# 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 'Song Gao' _publ_contact_author_email GAOSONG@PKU.EDU.CN _publ_section_title ; Synthesis, Magnetic and Photomagnetic Study of New Iron(II) Spin-Crossover Complexes with N4O2 Coordination Sphere ; loop_ _publ_author_name 'Song Gao' 'Valeriu Mereacre' 'Annie K Powell' 'Zhe-ming Wang' 'Guan-Cheng Xu' 'Hong-Bin Xu' 'Li Zhang' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 756912' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Fe N6 O2' _chemical_formula_sum 'C26 H20 Fe N6 O2' _chemical_formula_weight 504.33 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' Fe Fe 0.3463 0.8444 '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)/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 9.778(2) _cell_length_b 23.745(5) _cell_length_c 10.281(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.96(3) _cell_angle_gamma 90.00 _cell_volume 2316.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 15853 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description bolck _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 27205 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4073 _reflns_number_gt 2888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0407P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4073 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.35500(3) 0.106889(12) 0.60566(3) 0.03989(12) Uani 1 1 d . . . C1 C 0.0768(2) 0.07179(9) 0.7128(2) 0.0476(5) Uani 1 1 d . . . H1 H 0.0532 0.0488 0.6374 0.057 Uiso 1 1 calc R . . C2 C -0.0128(2) 0.07346(10) 0.7967(2) 0.0571(6) Uani 1 1 d . . . H2 H -0.0938 0.0514 0.7794 0.069 Uiso 1 1 calc R . . C3 C 0.0184(2) 0.10806(10) 0.9063(2) 0.0580(6) Uani 1 1 d . . . H3 H -0.0409 0.1099 0.9646 0.070 Uiso 1 1 calc R . . C4 C 0.1399(2) 0.14031(10) 0.9290(2) 0.0497(6) Uani 1 1 d . . . H4 H 0.1626 0.1647 1.0018 0.060 Uiso 1 1 calc R . . C5 C 0.22644(19) 0.13564(8) 0.84208(19) 0.0394(5) Uani 1 1 d . . . C6 C 0.3560(2) 0.16769(8) 0.8585(2) 0.0445(5) Uani 1 1 d . . . H6 H 0.3867 0.1920 0.9306 0.053 Uiso 1 1 calc R . . C7 C 0.60192(19) 0.17711(8) 0.67621(19) 0.0387(5) Uani 1 1 d . . . C8 C 0.7420(2) 0.20269(8) 0.67773(19) 0.0410(5) Uani 1 1 d . . . C9 C 0.80598(19) 0.24005(9) 0.7778(2) 0.0488(5) Uani 1 1 d . . . H9 H 0.7591 0.2506 0.8426 0.059 Uiso 1 1 calc R . . C10 C 0.9381(2) 0.26176(10) 0.7827(2) 0.0586(6) Uani 1 1 d . . . H10 H 0.9797 0.2870 0.8499 0.070 Uiso 1 1 calc R . . C11 C 1.0075(2) 0.24572(10) 0.6875(3) 0.0646(7) Uani 1 1 d . . . H11 H 1.0974 0.2596 0.6916 0.077 Uiso 1 1 calc R . . C12 C 0.9453(2) 0.20934(10) 0.5859(2) 0.0615(7) Uani 1 1 d . . . H12 H 0.9926 0.1991 0.5211 0.074 Uiso 1 1 calc R . . C13 C 0.8126(2) 0.18815(9) 0.5808(2) 0.0511(6) Uani 1 1 d . . . H13 H 0.7703 0.1639 0.5118 0.061 Uiso 1 1 calc R . . C14 C 0.5873(2) 0.03077(10) 0.8065(2) 0.0577(6) Uani 1 1 d . . . H14 H 0.6199 0.0647 0.8479 0.069 Uiso 1 1 calc R . . C15 C 0.6582(2) -0.01811(11) 0.8546(2) 0.0643(7) Uani 1 1 d . . . H15 H 0.7361 -0.0171 0.9274 0.077 Uiso 1 1 calc R . . C16 C 0.6118(2) -0.06807(11) 0.7932(2) 0.0605(6) Uani 1 1 d . . . H16 H 0.6578 -0.1016 0.8237 0.073 Uiso 1 1 calc R . . C17 C 0.4961(2) -0.06821(10) 0.6856(2) 0.0511(6) Uani 1 1 d . . . H17 H 0.4636 -0.1017 0.6419 0.061 Uiso 1 1 calc R . . C18 C 0.42917(19) -0.01789(9) 0.64385(19) 0.0398(5) Uani 1 1 d . . . C19 C 0.30689(19) -0.01374(10) 0.53087(18) 0.0434(5) Uani 1 1 d . . . H19 H 0.2648 -0.0454 0.4851 0.052 Uiso 1 1 calc R . . C20 C 0.12352(19) 0.09932(9) 0.37822(18) 0.0383(5) Uani 1 1 d . . . C21 C -0.00577(19) 0.11696(9) 0.27703(18) 0.0395(5) Uani 1 1 d . . . C22 C -0.1157(2) 0.07956(10) 0.2282(2) 0.0515(6) Uani 1 1 d . . . H22 H -0.1081 0.0424 0.2573 0.062 Uiso 1 1 calc R . . C23 C -0.2357(2) 0.09715(11) 0.1373(2) 0.0588(7) Uani 1 1 d . . . H23 H -0.3089 0.0719 0.1059 0.071 Uiso 1 1 calc R . . C24 C -0.2478(2) 0.15183(12) 0.0926(2) 0.0605(7) Uani 1 1 d . . . H24 H -0.3286 0.1635 0.0306 0.073 Uiso 1 1 calc R . . C25 C -0.1406(2) 0.18910(11) 0.1396(2) 0.0619(6) Uani 1 1 d . . . H25 H -0.1483 0.2260 0.1087 0.074 Uiso 1 1 calc R . . C26 C -0.0206(2) 0.17197(10) 0.2333(2) 0.0511(6) Uani 1 1 d . . . H26 H 0.0506 0.1979 0.2668 0.061 Uiso 1 1 calc R . . N1 N 0.19666(15) 0.10147(6) 0.73360(15) 0.0391(4) Uani 1 1 d . . . N2 N 0.42602(15) 0.16096(6) 0.76903(15) 0.0388(4) Uani 1 1 d . . . N3 N 0.55095(15) 0.18956(7) 0.78157(16) 0.0416(4) Uani 1 1 d . . . N4 N 0.47459(16) 0.03173(7) 0.70383(16) 0.0434(4) Uani 1 1 d . . . N5 N 0.26055(15) 0.03593(7) 0.49807(15) 0.0384(4) Uani 1 1 d . . . N6 N 0.14194(15) 0.04386(7) 0.39584(15) 0.0413(4) Uani 1 1 d . . . O1 O 0.54232(13) 0.14519(6) 0.57962(13) 0.0500(4) Uani 1 1 d . . . O2 O 0.20524(13) 0.13727(6) 0.44087(13) 0.0455(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 Fe1 0.04000(19) 0.0394(2) 0.03650(18) -0.00524(14) 0.00186(13) -0.00499(14) C1 0.0467(12) 0.0471(14) 0.0484(13) -0.0038(11) 0.0105(11) -0.0062(11) C2 0.0456(13) 0.0675(17) 0.0599(15) -0.0020(13) 0.0158(12) -0.0105(12) C3 0.0515(14) 0.0711(17) 0.0575(15) 0.0004(14) 0.0251(12) 0.0004(13) C4 0.0530(13) 0.0559(16) 0.0419(13) -0.0070(11) 0.0145(11) 0.0057(12) C5 0.0393(11) 0.0376(13) 0.0399(12) -0.0001(10) 0.0068(9) 0.0031(9) C6 0.0467(12) 0.0451(14) 0.0392(12) -0.0116(10) 0.0052(10) -0.0011(10) C7 0.0381(11) 0.0334(12) 0.0407(12) 0.0007(10) 0.0018(9) -0.0014(9) C8 0.0402(11) 0.0343(12) 0.0461(12) 0.0030(10) 0.0057(10) 0.0017(9) C9 0.0393(12) 0.0494(15) 0.0544(14) -0.0038(11) 0.0049(10) -0.0032(10) C10 0.0456(13) 0.0558(16) 0.0701(16) -0.0012(13) 0.0053(12) -0.0117(12) C11 0.0425(13) 0.0623(18) 0.0855(18) 0.0228(15) 0.0088(14) -0.0088(12) C12 0.0576(15) 0.0628(18) 0.0709(17) 0.0135(14) 0.0287(13) 0.0039(13) C13 0.0554(14) 0.0440(14) 0.0545(14) 0.0013(11) 0.0142(11) -0.0004(11) C14 0.0507(14) 0.0581(17) 0.0553(15) -0.0065(12) -0.0046(12) -0.0004(12) C15 0.0527(14) 0.073(2) 0.0569(15) -0.0002(14) -0.0076(12) 0.0112(13) C16 0.0625(15) 0.0569(17) 0.0584(15) 0.0057(13) 0.0077(13) 0.0190(13) C17 0.0604(14) 0.0430(14) 0.0486(13) -0.0011(11) 0.0105(12) 0.0062(11) C18 0.0409(11) 0.0404(14) 0.0388(11) -0.0012(10) 0.0108(9) 0.0007(10) C19 0.0473(12) 0.0389(14) 0.0409(12) -0.0074(10) 0.0049(10) -0.0051(10) C20 0.0377(11) 0.0441(14) 0.0330(11) -0.0008(10) 0.0086(9) -0.0030(10) C21 0.0394(11) 0.0454(14) 0.0328(11) -0.0031(10) 0.0072(9) -0.0029(10) C22 0.0461(13) 0.0583(16) 0.0466(13) 0.0027(12) 0.0042(11) -0.0072(11) C23 0.0405(13) 0.083(2) 0.0491(14) -0.0070(13) 0.0036(11) -0.0079(12) C24 0.0433(13) 0.086(2) 0.0462(14) -0.0083(14) -0.0008(11) 0.0191(13) C25 0.0705(16) 0.0521(16) 0.0562(15) 0.0001(12) 0.0015(13) 0.0143(13) C26 0.0495(13) 0.0495(15) 0.0478(13) -0.0042(11) -0.0009(11) -0.0010(11) N1 0.0389(9) 0.0369(10) 0.0395(10) -0.0021(8) 0.0058(7) -0.0004(8) N2 0.0371(9) 0.0377(11) 0.0390(9) -0.0024(8) 0.0038(8) -0.0010(8) N3 0.0373(9) 0.0418(11) 0.0438(10) -0.0086(8) 0.0063(8) -0.0091(8) N4 0.0417(10) 0.0450(12) 0.0402(10) -0.0027(9) 0.0035(8) 0.0004(8) N5 0.0389(9) 0.0389(11) 0.0357(9) -0.0034(8) 0.0055(8) -0.0012(8) N6 0.0401(9) 0.0414(11) 0.0372(9) -0.0044(8) -0.0005(8) -0.0037(8) O1 0.0513(8) 0.0545(10) 0.0437(8) -0.0139(8) 0.0104(7) -0.0157(7) O2 0.0451(8) 0.0401(9) 0.0437(8) -0.0018(7) -0.0040(6) -0.0070(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 Fe1 O2 2.0827(15) . ? Fe1 N2 2.0950(16) . ? Fe1 N5 2.1030(16) . ? Fe1 O1 2.1190(13) . ? Fe1 N4 2.2364(17) . ? Fe1 N1 2.2642(16) . ? C1 N1 1.340(2) . ? C1 C2 1.371(3) . ? C1 H1 0.9300 . ? C2 C3 1.368(3) . ? C2 H2 0.9300 . ? C3 C4 1.385(3) . ? C3 H3 0.9300 . ? C4 C5 1.375(3) . ? C4 H4 0.9300 . ? C5 N1 1.353(2) . ? C5 C6 1.452(3) . ? C6 N2 1.283(2) . ? C6 H6 0.9300 . ? C7 O1 1.273(2) . ? C7 N3 1.330(2) . ? C7 C8 1.495(3) . ? C8 C13 1.386(3) . ? C8 C9 1.388(3) . ? C9 C10 1.381(3) . ? C9 H9 0.9300 . ? C10 C11 1.373(3) . ? C10 H10 0.9300 . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 N4 1.330(2) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.369(3) . ? C15 H15 0.9300 . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 C18 1.380(3) . ? C17 H17 0.9300 . ? C18 N4 1.354(2) . ? C18 C19 1.455(3) . ? C19 N5 1.279(2) . ? C19 H19 0.9300 . ? C20 O2 1.272(2) . ? C20 N6 1.336(2) . ? C20 C21 1.490(3) . ? C21 C26 1.378(3) . ? C21 C22 1.391(3) . ? C22 C23 1.377(3) . ? C22 H22 0.9300 . ? C23 C24 1.372(3) . ? C23 H23 0.9300 . ? C24 C25 1.368(3) . ? C24 H24 0.9300 . ? C25 C26 1.388(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? N2 N3 1.3762(19) . ? N5 N6 1.377(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 O2 Fe1 N2 118.16(6) . . ? O2 Fe1 N5 73.52(6) . . ? N2 Fe1 N5 158.64(6) . . ? O2 Fe1 O1 102.01(6) . . ? N2 Fe1 O1 73.07(6) . . ? N5 Fe1 O1 124.11(5) . . ? O2 Fe1 N4 146.30(6) . . ? N2 Fe1 N4 95.23(6) . . ? N5 Fe1 N4 73.35(7) . . ? O1 Fe1 N4 91.47(6) . . ? O2 Fe1 N1 92.70(5) . . ? N2 Fe1 N1 73.14(6) . . ? N5 Fe1 N1 89.14(6) . . ? O1 Fe1 N1 146.18(6) . . ? N4 Fe1 N1 92.80(6) . . ? N1 C1 C2 123.5(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 122.70(18) . . ? N1 C5 C6 114.74(16) . . ? C4 C5 C6 122.56(19) . . ? N2 C6 C5 116.93(17) . . ? N2 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? O1 C7 N3 125.21(17) . . ? O1 C7 C8 119.72(17) . . ? N3 C7 C8 115.05(17) . . ? C13 C8 C9 118.58(18) . . ? C13 C8 C7 120.37(18) . . ? C9 C8 C7 121.03(17) . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 119.3(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.7(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 119.7(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 120.6(2) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? N4 C14 C15 123.2(2) . . ? N4 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? C14 C15 C16 118.7(2) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 119.3(2) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 118.9(2) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? N4 C18 C17 122.20(19) . . ? N4 C18 C19 114.87(18) . . ? C17 C18 C19 122.9(2) . . ? N5 C19 C18 116.32(19) . . ? N5 C19 H19 121.8 . . ? C18 C19 H19 121.8 . . ? O2 C20 N6 125.62(18) . . ? O2 C20 C21 118.55(18) . . ? N6 C20 C21 115.83(17) . . ? C26 C21 C22 118.45(19) . . ? C26 C21 C20 119.92(18) . . ? C22 C21 C20 121.59(19) . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.8(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C21 C26 C25 120.6(2) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C1 N1 C5 116.95(16) . . ? C1 N1 Fe1 129.15(13) . . ? C5 N1 Fe1 113.80(12) . . ? C6 N2 N3 119.13(16) . . ? C6 N2 Fe1 121.35(13) . . ? N3 N2 Fe1 119.51(11) . . ? C7 N3 N2 108.21(15) . . ? C14 N4 C18 117.68(18) . . ? C14 N4 Fe1 127.95(15) . . ? C18 N4 Fe1 114.24(13) . . ? C19 N5 N6 120.44(16) . . ? C19 N5 Fe1 121.16(13) . . ? N6 N5 Fe1 118.29(13) . . ? C20 N6 N5 107.42(15) . . ? C7 O1 Fe1 113.82(11) . . ? C20 O2 Fe1 113.52(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.213 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.055 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 756913' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Fe N6 O2' _chemical_formula_sum 'C28 H24 Fe N6 O2' _chemical_formula_weight 532.38 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 9.982(2) _cell_length_b 20.133(4) _cell_length_c 12.113(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.63(3) _cell_angle_gamma 90.00 _cell_volume 2433.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13858 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour 'blck green' _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 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_T_max 0.879 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4160 _diffrn_reflns_av_R_equivalents 0.0072 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4155 _reflns_number_gt 2836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1948P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(15) _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 0.46(5) _refine_ls_number_reflns 4155 _refine_ls_number_parameters 337 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1389 _refine_ls_R_factor_gt 0.1066 _refine_ls_wR_factor_ref 0.2654 _refine_ls_wR_factor_gt 0.2487 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 0.999 _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 Fe1 Fe 1.03728(13) 0.24154(5) 0.98534(11) 0.0470(5) Uani 1 1 d . . . C1 C 1.2633(10) 0.1466(6) 0.9868(9) 0.061(3) Uani 1 1 d . . . H1 H 1.2480 0.1421 0.9111 0.073 Uiso 1 1 calc R . . C2 C 1.3695(13) 0.1149(7) 1.0321(12) 0.084(4) Uani 1 1 d . . . H2 H 1.4247 0.0887 0.9895 0.101 Uiso 1 1 calc R . . C3 C 1.3950(13) 0.1227(7) 1.1477(11) 0.083(4) Uani 1 1 d . . . H3 H 1.4684 0.1019 1.1817 0.100 Uiso 1 1 calc R . . C4 C 1.3129(11) 0.1602(6) 1.2073(14) 0.084(4) Uani 1 1 d . . . H4 H 1.3260 0.1637 1.2834 0.101 Uiso 1 1 calc R . . C5 C 1.2075(10) 0.1938(6) 1.1538(9) 0.061(3) Uani 1 1 d . . . C6 C 1.1175(12) 0.2404(6) 1.2051(10) 0.062(3) Uani 1 1 d . . . C7 C 1.1147(16) 0.2546(7) 1.3278(11) 0.082(4) Uani 1 1 d . . . H7A H 1.0597 0.2928 1.3403 0.123 Uiso 1 1 calc R . . H7B H 1.2042 0.2631 1.3554 0.123 Uiso 1 1 calc R . . H7C H 1.0785 0.2170 1.3653 0.123 Uiso 1 1 calc R . . C8 C 0.8912(10) 0.3397(6) 1.0701(8) 0.055(3) Uani 1 1 d . . . C9 C 0.7992(10) 0.3991(5) 1.0863(9) 0.056(2) Uani 1 1 d . . . C10 C 0.7849(13) 0.4273(7) 1.1893(10) 0.084(4) Uani 1 1 d . . . H10 H 0.8334 0.4124 1.2512 0.101 Uiso 1 1 calc R . . C11 C 0.6923(15) 0.4798(7) 1.1949(10) 0.091(4) Uani 1 1 d . . . H11 H 0.6804 0.4994 1.2635 0.109 Uiso 1 1 calc R . . C12 C 0.6198(15) 0.5038(7) 1.1085(14) 0.092(4) Uani 1 1 d . . . H12 H 0.5591 0.5383 1.1172 0.110 Uiso 1 1 calc R . . C13 C 0.6388(11) 0.4754(6) 1.0073(15) 0.088(4) Uani 1 1 d . . . H13 H 0.5895 0.4916 0.9468 0.105 Uiso 1 1 calc R . . C14 C 0.7279(11) 0.4235(6) 0.9904(11) 0.067(3) Uani 1 1 d . . . H14 H 0.7405 0.4057 0.9207 0.081 Uiso 1 1 calc R . . C15 C 1.2543(11) 0.3403(6) 0.9693(11) 0.067(3) Uani 1 1 d . . . H15 H 1.2483 0.3472 1.0449 0.080 Uiso 1 1 calc R . . C16 C 1.3503(13) 0.3740(7) 0.9145(15) 0.093(4) Uani 1 1 d . . . H16 H 1.4109 0.4009 0.9534 0.111 Uiso 1 1 calc R . . C17 C 1.3578(14) 0.3681(8) 0.7988(13) 0.094(5) Uani 1 1 d . . . H17 H 1.4195 0.3925 0.7593 0.113 Uiso 1 1 calc R . . C18 C 1.2705(12) 0.3251(6) 0.7471(11) 0.070(3) Uani 1 1 d . . . H18 H 1.2747 0.3191 0.6711 0.084 Uiso 1 1 calc R . . C19 C 1.1780(11) 0.2911(7) 0.8040(10) 0.068(3) Uani 1 1 d . . . C20 C 1.0852(11) 0.2402(5) 0.7604(9) 0.060(3) Uani 1 1 d . . . C21 C 1.0692(14) 0.2238(7) 0.6426(8) 0.072(3) Uani 1 1 d . . . H21A H 1.1276 0.1877 0.6252 0.108 Uiso 1 1 calc R . . H21B H 1.0914 0.2619 0.5992 0.108 Uiso 1 1 calc R . . H21C H 0.9780 0.2112 0.6265 0.108 Uiso 1 1 calc R . . C22 C 0.8770(10) 0.1428(6) 0.9065(9) 0.061(3) Uani 1 1 d . . . C23 C 0.7794(10) 0.0859(5) 0.9052(9) 0.059(3) Uani 1 1 d . . . C24 C 0.7203(17) 0.0638(6) 0.8051(9) 0.089(4) Uani 1 1 d . . . H24 H 0.7465 0.0827 0.7390 0.107 Uiso 1 1 calc R . . C25 C 0.6247(16) 0.0150(9) 0.8032(12) 0.108(5) Uani 1 1 d . . . H25 H 0.5823 0.0032 0.7367 0.130 Uiso 1 1 calc R . . C26 C 0.5907(15) -0.0172(7) 0.9006(12) 0.087(4) Uani 1 1 d . . . H26 H 0.5295 -0.0521 0.8992 0.104 Uiso 1 1 calc R . . C27 C 0.6469(13) 0.0029(6) 0.9945(10) 0.073(3) Uani 1 1 d . . . H27 H 0.6234 -0.0177 1.0599 0.088 Uiso 1 1 calc R . . C28 C 0.7400(11) 0.0537(6) 0.9985(10) 0.069(3) Uani 1 1 d . . . H28 H 0.7770 0.0664 1.0666 0.083 Uiso 1 1 calc R . . N1 N 1.1798(9) 0.1834(5) 1.0409(7) 0.060(2) Uani 1 1 d . . . N2 N 1.0434(8) 0.2709(4) 1.1313(6) 0.0450(18) Uani 1 1 d . . . N3 N 0.9599(9) 0.3219(5) 1.1609(7) 0.058(2) Uani 1 1 d . . . N4 N 1.1683(8) 0.2977(5) 0.9205(6) 0.055(2) Uani 1 1 d . . . N5 N 1.0200(9) 0.2125(5) 0.8402(6) 0.059(2) Uani 1 1 d . . . N6 N 0.9304(8) 0.1594(5) 0.8166(6) 0.058(2) Uani 1 1 d . . . O1 O 0.9006(7) 0.3144(3) 0.9772(6) 0.0536(16) Uani 1 1 d . . . O2 O 0.9007(7) 0.1707(4) 1.0027(6) 0.0600(18) 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 Fe1 0.0684(9) 0.0474(7) 0.0250(6) -0.0022(8) -0.0019(5) 0.0008(9) C1 0.059(6) 0.073(7) 0.052(7) -0.001(5) -0.006(5) 0.022(5) C2 0.089(9) 0.082(8) 0.082(10) -0.008(7) 0.007(7) 0.020(7) C3 0.076(8) 0.101(10) 0.070(9) 0.016(7) -0.018(7) 0.010(7) C4 0.066(8) 0.071(7) 0.115(12) 0.043(8) -0.007(8) -0.011(6) C5 0.053(6) 0.080(8) 0.049(6) 0.017(5) -0.009(5) -0.005(5) C6 0.068(7) 0.077(7) 0.041(6) 0.003(5) 0.000(5) -0.014(6) C7 0.099(10) 0.097(9) 0.050(8) 0.003(6) -0.013(7) -0.010(7) C8 0.051(5) 0.083(8) 0.032(6) -0.006(5) -0.001(4) -0.011(5) C9 0.061(6) 0.063(6) 0.045(6) -0.006(5) 0.006(5) -0.006(5) C10 0.105(10) 0.101(10) 0.046(7) -0.003(7) 0.003(6) 0.004(8) C11 0.141(12) 0.101(10) 0.031(6) -0.020(6) 0.021(7) 0.013(9) C12 0.102(9) 0.076(8) 0.098(12) -0.007(8) 0.030(9) 0.017(7) C13 0.052(7) 0.074(8) 0.137(14) -0.008(8) -0.004(7) 0.004(6) C14 0.066(7) 0.065(7) 0.071(8) -0.022(6) -0.001(6) 0.002(5) C15 0.053(6) 0.073(7) 0.074(8) 0.014(6) 0.000(6) -0.001(5) C16 0.076(8) 0.076(8) 0.126(14) 0.027(9) 0.003(8) -0.002(6) C17 0.084(9) 0.114(11) 0.086(10) 0.057(9) 0.024(8) 0.024(8) C18 0.074(8) 0.072(7) 0.065(8) 0.000(6) 0.017(6) 0.000(6) C19 0.062(7) 0.093(9) 0.049(7) 0.004(6) 0.008(5) 0.013(6) C20 0.063(7) 0.077(7) 0.039(6) -0.007(5) -0.001(5) 0.020(5) C21 0.093(8) 0.101(8) 0.023(5) 0.011(5) 0.009(5) 0.034(7) C22 0.063(6) 0.082(8) 0.038(6) -0.016(5) -0.006(5) 0.004(5) C23 0.067(6) 0.065(6) 0.043(6) -0.011(5) -0.009(5) 0.007(5) C24 0.162(13) 0.076(8) 0.028(6) -0.007(5) -0.020(7) -0.020(8) C25 0.141(13) 0.123(13) 0.059(9) -0.005(8) -0.020(9) -0.041(11) C26 0.108(10) 0.073(8) 0.079(10) -0.009(7) 0.009(8) -0.010(7) C27 0.110(9) 0.063(7) 0.046(6) -0.003(5) -0.002(6) -0.011(6) C28 0.066(7) 0.084(8) 0.056(7) -0.013(6) -0.002(5) 0.003(6) N1 0.065(5) 0.066(6) 0.048(6) 0.026(4) -0.006(4) 0.000(4) N2 0.049(4) 0.061(5) 0.025(4) -0.006(3) -0.001(3) 0.001(4) N3 0.066(5) 0.069(6) 0.039(5) 0.006(4) 0.001(4) -0.001(4) N4 0.074(6) 0.069(6) 0.021(4) 0.016(4) 0.003(4) 0.004(4) N5 0.077(6) 0.091(7) 0.008(4) 0.008(4) 0.002(3) 0.006(5) N6 0.073(6) 0.081(6) 0.021(4) -0.006(4) -0.003(4) -0.004(4) O1 0.072(4) 0.048(4) 0.040(4) -0.005(3) -0.002(3) 0.002(3) O2 0.067(5) 0.067(5) 0.046(5) -0.006(4) -0.001(3) 0.007(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 Fe1 N5 1.857(8) . ? Fe1 N2 1.864(8) . ? Fe1 N4 1.914(9) . ? Fe1 N1 1.947(9) . ? Fe1 O2 1.988(8) . ? Fe1 O1 2.003(7) . ? C1 N1 1.305(14) . ? C1 C2 1.342(17) . ? C1 H1 0.9300 . ? C2 C3 1.425(18) . ? C2 H2 0.9300 . ? C3 C4 1.339(19) . ? C3 H3 0.9300 . ? C4 C5 1.396(15) . ? C4 H4 0.9300 . ? C5 N1 1.403(14) . ? C5 C6 1.451(16) . ? C6 N2 1.298(15) . ? C6 C7 1.514(18) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O1 1.241(12) . ? C8 N3 1.329(13) . ? C8 C9 1.524(15) . ? C9 C10 1.382(16) . ? C9 C14 1.432(16) . ? C10 C11 1.407(19) . ? C10 H10 0.9300 . ? C11 C12 1.35(2) . ? C11 H11 0.9300 . ? C12 C13 1.37(2) . ? C12 H12 0.9300 . ? C13 C14 1.390(17) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N4 1.338(15) . ? C15 C16 1.362(18) . ? C15 H15 0.9300 . ? C16 C17 1.41(2) . ? C16 H16 0.9300 . ? C17 C18 1.37(2) . ? C17 H17 0.9300 . ? C18 C19 1.354(17) . ? C18 H18 0.9300 . ? C19 N4 1.424(14) . ? C19 C20 1.470(18) . ? C20 N5 1.305(14) . ? C20 C21 1.468(15) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N6 1.270(13) . ? C22 O2 1.309(13) . ? C22 C23 1.504(16) . ? C23 C28 1.371(17) . ? C23 C24 1.405(14) . ? C24 C25 1.37(2) . ? C24 H24 0.9300 . ? C25 C26 1.40(2) . ? C25 H25 0.9300 . ? C26 C27 1.318(18) . ? C26 H26 0.9300 . ? C27 C28 1.381(17) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? N2 N3 1.375(12) . ? N5 N6 1.418(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Fe1 N2 176.5(4) . . ? N5 Fe1 N4 81.0(4) . . ? N2 Fe1 N4 101.4(4) . . ? N5 Fe1 N1 100.7(4) . . ? N2 Fe1 N1 81.9(4) . . ? N4 Fe1 N1 89.8(4) . . ? N5 Fe1 O2 80.1(4) . . ? N2 Fe1 O2 97.5(3) . . ? N4 Fe1 O2 161.0(3) . . ? N1 Fe1 O2 91.6(3) . . ? N5 Fe1 O1 98.0(4) . . ? N2 Fe1 O1 79.5(3) . . ? N4 Fe1 O1 91.1(3) . . ? N1 Fe1 O1 161.2(3) . . ? O2 Fe1 O1 93.6(3) . . ? N1 C1 C2 125.0(11) . . ? N1 C1 H1 117.5 . . ? C2 C1 H1 117.5 . . ? C1 C2 C3 117.8(12) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 119.8(12) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.2(15) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 N1 120.3(12) . . ? C4 C5 C6 125.6(12) . . ? N1 C5 C6 114.0(9) . . ? N2 C6 C5 111.0(10) . . ? N2 C6 C7 124.1(11) . . ? C5 C6 C7 124.8(11) . . ? 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 . . ? O1 C8 N3 126.1(10) . . ? O1 C8 C9 120.1(9) . . ? N3 C8 C9 113.8(9) . . ? C10 C9 C14 122.0(11) . . ? C10 C9 C8 121.2(10) . . ? C14 C9 C8 116.9(9) . . ? C9 C10 C11 115.9(12) . . ? C9 C10 H10 122.0 . . ? C11 C10 H10 122.0 . . ? C12 C11 C10 124.9(11) . . ? C12 C11 H11 117.6 . . ? C10 C11 H11 117.6 . . ? C11 C12 C13 117.5(12) . . ? C11 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? C12 C13 C14 123.4(15) . . ? C12 C13 H13 118.3 . . ? C14 C13 H13 118.3 . . ? C13 C14 C9 116.4(12) . . ? C13 C14 H14 121.8 . . ? C9 C14 H14 121.8 . . ? N4 C15 C16 123.8(13) . . ? N4 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C15 C16 C17 120.0(15) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 117.2(12) . . ? C18 C17 H17 121.4 . . ? C16 C17 H17 121.4 . . ? C19 C18 C17 121.4(12) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 N4 121.6(12) . . ? C18 C19 C20 127.0(11) . . ? N4 C19 C20 111.2(10) . . ? N5 C20 C21 125.5(11) . . ? N5 C20 C19 110.8(10) . . ? C21 C20 C19 123.8(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 . . ? N6 C22 O2 125.5(11) . . ? N6 C22 C23 118.6(9) . . ? O2 C22 C23 115.9(9) . . ? C28 C23 C24 116.0(11) . . ? C28 C23 C22 123.6(9) . . ? C24 C23 C22 120.4(11) . . ? C25 C24 C23 121.1(12) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 120.3(12) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C27 C26 C25 118.6(13) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C28 121.8(12) . . ? C26 C27 H27 119.1 . . ? C28 C27 H27 119.1 . . ? C23 C28 C27 122.0(11) . . ? C23 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? C1 N1 C5 117.6(9) . . ? C1 N1 Fe1 129.7(8) . . ? C5 N1 Fe1 111.6(7) . . ? C6 N2 N3 120.8(9) . . ? C6 N2 Fe1 120.4(7) . . ? N3 N2 Fe1 118.7(6) . . ? C8 N3 N2 106.7(8) . . ? C15 N4 C19 115.9(10) . . ? C15 N4 Fe1 129.4(7) . . ? C19 N4 Fe1 114.7(8) . . ? C20 N5 N6 119.9(8) . . ? C20 N5 Fe1 122.1(8) . . ? N6 N5 Fe1 118.0(6) . . ? C22 N6 N5 107.6(8) . . ? C8 O1 Fe1 109.0(7) . . ? C22 O2 Fe1 108.7(7) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.617 _refine_diff_density_min -0.673 _refine_diff_density_rms 0.145 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 756914' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28 Cl0 Fe N6 O2' _chemical_formula_sum 'C38 H28 Cl0 Fe N6 O2' _chemical_formula_weight 656.51 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.036(2) _cell_length_b 12.326(3) _cell_length_c 12.517(3) _cell_angle_alpha 66.63(3) _cell_angle_beta 83.03(3) _cell_angle_gamma 81.18(3) _cell_volume 1541.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 13954 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description platelet _exptl_crystal_colour 'black green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 24095 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5392 _reflns_number_gt 3474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0195P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5392 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.70272(3) 0.70425(3) 0.66060(3) 0.03320(12) Uani 1 1 d . . . C1 C 0.58740(19) 0.5014(2) 0.8486(2) 0.0472(6) Uani 1 1 d . . . H1 H 0.5674 0.5495 0.8911 0.057 Uiso 1 1 calc R . . C2 C 0.5574(2) 0.3875(2) 0.8976(2) 0.0622(8) Uani 1 1 d . . . H2 H 0.5175 0.3597 0.9716 0.075 Uiso 1 1 calc R . . C3 C 0.5863(2) 0.3147(2) 0.8371(2) 0.0633(8) Uani 1 1 d . . . H3 H 0.5664 0.2370 0.8693 0.076 Uiso 1 1 calc R . . C4 C 0.6455(2) 0.3585(2) 0.7273(2) 0.0517(7) Uani 1 1 d . . . H4 H 0.6661 0.3105 0.6848 0.062 Uiso 1 1 calc R . . C5 C 0.67386(17) 0.47504(18) 0.68110(18) 0.0346(5) Uani 1 1 d . . . C6 C 0.74171(17) 0.52887(18) 0.56959(18) 0.0320(5) Uani 1 1 d . . . C7 C 0.76432(19) 0.47373(17) 0.48230(18) 0.0343(5) Uani 1 1 d . . . C8 C 0.6683(2) 0.4729(2) 0.4222(2) 0.0560(7) Uani 1 1 d . . . H8 H 0.5908 0.5087 0.4358 0.067 Uiso 1 1 calc R . . C9 C 0.6850(2) 0.4199(2) 0.3420(2) 0.0655(8) Uani 1 1 d . . . H9 H 0.6189 0.4201 0.3023 0.079 Uiso 1 1 calc R . . C10 C 0.7984(2) 0.3673(2) 0.3211(2) 0.0611(7) Uani 1 1 d . . . H10 H 0.8096 0.3308 0.2677 0.073 Uiso 1 1 calc R . . C11 C 0.8945(2) 0.3685(2) 0.3783(2) 0.0606(7) Uani 1 1 d . . . H11 H 0.9721 0.3338 0.3630 0.073 Uiso 1 1 calc R . . C12 C 0.8781(2) 0.42104(19) 0.4593(2) 0.0509(7) Uani 1 1 d . . . H12 H 0.9447 0.4207 0.4984 0.061 Uiso 1 1 calc R . . C13 C 0.85330(17) 0.79870(18) 0.46677(18) 0.0337(5) Uani 1 1 d . . . C14 C 0.93808(18) 0.87572(18) 0.37789(17) 0.0347(5) Uani 1 1 d . . . C15 C 1.0055(2) 0.8381(2) 0.29624(19) 0.0516(7) Uani 1 1 d . . . H15 H 0.9936 0.7663 0.2933 0.062 Uiso 1 1 calc R . . C16 C 1.0905(2) 0.9062(2) 0.2190(2) 0.0595(7) Uani 1 1 d . . . H16 H 1.1358 0.8799 0.1644 0.071 Uiso 1 1 calc R . . C17 C 1.1090(2) 1.0128(2) 0.2219(2) 0.0538(7) Uani 1 1 d . . . H17 H 1.1669 1.0582 0.1698 0.065 Uiso 1 1 calc R . . C18 C 1.0418(2) 1.0518(2) 0.3021(2) 0.0493(6) Uani 1 1 d . . . H18 H 1.0534 1.1241 0.3041 0.059 Uiso 1 1 calc R . . C19 C 0.95653(18) 0.98325(19) 0.37993(18) 0.0409(6) Uani 1 1 d . . . H19 H 0.9111 1.0099 0.4342 0.049 Uiso 1 1 calc R . . C20 C 0.5336(2) 0.78485(18) 0.4682(2) 0.0414(6) Uani 1 1 d . . . H20 H 0.5898 0.7431 0.4327 0.050 Uiso 1 1 calc R . . C21 C 0.4314(2) 0.84961(19) 0.4104(2) 0.0458(6) Uani 1 1 d . . . H21 H 0.4182 0.8493 0.3386 0.055 Uiso 1 1 calc R . . C22 C 0.3495(2) 0.9146(2) 0.4601(2) 0.0489(6) Uani 1 1 d . . . H22 H 0.2810 0.9606 0.4217 0.059 Uiso 1 1 calc R . . C23 C 0.37056(19) 0.91035(19) 0.5674(2) 0.0424(6) Uani 1 1 d . . . H23 H 0.3162 0.9544 0.6021 0.051 Uiso 1 1 calc R . . C24 C 0.47219(18) 0.84097(17) 0.62465(19) 0.0332(5) Uani 1 1 d . . . C25 C 0.50586(18) 0.83132(17) 0.73740(18) 0.0335(5) Uani 1 1 d . . . C26 C 0.42235(18) 0.88352(18) 0.81120(17) 0.0348(6) Uani 1 1 d . . . C27 C 0.29963(19) 0.8631(2) 0.83250(19) 0.0488(7) Uani 1 1 d . . . H27 H 0.2727 0.8104 0.8067 0.059 Uiso 1 1 calc R . . C28 C 0.2169(2) 0.9196(2) 0.8912(2) 0.0575(7) Uani 1 1 d . . . H28 H 0.1354 0.9040 0.9059 0.069 Uiso 1 1 calc R . . C29 C 0.2559(2) 0.9986(2) 0.9275(2) 0.0578(7) Uani 1 1 d . . . H29 H 0.1996 1.0399 0.9635 0.069 Uiso 1 1 calc R . . C30 C 0.3769(2) 1.0174(2) 0.9113(2) 0.0561(7) Uani 1 1 d . . . H30 H 0.4032 1.0694 0.9385 0.067 Uiso 1 1 calc R . . C31 C 0.4601(2) 0.95914(19) 0.85451(18) 0.0439(6) Uani 1 1 d . . . H31 H 0.5426 0.9709 0.8453 0.053 Uiso 1 1 calc R . . C32 C 0.78026(19) 0.70009(17) 0.85936(19) 0.0342(5) Uani 1 1 d . . . C33 C 0.85785(19) 0.67787(17) 0.95669(19) 0.0370(6) Uani 1 1 d . . . C34 C 0.8085(2) 0.68696(19) 1.0601(2) 0.0506(7) Uani 1 1 d . . . H34 H 0.7245 0.7076 1.0700 0.061 Uiso 1 1 calc R . . C35 C 0.8830(3) 0.6657(2) 1.1486(2) 0.0672(8) Uani 1 1 d . . . H35 H 0.8488 0.6709 1.2184 0.081 Uiso 1 1 calc R . . C36 C 1.0074(3) 0.6368(2) 1.1344(3) 0.0659(8) Uani 1 1 d . . . H36 H 1.0577 0.6232 1.1940 0.079 Uiso 1 1 calc R . . C37 C 1.0567(2) 0.6283(2) 1.0325(3) 0.0639(8) Uani 1 1 d . . . H37 H 1.1410 0.6090 1.0225 0.077 Uiso 1 1 calc R . . C38 C 0.9827(2) 0.6479(2) 0.9439(2) 0.0520(7) Uani 1 1 d . . . H38 H 1.0172 0.6408 0.8750 0.062 Uiso 1 1 calc R . . N1 N 0.64440(14) 0.54701(14) 0.74213(14) 0.0347(4) Uani 1 1 d . . . N2 N 0.77249(13) 0.63216(14) 0.55727(14) 0.0317(4) Uani 1 1 d . . . N3 N 0.84113(14) 0.69637(15) 0.45824(14) 0.0345(4) Uani 1 1 d . . . N4 N 0.55574(14) 0.77922(14) 0.57315(15) 0.0342(4) Uani 1 1 d . . . N5 N 0.61653(14) 0.77509(14) 0.76044(15) 0.0318(4) Uani 1 1 d . . . N6 N 0.66791(15) 0.75868(14) 0.86195(15) 0.0360(5) Uani 1 1 d . . . O1 O 0.80023(12) 0.83084(11) 0.54861(11) 0.0370(4) Uani 1 1 d . . . O2 O 0.82502(11) 0.66512(12) 0.77710(12) 0.0394(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 Fe1 0.03435(19) 0.03416(19) 0.0319(2) -0.01503(15) -0.00012(14) -0.00161(13) C1 0.0557(15) 0.0499(16) 0.0363(16) -0.0174(13) 0.0072(12) -0.0127(12) C2 0.0801(18) 0.0548(18) 0.0458(17) -0.0145(15) 0.0152(14) -0.0197(15) C3 0.0810(19) 0.0417(16) 0.0607(19) -0.0118(15) 0.0150(15) -0.0259(14) C4 0.0624(16) 0.0411(15) 0.0553(18) -0.0226(14) 0.0055(14) -0.0128(12) C5 0.0355(12) 0.0318(13) 0.0379(14) -0.0151(12) -0.0014(11) -0.0041(10) C6 0.0306(12) 0.0326(13) 0.0348(14) -0.0161(12) -0.0034(10) 0.0000(10) C7 0.0347(13) 0.0338(13) 0.0362(15) -0.0153(11) 0.0020(11) -0.0073(10) C8 0.0347(14) 0.087(2) 0.0606(18) -0.0448(16) 0.0028(13) -0.0068(13) C9 0.0500(17) 0.104(2) 0.066(2) -0.0532(18) -0.0011(14) -0.0234(15) C10 0.0699(19) 0.0765(19) 0.062(2) -0.0513(16) 0.0098(16) -0.0233(15) C11 0.0509(16) 0.0745(19) 0.074(2) -0.0528(17) -0.0055(15) 0.0102(14) C12 0.0424(14) 0.0605(16) 0.0625(18) -0.0394(15) -0.0108(12) 0.0064(12) C13 0.0336(12) 0.0373(14) 0.0313(14) -0.0140(12) -0.0054(11) -0.0023(10) C14 0.0382(13) 0.0342(13) 0.0320(14) -0.0129(11) -0.0014(11) -0.0054(10) C15 0.0662(16) 0.0390(14) 0.0477(16) -0.0168(13) 0.0150(13) -0.0149(12) C16 0.0707(17) 0.0541(17) 0.0526(17) -0.0248(14) 0.0224(14) -0.0135(14) C17 0.0570(16) 0.0521(17) 0.0479(17) -0.0127(14) 0.0104(13) -0.0228(13) C18 0.0591(16) 0.0434(14) 0.0473(16) -0.0160(13) -0.0032(13) -0.0159(12) C19 0.0422(13) 0.0454(15) 0.0378(15) -0.0176(12) -0.0023(11) -0.0087(11) C20 0.0476(14) 0.0384(14) 0.0377(16) -0.0153(12) -0.0047(12) -0.0005(11) C21 0.0582(15) 0.0468(15) 0.0344(15) -0.0155(13) -0.0120(13) -0.0055(13) C22 0.0477(15) 0.0484(15) 0.0465(17) -0.0131(14) -0.0160(13) 0.0017(12) C23 0.0431(14) 0.0440(15) 0.0411(16) -0.0194(13) -0.0065(12) 0.0030(11) C24 0.0333(12) 0.0321(12) 0.0353(15) -0.0142(11) -0.0035(11) -0.0022(10) C25 0.0327(13) 0.0307(12) 0.0363(15) -0.0130(11) -0.0017(11) -0.0018(10) C26 0.0378(13) 0.0328(13) 0.0314(14) -0.0113(11) -0.0052(11) 0.0021(10) C27 0.0407(15) 0.0561(16) 0.0565(17) -0.0297(14) -0.0003(12) -0.0061(12) C28 0.0411(15) 0.0749(19) 0.0571(18) -0.0299(16) 0.0035(13) -0.0018(14) C29 0.0620(19) 0.0612(18) 0.0460(17) -0.0253(15) 0.0065(14) 0.0099(14) C30 0.0709(18) 0.0534(16) 0.0523(17) -0.0320(14) 0.0047(14) -0.0058(14) C31 0.0468(14) 0.0452(14) 0.0415(15) -0.0191(13) -0.0015(12) -0.0051(12) C32 0.0383(14) 0.0278(12) 0.0343(15) -0.0086(11) -0.0006(12) -0.0085(10) C33 0.0402(14) 0.0344(13) 0.0359(15) -0.0117(11) -0.0092(12) -0.0025(10) C34 0.0541(16) 0.0569(16) 0.0462(17) -0.0246(14) -0.0103(14) -0.0031(12) C35 0.080(2) 0.082(2) 0.0498(19) -0.0328(16) -0.0213(16) -0.0051(16) C36 0.071(2) 0.0660(19) 0.070(2) -0.0292(17) -0.0378(17) 0.0010(15) C37 0.0501(16) 0.0701(19) 0.075(2) -0.0298(17) -0.0209(17) 0.0019(14) C38 0.0473(15) 0.0603(17) 0.0478(17) -0.0199(14) -0.0110(13) -0.0011(13) N1 0.0352(10) 0.0372(11) 0.0295(11) -0.0113(9) 0.0013(9) -0.0047(8) N2 0.0315(10) 0.0306(11) 0.0322(11) -0.0122(9) 0.0005(8) -0.0030(8) N3 0.0374(10) 0.0346(11) 0.0316(11) -0.0138(9) 0.0040(9) -0.0065(8) N4 0.0392(10) 0.0325(10) 0.0314(12) -0.0122(9) -0.0048(9) -0.0044(8) N5 0.0308(10) 0.0350(10) 0.0297(11) -0.0128(9) -0.0017(9) -0.0027(8) N6 0.0367(11) 0.0410(11) 0.0322(12) -0.0155(9) -0.0056(9) -0.0036(9) O1 0.0428(8) 0.0354(8) 0.0360(9) -0.0178(7) 0.0017(7) -0.0057(7) O2 0.0338(8) 0.0476(9) 0.0367(9) -0.0175(8) -0.0049(7) 0.0012(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 Fe1 N2 1.8749(16) . ? Fe1 N5 1.8844(16) . ? Fe1 N4 1.9628(18) . ? Fe1 N1 1.9664(18) . ? Fe1 O2 1.9752(15) . ? Fe1 O1 1.9929(15) . ? C1 N1 1.341(2) . ? C1 C2 1.366(3) . ? C1 H1 0.9300 . ? C2 C3 1.370(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C5 N1 1.366(2) . ? C5 C6 1.454(3) . ? C6 N2 1.313(2) . ? C6 C7 1.480(3) . ? C7 C8 1.375(3) . ? C7 C12 1.376(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C10 1.364(3) . ? C9 H9 0.9300 . ? C10 C11 1.355(3) . ? C10 H10 0.9300 . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O1 1.286(2) . ? C13 N3 1.335(2) . ? C13 C14 1.482(3) . ? C14 C15 1.378(3) . ? C14 C19 1.382(3) . ? C15 C16 1.378(3) . ? C15 H15 0.9300 . ? C16 C17 1.375(3) . ? C16 H16 0.9300 . ? C17 C18 1.371(3) . ? C17 H17 0.9300 . ? C18 C19 1.385(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N4 1.338(3) . ? C20 C21 1.377(3) . ? C20 H20 0.9300 . ? C21 C22 1.372(3) . ? C21 H21 0.9300 . ? C22 C23 1.370(3) . ? C22 H22 0.9300 . ? C23 C24 1.385(3) . ? C23 H23 0.9300 . ? C24 N4 1.369(2) . ? C24 C25 1.458(3) . ? C25 N5 1.313(2) . ? C25 C26 1.483(3) . ? C26 C31 1.383(3) . ? C26 C27 1.390(3) . ? C27 C28 1.381(3) . ? C27 H27 0.9300 . ? C28 C29 1.366(3) . ? C28 H28 0.9300 . ? C29 C30 1.368(3) . ? C29 H29 0.9300 . ? C30 C31 1.381(3) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 O2 1.286(2) . ? C32 N6 1.339(2) . ? C32 C33 1.486(3) . ? C33 C38 1.377(3) . ? C33 C34 1.382(3) . ? C34 C35 1.377(3) . ? C34 H34 0.9300 . ? C35 C36 1.373(3) . ? C35 H35 0.9300 . ? C36 C37 1.362(3) . ? C36 H36 0.9300 . ? C37 C38 1.380(3) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? N2 N3 1.384(2) . ? N5 N6 1.383(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 N2 Fe1 N5 174.04(8) . . ? N2 Fe1 N4 94.06(8) . . ? N5 Fe1 N4 80.83(8) . . ? N2 Fe1 N1 80.69(8) . . ? N5 Fe1 N1 96.68(7) . . ? N4 Fe1 N1 95.55(7) . . ? N2 Fe1 O2 105.68(7) . . ? N5 Fe1 O2 79.62(7) . . ? N4 Fe1 O2 159.99(7) . . ? N1 Fe1 O2 90.92(7) . . ? N2 Fe1 O1 79.42(7) . . ? N5 Fe1 O1 103.60(6) . . ? N4 Fe1 O1 90.93(7) . . ? N1 Fe1 O1 159.46(6) . . ? O2 Fe1 O1 89.55(6) . . ? N1 C1 C2 123.1(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 118.9(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.3(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.27(19) . . ? N1 C5 C6 114.33(18) . . ? C4 C5 C6 124.3(2) . . ? N2 C6 C5 110.82(18) . . ? N2 C6 C7 126.61(18) . . ? C5 C6 C7 122.49(19) . . ? C8 C7 C12 117.9(2) . . ? C8 C7 C6 119.42(19) . . ? C12 C7 C6 122.6(2) . . ? C7 C8 C9 121.2(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 119.8(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.5(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 120.6(2) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? O1 C13 N3 124.14(18) . . ? O1 C13 C14 119.32(19) . . ? N3 C13 C14 116.49(18) . . ? C15 C14 C19 118.8(2) . . ? C15 C14 C13 120.6(2) . . ? C19 C14 C13 120.53(19) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 120.6(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 119.6(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 119.8(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 120.8(2) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? N4 C20 C21 123.1(2) . . ? N4 C20 H20 118.5 . . ? C21 C20 H20 118.5 . . ? C22 C21 C20 119.2(2) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 118.7(2) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? N4 C24 C23 120.7(2) . . ? N4 C24 C25 113.74(18) . . ? C23 C24 C25 125.50(19) . . ? N5 C25 C24 111.53(17) . . ? N5 C25 C26 126.7(2) . . ? C24 C25 C26 121.78(18) . . ? C31 C26 C27 117.78(19) . . ? C31 C26 C25 122.15(19) . . ? C27 C26 C25 119.9(2) . . ? C28 C27 C26 121.3(2) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C29 C28 C27 119.4(2) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C28 C29 C30 120.6(2) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C31 120.0(2) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C26 C31 C30 120.8(2) . . ? C26 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? O2 C32 N6 124.0(2) . . ? O2 C32 C33 118.81(18) . . ? N6 C32 C33 117.1(2) . . ? C38 C33 C34 118.7(2) . . ? C38 C33 C32 119.4(2) . . ? C34 C33 C32 121.9(2) . . ? C35 C34 C33 120.4(2) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 120.3(2) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C37 C36 C35 119.6(3) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C36 C37 C38 120.5(2) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C33 C38 C37 120.4(2) . . ? C33 C38 H38 119.8 . . ? C37 C38 H38 119.8 . . ? C1 N1 C5 117.81(18) . . ? C1 N1 Fe1 129.08(15) . . ? C5 N1 Fe1 113.01(13) . . ? C6 N2 N3 119.91(17) . . ? C6 N2 Fe1 120.04(13) . . ? N3 N2 Fe1 119.29(13) . . ? C13 N3 N2 106.79(15) . . ? C20 N4 C24 117.90(18) . . ? C20 N4 Fe1 128.26(14) . . ? C24 N4 Fe1 113.58(15) . . ? C25 N5 N6 121.07(17) . . ? C25 N5 Fe1 119.92(16) . . ? N6 N5 Fe1 118.82(12) . . ? C32 N6 N5 106.77(16) . . ? C13 O1 Fe1 109.97(13) . . ? C32 O2 Fe1 110.42(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.210 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.045 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 756915' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C26 H20 Fe N6 O4), H2O' _chemical_formula_sum 'C52 H42 Cl0 Fe2 N12 O9' _chemical_formula_weight 1090.68 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 18.485(4) _cell_length_b 24.520(5) _cell_length_c 11.575(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.70(3) _cell_angle_gamma 90.00 _cell_volume 5074.3(18) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 36966 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour 'black green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 34178 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4466 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al. 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0873P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4466 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 Fe1 Fe 0.19568(3) 0.37675(2) 0.50382(5) 0.0744(3) Uani 1 1 d . . . C1 C 0.0982(2) 0.41191(16) 0.2410(4) 0.0943(13) Uani 1 1 d . . . H1 H 0.0854 0.3752 0.2304 0.113 Uiso 1 1 calc R . . C2 C 0.0674(3) 0.44789(19) 0.1504(4) 0.1028(14) Uani 1 1 d . . . H2A H 0.0349 0.4355 0.0804 0.123 Uiso 1 1 calc R . . C3 C 0.0850(3) 0.50133(19) 0.1643(4) 0.0966(13) Uani 1 1 d . . . H3 H 0.0644 0.5262 0.1044 0.116 Uiso 1 1 calc R . . C4 C 0.1343(2) 0.51843(16) 0.2692(4) 0.0896(12) Uani 1 1 d . . . H4A H 0.1475 0.5550 0.2804 0.107 Uiso 1 1 calc R . . C5 C 0.1636(2) 0.48046(14) 0.3571(3) 0.0702(10) Uani 1 1 d . . . C6 C 0.2143(2) 0.49470(16) 0.4711(4) 0.0780(11) Uani 1 1 d . . . H6 H 0.2300 0.5304 0.4897 0.094 Uiso 1 1 calc R . . C7 C 0.2895(2) 0.41912(16) 0.7195(3) 0.0724(10) Uani 1 1 d . . . C8 C 0.3349(2) 0.42339(17) 0.8439(3) 0.0787(11) Uani 1 1 d . . . C9 C 0.3716(2) 0.47110(19) 0.8929(4) 0.0842(12) Uani 1 1 d . . . C10 C 0.4107(2) 0.4723(2) 1.0113(4) 0.1017(14) Uani 1 1 d . . . H10 H 0.4351 0.5041 1.0434 0.122 Uiso 1 1 calc R . . C11 C 0.4140(3) 0.4273(3) 1.0820(4) 0.1152(17) Uani 1 1 d . . . H11 H 0.4393 0.4290 1.1623 0.138 Uiso 1 1 calc R . . C12 C 0.3803(3) 0.3800(2) 1.0357(5) 0.131(2) Uani 1 1 d . . . H12 H 0.3840 0.3490 1.0832 0.157 Uiso 1 1 calc R . . C13 C 0.3406(3) 0.37846(19) 0.9171(4) 0.1111(16) Uani 1 1 d . . . H13 H 0.3172 0.3462 0.8859 0.133 Uiso 1 1 calc R . . C14 C 0.3485(3) 0.3604(2) 0.4244(5) 0.1048(15) Uani 1 1 d . . . H14 H 0.3630 0.3937 0.4616 0.126 Uiso 1 1 calc R . . C15 C 0.3981(3) 0.3335(3) 0.3745(5) 0.1138(17) Uani 1 1 d . . . H15 H 0.4448 0.3487 0.3781 0.137 Uiso 1 1 calc R . . C16 C 0.3789(3) 0.2841(2) 0.3194(4) 0.1043(14) Uani 1 1 d . . . H16 H 0.4120 0.2651 0.2855 0.125 Uiso 1 1 calc R . . C17 C 0.3091(3) 0.26369(19) 0.3160(4) 0.0908(12) Uani 1 1 d . . . H17 H 0.2940 0.2304 0.2789 0.109 Uiso 1 1 calc R . . C18 C 0.2612(2) 0.29262(16) 0.3677(3) 0.0768(11) Uani 1 1 d . . . C19 C 0.1874(2) 0.27420(16) 0.3699(3) 0.0747(10) Uani 1 1 d . . . H19 H 0.1680 0.2416 0.3342 0.090 Uiso 1 1 calc R . . C20 C 0.0548(2) 0.32588(15) 0.4972(3) 0.0727(10) Uani 1 1 d . . . C21 C -0.0212(2) 0.31559(15) 0.5109(3) 0.0743(10) Uani 1 1 d . . . C22 C -0.0483(3) 0.34555(18) 0.5921(5) 0.1091(16) Uani 1 1 d . . . H22 H -0.0171 0.3711 0.6395 0.131 Uiso 1 1 calc R . . C23 C -0.1194(4) 0.3389(2) 0.6050(6) 0.138(2) Uani 1 1 d . . . H23 H -0.1364 0.3595 0.6602 0.166 Uiso 1 1 calc R . . C24 C -0.1651(3) 0.3009(2) 0.5343(6) 0.134(2) Uani 1 1 d . . . H24 H -0.2135 0.2961 0.5423 0.160 Uiso 1 1 calc R . . C25 C -0.1414(3) 0.2708(2) 0.4539(5) 0.1122(16) Uani 1 1 d . . . H25 H -0.1735 0.2460 0.4060 0.135 Uiso 1 1 calc R . . C26 C -0.0691(3) 0.27697(17) 0.4427(4) 0.0853(12) Uani 1 1 d . . . N1 N 0.14505(17) 0.42717(12) 0.3426(3) 0.0761(8) Uani 1 1 d . . . N2 N 0.23609(17) 0.45544(12) 0.5444(3) 0.0710(8) Uani 1 1 d . . . N3 N 0.28224(17) 0.46462(12) 0.6561(3) 0.0761(9) Uani 1 1 d . . . N4 N 0.2808(2) 0.34164(13) 0.4224(3) 0.0825(9) Uani 1 1 d . . . N5 N 0.15005(19) 0.30456(12) 0.4229(3) 0.0691(8) Uani 1 1 d . . . N6 N 0.07986(19) 0.29019(12) 0.4288(3) 0.0736(8) Uani 1 1 d . . . O1 O 0.25921(17) 0.37384(10) 0.6806(2) 0.0924(9) Uani 1 1 d . . . O2 O 0.3708(2) 0.51660(13) 0.8273(3) 0.1178(11) Uani 1 1 d . . . H2 H 0.3448 0.5115 0.7594 0.177 Uiso 1 1 calc R . . O3 O 0.09197(15) 0.36672(10) 0.5487(2) 0.0849(8) Uani 1 1 d . . . O4 O -0.04773(18) 0.24438(14) 0.3631(3) 0.1102(10) Uani 1 1 d . . . H4 H -0.0023 0.2465 0.3731 0.165 Uiso 1 1 calc R . . O5 O 0.0000 0.1155(4) 0.2500 0.313(6) Uani 1 2 d S . . H5A H 0.0400 0.1307 0.2563 0.376 Uiso 0.50 1 d P . . H5B H -0.0084 0.1108 0.3188 0.376 Uiso 0.50 1 d P . . 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 Fe1 0.0935(5) 0.0564(4) 0.0627(4) -0.0032(2) 0.0000(3) -0.0146(3) C1 0.120(3) 0.067(2) 0.073(3) -0.003(2) -0.017(2) -0.012(2) C2 0.125(4) 0.085(3) 0.077(3) 0.005(2) -0.013(3) -0.007(3) C3 0.107(3) 0.090(3) 0.084(3) 0.018(2) 0.008(3) 0.010(3) C4 0.107(3) 0.068(2) 0.087(3) 0.007(2) 0.012(3) 0.002(2) C5 0.083(3) 0.060(2) 0.067(2) 0.0019(19) 0.017(2) 0.001(2) C6 0.093(3) 0.060(2) 0.076(3) -0.006(2) 0.014(2) -0.013(2) C7 0.073(3) 0.071(3) 0.066(2) -0.004(2) 0.0050(19) -0.011(2) C8 0.076(3) 0.090(3) 0.065(3) -0.004(2) 0.009(2) -0.010(2) C9 0.082(3) 0.095(3) 0.068(3) -0.018(2) 0.006(2) -0.007(2) C10 0.092(3) 0.120(4) 0.082(3) -0.030(3) 0.003(3) -0.008(3) C11 0.107(4) 0.152(5) 0.068(3) -0.015(4) -0.012(3) 0.006(4) C12 0.147(5) 0.137(5) 0.081(4) 0.019(3) -0.022(3) -0.011(4) C13 0.128(4) 0.107(4) 0.079(3) 0.012(3) -0.008(3) -0.030(3) C14 0.098(4) 0.095(3) 0.110(4) 0.016(3) 0.006(3) -0.018(3) C15 0.091(4) 0.120(5) 0.125(4) 0.028(4) 0.017(3) -0.015(4) C16 0.102(4) 0.107(4) 0.103(4) 0.027(3) 0.024(3) 0.011(3) C17 0.100(3) 0.088(3) 0.082(3) 0.011(2) 0.019(3) 0.006(3) C18 0.093(3) 0.067(3) 0.063(2) 0.008(2) 0.006(2) -0.002(2) C19 0.091(3) 0.061(2) 0.066(2) 0.0018(19) 0.008(2) -0.007(2) C20 0.095(3) 0.055(2) 0.061(2) 0.0035(19) 0.005(2) -0.004(2) C21 0.095(3) 0.060(2) 0.064(2) 0.0027(19) 0.014(2) -0.008(2) C22 0.135(4) 0.079(3) 0.130(4) -0.023(3) 0.065(4) -0.025(3) C23 0.163(6) 0.098(4) 0.187(6) -0.038(4) 0.106(5) -0.030(4) C24 0.129(4) 0.115(4) 0.179(6) -0.008(4) 0.079(5) -0.027(4) C25 0.105(4) 0.122(4) 0.116(4) -0.015(3) 0.040(3) -0.034(3) C26 0.104(4) 0.080(3) 0.072(3) 0.002(2) 0.023(2) -0.009(3) N1 0.093(2) 0.063(2) 0.067(2) -0.0003(15) 0.0092(17) -0.0053(17) N2 0.085(2) 0.0612(18) 0.063(2) -0.0048(16) 0.0106(17) -0.0142(16) N3 0.086(2) 0.068(2) 0.066(2) -0.0056(16) 0.0050(17) -0.0136(17) N4 0.086(3) 0.078(2) 0.075(2) 0.0135(17) 0.0058(18) -0.0143(19) N5 0.082(2) 0.0590(18) 0.0620(19) -0.0005(15) 0.0111(16) -0.0052(18) N6 0.091(2) 0.0608(19) 0.066(2) -0.0059(16) 0.0141(17) -0.0097(17) O1 0.115(2) 0.0737(18) 0.0720(18) 0.0038(14) -0.0063(15) -0.0241(15) O2 0.149(3) 0.092(2) 0.091(2) -0.0175(18) -0.007(2) -0.030(2) O3 0.102(2) 0.0707(16) 0.0783(17) -0.0174(14) 0.0168(15) -0.0147(15) O4 0.115(2) 0.119(2) 0.100(2) -0.0379(19) 0.034(2) -0.038(2) O5 0.239(9) 0.282(11) 0.495(19) 0.000 0.235(12) 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 Fe1 N2 2.079(3) . ? Fe1 N5 2.079(3) . ? Fe1 O1 2.086(3) . ? Fe1 O3 2.124(3) . ? Fe1 N4 2.204(4) . ? Fe1 N1 2.236(3) . ? C1 N1 1.325(4) . ? C1 C2 1.377(5) . ? C1 H1 0.9300 . ? C2 C3 1.350(6) . ? C2 H2A 0.9300 . ? C3 C4 1.385(6) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4A 0.9300 . ? C5 N1 1.351(4) . ? C5 C6 1.453(5) . ? C6 N2 1.279(4) . ? C6 H6 0.9300 . ? C7 O1 1.273(4) . ? C7 N3 1.323(4) . ? C7 C8 1.475(5) . ? C8 C13 1.377(5) . ? C8 C9 1.399(5) . ? C9 O2 1.348(5) . ? C9 C10 1.378(6) . ? C10 C11 1.367(6) . ? C10 H10 0.9300 . ? C11 C12 1.360(7) . ? C11 H11 0.9300 . ? C12 C13 1.383(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 N4 1.328(6) . ? C14 C15 1.371(7) . ? C14 H14 0.9300 . ? C15 C16 1.373(7) . ? C15 H15 0.9300 . ? C16 C17 1.376(6) . ? C16 H16 0.9300 . ? C17 C18 1.383(5) . ? C17 H17 0.9300 . ? C18 N4 1.364(5) . ? C18 C19 1.443(5) . ? C19 N5 1.273(4) . ? C19 H19 0.9300 . ? C20 O3 1.273(4) . ? C20 N6 1.338(4) . ? C20 C21 1.477(5) . ? C21 C22 1.382(5) . ? C21 C26 1.396(5) . ? C22 C23 1.370(7) . ? C22 H22 0.9300 . ? C23 C24 1.378(7) . ? C23 H23 0.9300 . ? C24 C25 1.346(7) . ? C24 H24 0.9300 . ? C25 C26 1.383(6) . ? C25 H25 0.9300 . ? C26 O4 1.352(5) . ? N2 N3 1.375(4) . ? N5 N6 1.363(4) . ? O2 H2 0.8200 . ? O4 H4 0.8200 . ? O5 H5A 0.8137 . ? O5 H5B 0.8567 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N5 166.74(12) . . ? N2 Fe1 O1 74.31(11) . . ? N5 Fe1 O1 118.43(11) . . ? N2 Fe1 O3 110.31(11) . . ? N5 Fe1 O3 73.95(12) . . ? O1 Fe1 O3 94.28(11) . . ? N2 Fe1 N4 101.79(13) . . ? N5 Fe1 N4 74.15(14) . . ? O1 Fe1 N4 96.93(12) . . ? O3 Fe1 N4 147.79(12) . . ? N2 Fe1 N1 74.08(12) . . ? N5 Fe1 N1 93.36(11) . . ? O1 Fe1 N1 148.17(10) . . ? O3 Fe1 N1 93.19(11) . . ? N4 Fe1 N1 92.99(11) . . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.4(4) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 119.3(4) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 121.3(3) . . ? N1 C5 C6 115.5(3) . . ? C4 C5 C6 123.2(4) . . ? N2 C6 C5 116.3(3) . . ? N2 C6 H6 121.8 . . ? C5 C6 H6 121.8 . . ? O1 C7 N3 124.4(3) . . ? O1 C7 C8 119.8(3) . . ? N3 C7 C8 115.7(3) . . ? C13 C8 C9 117.8(4) . . ? C13 C8 C7 118.7(4) . . ? C9 C8 C7 123.5(4) . . ? O2 C9 C10 118.1(4) . . ? O2 C9 C8 121.9(4) . . ? C10 C9 C8 120.0(5) . . ? C11 C10 C9 120.7(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.4(4) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.3(5) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 121.8(4) . . ? C8 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? N4 C14 C15 123.6(5) . . ? N4 C14 H14 118.2 . . ? C15 C14 H14 118.2 . . ? C14 C15 C16 119.9(5) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 117.6(5) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? C16 C17 C18 120.0(4) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? N4 C18 C17 122.0(4) . . ? N4 C18 C19 114.1(4) . . ? C17 C18 C19 123.9(4) . . ? N5 C19 C18 117.2(4) . . ? N5 C19 H19 121.4 . . ? C18 C19 H19 121.4 . . ? O3 C20 N6 124.4(4) . . ? O3 C20 C21 119.9(4) . . ? N6 C20 C21 115.7(3) . . ? C22 C21 C26 117.3(4) . . ? C22 C21 C20 120.1(4) . . ? C26 C21 C20 122.6(4) . . ? C23 C22 C21 122.2(5) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C24 C23 C22 118.5(5) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C25 C24 C23 121.5(5) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 119.8(5) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? O4 C26 C25 117.1(4) . . ? O4 C26 C21 122.2(4) . . ? C25 C26 C21 120.7(4) . . ? C1 N1 C5 118.1(3) . . ? C1 N1 Fe1 128.7(3) . . ? C5 N1 Fe1 113.1(2) . . ? C6 N2 N3 121.1(3) . . ? C6 N2 Fe1 120.9(3) . . ? N3 N2 Fe1 117.8(2) . . ? C7 N3 N2 109.6(3) . . ? C14 N4 C18 116.9(4) . . ? C14 N4 Fe1 129.0(4) . . ? C18 N4 Fe1 114.1(3) . . ? C19 N5 N6 120.9(3) . . ? C19 N5 Fe1 120.5(3) . . ? N6 N5 Fe1 118.7(2) . . ? C20 N6 N5 109.7(3) . . ? C7 O1 Fe1 113.9(2) . . ? C9 O2 H2 109.5 . . ? C20 O3 Fe1 112.9(2) . . ? C26 O4 H4 109.5 . . ? H5A O5 H5B 110.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.627 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.051 # Attachment '5-110K.cif' data_5b _database_code_depnum_ccdc_archive 'CCDC 756916' #TrackingRef '5-110K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Fe N6 O4' _chemical_formula_sum 'C28 H24 Fe N6 O4' _chemical_formula_weight 564.38 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 _symmetry_space_group_name_Hall 'A 2 -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 12.398(3) _cell_length_b 18.807(4) _cell_length_c 10.325(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2407.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 17623 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.373 _exptl_crystal_description block _exptl_crystal_colour 'black green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 110(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16624 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2353 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXu (Mackay et al. 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.301(18) _refine_ls_number_reflns 2353 _refine_ls_number_parameters 180 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0665 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.010 _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 Fe1 Fe 0.0000 1.0000 0.08512(5) 0.02648(13) Uani 1 2 d S . . C1 C 0.01271(19) 1.10128(13) -0.1320(3) 0.0354(6) Uani 1 1 d . . . H1 H -0.0624 1.1091 -0.1202 0.043 Uiso 1 1 calc R . . C2 C 0.0647(2) 1.13512(13) -0.2344(2) 0.0413(6) Uani 1 1 d . . . H2 H 0.0260 1.1654 -0.2915 0.050 Uiso 1 1 calc R . . C3 C 0.1738(2) 1.12358(14) -0.2510(2) 0.0440(7) Uani 1 1 d . . . H3 H 0.2109 1.1460 -0.3203 0.053 Uiso 1 1 calc R . . C4 C 0.2290(2) 1.07946(12) -0.1671(3) 0.0384(6) Uani 1 1 d . . . H4 H 0.3043 1.0718 -0.1773 0.046 Uiso 1 1 calc R . . C5 C 0.17269(18) 1.04661(12) -0.0679(2) 0.0314(5) Uani 1 1 d . . . C6 C 0.21744(19) 0.99403(12) 0.0213(2) 0.0301(5) Uani 1 1 d . . . C7 C 0.3344(2) 0.97504(15) 0.0315(3) 0.0409(6) Uani 1 1 d . . . H7A H 0.3650 0.9967 0.1096 0.061 Uiso 1 1 calc R . . H7B H 0.3729 0.9927 -0.0449 0.061 Uiso 1 1 calc R . . H7C H 0.3420 0.9232 0.0365 0.061 Uiso 1 1 calc R . . C8 C 0.07366(19) 0.89401(13) 0.2399(2) 0.0299(5) Uani 1 1 d . . . C9 C 0.08179(18) 0.83625(12) 0.3366(2) 0.0280(5) Uani 1 1 d . . . C10 C 0.18238(19) 0.80737(14) 0.3737(2) 0.0354(6) Uani 1 1 d . . . C11 C 0.1874(2) 0.75833(14) 0.4744(3) 0.0426(7) Uani 1 1 d . . . H11 H 0.2555 0.7405 0.5012 0.051 Uiso 1 1 calc R . . C12 C 0.0956(2) 0.73526(14) 0.5356(2) 0.0394(6) Uani 1 1 d . . . H12 H 0.1005 0.7023 0.6050 0.047 Uiso 1 1 calc R . . C13 C -0.0042(2) 0.76019(14) 0.4959(3) 0.0374(6) Uani 1 1 d . . . H13 H -0.0681 0.7427 0.5353 0.045 Uiso 1 1 calc R . . C14 C -0.01055(19) 0.81028(13) 0.3994(2) 0.0330(6) Uani 1 1 d . . . H14 H -0.0793 0.8278 0.3745 0.040 Uiso 1 1 calc R . . N1 N 0.06417(15) 1.05843(10) -0.05002(17) 0.0298(5) Uani 1 1 d . . . N2 N 0.14139(13) 0.96549(9) 0.0914(2) 0.0273(4) Uani 1 1 d . . . N3 N 0.16401(14) 0.91184(10) 0.17908(18) 0.0298(4) Uani 1 1 d . . . O1 O -0.01820(12) 0.92465(9) 0.21940(15) 0.0298(4) Uani 1 1 d . . . O2 O 0.27585(13) 0.82696(10) 0.31729(19) 0.0474(5) Uani 1 1 d . . . H2A H 0.2629 0.8548 0.2556 0.071 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 Fe1 0.0224(2) 0.0278(2) 0.0293(2) 0.000 0.000 -0.0004(2) C1 0.0363(15) 0.0338(15) 0.0362(15) 0.0011(12) -0.0010(12) -0.0043(12) C2 0.0465(18) 0.0392(16) 0.0383(14) 0.0061(13) -0.0012(12) -0.0040(13) C3 0.0591(19) 0.0355(15) 0.0374(15) -0.0006(12) 0.0082(12) -0.0147(13) C4 0.0391(17) 0.0319(12) 0.0441(14) -0.0068(13) 0.0081(12) -0.0111(12) C5 0.0294(13) 0.0298(14) 0.0351(13) -0.0067(11) 0.0025(11) -0.0023(11) C6 0.0281(13) 0.0295(14) 0.0327(12) -0.0098(11) 0.0001(11) -0.0036(10) C7 0.0290(14) 0.0443(15) 0.0494(16) -0.0096(12) 0.0102(12) -0.0019(12) C8 0.0280(14) 0.0301(13) 0.0317(13) -0.0074(10) -0.0055(10) 0.0013(11) C9 0.0299(13) 0.0249(12) 0.0291(12) -0.0040(10) -0.0026(10) 0.0007(10) C10 0.0295(14) 0.0348(15) 0.0419(14) 0.0013(11) -0.0020(12) 0.0017(11) C11 0.0339(16) 0.0412(16) 0.0526(17) 0.0084(13) -0.0131(13) 0.0038(12) C12 0.0439(16) 0.0375(15) 0.0369(14) 0.0066(11) -0.0041(12) 0.0006(12) C13 0.0360(14) 0.0346(14) 0.0416(15) 0.0024(11) 0.0041(12) 0.0001(12) C14 0.0319(14) 0.0332(14) 0.0338(14) 0.0023(10) -0.0020(11) 0.0042(11) N1 0.0312(13) 0.0278(11) 0.0304(11) -0.0021(9) 0.0020(9) -0.0062(10) N2 0.0233(9) 0.0265(9) 0.0320(9) -0.0075(11) 0.0022(10) 0.0006(7) N3 0.0250(11) 0.0298(11) 0.0345(11) 0.0006(9) -0.0008(8) 0.0028(8) O1 0.0268(9) 0.0312(10) 0.0314(9) 0.0019(7) 0.0001(7) 0.0015(7) O2 0.0273(11) 0.0545(12) 0.0602(14) 0.0179(10) -0.0030(9) 0.0036(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.8704(17) 2_575 ? Fe1 N2 1.8704(17) . ? Fe1 N1 1.9461(19) 2_575 ? Fe1 N1 1.9461(19) . ? Fe1 O1 1.9954(17) 2_575 ? Fe1 O1 1.9954(17) . ? C1 N1 1.332(3) . ? C1 C2 1.392(3) . ? C1 H1 0.9500 . ? C2 C3 1.381(4) . ? C2 H2 0.9500 . ? C3 C4 1.381(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 N1 1.376(3) . ? C5 C6 1.461(3) . ? C6 N2 1.304(3) . ? C6 C7 1.498(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O1 1.294(3) . ? C8 N3 1.327(3) . ? C8 C9 1.479(3) . ? C9 C14 1.403(3) . ? C9 C10 1.413(3) . ? C10 O2 1.348(3) . ? C10 C11 1.391(4) . ? C11 C12 1.372(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.373(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N2 N3 1.384(3) . ? O2 H2A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N2 176.03(15) 2_575 . ? N2 Fe1 N1 80.65(9) 2_575 2_575 ? N2 Fe1 N1 102.25(8) . 2_575 ? N2 Fe1 N1 102.25(8) 2_575 . ? N2 Fe1 N1 80.65(9) . . ? N1 Fe1 N1 88.39(11) 2_575 . ? N2 Fe1 O1 80.53(8) 2_575 2_575 ? N2 Fe1 O1 96.68(7) . 2_575 ? N1 Fe1 O1 160.99(7) 2_575 2_575 ? N1 Fe1 O1 92.92(7) . 2_575 ? N2 Fe1 O1 96.68(7) 2_575 . ? N2 Fe1 O1 80.53(8) . . ? N1 Fe1 O1 92.92(7) 2_575 . ? N1 Fe1 O1 160.99(7) . . ? O1 Fe1 O1 91.96(10) 2_575 . ? N1 C1 C2 122.5(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.4(2) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 118.8(2) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 121.3(2) . . ? N1 C5 C6 113.3(2) . . ? C4 C5 C6 125.2(2) . . ? N2 C6 C5 110.7(2) . . ? N2 C6 C7 124.3(2) . . ? C5 C6 C7 125.0(2) . . ? 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 . . ? O1 C8 N3 123.5(2) . . ? O1 C8 C9 119.9(2) . . ? N3 C8 C9 116.6(2) . . ? C14 C9 C10 117.4(2) . . ? C14 C9 C8 120.8(2) . . ? C10 C9 C8 121.7(2) . . ? O2 C10 C11 117.8(2) . . ? O2 C10 C9 122.4(2) . . ? C11 C10 C9 119.8(2) . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C9 121.8(2) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 119.1 . . ? C1 N1 C5 118.7(2) . . ? C1 N1 Fe1 126.99(16) . . ? C5 N1 Fe1 113.87(16) . . ? C6 N2 N3 121.09(18) . . ? C6 N2 Fe1 121.04(17) . . ? N3 N2 Fe1 117.74(14) . . ? C8 N3 N2 108.84(18) . . ? C8 O1 Fe1 109.31(15) . . ? C10 O2 H2A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.278 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.040 # Attachment '5-290K.cif' data_5a _database_code_depnum_ccdc_archive 'CCDC 756917' #TrackingRef '5-290K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Fe N6 O4' _chemical_formula_sum 'C28 H24 Fe N6 O4' _chemical_formula_weight 564.38 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 _symmetry_space_group_name_Hall 'A 2 -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 12.580(3) _cell_length_b 18.805(4) _cell_length_c 10.589(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2504.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 10399 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.373 _exptl_crystal_description block _exptl_crystal_colour 'black green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.651 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.926 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _diffrn_ambient_temperature 290(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 'NONIUS kappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2098 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2098 _reflns_number_gt 1055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al. 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0140P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00026(14) _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 0.49(2) _refine_ls_number_reflns 2098 _refine_ls_number_parameters 181 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.1407 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.0598 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.960 _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 Fe1 Fe 1.0000 0.5000 0.77915(7) 0.0614(3) Uani 1 2 d S . . C1 C 0.9611(5) 0.5988(3) 0.5544(5) 0.0977(18) Uani 1 1 d U . . H1 H 1.0337 0.6081 0.5586 0.117 Uiso 1 1 calc R . . C2 C 0.9015(7) 0.6318(3) 0.4597(6) 0.121(2) Uani 1 1 d U . . H2 H 0.9332 0.6621 0.4016 0.145 Uiso 1 1 calc R . . C3 C 0.7963(7) 0.6180(4) 0.4554(6) 0.137(3) Uani 1 1 d U . . H3 H 0.7552 0.6401 0.3939 0.165 Uiso 1 1 calc R . . C4 C 0.7479(6) 0.5725(3) 0.5390(6) 0.1132(19) Uani 1 1 d U . . H4 H 0.6755 0.5627 0.5346 0.136 Uiso 1 1 calc R . . C5 C 0.8125(5) 0.5417(3) 0.6307(5) 0.0801(15) Uani 1 1 d U . . C6 C 0.7733(4) 0.4893(3) 0.7235(5) 0.0761(14) Uani 1 1 d . . . C7 C 0.6563(3) 0.4720(2) 0.7417(5) 0.115(2) Uani 1 1 d . . . H7A H 0.6284 0.4999 0.8100 0.173 Uiso 1 1 calc R . . H7B H 0.6486 0.4224 0.7611 0.173 Uiso 1 1 calc R . . H7C H 0.6181 0.4827 0.6656 0.173 Uiso 1 1 calc R . . C8 C 0.9183(4) 0.3911(3) 0.9334(4) 0.0663(13) Uani 1 1 d . . . C9 C 0.9087(4) 0.3353(3) 1.0318(4) 0.0690(14) Uani 1 1 d . . . C10 C 0.8091(4) 0.3102(3) 1.0736(6) 0.0877(18) Uani 1 1 d . . . C11 C 0.8052(4) 0.2631(3) 1.1763(6) 0.1019(19) Uani 1 1 d . . . H11 H 0.7395 0.2480 1.2065 0.122 Uiso 1 1 calc R . . C12 C 0.8965(5) 0.2389(3) 1.2333(5) 0.0956(18) Uani 1 1 d . . . H12 H 0.8928 0.2075 1.3010 0.115 Uiso 1 1 calc R . . C13 C 0.9936(5) 0.2618(2) 1.1888(4) 0.0885(13) Uani 1 1 d . . . H13 H 1.0560 0.2448 1.2249 0.106 Uiso 1 1 calc R . . C14 C 0.9986(4) 0.3096(2) 1.0916(4) 0.0754(12) Uani 1 1 d . . . H14 H 1.0649 0.3254 1.0647 0.090 Uiso 1 1 calc R . . N1 N 0.9190(4) 0.5551(2) 0.6383(3) 0.0736(11) Uani 1 1 d . . . N2 N 0.8498(3) 0.4618(2) 0.7882(5) 0.0672(9) Uani 1 1 d . . . N3 N 0.8282(3) 0.4105(2) 0.8766(4) 0.0736(12) Uani 1 1 d . . . O1 O 1.0097(2) 0.41787(16) 0.9086(2) 0.0695(8) Uani 1 1 d . . . O2 O 0.7170(3) 0.3314(3) 1.0215(4) 0.1170(15) Uani 1 1 d . . . H2A H 0.7294 0.3540 0.9568 0.176 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 Fe1 0.0507(5) 0.0692(5) 0.0642(4) 0.000 0.000 0.0002(6) C1 0.135(5) 0.078(4) 0.080(4) 0.007(3) 0.010(3) 0.026(4) C2 0.193(7) 0.086(5) 0.083(4) 0.018(4) 0.000(5) 0.051(5) C3 0.212(7) 0.115(7) 0.085(5) -0.013(4) -0.044(6) 0.079(7) C4 0.142(5) 0.098(5) 0.100(5) -0.027(4) -0.052(4) 0.047(5) C5 0.087(4) 0.082(4) 0.071(3) -0.028(3) -0.028(3) 0.032(3) C6 0.081(4) 0.060(4) 0.087(4) -0.030(3) -0.016(3) 0.009(3) C7 0.048(3) 0.127(5) 0.170(6) -0.036(3) -0.036(3) 0.001(2) C8 0.074(4) 0.066(4) 0.058(3) -0.018(3) 0.003(3) 0.002(3) C9 0.064(4) 0.068(4) 0.075(4) -0.017(3) -0.001(3) -0.003(3) C10 0.070(4) 0.094(5) 0.100(5) -0.003(4) 0.007(4) 0.001(4) C11 0.072(5) 0.107(5) 0.126(5) 0.010(4) 0.025(4) -0.013(3) C12 0.088(4) 0.103(5) 0.096(5) 0.019(3) 0.007(3) -0.010(3) C13 0.077(4) 0.097(4) 0.091(3) 0.012(3) -0.009(4) -0.018(4) C14 0.063(3) 0.089(4) 0.075(3) 0.011(3) 0.003(4) -0.005(4) N1 0.100(3) 0.066(3) 0.055(3) -0.002(2) 0.001(3) 0.018(3) N2 0.062(2) 0.075(3) 0.065(2) -0.008(3) -0.020(3) 0.0075(19) N3 0.064(3) 0.079(3) 0.077(3) -0.011(3) -0.013(2) 0.005(2) O1 0.054(2) 0.082(2) 0.072(2) 0.0029(15) 0.0007(18) -0.0023(18) O2 0.067(3) 0.142(4) 0.142(4) 0.029(3) 0.002(3) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 2.024(3) . ? Fe1 N2 2.024(3) 2_765 ? Fe1 O1 2.068(3) 2_765 ? Fe1 O1 2.068(3) . ? Fe1 N1 2.083(4) 2_765 ? Fe1 N1 2.083(4) . ? C1 N1 1.322(5) . ? C1 C2 1.397(6) . ? C1 H1 0.9300 . ? C2 C3 1.349(8) . ? C2 H2 0.9300 . ? C3 C4 1.374(8) . ? C3 H3 0.9300 . ? C4 C5 1.393(7) . ? C4 H4 0.9300 . ? C5 N1 1.364(5) . ? C5 C6 1.476(6) . ? C6 N2 1.289(5) . ? C6 C7 1.520(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O1 1.282(5) . ? C8 N3 1.334(5) . ? C8 C9 1.484(6) . ? C9 C14 1.383(6) . ? C9 C10 1.410(7) . ? C10 O2 1.344(5) . ? C10 C11 1.403(7) . ? C11 C12 1.375(6) . ? C11 H11 0.9300 . ? C12 C13 1.379(6) . ? C12 H12 0.9300 . ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N2 N3 1.372(4) . ? O2 H2A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N2 174.6(3) . 2_765 ? N2 Fe1 O1 100.29(15) . 2_765 ? N2 Fe1 O1 76.03(16) 2_765 2_765 ? N2 Fe1 O1 76.03(16) . . ? N2 Fe1 O1 100.29(15) 2_765 . ? O1 Fe1 O1 97.01(14) 2_765 . ? N2 Fe1 N1 108.34(18) . 2_765 ? N2 Fe1 N1 75.7(2) 2_765 2_765 ? O1 Fe1 N1 151.00(15) 2_765 2_765 ? O1 Fe1 N1 94.28(13) . 2_765 ? N2 Fe1 N1 75.7(2) . . ? N2 Fe1 N1 108.34(18) 2_765 . ? O1 Fe1 N1 94.28(13) 2_765 . ? O1 Fe1 N1 151.00(15) . . ? N1 Fe1 N1 88.5(2) 2_765 . ? N1 C1 C2 122.8(6) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 117.8(7) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 122.2(7) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C3 C4 C5 116.7(7) . . ? C3 C4 H4 121.6 . . ? C5 C4 H4 121.6 . . ? N1 C5 C4 122.5(6) . . ? N1 C5 C6 114.3(4) . . ? C4 C5 C6 123.1(6) . . ? N2 C6 C5 111.9(4) . . ? N2 C6 C7 124.7(5) . . ? C5 C6 C7 123.5(5) . . ? 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 . . ? O1 C8 N3 124.2(5) . . ? O1 C8 C9 119.7(4) . . ? N3 C8 C9 116.1(5) . . ? C14 C9 C10 117.8(5) . . ? C14 C9 C8 120.1(5) . . ? C10 C9 C8 122.0(5) . . ? O2 C10 C11 118.4(6) . . ? O2 C10 C9 122.5(6) . . ? C11 C10 C9 119.0(5) . . ? C12 C11 C10 121.3(5) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 119.1(5) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 120.2(6) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 122.4(6) . . ? C13 C14 H14 118.8 . . ? C9 C14 H14 118.8 . . ? C1 N1 C5 118.0(5) . . ? C1 N1 Fe1 126.5(4) . . ? C5 N1 Fe1 115.5(4) . . ? C6 N2 N3 119.8(4) . . ? C6 N2 Fe1 121.9(4) . . ? N3 N2 Fe1 117.8(3) . . ? C8 N3 N2 109.4(4) . . ? C8 O1 Fe1 112.1(3) . . ? C10 O2 H2A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.155 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.035 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 756918' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28 Fe N6 O4' _chemical_formula_sum 'C38 H28 Fe N6 O4' _chemical_formula_weight 688.51 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' Fe Fe 0.3463 0.8444 '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 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.652(2) _cell_length_b 13.796(3) _cell_length_c 22.181(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.87(3) _cell_angle_gamma 90.00 _cell_volume 3257.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21318 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995, 1997) ; _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 'NONIUS KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 41687 _diffrn_reflns_av_R_equivalents 0.1053 _diffrn_reflns_av_sigmaI/netI 0.1044 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5695 _reflns_number_gt 2862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0160P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00030(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5695 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1190 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0585 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.50905(3) 0.75393(2) 0.329416(14) 0.04428(14) Uani 1 1 d . . . C1 C 0.6168(3) 0.86050(18) 0.22863(14) 0.0608(8) Uani 1 1 d . . . H1 H 0.6837 0.8764 0.2547 0.073 Uiso 1 1 calc R . . C2 C 0.6194(3) 0.89103(19) 0.16990(16) 0.0760(10) Uani 1 1 d . . . H2 H 0.6871 0.9268 0.1565 0.091 Uiso 1 1 calc R . . C3 C 0.5216(4) 0.8684(2) 0.13130(14) 0.0783(10) Uani 1 1 d . . . H3 H 0.5219 0.8891 0.0914 0.094 Uiso 1 1 calc R . . C4 C 0.4231(3) 0.81525(19) 0.15138(13) 0.0705(9) Uani 1 1 d . . . H4 H 0.3561 0.7993 0.1253 0.085 Uiso 1 1 calc R . . C5 C 0.4244(3) 0.78531(16) 0.21145(13) 0.0490(7) Uani 1 1 d . . . C6 C 0.3284(3) 0.72518(16) 0.23893(12) 0.0448(7) Uani 1 1 d . . . C7 C 0.2130(3) 0.6913(2) 0.20717(11) 0.0528(7) Uani 1 1 d . . . C8 C 0.1229(3) 0.7548(2) 0.18620(14) 0.1045(11) Uani 1 1 d . . . H8 H 0.1360 0.8209 0.1914 0.125 Uiso 1 1 calc R . . C9 C 0.0124(4) 0.7231(3) 0.15740(17) 0.1280(15) Uani 1 1 d . . . H9 H -0.0484 0.7673 0.1441 0.154 Uiso 1 1 calc R . . C10 C -0.0053(4) 0.6256(3) 0.14907(15) 0.1024(12) Uani 1 1 d . . . H10 H -0.0792 0.6028 0.1306 0.123 Uiso 1 1 calc R . . C11 C 0.0835(4) 0.5638(3) 0.16753(17) 0.1017(12) Uani 1 1 d . . . H11 H 0.0725 0.4979 0.1600 0.122 Uiso 1 1 calc R . . C12 C 0.1915(3) 0.5947(2) 0.19764(14) 0.0857(11) Uani 1 1 d . . . H12 H 0.2502 0.5494 0.2116 0.103 Uiso 1 1 calc R . . C13 C 0.3457(3) 0.63790(17) 0.38445(13) 0.0435(7) Uani 1 1 d . . . C14 C 0.2846(3) 0.57345(18) 0.42785(13) 0.0474(7) Uani 1 1 d . . . C15 C 0.1736(3) 0.5230(2) 0.41356(14) 0.0569(8) Uani 1 1 d . . . C16 C 0.1240(3) 0.4592(2) 0.45510(17) 0.0771(9) Uani 1 1 d . . . H16 H 0.0503 0.4256 0.4457 0.093 Uiso 1 1 calc R . . C17 C 0.1850(4) 0.4460(2) 0.51036(17) 0.0975(12) Uani 1 1 d . . . H17 H 0.1523 0.4028 0.5379 0.117 Uiso 1 1 calc R . . C18 C 0.2929(4) 0.4955(3) 0.52519(15) 0.1042(13) Uani 1 1 d . . . H18 H 0.3327 0.4868 0.5627 0.125 Uiso 1 1 calc R . . C19 C 0.3418(3) 0.5584(2) 0.48403(14) 0.0776(10) Uani 1 1 d . . . H19 H 0.4154 0.5917 0.4942 0.093 Uiso 1 1 calc R . . C20 C 0.6020(3) 0.57424(19) 0.27300(11) 0.0553(8) Uani 1 1 d . . . H20 H 0.5200 0.5631 0.2590 0.066 Uiso 1 1 calc R . . C21 C 0.6942(3) 0.50997(19) 0.25714(12) 0.0632(9) Uani 1 1 d . . . H21 H 0.6753 0.4581 0.2317 0.076 Uiso 1 1 calc R . . C22 C 0.8142(3) 0.5237(2) 0.27949(14) 0.0712(9) Uani 1 1 d . . . H22 H 0.8771 0.4798 0.2704 0.085 Uiso 1 1 calc R . . C23 C 0.8414(3) 0.6032(2) 0.31566(12) 0.0610(8) Uani 1 1 d . . . H23 H 0.9223 0.6129 0.3316 0.073 Uiso 1 1 calc R . . C24 C 0.7462(3) 0.66808(18) 0.32779(11) 0.0438(7) Uani 1 1 d . . . C25 C 0.7637(3) 0.75885(19) 0.36085(10) 0.0429(6) Uani 1 1 d . . . C26 C 0.8867(3) 0.79524(16) 0.38316(14) 0.0495(7) Uani 1 1 d . . . C27 C 0.9886(3) 0.79952(17) 0.34494(13) 0.0622(8) Uani 1 1 d . . . H27 H 0.9793 0.7781 0.3053 0.075 Uiso 1 1 calc R . . C28 C 1.1034(3) 0.8357(2) 0.36606(18) 0.0755(10) Uani 1 1 d . . . H28 H 1.1704 0.8390 0.3403 0.091 Uiso 1 1 calc R . . C29 C 1.1190(3) 0.8663(2) 0.4241(2) 0.0873(11) Uani 1 1 d . . . H29 H 1.1963 0.8904 0.4378 0.105 Uiso 1 1 calc R . . C30 C 1.0216(4) 0.8618(2) 0.46169(16) 0.0884(11) Uani 1 1 d . . . H30 H 1.0328 0.8823 0.5014 0.106 Uiso 1 1 calc R . . C31 C 0.9050(3) 0.8266(2) 0.44163(14) 0.0731(9) Uani 1 1 d . . . H31 H 0.8389 0.8244 0.4680 0.088 Uiso 1 1 calc R . . C32 C 0.5315(3) 0.92663(18) 0.38653(11) 0.0449(7) Uani 1 1 d . . . C33 C 0.5039(3) 1.02180(18) 0.41339(11) 0.0474(7) Uani 1 1 d . . . C34 C 0.5939(3) 1.0735(2) 0.44813(12) 0.0539(8) Uani 1 1 d . . . C35 C 0.5591(3) 1.1577(2) 0.47717(12) 0.0649(9) Uani 1 1 d . . . H35 H 0.6184 1.1907 0.5011 0.078 Uiso 1 1 calc R . . C36 C 0.4405(4) 1.1930(2) 0.47153(13) 0.0683(9) Uani 1 1 d . . . H36 H 0.4188 1.2491 0.4920 0.082 Uiso 1 1 calc R . . C37 C 0.3513(3) 1.1453(2) 0.43507(13) 0.0701(9) Uani 1 1 d . . . H37 H 0.2707 1.1706 0.4296 0.084 Uiso 1 1 calc R . . C38 C 0.3841(3) 1.0602(2) 0.40723(11) 0.0608(8) Uani 1 1 d . . . H38 H 0.3241 1.0276 0.3836 0.073 Uiso 1 1 calc R . . N1 N 0.5216(2) 0.80860(13) 0.24992(9) 0.0465(6) Uani 1 1 d . . . N2 N 0.36144(18) 0.70376(13) 0.29443(10) 0.0405(5) Uani 1 1 d . . . N3 N 0.28865(19) 0.64532(13) 0.32979(10) 0.0442(6) Uani 1 1 d . . . N4 N 0.6254(2) 0.65215(14) 0.30767(9) 0.0443(6) Uani 1 1 d . . . N5 N 0.6563(2) 0.80555(15) 0.36456(8) 0.0421(6) Uani 1 1 d . . . N6 N 0.6508(2) 0.89662(15) 0.39010(8) 0.0468(6) Uani 1 1 d . . . O1 O 0.44835(17) 0.68056(11) 0.39906(7) 0.0495(5) Uani 1 1 d . . . O2 O 0.11303(17) 0.53045(14) 0.35927(9) 0.0751(6) Uani 1 1 d . . . H2A H 0.1540 0.5646 0.3369 0.113 Uiso 1 1 calc R . . O3 O 0.44137(16) 0.87714(11) 0.36119(7) 0.0486(5) Uani 1 1 d . . . O4 O 0.7132(2) 1.04392(13) 0.45638(9) 0.0778(6) Uani 1 1 d . . . H4A H 0.7235 0.9931 0.4380 0.117 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 Fe1 0.0423(3) 0.0451(2) 0.0449(2) -0.0034(2) -0.00589(17) -0.0040(2) C1 0.063(2) 0.0588(19) 0.061(2) 0.0032(16) 0.0029(18) -0.0078(17) C2 0.090(3) 0.070(2) 0.068(2) 0.0120(19) 0.015(2) -0.0254(19) C3 0.105(3) 0.079(2) 0.051(2) 0.0156(18) 0.005(2) -0.024(2) C4 0.098(3) 0.067(2) 0.046(2) 0.0039(17) -0.0076(19) -0.010(2) C5 0.060(2) 0.0440(17) 0.0430(19) -0.0013(14) -0.0021(17) -0.0009(15) C6 0.046(2) 0.0437(17) 0.0444(18) -0.0034(14) -0.0075(16) -0.0040(14) C7 0.056(2) 0.053(2) 0.0476(18) 0.0020(15) -0.0146(16) -0.0001(18) C8 0.098(3) 0.074(2) 0.137(3) -0.012(2) -0.061(2) 0.010(3) C9 0.093(3) 0.113(3) 0.172(4) 0.003(3) -0.082(3) 0.014(3) C10 0.073(3) 0.120(3) 0.111(3) 0.005(3) -0.041(2) -0.021(3) C11 0.090(3) 0.075(3) 0.137(3) -0.010(2) -0.036(3) -0.017(3) C12 0.075(3) 0.059(2) 0.120(3) -0.0167(19) -0.037(2) -0.0070(19) C13 0.046(2) 0.0406(17) 0.044(2) -0.0006(15) 0.0038(18) 0.0076(15) C14 0.046(2) 0.0478(17) 0.049(2) 0.0002(15) 0.0082(17) 0.0027(16) C15 0.050(3) 0.063(2) 0.059(2) 0.0057(18) 0.009(2) 0.0105(18) C16 0.065(3) 0.082(2) 0.086(3) 0.010(2) 0.020(2) -0.0177(18) C17 0.121(4) 0.104(3) 0.069(3) 0.023(2) 0.023(3) -0.020(3) C18 0.130(4) 0.119(3) 0.063(3) 0.025(2) -0.009(2) -0.047(3) C19 0.099(3) 0.083(2) 0.051(2) 0.0113(18) -0.005(2) -0.028(2) C20 0.054(2) 0.0461(18) 0.066(2) -0.0072(16) -0.0024(17) -0.0048(17) C21 0.064(3) 0.0465(19) 0.079(2) -0.0160(15) 0.002(2) -0.0058(19) C22 0.063(3) 0.0459(19) 0.106(3) -0.0105(18) 0.009(2) 0.0042(18) C23 0.040(2) 0.0557(19) 0.087(2) -0.0009(17) -0.0081(17) 0.0042(17) C24 0.040(2) 0.0446(18) 0.0469(18) 0.0011(14) -0.0036(16) 0.0022(16) C25 0.037(2) 0.0489(18) 0.0427(16) 0.0001(15) -0.0070(13) -0.0007(17) C26 0.043(2) 0.0452(16) 0.059(2) -0.0039(14) -0.0106(18) 0.0011(14) C27 0.050(2) 0.0559(18) 0.081(2) -0.0097(15) -0.006(2) -0.0024(16) C28 0.043(3) 0.062(2) 0.121(3) -0.005(2) 0.000(2) -0.0001(18) C29 0.051(3) 0.083(2) 0.126(4) -0.002(2) -0.033(3) -0.010(2) C30 0.073(3) 0.113(3) 0.077(3) -0.017(2) -0.029(2) -0.014(2) C31 0.058(3) 0.094(2) 0.067(2) -0.0061(19) -0.0116(19) -0.0073(19) C32 0.053(2) 0.0430(18) 0.0386(17) -0.0030(13) -0.0023(16) -0.0019(17) C33 0.049(2) 0.0483(18) 0.0447(18) -0.0040(15) -0.0021(16) 0.0000(17) C34 0.054(3) 0.053(2) 0.054(2) -0.0050(16) -0.0066(19) 0.0051(19) C35 0.084(3) 0.050(2) 0.060(2) -0.0136(16) -0.0089(19) -0.0044(18) C36 0.084(3) 0.0518(19) 0.070(2) -0.0122(16) 0.004(2) 0.008(2) C37 0.067(3) 0.065(2) 0.079(2) -0.0117(18) 0.005(2) 0.0127(19) C38 0.061(3) 0.058(2) 0.063(2) -0.0164(16) -0.0017(18) 0.0001(18) N1 0.0461(17) 0.0426(13) 0.0505(15) -0.0065(11) -0.0010(14) -0.0066(12) N2 0.0403(16) 0.0415(12) 0.0392(14) -0.0008(11) -0.0047(12) -0.0002(10) N3 0.0458(16) 0.0437(13) 0.0431(15) 0.0054(11) -0.0006(13) -0.0025(11) N4 0.0455(18) 0.0420(14) 0.0449(14) -0.0030(11) -0.0055(12) -0.0048(12) N5 0.0403(17) 0.0431(14) 0.0426(13) -0.0053(11) -0.0046(12) -0.0021(12) N6 0.0406(17) 0.0466(15) 0.0525(14) -0.0092(11) -0.0072(12) -0.0003(12) O1 0.0471(14) 0.0563(11) 0.0447(11) 0.0017(9) -0.0050(10) -0.0098(10) O2 0.0447(15) 0.0934(16) 0.0868(16) 0.0190(12) -0.0046(13) -0.0117(11) O3 0.0418(13) 0.0524(11) 0.0511(12) -0.0099(9) -0.0065(10) -0.0017(10) O4 0.0747(17) 0.0674(14) 0.0895(17) -0.0290(11) -0.0260(13) -0.0015(13) _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 Fe1 N2 1.864(2) . ? Fe1 N5 1.870(2) . ? Fe1 N1 1.927(2) . ? Fe1 N4 1.944(2) . ? Fe1 O1 1.9733(16) . ? Fe1 O3 1.9846(15) . ? C1 N1 1.339(3) . ? C1 C2 1.370(3) . ? C1 H1 0.9300 . ? C2 C3 1.363(4) . ? C2 H2 0.9300 . ? C3 C4 1.366(3) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 H4 0.9300 . ? C5 N1 1.359(3) . ? C5 C6 1.465(3) . ? C6 N2 1.303(3) . ? C6 C7 1.473(3) . ? C7 C12 1.368(3) . ? C7 C8 1.369(3) . ? C8 C9 1.392(4) . ? C8 H8 0.9300 . ? C9 C10 1.371(4) . ? C9 H9 0.9300 . ? C10 C11 1.328(4) . ? C10 H10 0.9300 . ? C11 C12 1.379(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O1 1.274(3) . ? C13 N3 1.342(3) . ? C13 C14 1.477(3) . ? C14 C19 1.385(3) . ? C14 C15 1.399(3) . ? C15 O2 1.351(3) . ? C15 C16 1.392(3) . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C17 C18 1.368(4) . ? C17 H17 0.9300 . ? C18 C19 1.374(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N4 1.340(3) . ? C20 C21 1.378(3) . ? C20 H20 0.9300 . ? C21 C22 1.368(3) . ? C21 H21 0.9300 . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.386(3) . ? C23 H23 0.9300 . ? C24 N4 1.366(3) . ? C24 C25 1.460(3) . ? C25 N5 1.318(3) . ? C25 C26 1.473(3) . ? C26 C31 1.375(3) . ? C26 C27 1.400(3) . ? C27 C28 1.388(3) . ? C27 H27 0.9300 . ? C28 C29 1.359(4) . ? C28 H28 0.9300 . ? C29 C30 1.354(4) . ? C29 H29 0.9300 . ? C30 C31 1.393(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 O3 1.292(3) . ? C32 N6 1.336(3) . ? C32 C33 1.475(3) . ? C33 C38 1.384(3) . ? C33 C34 1.404(3) . ? C34 O4 1.342(3) . ? C34 C35 1.384(3) . ? C35 C36 1.356(3) . ? C35 H35 0.9300 . ? C36 C37 1.393(3) . ? C36 H36 0.9300 . ? C37 C38 1.377(3) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? N2 N3 1.381(2) . ? N5 N6 1.380(2) . ? O2 H2A 0.8200 . ? O4 H4A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N5 179.39(9) . . ? N2 Fe1 N1 81.21(10) . . ? N5 Fe1 N1 98.63(10) . . ? N2 Fe1 N4 99.46(9) . . ? N5 Fe1 N4 81.12(10) . . ? N1 Fe1 N4 89.53(8) . . ? N2 Fe1 O1 80.91(9) . . ? N5 Fe1 O1 99.26(8) . . ? N1 Fe1 O1 162.11(9) . . ? N4 Fe1 O1 92.95(7) . . ? N2 Fe1 O3 98.90(7) . . ? N5 Fe1 O3 80.52(9) . . ? N1 Fe1 O3 91.53(7) . . ? N4 Fe1 O3 161.55(9) . . ? O1 Fe1 O3 91.68(6) . . ? N1 C1 C2 122.6(3) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 120.9(3) . . ? N1 C5 C6 113.6(2) . . ? C4 C5 C6 125.4(3) . . ? N2 C6 C5 110.6(2) . . ? N2 C6 C7 125.1(2) . . ? C5 C6 C7 124.3(3) . . ? C12 C7 C8 117.3(3) . . ? C12 C7 C6 121.1(3) . . ? C8 C7 C6 121.6(3) . . ? C7 C8 C9 121.9(3) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C10 C9 C8 118.7(4) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C7 C12 C11 120.6(3) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? O1 C13 N3 123.6(2) . . ? O1 C13 C14 120.3(3) . . ? N3 C13 C14 116.0(3) . . ? C19 C14 C15 118.2(3) . . ? C19 C14 C13 119.1(3) . . ? C15 C14 C13 122.6(3) . . ? O2 C15 C16 117.2(3) . . ? O2 C15 C14 122.7(3) . . ? C16 C15 C14 120.1(3) . . ? C17 C16 C15 119.6(3) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 121.0(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.3(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C14 121.8(3) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? N4 C20 C21 122.8(3) . . ? N4 C20 H20 118.6 . . ? C21 C20 H20 118.6 . . ? C20 C21 C22 118.9(3) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C23 119.7(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 119.0(3) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? N4 C24 C23 121.3(2) . . ? N4 C24 C25 113.9(2) . . ? C23 C24 C25 124.7(3) . . ? N5 C25 C24 110.7(2) . . ? N5 C25 C26 125.2(2) . . ? C24 C25 C26 124.0(3) . . ? C31 C26 C27 118.0(3) . . ? C31 C26 C25 121.4(3) . . ? C27 C26 C25 120.6(3) . . ? C28 C27 C26 120.2(3) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C29 C28 C27 120.7(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 119.8(3) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C29 C30 C31 120.8(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C26 C31 C30 120.5(3) . . ? C26 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? O3 C32 N6 123.6(2) . . ? O3 C32 C33 119.4(3) . . ? N6 C32 C33 117.0(3) . . ? C38 C33 C34 118.0(3) . . ? C38 C33 C32 119.7(3) . . ? C34 C33 C32 122.2(3) . . ? O4 C34 C35 117.3(3) . . ? O4 C34 C33 123.1(3) . . ? C35 C34 C33 119.6(3) . . ? C36 C35 C34 121.4(3) . . ? C36 C35 H35 119.3 . . ? C34 C35 H35 119.3 . . ? C35 C36 C37 120.0(3) . . ? C35 C36 H36 120.0 . . ? C37 C36 H36 120.0 . . ? C38 C37 C36 119.0(3) . . ? C38 C37 H37 120.5 . . ? C36 C37 H37 120.5 . . ? C37 C38 C33 121.9(3) . . ? C37 C38 H38 119.0 . . ? C33 C38 H38 119.0 . . ? C1 N1 C5 118.3(2) . . ? C1 N1 Fe1 127.4(2) . . ? C5 N1 Fe1 114.08(18) . . ? C6 N2 N3 122.0(2) . . ? C6 N2 Fe1 120.47(18) . . ? N3 N2 Fe1 117.52(16) . . ? C13 N3 N2 108.2(2) . . ? C20 N4 C24 118.2(2) . . ? C20 N4 Fe1 127.8(2) . . ? C24 N4 Fe1 113.84(17) . . ? C25 N5 N6 121.3(2) . . ? C25 N5 Fe1 120.39(17) . . ? N6 N5 Fe1 118.11(16) . . ? C32 N6 N5 108.1(2) . . ? C13 O1 Fe1 109.77(16) . . ? C15 O2 H2A 109.5 . . ? C32 O3 Fe1 109.49(16) . . ? C34 O4 H4A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.407 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.044