# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'P Power' 'James C. Fettinger' 'Chengbao Ni' _publ_contact_author_name 'Philip Power' _publ_contact_author_email PPPOWER@UCDAVIS.EDU _publ_section_title ; Reactions of a Two-Coordinate Iron Diaryl with Dioxygen and Carbon Monoxide: Efficient Synthesis of Iron(II) aryloxides and Iron(II) Bis(acyl) Complex ; # Attachment 'D2FeOverallCif_2.cif' data_c2c_Dipp2Fe _database_code_depnum_ccdc_archive 'CCDC 737424' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H74 Fe' _chemical_formula_sum 'C60 H74 Fe' _chemical_formula_weight 851.04 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.6179(7) _cell_length_b 15.9094(7) _cell_length_c 19.8659(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.3490(10) _cell_angle_gamma 90.00 _cell_volume 4927.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 8542 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type 'Empirical, SADabs (multi-scan)' _exptl_absorpt_correction_T_min 0.9071 _exptl_absorpt_correction_T_max 0.9377 _exptl_absorpt_process_details 'SADABS 2007/3 (Sheldrick, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27139 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5667 _reflns_number_gt 5148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX SMART 1000' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+4.4635P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5667 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.0000 0.251616(14) 0.2500 0.01735(8) Uani 1 2 d S . . C1 C 0.07525(7) 0.22841(7) 0.33658(5) 0.0150(2) Uani 1 1 d . . . C2 C 0.06148(7) 0.17449(7) 0.39189(5) 0.0152(2) Uani 1 1 d . . . C3 C 0.13022(7) 0.14700(7) 0.43479(6) 0.0192(2) Uani 1 1 d . . . H3A H 0.1200 0.1079 0.4696 0.023 Uiso 1 1 calc R . . C4 C 0.21313(7) 0.17599(8) 0.42726(6) 0.0214(2) Uani 1 1 d . . . H4A H 0.2597 0.1552 0.4554 0.026 Uiso 1 1 calc R . . C5 C 0.22679(7) 0.23551(8) 0.37827(6) 0.0200(2) Uani 1 1 d . . . H5A H 0.2823 0.2591 0.3750 0.024 Uiso 1 1 calc R . . C6 C 0.15936(7) 0.26123(7) 0.33342(6) 0.0162(2) Uani 1 1 d . . . C7 C -0.02540(7) 0.15205(7) 0.41595(5) 0.0164(2) Uani 1 1 d . . . C8 C -0.06470(7) 0.07423(7) 0.40109(6) 0.0180(2) Uani 1 1 d . . . C9 C -0.13621(7) 0.05022(8) 0.43580(6) 0.0225(2) Uani 1 1 d . . . H9A H -0.1617 -0.0032 0.4270 0.027 Uiso 1 1 calc R . . C10 C -0.17039(8) 0.10294(9) 0.48269(6) 0.0249(3) Uani 1 1 d . . . H10A H -0.2185 0.0855 0.5063 0.030 Uiso 1 1 calc R . . C11 C -0.13401(8) 0.18124(8) 0.49501(6) 0.0233(2) Uani 1 1 d . . . H11A H -0.1592 0.2183 0.5257 0.028 Uiso 1 1 calc R . . C12 C -0.06083(7) 0.20671(7) 0.46313(6) 0.0188(2) Uani 1 1 d . . . C13 C -0.03152(7) 0.01533(7) 0.34865(6) 0.0203(2) Uani 1 1 d . . . H13A H 0.0161 0.0444 0.3264 0.024 Uiso 1 1 calc R . . C14 C -0.10182(9) -0.00534(11) 0.29440(7) 0.0353(3) Uani 1 1 d . . . H14A H -0.1232 0.0468 0.2732 0.053 Uiso 1 1 calc R . . H14B H -0.1490 -0.0345 0.3150 0.053 Uiso 1 1 calc R . . H14C H -0.0783 -0.0416 0.2601 0.053 Uiso 1 1 calc R . . C15 C 0.00424(14) -0.06483(10) 0.38117(8) 0.0493(5) Uani 1 1 d . . . H15A H 0.0513 -0.0507 0.4140 0.074 Uiso 1 1 calc R . . H15B H 0.0256 -0.1017 0.3463 0.074 Uiso 1 1 calc R . . H15C H -0.0412 -0.0937 0.4041 0.074 Uiso 1 1 calc R . . C16 C -0.01936(8) 0.29075(7) 0.48216(6) 0.0211(2) Uani 1 1 d . . . H16A H 0.0266 0.3014 0.4502 0.025 Uiso 1 1 calc R . . C17 C -0.08296(9) 0.36364(9) 0.47524(7) 0.0318(3) Uani 1 1 d . . . H17A H -0.1099 0.3643 0.4294 0.048 Uiso 1 1 calc R . . H17B H -0.0526 0.4168 0.4840 0.048 Uiso 1 1 calc R . . H17C H -0.1272 0.3566 0.5078 0.048 Uiso 1 1 calc R . . C18 C 0.02364(9) 0.28765(9) 0.55347(7) 0.0282(3) Uani 1 1 d . . . H18A H 0.0657 0.2419 0.5563 0.042 Uiso 1 1 calc R . . H18B H -0.0200 0.2779 0.5861 0.042 Uiso 1 1 calc R . . H18C H 0.0527 0.3412 0.5635 0.042 Uiso 1 1 calc R . . C19 C 0.17707(7) 0.32942(7) 0.28373(5) 0.0173(2) Uani 1 1 d . . . C20 C 0.14253(7) 0.41123(7) 0.29279(6) 0.0189(2) Uani 1 1 d . . . C21 C 0.16234(8) 0.47424(8) 0.24748(6) 0.0230(2) Uani 1 1 d . . . H21A H 0.1400 0.5292 0.2531 0.028 Uiso 1 1 calc R . . C22 C 0.21405(8) 0.45844(8) 0.19421(6) 0.0247(3) Uani 1 1 d . . . H22A H 0.2251 0.5017 0.1630 0.030 Uiso 1 1 calc R . . C23 C 0.24938(8) 0.37929(8) 0.18688(6) 0.0238(2) Uani 1 1 d . . . H23A H 0.2852 0.3690 0.1507 0.029 Uiso 1 1 calc R . . C24 C 0.23314(7) 0.31425(8) 0.23185(6) 0.0205(2) Uani 1 1 d . . . C25 C 0.09145(7) 0.43142(7) 0.35427(6) 0.0201(2) Uani 1 1 d . . . H25A H 0.0519 0.3831 0.3611 0.024 Uiso 1 1 calc R . . C26 C 0.15176(8) 0.43885(9) 0.41785(6) 0.0271(3) Uani 1 1 d . . . H26A H 0.1866 0.3878 0.4231 0.041 Uiso 1 1 calc R . . H26B H 0.1178 0.4459 0.4574 0.041 Uiso 1 1 calc R . . H26C H 0.1894 0.4876 0.4136 0.041 Uiso 1 1 calc R . . C27 C 0.03681(8) 0.51101(8) 0.34771(7) 0.0274(3) Uani 1 1 d . . . H27A H 0.0000 0.5084 0.3061 0.041 Uiso 1 1 calc R . . H27B H 0.0743 0.5603 0.3464 0.041 Uiso 1 1 calc R . . H27C H 0.0010 0.5154 0.3865 0.041 Uiso 1 1 calc R . . C28 C 0.27897(8) 0.23028(8) 0.22486(6) 0.0215(2) Uani 1 1 d . . . H28A H 0.2560 0.1905 0.2584 0.026 Uiso 1 1 calc R . . C29 C 0.26121(9) 0.19260(9) 0.15488(6) 0.0281(3) Uani 1 1 d . . . H29A H 0.1991 0.1890 0.1449 0.042 Uiso 1 1 calc R . . H29B H 0.2863 0.1362 0.1535 0.042 Uiso 1 1 calc R . . H29C H 0.2867 0.2284 0.1213 0.042 Uiso 1 1 calc R . . C30 C 0.37604(8) 0.23933(9) 0.24138(7) 0.0282(3) Uani 1 1 d . . . H30A H 0.3860 0.2632 0.2866 0.042 Uiso 1 1 calc R . . H30B H 0.4006 0.2766 0.2083 0.042 Uiso 1 1 calc R . . H30C H 0.4033 0.1839 0.2397 0.042 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 0.02159(13) 0.01737(12) 0.01261(12) 0.000 -0.00304(8) 0.000 C1 0.0165(5) 0.0151(5) 0.0134(5) -0.0028(4) 0.0006(4) -0.0003(4) C2 0.0161(5) 0.0151(5) 0.0146(5) -0.0030(4) 0.0017(4) -0.0004(4) C3 0.0203(5) 0.0205(5) 0.0169(5) 0.0027(4) 0.0019(4) 0.0019(4) C4 0.0169(5) 0.0273(6) 0.0197(5) 0.0016(5) -0.0016(4) 0.0031(4) C5 0.0142(5) 0.0251(6) 0.0208(6) -0.0011(4) 0.0014(4) -0.0020(4) C6 0.0180(5) 0.0163(5) 0.0143(5) -0.0022(4) 0.0024(4) -0.0009(4) C7 0.0154(5) 0.0201(5) 0.0137(5) 0.0019(4) 0.0003(4) 0.0004(4) C8 0.0164(5) 0.0204(5) 0.0170(5) 0.0013(4) -0.0007(4) -0.0002(4) C9 0.0187(5) 0.0258(6) 0.0227(6) 0.0026(5) -0.0002(4) -0.0040(4) C10 0.0171(5) 0.0371(7) 0.0208(6) 0.0031(5) 0.0037(4) -0.0029(5) C11 0.0193(5) 0.0332(7) 0.0178(5) -0.0025(5) 0.0037(4) 0.0027(5) C12 0.0185(5) 0.0227(6) 0.0150(5) -0.0001(4) 0.0001(4) 0.0010(4) C13 0.0208(5) 0.0184(5) 0.0217(5) -0.0017(4) 0.0019(4) -0.0026(4) C14 0.0277(7) 0.0521(9) 0.0262(7) -0.0123(6) 0.0026(5) -0.0097(6) C15 0.0810(13) 0.0325(8) 0.0347(8) 0.0031(6) 0.0070(8) 0.0273(8) C16 0.0239(6) 0.0212(6) 0.0185(5) -0.0038(4) 0.0033(4) 0.0014(4) C17 0.0368(7) 0.0267(6) 0.0317(7) -0.0024(5) -0.0010(6) 0.0090(5) C18 0.0320(7) 0.0271(6) 0.0247(6) -0.0045(5) -0.0047(5) -0.0009(5) C19 0.0167(5) 0.0192(5) 0.0159(5) -0.0006(4) -0.0009(4) -0.0040(4) C20 0.0173(5) 0.0207(5) 0.0184(5) -0.0012(4) -0.0019(4) -0.0022(4) C21 0.0237(6) 0.0201(5) 0.0248(6) 0.0021(5) -0.0022(4) -0.0006(4) C22 0.0275(6) 0.0251(6) 0.0213(6) 0.0060(5) -0.0006(5) -0.0059(5) C23 0.0259(6) 0.0277(6) 0.0180(5) 0.0007(5) 0.0031(4) -0.0064(5) C24 0.0216(5) 0.0221(6) 0.0180(5) -0.0015(4) 0.0015(4) -0.0048(4) C25 0.0201(5) 0.0188(5) 0.0213(5) -0.0027(4) 0.0010(4) -0.0012(4) C26 0.0297(6) 0.0283(6) 0.0229(6) -0.0056(5) -0.0021(5) 0.0036(5) C27 0.0262(6) 0.0267(6) 0.0293(6) -0.0033(5) 0.0007(5) 0.0047(5) C28 0.0219(6) 0.0231(6) 0.0198(6) -0.0019(4) 0.0037(4) -0.0028(4) C29 0.0317(7) 0.0302(6) 0.0226(6) -0.0057(5) 0.0041(5) -0.0027(5) C30 0.0213(6) 0.0298(6) 0.0335(7) -0.0040(5) 0.0007(5) -0.0017(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 2.0590(11) 2 ? Fe1 C1 2.0591(11) . ? C1 C6 1.4183(15) . ? C1 C2 1.4202(15) . ? C2 C3 1.4012(15) . ? C2 C7 1.5076(14) . ? C3 C4 1.3908(16) . ? C3 H3A 0.9500 . ? C4 C5 1.3834(17) . ? C4 H4A 0.9500 . ? C5 C6 1.4002(16) . ? C5 H5A 0.9500 . ? C6 C19 1.5034(15) . ? C7 C8 1.4056(16) . ? C7 C12 1.4147(15) . ? C8 C9 1.3996(16) . ? C8 C13 1.5149(16) . ? C9 C10 1.3835(18) . ? C9 H9A 0.9500 . ? C10 C11 1.3850(19) . ? C10 H10A 0.9500 . ? C11 C12 1.3987(16) . ? C11 H11A 0.9500 . ? C12 C16 1.5235(16) . ? C13 C15 1.5210(18) . ? C13 C14 1.5288(18) . ? C13 H13A 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.5279(17) . ? C16 C18 1.5327(17) . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.4116(16) . ? C19 C20 1.4243(16) . ? C20 C21 1.3941(16) . ? C20 C25 1.5312(16) . ? C21 C22 1.3912(18) . ? C21 H21A 0.9500 . ? C22 C23 1.3858(18) . ? C22 H22A 0.9500 . ? C23 C24 1.3998(16) . ? C23 H23A 0.9500 . ? C24 C28 1.5258(17) . ? C25 C27 1.5282(17) . ? C25 C26 1.5355(17) . ? C25 H25A 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.5244(17) . ? C28 C30 1.5390(17) . ? C28 H28A 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 C1 Fe1 C1 159.34(6) 2 . ? C6 C1 C2 116.04(10) . . ? C6 C1 Fe1 112.45(8) . . ? C2 C1 Fe1 130.52(8) . . ? C3 C2 C1 120.92(10) . . ? C3 C2 C7 113.89(9) . . ? C1 C2 C7 124.62(10) . . ? C4 C3 C2 121.07(10) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 119.04(10) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 120.43(10) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C1 121.90(10) . . ? C5 C6 C19 117.92(10) . . ? C1 C6 C19 120.08(10) . . ? C8 C7 C12 119.85(10) . . ? C8 C7 C2 122.14(10) . . ? C12 C7 C2 117.30(10) . . ? C9 C8 C7 119.22(11) . . ? C9 C8 C13 119.00(10) . . ? C7 C8 C13 121.78(10) . . ? C10 C9 C8 121.10(11) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C9 C10 C11 119.59(11) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C10 C11 C12 121.22(11) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C11 C12 C7 118.91(11) . . ? C11 C12 C16 119.26(10) . . ? C7 C12 C16 121.78(10) . . ? C8 C13 C15 111.01(11) . . ? C8 C13 C14 110.94(10) . . ? C15 C13 C14 110.48(13) . . ? C8 C13 H13A 108.1 . . ? C15 C13 H13A 108.1 . . ? C14 C13 H13A 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C17 112.27(10) . . ? C12 C16 C18 110.98(10) . . ? C17 C16 C18 110.79(10) . . ? C12 C16 H16A 107.5 . . ? C17 C16 H16A 107.5 . . ? C18 C16 H16A 107.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 120.28(10) . . ? C24 C19 C6 120.12(10) . . ? C20 C19 C6 119.39(10) . . ? C21 C20 C19 118.38(10) . . ? C21 C20 C25 120.65(11) . . ? C19 C20 C25 120.75(10) . . ? C22 C21 C20 121.46(11) . . ? C22 C21 H21A 119.3 . . ? C20 C21 H21A 119.3 . . ? C23 C22 C21 119.77(11) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? C22 C23 C24 121.10(11) . . ? C22 C23 H23A 119.5 . . ? C24 C23 H23A 119.5 . . ? C23 C24 C19 118.87(11) . . ? C23 C24 C28 119.05(10) . . ? C19 C24 C28 122.04(10) . . ? C27 C25 C20 114.85(10) . . ? C27 C25 C26 108.60(10) . . ? C20 C25 C26 110.43(10) . . ? C27 C25 H25A 107.6 . . ? C20 C25 H25A 107.6 . . ? C26 C25 H25A 107.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C24 111.47(11) . . ? C29 C28 C30 110.84(10) . . ? C24 C28 C30 111.12(10) . . ? C29 C28 H28A 107.7 . . ? C24 C28 H28A 107.7 . . ? C30 C28 H28A 107.7 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.455 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.046 #===END data_p21n _database_code_depnum_ccdc_archive 'CCDC 737425' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H74 Fe O2' _chemical_formula_sum 'C60 H74 Fe O2' _chemical_formula_weight 883.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8136(7) _cell_length_b 20.2033(14) _cell_length_c 11.1559(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.558(2) _cell_angle_gamma 90.00 _cell_volume 2437.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9901 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.75 _exptl_crystal_description block _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details 'SHELXTL 97 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25251 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5583 _reflns_number_gt 4830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+1.2166P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5583 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.0000 0.5000 0.02006(9) Uani 1 2 d S . . O1 O 0.55658(8) 0.07589(4) 0.42624(8) 0.01864(19) Uani 1 1 d . . . C1 C 0.67133(12) 0.10202(6) 0.42620(11) 0.0161(2) Uani 1 1 d . . . C2 C 0.77382(12) 0.06478(6) 0.46625(11) 0.0172(3) Uani 1 1 d . . . C3 C 0.89181(12) 0.09285(7) 0.46546(12) 0.0195(3) Uani 1 1 d . . . H3A H 0.9606 0.0679 0.4937 0.023 Uiso 1 1 calc R . . C4 C 0.90981(12) 0.15693(7) 0.42379(12) 0.0209(3) Uani 1 1 d . . . H4A H 0.9904 0.1757 0.4231 0.025 Uiso 1 1 calc R . . C5 C 0.80878(12) 0.19318(6) 0.38319(12) 0.0191(3) Uani 1 1 d . . . H5A H 0.8214 0.2369 0.3542 0.023 Uiso 1 1 calc R . . C6 C 0.68914(12) 0.16732(6) 0.38368(11) 0.0162(2) Uani 1 1 d . . . C7 C 0.75549(12) -0.00559(6) 0.50589(12) 0.0175(3) Uani 1 1 d . . . C8 C 0.75022(12) -0.02138(7) 0.62953(12) 0.0194(3) Uani 1 1 d . . . C9 C 0.73839(13) -0.08761(7) 0.66311(13) 0.0223(3) Uani 1 1 d . . . H9A H 0.7320 -0.0986 0.7456 0.027 Uiso 1 1 calc R . . C10 C 0.73580(13) -0.13766(7) 0.57833(14) 0.0234(3) Uani 1 1 d . . . H10A H 0.7286 -0.1825 0.6029 0.028 Uiso 1 1 calc R . . C11 C 0.74368(13) -0.12230(7) 0.45779(14) 0.0243(3) Uani 1 1 d . . . H11A H 0.7438 -0.1570 0.4004 0.029 Uiso 1 1 calc R . . C12 C 0.75140(12) -0.05666(7) 0.41881(13) 0.0207(3) Uani 1 1 d . . . C13 C 0.75600(14) 0.03317(7) 0.72416(12) 0.0233(3) Uani 1 1 d . . . H13A H 0.8156 0.0675 0.6957 0.028 Uiso 1 1 calc R . . C14 C 0.62979(17) 0.06631(9) 0.73589(15) 0.0366(4) Uani 1 1 d . . . H14A H 0.6350 0.1017 0.7958 0.055 Uiso 1 1 calc R . . H14B H 0.5687 0.0334 0.7611 0.055 Uiso 1 1 calc R . . H14C H 0.6047 0.0851 0.6583 0.055 Uiso 1 1 calc R . . C15 C 0.80109(15) 0.00928(7) 0.84794(14) 0.0264(3) Uani 1 1 d . . . H15A H 0.8772 -0.0165 0.8389 0.040 Uiso 1 1 calc R . . H15B H 0.7374 -0.0185 0.8843 0.040 Uiso 1 1 calc R . . H15C H 0.8174 0.0476 0.8996 0.040 Uiso 1 1 calc R . . C16 C 0.76087(14) -0.04087(7) 0.28562(13) 0.0249(3) Uani 1 1 d . . . H16A H 0.7171 0.0020 0.2710 0.030 Uiso 1 1 calc R . . C17 C 0.70104(15) -0.09329(9) 0.20380(15) 0.0327(3) Uani 1 1 d . . . H17A H 0.6178 -0.1035 0.2325 0.049 Uiso 1 1 calc R . . H17B H 0.7514 -0.1336 0.2051 0.049 Uiso 1 1 calc R . . H17C H 0.6957 -0.0762 0.1217 0.049 Uiso 1 1 calc R . . C18 C 0.89578(15) -0.03189(9) 0.24890(15) 0.0342(4) Uani 1 1 d . . . H18A H 0.9335 0.0035 0.2968 0.051 Uiso 1 1 calc R . . H18B H 0.8992 -0.0202 0.1637 0.051 Uiso 1 1 calc R . . H18C H 0.9411 -0.0733 0.2626 0.051 Uiso 1 1 calc R . . C19 C 0.58312(12) 0.20752(6) 0.33569(11) 0.0161(2) Uani 1 1 d . . . C20 C 0.53740(13) 0.19463(7) 0.21950(12) 0.0205(3) Uani 1 1 d . B . C21 C 0.43933(14) 0.23234(7) 0.17444(13) 0.0255(3) Uani 1 1 d . . . H21A H 0.4067 0.2230 0.0969 0.031 Uiso 1 1 calc R . . C22 C 0.38917(14) 0.28294(7) 0.24093(15) 0.0281(3) Uani 1 1 d . . . H22A H 0.3223 0.3082 0.2093 0.034 Uiso 1 1 calc R . . C23 C 0.43629(14) 0.29679(7) 0.35363(15) 0.0275(3) Uani 1 1 d . . . H23A H 0.4026 0.3325 0.3980 0.033 Uiso 1 1 calc R . . C24 C 0.53245(12) 0.25942(7) 0.40390(13) 0.0209(3) Uani 1 1 d . . . C25 C 0.59713(15) 0.14308(8) 0.13963(14) 0.0321(4) Uani 1 1 d . . . H25 H 0.6681 0.1235 0.1854 0.038 Uiso 1 1 calc R A 1 C26 C 0.5175(3) 0.08944(17) 0.1030(4) 0.0372(8) Uani 0.697(8) 1 d P B 1 H26A H 0.4861 0.0667 0.1741 0.056 Uiso 0.697(8) 1 calc PR B 1 H26B H 0.5643 0.0581 0.0540 0.056 Uiso 0.697(8) 1 calc PR B 1 H26C H 0.4479 0.1070 0.0558 0.056 Uiso 0.697(8) 1 calc PR B 1 C27 C 0.6526(4) 0.18010(14) 0.0252(4) 0.0432(11) Uani 0.697(8) 1 d P B 1 H27A H 0.7062 0.2165 0.0518 0.065 Uiso 0.697(8) 1 calc PR B 1 H27B H 0.5848 0.1978 -0.0241 0.065 Uiso 0.697(8) 1 calc PR B 1 H27C H 0.7009 0.1487 -0.0222 0.065 Uiso 0.697(8) 1 calc PR B 1 C26A C 0.4939(6) 0.1066(4) 0.0548(7) 0.0280(16) Uani 0.303(8) 1 d P B 2 H26D H 0.4202 0.0969 0.1021 0.042 Uiso 0.303(8) 1 calc PR B 2 H26E H 0.5281 0.0652 0.0235 0.042 Uiso 0.303(8) 1 calc PR B 2 H26F H 0.4714 0.1357 -0.0122 0.042 Uiso 0.303(8) 1 calc PR B 2 C27A C 0.7010(6) 0.1580(5) 0.0873(8) 0.047(3) Uani 0.303(8) 1 d P B 2 H27D H 0.7619 0.1719 0.1478 0.070 Uiso 0.303(8) 1 calc PR B 2 H27E H 0.6869 0.1941 0.0302 0.070 Uiso 0.303(8) 1 calc PR B 2 H27F H 0.7321 0.1191 0.0446 0.070 Uiso 0.303(8) 1 calc PR B 2 C28 C 0.57893(14) 0.27341(8) 0.53065(14) 0.0285(3) Uani 1 1 d . . . H28A H 0.6689 0.2621 0.5343 0.034 Uiso 1 1 calc R . . C29 C 0.51222(17) 0.22974(8) 0.62053(14) 0.0342(4) Uani 1 1 d . . . H29A H 0.5175 0.1834 0.5951 0.051 Uiso 1 1 calc R . . H29B H 0.4252 0.2430 0.6246 0.051 Uiso 1 1 calc R . . H29C H 0.5510 0.2347 0.6998 0.051 Uiso 1 1 calc R . . C30 C 0.5645(2) 0.34628(9) 0.56798(17) 0.0468(5) Uani 1 1 d . . . H30A H 0.6039 0.3748 0.5085 0.070 Uiso 1 1 calc R . . H30B H 0.6039 0.3532 0.6465 0.070 Uiso 1 1 calc R . . H30C H 0.4764 0.3573 0.5728 0.070 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 0.02349(15) 0.01537(14) 0.02129(15) 0.00236(10) -0.00118(11) -0.00522(10) O1 0.0161(4) 0.0163(4) 0.0235(5) 0.0027(4) -0.0023(4) -0.0013(3) C1 0.0166(6) 0.0164(6) 0.0153(6) -0.0002(5) -0.0009(5) -0.0014(5) C2 0.0192(6) 0.0154(6) 0.0171(6) 0.0006(5) -0.0014(5) -0.0002(5) C3 0.0175(6) 0.0204(6) 0.0207(6) 0.0010(5) -0.0029(5) 0.0012(5) C4 0.0173(6) 0.0224(7) 0.0228(7) 0.0003(5) -0.0016(5) -0.0045(5) C5 0.0230(7) 0.0157(6) 0.0186(6) 0.0018(5) -0.0011(5) -0.0039(5) C6 0.0190(6) 0.0152(6) 0.0145(6) -0.0005(4) -0.0015(5) -0.0002(5) C7 0.0139(6) 0.0154(6) 0.0233(7) 0.0020(5) -0.0026(5) 0.0011(4) C8 0.0177(6) 0.0167(6) 0.0237(7) 0.0017(5) -0.0004(5) 0.0016(5) C9 0.0216(7) 0.0188(6) 0.0265(7) 0.0046(5) -0.0002(5) 0.0007(5) C10 0.0209(6) 0.0145(6) 0.0346(8) 0.0035(5) -0.0036(6) -0.0001(5) C11 0.0243(7) 0.0168(6) 0.0319(8) -0.0034(5) -0.0038(6) 0.0016(5) C12 0.0173(6) 0.0195(6) 0.0251(7) -0.0003(5) -0.0032(5) 0.0019(5) C13 0.0309(7) 0.0171(6) 0.0221(7) 0.0023(5) 0.0015(6) 0.0019(5) C14 0.0451(10) 0.0390(9) 0.0257(8) -0.0013(7) -0.0002(7) 0.0200(8) C15 0.0313(8) 0.0225(7) 0.0253(7) 0.0018(6) -0.0031(6) -0.0015(6) C16 0.0285(7) 0.0231(7) 0.0232(7) -0.0024(5) -0.0020(6) 0.0022(6) C17 0.0296(8) 0.0391(9) 0.0293(8) -0.0069(7) -0.0047(6) 0.0000(7) C18 0.0323(8) 0.0418(10) 0.0285(8) -0.0073(7) 0.0038(6) -0.0045(7) C19 0.0188(6) 0.0123(6) 0.0173(6) 0.0022(5) -0.0004(5) -0.0012(4) C20 0.0243(7) 0.0192(6) 0.0180(6) 0.0018(5) -0.0019(5) 0.0017(5) C21 0.0271(7) 0.0276(7) 0.0217(7) 0.0072(6) -0.0049(6) 0.0019(6) C22 0.0239(7) 0.0218(7) 0.0386(9) 0.0087(6) -0.0025(6) 0.0043(6) C23 0.0249(7) 0.0167(6) 0.0411(9) -0.0045(6) 0.0050(6) 0.0029(5) C24 0.0204(6) 0.0184(6) 0.0238(7) -0.0043(5) 0.0022(5) -0.0039(5) C25 0.0353(8) 0.0384(9) 0.0223(7) -0.0117(6) -0.0100(6) 0.0131(7) C26 0.0429(18) 0.0293(15) 0.040(2) -0.0093(14) 0.0088(16) -0.0047(12) C27 0.056(2) 0.0362(15) 0.0375(19) -0.0107(12) 0.0237(16) -0.0144(13) C26A 0.027(3) 0.037(4) 0.020(3) -0.009(3) -0.003(2) -0.010(3) C27A 0.031(3) 0.076(6) 0.034(4) -0.030(4) 0.010(3) -0.017(3) C28 0.0248(7) 0.0348(8) 0.0258(7) -0.0134(6) -0.0007(6) -0.0025(6) C29 0.0515(10) 0.0270(8) 0.0239(7) -0.0013(6) -0.0078(7) -0.0008(7) C30 0.0728(14) 0.0332(9) 0.0345(9) -0.0129(7) 0.0059(9) -0.0202(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O1 1.8472(9) 3_656 ? Fe1 O1 1.8472(9) . ? O1 C1 1.3485(15) . ? C1 C2 1.4088(18) . ? C1 C6 1.4158(18) . ? C2 C3 1.3963(18) . ? C2 C7 1.5025(17) . ? C3 C4 1.3899(19) . ? C3 H3A 0.9500 . ? C4 C5 1.3877(19) . ? C4 H4A 0.9500 . ? C5 C6 1.3953(18) . ? C5 H5A 0.9500 . ? C6 C19 1.4996(17) . ? C7 C8 1.4174(19) . ? C7 C12 1.4177(19) . ? C8 C9 1.3958(19) . ? C8 C13 1.5270(19) . ? C9 C10 1.385(2) . ? C9 H9A 0.9500 . ? C10 C11 1.383(2) . ? C10 H10A 0.9500 . ? C11 C12 1.3982(19) . ? C11 H11A 0.9500 . ? C12 C16 1.524(2) . ? C13 C14 1.527(2) . ? C13 C15 1.538(2) . ? C13 H13A 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.530(2) . ? C16 C17 1.537(2) . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.4071(18) . ? C19 C24 1.4096(18) . ? C20 C21 1.3955(19) . ? C20 C25 1.519(2) . ? C21 C22 1.378(2) . ? C21 H21A 0.9500 . ? C22 C23 1.381(2) . ? C22 H22A 0.9500 . ? C23 C24 1.398(2) . ? C23 H23A 0.9500 . ? C24 C28 1.522(2) . ? C25 C27A 1.306(6) . ? C25 C26 1.441(4) . ? C25 C27 1.602(3) . ? C25 C26A 1.633(6) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C26A H26D 0.9800 . ? C26A H26E 0.9800 . ? C26A H26F 0.9800 . ? C27A H27D 0.9800 . ? C27A H27E 0.9800 . ? C27A H27F 0.9800 . ? C28 C29 1.523(2) . ? C28 C30 1.538(2) . ? C28 H28A 1.0000 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 O1 Fe1 O1 180.00(3) 3_656 . ? C1 O1 Fe1 129.33(8) . . ? O1 C1 C2 120.79(11) . . ? O1 C1 C6 119.55(11) . . ? C2 C1 C6 119.66(12) . . ? C3 C2 C1 119.81(12) . . ? C3 C2 C7 120.62(12) . . ? C1 C2 C7 119.54(11) . . ? C4 C3 C2 120.76(12) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C5 C4 C3 119.23(12) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 121.88(12) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C5 C6 C1 118.65(12) . . ? C5 C6 C19 120.10(11) . . ? C1 C6 C19 121.22(11) . . ? C8 C7 C12 120.11(12) . . ? C8 C7 C2 120.41(12) . . ? C12 C7 C2 119.36(12) . . ? C9 C8 C7 118.79(12) . . ? C9 C8 C13 120.64(12) . . ? C7 C8 C13 120.56(12) . . ? C10 C9 C8 121.21(13) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C11 C10 C9 119.94(13) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 121.30(13) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C11 C12 C7 118.60(13) . . ? C11 C12 C16 120.44(13) . . ? C7 C12 C16 120.91(12) . . ? C14 C13 C8 110.19(13) . . ? C14 C13 C15 109.67(12) . . ? C8 C13 C15 113.87(11) . . ? C14 C13 H13A 107.6 . . ? C8 C13 H13A 107.6 . . ? C15 C13 H13A 107.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 C18 111.05(12) . . ? C12 C16 C17 113.75(13) . . ? C18 C16 C17 108.65(12) . . ? C12 C16 H16A 107.7 . . ? C18 C16 H16A 107.7 . . ? C17 C16 H16A 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 120.01(12) . . ? C20 C19 C6 119.29(11) . . ? C24 C19 C6 120.66(11) . . ? C21 C20 C19 119.32(13) . . ? C21 C20 C25 119.28(12) . . ? C19 C20 C25 121.31(12) . . ? C22 C21 C20 120.87(14) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C21 C22 C23 119.80(13) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C22 C23 C24 121.50(13) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? C23 C24 C19 118.47(13) . . ? C23 C24 C28 120.66(13) . . ? C19 C24 C28 120.86(13) . . ? C27A C25 C20 118.5(4) . . ? C26 C25 C20 115.20(17) . . ? C26 C25 C27 110.6(2) . . ? C20 C25 C27 108.20(15) . . ? C27A C25 C26A 115.5(4) . . ? C20 C25 C26A 110.9(3) . . ? C27 C25 C26A 90.5(3) . . ? C27A C25 H25 70.2 . . ? C26 C25 H25 107.5 . . ? C20 C25 H25 107.5 . . ? C27 C25 H25 107.5 . . ? C26A C25 H25 129.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? C25 C26A H26D 109.5 . . ? C25 C26A H26E 109.5 . . ? H26D C26A H26E 109.5 . . ? C25 C26A H26F 109.5 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C25 C27A H27D 109.5 . . ? C25 C27A H27E 109.5 . . ? H27D C27A H27E 109.5 . . ? C25 C27A H27F 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? C24 C28 C29 110.48(12) . . ? C24 C28 C30 113.30(14) . . ? C29 C28 C30 109.04(13) . . ? C24 C28 H28A 107.9 . . ? C29 C28 H28A 107.9 . . ? C30 C28 H28A 107.9 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.401 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.048 #===END data_tw52 _database_code_depnum_ccdc_archive 'CCDC 737426' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C64 H74 Fe O4' _chemical_formula_sum 'C64 H74 Fe O4' _chemical_formula_weight 963.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.3259(8) _cell_length_b 19.1534(12) _cell_length_c 22.7301(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5366.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 8267 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.44 _exptl_crystal_description Plate _exptl_crystal_colour Red _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9166 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details 'TWINABS V2008/3 (Sheldrick, 2008)' _exptl_special_details ; A red plate with approximate orthogonal dimensions 0.27 x 0.21 x 0.12mm3 was placed and optically centered on the Bruker APEXII(1) CCD system at 90(2)K (-183C). The initial unit cell was indexed using a least-squares analysis of a random set of reflections collected from three series of 0.3?wide omega-scans, 10 seconds per frame, and 20 frames per series that were well distributed in reciprocal space. Four omega-scan data frame series were collected [MoKa] with 0.3?wide scans, 35 seconds per frame and 606, 455, 606, 382 frames were collected, at varying phi angles (phi=0? 90? 180? 270?, for each series, respectively. The crystal to detector distance was 5.32cm, thus providing a complete sphere of data with processing to 2ThetaMax=55.00? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8265 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8265 _reflns_number_gt 6986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Version 5.054) (Bruker, 2002)' _computing_cell_refinement 'SAINT (7.53A) (Bruker, 2006)' _computing_data_reduction 'SAINT (7.53A) (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL 5.1, XP (Sheldrick, 1994)' _computing_publication_material SHELXL97 _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. Structural determination and Refinement: All crystallographic calculations were performed on a Personal computer (PC) with a Pentium 3.20GHz processor and 4GB of extended memory. Data were collected based upon a single component, processed with SAINT(1), and corrected for Lorentz and polarization effects and absorption using Blessing's method as incorporated into the program SADABS(2,3). The SHELXTL(4) program package was now implemented to determine, based upon intensity statistics and systematic absences, the centrosymmetric, orthorhombic space group Pbcn (no.60). The structure was determined by direct methods using the program XS(5). Refinement of the structure was achieved using the program XL(5). All of the non-hydrogen atoms were located initially with XS or from a series of difference-Fourier map least-squares cycles and convergence proceeded quickly. One half molecule was located and refined; Iron atom at center of symmetry. The crystal appeared to be twinned and, due to the large estimated standard deviations for the cell parameters, reflections were thresholded and Cellnow6 now determined the relative orientations of the two major domains; the latter rotated 180.0 degrees about the real axis -1 1 0 and generated the orientation matrices for the components and output a useable multiple matrix input file for SAINT1. At the completion of the data processing with SAINT, the optimized merged matrix was re-input and the data were processed an additional two times. Cell parameter esd's decreased dramatically. Data collected were corrected for Lorentz and polarization effects and absorption using Blessing's method using TWINABS(3,7), merged and then output final HKLF5 and HKLF4 files. The two component structure was refined to convergence with BASF = 0.424 and R(F)=3.58%, wR(F2)=8.23% for those 6986 data with Fo > 4 (Fo) and R(F)=5.21%, wR(F2)=8.99%, GOF=1.075 for all 8265 reflections. During the final refinements, the command L.S. 9 was changed to L.S. 9 0 2100 to account for the 'extra' reflections and produce realistic esd's. A final difference-Fourier map was featureless indicating that the structure is therefore both correct and complete. An empirical correction for extinction was not attempted due to the twinning. References: 1. Bruker (2007) APEX (Version 2.020) and SAINT (Version 7.53a). Bruker AXS Inc., Madison, Wisconsin, USA. 2. Sheldrick, G.M., SADABS (2008) Version 2008/2, 'Siemens Area Detector Absorption Correction' Universit\"at G\"ottingen: G\"ottingen, Germany. 3. An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995). Acta Cryst., A51, 33-38. 4. Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. 5. Sheldrick, G. M., (1997). SHELXS97 and SHELXL97. Universit\"at G\"ottingen: G\"ottingen, Germany. 6. Sheldrick, G.M., CELLNOW v2008/3, Twin matrix determination program, Universit\"at G\"ottingen: G\"ottingen, Germany, 2008. 7. Sheldrick, G.M., TWINABS 'An Empirical Correction for Absorption Anisotropy applied to Twinned crystals' v2008/3. Universit\"at G\"ottingen: G\"ottingen, Germany, 2008. 021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.34 The ShelxL command L.S. 9 0 2100 was used to eliminate the underestimation of the parameter esd's. Data collected listed as 8265, unique 6165. 931_ALERT_5_G Check Twin Law ( 1-1 0)[ ] Estimated BASF 0.30 This twin law was determined with Cellnow and used when were data reduced with SAINT. ; _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^)+(0.0362P)^2^+4.0405P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8265 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.12724(2) 0.7500 0.01515(8) Uani 1 2 d S . . O1 O 0.65554(12) 0.01282(8) 0.75404(7) 0.0317(4) Uani 1 1 d . . . O2 O 0.58920(11) 0.20282(7) 0.71095(6) 0.0196(3) Uani 1 1 d . . . C1 C 0.59823(15) 0.05973(10) 0.75289(9) 0.0206(4) Uani 1 1 d . . . C2 C 0.53039(14) 0.17001(10) 0.67658(8) 0.0171(4) Uani 1 1 d . . . C3 C 0.52387(15) 0.18380(9) 0.61287(8) 0.0178(4) Uani 1 1 d . . . C4 C 0.43210(15) 0.16111(10) 0.58134(9) 0.0183(4) Uani 1 1 d . . . C5 C 0.42881(16) 0.17158(10) 0.52048(9) 0.0225(4) Uani 1 1 d . . . H5A H 0.3673 0.1565 0.4988 0.027 Uiso 1 1 calc R . . C6 C 0.51373(18) 0.20355(10) 0.49151(9) 0.0235(4) Uani 1 1 d . . . H6A H 0.5117 0.2086 0.4499 0.028 Uiso 1 1 calc R . . C7 C 0.60200(17) 0.22834(10) 0.52296(9) 0.0223(4) Uani 1 1 d . . . H7A H 0.6592 0.2513 0.5026 0.027 Uiso 1 1 calc R . . C8 C 0.60855(16) 0.22033(9) 0.58365(8) 0.0181(4) Uani 1 1 d . . . C9 C 0.33462(15) 0.12958(11) 0.61007(8) 0.0196(4) Uani 1 1 d . . . C10 C 0.30852(16) 0.05944(10) 0.59839(9) 0.0227(4) Uani 1 1 d . . . C11 C 0.21405(17) 0.03175(11) 0.62239(11) 0.0307(5) Uani 1 1 d . . . H11A H 0.1956 -0.0155 0.6147 0.037 Uiso 1 1 calc R . . C12 C 0.14670(18) 0.07172(12) 0.65713(12) 0.0345(5) Uani 1 1 d . . . H12A H 0.0826 0.0519 0.6733 0.041 Uiso 1 1 calc R . . C13 C 0.17253(17) 0.14099(12) 0.66857(10) 0.0284(5) Uani 1 1 d . . . H13A H 0.1256 0.1681 0.6926 0.034 Uiso 1 1 calc R . . C14 C 0.26601(16) 0.17150(11) 0.64550(9) 0.0221(4) Uani 1 1 d . . . C15 C 0.38441(17) 0.01213(10) 0.56313(9) 0.0247(4) Uani 1 1 d . . . H15A H 0.4377 0.0426 0.5422 0.030 Uiso 1 1 calc R . . C16 C 0.4481(2) -0.03549(13) 0.60453(11) 0.0378(6) Uani 1 1 d . . . H16A H 0.4909 -0.0070 0.6318 0.057 Uiso 1 1 calc R . . H16B H 0.4967 -0.0653 0.5815 0.057 Uiso 1 1 calc R . . H16C H 0.3974 -0.0647 0.6269 0.057 Uiso 1 1 calc R . . C17 C 0.32441(19) -0.03102(12) 0.51672(11) 0.0339(5) Uani 1 1 d . . . H17A H 0.2844 0.0003 0.4904 0.051 Uiso 1 1 calc R . . H17B H 0.2735 -0.0628 0.5362 0.051 Uiso 1 1 calc R . . H17C H 0.3769 -0.0582 0.4938 0.051 Uiso 1 1 calc R . . C18 C 0.29193(16) 0.24804(10) 0.65810(9) 0.0213(4) Uani 1 1 d . . . H18A H 0.3706 0.2505 0.6687 0.026 Uiso 1 1 calc R . . C19 C 0.2757(2) 0.29459(12) 0.60398(10) 0.0315(5) Uani 1 1 d . . . H19A H 0.2995 0.3422 0.6131 0.047 Uiso 1 1 calc R . . H19B H 0.1987 0.2951 0.5932 0.047 Uiso 1 1 calc R . . H19C H 0.3185 0.2762 0.5711 0.047 Uiso 1 1 calc R . . C20 C 0.22872(18) 0.27932(12) 0.70956(10) 0.0292(5) Uani 1 1 d . . . H20A H 0.2550 0.3267 0.7174 0.044 Uiso 1 1 calc R . . H20B H 0.2392 0.2503 0.7446 0.044 Uiso 1 1 calc R . . H20C H 0.1514 0.2810 0.6997 0.044 Uiso 1 1 calc R . . C21 C 0.70159(16) 0.25582(10) 0.61353(8) 0.0191(4) Uani 1 1 d . . . C22 C 0.69077(17) 0.32764(10) 0.62642(9) 0.0237(4) Uani 1 1 d . . . C23 C 0.78074(18) 0.36318(11) 0.64887(9) 0.0276(4) Uani 1 1 d . . . H23A H 0.7751 0.4116 0.6573 0.033 Uiso 1 1 calc R . . C24 C 0.87725(18) 0.32929(12) 0.65898(9) 0.0283(5) Uani 1 1 d . . . H24A H 0.9373 0.3543 0.6746 0.034 Uiso 1 1 calc R . . C25 C 0.88722(17) 0.25875(12) 0.64651(9) 0.0260(4) Uani 1 1 d . . . H25A H 0.9541 0.2357 0.6538 0.031 Uiso 1 1 calc R . . C26 C 0.79978(16) 0.22116(10) 0.62331(9) 0.0209(4) Uani 1 1 d . . . C27 C 0.58413(18) 0.36569(11) 0.61732(10) 0.0278(5) Uani 1 1 d . . . H27A H 0.5300 0.3307 0.6030 0.033 Uiso 1 1 calc R . . C28 C 0.5419(2) 0.39499(13) 0.67556(11) 0.0403(6) Uani 1 1 d . . . H28A H 0.5331 0.3568 0.7039 0.060 Uiso 1 1 calc R . . H28B H 0.4718 0.4178 0.6691 0.060 Uiso 1 1 calc R . . H28C H 0.5939 0.4291 0.6911 0.060 Uiso 1 1 calc R . . C29 C 0.5935(2) 0.42236(13) 0.57048(11) 0.0364(5) Uani 1 1 d . . . H29A H 0.6119 0.4010 0.5326 0.055 Uiso 1 1 calc R . . H29B H 0.6505 0.4555 0.5817 0.055 Uiso 1 1 calc R . . H29C H 0.5242 0.4470 0.5670 0.055 Uiso 1 1 calc R . . C30 C 0.81354(17) 0.14377(11) 0.61030(10) 0.0241(4) Uani 1 1 d . . . H30A H 0.7426 0.1257 0.5953 0.029 Uiso 1 1 calc R . . C31 C 0.89922(18) 0.13087(12) 0.56275(10) 0.0283(4) Uani 1 1 d . . . H31A H 0.8792 0.1562 0.5269 0.042 Uiso 1 1 calc R . . H31B H 0.9034 0.0808 0.5542 0.042 Uiso 1 1 calc R . . H31C H 0.9699 0.1474 0.5767 0.042 Uiso 1 1 calc R . . C32 C 0.84045(19) 0.10408(12) 0.66710(11) 0.0318(5) Uani 1 1 d . . . H32A H 0.7849 0.1139 0.6968 0.048 Uiso 1 1 calc R . . H32B H 0.9115 0.1191 0.6817 0.048 Uiso 1 1 calc R . . H32C H 0.8421 0.0538 0.6590 0.048 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 0.01434(18) 0.01418(18) 0.01694(16) 0.000 -0.00064(15) 0.000 O1 0.0292(8) 0.0259(8) 0.0399(9) 0.0039(7) 0.0032(7) 0.0097(6) O2 0.0194(7) 0.0200(7) 0.0193(6) 0.0016(5) -0.0018(5) -0.0041(5) C1 0.0192(9) 0.0226(9) 0.0200(9) 0.0028(8) 0.0019(8) -0.0004(7) C2 0.0150(8) 0.0146(8) 0.0218(9) -0.0004(7) -0.0008(7) 0.0029(6) C3 0.0208(9) 0.0116(8) 0.0210(9) -0.0011(7) -0.0001(7) 0.0026(6) C4 0.0201(9) 0.0115(8) 0.0234(9) -0.0019(7) -0.0029(7) 0.0044(7) C5 0.0240(10) 0.0200(10) 0.0235(10) -0.0031(8) -0.0058(8) 0.0043(7) C6 0.0348(11) 0.0199(9) 0.0159(9) -0.0012(7) -0.0019(8) 0.0068(8) C7 0.0276(10) 0.0175(10) 0.0218(9) 0.0016(7) 0.0047(8) 0.0007(8) C8 0.0212(10) 0.0119(9) 0.0214(9) -0.0015(7) 0.0000(8) 0.0028(7) C9 0.0163(9) 0.0196(9) 0.0229(9) 0.0004(8) -0.0053(7) 0.0021(7) C10 0.0189(10) 0.0196(10) 0.0296(11) -0.0019(8) -0.0056(8) 0.0014(7) C11 0.0223(10) 0.0209(11) 0.0490(14) -0.0019(10) -0.0046(10) -0.0032(8) C12 0.0176(10) 0.0317(12) 0.0543(16) 0.0019(11) 0.0016(10) -0.0023(8) C13 0.0193(10) 0.0298(12) 0.0360(12) -0.0018(10) -0.0004(8) 0.0056(8) C14 0.0177(9) 0.0230(10) 0.0256(10) -0.0001(8) -0.0064(8) 0.0034(8) C15 0.0235(10) 0.0187(10) 0.0319(11) -0.0028(8) -0.0043(9) 0.0006(8) C16 0.0374(13) 0.0416(14) 0.0343(13) -0.0110(11) -0.0121(11) 0.0196(11) C17 0.0370(13) 0.0300(12) 0.0348(12) -0.0074(10) -0.0109(10) 0.0024(10) C18 0.0205(9) 0.0201(9) 0.0233(10) -0.0025(8) -0.0034(8) 0.0064(7) C19 0.0458(14) 0.0232(10) 0.0255(11) -0.0013(9) -0.0051(10) 0.0112(10) C20 0.0289(12) 0.0289(11) 0.0297(11) -0.0050(9) -0.0021(9) 0.0087(9) C21 0.0228(10) 0.0180(9) 0.0165(9) 0.0015(7) 0.0028(7) -0.0032(7) C22 0.0301(11) 0.0193(10) 0.0217(10) 0.0005(8) 0.0065(8) -0.0023(8) C23 0.0368(12) 0.0203(10) 0.0256(10) -0.0016(8) 0.0064(9) -0.0089(8) C24 0.0309(12) 0.0298(11) 0.0242(10) -0.0011(9) 0.0036(9) -0.0160(9) C25 0.0216(10) 0.0309(11) 0.0254(10) 0.0026(9) 0.0025(8) -0.0051(8) C26 0.0218(10) 0.0197(10) 0.0211(10) 0.0009(8) 0.0013(8) -0.0037(7) C27 0.0323(11) 0.0165(10) 0.0348(12) 0.0000(9) 0.0037(9) 0.0010(8) C28 0.0464(15) 0.0337(13) 0.0407(14) 0.0014(11) 0.0138(12) 0.0113(11) C29 0.0459(14) 0.0272(12) 0.0362(13) 0.0057(10) 0.0022(11) 0.0040(10) C30 0.0205(10) 0.0186(10) 0.0332(11) -0.0001(8) 0.0007(8) -0.0007(7) C31 0.0329(11) 0.0235(11) 0.0283(11) 0.0003(9) 0.0019(9) 0.0019(9) C32 0.0302(12) 0.0277(11) 0.0374(13) 0.0072(10) 0.0091(10) 0.0033(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 1.773(2) 3_656 ? Fe1 C1 1.7726(19) . ? Fe1 C2 1.8964(18) 3_656 ? Fe1 C2 1.8965(19) . ? Fe1 O2 2.0230(13) . ? Fe1 O2 2.0230(13) 3_656 ? O1 C1 1.143(2) . ? O2 C2 1.237(2) . ? C2 C3 1.474(3) . ? C3 C4 1.408(3) . ? C3 C8 1.421(3) . ? C4 C5 1.399(3) . ? C4 C9 1.495(3) . ? C5 C6 1.380(3) . ? C5 H5A 0.9500 . ? C6 C7 1.386(3) . ? C6 H6A 0.9500 . ? C7 C8 1.390(3) . ? C7 H7A 0.9500 . ? C8 C21 1.496(3) . ? C9 C10 1.407(3) . ? C9 C14 1.417(3) . ? C10 C11 1.391(3) . ? C10 C15 1.529(3) . ? C11 C12 1.378(3) . ? C11 H11A 0.9500 . ? C12 C13 1.389(3) . ? C12 H12A 0.9500 . ? C13 C14 1.394(3) . ? C13 H13A 0.9500 . ? C14 C18 1.528(3) . ? C15 C16 1.527(3) . ? C15 C17 1.531(3) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C20 1.528(3) . ? C18 C19 1.532(3) . ? C18 H18A 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.398(3) . ? C21 C22 1.413(3) . ? C22 C23 1.398(3) . ? C22 C27 1.517(3) . ? C23 C24 1.374(3) . ? C23 H23A 0.9500 . ? C24 C25 1.386(3) . ? C24 H24A 0.9500 . ? C25 C26 1.399(3) . ? C25 H25A 0.9500 . ? C26 C30 1.521(3) . ? C27 C29 1.525(3) . ? C27 C28 1.529(3) . ? C27 H27A 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.531(3) . ? C30 C32 1.535(3) . ? C30 H30A 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 C1 Fe1 C1 86.33(12) 3_656 . ? C1 Fe1 C2 102.29(9) 3_656 3_656 ? C1 Fe1 C2 114.67(9) . 3_656 ? C1 Fe1 C2 114.67(9) 3_656 . ? C1 Fe1 C2 102.29(9) . . ? C2 Fe1 C2 128.81(11) 3_656 . ? C1 Fe1 O2 151.27(8) 3_656 . ? C1 Fe1 O2 99.62(7) . . ? C2 Fe1 O2 100.62(7) 3_656 . ? C2 Fe1 O2 36.62(7) . . ? C1 Fe1 O2 99.61(7) 3_656 3_656 ? C1 Fe1 O2 151.27(8) . 3_656 ? C2 Fe1 O2 36.62(6) 3_656 3_656 ? C2 Fe1 O2 100.62(7) . 3_656 ? O2 Fe1 O2 88.61(8) . 3_656 ? C2 O2 Fe1 66.12(10) . . ? O1 C1 Fe1 174.98(18) . . ? O2 C2 C3 124.13(17) . . ? O2 C2 Fe1 77.26(11) . . ? C3 C2 Fe1 158.60(14) . . ? C4 C3 C8 120.28(17) . . ? C4 C3 C2 119.24(17) . . ? C8 C3 C2 120.48(17) . . ? C5 C4 C3 118.85(18) . . ? C5 C4 C9 117.82(17) . . ? C3 C4 C9 123.24(17) . . ? C6 C5 C4 120.91(18) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C7 120.10(18) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C8 121.30(19) . . ? C6 C7 H7A 119.3 . . ? C8 C7 H7A 119.3 . . ? C7 C8 C3 118.38(18) . . ? C7 C8 C21 116.41(17) . . ? C3 C8 C21 125.06(17) . . ? C10 C9 C14 120.80(18) . . ? C10 C9 C4 119.16(17) . . ? C14 C9 C4 119.92(18) . . ? C11 C10 C9 118.79(19) . . ? C11 C10 C15 119.45(18) . . ? C9 C10 C15 121.67(18) . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 121.3(2) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C13 C14 C9 117.99(19) . . ? C13 C14 C18 120.30(18) . . ? C9 C14 C18 121.71(18) . . ? C16 C15 C10 110.20(18) . . ? C16 C15 C17 110.51(18) . . ? C10 C15 C17 112.68(18) . . ? C16 C15 H15A 107.8 . . ? C10 C15 H15A 107.8 . . ? C17 C15 H15A 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 C20 114.41(18) . . ? C14 C18 C19 112.37(17) . . ? C20 C18 C19 108.66(17) . . ? C14 C18 H18A 107.0 . . ? C20 C18 H18A 107.0 . . ? C19 C18 H18A 107.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 120.73(18) . . ? C26 C21 C8 121.33(17) . . ? C22 C21 C8 117.66(18) . . ? C23 C22 C21 118.4(2) . . ? C23 C22 C27 120.22(19) . . ? C21 C22 C27 121.41(18) . . ? C24 C23 C22 121.2(2) . . ? C24 C23 H23A 119.4 . . ? C22 C23 H23A 119.4 . . ? C23 C24 C25 120.19(19) . . ? C23 C24 H24A 119.9 . . ? C25 C24 H24A 119.9 . . ? C24 C25 C26 120.7(2) . . ? C24 C25 H25A 119.7 . . ? C26 C25 H25A 119.7 . . ? C21 C26 C25 118.84(19) . . ? C21 C26 C30 121.89(18) . . ? C25 C26 C30 119.27(19) . . ? C22 C27 C29 111.80(18) . . ? C22 C27 C28 110.67(19) . . ? C29 C27 C28 111.65(19) . . ? C22 C27 H27A 107.5 . . ? C29 C27 H27A 107.5 . . ? C28 C27 H27A 107.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 C31 111.80(17) . . ? C26 C30 C32 110.08(18) . . ? C31 C30 C32 111.40(17) . . ? C26 C30 H30A 107.8 . . ? C31 C30 H30A 107.8 . . ? C32 C30 H30A 107.8 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C1 Fe1 O2 C2 -2.3(2) 3_656 . . . ? C1 Fe1 O2 C2 97.70(13) . . . . ? C2 Fe1 O2 C2 -144.76(11) 3_656 . . . ? O2 Fe1 O2 C2 -109.98(12) 3_656 . . . ? Fe1 O2 C2 C3 179.7(2) . . . . ? C1 Fe1 C2 O2 178.77(11) 3_656 . . . ? C1 Fe1 C2 O2 -89.63(12) . . . . ? C2 Fe1 C2 O2 46.71(9) 3_656 . . . ? O2 Fe1 C2 O2 72.92(13) 3_656 . . . ? C1 Fe1 C2 C3 -0.6(4) 3_656 . . . ? C1 Fe1 C2 C3 91.0(4) . . . . ? C2 Fe1 C2 C3 -132.7(4) 3_656 . . . ? O2 Fe1 C2 C3 -179.4(5) . . . . ? O2 Fe1 C2 C3 -106.4(4) 3_656 . . . ? O2 C2 C3 C4 -159.14(18) . . . . ? Fe1 C2 C3 C4 20.1(5) . . . . ? O2 C2 C3 C8 20.1(3) . . . . ? Fe1 C2 C3 C8 -160.6(3) . . . . ? C8 C3 C4 C5 3.6(3) . . . . ? C2 C3 C4 C5 -177.12(17) . . . . ? C8 C3 C4 C9 -172.98(17) . . . . ? C2 C3 C4 C9 6.3(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C9 C4 C5 C6 176.81(17) . . . . ? C4 C5 C6 C7 -2.6(3) . . . . ? C5 C6 C7 C8 1.5(3) . . . . ? C6 C7 C8 C3 2.1(3) . . . . ? C6 C7 C8 C21 -173.66(18) . . . . ? C4 C3 C8 C7 -4.7(3) . . . . ? C2 C3 C8 C7 176.10(17) . . . . ? C4 C3 C8 C21 170.69(17) . . . . ? C2 C3 C8 C21 -8.5(3) . . . . ? C5 C4 C9 C10 68.4(2) . . . . ? C3 C4 C9 C10 -114.9(2) . . . . ? C5 C4 C9 C14 -107.5(2) . . . . ? C3 C4 C9 C14 69.1(2) . . . . ? C14 C9 C10 C11 -0.2(3) . . . . ? C4 C9 C10 C11 -176.09(19) . . . . ? C14 C9 C10 C15 -176.57(18) . . . . ? C4 C9 C10 C15 7.5(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C15 C10 C11 C12 176.4(2) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C12 C13 C14 C18 179.2(2) . . . . ? C10 C9 C14 C13 0.4(3) . . . . ? C4 C9 C14 C13 176.26(18) . . . . ? C10 C9 C14 C18 -179.17(17) . . . . ? C4 C9 C14 C18 -3.3(3) . . . . ? C11 C10 C15 C16 -75.2(3) . . . . ? C9 C10 C15 C16 101.2(2) . . . . ? C11 C10 C15 C17 48.8(3) . . . . ? C9 C10 C15 C17 -134.8(2) . . . . ? C13 C14 C18 C20 16.6(3) . . . . ? C9 C14 C18 C20 -163.91(18) . . . . ? C13 C14 C18 C19 -107.9(2) . . . . ? C9 C14 C18 C19 71.6(2) . . . . ? C7 C8 C21 C26 -92.2(2) . . . . ? C3 C8 C21 C26 92.4(2) . . . . ? C7 C8 C21 C22 81.8(2) . . . . ? C3 C8 C21 C22 -93.7(2) . . . . ? C26 C21 C22 C23 0.3(3) . . . . ? C8 C21 C22 C23 -173.66(18) . . . . ? C26 C21 C22 C27 -178.66(19) . . . . ? C8 C21 C22 C27 7.4(3) . . . . ? C21 C22 C23 C24 -0.8(3) . . . . ? C27 C22 C23 C24 178.19(19) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C22 C21 C26 C25 0.4(3) . . . . ? C8 C21 C26 C25 174.19(18) . . . . ? C22 C21 C26 C30 179.51(19) . . . . ? C8 C21 C26 C30 -6.7(3) . . . . ? C24 C25 C26 C21 -0.7(3) . . . . ? C24 C25 C26 C30 -179.84(19) . . . . ? C23 C22 C27 C29 65.0(3) . . . . ? C21 C22 C27 C29 -116.0(2) . . . . ? C23 C22 C27 C28 -60.1(3) . . . . ? C21 C22 C27 C28 118.8(2) . . . . ? C21 C26 C30 C31 117.6(2) . . . . ? C25 C26 C30 C31 -63.3(3) . . . . ? C21 C26 C30 C32 -118.0(2) . . . . ? C25 C26 C30 C32 61.1(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.053