# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Erhong Hao' _publ_contact_author_email HAOEHONG@MAIL.AHNU.EDU.CN _publ_section_title ; "Click" Tetradentate Ligands ; loop_ _publ_author_name 'Erhong Hao' 'Lijuan Jiao' 'Shaowu Wang' 'Zhaoyun Wang' # Attachment '4a-Mn.cif' data_mn-1 _database_code_depnum_ccdc_archive 'CCDC 734010' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 F6 Mn N8 O6 S2' _chemical_formula_weight 755.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' 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 19.148(7) _cell_length_b 8.570(3) _cell_length_c 20.170(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.082(4) _cell_angle_gamma 90.00 _cell_volume 3180.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5165 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7424 _exptl_absorpt_correction_T_max 0.8838 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10989 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2802 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0484P)^2^+2.0203P] 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 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2802 _refine_ls_number_parameters 243 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _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 C1 C 0.30288(14) -0.0324(3) 0.44799(13) 0.0641(7) Uani 1 1 d . . . H1 H 0.2966 -0.0087 0.4017 0.077 Uiso 1 1 calc R . . Mn1 Mn 0.0000 0.05217(5) 0.2500 0.03636(16) Uani 1 2 d S . . N1 N 0.17821(9) 0.0462(2) 0.43659(8) 0.0424(4) Uani 1 1 d . . . S1 S 0.09293(3) -0.17077(7) 0.15447(3) 0.04664(18) Uani 1 1 d . A . C2 C 0.36845(15) -0.0893(4) 0.48844(16) 0.0750(8) Uani 1 1 d . . . H2 H 0.4069 -0.1038 0.4692 0.090 Uiso 1 1 calc R . . F2 F 0.1826(9) -0.3253(17) 0.2492(7) 0.115(3) Uani 0.66(4) 1 d PU A 1 F1 F 0.2127(5) -0.086(2) 0.2455(7) 0.090(3) Uani 0.66(4) 1 d PU A 1 F3 F 0.2273(5) -0.2337(18) 0.1635(7) 0.084(2) Uani 0.66(4) 1 d PU A 1 F1' F 0.2164(11) -0.056(2) 0.2235(17) 0.093(5) Uani 0.34(4) 1 d PU A 2 F2' F 0.1979(10) -0.281(3) 0.2606(10) 0.089(5) Uani 0.34(4) 1 d PU A 2 F3' F 0.2268(11) -0.278(3) 0.1782(10) 0.072(4) Uani 0.34(4) 1 d PU A 2 N2 N 0.15313(10) 0.0036(2) 0.37049(9) 0.0451(4) Uani 1 1 d . . . O2 O 0.10076(12) -0.0553(2) 0.10640(10) 0.0795(6) Uani 1 1 d . . . C3 C 0.37743(15) -0.1246(3) 0.55654(14) 0.0703(8) Uani 1 1 d . . . H3 H 0.4216 -0.1639 0.5831 0.084 Uiso 1 1 calc R . . N3 N 0.08927(9) 0.0721(2) 0.34751(9) 0.0441(4) Uani 1 1 d . . . O3 O 0.06980(11) -0.3199(2) 0.12592(12) 0.0813(6) Uani 1 1 d . . . C4 C 0.32228(16) -0.1024(4) 0.58520(13) 0.0724(8) Uani 1 1 d . . . H4 H 0.3288 -0.1260 0.6315 0.087 Uiso 1 1 calc R . . N4 N 0.02959(9) 0.2655(2) 0.18889(10) 0.0462(5) Uani 1 1 d . . . C5 C 0.25604(14) -0.0449(3) 0.54606(12) 0.0607(7) Uani 1 1 d . . . H5 H 0.2181 -0.0291 0.5658 0.073 Uiso 1 1 calc R . . C6 C 0.24728(11) -0.0119(3) 0.47785(10) 0.0439(5) Uani 1 1 d . . . C7 C 0.13101(12) 0.1414(3) 0.45594(11) 0.0498(6) Uani 1 1 d . . . H7 H 0.1363 0.1863 0.4990 0.060 Uiso 1 1 calc R . . C8 C 0.07418(12) 0.1570(3) 0.39846(11) 0.0450(5) Uani 1 1 d . . . C9 C 0.00262(12) 0.2403(3) 0.38603(12) 0.0517(6) Uani 1 1 d . . . H9A H -0.0303 0.1786 0.4043 0.062 Uiso 1 1 calc R . . H9B H 0.0099 0.3399 0.4097 0.062 Uiso 1 1 calc R . . C10 C 0.10922(12) 0.2916(3) 0.20291(15) 0.0602(7) Uani 1 1 d . . . H10A H 0.1309 0.2033 0.1870 0.090 Uiso 1 1 calc R . . H10B H 0.1305 0.3046 0.2516 0.090 Uiso 1 1 calc R . . H10C H 0.1176 0.3837 0.1791 0.090 Uiso 1 1 calc R . . C11 C -0.00545(13) 0.4015(3) 0.21166(13) 0.0564(6) Uani 1 1 d . . . H11A H -0.0571 0.4001 0.1884 0.068 Uiso 1 1 calc R . . H11B H 0.0147 0.4967 0.1985 0.068 Uiso 1 1 calc R . . C12 C 0.18501(15) -0.2019(3) 0.20664(14) 0.0631(7) Uani 1 1 d . . . O1 O 0.05687(9) -0.1164(2) 0.20413(9) 0.0622(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0486(14) 0.094(2) 0.0507(14) 0.0062(13) 0.0147(11) 0.0145(14) Mn1 0.0301(2) 0.0387(3) 0.0389(3) 0.000 0.00723(18) 0.000 N1 0.0355(9) 0.0529(12) 0.0367(9) -0.0032(8) 0.0068(7) 0.0031(8) S1 0.0414(3) 0.0523(4) 0.0499(3) -0.0057(3) 0.0188(2) -0.0002(2) C2 0.0481(15) 0.101(2) 0.0746(18) -0.0007(17) 0.0147(13) 0.0188(15) F2 0.130(6) 0.095(5) 0.098(4) 0.027(3) -0.002(4) 0.030(4) F1 0.062(2) 0.117(6) 0.085(4) -0.043(4) 0.009(3) -0.012(3) F3 0.055(2) 0.105(5) 0.102(4) 0.004(4) 0.040(2) 0.017(3) F1' 0.065(5) 0.088(5) 0.114(10) -0.019(6) 0.004(6) -0.019(4) F2' 0.083(6) 0.108(9) 0.070(6) 0.028(5) 0.011(4) 0.025(5) F3' 0.064(4) 0.084(7) 0.073(6) -0.014(5) 0.024(4) 0.026(5) N2 0.0399(10) 0.0555(11) 0.0369(9) -0.0050(8) 0.0058(7) 0.0065(9) O2 0.0916(15) 0.0865(15) 0.0709(12) 0.0266(10) 0.0400(11) 0.0189(11) C3 0.0526(16) 0.0732(19) 0.0686(17) -0.0014(14) -0.0109(13) 0.0117(14) N3 0.0339(9) 0.0523(12) 0.0435(10) -0.0061(8) 0.0066(8) 0.0060(8) O3 0.0694(13) 0.0806(14) 0.1000(15) -0.0390(12) 0.0337(11) -0.0228(11) C4 0.0677(18) 0.097(2) 0.0437(13) 0.0081(14) 0.0002(13) 0.0074(16) N4 0.0317(9) 0.0433(11) 0.0614(11) 0.0065(9) 0.0091(8) -0.0027(8) C5 0.0524(15) 0.085(2) 0.0435(13) 0.0022(12) 0.0109(11) 0.0056(13) C6 0.0359(11) 0.0494(13) 0.0429(12) -0.0031(10) 0.0048(9) -0.0003(10) C7 0.0460(13) 0.0595(15) 0.0435(12) -0.0132(11) 0.0119(10) 0.0023(11) C8 0.0370(11) 0.0485(14) 0.0491(12) -0.0121(10) 0.0114(10) -0.0014(10) C9 0.0400(12) 0.0564(15) 0.0580(14) -0.0158(11) 0.0126(10) 0.0039(11) C10 0.0355(12) 0.0581(16) 0.0851(18) 0.0067(13) 0.0135(12) -0.0078(11) C11 0.0437(13) 0.0390(13) 0.0836(16) 0.0087(12) 0.0129(12) 0.0016(11) C12 0.0568(16) 0.0688(19) 0.0640(17) -0.0080(15) 0.0173(13) 0.0103(14) O1 0.0582(10) 0.0725(12) 0.0650(10) -0.0062(9) 0.0322(9) 0.0093(9) _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 C1 C6 1.372(3) . ? C1 C2 1.383(4) . ? C1 H1 0.9300 . ? Mn1 O1 2.1651(17) 2 ? Mn1 O1 2.1651(17) . ? Mn1 N3 2.2264(17) 2 ? Mn1 N3 2.2264(17) . ? Mn1 N4 2.3599(19) 2 ? Mn1 N4 2.3599(19) . ? N1 N2 1.337(2) . ? N1 C7 1.353(3) . ? N1 C6 1.442(3) . ? S1 O3 1.421(2) . ? S1 O2 1.4219(19) . ? S1 O1 1.4422(17) . ? S1 C12 1.805(3) . ? C2 C3 1.370(4) . ? C2 H2 0.9300 . ? F2 C12 1.371(12) . ? F1 C12 1.287(11) . ? F3 C12 1.369(10) . ? F1' C12 1.39(2) . ? F2' C12 1.247(17) . ? F3' C12 1.283(17) . ? N2 N3 1.319(2) . ? C3 C4 1.350(4) . ? C3 H3 0.9300 . ? N3 C8 1.354(3) . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? N4 C9 1.481(3) 2 ? N4 C11 1.480(3) . ? N4 C10 1.489(3) . ? C5 C6 1.369(3) . ? C5 H5 0.9300 . ? C7 C8 1.359(3) . ? C7 H7 0.9300 . ? C8 C9 1.503(3) . ? C9 N4 1.481(3) 2 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C11 1.502(5) 2 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 C1 C2 118.3(2) . . ? C6 C1 H1 120.8 . . ? C2 C1 H1 120.8 . . ? O1 Mn1 O1 96.27(10) 2 . ? O1 Mn1 N3 94.29(7) 2 2 ? O1 Mn1 N3 91.59(7) . 2 ? O1 Mn1 N3 91.59(7) 2 . ? O1 Mn1 N3 94.29(7) . . ? N3 Mn1 N3 171.18(10) 2 . ? O1 Mn1 N4 94.12(7) 2 2 ? O1 Mn1 N4 164.18(7) . 2 ? N3 Mn1 N4 99.51(7) 2 2 ? N3 Mn1 N4 73.48(6) . 2 ? O1 Mn1 N4 164.18(7) 2 . ? O1 Mn1 N4 94.12(7) . . ? N3 Mn1 N4 73.48(6) 2 . ? N3 Mn1 N4 99.51(7) . . ? N4 Mn1 N4 78.45(10) 2 . ? N2 N1 C7 111.62(17) . . ? N2 N1 C6 119.99(17) . . ? C7 N1 C6 128.38(18) . . ? O3 S1 O2 115.42(14) . . ? O3 S1 O1 114.60(12) . . ? O2 S1 O1 114.22(12) . . ? O3 S1 C12 104.36(13) . . ? O2 S1 C12 103.28(14) . . ? O1 S1 C12 102.77(12) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? N3 N2 N1 105.70(16) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N2 N3 C8 110.14(16) . . ? N2 N3 Mn1 133.32(13) . . ? C8 N3 Mn1 116.03(14) . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C9 N4 C11 109.58(18) 2 . ? C9 N4 C10 109.32(19) 2 . ? C11 N4 C10 110.55(19) . . ? C9 N4 Mn1 109.11(13) 2 . ? C11 N4 Mn1 104.65(14) . . ? C10 N4 Mn1 113.50(14) . . ? C6 C5 C4 119.0(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 121.4(2) . . ? C5 C6 N1 119.3(2) . . ? C1 C6 N1 119.34(19) . . ? N1 C7 C8 104.71(19) . . ? N1 C7 H7 127.6 . . ? C8 C7 H7 127.6 . . ? N3 C8 C7 107.83(19) . . ? N3 C8 C9 120.32(18) . . ? C7 C8 C9 131.8(2) . . ? N4 C9 C8 110.01(18) 2 . ? N4 C9 H9A 109.7 2 . ? C8 C9 H9A 109.7 . . ? N4 C9 H9B 109.7 2 . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 C11 111.95(16) . 2 ? N4 C11 H11A 109.2 . . ? C11 C11 H11A 109.2 2 . ? N4 C11 H11B 109.2 . . ? C11 C11 H11B 109.2 2 . ? H11A C11 H11B 107.9 . . ? F1 C12 F2' 86.6(10) . . ? F1 C12 F3' 117.5(10) . . ? F2' C12 F3' 96.8(11) . . ? F1 C12 F2 107.2(6) . . ? F2' C12 F2 21.2(11) . . ? F3' C12 F2 91.3(14) . . ? F1 C12 F1' 22.5(10) . . ? F2' C12 F1' 107.9(10) . . ? F3' C12 F1' 106.5(11) . . ? F2 C12 F1' 128.9(9) . . ? F1 C12 F3 108.9(6) . . ? F2' C12 F3 115.9(9) . . ? F3' C12 F3 20.5(10) . . ? F2 C12 F3 111.8(8) . . ? F1' C12 F3 92.5(12) . . ? F1 C12 S1 114.3(6) . . ? F2' C12 S1 120.9(10) . . ? F3' C12 S1 116.4(8) . . ? F2 C12 S1 106.4(7) . . ? F1' C12 S1 107.3(9) . . ? F3 C12 S1 108.2(6) . . ? S1 O1 Mn1 155.02(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(5) . . . . ? C7 N1 N2 N3 -0.1(2) . . . . ? C6 N1 N2 N3 178.75(18) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? N1 N2 N3 C8 0.0(2) . . . . ? N1 N2 N3 Mn1 -171.25(15) . . . . ? O1 Mn1 N3 N2 94.8(2) 2 . . . ? O1 Mn1 N3 N2 -1.6(2) . . . . ? N3 Mn1 N3 N2 -133.3(2) 2 . . . ? N4 Mn1 N3 N2 -171.4(2) 2 . . . ? N4 Mn1 N3 N2 -96.5(2) . . . . ? O1 Mn1 N3 C8 -76.04(17) 2 . . . ? O1 Mn1 N3 C8 -172.45(16) . . . . ? N3 Mn1 N3 C8 55.83(16) 2 . . . ? N4 Mn1 N3 C8 17.78(16) 2 . . . ? N4 Mn1 N3 C8 92.63(17) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? O1 Mn1 N4 C9 -68.8(3) 2 . . 2 ? O1 Mn1 N4 C9 62.15(15) . . . 2 ? N3 Mn1 N4 C9 -28.29(14) 2 . . 2 ? N3 Mn1 N4 C9 157.21(14) . . . 2 ? N4 Mn1 N4 C9 -131.96(16) 2 . . 2 ? O1 Mn1 N4 C11 48.4(3) 2 . . . ? O1 Mn1 N4 C11 179.35(14) . . . . ? N3 Mn1 N4 C11 88.91(14) 2 . . . ? N3 Mn1 N4 C11 -85.59(14) . . . . ? N4 Mn1 N4 C11 -14.76(10) 2 . . . ? O1 Mn1 N4 C10 169.0(2) 2 . . . ? O1 Mn1 N4 C10 -60.02(17) . . . . ? N3 Mn1 N4 C10 -150.46(18) 2 . . . ? N3 Mn1 N4 C10 35.04(17) . . . . ? N4 Mn1 N4 C10 105.86(18) 2 . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C4 C5 C6 N1 179.3(2) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? C2 C1 C6 N1 -179.6(3) . . . . ? N2 N1 C6 C5 -144.1(2) . . . . ? C7 N1 C6 C5 34.6(4) . . . . ? N2 N1 C6 C1 36.1(3) . . . . ? C7 N1 C6 C1 -145.3(3) . . . . ? N2 N1 C7 C8 0.1(3) . . . . ? C6 N1 C7 C8 -178.6(2) . . . . ? N2 N3 C8 C7 0.1(3) . . . . ? Mn1 N3 C8 C7 173.02(16) . . . . ? N2 N3 C8 C9 -177.1(2) . . . . ? Mn1 N3 C8 C9 -4.2(3) . . . . ? N1 C7 C8 N3 -0.2(3) . . . . ? N1 C7 C8 C9 176.6(2) . . . . ? N3 C8 C9 N4 -21.9(3) . . . 2 ? C7 C8 C9 N4 161.7(2) . . . 2 ? C9 N4 C11 C11 160.7(2) 2 . . 2 ? C10 N4 C11 C11 -78.7(3) . . . 2 ? Mn1 N4 C11 C11 43.8(2) . . . 2 ? O3 S1 C12 F1 -170.2(9) . . . . ? O2 S1 C12 F1 68.7(9) . . . . ? O1 S1 C12 F1 -50.3(9) . . . . ? O3 S1 C12 F2' -69.0(15) . . . . ? O2 S1 C12 F2' 170.0(15) . . . . ? O1 S1 C12 F2' 50.9(15) . . . . ? O3 S1 C12 F3' 47.8(15) . . . . ? O2 S1 C12 F3' -73.3(15) . . . . ? O1 S1 C12 F3' 167.7(15) . . . . ? O3 S1 C12 F2 -52.1(6) . . . . ? O2 S1 C12 F2 -173.1(6) . . . . ? O1 S1 C12 F2 67.8(6) . . . . ? O3 S1 C12 F1' 166.9(16) . . . . ? O2 S1 C12 F1' 45.8(16) . . . . ? O1 S1 C12 F1' -73.2(16) . . . . ? O3 S1 C12 F3 68.2(7) . . . . ? O2 S1 C12 F3 -52.8(7) . . . . ? O1 S1 C12 F3 -171.9(7) . . . . ? O3 S1 O1 Mn1 -132.4(3) . . . . ? O2 S1 O1 Mn1 4.0(3) . . . . ? C12 S1 O1 Mn1 115.1(3) . . . . ? O1 Mn1 O1 S1 153.8(3) 2 . . . ? N3 Mn1 O1 S1 59.3(3) 2 . . . ? N3 Mn1 O1 S1 -114.2(3) . . . . ? N4 Mn1 O1 S1 -75.5(4) 2 . . . ? N4 Mn1 O1 S1 -14.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.329 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.041 # Attachment '4b-Mn.cif' data_mn-2 _database_code_depnum_ccdc_archive 'CCDC 734011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H34 F6 Mn N8 O6 S2' _chemical_formula_weight 811.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'Pc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.3766(19) _cell_length_b 21.576(4) _cell_length_c 9.2436(17) _cell_angle_alpha 90.00 _cell_angle_beta 115.806(2) _cell_angle_gamma 90.00 _cell_volume 1863.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8738 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.44 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 0.546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7719 _exptl_absorpt_correction_T_max 0.8987 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12744 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5635 _reflns_number_gt 5278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1322P)^2^+1.2630P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(3) _refine_ls_number_reflns 5635 _refine_ls_number_parameters 530 _refine_ls_number_restraints 110 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1931 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.095 _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 C1 C 0.4375(12) 0.5118(4) 0.8706(14) 0.097(3) Uani 1 1 d . . . H1A H 0.4141 0.4826 0.9338 0.146 Uiso 1 1 calc R . . H1B H 0.4871 0.5465 0.9365 0.146 Uiso 1 1 calc R . . H1C H 0.4978 0.4923 0.8294 0.146 Uiso 1 1 calc R . . F1 F 0.2333(8) 0.0897(3) 0.2187(9) 0.124(2) Uani 1 1 d U . . Mn1 Mn 0.50317(9) 0.26770(4) 0.70754(10) 0.0480(3) Uani 1 1 d . . . N1 N 0.2335(7) 0.4286(3) 0.6446(8) 0.0632(14) Uani 1 1 d . . . S1 S 0.25227(18) 0.19770(8) 0.3529(2) 0.0617(5) Uani 1 1 d . . . C2 C 0.3042(10) 0.5337(3) 0.7349(12) 0.075(2) Uani 1 1 d . . . F2 F 0.4417(9) 0.1288(4) 0.3167(12) 0.139(3) Uani 1 1 d U . . N2 N 0.3466(6) 0.4042(3) 0.6287(8) 0.0583(13) Uani 1 1 d . . . S2 S 0.7189(2) 0.33432(10) 0.5469(2) 0.0699(5) Uani 1 1 d . . . C3 C 0.2693(11) 0.5966(4) 0.7138(12) 0.084(2) Uani 1 1 d . . . H3 H 0.3330 0.6253 0.7835 0.101 Uiso 1 1 calc R . . N3 N 0.3482(7) 0.3449(3) 0.6626(8) 0.0587(13) Uani 1 1 d . . . O3 O 0.3680(7) 0.2219(3) 0.4929(9) 0.099(2) Uani 1 1 d U A . C4 C 0.1440(13) 0.6169(5) 0.5934(15) 0.092(3) Uani 1 1 d . . . H4 H 0.1226 0.6590 0.5847 0.111 Uiso 1 1 calc R . . F4 F 0.7009(16) 0.2192(5) 0.4428(19) 0.093(4) Uani 0.589(18) 1 d PU A 1 F5 F 0.8963(15) 0.2805(8) 0.4699(19) 0.094(4) Uani 0.589(18) 1 d PU A 1 F6 F 0.8751(15) 0.2265(8) 0.6681(17) 0.104(4) Uani 0.589(18) 1 d PU A 1 O4 O 0.6168(15) 0.3466(6) 0.3775(12) 0.077(3) Uani 0.589(18) 1 d PU A 1 O6 O 0.8178(15) 0.3835(7) 0.6144(17) 0.096(4) Uani 0.589(18) 1 d PU A 1 O2 O 0.214(3) 0.2279(10) 0.199(3) 0.098(5) Uani 0.589(18) 1 d PU A 1 F6' F 0.737(3) 0.2167(12) 0.514(3) 0.108(7) Uani 0.411(18) 1 d PU A 2 F4' F 0.874(2) 0.2537(8) 0.452(2) 0.074(4) Uani 0.411(18) 1 d PU A 2 F5' F 0.9095(15) 0.2632(9) 0.7068(18) 0.083(4) Uani 0.411(18) 1 d PU A 2 O6' O 0.875(2) 0.3436(11) 0.695(3) 0.105(6) Uani 0.411(18) 1 d PU A 2 O4' O 0.702(3) 0.3587(10) 0.416(3) 0.101(6) Uani 0.411(18) 1 d PU A 2 O2' O 0.254(5) 0.219(2) 0.217(6) 0.131(15) Uani 0.411(18) 1 d PU A 2 O1 O 0.1312(7) 0.1833(3) 0.3763(10) 0.098(2) Uani 1 1 d U A . N4 N 0.3681(8) 0.2403(3) 0.8437(9) 0.0688(16) Uani 1 1 d . . . C5 C 0.0521(11) 0.5776(4) 0.4882(12) 0.083(2) Uani 1 1 d . . . H5 H -0.0316 0.5931 0.4066 0.099 Uiso 1 1 calc R . . N5 N 0.6607(8) 0.2937(3) 0.9729(7) 0.0695(17) Uani 1 1 d . . . O5 O 0.6373(7) 0.3180(3) 0.6313(9) 0.0874(17) Uani 1 1 d U A . C6 C 0.0773(9) 0.5133(4) 0.4965(10) 0.072(2) Uani 1 1 d . . . N6 N 0.6628(5) 0.1905(2) 0.8021(6) 0.0528(12) Uani 1 1 d . . . C7 C -0.0275(12) 0.4703(5) 0.3792(14) 0.099(3) Uani 1 1 d . . . H7A H 0.0226 0.4383 0.3522 0.148 Uiso 1 1 calc R . . H7B H -0.0878 0.4927 0.2839 0.148 Uiso 1 1 calc R . . H7C H -0.0852 0.4519 0.4256 0.148 Uiso 1 1 calc R . . N7 N 0.6659(6) 0.1315(2) 0.7647(6) 0.0551(13) Uani 1 1 d . . . C8 C 0.2048(9) 0.4955(4) 0.6241(10) 0.0685(18) Uani 1 1 d . . . N8 N 0.7854(6) 0.1074(3) 0.8812(7) 0.0609(14) Uani 1 1 d . . . C9 C 0.1647(8) 0.3850(3) 0.6895(11) 0.070(2) Uani 1 1 d . . . H9 H 0.0832 0.3900 0.7063 0.084 Uiso 1 1 calc R . . C10 C 0.2421(8) 0.3316(3) 0.7047(10) 0.0651(18) Uani 1 1 d . . . C11 C 0.2260(11) 0.2675(3) 0.7552(15) 0.086(3) Uani 1 1 d . . . H11A H 0.1762 0.2687 0.8228 0.103 Uiso 1 1 calc R . . H11B H 0.1704 0.2425 0.6613 0.103 Uiso 1 1 calc R . . C12 C 0.3534(12) 0.1724(4) 0.8577(15) 0.091(3) Uani 1 1 d . . . H12A H 0.2888 0.1645 0.9047 0.137 Uiso 1 1 calc R . . H12B H 0.4454 0.1549 0.9245 0.137 Uiso 1 1 calc R . . H12C H 0.3165 0.1539 0.7528 0.137 Uiso 1 1 calc R . . C13 C 0.4341(15) 0.2698(4) 1.0008(13) 0.092(3) Uani 1 1 d . . . H13A H 0.3840 0.2896 1.0499 0.110 Uiso 1 1 calc R . . C14 C 0.5945(13) 0.2638(4) 1.0731(10) 0.081(2) Uani 1 1 d . . . H14A H 0.6195 0.2201 1.0864 0.098 Uiso 1 1 calc R . . H14B H 0.6352 0.2826 1.1789 0.098 Uiso 1 1 calc R . . C15 C 0.6734(12) 0.3616(4) 1.0054(13) 0.094(3) Uani 1 1 d . . . H15A H 0.7406 0.3689 1.1150 0.141 Uiso 1 1 calc R . . H15B H 0.5816 0.3780 0.9874 0.141 Uiso 1 1 calc R . . H15C H 0.7061 0.3817 0.9348 0.141 Uiso 1 1 calc R . . C16 C 0.7987(10) 0.2681(4) 1.0061(10) 0.077(2) Uani 1 1 d . . . H16A H 0.8853 0.2888 1.0594 0.093 Uiso 1 1 calc R . . C17 C 0.7831(7) 0.2033(3) 0.9427(9) 0.0600(16) Uani 1 1 d . . . C18 C 0.8603(8) 0.1509(4) 0.9961(9) 0.0651(17) Uani 1 1 d . . . H18 H 0.9448 0.1455 1.0891 0.078 Uiso 1 1 calc R . . C19 C 0.8196(8) 0.0424(3) 0.8807(9) 0.0628(17) Uani 1 1 d . . . C20 C 0.9339(10) 0.0247(5) 0.8511(10) 0.080(2) Uani 1 1 d . . . C21 C 1.0294(13) 0.0709(6) 0.8169(15) 0.107(3) Uani 1 1 d . . . H21A H 0.9744 0.1069 0.7649 0.161 Uiso 1 1 calc R . . H21B H 1.0657 0.0519 0.7482 0.161 Uiso 1 1 calc R . . H21C H 1.1079 0.0829 0.9162 0.161 Uiso 1 1 calc R . . C22 C 0.9585(15) -0.0396(6) 0.8513(14) 0.104(4) Uani 1 1 d . . . H22 H 1.0330 -0.0536 0.8297 0.125 Uiso 1 1 calc R . . C23 C 0.8761(11) -0.0818(5) 0.8824(14) 0.093(3) Uani 1 1 d . . . H23 H 0.8970 -0.1238 0.8849 0.111 Uiso 1 1 calc R . . C24 C 0.7625(12) -0.0630(4) 0.9102(13) 0.092(3) Uani 1 1 d . . . H24 H 0.7049 -0.0922 0.9278 0.110 Uiso 1 1 calc R . . C25 C 0.7334(8) 0.0010(3) 0.9121(9) 0.0673(18) Uani 1 1 d . . . C26 C 0.6146(10) 0.0205(4) 0.9502(14) 0.085(2) Uani 1 1 d . . . H26A H 0.5665 -0.0155 0.9635 0.127 Uiso 1 1 calc R . . H26B H 0.5480 0.0454 0.8639 0.127 Uiso 1 1 calc R . . H26C H 0.6523 0.0443 1.0477 0.127 Uiso 1 1 calc R . . C27 C 0.3195(9) 0.1233(4) 0.3378(11) 0.077(2) Uani 1 1 d . A . C28 C 0.8067(12) 0.2606(7) 0.5374(14) 0.102(4) Uani 1 1 d . A . F3 F 0.3590(10) 0.0892(3) 0.4662(11) 0.137(3) Uani 1 1 d U . . H13B H 0.372(8) 0.248(3) 1.056(9) 0.050(17) Uiso 1 1 d . . . H16B H 0.829(10) 0.270(3) 1.141(11) 0.07(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.099(7) 0.074(5) 0.110(8) -0.030(5) 0.037(6) -0.007(5) F1 0.120(5) 0.103(4) 0.122(5) -0.049(4) 0.028(4) -0.001(3) Mn1 0.0417(4) 0.0553(4) 0.0492(5) -0.0074(4) 0.0218(3) -0.0102(3) N1 0.062(3) 0.059(3) 0.081(4) -0.012(3) 0.042(3) -0.005(2) S1 0.0468(8) 0.0653(9) 0.0612(10) -0.0088(7) 0.0125(7) -0.0055(7) C2 0.078(5) 0.060(4) 0.096(6) -0.017(4) 0.048(5) -0.006(3) F2 0.103(5) 0.151(5) 0.176(6) -0.024(5) 0.074(5) 0.018(4) N2 0.054(3) 0.063(3) 0.071(4) -0.001(3) 0.038(3) 0.000(2) S2 0.0714(11) 0.0897(12) 0.0592(10) -0.0173(9) 0.0382(9) -0.0302(10) C3 0.098(6) 0.061(4) 0.098(6) -0.005(4) 0.048(6) 0.003(4) N3 0.057(3) 0.059(3) 0.069(4) -0.013(2) 0.036(3) -0.012(2) O3 0.070(4) 0.101(4) 0.098(4) -0.042(3) 0.010(3) -0.014(3) C4 0.106(7) 0.076(5) 0.120(8) 0.015(5) 0.072(7) 0.014(5) F4 0.102(7) 0.067(5) 0.095(7) 0.009(5) 0.030(6) 0.002(4) F5 0.077(6) 0.114(8) 0.106(7) -0.004(7) 0.055(5) 0.009(6) F6 0.087(6) 0.130(8) 0.100(7) 0.035(6) 0.046(5) 0.032(6) O4 0.077(6) 0.092(6) 0.052(5) -0.002(4) 0.019(4) 0.024(5) O6 0.087(7) 0.104(7) 0.115(8) -0.020(6) 0.060(6) -0.045(6) O2 0.105(9) 0.097(8) 0.087(8) 0.020(6) 0.038(7) 0.011(7) F6' 0.097(10) 0.121(10) 0.116(11) -0.018(8) 0.056(8) 0.021(7) F4' 0.073(7) 0.079(7) 0.079(7) 0.001(6) 0.041(6) 0.001(6) F5' 0.059(6) 0.107(8) 0.074(7) 0.016(6) 0.021(5) 0.008(6) O6' 0.088(9) 0.119(10) 0.104(10) -0.022(8) 0.040(7) -0.028(7) O4' 0.118(11) 0.112(9) 0.099(10) 0.014(7) 0.071(8) 0.001(8) O2' 0.129(18) 0.141(17) 0.130(17) 0.001(9) 0.062(11) -0.002(10) O1 0.073(4) 0.103(4) 0.125(5) -0.018(4) 0.048(4) -0.024(3) N4 0.072(4) 0.063(3) 0.090(5) -0.002(3) 0.052(4) -0.012(3) C5 0.073(5) 0.092(6) 0.089(6) 0.022(5) 0.041(5) 0.014(5) N5 0.090(5) 0.057(3) 0.053(3) -0.018(3) 0.023(3) -0.023(3) O5 0.078(4) 0.089(3) 0.118(5) 0.014(3) 0.064(3) -0.006(3) C6 0.064(4) 0.080(5) 0.078(5) 0.001(4) 0.035(4) -0.003(3) N6 0.038(2) 0.061(3) 0.050(3) 0.000(2) 0.009(2) -0.010(2) C7 0.074(6) 0.107(7) 0.092(7) -0.007(5) 0.015(5) 0.010(5) N7 0.045(3) 0.060(3) 0.047(3) -0.006(2) 0.007(2) -0.006(2) C8 0.077(5) 0.071(4) 0.077(5) 0.000(3) 0.052(4) 0.005(3) N8 0.042(3) 0.073(3) 0.054(3) -0.002(2) 0.008(2) -0.003(2) C9 0.061(4) 0.070(4) 0.103(6) -0.009(4) 0.057(4) -0.005(3) C10 0.053(4) 0.066(4) 0.091(5) -0.010(3) 0.045(4) -0.012(3) C11 0.089(6) 0.058(4) 0.151(9) -0.010(4) 0.090(7) -0.018(4) C12 0.103(7) 0.064(4) 0.136(9) 0.015(5) 0.079(7) -0.005(4) C13 0.133(9) 0.090(6) 0.086(6) -0.007(4) 0.079(7) 0.001(5) C14 0.117(8) 0.084(5) 0.053(4) -0.006(3) 0.047(5) -0.013(5) C15 0.089(6) 0.066(4) 0.096(7) -0.019(4) 0.010(5) -0.013(4) C16 0.075(5) 0.083(5) 0.054(4) -0.018(3) 0.009(4) -0.022(4) C17 0.053(4) 0.063(4) 0.055(4) -0.001(3) 0.015(3) -0.013(3) C18 0.058(4) 0.072(4) 0.054(4) -0.003(3) 0.013(3) -0.009(3) C19 0.059(4) 0.064(4) 0.055(4) -0.001(3) 0.015(3) 0.006(3) C20 0.064(5) 0.100(6) 0.062(5) 0.002(4) 0.015(4) -0.002(4) C21 0.093(7) 0.143(10) 0.097(7) 0.002(7) 0.052(6) -0.016(6) C22 0.110(8) 0.117(8) 0.089(7) 0.001(6) 0.048(6) 0.043(7) C23 0.077(6) 0.081(5) 0.105(7) 0.001(5) 0.025(5) 0.018(5) C24 0.098(7) 0.063(4) 0.104(7) -0.010(4) 0.034(5) 0.007(4) C25 0.070(4) 0.060(4) 0.067(4) 0.002(3) 0.026(3) 0.011(3) C26 0.081(5) 0.078(5) 0.111(7) 0.005(5) 0.055(5) -0.001(4) C27 0.058(4) 0.084(5) 0.073(5) 0.001(4) 0.014(4) -0.003(4) C28 0.064(5) 0.169(12) 0.079(6) 0.046(7) 0.037(5) 0.039(7) F3 0.139(5) 0.105(4) 0.141(5) 0.026(4) 0.038(4) 0.030(4) _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 C1 C2 1.483(14) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? F1 C27 1.296(10) . ? Mn1 O3 2.111(6) . ? Mn1 O5 2.113(6) . ? Mn1 N3 2.226(6) . ? Mn1 N6 2.241(5) . ? Mn1 N4 2.331(7) . ? Mn1 N5 2.348(6) . ? N1 C9 1.351(10) . ? N1 N2 1.352(8) . ? N1 C8 1.469(10) . ? S1 O2' 1.35(5) . ? S1 O1 1.399(7) . ? S1 O3 1.427(6) . ? S1 O2 1.45(2) . ? S1 C27 1.780(9) . ? C2 C8 1.368(12) . ? C2 C3 1.395(12) . ? F2 C27 1.369(12) . ? N2 N3 1.315(8) . ? S2 O4' 1.26(2) . ? S2 O6 1.418(10) . ? S2 O5 1.424(6) . ? S2 O4 1.484(10) . ? S2 O6' 1.62(2) . ? S2 C28 1.853(14) . ? C3 C4 1.365(15) . ? C3 H3 0.9300 . ? N3 C10 1.349(9) . ? C4 C5 1.329(15) . ? C4 H4 0.9300 . ? F4 C28 1.39(2) . ? F5 C28 1.393(19) . ? F6 C28 1.326(15) . ? F6' C28 1.15(3) . ? F4' C28 1.27(2) . ? F5' C28 1.462(19) . ? N4 C13 1.454(13) . ? N4 C11 1.462(13) . ? N4 C12 1.485(10) . ? C5 C6 1.407(13) . ? C5 H5 0.9300 . ? N5 C16 1.438(13) . ? N5 C15 1.490(10) . ? N5 C14 1.516(11) . ? C6 C8 1.390(12) . ? C6 C7 1.481(13) . ? N6 N7 1.324(8) . ? N6 C17 1.382(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? N7 N8 1.343(8) . ? N8 C18 1.377(9) . ? N8 C19 1.447(9) . ? C9 C10 1.377(11) . ? C9 H9 0.9300 . ? C10 C11 1.491(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.505(17) . ? C13 H13A 0.9300 . ? C13 H13B 1.09(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.498(11) . ? C16 H16A 0.9300 . ? C16 H16B 1.15(9) . ? C17 C18 1.347(11) . ? C18 H18 0.9300 . ? C19 C25 1.381(12) . ? C19 C20 1.382(13) . ? C20 C22 1.411(15) . ? C20 C21 1.534(15) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.362(18) . ? C22 H22 0.9300 . ? C23 C24 1.372(16) . ? C23 H23 0.9300 . ? C24 C25 1.415(11) . ? C24 H24 0.9300 . ? C25 C26 1.482(12) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 F3 1.301(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O3 Mn1 O5 101.0(3) . . ? O3 Mn1 N3 92.5(3) . . ? O5 Mn1 N3 94.6(2) . . ? O3 Mn1 N6 95.4(2) . . ? O5 Mn1 N6 91.7(2) . . ? N3 Mn1 N6 168.7(2) . . ? O3 Mn1 N4 94.6(3) . . ? O5 Mn1 N4 161.5(3) . . ? N3 Mn1 N4 74.6(2) . . ? N6 Mn1 N4 96.7(2) . . ? O3 Mn1 N5 165.7(3) . . ? O5 Mn1 N5 88.0(3) . . ? N3 Mn1 N5 97.7(2) . . ? N6 Mn1 N5 73.1(2) . . ? N4 Mn1 N5 78.7(3) . . ? C9 N1 N2 111.2(6) . . ? C9 N1 C8 128.3(6) . . ? N2 N1 C8 120.4(6) . . ? O2' S1 O1 126.9(19) . . ? O2' S1 O3 112(2) . . ? O1 S1 O3 113.5(5) . . ? O2' S1 O2 17(2) . . ? O1 S1 O2 111.8(11) . . ? O3 S1 O2 119.0(10) . . ? O2' S1 C27 94(2) . . ? O1 S1 C27 102.7(4) . . ? O3 S1 C27 101.4(4) . . ? O2 S1 C27 106.0(10) . . ? C8 C2 C3 114.6(9) . . ? C8 C2 C1 124.2(7) . . ? C3 C2 C1 121.1(8) . . ? N3 N2 N1 105.9(5) . . ? O4' S2 O6 83.0(13) . . ? O4' S2 O5 139.9(13) . . ? O6 S2 O5 115.7(6) . . ? O4' S2 O4 34.6(11) . . ? O6 S2 O4 112.2(8) . . ? O5 S2 O4 107.5(7) . . ? O4' S2 O6' 115.4(15) . . ? O6 S2 O6' 42.9(8) . . ? O5 S2 O6' 100.5(9) . . ? O4 S2 O6' 149.9(10) . . ? O4' S2 C28 100.3(11) . . ? O6 S2 C28 112.7(8) . . ? O5 S2 C28 103.6(5) . . ? O4 S2 C28 104.1(5) . . ? O6' S2 C28 79.3(9) . . ? C4 C3 C2 121.6(9) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? N2 N3 C10 110.5(6) . . ? N2 N3 Mn1 134.9(4) . . ? C10 N3 Mn1 113.6(5) . . ? S1 O3 Mn1 167.4(5) . . ? C5 C4 C3 121.1(9) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C13 N4 C11 107.8(8) . . ? C13 N4 C12 111.5(8) . . ? C11 N4 C12 109.2(7) . . ? C13 N4 Mn1 107.2(5) . . ? C11 N4 Mn1 107.0(5) . . ? C12 N4 Mn1 113.9(5) . . ? C4 C5 C6 122.1(9) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C16 N5 C15 110.0(7) . . ? C16 N5 C14 112.3(7) . . ? C15 N5 C14 108.6(7) . . ? C16 N5 Mn1 107.9(5) . . ? C15 N5 Mn1 113.9(5) . . ? C14 N5 Mn1 104.0(5) . . ? S2 O5 Mn1 161.0(5) . . ? C8 C6 C5 113.9(8) . . ? C8 C6 C7 124.9(8) . . ? C5 C6 C7 121.2(8) . . ? N7 N6 C17 108.8(5) . . ? N7 N6 Mn1 135.3(4) . . ? C17 N6 Mn1 115.5(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N6 N7 N8 106.4(5) . . ? C2 C8 C6 126.7(7) . . ? C2 C8 N1 116.8(7) . . ? C6 C8 N1 116.5(7) . . ? N7 N8 C18 111.6(6) . . ? N7 N8 C19 121.0(5) . . ? C18 N8 C19 127.4(6) . . ? N1 C9 C10 104.6(6) . . ? N1 C9 H9 127.7 . . ? C10 C9 H9 127.7 . . ? N3 C10 C9 107.7(6) . . ? N3 C10 C11 120.3(7) . . ? C9 C10 C11 132.0(7) . . ? N4 C11 C10 109.0(6) . . ? N4 C11 H11A 109.9 . . ? C10 C11 H11A 109.9 . . ? N4 C11 H11B 109.9 . . ? C10 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N4 C13 C14 110.7(8) . . ? N4 C13 H13A 124.6 . . ? C14 C13 H13A 124.6 . . ? N4 C13 H13B 99(4) . . ? C14 C13 H13B 121(4) . . ? H13A C13 H13B 53.3 . . ? C13 C14 N5 113.6(8) . . ? C13 C14 H14A 108.9 . . ? N5 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? N5 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? N5 C15 H15A 109.5 . . ? N5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 C17 110.3(6) . . ? N5 C16 H16A 124.8 . . ? C17 C16 H16A 124.8 . . ? N5 C16 H16B 90(5) . . ? C17 C16 H16B 113(4) . . ? H16A C16 H16B 70.1 . . ? C18 C17 N6 109.1(6) . . ? C18 C17 C16 133.9(7) . . ? N6 C17 C16 117.0(7) . . ? C17 C18 N8 104.1(6) . . ? C17 C18 H18 128.0 . . ? N8 C18 H18 128.0 . . ? C25 C19 C20 123.6(7) . . ? C25 C19 N8 116.3(7) . . ? C20 C19 N8 120.1(7) . . ? C19 C20 C22 116.2(10) . . ? C19 C20 C21 123.2(9) . . ? C22 C20 C21 120.5(11) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C20 121.9(11) . . ? C23 C22 H22 119.1 . . ? C20 C22 H22 119.1 . . ? C22 C23 C24 120.7(9) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 119.8(10) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C19 C25 C24 117.8(8) . . ? C19 C25 C26 123.2(7) . . ? C24 C25 C26 118.9(8) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? F1 C27 F3 106.6(8) . . ? F1 C27 F2 105.4(8) . . ? F3 C27 F2 103.6(8) . . ? F1 C27 S1 115.0(6) . . ? F3 C27 S1 114.6(7) . . ? F2 C27 S1 110.6(7) . . ? F6' C28 F4' 104.8(19) . . ? F6' C28 F6 76.0(16) . . ? F4' C28 F6 106.3(12) . . ? F6' C28 F4 25.2(14) . . ? F4' C28 F4 91.8(13) . . ? F6 C28 F4 100.3(14) . . ? F6' C28 F5 130.8(18) . . ? F4' C28 F5 26.3(8) . . ? F6 C28 F5 112.5(11) . . ? F4 C28 F5 114.5(12) . . ? F6' C28 F5' 109.8(17) . . ? F4' C28 F5' 109.1(12) . . ? F6 C28 F5' 36.3(7) . . ? F4 C28 F5' 134.9(13) . . ? F5 C28 F5' 98.6(12) . . ? F6' C28 S2 115.7(14) . . ? F4' C28 S2 123.0(11) . . ? F6 C28 S2 120.8(11) . . ? F4 C28 S2 108.1(8) . . ? F5 C28 S2 101.2(10) . . ? F5' C28 S2 93.5(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 N3 0.4(8) . . . . ? C8 N1 N2 N3 176.5(7) . . . . ? C8 C2 C3 C4 1.3(14) . . . . ? C1 C2 C3 C4 -177.2(10) . . . . ? N1 N2 N3 C10 -2.0(8) . . . . ? N1 N2 N3 Mn1 -169.0(5) . . . . ? O3 Mn1 N3 N2 -112.0(7) . . . . ? O5 Mn1 N3 N2 -10.7(7) . . . . ? N6 Mn1 N3 N2 113.0(11) . . . . ? N4 Mn1 N3 N2 154.0(7) . . . . ? N5 Mn1 N3 N2 77.9(7) . . . . ? O3 Mn1 N3 C10 81.3(6) . . . . ? O5 Mn1 N3 C10 -177.4(5) . . . . ? N6 Mn1 N3 C10 -53.7(12) . . . . ? N4 Mn1 N3 C10 -12.7(5) . . . . ? N5 Mn1 N3 C10 -88.7(5) . . . . ? O2' S1 O3 Mn1 114(4) . . . . ? O1 S1 O3 Mn1 -38(3) . . . . ? O2 S1 O3 Mn1 97(3) . . . . ? C27 S1 O3 Mn1 -148(3) . . . . ? O5 Mn1 O3 S1 -123(3) . . . . ? N3 Mn1 O3 S1 -28(3) . . . . ? N6 Mn1 O3 S1 144(3) . . . . ? N4 Mn1 O3 S1 47(3) . . . . ? N5 Mn1 O3 S1 108(3) . . . . ? C2 C3 C4 C5 -2.1(16) . . . . ? O3 Mn1 N4 C13 -176.8(6) . . . . ? O5 Mn1 N4 C13 -29.2(12) . . . . ? N3 Mn1 N4 C13 -85.4(6) . . . . ? N6 Mn1 N4 C13 87.2(6) . . . . ? N5 Mn1 N4 C13 16.0(6) . . . . ? O3 Mn1 N4 C11 -61.3(5) . . . . ? O5 Mn1 N4 C11 86.2(10) . . . . ? N3 Mn1 N4 C11 30.1(5) . . . . ? N6 Mn1 N4 C11 -157.4(5) . . . . ? N5 Mn1 N4 C11 131.4(5) . . . . ? O3 Mn1 N4 C12 59.4(7) . . . . ? O5 Mn1 N4 C12 -153.1(9) . . . . ? N3 Mn1 N4 C12 150.8(7) . . . . ? N6 Mn1 N4 C12 -36.6(7) . . . . ? N5 Mn1 N4 C12 -107.9(7) . . . . ? C3 C4 C5 C6 1.0(16) . . . . ? O3 Mn1 N5 C16 69.0(14) . . . . ? O5 Mn1 N5 C16 -61.0(5) . . . . ? N3 Mn1 N5 C16 -155.4(5) . . . . ? N6 Mn1 N5 C16 31.3(5) . . . . ? N4 Mn1 N5 C16 132.0(5) . . . . ? O3 Mn1 N5 C15 -168.6(12) . . . . ? O5 Mn1 N5 C15 61.4(7) . . . . ? N3 Mn1 N5 C15 -33.0(7) . . . . ? N6 Mn1 N5 C15 153.7(7) . . . . ? N4 Mn1 N5 C15 -105.6(7) . . . . ? O3 Mn1 N5 C14 -50.5(15) . . . . ? O5 Mn1 N5 C14 179.5(6) . . . . ? N3 Mn1 N5 C14 85.1(5) . . . . ? N6 Mn1 N5 C14 -88.2(5) . . . . ? N4 Mn1 N5 C14 12.5(5) . . . . ? O4' S2 O5 Mn1 84(2) . . . . ? O6 S2 O5 Mn1 -165.0(15) . . . . ? O4 S2 O5 Mn1 68.7(16) . . . . ? O6' S2 O5 Mn1 -122.5(17) . . . . ? C28 S2 O5 Mn1 -41.1(16) . . . . ? O3 Mn1 O5 S2 -32.3(15) . . . . ? N3 Mn1 O5 S2 -125.8(15) . . . . ? N6 Mn1 O5 S2 63.6(15) . . . . ? N4 Mn1 O5 S2 -179.2(11) . . . . ? N5 Mn1 O5 S2 136.6(15) . . . . ? C4 C5 C6 C8 0.6(13) . . . . ? C4 C5 C6 C7 179.2(10) . . . . ? O3 Mn1 N6 N7 -13.2(7) . . . . ? O5 Mn1 N6 N7 -114.5(7) . . . . ? N3 Mn1 N6 N7 121.6(10) . . . . ? N4 Mn1 N6 N7 82.0(7) . . . . ? N5 Mn1 N6 N7 158.1(7) . . . . ? O3 Mn1 N6 C17 174.6(5) . . . . ? O5 Mn1 N6 C17 73.4(5) . . . . ? N3 Mn1 N6 C17 -50.6(12) . . . . ? N4 Mn1 N6 C17 -90.1(5) . . . . ? N5 Mn1 N6 C17 -14.1(5) . . . . ? C17 N6 N7 N8 0.8(8) . . . . ? Mn1 N6 N7 N8 -171.7(5) . . . . ? C3 C2 C8 C6 0.4(13) . . . . ? C1 C2 C8 C6 178.9(10) . . . . ? C3 C2 C8 N1 -177.6(8) . . . . ? C1 C2 C8 N1 0.9(13) . . . . ? C5 C6 C8 C2 -1.3(13) . . . . ? C7 C6 C8 C2 -179.9(10) . . . . ? C5 C6 C8 N1 176.7(7) . . . . ? C7 C6 C8 N1 -1.9(13) . . . . ? C9 N1 C8 C2 109.8(10) . . . . ? N2 N1 C8 C2 -65.6(10) . . . . ? C9 N1 C8 C6 -68.4(11) . . . . ? N2 N1 C8 C6 116.2(8) . . . . ? N6 N7 N8 C18 0.4(8) . . . . ? N6 N7 N8 C19 177.7(6) . . . . ? N2 N1 C9 C10 1.3(9) . . . . ? C8 N1 C9 C10 -174.4(8) . . . . ? N2 N3 C10 C9 2.9(9) . . . . ? Mn1 N3 C10 C9 172.8(6) . . . . ? N2 N3 C10 C11 -177.5(8) . . . . ? Mn1 N3 C10 C11 -7.5(10) . . . . ? N1 C9 C10 N3 -2.4(9) . . . . ? N1 C9 C10 C11 178.0(10) . . . . ? C13 N4 C11 C10 73.2(9) . . . . ? C12 N4 C11 C10 -165.6(8) . . . . ? Mn1 N4 C11 C10 -41.8(9) . . . . ? N3 C10 C11 N4 35.3(12) . . . . ? C9 C10 C11 N4 -145.2(9) . . . . ? C11 N4 C13 C14 -158.0(7) . . . . ? C12 N4 C13 C14 82.2(9) . . . . ? Mn1 N4 C13 C14 -43.1(8) . . . . ? N4 C13 C14 N5 60.4(9) . . . . ? C16 N5 C14 C13 -157.3(7) . . . . ? C15 N5 C14 C13 80.8(9) . . . . ? Mn1 N5 C14 C13 -40.9(8) . . . . ? C15 N5 C16 C17 -168.4(7) . . . . ? C14 N5 C16 C17 70.4(8) . . . . ? Mn1 N5 C16 C17 -43.6(8) . . . . ? N7 N6 C17 C18 -1.8(9) . . . . ? Mn1 N6 C17 C18 172.4(5) . . . . ? N7 N6 C17 C16 -179.5(7) . . . . ? Mn1 N6 C17 C16 -5.3(9) . . . . ? N5 C16 C17 C18 -142.6(9) . . . . ? N5 C16 C17 N6 34.4(10) . . . . ? N6 C17 C18 N8 1.9(9) . . . . ? C16 C17 C18 N8 179.1(9) . . . . ? N7 N8 C18 C17 -1.4(9) . . . . ? C19 N8 C18 C17 -178.6(7) . . . . ? N7 N8 C19 C25 -69.8(9) . . . . ? C18 N8 C19 C25 107.1(9) . . . . ? N7 N8 C19 C20 110.7(8) . . . . ? C18 N8 C19 C20 -72.4(10) . . . . ? C25 C19 C20 C22 1.1(12) . . . . ? N8 C19 C20 C22 -179.4(8) . . . . ? C25 C19 C20 C21 -179.8(8) . . . . ? N8 C19 C20 C21 -0.3(12) . . . . ? C19 C20 C22 C23 -1.4(15) . . . . ? C21 C20 C22 C23 179.5(10) . . . . ? C20 C22 C23 C24 1.9(17) . . . . ? C22 C23 C24 C25 -2.2(16) . . . . ? C20 C19 C25 C24 -1.4(11) . . . . ? N8 C19 C25 C24 179.1(7) . . . . ? C20 C19 C25 C26 177.5(8) . . . . ? N8 C19 C25 C26 -2.0(11) . . . . ? C23 C24 C25 C19 1.9(13) . . . . ? C23 C24 C25 C26 -177.1(9) . . . . ? O2' S1 C27 F1 -68(2) . . . . ? O1 S1 C27 F1 61.6(9) . . . . ? O3 S1 C27 F1 179.2(8) . . . . ? O2 S1 C27 F1 -55.8(13) . . . . ? O2' S1 C27 F3 168(2) . . . . ? O1 S1 C27 F3 -62.4(8) . . . . ? O3 S1 C27 F3 55.2(8) . . . . ? O2 S1 C27 F3 -179.9(12) . . . . ? O2' S1 C27 F2 52(2) . . . . ? O1 S1 C27 F2 -179.1(7) . . . . ? O3 S1 C27 F2 -61.5(8) . . . . ? O2 S1 C27 F2 63.4(12) . . . . ? O4' S2 C28 F6' -108(2) . . . . ? O6 S2 C28 F6' 165.4(19) . . . . ? O5 S2 C28 F6' 39.6(19) . . . . ? O4 S2 C28 F6' -73(2) . . . . ? O6' S2 C28 F6' 138(2) . . . . ? O4' S2 C28 F4' 23(2) . . . . ? O6 S2 C28 F4' -64.1(16) . . . . ? O5 S2 C28 F4' 170.1(14) . . . . ? O4 S2 C28 F4' 57.8(17) . . . . ? O6' S2 C28 F4' -91.6(17) . . . . ? O4' S2 C28 F6 164(2) . . . . ? O6 S2 C28 F6 76.8(15) . . . . ? O5 S2 C28 F6 -49.0(14) . . . . ? O4 S2 C28 F6 -161.3(15) . . . . ? O6' S2 C28 F6 49.3(16) . . . . ? O4' S2 C28 F4 -82.0(17) . . . . ? O6 S2 C28 F4 -168.7(11) . . . . ? O5 S2 C28 F4 65.5(10) . . . . ? O4 S2 C28 F4 -46.8(12) . . . . ? O6' S2 C28 F4 163.8(13) . . . . ? O4' S2 C28 F5 38.6(17) . . . . ? O6 S2 C28 F5 -48.1(12) . . . . ? O5 S2 C28 F5 -173.9(9) . . . . ? O4 S2 C28 F5 73.8(12) . . . . ? O6' S2 C28 F5 -75.6(12) . . . . ? O4' S2 C28 F5' 138.2(17) . . . . ? O6 S2 C28 F5' 51.5(11) . . . . ? O5 S2 C28 F5' -74.3(10) . . . . ? O4 S2 C28 F5' 173.4(11) . . . . ? O6' S2 C28 F5' 24.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.418 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.082 # Attachment '4d-Mn.cif' data_mn-3 _database_code_depnum_ccdc_archive 'CCDC 734012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H33 F6 Mn N9 O8 S2' _chemical_formula_weight 856.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 19.677(5) _cell_length_b 14.929(5) _cell_length_c 25.509(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 7493(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9923 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 22.34 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3512 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7698 _exptl_absorpt_correction_T_max 0.8976 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51351 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6611 _reflns_number_gt 4459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1533P)^2^+23.0794P] 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 0.009(2) _refine_ls_number_reflns 6611 _refine_ls_number_parameters 489 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2868 _refine_ls_wR_factor_gt 0.2497 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.092 _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 0.07505(5) -0.02230(6) 0.76862(4) 0.0457(3) Uani 1 1 d . . . N8 N 0.1038(3) -0.1529(3) 0.7237(2) 0.0482(12) Uani 1 1 d . . . N1 N 0.2510(3) -0.1080(3) 0.85575(19) 0.0460(12) Uani 1 1 d . . . O4 O 0.1364(3) 0.0599(4) 0.7181(2) 0.0704(14) Uani 1 1 d U . . N4 N -0.0144(3) 0.0188(4) 0.7213(2) 0.0499(13) Uani 1 1 d . . . N7 N -0.0148(3) -0.1178(4) 0.7927(2) 0.0533(13) Uani 1 1 d . . . N5 N -0.0216(2) 0.0719(4) 0.6797(2) 0.0506(13) Uani 1 1 d . . . N6 N -0.0887(2) 0.0756(3) 0.67062(19) 0.0422(11) Uani 1 1 d . . . N3 N 0.1638(3) -0.0800(4) 0.8103(2) 0.0588(14) Uani 1 1 d . . . C18 C 0.2973(3) -0.0972(4) 0.8988(2) 0.0473(14) Uani 1 1 d . . . O8 O 0.4362(3) -0.0659(4) 1.0177(2) 0.0799(16) Uani 1 1 d U . . N2 N 0.1951(3) -0.0578(4) 0.8543(2) 0.0581(14) Uani 1 1 d . . . O7 O -0.1876(3) 0.2851(4) 0.5078(2) 0.0861(17) Uani 1 1 d U . . C5 C -0.1130(3) 0.1287(4) 0.6274(2) 0.0442(14) Uani 1 1 d . . . C6 C -0.0689(3) 0.1590(5) 0.5908(3) 0.0560(16) Uani 1 1 d . . . H6 H -0.0230 0.1448 0.5935 0.067 Uiso 1 1 calc R . . C8 C -0.1237(3) 0.0260(4) 0.7059(2) 0.0476(14) Uani 1 1 d . . . H8 H -0.1705 0.0185 0.7078 0.057 Uiso 1 1 calc R . . C9 C -0.0798(3) -0.0686(5) 0.7854(3) 0.0568(17) Uani 1 1 d . . . H9A H -0.0889 -0.0319 0.8160 0.068 Uiso 1 1 calc R . . H9B H -0.1169 -0.1110 0.7816 0.068 Uiso 1 1 calc R . . C22 C 0.3879(4) -0.0728(5) 0.9798(3) 0.0571(17) Uani 1 1 d . . . O3 O 0.0552(3) 0.0654(5) 0.8319(2) 0.0942(19) Uani 1 1 d U . . C16 C 0.1993(3) -0.1424(4) 0.7837(3) 0.0490(15) Uani 1 1 d . . . C4 C -0.1817(3) 0.1477(5) 0.6241(3) 0.0541(16) Uani 1 1 d . . . H4 H -0.2121 0.1259 0.6489 0.065 Uiso 1 1 calc R . . C15 C -0.0756(3) -0.0107(4) 0.7380(2) 0.0471(14) Uani 1 1 d . . . C19 C 0.2805(4) -0.0445(5) 0.9405(3) 0.0581(17) Uani 1 1 d . . . H19 H 0.2382 -0.0169 0.9416 0.070 Uiso 1 1 calc R . . C3 C -0.2035(4) 0.2002(5) 0.5828(3) 0.0650(19) Uani 1 1 d . . . H3 H -0.2494 0.2139 0.5800 0.078 Uiso 1 1 calc R . . C17 C 0.2557(3) -0.1614(4) 0.8129(3) 0.0523(15) Uani 1 1 d . . . H17 H 0.2899 -0.2022 0.8050 0.063 Uiso 1 1 calc R . . C21 C 0.4048(4) -0.1275(5) 0.9381(3) 0.067(2) Uani 1 1 d . . . H21 H 0.4467 -0.1563 0.9377 0.080 Uiso 1 1 calc R . . C2 C -0.1590(4) 0.2327(5) 0.5455(3) 0.0615(18) Uani 1 1 d . . . C12 C 0.0622(4) -0.2238(4) 0.7478(3) 0.0586(17) Uani 1 1 d . . . H12A H 0.0819 -0.2405 0.7812 0.070 Uiso 1 1 calc R . . H12B H 0.0628 -0.2763 0.7254 0.070 Uiso 1 1 calc R . . C23 C 0.3256(4) -0.0320(5) 0.9810(3) 0.0607(18) Uani 1 1 d . . . H23 H 0.3138 0.0042 1.0092 0.073 Uiso 1 1 calc R . . C14 C 0.1765(3) -0.1732(5) 0.7314(3) 0.0586(17) Uani 1 1 d . . . H14A H 0.2031 -0.1437 0.7044 0.070 Uiso 1 1 calc R . . H14B H 0.1837 -0.2372 0.7283 0.070 Uiso 1 1 calc R . . C20 C 0.3597(3) -0.1401(5) 0.8967(3) 0.0603(17) Uani 1 1 d . . . H20 H 0.3711 -0.1764 0.8684 0.072 Uiso 1 1 calc R . . C7 C -0.0915(4) 0.2115(5) 0.5491(3) 0.0637(18) Uani 1 1 d . . . H7 H -0.0610 0.2319 0.5240 0.076 Uiso 1 1 calc R . . C13 C 0.0900(4) -0.1474(6) 0.6666(3) 0.0667(19) Uani 1 1 d . . . H13A H 0.1173 -0.1008 0.6514 0.100 Uiso 1 1 calc R . . H13B H 0.0428 -0.1342 0.6610 0.100 Uiso 1 1 calc R . . H13C H 0.1010 -0.2036 0.6503 0.100 Uiso 1 1 calc R . . C11 C -0.0103(4) -0.1944(5) 0.7560(3) 0.0617(18) Uani 1 1 d . . . H11A H -0.0300 -0.1774 0.7226 0.074 Uiso 1 1 calc R . . H11B H -0.0365 -0.2441 0.7699 0.074 Uiso 1 1 calc R . . C10 C -0.0103(4) -0.1502(6) 0.8470(3) 0.073(2) Uani 1 1 d . . . H10A H -0.0466 -0.1918 0.8536 0.110 Uiso 1 1 calc R . . H10B H -0.0141 -0.1004 0.8706 0.110 Uiso 1 1 calc R . . H10C H 0.0325 -0.1795 0.8522 0.110 Uiso 1 1 calc R . . C24 C 0.4256(5) 0.0002(7) 1.0576(3) 0.082(2) Uani 1 1 d . . . H24A H 0.4623 -0.0021 1.0823 0.123 Uiso 1 1 calc R . . H24B H 0.3835 -0.0117 1.0753 0.123 Uiso 1 1 calc R . . H24C H 0.4238 0.0585 1.0418 0.123 Uiso 1 1 calc R . . C1 C -0.1433(6) 0.3277(8) 0.4722(4) 0.115(4) Uani 1 1 d . . . H1A H -0.1108 0.3629 0.4912 0.173 Uiso 1 1 calc R . . H1B H -0.1690 0.3658 0.4493 0.173 Uiso 1 1 calc R . . H1C H -0.1199 0.2832 0.4518 0.173 Uiso 1 1 calc R . . C28 C 0.6615(8) 0.2309(11) 0.4470(7) 0.156(6) Uani 1 1 d . . . H28A H 0.6163 0.2138 0.4570 0.234 Uiso 1 1 calc R . . H28B H 0.6596 0.2673 0.4160 0.234 Uiso 1 1 calc R . . H28C H 0.6822 0.2642 0.4749 0.234 Uiso 1 1 calc R . . N9 N 0.7582(15) 0.1281(18) 0.4182(11) 0.286(11) Uani 1 1 d U . . C27 C 0.6985(16) 0.1570(19) 0.4372(8) 0.241(13) Uani 1 1 d . . . S2 S 0.18961(9) 0.12646(12) 0.71948(8) 0.0586(5) Uani 1 1 d . . . S1 S 0.0312(2) 0.12263(17) 0.86766(11) 0.1196(13) Uani 1 1 d . . . O6 O 0.2317(3) 0.1239(5) 0.7643(2) 0.0944(19) Uani 1 1 d U . . O5 O 0.1708(3) 0.2131(4) 0.7029(3) 0.108(2) Uani 1 1 d U . . C25 C 0.2459(5) 0.0864(7) 0.6682(4) 0.086(3) Uani 1 1 d . . . O1 O 0.0304(4) 0.2113(5) 0.8637(3) 0.124(3) Uani 1 1 d U . . F1 F 0.2174(4) 0.0781(5) 0.6235(2) 0.131(2) Uani 1 1 d U . . F2 F 0.2694(4) 0.0033(5) 0.6810(3) 0.132(2) Uani 1 1 d U . . F3 F 0.2993(3) 0.1369(5) 0.6631(3) 0.140(3) Uani 1 1 d U . . F4 F 0.0394(5) 0.1390(6) 0.9684(3) 0.157(3) Uani 1 1 d U . . F5 F 0.0672(6) 0.0078(7) 0.9390(3) 0.171(3) Uani 1 1 d U . . F6 F 0.1297(5) 0.1143(7) 0.9286(4) 0.184(4) Uani 1 1 d U . . C26 C 0.0535(10) 0.0871(10) 0.9302(5) 0.152(7) Uani 1 1 d . . . O2 O -0.0481(5) 0.0901(9) 0.8789(5) 0.182(4) Uani 1 1 d U . . 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 0.0430(6) 0.0439(6) 0.0501(6) 0.0010(4) -0.0087(4) 0.0022(4) N8 0.051(3) 0.045(3) 0.049(3) 0.000(2) -0.009(2) -0.002(2) N1 0.046(3) 0.045(3) 0.047(3) 0.003(2) -0.006(2) 0.001(2) O4 0.056(3) 0.076(3) 0.079(3) 0.008(3) -0.008(2) -0.025(2) N4 0.041(3) 0.058(3) 0.051(3) 0.010(3) -0.006(2) -0.004(2) N7 0.052(3) 0.053(3) 0.056(3) 0.010(3) -0.005(2) -0.001(2) N5 0.039(3) 0.057(3) 0.057(3) 0.007(3) -0.005(2) -0.002(2) N6 0.036(2) 0.044(3) 0.047(3) -0.003(2) -0.005(2) 0.002(2) N3 0.062(3) 0.060(3) 0.055(3) -0.009(3) -0.016(3) 0.017(3) C18 0.048(3) 0.041(3) 0.053(3) 0.006(3) -0.011(3) -0.001(3) O8 0.074(3) 0.093(4) 0.073(3) -0.013(3) -0.027(3) 0.011(3) N2 0.055(3) 0.061(3) 0.058(3) -0.007(3) -0.017(3) 0.016(3) O7 0.094(4) 0.097(4) 0.067(3) 0.028(3) -0.014(3) 0.015(3) C5 0.045(3) 0.043(3) 0.044(3) -0.005(3) -0.006(3) 0.006(3) C6 0.049(4) 0.062(4) 0.057(4) 0.002(3) -0.005(3) 0.007(3) C8 0.036(3) 0.055(4) 0.051(3) 0.001(3) 0.000(3) -0.001(3) C9 0.048(4) 0.062(4) 0.060(4) 0.011(3) 0.001(3) -0.002(3) C22 0.060(4) 0.054(4) 0.058(4) 0.003(3) -0.017(3) -0.001(3) O3 0.096(4) 0.118(5) 0.069(3) -0.032(3) -0.007(3) 0.021(4) C16 0.051(4) 0.043(3) 0.054(4) -0.002(3) -0.004(3) 0.006(3) C4 0.053(4) 0.059(4) 0.051(4) 0.001(3) 0.000(3) 0.011(3) C15 0.040(3) 0.049(4) 0.052(4) 0.001(3) -0.001(3) -0.002(3) C19 0.051(4) 0.064(4) 0.060(4) -0.004(3) -0.007(3) 0.009(3) C3 0.055(4) 0.072(5) 0.068(5) -0.001(4) -0.011(3) 0.018(4) C17 0.048(3) 0.050(4) 0.059(4) -0.004(3) -0.005(3) 0.005(3) C21 0.054(4) 0.067(5) 0.079(5) -0.011(4) -0.018(4) 0.016(3) C2 0.078(5) 0.062(4) 0.044(4) 0.001(3) -0.014(3) 0.011(4) C12 0.067(4) 0.038(3) 0.071(4) -0.001(3) -0.014(4) -0.001(3) C23 0.066(4) 0.060(4) 0.056(4) -0.007(3) -0.008(3) 0.008(3) C14 0.055(4) 0.060(4) 0.061(4) -0.008(3) -0.011(3) 0.007(3) C20 0.054(4) 0.065(4) 0.062(4) -0.006(3) -0.008(3) 0.012(3) C7 0.066(4) 0.075(5) 0.050(4) 0.010(4) 0.003(3) 0.002(4) C13 0.078(5) 0.070(5) 0.051(4) -0.006(3) -0.014(4) -0.003(4) C11 0.067(4) 0.043(4) 0.075(5) 0.004(3) -0.007(4) -0.005(3) C10 0.079(5) 0.078(5) 0.063(4) 0.024(4) 0.004(4) 0.000(4) C24 0.082(6) 0.094(6) 0.069(5) -0.016(5) -0.024(4) 0.005(5) C1 0.130(9) 0.117(9) 0.099(7) 0.051(7) -0.023(7) -0.005(7) C28 0.136(11) 0.141(13) 0.190(16) -0.016(11) 0.013(11) 0.018(10) N9 0.293(14) 0.282(14) 0.283(14) -0.010(10) -0.004(10) -0.002(10) C27 0.30(3) 0.28(3) 0.143(16) -0.073(17) -0.062(18) 0.11(3) S2 0.0449(9) 0.0590(11) 0.0719(11) -0.0020(8) -0.0020(8) -0.0077(7) S1 0.219(4) 0.0603(14) 0.0791(16) -0.0203(12) -0.0251(19) 0.0392(18) O6 0.075(4) 0.124(5) 0.083(4) -0.010(3) -0.025(3) -0.020(3) O5 0.083(4) 0.072(4) 0.168(6) 0.017(4) 0.011(4) 0.006(3) C25 0.075(6) 0.087(6) 0.096(7) -0.013(5) 0.004(5) -0.024(5) O1 0.154(6) 0.082(4) 0.134(5) -0.018(4) -0.053(5) 0.024(4) F1 0.140(5) 0.166(6) 0.088(4) -0.029(4) 0.004(4) -0.034(4) F2 0.120(5) 0.115(4) 0.162(6) -0.023(4) 0.015(4) 0.029(4) F3 0.106(4) 0.159(5) 0.154(5) -0.054(4) 0.059(4) -0.058(4) F4 0.177(6) 0.196(7) 0.099(4) -0.038(5) -0.002(4) 0.013(5) F5 0.225(8) 0.152(6) 0.137(6) 0.044(5) -0.026(5) -0.005(6) F6 0.146(6) 0.203(8) 0.202(7) -0.030(6) -0.057(6) 0.028(6) C26 0.26(2) 0.120(10) 0.077(7) -0.040(7) -0.040(9) 0.094(12) O2 0.109(6) 0.219(8) 0.217(8) -0.042(7) 0.012(6) -0.031(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.114(6) . ? Mn1 O4 2.150(5) . ? Mn1 N3 2.218(5) . ? Mn1 N4 2.220(5) . ? Mn1 N8 2.332(5) . ? Mn1 N7 2.352(6) . ? N8 C12 1.473(9) . ? N8 C14 1.474(8) . ? N8 C13 1.484(8) . ? N1 N2 1.331(7) . ? N1 C17 1.357(8) . ? N1 C18 1.438(8) . ? O4 S2 1.444(5) . ? N4 N5 1.333(7) . ? N4 C15 1.351(8) . ? N7 C10 1.470(9) . ? N7 C11 1.479(9) . ? N7 C9 1.488(8) . ? N5 N6 1.340(7) . ? N6 C8 1.354(8) . ? N6 C5 1.440(7) . ? N3 N2 1.323(7) . ? N3 C16 1.347(8) . ? C18 C19 1.364(9) . ? C18 C20 1.385(9) . ? O8 C22 1.359(8) . ? O8 C24 1.432(10) . ? O7 C2 1.359(8) . ? O7 C1 1.410(12) . ? C5 C6 1.352(9) . ? C5 C4 1.383(9) . ? C6 C7 1.394(10) . ? C6 H6 0.9300 . ? C8 C15 1.367(9) . ? C8 H8 0.9300 . ? C9 C15 1.489(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C22 C23 1.369(10) . ? C22 C21 1.381(10) . ? O3 S1 1.337(6) . ? C16 C17 1.366(9) . ? C16 C14 1.481(9) . ? C4 C3 1.382(10) . ? C4 H4 0.9300 . ? C19 C23 1.374(9) . ? C19 H19 0.9300 . ? C3 C2 1.381(11) . ? C3 H3 0.9300 . ? C17 H17 0.9300 . ? C21 C20 1.392(10) . ? C21 H21 0.9300 . ? C2 C7 1.369(10) . ? C12 C11 1.508(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C23 H23 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C20 H20 0.9300 . ? C7 H7 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C28 C27 1.34(2) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? N9 C27 1.34(3) . ? S2 O5 1.411(7) . ? S2 O6 1.411(6) . ? S2 C25 1.815(10) . ? S1 O1 1.327(8) . ? S1 O2 1.659(10) . ? S1 C26 1.738(13) . ? C25 F1 1.279(11) . ? C25 F3 1.299(10) . ? C25 F2 1.362(12) . ? F4 C26 1.275(12) . ? F5 C26 1.236(14) . ? F6 C26 1.55(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Mn1 O4 102.0(3) . . ? O3 Mn1 N3 91.2(2) . . ? O4 Mn1 N3 93.9(2) . . ? O3 Mn1 N4 95.6(2) . . ? O4 Mn1 N4 87.81(19) . . ? N3 Mn1 N4 172.6(2) . . ? O3 Mn1 N8 159.7(2) . . ? O4 Mn1 N8 92.7(2) . . ? N3 Mn1 N8 73.72(19) . . ? N4 Mn1 N8 98.99(19) . . ? O3 Mn1 N7 92.2(2) . . ? O4 Mn1 N7 157.55(19) . . ? N3 Mn1 N7 103.3(2) . . ? N4 Mn1 N7 73.36(19) . . ? N8 Mn1 N7 78.7(2) . . ? C12 N8 C14 109.6(5) . . ? C12 N8 C13 110.3(5) . . ? C14 N8 C13 108.7(6) . . ? C12 N8 Mn1 105.1(4) . . ? C14 N8 Mn1 110.0(4) . . ? C13 N8 Mn1 113.1(4) . . ? N2 N1 C17 111.4(5) . . ? N2 N1 C18 118.9(5) . . ? C17 N1 C18 129.7(5) . . ? S2 O4 Mn1 141.8(3) . . ? N5 N4 C15 110.4(5) . . ? N5 N4 Mn1 133.0(4) . . ? C15 N4 Mn1 116.5(4) . . ? C10 N7 C11 109.8(6) . . ? C10 N7 C9 109.3(6) . . ? C11 N7 C9 110.7(5) . . ? C10 N7 Mn1 113.6(4) . . ? C11 N7 Mn1 105.0(4) . . ? C9 N7 Mn1 108.3(4) . . ? N4 N5 N6 105.5(5) . . ? N5 N6 C8 111.3(5) . . ? N5 N6 C5 118.9(5) . . ? C8 N6 C5 129.8(5) . . ? N2 N3 C16 111.0(5) . . ? N2 N3 Mn1 132.6(4) . . ? C16 N3 Mn1 115.8(4) . . ? C19 C18 C20 120.8(6) . . ? C19 C18 N1 120.4(6) . . ? C20 C18 N1 118.7(6) . . ? C22 O8 C24 117.1(6) . . ? N3 N2 N1 105.6(5) . . ? C2 O7 C1 117.3(7) . . ? C6 C5 C4 121.1(6) . . ? C6 C5 N6 119.9(5) . . ? C4 C5 N6 119.0(6) . . ? C5 C6 C7 120.6(6) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? N6 C8 C15 105.4(5) . . ? N6 C8 H8 127.3 . . ? C15 C8 H8 127.3 . . ? N7 C9 C15 109.8(5) . . ? N7 C9 H9A 109.7 . . ? C15 C9 H9A 109.7 . . ? N7 C9 H9B 109.7 . . ? C15 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O8 C22 C23 125.2(7) . . ? O8 C22 C21 115.1(6) . . ? C23 C22 C21 119.7(6) . . ? S1 O3 Mn1 169.2(5) . . ? N3 C16 C17 106.9(6) . . ? N3 C16 C14 120.7(6) . . ? C17 C16 C14 132.3(6) . . ? C3 C4 C5 117.7(6) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N4 C15 C8 107.3(5) . . ? N4 C15 C9 119.6(5) . . ? C8 C15 C9 133.0(6) . . ? C18 C19 C23 120.4(6) . . ? C18 C19 H19 119.8 . . ? C23 C19 H19 119.8 . . ? C2 C3 C4 121.9(7) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? N1 C17 C16 105.1(5) . . ? N1 C17 H17 127.4 . . ? C16 C17 H17 127.4 . . ? C22 C21 C20 120.7(7) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? O7 C2 C7 125.6(7) . . ? O7 C2 C3 115.3(7) . . ? C7 C2 C3 119.1(6) . . ? N8 C12 C11 112.0(5) . . ? N8 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? N8 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C22 C23 C19 120.1(7) . . ? C22 C23 H23 119.9 . . ? C19 C23 H23 119.9 . . ? N8 C14 C16 110.5(5) . . ? N8 C14 H14A 109.5 . . ? C16 C14 H14A 109.5 . . ? N8 C14 H14B 109.5 . . ? C16 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C18 C20 C21 118.2(7) . . ? C18 C20 H20 120.9 . . ? C21 C20 H20 120.9 . . ? C2 C7 C6 119.5(7) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? N8 C13 H13A 109.5 . . ? N8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C11 C12 111.7(6) . . ? N7 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N7 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? N7 C10 H10A 109.5 . . ? N7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O8 C24 H24A 109.5 . . ? O8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O7 C1 H1A 109.5 . . ? O7 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O7 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N9 C27 C28 144(3) . . ? O5 S2 O6 115.0(5) . . ? O5 S2 O4 115.7(4) . . ? O6 S2 O4 115.2(4) . . ? O5 S2 C25 104.3(5) . . ? O6 S2 C25 102.5(5) . . ? O4 S2 C25 101.5(4) . . ? O1 S1 O3 126.1(6) . . ? O1 S1 O2 107.1(7) . . ? O3 S1 O2 105.3(6) . . ? O1 S1 C26 112.2(6) . . ? O3 S1 C26 110.1(5) . . ? O2 S1 C26 89.4(9) . . ? F1 C25 F3 108.8(9) . . ? F1 C25 F2 105.9(9) . . ? F3 C25 F2 106.2(9) . . ? F1 C25 S2 114.0(7) . . ? F3 C25 S2 111.9(7) . . ? F2 C25 S2 109.5(7) . . ? F5 C26 F4 119.4(13) . . ? F5 C26 F6 92.6(12) . . ? F4 C26 F6 94.1(12) . . ? F5 C26 S1 121.0(9) . . ? F4 C26 S1 117.5(9) . . ? F6 C26 S1 98.1(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Mn1 N8 C12 48.8(8) . . . . ? O4 Mn1 N8 C12 -174.8(4) . . . . ? N3 Mn1 N8 C12 91.9(4) . . . . ? N4 Mn1 N8 C12 -86.6(4) . . . . ? N7 Mn1 N8 C12 -15.7(4) . . . . ? O3 Mn1 N8 C14 -69.1(8) . . . . ? O4 Mn1 N8 C14 67.3(4) . . . . ? N3 Mn1 N8 C14 -25.9(4) . . . . ? N4 Mn1 N8 C14 155.5(4) . . . . ? N7 Mn1 N8 C14 -133.6(4) . . . . ? O3 Mn1 N8 C13 169.2(7) . . . . ? O4 Mn1 N8 C13 -54.4(5) . . . . ? N3 Mn1 N8 C13 -147.7(5) . . . . ? N4 Mn1 N8 C13 33.8(5) . . . . ? N7 Mn1 N8 C13 104.7(5) . . . . ? O3 Mn1 O4 S2 38.6(6) . . . . ? N3 Mn1 O4 S2 -53.4(6) . . . . ? N4 Mn1 O4 S2 133.8(6) . . . . ? N8 Mn1 O4 S2 -127.3(6) . . . . ? N7 Mn1 O4 S2 166.4(4) . . . . ? O3 Mn1 N4 N5 102.1(6) . . . . ? O4 Mn1 N4 N5 0.3(6) . . . . ? N3 Mn1 N4 N5 -102.8(17) . . . . ? N8 Mn1 N4 N5 -92.0(6) . . . . ? N7 Mn1 N4 N5 -167.3(6) . . . . ? O3 Mn1 N4 C15 -74.0(5) . . . . ? O4 Mn1 N4 C15 -175.8(5) . . . . ? N3 Mn1 N4 C15 81.1(18) . . . . ? N8 Mn1 N4 C15 91.9(5) . . . . ? N7 Mn1 N4 C15 16.6(5) . . . . ? O3 Mn1 N7 C10 -55.4(5) . . . . ? O4 Mn1 N7 C10 175.3(6) . . . . ? N3 Mn1 N7 C10 36.3(5) . . . . ? N4 Mn1 N7 C10 -150.6(5) . . . . ? N8 Mn1 N7 C10 106.4(5) . . . . ? O3 Mn1 N7 C11 -175.4(4) . . . . ? O4 Mn1 N7 C11 55.3(7) . . . . ? N3 Mn1 N7 C11 -83.7(4) . . . . ? N4 Mn1 N7 C11 89.4(4) . . . . ? N8 Mn1 N7 C11 -13.6(4) . . . . ? O3 Mn1 N7 C9 66.2(5) . . . . ? O4 Mn1 N7 C9 -63.1(7) . . . . ? N3 Mn1 N7 C9 158.0(4) . . . . ? N4 Mn1 N7 C9 -28.9(4) . . . . ? N8 Mn1 N7 C9 -132.0(4) . . . . ? C15 N4 N5 N6 0.3(7) . . . . ? Mn1 N4 N5 N6 -176.0(4) . . . . ? N4 N5 N6 C8 0.2(7) . . . . ? N4 N5 N6 C5 -180.0(5) . . . . ? O3 Mn1 N3 N2 -7.6(7) . . . . ? O4 Mn1 N3 N2 94.5(7) . . . . ? N4 Mn1 N3 N2 -162.7(14) . . . . ? N8 Mn1 N3 N2 -173.8(7) . . . . ? N7 Mn1 N3 N2 -100.0(7) . . . . ? O3 Mn1 N3 C16 -177.4(5) . . . . ? O4 Mn1 N3 C16 -75.3(5) . . . . ? N4 Mn1 N3 C16 27(2) . . . . ? N8 Mn1 N3 C16 16.3(5) . . . . ? N7 Mn1 N3 C16 90.1(5) . . . . ? N2 N1 C18 C19 7.7(9) . . . . ? C17 N1 C18 C19 -174.9(6) . . . . ? N2 N1 C18 C20 -171.2(6) . . . . ? C17 N1 C18 C20 6.2(10) . . . . ? C16 N3 N2 N1 -0.8(8) . . . . ? Mn1 N3 N2 N1 -171.0(5) . . . . ? C17 N1 N2 N3 0.4(7) . . . . ? C18 N1 N2 N3 178.3(5) . . . . ? N5 N6 C5 C6 13.1(8) . . . . ? C8 N6 C5 C6 -167.1(6) . . . . ? N5 N6 C5 C4 -167.0(6) . . . . ? C8 N6 C5 C4 12.9(9) . . . . ? C4 C5 C6 C7 0.9(10) . . . . ? N6 C5 C6 C7 -179.1(6) . . . . ? N5 N6 C8 C15 -0.6(7) . . . . ? C5 N6 C8 C15 179.6(6) . . . . ? C10 N7 C9 C15 161.4(6) . . . . ? C11 N7 C9 C15 -77.6(7) . . . . ? Mn1 N7 C9 C15 37.1(6) . . . . ? C24 O8 C22 C23 -10.6(11) . . . . ? C24 O8 C22 C21 170.9(7) . . . . ? O4 Mn1 O3 S1 102(3) . . . . ? N3 Mn1 O3 S1 -163(3) . . . . ? N4 Mn1 O3 S1 13(3) . . . . ? N8 Mn1 O3 S1 -122(3) . . . . ? N7 Mn1 O3 S1 -60(3) . . . . ? N2 N3 C16 C17 0.8(8) . . . . ? Mn1 N3 C16 C17 172.8(4) . . . . ? N2 N3 C16 C14 -175.8(6) . . . . ? Mn1 N3 C16 C14 -3.8(8) . . . . ? C6 C5 C4 C3 -1.2(10) . . . . ? N6 C5 C4 C3 178.8(6) . . . . ? N5 N4 C15 C8 -0.6(7) . . . . ? Mn1 N4 C15 C8 176.3(4) . . . . ? N5 N4 C15 C9 -177.7(6) . . . . ? Mn1 N4 C15 C9 -0.8(8) . . . . ? N6 C8 C15 N4 0.7(7) . . . . ? N6 C8 C15 C9 177.3(7) . . . . ? N7 C9 C15 N4 -26.0(9) . . . . ? N7 C9 C15 C8 157.8(7) . . . . ? C20 C18 C19 C23 0.9(11) . . . . ? N1 C18 C19 C23 -178.0(6) . . . . ? C5 C4 C3 C2 0.3(11) . . . . ? N2 N1 C17 C16 0.0(7) . . . . ? C18 N1 C17 C16 -177.5(6) . . . . ? N3 C16 C17 N1 -0.5(7) . . . . ? C14 C16 C17 N1 175.6(7) . . . . ? O8 C22 C21 C20 -179.9(7) . . . . ? C23 C22 C21 C20 1.5(12) . . . . ? C1 O7 C2 C7 -6.0(12) . . . . ? C1 O7 C2 C3 173.4(8) . . . . ? C4 C3 C2 O7 -178.5(7) . . . . ? C4 C3 C2 C7 0.9(12) . . . . ? C14 N8 C12 C11 162.4(6) . . . . ? C13 N8 C12 C11 -77.9(7) . . . . ? Mn1 N8 C12 C11 44.3(6) . . . . ? O8 C22 C23 C19 -179.4(7) . . . . ? C21 C22 C23 C19 -0.9(11) . . . . ? C18 C19 C23 C22 -0.2(11) . . . . ? C12 N8 C14 C16 -83.4(7) . . . . ? C13 N8 C14 C16 156.0(6) . . . . ? Mn1 N8 C14 C16 31.7(7) . . . . ? N3 C16 C14 N8 -20.0(9) . . . . ? C17 C16 C14 N8 164.4(7) . . . . ? C19 C18 C20 C21 -0.4(11) . . . . ? N1 C18 C20 C21 178.5(6) . . . . ? C22 C21 C20 C18 -0.8(12) . . . . ? O7 C2 C7 C6 178.1(7) . . . . ? C3 C2 C7 C6 -1.2(11) . . . . ? C5 C6 C7 C2 0.4(11) . . . . ? C10 N7 C11 C12 -80.5(7) . . . . ? C9 N7 C11 C12 158.8(6) . . . . ? Mn1 N7 C11 C12 42.0(6) . . . . ? N8 C12 C11 N7 -62.5(8) . . . . ? Mn1 O4 S2 O5 -112.8(6) . . . . ? Mn1 O4 S2 O6 25.3(7) . . . . ? Mn1 O4 S2 C25 135.1(6) . . . . ? Mn1 O3 S1 O1 -83(3) . . . . ? Mn1 O3 S1 O2 42(3) . . . . ? Mn1 O3 S1 C26 137(3) . . . . ? O5 S2 C25 F1 -63.5(8) . . . . ? O6 S2 C25 F1 176.4(8) . . . . ? O4 S2 C25 F1 57.0(8) . . . . ? O5 S2 C25 F3 60.5(9) . . . . ? O6 S2 C25 F3 -59.6(9) . . . . ? O4 S2 C25 F3 -179.0(8) . . . . ? O5 S2 C25 F2 178.0(6) . . . . ? O6 S2 C25 F2 57.9(7) . . . . ? O4 S2 C25 F2 -61.4(7) . . . . ? O1 S1 C26 F5 -168.6(16) . . . . ? O3 S1 C26 F5 -23(2) . . . . ? O2 S1 C26 F5 83.2(18) . . . . ? O1 S1 C26 F4 28.2(19) . . . . ? O3 S1 C26 F4 173.9(14) . . . . ? O2 S1 C26 F4 -80.0(16) . . . . ? O1 S1 C26 F6 -70.7(9) . . . . ? O3 S1 C26 F6 75.0(9) . . . . ? O2 S1 C26 F6 -178.9(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.700 _refine_diff_density_min -1.600 _refine_diff_density_rms 0.100 # Attachment '6a-Zn.cif' data_zn-1 _database_code_depnum_ccdc_archive 'CCDC 736726' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 Cl2 N8 O10 Zn' _chemical_formula_weight 702.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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(1)/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 16.1160(12) _cell_length_b 11.5326(8) _cell_length_c 18.0774(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.0980(10) _cell_angle_gamma 90.00 _cell_volume 3090.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9985 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.37 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 1.031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6266 _exptl_absorpt_correction_T_max 0.8203 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21604 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5453 _reflns_number_gt 4482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0855P)^2^+1.7446P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0.009(2) _refine_ls_number_reflns 5453 _refine_ls_number_parameters 400 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.023 _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 Zn1 Zn 0.34637(2) 0.67898(3) 0.09886(2) 0.04134(16) Uani 1 1 d . . . Cl1 Cl 0.45658(6) 0.23696(8) 0.12511(5) 0.0528(2) Uani 1 1 d . . . C6 C 0.7188(2) 0.6341(3) 0.2227(2) 0.0494(8) Uani 1 1 d . . . C19 C -0.1801(3) 0.7277(6) -0.0547(4) 0.0951(17) Uani 1 1 d . . . H19 H -0.2333 0.7161 -0.0995 0.114 Uiso 1 1 calc R . . C17 C -0.0220(2) 0.7100(4) 0.0083(2) 0.0546(9) Uani 1 1 d . . . C5 C 0.7282(3) 0.5275(4) 0.2590(2) 0.0665(11) Uani 1 1 d . . . H5 H 0.6787 0.4894 0.2619 0.080 Uiso 1 1 calc R . . C22 C -0.0232(3) 0.7565(6) 0.0765(3) 0.0915(16) Uani 1 1 d . . . H22 H 0.0299 0.7631 0.1222 0.110 Uiso 1 1 calc R . . C18 C -0.1001(3) 0.6918(5) -0.0571(3) 0.0821(14) Uani 1 1 d . . . H18 H -0.0991 0.6556 -0.1027 0.099 Uiso 1 1 calc R . . C1 C 0.7911(3) 0.6897(4) 0.2162(3) 0.0758(13) Uani 1 1 d . . . H1 H 0.7839 0.7612 0.1906 0.091 Uiso 1 1 calc R . . C3 C 0.8864(3) 0.5333(5) 0.2869(3) 0.0839(14) Uani 1 1 d . . . H3 H 0.9435 0.5003 0.3101 0.101 Uiso 1 1 calc R . . C20 C -0.1833(3) 0.7794(4) 0.0110(4) 0.0788(14) Uani 1 1 d . . . H20 H -0.2381 0.8044 0.0113 0.095 Uiso 1 1 calc R . . C4 C 0.8138(3) 0.4781(5) 0.2912(3) 0.0840(14) Uani 1 1 d . . . H4 H 0.8216 0.4061 0.3160 0.101 Uiso 1 1 calc R . . C2 C 0.8749(3) 0.6368(5) 0.2487(4) 0.0898(15) Uani 1 1 d . . . H2 H 0.9242 0.6730 0.2441 0.108 Uiso 1 1 calc R . . C21 C -0.1047(4) 0.7945(6) 0.0775(4) 0.1020(19) Uani 1 1 d . . . H21 H -0.1059 0.8302 0.1232 0.122 Uiso 1 1 calc R . . N8 N 0.06195(19) 0.6744(3) 0.00578(18) 0.0520(7) Uani 1 1 d . . . C16 C 0.0790(2) 0.6077(4) -0.0487(2) 0.0606(10) Uani 1 1 d . . . H16 H 0.0373 0.5713 -0.0939 0.073 Uiso 1 1 calc R . . C15 C 0.1701(2) 0.6059(3) -0.0226(2) 0.0517(8) Uani 1 1 d . . . N6 N 0.20386(18) 0.6685(3) 0.04533(17) 0.0500(7) Uani 1 1 d . . . N7 N 0.13878(19) 0.7127(3) 0.06314(17) 0.0518(7) Uani 1 1 d . . . N3 N 0.48924(19) 0.6943(2) 0.14624(18) 0.0460(7) Uani 1 1 d . . . N2 N 0.55783(18) 0.6228(2) 0.17502(16) 0.0460(6) Uani 1 1 d . . . N1 N 0.63096(19) 0.6871(2) 0.18871(17) 0.0453(7) Uani 1 1 d . . . C8 C 0.5184(2) 0.8028(3) 0.1411(2) 0.0498(8) Uani 1 1 d . . . C7 C 0.6090(3) 0.7990(3) 0.1686(2) 0.0521(9) Uani 1 1 d . . . H7 H 0.6481 0.8603 0.1729 0.063 Uiso 1 1 calc R . . N4 N 0.3641(2) 0.8478(3) 0.05193(18) 0.0501(7) Uani 1 1 d . . . C9 C 0.4499(3) 0.8977(3) 0.1099(3) 0.0624(10) Uani 1 1 d . . . H9A H 0.4399 0.9339 0.1542 0.075 Uiso 1 1 calc R . . H9B H 0.4717 0.9565 0.0835 0.075 Uiso 1 1 calc R . . C11 C 0.3727(3) 0.8194(3) -0.0250(2) 0.0592(10) Uani 1 1 d . . . H11A H 0.4334 0.7921 -0.0136 0.071 Uiso 1 1 calc R . . H11B H 0.3629 0.8889 -0.0575 0.071 Uiso 1 1 calc R . . C12 C 0.3059(3) 0.7278(4) -0.0715(2) 0.0594(10) Uani 1 1 d . . . H12A H 0.2451 0.7562 -0.0849 0.071 Uiso 1 1 calc R . . H12B H 0.3132 0.7116 -0.1213 0.071 Uiso 1 1 calc R . . N5 N 0.31935(19) 0.6196(3) -0.02390(16) 0.0485(7) Uani 1 1 d . . . O9 O 0.3317(2) 0.7488(3) 0.20167(16) 0.0576(7) Uani 1 1 d U . . H9 H 0.3775 0.7357 0.2417 0.086 Uiso 1 1 calc R . . O10 O 0.3512(2) 0.5098(2) 0.14334(19) 0.0644(7) Uani 1 1 d DU . . H10 H 0.3985 0.4786 0.1473 0.097 Uiso 1 1 calc R . . O1 O 0.53466(19) 0.1645(3) 0.15313(19) 0.0722(8) Uani 1 1 d U . . O2 O 0.3898(2) 0.1918(3) 0.1486(2) 0.0897(11) Uani 1 1 d U . . O3 O 0.4230(2) 0.2466(4) 0.04073(19) 0.1025(12) Uani 1 1 d U . . O4 O 0.4852(3) 0.3477(3) 0.1623(3) 0.1133(14) Uani 1 1 d U . . C13 C 0.3934(3) 0.5505(4) -0.0303(2) 0.0588(10) Uani 1 1 d . . . H13A H 0.3780 0.5289 -0.0854 0.088 Uiso 1 1 calc R . . H13B H 0.4026 0.4819 0.0020 0.088 Uiso 1 1 calc R . . H13C H 0.4477 0.5958 -0.0118 0.088 Uiso 1 1 calc R . . C10 C 0.2896(3) 0.9317(4) 0.0373(3) 0.0680(11) Uani 1 1 d . . . H10A H 0.2808 0.9438 0.0863 0.102 Uiso 1 1 calc R . . H10B H 0.2352 0.9016 -0.0031 0.102 Uiso 1 1 calc R . . H10C H 0.3046 1.0040 0.0194 0.102 Uiso 1 1 calc R . . C14 C 0.2354(2) 0.5495(4) -0.0520(2) 0.0607(10) Uani 1 1 d . . . H14A H 0.2486 0.4712 -0.0311 0.073 Uiso 1 1 calc R . . H14B H 0.2095 0.5456 -0.1103 0.073 Uiso 1 1 calc R . . O8 O 0.8101(3) 0.3411(3) 0.7474(2) 0.1056(13) Uani 1 1 d U . . O5 O 0.7743(3) 0.5191(4) 0.7860(3) 0.1202(15) Uani 1 1 d U . . O6 O 0.7901(4) 0.5053(4) 0.6667(2) 0.1276(16) Uani 1 1 d U . . O7 O 0.9145(3) 0.4933(5) 0.7866(3) 0.1377(18) Uani 1 1 d U . . Cl2 Cl 0.82451(7) 0.46189(10) 0.74605(6) 0.0646(3) Uani 1 1 d . . . H101 H 0.322(3) 0.484(5) 0.170(3) 0.099(18) Uiso 1 1 d D . . H100 H 0.294(3) 0.731(5) 0.207(3) 0.073(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0327(2) 0.0497(3) 0.0426(2) -0.00168(15) 0.01576(17) 0.00362(15) Cl1 0.0396(4) 0.0610(6) 0.0585(5) 0.0037(4) 0.0199(4) 0.0024(4) C6 0.0371(18) 0.058(2) 0.0535(19) -0.0036(16) 0.0184(15) 0.0023(15) C19 0.036(2) 0.125(5) 0.108(4) -0.013(4) 0.010(2) 0.005(3) C17 0.0328(18) 0.063(2) 0.066(2) -0.0024(18) 0.0167(16) 0.0029(16) C5 0.047(2) 0.081(3) 0.072(3) 0.021(2) 0.0244(19) 0.007(2) C22 0.046(2) 0.135(5) 0.093(3) -0.024(3) 0.026(2) 0.004(3) C18 0.040(2) 0.110(4) 0.081(3) -0.013(3) 0.008(2) 0.008(2) C1 0.046(2) 0.070(3) 0.114(4) 0.011(2) 0.034(2) 0.002(2) C3 0.046(2) 0.098(4) 0.100(3) 0.019(3) 0.019(2) 0.015(2) C20 0.040(2) 0.077(3) 0.123(4) 0.014(3) 0.036(3) 0.013(2) C4 0.057(3) 0.092(3) 0.098(3) 0.037(3) 0.025(2) 0.020(2) C2 0.048(3) 0.096(4) 0.126(4) 0.000(3) 0.035(3) -0.009(3) C21 0.059(3) 0.143(5) 0.115(4) -0.026(4) 0.046(3) 0.011(3) N8 0.0294(14) 0.069(2) 0.0521(16) -0.0090(14) 0.0099(12) 0.0004(13) C16 0.043(2) 0.079(3) 0.053(2) -0.0197(19) 0.0108(16) -0.0012(18) C15 0.0425(19) 0.061(2) 0.0492(18) -0.0109(16) 0.0151(15) 0.0046(16) N6 0.0312(14) 0.069(2) 0.0466(15) -0.0118(13) 0.0122(12) 0.0029(13) N7 0.0317(14) 0.074(2) 0.0488(16) -0.0115(14) 0.0148(12) 0.0007(14) N3 0.0366(15) 0.0457(16) 0.0559(17) -0.0026(12) 0.0184(13) 0.0004(12) N2 0.0376(15) 0.0483(16) 0.0524(15) -0.0023(13) 0.0178(12) 0.0004(13) N1 0.0351(15) 0.0521(17) 0.0502(15) -0.0045(12) 0.0184(12) -0.0016(12) C8 0.0459(19) 0.047(2) 0.059(2) -0.0033(16) 0.0229(16) -0.0012(15) C7 0.048(2) 0.046(2) 0.066(2) -0.0039(16) 0.0255(17) -0.0059(16) N4 0.0449(16) 0.0459(16) 0.0624(18) 0.0036(13) 0.0241(14) 0.0113(13) C9 0.056(2) 0.047(2) 0.086(3) -0.0034(19) 0.029(2) 0.0039(17) C11 0.062(2) 0.063(2) 0.062(2) 0.0184(18) 0.034(2) 0.0162(19) C12 0.060(2) 0.078(3) 0.0461(18) 0.0108(18) 0.0278(17) 0.021(2) N5 0.0441(16) 0.0587(18) 0.0462(15) -0.0060(13) 0.0214(12) 0.0107(13) O9 0.0401(15) 0.083(2) 0.0487(14) -0.0124(13) 0.0166(12) 0.0043(14) O10 0.0615(17) 0.0573(16) 0.0851(19) 0.0129(14) 0.0402(16) 0.0079(13) O1 0.0524(16) 0.0737(19) 0.084(2) -0.0054(15) 0.0194(14) 0.0131(14) O2 0.0538(18) 0.141(3) 0.082(2) 0.0194(19) 0.0355(16) -0.0099(18) O3 0.071(2) 0.173(4) 0.0625(18) 0.020(2) 0.0246(16) 0.006(2) O4 0.087(3) 0.071(2) 0.161(4) -0.023(2) 0.025(2) 0.0066(19) C13 0.052(2) 0.069(2) 0.062(2) -0.0064(18) 0.0295(18) 0.0158(19) C10 0.057(2) 0.064(2) 0.083(3) 0.006(2) 0.028(2) 0.022(2) C14 0.049(2) 0.074(3) 0.057(2) -0.0205(19) 0.0193(17) 0.0042(19) O8 0.133(3) 0.079(2) 0.096(3) -0.0142(19) 0.036(2) -0.015(2) O5 0.116(3) 0.129(3) 0.154(4) 0.007(3) 0.094(3) 0.012(3) O6 0.182(4) 0.121(3) 0.075(2) 0.006(2) 0.045(3) -0.026(3) O7 0.059(2) 0.162(4) 0.169(4) -0.058(3) 0.020(2) -0.024(2) Cl2 0.0559(6) 0.0741(7) 0.0614(6) -0.0079(5) 0.0206(4) -0.0117(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O10 2.100(3) . ? Zn1 N6 2.117(3) . ? Zn1 O9 2.122(3) . ? Zn1 N3 2.126(3) . ? Zn1 N4 2.187(3) . ? Zn1 N5 2.197(3) . ? Cl1 O2 1.403(3) . ? Cl1 O3 1.409(3) . ? Cl1 O1 1.428(3) . ? Cl1 O4 1.432(4) . ? C6 C5 1.373(6) . ? C6 C1 1.375(6) . ? C6 N1 1.440(4) . ? C19 C20 1.349(8) . ? C19 C18 1.370(7) . ? C19 H19 0.9300 . ? C17 C22 1.351(6) . ? C17 C18 1.364(6) . ? C17 N8 1.432(5) . ? C5 C4 1.392(6) . ? C5 H5 0.9300 . ? C22 C21 1.392(7) . ? C22 H22 0.9300 . ? C18 H18 0.9300 . ? C1 C2 1.385(7) . ? C1 H1 0.9300 . ? C3 C2 1.356(8) . ? C3 C4 1.359(7) . ? C3 H3 0.9300 . ? C20 C21 1.374(7) . ? C20 H20 0.9300 . ? C4 H4 0.9300 . ? C2 H2 0.9300 . ? C21 H21 0.9300 . ? N8 N7 1.340(4) . ? N8 C16 1.360(5) . ? C16 C15 1.354(5) . ? C16 H16 0.9300 . ? C15 N6 1.342(4) . ? C15 C14 1.501(5) . ? N6 N7 1.314(4) . ? N3 N2 1.312(4) . ? N3 C8 1.352(4) . ? N2 N1 1.331(4) . ? N1 C7 1.350(5) . ? C8 C7 1.346(5) . ? C8 C9 1.499(5) . ? C7 H7 0.9300 . ? N4 C10 1.483(5) . ? N4 C11 1.487(5) . ? N4 C9 1.485(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.507(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N5 1.482(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N5 C13 1.477(4) . ? N5 C14 1.485(5) . ? O9 H9 0.8200 . ? O9 H100 0.69(5) . ? O10 H10 0.8200 . ? O10 H101 0.85(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O8 Cl2 1.414(4) . ? O5 Cl2 1.438(4) . ? O6 Cl2 1.411(4) . ? O7 Cl2 1.392(4) . ? 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 O10 Zn1 N6 89.58(12) . . ? O10 Zn1 O9 91.00(13) . . ? N6 Zn1 O9 87.05(11) . . ? O10 Zn1 N3 92.93(11) . . ? N6 Zn1 N3 176.59(12) . . ? O9 Zn1 N3 95.20(11) . . ? O10 Zn1 N4 170.00(11) . . ? N6 Zn1 N4 99.02(12) . . ? O9 Zn1 N4 94.49(13) . . ? N3 Zn1 N4 78.28(11) . . ? O10 Zn1 N5 93.43(12) . . ? N6 Zn1 N5 76.75(11) . . ? O9 Zn1 N5 163.16(11) . . ? N3 Zn1 N5 100.77(11) . . ? N4 Zn1 N5 83.69(11) . . ? O2 Cl1 O3 110.1(2) . . ? O2 Cl1 O1 110.4(2) . . ? O3 Cl1 O1 109.9(2) . . ? O2 Cl1 O4 109.4(3) . . ? O3 Cl1 O4 110.7(3) . . ? O1 Cl1 O4 106.2(2) . . ? C5 C6 C1 121.3(4) . . ? C5 C6 N1 119.3(3) . . ? C1 C6 N1 119.3(4) . . ? C20 C19 C18 121.6(5) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C22 C17 C18 121.0(4) . . ? C22 C17 N8 119.7(4) . . ? C18 C17 N8 119.3(4) . . ? C6 C5 C4 118.1(4) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C17 C22 C21 119.2(5) . . ? C17 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C17 C18 C19 119.0(5) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C6 C1 C2 118.5(5) . . ? C6 C1 H1 120.8 . . ? C2 C1 H1 120.8 . . ? C2 C3 C4 119.5(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C19 C20 C21 119.0(4) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C3 C4 C5 121.2(5) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C3 C2 C1 121.3(5) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C20 C21 C22 120.0(5) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? N7 N8 C16 111.0(3) . . ? N7 N8 C17 118.6(3) . . ? C16 N8 C17 130.4(3) . . ? C15 C16 N8 104.8(3) . . ? C15 C16 H16 127.6 . . ? N8 C16 H16 127.6 . . ? N6 C15 C16 107.8(3) . . ? N6 C15 C14 118.0(3) . . ? C16 C15 C14 134.2(3) . . ? N7 N6 C15 110.9(3) . . ? N7 N6 Zn1 133.8(2) . . ? C15 N6 Zn1 115.3(2) . . ? N6 N7 N8 105.5(3) . . ? N2 N3 C8 110.3(3) . . ? N2 N3 Zn1 135.9(2) . . ? C8 N3 Zn1 113.5(2) . . ? N3 N2 N1 105.7(3) . . ? N2 N1 C7 111.3(3) . . ? N2 N1 C6 119.6(3) . . ? C7 N1 C6 129.1(3) . . ? C7 C8 N3 107.5(3) . . ? C7 C8 C9 134.0(3) . . ? N3 C8 C9 118.5(3) . . ? C8 C7 N1 105.2(3) . . ? C8 C7 H7 127.4 . . ? N1 C7 H7 127.4 . . ? C10 N4 C11 110.1(3) . . ? C10 N4 C9 109.7(3) . . ? C11 N4 C9 110.0(3) . . ? C10 N4 Zn1 115.5(3) . . ? C11 N4 Zn1 103.9(2) . . ? C9 N4 Zn1 107.4(2) . . ? N4 C9 C8 109.0(3) . . ? N4 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? N4 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N4 C11 C12 111.6(3) . . ? N4 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N4 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? N5 C12 C11 110.9(3) . . ? N5 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N5 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.0 . . ? C13 N5 C12 110.3(3) . . ? C13 N5 C14 109.6(3) . . ? C12 N5 C14 110.7(3) . . ? C13 N5 Zn1 113.7(2) . . ? C12 N5 Zn1 104.4(2) . . ? C14 N5 Zn1 108.0(2) . . ? Zn1 O9 H9 109.5 . . ? Zn1 O9 H100 115(4) . . ? H9 O9 H100 111.2 . . ? Zn1 O10 H10 109.5 . . ? Zn1 O10 H101 126(4) . . ? H10 O10 H101 120.2 . . ? N5 C13 H13A 109.5 . . ? N5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N5 C14 C15 108.3(3) . . ? N5 C14 H14A 110.0 . . ? C15 C14 H14A 110.0 . . ? N5 C14 H14B 110.0 . . ? C15 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? O7 Cl2 O8 113.0(3) . . ? O7 Cl2 O6 110.8(3) . . ? O8 Cl2 O6 111.4(3) . . ? O7 Cl2 O5 107.0(3) . . ? O8 Cl2 O5 108.4(3) . . ? O6 Cl2 O5 105.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C6 C5 C4 1.7(7) . . . . ? N1 C6 C5 C4 179.8(4) . . . . ? C18 C17 C22 C21 -5.0(9) . . . . ? N8 C17 C22 C21 177.8(5) . . . . ? C22 C17 C18 C19 3.8(8) . . . . ? N8 C17 C18 C19 -179.1(5) . . . . ? C20 C19 C18 C17 -0.6(10) . . . . ? C5 C6 C1 C2 -1.3(7) . . . . ? N1 C6 C1 C2 -179.4(4) . . . . ? C18 C19 C20 C21 -1.1(10) . . . . ? C2 C3 C4 C5 -1.9(9) . . . . ? C6 C5 C4 C3 -0.1(8) . . . . ? C4 C3 C2 C1 2.4(9) . . . . ? C6 C1 C2 C3 -0.8(9) . . . . ? C19 C20 C21 C22 -0.1(10) . . . . ? C17 C22 C21 C20 3.2(10) . . . . ? C22 C17 N8 N7 -15.9(6) . . . . ? C18 C17 N8 N7 166.9(4) . . . . ? C22 C17 N8 C16 166.5(5) . . . . ? C18 C17 N8 C16 -10.7(7) . . . . ? N7 N8 C16 C15 0.1(5) . . . . ? C17 N8 C16 C15 177.9(4) . . . . ? N8 C16 C15 N6 0.8(5) . . . . ? N8 C16 C15 C14 179.3(4) . . . . ? C16 C15 N6 N7 -1.5(5) . . . . ? C14 C15 N6 N7 179.7(3) . . . . ? C16 C15 N6 Zn1 179.8(3) . . . . ? C14 C15 N6 Zn1 1.0(5) . . . . ? O10 Zn1 N6 N7 104.8(4) . . . . ? O9 Zn1 N6 N7 13.8(4) . . . . ? N3 Zn1 N6 N7 -117.7(18) . . . . ? N4 Zn1 N6 N7 -80.3(4) . . . . ? N5 Zn1 N6 N7 -161.5(4) . . . . ? O10 Zn1 N6 C15 -76.9(3) . . . . ? O9 Zn1 N6 C15 -167.9(3) . . . . ? N3 Zn1 N6 C15 61(2) . . . . ? N4 Zn1 N6 C15 98.0(3) . . . . ? N5 Zn1 N6 C15 16.8(3) . . . . ? C15 N6 N7 N8 1.5(4) . . . . ? Zn1 N6 N7 N8 179.9(3) . . . . ? C16 N8 N7 N6 -1.0(4) . . . . ? C17 N8 N7 N6 -179.0(3) . . . . ? O10 Zn1 N3 N2 14.8(3) . . . . ? N6 Zn1 N3 N2 -122.6(18) . . . . ? O9 Zn1 N3 N2 106.1(3) . . . . ? N4 Zn1 N3 N2 -160.4(3) . . . . ? N5 Zn1 N3 N2 -79.3(3) . . . . ? O10 Zn1 N3 C8 -170.8(3) . . . . ? N6 Zn1 N3 C8 52(2) . . . . ? O9 Zn1 N3 C8 -79.5(3) . . . . ? N4 Zn1 N3 C8 14.0(2) . . . . ? N5 Zn1 N3 C8 95.2(3) . . . . ? C8 N3 N2 N1 0.4(4) . . . . ? Zn1 N3 N2 N1 175.0(2) . . . . ? N3 N2 N1 C7 -0.1(4) . . . . ? N3 N2 N1 C6 178.5(3) . . . . ? C5 C6 N1 N2 -16.3(5) . . . . ? C1 C6 N1 N2 161.9(4) . . . . ? C5 C6 N1 C7 162.0(4) . . . . ? C1 C6 N1 C7 -19.8(6) . . . . ? N2 N3 C8 C7 -0.7(4) . . . . ? Zn1 N3 C8 C7 -176.5(2) . . . . ? N2 N3 C8 C9 -179.6(3) . . . . ? Zn1 N3 C8 C9 4.5(4) . . . . ? N3 C8 C7 N1 0.6(4) . . . . ? C9 C8 C7 N1 179.3(4) . . . . ? N2 N1 C7 C8 -0.3(4) . . . . ? C6 N1 C7 C8 -178.8(3) . . . . ? O10 Zn1 N4 C10 180(30) . . . . ? N6 Zn1 N4 C10 30.4(3) . . . . ? O9 Zn1 N4 C10 -57.3(3) . . . . ? N3 Zn1 N4 C10 -151.7(3) . . . . ? N5 Zn1 N4 C10 105.9(3) . . . . ? O10 Zn1 N4 C11 58.8(8) . . . . ? N6 Zn1 N4 C11 -90.3(2) . . . . ? O9 Zn1 N4 C11 -178.0(2) . . . . ? N3 Zn1 N4 C11 87.6(2) . . . . ? N5 Zn1 N4 C11 -14.8(2) . . . . ? O10 Zn1 N4 C9 -57.8(8) . . . . ? N6 Zn1 N4 C9 153.1(2) . . . . ? O9 Zn1 N4 C9 65.4(2) . . . . ? N3 Zn1 N4 C9 -29.0(2) . . . . ? N5 Zn1 N4 C9 -131.4(2) . . . . ? C10 N4 C9 C8 164.8(3) . . . . ? C11 N4 C9 C8 -73.9(4) . . . . ? Zn1 N4 C9 C8 38.6(4) . . . . ? C7 C8 C9 N4 151.3(4) . . . . ? N3 C8 C9 N4 -30.1(5) . . . . ? C10 N4 C11 C12 -82.1(4) . . . . ? C9 N4 C11 C12 156.8(3) . . . . ? Zn1 N4 C11 C12 42.1(3) . . . . ? N4 C11 C12 N5 -59.4(4) . . . . ? C11 C12 N5 C13 -81.9(4) . . . . ? C11 C12 N5 C14 156.7(3) . . . . ? C11 C12 N5 Zn1 40.7(3) . . . . ? O10 Zn1 N5 C13 -63.7(3) . . . . ? N6 Zn1 N5 C13 -152.5(3) . . . . ? O9 Zn1 N5 C13 -168.7(4) . . . . ? N3 Zn1 N5 C13 29.9(3) . . . . ? N4 Zn1 N5 C13 106.7(3) . . . . ? O10 Zn1 N5 C12 176.0(2) . . . . ? N6 Zn1 N5 C12 87.3(2) . . . . ? O9 Zn1 N5 C12 71.0(5) . . . . ? N3 Zn1 N5 C12 -90.3(2) . . . . ? N4 Zn1 N5 C12 -13.6(2) . . . . ? O10 Zn1 N5 C14 58.1(2) . . . . ? N6 Zn1 N5 C14 -30.6(2) . . . . ? O9 Zn1 N5 C14 -46.8(5) . . . . ? N3 Zn1 N5 C14 151.8(2) . . . . ? N4 Zn1 N5 C14 -131.5(2) . . . . ? C13 N5 C14 C15 163.3(3) . . . . ? C12 N5 C14 C15 -74.8(4) . . . . ? Zn1 N5 C14 C15 39.0(3) . . . . ? N6 C15 C14 N5 -27.9(5) . . . . ? C16 C15 C14 N5 153.7(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.303 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.066 # Attachment '4c-Mn.cif' data_Mn-4 _database_code_depnum_ccdc_archive 'CCDC 736933' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 F6 Mn N10 O10 S2' _chemical_formula_sum 'C24 H24 F6 Mn N10 O10 S2' _chemical_formula_weight 845.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0524(11) _cell_length_b 26.257(3) _cell_length_c 15.0307(18) _cell_angle_alpha 90.00 _cell_angle_beta 97.368(2) _cell_angle_gamma 90.00 _cell_volume 3543.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2872 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 19.51 _exptl_crystal_description block _exptl_crystal_colour yelow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1716 _exptl_absorpt_coefficient_mu 0.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .87 _exptl_absorpt_correction_T_max .89 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26327 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0786 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6890 _reflns_number_gt 3421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.009(2) _refine_ls_number_reflns 6890 _refine_ls_number_parameters 480 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1406 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1813 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.970 _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 C1 C 0.5423(6) 0.26694(18) 0.7896(3) 0.0685(14) Uani 1 1 d . . . H1A H 0.6078 0.2933 0.7720 0.082 Uiso 1 1 calc R . . H1B H 0.4495 0.2685 0.7494 0.082 Uiso 1 1 calc R . . C2 C 0.3825(5) 0.24511(18) 0.9031(3) 0.0632(12) Uani 1 1 d . . . H2A H 0.3873 0.2115 0.8769 0.076 Uiso 1 1 calc R . . H2B H 0.2910 0.2612 0.8765 0.076 Uiso 1 1 calc R . . C3 C 0.3815(5) 0.24032(19) 1.0025(3) 0.0654(13) Uani 1 1 d . . . H3A H 0.3789 0.2741 1.0285 0.078 Uiso 1 1 calc R . . H3B H 0.2922 0.2224 1.0139 0.078 Uiso 1 1 calc R . . C4 C 0.5331(6) 0.22445(17) 1.1432(3) 0.0645(13) Uani 1 1 d . . . H4A H 0.5950 0.1987 1.1758 0.077 Uiso 1 1 calc R . . H4B H 0.4367 0.2242 1.1649 0.077 Uiso 1 1 calc R . . C5 C 0.6129(5) 0.21600(17) 0.7821(3) 0.0608(12) Uani 1 1 d . . . C6 C 0.6241(6) 0.18361(19) 0.7137(3) 0.0667(13) Uani 1 1 d . . . H6 H 0.5828 0.1874 0.6542 0.080 Uiso 1 1 calc R . . C7 C 0.7605(5) 0.09975(18) 0.7082(3) 0.0638(13) Uani 1 1 d . . . C8 C 0.7433(8) 0.0961(2) 0.6181(4) 0.105(2) Uani 1 1 d . . . H8 H 0.6972 0.1221 0.5829 0.126 Uiso 1 1 calc R . . C9 C 0.7948(8) 0.0532(2) 0.5785(4) 0.114(2) Uani 1 1 d . . . H9 H 0.7825 0.0499 0.5164 0.136 Uiso 1 1 calc R . . C10 C 0.8622(7) 0.0167(2) 0.6302(4) 0.0886(18) Uani 1 1 d . . . C11 C 0.8828(8) 0.0201(2) 0.7193(5) 0.115(2) Uani 1 1 d . . . H11 H 0.9316 -0.0057 0.7538 0.139 Uiso 1 1 calc R . . C12 C 0.8307(7) 0.0629(2) 0.7600(4) 0.100(2) Uani 1 1 d . . . H12 H 0.8439 0.0660 0.8221 0.121 Uiso 1 1 calc R . . C13 C 0.4832(6) 0.33086(17) 0.8944(4) 0.0781(15) Uani 1 1 d . . . H13A H 0.5685 0.3502 0.8824 0.117 Uiso 1 1 calc R . . H13B H 0.4641 0.3371 0.9548 0.117 Uiso 1 1 calc R . . H13C H 0.3981 0.3409 0.8533 0.117 Uiso 1 1 calc R . . C14 C 0.4949(6) 0.15705(17) 1.0345(4) 0.0774(15) Uani 1 1 d . . . H14A H 0.4163 0.1456 1.0669 0.116 Uiso 1 1 calc R . . H14B H 0.5859 0.1400 1.0571 0.116 Uiso 1 1 calc R . . H14C H 0.4699 0.1494 0.9720 0.116 Uiso 1 1 calc R . . C15 C 0.6039(5) 0.27553(17) 1.1593(3) 0.0543(11) Uani 1 1 d . . . C16 C 0.6086(5) 0.31079(18) 1.2255(3) 0.0596(12) Uani 1 1 d . . . H16 H 0.5595 0.3097 1.2761 0.071 Uiso 1 1 calc R . . C17 C 0.7502(6) 0.39400(19) 1.2480(3) 0.0688(14) Uani 1 1 d . . . C18 C 0.7296(7) 0.40027(19) 1.3354(4) 0.0826(16) Uani 1 1 d . . . H18 H 0.6801 0.3757 1.3649 0.099 Uiso 1 1 calc R . . C19 C 0.7845(7) 0.4445(2) 1.3802(4) 0.0889(18) Uani 1 1 d . . . H19 H 0.7690 0.4506 1.4393 0.107 Uiso 1 1 calc R . . C20 C 0.8600(9) 0.4780(2) 1.3356(4) 0.107(2) Uani 1 1 d U . . C21 C 0.8796(9) 0.4721(2) 1.2476(5) 0.128(2) Uani 1 1 d U . . H21 H 0.9292 0.4967 1.2182 0.153 Uiso 1 1 calc R . . C22 C 0.8247(8) 0.4292(2) 1.2039(4) 0.112(2) Uani 1 1 d U . . H22 H 0.8380 0.4240 1.1443 0.135 Uiso 1 1 calc R . . C23 C 0.9563(9) 0.3808(3) 0.8790(7) 0.125(3) Uani 1 1 d . . . C24 C 0.9872(10) 0.1090(3) 1.0782(7) 0.121(2) Uani 1 1 d . . . F1 F 0.8569(6) 0.3830(2) 0.8060(4) 0.191(3) Uani 1 1 d . . . F2 F 0.9085(8) 0.40761(18) 0.9382(5) 0.207(3) Uani 1 1 d . . . F3 F 1.0781(6) 0.3996(2) 0.8565(5) 0.246(4) Uani 1 1 d . . . F4 F 0.9425(7) 0.10279(19) 1.1556(4) 0.188(2) Uani 1 1 d . . . F5 F 1.1165(6) 0.0838(2) 1.0834(4) 0.201(3) Uani 1 1 d . . . F6 F 0.8959(7) 0.08462(19) 1.0198(5) 0.192(2) Uani 1 1 d . . . Mn1 Mn 0.71009(7) 0.24407(2) 0.98000(4) 0.0528(2) Uani 1 1 d . . . N1 N 0.5126(4) 0.27592(13) 0.8830(2) 0.0548(9) Uani 1 1 d . . . N2 N 0.5145(4) 0.21260(13) 1.0463(2) 0.0551(9) Uani 1 1 d . . . N3 N 0.6895(5) 0.19512(15) 0.8570(2) 0.0661(11) Uani 1 1 d . . . N4 N 0.7484(5) 0.15145(15) 0.8380(2) 0.0677(11) Uani 1 1 d . . . N5 N 0.7077(4) 0.14470(15) 0.7499(2) 0.0628(10) Uani 1 1 d . . . N6 N 0.9244(9) -0.0280(2) 0.5864(6) 0.120(2) Uani 1 1 d . . . N7 N 0.6914(4) 0.29348(14) 1.0993(2) 0.0604(10) Uani 1 1 d . . . N8 N 0.7490(4) 0.33744(15) 1.1253(3) 0.0635(10) Uani 1 1 d . . . N9 N 0.6999(4) 0.34793(14) 1.2023(2) 0.0595(10) Uani 1 1 d . . . N10 N 0.9261(10) 0.5242(2) 1.3863(5) 0.145(3) Uani 1 1 d . . . O1 O 0.8769(7) -0.03808(18) 0.5113(4) 0.145(2) Uani 1 1 d . . . O2 O 1.0218(8) -0.0517(2) 0.6322(4) 0.159(2) Uani 1 1 d . . . O3 O 1.0222(12) 0.5466(3) 1.3524(5) 0.264(5) Uani 1 1 d . . . O4 O 0.8857(7) 0.53332(19) 1.4565(4) 0.144(2) Uani 1 1 d . . . O5 O 0.8411(4) 0.30093(13) 0.9274(3) 0.0896(11) Uani 1 1 d . . . O6 O 1.0913(4) 0.31792(15) 0.9886(3) 0.0981(12) Uani 1 1 d . . . O7 O 1.0364(5) 0.2899(2) 0.8381(2) 0.1274(18) Uani 1 1 d . . . O8 O 0.8687(4) 0.19479(14) 1.0549(2) 0.0803(10) Uani 1 1 d . . . O9 O 1.0511(4) 0.17234(15) 0.9602(2) 0.0886(11) Uani 1 1 d . . . O10 O 1.1228(4) 0.19179(17) 1.1163(2) 0.1035(13) Uani 1 1 d . . . S1 S 0.98567(14) 0.31460(5) 0.91066(8) 0.0617(4) Uani 1 1 d . . . S2 S 1.01126(15) 0.17369(5) 1.04908(9) 0.0695(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.088(4) 0.061(3) 0.055(3) 0.006(2) 0.004(3) 0.019(3) C2 0.050(3) 0.072(3) 0.064(3) 0.001(2) -0.006(2) 0.003(2) C3 0.047(3) 0.075(3) 0.074(3) 0.005(3) 0.006(2) -0.001(2) C4 0.079(3) 0.053(3) 0.062(3) 0.001(2) 0.014(3) -0.013(2) C5 0.075(3) 0.058(3) 0.048(3) 0.005(2) 0.000(2) 0.009(2) C6 0.081(4) 0.068(3) 0.047(3) -0.004(3) -0.007(2) 0.015(3) C7 0.075(3) 0.055(3) 0.061(3) -0.005(3) 0.005(3) 0.009(3) C8 0.170(7) 0.079(4) 0.064(4) -0.012(3) 0.007(4) 0.037(4) C9 0.180(7) 0.089(5) 0.070(4) -0.017(4) 0.008(4) 0.031(5) C10 0.123(5) 0.059(4) 0.088(4) -0.016(3) 0.031(4) -0.005(3) C11 0.177(7) 0.064(4) 0.103(5) -0.002(4) 0.011(5) 0.044(4) C12 0.155(6) 0.077(4) 0.066(4) -0.009(3) -0.003(4) 0.028(4) C13 0.093(4) 0.046(3) 0.094(4) 0.005(3) 0.007(3) 0.018(3) C14 0.093(4) 0.056(3) 0.082(4) -0.002(3) 0.003(3) -0.015(3) C15 0.058(3) 0.056(3) 0.048(3) -0.003(2) 0.005(2) 0.005(2) C16 0.073(3) 0.068(3) 0.039(3) 0.001(2) 0.009(2) 0.003(3) C17 0.093(4) 0.054(3) 0.059(3) -0.002(2) 0.007(3) 0.005(3) C18 0.123(5) 0.059(3) 0.066(4) -0.003(3) 0.014(3) -0.007(3) C19 0.130(5) 0.062(4) 0.071(4) -0.015(3) -0.001(4) 0.004(3) C20 0.177(6) 0.049(3) 0.091(4) -0.010(3) 0.010(4) -0.026(4) C21 0.204(6) 0.079(4) 0.104(4) -0.009(4) 0.036(4) -0.041(4) C22 0.195(6) 0.063(4) 0.083(4) -0.016(3) 0.033(4) -0.047(4) C23 0.074(5) 0.138(8) 0.163(8) 0.074(6) 0.010(5) -0.006(5) C24 0.110(6) 0.104(6) 0.149(8) 0.029(6) 0.019(6) 0.022(5) F1 0.165(5) 0.186(5) 0.208(5) 0.121(4) -0.028(4) 0.011(4) F2 0.238(7) 0.080(3) 0.303(9) -0.013(4) 0.035(6) 0.039(3) F3 0.148(4) 0.200(5) 0.392(10) 0.181(6) 0.044(5) -0.030(4) F4 0.240(6) 0.165(5) 0.173(5) 0.100(4) 0.081(5) 0.023(4) F5 0.178(5) 0.146(4) 0.284(7) 0.068(4) 0.048(5) 0.080(4) F6 0.230(6) 0.102(4) 0.242(7) 0.003(4) 0.026(5) -0.055(4) Mn1 0.0572(4) 0.0535(4) 0.0468(4) -0.0040(3) 0.0030(3) 0.0030(3) N1 0.063(2) 0.049(2) 0.050(2) 0.0025(17) 0.0012(18) 0.0063(18) N2 0.065(2) 0.044(2) 0.056(2) -0.0039(17) 0.0024(19) -0.0067(18) N3 0.081(3) 0.062(3) 0.052(2) -0.008(2) -0.009(2) 0.017(2) N4 0.084(3) 0.064(3) 0.051(2) -0.013(2) -0.010(2) 0.020(2) N5 0.074(3) 0.062(3) 0.049(2) -0.007(2) -0.004(2) 0.003(2) N6 0.176(7) 0.055(4) 0.139(6) -0.011(4) 0.062(5) 0.017(4) N7 0.070(3) 0.053(2) 0.059(2) -0.0142(19) 0.012(2) -0.009(2) N8 0.075(3) 0.064(3) 0.052(2) -0.007(2) 0.010(2) -0.007(2) N9 0.074(3) 0.054(2) 0.049(2) -0.0003(19) 0.003(2) 0.000(2) N10 0.236(9) 0.076(4) 0.122(6) -0.010(4) 0.013(6) -0.044(5) O1 0.220(6) 0.099(4) 0.126(4) -0.055(3) 0.059(4) -0.014(4) O2 0.239(7) 0.075(4) 0.168(6) -0.013(3) 0.047(5) 0.050(4) O3 0.448(14) 0.156(6) 0.205(7) -0.073(5) 0.105(8) -0.177(8) O4 0.210(6) 0.091(4) 0.124(4) -0.045(3) -0.010(4) 0.011(3) O5 0.072(2) 0.084(3) 0.117(3) 0.026(2) 0.027(2) -0.0057(19) O6 0.104(3) 0.101(3) 0.080(3) -0.012(2) -0.024(2) 0.003(2) O7 0.136(4) 0.194(5) 0.055(2) -0.014(3) 0.022(2) 0.066(3) O8 0.078(2) 0.094(3) 0.070(2) 0.0171(19) 0.0141(18) 0.036(2) O9 0.092(3) 0.116(3) 0.059(2) -0.009(2) 0.013(2) -0.001(2) O10 0.079(3) 0.166(4) 0.062(2) -0.015(2) -0.005(2) -0.012(3) S1 0.0611(8) 0.0763(9) 0.0486(7) 0.0030(6) 0.0101(6) 0.0037(6) S2 0.0619(8) 0.0889(10) 0.0572(8) 0.0060(7) 0.0055(6) 0.0043(7) _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 C1 N1 1.482(5) . ? C1 C5 1.493(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N1 1.492(6) . ? C2 C3 1.500(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.486(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.477(5) . ? C4 C15 1.493(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.349(6) . ? C5 N3 1.359(5) . ? C6 N5 1.344(6) . ? C6 H6 0.9300 . ? C7 C8 1.347(7) . ? C7 C12 1.349(7) . ? C7 N5 1.445(6) . ? C8 C9 1.382(7) . ? C8 H8 0.9300 . ? C9 C10 1.331(8) . ? C9 H9 0.9300 . ? C10 C11 1.331(8) . ? C10 N6 1.491(8) . ? C11 C12 1.389(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N1 1.481(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.477(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.355(6) . ? C15 N7 1.359(5) . ? C16 N9 1.353(6) . ? C16 H16 0.9300 . ? C17 C18 1.361(7) . ? C17 C22 1.365(7) . ? C17 N9 1.436(6) . ? C18 C19 1.402(7) . ? C18 H18 0.9300 . ? C19 C20 1.345(8) . ? C19 H19 0.9300 . ? C20 C21 1.365(9) . ? C20 N10 1.514(8) . ? C21 C22 1.365(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 F2 1.255(10) . ? C23 F3 1.292(8) . ? C23 F1 1.328(9) . ? C23 S1 1.814(8) . ? C24 F4 1.290(9) . ? C24 F6 1.295(9) . ? C24 F5 1.338(8) . ? C24 S2 1.774(8) . ? Mn1 O5 2.122(3) . ? Mn1 O8 2.142(3) . ? Mn1 N7 2.237(4) . ? Mn1 N3 2.240(4) . ? Mn1 N2 2.295(4) . ? Mn1 N1 2.314(4) . ? N3 N4 1.311(5) . ? N4 N5 1.340(5) . ? N6 O1 1.185(8) . ? N6 O2 1.217(8) . ? N7 N8 1.306(5) . ? N8 N9 1.321(5) . ? N10 O4 1.184(8) . ? N10 O3 1.216(9) . ? O5 S1 1.410(3) . ? O6 S1 1.416(4) . ? O7 S1 1.396(4) . ? O8 S2 1.417(3) . ? O9 S2 1.428(3) . ? O10 S2 1.416(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C5 110.2(4) . . ? N1 C1 H1A 109.6 . . ? C5 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C5 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N1 C2 C3 110.7(4) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C2 112.0(4) . . ? N2 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C15 110.0(4) . . ? N2 C4 H4A 109.7 . . ? C15 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C15 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 C5 N3 107.3(4) . . ? C6 C5 C1 134.2(4) . . ? N3 C5 C1 118.5(4) . . ? N5 C6 C5 105.3(4) . . ? N5 C6 H6 127.3 . . ? C5 C6 H6 127.3 . . ? C8 C7 C12 120.9(5) . . ? C8 C7 N5 119.5(5) . . ? C12 C7 N5 119.6(4) . . ? C7 C8 C9 119.3(6) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 119.4(6) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 122.1(6) . . ? C11 C10 N6 119.1(7) . . ? C9 C10 N6 118.7(6) . . ? C10 C11 C12 119.1(6) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C7 C12 C11 119.2(5) . . ? C7 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 N7 106.5(4) . . ? C16 C15 C4 134.9(4) . . ? N7 C15 C4 118.6(4) . . ? N9 C16 C15 105.4(4) . . ? N9 C16 H16 127.3 . . ? C15 C16 H16 127.3 . . ? C18 C17 C22 121.6(5) . . ? C18 C17 N9 119.3(5) . . ? C22 C17 N9 119.0(5) . . ? C17 C18 C19 118.7(5) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 118.2(5) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? C19 C20 C21 123.2(6) . . ? C19 C20 N10 117.7(6) . . ? C21 C20 N10 119.1(7) . . ? C22 C21 C20 118.3(6) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? C17 C22 C21 119.9(6) . . ? C17 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? F2 C23 F3 110.8(10) . . ? F2 C23 F1 107.7(8) . . ? F3 C23 F1 106.2(8) . . ? F2 C23 S1 113.8(6) . . ? F3 C23 S1 109.5(6) . . ? F1 C23 S1 108.5(7) . . ? F4 C24 F6 107.6(8) . . ? F4 C24 F5 105.0(7) . . ? F6 C24 F5 105.8(8) . . ? F4 C24 S2 113.9(7) . . ? F6 C24 S2 113.2(6) . . ? F5 C24 S2 110.7(6) . . ? O5 Mn1 O8 104.59(15) . . ? O5 Mn1 N7 89.67(15) . . ? O8 Mn1 N7 92.50(13) . . ? O5 Mn1 N3 95.00(15) . . ? O8 Mn1 N3 93.79(13) . . ? N7 Mn1 N3 170.97(15) . . ? O5 Mn1 N2 156.18(14) . . ? O8 Mn1 N2 93.26(13) . . ? N7 Mn1 N2 73.67(13) . . ? N3 Mn1 N2 99.49(14) . . ? O5 Mn1 N1 86.23(14) . . ? O8 Mn1 N1 163.98(14) . . ? N7 Mn1 N1 99.43(13) . . ? N3 Mn1 N1 73.23(13) . . ? N2 Mn1 N1 80.03(13) . . ? C13 N1 C1 108.8(4) . . ? C13 N1 C2 110.3(4) . . ? C1 N1 C2 110.5(4) . . ? C13 N1 Mn1 114.5(3) . . ? C1 N1 Mn1 108.7(3) . . ? C2 N1 Mn1 104.0(2) . . ? C4 N2 C14 108.8(4) . . ? C4 N2 C3 108.5(4) . . ? C14 N2 C3 110.7(4) . . ? C4 N2 Mn1 110.8(3) . . ? C14 N2 Mn1 113.0(3) . . ? C3 N2 Mn1 104.9(2) . . ? N4 N3 C5 110.5(4) . . ? N4 N3 Mn1 133.5(3) . . ? C5 N3 Mn1 115.5(3) . . ? N3 N4 N5 105.3(4) . . ? N4 N5 C6 111.6(4) . . ? N4 N5 C7 118.2(4) . . ? C6 N5 C7 130.2(4) . . ? O1 N6 O2 125.0(7) . . ? O1 N6 C10 119.0(8) . . ? O2 N6 C10 116.0(7) . . ? N8 N7 C15 110.6(3) . . ? N8 N7 Mn1 133.2(3) . . ? C15 N7 Mn1 116.2(3) . . ? N7 N8 N9 106.3(4) . . ? N8 N9 C16 111.2(4) . . ? N8 N9 C17 118.2(4) . . ? C16 N9 C17 130.6(4) . . ? O4 N10 O3 126.5(8) . . ? O4 N10 C20 117.7(8) . . ? O3 N10 C20 115.7(8) . . ? S1 O5 Mn1 145.2(2) . . ? S2 O8 Mn1 139.3(2) . . ? O7 S1 O5 115.3(3) . . ? O7 S1 O6 114.8(3) . . ? O5 S1 O6 114.3(3) . . ? O7 S1 C23 107.0(4) . . ? O5 S1 C23 100.5(3) . . ? O6 S1 C23 102.6(4) . . ? O10 S2 O8 113.3(2) . . ? O10 S2 O9 115.7(2) . . ? O8 S2 O9 114.1(2) . . ? O10 S2 C24 104.1(4) . . ? O8 S2 C24 102.6(3) . . ? O9 S2 C24 105.1(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.356 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.060 # Attachment '7a-Fe.cif' data_fe-1 _database_code_depnum_ccdc_archive 'CCDC 736996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 F12 Fe N10 Sb2' _chemical_formula_weight 1011.97 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pcca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 30.139(5) _cell_length_b 11.190(5) _cell_length_c 22.140(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 7467(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8738 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.44 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3952 _exptl_absorpt_coefficient_mu 1.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4479 _exptl_absorpt_correction_T_max 0.7008 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33857 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_sigmaI/netI 0.0810 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6584 _reflns_number_gt 3142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.009(2) _refine_ls_number_reflns 6584 _refine_ls_number_parameters 467 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.1685 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.2509 _refine_ls_wR_factor_gt 0.2089 _refine_ls_goodness_of_fit_ref 1.232 _refine_ls_restrained_S_all 1.279 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.003 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 F10 F 0.1731(6) 0.4553(18) 0.5690(7) 0.277(8) Uani 1 1 d U . . Sb1 Sb 0.0000 0.66384(14) 0.2500 0.0878(5) Uani 1 2 d S . . Sb2 Sb 0.2500 0.0000 0.41367(5) 0.0774(5) Uani 1 2 d S . . Fe1 Fe 0.12544(5) 0.14620(13) 0.17586(6) 0.0479(4) Uani 1 1 d . . . Sb4 Sb 0.13439(6) 0.41555(11) 0.50223(5) 0.1342(6) Uani 1 1 d . . . N5 N 0.0350(3) 0.0587(8) 0.1136(4) 0.050(2) Uani 1 1 d . . . N4 N 0.0759(3) 0.0386(8) 0.1323(4) 0.052(2) Uani 1 1 d . . . N8 N 0.2317(3) 0.3163(7) 0.2687(4) 0.047(2) Uani 1 1 d . . . N7 N 0.2167(3) 0.2732(8) 0.2167(4) 0.055(2) Uani 1 1 d . . . N6 N 0.0199(3) -0.0470(8) 0.0932(3) 0.049(2) Uani 1 1 d . . . N2 N 0.1034(3) 0.1235(8) 0.2732(4) 0.059(2) Uani 1 1 d . . . N1 N 0.1751(3) 0.2372(7) 0.2276(4) 0.052(2) Uani 1 1 d . . . C15 C 0.2763(4) 0.3572(9) 0.2701(5) 0.055(3) Uani 1 1 d . . . C9 C 0.1328(4) -0.1129(11) 0.1366(6) 0.073(4) Uani 1 1 d . . . H9A H 0.1519 -0.0971 0.1022 0.087 Uiso 1 1 calc R . . H9B H 0.1337 -0.1979 0.1452 0.087 Uiso 1 1 calc R . . N3 N 0.1484(3) -0.0421(8) 0.1911(4) 0.056(2) Uani 1 1 d . . . N15 N 0.0826(4) 0.2975(9) 0.1596(5) 0.072(3) Uani 1 1 d . . . C12 C 0.1196(4) 0.2236(12) 0.3084(5) 0.070(4) Uani 1 1 d . . . H12A H 0.1208 0.2015 0.3508 0.084 Uiso 1 1 calc R . . H12B H 0.0994 0.2906 0.3043 0.084 Uiso 1 1 calc R . . C14 C 0.2012(4) 0.3100(9) 0.3123(5) 0.052(3) Uani 1 1 d . . . H14 H 0.2043 0.3354 0.3520 0.062 Uiso 1 1 calc R . . C21 C 0.1944(4) 0.2291(11) 0.0731(5) 0.067(3) Uani 1 1 d . . . F7 F 0.2868(4) 0.1303(10) 0.4154(5) 0.168(4) Uani 1 1 d U . . N20 N 0.1676(3) 0.1805(9) 0.0994(4) 0.066(3) Uani 1 1 d . . . C23 C 0.0566(5) 0.3476(12) 0.1354(6) 0.075(4) Uani 1 1 d . . . F6 F 0.2500 0.0000 0.4948(6) 0.144(5) Uani 1 2 d SU . . C7 C 0.0507(4) -0.1296(10) 0.0987(4) 0.057(3) Uani 1 1 d . . . H7 H 0.0482 -0.2096 0.0880 0.068 Uiso 1 1 calc R . . C1 C -0.0256(4) -0.0584(13) 0.0711(4) 0.066(3) Uani 1 1 d . . . C10 C 0.1261(4) -0.0829(11) 0.2470(6) 0.075(4) Uani 1 1 d . . . H10A H 0.1411 -0.1537 0.2621 0.090 Uiso 1 1 calc R . . H10B H 0.0957 -0.1045 0.2378 0.090 Uiso 1 1 calc R . . F13 F 0.1100(6) 0.3739(18) 0.4366(8) 0.260(7) Uani 1 1 d U . . C13 C 0.1650(4) 0.2593(9) 0.2872(4) 0.054(3) Uani 1 1 d . . . C20 C 0.2956(4) 0.4019(10) 0.2181(5) 0.062(3) Uani 1 1 d . . . H20 H 0.2793 0.4065 0.1825 0.074 Uiso 1 1 calc R . . C2 C -0.0480(4) 0.0467(13) 0.0548(5) 0.066(3) Uani 1 1 d . . . H2 H -0.0347 0.1214 0.0575 0.079 Uiso 1 1 calc R . . C18 C 0.3617(4) 0.4377(12) 0.2729(8) 0.083(4) Uani 1 1 d . . . H18 H 0.3909 0.4649 0.2745 0.099 Uiso 1 1 calc R . . C11 C 0.1265(4) 0.0134(11) 0.2958(5) 0.066(3) Uani 1 1 d . . . H11A H 0.1116 -0.0159 0.3317 0.079 Uiso 1 1 calc R . . H11B H 0.1569 0.0327 0.3066 0.079 Uiso 1 1 calc R . . C8 C 0.0870(3) -0.0755(9) 0.1231(4) 0.049(3) Uani 1 1 d . . . F14 F 0.1531(5) 0.2656(13) 0.5224(6) 0.211(5) Uani 1 1 d U . . C16 C 0.2987(4) 0.3555(10) 0.3239(6) 0.068(3) Uani 1 1 d . . . H16 H 0.2851 0.3277 0.3589 0.082 Uiso 1 1 calc R . . C24 C 0.0206(5) 0.4098(14) 0.1034(7) 0.116(5) Uani 1 1 d . . . H24A H 0.0212 0.3883 0.0614 0.174 Uiso 1 1 calc R . . H24B H 0.0245 0.4946 0.1073 0.174 Uiso 1 1 calc R . . H24C H -0.0074 0.3872 0.1205 0.174 Uiso 1 1 calc R . . F11 F 0.1246(6) 0.560(2) 0.4955(9) 0.297(10) Uani 1 1 d U . . C6 C -0.0446(5) -0.1643(13) 0.0670(6) 0.089(4) Uani 1 1 d . . . H6 H -0.0290 -0.2327 0.0779 0.106 Uiso 1 1 calc R . . F2 F 0.0480(3) 0.6630(9) 0.1967(4) 0.143(3) Uani 1 1 d U . . C3 C -0.0907(4) 0.0333(16) 0.0347(5) 0.082(4) Uani 1 1 d . . . H3 H -0.1065 0.1018 0.0243 0.099 Uiso 1 1 calc R . . C4 C -0.1107(6) -0.070(2) 0.0291(7) 0.106(6) Uani 1 1 d . . . H4 H -0.1394 -0.0744 0.0140 0.127 Uiso 1 1 calc R . . C22 C 0.2287(5) 0.2844(13) 0.0407(7) 0.123(6) Uani 1 1 d . . . H22A H 0.2563 0.2453 0.0496 0.185 Uiso 1 1 calc R . . H22B H 0.2305 0.3670 0.0522 0.185 Uiso 1 1 calc R . . H22C H 0.2227 0.2787 -0.0018 0.185 Uiso 1 1 calc R . . F1 F -0.0363(4) 0.6622(13) 0.1845(5) 0.196(5) Uani 1 1 d U . . F12 F 0.1851(5) 0.4389(15) 0.4561(7) 0.247(6) Uani 1 1 d U . . C19 C 0.3402(4) 0.4403(11) 0.2192(8) 0.086(4) Uani 1 1 d . . . H19 H 0.3543 0.4666 0.1843 0.103 Uiso 1 1 calc R . . F9 F 0.0911(6) 0.3927(15) 0.5505(8) 0.258(7) Uani 1 1 d U . . C17 C 0.3426(5) 0.3968(14) 0.3248(7) 0.097(5) Uani 1 1 d . . . H17 H 0.3587 0.3964 0.3606 0.116 Uiso 1 1 calc R . . F5 F 0.2008(3) 0.0993(10) 0.4119(4) 0.151(4) Uani 1 1 d U . . C5 C -0.0878(6) -0.174(2) 0.0464(7) 0.117(6) Uani 1 1 d . . . H5 H -0.1016 -0.2478 0.0441 0.140 Uiso 1 1 calc R . . F3 F 0.0000 0.5108(18) 0.2500 0.202(7) Uani 1 2 d SU . . F4 F 0.0000 0.8280(18) 0.2500 0.220(8) Uani 1 2 d SU . . F15 F 0.2500 0.0000 0.3308(6) 0.152(5) Uani 1 2 d SU . . C25 C 0.1968(4) -0.0527(10) 0.1952(6) 0.077(4) Uani 1 1 d . . . H25A H 0.2070 -0.0155 0.2318 0.115 Uiso 1 1 calc R . . H25B H 0.2102 -0.0138 0.1611 0.115 Uiso 1 1 calc R . . H25C H 0.2050 -0.1356 0.1954 0.115 Uiso 1 1 calc R . . C26 C 0.0546(4) 0.1100(13) 0.2785(5) 0.083(4) Uani 1 1 d . . . H26A H 0.0462 0.1138 0.3203 0.124 Uiso 1 1 calc R . . H26B H 0.0458 0.0343 0.2620 0.124 Uiso 1 1 calc R . . H26C H 0.0402 0.1732 0.2567 0.124 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 F10 0.318(11) 0.281(11) 0.230(10) -0.015(8) -0.014(9) -0.018(9) Sb1 0.0737(10) 0.1078(13) 0.0818(9) 0.000 0.0014(7) 0.000 Sb2 0.0764(9) 0.0834(10) 0.0725(8) 0.000 0.000 -0.0054(7) Fe1 0.0454(9) 0.0474(10) 0.0509(9) -0.0015(7) -0.0031(7) -0.0031(7) Sb4 0.2500(18) 0.0712(8) 0.0813(8) 0.0004(6) 0.0395(9) -0.0061(9) N5 0.049(6) 0.047(6) 0.053(5) -0.006(4) 0.007(4) 0.000(4) N4 0.045(6) 0.049(6) 0.062(6) -0.002(4) -0.008(5) 0.006(4) N8 0.050(6) 0.044(5) 0.046(5) 0.000(4) -0.006(5) -0.005(4) N7 0.060(6) 0.049(6) 0.057(6) -0.009(4) -0.001(5) -0.007(5) N6 0.046(5) 0.055(6) 0.047(5) 0.004(4) 0.000(4) 0.003(5) N2 0.056(6) 0.061(6) 0.062(6) 0.000(5) 0.012(5) -0.011(5) N1 0.050(6) 0.051(6) 0.056(5) 0.007(4) 0.001(4) -0.011(4) C15 0.065(8) 0.038(7) 0.063(7) -0.022(6) -0.014(6) 0.001(6) C9 0.075(9) 0.058(8) 0.085(9) -0.018(7) -0.001(7) 0.012(6) N3 0.039(5) 0.058(6) 0.070(6) 0.007(5) -0.003(5) 0.011(4) N15 0.069(8) 0.059(7) 0.089(8) -0.008(6) -0.009(6) 0.004(5) C12 0.066(8) 0.083(9) 0.061(7) -0.023(7) 0.027(6) -0.026(7) C14 0.064(8) 0.041(6) 0.050(6) -0.007(5) -0.011(6) 0.000(5) C21 0.075(9) 0.063(9) 0.064(8) -0.009(6) 0.007(7) -0.017(7) F7 0.176(8) 0.149(7) 0.180(8) 0.040(6) -0.008(6) -0.055(6) N20 0.074(7) 0.073(7) 0.052(6) -0.017(5) -0.010(5) -0.007(6) C23 0.080(10) 0.058(9) 0.087(10) -0.017(7) 0.002(8) -0.005(8) F6 0.180(9) 0.125(8) 0.127(8) 0.000 0.000 -0.001(7) C7 0.069(8) 0.051(7) 0.050(6) -0.010(5) -0.009(6) -0.013(7) C1 0.072(9) 0.093(10) 0.035(6) -0.013(6) -0.002(6) -0.024(8) C10 0.084(9) 0.050(8) 0.092(9) 0.006(7) -0.018(7) -0.003(7) F13 0.279(11) 0.265(11) 0.237(10) -0.022(8) -0.052(9) -0.010(8) C13 0.063(8) 0.053(7) 0.047(6) -0.006(5) 0.002(6) -0.005(6) C20 0.050(7) 0.063(8) 0.071(8) -0.013(6) -0.005(6) -0.006(6) C2 0.048(8) 0.096(10) 0.055(7) 0.001(7) -0.014(6) 0.003(7) C18 0.054(9) 0.067(10) 0.127(13) -0.033(9) -0.011(9) 0.000(7) C11 0.072(8) 0.070(9) 0.056(7) 0.015(6) -0.009(6) -0.015(7) C8 0.053(7) 0.034(6) 0.059(6) -0.010(5) -0.005(5) 0.010(5) F14 0.234(9) 0.179(9) 0.220(9) 0.040(7) -0.001(8) -0.023(8) C16 0.066(8) 0.058(8) 0.081(9) -0.004(6) -0.011(7) 0.006(6) C24 0.084(11) 0.114(14) 0.151(14) 0.019(11) -0.029(10) 0.023(10) F11 0.321(13) 0.264(13) 0.307(13) 0.004(9) 0.004(9) 0.035(9) C6 0.081(10) 0.092(11) 0.093(10) -0.019(8) -0.027(8) -0.026(8) F2 0.124(6) 0.166(8) 0.139(6) 0.017(6) 0.028(5) 0.019(6) C3 0.053(9) 0.130(14) 0.063(8) 0.000(8) -0.003(7) 0.007(8) C4 0.072(12) 0.17(2) 0.072(10) -0.018(12) 0.008(8) -0.028(13) C22 0.141(14) 0.093(12) 0.136(13) -0.022(10) 0.066(12) -0.043(11) F1 0.173(8) 0.257(10) 0.157(7) 0.020(7) -0.033(7) -0.022(7) F12 0.266(10) 0.261(10) 0.213(9) 0.049(8) 0.042(8) -0.011(8) C19 0.066(9) 0.060(9) 0.131(13) -0.022(8) 0.031(9) -0.010(7) F9 0.275(10) 0.239(10) 0.261(10) 0.028(8) 0.084(9) 0.017(8) C17 0.089(12) 0.101(12) 0.100(12) -0.024(10) -0.042(10) 0.011(9) F5 0.135(7) 0.165(8) 0.152(7) 0.009(6) 0.005(6) 0.040(6) C5 0.098(14) 0.160(19) 0.093(12) -0.026(12) -0.005(10) -0.069(13) F3 0.226(11) 0.194(11) 0.186(10) 0.000 0.054(8) 0.000 F4 0.217(11) 0.196(11) 0.248(12) 0.000 0.043(9) 0.000 F15 0.151(9) 0.194(10) 0.112(8) 0.000 0.000 0.016(7) C25 0.071(9) 0.058(8) 0.101(10) 0.008(7) -0.021(7) 0.009(6) C26 0.053(8) 0.116(12) 0.080(9) -0.003(8) 0.010(7) -0.007(7) _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 F10 Sb4 1.934(17) . ? Sb1 F3 1.71(2) . ? Sb1 F1 1.817(11) 4 ? Sb1 F1 1.817(11) . ? Sb1 F4 1.84(2) . ? Sb1 F2 1.866(9) . ? Sb1 F2 1.866(9) 4 ? Sb2 F6 1.796(13) . ? Sb2 F7 1.833(10) . ? Sb2 F7 1.833(10) 2 ? Sb2 F15 1.834(13) . ? Sb2 F5 1.853(9) . ? Sb2 F5 1.853(10) 2 ? Fe1 N1 2.142(8) . ? Fe1 N4 2.148(8) . ? Fe1 N20 2.152(11) . ? Fe1 N15 2.160(11) . ? Fe1 N3 2.243(9) . ? Fe1 N2 2.268(8) . ? Sb4 F11 1.66(2) . ? Sb4 F13 1.693(16) . ? Sb4 F9 1.705(15) . ? Sb4 F14 1.826(14) . ? Sb4 F12 1.857(15) . ? N5 N4 1.320(10) . ? N5 N6 1.345(11) . ? N4 C8 1.336(12) . ? N8 N7 1.327(10) . ? N8 C14 1.335(12) . ? N8 C15 1.418(13) . ? N7 N1 1.339(11) . ? N6 C7 1.317(13) . ? N6 C1 1.460(14) . ? N2 C12 1.450(13) . ? N2 C26 1.484(13) . ? N2 C11 1.501(14) . ? N1 C13 1.377(12) . ? C15 C16 1.369(14) . ? C15 C20 1.385(15) . ? C9 C8 1.472(14) . ? C9 N3 1.518(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? N3 C25 1.469(13) . ? N3 C10 1.479(14) . ? N15 C23 1.101(15) . ? C12 C13 1.501(14) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C13 1.350(13) . ? C14 H14 0.9300 . ? C21 N20 1.135(13) . ? C21 C22 1.400(17) . ? C23 C24 1.472(19) . ? C7 C8 1.363(13) . ? C7 H7 0.9300 . ? C1 C6 1.320(17) . ? C1 C2 1.404(16) . ? C10 C11 1.527(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C20 C19 1.411(15) . ? C20 H20 0.9300 . ? C2 C3 1.369(15) . ? C2 H2 0.9300 . ? C18 C19 1.356(18) . ? C18 C17 1.363(19) . ? C18 H18 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C16 C17 1.404(18) . ? C16 H16 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C6 C5 1.382(19) . ? C6 H6 0.9300 . ? C3 C4 1.31(2) . ? C3 H3 0.9300 . ? C4 C5 1.40(2) . ? C4 H4 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C19 H19 0.9300 . ? C17 H17 0.9300 . ? C5 H5 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3 Sb1 F1 89.4(5) . 4 ? F3 Sb1 F1 89.4(5) . . ? F1 Sb1 F1 178.9(9) 4 . ? F3 Sb1 F4 180.000(6) . . ? F1 Sb1 F4 90.6(5) 4 . ? F1 Sb1 F4 90.6(5) . . ? F3 Sb1 F2 89.7(3) . . ? F1 Sb1 F2 92.2(5) 4 . ? F1 Sb1 F2 87.8(5) . . ? F4 Sb1 F2 90.3(3) . . ? F3 Sb1 F2 89.7(3) . 4 ? F1 Sb1 F2 87.8(5) 4 4 ? F1 Sb1 F2 92.2(5) . 4 ? F4 Sb1 F2 90.3(3) . 4 ? F2 Sb1 F2 179.4(7) . 4 ? F6 Sb2 F7 88.8(3) . . ? F6 Sb2 F7 88.8(3) . 2 ? F7 Sb2 F7 177.6(7) . 2 ? F6 Sb2 F15 180.000(2) . . ? F7 Sb2 F15 91.2(3) . . ? F7 Sb2 F15 91.2(3) 2 . ? F6 Sb2 F5 91.2(3) . . ? F7 Sb2 F5 90.5(5) . . ? F7 Sb2 F5 89.6(5) 2 . ? F15 Sb2 F5 88.8(3) . . ? F6 Sb2 F5 91.2(3) . 2 ? F7 Sb2 F5 89.6(5) . 2 ? F7 Sb2 F5 90.5(5) 2 2 ? F15 Sb2 F5 88.8(3) . 2 ? F5 Sb2 F5 177.6(6) . 2 ? N1 Fe1 N4 173.1(3) . . ? N1 Fe1 N20 85.6(3) . . ? N4 Fe1 N20 99.1(3) . . ? N1 Fe1 N15 97.7(4) . . ? N4 Fe1 N15 87.0(4) . . ? N20 Fe1 N15 94.7(4) . . ? N1 Fe1 N3 98.7(3) . . ? N4 Fe1 N3 75.8(3) . . ? N20 Fe1 N3 96.0(4) . . ? N15 Fe1 N3 161.0(4) . . ? N1 Fe1 N2 75.5(3) . . ? N4 Fe1 N2 99.2(3) . . ? N20 Fe1 N2 160.1(3) . . ? N15 Fe1 N2 94.1(4) . . ? N3 Fe1 N2 80.9(3) . . ? F11 Sb4 F13 96.6(10) . . ? F11 Sb4 F9 93.8(9) . . ? F13 Sb4 F9 99.5(9) . . ? F11 Sb4 F14 167.9(8) . . ? F13 Sb4 F14 95.2(8) . . ? F9 Sb4 F14 86.9(7) . . ? F11 Sb4 F12 87.7(8) . . ? F13 Sb4 F12 85.6(8) . . ? F9 Sb4 F12 174.5(8) . . ? F14 Sb4 F12 90.5(7) . . ? F11 Sb4 F10 87.2(9) . . ? F13 Sb4 F10 168.6(8) . . ? F9 Sb4 F10 91.0(9) . . ? F14 Sb4 F10 80.7(8) . . ? F12 Sb4 F10 83.8(7) . . ? N4 N5 N6 105.7(8) . . ? N5 N4 C8 110.5(8) . . ? N5 N4 Fe1 134.0(7) . . ? C8 N4 Fe1 115.4(7) . . ? N7 N8 C14 111.9(8) . . ? N7 N8 C15 117.3(9) . . ? C14 N8 C15 130.8(9) . . ? N8 N7 N1 105.8(8) . . ? C7 N6 N5 110.3(8) . . ? C7 N6 C1 129.2(10) . . ? N5 N6 C1 120.5(9) . . ? C12 N2 C26 111.6(9) . . ? C12 N2 C11 107.3(9) . . ? C26 N2 C11 110.4(9) . . ? C12 N2 Fe1 109.1(6) . . ? C26 N2 Fe1 112.2(7) . . ? C11 N2 Fe1 105.9(6) . . ? N7 N1 C13 109.0(8) . . ? N7 N1 Fe1 134.5(7) . . ? C13 N1 Fe1 116.3(7) . . ? C16 C15 C20 121.3(11) . . ? C16 C15 N8 118.8(11) . . ? C20 C15 N8 119.8(10) . . ? C8 C9 N3 107.5(9) . . ? C8 C9 H9A 110.2 . . ? N3 C9 H9A 110.2 . . ? C8 C9 H9B 110.2 . . ? N3 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? C25 N3 C10 112.0(9) . . ? C25 N3 C9 108.3(9) . . ? C10 N3 C9 111.4(9) . . ? C25 N3 Fe1 113.0(7) . . ? C10 N3 Fe1 106.1(7) . . ? C9 N3 Fe1 106.0(6) . . ? C23 N15 Fe1 154.8(11) . . ? N2 C12 C13 110.1(8) . . ? N2 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N2 C12 H12B 109.6 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N8 C14 C13 106.4(9) . . ? N8 C14 H14 126.8 . . ? C13 C14 H14 126.8 . . ? N20 C21 C22 177.4(15) . . ? C21 N20 Fe1 155.5(9) . . ? N15 C23 C24 177.4(16) . . ? N6 C7 C8 107.0(10) . . ? N6 C7 H7 126.5 . . ? C8 C7 H7 126.5 . . ? C6 C1 C2 121.7(13) . . ? C6 C1 N6 120.7(13) . . ? C2 C1 N6 117.7(11) . . ? N3 C10 C11 111.8(9) . . ? N3 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? N3 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C14 C13 N1 106.9(9) . . ? C14 C13 C12 136.1(10) . . ? N1 C13 C12 117.0(9) . . ? C15 C20 C19 119.8(12) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C3 C2 C1 116.4(13) . . ? C3 C2 H2 121.8 . . ? C1 C2 H2 121.8 . . ? C19 C18 C17 123.0(13) . . ? C19 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? N2 C11 C10 109.9(9) . . ? N2 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N2 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N4 C8 C7 106.4(9) . . ? N4 C8 C9 118.5(9) . . ? C7 C8 C9 135.0(10) . . ? C15 C16 C17 118.2(13) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C1 C6 C5 119.9(16) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C4 C3 C2 124.1(16) . . ? C4 C3 H3 118.0 . . ? C2 C3 H3 118.0 . . ? C3 C4 C5 118.5(17) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C18 C19 C20 117.7(13) . . ? C18 C19 H19 121.2 . . ? C20 C19 H19 121.2 . . ? C18 C17 C16 119.9(13) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C6 C5 C4 119.4(17) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N3 C25 H25A 109.5 . . ? N3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N2 C26 H26A 109.5 . . ? N2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 N5 N4 C8 1.2(10) . . . . ? N6 N5 N4 Fe1 -176.1(6) . . . . ? N1 Fe1 N4 N5 125(3) . . . . ? N20 Fe1 N4 N5 -103.4(9) . . . . ? N15 Fe1 N4 N5 -9.1(9) . . . . ? N3 Fe1 N4 N5 162.7(9) . . . . ? N2 Fe1 N4 N5 84.6(9) . . . . ? N1 Fe1 N4 C8 -53(3) . . . . ? N20 Fe1 N4 C8 79.3(7) . . . . ? N15 Fe1 N4 C8 173.6(8) . . . . ? N3 Fe1 N4 C8 -14.6(7) . . . . ? N2 Fe1 N4 C8 -92.7(7) . . . . ? C14 N8 N7 N1 -0.4(11) . . . . ? C15 N8 N7 N1 177.8(8) . . . . ? N4 N5 N6 C7 -0.5(10) . . . . ? N4 N5 N6 C1 177.5(8) . . . . ? N1 Fe1 N2 C12 27.9(7) . . . . ? N4 Fe1 N2 C12 -156.7(8) . . . . ? N20 Fe1 N2 C12 47.1(15) . . . . ? N15 Fe1 N2 C12 -69.0(8) . . . . ? N3 Fe1 N2 C12 129.4(8) . . . . ? N1 Fe1 N2 C26 152.1(8) . . . . ? N4 Fe1 N2 C26 -32.5(8) . . . . ? N20 Fe1 N2 C26 171.3(10) . . . . ? N15 Fe1 N2 C26 55.2(8) . . . . ? N3 Fe1 N2 C26 -106.4(8) . . . . ? N1 Fe1 N2 C11 -87.3(7) . . . . ? N4 Fe1 N2 C11 88.1(7) . . . . ? N20 Fe1 N2 C11 -68.2(13) . . . . ? N15 Fe1 N2 C11 175.7(7) . . . . ? N3 Fe1 N2 C11 14.2(6) . . . . ? N8 N7 N1 C13 0.1(11) . . . . ? N8 N7 N1 Fe1 -175.0(7) . . . . ? N4 Fe1 N1 N7 120(3) . . . . ? N20 Fe1 N1 N7 -12.2(9) . . . . ? N15 Fe1 N1 N7 -106.4(9) . . . . ? N3 Fe1 N1 N7 83.1(9) . . . . ? N2 Fe1 N1 N7 161.3(10) . . . . ? N4 Fe1 N1 C13 -55(3) . . . . ? N20 Fe1 N1 C13 173.0(8) . . . . ? N15 Fe1 N1 C13 78.8(8) . . . . ? N3 Fe1 N1 C13 -91.7(7) . . . . ? N2 Fe1 N1 C13 -13.5(7) . . . . ? N7 N8 C15 C16 -153.4(9) . . . . ? C14 N8 C15 C16 24.4(15) . . . . ? N7 N8 C15 C20 29.0(13) . . . . ? C14 N8 C15 C20 -153.2(10) . . . . ? C8 C9 N3 C25 -164.7(9) . . . . ? C8 C9 N3 C10 71.8(12) . . . . ? C8 C9 N3 Fe1 -43.1(10) . . . . ? N1 Fe1 N3 C25 -34.6(8) . . . . ? N4 Fe1 N3 C25 149.7(8) . . . . ? N20 Fe1 N3 C25 51.8(8) . . . . ? N15 Fe1 N3 C25 175.8(10) . . . . ? N2 Fe1 N3 C25 -108.3(8) . . . . ? N1 Fe1 N3 C10 88.4(7) . . . . ? N4 Fe1 N3 C10 -87.3(7) . . . . ? N20 Fe1 N3 C10 174.9(7) . . . . ? N15 Fe1 N3 C10 -61.2(14) . . . . ? N2 Fe1 N3 C10 14.7(7) . . . . ? N1 Fe1 N3 C9 -153.1(7) . . . . ? N4 Fe1 N3 C9 31.2(7) . . . . ? N20 Fe1 N3 C9 -66.6(7) . . . . ? N15 Fe1 N3 C9 57.3(14) . . . . ? N2 Fe1 N3 C9 133.2(7) . . . . ? N1 Fe1 N15 C23 159(3) . . . . ? N4 Fe1 N15 C23 -26(3) . . . . ? N20 Fe1 N15 C23 72(3) . . . . ? N3 Fe1 N15 C23 -52(3) . . . . ? N2 Fe1 N15 C23 -125(3) . . . . ? C26 N2 C12 C13 -161.8(10) . . . . ? C11 N2 C12 C13 77.0(11) . . . . ? Fe1 N2 C12 C13 -37.3(12) . . . . ? N7 N8 C14 C13 0.6(11) . . . . ? C15 N8 C14 C13 -177.3(10) . . . . ? C22 C21 N20 Fe1 114(29) . . . . ? N1 Fe1 N20 C21 -23(3) . . . . ? N4 Fe1 N20 C21 162(2) . . . . ? N15 Fe1 N20 C21 74(3) . . . . ? N3 Fe1 N20 C21 -121(3) . . . . ? N2 Fe1 N20 C21 -42(3) . . . . ? Fe1 N15 C23 C24 52(36) . . . . ? N5 N6 C7 C8 -0.4(11) . . . . ? C1 N6 C7 C8 -178.1(9) . . . . ? C7 N6 C1 C6 16.6(16) . . . . ? N5 N6 C1 C6 -161.0(10) . . . . ? C7 N6 C1 C2 -163.7(10) . . . . ? N5 N6 C1 C2 18.7(13) . . . . ? C25 N3 C10 C11 81.1(12) . . . . ? C9 N3 C10 C11 -157.4(9) . . . . ? Fe1 N3 C10 C11 -42.5(11) . . . . ? N8 C14 C13 N1 -0.5(11) . . . . ? N8 C14 C13 C12 179.0(13) . . . . ? N7 N1 C13 C14 0.3(11) . . . . ? Fe1 N1 C13 C14 176.3(7) . . . . ? N7 N1 C13 C12 -179.3(9) . . . . ? Fe1 N1 C13 C12 -3.3(12) . . . . ? N2 C12 C13 C14 -151.2(13) . . . . ? N2 C12 C13 N1 28.3(15) . . . . ? C16 C15 C20 C19 3.7(17) . . . . ? N8 C15 C20 C19 -178.8(10) . . . . ? C6 C1 C2 C3 0.2(17) . . . . ? N6 C1 C2 C3 -179.5(9) . . . . ? C12 N2 C11 C10 -157.3(9) . . . . ? C26 N2 C11 C10 80.8(11) . . . . ? Fe1 N2 C11 C10 -40.8(10) . . . . ? N3 C10 C11 N2 59.0(12) . . . . ? N5 N4 C8 C7 -1.5(11) . . . . ? Fe1 N4 C8 C7 176.4(7) . . . . ? N5 N4 C8 C9 175.0(9) . . . . ? Fe1 N4 C8 C9 -7.1(12) . . . . ? N6 C7 C8 N4 1.1(11) . . . . ? N6 C7 C8 C9 -174.5(12) . . . . ? N3 C9 C8 N4 35.1(14) . . . . ? N3 C9 C8 C7 -149.7(12) . . . . ? C20 C15 C16 C17 -2.1(17) . . . . ? N8 C15 C16 C17 -179.6(10) . . . . ? C2 C1 C6 C5 -0.2(19) . . . . ? N6 C1 C6 C5 179.5(11) . . . . ? C1 C2 C3 C4 -1.2(19) . . . . ? C2 C3 C4 C5 2(2) . . . . ? C17 C18 C19 C20 2(2) . . . . ? C15 C20 C19 C18 -3.5(18) . . . . ? C19 C18 C17 C16 0(2) . . . . ? C15 C16 C17 C18 0.3(19) . . . . ? C1 C6 C5 C4 1(2) . . . . ? C3 C4 C5 C6 -2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.300 _refine_diff_density_min -1.595 _refine_diff_density_rms 0.130 # Attachment '5a-Ni.cif' data_Ni-1 _database_code_depnum_ccdc_archive 'CCDC 736997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Cl2 N8 Ni O12' _chemical_formula_weight 734.20 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' Cl Cl 0.1484 0.1585 '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' Ni Ni 0.3393 1.1124 '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 C2/c 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 7.899(5) _cell_length_b 18.312(5) _cell_length_c 22.243(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.183(5) _cell_angle_gamma 90.00 _cell_volume 3215(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2853 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 25 _exptl_crystal_description rectangular _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7300 _exptl_absorpt_correction_T_max 0.8500 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11232 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2835 _reflns_number_gt 1523 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2835 _refine_ls_number_parameters 223 _refine_ls_number_restraints 49 _refine_ls_R_factor_all 0.1593 _refine_ls_R_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.3302 _refine_ls_wR_factor_gt 0.2752 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.114 _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 Ni1 Ni 1.0000 0.08202(8) 0.2500 0.0682(7) Uani 1 2 d S . . O5 O 0.8471(9) 0.0038(4) 0.2886(3) 0.105(2) Uani 1 1 d DU . . N1 N 0.6756(8) 0.0940(4) 0.0968(3) 0.0683(18) Uani 1 1 d . . . N2 N 0.6993(8) 0.0682(4) 0.1530(3) 0.0706(18) Uani 1 1 d . . . N3 N 0.8539(8) 0.0850(3) 0.1694(3) 0.0681(17) Uani 1 1 d . . . N4 N 1.1232(8) 0.1669(4) 0.2043(3) 0.0727(19) Uani 1 1 d . . . C1 C 0.4249(10) 0.0224(5) 0.0721(4) 0.075(2) Uani 1 1 d . . . H1 H 0.4619 -0.0133 0.0992 0.090 Uiso 1 1 calc R . . C2 C 0.2768(11) 0.0134(5) 0.0396(4) 0.084(3) Uani 1 1 d . . . H2 H 0.2131 -0.0288 0.0443 0.101 Uiso 1 1 calc R . . C3 C 0.2204(12) 0.0671(6) -0.0006(4) 0.085(3) Uani 1 1 d . . . H3 H 0.1203 0.0608 -0.0233 0.102 Uiso 1 1 calc R . . C4 C 0.3117(13) 0.1276(6) -0.0060(4) 0.096(3) Uani 1 1 d . . . H4 H 0.2708 0.1638 -0.0320 0.115 Uiso 1 1 calc R . . C5 C 0.4650(11) 0.1395(5) 0.0252(4) 0.085(3) Uani 1 1 d . . . H5 H 0.5272 0.1820 0.0199 0.102 Uiso 1 1 calc R . . C6 C 0.5207(10) 0.0852(4) 0.0645(3) 0.068(2) Uani 1 1 d . . . C7 C 0.8146(9) 0.1312(5) 0.0800(3) 0.068(2) Uani 1 1 d . . . H7 H 0.8285 0.1564 0.0442 0.082 Uiso 1 1 calc R . . C8 C 0.9289(9) 0.1237(5) 0.1267(3) 0.071(2) Uani 1 1 d . . . C9 C 1.0999(10) 0.1535(6) 0.1376(4) 0.082(3) Uani 1 1 d . . . H9A H 1.1126 0.1988 0.1156 0.099 Uiso 1 1 calc R . . H9B H 1.1840 0.1190 0.1243 0.099 Uiso 1 1 calc R . . C10 C 1.0219(11) 0.2339(5) 0.2190(4) 0.078(2) Uani 1 1 d . . . H10A H 1.0877 0.2772 0.2108 0.094 Uiso 1 1 calc R . . H10B H 0.9194 0.2352 0.1936 0.094 Uiso 1 1 calc R . . C21 C 1.3013(9) 0.1770(5) 0.2198(4) 0.083(3) Uani 1 1 d . . . H21A H 1.3456 0.2155 0.1956 0.125 Uiso 1 1 calc R . . H21B H 1.3615 0.1326 0.2125 0.125 Uiso 1 1 calc R . . H21C H 1.3149 0.1898 0.2616 0.125 Uiso 1 1 calc R . . Cl1 Cl 0.8669(5) 0.16860(16) 0.88296(13) 0.1142(11) Uani 1 1 d . . . O4 O 0.697(2) 0.1465(8) 0.8671(7) 0.233(6) Uani 1 1 d U . . O1 O 0.8901(13) 0.2298(6) 0.8519(5) 0.173(4) Uani 1 1 d U . . O2 O 0.8773(15) 0.1810(6) 0.9415(5) 0.170(4) Uani 1 1 d U . . O3 O 0.9664(13) 0.1043(6) 0.8722(5) 0.150(3) Uani 1 1 d U . . O7 O 0.254(3) 0.8993(16) 0.3060(15) 0.228(11) Uani 0.50 1 d PDU . . H7B H 0.1597 0.9063 0.3224 0.273 Uiso 1 1 d RD . . O6 O 0.5000 0.9626(12) 0.2500 0.214(7) Uani 1 2 d SDU . . H7A H 0.236(5) 0.879(10) 0.272(4) 0.257 Uiso 1 1 d D . . H5A H 0.752(10) -0.012(9) 0.274(8) 0.257 Uiso 1 1 d D . . H5B H 0.926(13) -0.025(7) 0.278(9) 0.257 Uiso 1 1 d D . . H6A H 0.55(2) 0.928(6) 0.231(9) 0.257 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0688(10) 0.0882(12) 0.0473(9) 0.000 -0.0010(6) 0.000 O5 0.116(5) 0.111(5) 0.087(4) 0.026(4) -0.011(4) -0.021(4) N1 0.074(4) 0.089(5) 0.042(3) 0.001(3) 0.001(3) -0.006(3) N2 0.073(4) 0.090(5) 0.048(4) 0.008(3) 0.000(3) -0.015(3) N3 0.063(4) 0.096(5) 0.045(4) 0.000(3) -0.004(3) -0.004(3) N4 0.063(4) 0.099(5) 0.055(4) -0.003(3) -0.003(3) -0.010(3) C1 0.083(6) 0.091(6) 0.051(5) -0.004(4) -0.003(4) -0.006(5) C2 0.083(6) 0.100(7) 0.068(6) -0.010(5) 0.007(5) -0.022(5) C3 0.076(6) 0.113(8) 0.067(6) -0.023(5) -0.008(5) -0.012(5) C4 0.102(7) 0.120(8) 0.064(6) 0.012(6) -0.009(5) 0.004(7) C5 0.079(6) 0.108(7) 0.067(5) 0.008(5) -0.010(4) -0.009(5) C6 0.067(5) 0.087(6) 0.048(4) -0.006(4) -0.003(4) -0.016(4) C7 0.065(5) 0.105(6) 0.035(4) 0.002(4) 0.005(3) -0.008(4) C8 0.064(5) 0.099(6) 0.050(5) 0.000(4) 0.011(4) 0.001(4) C9 0.062(5) 0.136(8) 0.050(5) -0.014(5) 0.010(4) -0.010(5) C10 0.071(5) 0.092(6) 0.072(5) 0.010(4) 0.001(4) 0.003(4) C21 0.055(5) 0.128(8) 0.067(5) 0.004(5) 0.003(4) -0.008(5) Cl1 0.169(3) 0.095(2) 0.0766(18) 0.0188(14) -0.0087(17) -0.0003(18) O4 0.217(9) 0.228(9) 0.253(10) 0.015(8) -0.024(8) 0.005(8) O1 0.186(7) 0.172(7) 0.162(7) 0.060(6) 0.030(6) 0.013(6) O2 0.206(8) 0.166(7) 0.140(7) -0.006(6) 0.038(6) -0.001(6) O3 0.163(6) 0.148(6) 0.139(7) -0.017(5) -0.007(5) 0.023(6) O7 0.224(14) 0.225(14) 0.235(14) -0.007(10) 0.024(10) 0.013(10) O6 0.216(11) 0.218(11) 0.207(11) 0.000 0.001(9) 0.000 _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 Ni1 O5 2.079(7) 2_755 ? Ni1 O5 2.079(7) . ? Ni1 N3 2.095(6) . ? Ni1 N3 2.095(6) 2_755 ? Ni1 N4 2.114(7) . ? Ni1 N4 2.114(6) 2_755 ? O5 H5A 0.86(9) . ? O5 H5B 0.86(11) . ? N1 N2 1.343(8) . ? N1 C7 1.357(9) . ? N1 C6 1.404(9) . ? N2 N3 1.299(8) . ? N3 C8 1.342(10) . ? N4 C21 1.448(10) . ? N4 C10 1.507(10) . ? N4 C9 1.509(10) . ? C1 C2 1.361(11) . ? C1 C6 1.389(11) . ? C1 H1 0.9300 . ? C2 C3 1.390(13) . ? C2 H2 0.9300 . ? C3 C4 1.329(13) . ? C3 H3 0.9300 . ? C4 C5 1.389(13) . ? C4 H4 0.9300 . ? C5 C6 1.385(11) . ? C5 H5 0.9300 . ? C7 C8 1.357(10) . ? C7 H7 0.9300 . ? C8 C9 1.468(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.433(17) 2_755 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cl1 O2 1.321(11) . ? Cl1 O1 1.332(10) . ? Cl1 O4 1.436(15) . ? Cl1 O3 1.440(9) . ? O7 H7B 0.8500 . ? O7 H7A 0.850(11) . ? O6 H6A 0.87(14) . ? 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 O5 Ni1 O5 93.0(4) 2_755 . ? O5 Ni1 N3 88.5(3) 2_755 . ? O5 Ni1 N3 93.5(3) . . ? O5 Ni1 N3 93.5(3) 2_755 2_755 ? O5 Ni1 N3 88.5(3) . 2_755 ? N3 Ni1 N3 177.0(4) . 2_755 ? O5 Ni1 N4 91.3(3) 2_755 . ? O5 Ni1 N4 171.8(3) . . ? N3 Ni1 N4 79.6(2) . . ? N3 Ni1 N4 98.2(2) 2_755 . ? O5 Ni1 N4 171.8(3) 2_755 2_755 ? O5 Ni1 N4 91.3(3) . 2_755 ? N3 Ni1 N4 98.2(2) . 2_755 ? N3 Ni1 N4 79.6(2) 2_755 2_755 ? N4 Ni1 N4 85.4(4) . 2_755 ? Ni1 O5 H5A 127(10) . . ? Ni1 O5 H5B 82(10) . . ? H5A O5 H5B 109(14) . . ? N2 N1 C7 110.3(6) . . ? N2 N1 C6 121.6(6) . . ? C7 N1 C6 128.0(6) . . ? N3 N2 N1 106.0(6) . . ? N2 N3 C8 111.2(6) . . ? N2 N3 Ni1 135.8(5) . . ? C8 N3 Ni1 112.1(5) . . ? C21 N4 C10 111.3(7) . . ? C21 N4 C9 109.6(6) . . ? C10 N4 C9 107.4(6) . . ? C21 N4 Ni1 116.2(5) . . ? C10 N4 Ni1 103.7(5) . . ? C9 N4 Ni1 108.2(5) . . ? C2 C1 C6 119.8(8) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? C1 C2 C3 120.2(9) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.1(9) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 123.4(9) . . ? C3 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 116.9(9) . . ? C6 C5 H5 121.6 . . ? C4 C5 H5 121.6 . . ? C5 C6 C1 120.6(7) . . ? C5 C6 N1 119.3(7) . . ? C1 C6 N1 120.1(7) . . ? N1 C7 C8 105.1(7) . . ? N1 C7 H7 127.5 . . ? C8 C7 H7 127.5 . . ? N3 C8 C7 107.3(7) . . ? N3 C8 C9 120.5(7) . . ? C7 C8 C9 132.1(8) . . ? C8 C9 N4 107.4(6) . . ? C8 C9 H9A 110.2 . . ? N4 C9 H9A 110.2 . . ? C8 C9 H9B 110.2 . . ? N4 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? C10 C10 N4 111.0(5) 2_755 . ? C10 C10 H10A 109.4 2_755 . ? N4 C10 H10A 109.4 . . ? C10 C10 H10B 109.4 2_755 . ? N4 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N4 C21 H21A 109.5 . . ? N4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 Cl1 O1 111.1(7) . . ? O2 Cl1 O4 108.3(9) . . ? O1 Cl1 O4 104.8(8) . . ? O2 Cl1 O3 106.9(7) . . ? O1 Cl1 O3 121.0(7) . . ? O4 Cl1 O3 104.0(8) . . ? H7B O7 H7A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 N2 N3 -3.9(9) . . . . ? C6 N1 N2 N3 179.7(7) . . . . ? N1 N2 N3 C8 2.8(8) . . . . ? N1 N2 N3 Ni1 170.2(5) . . . . ? O5 Ni1 N3 N2 114.9(8) 2_755 . . . ? O5 Ni1 N3 N2 22.1(8) . . . . ? N3 Ni1 N3 N2 -111.5(7) 2_755 . . . ? N4 Ni1 N3 N2 -153.5(8) . . . . ? N4 Ni1 N3 N2 -69.8(8) 2_755 . . . ? O5 Ni1 N3 C8 -77.7(6) 2_755 . . . ? O5 Ni1 N3 C8 -170.6(6) . . . . ? N3 Ni1 N3 C8 55.9(5) 2_755 . . . ? N4 Ni1 N3 C8 13.9(5) . . . . ? N4 Ni1 N3 C8 97.6(5) 2_755 . . . ? O5 Ni1 N4 C21 -63.7(6) 2_755 . . . ? O5 Ni1 N4 C21 175.1(17) . . . . ? N3 Ni1 N4 C21 -152.0(6) . . . . ? N3 Ni1 N4 C21 30.1(6) 2_755 . . . ? N4 Ni1 N4 C21 108.8(6) 2_755 . . . ? O5 Ni1 N4 C10 173.9(5) 2_755 . . . ? O5 Ni1 N4 C10 53(2) . . . . ? N3 Ni1 N4 C10 85.7(5) . . . . ? N3 Ni1 N4 C10 -92.3(5) 2_755 . . . ? N4 Ni1 N4 C10 -13.6(4) 2_755 . . . ? O5 Ni1 N4 C9 60.1(5) 2_755 . . . ? O5 Ni1 N4 C9 -61(2) . . . . ? N3 Ni1 N4 C9 -28.2(5) . . . . ? N3 Ni1 N4 C9 153.8(5) 2_755 . . . ? N4 Ni1 N4 C9 -127.5(6) 2_755 . . . ? C6 C1 C2 C3 -0.6(13) . . . . ? C1 C2 C3 C4 -1.1(14) . . . . ? C2 C3 C4 C5 2.1(15) . . . . ? C3 C4 C5 C6 -1.3(15) . . . . ? C4 C5 C6 C1 -0.5(13) . . . . ? C4 C5 C6 N1 179.4(8) . . . . ? C2 C1 C6 C5 1.5(13) . . . . ? C2 C1 C6 N1 -178.5(7) . . . . ? N2 N1 C6 C5 145.7(8) . . . . ? C7 N1 C6 C5 -30.0(12) . . . . ? N2 N1 C6 C1 -34.4(11) . . . . ? C7 N1 C6 C1 149.9(8) . . . . ? N2 N1 C7 C8 3.5(9) . . . . ? C6 N1 C7 C8 179.6(7) . . . . ? N2 N3 C8 C7 -0.7(9) . . . . ? Ni1 N3 C8 C7 -171.3(6) . . . . ? N2 N3 C8 C9 175.3(7) . . . . ? Ni1 N3 C8 C9 4.7(10) . . . . ? N1 C7 C8 N3 -1.7(9) . . . . ? N1 C7 C8 C9 -177.0(9) . . . . ? N3 C8 C9 N4 -28.5(11) . . . . ? C7 C8 C9 N4 146.2(9) . . . . ? C21 N4 C9 C8 164.6(7) . . . . ? C10 N4 C9 C8 -74.4(9) . . . . ? Ni1 N4 C9 C8 37.0(8) . . . . ? C21 N4 C10 C10 -84.1(9) . . . 2_755 ? C9 N4 C10 C10 155.9(8) . . . 2_755 ? Ni1 N4 C10 C10 41.5(9) . . . 2_755 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.197 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.114