data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Fe O6' _chemical_formula_weight 308.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.058(6) _cell_length_b 6.386(3) _cell_length_c 7.409(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.001(7) _cell_angle_gamma 90.00 _cell_volume 617.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1604 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 26.39 _exptl_crystal_description 'prism' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 1.240 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8358 _exptl_absorpt_correction_T_max 0.9073 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3712 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 26.71 _reflns_number_total 1280 _reflns_number_gt 916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0136P)^2^+3.4546P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1280 _refine_ls_number_parameters 94 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1810 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 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 0.0199(4) Uani 1 2 d S . . C1 C 0.3552(5) 0.2471(10) 0.2500(9) 0.0191(13) Uani 1 1 d . . . O1 O 0.4105(4) 0.0892(8) 0.2698(7) 0.0329(13) Uani 1 1 d . . . C3 C 0.2062(6) 0.0625(13) 0.3762(11) 0.0357(18) Uani 1 1 d . . . H3A H 0.2489 -0.0535 0.3850 0.043 Uiso 1 1 calc R . . C5 C 0.0733(6) -0.1515(12) 0.5219(12) 0.0364(19) Uani 1 1 d . . . H5A H 0.1219 -0.2572 0.5332 0.044 Uiso 1 1 calc R . . C4 C 0.1002(6) 0.0359(13) 0.4382(12) 0.0365(18) Uani 1 1 d . . . C2 C 0.2470(6) 0.2364(13) 0.3088(12) 0.0374(19) Uani 1 1 d . . . H2A H 0.2063 0.3552 0.2982 0.045 Uiso 1 1 calc R . . O2 O 0.3870(5) 0.4193(8) 0.1875(8) 0.0384(14) Uani 1 1 d . . . C6 C 0.0239(7) 0.1830(14) 0.4120(13) 0.044(2) Uani 1 1 d . . . H6A H 0.0385 0.3051 0.3486 0.053 Uiso 1 1 calc R . . O3 O 0.4203(5) -0.2914(7) 0.4925(8) 0.0339(12) Uani 1 1 d D . . H32 H 0.413(7) -0.384(10) 0.574(7) 0.051 Uiso 1 1 d D . . H31 H 0.400(7) -0.346(12) 0.393(6) 0.051 Uiso 1 1 d 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 0.0156(6) 0.0187(7) 0.0254(7) 0.0006(6) 0.0026(5) 0.0024(5) C1 0.014(3) 0.023(3) 0.021(3) 0.002(3) 0.001(2) -0.002(3) O1 0.037(3) 0.027(3) 0.035(3) 0.005(2) -0.006(2) 0.005(2) C3 0.027(4) 0.042(4) 0.037(4) 0.003(3) 0.011(3) -0.003(3) C5 0.019(3) 0.033(4) 0.058(5) 0.011(4) 0.003(4) 0.001(3) C4 0.023(4) 0.038(4) 0.048(5) 0.008(4) 0.009(3) -0.008(3) C2 0.024(4) 0.037(4) 0.051(5) 0.008(4) 0.009(4) -0.002(3) O2 0.043(3) 0.025(3) 0.047(3) 0.004(2) 0.024(3) -0.004(2) C6 0.039(5) 0.039(5) 0.053(5) 0.016(4) 0.015(4) -0.009(4) O3 0.049(3) 0.019(2) 0.033(3) -0.002(2) 0.003(3) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O2 2.091(6) 2_645 ? Fe1 O2 2.091(6) 4_566 ? Fe1 O3 2.133(5) 3_656 ? Fe1 O3 2.133(5) . ? Fe1 O1 2.145(5) 3_656 ? Fe1 O1 2.145(5) . ? C1 O1 1.248(8) . ? C1 O2 1.263(8) . ? C1 C2 1.480(9) . ? C3 C2 1.329(11) . ? C3 C4 1.468(10) . ? C3 H3A 0.9300 . ? C5 C6 1.375(11) 3_556 ? C5 C4 1.393(11) . ? C5 H5A 0.9300 . ? C4 C6 1.384(12) . ? C2 H2A 0.9300 . ? O2 Fe1 2.091(6) 2_655 ? C6 C5 1.375(11) 3_556 ? C6 H6A 0.9300 . ? O3 H32 0.85(2) . ? O3 H31 0.85(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 O2 Fe1 O2 180.0(2) 2_645 4_566 ? O2 Fe1 O3 83.6(2) 2_645 3_656 ? O2 Fe1 O3 96.4(2) 4_566 3_656 ? O2 Fe1 O3 96.4(2) 2_645 . ? O2 Fe1 O3 83.6(2) 4_566 . ? O3 Fe1 O3 180.0(3) 3_656 . ? O2 Fe1 O1 94.5(2) 2_645 3_656 ? O2 Fe1 O1 85.5(2) 4_566 3_656 ? O3 Fe1 O1 86.9(2) 3_656 3_656 ? O3 Fe1 O1 93.1(2) . 3_656 ? O2 Fe1 O1 85.5(2) 2_645 . ? O2 Fe1 O1 94.5(2) 4_566 . ? O3 Fe1 O1 93.1(2) 3_656 . ? O3 Fe1 O1 86.9(2) . . ? O1 Fe1 O1 180.0 3_656 . ? O1 C1 O2 123.8(6) . . ? O1 C1 C2 118.7(6) . . ? O2 C1 C2 117.5(6) . . ? C1 O1 Fe1 128.5(5) . . ? C2 C3 C4 126.3(8) . . ? C2 C3 H3A 116.8 . . ? C4 C3 H3A 116.8 . . ? C6 C5 C4 121.1(7) 3_556 . ? C6 C5 H5A 119.4 3_556 . ? C4 C5 H5A 119.4 . . ? C6 C4 C5 117.6(7) . . ? C6 C4 C3 123.8(7) . . ? C5 C4 C3 118.5(7) . . ? C3 C2 C1 122.1(7) . . ? C3 C2 H2A 118.9 . . ? C1 C2 H2A 118.9 . . ? C1 O2 Fe1 133.6(5) . 2_655 ? C5 C6 C4 121.0(7) 3_556 . ? C5 C6 H6A 119.5 3_556 . ? C4 C6 H6A 119.5 . . ? Fe1 O3 H32 130(5) . . ? Fe1 O3 H31 122(5) . . ? H32 O3 H31 107(3) . . ? 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 O2 C1 O1 Fe1 89.8(8) . . . . ? C2 C1 O1 Fe1 -87.9(8) . . . . ? O2 Fe1 O1 C1 -137.8(6) 2_645 . . . ? O2 Fe1 O1 C1 42.2(6) 4_566 . . . ? O3 Fe1 O1 C1 -54.5(6) 3_656 . . . ? O3 Fe1 O1 C1 125.5(6) . . . . ? O1 Fe1 O1 C1 51(70) 3_656 . . . ? C6 C5 C4 C6 -4.7(15) 3_556 . . . ? C6 C5 C4 C3 177.8(9) 3_556 . . . ? C2 C3 C4 C6 9.1(15) . . . . ? C2 C3 C4 C5 -173.6(9) . . . . ? C4 C3 C2 C1 180.0(8) . . . . ? O1 C1 C2 C3 -2.2(12) . . . . ? O2 C1 C2 C3 179.9(8) . . . . ? O1 C1 O2 Fe1 31.2(11) . . . 2_655 ? C2 C1 O2 Fe1 -151.1(6) . . . 2_655 ? C5 C4 C6 C5 4.7(15) . . . 3_556 ? C3 C4 C6 C5 -178.0(9) . . . 3_556 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.965 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.132