# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr W Donaldson' _publ_contact_author_email william.donaldson@mu.edu _publ_contact_author_address ;Department of Chemistry Marquette University P. O. Box 1881 Milwaukee, WI 53201-1881 USA ; _publ_contact_author_phone 414-288-7374 _publ_contact_author_fax 414-288-7066 loop_ _publ_author_name _publ_author_address 'William A. Donaldson' ;Department of Chemistry Marquette University P. O. Box 1881 Milwaukee, WI 53201-1881 USA ; D.W.Lee ;Department of Chemistry Marquette University P. O. Box 1881 Milwaukee, WI 53201-1881 USA ; R.K.Pandey ;Department of Chemistry Marquette University P. O. Box 1881 Milwaukee, WI 53201-1881 USA ; S.Lindeman ;Department of Chemistry Marquette University P. O. Box 1881 Milwaukee, WI 53201-1881 USA ; _publ_section_title ; Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins ; data_DON1K _database_code_depnum_ccdc_archive 'CCDC 823811' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C19 H18 Cl2 Fe O7' _chemical_formula_sum 'C19 H18 Cl2 Fe O7' _chemical_formula_weight 485.08 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _space_group_IT_number 15 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 100.442(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 30.3355(8) _cell_length_b 7.26159(18) _cell_length_c 18.3813(5) _cell_measurement_reflns_used 18084 _cell_measurement_temperature 100 _cell_measurement_theta_max 29.4785 _cell_measurement_theta_min 3.3742 _cell_volume 3982.06(18) _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.81463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 1984 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_special_details ? _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.918 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -62.00 38.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 11.5134 -37.0000 -180.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -15.00 78.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 11.5134 37.0000 0.0000 93 #__ type_ start__ end____ width___ exp.time_ 3 omega 4.00 53.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 11.5134 -105.0000 65.0000 49 #__ type_ start__ end____ width___ exp.time_ 4 omega 5.00 46.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 11.5134 77.0000 150.0000 41 #__ type_ start__ end____ width___ exp.time_ 5 omega -15.00 31.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -11.6697 -105.0000 65.0000 46 #__ type_ start__ end____ width___ exp.time_ 6 omega -67.00 45.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 11.5134 -77.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 7 omega -57.00 -7.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -11.6697 105.0000 114.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega -28.00 -3.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -11.6697 37.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 9 omega -15.00 34.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -11.6697 -105.0000 -166.0000 49 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0034341 _diffrn_orient_matrix_UB_12 0.0881552 _diffrn_orient_matrix_UB_13 0.0167377 _diffrn_orient_matrix_UB_21 -0.0096502 _diffrn_orient_matrix_UB_22 0.0418615 _diffrn_orient_matrix_UB_23 -0.0340292 _diffrn_orient_matrix_UB_31 -0.0214483 _diffrn_orient_matrix_UB_32 -0.0046461 _diffrn_orient_matrix_UB_33 0.0100937 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 28525 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 29.54 _diffrn_reflns_theta_min 3.47 _reflns_number_gt 4490 _reflns_number_total 5113 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.382 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.053 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0233 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 5113 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.0630 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+3.1597P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.151064(6) 0.28866(2) 0.457193(10) 0.01236(6) Uani 1 1 d . . . Cl1 Cl 0.051902(11) 0.52130(5) 0.225403(19) 0.02271(8) Uani 1 1 d . . . Cl2 Cl 0.142456(11) 0.62524(5) 0.209297(19) 0.02125(8) Uani 1 1 d . . . O1 O 0.08046(3) 0.20630(14) 0.54284(6) 0.0217(2) Uani 1 1 d . . . O2 O 0.22485(3) 0.27724(15) 0.58601(6) 0.0265(2) Uani 1 1 d . . . O3 O 0.18440(4) -0.05687(14) 0.40395(6) 0.0280(2) Uani 1 1 d . . . O4 O 0.09286(3) 0.01741(14) 0.30158(6) 0.0238(2) Uani 1 1 d . . . O5 O 0.04233(3) 0.08512(13) 0.37331(5) 0.0192(2) Uani 1 1 d . . . O6 O 0.06714(3) 0.66608(14) 0.52008(5) 0.0185(2) Uani 1 1 d . . . O7 O 0.23190(3) 0.89417(13) 0.67401(5) 0.01738(19) Uani 1 1 d . . . C1 C 0.10866(4) 0.23435(18) 0.51135(7) 0.0158(2) Uani 1 1 d . . . C2 C 0.19679(4) 0.28438(18) 0.53570(8) 0.0177(3) Uani 1 1 d . . . C3 C 0.16940(4) 0.07286(19) 0.42445(8) 0.0184(3) Uani 1 1 d . . . C4 C 0.07830(4) 0.12414(18) 0.34211(7) 0.0160(2) Uani 1 1 d . . . C5 C 0.09740(4) 0.30606(17) 0.36661(7) 0.0140(2) Uani 1 1 d . . . H5 H 0.0738 0.3937 0.3766 0.017 Uiso 1 1 calc R . . C6 C 0.12655(4) 0.39072(17) 0.31605(7) 0.0135(2) Uani 1 1 d . . . H6 H 0.1312 0.2953 0.2790 0.016 Uiso 1 1 calc R . . C7 C 0.17145(4) 0.42745(17) 0.36545(7) 0.0137(2) Uani 1 1 d . . . H7 H 0.1976(5) 0.393(2) 0.3484(9) 0.016 Uiso 1 1 d . . . C8 C 0.17651(4) 0.53998(17) 0.42788(7) 0.0137(2) Uani 1 1 d . . . H8 H 0.2069(5) 0.572(2) 0.4505(9) 0.016 Uiso 1 1 d . . . C9 C 0.14053(4) 0.58381(17) 0.46410(7) 0.0134(2) Uani 1 1 d . . . H9 H 0.1115(5) 0.595(2) 0.4350(9) 0.016 Uiso 1 1 d . . . C10 C 0.02300(5) -0.0953(2) 0.35711(9) 0.0249(3) Uani 1 1 d . . . H10A H 0.0209 -0.1217 0.3043 0.037 Uiso 1 1 calc R . . H10B H -0.0070 -0.0986 0.3698 0.037 Uiso 1 1 calc R . . H10C H 0.0420 -0.1879 0.3862 0.037 Uiso 1 1 calc R . . C11 C 0.14576(4) 0.68543(17) 0.53440(7) 0.0133(2) Uani 1 1 d . . . C12 C 0.10645(4) 0.73128(17) 0.56149(7) 0.0144(2) Uani 1 1 d . . . C13 C 0.10909(4) 0.83354(18) 0.62537(7) 0.0155(2) Uani 1 1 d . . . H13 H 0.0824 0.8641 0.6430 0.019 Uiso 1 1 calc R . . C14 C 0.15046(4) 0.89258(17) 0.66446(7) 0.0152(2) Uani 1 1 d . . . H14 H 0.1519 0.9648 0.7079 0.018 Uiso 1 1 calc R . . C15 C 0.18946(4) 0.84487(17) 0.63928(7) 0.0143(2) Uani 1 1 d . . . C16 C 0.18690(4) 0.74242(17) 0.57476(7) 0.0150(2) Uani 1 1 d . . . H16 H 0.2137 0.7106 0.5579 0.018 Uiso 1 1 calc R . . C17 C 0.02639(4) 0.7273(2) 0.54045(8) 0.0217(3) Uani 1 1 d . . . H17A H 0.0009 0.6765 0.5059 0.033 Uiso 1 1 calc R . . H17B H 0.0251 0.8621 0.5387 0.033 Uiso 1 1 calc R . . H17C H 0.0252 0.6854 0.5907 0.033 Uiso 1 1 calc R . . C18 C 0.23500(5) 0.9925(2) 0.74204(8) 0.0200(3) Uani 1 1 d . . . H18A H 0.2185 1.1086 0.7331 0.030 Uiso 1 1 calc R . . H18C H 0.2665 1.0183 0.7623 0.030 Uiso 1 1 calc R . . H18B H 0.2221 0.9178 0.7774 0.030 Uiso 1 1 calc R . . C19 C 0.10758(4) 0.56247(18) 0.27374(7) 0.0159(2) Uani 1 1 d . . . H19 H 0.1071 0.6658 0.3095 0.019 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 0.01349(9) 0.00981(9) 0.01439(10) 0.00042(7) 0.00414(6) 0.00066(6) Cl1 0.01687(15) 0.02492(17) 0.02453(17) 0.00009(13) -0.00108(12) 0.00265(12) Cl2 0.02403(16) 0.01887(16) 0.02140(17) 0.00625(13) 0.00554(12) -0.00142(12) O1 0.0192(5) 0.0256(5) 0.0218(5) 0.0051(4) 0.0075(4) -0.0003(4) O2 0.0234(5) 0.0276(6) 0.0257(6) 0.0045(4) -0.0036(4) 0.0014(4) O3 0.0391(6) 0.0137(5) 0.0356(6) 0.0010(4) 0.0183(5) 0.0051(4) O4 0.0316(5) 0.0171(5) 0.0263(5) -0.0083(4) 0.0149(4) -0.0069(4) O5 0.0182(4) 0.0175(5) 0.0236(5) -0.0054(4) 0.0081(4) -0.0065(4) O6 0.0124(4) 0.0216(5) 0.0215(5) -0.0051(4) 0.0026(3) 0.0007(4) O7 0.0171(4) 0.0187(5) 0.0162(5) -0.0047(4) 0.0025(3) -0.0025(4) C1 0.0184(6) 0.0122(6) 0.0159(6) 0.0005(5) 0.0005(5) 0.0012(5) C2 0.0185(6) 0.0131(6) 0.0227(7) 0.0023(5) 0.0069(5) 0.0010(5) C3 0.0211(6) 0.0149(6) 0.0206(7) 0.0036(5) 0.0075(5) -0.0003(5) C4 0.0168(6) 0.0160(6) 0.0156(6) -0.0008(5) 0.0039(5) -0.0022(5) C5 0.0145(6) 0.0127(6) 0.0152(6) -0.0012(5) 0.0035(4) -0.0004(4) C6 0.0154(6) 0.0112(6) 0.0146(6) -0.0012(5) 0.0044(4) 0.0002(4) C7 0.0146(6) 0.0113(6) 0.0160(6) 0.0021(5) 0.0052(4) 0.0006(4) C8 0.0143(6) 0.0102(6) 0.0168(6) 0.0024(5) 0.0035(5) -0.0004(4) C9 0.0154(6) 0.0099(6) 0.0148(6) -0.0001(5) 0.0025(4) 0.0003(4) C10 0.0278(7) 0.0209(7) 0.0270(8) -0.0057(6) 0.0079(6) -0.0122(6) C11 0.0162(6) 0.0092(5) 0.0151(6) 0.0008(5) 0.0042(4) 0.0010(4) C12 0.0141(6) 0.0117(6) 0.0174(6) 0.0016(5) 0.0026(5) 0.0003(4) C13 0.0168(6) 0.0131(6) 0.0179(6) 0.0010(5) 0.0065(5) 0.0019(5) C14 0.0218(6) 0.0104(6) 0.0142(6) 0.0000(5) 0.0054(5) 0.0005(5) C15 0.0164(6) 0.0105(6) 0.0158(6) 0.0020(5) 0.0027(4) -0.0014(4) C16 0.0160(6) 0.0125(6) 0.0173(6) 0.0008(5) 0.0055(5) 0.0004(4) C17 0.0142(6) 0.0272(7) 0.0245(7) 0.0002(6) 0.0051(5) 0.0029(5) C18 0.0212(6) 0.0210(7) 0.0171(7) -0.0053(5) 0.0011(5) -0.0010(5) C19 0.0159(6) 0.0152(6) 0.0161(6) -0.0007(5) 0.0019(4) 0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 1.8070(13) . ? Fe1 C2 1.8116(14) . ? Fe1 C3 1.8023(14) . ? Fe1 C5 2.1108(13) . ? Fe1 C7 2.1494(12) . ? Fe1 C8 2.0900(12) . ? Fe1 C9 2.1741(12) . ? Cl1 C19 1.7855(13) . ? Cl2 C19 1.7844(13) . ? O1 C1 1.1349(16) . ? O2 C2 1.1389(17) . ? O3 C3 1.1397(17) . ? O4 C4 1.2125(16) . ? O5 C4 1.3517(15) . ? O5 C10 1.4440(16) . ? O6 C12 1.3772(15) . ? O6 C17 1.4263(15) . ? O7 C15 1.3766(15) . ? O7 C18 1.4281(16) . ? C4 C5 1.4796(18) . ? C5 H5 1.0000 . ? C5 C6 1.5235(17) . ? C6 H6 1.0000 . ? C6 C7 1.5177(17) . ? C6 C19 1.5261(18) . ? C7 H7 0.939(16) . ? C7 C8 1.3943(18) . ? C8 H8 0.969(16) . ? C8 C9 1.4142(17) . ? C9 H9 0.947(16) . ? C9 C11 1.4713(17) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4130(17) . ? C11 C16 1.3940(18) . ? C12 C13 1.3792(18) . ? C13 H13 0.9500 . ? C13 C14 1.3957(18) . ? C14 H14 0.9500 . ? C14 C15 1.3903(17) . ? C15 C16 1.3902(18) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18C 0.9800 . ? C18 H18B 0.9800 . ? C19 H19 1.0000 . ? 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 Fe1 C5 H5 111.7 . . ? Fe1 C7 H7 121.1(10) . . ? Fe1 C8 H8 117.7(9) . . ? Fe1 C9 H9 100.3(10) . . ? Cl1 C19 H19 109.1 . . ? Cl2 C19 Cl1 109.49(7) . . ? Cl2 C19 H19 109.1 . . ? O1 C1 Fe1 176.23(12) . . ? O2 C2 Fe1 177.80(12) . . ? O3 C3 Fe1 174.27(12) . . ? O4 C4 O5 122.60(12) . . ? O4 C4 C5 126.27(12) . . ? O5 C4 C5 111.09(11) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? O6 C12 C11 115.20(11) . . ? O6 C12 C13 124.51(11) . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? O6 C17 H17C 109.5 . . ? O7 C15 C14 124.17(12) . . ? O7 C15 C16 115.96(11) . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18C 109.5 . . ? O7 C18 H18B 109.5 . . ? C1 Fe1 C2 94.37(6) . . ? C1 Fe1 C5 85.61(5) . . ? C1 Fe1 C7 150.38(5) . . ? C1 Fe1 C8 131.74(5) . . ? C1 Fe1 C9 93.21(5) . . ? C2 Fe1 C5 177.48(6) . . ? C2 Fe1 C7 110.20(5) . . ? C2 Fe1 C8 87.42(5) . . ? C2 Fe1 C9 94.00(5) . . ? C3 Fe1 C1 106.72(6) . . ? C3 Fe1 C2 90.75(6) . . ? C3 Fe1 C5 91.67(6) . . ? C3 Fe1 C7 89.75(5) . . ? C3 Fe1 C8 121.49(5) . . ? C3 Fe1 C9 159.09(5) . . ? C4 O5 C10 115.56(11) . . ? C4 C5 Fe1 112.96(9) . . ? C4 C5 H5 111.7 . . ? C4 C5 C6 114.40(10) . . ? C5 Fe1 C7 69.12(5) . . ? C5 Fe1 C9 83.48(5) . . ? C5 C6 H6 107.8 . . ? C5 C6 C19 115.71(10) . . ? C6 C5 Fe1 93.19(7) . . ? C6 C5 H5 111.7 . . ? C6 C7 Fe1 91.85(7) . . ? C6 C7 H7 118.4(10) . . ? C6 C19 Cl1 110.61(9) . . ? C6 C19 Cl2 109.45(9) . . ? C6 C19 H19 109.1 . . ? C7 Fe1 C9 69.50(5) . . ? C7 C6 C5 105.25(10) . . ? C7 C6 H6 107.8 . . ? C7 C6 C19 112.08(10) . . ? C7 C8 Fe1 73.12(7) . . ? C7 C8 H8 116.6(9) . . ? C7 C8 C9 122.69(11) . . ? C8 Fe1 C5 90.71(5) . . ? C8 Fe1 C7 38.37(5) . . ? C8 Fe1 C9 38.67(5) . . ? C8 C7 Fe1 68.51(7) . . ? C8 C7 C6 123.26(11) . . ? C8 C7 H7 117.2(10) . . ? C8 C9 Fe1 67.44(7) . . ? C8 C9 H9 118.1(9) . . ? C8 C9 C11 123.82(11) . . ? C9 C8 Fe1 73.88(7) . . ? C9 C8 H8 120.0(9) . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C9 Fe1 123.51(9) . . ? C11 C9 H9 113.4(10) . . ? C11 C16 H16 119.4 . . ? C12 O6 C17 116.91(10) . . ? C12 C11 C9 117.64(11) . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.78(12) . . ? C13 C12 C11 120.29(12) . . ? C13 C14 H14 120.3 . . ? C14 C13 H13 119.6 . . ? C14 C15 C16 119.86(12) . . ? C15 O7 C18 116.33(10) . . ? C15 C14 C13 119.48(12) . . ? C15 C14 H14 120.3 . . ? C15 C16 C11 121.28(12) . . ? C15 C16 H16 119.4 . . ? C16 C11 C9 124.06(11) . . ? C16 C11 C12 118.28(12) . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? C19 C6 H6 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Fe1 C5 C6 C7 -6.87(9) . . . . ? Fe1 C5 C6 C19 -131.18(10) . . . . ? Fe1 C7 C8 C9 -57.35(11) . . . . ? Fe1 C8 C9 C11 116.19(12) . . . . ? Fe1 C9 C11 C12 -100.86(12) . . . . ? Fe1 C9 C11 C16 80.63(15) . . . . ? O4 C4 C5 Fe1 -82.33(16) . . . . ? O4 C4 C5 C6 22.65(19) . . . . ? O5 C4 C5 Fe1 95.27(11) . . . . ? O5 C4 C5 C6 -159.75(11) . . . . ? O6 C12 C13 C14 179.31(12) . . . . ? O7 C15 C16 C11 -179.56(11) . . . . ? C1 Fe1 C2 O2 35(3) . . . . ? C1 Fe1 C3 O3 -149.4(13) . . . . ? C1 Fe1 C5 C4 -72.51(9) . . . . ? C1 Fe1 C5 C6 169.26(8) . . . . ? C1 Fe1 C7 C6 -38.20(14) . . . . ? C1 Fe1 C7 C8 87.04(13) . . . . ? C1 Fe1 C8 C7 -138.59(8) . . . . ? C1 Fe1 C8 C9 -6.12(11) . . . . ? C1 Fe1 C9 C8 175.43(8) . . . . ? C1 Fe1 C9 C11 58.82(11) . . . . ? C2 Fe1 C1 O1 145.4(19) . . . . ? C2 Fe1 C3 O3 -54.7(13) . . . . ? C2 Fe1 C5 C4 -162.1(12) . . . . ? C2 Fe1 C5 C6 79.7(12) . . . . ? C2 Fe1 C7 C6 177.57(7) . . . . ? C2 Fe1 C7 C8 -57.19(9) . . . . ? C2 Fe1 C8 C7 127.85(8) . . . . ? C2 Fe1 C8 C9 -99.68(8) . . . . ? C2 Fe1 C9 C8 80.82(8) . . . . ? C2 Fe1 C9 C11 -35.79(11) . . . . ? C3 Fe1 C1 O1 -122.5(19) . . . . ? C3 Fe1 C2 O2 -72(3) . . . . ? C3 Fe1 C5 C4 34.14(9) . . . . ? C3 Fe1 C5 C6 -84.09(8) . . . . ? C3 Fe1 C7 C6 86.87(8) . . . . ? C3 Fe1 C7 C8 -147.89(8) . . . . ? C3 Fe1 C8 C7 38.56(10) . . . . ? C3 Fe1 C8 C9 171.03(8) . . . . ? C3 Fe1 C9 C8 -21.88(19) . . . . ? C3 Fe1 C9 C11 -138.48(15) . . . . ? C4 C5 C6 C7 -123.89(11) . . . . ? C4 C5 C6 C19 111.80(13) . . . . ? C5 Fe1 C1 O1 -32.0(19) . . . . ? C5 Fe1 C2 O2 124(3) . . . . ? C5 Fe1 C3 O3 124.6(13) . . . . ? C5 Fe1 C7 C6 -5.02(7) . . . . ? C5 Fe1 C7 C8 120.22(8) . . . . ? C5 Fe1 C8 C7 -53.84(8) . . . . ? C5 Fe1 C8 C9 78.63(8) . . . . ? C5 Fe1 C9 C8 -99.37(8) . . . . ? C5 Fe1 C9 C11 144.03(11) . . . . ? C5 C6 C7 Fe1 6.74(9) . . . . ? C5 C6 C7 C8 -58.60(15) . . . . ? C5 C6 C19 Cl1 -52.12(13) . . . . ? C5 C6 C19 Cl2 -172.83(9) . . . . ? C6 C7 C8 Fe1 77.48(11) . . . . ? C6 C7 C8 C9 20.13(19) . . . . ? C7 Fe1 C1 O1 -1.2(19) . . . . ? C7 Fe1 C2 O2 -162(3) . . . . ? C7 Fe1 C3 O3 55.5(13) . . . . ? C7 Fe1 C5 C4 123.23(10) . . . . ? C7 Fe1 C5 C6 5.01(7) . . . . ? C7 Fe1 C8 C9 132.47(11) . . . . ? C7 Fe1 C9 C8 -29.26(7) . . . . ? C7 Fe1 C9 C11 -145.87(11) . . . . ? C7 C6 C19 Cl1 -172.80(9) . . . . ? C7 C6 C19 Cl2 66.48(12) . . . . ? C7 C8 C9 Fe1 57.01(11) . . . . ? C7 C8 C9 C11 173.19(12) . . . . ? C8 Fe1 C1 O1 55.0(19) . . . . ? C8 Fe1 C2 O2 167(3) . . . . ? C8 Fe1 C3 O3 32.8(13) . . . . ? C8 Fe1 C5 C4 155.67(9) . . . . ? C8 Fe1 C5 C6 37.45(8) . . . . ? C8 Fe1 C7 C6 -125.24(11) . . . . ? C8 Fe1 C9 C11 -116.60(13) . . . . ? C8 C9 C11 C12 175.47(12) . . . . ? C8 C9 C11 C16 -3.0(2) . . . . ? C9 Fe1 C1 O1 51.2(19) . . . . ? C9 Fe1 C2 O2 128(3) . . . . ? C9 Fe1 C3 O3 48.6(14) . . . . ? C9 Fe1 C5 C4 -166.26(9) . . . . ? C9 Fe1 C5 C6 75.52(7) . . . . ? C9 Fe1 C7 C6 -95.76(8) . . . . ? C9 Fe1 C7 C8 29.48(7) . . . . ? C9 Fe1 C8 C7 -132.47(11) . . . . ? C9 C11 C12 O6 3.23(17) . . . . ? C9 C11 C12 C13 -177.10(11) . . . . ? C9 C11 C16 C15 177.24(12) . . . . ? C10 O5 C4 O4 1.87(19) . . . . ? C10 O5 C4 C5 -175.83(11) . . . . ? C11 C12 C13 C14 -0.32(19) . . . . ? C12 C11 C16 C15 -1.26(19) . . . . ? C12 C13 C14 C15 -1.12(19) . . . . ? C13 C14 C15 O7 -179.30(12) . . . . ? C13 C14 C15 C16 1.35(19) . . . . ? C14 C15 C16 C11 -0.16(19) . . . . ? C16 C11 C12 O6 -178.18(11) . . . . ? C16 C11 C12 C13 1.49(19) . . . . ? C17 O6 C12 C11 -172.79(11) . . . . ? C17 O6 C12 C13 7.56(19) . . . . ? C18 O7 C15 C14 3.29(18) . . . . ? C18 O7 C15 C16 -177.34(11) . . . . ? C19 C6 C7 Fe1 133.31(9) . . . . ? C19 C6 C7 C8 67.97(15) . . . . ? # Attachment '2-(1-cyclohexenyl)-3-pentene-1,5-diyl)iron.cif' data_don1l _database_code_depnum_ccdc_archive 'CCDC 823812' _audit_creation_date 2010-10-27 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.26 svn.r1482, GUI svn.r3310) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H26 Fe O7' _chemical_formula_sum 'C24 H26 Fe O7' _chemical_formula_weight 482.30 _chemical_melting_point ? _chemical_oxdiff_formula 'Fe C24 H26 O7' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.1269(4) _cell_length_b 10.2163(3) _cell_length_c 12.6671(3) _cell_angle_alpha 100.953(2) _cell_angle_beta 106.792(3) _cell_angle_gamma 110.272(3) _cell_volume 1113.83(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8687 _cell_measurement_temperature 100.2 _cell_measurement_theta_max 29.3959 _cell_measurement_theta_min 3.4062 _exptl_absorpt_coefficient_mu 0.720 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 15144 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.46 _diffrn_reflns_theta_min 3.41 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.883 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 86.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 11.7214 37.0000 -60.0000 96 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 82.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 11.7214 77.0000 30.0000 104 #__ type_ start__ end____ width___ exp.time_ 3 omega -55.00 45.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 11.7214 -77.0000 150.0000 100 #__ type_ start__ end____ width___ exp.time_ 4 omega -67.00 45.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 11.7214 -77.0000 -60.0000 112 #__ type_ start__ end____ width___ exp.time_ 5 omega -28.00 64.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - -11.8777 37.0000 30.0000 92 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0484698000 _diffrn_orient_matrix_UB_12 0.0702760000 _diffrn_orient_matrix_UB_13 0.0013289000 _diffrn_orient_matrix_UB_21 0.0607971000 _diffrn_orient_matrix_UB_22 -0.0214418000 _diffrn_orient_matrix_UB_23 0.0080765000 _diffrn_orient_matrix_UB_31 -0.0223732000 _diffrn_orient_matrix_UB_32 -0.0267898000 _diffrn_orient_matrix_UB_33 -0.0612585000 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _reflns_number_gt 4755 _reflns_number_total 5448 _reflns_odcompleteness_completeness 95.11 _reflns_odcompleteness_iscentric 0 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.436 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.057 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 5448 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0310 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+0.6228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.0723 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.73898(2) 0.83636(2) 0.641115(18) 0.01314(6) Uani 1 1 d . . . O1 O 0.50672(13) 0.61082(13) 0.41876(10) 0.0263(3) Uani 1 1 d . . . O2 O 0.63652(14) 0.67071(12) 0.79040(10) 0.0245(3) Uani 1 1 d . . . O3 O 0.56835(14) 1.01734(13) 0.62268(11) 0.0284(3) Uani 1 1 d . . . O4 O 0.83987(14) 1.19044(12) 0.85931(10) 0.0211(2) Uani 1 1 d . . . O5 O 0.82229(12) 1.01705(11) 0.94687(9) 0.0175(2) Uani 1 1 d . . . O6 O 0.91307(13) 0.59653(11) 0.78352(9) 0.0196(2) Uani 1 1 d . . . O7 O 0.72730(16) 0.28552(15) 0.31987(11) 0.0368(3) Uani 1 1 d . . . C1 C 0.59669(18) 0.69802(17) 0.50405(14) 0.0179(3) Uani 1 1 d . . . C2 C 0.67428(17) 0.73250(16) 0.73104(13) 0.0164(3) Uani 1 1 d . . . C3 C 0.63502(18) 0.94786(17) 0.63225(13) 0.0184(3) Uani 1 1 d . . . C4 C 0.85705(17) 1.08050(16) 0.86788(12) 0.0150(3) Uani 1 1 d . . . C5 C 0.91335(17) 0.99887(16) 0.79658(13) 0.0140(3) Uani 1 1 d . . . H5 H 0.965(2) 0.9520(19) 0.8416(15) 0.018(4) Uiso 1 1 d . . . C6 C 0.99841(17) 1.08569(16) 0.73210(13) 0.0146(3) Uani 1 1 d . . . H6 H 0.9759 1.1740 0.7361 0.018 Uiso 1 1 calc R . . C7 C 0.91665(17) 0.98806(16) 0.60599(13) 0.0159(3) Uani 1 1 d . . . H7 H 0.8917(19) 1.0307(18) 0.5470(15) 0.015(4) Uiso 1 1 d . . . C8 C 0.89836(17) 0.84341(16) 0.56479(13) 0.0153(3) Uani 1 1 d . . . H8 H 0.8574(19) 0.7983(18) 0.4832(15) 0.012(4) Uiso 1 1 d . . . C9 C 0.91040(17) 0.75434(16) 0.63638(13) 0.0140(3) Uani 1 1 d . . . H9 H 0.978(2) 0.8002(18) 0.7136(15) 0.014(4) Uiso 1 1 d . . . C10 C 0.76250(19) 1.08895(18) 1.01757(14) 0.0210(3) Uani 1 1 d . . . H10A H 0.6636 1.0805 0.9681 0.032 Uiso 1 1 calc R . . H10C H 0.8336 1.1933 1.0558 0.032 Uiso 1 1 calc R . . H10B H 0.7497 1.0419 1.0768 0.032 Uiso 1 1 calc R . . C11 C 0.86624(16) 0.59478(16) 0.59094(13) 0.0155(3) Uani 1 1 d . . . C12 C 0.86740(17) 0.51503(16) 0.66941(13) 0.0169(3) Uani 1 1 d . . . C13 C 0.82216(18) 0.36335(17) 0.63083(15) 0.0229(3) Uani 1 1 d . . . H13 H 0.8230 0.3100 0.6846 0.027 Uiso 1 1 calc R . . C14 C 0.77592(19) 0.29093(18) 0.51325(16) 0.0272(4) Uani 1 1 d . . . H14 H 0.7447 0.1875 0.4865 0.033 Uiso 1 1 calc R . . C15 C 0.77490(19) 0.36817(19) 0.43443(15) 0.0249(4) Uani 1 1 d . . . C16 C 0.82010(18) 0.51933(18) 0.47262(14) 0.0204(3) Uani 1 1 d . . . H16 H 0.8198 0.5719 0.4183 0.025 Uiso 1 1 calc R . . C17 C 0.9026(2) 0.51813(19) 0.86474(16) 0.0320(4) Uani 1 1 d . . . H17A H 0.7969 0.4457 0.8400 0.048 Uiso 1 1 calc R . . H17C H 0.9346 0.5875 0.9421 0.048 Uiso 1 1 calc R . . H17B H 0.9690 0.4672 0.8680 0.048 Uiso 1 1 calc R . . C18 C 0.7250(2) 0.3618(2) 0.23732(16) 0.0367(5) Uani 1 1 d . . . H18B H 0.6864 0.2914 0.1592 0.055 Uiso 1 1 calc R . . H18C H 0.8286 0.4348 0.2561 0.055 Uiso 1 1 calc R . . H18A H 0.6584 0.4117 0.2396 0.055 Uiso 1 1 calc R . . C19 C 1.17065(18) 1.14422(16) 0.78340(13) 0.0163(3) Uani 1 1 d . . . C20 C 1.25015(18) 1.09674(17) 0.73175(14) 0.0198(3) Uani 1 1 d . . . H20 H 1.1950 1.0191 0.6594 0.024 Uiso 1 1 calc R . . C21 C 1.42128(19) 1.1574(2) 0.77982(15) 0.0260(4) Uani 1 1 d . . . H21B H 1.4578 1.1721 0.7166 0.031 Uiso 1 1 calc R . . H21A H 1.4523 1.0849 0.8088 0.031 Uiso 1 1 calc R . . C22 C 1.4960(2) 1.30306(19) 0.87850(15) 0.0273(4) Uani 1 1 d . . . H22B H 1.6043 1.3261 0.9210 0.033 Uiso 1 1 calc R . . H22A H 1.4926 1.3831 0.8458 0.033 Uiso 1 1 calc R . . C23 C 1.41455(19) 1.29550(18) 0.96253(14) 0.0239(4) Uani 1 1 d . . . H23B H 1.4666 1.3902 1.0271 0.029 Uiso 1 1 calc R . . H23A H 1.4196 1.2167 0.9962 0.029 Uiso 1 1 calc R . . C24 C 1.24813(18) 1.26432(17) 0.90094(14) 0.0211(3) Uani 1 1 d . . . H24A H 1.1921 1.2345 0.9511 0.025 Uiso 1 1 calc R . . H24B H 1.2429 1.3560 0.8899 0.025 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 0.01451(11) 0.01260(11) 0.01249(11) 0.00400(8) 0.00493(8) 0.00625(8) O1 0.0220(6) 0.0246(6) 0.0217(6) -0.0013(5) 0.0016(5) 0.0083(5) O2 0.0286(6) 0.0217(6) 0.0240(6) 0.0091(5) 0.0150(5) 0.0068(5) O3 0.0303(7) 0.0276(6) 0.0275(6) 0.0045(5) 0.0051(5) 0.0197(6) O4 0.0320(6) 0.0165(5) 0.0212(6) 0.0076(5) 0.0133(5) 0.0144(5) O5 0.0238(6) 0.0175(5) 0.0168(5) 0.0072(4) 0.0115(5) 0.0111(5) O6 0.0270(6) 0.0147(5) 0.0177(5) 0.0073(4) 0.0081(5) 0.0090(5) O7 0.0394(8) 0.0327(7) 0.0243(6) -0.0104(6) 0.0004(6) 0.0198(6) C1 0.0194(8) 0.0183(7) 0.0205(8) 0.0070(6) 0.0096(7) 0.0109(6) C2 0.0153(7) 0.0142(7) 0.0166(7) 0.0007(6) 0.0051(6) 0.0061(6) C3 0.0182(8) 0.0173(7) 0.0139(7) 0.0022(6) 0.0024(6) 0.0056(6) C4 0.0140(7) 0.0138(7) 0.0123(7) 0.0026(6) 0.0025(6) 0.0035(6) C5 0.0164(7) 0.0127(7) 0.0130(7) 0.0045(6) 0.0050(6) 0.0066(6) C6 0.0176(7) 0.0129(7) 0.0151(7) 0.0061(6) 0.0069(6) 0.0070(6) C7 0.0163(7) 0.0180(7) 0.0148(7) 0.0083(6) 0.0064(6) 0.0068(6) C8 0.0153(7) 0.0185(7) 0.0111(7) 0.0037(6) 0.0061(6) 0.0058(6) C9 0.0138(7) 0.0157(7) 0.0127(7) 0.0036(6) 0.0055(6) 0.0066(6) C10 0.0251(8) 0.0222(8) 0.0199(8) 0.0059(6) 0.0134(7) 0.0115(7) C11 0.0120(7) 0.0159(7) 0.0180(7) 0.0032(6) 0.0048(6) 0.0073(6) C12 0.0133(7) 0.0160(7) 0.0202(7) 0.0036(6) 0.0049(6) 0.0074(6) C13 0.0173(8) 0.0164(8) 0.0318(9) 0.0067(7) 0.0038(7) 0.0090(6) C14 0.0193(8) 0.0156(8) 0.0374(10) -0.0015(7) 0.0023(7) 0.0095(7) C15 0.0185(8) 0.0241(8) 0.0228(8) -0.0060(7) 0.0011(7) 0.0114(7) C16 0.0180(8) 0.0231(8) 0.0190(8) 0.0028(6) 0.0044(6) 0.0118(7) C17 0.0491(12) 0.0232(9) 0.0271(9) 0.0150(8) 0.0175(9) 0.0133(8) C18 0.0281(10) 0.0525(12) 0.0206(9) -0.0069(8) 0.0036(8) 0.0220(9) C19 0.0188(7) 0.0146(7) 0.0145(7) 0.0064(6) 0.0060(6) 0.0055(6) C20 0.0212(8) 0.0209(8) 0.0162(7) 0.0058(6) 0.0068(6) 0.0082(6) C21 0.0217(8) 0.0328(9) 0.0264(9) 0.0094(8) 0.0114(7) 0.0132(7) C22 0.0189(8) 0.0284(9) 0.0285(9) 0.0078(7) 0.0084(7) 0.0046(7) C23 0.0212(8) 0.0206(8) 0.0204(8) 0.0044(7) 0.0047(7) 0.0023(7) C24 0.0207(8) 0.0183(8) 0.0191(8) 0.0021(6) 0.0082(7) 0.0044(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 C1 1.8163(16) . ? Fe1 C2 1.8059(16) . ? Fe1 C3 1.7972(16) . ? Fe1 C5 2.1141(15) . ? Fe1 C7 2.1515(15) . ? Fe1 C8 2.0958(15) . ? Fe1 C9 2.1836(15) . ? O1 C1 1.1376(19) . ? O2 C2 1.1356(18) . ? O3 C3 1.1366(19) . ? O4 C4 1.2142(18) . ? O5 C4 1.3554(17) . ? O5 C10 1.4422(18) . ? O6 C12 1.3733(18) . ? O6 C17 1.4243(19) . ? O7 C15 1.378(2) . ? O7 C18 1.417(3) . ? C4 C5 1.475(2) . ? C5 H5 0.967(18) . ? C5 C6 1.532(2) . ? C6 H6 1.0000 . ? C6 C7 1.513(2) . ? C6 C19 1.516(2) . ? C7 H7 0.950(17) . ? C7 C8 1.397(2) . ? C8 H8 0.944(17) . ? C8 C9 1.411(2) . ? C9 H9 0.930(17) . ? C9 C11 1.476(2) . ? C10 H10A 0.9800 . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? C11 C12 1.400(2) . ? C11 C16 1.402(2) . ? C12 C13 1.393(2) . ? C13 H13 0.9500 . ? C13 C14 1.387(2) . ? C14 H14 0.9500 . ? C14 C15 1.385(3) . ? C15 C16 1.388(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18A 0.9800 . ? C19 C20 1.329(2) . ? C19 C24 1.517(2) . ? C20 H20 0.9500 . ? C20 C21 1.504(2) . ? C21 H21B 0.9900 . ? C21 H21A 0.9900 . ? C21 C22 1.522(2) . ? C22 H22B 0.9900 . ? C22 H22A 0.9900 . ? C22 C23 1.521(2) . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? C23 C24 1.525(2) . ? C24 H24A 0.9900 . ? C24 H24B 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 Fe1 C5 H5 108.7(10) . . ? Fe1 C7 H7 120.2(11) . . ? Fe1 C8 H8 115.7(10) . . ? Fe1 C9 H9 99.8(11) . . ? O1 C1 Fe1 179.34(15) . . ? O2 C2 Fe1 177.98(14) . . ? O3 C3 Fe1 177.65(14) . . ? O4 C4 O5 121.72(13) . . ? O4 C4 C5 126.35(13) . . ? O5 C4 C5 111.93(12) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10C 109.5 . . ? O5 C10 H10B 109.5 . . ? O6 C12 C11 115.24(13) . . ? O6 C12 C13 123.94(14) . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17C 109.5 . . ? O6 C17 H17B 109.5 . . ? O7 C15 C14 115.78(15) . . ? O7 C15 C16 124.08(17) . . ? O7 C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? O7 C18 H18A 109.5 . . ? C1 Fe1 C5 176.94(6) . . ? C1 Fe1 C7 108.60(6) . . ? C1 Fe1 C8 86.26(6) . . ? C1 Fe1 C9 93.30(6) . . ? C2 Fe1 C1 94.95(7) . . ? C2 Fe1 C5 87.30(6) . . ? C2 Fe1 C7 151.61(7) . . ? C2 Fe1 C8 132.36(6) . . ? C2 Fe1 C9 94.10(6) . . ? C3 Fe1 C1 91.30(7) . . ? C3 Fe1 C2 102.80(7) . . ? C3 Fe1 C5 90.22(6) . . ? C3 Fe1 C7 92.54(7) . . ? C3 Fe1 C8 124.81(7) . . ? C3 Fe1 C9 162.03(6) . . ? C4 O5 C10 114.91(12) . . ? C4 C5 Fe1 113.44(10) . . ? C4 C5 H5 109.8(10) . . ? C4 C5 C6 114.70(12) . . ? C5 Fe1 C7 68.67(6) . . ? C5 Fe1 C9 84.46(6) . . ? C5 C6 H6 106.2 . . ? C6 C5 Fe1 93.53(9) . . ? C6 C5 H5 115.8(10) . . ? C6 C7 Fe1 92.62(9) . . ? C6 C7 H7 119.2(10) . . ? C6 C19 C24 114.34(13) . . ? C7 Fe1 C9 69.53(6) . . ? C7 C6 C5 104.37(12) . . ? C7 C6 H6 106.2 . . ? C7 C6 C19 116.95(12) . . ? C7 C8 Fe1 72.97(9) . . ? C7 C8 H8 117.1(10) . . ? C7 C8 C9 123.36(14) . . ? C8 Fe1 C5 90.70(6) . . ? C8 Fe1 C7 38.38(6) . . ? C8 Fe1 C9 38.44(6) . . ? C8 C7 Fe1 68.65(8) . . ? C8 C7 C6 125.09(13) . . ? C8 C7 H7 114.6(10) . . ? C8 C9 Fe1 67.41(8) . . ? C8 C9 H9 118.0(10) . . ? C8 C9 C11 123.63(13) . . ? C9 C8 Fe1 74.15(9) . . ? C9 C8 H8 118.4(10) . . ? H10A C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C11 C9 Fe1 120.70(10) . . ? C11 C9 H9 114.9(11) . . ? C11 C16 H16 119.8 . . ? C12 O6 C17 117.20(12) . . ? C12 C11 C9 118.33(13) . . ? C12 C11 C16 118.72(14) . . ? C12 C13 H13 120.3 . . ? C13 C12 C11 120.81(14) . . ? C13 C14 H14 119.7 . . ? C14 C13 C12 119.43(16) . . ? C14 C13 H13 120.3 . . ? C14 C15 C16 120.13(15) . . ? C15 O7 C18 116.97(14) . . ? C15 C14 C13 120.57(15) . . ? C15 C14 H14 119.7 . . ? C15 C16 C11 120.34(16) . . ? C15 C16 H16 119.8 . . ? C16 C11 C9 122.94(14) . . ? H17A C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? H18B C18 H18C 109.5 . . ? H18B C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? C19 C6 C5 116.08(12) . . ? C19 C6 H6 106.2 . . ? C19 C20 H20 117.7 . . ? C19 C20 C21 124.58(15) . . ? C19 C24 C23 112.85(13) . . ? C19 C24 H24A 109.0 . . ? C19 C24 H24B 109.0 . . ? C20 C19 C6 124.07(14) . . ? C20 C19 C24 121.59(14) . . ? C20 C21 H21B 109.2 . . ? C20 C21 H21A 109.2 . . ? C20 C21 C22 112.06(14) . . ? C21 C20 H20 117.7 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22A 109.5 . . ? H21B C21 H21A 107.9 . . ? C22 C21 H21B 109.2 . . ? C22 C21 H21A 109.2 . . ? C22 C23 H23B 109.4 . . ? C22 C23 H23A 109.4 . . ? C22 C23 C24 111.05(14) . . ? H22B C22 H22A 108.1 . . ? C23 C22 C21 110.75(14) . . ? C23 C22 H22B 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C24 H24A 109.0 . . ? C23 C24 H24B 109.0 . . ? H23B C23 H23A 108.0 . . ? C24 C23 H23B 109.4 . . ? C24 C23 H23A 109.4 . . ? H24A C24 H24B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Fe1 C5 C6 C7 -8.02(11) . . . . ? Fe1 C5 C6 C19 -138.28(11) . . . . ? Fe1 C7 C8 C9 -57.07(14) . . . . ? Fe1 C8 C9 C11 112.79(14) . . . . ? Fe1 C9 C11 C12 -91.17(15) . . . . ? Fe1 C9 C11 C16 87.38(16) . . . . ? O4 C4 C5 Fe1 -87.58(17) . . . . ? O4 C4 C5 C6 18.3(2) . . . . ? O5 C4 C5 Fe1 91.47(13) . . . . ? O5 C4 C5 C6 -162.66(12) . . . . ? O6 C12 C13 C14 179.08(15) . . . . ? O7 C15 C16 C11 179.69(15) . . . . ? C1 Fe1 C2 O2 -173(4) . . . . ? C1 Fe1 C3 O3 -42(4) . . . . ? C1 Fe1 C5 C4 151.9(12) . . . . ? C1 Fe1 C5 C6 33.0(12) . . . . ? C1 Fe1 C7 C6 175.54(9) . . . . ? C1 Fe1 C7 C8 -57.59(10) . . . . ? C1 Fe1 C8 C7 126.70(10) . . . . ? C1 Fe1 C8 C9 -100.09(9) . . . . ? C1 Fe1 C9 C8 79.76(10) . . . . ? C1 Fe1 C9 C11 -37.02(12) . . . . ? C2 Fe1 C1 O1 22(14) . . . . ? C2 Fe1 C3 O3 -137(3) . . . . ? C2 Fe1 C5 C4 -70.69(11) . . . . ? C2 Fe1 C5 C6 170.42(10) . . . . ? C2 Fe1 C7 C6 -39.94(17) . . . . ? C2 Fe1 C7 C8 86.93(15) . . . . ? C2 Fe1 C8 C7 -140.02(10) . . . . ? C2 Fe1 C8 C9 -6.80(12) . . . . ? C2 Fe1 C9 C8 174.97(9) . . . . ? C2 Fe1 C9 C11 58.19(12) . . . . ? C3 Fe1 C1 O1 -81(14) . . . . ? C3 Fe1 C2 O2 -81(4) . . . . ? C3 Fe1 C5 C4 32.11(11) . . . . ? C3 Fe1 C5 C6 -86.78(10) . . . . ? C3 Fe1 C7 C6 83.32(10) . . . . ? C3 Fe1 C7 C8 -149.81(10) . . . . ? C3 Fe1 C8 C7 37.72(12) . . . . ? C3 Fe1 C8 C9 170.94(9) . . . . ? C3 Fe1 C9 C8 -24.8(2) . . . . ? C3 Fe1 C9 C11 -141.56(19) . . . . ? C4 C5 C6 C7 -125.87(13) . . . . ? C4 C5 C6 C19 103.88(15) . . . . ? C5 Fe1 C1 O1 159(13) . . . . ? C5 Fe1 C2 O2 9(4) . . . . ? C5 Fe1 C3 O3 136(4) . . . . ? C5 Fe1 C7 C6 -5.93(8) . . . . ? C5 Fe1 C7 C8 120.94(10) . . . . ? C5 Fe1 C8 C7 -53.04(9) . . . . ? C5 Fe1 C8 C9 80.18(9) . . . . ? C5 Fe1 C9 C8 -98.15(9) . . . . ? C5 Fe1 C9 C11 145.07(12) . . . . ? C5 C6 C7 Fe1 7.88(11) . . . . ? C5 C6 C7 C8 -57.71(18) . . . . ? C5 C6 C19 C20 112.56(17) . . . . ? C5 C6 C19 C24 -67.56(17) . . . . ? C6 C7 C8 Fe1 77.60(14) . . . . ? C6 C7 C8 C9 20.5(2) . . . . ? C6 C19 C20 C21 177.86(14) . . . . ? C6 C19 C24 C23 166.72(13) . . . . ? C7 Fe1 C1 O1 -175(100) . . . . ? C7 Fe1 C2 O2 40(4) . . . . ? C7 Fe1 C3 O3 67(4) . . . . ? C7 Fe1 C5 C4 124.75(12) . . . . ? C7 Fe1 C5 C6 5.86(8) . . . . ? C7 Fe1 C8 C9 133.22(13) . . . . ? C7 Fe1 C9 C8 -28.88(9) . . . . ? C7 Fe1 C9 C11 -145.66(13) . . . . ? C7 C6 C19 C20 -11.4(2) . . . . ? C7 C6 C19 C24 168.47(13) . . . . ? C7 C8 C9 Fe1 56.54(14) . . . . ? C7 C8 C9 C11 169.33(14) . . . . ? C8 Fe1 C1 O1 154(14) . . . . ? C8 Fe1 C2 O2 97(4) . . . . ? C8 Fe1 C3 O3 44(4) . . . . ? C8 Fe1 C5 C4 156.93(11) . . . . ? C8 Fe1 C5 C6 38.04(9) . . . . ? C8 Fe1 C7 C6 -126.87(13) . . . . ? C8 Fe1 C9 C11 -116.78(15) . . . . ? C8 C9 C11 C12 -173.02(14) . . . . ? C8 C9 C11 C16 5.5(2) . . . . ? C9 Fe1 C1 O1 116(14) . . . . ? C9 Fe1 C2 O2 93(4) . . . . ? C9 Fe1 C3 O3 63(4) . . . . ? C9 Fe1 C5 C4 -165.08(11) . . . . ? C9 Fe1 C5 C6 76.03(9) . . . . ? C9 Fe1 C7 C6 -97.94(9) . . . . ? C9 Fe1 C7 C8 28.92(9) . . . . ? C9 Fe1 C8 C7 -133.22(13) . . . . ? C9 C11 C12 O6 -1.0(2) . . . . ? C9 C11 C12 C13 177.96(14) . . . . ? C9 C11 C16 C15 -177.81(14) . . . . ? C10 O5 C4 O4 0.7(2) . . . . ? C10 O5 C4 C5 -178.39(12) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C11 C16 C15 0.7(2) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? C13 C14 C15 O7 179.84(15) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 -0.4(2) . . . . ? C16 C11 C12 O6 -179.63(13) . . . . ? C16 C11 C12 C13 -0.7(2) . . . . ? C17 O6 C12 C11 174.33(14) . . . . ? C17 O6 C12 C13 -4.6(2) . . . . ? C18 O7 C15 C14 179.94(15) . . . . ? C18 O7 C15 C16 -0.1(2) . . . . ? C19 C6 C7 Fe1 137.61(11) . . . . ? C19 C6 C7 C8 72.02(19) . . . . ? C19 C20 C21 C22 -14.0(2) . . . . ? C20 C19 C24 C23 -13.4(2) . . . . ? C20 C21 C22 C23 44.5(2) . . . . ? C21 C22 C23 C24 -60.70(19) . . . . ? C22 C23 C24 C19 44.16(19) . . . . ? C24 C19 C20 C21 -2.0(2) . . . . ? data_donsa _database_code_depnum_ccdc_archive 'CCDC 823813' #TrackingRef '2-(1-methylethenyl)-3-pentene-1,5-diyl)iron.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 Fe O7' _chemical_formula_weight 442.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7069(2) _cell_length_b 13.1541(3) _cell_length_c 16.1134(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.2680(10) _cell_angle_gamma 90.00 _cell_volume 2056.94(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7881 _cell_measurement_theta_min 3 _cell_measurement_theta_max 66 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 6.229 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1132 _exptl_absorpt_correction_T_max 0.5219 _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13223 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 66.98 _reflns_number_total 3404 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_molecular_graphics 'XP v5.1 (Bruker, 1998)' _computing_publication_material 'XCIF v6.12 (Bruker, 2001)' _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^)+(0.0433P)^2^+0.7916P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00130(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3404 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _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 0.21257(2) 0.319648(18) 0.870671(15) 0.01299(10) Uani 1 1 d . . . O1 O 0.33162(13) 0.58627(9) 0.83291(7) 0.0224(3) Uani 1 1 d . . . O2 O 0.31735(12) 0.54913(8) 0.96875(7) 0.0210(3) Uani 1 1 d . . . O3 O 0.44432(12) 0.19194(8) 1.05976(7) 0.0192(3) Uani 1 1 d . . . O4 O 0.15448(12) -0.13699(8) 0.93221(8) 0.0206(3) Uani 1 1 d . . . O5 O -0.01972(13) 0.17721(9) 0.84555(9) 0.0265(3) Uani 1 1 d . . . O6 O 0.05198(13) 0.48543(9) 0.79338(8) 0.0260(3) Uani 1 1 d . . . O7 O 0.16391(14) 0.35378(10) 1.04846(9) 0.0304(3) Uani 1 1 d . . . C1 C 0.34424(17) 0.52502(12) 0.88912(11) 0.0175(4) Uani 1 1 d . . . C2 C 0.38478(16) 0.41727(12) 0.88101(11) 0.0153(3) Uani 1 1 d . . . C3 C 0.44084(17) 0.38732(12) 0.79681(11) 0.0169(4) Uani 1 1 d . . . C4 C 0.35065(17) 0.29935(13) 0.76804(11) 0.0164(4) Uani 1 1 d . . . C5 C 0.33459(17) 0.20963(13) 0.81264(11) 0.0164(4) Uani 1 1 d . . . C6 C 0.36496(17) 0.20137(12) 0.89826(11) 0.0151(3) Uani 1 1 d . . . C7 C 0.59581(17) 0.37026(14) 0.79528(11) 0.0227(4) Uani 1 1 d . . . C8 C 0.6531(2) 0.28069(17) 0.78178(13) 0.0296(5) Uani 1 1 d . . . C9 C 0.6775(2) 0.46582(17) 0.81075(15) 0.0331(5) Uani 1 1 d . . . C10 C 0.2605(2) 0.64913(14) 0.98137(14) 0.0255(4) Uani 1 1 d . . . C11 C 0.33069(16) 0.11119(12) 0.94806(10) 0.0149(3) Uani 1 1 d . . . C12 C 0.37664(16) 0.10686(12) 1.03120(11) 0.0155(3) Uani 1 1 d . . . C13 C 0.35226(17) 0.02112(12) 1.07960(11) 0.0170(4) Uani 1 1 d . . . C14 C 0.27784(17) -0.06024(12) 1.04614(11) 0.0181(4) Uani 1 1 d . . . C15 C 0.22839(16) -0.05553(12) 0.96545(11) 0.0162(3) Uani 1 1 d . . . C16 C 0.25585(17) 0.02841(12) 0.91629(11) 0.0154(3) Uani 1 1 d . . . C18 C 0.00948(18) -0.11827(14) 0.92455(13) 0.0208(4) Uani 1 1 d . . . C19 C 0.4948(2) 0.19016(14) 1.14361(12) 0.0225(4) Uani 1 1 d . . . C20 C 0.07146(17) 0.23098(12) 0.85501(11) 0.0172(4) Uani 1 1 d . . . C21 C 0.11588(17) 0.42167(13) 0.82298(11) 0.0182(4) Uani 1 1 d . . . C22 C 0.18191(18) 0.34038(12) 0.97977(12) 0.0200(4) Uani 1 1 d . . . H2 H 0.441(2) 0.3975(14) 0.9283(12) 0.022(5) Uiso 1 1 d . . . H3 H 0.4217(18) 0.4446(14) 0.7590(11) 0.015(4) Uiso 1 1 d . . . H4 H 0.321(2) 0.2985(14) 0.7143(13) 0.019(5) Uiso 1 1 d . . . H5 H 0.2913(19) 0.1585(13) 0.7857(11) 0.012(4) Uiso 1 1 d . . . H6 H 0.4393(18) 0.2404(12) 0.9213(10) 0.007(4) Uiso 1 1 d . . . H8A H 0.749(2) 0.2750(16) 0.7810(13) 0.035(6) Uiso 1 1 d . . . H8B H 0.599(2) 0.2190(16) 0.7672(12) 0.027(5) Uiso 1 1 d . . . H9A H 0.653(2) 0.4990(17) 0.8649(15) 0.036(6) Uiso 1 1 d . . . H9B H 0.774(3) 0.4533(17) 0.8115(15) 0.045(7) Uiso 1 1 d . . . H9C H 0.658(2) 0.5147(18) 0.7673(16) 0.045(7) Uiso 1 1 d . . . H10A H 0.235(2) 0.6500(17) 1.0381(15) 0.034(6) Uiso 1 1 d . . . H10B H 0.176(3) 0.6570(18) 0.9451(16) 0.048(7) Uiso 1 1 d . . . H10C H 0.323(2) 0.7026(16) 0.9715(13) 0.027(5) Uiso 1 1 d . . . H13 H 0.3842(19) 0.0195(14) 1.1335(12) 0.020(5) Uiso 1 1 d . . . H14 H 0.2595(18) -0.1178(14) 1.0788(11) 0.012(4) Uiso 1 1 d . . . H16 H 0.2211(17) 0.0312(13) 0.8595(11) 0.008(4) Uiso 1 1 d . . . H18A H -0.028(2) -0.1763(14) 0.8957(12) 0.019(5) Uiso 1 1 d . . . H18B H -0.028(2) -0.1100(14) 0.9787(13) 0.025(5) Uiso 1 1 d . . . H18C H -0.009(2) -0.0550(15) 0.8918(13) 0.026(5) Uiso 1 1 d . . . H19A H 0.419(2) 0.1797(14) 1.1841(14) 0.030(6) Uiso 1 1 d . . . H19B H 0.536(2) 0.2567(16) 1.1531(12) 0.025(5) Uiso 1 1 d . . . H19C H 0.562(2) 0.1343(16) 1.1520(13) 0.030(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01179(15) 0.01435(15) 0.01277(17) 0.00073(9) -0.00113(10) -0.00084(9) O1 0.0282(7) 0.0181(6) 0.0206(7) 0.0058(5) -0.0073(5) -0.0038(5) O2 0.0283(7) 0.0154(6) 0.0190(7) 0.0002(5) -0.0014(5) 0.0020(5) O3 0.0231(7) 0.0185(6) 0.0158(7) -0.0007(4) -0.0045(5) -0.0060(5) O4 0.0207(6) 0.0128(6) 0.0282(7) -0.0048(5) -0.0020(5) -0.0010(5) O5 0.0187(7) 0.0272(7) 0.0333(8) 0.0032(5) -0.0041(6) -0.0069(5) O6 0.0213(7) 0.0219(6) 0.0345(8) 0.0041(5) -0.0069(6) 0.0031(5) O7 0.0415(8) 0.0312(7) 0.0188(9) -0.0039(6) 0.0075(6) -0.0093(6) C1 0.0138(8) 0.0192(8) 0.0192(10) 0.0020(7) -0.0044(7) -0.0052(6) C2 0.0124(8) 0.0172(8) 0.0162(9) 0.0036(6) -0.0034(7) -0.0037(6) C3 0.0154(8) 0.0200(9) 0.0152(9) 0.0050(7) -0.0022(7) -0.0013(6) C4 0.0127(8) 0.0248(9) 0.0116(10) -0.0007(7) -0.0003(7) 0.0020(6) C5 0.0149(8) 0.0173(8) 0.0170(9) -0.0043(7) 0.0000(7) 0.0010(7) C6 0.0114(8) 0.0149(8) 0.0189(10) -0.0014(6) -0.0003(7) 0.0011(6) C7 0.0157(9) 0.0376(10) 0.0147(10) 0.0084(8) 0.0004(7) -0.0022(8) C8 0.0177(10) 0.0423(12) 0.0291(12) 0.0089(9) 0.0039(8) 0.0057(9) C9 0.0190(11) 0.0453(12) 0.0348(14) 0.0072(10) -0.0022(9) -0.0103(9) C10 0.0321(11) 0.0177(9) 0.0268(12) -0.0022(8) 0.0016(9) 0.0025(8) C11 0.0139(8) 0.0151(8) 0.0157(9) -0.0006(6) 0.0005(6) 0.0031(6) C12 0.0124(8) 0.0149(8) 0.0193(10) -0.0030(6) 0.0011(7) -0.0001(6) C13 0.0178(9) 0.0205(8) 0.0127(10) 0.0013(7) -0.0015(7) 0.0009(7) C14 0.0173(9) 0.0156(8) 0.0216(10) 0.0038(7) 0.0030(7) 0.0005(6) C15 0.0133(8) 0.0133(8) 0.0220(10) -0.0051(6) 0.0015(7) 0.0022(6) C16 0.0147(8) 0.0150(8) 0.0163(10) -0.0028(6) -0.0011(7) 0.0024(6) C18 0.0190(9) 0.0227(9) 0.0209(11) -0.0045(8) 0.0016(7) -0.0054(7) C19 0.0263(10) 0.0262(10) 0.0148(10) -0.0020(7) -0.0023(8) -0.0076(8) C20 0.0173(9) 0.0177(8) 0.0165(9) 0.0032(7) -0.0008(7) 0.0025(7) C21 0.0150(8) 0.0221(9) 0.0176(10) -0.0028(7) -0.0003(7) -0.0047(7) C22 0.0186(9) 0.0160(8) 0.0254(12) 0.0020(7) 0.0003(7) -0.0041(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 C21 1.8002(18) . ? Fe1 C22 1.810(2) . ? Fe1 C20 1.8125(17) . ? Fe1 C5 2.1025(16) . ? Fe1 C2 2.1115(16) . ? Fe1 C4 2.1681(17) . ? Fe1 C6 2.1857(16) . ? O1 C1 1.216(2) . ? O2 C1 1.353(2) . ? O2 C10 1.443(2) . ? O3 C12 1.3720(19) . ? O3 C19 1.427(2) . ? O4 C15 1.3903(19) . ? O4 C18 1.431(2) . ? O5 C20 1.141(2) . ? O6 C21 1.141(2) . ? O7 C22 1.138(2) . ? C1 C2 1.477(2) . ? C2 C3 1.525(2) . ? C2 H2 0.96(2) . ? C3 C4 1.517(2) . ? C3 C7 1.522(2) . ? C3 H3 0.984(18) . ? C4 C5 1.392(2) . ? C4 H4 0.91(2) . ? C5 C6 1.409(2) . ? C5 H5 0.899(19) . ? C6 C11 1.474(2) . ? C6 H6 0.954(18) . ? C7 C8 1.323(3) . ? C7 C9 1.504(3) . ? C8 H8A 0.94(2) . ? C8 H8B 0.99(2) . ? C9 H9A 1.01(2) . ? C9 H9B 0.95(3) . ? C9 H9C 0.97(3) . ? C10 H10A 0.95(2) . ? C10 H10B 1.00(3) . ? C10 H10C 0.95(2) . ? C11 C16 1.400(2) . ? C11 C12 1.404(2) . ? C12 C13 1.394(2) . ? C13 C14 1.393(2) . ? C13 H13 0.92(2) . ? C14 C15 1.377(2) . ? C14 H14 0.942(18) . ? C15 C16 1.388(2) . ? C16 H16 0.969(17) . ? C18 H18A 0.963(19) . ? C18 H18B 0.96(2) . ? C18 H18C 1.00(2) . ? C19 H19A 1.00(2) . ? C19 H19B 0.97(2) . ? C19 H19C 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 Fe1 C22 101.94(8) . . ? C21 Fe1 C20 92.00(7) . . ? C22 Fe1 C20 95.29(8) . . ? C21 Fe1 C5 128.08(7) . . ? C22 Fe1 C5 129.94(7) . . ? C20 Fe1 C5 85.79(7) . . ? C21 Fe1 C2 89.12(7) . . ? C22 Fe1 C2 88.78(7) . . ? C20 Fe1 C2 175.46(7) . . ? C5 Fe1 C2 90.05(7) . . ? C21 Fe1 C4 95.25(7) . . ? C22 Fe1 C4 151.29(7) . . ? C20 Fe1 C4 107.02(7) . . ? C5 Fe1 C4 38.02(6) . . ? C2 Fe1 C4 68.49(7) . . ? C21 Fe1 C6 164.07(7) . . ? C22 Fe1 C6 91.99(7) . . ? C20 Fe1 C6 94.37(7) . . ? C5 Fe1 C6 38.29(7) . . ? C2 Fe1 C6 83.45(6) . . ? C4 Fe1 C6 68.93(6) . . ? C1 O2 C10 115.46(14) . . ? C12 O3 C19 117.12(13) . . ? C15 O4 C18 113.49(12) . . ? O1 C1 O2 122.18(15) . . ? O1 C1 C2 126.32(16) . . ? O2 C1 C2 111.48(14) . . ? C1 C2 C3 115.31(14) . . ? C1 C2 Fe1 112.24(11) . . ? C3 C2 Fe1 94.03(10) . . ? C1 C2 H2 109.6(11) . . ? C3 C2 H2 115.5(12) . . ? Fe1 C2 H2 109.2(11) . . ? C4 C3 C7 116.51(14) . . ? C4 C3 C2 104.71(13) . . ? C7 C3 C2 115.15(14) . . ? C4 C3 H3 107.2(11) . . ? C7 C3 H3 106.0(10) . . ? C2 C3 H3 106.6(10) . . ? C5 C4 C3 124.00(16) . . ? C5 C4 Fe1 68.44(9) . . ? C3 C4 Fe1 92.02(10) . . ? C5 C4 H4 116.5(12) . . ? C3 C4 H4 118.0(12) . . ? Fe1 C4 H4 122.9(12) . . ? C4 C5 C6 123.20(16) . . ? C4 C5 Fe1 73.54(10) . . ? C6 C5 Fe1 74.05(9) . . ? C4 C5 H5 116.2(12) . . ? C6 C5 H5 120.0(12) . . ? Fe1 C5 H5 117.9(11) . . ? C5 C6 C11 123.39(15) . . ? C5 C6 Fe1 67.66(9) . . ? C11 C6 Fe1 121.57(11) . . ? C5 C6 H6 118.6(10) . . ? C11 C6 H6 113.5(10) . . ? Fe1 C6 H6 101.5(10) . . ? C8 C7 C9 123.31(18) . . ? C8 C7 C3 123.61(17) . . ? C9 C7 C3 113.07(16) . . ? C7 C8 H8A 119.8(14) . . ? C7 C8 H8B 122.8(12) . . ? H8A C8 H8B 117.2(18) . . ? C7 C9 H9A 111.9(13) . . ? C7 C9 H9B 111.9(14) . . ? H9A C9 H9B 108.3(19) . . ? C7 C9 H9C 110.0(14) . . ? H9A C9 H9C 107.1(19) . . ? H9B C9 H9C 107(2) . . ? O2 C10 H10A 104.8(13) . . ? O2 C10 H10B 108.9(14) . . ? H10A C10 H10B 109(2) . . ? O2 C10 H10C 113.9(13) . . ? H10A C10 H10C 109.7(19) . . ? H10B C10 H10C 110.3(19) . . ? C16 C11 C12 117.97(15) . . ? C16 C11 C6 123.26(15) . . ? C12 C11 C6 118.77(14) . . ? O3 C12 C13 123.93(16) . . ? O3 C12 C11 115.25(14) . . ? C13 C12 C11 120.81(15) . . ? C14 C13 C12 119.86(16) . . ? C14 C13 H13 120.7(12) . . ? C12 C13 H13 119.4(12) . . ? C15 C14 C13 119.85(15) . . ? C15 C14 H14 119.9(11) . . ? C13 C14 H14 120.3(11) . . ? C14 C15 C16 120.48(15) . . ? C14 C15 O4 119.67(15) . . ? C16 C15 O4 119.81(15) . . ? C15 C16 C11 120.97(16) . . ? C15 C16 H16 120.1(10) . . ? C11 C16 H16 118.9(10) . . ? O4 C18 H18A 105.6(11) . . ? O4 C18 H18B 109.6(12) . . ? H18A C18 H18B 112.3(16) . . ? O4 C18 H18C 110.6(11) . . ? H18A C18 H18C 110.2(16) . . ? H18B C18 H18C 108.5(16) . . ? O3 C19 H19A 112.3(13) . . ? O3 C19 H19B 105.4(12) . . ? H19A C19 H19B 108.8(16) . . ? O3 C19 H19C 110.7(12) . . ? H19A C19 H19C 107.5(16) . . ? H19B C19 H19C 112.3(17) . . ? O5 C20 Fe1 178.20(15) . . ? O6 C21 Fe1 178.49(15) . . ? O7 C22 Fe1 179.33(16) . . ? 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 C10 O2 C1 O1 5.6(2) . . . . ? C10 O2 C1 C2 -172.61(14) . . . . ? O1 C1 C2 C3 12.0(2) . . . . ? O2 C1 C2 C3 -169.91(13) . . . . ? O1 C1 C2 Fe1 -94.11(18) . . . . ? O2 C1 C2 Fe1 83.99(15) . . . . ? C21 Fe1 C2 C1 29.07(13) . . . . ? C22 Fe1 C2 C1 -72.90(13) . . . . ? C20 Fe1 C2 C1 133.5(8) . . . . ? C5 Fe1 C2 C1 157.15(13) . . . . ? C4 Fe1 C2 C1 125.06(14) . . . . ? C6 Fe1 C2 C1 -165.05(13) . . . . ? C21 Fe1 C2 C3 -90.39(11) . . . . ? C22 Fe1 C2 C3 167.64(11) . . . . ? C20 Fe1 C2 C3 14.0(9) . . . . ? C5 Fe1 C2 C3 37.69(10) . . . . ? C4 Fe1 C2 C3 5.60(9) . . . . ? C6 Fe1 C2 C3 75.49(10) . . . . ? C1 C2 C3 C4 -124.64(15) . . . . ? Fe1 C2 C3 C4 -7.70(13) . . . . ? C1 C2 C3 C7 106.07(17) . . . . ? Fe1 C2 C3 C7 -136.99(13) . . . . ? C7 C3 C4 C5 70.8(2) . . . . ? C2 C3 C4 C5 -57.7(2) . . . . ? C7 C3 C4 Fe1 135.95(13) . . . . ? C2 C3 C4 Fe1 7.49(12) . . . . ? C21 Fe1 C4 C5 -152.65(11) . . . . ? C22 Fe1 C4 C5 80.47(17) . . . . ? C20 Fe1 C4 C5 -58.93(12) . . . . ? C2 Fe1 C4 C5 120.38(12) . . . . ? C6 Fe1 C4 C5 29.21(10) . . . . ? C21 Fe1 C4 C3 81.36(11) . . . . ? C22 Fe1 C4 C3 -45.52(18) . . . . ? C20 Fe1 C4 C3 175.08(10) . . . . ? C5 Fe1 C4 C3 -125.99(15) . . . . ? C2 Fe1 C4 C3 -5.61(9) . . . . ? C6 Fe1 C4 C3 -96.78(11) . . . . ? C3 C4 C5 C6 19.6(3) . . . . ? Fe1 C4 C5 C6 -57.61(14) . . . . ? C3 C4 C5 Fe1 77.25(15) . . . . ? C21 Fe1 C5 C4 35.54(14) . . . . ? C22 Fe1 C5 C4 -141.83(11) . . . . ? C20 Fe1 C5 C4 124.79(11) . . . . ? C2 Fe1 C5 C4 -53.38(11) . . . . ? C6 Fe1 C5 C4 -132.70(15) . . . . ? C21 Fe1 C5 C6 168.24(10) . . . . ? C22 Fe1 C5 C6 -9.13(14) . . . . ? C20 Fe1 C5 C6 -102.51(11) . . . . ? C2 Fe1 C5 C6 79.32(10) . . . . ? C4 Fe1 C5 C6 132.70(15) . . . . ? C4 C5 C6 C11 171.40(15) . . . . ? Fe1 C5 C6 C11 114.02(15) . . . . ? C4 C5 C6 Fe1 57.38(15) . . . . ? C21 Fe1 C6 C5 -35.8(3) . . . . ? C22 Fe1 C6 C5 173.01(11) . . . . ? C20 Fe1 C6 C5 77.55(11) . . . . ? C2 Fe1 C6 C5 -98.45(11) . . . . ? C4 Fe1 C6 C5 -29.02(10) . . . . ? C21 Fe1 C6 C11 -152.2(2) . . . . ? C22 Fe1 C6 C11 56.53(14) . . . . ? C20 Fe1 C6 C11 -38.93(14) . . . . ? C5 Fe1 C6 C11 -116.47(18) . . . . ? C2 Fe1 C6 C11 145.07(14) . . . . ? C4 Fe1 C6 C11 -145.49(15) . . . . ? C4 C3 C7 C8 -9.7(3) . . . . ? C2 C3 C7 C8 113.5(2) . . . . ? C4 C3 C7 C9 170.32(16) . . . . ? C2 C3 C7 C9 -66.5(2) . . . . ? C5 C6 C11 C16 -4.8(2) . . . . ? Fe1 C6 C11 C16 77.74(19) . . . . ? C5 C6 C11 C12 174.26(15) . . . . ? Fe1 C6 C11 C12 -103.18(16) . . . . ? C19 O3 C12 C13 1.5(2) . . . . ? C19 O3 C12 C11 -179.02(14) . . . . ? C16 C11 C12 O3 -177.38(13) . . . . ? C6 C11 C12 O3 3.5(2) . . . . ? C16 C11 C12 C13 2.1(2) . . . . ? C6 C11 C12 C13 -177.00(15) . . . . ? O3 C12 C13 C14 177.50(15) . . . . ? C11 C12 C13 C14 -2.0(2) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 2.0(2) . . . . ? C13 C14 C15 O4 179.83(14) . . . . ? C18 O4 C15 C14 105.52(17) . . . . ? C18 O4 C15 C16 -76.67(19) . . . . ? C14 C15 C16 C11 -1.9(2) . . . . ? O4 C15 C16 C11 -179.64(14) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? C6 C11 C16 C15 178.85(15) . . . . ? C21 Fe1 C20 O5 -36(5) . . . . ? C22 Fe1 C20 O5 66(5) . . . . ? C5 Fe1 C20 O5 -164(5) . . . . ? C2 Fe1 C20 O5 -140(5) . . . . ? C4 Fe1 C20 O5 -132(5) . . . . ? C6 Fe1 C20 O5 159(5) . . . . ? C22 Fe1 C21 O6 -64(6) . . . . ? C20 Fe1 C21 O6 32(6) . . . . ? C5 Fe1 C21 O6 118(6) . . . . ? C2 Fe1 C21 O6 -153(6) . . . . ? C4 Fe1 C21 O6 139(6) . . . . ? C6 Fe1 C21 O6 145(6) . . . . ? C21 Fe1 C22 O7 -105(15) . . . . ? C20 Fe1 C22 O7 162(15) . . . . ? C5 Fe1 C22 O7 73(15) . . . . ? C2 Fe1 C22 O7 -16(15) . . . . ? C4 Fe1 C22 O7 21(15) . . . . ? C6 Fe1 C22 O7 67(15) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.281 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.043 # Attachment 'compound-16b.cif' data_don1n _database_code_depnum_ccdc_archive 'CCDC 823814' #TrackingRef 'compound-16b.cif' _audit_creation_date 2010-11-10 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.10.26 svn.r1482, GUI svn.r3310) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H30 Fe O7' _chemical_formula_sum 'C26 H30 Fe O7' _chemical_formula_weight 510.35 _chemical_melting_point ? _chemical_oxdiff_formula 'C26 H30 O7 Fe' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.2155(4) _cell_length_b 10.6315(4) _cell_length_c 13.0110(5) _cell_angle_alpha 102.007(3) _cell_angle_beta 106.062(3) _cell_angle_gamma 110.218(3) _cell_volume 1199.83(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8656 _cell_measurement_temperature 100.1 _cell_measurement_theta_max 29.4202 _cell_measurement_theta_min 3.3424 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0427 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 18938 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.49 _diffrn_reflns_theta_min 3.35 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.896 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -21.00 88.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - 11.6697 77.0000 120.0000 109 #__ type_ start__ end____ width___ exp.time_ 2 omega -1.00 90.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - 11.6697 77.0000 -30.0000 91 #__ type_ start__ end____ width___ exp.time_ 3 omega -42.00 63.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - -11.8259 77.0000 -150.0000 105 #__ type_ start__ end____ width___ exp.time_ 4 omega -32.00 50.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - 11.6697 -90.0000 27.0000 82 #__ type_ start__ end____ width___ exp.time_ 5 omega -15.00 88.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - 11.6697 37.0000 -120.0000 103 #__ type_ start__ end____ width___ exp.time_ 6 omega -28.00 64.00 1.0000 16.0700 omega____ theta____ kappa____ phi______ frames - -11.8259 37.0000 120.0000 92 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0041693000 _diffrn_orient_matrix_UB_12 0.0692293000 _diffrn_orient_matrix_UB_13 0.0056153000 _diffrn_orient_matrix_UB_21 0.0023905000 _diffrn_orient_matrix_UB_22 -0.0079770000 _diffrn_orient_matrix_UB_23 -0.0548568000 _diffrn_orient_matrix_UB_31 -0.0798408000 _diffrn_orient_matrix_UB_32 -0.0290680000 _diffrn_orient_matrix_UB_33 -0.0242712000 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _reflns_number_gt 4998 _reflns_number_total 5984 _reflns_odcompleteness_completeness 96.14 _reflns_odcompleteness_iscentric 0 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.849 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.075 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 5984 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0450 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+1.1905P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1155 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.25740(3) 0.18289(3) 0.36302(3) 0.01608(10) Uani 1 1 d . . . O1 O 0.49234(19) 0.40122(18) 0.57850(14) 0.0295(4) Uani 1 1 d . . . O2 O 0.37187(19) 0.33076(18) 0.21713(14) 0.0283(4) Uani 1 1 d . . . O3 O 0.41298(19) -0.00040(19) 0.39304(15) 0.0298(4) Uani 1 1 d . . . O4 O 0.16567(19) -0.16131(17) 0.16037(14) 0.0240(3) Uani 1 1 d . . . O5 O 0.17247(17) -0.00339(16) 0.06846(13) 0.0209(3) Uani 1 1 d . . . O6 O 0.07630(19) 0.40551(16) 0.20713(13) 0.0240(3) Uani 1 1 d . . . O7 O 0.2788(2) 0.74237(18) 0.65395(15) 0.0341(4) Uani 1 1 d . . . C1 C 0.4003(3) 0.3180(2) 0.49546(19) 0.0209(4) Uani 1 1 d . . . C2 C 0.3287(2) 0.2744(2) 0.27423(18) 0.0200(4) Uani 1 1 d . . . C3 C 0.3527(2) 0.0696(2) 0.37803(19) 0.0215(4) Uani 1 1 d . . . C4 C 0.1417(2) -0.0597(2) 0.14794(18) 0.0183(4) Uani 1 1 d . . . C5 C 0.0822(2) 0.0199(2) 0.21456(18) 0.0170(4) Uani 1 1 d . . . C6 C -0.0013(2) -0.0562(2) 0.28138(19) 0.0190(4) Uani 1 1 d . . . H6 H 0.0224 -0.1398 0.2824 0.023 Uiso 1 1 calc R . . C7 C 0.0798(2) 0.0487(2) 0.40157(19) 0.0194(4) Uani 1 1 d . . . C8 C 0.1007(2) 0.1911(2) 0.43539(19) 0.0196(4) Uani 1 1 d . . . C9 C 0.0926(2) 0.2701(2) 0.36088(19) 0.0179(4) Uani 1 1 d . . . C10 C 0.2380(3) -0.0691(3) 0.0024(2) 0.0276(5) Uani 1 1 d . . . H10B H 0.2593 -0.0191 -0.0505 0.041 Uiso 1 1 calc R . . H10A H 0.1673 -0.1690 -0.0404 0.041 Uiso 1 1 calc R . . H10C H 0.3320 -0.0641 0.0532 0.041 Uiso 1 1 calc R . . C11 C 0.1372(2) 0.4248(2) 0.39961(19) 0.0183(4) Uani 1 1 d . . . C12 C 0.1279(2) 0.4925(2) 0.31758(19) 0.0195(4) Uani 1 1 d . . . C13 C 0.1710(3) 0.6385(2) 0.3495(2) 0.0225(5) Uani 1 1 d . . . H13 H 0.1662 0.6836 0.2936 0.027 Uiso 1 1 calc R . . C14 C 0.2208(3) 0.7177(2) 0.4625(2) 0.0256(5) Uani 1 1 d . . . H14 H 0.2498 0.8174 0.4841 0.031 Uiso 1 1 calc R . . C15 C 0.2289(3) 0.6529(2) 0.5448(2) 0.0240(5) Uani 1 1 d . . . C16 C 0.1879(3) 0.5075(2) 0.51355(19) 0.0211(4) Uani 1 1 d . . . H16 H 0.1944 0.4637 0.5702 0.025 Uiso 1 1 calc R . . C17 C 0.0587(3) 0.4702(3) 0.1218(2) 0.0345(6) Uani 1 1 d . . . H17A H 0.0136 0.3971 0.0466 0.052 Uiso 1 1 calc R . . H17B H 0.1575 0.5405 0.1318 0.052 Uiso 1 1 calc R . . H17C H -0.0072 0.5175 0.1282 0.052 Uiso 1 1 calc R . . C18 C 0.2801(3) 0.6811(3) 0.7404(2) 0.0292(5) Uani 1 1 d . . . H18B H 0.1779 0.6108 0.7233 0.044 Uiso 1 1 calc R . . H18C H 0.3152 0.7557 0.8134 0.044 Uiso 1 1 calc R . . H18A H 0.3479 0.6343 0.7447 0.044 Uiso 1 1 calc R . . C19 C -0.1730(3) -0.1140(2) 0.2364(2) 0.0243(5) Uani 1 1 d . . . C20 C -0.2412(3) -0.0385(3) 0.2760(2) 0.0349(6) Uani 1 1 d . . . H20 H -0.1780 0.0521 0.3330 0.042 Uiso 1 1 calc R . . C21 C -0.4072(3) -0.0844(3) 0.2385(4) 0.0613(11) Uani 1 1 d . . . H21A H -0.4363 -0.0298 0.1907 0.074 Uiso 1 1 calc R . . H21B H -0.4323 -0.0614 0.3062 0.074 Uiso 1 1 calc R . . C22 C -0.4974(3) -0.2405(3) 0.1726(3) 0.0459(8) Uani 1 1 d . . . H22A H -0.6034 -0.2603 0.1311 0.055 Uiso 1 1 calc R . . H22B H -0.4962 -0.2956 0.2253 0.055 Uiso 1 1 calc R . . C23 C -0.4305(3) -0.2848(3) 0.0896(3) 0.0429(7) Uani 1 1 d . . . H23A H -0.4326 -0.2292 0.0373 0.052 Uiso 1 1 calc R . . H23B H -0.4934 -0.3866 0.0436 0.052 Uiso 1 1 calc R . . C24 C -0.2652(3) -0.2620(3) 0.1493(2) 0.0313(6) Uani 1 1 d . . . C25 C -0.2631(3) -0.3725(3) 0.2069(3) 0.0413(7) Uani 1 1 d . . . H25B H -0.3197 -0.4681 0.1497 0.062 Uiso 1 1 calc R . . H25C H -0.3096 -0.3642 0.2630 0.062 Uiso 1 1 calc R . . H25A H -0.1586 -0.3565 0.2450 0.062 Uiso 1 1 calc R . . C26 C -0.2035(3) -0.2861(3) 0.0551(2) 0.0378(6) Uani 1 1 d . . . H26A H -0.1901 -0.2080 0.0242 0.057 Uiso 1 1 calc R . . H26C H -0.2749 -0.3765 -0.0057 0.057 Uiso 1 1 calc R . . H26B H -0.1062 -0.2893 0.0868 0.057 Uiso 1 1 calc R . . H5 H 0.031(2) 0.062(2) 0.1688(19) 0.010(5) Uiso 1 1 d . . . H9 H 0.025(3) 0.222(3) 0.288(2) 0.021(6) Uiso 1 1 d . . . H8 H 0.146(3) 0.239(3) 0.516(2) 0.022(6) Uiso 1 1 d . . . H7 H 0.104(3) 0.013(3) 0.460(2) 0.020(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01703(16) 0.01455(15) 0.01837(16) 0.00627(12) 0.00769(12) 0.00748(12) O1 0.0285(9) 0.0251(9) 0.0243(9) 0.0027(7) 0.0040(7) 0.0076(7) O2 0.0289(9) 0.0261(9) 0.0270(9) 0.0108(7) 0.0137(7) 0.0052(7) O3 0.0313(9) 0.0325(9) 0.0313(9) 0.0119(8) 0.0087(8) 0.0217(8) O4 0.0313(9) 0.0204(8) 0.0285(9) 0.0099(7) 0.0144(7) 0.0170(7) O5 0.0250(8) 0.0205(8) 0.0220(8) 0.0077(6) 0.0129(6) 0.0117(6) O6 0.0319(9) 0.0190(8) 0.0215(8) 0.0078(6) 0.0095(7) 0.0111(7) O7 0.0538(12) 0.0205(8) 0.0253(9) 0.0030(7) 0.0140(8) 0.0163(8) C1 0.0234(11) 0.0210(11) 0.0246(11) 0.0110(9) 0.0128(9) 0.0119(9) C2 0.0166(10) 0.0175(10) 0.0216(11) 0.0027(8) 0.0054(9) 0.0059(8) C3 0.0205(10) 0.0220(11) 0.0204(11) 0.0062(9) 0.0065(9) 0.0089(9) C4 0.0161(10) 0.0168(10) 0.0188(10) 0.0034(8) 0.0051(8) 0.0061(8) C5 0.0160(9) 0.0138(9) 0.0211(10) 0.0061(8) 0.0071(8) 0.0060(8) C6 0.0202(10) 0.0144(9) 0.0281(11) 0.0086(8) 0.0131(9) 0.0098(8) C7 0.0213(10) 0.0186(10) 0.0254(11) 0.0109(9) 0.0138(9) 0.0103(9) C8 0.0215(10) 0.0182(10) 0.0226(11) 0.0073(9) 0.0130(9) 0.0085(9) C9 0.0180(10) 0.0150(10) 0.0225(11) 0.0050(8) 0.0097(9) 0.0083(8) C10 0.0318(12) 0.0309(13) 0.0258(12) 0.0072(10) 0.0173(10) 0.0162(11) C11 0.0172(10) 0.0151(9) 0.0257(11) 0.0073(8) 0.0098(9) 0.0086(8) C12 0.0195(10) 0.0187(10) 0.0223(11) 0.0069(8) 0.0081(9) 0.0105(8) C13 0.0239(11) 0.0193(11) 0.0282(12) 0.0113(9) 0.0105(9) 0.0112(9) C14 0.0283(12) 0.0150(10) 0.0329(13) 0.0070(9) 0.0110(10) 0.0097(9) C15 0.0262(11) 0.0185(11) 0.0264(12) 0.0045(9) 0.0102(10) 0.0101(9) C16 0.0259(11) 0.0181(10) 0.0236(11) 0.0085(9) 0.0107(9) 0.0124(9) C17 0.0529(17) 0.0275(13) 0.0255(13) 0.0133(10) 0.0149(12) 0.0172(12) C18 0.0310(13) 0.0296(13) 0.0251(12) 0.0050(10) 0.0106(10) 0.0133(11) C19 0.0218(11) 0.0160(10) 0.0361(13) 0.0090(9) 0.0135(10) 0.0071(9) C20 0.0249(12) 0.0294(13) 0.0457(16) 0.0015(11) 0.0164(12) 0.0105(11) C21 0.0240(14) 0.0358(16) 0.104(3) -0.0073(18) 0.0250(17) 0.0079(12) C22 0.0218(13) 0.0336(15) 0.075(2) 0.0114(15) 0.0160(14) 0.0093(11) C23 0.0323(14) 0.0305(14) 0.0550(19) 0.0083(13) 0.0077(13) 0.0118(12) C24 0.0246(12) 0.0199(11) 0.0416(15) 0.0048(10) 0.0085(11) 0.0073(10) C25 0.0439(16) 0.0265(13) 0.0448(17) 0.0122(12) 0.0102(13) 0.0106(12) C26 0.0399(15) 0.0271(13) 0.0343(14) 0.0038(11) 0.0083(12) 0.0095(12) _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 1.815(2) . ? Fe1 C2 1.804(2) . ? Fe1 C3 1.800(2) . ? Fe1 C5 2.119(2) . ? Fe1 C7 2.142(2) . ? Fe1 C8 2.086(2) . ? Fe1 C9 2.181(2) . ? O1 C1 1.140(3) . ? O2 C2 1.136(3) . ? O3 C3 1.133(3) . ? O4 C4 1.219(3) . ? O5 C4 1.354(3) . ? O5 C10 1.437(3) . ? O6 C12 1.374(3) . ? O6 C17 1.426(3) . ? O7 C15 1.372(3) . ? O7 C18 1.412(3) . ? C4 C5 1.476(3) . ? C5 C6 1.537(3) . ? C5 H5 0.96(2) . ? C6 H6 1.0000 . ? C6 C7 1.515(3) . ? C6 C19 1.528(3) . ? C7 C8 1.406(3) . ? C7 H7 0.93(3) . ? C8 C9 1.413(3) . ? C8 H8 0.95(3) . ? C9 C11 1.475(3) . ? C9 H9 0.91(3) . ? C10 H10B 0.9800 . ? C10 H10A 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.406(3) . ? C11 C16 1.399(3) . ? C12 C13 1.391(3) . ? C13 H13 0.9500 . ? C13 C14 1.380(3) . ? C14 H14 0.9500 . ? C14 C15 1.387(3) . ? C15 C16 1.388(3) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 H18A 0.9800 . ? C19 C20 1.344(3) . ? C19 C24 1.514(3) . ? C20 H20 0.9500 . ? C20 C21 1.491(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.501(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.508(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.558(4) . ? C24 C25 1.522(4) . ? C24 C26 1.541(4) . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25 H25A 0.9800 . ? C26 H26A 0.9800 . ? C26 H26C 0.9800 . ? C26 H26B 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 Fe1 C5 H5 109.0(14) . . ? Fe1 C7 H7 119.0(15) . . ? Fe1 C8 H8 113.2(15) . . ? Fe1 C9 H9 100.9(16) . . ? O1 C1 Fe1 178.3(2) . . ? O2 C2 Fe1 179.1(2) . . ? O3 C3 Fe1 176.5(2) . . ? O4 C4 O5 121.65(19) . . ? O4 C4 C5 127.1(2) . . ? O5 C4 C5 111.18(18) . . ? O5 C10 H10B 109.5 . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10C 109.5 . . ? O6 C12 C11 115.61(18) . . ? O6 C12 C13 123.7(2) . . ? O6 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? O6 C17 H17C 109.5 . . ? O7 C15 C14 115.2(2) . . ? O7 C15 C16 125.0(2) . . ? O7 C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? O7 C18 H18A 109.5 . . ? C1 Fe1 C5 176.26(9) . . ? C1 Fe1 C7 107.82(9) . . ? C1 Fe1 C8 86.50(9) . . ? C1 Fe1 C9 94.57(9) . . ? C2 Fe1 C1 94.66(10) . . ? C2 Fe1 C5 88.93(9) . . ? C2 Fe1 C7 153.02(9) . . ? C2 Fe1 C8 132.09(9) . . ? C2 Fe1 C9 93.82(9) . . ? C3 Fe1 C1 90.31(10) . . ? C3 Fe1 C2 103.73(10) . . ? C3 Fe1 C5 89.86(9) . . ? C3 Fe1 C7 91.16(9) . . ? C3 Fe1 C8 124.17(9) . . ? C3 Fe1 C9 161.35(9) . . ? C4 O5 C10 115.59(17) . . ? C4 C5 Fe1 111.32(14) . . ? C4 C5 C6 116.44(17) . . ? C4 C5 H5 109.4(14) . . ? C5 Fe1 C7 68.44(8) . . ? C5 Fe1 C9 84.12(8) . . ? C5 C6 H6 106.5 . . ? C6 C5 Fe1 93.54(13) . . ? C6 C5 H5 116.0(13) . . ? C6 C7 Fe1 93.27(13) . . ? C6 C7 H7 117.7(16) . . ? C7 Fe1 C9 70.21(8) . . ? C7 C6 C5 103.45(17) . . ? C7 C6 H6 106.5 . . ? C7 C6 C19 114.85(18) . . ? C7 C8 Fe1 72.74(12) . . ? C7 C8 C9 123.8(2) . . ? C7 C8 H8 114.7(15) . . ? C8 Fe1 C5 90.31(8) . . ? C8 Fe1 C7 38.82(8) . . ? C8 Fe1 C9 38.58(8) . . ? C8 C7 Fe1 68.44(12) . . ? C8 C7 C6 125.9(2) . . ? C8 C7 H7 115.5(16) . . ? C8 C9 Fe1 67.08(12) . . ? C8 C9 C11 123.4(2) . . ? C8 C9 H9 116.9(16) . . ? C9 C8 Fe1 74.34(12) . . ? C9 C8 H8 119.8(15) . . ? H10B C10 H10A 109.5 . . ? H10B C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? C11 C9 Fe1 122.02(15) . . ? C11 C9 H9 115.2(16) . . ? C11 C16 H16 119.6 . . ? C12 O6 C17 116.73(18) . . ? C12 C11 C9 118.21(19) . . ? C12 C13 H13 120.1 . . ? C13 C12 C11 120.7(2) . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.5(2) . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C14 C15 C16 119.9(2) . . ? C15 O7 C18 117.75(18) . . ? C15 C14 H14 119.7 . . ? C15 C16 C11 120.8(2) . . ? C15 C16 H16 119.6 . . ? C16 C11 C9 123.50(19) . . ? C16 C11 C12 118.29(19) . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H18B C18 H18C 109.5 . . ? H18B C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? C19 C6 C5 118.18(19) . . ? C19 C6 H6 106.5 . . ? C19 C20 H20 117.1 . . ? C19 C20 C21 125.8(3) . . ? C19 C24 C23 110.1(2) . . ? C19 C24 C25 109.8(2) . . ? C19 C24 C26 112.0(2) . . ? C20 C19 C6 121.3(2) . . ? C20 C19 C24 120.6(2) . . ? C20 C21 H21A 108.9 . . ? C20 C21 H21B 108.9 . . ? C20 C21 C22 113.2(2) . . ? C21 C20 H20 117.1 . . ? C21 C22 H22A 109.8 . . ? C21 C22 H22B 109.8 . . ? C21 C22 C23 109.3(3) . . ? H21A C21 H21B 107.8 . . ? C22 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C22 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C22 C23 C24 112.7(3) . . ? H22A C22 H22B 108.3 . . ? C23 C22 H22A 109.8 . . ? C23 C22 H22B 109.8 . . ? H23A C23 H23B 107.8 . . ? C24 C19 C6 118.09(19) . . ? C24 C23 H23A 109.1 . . ? C24 C23 H23B 109.1 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26C 109.5 . . ? C24 C26 H26B 109.5 . . ? C25 C24 C23 110.1(2) . . ? C25 C24 C26 108.1(2) . . ? H25B C25 H25C 109.5 . . ? H25B C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? C26 C24 C23 106.7(2) . . ? H26A C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26C C26 H26B 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 Fe1 C5 C6 C7 10.04(16) . . . . ? Fe1 C5 C6 C19 138.23(17) . . . . ? Fe1 C7 C8 C9 56.8(2) . . . . ? Fe1 C8 C9 C11 -114.3(2) . . . . ? Fe1 C9 C11 C12 96.3(2) . . . . ? Fe1 C9 C11 C16 -83.8(2) . . . . ? O4 C4 C5 Fe1 86.0(2) . . . . ? O4 C4 C5 C6 -19.5(3) . . . . ? O5 C4 C5 Fe1 -92.35(18) . . . . ? O5 C4 C5 C6 162.10(17) . . . . ? O6 C12 C13 C14 179.7(2) . . . . ? O7 C15 C16 C11 179.5(2) . . . . ? C1 Fe1 C2 O2 -170(100) . . . . ? C1 Fe1 C3 O3 49(3) . . . . ? C1 Fe1 C5 C4 -128.9(13) . . . . ? C1 Fe1 C5 C6 -8.7(14) . . . . ? C1 Fe1 C7 C6 -172.58(13) . . . . ? C1 Fe1 C7 C8 59.88(15) . . . . ? C1 Fe1 C8 C7 -124.41(15) . . . . ? C1 Fe1 C8 C9 101.81(14) . . . . ? C1 Fe1 C9 C8 -78.55(14) . . . . ? C1 Fe1 C9 C11 37.60(19) . . . . ? C2 Fe1 C1 O1 -89(7) . . . . ? C2 Fe1 C3 O3 143(3) . . . . ? C2 Fe1 C5 C4 67.43(16) . . . . ? C2 Fe1 C5 C6 -172.37(13) . . . . ? C2 Fe1 C7 C6 42.4(3) . . . . ? C2 Fe1 C7 C8 -85.2(2) . . . . ? C2 Fe1 C8 C7 142.47(14) . . . . ? C2 Fe1 C8 C9 8.69(19) . . . . ? C2 Fe1 C9 C8 -173.55(14) . . . . ? C2 Fe1 C9 C11 -57.39(19) . . . . ? C3 Fe1 C1 O1 15(7) . . . . ? C3 Fe1 C2 O2 98(13) . . . . ? C3 Fe1 C5 C4 -36.30(16) . . . . ? C3 Fe1 C5 C6 83.90(13) . . . . ? C3 Fe1 C7 C6 -81.88(14) . . . . ? C3 Fe1 C7 C8 150.58(15) . . . . ? C3 Fe1 C8 C7 -36.41(18) . . . . ? C3 Fe1 C8 C9 -170.19(13) . . . . ? C3 Fe1 C9 C8 26.2(3) . . . . ? C3 Fe1 C9 C11 142.3(3) . . . . ? C4 C5 C6 C7 125.98(19) . . . . ? C4 C5 C6 C19 -105.8(2) . . . . ? C5 Fe1 C1 O1 108(7) . . . . ? C5 Fe1 C2 O2 9(13) . . . . ? C5 Fe1 C3 O3 -128(3) . . . . ? C5 Fe1 C7 C6 7.51(12) . . . . ? C5 Fe1 C7 C8 -120.03(15) . . . . ? C5 Fe1 C8 C7 53.63(14) . . . . ? C5 Fe1 C8 C9 -80.15(13) . . . . ? C5 Fe1 C9 C8 97.93(14) . . . . ? C5 Fe1 C9 C11 -145.92(18) . . . . ? C5 C6 C7 Fe1 -9.92(15) . . . . ? C5 C6 C7 C8 55.7(3) . . . . ? C5 C6 C19 C20 -95.8(3) . . . . ? C5 C6 C19 C24 86.8(3) . . . . ? C6 C7 C8 Fe1 -77.8(2) . . . . ? C6 C7 C8 C9 -21.1(3) . . . . ? C6 C19 C20 C21 -179.9(3) . . . . ? C6 C19 C24 C23 -164.0(2) . . . . ? C6 C19 C24 C25 74.6(3) . . . . ? C6 C19 C24 C26 -45.5(3) . . . . ? C7 Fe1 C1 O1 106(7) . . . . ? C7 Fe1 C2 O2 -24(14) . . . . ? C7 Fe1 C3 O3 -59(3) . . . . ? C7 Fe1 C5 C4 -127.60(17) . . . . ? C7 Fe1 C5 C6 -7.40(12) . . . . ? C7 Fe1 C8 C9 -133.8(2) . . . . ? C7 Fe1 C9 C8 28.76(13) . . . . ? C7 Fe1 C9 C11 144.9(2) . . . . ? C7 C6 C19 C20 26.8(3) . . . . ? C7 C6 C19 C24 -150.6(2) . . . . ? C7 C8 C9 Fe1 -56.06(19) . . . . ? C7 C8 C9 C11 -170.3(2) . . . . ? C8 Fe1 C1 O1 139(7) . . . . ? C8 Fe1 C2 O2 -81(13) . . . . ? C8 Fe1 C3 O3 -37(3) . . . . ? C8 Fe1 C5 C4 -160.48(15) . . . . ? C8 Fe1 C5 C6 -40.28(13) . . . . ? C8 Fe1 C7 C6 127.5(2) . . . . ? C8 Fe1 C9 C11 116.2(2) . . . . ? C8 C9 C11 C12 178.4(2) . . . . ? C8 C9 C11 C16 -1.8(3) . . . . ? C9 Fe1 C1 O1 177(100) . . . . ? C9 Fe1 C2 O2 -75(13) . . . . ? C9 Fe1 C3 O3 -57(3) . . . . ? C9 Fe1 C5 C4 161.38(16) . . . . ? C9 Fe1 C5 C6 -78.42(12) . . . . ? C9 Fe1 C7 C6 98.95(14) . . . . ? C9 Fe1 C7 C8 -28.59(13) . . . . ? C9 Fe1 C8 C7 133.8(2) . . . . ? C9 C11 C12 O6 0.3(3) . . . . ? C9 C11 C12 C13 -178.8(2) . . . . ? C9 C11 C16 C15 179.7(2) . . . . ? C10 O5 C4 O4 -1.4(3) . . . . ? C10 O5 C4 C5 177.13(18) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 O7 -179.5(2) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? C14 C15 C16 C11 -0.5(3) . . . . ? C16 C11 C12 O6 -179.56(19) . . . . ? C16 C11 C12 C13 1.3(3) . . . . ? C17 O6 C12 C11 177.0(2) . . . . ? C17 O6 C12 C13 -3.9(3) . . . . ? C18 O7 C15 C14 176.0(2) . . . . ? C18 O7 C15 C16 -4.1(4) . . . . ? C19 C6 C7 Fe1 -140.15(16) . . . . ? C19 C6 C7 C8 -74.6(3) . . . . ? C19 C20 C21 C22 15.0(5) . . . . ? C20 C19 C24 C23 18.6(4) . . . . ? C20 C19 C24 C25 -102.8(3) . . . . ? C20 C19 C24 C26 137.2(3) . . . . ? C20 C21 C22 C23 -42.9(4) . . . . ? C21 C22 C23 C24 61.6(4) . . . . ? C22 C23 C24 C19 -48.4(3) . . . . ? C22 C23 C24 C25 72.7(3) . . . . ? C22 C23 C24 C26 -170.2(2) . . . . ? C24 C19 C20 C21 -2.6(5) . . . . ? # Attachment '4-(1-methylethenyl)-2-pentene-1,5-diyl)iron.cif' data_DON1H _database_code_depnum_ccdc_archive 'CCDC 823815' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C21 H22 Fe O7' _chemical_formula_sum 'C21 H22 Fe O7' _chemical_formula_weight 442.24 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 93.4868(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 6.94866(9) _cell_length_b 15.94213(19) _cell_length_c 36.7435(5) _cell_measurement_reflns_used 37708 _cell_measurement_temperature 100 _cell_measurement_theta_max 32.7622 _cell_measurement_theta_min 3.2811 _cell_volume 4062.78(9) _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.87741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_F_000 1840 _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_special_details ? _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.950 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -13.00 24.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 77.0000 60.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega -7.00 95.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 37.0000 -180.0000 102 #__ type_ start__ end____ width___ exp.time_ 3 omega -69.00 -35.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - -19.9198 118.0000 125.0000 34 #__ type_ start__ end____ width___ exp.time_ 4 omega -93.00 -19.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - -19.9198 -37.0000 -60.0000 74 #__ type_ start__ end____ width___ exp.time_ 5 omega -56.00 46.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 -150.0000 102 #__ type_ start__ end____ width___ exp.time_ 6 omega -56.00 46.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 30.0000 102 #__ type_ start__ end____ width___ exp.time_ 7 omega -14.00 98.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 77.0000 -90.0000 112 #__ type_ start__ end____ width___ exp.time_ 8 omega -56.00 -19.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - 19.7635 -37.0000 120.0000 37 #__ type_ start__ end____ width___ exp.time_ 9 omega -73.00 -18.00 1.0000 42.7300 omega____ theta____ kappa____ phi______ frames - -19.9198 118.0000 -54.0000 55 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1005813 _diffrn_orient_matrix_UB_12 0.0058535 _diffrn_orient_matrix_UB_13 -0.0012297 _diffrn_orient_matrix_UB_21 0.0114203 _diffrn_orient_matrix_UB_22 -0.043699 _diffrn_orient_matrix_UB_23 -0.0028 _diffrn_orient_matrix_UB_31 -0.0144888 _diffrn_orient_matrix_UB_32 0.0060484 _diffrn_orient_matrix_UB_33 -0.019094 _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_number 80589 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 32.84 _diffrn_reflns_theta_min 3.33 _reflns_number_gt 11759 _reflns_number_total 14384 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.490 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.064 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0364 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 575 _refine_ls_number_reflns 14384 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.141 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.0890 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+3.0055P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.50610(3) 0.118353(12) 0.138391(5) 0.01102(4) Uani 1 1 d . . . O1 O 0.36277(17) 0.21358(7) 0.22107(3) 0.0218(2) Uani 1 1 d . . . O2 O 0.16903(15) 0.10147(7) 0.22478(3) 0.0161(2) Uani 1 1 d . . . O3 O 0.21264(15) -0.10173(7) 0.10423(3) 0.0174(2) Uani 1 1 d . . . O4 O 0.81516(17) -0.06103(8) 0.01449(3) 0.0236(2) Uani 1 1 d . . . O5 O 0.70527(18) 0.15810(8) 0.07242(3) 0.0239(2) Uani 1 1 d . . . O6 O 0.48119(19) 0.30257(7) 0.14875(4) 0.0260(3) Uani 1 1 d . . . O7 O 0.11374(16) 0.08979(7) 0.10703(3) 0.0205(2) Uani 1 1 d . . . C1 C 0.3255(2) 0.14120(9) 0.21376(4) 0.0143(2) Uani 1 1 d . . . C2 C 0.4450(2) 0.08452(9) 0.19239(4) 0.0139(2) Uani 1 1 d . . . H2 H 0.407(3) 0.0266(12) 0.1932(5) 0.017 Uiso 1 1 d . . . C3 C 0.6414(2) 0.10809(9) 0.19030(4) 0.0136(2) Uani 1 1 d . . . H3 H 0.680(3) 0.1618(12) 0.2016(5) 0.016 Uiso 1 1 d . . . C4 C 0.7655(2) 0.06912(9) 0.16715(4) 0.0133(2) Uani 1 1 d . . . H4 H 0.886(3) 0.0947(12) 0.1656(5) 0.016 Uiso 1 1 d . . . C5 C 0.7343(2) -0.01769(8) 0.15064(4) 0.0121(2) Uani 1 1 d . . . H5 H 0.8305 -0.0241 0.1317 0.014 Uiso 1 1 calc R . . C6 C 0.53629(19) -0.01402(8) 0.13041(4) 0.0112(2) Uani 1 1 d . . . H6 H 0.441(3) -0.0380(12) 0.1446(5) 0.013 Uiso 1 1 d . . . C7 C 0.7712(2) -0.08898(9) 0.17767(4) 0.0149(3) Uani 1 1 d . . . C8 C 0.6534(2) -0.15398(10) 0.18010(4) 0.0218(3) Uani 1 1 d . . . H8B H 0.6872 -0.1989 0.1962 0.026 Uiso 1 1 calc R . . H8A H 0.5352 -0.1556 0.1657 0.026 Uiso 1 1 calc R . . C9 C 0.9595(3) -0.08388(11) 0.19995(5) 0.0284(4) Uani 1 1 d . . . H9A H 1.0662 -0.0841 0.1837 0.043 Uiso 1 1 calc R . . H9C H 0.9716 -0.1322 0.2164 0.043 Uiso 1 1 calc R . . H9B H 0.9635 -0.0320 0.2143 0.043 Uiso 1 1 calc R . . C10 C 0.0523(2) 0.15021(10) 0.24819(4) 0.0190(3) Uani 1 1 d . . . H10A H 0.0054 0.2006 0.2352 0.028 Uiso 1 1 calc R . . H10C H 0.1300 0.1666 0.2702 0.028 Uiso 1 1 calc R . . H10B H -0.0578 0.1165 0.2550 0.028 Uiso 1 1 calc R . . C11 C 0.5209(2) -0.04774(8) 0.09263(4) 0.0127(2) Uani 1 1 d . . . C12 C 0.3532(2) -0.09186(9) 0.07971(4) 0.0143(2) Uani 1 1 d . . . C13 C 0.3375(2) -0.12347(10) 0.04434(4) 0.0178(3) Uani 1 1 d . . . H13 H 0.2234 -0.1521 0.0359 0.021 Uiso 1 1 calc R . . C14 C 0.4875(2) -0.11360(10) 0.02110(4) 0.0191(3) Uani 1 1 d . . . H14 H 0.4753 -0.1348 -0.0031 0.023 Uiso 1 1 calc R . . C15 C 0.6543(2) -0.07263(10) 0.03365(4) 0.0169(3) Uani 1 1 d . . . C16 C 0.6680(2) -0.03974(9) 0.06887(4) 0.0149(3) Uani 1 1 d . . . H16 H 0.7823 -0.0108 0.0769 0.018 Uiso 1 1 calc R . . C17 C 0.0680(2) -0.16329(10) 0.09512(4) 0.0193(3) Uani 1 1 d . . . H17A H -0.0087 -0.1455 0.0732 0.029 Uiso 1 1 calc R . . H17C H -0.0161 -0.1694 0.1154 0.029 Uiso 1 1 calc R . . H17B H 0.1298 -0.2172 0.0905 0.029 Uiso 1 1 calc R . . C18 C 0.8072(3) -0.08969(12) -0.02224(4) 0.0263(3) Uani 1 1 d . . . H18A H 0.7000 -0.0622 -0.0361 0.040 Uiso 1 1 calc R . . H18B H 0.7878 -0.1506 -0.0227 0.040 Uiso 1 1 calc R . . H18C H 0.9285 -0.0760 -0.0332 0.040 Uiso 1 1 calc R . . C19 C 0.6291(2) 0.13976(9) 0.09783(4) 0.0159(3) Uani 1 1 d . . . C20 C 0.4896(2) 0.23107(9) 0.14634(4) 0.0161(3) Uani 1 1 d . . . C21 C 0.2653(2) 0.10276(9) 0.11908(4) 0.0144(2) Uani 1 1 d . . . Fe1A Fe 0.00715(3) 0.429499(13) 0.131851(5) 0.01251(5) Uani 1 1 d . . . O1A O -0.13551(17) 0.33516(7) 0.21491(3) 0.0209(2) Uani 1 1 d . . . O2A O -0.32728(16) 0.44786(7) 0.21887(3) 0.0170(2) Uani 1 1 d . . . O3A O -0.28423(16) 0.65377(7) 0.10042(3) 0.0195(2) Uani 1 1 d . . . O4A O 0.3135(8) 0.6210(4) 0.00911(13) 0.0257(9) Uani 0.499(5) 1 d P A 1 C18A C 0.3135(6) 0.6657(3) -0.02419(9) 0.0318(10) Uani 0.499(5) 1 d P A 1 H18D H 0.2104 0.6443 -0.0411 0.048 Uiso 0.499(5) 1 calc PR A 1 H18E H 0.4381 0.6583 -0.0349 0.048 Uiso 0.499(5) 1 calc PR A 1 H18F H 0.2919 0.7254 -0.0196 0.048 Uiso 0.499(5) 1 calc PR A 1 O4B O 0.2669(9) 0.6131(5) -0.00100(14) 0.0341(12) Uani 0.501(5) 1 d P A -2 C18B C 0.4036(6) 0.5465(3) 0.00315(10) 0.0337(10) Uani 0.501(5) 1 d P A -2 H18I H 0.4864 0.5555 0.0254 0.051 Uiso 0.501(5) 1 calc PR A -2 H18H H 0.4829 0.5452 -0.0180 0.051 Uiso 0.501(5) 1 calc PR A -2 H18G H 0.3354 0.4930 0.0050 0.051 Uiso 0.501(5) 1 calc PR A -2 O5A O 0.21610(19) 0.38712(9) 0.06732(3) 0.0303(3) Uani 1 1 d . . . O6A O -0.02524(19) 0.24657(8) 0.14388(4) 0.0289(3) Uani 1 1 d . . . O7A O -0.38175(17) 0.45815(8) 0.09870(3) 0.0254(2) Uani 1 1 d . . . C1A C -0.1724(2) 0.40776(9) 0.20759(4) 0.0150(3) Uani 1 1 d . . . C2A C -0.0536(2) 0.46412(9) 0.18592(4) 0.0147(2) Uani 1 1 d . . . H2A H -0.095(3) 0.5185(13) 0.1860(5) 0.018 Uiso 1 1 d . . . C3A C 0.1428(2) 0.44052(9) 0.18369(4) 0.0153(3) Uani 1 1 d . . . H3A H 0.181(3) 0.3889(12) 0.1960(5) 0.018 Uiso 1 1 d . . . C4A C 0.2662(2) 0.47920(9) 0.16032(4) 0.0151(3) Uani 1 1 d . . . H4A H 0.387(3) 0.4534(12) 0.1580(5) 0.018 Uiso 1 1 d . . . C5A C 0.2344(2) 0.56601(9) 0.14377(4) 0.0143(2) Uani 1 1 d . . . H5A H 0.3304 0.5726 0.1248 0.017 Uiso 1 1 calc R . . C6A C 0.0361(2) 0.56171(9) 0.12368(4) 0.0148(2) Uani 1 1 d . . . H6A H -0.062(3) 0.5849(12) 0.1379(5) 0.018 Uiso 1 1 d . . . C7A C 0.2709(2) 0.63696(9) 0.17089(4) 0.0163(3) Uani 1 1 d . . . C8A C 0.1508(3) 0.70116(10) 0.17389(4) 0.0222(3) Uani 1 1 d . . . H8AB H 0.1831 0.7454 0.1905 0.027 Uiso 1 1 calc R . . H8AA H 0.0326 0.7028 0.1595 0.027 Uiso 1 1 calc R . . C9A C 0.4596(3) 0.63196(11) 0.19323(5) 0.0295(4) Uani 1 1 d . . . H9AA H 0.4637 0.5801 0.2076 0.044 Uiso 1 1 calc R . . H9AC H 0.4716 0.6803 0.2097 0.044 Uiso 1 1 calc R . . H9AB H 0.5663 0.6323 0.1770 0.044 Uiso 1 1 calc R . . C10A C -0.4439(2) 0.39983(10) 0.24251(4) 0.0195(3) Uani 1 1 d . . . H10D H -0.4895 0.3487 0.2299 0.029 Uiso 1 1 calc R . . H10F H -0.5548 0.4335 0.2489 0.029 Uiso 1 1 calc R . . H10E H -0.3666 0.3846 0.2647 0.029 Uiso 1 1 calc R . . C11A C 0.0172(2) 0.59775(9) 0.08622(4) 0.0152(3) Uani 1 1 d . . . C12A C -0.1474(2) 0.64520(9) 0.07514(4) 0.0155(3) Uani 1 1 d . . . C13A C -0.1632(2) 0.68212(10) 0.04076(4) 0.0199(3) Uani 1 1 d . . . H13A H -0.2750 0.7138 0.0336 0.024 Uiso 1 1 calc R . . C14A C -0.0175(3) 0.67314(11) 0.01680(4) 0.0227(3) Uani 1 1 d . A . H14A H -0.0291 0.6989 -0.0065 0.027 Uiso 1 1 calc R . . C15A C 0.1448(3) 0.62640(11) 0.02715(5) 0.0256(3) Uani 1 1 d . . . C16A C 0.1604(2) 0.58898(11) 0.06143(4) 0.0221(3) Uani 1 1 d . A . H16A H 0.2717 0.5566 0.0682 0.026 Uiso 1 1 calc R . . C17A C -0.4293(2) 0.71598(10) 0.09286(5) 0.0207(3) Uani 1 1 d . . . H17D H -0.5106 0.6993 0.0713 0.031 Uiso 1 1 calc R . . H17F H -0.3678 0.7699 0.0882 0.031 Uiso 1 1 calc R . . H17E H -0.5089 0.7214 0.1138 0.031 Uiso 1 1 calc R . . C19A C 0.1346(2) 0.40694(10) 0.09196(4) 0.0191(3) Uani 1 1 d . . . C20A C -0.0134(2) 0.31624(9) 0.14069(4) 0.0182(3) Uani 1 1 d . . . C21A C -0.2315(2) 0.44507(9) 0.11151(4) 0.0169(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01091(9) 0.00980(8) 0.01223(8) 0.00073(6) -0.00030(6) -0.00001(7) O1 0.0230(6) 0.0155(5) 0.0274(6) -0.0068(4) 0.0064(4) -0.0042(4) O2 0.0167(5) 0.0151(5) 0.0169(5) -0.0018(4) 0.0030(4) -0.0018(4) O3 0.0147(5) 0.0178(5) 0.0197(5) -0.0039(4) 0.0021(4) -0.0054(4) O4 0.0232(6) 0.0349(7) 0.0131(5) -0.0011(4) 0.0052(4) -0.0004(5) O5 0.0266(6) 0.0247(6) 0.0209(5) 0.0062(4) 0.0060(4) -0.0013(5) O6 0.0303(7) 0.0124(5) 0.0352(6) 0.0003(4) 0.0021(5) 0.0033(5) O7 0.0149(5) 0.0248(6) 0.0217(5) -0.0045(4) -0.0007(4) 0.0012(4) C1 0.0152(6) 0.0149(6) 0.0126(6) -0.0010(5) 0.0000(5) -0.0004(5) C2 0.0180(7) 0.0117(6) 0.0119(5) -0.0011(4) 0.0000(5) -0.0006(5) C3 0.0158(6) 0.0117(6) 0.0128(6) 0.0000(4) -0.0034(5) 0.0001(5) C4 0.0124(6) 0.0113(6) 0.0158(6) 0.0011(5) -0.0028(5) -0.0008(5) C5 0.0130(6) 0.0107(5) 0.0124(5) 0.0000(4) -0.0005(4) 0.0001(5) C6 0.0121(6) 0.0085(5) 0.0131(5) -0.0002(4) 0.0004(4) -0.0002(4) C7 0.0191(7) 0.0123(6) 0.0130(6) -0.0012(5) -0.0013(5) 0.0028(5) C8 0.0258(8) 0.0151(7) 0.0243(7) 0.0046(5) -0.0003(6) -0.0007(6) C9 0.0335(9) 0.0174(7) 0.0321(9) 0.0029(6) -0.0175(7) 0.0009(7) C10 0.0165(7) 0.0217(7) 0.0190(7) -0.0026(5) 0.0032(5) 0.0016(6) C11 0.0149(6) 0.0112(6) 0.0119(5) 0.0003(4) -0.0009(5) 0.0006(5) C12 0.0150(6) 0.0129(6) 0.0150(6) -0.0005(5) -0.0001(5) 0.0010(5) C13 0.0190(7) 0.0174(6) 0.0164(6) -0.0025(5) -0.0035(5) 0.0001(5) C14 0.0242(8) 0.0202(7) 0.0125(6) -0.0016(5) -0.0029(5) 0.0025(6) C15 0.0194(7) 0.0189(7) 0.0124(6) 0.0013(5) 0.0018(5) 0.0032(5) C16 0.0165(6) 0.0154(6) 0.0126(6) 0.0002(5) -0.0007(5) -0.0003(5) C17 0.0138(6) 0.0161(6) 0.0276(7) -0.0022(5) -0.0007(5) -0.0028(5) C18 0.0350(9) 0.0311(9) 0.0134(6) -0.0010(6) 0.0066(6) 0.0049(7) C19 0.0159(7) 0.0139(6) 0.0179(6) 0.0023(5) -0.0003(5) 0.0005(5) C20 0.0142(6) 0.0140(6) 0.0197(6) 0.0022(5) -0.0007(5) -0.0005(5) C21 0.0150(6) 0.0152(6) 0.0132(6) -0.0003(5) 0.0023(5) 0.0022(5) Fe1A 0.01080(9) 0.01119(9) 0.01543(9) -0.00085(7) -0.00024(7) 0.00010(7) O1A 0.0230(6) 0.0134(5) 0.0265(6) 0.0059(4) 0.0027(4) 0.0023(4) O2A 0.0186(5) 0.0146(5) 0.0181(5) 0.0011(4) 0.0029(4) 0.0008(4) O3A 0.0166(5) 0.0192(5) 0.0227(5) 0.0046(4) 0.0028(4) 0.0067(4) O4A 0.024(2) 0.0336(17) 0.020(2) 0.0074(18) 0.0085(14) 0.0038(16) C18A 0.034(2) 0.045(2) 0.0171(15) 0.0055(14) 0.0078(13) -0.0011(17) O4B 0.040(3) 0.040(2) 0.024(3) 0.010(2) 0.0139(17) 0.014(2) C18B 0.039(2) 0.037(2) 0.0271(18) 0.0025(15) 0.0145(15) 0.0075(17) O5A 0.0255(6) 0.0389(7) 0.0274(6) -0.0113(5) 0.0081(5) -0.0051(6) O6A 0.0302(7) 0.0153(5) 0.0416(7) -0.0037(5) 0.0062(5) -0.0019(5) O7A 0.0147(5) 0.0292(6) 0.0317(6) 0.0021(5) -0.0032(4) 0.0003(5) C1A 0.0166(6) 0.0141(6) 0.0141(6) 0.0005(5) -0.0018(5) 0.0004(5) C2A 0.0175(7) 0.0112(6) 0.0150(6) 0.0011(5) -0.0009(5) 0.0004(5) C3A 0.0169(7) 0.0117(6) 0.0165(6) 0.0006(5) -0.0043(5) -0.0008(5) C4A 0.0135(6) 0.0110(6) 0.0202(6) -0.0008(5) -0.0037(5) 0.0007(5) C5A 0.0128(6) 0.0119(6) 0.0180(6) 0.0012(5) 0.0004(5) 0.0007(5) C6A 0.0135(6) 0.0140(6) 0.0168(6) 0.0019(5) 0.0007(5) 0.0017(5) C7A 0.0207(7) 0.0103(6) 0.0179(6) 0.0019(5) 0.0005(5) -0.0025(5) C8A 0.0278(8) 0.0148(7) 0.0243(7) -0.0012(5) 0.0042(6) -0.0001(6) C9A 0.0318(9) 0.0175(7) 0.0370(9) -0.0009(6) -0.0155(7) -0.0031(7) C10A 0.0192(7) 0.0198(7) 0.0196(7) 0.0010(5) 0.0026(5) -0.0024(6) C11A 0.0155(6) 0.0123(6) 0.0178(6) 0.0020(5) 0.0006(5) 0.0007(5) C12A 0.0152(6) 0.0143(6) 0.0169(6) 0.0000(5) -0.0005(5) 0.0000(5) C13A 0.0210(7) 0.0185(7) 0.0196(7) 0.0020(5) -0.0038(5) 0.0021(6) C14A 0.0298(9) 0.0224(7) 0.0158(6) 0.0043(5) -0.0004(6) 0.0017(6) C15A 0.0269(9) 0.0282(8) 0.0225(7) 0.0066(6) 0.0091(6) 0.0052(7) C16A 0.0191(7) 0.0239(8) 0.0238(7) 0.0077(6) 0.0057(6) 0.0055(6) C17A 0.0150(7) 0.0180(7) 0.0288(8) 0.0029(6) -0.0001(6) 0.0048(5) C19A 0.0154(7) 0.0197(7) 0.0221(7) -0.0034(5) 0.0000(5) -0.0028(5) C20A 0.0166(7) 0.0155(6) 0.0227(7) -0.0025(5) 0.0024(5) -0.0033(5) C21A 0.0157(7) 0.0167(6) 0.0184(6) -0.0003(5) 0.0016(5) -0.0015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C2 2.1239(14) . ? Fe1 C3 2.0810(13) . ? Fe1 C4 2.1792(14) . ? Fe1 C6 2.1426(13) . ? Fe1 C19 1.7952(15) . ? Fe1 C20 1.8253(15) . ? Fe1 C21 1.7946(15) . ? O1 C1 1.2092(18) . ? O2 C1 1.3418(17) . ? O2 C10 1.4446(18) . ? O3 C12 1.3777(17) . ? O3 C17 1.4295(18) . ? O4 C15 1.3694(18) . ? O4 C18 1.4225(18) . ? O5 C19 1.1393(18) . ? O6 C20 1.1450(18) . ? O7 C21 1.1362(18) . ? C1 C2 1.484(2) . ? C2 H2 0.96(2) . ? C2 C3 1.422(2) . ? C3 H3 0.981(19) . ? C3 C4 1.394(2) . ? C4 H4 0.936(19) . ? C4 C5 1.5211(19) . ? C5 H5 1.0000 . ? C5 C6 1.5245(19) . ? C5 C7 1.5207(19) . ? C6 H6 0.950(19) . ? C6 C11 1.4866(18) . ? C7 C8 1.327(2) . ? C7 C9 1.503(2) . ? C8 H8B 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9C 0.9800 . ? C9 H9B 0.9800 . ? C10 H10A 0.9800 . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? C11 C12 1.418(2) . ? C11 C16 1.390(2) . ? C12 C13 1.3919(19) . ? C13 H13 0.9500 . ? C13 C14 1.396(2) . ? C14 H14 0.9500 . ? C14 C15 1.385(2) . ? C15 C16 1.3943(19) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Fe1A C2A 2.1290(14) . ? Fe1A C3A 2.0804(14) . ? Fe1A C4A 2.1754(14) . ? Fe1A C6A 2.1401(14) . ? Fe1A C19A 1.7946(16) . ? Fe1A C20A 1.8416(15) . ? Fe1A C21A 1.7944(15) . ? O1A C1A 1.2122(18) . ? O2A C1A 1.3387(18) . ? O2A C10A 1.4433(18) . ? O3A C12A 1.3761(18) . ? O3A C17A 1.4291(18) . ? O4A C18A 1.416(6) . ? O4A C15A 1.384(6) . ? C18A H18D 0.9800 . ? C18A H18E 0.9800 . ? C18A H18F 0.9800 . ? O4B C18B 1.427(8) . ? O4B C15A 1.393(6) . ? C18B H18I 0.9800 . ? C18B H18H 0.9800 . ? C18B H18G 0.9800 . ? O5A C19A 1.1412(19) . ? O6A C20A 1.1204(19) . ? O7A C21A 1.1380(19) . ? C1A C2A 1.484(2) . ? C2A H2A 0.91(2) . ? C2A C3A 1.423(2) . ? C3A H3A 0.97(2) . ? C3A C4A 1.394(2) . ? C4A H4A 0.94(2) . ? C4A C5A 1.5223(19) . ? C5A H5A 1.0000 . ? C5A C6A 1.525(2) . ? C5A C7A 1.518(2) . ? C6A H6A 0.960(19) . ? C6A C11A 1.490(2) . ? C7A C8A 1.330(2) . ? C7A C9A 1.506(2) . ? C8A H8AB 0.9500 . ? C8A H8AA 0.9500 . ? C9A H9AA 0.9800 . ? C9A H9AC 0.9800 . ? C9A H9AB 0.9800 . ? C10A H10D 0.9800 . ? C10A H10F 0.9800 . ? C10A H10E 0.9800 . ? C11A C12A 1.410(2) . ? C11A C16A 1.396(2) . ? C12A C13A 1.392(2) . ? C13A H13A 0.9500 . ? C13A C14A 1.389(2) . ? C14A H14A 0.9500 . ? C14A C15A 1.386(2) . ? C15A C16A 1.392(2) . ? C16A H16A 0.9500 . ? C17A H17D 0.9800 . ? C17A H17F 0.9800 . ? C17A H17E 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 Fe1 C2 H2 110.0(11) . . ? Fe1 C3 H3 114.5(11) . . ? Fe1 C4 H4 122.0(12) . . ? Fe1 C6 H6 104.0(11) . . ? O1 C1 O2 123.37(13) . . ? O1 C1 C2 125.41(14) . . ? O2 C1 C2 111.21(12) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10C 109.5 . . ? O2 C10 H10B 109.5 . . ? O3 C12 C11 116.02(12) . . ? O3 C12 C13 123.42(13) . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17C 109.5 . . ? O3 C17 H17B 109.5 . . ? O4 C15 C14 125.83(13) . . ? O4 C15 C16 114.49(14) . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? O5 C19 Fe1 176.08(14) . . ? O6 C20 Fe1 175.13(14) . . ? O7 C21 Fe1 177.47(13) . . ? C1 O2 C10 114.86(12) . . ? C1 C2 Fe1 119.34(10) . . ? C1 C2 H2 113.9(11) . . ? C2 Fe1 C4 70.25(5) . . ? C2 Fe1 C6 84.52(5) . . ? C2 C3 Fe1 71.87(8) . . ? C2 C3 H3 116.5(11) . . ? C3 Fe1 C2 39.52(6) . . ? C3 Fe1 C4 38.10(5) . . ? C3 Fe1 C6 90.31(5) . . ? C3 C2 Fe1 68.61(8) . . ? C3 C2 C1 115.94(12) . . ? C3 C2 H2 121.5(11) . . ? C3 C4 Fe1 67.13(8) . . ? C3 C4 H4 115.6(12) . . ? C3 C4 C5 124.79(13) . . ? C4 C3 Fe1 74.77(8) . . ? C4 C3 C2 123.13(13) . . ? C4 C3 H3 118.9(11) . . ? C4 C5 H5 106.6 . . ? C4 C5 C6 105.18(11) . . ? C5 C4 Fe1 92.34(8) . . ? C5 C4 H4 118.5(12) . . ? C5 C6 Fe1 93.67(8) . . ? C5 C6 H6 111.0(11) . . ? C6 Fe1 C4 68.07(5) . . ? C6 C5 H5 106.6 . . ? C7 C5 C4 113.91(11) . . ? C7 C5 H5 106.6 . . ? C7 C5 C6 117.30(12) . . ? C7 C8 H8B 120.0 . . ? C7 C8 H8A 120.0 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9C 109.5 . . ? C7 C9 H9B 109.5 . . ? C8 C7 C5 123.18(13) . . ? C8 C7 C9 121.72(14) . . ? H8B C8 H8A 120.0 . . ? C9 C7 C5 114.97(13) . . ? H9A C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C11 C6 Fe1 118.81(9) . . ? C11 C6 C5 116.93(11) . . ? C11 C6 H6 110.8(11) . . ? C11 C16 C15 122.48(14) . . ? C11 C16 H16 118.8 . . ? C12 O3 C17 116.20(11) . . ? C12 C11 C6 120.19(12) . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.75(14) . . ? C13 C12 C11 120.55(13) . . ? C13 C14 H14 120.3 . . ? C14 C13 H13 119.6 . . ? C14 C15 C16 119.68(14) . . ? C15 O4 C18 117.30(13) . . ? C15 C14 C13 119.37(13) . . ? C15 C14 H14 120.3 . . ? C15 C16 H16 118.8 . . ? C16 C11 C6 122.66(13) . . ? C16 C11 C12 117.13(12) . . ? H17A C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 Fe1 C2 162.98(6) . . ? C19 Fe1 C3 124.37(6) . . ? C19 Fe1 C4 92.85(6) . . ? C19 Fe1 C6 91.04(6) . . ? C19 Fe1 C20 89.05(7) . . ? C20 Fe1 C2 94.72(6) . . ? C20 Fe1 C3 87.70(6) . . ? C20 Fe1 C4 109.58(6) . . ? C20 Fe1 C6 177.65(6) . . ? C21 Fe1 C2 95.71(6) . . ? C21 Fe1 C3 135.22(6) . . ? C21 Fe1 C4 149.94(6) . . ? C21 Fe1 C6 84.62(6) . . ? C21 Fe1 C19 100.23(6) . . ? C21 Fe1 C20 97.68(6) . . ? Fe1A C2A H2A 109.3(12) . . ? Fe1A C3A H3A 117.0(11) . . ? Fe1A C4A H4A 120.9(12) . . ? Fe1A C6A H6A 103.1(12) . . ? O1A C1A O2A 123.40(14) . . ? O1A C1A C2A 125.45(14) . . ? O2A C1A C2A 111.14(12) . . ? O2A C10A H10D 109.5 . . ? O2A C10A H10F 109.5 . . ? O2A C10A H10E 109.5 . . ? O3A C12A C11A 116.10(12) . . ? O3A C12A C13A 123.42(14) . . ? O3A C17A H17D 109.5 . . ? O3A C17A H17F 109.5 . . ? O3A C17A H17E 109.5 . . ? O4A C15A O4B 20.5(2) . . ? O4A C15A C14A 127.0(3) . . ? O4A C15A C16A 112.6(3) . . ? O4B C18B H18I 109.5 . . ? O4B C18B H18H 109.5 . . ? O4B C18B H18G 109.5 . . ? H18I C18B H18H 109.5 . . ? H18I C18B H18G 109.5 . . ? H18H C18B H18G 109.5 . . ? O5A C19A Fe1A 175.41(15) . . ? O6A C20A Fe1A 175.83(15) . . ? O7A C21A Fe1A 177.39(14) . . ? C1A O2A C10A 115.10(12) . . ? C1A C2A Fe1A 119.48(10) . . ? C1A C2A H2A 112.8(12) . . ? C2A Fe1A C4A 70.26(6) . . ? C2A Fe1A C6A 84.33(5) . . ? C2A C3A Fe1A 72.09(8) . . ? C2A C3A H3A 115.8(12) . . ? C3A Fe1A C2A 39.49(6) . . ? C3A Fe1A C4A 38.15(6) . . ? C3A Fe1A C6A 90.23(5) . . ? C3A C2A Fe1A 68.41(8) . . ? C3A C2A C1A 115.96(12) . . ? C3A C2A H2A 123.7(12) . . ? C3A C4A Fe1A 67.23(8) . . ? C3A C4A H4A 116.5(12) . . ? C3A C4A C5A 124.66(13) . . ? C4A C3A Fe1A 74.62(8) . . ? C4A C3A C2A 123.16(13) . . ? C4A C3A H3A 120.1(12) . . ? C4A C5A H5A 106.7 . . ? C4A C5A C6A 104.90(11) . . ? C5A C4A Fe1A 92.50(8) . . ? C5A C4A H4A 118.0(12) . . ? C5A C6A Fe1A 93.80(9) . . ? C5A C6A H6A 111.8(11) . . ? C6A Fe1A C4A 68.08(5) . . ? C6A C5A H5A 106.7 . . ? C7A C5A C4A 113.63(12) . . ? C7A C5A H5A 106.7 . . ? C7A C5A C6A 117.44(12) . . ? C7A C8A H8AB 120.0 . . ? C7A C8A H8AA 120.0 . . ? C7A C9A H9AA 109.5 . . ? C7A C9A H9AC 109.5 . . ? C7A C9A H9AB 109.5 . . ? C8A C7A C5A 123.20(14) . . ? C8A C7A C9A 121.70(15) . . ? H8AB C8A H8AA 120.0 . . ? C9A C7A C5A 115.03(13) . . ? H9AA C9A H9AC 109.5 . . ? H9AA C9A H9AB 109.5 . . ? H9AC C9A H9AB 109.5 . . ? H10D C10A H10F 109.5 . . ? H10D C10A H10E 109.5 . . ? H10F C10A H10E 109.5 . . ? C11A C6A Fe1A 120.37(10) . . ? C11A C6A C5A 117.13(12) . . ? C11A C6A H6A 109.3(11) . . ? C11A C16A H16A 119.1 . . ? C12A O3A C17A 116.48(12) . . ? C12A C11A C6A 119.86(13) . . ? C12A C13A H13A 119.6 . . ? C13A C12A C11A 120.46(14) . . ? C13A C14A H14A 120.2 . . ? C14A C13A C12A 120.74(15) . . ? C14A C13A H13A 119.6 . . ? C14A C15A O4B 113.6(3) . . ? C14A C15A C16A 119.74(15) . . ? C15A O4A C18A 115.3(4) . . ? C15A O4B C18B 117.7(4) . . ? C15A C14A C13A 119.61(14) . . ? C15A C14A H14A 120.2 . . ? C15A C16A C11A 121.86(15) . . ? C15A C16A H16A 119.1 . . ? C16A C11A C6A 122.52(13) . . ? C16A C11A C12A 117.59(13) . . ? C16A C15A O4B 126.1(3) . . ? H17D C17A H17F 109.5 . . ? H17D C17A H17E 109.5 . . ? H17F C17A H17E 109.5 . . ? C19A Fe1A C2A 161.81(6) . . ? C19A Fe1A C3A 123.10(7) . . ? C19A Fe1A C4A 91.76(6) . . ? C19A Fe1A C6A 91.58(6) . . ? C19A Fe1A C20A 89.71(7) . . ? C20A Fe1A C2A 93.89(6) . . ? C20A Fe1A C3A 87.54(6) . . ? C20A Fe1A C4A 110.07(6) . . ? C20A Fe1A C6A 177.77(6) . . ? C21A Fe1A C2A 97.01(6) . . ? C21A Fe1A C3A 136.50(6) . . ? C21A Fe1A C4A 150.07(6) . . ? C21A Fe1A C6A 84.13(6) . . ? C21A Fe1A C19A 100.19(7) . . ? C21A Fe1A C20A 97.43(7) . . ? 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 Fe1 C2 C3 C4 -57.05(12) . . . . ? Fe1 C3 C4 C5 -76.17(12) . . . . ? Fe1 C4 C5 C6 -7.48(10) . . . . ? Fe1 C4 C5 C7 -137.28(10) . . . . ? Fe1 C6 C11 C12 -105.84(13) . . . . ? Fe1 C6 C11 C16 75.67(16) . . . . ? O1 C1 C2 Fe1 -58.52(18) . . . . ? O1 C1 C2 C3 20.4(2) . . . . ? O2 C1 C2 Fe1 122.46(11) . . . . ? O2 C1 C2 C3 -158.60(12) . . . . ? O3 C12 C13 C14 -178.05(14) . . . . ? O4 C15 C16 C11 -178.11(13) . . . . ? C1 C2 C3 Fe1 -113.25(12) . . . . ? C1 C2 C3 C4 -170.30(13) . . . . ? C2 Fe1 C3 C4 133.25(12) . . . . ? C2 Fe1 C4 C3 -29.50(8) . . . . ? C2 Fe1 C4 C5 97.55(9) . . . . ? C2 Fe1 C6 C5 -76.42(8) . . . . ? C2 Fe1 C6 C11 159.99(11) . . . . ? C2 Fe1 C19 O5 -108(2) . . . . ? C2 Fe1 C20 O6 -175.8(16) . . . . ? C2 Fe1 C21 O7 -70(3) . . . . ? C2 C3 C4 Fe1 55.74(12) . . . . ? C2 C3 C4 C5 -20.4(2) . . . . ? C3 Fe1 C2 C1 108.59(14) . . . . ? C3 Fe1 C4 C5 127.05(12) . . . . ? C3 Fe1 C6 C5 -37.26(8) . . . . ? C3 Fe1 C6 C11 -160.85(11) . . . . ? C3 Fe1 C19 O5 -92(2) . . . . ? C3 Fe1 C20 O6 145.3(16) . . . . ? C3 Fe1 C21 O7 -71(3) . . . . ? C3 C4 C5 C6 56.08(16) . . . . ? C3 C4 C5 C7 -73.72(17) . . . . ? C4 Fe1 C2 C1 137.11(12) . . . . ? C4 Fe1 C2 C3 28.53(8) . . . . ? C4 Fe1 C3 C2 -133.25(12) . . . . ? C4 Fe1 C6 C5 -5.52(7) . . . . ? C4 Fe1 C6 C11 -129.11(12) . . . . ? C4 Fe1 C19 O5 -115(2) . . . . ? C4 Fe1 C20 O6 113.5(16) . . . . ? C4 Fe1 C21 O7 -11(3) . . . . ? C4 C5 C6 Fe1 7.62(10) . . . . ? C4 C5 C6 C11 132.66(12) . . . . ? C4 C5 C7 C8 134.39(15) . . . . ? C4 C5 C7 C9 -49.73(17) . . . . ? C5 C6 C11 C12 142.98(13) . . . . ? C5 C6 C11 C16 -35.52(19) . . . . ? C6 Fe1 C2 C1 -154.24(11) . . . . ? C6 Fe1 C2 C3 97.17(8) . . . . ? C6 Fe1 C3 C2 -80.99(8) . . . . ? C6 Fe1 C3 C4 52.26(9) . . . . ? C6 Fe1 C4 C3 -121.52(9) . . . . ? C6 Fe1 C4 C5 5.53(8) . . . . ? C6 Fe1 C19 O5 177(72) . . . . ? C6 Fe1 C20 O6 113.1(19) . . . . ? C6 Fe1 C21 O7 14(3) . . . . ? C6 C5 C7 C8 10.9(2) . . . . ? C6 C5 C7 C9 -173.18(13) . . . . ? C6 C11 C12 O3 -0.98(19) . . . . ? C6 C11 C12 C13 179.85(13) . . . . ? C6 C11 C16 C15 178.95(13) . . . . ? C7 C5 C6 Fe1 135.40(10) . . . . ? C7 C5 C6 C11 -99.56(14) . . . . ? C10 O2 C1 O1 -3.6(2) . . . . ? C10 O2 C1 C2 175.42(12) . . . . ? C11 C12 C13 C14 1.1(2) . . . . ? C12 C11 C16 C15 0.4(2) . . . . ? C12 C13 C14 C15 0.7(2) . . . . ? C13 C14 C15 O4 177.50(14) . . . . ? C13 C14 C15 C16 -1.8(2) . . . . ? C14 C15 C16 C11 1.3(2) . . . . ? C16 C11 C12 O3 177.59(12) . . . . ? C16 C11 C12 C13 -1.6(2) . . . . ? C17 O3 C12 C11 -164.44(13) . . . . ? C17 O3 C12 C13 14.7(2) . . . . ? C18 O4 C15 C14 3.5(2) . . . . ? C18 O4 C15 C16 -177.17(14) . . . . ? C19 Fe1 C2 C1 130.3(2) . . . . ? C19 Fe1 C2 C3 21.7(2) . . . . ? C19 Fe1 C3 C2 -172.46(9) . . . . ? C19 Fe1 C3 C4 -39.21(11) . . . . ? C19 Fe1 C4 C3 148.50(9) . . . . ? C19 Fe1 C4 C5 -84.45(9) . . . . ? C19 Fe1 C6 C5 87.12(9) . . . . ? C19 Fe1 C6 C11 -36.47(11) . . . . ? C19 Fe1 C20 O6 20.8(16) . . . . ? C19 Fe1 C21 O7 104(3) . . . . ? C20 Fe1 C2 C1 27.99(12) . . . . ? C20 Fe1 C2 C3 -80.59(9) . . . . ? C20 Fe1 C3 C2 100.26(9) . . . . ? C20 Fe1 C3 C4 -126.48(9) . . . . ? C20 Fe1 C4 C3 58.50(10) . . . . ? C20 Fe1 C4 C5 -174.45(8) . . . . ? C20 Fe1 C6 C5 -5.1(16) . . . . ? C20 Fe1 C6 C11 -128.7(15) . . . . ? C20 Fe1 C19 O5 -5(2) . . . . ? C20 Fe1 C21 O7 -166(52) . . . . ? C21 Fe1 C2 C1 -70.23(12) . . . . ? C21 Fe1 C2 C3 -178.81(9) . . . . ? C21 Fe1 C3 C2 1.68(12) . . . . ? C21 Fe1 C3 C4 134.93(10) . . . . ? C21 Fe1 C4 C3 -95.34(13) . . . . ? C21 Fe1 C4 C5 31.71(15) . . . . ? C21 Fe1 C6 C5 -172.70(9) . . . . ? C21 Fe1 C6 C11 63.71(11) . . . . ? C21 Fe1 C19 O5 93(2) . . . . ? C21 Fe1 C20 O6 -79.4(16) . . . . ? Fe1A C2A C3A C4A 57.05(13) . . . . ? Fe1A C3A C4A C5A 76.54(13) . . . . ? Fe1A C4A C5A C6A 7.44(11) . . . . ? Fe1A C4A C5A C7A 137.00(11) . . . . ? Fe1A C6A C11A C12A 108.35(14) . . . . ? Fe1A C6A C11A C16A -73.85(18) . . . . ? O1A C1A C2A Fe1A 57.87(19) . . . . ? O1A C1A C2A C3A -20.9(2) . . . . ? O2A C1A C2A Fe1A -123.14(11) . . . . ? O2A C1A C2A C3A 158.10(12) . . . . ? O3A C12A C13A C14A 178.15(15) . . . . ? O4A C15A C16A C11A 170.6(3) . . . . ? C18A O4A C15A O4B 51.5(13) . . . . ? C18A O4A C15A C14A -2.9(6) . . . . ? C18A O4A C15A C16A -173.5(4) . . . . ? O4B C15A C16A C11A -171.5(4) . . . . ? C18B O4B C15A O4A 63.7(13) . . . . ? C18B O4B C15A C14A -161.4(4) . . . . ? C18B O4B C15A C16A 9.9(7) . . . . ? C1A C2A C3A Fe1A 113.32(12) . . . . ? C1A C2A C3A C4A 170.37(13) . . . . ? C2A Fe1A C3A C4A -133.23(12) . . . . ? C2A Fe1A C4A C3A 29.49(8) . . . . ? C2A Fe1A C4A C5A -97.31(9) . . . . ? C2A Fe1A C6A C5A 76.49(9) . . . . ? C2A Fe1A C6A C11A -158.86(12) . . . . ? C2A Fe1A C19A O5A 92.8(18) . . . . ? C2A Fe1A C20A O6A 171(2) . . . . ? C2A Fe1A C21A O7A 74(3) . . . . ? C2A C3A C4A Fe1A -55.91(13) . . . . ? C2A C3A C4A C5A 20.6(2) . . . . ? C3A Fe1A C2A C1A -108.48(14) . . . . ? C3A Fe1A C4A C5A -126.80(13) . . . . ? C3A Fe1A C6A C5A 37.37(9) . . . . ? C3A Fe1A C6A C11A 162.03(12) . . . . ? C3A Fe1A C19A O5A 78.0(18) . . . . ? C3A Fe1A C20A O6A -150(2) . . . . ? C3A Fe1A C21A O7A 75(3) . . . . ? C3A C4A C5A C6A -56.41(17) . . . . ? C3A C4A C5A C7A 73.15(18) . . . . ? C4A Fe1A C2A C1A -137.05(12) . . . . ? C4A Fe1A C2A C3A -28.56(8) . . . . ? C4A Fe1A C3A C2A 133.23(12) . . . . ? C4A Fe1A C6A C5A 5.51(8) . . . . ? C4A Fe1A C6A C11A 130.17(13) . . . . ? C4A Fe1A C19A O5A 101.2(18) . . . . ? C4A Fe1A C20A O6A -118(2) . . . . ? C4A Fe1A C21A O7A 12(3) . . . . ? C4A C5A C6A Fe1A -7.57(11) . . . . ? C4A C5A C6A C11A -134.69(13) . . . . ? C4A C5A C7A C8A -133.09(15) . . . . ? C4A C5A C7A C9A 49.83(18) . . . . ? C5A C6A C11A C12A -138.91(14) . . . . ? C5A C6A C11A C16A 38.9(2) . . . . ? C6A Fe1A C2A C1A 154.23(12) . . . . ? C6A Fe1A C2A C3A -97.29(9) . . . . ? C6A Fe1A C3A C2A 80.78(9) . . . . ? C6A Fe1A C3A C4A -52.45(9) . . . . ? C6A Fe1A C4A C3A 121.28(10) . . . . ? C6A Fe1A C4A C5A -5.52(8) . . . . ? C6A Fe1A C19A O5A 169.3(18) . . . . ? C6A Fe1A C20A O6A -151.8(17) . . . . ? C6A Fe1A C21A O7A -10(3) . . . . ? C6A C5A C7A C8A -10.2(2) . . . . ? C6A C5A C7A C9A 172.75(14) . . . . ? C6A C11A C12A O3A -1.1(2) . . . . ? C6A C11A C12A C13A 177.35(14) . . . . ? C6A C11A C16A C15A -176.87(16) . . . . ? C7A C5A C6A Fe1A -134.83(11) . . . . ? C7A C5A C6A C11A 98.05(15) . . . . ? C10A O2A C1A O1A 3.5(2) . . . . ? C10A O2A C1A C2A -175.51(12) . . . . ? C11A C12A C13A C14A -0.2(2) . . . . ? C12A C11A C16A C15A 1.0(2) . . . . ? C12A C13A C14A C15A 0.5(3) . . . . ? C13A C14A C15A O4A -170.0(3) . . . . ? C13A C14A C15A O4B 171.9(3) . . . . ? C13A C14A C15A C16A 0.0(3) . . . . ? C14A C15A C16A C11A -0.7(3) . . . . ? C16A C11A C12A O3A -178.97(14) . . . . ? C16A C11A C12A C13A -0.5(2) . . . . ? C17A O3A C12A C11A 166.63(13) . . . . ? C17A O3A C12A C13A -11.7(2) . . . . ? C19A Fe1A C2A C1A -128.1(2) . . . . ? C19A Fe1A C2A C3A -19.6(2) . . . . ? C19A Fe1A C3A C2A 172.81(9) . . . . ? C19A Fe1A C3A C4A 39.58(11) . . . . ? C19A Fe1A C4A C3A -147.72(10) . . . . ? C19A Fe1A C4A C5A 85.48(9) . . . . ? C19A Fe1A C6A C5A -85.75(9) . . . . ? C19A Fe1A C6A C11A 38.90(12) . . . . ? C19A Fe1A C20A O6A -26(2) . . . . ? C19A Fe1A C21A O7A -100(3) . . . . ? C20A Fe1A C2A C1A -27.11(12) . . . . ? C20A Fe1A C2A C3A 81.38(9) . . . . ? C20A Fe1A C3A C2A -99.13(9) . . . . ? C20A Fe1A C3A C4A 127.64(9) . . . . ? C20A Fe1A C4A C3A -57.39(10) . . . . ? C20A Fe1A C4A C5A 175.81(9) . . . . ? C20A Fe1A C6A C5A 39.7(17) . . . . ? C20A Fe1A C6A C11A 164.3(16) . . . . ? C20A Fe1A C19A O5A -8.9(18) . . . . ? C20A Fe1A C21A O7A 169(56) . . . . ? C21A Fe1A C2A C1A 70.88(12) . . . . ? C21A Fe1A C2A C3A 179.37(9) . . . . ? C21A Fe1A C3A C2A -0.92(13) . . . . ? C21A Fe1A C3A C4A -134.15(10) . . . . ? C21A Fe1A C4A C3A 98.18(14) . . . . ? C21A Fe1A C4A C5A -28.62(16) . . . . ? C21A Fe1A C6A C5A 174.16(9) . . . . ? C21A Fe1A C6A C11A -61.19(12) . . . . ? C21A Fe1A C19A O5A -106.4(18) . . . . ? C21A Fe1A C20A O6A 74(2) . . . . ?