# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Antonio Urbano' _publ_contact_author_email antonio.urbano@uam.es loop_ _publ_author_name 'M. Carmen Carreno' 'Antonio Urbano' 'Alfonso Latorre' data_datos_m _database_code_depnum_ccdc_archive 'CCDC 766362' #TrackingRef 'rac-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 Fe O2' _chemical_formula_weight 384.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5881(13) _cell_length_b 11.7105(13) _cell_length_c 13.7906(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.192(4) _cell_angle_gamma 90.00 _cell_volume 1702.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 7.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14376 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 71.98 _reflns_number_total 3248 _reflns_number_gt 3087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.7287P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3248 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.67494(2) 0.13849(2) -0.082503(17) 0.01513(10) Uani 1 1 d . . . O1 O 1.02342(10) 0.20742(10) 0.02840(8) 0.0212(3) Uani 1 1 d . . . O2 O 1.05661(11) 0.56767(10) 0.25515(9) 0.0229(3) Uani 1 1 d . . . C1 C 0.80048(19) 0.13878(16) -0.18589(14) 0.0280(4) Uani 1 1 d . . . C2 C 0.6742(2) 0.13999(16) -0.23093(14) 0.0288(4) Uani 1 1 d . . . C3 C 0.61243(18) 0.04103(17) -0.20010(13) 0.0279(4) Uani 1 1 d . . . C4 C 0.69982(18) -0.02133(16) -0.13729(13) 0.0273(4) Uani 1 1 d . . . C5 C 0.81663(17) 0.03920(16) -0.12838(14) 0.0273(4) Uani 1 1 d . . . C6 C 0.52320(15) 0.19290(14) -0.01303(12) 0.0177(3) Uani 1 1 d . . . C7 C 0.60407(16) 0.12271(14) 0.04981(12) 0.0182(3) Uani 1 1 d . . . C8 C 0.72690(15) 0.17412(14) 0.06033(11) 0.0162(3) Uani 1 1 d . . . C9 C 0.72136(14) 0.27665(13) 0.00391(11) 0.0148(3) Uani 1 1 d . . . C10 C 0.59492(14) 0.28861(13) -0.04164(11) 0.0164(3) Uani 1 1 d . . . C11 C 0.54943(15) 0.38931(15) -0.10262(13) 0.0199(3) Uani 1 1 d . . . C12 C 0.66146(15) 0.46615(15) -0.12561(12) 0.0198(3) Uani 1 1 d . . . C13 C 0.75521(14) 0.47592(14) -0.03720(12) 0.0172(3) Uani 1 1 d . . . C14 C 0.76821(14) 0.56802(14) 0.01881(12) 0.0181(3) Uani 1 1 d . . . C15 C 0.85093(15) 0.57353(14) 0.11273(12) 0.0187(3) Uani 1 1 d . . . C16 C 0.93424(14) 0.47034(13) 0.12965(11) 0.0159(3) Uani 1 1 d . . . C17 C 1.03556(14) 0.47773(14) 0.21158(11) 0.0168(3) Uani 1 1 d . . . C18 C 1.11259(15) 0.37386(13) 0.23881(12) 0.0181(3) Uani 1 1 d . . . C19 C 1.10267(15) 0.28367(14) 0.17918(12) 0.0183(3) Uani 1 1 d . . . C20 C 1.01612(14) 0.28260(13) 0.08921(12) 0.0169(3) Uani 1 1 d . . . C21 C 0.92210(14) 0.37689(13) 0.07355(12) 0.0153(3) Uani 1 1 d . . . C22 C 0.82347(15) 0.36521(13) -0.01153(12) 0.0157(3) Uani 1 1 d . . . C23 C 1.19969(18) 0.37919(16) 0.33014(14) 0.0233(4) Uani 1 1 d . . . H1 H 0.863(2) 0.196(2) -0.1910(17) 0.039(6) Uiso 1 1 d . . . H2 H 0.638(2) 0.197(2) -0.2747(18) 0.046(7) Uiso 1 1 d . . . H3 H 0.523(2) 0.024(2) -0.2140(17) 0.040(6) Uiso 1 1 d . . . H4 H 0.681(2) -0.091(2) -0.1032(17) 0.037(6) Uiso 1 1 d . . . H5 H 0.887(2) 0.0181(19) -0.0896(16) 0.034(6) Uiso 1 1 d . . . H6 H 0.4372(19) 0.1764(16) -0.0338(14) 0.018(4) Uiso 1 1 d . . . H7 H 0.5831(18) 0.0513(17) 0.0773(14) 0.021(5) Uiso 1 1 d . . . H8 H 0.799(2) 0.1426(16) 0.0988(15) 0.023(5) Uiso 1 1 d . . . H11A H 0.498(2) 0.3610(16) -0.1636(16) 0.023(5) Uiso 1 1 d . . . H11B H 0.4906(18) 0.4338(16) -0.0671(14) 0.018(4) Uiso 1 1 d . . . H12A H 0.7018(18) 0.4298(16) -0.1796(14) 0.021(5) Uiso 1 1 d . . . H12B H 0.631(2) 0.544(2) -0.1457(16) 0.032(5) Uiso 1 1 d . . . H14 H 0.7240(19) 0.6358(16) -0.0012(14) 0.018(5) Uiso 1 1 d . . . H15A H 0.903(2) 0.6431(17) 0.1158(16) 0.024(5) Uiso 1 1 d . . . H15B H 0.7971(19) 0.5831(17) 0.1679(15) 0.023(5) Uiso 1 1 d . . . H19 H 1.1518(18) 0.2184(17) 0.1908(14) 0.019(5) Uiso 1 1 d . . . H22 H 0.8684(18) 0.3411(16) -0.0666(15) 0.017(5) Uiso 1 1 d . . . H23A H 1.252(2) 0.311(2) 0.3360(17) 0.042(6) Uiso 1 1 d . . . H23B H 1.254(2) 0.446(2) 0.3287(16) 0.038(6) Uiso 1 1 d . . . H23C H 1.152(2) 0.3853(19) 0.3862(19) 0.035(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01412(14) 0.01722(16) 0.01364(16) -0.00120(8) -0.00105(10) -0.00030(8) O1 0.0204(6) 0.0217(6) 0.0208(6) -0.0027(5) -0.0019(5) 0.0030(4) O2 0.0220(6) 0.0219(6) 0.0238(6) -0.0043(5) -0.0036(5) -0.0019(5) C1 0.0297(10) 0.0296(10) 0.0268(10) -0.0096(7) 0.0149(8) -0.0069(7) C2 0.0393(11) 0.0332(11) 0.0140(9) -0.0011(7) 0.0025(8) 0.0054(8) C3 0.0266(9) 0.0355(10) 0.0210(9) -0.0136(7) -0.0006(7) -0.0041(7) C4 0.0386(10) 0.0201(9) 0.0243(10) -0.0065(7) 0.0092(8) -0.0005(7) C5 0.0228(9) 0.0340(10) 0.0249(9) -0.0095(7) 0.0015(7) 0.0092(7) C6 0.0134(7) 0.0224(8) 0.0170(8) -0.0019(6) 0.0002(6) -0.0007(6) C7 0.0197(8) 0.0195(8) 0.0154(8) 0.0014(6) 0.0014(6) -0.0011(6) C8 0.0169(7) 0.0184(8) 0.0127(8) -0.0002(6) -0.0015(6) 0.0010(6) C9 0.0141(7) 0.0170(8) 0.0129(7) -0.0019(6) 0.0001(6) 0.0003(6) C10 0.0144(7) 0.0192(8) 0.0153(8) -0.0008(6) -0.0003(6) 0.0011(6) C11 0.0155(7) 0.0206(8) 0.0226(9) 0.0023(7) -0.0042(7) 0.0014(6) C12 0.0175(8) 0.0218(9) 0.0192(9) 0.0046(6) -0.0037(6) 0.0000(6) C13 0.0125(7) 0.0206(8) 0.0181(8) 0.0049(6) -0.0005(6) -0.0012(6) C14 0.0139(7) 0.0175(8) 0.0224(9) 0.0047(6) -0.0004(6) 0.0001(6) C15 0.0179(7) 0.0178(8) 0.0201(9) -0.0012(6) 0.0002(7) 0.0001(6) C16 0.0132(7) 0.0190(8) 0.0154(8) 0.0024(6) 0.0015(6) -0.0014(6) C17 0.0145(7) 0.0192(8) 0.0164(8) 0.0002(6) 0.0011(6) -0.0025(6) C18 0.0151(7) 0.0207(9) 0.0179(9) 0.0044(6) -0.0010(6) -0.0031(6) C19 0.0149(7) 0.0194(8) 0.0201(9) 0.0042(6) -0.0011(6) 0.0011(6) C20 0.0141(7) 0.0178(8) 0.0188(8) 0.0019(6) 0.0014(6) -0.0015(6) C21 0.0119(7) 0.0186(8) 0.0151(8) 0.0024(6) 0.0002(6) -0.0015(6) C22 0.0138(7) 0.0183(8) 0.0145(8) 0.0009(6) -0.0011(6) 0.0007(5) C23 0.0248(9) 0.0224(9) 0.0209(10) 0.0021(7) -0.0073(8) -0.0035(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 C1 2.0354(19) . ? Fe1 C8 2.0398(16) . ? Fe1 C9 2.0429(15) . ? Fe1 C7 2.0431(17) . ? Fe1 C5 2.0433(17) . ? Fe1 C3 2.0436(17) . ? Fe1 C4 2.0442(18) . ? Fe1 C6 2.0454(16) . ? Fe1 C2 2.0462(19) . ? Fe1 C10 2.0524(16) . ? O1 C20 1.223(2) . ? O2 C17 1.223(2) . ? C1 C5 1.412(3) . ? C1 C2 1.422(3) . ? C1 H1 0.95(2) . ? C2 C3 1.415(3) . ? C2 H2 0.96(3) . ? C3 C4 1.412(3) . ? C3 H3 0.97(2) . ? C4 C5 1.421(3) . ? C4 H4 0.97(3) . ? C5 H5 0.91(2) . ? C6 C7 1.423(2) . ? C6 C10 1.429(2) . ? C6 H6 0.95(2) . ? C7 C8 1.429(2) . ? C7 H7 0.95(2) . ? C8 C9 1.429(2) . ? C8 H8 0.97(2) . ? C9 C10 1.433(2) . ? C9 C22 1.527(2) . ? C10 C11 1.502(2) . ? C11 C12 1.544(2) . ? C11 H11A 1.01(2) . ? C11 H11B 0.98(2) . ? C12 C13 1.505(2) . ? C12 H12A 0.99(2) . ? C12 H12B 0.99(2) . ? C13 C14 1.327(2) . ? C13 C22 1.511(2) . ? C14 C15 1.498(2) . ? C14 H14 0.950(19) . ? C15 C16 1.502(2) . ? C15 H15A 0.98(2) . ? C15 H15B 1.00(2) . ? C16 C21 1.340(2) . ? C16 C17 1.489(2) . ? C17 C18 1.493(2) . ? C18 C19 1.337(2) . ? C18 C23 1.493(2) . ? C19 C20 1.474(2) . ? C19 H19 0.93(2) . ? C20 C21 1.489(2) . ? C21 C22 1.505(2) . ? C22 H22 0.97(2) . ? C23 H23A 0.96(3) . ? C23 H23B 0.97(2) . ? C23 H23C 0.96(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 C1 Fe1 C8 122.68(7) . . ? C1 Fe1 C9 105.63(7) . . ? C8 Fe1 C9 40.98(6) . . ? C1 Fe1 C7 160.33(8) . . ? C8 Fe1 C7 40.96(6) . . ? C9 Fe1 C7 68.84(6) . . ? C1 Fe1 C5 40.51(8) . . ? C8 Fe1 C5 105.90(7) . . ? C9 Fe1 C5 119.12(7) . . ? C7 Fe1 C5 124.36(7) . . ? C1 Fe1 C3 68.30(8) . . ? C8 Fe1 C3 156.97(8) . . ? C9 Fe1 C3 161.58(7) . . ? C7 Fe1 C3 122.65(7) . . ? C5 Fe1 C3 68.32(7) . . ? C1 Fe1 C4 68.19(7) . . ? C8 Fe1 C4 120.78(7) . . ? C9 Fe1 C4 155.29(7) . . ? C7 Fe1 C4 108.50(7) . . ? C5 Fe1 C4 40.69(8) . . ? C3 Fe1 C4 40.42(8) . . ? C1 Fe1 C6 156.64(8) . . ? C8 Fe1 C6 68.81(6) . . ? C9 Fe1 C6 68.76(6) . . ? C7 Fe1 C6 40.74(6) . . ? C5 Fe1 C6 162.21(8) . . ? C3 Fe1 C6 109.51(7) . . ? C4 Fe1 C6 126.25(7) . . ? C1 Fe1 C2 40.79(8) . . ? C8 Fe1 C2 160.13(8) . . ? C9 Fe1 C2 123.75(7) . . ? C7 Fe1 C2 157.77(8) . . ? C5 Fe1 C2 68.38(8) . . ? C3 Fe1 C2 40.48(8) . . ? C4 Fe1 C2 68.11(7) . . ? C6 Fe1 C2 122.26(7) . . ? C1 Fe1 C10 120.19(7) . . ? C8 Fe1 C10 69.00(6) . . ? C9 Fe1 C10 40.97(6) . . ? C7 Fe1 C10 68.79(6) . . ? C5 Fe1 C10 154.87(7) . . ? C3 Fe1 C10 125.74(7) . . ? C4 Fe1 C10 162.92(7) . . ? C6 Fe1 C10 40.83(6) . . ? C2 Fe1 C10 107.64(7) . . ? C5 C1 C2 108.35(16) . . ? C5 C1 Fe1 70.05(10) . . ? C2 C1 Fe1 70.01(11) . . ? C5 C1 H1 124.9(14) . . ? C2 C1 H1 126.7(14) . . ? Fe1 C1 H1 124.0(14) . . ? C3 C2 C1 107.61(17) . . ? C3 C2 Fe1 69.66(10) . . ? C1 C2 Fe1 69.19(11) . . ? C3 C2 H2 126.4(15) . . ? C1 C2 H2 126.0(15) . . ? Fe1 C2 H2 127.1(15) . . ? C4 C3 C2 108.22(16) . . ? C4 C3 Fe1 69.81(10) . . ? C2 C3 Fe1 69.86(10) . . ? C4 C3 H3 125.8(14) . . ? C2 C3 H3 125.6(14) . . ? Fe1 C3 H3 121.0(14) . . ? C3 C4 C5 108.18(17) . . ? C3 C4 Fe1 69.77(10) . . ? C5 C4 Fe1 69.62(10) . . ? C3 C4 H4 125.6(13) . . ? C5 C4 H4 126.1(13) . . ? Fe1 C4 H4 123.7(14) . . ? C1 C5 C4 107.64(16) . . ? C1 C5 Fe1 69.45(10) . . ? C4 C5 Fe1 69.69(10) . . ? C1 C5 H5 127.0(14) . . ? C4 C5 H5 125.2(14) . . ? Fe1 C5 H5 123.9(14) . . ? C7 C6 C10 108.40(14) . . ? C7 C6 Fe1 69.54(9) . . ? C10 C6 Fe1 69.85(9) . . ? C7 C6 H6 125.0(12) . . ? C10 C6 H6 126.6(12) . . ? Fe1 C6 H6 124.6(12) . . ? C6 C7 C8 108.09(14) . . ? C6 C7 Fe1 69.72(9) . . ? C8 C7 Fe1 69.40(9) . . ? C6 C7 H7 126.9(11) . . ? C8 C7 H7 124.9(11) . . ? Fe1 C7 H7 123.5(12) . . ? C7 C8 C9 107.86(13) . . ? C7 C8 Fe1 69.64(9) . . ? C9 C8 Fe1 69.63(9) . . ? C7 C8 H8 124.5(12) . . ? C9 C8 H8 127.7(12) . . ? Fe1 C8 H8 125.7(12) . . ? C8 C9 C10 108.15(13) . . ? C8 C9 C22 130.68(13) . . ? C10 C9 C22 121.17(13) . . ? C8 C9 Fe1 69.39(9) . . ? C10 C9 Fe1 69.87(9) . . ? C22 C9 Fe1 126.34(11) . . ? C6 C10 C9 107.51(13) . . ? C6 C10 C11 128.22(14) . . ? C9 C10 C11 124.16(14) . . ? C6 C10 Fe1 69.32(9) . . ? C9 C10 Fe1 69.16(9) . . ? C11 C10 Fe1 129.66(12) . . ? C10 C11 C12 111.04(13) . . ? C10 C11 H11A 109.1(11) . . ? C12 C11 H11A 112.5(12) . . ? C10 C11 H11B 108.9(11) . . ? C12 C11 H11B 109.2(11) . . ? H11A C11 H11B 105.8(16) . . ? C13 C12 C11 109.90(14) . . ? C13 C12 H12A 110.2(11) . . ? C11 C12 H12A 107.2(11) . . ? C13 C12 H12B 109.3(12) . . ? C11 C12 H12B 110.7(13) . . ? H12A C12 H12B 109.6(17) . . ? C14 C13 C12 124.02(14) . . ? C14 C13 C22 122.62(14) . . ? C12 C13 C22 113.02(14) . . ? C13 C14 C15 124.08(14) . . ? C13 C14 H14 119.2(12) . . ? C15 C14 H14 116.7(12) . . ? C14 C15 C16 112.89(14) . . ? C14 C15 H15A 110.7(13) . . ? C16 C15 H15A 110.1(12) . . ? C14 C15 H15B 109.6(11) . . ? C16 C15 H15B 109.9(11) . . ? H15A C15 H15B 103.3(17) . . ? C21 C16 C17 120.72(14) . . ? C21 C16 C15 122.91(14) . . ? C17 C16 C15 116.36(13) . . ? O2 C17 C16 120.65(14) . . ? O2 C17 C18 120.45(14) . . ? C16 C17 C18 118.89(14) . . ? C19 C18 C23 124.05(15) . . ? C19 C18 C17 118.56(15) . . ? C23 C18 C17 117.35(14) . . ? C18 C19 C20 122.18(15) . . ? C18 C19 H19 122.2(12) . . ? C20 C19 H19 115.6(12) . . ? O1 C20 C19 120.67(14) . . ? O1 C20 C21 121.14(14) . . ? C19 C20 C21 118.17(14) . . ? C16 C21 C20 119.60(14) . . ? C16 C21 C22 123.24(14) . . ? C20 C21 C22 116.95(13) . . ? C21 C22 C13 112.84(13) . . ? C21 C22 C9 113.78(13) . . ? C13 C22 C9 106.60(12) . . ? C21 C22 H22 106.3(11) . . ? C13 C22 H22 108.9(11) . . ? C9 C22 H22 108.3(11) . . ? C18 C23 H23A 109.9(14) . . ? C18 C23 H23B 109.8(13) . . ? H23A C23 H23B 109(2) . . ? C18 C23 H23C 110.6(14) . . ? H23A C23 H23C 109(2) . . ? H23B C23 H23C 108.1(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 C8 Fe1 C1 C5 75.54(12) . . . . ? C9 Fe1 C1 C5 116.78(11) . . . . ? C7 Fe1 C1 C5 46.1(2) . . . . ? C3 Fe1 C1 C5 -81.60(12) . . . . ? C4 Fe1 C1 C5 -37.92(11) . . . . ? C6 Fe1 C1 C5 -170.74(15) . . . . ? C2 Fe1 C1 C5 -119.23(15) . . . . ? C10 Fe1 C1 C5 158.68(10) . . . . ? C8 Fe1 C1 C2 -165.23(10) . . . . ? C9 Fe1 C1 C2 -123.99(11) . . . . ? C7 Fe1 C1 C2 165.34(18) . . . . ? C5 Fe1 C1 C2 119.23(15) . . . . ? C3 Fe1 C1 C2 37.64(11) . . . . ? C4 Fe1 C1 C2 81.31(11) . . . . ? C6 Fe1 C1 C2 -51.5(2) . . . . ? C10 Fe1 C1 C2 -82.09(12) . . . . ? C5 C1 C2 C3 0.5(2) . . . . ? Fe1 C1 C2 C3 -59.29(13) . . . . ? C5 C1 C2 Fe1 59.79(13) . . . . ? C1 Fe1 C2 C3 119.07(16) . . . . ? C8 Fe1 C2 C3 158.24(19) . . . . ? C9 Fe1 C2 C3 -167.10(10) . . . . ? C7 Fe1 C2 C3 -47.9(2) . . . . ? C5 Fe1 C2 C3 81.51(12) . . . . ? C4 Fe1 C2 C3 37.54(11) . . . . ? C6 Fe1 C2 C3 -82.46(13) . . . . ? C10 Fe1 C2 C3 -124.87(11) . . . . ? C8 Fe1 C2 C1 39.2(3) . . . . ? C9 Fe1 C2 C1 73.83(12) . . . . ? C7 Fe1 C2 C1 -166.99(17) . . . . ? C5 Fe1 C2 C1 -37.57(11) . . . . ? C3 Fe1 C2 C1 -119.07(16) . . . . ? C4 Fe1 C2 C1 -81.54(11) . . . . ? C6 Fe1 C2 C1 158.47(10) . . . . ? C10 Fe1 C2 C1 116.05(11) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? Fe1 C2 C3 C4 -59.48(13) . . . . ? C1 C2 C3 Fe1 59.00(13) . . . . ? C1 Fe1 C3 C4 81.41(12) . . . . ? C8 Fe1 C3 C4 -41.9(2) . . . . ? C9 Fe1 C3 C4 155.30(19) . . . . ? C7 Fe1 C3 C4 -80.15(12) . . . . ? C5 Fe1 C3 C4 37.66(11) . . . . ? C6 Fe1 C3 C4 -123.47(11) . . . . ? C2 Fe1 C3 C4 119.33(16) . . . . ? C10 Fe1 C3 C4 -166.24(10) . . . . ? C1 Fe1 C3 C2 -37.92(12) . . . . ? C8 Fe1 C3 C2 -161.22(16) . . . . ? C9 Fe1 C3 C2 36.0(3) . . . . ? C7 Fe1 C3 C2 160.52(11) . . . . ? C5 Fe1 C3 C2 -81.67(12) . . . . ? C4 Fe1 C3 C2 -119.33(16) . . . . ? C6 Fe1 C3 C2 117.21(12) . . . . ? C10 Fe1 C3 C2 74.44(13) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? Fe1 C3 C4 C5 -59.22(12) . . . . ? C2 C3 C4 Fe1 59.51(13) . . . . ? C1 Fe1 C4 C3 -81.69(12) . . . . ? C8 Fe1 C4 C3 162.30(11) . . . . ? C9 Fe1 C4 C3 -161.58(15) . . . . ? C7 Fe1 C4 C3 118.98(11) . . . . ? C5 Fe1 C4 C3 -119.45(16) . . . . ? C6 Fe1 C4 C3 77.17(13) . . . . ? C2 Fe1 C4 C3 -37.59(12) . . . . ? C10 Fe1 C4 C3 41.1(3) . . . . ? C1 Fe1 C4 C5 37.75(12) . . . . ? C8 Fe1 C4 C5 -78.26(12) . . . . ? C9 Fe1 C4 C5 -42.1(2) . . . . ? C7 Fe1 C4 C5 -121.58(11) . . . . ? C3 Fe1 C4 C5 119.45(16) . . . . ? C6 Fe1 C4 C5 -163.39(10) . . . . ? C2 Fe1 C4 C5 81.86(12) . . . . ? C10 Fe1 C4 C5 160.5(2) . . . . ? C2 C1 C5 C4 -0.3(2) . . . . ? Fe1 C1 C5 C4 59.45(12) . . . . ? C2 C1 C5 Fe1 -59.77(13) . . . . ? C3 C4 C5 C1 0.0(2) . . . . ? Fe1 C4 C5 C1 -59.30(12) . . . . ? C3 C4 C5 Fe1 59.32(12) . . . . ? C8 Fe1 C5 C1 -122.06(11) . . . . ? C9 Fe1 C5 C1 -79.78(12) . . . . ? C7 Fe1 C5 C1 -162.91(11) . . . . ? C3 Fe1 C5 C1 81.53(12) . . . . ? C4 Fe1 C5 C1 118.94(16) . . . . ? C6 Fe1 C5 C1 167.9(2) . . . . ? C2 Fe1 C5 C1 37.82(11) . . . . ? C10 Fe1 C5 C1 -47.7(2) . . . . ? C1 Fe1 C5 C4 -118.94(16) . . . . ? C8 Fe1 C5 C4 119.00(11) . . . . ? C9 Fe1 C5 C4 161.28(10) . . . . ? C7 Fe1 C5 C4 78.14(13) . . . . ? C3 Fe1 C5 C4 -37.42(11) . . . . ? C6 Fe1 C5 C4 49.0(3) . . . . ? C2 Fe1 C5 C4 -81.12(12) . . . . ? C10 Fe1 C5 C4 -166.68(14) . . . . ? C1 Fe1 C6 C7 -161.98(17) . . . . ? C8 Fe1 C6 C7 -37.72(10) . . . . ? C9 Fe1 C6 C7 -81.83(10) . . . . ? C5 Fe1 C6 C7 38.0(3) . . . . ? C3 Fe1 C6 C7 117.75(11) . . . . ? C4 Fe1 C6 C7 75.62(12) . . . . ? C2 Fe1 C6 C7 160.81(10) . . . . ? C10 Fe1 C6 C7 -119.72(13) . . . . ? C1 Fe1 C6 C10 -42.3(2) . . . . ? C8 Fe1 C6 C10 81.99(10) . . . . ? C9 Fe1 C6 C10 37.88(9) . . . . ? C7 Fe1 C6 C10 119.72(13) . . . . ? C5 Fe1 C6 C10 157.7(2) . . . . ? C3 Fe1 C6 C10 -122.54(10) . . . . ? C4 Fe1 C6 C10 -164.66(10) . . . . ? C2 Fe1 C6 C10 -79.48(11) . . . . ? C10 C6 C7 C8 -0.25(19) . . . . ? Fe1 C6 C7 C8 58.98(11) . . . . ? C10 C6 C7 Fe1 -59.23(11) . . . . ? C1 Fe1 C7 C6 158.63(19) . . . . ? C8 Fe1 C7 C6 119.51(14) . . . . ? C9 Fe1 C7 C6 81.61(10) . . . . ? C5 Fe1 C7 C6 -166.82(10) . . . . ? C3 Fe1 C7 C6 -82.18(12) . . . . ? C4 Fe1 C7 C6 -124.54(10) . . . . ? C2 Fe1 C7 C6 -47.3(2) . . . . ? C10 Fe1 C7 C6 37.52(9) . . . . ? C1 Fe1 C7 C8 39.1(2) . . . . ? C9 Fe1 C7 C8 -37.90(9) . . . . ? C5 Fe1 C7 C8 73.67(12) . . . . ? C3 Fe1 C7 C8 158.31(10) . . . . ? C4 Fe1 C7 C8 115.96(10) . . . . ? C6 Fe1 C7 C8 -119.51(14) . . . . ? C2 Fe1 C7 C8 -166.79(17) . . . . ? C10 Fe1 C7 C8 -81.99(10) . . . . ? C6 C7 C8 C9 0.18(18) . . . . ? Fe1 C7 C8 C9 59.36(11) . . . . ? C6 C7 C8 Fe1 -59.18(12) . . . . ? C1 Fe1 C8 C7 -165.38(10) . . . . ? C9 Fe1 C8 C7 119.12(13) . . . . ? C5 Fe1 C8 C7 -124.54(10) . . . . ? C3 Fe1 C8 C7 -52.7(2) . . . . ? C4 Fe1 C8 C7 -82.95(11) . . . . ? C6 Fe1 C8 C7 37.53(9) . . . . ? C2 Fe1 C8 C7 165.3(2) . . . . ? C10 Fe1 C8 C7 81.43(10) . . . . ? C1 Fe1 C8 C9 75.49(11) . . . . ? C7 Fe1 C8 C9 -119.12(13) . . . . ? C5 Fe1 C8 C9 116.34(10) . . . . ? C3 Fe1 C8 C9 -171.81(16) . . . . ? C4 Fe1 C8 C9 157.93(9) . . . . ? C6 Fe1 C8 C9 -81.59(9) . . . . ? C2 Fe1 C8 C9 46.1(2) . . . . ? C10 Fe1 C8 C9 -37.69(9) . . . . ? C7 C8 C9 C10 -0.04(18) . . . . ? Fe1 C8 C9 C10 59.33(11) . . . . ? C7 C8 C9 C22 179.86(15) . . . . ? Fe1 C8 C9 C22 -120.77(17) . . . . ? C7 C8 C9 Fe1 -59.37(11) . . . . ? C1 Fe1 C9 C8 -122.20(10) . . . . ? C7 Fe1 C9 C8 37.88(9) . . . . ? C5 Fe1 C9 C8 -80.61(11) . . . . ? C3 Fe1 C9 C8 169.8(2) . . . . ? C4 Fe1 C9 C8 -50.6(2) . . . . ? C6 Fe1 C9 C8 81.73(10) . . . . ? C2 Fe1 C9 C8 -162.86(10) . . . . ? C10 Fe1 C9 C8 119.49(13) . . . . ? C1 Fe1 C9 C10 118.31(10) . . . . ? C8 Fe1 C9 C10 -119.49(13) . . . . ? C7 Fe1 C9 C10 -81.60(10) . . . . ? C5 Fe1 C9 C10 159.90(10) . . . . ? C3 Fe1 C9 C10 50.4(2) . . . . ? C4 Fe1 C9 C10 -170.05(16) . . . . ? C6 Fe1 C9 C10 -37.76(9) . . . . ? C2 Fe1 C9 C10 77.65(12) . . . . ? C1 Fe1 C9 C22 3.81(15) . . . . ? C8 Fe1 C9 C22 126.01(16) . . . . ? C7 Fe1 C9 C22 163.89(14) . . . . ? C5 Fe1 C9 C22 45.40(15) . . . . ? C3 Fe1 C9 C22 -64.1(3) . . . . ? C4 Fe1 C9 C22 75.4(2) . . . . ? C6 Fe1 C9 C22 -152.26(14) . . . . ? C2 Fe1 C9 C22 -36.85(16) . . . . ? C10 Fe1 C9 C22 -114.50(16) . . . . ? C7 C6 C10 C9 0.23(18) . . . . ? Fe1 C6 C10 C9 -58.81(11) . . . . ? C7 C6 C10 C11 -176.14(16) . . . . ? Fe1 C6 C10 C11 124.82(17) . . . . ? C7 C6 C10 Fe1 59.04(11) . . . . ? C8 C9 C10 C6 -0.11(17) . . . . ? C22 C9 C10 C6 179.98(14) . . . . ? Fe1 C9 C10 C6 58.92(11) . . . . ? C8 C9 C10 C11 176.43(15) . . . . ? C22 C9 C10 C11 -3.5(2) . . . . ? Fe1 C9 C10 C11 -124.54(16) . . . . ? C8 C9 C10 Fe1 -59.03(11) . . . . ? C22 C9 C10 Fe1 121.06(14) . . . . ? C1 Fe1 C10 C6 162.03(10) . . . . ? C8 Fe1 C10 C6 -81.50(10) . . . . ? C9 Fe1 C10 C6 -119.20(13) . . . . ? C7 Fe1 C10 C6 -37.45(9) . . . . ? C5 Fe1 C10 C6 -164.18(15) . . . . ? C3 Fe1 C10 C6 78.25(12) . . . . ? C4 Fe1 C10 C6 46.6(3) . . . . ? C2 Fe1 C10 C6 119.26(10) . . . . ? C1 Fe1 C10 C9 -78.77(11) . . . . ? C8 Fe1 C10 C9 37.70(9) . . . . ? C7 Fe1 C10 C9 81.75(10) . . . . ? C5 Fe1 C10 C9 -45.0(2) . . . . ? C3 Fe1 C10 C9 -162.55(10) . . . . ? C4 Fe1 C10 C9 165.8(2) . . . . ? C6 Fe1 C10 C9 119.20(13) . . . . ? C2 Fe1 C10 C9 -121.54(10) . . . . ? C1 Fe1 C10 C11 38.93(17) . . . . ? C8 Fe1 C10 C11 155.40(16) . . . . ? C9 Fe1 C10 C11 117.70(18) . . . . ? C7 Fe1 C10 C11 -160.55(16) . . . . ? C5 Fe1 C10 C11 72.7(2) . . . . ? C3 Fe1 C10 C11 -44.85(17) . . . . ? C4 Fe1 C10 C11 -76.5(3) . . . . ? C6 Fe1 C10 C11 -123.10(18) . . . . ? C2 Fe1 C10 C11 -3.84(16) . . . . ? C6 C10 C11 C12 -173.52(16) . . . . ? C9 C10 C11 C12 10.7(2) . . . . ? Fe1 C10 C11 C12 -79.56(18) . . . . ? C10 C11 C12 C13 -40.18(19) . . . . ? C11 C12 C13 C14 -105.23(18) . . . . ? C11 C12 C13 C22 68.21(18) . . . . ? C12 C13 C14 C15 172.94(15) . . . . ? C22 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C16 9.3(2) . . . . ? C14 C15 C16 C21 -9.0(2) . . . . ? C14 C15 C16 C17 169.28(13) . . . . ? C21 C16 C17 O2 171.00(15) . . . . ? C15 C16 C17 O2 -7.3(2) . . . . ? C21 C16 C17 C18 -8.1(2) . . . . ? C15 C16 C17 C18 173.59(14) . . . . ? O2 C17 C18 C19 -168.13(15) . . . . ? C16 C17 C18 C19 10.9(2) . . . . ? O2 C17 C18 C23 9.9(2) . . . . ? C16 C17 C18 C23 -171.06(14) . . . . ? C23 C18 C19 C20 -179.43(16) . . . . ? C17 C18 C19 C20 -1.6(2) . . . . ? C18 C19 C20 O1 168.14(15) . . . . ? C18 C19 C20 C21 -10.4(2) . . . . ? C17 C16 C21 C20 -4.0(2) . . . . ? C15 C16 C21 C20 174.19(14) . . . . ? C17 C16 C21 C22 -178.69(14) . . . . ? C15 C16 C21 C22 -0.5(2) . . . . ? O1 C20 C21 C16 -165.29(15) . . . . ? C19 C20 C21 C16 13.2(2) . . . . ? O1 C20 C21 C22 9.7(2) . . . . ? C19 C20 C21 C22 -171.76(14) . . . . ? C16 C21 C22 C13 9.7(2) . . . . ? C20 C21 C22 C13 -165.05(13) . . . . ? C16 C21 C22 C9 -111.89(17) . . . . ? C20 C21 C22 C9 73.32(18) . . . . ? C14 C13 C22 C21 -9.6(2) . . . . ? C12 C13 C22 C21 176.89(13) . . . . ? C14 C13 C22 C9 116.04(16) . . . . ? C12 C13 C22 C9 -57.51(17) . . . . ? C8 C9 C22 C21 -29.8(2) . . . . ? C10 C9 C22 C21 150.13(14) . . . . ? Fe1 C9 C22 C21 -122.98(13) . . . . ? C8 C9 C22 C13 -154.80(16) . . . . ? C10 C9 C22 C13 25.1(2) . . . . ? Fe1 C9 C22 C13 111.98(13) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 71.98 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.271 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.051 # Attachment '(pS,M)-6.cif' data_datos_0m _database_code_depnum_ccdc_archive 'CCDC 766363' #TrackingRef '(pS,M)-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 Fe O2' _chemical_formula_weight 382.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3174(4) _cell_length_b 9.4739(5) _cell_length_c 12.2845(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.793(3) _cell_angle_gamma 90.00 _cell_volume 845.64(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9234 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 34.08 _exptl_crystal_description prismatic _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8396 _exptl_absorpt_correction_T_max 0.8761 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55241 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 32.03 _reflns_number_total 5882 _reflns_number_gt 5545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^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 mixed _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 -0.006(7) _refine_ls_number_reflns 5882 _refine_ls_number_parameters 307 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.69404(2) 1.147737(18) 0.155774(12) 0.01312(4) Uani 1 1 d . . . C1 C 0.6010(2) 1.30245(19) 0.25128(15) 0.0361(4) Uani 1 1 d . . . C2 C 0.7152(3) 1.20903(18) 0.31627(12) 0.0336(4) Uani 1 1 d . . . C3 C 0.8881(2) 1.20933(17) 0.27881(14) 0.0334(4) Uani 1 1 d . . . C4 C 0.8823(3) 1.3034(2) 0.18977(15) 0.0372(4) Uani 1 1 d . . . C5 C 0.7034(3) 1.36154(18) 0.17277(14) 0.0396(5) Uani 1 1 d . . . C6 C 0.63882(18) 0.93514(13) 0.14068(10) 0.0127(2) Uani 1 1 d . . . C7 C 0.79438(17) 0.97376(13) 0.08660(10) 0.0142(2) Uani 1 1 d . . . C8 C 0.73591(18) 1.07576(14) 0.00481(10) 0.0171(2) Uani 1 1 d . . . C9 C 0.54473(18) 1.10305(14) 0.00846(10) 0.0167(2) Uani 1 1 d . . . C10 C 0.48536(17) 1.01677(14) 0.09189(10) 0.0149(2) Uani 1 1 d . . . C11 C 0.29848(17) 0.99738(15) 0.12642(11) 0.0187(2) Uani 1 1 d . . . C12 C 0.31708(18) 0.97141(15) 0.25041(11) 0.0195(2) Uani 1 1 d . . . C13 C 0.46145(16) 0.86262(14) 0.28917(10) 0.0152(2) Uani 1 1 d . . . C14 C 0.44059(18) 0.78669(15) 0.38423(10) 0.0192(2) Uani 1 1 d . . . C15 C 0.57179(18) 0.69204(15) 0.42748(10) 0.0189(2) Uani 1 1 d . . . C16 C 0.72611(16) 0.66665(13) 0.37434(9) 0.0150(2) Uani 1 1 d . . . C17 C 0.86806(19) 0.56797(14) 0.42694(10) 0.0183(2) Uani 1 1 d . . . C18 C 1.03868(18) 0.54676(14) 0.37550(10) 0.0174(2) Uani 1 1 d . . . C19 C 1.05162(18) 0.60711(13) 0.27781(10) 0.0175(2) Uani 1 1 d . . . C20 C 0.89909(16) 0.68420(12) 0.21536(10) 0.0134(2) Uani 1 1 d . . . C21 C 0.74683(16) 0.73648(13) 0.27501(9) 0.0124(2) Uani 1 1 d . . . C22 C 0.61966(16) 0.84126(13) 0.23438(9) 0.0126(2) Uani 1 1 d . . . C23 C 1.1822(2) 0.45161(16) 0.43235(13) 0.0241(3) Uani 1 1 d . . . O1 O 0.84821(16) 0.50924(12) 0.51330(9) 0.0278(2) Uani 1 1 d . . . O2 O 0.89631(13) 0.69393(10) 0.11571(7) 0.01729(17) Uani 1 1 d . . . H1 H 0.464(4) 1.314(3) 0.261(2) 0.064(8) Uiso 1 1 d . . . H2 H 0.676(3) 1.160(3) 0.3767(16) 0.037(5) Uiso 1 1 d . . . H3 H 0.987(3) 1.159(3) 0.3026(19) 0.053(6) Uiso 1 1 d . . . H4 H 0.981(4) 1.321(3) 0.145(2) 0.057(7) Uiso 1 1 d . . . H5 H 0.653(4) 1.424(3) 0.113(2) 0.061(8) Uiso 1 1 d . . . H7 H 0.915(2) 0.9413(17) 0.1037(13) 0.009(4) Uiso 1 1 d . . . H8 H 0.813(2) 1.124(2) -0.0422(13) 0.020(4) Uiso 1 1 d . . . H9 H 0.477(2) 1.1674(19) -0.0342(13) 0.015(4) Uiso 1 1 d . . . H11A H 0.213(3) 1.079(2) 0.1055(16) 0.027(5) Uiso 1 1 d . . . H11B H 0.244(2) 0.9112(19) 0.0901(14) 0.017(4) Uiso 1 1 d . . . H12A H 0.350(3) 1.059(2) 0.2839(15) 0.027(5) Uiso 1 1 d . . . H12B H 0.204(3) 0.939(2) 0.2735(15) 0.027(5) Uiso 1 1 d . . . H14 H 0.326(3) 0.797(2) 0.4227(14) 0.020(4) Uiso 1 1 d . . . H15 H 0.559(2) 0.636(3) 0.4906(15) 0.027(4) Uiso 1 1 d . . . H19 H 1.162(2) 0.6001(18) 0.2395(14) 0.020(4) Uiso 1 1 d . . . H23A H 1.298(4) 0.463(3) 0.402(2) 0.048(7) Uiso 1 1 d . . . H23B H 1.141(3) 0.360(3) 0.4230(16) 0.032(5) Uiso 1 1 d . . . H23C H 1.210(3) 0.473(3) 0.5026(19) 0.041(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01494(7) 0.01111(7) 0.01259(7) -0.00029(6) -0.00139(5) -0.00042(7) C1 0.0330(8) 0.0307(8) 0.0431(9) -0.0228(7) -0.0020(7) 0.0062(7) C2 0.0606(11) 0.0233(7) 0.0165(6) -0.0067(5) 0.0026(7) -0.0053(7) C3 0.0355(9) 0.0227(7) 0.0363(8) -0.0105(6) -0.0195(7) 0.0061(6) C4 0.0416(9) 0.0318(8) 0.0386(9) -0.0142(7) 0.0065(7) -0.0214(7) C5 0.0740(15) 0.0095(6) 0.0287(8) 0.0003(6) -0.0209(8) -0.0010(7) C6 0.0124(5) 0.0132(5) 0.0127(5) -0.0019(4) 0.0026(4) -0.0018(4) C7 0.0129(5) 0.0152(5) 0.0151(5) -0.0006(4) 0.0040(4) -0.0003(4) C8 0.0179(6) 0.0182(6) 0.0154(5) 0.0012(4) 0.0037(4) -0.0033(5) C9 0.0187(6) 0.0174(5) 0.0130(5) -0.0009(4) -0.0030(4) -0.0004(4) C10 0.0123(5) 0.0174(6) 0.0145(5) -0.0025(4) -0.0001(4) -0.0003(4) C11 0.0125(5) 0.0233(6) 0.0203(6) -0.0015(5) 0.0014(4) 0.0006(5) C12 0.0139(5) 0.0239(6) 0.0220(6) -0.0027(5) 0.0074(5) 0.0012(5) C13 0.0130(5) 0.0167(5) 0.0167(5) -0.0041(4) 0.0044(4) -0.0033(4) C14 0.0176(6) 0.0243(6) 0.0170(5) -0.0031(5) 0.0073(4) -0.0054(5) C15 0.0208(6) 0.0229(6) 0.0140(5) 0.0001(4) 0.0061(4) -0.0066(5) C16 0.0178(5) 0.0144(6) 0.0130(4) -0.0004(4) 0.0019(4) -0.0037(4) C17 0.0227(6) 0.0159(6) 0.0154(5) -0.0003(4) -0.0016(4) -0.0062(5) C18 0.0196(6) 0.0134(5) 0.0176(5) -0.0017(4) -0.0041(4) -0.0012(4) C19 0.0172(6) 0.0162(5) 0.0188(5) -0.0010(4) 0.0010(4) 0.0016(4) C20 0.0144(5) 0.0111(5) 0.0148(5) -0.0011(4) 0.0018(4) -0.0011(4) C21 0.0130(5) 0.0125(5) 0.0119(5) -0.0021(4) 0.0025(4) -0.0030(4) C22 0.0125(5) 0.0130(5) 0.0125(5) -0.0030(4) 0.0029(4) -0.0027(4) C23 0.0259(7) 0.0203(7) 0.0236(7) 0.0018(5) -0.0080(5) 0.0006(5) O1 0.0321(6) 0.0305(5) 0.0207(5) 0.0103(4) 0.0029(4) -0.0024(5) O2 0.0199(4) 0.0182(4) 0.0142(4) -0.0001(3) 0.0041(3) 0.0035(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C4 2.0274(16) . ? Fe1 C7 2.0311(12) . ? Fe1 C8 2.0329(12) . ? Fe1 C3 2.0334(15) . ? Fe1 C5 2.0366(17) . ? Fe1 C2 2.0436(14) . ? Fe1 C1 2.0438(15) . ? Fe1 C9 2.0445(12) . ? Fe1 C10 2.0502(13) . ? Fe1 C6 2.0583(13) . ? C1 C2 1.401(3) . ? C1 C5 1.406(3) . ? C1 H1 1.03(3) . ? C2 C3 1.397(3) . ? C2 H2 0.95(2) . ? C3 C4 1.408(3) . ? C3 H3 0.89(3) . ? C4 C5 1.413(3) . ? C4 H4 0.97(3) . ? C5 H5 0.97(3) . ? C6 C7 1.4317(16) . ? C6 C10 1.4350(18) . ? C6 C22 1.4743(17) . ? C7 C8 1.4229(18) . ? C7 H7 0.932(17) . ? C8 C9 1.4286(18) . ? C8 H8 0.968(17) . ? C9 C10 1.4187(18) . ? C9 H9 0.911(17) . ? C10 C11 1.4902(17) . ? C11 C12 1.5330(19) . ? C11 H11A 1.01(2) . ? C11 H11B 0.992(18) . ? C12 C13 1.5120(19) . ? C12 H12A 0.94(2) . ? C12 H12B 0.96(2) . ? C13 C14 1.3953(17) . ? C13 C22 1.4207(15) . ? C14 C15 1.374(2) . ? C14 H14 1.012(18) . ? C15 C16 1.3905(16) . ? C15 H15 0.95(2) . ? C16 C21 1.4118(16) . ? C16 C17 1.4872(19) . ? C17 O1 1.2217(16) . ? C17 C18 1.4782(19) . ? C18 C19 1.3428(18) . ? C18 C23 1.493(2) . ? C19 C20 1.4714(17) . ? C19 H19 0.985(17) . ? C20 O2 1.2254(14) . ? C20 C21 1.4888(16) . ? C21 C22 1.4109(18) . ? C23 H23A 0.98(3) . ? C23 H23B 0.92(2) . ? C23 H23C 0.89(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 C4 Fe1 C7 113.95(7) . . ? C4 Fe1 C8 105.06(6) . . ? C7 Fe1 C8 40.99(5) . . ? C4 Fe1 C3 40.56(8) . . ? C7 Fe1 C3 106.77(6) . . ? C8 Fe1 C3 127.37(7) . . ? C4 Fe1 C5 40.68(9) . . ? C7 Fe1 C5 147.19(7) . . ? C8 Fe1 C5 114.85(7) . . ? C3 Fe1 C5 68.05(7) . . ? C4 Fe1 C2 67.82(7) . . ? C7 Fe1 C2 130.11(6) . . ? C8 Fe1 C2 166.67(7) . . ? C3 Fe1 C2 40.07(8) . . ? C5 Fe1 C2 67.71(7) . . ? C4 Fe1 C1 67.95(8) . . ? C7 Fe1 C1 169.59(7) . . ? C8 Fe1 C1 149.39(7) . . ? C3 Fe1 C1 67.56(7) . . ? C5 Fe1 C1 40.31(8) . . ? C2 Fe1 C1 40.08(8) . . ? C4 Fe1 C9 127.72(7) . . ? C7 Fe1 C9 69.11(5) . . ? C8 Fe1 C9 41.02(5) . . ? C3 Fe1 C9 166.05(7) . . ? C5 Fe1 C9 107.74(6) . . ? C2 Fe1 C9 152.18(7) . . ? C1 Fe1 C9 118.50(6) . . ? C4 Fe1 C10 167.46(7) . . ? C7 Fe1 C10 68.81(5) . . ? C8 Fe1 C10 68.51(5) . . ? C3 Fe1 C10 151.80(7) . . ? C5 Fe1 C10 130.97(7) . . ? C2 Fe1 C10 120.62(6) . . ? C1 Fe1 C10 111.72(6) . . ? C9 Fe1 C10 40.54(5) . . ? C4 Fe1 C6 148.39(8) . . ? C7 Fe1 C6 40.98(5) . . ? C8 Fe1 C6 68.82(5) . . ? C3 Fe1 C6 117.40(6) . . ? C5 Fe1 C6 170.52(8) . . ? C2 Fe1 C6 110.89(6) . . ? C1 Fe1 C6 132.71(7) . . ? C9 Fe1 C6 68.84(5) . . ? C10 Fe1 C6 40.88(5) . . ? C2 C1 C5 108.18(16) . . ? C2 C1 Fe1 69.95(9) . . ? C5 C1 Fe1 69.57(10) . . ? C2 C1 H1 121.6(15) . . ? C5 C1 H1 130.0(15) . . ? Fe1 C1 H1 122.6(16) . . ? C3 C2 C1 108.28(15) . . ? C3 C2 Fe1 69.57(9) . . ? C1 C2 Fe1 69.97(9) . . ? C3 C2 H2 129.0(13) . . ? C1 C2 H2 122.7(13) . . ? Fe1 C2 H2 128.6(14) . . ? C2 C3 C4 108.18(16) . . ? C2 C3 Fe1 70.36(9) . . ? C4 C3 Fe1 69.49(9) . . ? C2 C3 H3 128.7(16) . . ? C4 C3 H3 123.1(16) . . ? Fe1 C3 H3 124.0(17) . . ? C3 C4 C5 107.71(16) . . ? C3 C4 Fe1 69.95(9) . . ? C5 C4 Fe1 70.01(10) . . ? C3 C4 H4 125.9(15) . . ? C5 C4 H4 126.3(15) . . ? Fe1 C4 H4 122.7(15) . . ? C1 C5 C4 107.64(16) . . ? C1 C5 Fe1 70.13(10) . . ? C4 C5 Fe1 69.31(10) . . ? C1 C5 H5 124.7(16) . . ? C4 C5 H5 127.3(16) . . ? Fe1 C5 H5 121.3(17) . . ? C7 C6 C10 107.12(11) . . ? C7 C6 C22 132.12(12) . . ? C10 C6 C22 120.61(11) . . ? C7 C6 Fe1 68.49(7) . . ? C10 C6 Fe1 69.25(7) . . ? C22 C6 Fe1 123.76(9) . . ? C8 C7 C6 108.19(11) . . ? C8 C7 Fe1 69.57(7) . . ? C6 C7 Fe1 70.53(7) . . ? C8 C7 H7 125.4(10) . . ? C6 C7 H7 126.3(10) . . ? Fe1 C7 H7 123.5(10) . . ? C7 C8 C9 108.33(11) . . ? C7 C8 Fe1 69.44(7) . . ? C9 C8 Fe1 69.93(7) . . ? C7 C8 H8 126.7(10) . . ? C9 C8 H8 124.8(10) . . ? Fe1 C8 H8 123.1(10) . . ? C10 C9 C8 107.64(11) . . ? C10 C9 Fe1 69.94(7) . . ? C8 C9 Fe1 69.05(7) . . ? C10 C9 H9 127.5(10) . . ? C8 C9 H9 124.8(10) . . ? Fe1 C9 H9 124.6(10) . . ? C9 C10 C6 108.72(11) . . ? C9 C10 C11 130.27(12) . . ? C6 C10 C11 120.92(11) . . ? C9 C10 Fe1 69.51(7) . . ? C6 C10 Fe1 69.86(7) . . ? C11 C10 Fe1 129.24(9) . . ? C10 C11 C12 109.02(11) . . ? C10 C11 H11A 113.4(11) . . ? C12 C11 H11A 110.9(11) . . ? C10 C11 H11B 108.0(10) . . ? C12 C11 H11B 107.3(10) . . ? H11A C11 H11B 108.0(15) . . ? C13 C12 C11 113.51(10) . . ? C13 C12 H12A 109.1(12) . . ? C11 C12 H12A 106.3(11) . . ? C13 C12 H12B 106.7(12) . . ? C11 C12 H12B 111.6(11) . . ? H12A C12 H12B 109.6(17) . . ? C14 C13 C22 119.93(12) . . ? C14 C13 C12 118.26(11) . . ? C22 C13 C12 121.74(11) . . ? C15 C14 C13 121.31(11) . . ? C15 C14 H14 117.5(11) . . ? C13 C14 H14 121.2(11) . . ? C14 C15 C16 120.03(11) . . ? C14 C15 H15 123.2(11) . . ? C16 C15 H15 116.6(11) . . ? C15 C16 C21 120.06(12) . . ? C15 C16 C17 117.97(11) . . ? C21 C16 C17 121.95(11) . . ? O1 C17 C18 120.17(13) . . ? O1 C17 C16 120.99(12) . . ? C18 C17 C16 118.79(11) . . ? C19 C18 C17 118.46(12) . . ? C19 C18 C23 123.71(13) . . ? C17 C18 C23 117.71(12) . . ? C18 C19 C20 123.23(12) . . ? C18 C19 H19 123.2(10) . . ? C20 C19 H19 113.5(10) . . ? O2 C20 C19 118.69(11) . . ? O2 C20 C21 122.80(11) . . ? C19 C20 C21 118.30(10) . . ? C22 C21 C16 120.11(11) . . ? C22 C21 C20 124.10(10) . . ? C16 C21 C20 115.63(11) . . ? C21 C22 C13 118.22(11) . . ? C21 C22 C6 125.52(11) . . ? C13 C22 C6 116.23(11) . . ? C18 C23 H23A 110.6(15) . . ? C18 C23 H23B 108.0(13) . . ? H23A C23 H23B 110(2) . . ? C18 C23 H23C 112.4(15) . . ? H23A C23 H23C 104(2) . . ? H23B C23 H23C 112(2) . . ? 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 C4 Fe1 C1 C2 -81.30(12) . . . . ? C7 Fe1 C1 C2 21.3(4) . . . . ? C8 Fe1 C1 C2 -163.59(12) . . . . ? C3 Fe1 C1 C2 -37.32(11) . . . . ? C5 Fe1 C1 C2 -119.37(16) . . . . ? C9 Fe1 C1 C2 156.61(10) . . . . ? C10 Fe1 C1 C2 112.21(11) . . . . ? C6 Fe1 C1 C2 69.92(13) . . . . ? C4 Fe1 C1 C5 38.07(11) . . . . ? C7 Fe1 C1 C5 140.7(3) . . . . ? C8 Fe1 C1 C5 -44.22(17) . . . . ? C3 Fe1 C1 C5 82.05(12) . . . . ? C2 Fe1 C1 C5 119.37(16) . . . . ? C9 Fe1 C1 C5 -84.02(11) . . . . ? C10 Fe1 C1 C5 -128.42(10) . . . . ? C6 Fe1 C1 C5 -170.71(11) . . . . ? C5 C1 C2 C3 -0.04(18) . . . . ? Fe1 C1 C2 C3 59.23(11) . . . . ? C5 C1 C2 Fe1 -59.27(12) . . . . ? C4 Fe1 C2 C3 -37.83(11) . . . . ? C7 Fe1 C2 C3 65.45(12) . . . . ? C8 Fe1 C2 C3 21.9(3) . . . . ? C5 Fe1 C2 C3 -81.94(12) . . . . ? C1 Fe1 C2 C3 -119.48(15) . . . . ? C9 Fe1 C2 C3 -167.86(12) . . . . ? C10 Fe1 C2 C3 152.55(9) . . . . ? C6 Fe1 C2 C3 108.14(10) . . . . ? C4 Fe1 C2 C1 81.65(12) . . . . ? C7 Fe1 C2 C1 -175.07(10) . . . . ? C8 Fe1 C2 C1 141.4(2) . . . . ? C3 Fe1 C2 C1 119.48(15) . . . . ? C5 Fe1 C2 C1 37.53(12) . . . . ? C9 Fe1 C2 C1 -48.38(18) . . . . ? C10 Fe1 C2 C1 -87.97(12) . . . . ? C6 Fe1 C2 C1 -132.38(11) . . . . ? C1 C2 C3 C4 -0.05(18) . . . . ? Fe1 C2 C3 C4 59.42(11) . . . . ? C1 C2 C3 Fe1 -59.47(11) . . . . ? C4 Fe1 C3 C2 119.15(15) . . . . ? C7 Fe1 C3 C2 -133.40(10) . . . . ? C8 Fe1 C3 C2 -173.78(9) . . . . ? C5 Fe1 C3 C2 81.01(11) . . . . ? C1 Fe1 C3 C2 37.33(11) . . . . ? C9 Fe1 C3 C2 156.0(2) . . . . ? C10 Fe1 C3 C2 -57.10(17) . . . . ? C6 Fe1 C3 C2 -90.44(10) . . . . ? C7 Fe1 C3 C4 107.45(11) . . . . ? C8 Fe1 C3 C4 67.07(13) . . . . ? C5 Fe1 C3 C4 -38.14(12) . . . . ? C2 Fe1 C3 C4 -119.15(15) . . . . ? C1 Fe1 C3 C4 -81.82(12) . . . . ? C9 Fe1 C3 C4 36.8(3) . . . . ? C10 Fe1 C3 C4 -176.25(12) . . . . ? C6 Fe1 C3 C4 150.40(10) . . . . ? C2 C3 C4 C5 0.12(18) . . . . ? Fe1 C3 C4 C5 60.09(11) . . . . ? C2 C3 C4 Fe1 -59.97(11) . . . . ? C7 Fe1 C4 C3 -88.09(11) . . . . ? C8 Fe1 C4 C3 -130.71(11) . . . . ? C5 Fe1 C4 C3 118.52(15) . . . . ? C2 Fe1 C4 C3 37.38(11) . . . . ? C1 Fe1 C4 C3 80.79(12) . . . . ? C9 Fe1 C4 C3 -169.48(10) . . . . ? C10 Fe1 C4 C3 171.8(3) . . . . ? C6 Fe1 C4 C3 -56.77(16) . . . . ? C7 Fe1 C4 C5 153.39(10) . . . . ? C8 Fe1 C4 C5 110.77(11) . . . . ? C3 Fe1 C4 C5 -118.52(15) . . . . ? C2 Fe1 C4 C5 -81.14(11) . . . . ? C1 Fe1 C4 C5 -37.73(11) . . . . ? C9 Fe1 C4 C5 72.00(12) . . . . ? C10 Fe1 C4 C5 53.3(3) . . . . ? C6 Fe1 C4 C5 -175.29(11) . . . . ? C2 C1 C5 C4 0.12(19) . . . . ? Fe1 C1 C5 C4 -59.39(12) . . . . ? C2 C1 C5 Fe1 59.51(11) . . . . ? C3 C4 C5 C1 -0.15(19) . . . . ? Fe1 C4 C5 C1 59.90(12) . . . . ? C3 C4 C5 Fe1 -60.05(11) . . . . ? C4 Fe1 C5 C1 -118.75(15) . . . . ? C7 Fe1 C5 C1 -167.81(11) . . . . ? C8 Fe1 C5 C1 156.96(10) . . . . ? C3 Fe1 C5 C1 -80.73(12) . . . . ? C2 Fe1 C5 C1 -37.33(11) . . . . ? C9 Fe1 C5 C1 113.41(10) . . . . ? C10 Fe1 C5 C1 74.58(12) . . . . ? C6 Fe1 C5 C1 46.1(4) . . . . ? C7 Fe1 C5 C4 -49.06(16) . . . . ? C8 Fe1 C5 C4 -84.29(11) . . . . ? C3 Fe1 C5 C4 38.02(11) . . . . ? C2 Fe1 C5 C4 81.42(11) . . . . ? C1 Fe1 C5 C4 118.75(15) . . . . ? C9 Fe1 C5 C4 -127.83(10) . . . . ? C10 Fe1 C5 C4 -166.67(10) . . . . ? C6 Fe1 C5 C4 164.8(4) . . . . ? C4 Fe1 C6 C7 -46.42(14) . . . . ? C8 Fe1 C6 C7 37.97(7) . . . . ? C3 Fe1 C6 C7 -84.20(10) . . . . ? C5 Fe1 C6 C7 152.6(4) . . . . ? C2 Fe1 C6 C7 -127.75(9) . . . . ? C1 Fe1 C6 C7 -168.08(9) . . . . ? C9 Fe1 C6 C7 82.10(8) . . . . ? C10 Fe1 C6 C7 119.18(10) . . . . ? C4 Fe1 C6 C10 -165.60(12) . . . . ? C7 Fe1 C6 C10 -119.18(10) . . . . ? C8 Fe1 C6 C10 -81.21(8) . . . . ? C3 Fe1 C6 C10 156.62(9) . . . . ? C5 Fe1 C6 C10 33.4(4) . . . . ? C2 Fe1 C6 C10 113.08(9) . . . . ? C1 Fe1 C6 C10 72.74(11) . . . . ? C9 Fe1 C6 C10 -37.08(7) . . . . ? C4 Fe1 C6 C22 80.71(15) . . . . ? C7 Fe1 C6 C22 127.13(14) . . . . ? C8 Fe1 C6 C22 165.10(12) . . . . ? C3 Fe1 C6 C22 42.93(13) . . . . ? C5 Fe1 C6 C22 -80.3(4) . . . . ? C2 Fe1 C6 C22 -0.61(13) . . . . ? C1 Fe1 C6 C22 -40.95(15) . . . . ? C9 Fe1 C6 C22 -150.76(12) . . . . ? C10 Fe1 C6 C22 -113.69(13) . . . . ? C10 C6 C7 C8 -0.93(14) . . . . ? C22 C6 C7 C8 -176.30(13) . . . . ? Fe1 C6 C7 C8 -59.62(9) . . . . ? C10 C6 C7 Fe1 58.69(9) . . . . ? C22 C6 C7 Fe1 -116.68(14) . . . . ? C4 Fe1 C7 C8 -85.54(10) . . . . ? C3 Fe1 C7 C8 -128.29(9) . . . . ? C5 Fe1 C7 C8 -52.94(14) . . . . ? C2 Fe1 C7 C8 -165.99(9) . . . . ? C1 Fe1 C7 C8 176.2(3) . . . . ? C9 Fe1 C7 C8 37.62(7) . . . . ? C10 Fe1 C7 C8 81.20(8) . . . . ? C6 Fe1 C7 C8 119.01(11) . . . . ? C4 Fe1 C7 C6 155.45(9) . . . . ? C8 Fe1 C7 C6 -119.01(11) . . . . ? C3 Fe1 C7 C6 112.70(9) . . . . ? C5 Fe1 C7 C6 -171.95(12) . . . . ? C2 Fe1 C7 C6 75.00(11) . . . . ? C1 Fe1 C7 C6 57.2(4) . . . . ? C9 Fe1 C7 C6 -81.38(8) . . . . ? C10 Fe1 C7 C6 -37.80(7) . . . . ? C6 C7 C8 C9 0.91(14) . . . . ? Fe1 C7 C8 C9 -59.31(9) . . . . ? C6 C7 C8 Fe1 60.22(9) . . . . ? C4 Fe1 C8 C7 109.34(9) . . . . ? C3 Fe1 C8 C7 71.01(10) . . . . ? C5 Fe1 C8 C7 151.54(9) . . . . ? C2 Fe1 C8 C7 53.4(3) . . . . ? C1 Fe1 C8 C7 -178.64(12) . . . . ? C9 Fe1 C8 C7 -119.65(11) . . . . ? C10 Fe1 C8 C7 -82.00(8) . . . . ? C6 Fe1 C8 C7 -37.96(7) . . . . ? C4 Fe1 C8 C9 -131.01(9) . . . . ? C7 Fe1 C8 C9 119.65(11) . . . . ? C3 Fe1 C8 C9 -169.33(9) . . . . ? C5 Fe1 C8 C9 -88.81(10) . . . . ? C2 Fe1 C8 C9 173.1(2) . . . . ? C1 Fe1 C8 C9 -58.99(15) . . . . ? C10 Fe1 C8 C9 37.65(7) . . . . ? C6 Fe1 C8 C9 81.69(8) . . . . ? C7 C8 C9 C10 -0.53(14) . . . . ? Fe1 C8 C9 C10 -59.53(9) . . . . ? C7 C8 C9 Fe1 59.00(9) . . . . ? C4 Fe1 C9 C10 -173.85(10) . . . . ? C7 Fe1 C9 C10 81.43(8) . . . . ? C8 Fe1 C9 C10 119.03(11) . . . . ? C3 Fe1 C9 C10 156.6(2) . . . . ? C5 Fe1 C9 C10 -133.24(9) . . . . ? C2 Fe1 C9 C10 -57.55(15) . . . . ? C1 Fe1 C9 C10 -90.75(10) . . . . ? C6 Fe1 C9 C10 37.38(7) . . . . ? C4 Fe1 C9 C8 67.12(11) . . . . ? C7 Fe1 C9 C8 -37.60(7) . . . . ? C3 Fe1 C9 C8 37.6(3) . . . . ? C5 Fe1 C9 C8 107.73(10) . . . . ? C2 Fe1 C9 C8 -176.57(12) . . . . ? C1 Fe1 C9 C8 150.22(9) . . . . ? C10 Fe1 C9 C8 -119.03(11) . . . . ? C6 Fe1 C9 C8 -81.65(8) . . . . ? C8 C9 C10 C6 -0.05(14) . . . . ? Fe1 C9 C10 C6 -59.03(9) . . . . ? C8 C9 C10 C11 -176.38(13) . . . . ? Fe1 C9 C10 C11 124.65(14) . . . . ? C8 C9 C10 Fe1 58.97(9) . . . . ? C7 C6 C10 C9 0.61(14) . . . . ? C22 C6 C10 C9 176.61(11) . . . . ? Fe1 C6 C10 C9 58.81(9) . . . . ? C7 C6 C10 C11 177.34(11) . . . . ? C22 C6 C10 C11 -6.66(18) . . . . ? Fe1 C6 C10 C11 -124.46(12) . . . . ? C7 C6 C10 Fe1 -58.20(9) . . . . ? C22 C6 C10 Fe1 117.80(11) . . . . ? C4 Fe1 C10 C9 23.0(3) . . . . ? C7 Fe1 C10 C9 -82.24(8) . . . . ? C8 Fe1 C10 C9 -38.08(8) . . . . ? C3 Fe1 C10 C9 -168.33(12) . . . . ? C5 Fe1 C10 C9 66.77(11) . . . . ? C2 Fe1 C10 C9 152.77(9) . . . . ? C1 Fe1 C10 C9 108.93(9) . . . . ? C6 Fe1 C10 C9 -120.12(10) . . . . ? C4 Fe1 C10 C6 143.1(3) . . . . ? C7 Fe1 C10 C6 37.89(7) . . . . ? C8 Fe1 C10 C6 82.05(7) . . . . ? C3 Fe1 C10 C6 -48.21(15) . . . . ? C5 Fe1 C10 C6 -173.11(9) . . . . ? C2 Fe1 C10 C6 -87.11(9) . . . . ? C1 Fe1 C10 C6 -130.95(9) . . . . ? C9 Fe1 C10 C6 120.12(10) . . . . ? C4 Fe1 C10 C11 -102.9(3) . . . . ? C7 Fe1 C10 C11 151.91(13) . . . . ? C8 Fe1 C10 C11 -163.93(13) . . . . ? C3 Fe1 C10 C11 65.81(19) . . . . ? C5 Fe1 C10 C11 -59.09(15) . . . . ? C2 Fe1 C10 C11 26.91(15) . . . . ? C1 Fe1 C10 C11 -16.93(14) . . . . ? C9 Fe1 C10 C11 -125.86(15) . . . . ? C6 Fe1 C10 C11 114.02(14) . . . . ? C9 C10 C11 C12 -146.40(13) . . . . ? C6 C10 C11 C12 37.66(16) . . . . ? Fe1 C10 C11 C12 -50.68(16) . . . . ? C10 C11 C12 C13 -47.40(15) . . . . ? C11 C12 C13 C14 -153.03(12) . . . . ? C11 C12 C13 C22 29.89(17) . . . . ? C22 C13 C14 C15 0.86(19) . . . . ? C12 C13 C14 C15 -176.28(12) . . . . ? C13 C14 C15 C16 -2.3(2) . . . . ? C14 C15 C16 C21 -0.96(19) . . . . ? C14 C15 C16 C17 177.40(12) . . . . ? C15 C16 C17 O1 1.19(19) . . . . ? C21 C16 C17 O1 179.51(12) . . . . ? C15 C16 C17 C18 -176.05(11) . . . . ? C21 C16 C17 C18 2.27(18) . . . . ? O1 C17 C18 C19 176.59(13) . . . . ? C16 C17 C18 C19 -6.15(18) . . . . ? O1 C17 C18 C23 0.34(19) . . . . ? C16 C17 C18 C23 177.61(11) . . . . ? C17 C18 C19 C20 -4.89(19) . . . . ? C23 C18 C19 C20 171.12(12) . . . . ? C18 C19 C20 O2 -155.40(12) . . . . ? C18 C19 C20 C21 19.55(18) . . . . ? C15 C16 C21 C22 5.59(18) . . . . ? C17 C16 C21 C22 -172.70(11) . . . . ? C15 C16 C21 C20 -169.99(11) . . . . ? C17 C16 C21 C20 11.72(17) . . . . ? O2 C20 C21 C22 -22.67(19) . . . . ? C19 C20 C21 C22 162.60(11) . . . . ? O2 C20 C21 C16 152.71(12) . . . . ? C19 C20 C21 C16 -22.02(16) . . . . ? C16 C21 C22 C13 -6.86(17) . . . . ? C20 C21 C22 C13 168.33(11) . . . . ? C16 C21 C22 C6 171.19(12) . . . . ? C20 C21 C22 C6 -13.62(19) . . . . ? C14 C13 C22 C21 3.70(17) . . . . ? C12 C13 C22 C21 -179.27(11) . . . . ? C14 C13 C22 C6 -174.53(12) . . . . ? C12 C13 C22 C6 2.50(17) . . . . ? C7 C6 C22 C21 -18.4(2) . . . . ? C10 C6 C22 C21 166.78(11) . . . . ? Fe1 C6 C22 C21 -108.93(12) . . . . ? C7 C6 C22 C13 159.71(13) . . . . ? C10 C6 C22 C13 -15.14(17) . . . . ? Fe1 C6 C22 C13 69.15(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.053