# Electronic Supplementary Material (ESI) for Analyst # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'The Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email caoqianyong@163.com _publ_contact_author_name 'Qian-Yong Cao' loop_ _publ_author_name 'Qian Cao' T.Pradhan 'Min Hee Lee' 'Kwanghyun No' 'Jong Seung Kim' data_cao-2 _database_code_depnum_ccdc_archive 'CCDC 847714' #TrackingRef 'Br.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H33 Fe N4 O, Br' _chemical_formula_sum 'C31 H33 Br Fe N4 O' _chemical_formula_weight 613.37 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.3791(17) _cell_length_b 19.3945(15) _cell_length_c 16.8449(14) _cell_angle_alpha 90.00 _cell_angle_beta 121.230(4) _cell_angle_gamma 90.00 _cell_volume 5693.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 895 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 26.2 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.463 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.124 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 1.964 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.615 _exptl_absorpt_correction_T_max 0.784 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23187 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6493 _reflns_number_gt 4127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART (Bruker, 1998)' _computing_data_reduction 'Bruker SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1998)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1998)' _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^)+(0.0356P)^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_number_reflns 6493 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.36581(2) 0.996964(19) 1.01240(3) 0.04136(12) Uani 1 1 d . . . O1 O 0.25605(12) 0.98375(10) 0.74180(14) 0.0600(6) Uani 1 1 d . . . N1 N 0.17858(13) 0.95561(11) 0.79544(14) 0.0444(6) Uani 1 1 d . . . H1A H 0.1752 0.9433 0.8422 0.053 Uiso 1 1 calc R . . N2 N 0.08095(12) 0.85033(10) 0.63669(14) 0.0364(5) Uani 1 1 d . . . N3 N 0.08108(12) 0.81435(11) 0.57020(14) 0.0401(5) Uani 1 1 d . . . N4 N 0.10150(12) 0.85960(11) 0.52805(13) 0.0362(5) Uani 1 1 d . . . C1 C 0.3704(3) 1.04089(19) 1.1241(3) 0.0839(12) Uani 1 1 d . . . H1B H 0.3799 1.0168 1.1803 0.101 Uiso 1 1 calc R . . C2 C 0.2993(2) 1.0526(2) 1.0455(4) 0.0865(14) Uani 1 1 d . . . H2A H 0.2496 1.0384 1.0361 0.104 Uiso 1 1 calc R . . C3 C 0.3109(2) 1.08843(17) 0.9824(3) 0.0775(11) Uani 1 1 d . . . H3A H 0.2706 1.1039 0.9206 0.093 Uiso 1 1 calc R . . C4 C 0.3891(2) 1.09924(15) 1.0221(3) 0.0646(9) Uani 1 1 d . . . H4A H 0.4138 1.1236 0.9935 0.077 Uiso 1 1 calc R . . C5 C 0.4259(2) 1.06976(17) 1.1099(3) 0.0691(10) Uani 1 1 d . . . H5A H 0.4814 1.0694 1.1542 0.083 Uiso 1 1 calc R . . C7 C 0.43920(18) 0.92524(14) 1.0123(2) 0.0563(8) Uani 1 1 d . . . H7A H 0.4954 0.9276 1.0489 0.068 Uiso 1 1 calc R . . C8 C 0.39195(17) 0.89425(15) 1.0408(2) 0.0524(8) Uani 1 1 d . . . H8A H 0.4096 0.8715 1.1005 0.063 Uiso 1 1 calc R . . C9 C 0.31510(17) 0.90338(14) 0.96922(19) 0.0488(7) Uani 1 1 d . . . H9A H 0.2698 0.8874 0.9698 0.059 Uiso 1 1 calc R . . C10 C 0.31483(16) 0.93954(13) 0.89499(19) 0.0408(7) Uani 1 1 d . . . C11 C 0.24862(17) 0.96205(13) 0.80501(19) 0.0436(7) Uani 1 1 d . . . C12 C 0.10991(16) 0.96929(13) 0.70758(18) 0.0427(7) Uani 1 1 d . . . H12A H 0.1128 1.0152 0.6867 0.051 Uiso 1 1 calc R . . H12B H 0.0659 0.9678 0.7152 0.051 Uiso 1 1 calc R . . C13 C 0.09947(15) 0.91787(13) 0.63623(17) 0.0371(6) Uani 1 1 d . . . C15 C 0.11147(15) 0.83640(13) 0.45395(17) 0.0367(6) Uani 1 1 d . . . C16 C 0.09449(16) 0.87950(14) 0.38092(18) 0.0445(7) Uani 1 1 d . . . H16A H 0.0774 0.9243 0.3791 0.053 Uiso 1 1 calc R . . C17 C 0.10348(16) 0.85469(14) 0.31049(18) 0.0453(7) Uani 1 1 d . . . H17A H 0.0928 0.8839 0.2614 0.054 Uiso 1 1 calc R . . C18 C 0.12778(15) 0.78806(13) 0.30955(17) 0.0367(6) Uani 1 1 d . . . C21 C 0.13339(16) 0.75845(15) 0.22934(18) 0.0452(7) Uani 1 1 d . . . C24 C 0.07236(19) 0.70206(17) 0.1832(2) 0.0747(10) Uani 1 1 d . . . H24A H 0.0224 0.7217 0.1601 0.112 Uiso 1 1 calc R . . H24B H 0.0815 0.6669 0.2279 0.112 Uiso 1 1 calc R . . H24C H 0.0749 0.6822 0.1326 0.112 Uiso 1 1 calc R . . C23 C 0.21287(18) 0.72642(17) 0.2659(2) 0.0656(9) Uani 1 1 d . . . H23A H 0.2223 0.6921 0.3118 0.098 Uiso 1 1 calc R . . H23B H 0.2514 0.7617 0.2934 0.098 Uiso 1 1 calc R . . H23C H 0.2147 0.7054 0.2155 0.098 Uiso 1 1 calc R . . C22 C 0.11891(19) 0.81316(16) 0.1562(2) 0.0661(9) Uani 1 1 d . . . H22A H 0.0693 0.8335 0.1330 0.099 Uiso 1 1 calc R . . H22B H 0.1208 0.7920 0.1059 0.099 Uiso 1 1 calc R . . H22C H 0.1576 0.8483 0.1839 0.099 Uiso 1 1 calc R . . C19 C 0.14584(16) 0.74728(14) 0.38609(19) 0.0473(7) Uani 1 1 d . . . H19A H 0.1634 0.7026 0.3888 0.057 Uiso 1 1 calc R . . C20 C 0.13848(17) 0.77108(14) 0.45784(18) 0.0468(7) Uani 1 1 d . . . H20A H 0.1518 0.7430 0.5088 0.056 Uiso 1 1 calc R . . C14 C 0.11289(15) 0.92316(13) 0.56547(18) 0.0385(6) Uani 1 1 d . . . H14A H 0.1271 0.9626 0.5466 0.046 Uiso 1 1 calc R . . C25 C 0.05785(16) 0.81466(13) 0.69639(18) 0.0426(7) Uani 1 1 d . . . H25A H 0.0047 0.8003 0.6587 0.051 Uiso 1 1 calc R . . H25B H 0.0617 0.8466 0.7429 0.051 Uiso 1 1 calc R . . C26 C 0.10714(15) 0.75265(13) 0.74383(18) 0.0374(6) Uani 1 1 d . . . C27 C 0.16670(17) 0.75667(15) 0.83455(19) 0.0478(7) Uani 1 1 d . . . H27A H 0.1749 0.7976 0.8672 0.057 Uiso 1 1 calc R . . C28 C 0.21437(18) 0.70127(17) 0.8780(2) 0.0569(8) Uani 1 1 d . . . H28A H 0.2549 0.7050 0.9390 0.068 Uiso 1 1 calc R . . C29 C 0.2015(2) 0.64052(16) 0.8304(2) 0.0611(9) Uani 1 1 d . . . H29A H 0.2333 0.6028 0.8592 0.073 Uiso 1 1 calc R . . C30 C 0.1420(2) 0.63563(16) 0.7404(2) 0.0628(9) Uani 1 1 d . . . H30A H 0.1334 0.5945 0.7082 0.075 Uiso 1 1 calc R . . C31 C 0.09477(18) 0.69108(15) 0.6975(2) 0.0521(8) Uani 1 1 d . . . H31A H 0.0541 0.6870 0.6365 0.062 Uiso 1 1 calc R . . C6 C 0.39217(17) 0.95245(14) 0.9231(2) 0.0485(7) Uani 1 1 d . . . H6A H 0.4099 0.9768 0.8866 0.058 Uiso 1 1 calc R . . Br1 Br 0.104635(17) 0.924697(15) 0.92891(2) 0.05017(11) 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 0.0368(2) 0.0386(2) 0.0490(2) -0.00829(19) 0.0224(2) -0.00516(19) O1 0.0699(15) 0.0674(14) 0.0540(12) -0.0026(11) 0.0401(12) -0.0201(11) N1 0.0455(15) 0.0560(15) 0.0368(13) -0.0060(11) 0.0250(12) -0.0108(12) N2 0.0421(14) 0.0318(12) 0.0401(12) 0.0001(10) 0.0247(11) 0.0014(11) N3 0.0492(15) 0.0345(12) 0.0434(13) -0.0007(10) 0.0289(12) -0.0027(11) N4 0.0413(14) 0.0335(12) 0.0352(12) -0.0011(10) 0.0209(11) -0.0037(10) C1 0.137(4) 0.069(3) 0.073(3) -0.025(2) 0.074(3) -0.025(3) C2 0.070(3) 0.075(3) 0.146(4) -0.052(3) 0.078(3) -0.021(2) C3 0.076(3) 0.053(2) 0.081(3) -0.018(2) 0.025(2) 0.018(2) C4 0.093(3) 0.0334(17) 0.097(3) -0.0170(19) 0.070(3) -0.0100(19) C5 0.059(2) 0.062(2) 0.069(2) -0.0253(19) 0.022(2) -0.0115(19) C7 0.0402(18) 0.0477(18) 0.082(2) -0.0067(17) 0.0321(18) -0.0004(16) C8 0.048(2) 0.0417(17) 0.0595(19) 0.0060(15) 0.0224(16) 0.0009(15) C9 0.0508(19) 0.0400(16) 0.0547(18) -0.0016(14) 0.0267(16) -0.0108(15) C10 0.0444(18) 0.0323(15) 0.0503(17) -0.0116(13) 0.0278(15) -0.0095(13) C11 0.0539(19) 0.0346(16) 0.0479(17) -0.0123(14) 0.0303(16) -0.0124(14) C12 0.0523(19) 0.0370(15) 0.0436(16) -0.0044(13) 0.0283(15) -0.0006(14) C13 0.0379(16) 0.0356(15) 0.0376(14) 0.0005(12) 0.0194(13) 0.0016(13) C15 0.0423(17) 0.0347(15) 0.0361(14) -0.0042(12) 0.0225(13) -0.0049(13) C16 0.0575(19) 0.0343(15) 0.0462(16) 0.0015(14) 0.0299(15) 0.0018(14) C17 0.057(2) 0.0412(16) 0.0424(16) 0.0088(13) 0.0294(15) 0.0033(15) C18 0.0369(16) 0.0374(15) 0.0396(14) -0.0041(12) 0.0225(13) -0.0083(13) C21 0.0463(18) 0.0523(18) 0.0435(16) -0.0040(14) 0.0278(15) -0.0016(15) C24 0.077(3) 0.082(2) 0.073(2) -0.039(2) 0.044(2) -0.026(2) C23 0.066(2) 0.083(2) 0.066(2) 0.0036(18) 0.0468(19) 0.0135(19) C22 0.078(2) 0.082(2) 0.0515(19) 0.0038(17) 0.0430(19) 0.011(2) C19 0.066(2) 0.0302(15) 0.0559(17) 0.0022(14) 0.0388(17) 0.0031(14) C20 0.070(2) 0.0358(16) 0.0464(16) 0.0052(14) 0.0390(16) 0.0021(15) C14 0.0463(17) 0.0285(14) 0.0408(15) -0.0004(12) 0.0226(14) -0.0048(13) C25 0.0492(18) 0.0437(16) 0.0501(16) 0.0032(14) 0.0364(15) 0.0032(14) C26 0.0459(17) 0.0354(15) 0.0438(16) 0.0020(13) 0.0323(14) -0.0044(13) C27 0.061(2) 0.0433(17) 0.0442(16) -0.0012(14) 0.0304(16) -0.0070(16) C28 0.061(2) 0.061(2) 0.0467(17) 0.0123(17) 0.0266(16) -0.0016(18) C29 0.075(3) 0.050(2) 0.077(2) 0.0230(19) 0.052(2) 0.0159(18) C30 0.090(3) 0.0353(18) 0.069(2) -0.0005(17) 0.045(2) 0.0010(18) C31 0.059(2) 0.0421(17) 0.0482(17) -0.0034(15) 0.0229(16) -0.0057(16) C6 0.054(2) 0.0385(16) 0.067(2) -0.0082(15) 0.0410(18) -0.0041(15) Br1 0.0526(2) 0.04910(19) 0.05593(19) -0.00952(15) 0.03320(16) -0.00724(15) _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 C3 2.017(3) . ? Fe1 C1 2.023(3) . ? Fe1 C2 2.024(3) . ? Fe1 C10 2.025(3) . ? Fe1 C5 2.026(3) . ? Fe1 C4 2.026(3) . ? Fe1 C9 2.028(3) . ? Fe1 C6 2.033(3) . ? Fe1 C7 2.043(3) . ? Fe1 C8 2.053(3) . ? O1 C11 1.225(3) . ? N1 C11 1.357(3) . ? N1 C12 1.439(3) . ? N1 H1A 0.8600 . ? N2 N3 1.321(3) . ? N2 C13 1.364(3) . ? N2 C25 1.484(3) . ? N3 N4 1.324(3) . ? N4 C14 1.349(3) . ? N4 C15 1.437(3) . ? C1 C2 1.384(5) . ? C1 C5 1.389(5) . ? C1 H1B 0.9800 . ? C2 C3 1.388(5) . ? C2 H2A 0.9800 . ? C3 C4 1.388(5) . ? C3 H3A 0.9800 . ? C4 C5 1.388(5) . ? C4 H4A 0.9800 . ? C5 H5A 0.9800 . ? C7 C6 1.400(4) . ? C7 C8 1.414(4) . ? C7 H7A 0.9800 . ? C8 C9 1.407(4) . ? C8 H8A 0.9800 . ? C9 C10 1.431(4) . ? C9 H9A 0.9800 . ? C10 C6 1.413(4) . ? C10 C11 1.479(4) . ? C12 C13 1.490(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.358(3) . ? C15 C20 1.369(3) . ? C15 C16 1.375(3) . ? C16 C17 1.378(3) . ? C16 H16A 0.9300 . ? C17 C18 1.387(3) . ? C17 H17A 0.9300 . ? C18 C19 1.390(3) . ? C18 C21 1.526(3) . ? C21 C24 1.531(4) . ? C21 C22 1.534(4) . ? C21 C23 1.534(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C19 C20 1.373(3) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C14 H14A 0.9300 . ? C25 C26 1.504(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.375(4) . ? C26 C31 1.377(4) . ? C27 C28 1.377(4) . ? C27 H27A 0.9300 . ? C28 C29 1.372(4) . ? C28 H28A 0.9300 . ? C29 C30 1.368(4) . ? C29 H29A 0.9300 . ? C30 C31 1.373(4) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C6 H6A 0.9800 . ? 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 C3 Fe1 C1 67.34(16) . . ? C3 Fe1 C2 40.18(15) . . ? C1 Fe1 C2 40.01(16) . . ? C3 Fe1 C10 107.58(13) . . ? C1 Fe1 C10 153.25(16) . . ? C2 Fe1 C10 118.98(16) . . ? C3 Fe1 C5 67.28(15) . . ? C1 Fe1 C5 40.14(14) . . ? C2 Fe1 C5 67.34(15) . . ? C10 Fe1 C5 164.45(15) . . ? C3 Fe1 C4 40.16(13) . . ? C1 Fe1 C4 67.49(14) . . ? C2 Fe1 C4 67.56(14) . . ? C10 Fe1 C4 126.66(14) . . ? C5 Fe1 C4 40.07(13) . . ? C3 Fe1 C9 125.72(15) . . ? C1 Fe1 C9 118.67(14) . . ? C2 Fe1 C9 106.65(14) . . ? C10 Fe1 C9 41.36(10) . . ? C5 Fe1 C9 153.64(14) . . ? C4 Fe1 C9 163.65(15) . . ? C3 Fe1 C6 120.88(15) . . ? C1 Fe1 C6 164.64(18) . . ? C2 Fe1 C6 154.37(18) . . ? C10 Fe1 C6 40.76(10) . . ? C5 Fe1 C6 127.96(14) . . ? C4 Fe1 C6 109.54(13) . . ? C9 Fe1 C6 68.63(12) . . ? C3 Fe1 C7 155.48(17) . . ? C1 Fe1 C7 127.35(17) . . ? C2 Fe1 C7 163.43(19) . . ? C10 Fe1 C7 68.26(12) . . ? C5 Fe1 C7 109.89(14) . . ? C4 Fe1 C7 121.69(13) . . ? C9 Fe1 C7 68.13(12) . . ? C6 Fe1 C7 40.17(11) . . ? C3 Fe1 C8 162.70(16) . . ? C1 Fe1 C8 108.09(15) . . ? C2 Fe1 C8 125.68(17) . . ? C10 Fe1 C8 68.51(11) . . ? C5 Fe1 C8 120.83(14) . . ? C4 Fe1 C8 155.40(15) . . ? C9 Fe1 C8 40.33(10) . . ? C6 Fe1 C8 67.93(12) . . ? C7 Fe1 C8 40.38(11) . . ? C11 N1 C12 120.5(2) . . ? C11 N1 H1A 119.8 . . ? C12 N1 H1A 119.8 . . ? N3 N2 C13 112.4(2) . . ? N3 N2 C25 118.0(2) . . ? C13 N2 C25 129.6(2) . . ? N2 N3 N4 104.10(19) . . ? N3 N4 C14 112.4(2) . . ? N3 N4 C15 118.9(2) . . ? C14 N4 C15 128.6(2) . . ? C2 C1 C5 108.1(4) . . ? C2 C1 Fe1 70.0(2) . . ? C5 C1 Fe1 70.04(19) . . ? C2 C1 H1B 126.0 . . ? C5 C1 H1B 126.0 . . ? Fe1 C1 H1B 126.0 . . ? C1 C2 C3 107.8(4) . . ? C1 C2 Fe1 70.0(2) . . ? C3 C2 Fe1 69.7(2) . . ? C1 C2 H2A 126.1 . . ? C3 C2 H2A 126.1 . . ? Fe1 C2 H2A 126.1 . . ? C2 C3 C4 108.4(4) . . ? C2 C3 Fe1 70.2(2) . . ? C4 C3 Fe1 70.28(19) . . ? C2 C3 H3A 125.8 . . ? C4 C3 H3A 125.8 . . ? Fe1 C3 H3A 125.8 . . ? C3 C4 C5 107.6(3) . . ? C3 C4 Fe1 69.56(18) . . ? C5 C4 Fe1 69.94(18) . . ? C3 C4 H4A 126.2 . . ? C5 C4 H4A 126.2 . . ? Fe1 C4 H4A 126.2 . . ? C4 C5 C1 108.2(4) . . ? C4 C5 Fe1 69.99(19) . . ? C1 C5 Fe1 69.83(19) . . ? C4 C5 H5A 125.9 . . ? C1 C5 H5A 125.9 . . ? Fe1 C5 H5A 125.9 . . ? C6 C7 C8 108.5(3) . . ? C6 C7 Fe1 69.52(16) . . ? C8 C7 Fe1 70.19(17) . . ? C6 C7 H7A 125.8 . . ? C8 C7 H7A 125.8 . . ? Fe1 C7 H7A 125.8 . . ? C9 C8 C7 107.9(3) . . ? C9 C8 Fe1 68.86(16) . . ? C7 C8 Fe1 69.43(16) . . ? C9 C8 H8A 126.1 . . ? C7 C8 H8A 126.1 . . ? Fe1 C8 H8A 126.1 . . ? C8 C9 C10 108.0(3) . . ? C8 C9 Fe1 70.82(16) . . ? C10 C9 Fe1 69.22(15) . . ? C8 C9 H9A 126.0 . . ? C10 C9 H9A 126.0 . . ? Fe1 C9 H9A 126.0 . . ? C6 C10 C9 107.2(3) . . ? C6 C10 C11 123.9(3) . . ? C9 C10 C11 128.9(3) . . ? C6 C10 Fe1 69.94(16) . . ? C9 C10 Fe1 69.43(15) . . ? C11 C10 Fe1 124.89(18) . . ? O1 C11 N1 121.7(3) . . ? O1 C11 C10 122.3(3) . . ? N1 C11 C10 116.1(2) . . ? N1 C12 C13 111.2(2) . . ? N1 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N1 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 N2 105.0(2) . . ? C14 C13 C12 130.4(2) . . ? N2 C13 C12 124.2(2) . . ? C20 C15 C16 120.9(2) . . ? C20 C15 N4 118.9(2) . . ? C16 C15 N4 120.2(2) . . ? C15 C16 C17 118.3(2) . . ? C15 C16 H16A 120.9 . . ? C17 C16 H16A 120.9 . . ? C16 C17 C18 122.9(2) . . ? C16 C17 H17A 118.6 . . ? C18 C17 H17A 118.6 . . ? C17 C18 C19 116.4(2) . . ? C17 C18 C21 123.5(2) . . ? C19 C18 C21 120.1(2) . . ? C18 C21 C24 107.7(2) . . ? C18 C21 C22 112.3(2) . . ? C24 C21 C22 108.6(2) . . ? C18 C21 C23 110.2(2) . . ? C24 C21 C23 109.0(3) . . ? C22 C21 C23 109.0(2) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C19 C18 121.9(2) . . ? C20 C19 H19A 119.1 . . ? C18 C19 H19A 119.1 . . ? C15 C20 C19 119.6(2) . . ? C15 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? N4 C14 C13 106.1(2) . . ? N4 C14 H14A 127.0 . . ? C13 C14 H14A 127.0 . . ? N2 C25 C26 112.0(2) . . ? N2 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? N2 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C27 C26 C31 118.4(3) . . ? C27 C26 C25 120.4(2) . . ? C31 C26 C25 121.1(2) . . ? C26 C27 C28 121.3(3) . . ? C26 C27 H27A 119.4 . . ? C28 C27 H27A 119.4 . . ? C29 C28 C27 119.4(3) . . ? C29 C28 H28A 120.3 . . ? C27 C28 H28A 120.3 . . ? C30 C29 C28 119.8(3) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C29 C30 C31 120.4(3) . . ? C29 C30 H30A 119.8 . . ? C31 C30 H30A 119.8 . . ? C30 C31 C26 120.6(3) . . ? C30 C31 H31A 119.7 . . ? C26 C31 H31A 119.7 . . ? C7 C6 C10 108.5(3) . . ? C7 C6 Fe1 70.31(17) . . ? C10 C6 Fe1 69.31(15) . . ? C7 C6 H6A 125.8 . . ? C10 C6 H6A 125.8 . . ? Fe1 C6 H6A 125.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 N2 N3 N4 1.2(3) . . . . ? C25 N2 N3 N4 178.2(2) . . . . ? N2 N3 N4 C14 -1.0(3) . . . . ? N2 N3 N4 C15 176.7(2) . . . . ? C3 Fe1 C1 C2 37.8(2) . . . . ? C10 Fe1 C1 C2 -46.4(4) . . . . ? C5 Fe1 C1 C2 118.9(3) . . . . ? C4 Fe1 C1 C2 81.4(3) . . . . ? C9 Fe1 C1 C2 -81.8(3) . . . . ? C6 Fe1 C1 C2 163.2(4) . . . . ? C7 Fe1 C1 C2 -165.0(2) . . . . ? C8 Fe1 C1 C2 -124.4(3) . . . . ? C3 Fe1 C1 C5 -81.1(2) . . . . ? C2 Fe1 C1 C5 -118.9(3) . . . . ? C10 Fe1 C1 C5 -165.3(3) . . . . ? C4 Fe1 C1 C5 -37.5(2) . . . . ? C9 Fe1 C1 C5 159.3(2) . . . . ? C6 Fe1 C1 C5 44.3(6) . . . . ? C7 Fe1 C1 C5 76.0(3) . . . . ? C8 Fe1 C1 C5 116.7(2) . . . . ? C5 C1 C2 C3 0.3(4) . . . . ? Fe1 C1 C2 C3 -59.6(2) . . . . ? C5 C1 C2 Fe1 59.9(2) . . . . ? C3 Fe1 C2 C1 -118.8(3) . . . . ? C10 Fe1 C2 C1 158.1(2) . . . . ? C5 Fe1 C2 C1 -37.7(2) . . . . ? C4 Fe1 C2 C1 -81.2(2) . . . . ? C9 Fe1 C2 C1 115.0(2) . . . . ? C6 Fe1 C2 C1 -169.8(3) . . . . ? C7 Fe1 C2 C1 46.0(6) . . . . ? C8 Fe1 C2 C1 74.9(3) . . . . ? C1 Fe1 C2 C3 118.8(3) . . . . ? C10 Fe1 C2 C3 -83.1(3) . . . . ? C5 Fe1 C2 C3 81.1(2) . . . . ? C4 Fe1 C2 C3 37.6(2) . . . . ? C9 Fe1 C2 C3 -126.2(2) . . . . ? C6 Fe1 C2 C3 -51.0(4) . . . . ? C7 Fe1 C2 C3 164.8(4) . . . . ? C8 Fe1 C2 C3 -166.3(2) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? Fe1 C2 C3 C4 -60.1(2) . . . . ? C1 C2 C3 Fe1 59.8(3) . . . . ? C1 Fe1 C3 C2 -37.6(2) . . . . ? C10 Fe1 C3 C2 114.4(2) . . . . ? C5 Fe1 C3 C2 -81.3(3) . . . . ? C4 Fe1 C3 C2 -119.1(3) . . . . ? C9 Fe1 C3 C2 72.3(3) . . . . ? C6 Fe1 C3 C2 156.9(2) . . . . ? C7 Fe1 C3 C2 -169.6(3) . . . . ? C8 Fe1 C3 C2 40.3(6) . . . . ? C1 Fe1 C3 C4 81.5(2) . . . . ? C2 Fe1 C3 C4 119.1(3) . . . . ? C10 Fe1 C3 C4 -126.6(2) . . . . ? C5 Fe1 C3 C4 37.8(2) . . . . ? C9 Fe1 C3 C4 -168.7(2) . . . . ? C6 Fe1 C3 C4 -84.0(2) . . . . ? C7 Fe1 C3 C4 -50.5(4) . . . . ? C8 Fe1 C3 C4 159.4(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? Fe1 C3 C4 C5 -59.9(2) . . . . ? C2 C3 C4 Fe1 60.1(2) . . . . ? C1 Fe1 C4 C3 -81.1(3) . . . . ? C2 Fe1 C4 C3 -37.6(2) . . . . ? C10 Fe1 C4 C3 72.6(3) . . . . ? C5 Fe1 C4 C3 -118.6(3) . . . . ? C9 Fe1 C4 C3 34.5(5) . . . . ? C6 Fe1 C4 C3 115.1(2) . . . . ? C7 Fe1 C4 C3 157.9(2) . . . . ? C8 Fe1 C4 C3 -165.5(3) . . . . ? C3 Fe1 C4 C5 118.6(3) . . . . ? C1 Fe1 C4 C5 37.5(2) . . . . ? C2 Fe1 C4 C5 81.0(3) . . . . ? C10 Fe1 C4 C5 -168.8(2) . . . . ? C9 Fe1 C4 C5 153.2(4) . . . . ? C6 Fe1 C4 C5 -126.3(2) . . . . ? C7 Fe1 C4 C5 -83.5(2) . . . . ? C8 Fe1 C4 C5 -46.8(4) . . . . ? C3 C4 C5 C1 0.0(4) . . . . ? Fe1 C4 C5 C1 -59.6(2) . . . . ? C3 C4 C5 Fe1 59.6(2) . . . . ? C2 C1 C5 C4 -0.2(4) . . . . ? Fe1 C1 C5 C4 59.7(2) . . . . ? C2 C1 C5 Fe1 -59.9(2) . . . . ? C3 Fe1 C5 C4 -37.9(2) . . . . ? C1 Fe1 C5 C4 -119.2(3) . . . . ? C2 Fe1 C5 C4 -81.6(3) . . . . ? C10 Fe1 C5 C4 35.7(6) . . . . ? C9 Fe1 C5 C4 -163.4(3) . . . . ? C6 Fe1 C5 C4 74.4(3) . . . . ? C7 Fe1 C5 C4 116.0(2) . . . . ? C8 Fe1 C5 C4 159.3(2) . . . . ? C3 Fe1 C5 C1 81.3(3) . . . . ? C2 Fe1 C5 C1 37.6(2) . . . . ? C10 Fe1 C5 C1 154.8(5) . . . . ? C4 Fe1 C5 C1 119.2(3) . . . . ? C9 Fe1 C5 C1 -44.2(4) . . . . ? C6 Fe1 C5 C1 -166.4(2) . . . . ? C7 Fe1 C5 C1 -124.9(3) . . . . ? C8 Fe1 C5 C1 -81.6(3) . . . . ? C3 Fe1 C7 C6 -47.2(4) . . . . ? C1 Fe1 C7 C6 -167.5(2) . . . . ? C2 Fe1 C7 C6 156.9(5) . . . . ? C10 Fe1 C7 C6 37.63(16) . . . . ? C5 Fe1 C7 C6 -125.8(2) . . . . ? C4 Fe1 C7 C6 -83.0(2) . . . . ? C9 Fe1 C7 C6 82.34(18) . . . . ? C8 Fe1 C7 C6 119.6(3) . . . . ? C3 Fe1 C7 C8 -166.7(3) . . . . ? C1 Fe1 C7 C8 72.9(2) . . . . ? C2 Fe1 C7 C8 37.3(6) . . . . ? C10 Fe1 C7 C8 -81.95(18) . . . . ? C5 Fe1 C7 C8 114.6(2) . . . . ? C4 Fe1 C7 C8 157.4(2) . . . . ? C9 Fe1 C7 C8 -37.24(17) . . . . ? C6 Fe1 C7 C8 -119.6(3) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? Fe1 C7 C8 C9 58.3(2) . . . . ? C6 C7 C8 Fe1 -59.2(2) . . . . ? C3 Fe1 C8 C9 41.6(5) . . . . ? C1 Fe1 C8 C9 113.3(2) . . . . ? C2 Fe1 C8 C9 72.5(3) . . . . ? C10 Fe1 C8 C9 -38.49(17) . . . . ? C5 Fe1 C8 C9 155.4(2) . . . . ? C4 Fe1 C8 C9 -171.4(3) . . . . ? C6 Fe1 C8 C9 -82.53(19) . . . . ? C7 Fe1 C8 C9 -119.8(3) . . . . ? C3 Fe1 C8 C7 161.3(4) . . . . ? C1 Fe1 C8 C7 -126.9(2) . . . . ? C2 Fe1 C8 C7 -167.7(2) . . . . ? C10 Fe1 C8 C7 81.29(19) . . . . ? C5 Fe1 C8 C7 -84.8(2) . . . . ? C4 Fe1 C8 C7 -51.7(4) . . . . ? C9 Fe1 C8 C7 119.8(3) . . . . ? C6 Fe1 C8 C7 37.25(18) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? Fe1 C8 C9 C10 59.48(18) . . . . ? C7 C8 C9 Fe1 -58.6(2) . . . . ? C3 Fe1 C9 C8 -165.9(2) . . . . ? C1 Fe1 C9 C8 -84.4(2) . . . . ? C2 Fe1 C9 C8 -126.0(2) . . . . ? C10 Fe1 C9 C8 118.8(3) . . . . ? C5 Fe1 C9 C8 -53.6(4) . . . . ? C4 Fe1 C9 C8 167.3(4) . . . . ? C6 Fe1 C9 C8 80.65(19) . . . . ? C7 Fe1 C9 C8 37.29(18) . . . . ? C3 Fe1 C9 C10 75.3(2) . . . . ? C1 Fe1 C9 C10 156.8(2) . . . . ? C2 Fe1 C9 C10 115.2(2) . . . . ? C5 Fe1 C9 C10 -172.4(3) . . . . ? C4 Fe1 C9 C10 48.5(5) . . . . ? C6 Fe1 C9 C10 -38.14(17) . . . . ? C7 Fe1 C9 C10 -81.49(18) . . . . ? C8 Fe1 C9 C10 -118.8(3) . . . . ? C8 C9 C10 C6 -0.5(3) . . . . ? Fe1 C9 C10 C6 60.02(18) . . . . ? C8 C9 C10 C11 -179.3(3) . . . . ? Fe1 C9 C10 C11 -118.8(3) . . . . ? C8 C9 C10 Fe1 -60.5(2) . . . . ? C3 Fe1 C10 C6 117.2(2) . . . . ? C1 Fe1 C10 C6 -168.4(3) . . . . ? C2 Fe1 C10 C6 159.4(2) . . . . ? C5 Fe1 C10 C6 49.1(5) . . . . ? C4 Fe1 C10 C6 77.0(2) . . . . ? C9 Fe1 C10 C6 -118.2(2) . . . . ? C7 Fe1 C10 C6 -37.11(17) . . . . ? C8 Fe1 C10 C6 -80.69(19) . . . . ? C3 Fe1 C10 C9 -124.6(2) . . . . ? C1 Fe1 C10 C9 -50.2(4) . . . . ? C2 Fe1 C10 C9 -82.3(2) . . . . ? C5 Fe1 C10 C9 167.3(5) . . . . ? C4 Fe1 C10 C9 -164.76(19) . . . . ? C6 Fe1 C10 C9 118.2(2) . . . . ? C7 Fe1 C10 C9 81.14(18) . . . . ? C8 Fe1 C10 C9 37.56(17) . . . . ? C3 Fe1 C10 C11 -0.7(3) . . . . ? C1 Fe1 C10 C11 73.6(4) . . . . ? C2 Fe1 C10 C11 41.5(3) . . . . ? C5 Fe1 C10 C11 -68.9(6) . . . . ? C4 Fe1 C10 C11 -41.0(3) . . . . ? C9 Fe1 C10 C11 123.8(3) . . . . ? C6 Fe1 C10 C11 -118.0(3) . . . . ? C7 Fe1 C10 C11 -155.1(3) . . . . ? C8 Fe1 C10 C11 161.4(3) . . . . ? C12 N1 C11 O1 4.8(4) . . . . ? C12 N1 C11 C10 -173.6(2) . . . . ? C6 C10 C11 O1 12.2(4) . . . . ? C9 C10 C11 O1 -169.1(3) . . . . ? Fe1 C10 C11 O1 100.2(3) . . . . ? C6 C10 C11 N1 -169.4(2) . . . . ? C9 C10 C11 N1 9.2(4) . . . . ? Fe1 C10 C11 N1 -81.5(3) . . . . ? C11 N1 C12 C13 66.1(3) . . . . ? N3 N2 C13 C14 -0.9(3) . . . . ? C25 N2 C13 C14 -177.5(2) . . . . ? N3 N2 C13 C12 -174.9(2) . . . . ? C25 N2 C13 C12 8.5(4) . . . . ? N1 C12 C13 C14 -102.3(3) . . . . ? N1 C12 C13 N2 70.1(3) . . . . ? N3 N4 C15 C20 -33.2(3) . . . . ? C14 N4 C15 C20 144.1(3) . . . . ? N3 N4 C15 C16 147.2(2) . . . . ? C14 N4 C15 C16 -35.5(4) . . . . ? C20 C15 C16 C17 1.6(4) . . . . ? N4 C15 C16 C17 -178.8(2) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? C16 C17 C18 C19 -2.4(4) . . . . ? C16 C17 C18 C21 176.2(3) . . . . ? C17 C18 C21 C24 -112.4(3) . . . . ? C19 C18 C21 C24 66.1(3) . . . . ? C17 C18 C21 C22 7.1(4) . . . . ? C19 C18 C21 C22 -174.4(3) . . . . ? C17 C18 C21 C23 128.9(3) . . . . ? C19 C18 C21 C23 -52.6(3) . . . . ? C17 C18 C19 C20 1.4(4) . . . . ? C21 C18 C19 C20 -177.3(3) . . . . ? C16 C15 C20 C19 -2.6(4) . . . . ? N4 C15 C20 C19 177.8(2) . . . . ? C18 C19 C20 C15 1.1(4) . . . . ? N3 N4 C14 C13 0.5(3) . . . . ? C15 N4 C14 C13 -177.0(2) . . . . ? N2 C13 C14 N4 0.3(3) . . . . ? C12 C13 C14 N4 173.7(3) . . . . ? N3 N2 C25 C26 57.4(3) . . . . ? C13 N2 C25 C26 -126.2(3) . . . . ? N2 C25 C26 C27 99.3(3) . . . . ? N2 C25 C26 C31 -79.5(3) . . . . ? C31 C26 C27 C28 1.6(4) . . . . ? C25 C26 C27 C28 -177.3(2) . . . . ? C26 C27 C28 C29 -1.0(4) . . . . ? C27 C28 C29 C30 0.3(5) . . . . ? C28 C29 C30 C31 -0.1(5) . . . . ? C29 C30 C31 C26 0.7(5) . . . . ? C27 C26 C31 C30 -1.4(4) . . . . ? C25 C26 C31 C30 177.5(3) . . . . ? C8 C7 C6 C10 0.6(3) . . . . ? Fe1 C7 C6 C10 -58.98(18) . . . . ? C8 C7 C6 Fe1 59.6(2) . . . . ? C9 C10 C6 C7 -0.1(3) . . . . ? C11 C10 C6 C7 178.8(2) . . . . ? Fe1 C10 C6 C7 59.60(19) . . . . ? C9 C10 C6 Fe1 -59.69(18) . . . . ? C11 C10 C6 Fe1 119.2(2) . . . . ? C3 Fe1 C6 C7 159.2(2) . . . . ? C1 Fe1 C6 C7 40.4(6) . . . . ? C2 Fe1 C6 C7 -165.0(3) . . . . ? C10 Fe1 C6 C7 -119.7(2) . . . . ? C5 Fe1 C6 C7 75.2(2) . . . . ? C4 Fe1 C6 C7 116.4(2) . . . . ? C9 Fe1 C6 C7 -80.99(18) . . . . ? C8 Fe1 C6 C7 -37.44(17) . . . . ? C3 Fe1 C6 C10 -81.1(2) . . . . ? C1 Fe1 C6 C10 160.1(5) . . . . ? C2 Fe1 C6 C10 -45.3(4) . . . . ? C5 Fe1 C6 C10 -165.11(19) . . . . ? C4 Fe1 C6 C10 -123.97(19) . . . . ? C9 Fe1 C6 C10 38.69(16) . . . . ? C7 Fe1 C6 C10 119.7(2) . . . . ? C8 Fe1 C6 C10 82.24(18) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.346 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.080 # Attachment 'PF6.CIF' data_cao-4 _database_code_depnum_ccdc_archive 'CCDC 847715' #TrackingRef 'PF6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H33 Fe N4 O, F6 P' _chemical_formula_sum 'C31 H33 F6 Fe N4 O P' _chemical_formula_weight 678.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.9857(11) _cell_length_b 20.1226(11) _cell_length_c 17.2110(9) _cell_angle_alpha 90.00 _cell_angle_beta 117.802(2) _cell_angle_gamma 90.00 _cell_volume 6429.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 26.8 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.244 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.059 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27474 _diffrn_reflns_av_R_equivalents 0.1092 _diffrn_reflns_av_sigmaI/netI 0.2170 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.47 _reflns_number_total 7853 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART (Bruker, 1998)' _computing_data_reduction 'Bruker SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1998)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1998)' _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^)+(0.0615P)^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 0.00033(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7853 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2762 _refine_ls_R_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1429 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.36484(4) 0.50491(4) 0.50305(5) 0.0660(3) Uani 1 1 d . . . O1 O 0.27228(19) 0.53441(18) 0.2492(3) 0.0801(12) Uani 1 1 d . . . N1 N 0.1979(2) 0.56205(19) 0.3043(3) 0.0636(12) Uani 1 1 d . . . H1A H 0.1936 0.5756 0.3491 0.076 Uiso 1 1 calc R . . N2 N 0.1008(2) 0.6642(2) 0.1551(3) 0.0600(12) Uani 1 1 d . . . N3 N 0.0968(2) 0.6997(2) 0.0879(3) 0.0603(12) Uani 1 1 d . . . N4 N 0.11704(19) 0.6571(2) 0.0450(3) 0.0549(11) Uani 1 1 d . . . C24 C 0.1146(4) 0.6964(3) -0.3319(4) 0.115(2) Uani 1 1 d . . . H24A H 0.1502 0.6620 -0.3072 0.173 Uiso 1 1 calc R . . H24B H 0.1170 0.7158 -0.3814 0.173 Uiso 1 1 calc R . . H24C H 0.0676 0.6778 -0.3505 0.173 Uiso 1 1 calc R . . C25 C 0.0775(3) 0.6958(3) 0.2150(3) 0.0716(16) Uani 1 1 d . . . H25A H 0.0871 0.6658 0.2634 0.086 Uiso 1 1 calc R . . H25B H 0.0260 0.7037 0.1838 0.086 Uiso 1 1 calc R . . C6 C 0.3247(3) 0.5984(2) 0.4723(4) 0.0679(15) Uani 1 1 d . . . H6A H 0.2822 0.6153 0.4754 0.082 Uiso 1 1 calc R . . C10 C 0.3249(3) 0.5672(2) 0.3985(4) 0.0592(14) Uani 1 1 d . . . C11 C 0.2643(3) 0.5524(3) 0.3116(4) 0.0608(15) Uani 1 1 d . . . C12 C 0.1341(3) 0.5498(2) 0.2221(3) 0.0647(15) Uani 1 1 d . . . H12A H 0.0925 0.5486 0.2324 0.078 Uiso 1 1 calc R . . H12B H 0.1383 0.5066 0.1998 0.078 Uiso 1 1 calc R . . C13 C 0.1227(2) 0.6010(3) 0.1550(4) 0.0545(14) Uani 1 1 d . . . C15 C 0.1200(2) 0.6798(3) -0.0330(4) 0.0515(13) Uani 1 1 d . . . C20 C 0.0966(3) 0.6387(3) -0.1037(4) 0.0690(16) Uani 1 1 d . . . H20A H 0.0782 0.5968 -0.1029 0.083 Uiso 1 1 calc R . . C19 C 0.1011(3) 0.6612(3) -0.1772(4) 0.0679(15) Uani 1 1 d . . . H19A H 0.0860 0.6332 -0.2256 0.082 Uiso 1 1 calc R . . C18 C 0.1269(3) 0.7231(3) -0.1815(4) 0.0572(14) Uani 1 1 d . . . C21 C 0.1289(3) 0.7496(3) -0.2631(4) 0.0701(16) Uani 1 1 d . . . C23 C 0.2019(3) 0.7824(3) -0.2391(4) 0.106(2) Uani 1 1 d . . . H23A H 0.2394 0.7497 -0.2145 0.159 Uiso 1 1 calc R . . H23B H 0.2107 0.8171 -0.1969 0.159 Uiso 1 1 calc R . . H23C H 0.2010 0.8010 -0.2910 0.159 Uiso 1 1 calc R . . C22 C 0.0707(3) 0.8038(3) -0.3048(4) 0.128(3) Uani 1 1 d . . . H22A H 0.0241 0.7848 -0.3217 0.193 Uiso 1 1 calc R . . H22B H 0.0721 0.8216 -0.3557 0.193 Uiso 1 1 calc R . . H22C H 0.0796 0.8387 -0.2630 0.193 Uiso 1 1 calc R . . C17 C 0.1491(3) 0.7633(3) -0.1083(4) 0.0708(16) Uani 1 1 d . . . H17A H 0.1663 0.8057 -0.1093 0.085 Uiso 1 1 calc R . . C16 C 0.1464(3) 0.7419(3) -0.0338(3) 0.0629(15) Uani 1 1 d . . . H16A H 0.1622 0.7693 0.0153 0.075 Uiso 1 1 calc R . . C14 C 0.1331(2) 0.5972(3) 0.0829(4) 0.0565(14) Uani 1 1 d . . . H14A H 0.1485 0.5602 0.0638 0.068 Uiso 1 1 calc R . . C26 C 0.1157(3) 0.7602(3) 0.2507(3) 0.0548(13) Uani 1 1 d . . . C9 C 0.3975(3) 0.5504(2) 0.4217(4) 0.0686(16) Uani 1 1 d . . . H9A H 0.4141 0.5281 0.3838 0.082 Uiso 1 1 calc R . . C8 C 0.4404(3) 0.5707(3) 0.5078(5) 0.0812(18) Uani 1 1 d . . . H8A H 0.4926 0.5644 0.5411 0.097 Uiso 1 1 calc R . . C7 C 0.3966(3) 0.6010(3) 0.5407(4) 0.0761(17) Uani 1 1 d . . . H7A H 0.4129 0.6198 0.5995 0.091 Uiso 1 1 calc R . . C5 C 0.3017(7) 0.4226(5) 0.4697(7) 0.138(4) Uani 1 1 d . . . H5A H 0.2594 0.4134 0.4133 0.166 Uiso 1 1 calc R . . C4 C 0.3028(6) 0.4530(4) 0.5402(11) 0.125(4) Uani 1 1 d . . . H4A H 0.2602 0.4708 0.5422 0.150 Uiso 1 1 calc R . . C3 C 0.3698(8) 0.4554(4) 0.6074(6) 0.116(3) Uani 1 1 d . . . H3A H 0.3841 0.4735 0.6661 0.140 Uiso 1 1 calc R . . C2 C 0.4140(4) 0.4251(5) 0.5787(9) 0.112(3) Uani 1 1 d . . . H2A H 0.4661 0.4187 0.6133 0.135 Uiso 1 1 calc R . . C1 C 0.3729(9) 0.4057(3) 0.4943(10) 0.123(3) Uani 1 1 d . . . H1B H 0.3901 0.3827 0.4575 0.147 Uiso 1 1 calc R . . C31 C 0.1762(3) 0.7605(3) 0.3299(4) 0.0856(18) Uiso 1 1 d . . . H31A H 0.1908 0.7214 0.3625 0.103 Uiso 1 1 calc R . . C30 C 0.2165(3) 0.8179(3) 0.3628(4) 0.107(2) Uiso 1 1 d . . . H30A H 0.2584 0.8178 0.4162 0.128 Uiso 1 1 calc R . . C28 C 0.1351(4) 0.8783(3) 0.2414(5) 0.119(2) Uiso 1 1 d . . . H28A H 0.1217 0.9188 0.2122 0.142 Uiso 1 1 calc R . . C29 C 0.1935(3) 0.8726(3) 0.3157(4) 0.105(2) Uiso 1 1 d . . . H29A H 0.2215 0.9106 0.3377 0.126 Uiso 1 1 calc R . . C27 C 0.0913(3) 0.8188(3) 0.2052(4) 0.102(2) Uiso 1 1 d . . . H27A H 0.0483 0.8204 0.1531 0.122 Uiso 1 1 calc R . . P1 P 0.09171(7) 0.57595(8) 0.44688(10) 0.0643(5) Uani 1 1 d . . . F1 F 0.13903(17) 0.56153(16) 0.5476(2) 0.1124(12) Uani 1 1 d . . . F2 F 0.04497(16) 0.59014(15) 0.34507(18) 0.0952(10) Uani 1 1 d . . . F3 F 0.04998(19) 0.63088(18) 0.4676(2) 0.1226(13) Uani 1 1 d . . . F4 F 0.03571(16) 0.52196(17) 0.4408(2) 0.1084(11) Uani 1 1 d . . . F5 F 0.13372(18) 0.51918(15) 0.4249(2) 0.1108(12) Uani 1 1 d . . . F6 F 0.14889(17) 0.62655(16) 0.4474(2) 0.1220(13) 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 0.0567(5) 0.0685(6) 0.0770(6) 0.0172(5) 0.0346(4) 0.0079(4) O1 0.087(3) 0.095(3) 0.070(3) -0.001(2) 0.047(2) 0.011(2) N1 0.061(3) 0.081(3) 0.046(3) -0.001(2) 0.023(2) 0.008(2) N2 0.073(3) 0.053(3) 0.062(3) -0.009(3) 0.039(3) -0.013(2) N3 0.070(3) 0.049(3) 0.074(3) -0.005(3) 0.044(3) -0.002(2) N4 0.059(3) 0.052(3) 0.057(3) -0.002(3) 0.031(2) -0.001(2) C24 0.162(6) 0.122(6) 0.095(5) -0.026(5) 0.087(5) -0.045(5) C25 0.091(4) 0.072(4) 0.082(4) -0.022(4) 0.065(4) -0.016(3) C6 0.066(4) 0.069(4) 0.073(4) -0.003(3) 0.036(4) 0.005(3) C10 0.059(4) 0.053(4) 0.072(4) 0.018(3) 0.036(3) 0.012(3) C11 0.071(4) 0.055(4) 0.061(4) 0.015(3) 0.035(4) 0.011(3) C12 0.068(4) 0.062(4) 0.068(4) 0.000(3) 0.035(3) -0.001(3) C13 0.052(3) 0.053(4) 0.059(4) 0.003(3) 0.026(3) 0.000(3) C15 0.062(3) 0.046(4) 0.051(4) 0.004(3) 0.030(3) 0.000(3) C20 0.094(4) 0.059(4) 0.057(4) -0.002(4) 0.037(4) -0.006(3) C19 0.085(4) 0.053(4) 0.062(4) -0.015(3) 0.032(3) -0.006(3) C18 0.063(3) 0.050(4) 0.063(4) -0.005(3) 0.034(3) 0.004(3) C21 0.086(4) 0.066(4) 0.076(4) 0.002(4) 0.053(4) -0.008(3) C23 0.109(5) 0.135(6) 0.099(5) 0.002(4) 0.069(4) -0.030(4) C22 0.127(6) 0.172(7) 0.106(5) 0.067(5) 0.071(5) 0.056(6) C17 0.095(4) 0.051(4) 0.079(4) 0.001(4) 0.051(4) -0.012(3) C16 0.079(4) 0.057(4) 0.055(4) -0.009(3) 0.033(3) -0.009(3) C14 0.061(3) 0.046(4) 0.066(4) 0.002(3) 0.032(3) 0.003(3) C26 0.066(3) 0.055(4) 0.049(3) -0.010(3) 0.032(3) -0.001(3) C9 0.073(4) 0.056(4) 0.083(5) 0.015(4) 0.041(4) 0.009(3) C8 0.065(4) 0.081(5) 0.105(5) 0.016(4) 0.045(4) 0.003(4) C7 0.080(4) 0.071(4) 0.069(4) -0.008(3) 0.028(4) -0.013(3) C5 0.157(11) 0.086(7) 0.110(8) 0.023(6) 0.011(7) -0.064(7) C4 0.077(6) 0.105(7) 0.206(11) 0.066(8) 0.077(8) 0.018(5) C3 0.184(9) 0.095(6) 0.098(7) 0.033(5) 0.089(8) 0.015(7) C2 0.072(5) 0.085(6) 0.170(9) 0.062(6) 0.048(7) 0.020(5) C1 0.204(11) 0.054(5) 0.178(11) 0.002(7) 0.145(10) -0.008(7) P1 0.0569(9) 0.0710(11) 0.0631(11) 0.0106(9) 0.0264(8) 0.0035(9) F1 0.105(2) 0.132(3) 0.068(2) 0.019(2) 0.013(2) 0.003(2) F2 0.097(2) 0.120(3) 0.055(2) 0.011(2) 0.0236(18) 0.013(2) F3 0.141(3) 0.133(3) 0.094(3) -0.005(2) 0.054(2) 0.063(3) F4 0.086(2) 0.127(3) 0.118(3) 0.010(2) 0.053(2) -0.031(2) F5 0.109(3) 0.089(2) 0.159(3) 0.013(2) 0.084(3) 0.030(2) F6 0.104(3) 0.104(3) 0.139(3) 0.024(2) 0.041(2) -0.038(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 C4 1.992(7) . ? Fe1 C3 2.014(6) . ? Fe1 C1 2.015(7) . ? Fe1 C2 2.021(6) . ? Fe1 C10 2.026(5) . ? Fe1 C6 2.028(5) . ? Fe1 C5 2.030(7) . ? Fe1 C8 2.038(5) . ? Fe1 C9 2.041(5) . ? Fe1 C7 2.049(5) . ? O1 C11 1.217(5) . ? N1 C11 1.353(6) . ? N1 C12 1.445(5) . ? N1 H1A 0.8600 . ? N2 N3 1.328(5) . ? N2 C13 1.351(6) . ? N2 C25 1.475(5) . ? N3 N4 1.324(5) . ? N4 C14 1.336(5) . ? N4 C15 1.446(6) . ? C24 C21 1.518(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.498(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C6 C7 1.416(6) . ? C6 C10 1.418(6) . ? C6 H6A 0.9800 . ? C10 C9 1.423(6) . ? C10 C11 1.473(7) . ? C12 C13 1.483(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.359(6) . ? C15 C20 1.360(6) . ? C15 C16 1.371(6) . ? C20 C19 1.387(6) . ? C20 H20A 0.9300 . ? C19 C18 1.373(6) . ? C19 H19A 0.9300 . ? C18 C17 1.384(6) . ? C18 C21 1.522(7) . ? C21 C23 1.536(6) . ? C21 C22 1.543(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C17 C16 1.379(6) . ? C17 H17A 0.9300 . ? C16 H16A 0.9300 . ? C14 H14A 0.9300 . ? C26 C31 1.362(6) . ? C26 C27 1.374(7) . ? C9 C8 1.390(7) . ? C9 H9A 0.9800 . ? C8 C7 1.422(7) . ? C8 H8A 0.9800 . ? C7 H7A 0.9800 . ? C5 C4 1.349(10) . ? C5 C1 1.392(11) . ? C5 H5A 0.9800 . ? C4 C3 1.340(10) . ? C4 H4A 0.9800 . ? C3 C2 1.381(9) . ? C3 H3A 0.9800 . ? C2 C1 1.356(10) . ? C2 H2A 0.9800 . ? C1 H1B 0.9800 . ? C31 C30 1.387(7) . ? C31 H31A 0.9300 . ? C30 C29 1.318(7) . ? C30 H30A 0.9300 . ? C28 C29 1.299(7) . ? C28 C27 1.460(7) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? C27 H27A 0.9300 . ? P1 F3 1.551(3) . ? P1 F4 1.568(3) . ? P1 F6 1.571(3) . ? P1 F1 1.572(3) . ? P1 F2 1.585(3) . ? P1 F5 1.593(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 Fe1 C3 39.1(3) . . ? C4 Fe1 C1 66.1(3) . . ? C3 Fe1 C1 66.8(3) . . ? C4 Fe1 C2 65.8(3) . . ? C3 Fe1 C2 40.0(3) . . ? C1 Fe1 C2 39.3(3) . . ? C4 Fe1 C10 123.2(4) . . ? C3 Fe1 C10 157.8(4) . . ? C1 Fe1 C10 124.1(5) . . ? C2 Fe1 C10 159.9(5) . . ? C4 Fe1 C6 108.5(3) . . ? C3 Fe1 C6 122.3(3) . . ? C1 Fe1 C6 159.8(5) . . ? C2 Fe1 C6 158.5(5) . . ? C10 Fe1 C6 40.97(18) . . ? C4 Fe1 C5 39.2(3) . . ? C3 Fe1 C5 66.7(4) . . ? C1 Fe1 C5 40.3(3) . . ? C2 Fe1 C5 66.6(3) . . ? C10 Fe1 C5 108.0(3) . . ? C6 Fe1 C5 123.1(5) . . ? C4 Fe1 C8 160.1(5) . . ? C3 Fe1 C8 124.8(4) . . ? C1 Fe1 C8 123.8(4) . . ? C2 Fe1 C8 109.7(3) . . ? C10 Fe1 C8 68.0(2) . . ? C6 Fe1 C8 68.2(2) . . ? C5 Fe1 C8 159.2(6) . . ? C4 Fe1 C9 159.1(5) . . ? C3 Fe1 C9 160.1(5) . . ? C1 Fe1 C9 109.0(3) . . ? C2 Fe1 C9 124.4(4) . . ? C10 Fe1 C9 40.97(18) . . ? C6 Fe1 C9 68.7(2) . . ? C5 Fe1 C9 123.8(4) . . ? C8 Fe1 C9 39.85(19) . . ? C4 Fe1 C7 123.9(4) . . ? C3 Fe1 C7 108.1(3) . . ? C1 Fe1 C7 158.8(5) . . ? C2 Fe1 C7 123.6(4) . . ? C10 Fe1 C7 68.6(2) . . ? C6 Fe1 C7 40.65(19) . . ? C5 Fe1 C7 158.8(6) . . ? C8 Fe1 C7 40.74(19) . . ? C9 Fe1 C7 68.3(2) . . ? C11 N1 C12 120.6(4) . . ? C11 N1 H1A 119.7 . . ? C12 N1 H1A 119.7 . . ? N3 N2 C13 112.9(4) . . ? N3 N2 C25 118.0(5) . . ? C13 N2 C25 129.0(5) . . ? N4 N3 N2 103.4(4) . . ? N3 N4 C14 112.6(4) . . ? N3 N4 C15 118.5(5) . . ? C14 N4 C15 128.9(5) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 111.8(4) . . ? N2 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? N2 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? C7 C6 C10 108.3(5) . . ? C7 C6 Fe1 70.5(3) . . ? C10 C6 Fe1 69.4(3) . . ? C7 C6 H6A 125.9 . . ? C10 C6 H6A 125.9 . . ? Fe1 C6 H6A 125.9 . . ? C6 C10 C9 107.7(5) . . ? C6 C10 C11 129.6(5) . . ? C9 C10 C11 122.8(5) . . ? C6 C10 Fe1 69.6(3) . . ? C9 C10 Fe1 70.1(3) . . ? C11 C10 Fe1 125.5(4) . . ? O1 C11 N1 121.4(5) . . ? O1 C11 C10 123.2(5) . . ? N1 C11 C10 115.4(5) . . ? N1 C12 C13 112.5(4) . . ? N1 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N1 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? N2 C13 C14 104.7(5) . . ? N2 C13 C12 125.8(5) . . ? C14 C13 C12 129.4(5) . . ? C20 C15 C16 121.6(5) . . ? C20 C15 N4 119.0(5) . . ? C16 C15 N4 119.4(5) . . ? C15 C20 C19 117.9(5) . . ? C15 C20 H20A 121.0 . . ? C19 C20 H20A 121.0 . . ? C18 C19 C20 122.7(5) . . ? C18 C19 H19A 118.6 . . ? C20 C19 H19A 118.6 . . ? C19 C18 C17 117.2(5) . . ? C19 C18 C21 123.3(5) . . ? C17 C18 C21 119.5(5) . . ? C24 C21 C18 113.1(5) . . ? C24 C21 C23 108.8(5) . . ? C18 C21 C23 110.9(5) . . ? C24 C21 C22 108.0(5) . . ? C18 C21 C22 108.7(5) . . ? C23 C21 C22 107.1(5) . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C17 C18 121.4(5) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 119.3 . . ? C15 C16 C17 119.2(5) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? N4 C14 C13 106.5(5) . . ? N4 C14 H14A 126.8 . . ? C13 C14 H14A 126.8 . . ? C31 C26 C27 119.6(5) . . ? C31 C26 C25 118.9(5) . . ? C27 C26 C25 121.5(5) . . ? C8 C9 C10 107.8(5) . . ? C8 C9 Fe1 70.0(3) . . ? C10 C9 Fe1 68.9(3) . . ? C8 C9 H9A 126.1 . . ? C10 C9 H9A 126.1 . . ? Fe1 C9 H9A 126.1 . . ? C9 C8 C7 109.4(5) . . ? C9 C8 Fe1 70.2(3) . . ? C7 C8 Fe1 70.0(3) . . ? C9 C8 H8A 125.3 . . ? C7 C8 H8A 125.3 . . ? Fe1 C8 H8A 125.3 . . ? C6 C7 C8 106.8(5) . . ? C6 C7 Fe1 68.9(3) . . ? C8 C7 Fe1 69.2(3) . . ? C6 C7 H7A 126.6 . . ? C8 C7 H7A 126.6 . . ? Fe1 C7 H7A 126.6 . . ? C4 C5 C1 105.7(9) . . ? C4 C5 Fe1 68.9(5) . . ? C1 C5 Fe1 69.3(5) . . ? C4 C5 H5A 127.1 . . ? C1 C5 H5A 127.1 . . ? Fe1 C5 H5A 127.1 . . ? C3 C4 C5 111.4(9) . . ? C3 C4 Fe1 71.3(4) . . ? C5 C4 Fe1 71.9(5) . . ? C3 C4 H4A 124.3 . . ? C5 C4 H4A 124.3 . . ? Fe1 C4 H4A 124.3 . . ? C4 C3 C2 106.5(8) . . ? C4 C3 Fe1 69.6(4) . . ? C2 C3 Fe1 70.3(4) . . ? C4 C3 H3A 126.7 . . ? C2 C3 H3A 126.7 . . ? Fe1 C3 H3A 126.7 . . ? C1 C2 C3 108.2(8) . . ? C1 C2 Fe1 70.1(5) . . ? C3 C2 Fe1 69.7(4) . . ? C1 C2 H2A 125.9 . . ? C3 C2 H2A 125.9 . . ? Fe1 C2 H2A 125.9 . . ? C2 C1 C5 108.2(9) . . ? C2 C1 Fe1 70.6(5) . . ? C5 C1 Fe1 70.5(5) . . ? C2 C1 H1B 125.9 . . ? C5 C1 H1B 125.9 . . ? Fe1 C1 H1B 125.9 . . ? C26 C31 C30 121.1(6) . . ? C26 C31 H31A 119.4 . . ? C30 C31 H31A 119.4 . . ? C29 C30 C31 117.8(7) . . ? C29 C30 H30A 121.1 . . ? C31 C30 H30A 121.1 . . ? C29 C28 C27 117.7(7) . . ? C29 C28 H28A 121.1 . . ? C27 C28 H28A 121.1 . . ? C28 C29 C30 125.8(7) . . ? C28 C29 H29A 117.1 . . ? C30 C29 H29A 117.1 . . ? C26 C27 C28 117.8(6) . . ? C26 C27 H27A 121.1 . . ? C28 C27 H27A 121.1 . . ? F3 P1 F4 91.3(2) . . ? F3 P1 F6 92.8(2) . . ? F4 P1 F6 175.3(2) . . ? F3 P1 F1 90.71(19) . . ? F4 P1 F1 90.78(19) . . ? F6 P1 F1 91.48(19) . . ? F3 P1 F2 90.05(18) . . ? F4 P1 F2 89.61(18) . . ? F6 P1 F2 88.08(19) . . ? F1 P1 F2 179.1(2) . . ? F3 P1 F5 179.3(2) . . ? F4 P1 F5 88.17(19) . . ? F6 P1 F5 87.71(19) . . ? F1 P1 F5 89.7(2) . . ? F2 P1 F5 89.54(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 N2 N3 N4 -0.1(5) . . . . ? C25 N2 N3 N4 -176.6(4) . . . . ? N2 N3 N4 C14 0.1(5) . . . . ? N2 N3 N4 C15 -179.2(4) . . . . ? N3 N2 C25 C26 -54.2(6) . . . . ? C13 N2 C25 C26 130.0(5) . . . . ? C4 Fe1 C6 C7 120.9(6) . . . . ? C3 Fe1 C6 C7 80.1(6) . . . . ? C1 Fe1 C6 C7 -168.4(8) . . . . ? C2 Fe1 C6 C7 50.3(8) . . . . ? C10 Fe1 C6 C7 -119.3(5) . . . . ? C5 Fe1 C6 C7 161.7(6) . . . . ? C8 Fe1 C6 C7 -38.1(3) . . . . ? C9 Fe1 C6 C7 -81.1(3) . . . . ? C4 Fe1 C6 C10 -119.8(6) . . . . ? C3 Fe1 C6 C10 -160.6(5) . . . . ? C1 Fe1 C6 C10 -49.1(9) . . . . ? C2 Fe1 C6 C10 169.6(6) . . . . ? C5 Fe1 C6 C10 -79.1(6) . . . . ? C8 Fe1 C6 C10 81.1(3) . . . . ? C9 Fe1 C6 C10 38.1(3) . . . . ? C7 Fe1 C6 C10 119.3(5) . . . . ? C7 C6 C10 C9 0.0(6) . . . . ? Fe1 C6 C10 C9 -60.0(3) . . . . ? C7 C6 C10 C11 179.7(5) . . . . ? Fe1 C6 C10 C11 119.7(5) . . . . ? C7 C6 C10 Fe1 60.0(4) . . . . ? C4 Fe1 C10 C6 79.8(6) . . . . ? C3 Fe1 C10 C6 48.1(9) . . . . ? C1 Fe1 C10 C6 161.6(5) . . . . ? C2 Fe1 C10 C6 -168.9(7) . . . . ? C5 Fe1 C10 C6 120.2(6) . . . . ? C8 Fe1 C10 C6 -81.6(3) . . . . ? C9 Fe1 C10 C6 -118.7(5) . . . . ? C7 Fe1 C10 C6 -37.6(3) . . . . ? C4 Fe1 C10 C9 -161.6(6) . . . . ? C3 Fe1 C10 C9 166.8(8) . . . . ? C1 Fe1 C10 C9 -79.7(6) . . . . ? C2 Fe1 C10 C9 -50.2(9) . . . . ? C6 Fe1 C10 C9 118.7(5) . . . . ? C5 Fe1 C10 C9 -121.2(7) . . . . ? C8 Fe1 C10 C9 37.1(3) . . . . ? C7 Fe1 C10 C9 81.1(3) . . . . ? C4 Fe1 C10 C11 -44.9(7) . . . . ? C3 Fe1 C10 C11 -76.6(10) . . . . ? C1 Fe1 C10 C11 36.9(7) . . . . ? C2 Fe1 C10 C11 66.4(9) . . . . ? C6 Fe1 C10 C11 -124.7(6) . . . . ? C5 Fe1 C10 C11 -4.5(8) . . . . ? C8 Fe1 C10 C11 153.7(6) . . . . ? C9 Fe1 C10 C11 116.6(6) . . . . ? C7 Fe1 C10 C11 -162.3(6) . . . . ? C12 N1 C11 O1 1.4(8) . . . . ? C12 N1 C11 C10 179.5(4) . . . . ? C6 C10 C11 O1 168.6(5) . . . . ? C9 C10 C11 O1 -11.7(8) . . . . ? Fe1 C10 C11 O1 -99.4(6) . . . . ? C6 C10 C11 N1 -9.5(8) . . . . ? C9 C10 C11 N1 170.2(4) . . . . ? Fe1 C10 C11 N1 82.4(6) . . . . ? C11 N1 C12 C13 -72.6(6) . . . . ? N3 N2 C13 C14 0.2(5) . . . . ? C25 N2 C13 C14 176.2(4) . . . . ? N3 N2 C13 C12 178.5(4) . . . . ? C25 N2 C13 C12 -5.5(8) . . . . ? N1 C12 C13 N2 -72.4(6) . . . . ? N1 C12 C13 C14 105.4(6) . . . . ? N3 N4 C15 C20 -139.7(5) . . . . ? C14 N4 C15 C20 41.2(7) . . . . ? N3 N4 C15 C16 40.6(6) . . . . ? C14 N4 C15 C16 -138.5(5) . . . . ? C16 C15 C20 C19 0.8(8) . . . . ? N4 C15 C20 C19 -178.9(4) . . . . ? C15 C20 C19 C18 -1.0(8) . . . . ? C20 C19 C18 C17 0.3(8) . . . . ? C20 C19 C18 C21 -177.1(5) . . . . ? C19 C18 C21 C24 -12.0(7) . . . . ? C17 C18 C21 C24 170.6(5) . . . . ? C19 C18 C21 C23 -134.5(5) . . . . ? C17 C18 C21 C23 48.1(7) . . . . ? C19 C18 C21 C22 108.0(6) . . . . ? C17 C18 C21 C22 -69.4(6) . . . . ? C19 C18 C17 C16 0.8(7) . . . . ? C21 C18 C17 C16 178.3(5) . . . . ? C20 C15 C16 C17 0.2(7) . . . . ? N4 C15 C16 C17 179.9(4) . . . . ? C18 C17 C16 C15 -1.0(8) . . . . ? N3 N4 C14 C13 0.0(5) . . . . ? C15 N4 C14 C13 179.2(4) . . . . ? N2 C13 C14 N4 -0.1(5) . . . . ? C12 C13 C14 N4 -178.3(4) . . . . ? N2 C25 C26 C31 -94.5(6) . . . . ? N2 C25 C26 C27 85.2(6) . . . . ? C6 C10 C9 C8 0.3(6) . . . . ? C11 C10 C9 C8 -179.5(5) . . . . ? Fe1 C10 C9 C8 -59.4(4) . . . . ? C6 C10 C9 Fe1 59.7(4) . . . . ? C11 C10 C9 Fe1 -120.1(5) . . . . ? C4 Fe1 C9 C8 167.1(8) . . . . ? C3 Fe1 C9 C8 -46.0(9) . . . . ? C1 Fe1 C9 C8 -120.3(6) . . . . ? C2 Fe1 C9 C8 -79.4(6) . . . . ? C10 Fe1 C9 C8 119.3(5) . . . . ? C6 Fe1 C9 C8 81.1(3) . . . . ? C5 Fe1 C9 C8 -162.5(6) . . . . ? C7 Fe1 C9 C8 37.3(3) . . . . ? C4 Fe1 C9 C10 47.8(9) . . . . ? C3 Fe1 C9 C10 -165.3(7) . . . . ? C1 Fe1 C9 C10 120.5(6) . . . . ? C2 Fe1 C9 C10 161.3(5) . . . . ? C6 Fe1 C9 C10 -38.1(3) . . . . ? C5 Fe1 C9 C10 78.2(6) . . . . ? C8 Fe1 C9 C10 -119.3(5) . . . . ? C7 Fe1 C9 C10 -82.0(3) . . . . ? C10 C9 C8 C7 -0.5(6) . . . . ? Fe1 C9 C8 C7 -59.2(4) . . . . ? C10 C9 C8 Fe1 58.8(4) . . . . ? C4 Fe1 C8 C9 -166.5(8) . . . . ? C3 Fe1 C8 C9 162.6(5) . . . . ? C1 Fe1 C8 C9 79.1(6) . . . . ? C2 Fe1 C8 C9 120.5(6) . . . . ? C10 Fe1 C8 C9 -38.1(3) . . . . ? C6 Fe1 C8 C9 -82.4(3) . . . . ? C5 Fe1 C8 C9 44.7(10) . . . . ? C7 Fe1 C8 C9 -120.4(5) . . . . ? C4 Fe1 C8 C7 -46.0(9) . . . . ? C3 Fe1 C8 C7 -76.9(5) . . . . ? C1 Fe1 C8 C7 -160.4(6) . . . . ? C2 Fe1 C8 C7 -119.0(6) . . . . ? C10 Fe1 C8 C7 82.4(3) . . . . ? C6 Fe1 C8 C7 38.0(3) . . . . ? C5 Fe1 C8 C7 165.1(9) . . . . ? C9 Fe1 C8 C7 120.4(5) . . . . ? C10 C6 C7 C8 -0.3(6) . . . . ? Fe1 C6 C7 C8 59.1(4) . . . . ? C10 C6 C7 Fe1 -59.4(4) . . . . ? C9 C8 C7 C6 0.5(6) . . . . ? Fe1 C8 C7 C6 -58.8(4) . . . . ? C9 C8 C7 Fe1 59.3(4) . . . . ? C4 Fe1 C7 C6 -78.6(6) . . . . ? C3 Fe1 C7 C6 -118.8(5) . . . . ? C1 Fe1 C7 C6 168.9(8) . . . . ? C2 Fe1 C7 C6 -160.2(5) . . . . ? C10 Fe1 C7 C6 37.9(3) . . . . ? C5 Fe1 C7 C6 -46.8(10) . . . . ? C8 Fe1 C7 C6 118.6(5) . . . . ? C9 Fe1 C7 C6 82.1(3) . . . . ? C4 Fe1 C7 C8 162.8(5) . . . . ? C3 Fe1 C7 C8 122.7(6) . . . . ? C1 Fe1 C7 C8 50.4(10) . . . . ? C2 Fe1 C7 C8 81.3(6) . . . . ? C10 Fe1 C7 C8 -80.7(4) . . . . ? C6 Fe1 C7 C8 -118.6(5) . . . . ? C5 Fe1 C7 C8 -165.4(8) . . . . ? C9 Fe1 C7 C8 -36.5(3) . . . . ? C3 Fe1 C5 C4 36.0(5) . . . . ? C1 Fe1 C5 C4 117.1(9) . . . . ? C2 Fe1 C5 C4 79.8(6) . . . . ? C10 Fe1 C5 C4 -120.9(7) . . . . ? C6 Fe1 C5 C4 -78.3(7) . . . . ? C8 Fe1 C5 C4 163.8(7) . . . . ? C9 Fe1 C5 C4 -163.4(6) . . . . ? C7 Fe1 C5 C4 -43.8(12) . . . . ? C4 Fe1 C5 C1 -117.1(9) . . . . ? C3 Fe1 C5 C1 -81.1(6) . . . . ? C2 Fe1 C5 C1 -37.3(6) . . . . ? C10 Fe1 C5 C1 121.9(8) . . . . ? C6 Fe1 C5 C1 164.5(7) . . . . ? C8 Fe1 C5 C1 46.7(12) . . . . ? C9 Fe1 C5 C1 79.5(8) . . . . ? C7 Fe1 C5 C1 -160.9(8) . . . . ? C1 C5 C4 C3 -0.8(10) . . . . ? Fe1 C5 C4 C3 -60.7(6) . . . . ? C1 C5 C4 Fe1 59.9(6) . . . . ? C1 Fe1 C4 C3 82.1(6) . . . . ? C2 Fe1 C4 C3 38.9(5) . . . . ? C10 Fe1 C4 C3 -161.7(5) . . . . ? C6 Fe1 C4 C3 -118.8(6) . . . . ? C5 Fe1 C4 C3 121.0(9) . . . . ? C8 Fe1 C4 C3 -42.0(11) . . . . ? C9 Fe1 C4 C3 162.8(6) . . . . ? C7 Fe1 C4 C3 -76.5(7) . . . . ? C3 Fe1 C4 C5 -121.0(9) . . . . ? C1 Fe1 C4 C5 -39.0(6) . . . . ? C2 Fe1 C4 C5 -82.2(6) . . . . ? C10 Fe1 C4 C5 77.3(8) . . . . ? C6 Fe1 C4 C5 120.2(7) . . . . ? C8 Fe1 C4 C5 -163.1(8) . . . . ? C9 Fe1 C4 C5 41.8(12) . . . . ? C7 Fe1 C4 C5 162.5(7) . . . . ? C5 C4 C3 C2 0.1(10) . . . . ? Fe1 C4 C3 C2 -61.0(5) . . . . ? C5 C4 C3 Fe1 61.0(6) . . . . ? C1 Fe1 C3 C4 -80.1(6) . . . . ? C2 Fe1 C3 C4 -117.1(8) . . . . ? C10 Fe1 C3 C4 44.2(11) . . . . ? C6 Fe1 C3 C4 79.4(7) . . . . ? C5 Fe1 C3 C4 -36.1(6) . . . . ? C8 Fe1 C3 C4 163.9(6) . . . . ? C9 Fe1 C3 C4 -162.0(8) . . . . ? C7 Fe1 C3 C4 121.9(7) . . . . ? C4 Fe1 C3 C2 117.1(8) . . . . ? C1 Fe1 C3 C2 36.9(5) . . . . ? C10 Fe1 C3 C2 161.2(7) . . . . ? C6 Fe1 C3 C2 -163.5(6) . . . . ? C5 Fe1 C3 C2 80.9(5) . . . . ? C8 Fe1 C3 C2 -79.1(7) . . . . ? C9 Fe1 C3 C2 -44.9(11) . . . . ? C7 Fe1 C3 C2 -121.0(7) . . . . ? C4 C3 C2 C1 0.7(9) . . . . ? Fe1 C3 C2 C1 -59.8(6) . . . . ? C4 C3 C2 Fe1 60.5(5) . . . . ? C4 Fe1 C2 C1 81.2(6) . . . . ? C3 Fe1 C2 C1 119.2(8) . . . . ? C10 Fe1 C2 C1 -40.1(10) . . . . ? C6 Fe1 C2 C1 160.1(7) . . . . ? C5 Fe1 C2 C1 38.3(6) . . . . ? C8 Fe1 C2 C1 -119.7(6) . . . . ? C9 Fe1 C2 C1 -77.7(6) . . . . ? C7 Fe1 C2 C1 -162.9(6) . . . . ? C4 Fe1 C2 C3 -38.0(5) . . . . ? C1 Fe1 C2 C3 -119.2(8) . . . . ? C10 Fe1 C2 C3 -159.3(7) . . . . ? C6 Fe1 C2 C3 40.8(10) . . . . ? C5 Fe1 C2 C3 -81.0(6) . . . . ? C8 Fe1 C2 C3 121.1(7) . . . . ? C9 Fe1 C2 C3 163.0(6) . . . . ? C7 Fe1 C2 C3 77.8(7) . . . . ? C3 C2 C1 C5 -1.2(9) . . . . ? Fe1 C2 C1 C5 -60.7(6) . . . . ? C3 C2 C1 Fe1 59.5(5) . . . . ? C4 C5 C1 C2 1.3(10) . . . . ? Fe1 C5 C1 C2 60.8(6) . . . . ? C4 C5 C1 Fe1 -59.6(6) . . . . ? C4 Fe1 C1 C2 -80.4(6) . . . . ? C3 Fe1 C1 C2 -37.6(5) . . . . ? C10 Fe1 C1 C2 164.5(5) . . . . ? C6 Fe1 C1 C2 -158.7(7) . . . . ? C5 Fe1 C1 C2 -118.4(9) . . . . ? C8 Fe1 C1 C2 79.7(6) . . . . ? C9 Fe1 C1 C2 121.5(6) . . . . ? C7 Fe1 C1 C2 42.5(11) . . . . ? C4 Fe1 C1 C5 38.0(6) . . . . ? C3 Fe1 C1 C5 80.8(6) . . . . ? C2 Fe1 C1 C5 118.4(9) . . . . ? C10 Fe1 C1 C5 -77.1(8) . . . . ? C6 Fe1 C1 C5 -40.3(13) . . . . ? C8 Fe1 C1 C5 -161.9(7) . . . . ? C9 Fe1 C1 C5 -120.1(8) . . . . ? C7 Fe1 C1 C5 160.9(7) . . . . ? C27 C26 C31 C30 -4.5(8) . . . . ? C25 C26 C31 C30 175.2(5) . . . . ? C26 C31 C30 C29 1.4(9) . . . . ? C27 C28 C29 C30 -1.2(11) . . . . ? C31 C30 C29 C28 1.5(10) . . . . ? C31 C26 C27 C28 4.7(8) . . . . ? C25 C26 C27 C28 -175.0(5) . . . . ? C29 C28 C27 C26 -1.9(9) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 28.47 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.516 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.078