1 1 d . . . C21 C 0.7134(2) 0.0448(4) 0.6454(3) 0.0808(15) Uani 1 1 d . . . H21 H 0.7143 0.0109 0.6922 0.097 Uiso 1 1 calc R . . C22 C 0.6803(3) 0.0077(4) 0.5670(4) 0.0996(19) Uani 1 1 d . . . H22 H 0.6599 -0.0520 0.5603 0.119 Uiso 1 1 calc R . . C23 C 0.6780(2) 0.0600(4) 0.4999(3) 0.0834(15) Uani 1 1 d . . . H23 H 0.6555 0.0379 0.4460 0.100 Uiso 1 1 calc R . . C24 C 0.7097(2) 0.1456(4) 0.5142(3) 0.0749(14) Uani 1 1 d . . . H24 H 0.7076 0.1818 0.4680 0.090 Uiso 1 1 calc R . . C25A C 0.4057(8) 0.3254(16) 0.4938(13) 0.069(8) Uiso 0.30 1 d PD A 1 S1A S 0.3394(6) 0.2646(10) 0.5009(9) 0.163(4) Uiso 0.30 1 d PD A 1 C25 C 0.4201(4) 0.3079(5) 0.5241(6) 0.063(2) Uani 0.70 1 d P A 2 S1 S 0.38845(18) 0.22489(19) 0.5633(3) 0.1443(12) Uani 0.70 1 d P 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 0.0394(5) 0.0488(5) 0.0556(5) -0.0064(4) 0.0158(4) 0.0092(3) N1 0.0468(19) 0.056(2) 0.0555(19) -0.0016(17) 0.0170(15) 0.0078(15) N2 0.080(3) 0.077(3) 0.091(3) -0.016(3) 0.037(2) -0.012(2) N3 0.0504(18) 0.054(2) 0.0530(19) -0.0078(16) 0.0176(16) 0.0095(15) N4 0.083(2) 0.053(2) 0.0449(18) 0.0013(16) 0.0202(18) -0.0089(18) N5 0.053(2) 0.056(2) 0.085(3) -0.009(2) 0.0276(19) 0.0008(17) C1 0.054(2) 0.066(3) 0.042(2) -0.0002(18) 0.0184(18) 0.0180(19) C2 0.053(2) 0.064(3) 0.0401(19) -0.0059(18) 0.0144(17) 0.0166(19) C3 0.052(2) 0.062(3) 0.043(2) -0.0015(18) 0.0141(18) 0.0168(18) C4 0.060(2) 0.063(3) 0.044(2) 0.0109(19) 0.0218(19) 0.015(2) C5 0.050(2) 0.057(3) 0.050(2) -0.0046(19) 0.0190(18) 0.0146(18) C6 0.061(3) 0.073(3) 0.078(3) 0.018(2) 0.031(2) 0.014(2) C7 0.049(2) 0.074(3) 0.084(3) 0.004(3) 0.028(2) 0.009(2) C8 0.049(2) 0.056(3) 0.063(2) 0.004(2) 0.015(2) 0.0082(19) C9 0.040(2) 0.062(3) 0.061(2) 0.002(2) 0.0125(19) 0.0079(18) C10 0.056(2) 0.066(3) 0.057(2) -0.015(2) 0.021(2) 0.011(2) C11 0.076(3) 0.087(4) 0.067(3) -0.027(3) 0.000(3) 0.013(3) C12 0.086(4) 0.133(6) 0.101(5) -0.054(5) 0.001(4) 0.001(4) C13 0.092(5) 0.145(7) 0.139(7) -0.074(6) 0.043(5) -0.044(5) C14 0.114(5) 0.099(5) 0.139(6) -0.016(4) 0.069(5) -0.012(4) C15 0.045(2) 0.058(3) 0.042(2) -0.0031(18) 0.0115(17) 0.0103(18) C16 0.075(3) 0.057(3) 0.067(3) 0.007(2) 0.039(2) 0.018(2) C17 0.075(3) 0.047(3) 0.070(3) 0.000(2) 0.029(2) 0.016(2) C18 0.058(2) 0.051(3) 0.064(2) -0.009(2) 0.031(2) 0.0028(18) C19 0.061(2) 0.051(3) 0.068(3) -0.012(2) 0.022(2) 0.009(2) C20 0.049(2) 0.055(3) 0.055(2) 0.0103(19) 0.0251(19) 0.0030(18) C21 0.088(3) 0.082(4) 0.074(3) 0.019(3) 0.032(3) -0.021(3) C22 0.118(5) 0.085(4) 0.090(4) 0.000(3) 0.030(4) -0.052(3) C23 0.088(3) 0.086(4) 0.071(3) -0.006(3) 0.022(3) -0.034(3) C24 0.091(3) 0.070(3) 0.055(3) 0.004(2) 0.017(2) -0.023(3) C25 0.067(4) 0.037(4) 0.083(6) -0.002(4) 0.024(4) 0.004(3) S1 0.178(3) 0.0763(17) 0.213(3) 0.0136(19) 0.113(3) -0.0344(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 N5 2.172(4) . ? Mn1 N5 2.172(4) 5_666 ? Mn1 N1 2.324(3) . ? Mn1 N1 2.324(3) 5_666 ? Mn1 N3 2.327(3) 3_455 ? Mn1 N3 2.327(3) 7_656 ? N1 C7 1.331(5) . ? N1 C8 1.340(5) . ? N2 C10 1.341(6) . ? N2 C14 1.346(8) . ? N3 C18 1.331(5) . ? N3 C17 1.332(5) . ? N3 Mn1 2.327(3) 3_545 ? N4 C20 1.324(5) . ? N4 C24 1.329(5) . ? N5 C25A 1.000(13) . ? N5 C25 1.201(8) . ? C1 C5 1.505(5) . ? C1 C2 1.550(5) . ? C1 C4 1.567(6) . ? C1 H1 0.9800 . ? C2 C10 1.497(6) . ? C2 C3 1.540(5) . ? C2 H2 0.9800 . ? C3 C15 1.500(5) . ? C3 C4 1.573(5) . ? C3 H3 0.9800 . ? C4 C20 1.499(5) . ? C4 H4 0.9800 . ? C5 C9 1.377(6) . ? C5 C6 1.387(6) . ? C6 C7 1.389(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.375(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.379(6) . ? C11 C12 1.393(8) . ? C11 H11 0.9300 . ? C12 C13 1.358(10) . ? C12 H12 0.9300 . ? C13 C14 1.405(10) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.370(6) . ? C15 C19 1.381(6) . ? C16 C17 1.387(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.378(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.360(6) . ? C21 C22 1.377(7) . ? C21 H21 0.9300 . ? C22 C23 1.355(7) . ? C22 H22 0.9300 . ? C23 C24 1.353(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25A S1A 1.680(2) . ? C25 S1 1.608(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Mn1 N5 180.0 . 5_666 ? N5 Mn1 N1 88.53(13) . . ? N5 Mn1 N1 91.47(13) 5_666 . ? N5 Mn1 N1 91.47(13) . 5_666 ? N5 Mn1 N1 88.53(13) 5_666 5_666 ? N1 Mn1 N1 180.000(1) . 5_666 ? N5 Mn1 N3 88.92(13) . 3_455 ? N5 Mn1 N3 91.08(13) 5_666 3_455 ? N1 Mn1 N3 94.79(11) . 3_455 ? N1 Mn1 N3 85.21(11) 5_666 3_455 ? N5 Mn1 N3 91.08(13) . 7_656 ? N5 Mn1 N3 88.92(13) 5_666 7_656 ? N1 Mn1 N3 85.21(11) . 7_656 ? N1 Mn1 N3 94.79(11) 5_666 7_656 ? N3 Mn1 N3 180.00(8) 3_455 7_656 ? C7 N1 C8 115.4(3) . . ? C7 N1 Mn1 126.6(3) . . ? C8 N1 Mn1 117.6(3) . . ? C10 N2 C14 118.0(5) . . ? C18 N3 C17 116.0(3) . . ? C18 N3 Mn1 116.8(3) . 3_545 ? C17 N3 Mn1 127.0(3) . 3_545 ? C20 N4 C24 117.2(4) . . ? C25A N5 Mn1 161.2(15) . . ? C25 N5 Mn1 152.6(5) . . ? C5 C1 C2 118.3(3) . . ? C5 C1 C4 121.0(3) . . ? C2 C1 C4 89.1(3) . . ? C5 C1 H1 108.9 . . ? C2 C1 H1 108.9 . . ? C4 C1 H1 108.9 . . ? C10 C2 C3 121.2(3) . . ? C10 C2 C1 121.2(3) . . ? C3 C2 C1 89.1(3) . . ? C10 C2 H2 107.9 . . ? C3 C2 H2 107.9 . . ? C1 C2 H2 107.9 . . ? C15 C3 C2 117.9(3) . . ? C15 C3 C4 120.4(3) . . ? C2 C3 C4 89.3(3) . . ? C15 C3 H3 109.2 . . ? C2 C3 H3 109.2 . . ? C4 C3 H3 109.2 . . ? C20 C4 C1 117.0(3) . . ? C20 C4 C3 114.4(3) . . ? C1 C4 C3 87.3(3) . . ? C20 C4 H4 112.0 . . ? C1 C4 H4 112.0 . . ? C3 C4 H4 112.0 . . ? C9 C5 C6 116.2(4) . . ? C9 C5 C1 122.5(4) . . ? C6 C5 C1 121.3(4) . . ? C5 C6 C7 119.5(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? N1 C7 C6 124.3(4) . . ? N1 C7 H7 117.9 . . ? C6 C7 H7 117.9 . . ? N1 C8 C9 123.9(4) . . ? N1 C8 H8 118.0 . . ? C9 C8 H8 118.0 . . ? C8 C9 C5 120.6(4) . . ? C8 C9 H9 119.7 . . ? C5 C9 H9 119.7 . . ? N2 C10 C11 122.7(4) . . ? N2 C10 C2 115.7(4) . . ? C11 C10 C2 121.6(5) . . ? C10 C11 C12 118.6(6) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 119.9(6) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 118.3(6) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? N2 C14 C13 122.4(7) . . ? N2 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C16 C15 C19 115.9(4) . . ? C16 C15 C3 122.4(4) . . ? C19 C15 C3 121.7(4) . . ? C15 C16 C17 119.7(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? N3 C17 C16 124.2(4) . . ? N3 C17 H17 117.9 . . ? C16 C17 H17 117.9 . . ? N3 C18 C19 122.7(4) . . ? N3 C18 H18 118.6 . . ? C19 C18 H18 118.6 . . ? C18 C19 C15 121.4(4) . . ? C18 C19 H19 119.3 . . ? C15 C19 H19 119.3 . . ? N4 C20 C21 121.4(4) . . ? N4 C20 C4 116.5(3) . . ? C21 C20 C4 122.0(4) . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 118.6(5) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C24 C23 C22 117.7(5) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? N4 C24 C23 124.9(4) . . ? N4 C24 H24 117.6 . . ? C23 C24 H24 117.6 . . ? N5 C25A S1A 171(2) . . ? N5 C25 S1 178.6(9) . . ? _diffrn_measured_fraction_theta_max 0.795 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.620 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.066