# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Dr H. Schmalz' _publ_contact_author_email schmalz@uni-koeln.de loop_ _publ_author_name H.Schmalz S.Romanski S.Amslinger B.Kraus M.Guttentag ; W.Schlundt ; H.Rucker A.Adler R.Alberto J.Neudoerfl # Attachment '- rac11.cif' data_rac11 _database_code_depnum_ccdc_archive 'CCDC 872868' #TrackingRef '- rac11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 Fe O5' _chemical_formula_sum 'C13 H14 Fe O5' _chemical_formula_weight 306.09 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6264(7) _cell_length_b 14.1259(7) _cell_length_c 11.9873(6) _cell_angle_alpha 90.00 _cell_angle_beta 124.757(4) _cell_angle_gamma 90.00 _cell_volume 1339.21(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6848 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.99 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .07 _exptl_crystal_size_min .02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.138 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6848 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2918 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H7, H8 and H11 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0337P)^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 2918 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.91645(3) 0.252682(17) 0.69824(3) 0.01767(11) Uani 1 1 d . . . O1 O 0.66031(18) 0.29843(10) 0.41076(15) 0.0301(4) Uani 1 1 d . . . O2 O 0.76254(17) 0.37644(9) 0.79676(14) 0.0250(3) Uani 1 1 d . . . O3 O 1.19682(18) 0.37323(10) 0.75235(15) 0.0316(4) Uani 1 1 d . . . O4 O 0.72899(15) 0.07505(9) 0.54687(13) 0.0195(3) Uani 1 1 d . . . O5 O 0.86460(17) -0.05090(9) 0.53397(14) 0.0229(3) Uani 1 1 d . . . C1 C 0.7602(3) 0.28095(14) 0.5229(2) 0.0225(5) Uani 1 1 d . . . C2 C 0.8218(2) 0.32884(13) 0.7572(2) 0.0204(5) Uani 1 1 d . . . C3 C 1.0867(3) 0.32677(14) 0.7326(2) 0.0224(5) Uani 1 1 d . . . C4 C 0.8819(2) 0.10929(13) 0.6623(2) 0.0175(4) Uani 1 1 d . . . C5 C 0.7368(2) -0.00722(13) 0.48884(19) 0.0187(4) Uani 1 1 d . . . C6 C 0.5650(2) -0.03176(14) 0.3688(2) 0.0247(5) Uani 1 1 d . . . H6A H 0.5733 -0.0839 0.3189 0.037 Uiso 1 1 calc R . . H6B H 0.5148 0.0236 0.3093 0.037 Uiso 1 1 calc R . . H6C H 0.4938 -0.0511 0.3991 0.037 Uiso 1 1 calc R . . C7 C 0.8879(2) 0.13205(13) 0.7786(2) 0.0189(4) Uani 1 1 d . . . H7 H 0.7941 0.1229 0.7838 0.023 Uiso 1 1 d R . . C8 C 1.0434(2) 0.17698(13) 0.8804(2) 0.0204(5) Uani 1 1 d . . . H8 H 1.0490 0.2017 0.9568 0.024 Uiso 1 1 d R . . C9 C 1.2088(2) 0.13273(14) 0.9163(2) 0.0221(5) Uani 1 1 d . . . C10 C 1.1999(2) 0.12066(14) 0.7843(2) 0.0210(5) Uani 1 1 d . . . H10A H 1.2769 0.1668 0.7837 0.025 Uiso 1 1 calc R . . H10B H 1.2384 0.0562 0.7817 0.025 Uiso 1 1 calc R . . C11 C 1.0217(2) 0.13568(12) 0.6594(2) 0.0190(4) Uani 1 1 d . . . H11 H 1.0087 0.1312 0.5747 0.023 Uiso 1 1 d R . . C12 C 1.3587(3) 0.19549(15) 1.0185(2) 0.0321(6) Uani 1 1 d . . . H12A H 1.3437 0.2589 0.9801 0.048 Uiso 1 1 calc R . . H12B H 1.4638 0.1678 1.0382 0.048 Uiso 1 1 calc R . . H12C H 1.3644 0.1999 1.1026 0.048 Uiso 1 1 calc R . . C13 C 1.2293(3) 0.03542(14) 0.9825(2) 0.0301(5) Uani 1 1 d . . . H13A H 1.2220 0.0431 1.0603 0.045 Uiso 1 1 calc R . . H13B H 1.3395 0.0085 1.0133 0.045 Uiso 1 1 calc R . . H13C H 1.1393 -0.0071 0.9159 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01817(18) 0.01974(17) 0.01490(18) -0.00103(11) 0.00931(14) -0.00012(11) O1 0.0323(9) 0.0355(9) 0.0177(9) 0.0023(7) 0.0115(8) 0.0050(7) O2 0.0244(8) 0.0289(8) 0.0232(9) -0.0035(6) 0.0144(7) 0.0012(6) O3 0.0322(9) 0.0344(9) 0.0338(10) -0.0042(7) 0.0221(8) -0.0095(7) O4 0.0163(7) 0.0223(7) 0.0168(8) -0.0047(6) 0.0077(6) -0.0018(6) O5 0.0234(8) 0.0225(7) 0.0212(8) 0.0001(6) 0.0118(7) 0.0032(6) C1 0.0261(12) 0.0205(10) 0.0255(13) -0.0029(9) 0.0174(11) -0.0012(9) C2 0.0187(10) 0.0223(11) 0.0150(11) 0.0018(8) 0.0066(9) 0.0002(9) C3 0.0264(12) 0.0241(11) 0.0157(12) -0.0016(8) 0.0114(10) 0.0029(9) C4 0.0176(10) 0.0178(9) 0.0152(11) -0.0008(8) 0.0082(9) 0.0005(8) C5 0.0232(11) 0.0199(10) 0.0161(11) -0.0010(8) 0.0132(10) -0.0054(9) C6 0.0217(11) 0.0279(11) 0.0233(12) -0.0060(9) 0.0121(10) -0.0048(9) C7 0.0209(10) 0.0187(10) 0.0197(12) 0.0022(8) 0.0131(9) 0.0007(8) C8 0.0236(11) 0.0224(10) 0.0132(11) -0.0002(8) 0.0093(9) 0.0003(8) C9 0.0175(10) 0.0258(11) 0.0171(11) -0.0019(8) 0.0064(9) 0.0014(9) C10 0.0171(10) 0.0226(10) 0.0204(12) -0.0019(8) 0.0091(9) 0.0018(8) C11 0.0213(11) 0.0192(10) 0.0191(11) -0.0020(8) 0.0130(9) 0.0022(8) C12 0.0248(12) 0.0374(13) 0.0248(13) -0.0047(10) 0.0087(11) -0.0020(10) C13 0.0298(12) 0.0293(12) 0.0214(12) 0.0025(9) 0.0089(11) 0.0047(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C3 1.783(2) . ? Fe1 C2 1.794(2) . ? Fe1 C1 1.799(2) . ? Fe1 C7 2.0518(19) . ? Fe1 C4 2.0581(18) . ? Fe1 C8 2.0888(19) . ? Fe1 C11 2.1244(18) . ? O1 C1 1.148(2) . ? O2 C2 1.146(2) . ? O3 C3 1.151(2) . ? O4 C5 1.378(2) . ? O4 C4 1.412(2) . ? O5 C5 1.195(2) . ? C4 C7 1.400(3) . ? C4 C11 1.416(3) . ? C5 C6 1.487(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.432(3) . ? C7 H7 0.9482 . ? C8 C9 1.526(3) . ? C8 H8 0.9517 . ? C9 C12 1.534(3) . ? C9 C13 1.542(3) . ? C9 C10 1.545(3) . ? C10 C11 1.517(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11 0.9510 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 C2 99.38(9) . . ? C3 Fe1 C1 100.72(9) . . ? C2 Fe1 C1 93.03(9) . . ? C3 Fe1 C7 136.91(9) . . ? C2 Fe1 C7 94.53(9) . . ? C1 Fe1 C7 119.11(9) . . ? C3 Fe1 C4 130.05(8) . . ? C2 Fe1 C4 127.94(8) . . ? C1 Fe1 C4 92.65(8) . . ? C7 Fe1 C4 39.83(7) . . ? C3 Fe1 C8 98.40(8) . . ? C2 Fe1 C8 91.20(8) . . ? C1 Fe1 C8 159.46(8) . . ? C7 Fe1 C8 40.44(7) . . ? C4 Fe1 C8 69.11(8) . . ? C3 Fe1 C11 90.97(8) . . ? C2 Fe1 C11 164.87(8) . . ? C1 Fe1 C11 95.87(8) . . ? C7 Fe1 C11 70.44(8) . . ? C4 Fe1 C11 39.54(7) . . ? C8 Fe1 C11 76.29(8) . . ? C5 O4 C4 117.20(14) . . ? O1 C1 Fe1 179.59(18) . . ? O2 C2 Fe1 178.78(18) . . ? O3 C3 Fe1 178.17(19) . . ? C7 C4 O4 118.86(17) . . ? C7 C4 C11 117.65(17) . . ? O4 C4 C11 122.75(18) . . ? C7 C4 Fe1 69.84(11) . . ? O4 C4 Fe1 119.74(12) . . ? C11 C4 Fe1 72.76(11) . . ? O5 C5 O4 123.04(17) . . ? O5 C5 C6 127.40(17) . . ? O4 C5 C6 109.53(16) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 C8 112.34(18) . . ? C4 C7 Fe1 70.33(11) . . ? C8 C7 Fe1 71.17(11) . . ? C4 C7 H7 122.3 . . ? C8 C7 H7 125.2 . . ? Fe1 C7 H7 122.1 . . ? C7 C8 C9 118.33(17) . . ? C7 C8 Fe1 68.39(11) . . ? C9 C8 Fe1 113.51(14) . . ? C7 C8 H8 116.2 . . ? C9 C8 H8 113.6 . . ? Fe1 C8 H8 119.8 . . ? C8 C9 C12 110.11(16) . . ? C8 C9 C13 108.49(17) . . ? C12 C9 C13 108.55(17) . . ? C8 C9 C10 108.45(16) . . ? C12 C9 C10 111.06(18) . . ? C13 C9 C10 110.16(16) . . ? C11 C10 C9 111.53(16) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C4 C11 C10 119.65(18) . . ? C4 C11 Fe1 67.71(10) . . ? C10 C11 Fe1 107.74(13) . . ? C4 C11 H11 117.4 . . ? C10 C11 H11 115.6 . . ? Fe1 C11 H11 119.7 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O4 C4 C7 -129.24(18) . . . . ? C5 O4 C4 C11 60.9(2) . . . . ? C5 O4 C4 Fe1 148.71(13) . . . . ? C3 Fe1 C4 C7 118.80(14) . . . . ? C2 Fe1 C4 C7 -38.90(15) . . . . ? C1 Fe1 C4 C7 -134.82(13) . . . . ? C8 Fe1 C4 C7 35.49(12) . . . . ? C11 Fe1 C4 C7 129.16(17) . . . . ? C3 Fe1 C4 O4 -128.72(15) . . . . ? C2 Fe1 C4 O4 73.58(18) . . . . ? C1 Fe1 C4 O4 -22.34(16) . . . . ? C7 Fe1 C4 O4 112.48(19) . . . . ? C8 Fe1 C4 O4 147.97(17) . . . . ? C11 Fe1 C4 O4 -118.4(2) . . . . ? C3 Fe1 C4 C11 -10.36(17) . . . . ? C2 Fe1 C4 C11 -168.06(12) . . . . ? C1 Fe1 C4 C11 96.02(12) . . . . ? C7 Fe1 C4 C11 -129.16(17) . . . . ? C8 Fe1 C4 C11 -93.67(12) . . . . ? C4 O4 C5 O5 2.1(3) . . . . ? C4 O4 C5 C6 -179.60(16) . . . . ? O4 C4 C7 C8 -172.48(15) . . . . ? C11 C4 C7 C8 -2.1(2) . . . . ? Fe1 C4 C7 C8 -58.83(13) . . . . ? O4 C4 C7 Fe1 -113.65(16) . . . . ? C11 C4 C7 Fe1 56.72(15) . . . . ? C3 Fe1 C7 C4 -100.88(15) . . . . ? C2 Fe1 C7 C4 150.21(12) . . . . ? C1 Fe1 C7 C4 54.19(14) . . . . ? C8 Fe1 C7 C4 -123.26(17) . . . . ? C11 Fe1 C7 C4 -31.59(11) . . . . ? C3 Fe1 C7 C8 22.38(19) . . . . ? C2 Fe1 C7 C8 -86.53(12) . . . . ? C1 Fe1 C7 C8 177.45(12) . . . . ? C4 Fe1 C7 C8 123.26(17) . . . . ? C11 Fe1 C7 C8 91.67(12) . . . . ? C4 C7 C8 C9 -47.5(2) . . . . ? Fe1 C7 C8 C9 -105.90(17) . . . . ? C4 C7 C8 Fe1 58.35(14) . . . . ? C3 Fe1 C8 C7 -164.76(13) . . . . ? C2 Fe1 C8 C7 95.58(12) . . . . ? C1 Fe1 C8 C7 -6.4(3) . . . . ? C4 Fe1 C8 C7 -34.98(11) . . . . ? C11 Fe1 C8 C7 -75.81(12) . . . . ? C3 Fe1 C8 C9 -52.16(14) . . . . ? C2 Fe1 C8 C9 -151.82(14) . . . . ? C1 Fe1 C8 C9 106.2(3) . . . . ? C7 Fe1 C8 C9 112.60(18) . . . . ? C4 Fe1 C8 C9 77.62(14) . . . . ? C11 Fe1 C8 C9 36.79(13) . . . . ? C7 C8 C9 C12 175.54(19) . . . . ? Fe1 C8 C9 C12 98.35(18) . . . . ? C7 C8 C9 C13 -65.8(2) . . . . ? Fe1 C8 C9 C13 -142.99(14) . . . . ? C7 C8 C9 C10 53.8(2) . . . . ? Fe1 C8 C9 C10 -23.35(18) . . . . ? C8 C9 C10 C11 -12.2(2) . . . . ? C12 C9 C10 C11 -133.28(17) . . . . ? C13 C9 C10 C11 106.43(18) . . . . ? C7 C4 C11 C10 43.1(2) . . . . ? O4 C4 C11 C10 -146.92(17) . . . . ? Fe1 C4 C11 C10 98.37(16) . . . . ? C7 C4 C11 Fe1 -55.26(15) . . . . ? O4 C4 C11 Fe1 114.71(17) . . . . ? C9 C10 C11 C4 -32.8(2) . . . . ? C9 C10 C11 Fe1 41.13(18) . . . . ? C3 Fe1 C11 C4 172.08(13) . . . . ? C2 Fe1 C11 C4 38.7(3) . . . . ? C1 Fe1 C11 C4 -87.04(12) . . . . ? C7 Fe1 C11 C4 31.81(11) . . . . ? C8 Fe1 C11 C4 73.67(12) . . . . ? C3 Fe1 C11 C10 56.60(14) . . . . ? C2 Fe1 C11 C10 -76.8(3) . . . . ? C1 Fe1 C11 C10 157.48(14) . . . . ? C7 Fe1 C11 C10 -83.67(14) . . . . ? C4 Fe1 C11 C10 -115.48(18) . . . . ? C8 Fe1 C11 C10 -41.81(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.533 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.066 # Attachment '- rac14.cif' data_rac-14 _database_code_depnum_ccdc_archive 'CCDC 872869' #TrackingRef '- rac14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H28 Fe O7' _chemical_formula_sum 'C21 H28 Fe O7' _chemical_formula_weight 448.28 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0195(8) _cell_length_b 13.4293(8) _cell_length_c 16.2464(10) _cell_angle_alpha 75.189(4) _cell_angle_beta 86.972(3) _cell_angle_gamma 89.571(3) _cell_volume 2321.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15189 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15189 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.1434 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 27.00 _reflns_number_total 10119 _reflns_number_gt 5007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _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^)+(0.0848P)^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 10119 _refine_ls_number_parameters 539 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1565 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1848 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.006 _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 0.64337(6) 0.14582(5) 0.26419(4) 0.0374(2) Uani 1 1 d . . . O1 O 0.7477(4) -0.0361(3) 0.3811(2) 0.0654(11) Uani 1 1 d . . . O2 O 0.5505(4) 0.0687(3) 0.1263(2) 0.0702(12) Uani 1 1 d . . . O3 O 0.4081(4) 0.1269(3) 0.3600(2) 0.0708(11) Uani 1 1 d . . . O4 O 0.8472(3) 0.2070(2) 0.35591(17) 0.0413(8) Uani 1 1 d . . . O5 O 0.9708(3) 0.3424(3) 0.3062(2) 0.0553(10) Uani 1 1 d . . . O6 O 0.4991(3) 0.3358(2) 0.19255(17) 0.0402(8) Uani 1 1 d . . . O7 O 0.5670(4) 0.4898(3) 0.2006(3) 0.0647(11) Uani 1 1 d . . . C1 C 0.7048(5) 0.0318(4) 0.3355(3) 0.0471(13) Uani 1 1 d . . . C2 C 0.5901(5) 0.0958(4) 0.1801(3) 0.0484(13) Uani 1 1 d . . . C3 C 0.5017(5) 0.1342(3) 0.3238(3) 0.0479(13) Uani 1 1 d . . . C4 C 0.7862(4) 0.2333(3) 0.2791(2) 0.0336(11) Uani 1 1 d . . . C5 C 0.9439(4) 0.2680(4) 0.3603(3) 0.0356(11) Uani 1 1 d . . . C6 C 1.0115(4) 0.2237(4) 0.4406(3) 0.0458(13) Uani 1 1 d . . . C7 C 0.9258(5) 0.1712(4) 0.5162(3) 0.0632(16) Uani 1 1 d . . . H7A H 0.8692 0.2220 0.5298 0.095 Uiso 1 1 calc R . . H7B H 0.9734 0.1414 0.5658 0.095 Uiso 1 1 calc R . . H7C H 0.8800 0.1164 0.5015 0.095 Uiso 1 1 calc R . . C8 C 1.0808(6) 0.3124(5) 0.4614(3) 0.0726(18) Uani 1 1 d . . . H8A H 1.1366 0.3445 0.4131 0.109 Uiso 1 1 calc R . . H8B H 1.1272 0.2855 0.5121 0.109 Uiso 1 1 calc R . . H8C H 1.0228 0.3639 0.4723 0.109 Uiso 1 1 calc R . . C9 C 1.0999(6) 0.1442(5) 0.4191(4) 0.083(2) Uani 1 1 d . . . H9A H 1.0541 0.0901 0.4036 0.124 Uiso 1 1 calc R . . H9B H 1.1468 0.1137 0.4689 0.124 Uiso 1 1 calc R . . H9C H 1.1554 0.1781 0.3712 0.124 Uiso 1 1 calc R . . C10 C 0.6796(4) 0.2918(3) 0.2738(3) 0.0346(11) Uani 1 1 d . . . H10 H 0.6488 0.3167 0.3205 0.042 Uiso 1 1 d R . . C11 C 0.6207(4) 0.2967(3) 0.1976(3) 0.0353(11) Uani 1 1 d . . . C12 C 0.4843(5) 0.4371(4) 0.1922(3) 0.0425(12) Uani 1 1 d . . . C13 C 0.3537(5) 0.4694(3) 0.1795(3) 0.0423(12) Uani 1 1 d . . . C14 C 0.3473(7) 0.5880(5) 0.1666(6) 0.122(3) Uani 1 1 d . . . H14A H 0.2685 0.6130 0.1448 0.183 Uiso 1 1 calc R . . H14B H 0.4125 0.6212 0.1257 0.183 Uiso 1 1 calc R . . H14C H 0.3568 0.6046 0.2213 0.183 Uiso 1 1 calc R . . C15 C 0.3112(7) 0.4494(6) 0.0984(4) 0.113(3) Uani 1 1 d . . . H15A H 0.3269 0.3774 0.0985 0.170 Uiso 1 1 calc R . . H15B H 0.3553 0.4949 0.0493 0.170 Uiso 1 1 calc R . . H15C H 0.2239 0.4628 0.0948 0.170 Uiso 1 1 calc R . . C16 C 0.2770(7) 0.4188(6) 0.2547(4) 0.121(3) Uani 1 1 d . . . H16A H 0.1975 0.4522 0.2521 0.181 Uiso 1 1 calc R . . H16B H 0.3158 0.4243 0.3063 0.181 Uiso 1 1 calc R . . H16C H 0.2665 0.3460 0.2560 0.181 Uiso 1 1 calc R . . C17 C 0.6893(5) 0.3209(4) 0.1118(3) 0.0450(13) Uani 1 1 d . . . H17A H 0.7031 0.3961 0.0912 0.054 Uiso 1 1 calc R . . H17B H 0.6406 0.2987 0.0700 0.054 Uiso 1 1 calc R . . C18 C 0.8137(5) 0.2640(4) 0.1192(3) 0.0420(12) Uani 1 1 d . . . C19 C 0.8179(4) 0.1948(3) 0.2086(2) 0.0360(11) Uani 1 1 d . . . H19 H 0.8793 0.1436 0.2154 0.043 Uiso 1 1 d R . . C20 C 0.9190(5) 0.3421(4) 0.1048(3) 0.0626(16) Uani 1 1 d . . . H20A H 0.9092 0.3841 0.1459 0.094 Uiso 1 1 calc R . . H20B H 0.9185 0.3867 0.0468 0.094 Uiso 1 1 calc R . . H20C H 0.9963 0.3051 0.1126 0.094 Uiso 1 1 calc R . . C21 C 0.8288(5) 0.2019(4) 0.0522(3) 0.0580(15) Uani 1 1 d . . . H21A H 0.9069 0.1661 0.0580 0.087 Uiso 1 1 calc R . . H21B H 0.8265 0.2486 -0.0049 0.087 Uiso 1 1 calc R . . H21C H 0.7627 0.1513 0.0608 0.087 Uiso 1 1 calc R . . Fe2 Fe 0.10249(6) 0.35655(5) 0.72945(4) 0.0360(2) Uani 1 1 d . . . O8 O -0.1166(4) 0.3723(3) 0.6331(2) 0.0715(12) Uani 1 1 d . . . O9 O 0.2193(4) 0.5381(3) 0.6122(2) 0.0682(12) Uani 1 1 d . . . O10 O -0.0140(4) 0.4357(3) 0.8659(2) 0.0615(11) Uani 1 1 d . . . O11 O 0.3205(3) 0.2920(2) 0.63869(17) 0.0397(8) Uani 1 1 d . . . O12 O 0.4403(3) 0.1582(3) 0.6904(2) 0.0562(10) Uani 1 1 d . . . O13 O -0.0489(3) 0.1677(2) 0.80646(18) 0.0401(8) Uani 1 1 d . . . O14 O 0.0232(4) 0.0115(3) 0.8062(3) 0.0684(11) Uani 1 1 d . . . C22 C -0.0302(5) 0.3659(4) 0.6698(3) 0.0451(13) Uani 1 1 d . . . C23 C 0.1719(5) 0.4695(4) 0.6579(3) 0.0443(13) Uani 1 1 d . . . C24 C 0.0347(5) 0.4081(3) 0.8119(3) 0.0464(13) Uani 1 1 d . . . C25 C 0.2489(4) 0.2675(3) 0.7161(3) 0.0341(11) Uani 1 1 d . . . C26 C 0.4193(4) 0.2317(4) 0.6354(3) 0.0391(11) Uani 1 1 d . . . C27 C 0.5000(5) 0.2743(4) 0.5546(3) 0.0500(14) Uani 1 1 d . . . C28 C 0.4252(5) 0.3260(4) 0.4790(3) 0.0631(17) Uani 1 1 d . . . H28A H 0.3771 0.3817 0.4931 0.095 Uiso 1 1 calc R . . H28B H 0.3706 0.2751 0.4665 0.095 Uiso 1 1 calc R . . H28C H 0.4798 0.3544 0.4290 0.095 Uiso 1 1 calc R . . C29 C 0.5722(5) 0.1846(5) 0.5349(3) 0.079(2) Uani 1 1 d . . . H29A H 0.6286 0.2107 0.4854 0.118 Uiso 1 1 calc R . . H29B H 0.5161 0.1348 0.5223 0.118 Uiso 1 1 calc R . . H29C H 0.6182 0.1508 0.5843 0.118 Uiso 1 1 calc R . . C30 C 0.5837(6) 0.3529(5) 0.5779(4) 0.087(2) Uani 1 1 d . . . H30A H 0.6301 0.3184 0.6269 0.131 Uiso 1 1 calc R . . H30B H 0.5345 0.4077 0.5925 0.131 Uiso 1 1 calc R . . H30C H 0.6399 0.3829 0.5292 0.131 Uiso 1 1 calc R . . C31 C 0.1430(4) 0.2081(3) 0.7238(3) 0.0332(11) Uani 1 1 d . . . H31 H 0.1133 0.1810 0.6801 0.040 Uiso 1 1 d R . . C32 C 0.0735(4) 0.2062(3) 0.8009(3) 0.0366(11) Uani 1 1 d . . . C33 C -0.0624(5) 0.0652(4) 0.8104(3) 0.0436(12) Uani 1 1 d . . . C34 C -0.1944(5) 0.0338(3) 0.8188(3) 0.0428(12) Uani 1 1 d . . . C35 C -0.2564(6) 0.0649(5) 0.8947(4) 0.0817(19) Uani 1 1 d . . . H35A H -0.2086 0.0402 0.9450 0.123 Uiso 1 1 calc R . . H35B H -0.3381 0.0344 0.9062 0.123 Uiso 1 1 calc R . . H35C H -0.2625 0.1401 0.8816 0.123 Uiso 1 1 calc R . . C36 C -0.2030(7) -0.0840(4) 0.8373(4) 0.089(2) Uani 1 1 d . . . H36A H -0.1694 -0.1061 0.7879 0.134 Uiso 1 1 calc R . . H36B H -0.2884 -0.1056 0.8486 0.134 Uiso 1 1 calc R . . H36C H -0.1569 -0.1155 0.8872 0.134 Uiso 1 1 calc R . . C37 C -0.2525(6) 0.0823(5) 0.7380(3) 0.085(2) Uani 1 1 d . . . H37A H -0.2770 0.1526 0.7379 0.128 Uiso 1 1 calc R . . H37B H -0.3244 0.0420 0.7331 0.128 Uiso 1 1 calc R . . H37C H -0.1947 0.0842 0.6897 0.128 Uiso 1 1 calc R . . C38 C 0.1318(4) 0.1860(3) 0.8850(3) 0.0405(12) Uani 1 1 d . . . H38A H 0.1457 0.1111 0.9067 0.049 Uiso 1 1 calc R . . H38B H 0.0766 0.2083 0.9268 0.049 Uiso 1 1 calc R . . C39 C 0.2539(5) 0.2443(3) 0.8757(3) 0.0424(12) Uani 1 1 d . . . C40 C 0.2704(4) 0.3111(3) 0.7840(3) 0.0374(11) Uani 1 1 d . . . H40 H 0.3270 0.3660 0.7763 0.045 Uiso 1 1 d R . . C41 C 0.3607(5) 0.1685(4) 0.8907(3) 0.0570(15) Uani 1 1 d . . . H41A H 0.3551 0.1267 0.9498 0.085 Uiso 1 1 calc R . . H41B H 0.4375 0.2070 0.8798 0.085 Uiso 1 1 calc R . . H41C H 0.3574 0.1234 0.8520 0.085 Uiso 1 1 calc R . . C42 C 0.2595(5) 0.3109(4) 0.9388(3) 0.0548(14) Uani 1 1 d . . . H42A H 0.1889 0.3565 0.9332 0.082 Uiso 1 1 calc R . . H42B H 0.3342 0.3523 0.9268 0.082 Uiso 1 1 calc R . . H42C H 0.2589 0.2665 0.9970 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0381(5) 0.0323(4) 0.0432(4) -0.0119(3) -0.0038(3) 0.0009(3) O1 0.072(3) 0.043(2) 0.075(2) -0.0004(18) -0.021(2) 0.011(2) O2 0.080(3) 0.070(3) 0.074(3) -0.040(2) -0.016(2) -0.007(2) O3 0.050(3) 0.081(3) 0.083(3) -0.027(2) 0.014(2) -0.014(2) O4 0.042(2) 0.0454(18) 0.0341(17) -0.0048(14) -0.0069(16) -0.0037(17) O5 0.054(3) 0.057(2) 0.050(2) -0.0017(18) -0.0122(19) -0.0123(19) O6 0.037(2) 0.0337(17) 0.0514(19) -0.0133(14) -0.0089(16) 0.0028(15) O7 0.049(3) 0.040(2) 0.110(3) -0.027(2) -0.013(2) -0.0012(19) C1 0.050(4) 0.040(3) 0.053(3) -0.016(2) -0.002(3) -0.008(3) C2 0.054(4) 0.042(3) 0.051(3) -0.015(2) -0.005(3) 0.001(3) C3 0.047(4) 0.035(3) 0.060(3) -0.010(2) 0.001(3) -0.002(3) C4 0.030(3) 0.038(2) 0.032(2) -0.008(2) -0.007(2) -0.003(2) C5 0.029(3) 0.044(3) 0.035(3) -0.013(2) 0.000(2) 0.000(2) C6 0.028(3) 0.073(3) 0.035(3) -0.010(2) -0.006(2) -0.005(3) C7 0.050(4) 0.095(4) 0.039(3) -0.005(3) -0.009(3) -0.014(3) C8 0.056(4) 0.116(5) 0.042(3) -0.009(3) -0.013(3) -0.035(4) C9 0.060(5) 0.103(5) 0.074(4) -0.001(4) -0.013(3) 0.042(4) C10 0.041(3) 0.032(2) 0.033(2) -0.0112(19) 0.001(2) -0.003(2) C11 0.033(3) 0.031(2) 0.043(3) -0.012(2) -0.006(2) 0.003(2) C12 0.049(4) 0.041(3) 0.040(3) -0.015(2) -0.007(2) 0.005(3) C13 0.041(3) 0.045(3) 0.040(3) -0.010(2) -0.003(2) 0.011(2) C14 0.071(6) 0.059(4) 0.245(9) -0.052(5) -0.017(6) 0.019(4) C15 0.105(7) 0.172(7) 0.086(4) -0.067(5) -0.058(4) 0.078(6) C16 0.064(6) 0.144(7) 0.112(6) 0.040(5) 0.017(5) 0.033(5) C17 0.055(4) 0.046(3) 0.034(3) -0.010(2) -0.004(2) 0.000(3) C18 0.037(3) 0.054(3) 0.036(3) -0.015(2) -0.003(2) 0.006(3) C19 0.029(3) 0.043(3) 0.036(2) -0.011(2) -0.002(2) 0.001(2) C20 0.051(4) 0.079(4) 0.050(3) -0.004(3) 0.003(3) -0.010(3) C21 0.053(4) 0.084(4) 0.044(3) -0.030(3) 0.000(3) 0.007(3) Fe2 0.0368(5) 0.0313(4) 0.0401(4) -0.0104(3) 0.0035(3) -0.0010(3) O8 0.056(3) 0.090(3) 0.076(3) -0.031(2) -0.023(2) 0.016(2) O9 0.075(3) 0.049(2) 0.070(2) 0.0004(19) 0.024(2) -0.005(2) O10 0.066(3) 0.065(2) 0.058(2) -0.0273(19) 0.012(2) 0.008(2) O11 0.036(2) 0.0468(18) 0.0348(16) -0.0095(14) 0.0054(15) 0.0029(16) O12 0.054(3) 0.055(2) 0.052(2) -0.0026(17) 0.0064(18) 0.0139(19) O13 0.034(2) 0.0326(17) 0.0539(19) -0.0116(14) 0.0032(16) -0.0078(15) O14 0.041(3) 0.039(2) 0.127(3) -0.024(2) 0.004(2) 0.0009(18) C22 0.046(4) 0.042(3) 0.046(3) -0.009(2) -0.001(3) 0.006(3) C23 0.046(4) 0.037(3) 0.050(3) -0.013(2) 0.007(3) 0.001(3) C24 0.051(4) 0.037(3) 0.046(3) -0.004(2) 0.004(3) -0.003(2) C25 0.035(3) 0.033(2) 0.033(2) -0.0072(19) 0.006(2) 0.003(2) C26 0.024(3) 0.055(3) 0.043(3) -0.020(2) -0.003(2) -0.002(2) C27 0.031(3) 0.083(4) 0.034(3) -0.012(3) 0.002(2) 0.002(3) C28 0.050(4) 0.092(4) 0.041(3) -0.007(3) 0.002(3) 0.016(3) C29 0.050(4) 0.134(6) 0.050(3) -0.022(3) -0.002(3) 0.046(4) C30 0.063(5) 0.126(6) 0.060(4) -0.002(4) 0.014(3) -0.044(4) C31 0.031(3) 0.031(2) 0.041(3) -0.0135(19) -0.006(2) 0.008(2) C32 0.035(3) 0.030(2) 0.046(3) -0.012(2) 0.001(2) -0.004(2) C33 0.045(4) 0.040(3) 0.047(3) -0.012(2) -0.003(2) -0.002(3) C34 0.040(3) 0.042(3) 0.044(3) -0.007(2) -0.001(2) -0.006(2) C35 0.058(5) 0.105(5) 0.093(4) -0.049(4) 0.020(4) -0.029(4) C36 0.077(5) 0.052(4) 0.139(6) -0.025(4) -0.009(5) -0.021(3) C37 0.074(5) 0.095(5) 0.072(4) 0.011(4) -0.024(4) -0.026(4) C38 0.039(3) 0.040(3) 0.042(3) -0.010(2) 0.002(2) -0.006(2) C39 0.042(3) 0.046(3) 0.039(3) -0.011(2) 0.000(2) -0.005(2) C40 0.032(3) 0.041(3) 0.039(3) -0.010(2) 0.002(2) -0.008(2) C41 0.052(4) 0.069(4) 0.045(3) -0.005(3) -0.007(3) 0.003(3) C42 0.065(4) 0.067(3) 0.034(3) -0.016(2) -0.001(3) -0.018(3) _geom_special_details ; H10, H19, H31 and H40 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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 1.780(6) . ? Fe1 C2 1.795(6) . ? Fe1 C1 1.818(5) . ? Fe1 C4 2.032(5) . ? Fe1 C10 2.050(4) . ? Fe1 C11 2.058(4) . ? Fe1 C19 2.116(5) . ? O1 C1 1.135(5) . ? O2 C2 1.137(5) . ? O3 C3 1.152(6) . ? O4 C5 1.365(6) . ? O4 C4 1.413(5) . ? O5 C5 1.178(5) . ? O6 C12 1.366(5) . ? O6 C11 1.434(5) . ? O7 C12 1.193(6) . ? C4 C19 1.399(5) . ? C4 C10 1.402(6) . ? C5 C6 1.521(6) . ? C6 C7 1.530(7) . ? C6 C9 1.532(7) . ? C6 C8 1.538(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.414(6) . ? C10 H10 0.9493 . ? C11 C17 1.511(6) . ? C12 C13 1.510(7) . ? C13 C16 1.463(7) . ? C13 C15 1.508(7) . ? C13 C14 1.555(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.560(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.513(6) . ? C18 C21 1.533(6) . ? C18 C20 1.536(7) . ? C19 H19 0.9517 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Fe2 C22 1.782(6) . ? Fe2 C24 1.786(5) . ? Fe2 C23 1.806(5) . ? Fe2 C25 2.037(4) . ? Fe2 C31 2.064(4) . ? Fe2 C32 2.074(4) . ? Fe2 C40 2.112(5) . ? O8 C22 1.141(6) . ? O9 C23 1.135(5) . ? O10 C24 1.144(5) . ? O11 C26 1.359(5) . ? O11 C25 1.415(5) . ? O12 C26 1.180(5) . ? O13 C33 1.371(5) . ? O13 C32 1.437(6) . ? O14 C33 1.192(5) . ? C25 C31 1.400(6) . ? C25 C40 1.406(6) . ? C26 C27 1.531(6) . ? C27 C28 1.527(6) . ? C27 C29 1.530(7) . ? C27 C30 1.539(8) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.428(6) . ? C31 H31 0.9498 . ? C32 C38 1.501(6) . ? C33 C34 1.507(7) . ? C34 C37 1.484(7) . ? C34 C35 1.527(7) . ? C34 C36 1.536(7) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.542(7) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C42 1.527(6) . ? C39 C40 1.532(6) . ? C39 C41 1.539(7) . ? C40 H40 0.9485 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 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 C2 95.8(2) . . ? C3 Fe1 C1 92.9(2) . . ? C2 Fe1 C1 102.3(2) . . ? C3 Fe1 C4 125.1(2) . . ? C2 Fe1 C4 136.1(2) . . ? C1 Fe1 C4 91.7(2) . . ? C3 Fe1 C10 94.93(19) . . ? C2 Fe1 C10 133.25(19) . . ? C1 Fe1 C10 122.4(2) . . ? C4 Fe1 C10 40.19(17) . . ? C3 Fe1 C11 95.89(19) . . ? C2 Fe1 C11 93.34(19) . . ? C1 Fe1 C11 161.2(2) . . ? C4 Fe1 C11 69.64(17) . . ? C10 Fe1 C11 40.27(16) . . ? C3 Fe1 C19 163.9(2) . . ? C2 Fe1 C19 98.1(2) . . ? C1 Fe1 C19 92.1(2) . . ? C4 Fe1 C19 39.36(16) . . ? C10 Fe1 C19 69.54(17) . . ? C11 Fe1 C19 75.23(17) . . ? C5 O4 C4 116.0(3) . . ? C12 O6 C11 117.1(4) . . ? O1 C1 Fe1 176.3(5) . . ? O2 C2 Fe1 175.5(5) . . ? O3 C3 Fe1 177.7(5) . . ? C19 C4 C10 116.0(4) . . ? C19 C4 O4 123.7(4) . . ? C10 C4 O4 119.9(3) . . ? C19 C4 Fe1 73.6(3) . . ? C10 C4 Fe1 70.6(3) . . ? O4 C4 Fe1 119.5(3) . . ? O5 C5 O4 122.7(4) . . ? O5 C5 C6 126.5(5) . . ? O4 C5 C6 110.8(4) . . ? C5 C6 C7 112.3(4) . . ? C5 C6 C9 106.1(4) . . ? C7 C6 C9 109.6(4) . . ? C5 C6 C8 107.8(4) . . ? C7 C6 C8 110.2(4) . . ? C9 C6 C8 110.8(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 C11 112.0(4) . . ? C4 C10 Fe1 69.2(2) . . ? C11 C10 Fe1 70.2(2) . . ? C4 C10 H10 121.3 . . ? C11 C10 H10 126.3 . . ? Fe1 C10 H10 122.3 . . ? C10 C11 O6 117.1(3) . . ? C10 C11 C17 121.9(4) . . ? O6 C11 C17 112.4(3) . . ? C10 C11 Fe1 69.5(2) . . ? O6 C11 Fe1 117.4(3) . . ? C17 C11 Fe1 111.7(3) . . ? O7 C12 O6 122.1(5) . . ? O7 C12 C13 126.8(4) . . ? O6 C12 C13 111.0(5) . . ? C16 C13 C15 112.8(6) . . ? C16 C13 C12 110.2(4) . . ? C15 C13 C12 110.6(4) . . ? C16 C13 C14 109.2(5) . . ? C15 C13 C14 105.8(5) . . ? C12 C13 C14 108.1(5) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C18 110.0(3) . . ? C11 C17 H17A 109.7 . . ? C18 C17 H17A 109.7 . . ? C11 C17 H17B 109.7 . . ? C18 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C19 C18 C21 111.2(4) . . ? C19 C18 C20 108.4(4) . . ? C21 C18 C20 108.4(4) . . ? C19 C18 C17 108.1(4) . . ? C21 C18 C17 110.4(4) . . ? C20 C18 C17 110.4(4) . . ? C4 C19 C18 120.2(4) . . ? C4 C19 Fe1 67.0(3) . . ? C18 C19 Fe1 112.9(3) . . ? C4 C19 H19 117.2 . . ? C18 C19 H19 114.5 . . ? Fe1 C19 H19 116.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 Fe2 C24 95.8(2) . . ? C22 Fe2 C23 93.2(2) . . ? C24 Fe2 C23 102.0(2) . . ? C22 Fe2 C25 124.60(19) . . ? C24 Fe2 C25 136.4(2) . . ? C23 Fe2 C25 92.40(19) . . ? C22 Fe2 C31 94.97(19) . . ? C24 Fe2 C31 132.41(18) . . ? C23 Fe2 C31 123.52(18) . . ? C25 Fe2 C31 39.91(17) . . ? C22 Fe2 C32 96.6(2) . . ? C24 Fe2 C32 92.30(19) . . ? C23 Fe2 C32 161.77(19) . . ? C25 Fe2 C32 69.38(17) . . ? C31 Fe2 C32 40.38(16) . . ? C22 Fe2 C40 163.84(18) . . ? C24 Fe2 C40 98.5(2) . . ? C23 Fe2 C40 91.1(2) . . ? C25 Fe2 C40 39.57(16) . . ? C31 Fe2 C40 69.77(17) . . ? C32 Fe2 C40 75.40(19) . . ? C26 O11 C25 115.9(3) . . ? C33 O13 C32 116.7(3) . . ? O8 C22 Fe2 178.5(4) . . ? O9 C23 Fe2 177.2(4) . . ? O10 C24 Fe2 175.5(5) . . ? C31 C25 C40 116.7(4) . . ? C31 C25 O11 120.3(4) . . ? C40 C25 O11 122.5(4) . . ? C31 C25 Fe2 71.1(2) . . ? C40 C25 Fe2 73.1(2) . . ? O11 C25 Fe2 119.1(3) . . ? O12 C26 O11 123.0(4) . . ? O12 C26 C27 125.5(4) . . ? O11 C26 C27 111.5(4) . . ? C28 C27 C29 110.1(4) . . ? C28 C27 C26 111.7(4) . . ? C29 C27 C26 108.0(4) . . ? C28 C27 C30 110.8(5) . . ? C29 C27 C30 111.6(5) . . ? C26 C27 C30 104.6(4) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C25 C31 C32 111.7(4) . . ? C25 C31 Fe2 69.0(2) . . ? C32 C31 Fe2 70.2(2) . . ? C25 C31 H31 125.0 . . ? C32 C31 H31 122.6 . . ? Fe2 C31 H31 120.8 . . ? C31 C32 O13 116.1(4) . . ? C31 C32 C38 121.5(4) . . ? O13 C32 C38 114.2(4) . . ? C31 C32 Fe2 69.4(2) . . ? O13 C32 Fe2 116.2(3) . . ? C38 C32 Fe2 111.7(3) . . ? O14 C33 O13 121.6(5) . . ? O14 C33 C34 126.9(5) . . ? O13 C33 C34 111.6(4) . . ? C37 C34 C33 109.2(4) . . ? C37 C34 C35 111.9(5) . . ? C33 C34 C35 109.5(4) . . ? C37 C34 C36 109.9(5) . . ? C33 C34 C36 109.0(4) . . ? C35 C34 C36 107.4(5) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C32 C38 C39 110.8(4) . . ? C32 C38 H38A 109.5 . . ? C39 C38 H38A 109.5 . . ? C32 C38 H38B 109.5 . . ? C39 C38 H38B 109.5 . . ? H38A C38 H38B 108.1 . . ? C42 C39 C40 110.3(4) . . ? C42 C39 C41 108.0(4) . . ? C40 C39 C41 107.3(4) . . ? C42 C39 C38 112.0(4) . . ? C40 C39 C38 108.3(4) . . ? C41 C39 C38 110.8(4) . . ? C25 C40 C39 119.2(4) . . ? C25 C40 Fe2 67.3(2) . . ? C39 C40 Fe2 112.2(3) . . ? C25 C40 H40 120.1 . . ? C39 C40 H40 114.7 . . ? Fe2 C40 H40 113.7 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O4 C4 C19 89.3(5) . . . . ? C5 O4 C4 C10 -98.1(5) . . . . ? C5 O4 C4 Fe1 178.5(3) . . . . ? C3 Fe1 C4 C19 -174.1(3) . . . . ? C2 Fe1 C4 C19 -18.6(4) . . . . ? C1 Fe1 C4 C19 91.2(3) . . . . ? C10 Fe1 C4 C19 -126.1(3) . . . . ? C11 Fe1 C4 C19 -91.4(3) . . . . ? C3 Fe1 C4 C10 -48.0(3) . . . . ? C2 Fe1 C4 C10 107.5(3) . . . . ? C1 Fe1 C4 C10 -142.7(3) . . . . ? C11 Fe1 C4 C10 34.7(2) . . . . ? C19 Fe1 C4 C10 126.1(3) . . . . ? C3 Fe1 C4 O4 66.1(4) . . . . ? C2 Fe1 C4 O4 -138.4(3) . . . . ? C1 Fe1 C4 O4 -28.6(3) . . . . ? C10 Fe1 C4 O4 114.1(4) . . . . ? C11 Fe1 C4 O4 148.8(3) . . . . ? C19 Fe1 C4 O4 -119.8(4) . . . . ? C4 O4 C5 O5 5.0(6) . . . . ? C4 O4 C5 C6 -172.4(3) . . . . ? O5 C5 C6 C7 147.5(5) . . . . ? O4 C5 C6 C7 -35.1(5) . . . . ? O5 C5 C6 C9 -92.8(6) . . . . ? O4 C5 C6 C9 84.6(5) . . . . ? O5 C5 C6 C8 26.0(6) . . . . ? O4 C5 C6 C8 -156.6(4) . . . . ? C19 C4 C10 C11 2.7(6) . . . . ? O4 C4 C10 C11 -170.5(4) . . . . ? Fe1 C4 C10 C11 -57.0(3) . . . . ? C19 C4 C10 Fe1 59.6(4) . . . . ? O4 C4 C10 Fe1 -113.5(4) . . . . ? C3 Fe1 C10 C4 142.4(3) . . . . ? C2 Fe1 C10 C4 -114.8(3) . . . . ? C1 Fe1 C10 C4 45.8(3) . . . . ? C11 Fe1 C10 C4 -124.3(4) . . . . ? C19 Fe1 C10 C4 -33.2(2) . . . . ? C3 Fe1 C10 C11 -93.3(3) . . . . ? C2 Fe1 C10 C11 9.4(4) . . . . ? C1 Fe1 C10 C11 170.1(3) . . . . ? C4 Fe1 C10 C11 124.3(4) . . . . ? C19 Fe1 C10 C11 91.1(3) . . . . ? C4 C10 C11 O6 167.6(4) . . . . ? Fe1 C10 C11 O6 111.1(4) . . . . ? C4 C10 C11 C17 -47.1(5) . . . . ? Fe1 C10 C11 C17 -103.5(4) . . . . ? C4 C10 C11 Fe1 56.4(3) . . . . ? C12 O6 C11 C10 65.9(5) . . . . ? C12 O6 C11 C17 -82.6(5) . . . . ? C12 O6 C11 Fe1 145.8(3) . . . . ? C3 Fe1 C11 C10 90.7(3) . . . . ? C2 Fe1 C11 C10 -173.1(3) . . . . ? C1 Fe1 C11 C10 -26.7(7) . . . . ? C4 Fe1 C11 C10 -34.7(3) . . . . ? C19 Fe1 C11 C10 -75.6(3) . . . . ? C3 Fe1 C11 C17 -152.1(4) . . . . ? C2 Fe1 C11 C17 -55.9(4) . . . . ? C1 Fe1 C11 C17 90.6(6) . . . . ? C4 Fe1 C11 C17 82.6(4) . . . . ? C10 Fe1 C11 C17 117.3(5) . . . . ? C19 Fe1 C11 C17 41.6(3) . . . . ? C11 O6 C12 O7 -4.2(6) . . . . ? C11 O6 C12 C13 175.5(3) . . . . ? O7 C12 C13 C16 -111.5(7) . . . . ? O6 C12 C13 C16 68.8(6) . . . . ? O7 C12 C13 C15 123.1(6) . . . . ? O6 C12 C13 C15 -56.6(6) . . . . ? O7 C12 C13 C14 7.8(7) . . . . ? O6 C12 C13 C14 -171.9(5) . . . . ? C10 C11 C17 C18 40.8(6) . . . . ? O6 C11 C17 C18 -172.4(4) . . . . ? Fe1 C11 C17 C18 -38.0(5) . . . . ? C11 C17 C18 C19 5.8(6) . . . . ? C11 C17 C18 C21 127.5(4) . . . . ? C11 C17 C18 C20 -112.7(4) . . . . ? C10 C4 C19 C18 46.0(6) . . . . ? O4 C4 C19 C18 -141.2(4) . . . . ? Fe1 C4 C19 C18 104.0(4) . . . . ? C10 C4 C19 Fe1 -58.0(4) . . . . ? O4 C4 C19 Fe1 114.8(4) . . . . ? C21 C18 C19 C4 -169.5(4) . . . . ? C20 C18 C19 C4 71.4(5) . . . . ? C17 C18 C19 C4 -48.3(6) . . . . ? C21 C18 C19 Fe1 -93.6(4) . . . . ? C20 C18 C19 Fe1 147.3(3) . . . . ? C17 C18 C19 Fe1 27.6(5) . . . . ? C3 Fe1 C19 C4 17.8(8) . . . . ? C2 Fe1 C19 C4 167.1(3) . . . . ? C1 Fe1 C19 C4 -90.1(3) . . . . ? C10 Fe1 C19 C4 33.8(2) . . . . ? C11 Fe1 C19 C4 75.8(2) . . . . ? C3 Fe1 C19 C18 -96.7(7) . . . . ? C2 Fe1 C19 C18 52.7(3) . . . . ? C1 Fe1 C19 C18 155.4(3) . . . . ? C4 Fe1 C19 C18 -114.4(4) . . . . ? C10 Fe1 C19 C18 -80.6(3) . . . . ? C11 Fe1 C19 C18 -38.7(3) . . . . ? C26 O11 C25 C31 -98.4(5) . . . . ? C26 O11 C25 C40 89.9(5) . . . . ? C26 O11 C25 Fe2 177.7(3) . . . . ? C22 Fe2 C25 C31 -48.6(3) . . . . ? C24 Fe2 C25 C31 105.6(3) . . . . ? C23 Fe2 C25 C31 -144.2(3) . . . . ? C32 Fe2 C25 C31 35.0(2) . . . . ? C40 Fe2 C25 C31 126.9(4) . . . . ? C22 Fe2 C25 C40 -175.5(3) . . . . ? C24 Fe2 C25 C40 -21.3(4) . . . . ? C23 Fe2 C25 C40 88.9(3) . . . . ? C31 Fe2 C25 C40 -126.9(4) . . . . ? C32 Fe2 C25 C40 -91.9(3) . . . . ? C25 O11 C26 O12 5.7(7) . . . . ? C25 O11 C26 C27 -171.6(4) . . . . ? O12 C26 C27 C28 148.7(5) . . . . ? O11 C26 C27 C28 -34.0(6) . . . . ? O12 C26 C27 C29 27.5(7) . . . . ? O11 C26 C27 C29 -155.2(4) . . . . ? O12 C26 C27 C30 -91.4(6) . . . . ? O11 C26 C27 C30 85.8(5) . . . . ? C40 C25 C31 C32 1.8(5) . . . . ? O11 C25 C31 C32 -170.3(3) . . . . ? Fe2 C25 C31 C32 -57.1(3) . . . . ? C40 C25 C31 Fe2 58.9(3) . . . . ? O11 C25 C31 Fe2 -113.2(3) . . . . ? C22 Fe2 C31 C25 141.7(3) . . . . ? C24 Fe2 C31 C25 -115.8(3) . . . . ? C23 Fe2 C31 C25 44.5(3) . . . . ? C32 Fe2 C31 C25 -124.0(4) . . . . ? C40 Fe2 C31 C25 -32.9(2) . . . . ? C22 Fe2 C31 C32 -94.4(3) . . . . ? C24 Fe2 C31 C32 8.1(4) . . . . ? C23 Fe2 C31 C32 168.4(3) . . . . ? C25 Fe2 C31 C32 124.0(4) . . . . ? C40 Fe2 C31 C32 91.1(3) . . . . ? C25 C31 C32 O13 166.4(3) . . . . ? Fe2 C31 C32 O13 109.9(3) . . . . ? C25 C31 C32 C38 -47.0(5) . . . . ? Fe2 C31 C32 C38 -103.5(4) . . . . ? C25 C31 C32 Fe2 56.4(3) . . . . ? C33 O13 C32 C31 67.4(5) . . . . ? C33 O13 C32 C38 -81.6(4) . . . . ? C33 O13 C32 Fe2 146.2(3) . . . . ? C22 Fe2 C32 C31 89.9(3) . . . . ? C24 Fe2 C32 C31 -174.0(3) . . . . ? C23 Fe2 C32 C31 -32.3(8) . . . . ? C25 Fe2 C32 C31 -34.7(3) . . . . ? C40 Fe2 C32 C31 -75.8(3) . . . . ? C22 Fe2 C32 O13 -20.0(3) . . . . ? C24 Fe2 C32 O13 76.1(3) . . . . ? C23 Fe2 C32 O13 -142.2(6) . . . . ? C25 Fe2 C32 O13 -144.5(3) . . . . ? C31 Fe2 C32 O13 -109.9(4) . . . . ? C40 Fe2 C32 O13 174.3(3) . . . . ? C22 Fe2 C32 C38 -153.3(3) . . . . ? C24 Fe2 C32 C38 -57.2(3) . . . . ? C23 Fe2 C32 C38 84.5(7) . . . . ? C25 Fe2 C32 C38 82.1(3) . . . . ? C31 Fe2 C32 C38 116.8(4) . . . . ? C40 Fe2 C32 C38 41.0(3) . . . . ? C32 O13 C33 O14 -2.8(6) . . . . ? C32 O13 C33 C34 178.2(3) . . . . ? O14 C33 C34 C37 -110.0(6) . . . . ? O13 C33 C34 C37 68.9(5) . . . . ? O14 C33 C34 C35 127.3(6) . . . . ? O13 C33 C34 C35 -53.9(5) . . . . ? O14 C33 C34 C36 10.1(7) . . . . ? O13 C33 C34 C36 -171.0(4) . . . . ? C31 C32 C38 C39 41.9(5) . . . . ? O13 C32 C38 C39 -170.9(3) . . . . ? Fe2 C32 C38 C39 -36.5(4) . . . . ? C32 C38 C39 C42 126.4(4) . . . . ? C32 C38 C39 C40 4.5(5) . . . . ? C32 C38 C39 C41 -112.9(4) . . . . ? C31 C25 C40 C39 45.7(6) . . . . ? O11 C25 C40 C39 -142.3(4) . . . . ? Fe2 C25 C40 C39 103.6(4) . . . . ? C31 C25 C40 Fe2 -57.9(3) . . . . ? O11 C25 C40 Fe2 114.1(4) . . . . ? C42 C39 C40 C25 -169.9(4) . . . . ? C41 C39 C40 C25 72.6(6) . . . . ? C38 C39 C40 C25 -47.1(5) . . . . ? C42 C39 C40 Fe2 -94.4(4) . . . . ? C41 C39 C40 Fe2 148.2(3) . . . . ? C38 C39 C40 Fe2 28.5(4) . . . . ? C22 Fe2 C40 C25 13.3(8) . . . . ? C24 Fe2 C40 C25 165.3(3) . . . . ? C23 Fe2 C40 C25 -92.4(3) . . . . ? C31 Fe2 C40 C25 33.1(3) . . . . ? C32 Fe2 C40 C25 75.2(3) . . . . ? C22 Fe2 C40 C39 -100.3(7) . . . . ? C24 Fe2 C40 C39 51.7(3) . . . . ? C23 Fe2 C40 C39 154.0(3) . . . . ? C25 Fe2 C40 C39 -113.6(4) . . . . ? C31 Fe2 C40 C39 -80.4(3) . . . . ? C32 Fe2 C40 C39 -38.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.560 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.077 data_rac-10 _database_code_depnum_ccdc_archive 'CCDC 872870' #TrackingRef '- rac10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Fe O5' _chemical_formula_sum 'C14 H16 Fe O5' _chemical_formula_weight 320.12 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.4124(4) _cell_length_b 6.4417(2) _cell_length_c 18.6015(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.644(2) _cell_angle_gamma 90.00 _cell_volume 1439.00(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13203 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 26.99 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max .2 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 1.063 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5014 _exptl_absorpt_correction_T_max 0.9080 _exptl_absorpt_process_details ; The absorption correction (X-RED; Stoe & Cie, 2001) was performed after optimizing the crystal shape using X-SHAPE (Stoe & Cie, 1999). ; _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13203 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3140 _reflns_number_gt 2687 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H11 and H12 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0301P)^2^+0.3528P] 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 3140 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.323441(18) 0.91001(3) 0.111445(13) 0.01449(9) Uani 1 1 d . . . O1 O 0.46622(10) 1.19891(19) 0.05513(8) 0.0285(3) Uani 1 1 d . . . O2 O 0.46457(12) 0.8865(2) 0.26425(8) 0.0320(3) Uani 1 1 d . . . O3 O 0.13986(10) 1.17011(19) 0.13162(7) 0.0236(3) Uani 1 1 d . . . O4 O 0.24800(9) 0.93430(16) -0.06081(6) 0.0174(3) Uani 1 1 d . . . O5 O 0.16641(10) 1.22674(18) -0.03265(7) 0.0226(3) Uani 1 1 d . . . C1 C 0.41208(14) 1.0856(3) 0.07840(10) 0.0197(4) Uani 1 1 d . . . C2 C 0.41127(15) 0.8980(2) 0.20422(11) 0.0217(4) Uani 1 1 d . . . C3 C 0.21426(14) 1.0761(2) 0.12376(9) 0.0177(4) Uani 1 1 d . . . C4 C 0.23526(13) 0.8278(2) 0.00340(9) 0.0157(3) Uani 1 1 d . . . C5 C 0.20376(14) 1.1285(2) -0.07585(10) 0.0172(4) Uani 1 1 d . . . C6 C 0.20429(14) 1.1946(3) -0.15420(9) 0.0186(4) Uani 1 1 d . . . C7 C 0.10977(15) 1.0733(3) -0.20697(10) 0.0244(4) Uani 1 1 d . . . H7A H 0.1255 0.9242 -0.2017 0.037 Uiso 1 1 calc R . . H7B H 0.1044 1.1158 -0.2583 0.037 Uiso 1 1 calc R . . H7C H 0.0392 1.1026 -0.1944 0.037 Uiso 1 1 calc R . . C8 C 0.18072(18) 1.4278(3) -0.16234(11) 0.0282(4) Uani 1 1 d . . . H8A H 0.1085 1.4574 -0.1523 0.042 Uiso 1 1 calc R . . H8B H 0.1793 1.4714 -0.2130 0.042 Uiso 1 1 calc R . . H8C H 0.2393 1.5038 -0.1269 0.042 Uiso 1 1 calc R . . C9 C 0.31593(15) 1.1448(3) -0.17141(11) 0.0263(4) Uani 1 1 d . . . H9A H 0.3762 1.2138 -0.1350 0.039 Uiso 1 1 calc R . . H9B H 0.3148 1.1944 -0.2214 0.039 Uiso 1 1 calc R . . H9C H 0.3281 0.9944 -0.1689 0.039 Uiso 1 1 calc R . . C10 C 0.32541(13) 0.6884(2) 0.03224(9) 0.0168(3) Uani 1 1 d . . . H10 H 0.3831 0.6623 0.0083 0.020 Uiso 1 1 calc R . . C11 C 0.32065(14) 0.5936(2) 0.09933(10) 0.0185(4) Uani 1 1 d . . . H11 H 0.3757 0.4987 0.1248 0.022 Uiso 1 1 calc R . . C12 C 0.22734(14) 0.6502(2) 0.12631(10) 0.0183(4) Uani 1 1 d . . . H12A H 0.2285 0.6127 0.1759 0.022 Uiso 1 1 d R . . C13 C 0.11240(14) 0.6616(3) 0.07330(10) 0.0209(4) Uani 1 1 d . . . H13A H 0.0622 0.7416 0.0967 0.025 Uiso 1 1 calc R . . H13B H 0.0817 0.5197 0.0631 0.025 Uiso 1 1 calc R . . C14 C 0.11725(13) 0.7655(3) 0.00008(10) 0.0187(4) Uani 1 1 d . . . H14A H 0.0900 0.6679 -0.0417 0.022 Uiso 1 1 calc R . . H14B H 0.0687 0.8896 -0.0085 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01385(14) 0.01558(14) 0.01320(14) -0.00013(9) 0.00189(10) -0.00052(8) O1 0.0267(7) 0.0254(7) 0.0379(9) 0.0011(6) 0.0164(6) -0.0041(5) O2 0.0334(8) 0.0359(8) 0.0196(8) -0.0006(6) -0.0065(6) -0.0012(6) O3 0.0256(7) 0.0245(6) 0.0223(7) -0.0008(5) 0.0092(5) 0.0057(6) O4 0.0206(6) 0.0189(6) 0.0131(6) 0.0022(5) 0.0049(5) 0.0040(5) O5 0.0288(7) 0.0229(6) 0.0168(7) 0.0006(5) 0.0074(5) 0.0074(5) C1 0.0173(8) 0.0214(9) 0.0194(9) -0.0042(7) 0.0027(7) 0.0028(7) C2 0.0212(9) 0.0181(8) 0.0248(10) -0.0014(7) 0.0041(8) -0.0024(7) C3 0.0224(9) 0.0187(8) 0.0108(8) 0.0000(6) 0.0020(7) -0.0039(7) C4 0.0184(8) 0.0162(8) 0.0124(8) -0.0012(7) 0.0036(7) 0.0000(6) C5 0.0150(8) 0.0192(8) 0.0160(9) 0.0002(7) 0.0015(7) 0.0012(6) C6 0.0203(8) 0.0205(8) 0.0150(9) 0.0014(7) 0.0045(7) 0.0026(7) C7 0.0246(10) 0.0325(10) 0.0146(9) 0.0002(7) 0.0024(8) -0.0014(7) C8 0.0422(11) 0.0233(9) 0.0192(10) 0.0034(7) 0.0079(9) 0.0045(8) C9 0.0232(9) 0.0348(10) 0.0228(10) 0.0057(8) 0.0093(8) 0.0027(8) C10 0.0164(8) 0.0160(8) 0.0173(9) -0.0043(7) 0.0028(7) -0.0002(6) C11 0.0197(9) 0.0145(8) 0.0190(9) -0.0002(6) 0.0005(7) 0.0008(6) C12 0.0211(9) 0.0171(8) 0.0161(9) 0.0014(7) 0.0035(7) -0.0042(7) C13 0.0166(8) 0.0206(8) 0.0254(10) 0.0007(7) 0.0051(7) -0.0026(7) C14 0.0151(8) 0.0211(8) 0.0177(9) -0.0020(7) -0.0001(7) 0.0002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C3 1.7863(18) . ? Fe1 C1 1.7916(19) . ? Fe1 C2 1.7947(19) . ? Fe1 C11 2.0498(16) . ? Fe1 C10 2.0561(16) . ? Fe1 C4 2.0990(16) . ? Fe1 C12 2.1137(16) . ? O1 C1 1.148(2) . ? O2 C2 1.147(2) . ? O3 C3 1.144(2) . ? O4 C5 1.3666(19) . ? O4 C4 1.420(2) . ? O5 C5 1.204(2) . ? C4 C10 1.429(2) . ? C4 C14 1.505(2) . ? C5 C6 1.520(2) . ? C6 C8 1.531(2) . ? C6 C9 1.533(2) . ? C6 C7 1.539(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.404(2) . ? C10 H10 0.9500 . ? C11 C12 1.421(2) . ? C11 H11 0.9500 . ? C12 C13 1.517(2) . ? C12 H12A 0.9495 . ? C13 C14 1.532(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 102.56(8) . . ? C3 Fe1 C2 101.45(8) . . ? C1 Fe1 C2 94.63(8) . . ? C3 Fe1 C11 128.12(7) . . ? C1 Fe1 C11 125.79(7) . . ? C2 Fe1 C11 92.99(7) . . ? C3 Fe1 C10 130.89(7) . . ? C1 Fe1 C10 94.19(7) . . ? C2 Fe1 C10 123.01(7) . . ? C11 Fe1 C10 39.99(7) . . ? C3 Fe1 C4 92.58(7) . . ? C1 Fe1 C4 92.73(7) . . ? C2 Fe1 C4 162.32(7) . . ? C11 Fe1 C4 69.74(6) . . ? C10 Fe1 C4 40.22(6) . . ? C3 Fe1 C12 89.20(7) . . ? C1 Fe1 C12 163.88(7) . . ? C2 Fe1 C12 93.77(7) . . ? C11 Fe1 C12 39.88(7) . . ? C10 Fe1 C12 69.71(7) . . ? C4 Fe1 C12 75.56(7) . . ? C5 O4 C4 119.34(13) . . ? O1 C1 Fe1 177.78(16) . . ? O2 C2 Fe1 177.61(17) . . ? O3 C3 Fe1 175.14(15) . . ? O4 C4 C10 112.10(14) . . ? O4 C4 C14 114.11(13) . . ? C10 C4 C14 120.61(14) . . ? O4 C4 Fe1 122.77(10) . . ? C10 C4 Fe1 68.28(9) . . ? C14 C4 Fe1 111.90(11) . . ? O5 C5 O4 123.17(16) . . ? O5 C5 C6 126.07(15) . . ? O4 C5 C6 110.70(14) . . ? C5 C6 C8 108.81(14) . . ? C5 C6 C9 111.41(14) . . ? C8 C6 C9 110.18(15) . . ? C5 C6 C7 106.39(14) . . ? C8 C6 C7 109.84(14) . . ? C9 C6 C7 110.14(15) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C4 113.71(15) . . ? C11 C10 Fe1 69.76(9) . . ? C4 C10 Fe1 71.50(9) . . ? C11 C10 H10 123.1 . . ? C4 C10 H10 123.1 . . ? Fe1 C10 H10 127.3 . . ? C10 C11 C12 115.07(14) . . ? C10 C11 Fe1 70.25(9) . . ? C12 C11 Fe1 72.48(9) . . ? C10 C11 H11 122.5 . . ? C12 C11 H11 122.5 . . ? Fe1 C11 H11 126.5 . . ? C11 C12 C13 119.95(16) . . ? C11 C12 Fe1 67.64(9) . . ? C13 C12 Fe1 110.23(11) . . ? C11 C12 H12A 117.6 . . ? C13 C12 H12A 115.1 . . ? Fe1 C12 H12A 117.2 . . ? C12 C13 C14 110.92(14) . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? C4 C14 C13 109.67(13) . . ? C4 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? C4 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? 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 C5 O4 C4 C10 -150.60(14) . . . . ? C5 O4 C4 C14 67.78(18) . . . . ? C5 O4 C4 Fe1 -72.94(16) . . . . ? C3 Fe1 C4 O4 92.96(13) . . . . ? C1 Fe1 C4 O4 -9.75(13) . . . . ? C2 Fe1 C4 O4 -124.3(2) . . . . ? C11 Fe1 C4 O4 -137.09(14) . . . . ? C10 Fe1 C4 O4 -103.01(16) . . . . ? C12 Fe1 C4 O4 -178.53(14) . . . . ? C3 Fe1 C4 C10 -164.03(11) . . . . ? C1 Fe1 C4 C10 93.26(11) . . . . ? C2 Fe1 C4 C10 -21.3(3) . . . . ? C11 Fe1 C4 C10 -34.08(10) . . . . ? C12 Fe1 C4 C10 -75.52(10) . . . . ? C3 Fe1 C4 C14 -48.52(12) . . . . ? C1 Fe1 C4 C14 -151.23(12) . . . . ? C2 Fe1 C4 C14 94.2(3) . . . . ? C11 Fe1 C4 C14 81.43(12) . . . . ? C10 Fe1 C4 C14 115.51(15) . . . . ? C12 Fe1 C4 C14 39.98(11) . . . . ? C4 O4 C5 O5 9.8(2) . . . . ? C4 O4 C5 C6 -167.67(13) . . . . ? O5 C5 C6 C8 15.9(2) . . . . ? O4 C5 C6 C8 -166.69(14) . . . . ? O5 C5 C6 C9 137.57(18) . . . . ? O4 C5 C6 C9 -45.03(18) . . . . ? O5 C5 C6 C7 -102.38(19) . . . . ? O4 C5 C6 C7 75.02(16) . . . . ? O4 C4 C10 C11 174.80(13) . . . . ? C14 C4 C10 C11 -46.4(2) . . . . ? Fe1 C4 C10 C11 56.96(12) . . . . ? O4 C4 C10 Fe1 117.85(12) . . . . ? C14 C4 C10 Fe1 -103.34(15) . . . . ? C3 Fe1 C10 C11 -103.79(12) . . . . ? C1 Fe1 C10 C11 145.62(10) . . . . ? C2 Fe1 C10 C11 47.34(12) . . . . ? C4 Fe1 C10 C11 -125.11(14) . . . . ? C12 Fe1 C10 C11 -33.66(9) . . . . ? C3 Fe1 C10 C4 21.33(14) . . . . ? C1 Fe1 C10 C4 -89.27(11) . . . . ? C2 Fe1 C10 C4 172.45(10) . . . . ? C11 Fe1 C10 C4 125.11(14) . . . . ? C12 Fe1 C10 C4 91.45(10) . . . . ? C4 C10 C11 C12 0.7(2) . . . . ? Fe1 C10 C11 C12 58.60(12) . . . . ? C4 C10 C11 Fe1 -57.91(12) . . . . ? C3 Fe1 C11 C10 111.05(11) . . . . ? C1 Fe1 C11 C10 -43.98(13) . . . . ? C2 Fe1 C11 C10 -141.87(11) . . . . ? C4 Fe1 C11 C10 34.27(9) . . . . ? C12 Fe1 C11 C10 125.83(14) . . . . ? C3 Fe1 C11 C12 -14.78(14) . . . . ? C1 Fe1 C11 C12 -169.81(10) . . . . ? C2 Fe1 C11 C12 92.31(11) . . . . ? C10 Fe1 C11 C12 -125.83(14) . . . . ? C4 Fe1 C11 C12 -91.56(10) . . . . ? C10 C11 C12 C13 43.8(2) . . . . ? Fe1 C11 C12 C13 101.21(14) . . . . ? C10 C11 C12 Fe1 -57.40(12) . . . . ? C3 Fe1 C12 C11 168.42(11) . . . . ? C1 Fe1 C12 C11 31.1(3) . . . . ? C2 Fe1 C12 C11 -90.15(11) . . . . ? C10 Fe1 C12 C11 33.74(10) . . . . ? C4 Fe1 C12 C11 75.55(10) . . . . ? C3 Fe1 C12 C13 53.35(13) . . . . ? C1 Fe1 C12 C13 -83.9(3) . . . . ? C2 Fe1 C12 C13 154.78(13) . . . . ? C11 Fe1 C12 C13 -115.07(16) . . . . ? C10 Fe1 C12 C13 -81.33(13) . . . . ? C4 Fe1 C12 C13 -39.52(12) . . . . ? C11 C12 C13 C14 -42.3(2) . . . . ? Fe1 C12 C13 C14 32.90(17) . . . . ? O4 C4 C14 C13 -177.32(13) . . . . ? C10 C4 C14 C13 44.6(2) . . . . ? Fe1 C4 C14 C13 -32.32(16) . . . . ? C12 C13 C14 C4 -0.76(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.452 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.059 # Attachment '- rac12.cif' data_rac12 _database_code_depnum_ccdc_archive 'CCDC 872871' #TrackingRef '- rac12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 Fe O5' _chemical_formula_sum 'C13 H14 Fe O5' _chemical_formula_weight 306.09 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1260(4) _cell_length_b 7.5018(5) _cell_length_c 15.0179(10) _cell_angle_alpha 77.693(4) _cell_angle_beta 89.267(3) _cell_angle_gamma 78.463(3) _cell_volume 660.36(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4112 _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 26.99 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 1.154 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4112 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2877 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H7 and H8 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0213P)^2^+0.3503P] 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 2877 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0572 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.86468(4) -0.14505(3) 0.267502(14) 0.01510(8) Uani 1 1 d . . . O1 O 1.1961(2) -0.27940(17) 0.14109(8) 0.0258(3) Uani 1 1 d . . . O2 O 1.1430(2) -0.1541(2) 0.42645(9) 0.0353(3) Uani 1 1 d . . . O3 O 0.7363(2) -0.49840(17) 0.35271(9) 0.0330(3) Uani 1 1 d . . . O4 O 0.58505(18) 0.13034(15) 0.36372(7) 0.0171(2) Uani 1 1 d . . . O5 O 0.2863(2) 0.34125(17) 0.29515(8) 0.0263(3) Uani 1 1 d . . . C1 C 1.0710(3) -0.2261(2) 0.19147(11) 0.0189(3) Uani 1 1 d . . . C2 C 1.0331(3) -0.1540(2) 0.36526(11) 0.0219(3) Uani 1 1 d . . . C3 C 0.7867(3) -0.3622(2) 0.31758(11) 0.0215(3) Uani 1 1 d . . . C4 C 0.6484(3) 0.0943(2) 0.27752(10) 0.0157(3) Uani 1 1 d . . . C5 C 0.3941(3) 0.2618(2) 0.36334(11) 0.0182(3) Uani 1 1 d . . . C6 C 0.3439(3) 0.2870(2) 0.45788(11) 0.0247(4) Uani 1 1 d . . . H6A H 0.2036 0.3773 0.4570 0.037 Uiso 1 1 calc R . . H6B H 0.4649 0.3329 0.4819 0.037 Uiso 1 1 calc R . . H6C H 0.3302 0.1673 0.4968 0.037 Uiso 1 1 calc R . . C7 C 0.5371(3) -0.0142(2) 0.23590(11) 0.0175(3) Uani 1 1 d . . . H7X H 0.4179 -0.0668 0.2638 0.021 Uiso 1 1 d R . . C8 C 0.6357(3) -0.0551(2) 0.15425(10) 0.0176(3) Uani 1 1 d . . . H8X H 0.5847 -0.1471 0.1300 0.021 Uiso 1 1 d R . . C9 C 0.7127(3) 0.0962(2) 0.08472(10) 0.0178(3) Uani 1 1 d . . . H9A H 0.5830 0.1729 0.0465 0.021 Uiso 1 1 calc R . . H9B H 0.8201 0.0377 0.0444 0.021 Uiso 1 1 calc R . . C10 C 0.8246(3) 0.2239(2) 0.13009(10) 0.0161(3) Uani 1 1 d . . . C11 C 0.8400(3) 0.1465(2) 0.23312(10) 0.0155(3) Uani 1 1 d . . . H11X H 0.9303 0.1991 0.2669 0.019 Uiso 1 1 d R . . C12 C 1.0574(3) 0.2336(2) 0.09317(11) 0.0201(3) Uani 1 1 d . . . H12A H 1.1268 0.3106 0.1248 0.030 Uiso 1 1 calc R . . H12B H 1.0449 0.2885 0.0277 0.030 Uiso 1 1 calc R . . H12C H 1.1494 0.1077 0.1035 0.030 Uiso 1 1 calc R . . C13 C 0.6835(3) 0.4232(2) 0.11271(11) 0.0214(3) Uani 1 1 d . . . H13A H 0.7524 0.4991 0.1452 0.032 Uiso 1 1 calc R . . H13B H 0.5328 0.4192 0.1347 0.032 Uiso 1 1 calc R . . H13C H 0.6753 0.4780 0.0472 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01523(12) 0.01280(12) 0.01706(12) -0.00316(8) 0.00256(8) -0.00247(8) O1 0.0250(6) 0.0230(6) 0.0276(6) -0.0064(5) 0.0092(5) 0.0001(5) O2 0.0306(7) 0.0481(9) 0.0263(7) -0.0049(6) -0.0071(6) -0.0084(6) O3 0.0469(8) 0.0211(7) 0.0341(7) -0.0054(5) 0.0113(6) -0.0151(6) O4 0.0187(6) 0.0176(5) 0.0142(5) -0.0047(4) 0.0034(4) -0.0005(4) O5 0.0245(6) 0.0283(7) 0.0222(6) -0.0065(5) -0.0008(5) 0.0050(5) C1 0.0195(8) 0.0127(7) 0.0226(8) 0.0001(6) -0.0015(6) -0.0031(6) C2 0.0193(8) 0.0201(8) 0.0240(8) -0.0021(6) 0.0040(7) -0.0022(7) C3 0.0241(9) 0.0201(8) 0.0213(8) -0.0074(7) 0.0044(6) -0.0039(7) C4 0.0167(7) 0.0144(7) 0.0145(7) -0.0032(6) 0.0024(6) 0.0006(6) C5 0.0180(8) 0.0156(7) 0.0219(8) -0.0060(6) 0.0045(6) -0.0034(6) C6 0.0261(9) 0.0258(9) 0.0213(8) -0.0074(7) 0.0071(7) -0.0007(7) C7 0.0136(7) 0.0173(8) 0.0212(8) -0.0036(6) 0.0016(6) -0.0026(6) C8 0.0157(8) 0.0182(8) 0.0205(8) -0.0069(6) 0.0000(6) -0.0044(6) C9 0.0191(8) 0.0190(8) 0.0152(7) -0.0044(6) 0.0007(6) -0.0032(6) C10 0.0188(8) 0.0148(7) 0.0145(7) -0.0027(6) 0.0011(6) -0.0033(6) C11 0.0171(7) 0.0132(7) 0.0164(7) -0.0036(6) 0.0002(6) -0.0030(6) C12 0.0201(8) 0.0216(8) 0.0190(8) -0.0040(6) 0.0040(6) -0.0061(6) C13 0.0247(9) 0.0163(8) 0.0208(8) -0.0018(6) 0.0012(6) -0.0009(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 C2 1.7871(17) . ? Fe1 C1 1.7952(17) . ? Fe1 C3 1.7964(17) . ? Fe1 C4 2.0401(15) . ? Fe1 C7 2.0625(15) . ? Fe1 C11 2.1123(15) . ? Fe1 C8 2.1232(15) . ? O1 C1 1.145(2) . ? O2 C2 1.146(2) . ? O3 C3 1.145(2) . ? O4 C5 1.3703(19) . ? O4 C4 1.4119(18) . ? O5 C5 1.200(2) . ? C4 C7 1.403(2) . ? C4 C11 1.425(2) . ? C5 C6 1.492(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.425(2) . ? C7 H7X 0.9495 . ? C8 C9 1.515(2) . ? C8 H8X 0.9510 . ? C9 C10 1.551(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.529(2) . ? C10 C12 1.533(2) . ? C10 C13 1.540(2) . ? C11 H11X 0.9476 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 C2 Fe1 C1 101.49(7) . . ? C2 Fe1 C3 92.30(8) . . ? C1 Fe1 C3 99.06(7) . . ? C2 Fe1 C4 95.38(7) . . ? C1 Fe1 C4 138.86(7) . . ? C3 Fe1 C4 117.58(7) . . ? C2 Fe1 C7 129.28(7) . . ? C1 Fe1 C7 127.52(7) . . ? C3 Fe1 C7 92.04(7) . . ? C4 Fe1 C7 39.98(6) . . ? C2 Fe1 C11 88.86(7) . . ? C1 Fe1 C11 102.66(6) . . ? C3 Fe1 C11 157.56(7) . . ? C4 Fe1 C11 40.08(6) . . ? C7 Fe1 C11 70.24(6) . . ? C2 Fe1 C8 163.84(7) . . ? C1 Fe1 C8 87.76(7) . . ? C3 Fe1 C8 99.37(7) . . ? C4 Fe1 C8 69.33(6) . . ? C7 Fe1 C8 39.77(6) . . ? C11 Fe1 C8 76.09(6) . . ? C5 O4 C4 115.26(12) . . ? O1 C1 Fe1 177.29(14) . . ? O2 C2 Fe1 177.66(16) . . ? O3 C3 Fe1 177.30(15) . . ? C7 C4 O4 120.57(14) . . ? C7 C4 C11 116.34(14) . . ? O4 C4 C11 122.73(13) . . ? C7 C4 Fe1 70.87(9) . . ? O4 C4 Fe1 120.56(10) . . ? C11 C4 Fe1 72.69(9) . . ? O5 C5 O4 123.00(14) . . ? O5 C5 C6 126.67(15) . . ? O4 C5 C6 110.33(13) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 C8 113.82(14) . . ? C4 C7 Fe1 69.15(9) . . ? C8 C7 Fe1 72.41(9) . . ? C4 C7 H7X 122.3 . . ? C8 C7 H7X 123.5 . . ? Fe1 C7 H7X 121.2 . . ? C7 C8 C9 120.08(14) . . ? C7 C8 Fe1 67.82(9) . . ? C9 C8 Fe1 109.48(10) . . ? C7 C8 H8X 116.8 . . ? C9 C8 H8X 115.5 . . ? Fe1 C8 H8X 118.2 . . ? C8 C9 C10 112.28(12) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C12 110.19(13) . . ? C11 C10 C13 107.72(12) . . ? C12 C10 C13 108.40(13) . . ? C11 C10 C9 108.37(12) . . ? C12 C10 C9 111.14(13) . . ? C13 C10 C9 110.97(13) . . ? C4 C11 C10 118.60(13) . . ? C4 C11 Fe1 67.23(8) . . ? C10 C11 Fe1 112.62(10) . . ? C4 C11 H11X 116.0 . . ? C10 C11 H11X 115.7 . . ? Fe1 C11 H11X 117.9 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O4 C4 C7 -76.48(17) . . . . ? C5 O4 C4 C11 110.67(16) . . . . ? C5 O4 C4 Fe1 -161.13(11) . . . . ? C2 Fe1 C4 C7 -151.34(10) . . . . ? C1 Fe1 C4 C7 94.34(13) . . . . ? C3 Fe1 C4 C7 -55.91(11) . . . . ? C11 Fe1 C4 C7 126.88(13) . . . . ? C8 Fe1 C4 C7 34.04(9) . . . . ? C2 Fe1 C4 C11 81.78(10) . . . . ? C1 Fe1 C4 C11 -32.53(14) . . . . ? C3 Fe1 C4 C11 177.21(9) . . . . ? C7 Fe1 C4 C11 -126.88(13) . . . . ? C8 Fe1 C4 C11 -92.83(9) . . . . ? C4 O4 C5 O5 0.3(2) . . . . ? C4 O4 C5 C6 179.72(13) . . . . ? O4 C4 C7 C8 -173.40(13) . . . . ? C11 C4 C7 C8 -0.1(2) . . . . ? Fe1 C4 C7 C8 -58.56(12) . . . . ? O4 C4 C7 Fe1 -114.84(13) . . . . ? C11 C4 C7 Fe1 58.45(12) . . . . ? C2 Fe1 C7 C4 38.09(13) . . . . ? C1 Fe1 C7 C4 -124.20(10) . . . . ? C3 Fe1 C7 C4 132.74(10) . . . . ? C11 Fe1 C7 C4 -33.18(9) . . . . ? C8 Fe1 C7 C4 -125.03(13) . . . . ? C2 Fe1 C7 C8 163.12(10) . . . . ? C1 Fe1 C7 C8 0.84(12) . . . . ? C3 Fe1 C7 C8 -102.23(10) . . . . ? C4 Fe1 C7 C8 125.03(13) . . . . ? C11 Fe1 C7 C8 91.85(10) . . . . ? C4 C7 C8 C9 -43.6(2) . . . . ? Fe1 C7 C8 C9 -100.38(13) . . . . ? C4 C7 C8 Fe1 56.76(12) . . . . ? C2 Fe1 C8 C7 -53.8(3) . . . . ? C1 Fe1 C8 C7 -179.33(10) . . . . ? C3 Fe1 C8 C7 81.85(10) . . . . ? C4 Fe1 C8 C7 -34.22(9) . . . . ? C11 Fe1 C8 C7 -75.71(9) . . . . ? C2 Fe1 C8 C9 61.6(3) . . . . ? C1 Fe1 C8 C9 -63.88(11) . . . . ? C3 Fe1 C8 C9 -162.70(11) . . . . ? C4 Fe1 C8 C9 81.24(11) . . . . ? C7 Fe1 C8 C9 115.46(14) . . . . ? C11 Fe1 C8 C9 39.75(10) . . . . ? C7 C8 C9 C10 39.7(2) . . . . ? Fe1 C8 C9 C10 -35.37(15) . . . . ? C8 C9 C10 C11 4.62(18) . . . . ? C8 C9 C10 C12 125.83(14) . . . . ? C8 C9 C10 C13 -113.46(14) . . . . ? C7 C4 C11 C10 46.8(2) . . . . ? O4 C4 C11 C10 -140.11(14) . . . . ? Fe1 C4 C11 C10 104.26(13) . . . . ? C7 C4 C11 Fe1 -57.49(12) . . . . ? O4 C4 C11 Fe1 115.64(14) . . . . ? C12 C10 C11 C4 -168.50(13) . . . . ? C13 C10 C11 C4 73.43(17) . . . . ? C9 C10 C11 C4 -46.70(18) . . . . ? C12 C10 C11 Fe1 -93.00(13) . . . . ? C13 C10 C11 Fe1 148.93(10) . . . . ? C9 C10 C11 Fe1 28.80(15) . . . . ? C2 Fe1 C11 C4 -99.74(10) . . . . ? C1 Fe1 C11 C4 158.74(9) . . . . ? C3 Fe1 C11 C4 -6.5(2) . . . . ? C7 Fe1 C11 C4 33.10(9) . . . . ? C8 Fe1 C11 C4 74.30(9) . . . . ? C2 Fe1 C11 C10 147.46(12) . . . . ? C1 Fe1 C11 C10 45.94(12) . . . . ? C3 Fe1 C11 C10 -119.28(18) . . . . ? C4 Fe1 C11 C10 -112.80(14) . . . . ? C7 Fe1 C11 C10 -79.69(11) . . . . ? C8 Fe1 C11 C10 -38.50(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.360 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.054 # Attachment '- rac15.cif' data_rac-15 _database_code_depnum_ccdc_archive 'CCDC 872872' #TrackingRef '- rac15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 Fe O7' _chemical_formula_sum 'C19 H24 Fe O7' _chemical_formula_weight 420.23 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5179(16) _cell_length_b 12.1754(7) _cell_length_c 12.5175(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.201(3) _cell_angle_gamma 90.00 _cell_volume 2027.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12099 _cell_measurement_theta_min 1.53 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour yellowish _exptl_crystal_size_max .3 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12099 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3374 _reflns_number_gt 2484 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H10 and H19 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0678P)^2^+5.7318P] 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 3374 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1803 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.214 _refine_ls_restrained_S_all 1.214 _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 0.14687(6) 0.22816(6) -0.02658(6) 0.0187(3) Uani 1 1 d . . . O1 O 0.0746(3) 0.4198(4) -0.1605(3) 0.0311(10) Uani 1 1 d . . . O2 O -0.0163(3) 0.0723(3) -0.1039(3) 0.0298(10) Uani 1 1 d . . . O3 O 0.2989(3) 0.1342(3) -0.1422(3) 0.0314(10) Uani 1 1 d . . . O4 O 0.3323(3) 0.1515(3) 0.1288(3) 0.0251(9) Uani 1 1 d . . . O5 O 0.3165(3) 0.1122(4) 0.3012(4) 0.0439(13) Uani 1 1 d . . . O6 O -0.0148(3) 0.2449(3) 0.1204(3) 0.0205(9) Uani 1 1 d . . . O7 O -0.0948(3) 0.3439(3) -0.0214(3) 0.0265(10) Uani 1 1 d . . . C1 C 0.1014(4) 0.3430(5) -0.1114(5) 0.0232(13) Uani 1 1 d . . . C2 C 0.0483(4) 0.1319(5) -0.0732(5) 0.0235(13) Uani 1 1 d . . . C3 C 0.2371(4) 0.1700(5) -0.0990(5) 0.0245(14) Uani 1 1 d . . . C4 C 0.2501(4) 0.2239(5) 0.1154(4) 0.0212(12) Uani 1 1 d . . . C5 C 0.3612(4) 0.1015(5) 0.2273(5) 0.0242(13) Uani 1 1 d . . . C6 C 0.4565(4) 0.0355(5) 0.2281(5) 0.0264(14) Uani 1 1 d . . . C7 C 0.4855(5) -0.0198(7) 0.3371(6) 0.056(2) Uani 1 1 d . . . H7A H 0.4932 0.0357 0.3947 0.084 Uiso 1 1 calc R . . H7B H 0.5492 -0.0590 0.3396 0.084 Uiso 1 1 calc R . . H7C H 0.4330 -0.0721 0.3477 0.084 Uiso 1 1 calc R . . C8 C 0.4360(5) -0.0517(6) 0.1388(7) 0.052(2) Uani 1 1 d . . . H8A H 0.3785 -0.0968 0.1496 0.078 Uiso 1 1 calc R . . H8B H 0.4954 -0.0985 0.1419 0.078 Uiso 1 1 calc R . . H8C H 0.4209 -0.0157 0.0678 0.078 Uiso 1 1 calc R . . C9 C 0.5398(5) 0.1119(6) 0.2072(7) 0.047(2) Uani 1 1 d . . . H9A H 0.5190 0.1492 0.1374 0.071 Uiso 1 1 calc R . . H9B H 0.6009 0.0692 0.2052 0.071 Uiso 1 1 calc R . . H9C H 0.5532 0.1666 0.2653 0.071 Uiso 1 1 calc R . . C10 C 0.1549(4) 0.1941(5) 0.1354(5) 0.0225(13) Uani 1 1 d . . . H10X H 0.1358 0.1257 0.1621 0.027 Uiso 1 1 d R . . C11 C 0.0825(4) 0.2792(5) 0.1039(4) 0.0185(12) Uani 1 1 d . . . C12 C -0.0981(4) 0.2855(5) 0.0539(5) 0.0222(13) Uani 1 1 d . . . C13 C -0.1930(4) 0.2432(5) 0.0918(5) 0.0208(13) Uani 1 1 d . . . C14 C -0.1930(5) 0.2819(6) 0.2083(5) 0.0385(17) Uani 1 1 d . . . H14A H -0.2547 0.2570 0.2318 0.058 Uiso 1 1 calc R . . H14B H -0.1898 0.3623 0.2111 0.058 Uiso 1 1 calc R . . H14C H -0.1345 0.2512 0.2566 0.058 Uiso 1 1 calc R . . C15 C -0.2846(4) 0.2901(5) 0.0162(5) 0.0351(16) Uani 1 1 d . . . H15A H -0.2802 0.2724 -0.0592 0.053 Uiso 1 1 calc R . . H15B H -0.2863 0.3700 0.0250 0.053 Uiso 1 1 calc R . . H15C H -0.3460 0.2579 0.0343 0.053 Uiso 1 1 calc R . . C16 C -0.1939(5) 0.1191(5) 0.0880(6) 0.0382(17) Uani 1 1 d . . . H16A H -0.1916 0.0946 0.0140 0.057 Uiso 1 1 calc R . . H16B H -0.2555 0.0918 0.1100 0.057 Uiso 1 1 calc R . . H16C H -0.1353 0.0906 0.1377 0.057 Uiso 1 1 calc R . . C17 C 0.1058(4) 0.3977(5) 0.1324(5) 0.0248(13) Uani 1 1 d . . . H17A H 0.1063 0.4096 0.2107 0.030 Uiso 1 1 calc R . . H17B H 0.0534 0.4455 0.0908 0.030 Uiso 1 1 calc R . . C18 C 0.2095(4) 0.4272(5) 0.1049(5) 0.0249(13) Uani 1 1 d . . . H18A H 0.2013 0.4852 0.0486 0.030 Uiso 1 1 calc R . . H18B H 0.2533 0.4564 0.1705 0.030 Uiso 1 1 calc R . . C19 C 0.2584(4) 0.3278(5) 0.0644(4) 0.0217(13) Uani 1 1 d . . . H19X H 0.3156 0.3461 0.0336 0.026 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0154(4) 0.0229(5) 0.0184(4) 0.0020(4) 0.0044(3) 0.0025(3) O1 0.036(3) 0.034(3) 0.026(2) 0.008(2) 0.013(2) 0.012(2) O2 0.025(2) 0.030(3) 0.034(2) 0.0000(19) 0.0017(19) -0.0033(19) O3 0.024(2) 0.039(3) 0.032(3) -0.005(2) 0.009(2) 0.0087(19) O4 0.018(2) 0.033(2) 0.025(2) 0.0073(18) 0.0056(17) 0.0089(17) O5 0.038(3) 0.070(3) 0.027(3) 0.008(2) 0.013(2) 0.028(2) O6 0.0120(18) 0.025(2) 0.025(2) 0.0043(17) 0.0057(15) 0.0025(15) O7 0.020(2) 0.029(3) 0.031(2) 0.0076(19) 0.0065(18) 0.0033(17) C1 0.017(3) 0.036(4) 0.018(3) -0.001(3) 0.008(2) 0.003(3) C2 0.024(3) 0.027(4) 0.021(3) 0.002(3) 0.008(3) 0.007(3) C3 0.025(3) 0.026(4) 0.022(3) 0.005(3) 0.003(3) -0.001(3) C4 0.016(3) 0.026(3) 0.022(3) 0.004(3) 0.004(2) 0.004(2) C5 0.022(3) 0.027(4) 0.023(3) 0.003(3) 0.000(3) 0.000(2) C6 0.019(3) 0.030(4) 0.031(3) 0.003(3) 0.005(3) 0.005(2) C7 0.034(4) 0.079(6) 0.057(5) 0.037(4) 0.015(4) 0.026(4) C8 0.035(4) 0.046(5) 0.070(6) -0.016(4) -0.002(4) 0.017(3) C9 0.016(3) 0.046(5) 0.078(6) 0.013(4) 0.005(3) 0.003(3) C10 0.019(3) 0.027(3) 0.021(3) 0.002(2) 0.004(2) -0.001(2) C11 0.017(3) 0.026(3) 0.013(3) 0.004(2) 0.003(2) -0.001(2) C12 0.021(3) 0.021(3) 0.025(3) -0.004(3) 0.005(2) 0.003(2) C13 0.014(3) 0.021(3) 0.028(3) 0.001(2) 0.007(2) 0.002(2) C14 0.024(3) 0.062(5) 0.034(4) -0.008(3) 0.014(3) -0.007(3) C15 0.022(3) 0.041(4) 0.043(4) 0.012(3) 0.008(3) 0.001(3) C16 0.024(3) 0.034(4) 0.058(5) -0.001(3) 0.014(3) -0.004(3) C17 0.019(3) 0.026(4) 0.030(3) 0.000(3) 0.005(3) 0.002(2) C18 0.022(3) 0.024(4) 0.029(3) -0.002(3) 0.005(3) 0.000(2) C19 0.019(3) 0.026(3) 0.021(3) 0.001(2) 0.006(2) -0.002(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 C3 1.790(6) . ? Fe1 C2 1.793(6) . ? Fe1 C1 1.798(6) . ? Fe1 C10 2.054(6) . ? Fe1 C4 2.057(5) . ? Fe1 C11 2.077(5) . ? Fe1 C19 2.105(6) . ? O1 C1 1.142(7) . ? O2 C2 1.148(7) . ? O3 C3 1.158(7) . ? O4 C5 1.369(7) . ? O4 C4 1.404(6) . ? O5 C5 1.199(7) . ? O6 C12 1.368(7) . ? O6 C11 1.429(6) . ? O7 C12 1.189(7) . ? C4 C10 1.402(8) . ? C4 C19 1.430(8) . ? C5 C6 1.516(8) . ? C6 C7 1.509(9) . ? C6 C9 1.519(8) . ? C6 C8 1.531(9) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.431(8) . ? C10 H10X 0.9499 . ? C11 C17 1.507(8) . ? C12 C13 1.533(8) . ? C13 C16 1.512(9) . ? C13 C15 1.529(8) . ? C13 C14 1.533(8) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.544(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.510(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19X 0.9507 . ? 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 C2 96.3(3) . . ? C3 Fe1 C1 101.6(3) . . ? C2 Fe1 C1 99.2(3) . . ? C3 Fe1 C10 119.9(2) . . ? C2 Fe1 C10 95.5(2) . . ? C1 Fe1 C10 133.9(2) . . ? C3 Fe1 C4 90.5(2) . . ? C2 Fe1 C4 128.0(2) . . ? C1 Fe1 C4 129.7(2) . . ? C10 Fe1 C4 39.9(2) . . ? C3 Fe1 C11 159.2(2) . . ? C2 Fe1 C11 93.5(2) . . ? C1 Fe1 C11 94.8(2) . . ? C10 Fe1 C11 40.5(2) . . ? C4 Fe1 C11 69.1(2) . . ? C3 Fe1 C19 90.9(2) . . ? C2 Fe1 C19 166.5(2) . . ? C1 Fe1 C19 90.5(2) . . ? C10 Fe1 C19 71.0(2) . . ? C4 Fe1 C19 40.2(2) . . ? C11 Fe1 C19 76.2(2) . . ? C5 O4 C4 118.7(4) . . ? C12 O6 C11 119.1(4) . . ? O1 C1 Fe1 176.1(5) . . ? O2 C2 Fe1 178.3(5) . . ? O3 C3 Fe1 176.8(5) . . ? C10 C4 O4 123.2(5) . . ? C10 C4 C19 117.1(5) . . ? O4 C4 C19 119.0(5) . . ? C10 C4 Fe1 69.9(3) . . ? O4 C4 Fe1 121.3(4) . . ? C19 C4 Fe1 71.7(3) . . ? O5 C5 O4 123.0(5) . . ? O5 C5 C6 126.6(5) . . ? O4 C5 C6 110.4(5) . . ? C7 C6 C5 109.1(5) . . ? C7 C6 C9 110.3(6) . . ? C5 C6 C9 109.2(5) . . ? C7 C6 C8 109.5(6) . . ? C5 C6 C8 108.6(5) . . ? C9 C6 C8 110.0(6) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 C11 111.6(5) . . ? C4 C10 Fe1 70.2(3) . . ? C11 C10 Fe1 70.6(3) . . ? C4 C10 H10X 127.1 . . ? C11 C10 H10X 121.1 . . ? Fe1 C10 H10X 123.6 . . ? O6 C11 C10 110.5(4) . . ? O6 C11 C17 113.9(4) . . ? C10 C11 C17 121.6(5) . . ? O6 C11 Fe1 123.4(4) . . ? C10 C11 Fe1 68.9(3) . . ? C17 C11 Fe1 111.9(4) . . ? O7 C12 O6 123.8(5) . . ? O7 C12 C13 126.7(5) . . ? O6 C12 C13 109.5(5) . . ? C16 C13 C15 110.6(5) . . ? C16 C13 C12 109.2(5) . . ? C15 C13 C12 108.3(5) . . ? C16 C13 C14 109.6(5) . . ? C15 C13 C14 109.8(5) . . ? C12 C13 C14 109.4(5) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C18 109.3(5) . . ? C11 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? C11 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? C19 C18 C17 110.9(5) . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 108.0 . . ? C4 C19 C18 119.1(5) . . ? C4 C19 Fe1 68.1(3) . . ? C18 C19 Fe1 109.2(4) . . ? C4 C19 H19X 121.5 . . ? C18 C19 H19X 112.6 . . ? Fe1 C19 H19X 118.2 . . ? 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 C5 O4 C4 C10 -55.6(7) . . . . ? C5 O4 C4 C19 133.7(5) . . . . ? C5 O4 C4 Fe1 -141.0(4) . . . . ? C3 Fe1 C4 C10 -140.1(4) . . . . ? C2 Fe1 C4 C10 -41.7(5) . . . . ? C1 Fe1 C4 C10 114.2(4) . . . . ? C11 Fe1 C4 C10 35.8(3) . . . . ? C19 Fe1 C4 C10 129.1(5) . . . . ? C3 Fe1 C4 O4 -22.7(4) . . . . ? C2 Fe1 C4 O4 75.8(5) . . . . ? C1 Fe1 C4 O4 -128.3(4) . . . . ? C10 Fe1 C4 O4 117.5(6) . . . . ? C11 Fe1 C4 O4 153.2(5) . . . . ? C19 Fe1 C4 O4 -113.4(5) . . . . ? C3 Fe1 C4 C19 90.7(3) . . . . ? C2 Fe1 C4 C19 -170.8(3) . . . . ? C1 Fe1 C4 C19 -14.9(4) . . . . ? C10 Fe1 C4 C19 -129.1(5) . . . . ? C11 Fe1 C4 C19 -93.3(3) . . . . ? C4 O4 C5 O5 4.0(8) . . . . ? C4 O4 C5 C6 -174.7(5) . . . . ? O5 C5 C6 C7 2.2(9) . . . . ? O4 C5 C6 C7 -179.2(5) . . . . ? O5 C5 C6 C9 -118.5(7) . . . . ? O4 C5 C6 C9 60.2(7) . . . . ? O5 C5 C6 C8 121.5(7) . . . . ? O4 C5 C6 C8 -59.8(7) . . . . ? O4 C4 C10 C11 -173.5(5) . . . . ? C19 C4 C10 C11 -2.6(7) . . . . ? Fe1 C4 C10 C11 -58.5(4) . . . . ? O4 C4 C10 Fe1 -115.0(5) . . . . ? C19 C4 C10 Fe1 55.8(4) . . . . ? C3 Fe1 C10 C4 47.7(4) . . . . ? C2 Fe1 C10 C4 148.2(4) . . . . ? C1 Fe1 C10 C4 -103.4(4) . . . . ? C11 Fe1 C10 C4 -122.8(5) . . . . ? C19 Fe1 C10 C4 -32.0(3) . . . . ? C3 Fe1 C10 C11 170.5(3) . . . . ? C2 Fe1 C10 C11 -88.9(3) . . . . ? C1 Fe1 C10 C11 19.4(5) . . . . ? C4 Fe1 C10 C11 122.8(5) . . . . ? C19 Fe1 C10 C11 90.9(3) . . . . ? C12 O6 C11 C10 -149.8(5) . . . . ? C12 O6 C11 C17 69.2(6) . . . . ? C12 O6 C11 Fe1 -72.2(6) . . . . ? C4 C10 C11 O6 177.3(4) . . . . ? Fe1 C10 C11 O6 119.1(4) . . . . ? C4 C10 C11 C17 -45.2(7) . . . . ? Fe1 C10 C11 C17 -103.4(5) . . . . ? C4 C10 C11 Fe1 58.2(4) . . . . ? C3 Fe1 C11 O6 -124.9(7) . . . . ? C2 Fe1 C11 O6 -6.9(4) . . . . ? C1 Fe1 C11 O6 92.7(4) . . . . ? C10 Fe1 C11 O6 -101.2(5) . . . . ? C4 Fe1 C11 O6 -136.5(5) . . . . ? C19 Fe1 C11 O6 -178.0(5) . . . . ? C3 Fe1 C11 C10 -23.7(8) . . . . ? C2 Fe1 C11 C10 94.4(3) . . . . ? C1 Fe1 C11 C10 -166.1(3) . . . . ? C4 Fe1 C11 C10 -35.2(3) . . . . ? C19 Fe1 C11 C10 -76.8(3) . . . . ? C3 Fe1 C11 C17 93.1(8) . . . . ? C2 Fe1 C11 C17 -148.9(4) . . . . ? C1 Fe1 C11 C17 -49.4(4) . . . . ? C10 Fe1 C11 C17 116.7(5) . . . . ? C4 Fe1 C11 C17 81.5(4) . . . . ? C19 Fe1 C11 C17 40.0(4) . . . . ? C11 O6 C12 O7 4.1(8) . . . . ? C11 O6 C12 C13 -176.2(4) . . . . ? O7 C12 C13 C16 120.0(6) . . . . ? O6 C12 C13 C16 -59.6(6) . . . . ? O7 C12 C13 C15 -0.5(8) . . . . ? O6 C12 C13 C15 179.9(5) . . . . ? O7 C12 C13 C14 -120.1(6) . . . . ? O6 C12 C13 C14 60.3(6) . . . . ? O6 C11 C17 C18 -176.6(4) . . . . ? C10 C11 C17 C18 47.2(7) . . . . ? Fe1 C11 C17 C18 -30.8(6) . . . . ? C11 C17 C18 C19 -3.3(7) . . . . ? C10 C4 C19 C18 45.6(7) . . . . ? O4 C4 C19 C18 -143.2(5) . . . . ? Fe1 C4 C19 C18 100.5(5) . . . . ? C10 C4 C19 Fe1 -54.9(4) . . . . ? O4 C4 C19 Fe1 116.3(5) . . . . ? C17 C18 C19 C4 -40.1(7) . . . . ? C17 C18 C19 Fe1 35.0(6) . . . . ? C3 Fe1 C19 C4 -89.8(3) . . . . ? C2 Fe1 C19 C4 32.5(11) . . . . ? C1 Fe1 C19 C4 168.6(3) . . . . ? C10 Fe1 C19 C4 31.7(3) . . . . ? C11 Fe1 C19 C4 73.7(3) . . . . ? C3 Fe1 C19 C18 155.8(4) . . . . ? C2 Fe1 C19 C18 -81.9(11) . . . . ? C1 Fe1 C19 C18 54.1(4) . . . . ? C10 Fe1 C19 C18 -82.7(4) . . . . ? C4 Fe1 C19 C18 -114.5(5) . . . . ? C11 Fe1 C19 C18 -40.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 1.017 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.143 # Attachment '- rac18.cif' data_rac-18 _database_code_depnum_ccdc_archive 'CCDC 872873' #TrackingRef '- rac18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H38 Fe O5' _chemical_formula_sum 'C25 H38 Fe O5' _chemical_formula_weight 474.40 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6635(14) _cell_length_b 6.7003(15) _cell_length_c 28.213(6) _cell_angle_alpha 85.849(5) _cell_angle_beta 86.939(6) _cell_angle_gamma 82.030(7) _cell_volume 1243.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5290 _cell_measurement_theta_min 1.45 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.638 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5290 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.1047 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4158 _reflns_number_gt 2396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H22 and H23 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0834P)^2^+2.0578P] 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 4158 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1435 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.2007 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.78014(15) 0.65454(14) 0.07763(3) 0.0506(4) Uani 1 1 d . . . O1 O 0.4526(9) 0.9532(8) 0.11453(19) 0.0848(17) Uani 1 1 d . . . O2 O 0.5720(9) 0.3288(8) 0.04714(18) 0.0883(18) Uani 1 1 d . . . O3 O 0.8254(10) 0.8318(9) -0.01973(17) 0.098(2) Uani 1 1 d . . . O4 O 0.7263(7) 0.3772(6) 0.16834(14) 0.0545(12) Uani 1 1 d . . . O5 O 0.4317(7) 0.5700(7) 0.18793(18) 0.0661(13) Uani 1 1 d . . . C1 C 0.5870(13) 0.8295(14) 0.1011(3) 0.090(3) Uani 1 1 d . . . C2 C 0.6492(12) 0.4602(11) 0.0594(2) 0.066(2) Uani 1 1 d . . . C3 C 0.8045(12) 0.7610(11) 0.0184(3) 0.074(2) Uani 1 1 d . . . C4 C 0.8221(11) 0.5390(10) 0.1466(2) 0.0614(19) Uani 1 1 d . . . C5 C 0.5366(10) 0.4123(9) 0.1895(2) 0.0451(15) Uani 1 1 d . . . C6 C 0.4860(9) 0.2214(8) 0.2165(2) 0.0411(14) Uani 1 1 d . . . H6A H 0.5690 0.1969 0.2450 0.049 Uiso 1 1 calc R . . H6B H 0.5268 0.1071 0.1961 0.049 Uiso 1 1 calc R . . C7 C 0.2659(8) 0.2205(8) 0.23250(19) 0.0370(14) Uani 1 1 d . . . H7A H 0.1813 0.2396 0.2043 0.044 Uiso 1 1 calc R . . H7B H 0.2224 0.3347 0.2528 0.044 Uiso 1 1 calc R . . C8 C 0.2329(8) 0.0239(7) 0.26020(19) 0.0344(13) Uani 1 1 d . . . H8A H 0.3120 0.0102 0.2893 0.041 Uiso 1 1 calc R . . H8B H 0.2868 -0.0898 0.2406 0.041 Uiso 1 1 calc R . . C9 C 0.0121(8) 0.0066(7) 0.27466(18) 0.0328(13) Uani 1 1 d . . . H9A H -0.0685 0.0254 0.2458 0.039 Uiso 1 1 calc R . . H9B H -0.0405 0.1164 0.2955 0.039 Uiso 1 1 calc R . . C10 C -0.0170(8) -0.1962(7) 0.30068(18) 0.0331(13) Uani 1 1 d . . . H10A H 0.0465 -0.3060 0.2809 0.040 Uiso 1 1 calc R . . H10B H 0.0549 -0.2096 0.3308 0.040 Uiso 1 1 calc R . . C11 C -0.2379(8) -0.2237(8) 0.31195(19) 0.0341(13) Uani 1 1 d . . . H11A H -0.2982 -0.1209 0.3340 0.041 Uiso 1 1 calc R . . H11B H -0.3123 -0.1988 0.2822 0.041 Uiso 1 1 calc R . . C12 C -0.2679(8) -0.4307(8) 0.33405(19) 0.0353(13) Uani 1 1 d . . . H12A H -0.2059 -0.5336 0.3122 0.042 Uiso 1 1 calc R . . H12B H -0.1951 -0.4548 0.3640 0.042 Uiso 1 1 calc R . . C13 C -0.4873(8) -0.4588(8) 0.3446(2) 0.0367(13) Uani 1 1 d . . . H13A H -0.5592 -0.4382 0.3145 0.044 Uiso 1 1 calc R . . H13B H -0.5503 -0.3536 0.3657 0.044 Uiso 1 1 calc R . . C14 C -0.5176(8) -0.6660(7) 0.36810(19) 0.0341(13) Uani 1 1 d . . . H14A H -0.4550 -0.7713 0.3469 0.041 Uiso 1 1 calc R . . H14B H -0.4454 -0.6868 0.3982 0.041 Uiso 1 1 calc R . . C15 C -0.7391(8) -0.6940(7) 0.37886(19) 0.0327(13) Uani 1 1 d . . . H15A H -0.8025 -0.5865 0.3993 0.039 Uiso 1 1 calc R . . H15B H -0.8104 -0.6766 0.3486 0.039 Uiso 1 1 calc R . . C16 C -0.7697(8) -0.8971(7) 0.40326(18) 0.0330(13) Uani 1 1 d . . . H16A H -0.7116 -1.0045 0.3822 0.040 Uiso 1 1 calc R . . H16B H -0.6939 -0.9170 0.4328 0.040 Uiso 1 1 calc R . . C17 C -0.9890(7) -0.9201(7) 0.41555(18) 0.0313(13) Uani 1 1 d . . . H17A H -1.0641 -0.9021 0.3858 0.038 Uiso 1 1 calc R . . H17B H -1.0475 -0.8108 0.4360 0.038 Uiso 1 1 calc R . . C18 C -1.0233(8) -1.1230(7) 0.44100(18) 0.0334(13) Uani 1 1 d . . . H18A H -0.9668 -1.2329 0.4205 0.040 Uiso 1 1 calc R . . H18B H -0.9485 -1.1421 0.4707 0.040 Uiso 1 1 calc R . . C19 C -1.2449(8) -1.1389(8) 0.45294(19) 0.0377(14) Uani 1 1 d . . . H19A H -1.3196 -1.1181 0.4232 0.045 Uiso 1 1 calc R . . H19B H -1.3007 -1.0294 0.4736 0.045 Uiso 1 1 calc R . . C20 C -1.2821(9) -1.3411(8) 0.4779(2) 0.0479(15) Uani 1 1 d . . . H20A H -1.2297 -1.4505 0.4575 0.072 Uiso 1 1 calc R . . H20B H -1.4280 -1.3416 0.4844 0.072 Uiso 1 1 calc R . . H20C H -1.2125 -1.3612 0.5080 0.072 Uiso 1 1 calc R . . C21 C 0.9942(11) 0.4637(10) 0.1111(2) 0.0624(19) Uani 1 1 d . . . H21 H 1.0377 0.3247 0.1070 0.075 Uiso 1 1 calc R . . C22 C 1.0754(11) 0.6101(13) 0.0870(2) 0.072(2) Uani 1 1 d . . . H22 H 1.1793 0.5850 0.0630 0.086 Uiso 1 1 d R . . C23 C 0.9913(13) 0.8202(12) 0.1003(2) 0.075(2) Uani 1 1 d . . . H23 H 1.0454 0.9229 0.0806 0.090 Uiso 1 1 d R . . C24 C 0.9639(9) 0.8592(8) 0.15208(19) 0.0403(14) Uani 1 1 d . . . H24A H 0.8784 0.9906 0.1559 0.048 Uiso 1 1 calc R . . H24B H 1.0976 0.8659 0.1652 0.048 Uiso 1 1 calc R . . C25 C 0.8628(8) 0.6896(8) 0.17975(18) 0.0368(13) Uani 1 1 d . . . H25A H 0.9531 0.6228 0.2046 0.044 Uiso 1 1 calc R . . H25B H 0.7339 0.7480 0.1955 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0685(7) 0.0502(6) 0.0379(5) 0.0042(4) -0.0068(4) -0.0270(5) O1 0.086(4) 0.080(4) 0.091(4) 0.035(3) -0.026(3) -0.033(3) O2 0.127(5) 0.065(4) 0.086(4) 0.012(3) -0.040(3) -0.053(3) O3 0.153(6) 0.111(5) 0.042(3) 0.017(3) -0.013(3) -0.073(4) O4 0.077(3) 0.043(3) 0.047(2) -0.0056(19) 0.017(2) -0.023(2) O5 0.051(3) 0.033(3) 0.112(4) 0.014(2) -0.020(3) 0.000(2) C1 0.068(6) 0.112(7) 0.083(6) -0.058(5) -0.025(4) 0.053(5) C2 0.091(6) 0.067(5) 0.046(4) 0.021(3) -0.019(4) -0.034(4) C3 0.108(6) 0.073(5) 0.052(4) -0.002(4) -0.012(4) -0.054(5) C4 0.091(6) 0.063(5) 0.037(4) -0.003(3) 0.011(3) -0.040(4) C5 0.050(4) 0.032(4) 0.054(4) 0.001(3) -0.021(3) -0.004(3) C6 0.052(4) 0.026(3) 0.044(3) 0.001(3) 0.003(3) -0.005(3) C7 0.038(4) 0.032(3) 0.041(3) -0.001(2) -0.005(3) -0.003(3) C8 0.038(4) 0.021(3) 0.043(3) -0.003(2) -0.004(3) 0.004(2) C9 0.039(4) 0.025(3) 0.033(3) -0.005(2) -0.003(2) 0.003(2) C10 0.037(4) 0.027(3) 0.034(3) -0.005(2) -0.004(2) 0.002(2) C11 0.032(3) 0.029(3) 0.040(3) -0.005(2) -0.004(2) 0.003(2) C12 0.033(4) 0.029(3) 0.042(3) -0.004(2) -0.001(3) 0.003(3) C13 0.032(4) 0.027(3) 0.051(3) -0.007(3) -0.004(3) -0.001(2) C14 0.027(3) 0.024(3) 0.050(3) -0.004(2) -0.002(3) 0.003(2) C15 0.031(3) 0.022(3) 0.043(3) -0.005(2) -0.002(2) 0.007(2) C16 0.032(3) 0.028(3) 0.036(3) -0.005(2) -0.003(2) 0.005(2) C17 0.028(3) 0.023(3) 0.039(3) -0.002(2) 0.000(2) 0.007(2) C18 0.033(3) 0.028(3) 0.037(3) -0.003(2) -0.001(2) 0.002(2) C19 0.037(4) 0.034(3) 0.042(3) -0.003(3) 0.000(3) -0.005(3) C20 0.050(4) 0.037(4) 0.057(4) -0.004(3) 0.004(3) -0.010(3) C21 0.083(5) 0.041(4) 0.066(5) -0.006(3) -0.020(4) -0.008(4) C22 0.072(5) 0.094(6) 0.053(4) -0.008(4) 0.005(4) -0.029(5) C23 0.120(7) 0.069(5) 0.047(4) 0.003(4) -0.002(4) -0.055(5) C24 0.037(4) 0.037(3) 0.047(3) -0.007(3) 0.000(3) -0.006(3) C25 0.037(4) 0.034(3) 0.038(3) -0.003(2) -0.001(3) -0.004(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 C1 1.752(8) . ? Fe1 C3 1.777(7) . ? Fe1 C2 1.784(7) . ? Fe1 C22 1.978(7) . ? Fe1 C21 2.006(7) . ? Fe1 C4 2.061(6) . ? Fe1 C23 2.062(7) . ? O1 C1 1.199(8) . ? O2 C2 1.161(7) . ? O3 C3 1.154(7) . ? O4 C5 1.367(7) . ? O4 C4 1.419(7) . ? O5 C5 1.182(7) . ? C4 C25 1.484(8) . ? C4 C21 1.538(9) . ? C5 C6 1.510(8) . ? C6 C7 1.512(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.523(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.529(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.523(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.513(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.511(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.529(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.525(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.515(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.510(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.530(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.514(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.527(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.314(9) . ? C21 H21 0.9500 . ? C22 C23 1.507(11) . ? C22 H22 0.9500 . ? C23 C24 1.500(8) . ? C23 H23 0.9504 . ? C24 C25 1.543(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? 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 C3 100.5(4) . . ? C1 Fe1 C2 104.0(4) . . ? C3 Fe1 C2 92.2(3) . . ? C1 Fe1 C22 131.0(3) . . ? C3 Fe1 C22 94.4(3) . . ? C2 Fe1 C22 121.9(4) . . ? C1 Fe1 C21 129.7(3) . . ? C3 Fe1 C21 125.3(4) . . ? C2 Fe1 C21 94.7(3) . . ? C22 Fe1 C21 38.5(3) . . ? C1 Fe1 C4 86.7(4) . . ? C3 Fe1 C4 166.6(3) . . ? C2 Fe1 C4 97.0(3) . . ? C22 Fe1 C4 72.5(3) . . ? C21 Fe1 C4 44.4(3) . . ? C1 Fe1 C23 89.1(4) . . ? C3 Fe1 C23 91.6(3) . . ? C2 Fe1 C23 165.5(3) . . ? C22 Fe1 C23 43.7(3) . . ? C21 Fe1 C23 71.7(3) . . ? C4 Fe1 C23 77.1(3) . . ? C5 O4 C4 120.7(5) . . ? O1 C1 Fe1 176.3(7) . . ? O2 C2 Fe1 177.1(8) . . ? O3 C3 Fe1 178.1(6) . . ? O4 C4 C25 114.6(5) . . ? O4 C4 C21 111.5(5) . . ? C25 C4 C21 117.6(5) . . ? O4 C4 Fe1 124.0(4) . . ? C25 C4 Fe1 114.2(4) . . ? C21 C4 Fe1 65.9(3) . . ? O5 C5 O4 124.8(6) . . ? O5 C5 C6 125.7(6) . . ? O4 C5 C6 109.5(5) . . ? C5 C6 C7 115.8(5) . . ? C5 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? C5 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C6 C7 C8 111.5(4) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 114.4(4) . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 113.1(4) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.1(4) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 114.2(4) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 114.1(4) . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 114.2(4) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 114.1(4) . . ? C15 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C16 C15 C14 114.3(4) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 113.9(4) . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C15 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 114.8(4) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C17 113.0(4) . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 C20 113.7(5) . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C4 113.6(6) . . ? C22 C21 Fe1 69.6(4) . . ? C4 C21 Fe1 69.7(4) . . ? C22 C21 H21 123.2 . . ? C4 C21 H21 123.2 . . ? Fe1 C21 H21 129.4 . . ? C21 C22 C23 115.1(7) . . ? C21 C22 Fe1 71.9(4) . . ? C23 C22 Fe1 71.1(4) . . ? C21 C22 H22 122.3 . . ? C23 C22 H22 122.5 . . ? Fe1 C22 H22 126.1 . . ? C24 C23 C22 118.2(6) . . ? C24 C23 Fe1 113.3(4) . . ? C22 C23 Fe1 65.1(4) . . ? C24 C23 H23 115.1 . . ? C22 C23 H23 113.1 . . ? Fe1 C23 H23 122.9 . . ? C23 C24 C25 110.4(5) . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C4 C25 C24 109.9(4) . . ? C4 C25 H25A 109.7 . . ? C24 C25 H25A 109.7 . . ? C4 C25 H25B 109.7 . . ? C24 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? 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 C5 O4 C4 C25 62.9(8) . . . . ? C5 O4 C4 C21 -160.3(5) . . . . ? C5 O4 C4 Fe1 -85.6(6) . . . . ? C1 Fe1 C4 O4 92.8(6) . . . . ? C3 Fe1 C4 O4 -144.2(12) . . . . ? C2 Fe1 C4 O4 -10.9(6) . . . . ? C22 Fe1 C4 O4 -132.2(6) . . . . ? C21 Fe1 C4 O4 -100.5(7) . . . . ? C23 Fe1 C4 O4 -177.4(6) . . . . ? C1 Fe1 C4 C25 -55.9(6) . . . . ? C3 Fe1 C4 C25 67.1(16) . . . . ? C2 Fe1 C4 C25 -159.6(5) . . . . ? C22 Fe1 C4 C25 79.1(5) . . . . ? C21 Fe1 C4 C25 110.8(6) . . . . ? C23 Fe1 C4 C25 33.9(5) . . . . ? C1 Fe1 C4 C21 -166.7(4) . . . . ? C3 Fe1 C4 C21 -43.7(15) . . . . ? C2 Fe1 C4 C21 89.6(4) . . . . ? C22 Fe1 C4 C21 -31.7(4) . . . . ? C23 Fe1 C4 C21 -76.9(4) . . . . ? C4 O4 C5 O5 7.3(9) . . . . ? C4 O4 C5 C6 -170.7(5) . . . . ? O5 C5 C6 C7 15.5(9) . . . . ? O4 C5 C6 C7 -166.5(5) . . . . ? C5 C6 C7 C8 -178.7(5) . . . . ? C6 C7 C8 C9 -176.2(4) . . . . ? C7 C8 C9 C10 177.6(4) . . . . ? C8 C9 C10 C11 -175.3(4) . . . . ? C9 C10 C11 C12 175.2(4) . . . . ? C10 C11 C12 C13 -179.2(4) . . . . ? C11 C12 C13 C14 -178.5(5) . . . . ? C12 C13 C14 C15 179.8(4) . . . . ? C13 C14 C15 C16 -178.5(4) . . . . ? C14 C15 C16 C17 177.7(4) . . . . ? C15 C16 C17 C18 -179.0(4) . . . . ? C16 C17 C18 C19 179.6(4) . . . . ? C17 C18 C19 C20 179.5(5) . . . . ? O4 C4 C21 C22 174.3(6) . . . . ? C25 C4 C21 C22 -50.4(8) . . . . ? Fe1 C4 C21 C22 55.4(5) . . . . ? O4 C4 C21 Fe1 118.8(5) . . . . ? C25 C4 C21 Fe1 -105.9(5) . . . . ? C1 Fe1 C21 C22 -109.0(6) . . . . ? C3 Fe1 C21 C22 42.4(6) . . . . ? C2 Fe1 C21 C22 138.4(5) . . . . ? C4 Fe1 C21 C22 -126.3(6) . . . . ? C23 Fe1 C21 C22 -36.2(4) . . . . ? C1 Fe1 C21 C4 17.3(6) . . . . ? C3 Fe1 C21 C4 168.7(4) . . . . ? C2 Fe1 C21 C4 -95.2(4) . . . . ? C22 Fe1 C21 C4 126.3(6) . . . . ? C23 Fe1 C21 C4 90.1(4) . . . . ? C4 C21 C22 C23 2.5(9) . . . . ? Fe1 C21 C22 C23 58.0(5) . . . . ? C4 C21 C22 Fe1 -55.5(5) . . . . ? C1 Fe1 C22 C21 105.5(6) . . . . ? C3 Fe1 C22 C21 -146.5(5) . . . . ? C2 Fe1 C22 C21 -51.2(5) . . . . ? C4 Fe1 C22 C21 36.2(4) . . . . ? C23 Fe1 C22 C21 125.7(6) . . . . ? C1 Fe1 C22 C23 -20.3(6) . . . . ? C3 Fe1 C22 C23 87.7(4) . . . . ? C2 Fe1 C22 C23 -176.9(4) . . . . ? C21 Fe1 C22 C23 -125.7(6) . . . . ? C4 Fe1 C22 C23 -89.5(4) . . . . ? C21 C22 C23 C24 45.8(9) . . . . ? Fe1 C22 C23 C24 104.2(6) . . . . ? C21 C22 C23 Fe1 -58.5(6) . . . . ? C1 Fe1 C23 C24 53.2(6) . . . . ? C3 Fe1 C23 C24 153.7(6) . . . . ? C2 Fe1 C23 C24 -101.1(12) . . . . ? C22 Fe1 C23 C24 -111.6(7) . . . . ? C21 Fe1 C23 C24 -79.4(5) . . . . ? C4 Fe1 C23 C24 -33.6(5) . . . . ? C1 Fe1 C23 C22 164.8(5) . . . . ? C3 Fe1 C23 C22 -94.7(4) . . . . ? C2 Fe1 C23 C22 10.4(13) . . . . ? C21 Fe1 C23 C22 32.2(4) . . . . ? C4 Fe1 C23 C22 78.0(4) . . . . ? C22 C23 C24 C25 -45.6(8) . . . . ? Fe1 C23 C24 C25 27.6(7) . . . . ? O4 C4 C25 C24 -179.2(5) . . . . ? C21 C4 C25 C24 46.9(7) . . . . ? Fe1 C4 C25 C24 -27.5(7) . . . . ? C23 C24 C25 C4 -0.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 1.091 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.076 # Attachment '- rac17.cif' data_rac-17 _database_code_depnum_ccdc_archive 'CCDC 872874' #TrackingRef '- rac17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H38 Fe O5' _chemical_formula_sum 'C25 H38 Fe O5' _chemical_formula_weight 474.40 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6905(3) _cell_length_b 10.0025(4) _cell_length_c 28.6690(12) _cell_angle_alpha 89.975(2) _cell_angle_beta 87.653(2) _cell_angle_gamma 82.287(2) _cell_volume 2467.45(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16558 _cell_measurement_theta_min 1.42 _cell_measurement_theta_max 27.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Nonius KappaCCD' _diffrn_measurement_method Phi/Omega-Scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16558 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.00 _reflns_number_total 10724 _reflns_number_gt 7271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_data_reduction 'Nonius DENZO (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2004)' _refine_special_details ; H21, H22, H25, H46, H47 and H50 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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^)+(0.0736P)^2^+1.2533P] 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 10724 _refine_ls_number_parameters 561 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.74504(5) -0.14812(5) 0.406876(16) 0.02103(13) Uani 1 1 d . . . O1 O 0.7742(3) -0.4229(3) 0.44458(9) 0.0325(6) Uani 1 1 d . . . O2 O 0.4160(2) -0.1396(3) 0.38498(9) 0.0363(6) Uani 1 1 d . . . O3 O 0.7259(3) 0.0162(3) 0.49198(9) 0.0379(6) Uani 1 1 d . . . O4 O 0.7259(2) -0.1382(2) 0.30196(8) 0.0245(5) Uani 1 1 d . . . O5 O 0.8456(3) 0.0077(3) 0.25817(8) 0.0338(6) Uani 1 1 d . . . C1 C 0.7602(3) -0.3157(4) 0.42997(12) 0.0250(7) Uani 1 1 d . . . C2 C 0.5442(4) -0.1441(4) 0.39361(12) 0.0261(8) Uani 1 1 d . . . C3 C 0.7310(4) -0.0498(4) 0.45889(12) 0.0257(8) Uani 1 1 d . . . C4 C 0.8106(3) -0.1034(3) 0.33991(11) 0.0212(7) Uani 1 1 d . . . C5 C 0.7527(3) -0.0698(3) 0.26170(11) 0.0239(7) Uani 1 1 d . . . C6 C 0.6540(4) -0.1108(3) 0.22394(11) 0.0244(7) Uani 1 1 d . . . H6A H 0.5531 -0.1292 0.2381 0.029 Uiso 1 1 calc R . . H6B H 0.7060 -0.1954 0.2093 0.029 Uiso 1 1 calc R . . C7 C 0.6239(3) -0.0035(3) 0.18623(11) 0.0233(7) Uani 1 1 d . . . H7A H 0.5724 0.0814 0.2008 0.028 Uiso 1 1 calc R . . H7B H 0.7245 0.0144 0.1718 0.028 Uiso 1 1 calc R . . C8 C 0.5223(3) -0.0468(3) 0.14836(11) 0.0228(7) Uani 1 1 d . . . H8A H 0.5773 -0.1282 0.1324 0.027 Uiso 1 1 calc R . . H8B H 0.4250 -0.0711 0.1632 0.027 Uiso 1 1 calc R . . C9 C 0.4818(4) 0.0626(3) 0.11221(11) 0.0240(7) Uani 1 1 d . . . H9A H 0.5792 0.0865 0.0973 0.029 Uiso 1 1 calc R . . H9B H 0.4275 0.1443 0.1282 0.029 Uiso 1 1 calc R . . C10 C 0.3792(4) 0.0204(3) 0.07429(11) 0.0235(7) Uani 1 1 d . . . H10A H 0.4341 -0.0605 0.0580 0.028 Uiso 1 1 calc R . . H10B H 0.2824 -0.0046 0.0892 0.028 Uiso 1 1 calc R . . C11 C 0.3370(4) 0.1308(3) 0.03845(11) 0.0231(7) Uani 1 1 d . . . H11A H 0.4338 0.1568 0.0238 0.028 Uiso 1 1 calc R . . H11B H 0.2807 0.2113 0.0547 0.028 Uiso 1 1 calc R . . C12 C 0.2361(3) 0.0873(3) 0.00022(11) 0.0225(7) Uani 1 1 d . . . H12A H 0.1389 0.0621 0.0148 0.027 Uiso 1 1 calc R . . H12B H 0.2920 0.0063 -0.0158 0.027 Uiso 1 1 calc R . . C13 C 0.1948(4) 0.1975(3) -0.03601(11) 0.0249(7) Uani 1 1 d . . . H13A H 0.1387 0.2784 -0.0200 0.030 Uiso 1 1 calc R . . H13B H 0.2919 0.2228 -0.0506 0.030 Uiso 1 1 calc R . . C14 C 0.0946(4) 0.1540(3) -0.07405(11) 0.0245(7) Uani 1 1 d . . . H14A H -0.0029 0.1297 -0.0594 0.029 Uiso 1 1 calc R . . H14B H 0.1502 0.0722 -0.0897 0.029 Uiso 1 1 calc R . . C15 C 0.0540(4) 0.2618(3) -0.11075(11) 0.0250(7) Uani 1 1 d . . . H15A H -0.0028 0.3433 -0.0952 0.030 Uiso 1 1 calc R . . H15B H 0.1514 0.2869 -0.1252 0.030 Uiso 1 1 calc R . . C16 C -0.0447(4) 0.2168(3) -0.14891(11) 0.0246(7) Uani 1 1 d . . . H16A H -0.1424 0.1926 -0.1343 0.030 Uiso 1 1 calc R . . H16B H 0.0116 0.1344 -0.1640 0.030 Uiso 1 1 calc R . . C17 C -0.0854(4) 0.3225(3) -0.18657(11) 0.0245(7) Uani 1 1 d . . . H17A H -0.1460 0.4038 -0.1720 0.029 Uiso 1 1 calc R . . H17B H 0.0117 0.3492 -0.2007 0.029 Uiso 1 1 calc R . . C18 C -0.1791(4) 0.2704(3) -0.22473(12) 0.0259(8) Uani 1 1 d . . . H18A H -0.1199 0.1864 -0.2379 0.031 Uiso 1 1 calc R . . H18B H -0.2773 0.2468 -0.2104 0.031 Uiso 1 1 calc R . . C19 C -0.2179(4) 0.3673(4) -0.26425(12) 0.0287(8) Uani 1 1 d . . . H19A H -0.1208 0.3955 -0.2779 0.034 Uiso 1 1 calc R . . H19B H -0.2841 0.4489 -0.2519 0.034 Uiso 1 1 calc R . . C20 C -0.3024(4) 0.3039(4) -0.30236(12) 0.0332(9) Uani 1 1 d . . . H20A H -0.2442 0.2164 -0.3115 0.050 Uiso 1 1 calc R . . H20B H -0.3106 0.3635 -0.3295 0.050 Uiso 1 1 calc R . . H20C H -0.4067 0.2909 -0.2905 0.050 Uiso 1 1 calc R . . C21 C 0.9240(3) -0.2021(4) 0.35823(12) 0.0266(8) Uani 1 1 d . . . H21 H 0.9412 -0.2912 0.3459 0.032 Uiso 1 1 d R . . C22 C 0.9868(3) -0.1564(4) 0.39983(12) 0.0268(8) Uani 1 1 d . . . H22 H 1.0516 -0.2235 0.4161 0.032 Uiso 1 1 d R . . C23 C 1.0336(3) -0.0176(4) 0.40192(13) 0.0301(8) Uani 1 1 d . . . H23A H 1.1347 -0.0170 0.3847 0.036 Uiso 1 1 calc R . . H23B H 1.0468 0.0068 0.4348 0.036 Uiso 1 1 calc R . . C24 C 0.9106(3) 0.0881(4) 0.38050(12) 0.0267(8) Uani 1 1 d . . . H24A H 0.8717 0.1580 0.4041 0.032 Uiso 1 1 calc R . . H24B H 0.9583 0.1327 0.3538 0.032 Uiso 1 1 calc R . . C25 C 0.7767(3) 0.0197(3) 0.36410(11) 0.0218(7) Uani 1 1 d . . . H25 H 0.6883 0.0774 0.3541 0.026 Uiso 1 1 d R . . Fe2 Fe 0.22513(5) 0.37417(5) 0.416087(16) 0.02170(13) Uani 1 1 d . . . O6 O 0.3126(3) 0.6272(3) 0.45214(9) 0.0340(6) Uani 1 1 d . . . O7 O -0.0043(3) 0.3009(3) 0.48648(9) 0.0386(7) Uani 1 1 d . . . O8 O -0.0208(3) 0.4521(3) 0.35007(9) 0.0351(6) Uani 1 1 d . . . O9 O 0.2602(2) 0.1804(2) 0.33607(7) 0.0233(5) Uani 1 1 d . . . O10 O 0.4801(2) 0.1286(3) 0.29210(8) 0.0327(6) Uani 1 1 d . . . C26 C 0.2725(4) 0.5308(4) 0.43855(12) 0.0281(8) Uani 1 1 d . . . C27 C 0.0859(4) 0.3311(4) 0.45921(12) 0.0267(8) Uani 1 1 d . . . C28 C 0.0745(4) 0.4233(3) 0.37609(12) 0.0264(8) Uani 1 1 d . . . C29 C 0.3440(3) 0.2387(3) 0.36999(11) 0.0209(7) Uani 1 1 d . . . C30 C 0.3417(3) 0.1334(3) 0.29621(11) 0.0216(7) Uani 1 1 d . . . C31 C 0.2351(3) 0.0950(3) 0.26031(11) 0.0228(7) Uani 1 1 d . . . H31A H 0.1394 0.0701 0.2760 0.027 Uiso 1 1 calc R . . H31B H 0.2865 0.0153 0.2425 0.027 Uiso 1 1 calc R . . C32 C 0.1919(4) 0.2125(3) 0.22650(11) 0.0243(7) Uani 1 1 d . . . H32A H 0.1340 0.2899 0.2440 0.029 Uiso 1 1 calc R . . H32B H 0.2880 0.2416 0.2126 0.029 Uiso 1 1 calc R . . C33 C 0.0925(3) 0.1711(3) 0.18769(11) 0.0226(7) Uani 1 1 d . . . H33A H -0.0045 0.1443 0.2019 0.027 Uiso 1 1 calc R . . H33B H 0.1494 0.0914 0.1712 0.027 Uiso 1 1 calc R . . C34 C 0.0504(3) 0.2832(3) 0.15206(11) 0.0230(7) Uani 1 1 d . . . H34A H -0.0065 0.3631 0.1684 0.028 Uiso 1 1 calc R . . H34B H 0.1472 0.3098 0.1376 0.028 Uiso 1 1 calc R . . C35 C -0.0495(4) 0.2394(3) 0.11371(11) 0.0242(7) Uani 1 1 d . . . H35A H -0.1461 0.2131 0.1283 0.029 Uiso 1 1 calc R . . H35B H 0.0074 0.1588 0.0977 0.029 Uiso 1 1 calc R . . C36 C -0.0927(3) 0.3487(3) 0.07731(11) 0.0237(7) Uani 1 1 d . . . H36A H -0.1505 0.4290 0.0932 0.028 Uiso 1 1 calc R . . H36B H 0.0039 0.3756 0.0629 0.028 Uiso 1 1 calc R . . C37 C -0.1913(3) 0.3038(3) 0.03889(11) 0.0229(7) Uani 1 1 d . . . H37A H -0.2883 0.2778 0.0533 0.028 Uiso 1 1 calc R . . H37B H -0.1339 0.2230 0.0231 0.028 Uiso 1 1 calc R . . C38 C -0.2331(4) 0.4129(3) 0.00225(11) 0.0245(7) Uani 1 1 d . . . H38A H -0.1361 0.4392 -0.0121 0.029 Uiso 1 1 calc R . . H38B H -0.2909 0.4936 0.0180 0.029 Uiso 1 1 calc R . . C39 C -0.3317(3) 0.3674(3) -0.03641(11) 0.0232(7) Uani 1 1 d . . . H39A H -0.2742 0.2864 -0.0520 0.028 Uiso 1 1 calc R . . H39B H -0.4290 0.3417 -0.0221 0.028 Uiso 1 1 calc R . . C40 C -0.3724(3) 0.4765(3) -0.07312(11) 0.0237(7) Uani 1 1 d . . . H40A H -0.4303 0.5572 -0.0574 0.028 Uiso 1 1 calc R . . H40B H -0.2749 0.5026 -0.0872 0.028 Uiso 1 1 calc R . . C41 C -0.4693(3) 0.4325(3) -0.11186(11) 0.0237(7) Uani 1 1 d . . . H41A H -0.5668 0.4062 -0.0979 0.028 Uiso 1 1 calc R . . H41B H -0.4113 0.3519 -0.1276 0.028 Uiso 1 1 calc R . . C42 C -0.5098(4) 0.5421(3) -0.14832(11) 0.0251(7) Uani 1 1 d . . . H42A H -0.5672 0.6228 -0.1325 0.030 Uiso 1 1 calc R . . H42B H -0.4122 0.5681 -0.1624 0.030 Uiso 1 1 calc R . . C43 C -0.6079(4) 0.4988(4) -0.18724(12) 0.0267(8) Uani 1 1 d . . . H43A H -0.7047 0.4713 -0.1732 0.032 Uiso 1 1 calc R . . H43B H -0.5498 0.4194 -0.2036 0.032 Uiso 1 1 calc R . . C44 C -0.6500(4) 0.6105(4) -0.22284(12) 0.0309(8) Uani 1 1 d . . . H44A H -0.7074 0.6902 -0.2064 0.037 Uiso 1 1 calc R . . H44B H -0.5531 0.6376 -0.2370 0.037 Uiso 1 1 calc R . . C45 C -0.7485(4) 0.5684(5) -0.26152(13) 0.0440(11) Uani 1 1 d . . . H45A H -0.6880 0.4963 -0.2802 0.066 Uiso 1 1 calc R . . H45B H -0.7796 0.6460 -0.2815 0.066 Uiso 1 1 calc R . . H45C H -0.8415 0.5357 -0.2477 0.066 Uiso 1 1 calc R . . C46 C 0.3521(3) 0.1851(3) 0.41545(11) 0.0230(7) Uani 1 1 d . . . H46 H 0.3037 0.1082 0.4235 0.028 Uiso 1 1 d R . . C47 C 0.4184(3) 0.2673(3) 0.44749(12) 0.0218(7) Uani 1 1 d . . . H47 H 0.4072 0.2495 0.4799 0.026 Uiso 1 1 d R . . C48 C 0.5628(3) 0.3307(4) 0.43357(12) 0.0250(7) Uani 1 1 d . . . H48A H 0.6561 0.2630 0.4365 0.030 Uiso 1 1 calc R . . H48B H 0.5718 0.4067 0.4550 0.030 Uiso 1 1 calc R . . C49 C 0.5563(3) 0.3821(4) 0.38332(12) 0.0272(8) Uani 1 1 d . . . H49A H 0.5690 0.4790 0.3828 0.033 Uiso 1 1 calc R . . H49B H 0.6426 0.3324 0.3641 0.033 Uiso 1 1 calc R . . C50 C 0.4027(3) 0.3632(4) 0.36281(11) 0.0229(7) Uani 1 1 d . . . H50 H 0.3845 0.4103 0.3345 0.027 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0169(2) 0.0240(3) 0.0227(3) 0.0005(2) -0.00241(17) -0.00395(18) O1 0.0396(14) 0.0272(15) 0.0325(15) 0.0033(12) -0.0034(11) -0.0103(11) O2 0.0182(12) 0.0416(16) 0.0498(17) -0.0120(13) -0.0048(10) -0.0052(11) O3 0.0519(16) 0.0360(16) 0.0273(15) -0.0030(13) -0.0027(11) -0.0110(13) O4 0.0309(12) 0.0236(13) 0.0198(13) 0.0015(10) -0.0026(9) -0.0057(10) O5 0.0293(12) 0.0494(17) 0.0266(14) 0.0030(12) -0.0015(10) -0.0189(12) C1 0.0221(16) 0.031(2) 0.0229(19) -0.0048(16) -0.0004(13) -0.0084(14) C2 0.0298(18) 0.027(2) 0.0224(19) -0.0051(15) 0.0007(13) -0.0059(14) C3 0.0249(16) 0.027(2) 0.027(2) 0.0045(16) -0.0022(13) -0.0098(14) C4 0.0204(15) 0.0248(18) 0.0186(17) 0.0027(14) -0.0005(12) -0.0045(13) C5 0.0221(16) 0.0269(19) 0.0211(18) 0.0008(15) 0.0025(12) 0.0017(14) C6 0.0263(16) 0.0241(19) 0.0234(19) -0.0016(15) -0.0001(13) -0.0056(14) C7 0.0220(15) 0.0253(19) 0.0234(18) -0.0004(15) 0.0002(12) -0.0068(13) C8 0.0249(16) 0.0229(18) 0.0210(18) -0.0021(14) 0.0004(12) -0.0048(13) C9 0.0249(16) 0.0227(18) 0.0258(19) -0.0005(15) -0.0022(13) -0.0074(13) C10 0.0249(16) 0.0242(19) 0.0222(18) -0.0020(15) -0.0003(13) -0.0062(13) C11 0.0262(16) 0.0229(18) 0.0213(18) -0.0024(14) -0.0017(13) -0.0074(13) C12 0.0239(16) 0.0216(18) 0.0235(18) -0.0026(14) -0.0035(13) -0.0081(13) C13 0.0258(16) 0.0247(19) 0.0253(19) -0.0015(15) -0.0036(13) -0.0061(14) C14 0.0222(16) 0.0257(19) 0.0260(19) -0.0007(15) -0.0010(13) -0.0051(13) C15 0.0262(16) 0.0246(19) 0.0250(19) 0.0005(15) -0.0032(13) -0.0063(14) C16 0.0241(16) 0.0246(19) 0.0261(19) -0.0025(15) -0.0025(13) -0.0065(14) C17 0.0254(16) 0.0252(19) 0.0243(19) -0.0015(15) -0.0037(13) -0.0079(14) C18 0.0242(16) 0.0252(19) 0.029(2) -0.0005(15) -0.0011(13) -0.0063(14) C19 0.0334(18) 0.025(2) 0.028(2) -0.0001(16) -0.0024(14) -0.0053(15) C20 0.040(2) 0.033(2) 0.027(2) 0.0025(17) -0.0072(15) -0.0060(16) C21 0.0243(16) 0.0257(19) 0.028(2) -0.0021(15) 0.0062(13) 0.0012(14) C22 0.0154(15) 0.035(2) 0.029(2) 0.0040(16) -0.0016(13) 0.0013(14) C23 0.0155(15) 0.039(2) 0.037(2) 0.0031(17) -0.0040(13) -0.0067(14) C24 0.0215(16) 0.029(2) 0.030(2) -0.0022(16) -0.0008(13) -0.0044(14) C25 0.0161(14) 0.0240(18) 0.0243(18) 0.0018(14) -0.0011(12) 0.0005(13) Fe2 0.0196(2) 0.0230(3) 0.0219(3) -0.0024(2) -0.00088(17) -0.00081(18) O6 0.0371(14) 0.0249(15) 0.0401(16) -0.0078(12) -0.0049(11) -0.0036(11) O7 0.0262(13) 0.0574(19) 0.0311(15) 0.0021(13) 0.0038(11) -0.0031(12) O8 0.0338(13) 0.0349(16) 0.0357(16) -0.0008(12) -0.0099(11) 0.0014(11) O9 0.0210(11) 0.0282(14) 0.0213(13) -0.0074(10) 0.0016(9) -0.0062(9) O10 0.0198(12) 0.0494(17) 0.0279(14) -0.0132(12) -0.0001(9) -0.0010(11) C26 0.0237(17) 0.033(2) 0.026(2) -0.0004(16) -0.0032(13) 0.0045(15) C27 0.0238(16) 0.028(2) 0.028(2) -0.0034(16) -0.0051(14) -0.0017(14) C28 0.0290(17) 0.0220(19) 0.027(2) -0.0071(15) 0.0027(14) -0.0008(14) C29 0.0154(14) 0.0227(18) 0.0250(18) -0.0065(14) -0.0001(12) -0.0041(12) C30 0.0242(16) 0.0219(18) 0.0183(17) -0.0003(14) 0.0008(12) -0.0022(13) C31 0.0221(15) 0.0275(19) 0.0189(18) -0.0036(14) -0.0014(12) -0.0033(13) C32 0.0237(16) 0.0248(19) 0.0255(19) -0.0019(15) -0.0044(13) -0.0062(13) C33 0.0218(15) 0.0255(19) 0.0217(18) -0.0043(14) -0.0032(12) -0.0070(13) C34 0.0220(15) 0.0204(18) 0.0276(19) -0.0013(14) -0.0027(13) -0.0063(13) C35 0.0257(16) 0.0245(19) 0.0237(19) -0.0003(15) -0.0019(13) -0.0073(14) C36 0.0225(15) 0.0255(19) 0.0239(19) 0.0005(15) -0.0029(12) -0.0058(13) C37 0.0213(15) 0.0241(19) 0.0243(18) -0.0004(15) -0.0026(12) -0.0059(13) C38 0.0236(16) 0.0241(19) 0.0269(19) -0.0021(15) -0.0021(13) -0.0073(13) C39 0.0212(15) 0.0249(19) 0.0252(19) 0.0000(15) -0.0039(12) -0.0079(13) C40 0.0228(16) 0.0238(19) 0.0256(19) -0.0017(15) -0.0035(13) -0.0064(13) C41 0.0229(16) 0.0247(19) 0.0244(19) -0.0011(15) -0.0023(13) -0.0063(13) C42 0.0238(16) 0.0253(19) 0.0266(19) 0.0003(15) -0.0029(13) -0.0047(14) C43 0.0260(17) 0.030(2) 0.0253(19) -0.0009(15) -0.0035(13) -0.0075(14) C44 0.0269(17) 0.040(2) 0.026(2) 0.0046(17) -0.0028(14) -0.0067(15) C45 0.042(2) 0.067(3) 0.025(2) 0.005(2) -0.0084(16) -0.012(2) C46 0.0168(15) 0.0226(18) 0.0287(19) -0.0027(15) 0.0036(12) -0.0010(13) C47 0.0215(15) 0.0207(18) 0.0229(18) 0.0025(14) -0.0001(12) -0.0017(13) C48 0.0190(15) 0.0273(19) 0.029(2) -0.0031(15) -0.0047(13) -0.0037(13) C49 0.0211(16) 0.035(2) 0.027(2) -0.0047(16) 0.0010(13) -0.0099(14) C50 0.0208(15) 0.033(2) 0.0154(17) -0.0005(14) -0.0008(12) -0.0063(14) _geom_special_details ; H22 and H23 are refined at the located positions using a riding Model, all other hydrogen atoms were placed in geometrical idealized positions and refined using a riding model. 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 1.778(4) . ? Fe1 C1 1.792(4) . ? Fe1 C2 1.796(3) . ? Fe1 C4 2.047(3) . ? Fe1 C21 2.062(3) . ? Fe1 C22 2.093(3) . ? Fe1 C25 2.119(3) . ? O1 C1 1.144(4) . ? O2 C2 1.147(4) . ? O3 C3 1.152(4) . ? O4 C5 1.369(4) . ? O4 C4 1.408(4) . ? O5 C5 1.193(4) . ? C4 C25 1.404(5) . ? C4 C21 1.415(4) . ? C5 C6 1.499(5) . ? C6 C7 1.528(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.526(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.523(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.528(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.526(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.530(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.531(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.522(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.523(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.522(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.529(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.510(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.526(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.432(5) . ? C21 H21 0.9495 . ? C22 C23 1.500(5) . ? C22 H22 0.9508 . ? C23 C24 1.545(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.517(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25 0.9507 . ? Fe2 C27 1.788(3) . ? Fe2 C28 1.794(3) . ? Fe2 C26 1.798(4) . ? Fe2 C29 2.040(3) . ? Fe2 C46 2.058(3) . ? Fe2 C47 2.101(3) . ? Fe2 C50 2.118(3) . ? O6 C26 1.143(4) . ? O7 C27 1.153(4) . ? O8 C28 1.145(4) . ? O9 C30 1.369(4) . ? O9 C29 1.410(4) . ? O10 C30 1.199(4) . ? C29 C46 1.410(4) . ? C29 C50 1.419(4) . ? C30 C31 1.496(4) . ? C31 C32 1.541(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.527(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.534(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.528(4) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.532(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.526(4) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.533(4) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.533(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.532(4) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.520(4) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.532(4) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.528(4) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.531(5) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.522(5) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.422(5) . ? C46 H46 0.9491 . ? C47 C48 1.520(4) . ? C47 H47 0.9503 . ? C48 C49 1.531(5) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C50 1.515(4) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50 0.9478 . ? 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 101.38(15) . . ? C3 Fe1 C2 101.75(15) . . ? C1 Fe1 C2 93.65(15) . . ? C3 Fe1 C4 130.87(14) . . ? C1 Fe1 C4 124.16(15) . . ? C2 Fe1 C4 93.43(13) . . ? C3 Fe1 C21 132.68(14) . . ? C1 Fe1 C21 92.14(14) . . ? C2 Fe1 C21 122.59(15) . . ? C4 Fe1 C21 40.28(12) . . ? C3 Fe1 C22 93.57(14) . . ? C1 Fe1 C22 92.08(14) . . ? C2 Fe1 C22 162.23(14) . . ? C4 Fe1 C22 69.53(12) . . ? C21 Fe1 C22 40.30(13) . . ? C3 Fe1 C25 92.72(14) . . ? C1 Fe1 C25 162.34(14) . . ? C2 Fe1 C25 93.83(13) . . ? C4 Fe1 C25 39.34(13) . . ? C21 Fe1 C25 70.38(13) . . ? C22 Fe1 C25 76.33(12) . . ? C5 O4 C4 114.2(2) . . ? O1 C1 Fe1 178.1(3) . . ? O2 C2 Fe1 179.0(3) . . ? O3 C3 Fe1 177.7(3) . . ? C25 C4 O4 123.2(3) . . ? C25 C4 C21 117.5(3) . . ? O4 C4 C21 118.9(3) . . ? C25 C4 Fe1 73.13(18) . . ? O4 C4 Fe1 120.79(19) . . ? C21 C4 Fe1 70.45(18) . . ? O5 C5 O4 123.2(3) . . ? O5 C5 C6 126.6(3) . . ? O4 C5 C6 110.1(3) . . ? C5 C6 C7 113.0(3) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 112.1(3) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 113.0(3) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 113.3(3) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 113.2(3) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 113.0(3) . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 113.1(3) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.0(3) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 113.7(3) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 113.3(3) . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 114.4(3) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 112.1(3) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 115.2(3) . . ? C19 C18 H18A 108.5 . . ? C17 C18 H18A 108.5 . . ? C19 C18 H18B 108.5 . . ? C17 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 111.7(3) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 C21 C22 112.1(3) . . ? C4 C21 Fe1 69.27(18) . . ? C22 C21 Fe1 71.02(18) . . ? C4 C21 H21 121.0 . . ? C22 C21 H21 126.3 . . ? Fe1 C21 H21 120.0 . . ? C21 C22 C23 120.1(3) . . ? C21 C22 Fe1 68.68(17) . . ? C23 C22 Fe1 110.8(2) . . ? C21 C22 H22 115.2 . . ? C23 C22 H22 114.7 . . ? Fe1 C22 H22 119.6 . . ? C22 C23 C24 111.3(3) . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C23 109.8(3) . . ? C25 C24 H24A 109.7 . . ? C23 C24 H24A 109.7 . . ? C25 C24 H24B 109.7 . . ? C23 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? C4 C25 C24 118.5(3) . . ? C4 C25 Fe1 67.53(17) . . ? C24 C25 Fe1 110.5(2) . . ? C4 C25 H25 115.3 . . ? C24 C25 H25 116.5 . . ? Fe1 C25 H25 119.5 . . ? C27 Fe2 C28 91.04(15) . . ? C27 Fe2 C26 101.96(16) . . ? C28 Fe2 C26 104.54(15) . . ? C27 Fe2 C29 123.67(15) . . ? C28 Fe2 C29 92.71(14) . . ? C26 Fe2 C29 130.90(14) . . ? C27 Fe2 C46 93.80(14) . . ? C28 Fe2 C46 122.77(15) . . ? C26 Fe2 C46 129.71(13) . . ? C29 Fe2 C46 40.25(12) . . ? C27 Fe2 C47 95.23(13) . . ? C28 Fe2 C47 161.92(15) . . ? C26 Fe2 C47 90.74(14) . . ? C29 Fe2 C47 69.72(13) . . ? C46 Fe2 C47 39.98(13) . . ? C27 Fe2 C50 163.21(15) . . ? C28 Fe2 C50 92.90(14) . . ? C26 Fe2 C50 92.83(14) . . ? C29 Fe2 C50 39.85(13) . . ? C46 Fe2 C50 70.40(13) . . ? C47 Fe2 C50 76.48(12) . . ? C30 O9 C29 116.7(2) . . ? O6 C26 Fe2 175.5(3) . . ? O7 C27 Fe2 178.6(3) . . ? O8 C28 Fe2 178.5(3) . . ? O9 C29 C46 120.2(3) . . ? O9 C29 C50 122.5(3) . . ? C46 C29 C50 116.6(3) . . ? O9 C29 Fe2 118.55(19) . . ? C46 C29 Fe2 70.53(19) . . ? C50 C29 Fe2 73.05(19) . . ? O10 C30 O9 122.0(3) . . ? O10 C30 C31 126.9(3) . . ? O9 C30 C31 111.1(3) . . ? C30 C31 C32 110.8(3) . . ? C30 C31 H31A 109.5 . . ? C32 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? C33 C32 C31 111.2(3) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C32 C33 C34 113.4(3) . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33B 108.9 . . ? C34 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C35 C34 C33 112.4(3) . . ? C35 C34 H34A 109.1 . . ? C33 C34 H34A 109.1 . . ? C35 C34 H34B 109.1 . . ? C33 C34 H34B 109.1 . . ? H34A C34 H34B 107.9 . . ? C34 C35 C36 113.7(3) . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35B 108.8 . . ? C36 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 113.4(3) . . ? C37 C36 H36A 108.9 . . ? C35 C36 H36A 108.9 . . ? C37 C36 H36B 108.9 . . ? C35 C36 H36B 108.9 . . ? H36A C36 H36B 107.7 . . ? C36 C37 C38 113.4(3) . . ? C36 C37 H37A 108.9 . . ? C38 C37 H37A 108.9 . . ? C36 C37 H37B 108.9 . . ? C38 C37 H37B 108.9 . . ? H37A C37 H37B 107.7 . . ? C37 C38 C39 113.3(3) . . ? C37 C38 H38A 108.9 . . ? C39 C38 H38A 108.9 . . ? C37 C38 H38B 108.9 . . ? C39 C38 H38B 108.9 . . ? H38A C38 H38B 107.7 . . ? C40 C39 C38 113.1(3) . . ? C40 C39 H39A 109.0 . . ? C38 C39 H39A 109.0 . . ? C40 C39 H39B 109.0 . . ? C38 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? C41 C40 C39 113.7(3) . . ? C41 C40 H40A 108.8 . . ? C39 C40 H40A 108.8 . . ? C41 C40 H40B 108.8 . . ? C39 C40 H40B 108.8 . . ? H40A C40 H40B 107.7 . . ? C40 C41 C42 113.4(3) . . ? C40 C41 H41A 108.9 . . ? C42 C41 H41A 108.9 . . ? C40 C41 H41B 108.9 . . ? C42 C41 H41B 108.9 . . ? H41A C41 H41B 107.7 . . ? C43 C42 C41 113.7(3) . . ? C43 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? C43 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? C42 C43 C44 113.0(3) . . ? C42 C43 H43A 109.0 . . ? C44 C43 H43A 109.0 . . ? C42 C43 H43B 109.0 . . ? C44 C43 H43B 109.0 . . ? H43A C43 H43B 107.8 . . ? C45 C44 C43 113.2(3) . . ? C45 C44 H44A 108.9 . . ? C43 C44 H44A 108.9 . . ? C45 C44 H44B 108.9 . . ? C43 C44 H44B 108.9 . . ? H44A C44 H44B 107.7 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C29 C46 C47 113.4(3) . . ? C29 C46 Fe2 69.21(18) . . ? C47 C46 Fe2 71.66(18) . . ? C29 C46 H46 120.8 . . ? C47 C46 H46 125.2 . . ? Fe2 C46 H46 120.4 . . ? C46 C47 C48 120.7(3) . . ? C46 C47 Fe2 68.36(17) . . ? C48 C47 Fe2 109.3(2) . . ? C46 C47 H47 118.6 . . ? C48 C47 H47 114.3 . . ? Fe2 C47 H47 116.8 . . ? C47 C48 C49 111.1(3) . . ? C47 C48 H48A 109.4 . . ? C49 C48 H48A 109.4 . . ? C47 C48 H48B 109.4 . . ? C49 C48 H48B 109.4 . . ? H48A C48 H48B 108.0 . . ? C50 C49 C48 110.6(2) . . ? C50 C49 H49A 109.5 . . ? C48 C49 H49A 109.5 . . ? C50 C49 H49B 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 108.1 . . ? C29 C50 C49 118.7(3) . . ? C29 C50 Fe2 67.10(17) . . ? C49 C50 Fe2 110.3(2) . . ? C29 C50 H50 119.5 . . ? C49 C50 H50 113.3 . . ? Fe2 C50 H50 120.0 . . ? 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 C5 O4 C4 C25 72.6(4) . . . . ? C5 O4 C4 C21 -114.8(3) . . . . ? C5 O4 C4 Fe1 161.9(2) . . . . ? C3 Fe1 C4 C25 -16.9(2) . . . . ? C1 Fe1 C4 C25 -171.38(18) . . . . ? C2 Fe1 C4 C25 91.9(2) . . . . ? C21 Fe1 C4 C25 -128.3(3) . . . . ? C22 Fe1 C4 C25 -93.3(2) . . . . ? C3 Fe1 C4 C21 111.4(2) . . . . ? C1 Fe1 C4 C21 -43.0(3) . . . . ? C2 Fe1 C4 C21 -139.8(2) . . . . ? C22 Fe1 C4 C21 35.0(2) . . . . ? C25 Fe1 C4 C21 128.3(3) . . . . ? C4 O4 C5 O5 3.7(4) . . . . ? C4 O4 C5 C6 -178.3(3) . . . . ? O5 C5 C6 C7 -26.2(5) . . . . ? O4 C5 C6 C7 155.9(3) . . . . ? C5 C6 C7 C8 -179.6(3) . . . . ? C6 C7 C8 C9 176.1(3) . . . . ? C7 C8 C9 C10 -179.7(3) . . . . ? C8 C9 C10 C11 179.3(3) . . . . ? C9 C10 C11 C12 179.2(3) . . . . ? C10 C11 C12 C13 -179.5(3) . . . . ? C11 C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C15 -179.3(3) . . . . ? C13 C14 C15 C16 179.4(3) . . . . ? C14 C15 C16 C17 -179.2(3) . . . . ? C15 C16 C17 C18 177.9(3) . . . . ? C16 C17 C18 C19 -177.6(3) . . . . ? C17 C18 C19 C20 176.3(3) . . . . ? C25 C4 C21 C22 -0.2(4) . . . . ? O4 C4 C21 C22 -173.2(2) . . . . ? Fe1 C4 C21 C22 -58.1(2) . . . . ? C25 C4 C21 Fe1 57.8(2) . . . . ? O4 C4 C21 Fe1 -115.1(3) . . . . ? C3 Fe1 C21 C4 -106.8(2) . . . . ? C1 Fe1 C21 C4 145.6(2) . . . . ? C2 Fe1 C21 C4 49.9(3) . . . . ? C22 Fe1 C21 C4 -123.7(3) . . . . ? C25 Fe1 C21 C4 -31.86(19) . . . . ? C3 Fe1 C21 C22 16.9(3) . . . . ? C1 Fe1 C21 C22 -90.7(2) . . . . ? C2 Fe1 C21 C22 173.6(2) . . . . ? C4 Fe1 C21 C22 123.7(3) . . . . ? C25 Fe1 C21 C22 91.9(2) . . . . ? C4 C21 C22 C23 -45.3(4) . . . . ? Fe1 C21 C22 C23 -102.4(3) . . . . ? C4 C21 C22 Fe1 57.1(2) . . . . ? C3 Fe1 C22 C21 -167.6(2) . . . . ? C1 Fe1 C22 C21 90.9(2) . . . . ? C2 Fe1 C22 C21 -18.0(6) . . . . ? C4 Fe1 C22 C21 -35.0(2) . . . . ? C25 Fe1 C22 C21 -75.7(2) . . . . ? C3 Fe1 C22 C23 -52.3(3) . . . . ? C1 Fe1 C22 C23 -153.9(3) . . . . ? C2 Fe1 C22 C23 97.3(5) . . . . ? C4 Fe1 C22 C23 80.3(2) . . . . ? C21 Fe1 C22 C23 115.3(3) . . . . ? C25 Fe1 C22 C23 39.6(2) . . . . ? C21 C22 C23 C24 43.7(4) . . . . ? Fe1 C22 C23 C24 -33.0(3) . . . . ? C22 C23 C24 C25 0.7(4) . . . . ? O4 C4 C25 C24 -141.9(3) . . . . ? C21 C4 C25 C24 45.4(4) . . . . ? Fe1 C4 C25 C24 101.9(3) . . . . ? O4 C4 C25 Fe1 116.2(3) . . . . ? C21 C4 C25 Fe1 -56.5(2) . . . . ? C23 C24 C25 C4 -43.5(4) . . . . ? C23 C24 C25 Fe1 31.3(3) . . . . ? C3 Fe1 C25 C4 167.28(19) . . . . ? C1 Fe1 C25 C4 24.1(5) . . . . ? C2 Fe1 C25 C4 -90.7(2) . . . . ? C21 Fe1 C25 C4 32.57(18) . . . . ? C22 Fe1 C25 C4 74.27(19) . . . . ? C3 Fe1 C25 C24 53.9(2) . . . . ? C1 Fe1 C25 C24 -89.3(5) . . . . ? C2 Fe1 C25 C24 155.8(2) . . . . ? C4 Fe1 C25 C24 -113.4(3) . . . . ? C21 Fe1 C25 C24 -80.8(2) . . . . ? C22 Fe1 C25 C24 -39.1(2) . . . . ? C30 O9 C29 C46 -121.2(3) . . . . ? C30 O9 C29 C50 68.6(4) . . . . ? C30 O9 C29 Fe2 155.8(2) . . . . ? C27 Fe2 C29 C46 -48.4(2) . . . . ? C28 Fe2 C29 C46 -141.50(19) . . . . ? C26 Fe2 C29 C46 106.6(2) . . . . ? C47 Fe2 C29 C46 34.13(17) . . . . ? C50 Fe2 C29 C46 127.2(3) . . . . ? C27 Fe2 C29 C50 -175.66(18) . . . . ? C28 Fe2 C29 C50 91.3(2) . . . . ? C26 Fe2 C29 C50 -20.7(3) . . . . ? C46 Fe2 C29 C50 -127.2(3) . . . . ? C47 Fe2 C29 C50 -93.09(19) . . . . ? C29 O9 C30 O10 7.7(4) . . . . ? C29 O9 C30 C31 -170.8(3) . . . . ? O10 C30 C31 C32 -83.9(4) . . . . ? O9 C30 C31 C32 94.5(3) . . . . ? C30 C31 C32 C33 176.0(3) . . . . ? C31 C32 C33 C34 -178.1(3) . . . . ? C32 C33 C34 C35 -179.8(3) . . . . ? C33 C34 C35 C36 -179.6(3) . . . . ? C34 C35 C36 C37 179.5(3) . . . . ? C35 C36 C37 C38 -179.5(3) . . . . ? C36 C37 C38 C39 179.8(3) . . . . ? C37 C38 C39 C40 -179.7(3) . . . . ? C38 C39 C40 C41 179.6(3) . . . . ? C39 C40 C41 C42 179.9(3) . . . . ? C40 C41 C42 C43 -179.7(3) . . . . ? C41 C42 C43 C44 178.9(3) . . . . ? C42 C43 C44 C45 -179.6(3) . . . . ? O9 C29 C46 C47 -170.3(3) . . . . ? C50 C29 C46 C47 0.5(4) . . . . ? Fe2 C29 C46 C47 -57.9(2) . . . . ? O9 C29 C46 Fe2 -112.4(3) . . . . ? C50 C29 C46 Fe2 58.4(2) . . . . ? C27 Fe2 C46 C29 141.39(19) . . . . ? C28 Fe2 C46 C29 47.7(2) . . . . ? C26 Fe2 C46 C29 -109.6(2) . . . . ? C47 Fe2 C46 C29 -125.0(3) . . . . ? C50 Fe2 C46 C29 -32.80(17) . . . . ? C27 Fe2 C46 C47 -93.6(2) . . . . ? C28 Fe2 C46 C47 172.69(19) . . . . ? C26 Fe2 C46 C47 15.4(3) . . . . ? C29 Fe2 C46 C47 125.0(3) . . . . ? C50 Fe2 C46 C47 92.21(19) . . . . ? C29 C46 C47 C48 -43.7(4) . . . . ? Fe2 C46 C47 C48 -100.2(3) . . . . ? C29 C46 C47 Fe2 56.6(2) . . . . ? C27 Fe2 C47 C46 89.7(2) . . . . ? C28 Fe2 C47 C46 -20.2(5) . . . . ? C26 Fe2 C47 C46 -168.2(2) . . . . ? C29 Fe2 C47 C46 -34.35(18) . . . . ? C50 Fe2 C47 C46 -75.51(19) . . . . ? C27 Fe2 C47 C48 -154.0(2) . . . . ? C28 Fe2 C47 C48 96.1(5) . . . . ? C26 Fe2 C47 C48 -51.9(2) . . . . ? C29 Fe2 C47 C48 81.9(2) . . . . ? C46 Fe2 C47 C48 116.3(3) . . . . ? C50 Fe2 C47 C48 40.8(2) . . . . ? C46 C47 C48 C49 40.1(4) . . . . ? Fe2 C47 C48 C49 -35.6(3) . . . . ? C47 C48 C49 C50 3.6(4) . . . . ? O9 C29 C50 C49 -145.1(3) . . . . ? C46 C29 C50 C49 44.3(4) . . . . ? Fe2 C29 C50 C49 101.4(3) . . . . ? O9 C29 C50 Fe2 113.5(3) . . . . ? C46 C29 C50 Fe2 -57.1(2) . . . . ? C48 C49 C50 C29 -44.6(4) . . . . ? C48 C49 C50 Fe2 29.8(3) . . . . ? C27 Fe2 C50 C29 12.6(5) . . . . ? C28 Fe2 C50 C29 -90.8(2) . . . . ? C26 Fe2 C50 C29 164.51(19) . . . . ? C46 Fe2 C50 C29 33.11(18) . . . . ? C47 Fe2 C50 C29 74.43(19) . . . . ? C27 Fe2 C50 C49 -101.0(5) . . . . ? C28 Fe2 C50 C49 155.6(2) . . . . ? C26 Fe2 C50 C49 50.9(3) . . . . ? C29 Fe2 C50 C49 -113.6(3) . . . . ? C46 Fe2 C50 C49 -80.5(2) . . . . ? C47 Fe2 C50 C49 -39.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.027 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.083