Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ime119 _database_code_depnum_ccdc_archive 'CCDC 640141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 Fe I O4' _chemical_formula_weight 361.90 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' I I -0.4742 1.8119 '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)/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 7.0434(18) _cell_length_b 8.121(2) _cell_length_c 19.607(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.262(4) _cell_angle_gamma 90.00 _cell_volume 1103.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4169 _cell_measurement_theta_min 5.442 _cell_measurement_theta_max 54.946 _exptl_crystal_description BLOCK _exptl_crystal_colour RED _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 4.153 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2942 _exptl_absorpt_correction_T_max 0.4619 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11922 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2509 _reflns_number_gt 1857 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2509 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.83611(9) 0.76008(6) 0.35838(3) 0.01975(16) Uani 1 1 d . . . I1 I 0.48490(4) 0.76063(3) 0.288644(15) 0.02868(13) Uani 1 1 d . . . O1 O 0.8068(5) 0.4076(4) 0.38167(19) 0.0424(9) Uani 1 1 d . . . O2 O 0.9785(6) 0.7339(4) 0.22725(19) 0.0374(8) Uani 1 1 d . . . O3 O 0.5205(5) 0.8009(5) 0.5001(2) 0.0453(9) Uani 1 1 d . . . O4 O 0.7790(5) 0.6481(4) 0.54362(18) 0.0399(9) Uani 1 1 d . . . C1 C 0.8191(7) 0.5445(5) 0.3713(2) 0.0300(10) Uani 1 1 d . . . C2 C 0.9230(7) 0.7431(5) 0.2781(2) 0.0238(9) Uani 1 1 d . . . C3 C 1.0105(6) 0.7899(5) 0.4554(2) 0.0258(9) Uani 1 1 d . . . H3A H 1.0871 0.7015 0.4832 0.031 Uiso 1 1 calc R . . C4 C 1.0769(7) 0.8943(6) 0.4071(2) 0.0329(11) Uani 1 1 d . . . H4A H 1.2083 0.8923 0.3945 0.040 Uiso 1 1 calc R . . C5 C 0.9240(8) 1.0064(5) 0.3805(2) 0.0341(11) Uani 1 1 d . . . H5A H 0.9303 1.0945 0.3453 0.041 Uiso 1 1 calc R . . C6 C 0.7671(7) 0.9738(5) 0.4120(2) 0.0303(10) Uani 1 1 d . . . H6A H 0.6410 1.0336 0.4029 0.036 Uiso 1 1 calc R . . C7 C 0.8138(6) 0.8370(5) 0.4593(2) 0.0255(9) Uani 1 1 d . . . C8 C 0.6857(7) 0.7630(5) 0.5019(2) 0.0268(10) Uani 1 1 d . . . C9 C 0.6701(7) 0.5709(7) 0.5917(3) 0.0454(13) Uani 1 1 d . . . H9A H 0.7588 0.5109 0.6274 0.068 Uiso 1 1 calc R . . H9B H 0.5757 0.4941 0.5664 0.068 Uiso 1 1 calc R . . H9C H 0.6027 0.6559 0.6137 0.068 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 0.0189(3) 0.0231(3) 0.0172(3) -0.0009(2) 0.0031(2) 0.0014(2) I1 0.02009(18) 0.0409(2) 0.02414(19) -0.00050(13) 0.00150(12) 0.00234(11) O1 0.046(2) 0.0279(18) 0.049(2) 0.0039(16) -0.0037(18) 0.0012(15) O2 0.038(2) 0.053(2) 0.0232(18) 0.0022(15) 0.0106(16) 0.0016(14) O3 0.032(2) 0.062(2) 0.045(2) 0.005(2) 0.0141(18) 0.0099(17) O4 0.0325(19) 0.051(2) 0.037(2) 0.0117(17) 0.0085(16) 0.0001(16) C1 0.027(2) 0.031(2) 0.031(3) -0.004(2) 0.001(2) 0.0038(18) C2 0.019(2) 0.029(2) 0.023(2) -0.0003(17) 0.0014(18) 0.0008(15) C3 0.022(2) 0.035(2) 0.019(2) -0.0030(18) 0.0002(18) -0.0029(17) C4 0.026(2) 0.042(3) 0.029(3) -0.011(2) 0.001(2) -0.0077(19) C5 0.053(3) 0.028(2) 0.022(2) -0.0009(19) 0.007(2) -0.002(2) C6 0.037(3) 0.024(2) 0.027(2) -0.0056(18) -0.001(2) 0.0051(18) C7 0.026(2) 0.029(2) 0.021(2) -0.0046(18) 0.0031(19) -0.0011(17) C8 0.028(3) 0.030(2) 0.023(2) -0.0038(18) 0.007(2) -0.0006(17) C9 0.046(3) 0.060(3) 0.034(3) 0.016(3) 0.016(2) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 1.776(5) . ? Fe1 C2 1.793(5) . ? Fe1 C3 2.086(4) . ? Fe1 C4 2.098(4) . ? Fe1 C7 2.106(4) . ? Fe1 C5 2.116(4) . ? Fe1 C6 2.130(4) . ? Fe1 I1 2.6046(9) . ? O1 C1 1.136(5) . ? O2 C2 1.136(6) . ? O3 C8 1.198(6) . ? O4 C8 1.334(5) . ? O4 C9 1.459(5) . ? C3 C4 1.411(7) . ? C3 C7 1.452(6) . ? C3 H3A 1.0000 . ? C4 C5 1.436(7) . ? C4 H4A 1.0000 . ? C5 C6 1.385(7) . ? C5 H5A 1.0000 . ? C6 C7 1.446(6) . ? C6 H6A 1.0000 . ? C7 C8 1.464(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C2 95.26(19) . . ? C1 Fe1 C3 91.63(19) . . ? C2 Fe1 C3 124.9(2) . . ? C1 Fe1 C4 121.13(19) . . ? C2 Fe1 C4 93.7(2) . . ? C3 Fe1 C4 39.40(18) . . ? C1 Fe1 C7 98.06(19) . . ? C2 Fe1 C7 160.28(18) . . ? C3 Fe1 C7 40.52(17) . . ? C4 Fe1 C7 66.89(18) . . ? C1 Fe1 C5 158.1(2) . . ? C2 Fe1 C5 96.83(18) . . ? C3 Fe1 C5 66.44(18) . . ? C4 Fe1 C5 39.84(18) . . ? C7 Fe1 C5 66.15(17) . . ? C1 Fe1 C6 134.9(2) . . ? C2 Fe1 C6 129.76(17) . . ? C3 Fe1 C6 66.69(17) . . ? C4 Fe1 C6 65.71(18) . . ? C7 Fe1 C6 39.92(16) . . ? C5 Fe1 C6 38.08(18) . . ? C1 Fe1 I1 89.69(14) . . ? C2 Fe1 I1 88.85(15) . . ? C3 Fe1 I1 145.92(13) . . ? C4 Fe1 I1 148.59(13) . . ? C7 Fe1 I1 105.65(12) . . ? C5 Fe1 I1 108.76(14) . . ? C6 Fe1 I1 88.79(13) . . ? C8 O4 C9 116.0(4) . . ? O1 C1 Fe1 177.7(4) . . ? O2 C2 Fe1 179.4(4) . . ? C4 C3 C7 108.1(4) . . ? C4 C3 Fe1 70.7(3) . . ? C7 C3 Fe1 70.5(2) . . ? C4 C3 H3A 126.0 . . ? C7 C3 H3A 126.0 . . ? Fe1 C3 H3A 126.0 . . ? C3 C4 C5 108.0(4) . . ? C3 C4 Fe1 69.9(2) . . ? C5 C4 Fe1 70.8(3) . . ? C3 C4 H4A 126.0 . . ? C5 C4 H4A 126.0 . . ? Fe1 C4 H4A 126.0 . . ? C6 C5 C4 108.8(4) . . ? C6 C5 Fe1 71.5(3) . . ? C4 C5 Fe1 69.4(3) . . ? C6 C5 H5A 125.6 . . ? C4 C5 H5A 125.6 . . ? Fe1 C5 H5A 125.6 . . ? C5 C6 C7 108.9(4) . . ? C5 C6 Fe1 70.4(3) . . ? C7 C6 Fe1 69.2(2) . . ? C5 C6 H6A 125.5 . . ? C7 C6 H6A 125.5 . . ? Fe1 C6 H6A 125.5 . . ? C6 C7 C3 106.2(4) . . ? C6 C7 C8 126.0(4) . . ? C3 C7 C8 127.8(4) . . ? C6 C7 Fe1 70.9(2) . . ? C3 C7 Fe1 69.0(2) . . ? C8 C7 Fe1 124.8(3) . . ? O3 C8 O4 124.5(4) . . ? O3 C8 C7 124.9(4) . . ? O4 C8 C7 110.5(4) . . ? O4 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.376 _refine_diff_density_min -0.657 _refine_diff_density_rms 0.162 data_ime127 _database_code_depnum_ccdc_archive 'CCDC 640142' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 Fe N O7' _chemical_formula_weight 297.01 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' N N 0.0061 0.0033 '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 P2(1)/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 7.037(2) _cell_length_b 8.134(2) _cell_length_c 19.058(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.053(18) _cell_angle_gamma 90.00 _cell_volume 1084.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5550 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 34.17 _exptl_crystal_description PLATE _exptl_crystal_colour RED _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 1.418 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7550 _exptl_absorpt_correction_T_max 0.9325 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10058 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1878 _reflns_number_gt 1710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1878 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 1.00332(5) 1.11327(4) 0.136060(17) 0.0104(2) Uani 1 1 d . . . N2 N 1.0234(3) 0.7627(2) 0.11743(11) 0.0131(4) Uani 1 1 d . . . O1 O 1.3387(3) 1.2859(2) 0.09378(12) 0.0270(5) Uani 1 1 d . . . O2 O 1.1822(3) 1.0251(2) 0.27810(10) 0.0260(5) Uani 1 1 d . . . O3 O 0.5325(3) 0.87981(18) 0.18527(10) 0.0174(4) Uani 1 1 d . . . O4 O 0.6104(3) 0.82701(19) 0.07567(9) 0.0149(4) Uani 1 1 d . . . O5 O 0.9613(3) 0.7572(2) 0.17514(9) 0.0173(4) Uani 1 1 d . . . O6 O 1.0477(3) 0.6399(2) 0.08148(11) 0.0198(4) Uani 1 1 d . . . O7 O 1.0674(3) 0.90534(18) 0.09072(10) 0.0136(4) Uani 1 1 d . . . C1 C 1.2128(4) 1.2131(3) 0.11098(14) 0.0186(6) Uani 1 1 d . . . C2 C 1.1152(4) 1.0562(3) 0.22305(14) 0.0173(5) Uani 1 1 d . . . C3 C 0.7571(3) 1.1921(3) 0.18082(13) 0.0136(5) Uani 1 1 d . . . H3 H 0.7329 1.1790 0.2313 0.016 Uiso 1 1 calc R . . C4 C 0.8490(3) 1.3280(3) 0.15191(13) 0.0144(5) Uani 1 1 d . . . H4 H 0.8989 1.4283 0.1781 0.017 Uiso 1 1 calc R . . C5 C 0.8471(4) 1.2992(3) 0.07760(14) 0.0149(5) Uani 1 1 d . . . H5 H 0.8989 1.3752 0.0430 0.018 Uiso 1 1 calc R . . C6 C 0.7621(4) 1.1445(3) 0.06153(13) 0.0128(5) Uani 1 1 d . . . H6 H 0.7417 1.0927 0.0138 0.015 Uiso 1 1 calc R . . C7 C 0.7053(3) 1.0776(3) 0.12544(13) 0.0119(5) Uani 1 1 d . . . C8 C 0.6074(4) 0.9191(3) 0.13369(13) 0.0127(5) Uani 1 1 d . . . C9 C 0.5328(4) 0.6625(3) 0.08024(14) 0.0190(5) Uani 1 1 d . . . H9A H 0.5945 0.6075 0.1224 0.028 Uiso 1 1 calc R . . H9B H 0.5565 0.5998 0.0381 0.028 Uiso 1 1 calc R . . H9C H 0.3949 0.6693 0.0833 0.028 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 0.0104(3) 0.0097(3) 0.0114(3) -0.00003(10) 0.00224(17) 0.00021(11) N2 0.0112(10) 0.0133(10) 0.0149(11) 0.0007(8) 0.0023(8) 0.0011(8) O1 0.0162(10) 0.0236(9) 0.0430(13) 0.0035(8) 0.0109(9) -0.0024(8) O2 0.0275(11) 0.0324(10) 0.0166(10) -0.0005(7) -0.0043(8) 0.0089(8) O3 0.0173(10) 0.0187(9) 0.0174(10) 0.0015(6) 0.0069(8) -0.0015(7) O4 0.0161(9) 0.0129(8) 0.0158(9) -0.0014(6) 0.0022(7) -0.0042(7) O5 0.0200(9) 0.0166(8) 0.0165(10) 0.0040(6) 0.0075(7) 0.0009(7) O6 0.0242(10) 0.0112(8) 0.0249(10) -0.0055(7) 0.0063(8) 0.0005(7) O7 0.0160(9) 0.0106(7) 0.0152(9) 0.0013(6) 0.0062(7) -0.0002(6) C1 0.0190(14) 0.0149(10) 0.0220(13) -0.0028(9) 0.0022(11) 0.0040(11) C2 0.0148(12) 0.0161(11) 0.0214(14) -0.0046(9) 0.0039(10) 0.0012(10) C3 0.0124(12) 0.0137(11) 0.0148(12) -0.0018(8) 0.0017(9) 0.0025(9) C4 0.0136(12) 0.0103(10) 0.0194(13) -0.0002(9) 0.0017(10) 0.0027(9) C5 0.0143(12) 0.0120(10) 0.0185(12) 0.0037(9) 0.0019(9) 0.0034(9) C6 0.0119(12) 0.0136(9) 0.0129(12) 0.0012(8) 0.0020(9) 0.0021(9) C7 0.0101(11) 0.0137(10) 0.0121(12) 0.0008(9) 0.0023(9) 0.0028(9) C8 0.0105(12) 0.0140(10) 0.0132(12) 0.0010(9) -0.0005(9) 0.0028(9) C9 0.0205(13) 0.0128(10) 0.0239(14) -0.0014(10) 0.0033(10) -0.0047(10) _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 1.791(3) . ? Fe1 C2 1.819(3) . ? Fe1 O7 1.9729(17) . ? Fe1 C4 2.095(2) . ? Fe1 C7 2.105(3) . ? Fe1 C3 2.110(3) . ? Fe1 C6 2.111(3) . ? Fe1 C5 2.116(2) . ? N2 O5 1.226(3) . ? N2 O6 1.233(3) . ? N2 O7 1.317(3) . ? O1 C1 1.142(3) . ? O2 C2 1.133(3) . ? O3 C8 1.206(3) . ? O4 C8 1.337(3) . ? O4 C9 1.451(3) . ? C3 C4 1.421(4) . ? C3 C7 1.426(3) . ? C3 H3 1.0000 . ? C4 C5 1.434(4) . ? C4 H4 1.0000 . ? C5 C6 1.413(3) . ? C5 H5 1.0000 . ? C6 C7 1.429(4) . ? C6 H6 1.0000 . ? C7 C8 1.479(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C2 94.00(12) . . ? C1 Fe1 O7 92.25(10) . . ? C2 Fe1 O7 94.80(9) . . ? C1 Fe1 C4 96.55(11) . . ? C2 Fe1 C4 105.20(10) . . ? O7 Fe1 C4 157.45(9) . . ? C1 Fe1 C7 151.15(10) . . ? C2 Fe1 C7 112.55(11) . . ? O7 Fe1 C7 96.38(9) . . ? C4 Fe1 C7 66.58(9) . . ? C1 Fe1 C3 134.74(10) . . ? C2 Fe1 C3 90.23(11) . . ? O7 Fe1 C3 132.28(8) . . ? C4 Fe1 C3 39.49(10) . . ? C7 Fe1 C3 39.53(9) . . ? C1 Fe1 C6 113.07(11) . . ? C2 Fe1 C6 152.14(11) . . ? O7 Fe1 C6 90.76(9) . . ? C4 Fe1 C6 66.69(9) . . ? C7 Fe1 C6 39.61(10) . . ? C3 Fe1 C6 66.35(10) . . ? C1 Fe1 C5 86.10(11) . . ? C2 Fe1 C5 144.39(10) . . ? O7 Fe1 C5 120.80(9) . . ? C4 Fe1 C5 39.81(10) . . ? C7 Fe1 C5 65.85(9) . . ? C3 Fe1 C5 65.95(10) . . ? C6 Fe1 C5 39.04(10) . . ? O5 N2 O6 123.5(2) . . ? O5 N2 O7 119.92(19) . . ? O6 N2 O7 116.6(2) . . ? C8 O4 C9 115.31(19) . . ? N2 O7 Fe1 120.81(15) . . ? O1 C1 Fe1 175.3(2) . . ? O2 C2 Fe1 177.8(2) . . ? C4 C3 C7 108.2(2) . . ? C4 C3 Fe1 69.68(14) . . ? C7 C3 Fe1 70.04(14) . . ? C4 C3 H3 125.9 . . ? C7 C3 H3 125.9 . . ? Fe1 C3 H3 125.9 . . ? C3 C4 C5 107.4(2) . . ? C3 C4 Fe1 70.83(13) . . ? C5 C4 Fe1 70.89(13) . . ? C3 C4 H4 126.3 . . ? C5 C4 H4 126.3 . . ? Fe1 C4 H4 126.3 . . ? C6 C5 C4 108.6(2) . . ? C6 C5 Fe1 70.27(13) . . ? C4 C5 Fe1 69.30(13) . . ? C6 C5 H5 125.7 . . ? C4 C5 H5 125.7 . . ? Fe1 C5 H5 125.7 . . ? C5 C6 C7 107.7(2) . . ? C5 C6 Fe1 70.69(13) . . ? C7 C6 Fe1 69.98(14) . . ? C5 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe1 C6 H6 126.1 . . ? C3 C7 C6 108.1(2) . . ? C3 C7 C8 125.2(2) . . ? C6 C7 C8 126.7(2) . . ? C3 C7 Fe1 70.42(14) . . ? C6 C7 Fe1 70.41(14) . . ? C8 C7 Fe1 125.50(16) . . ? O3 C8 O4 124.9(2) . . ? O3 C8 C7 124.5(2) . . ? O4 C8 C7 110.6(2) . . ? O4 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.647 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.172 data_ime76m _database_code_depnum_ccdc_archive 'CCDC 640143' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Fe O6' _chemical_formula_weight 294.04 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 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 6.5711(14) _cell_length_b 12.667(3) _cell_length_c 14.092(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.571(4) _cell_angle_gamma 90.00 _cell_volume 1162.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5795 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 1.313 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6085 _exptl_absorpt_correction_T_max 0.7700 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12813 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2638 _reflns_number_gt 2218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker smart' _computing_cell_refinement 'Bruker smart' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.0932P] 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 2638 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.51110(3) 0.756383(17) 0.396425(18) 0.01266(10) Uani 1 1 d . . . O1 O 0.3665(2) 0.89707(10) 0.53648(10) 0.0271(3) Uani 1 1 d . . . O2 O 0.8740(2) 0.88358(10) 0.38201(11) 0.0283(3) Uani 1 1 d . . . O3 O 0.77254(18) 0.66479(9) 0.18236(9) 0.0186(3) Uani 1 1 d . . . O4 O 0.7333(2) 0.51538(10) 0.26452(10) 0.0253(3) Uani 1 1 d . . . O5 O 0.85612(18) 0.66368(9) 0.50418(9) 0.0195(3) Uani 1 1 d . . . O6 O 0.56116(19) 0.62143(9) 0.55832(9) 0.0199(3) Uani 1 1 d . . . C1 C 0.4241(3) 0.84113(13) 0.48239(14) 0.0179(4) Uani 1 1 d . . . C2 C 0.7333(3) 0.83265(13) 0.38855(13) 0.0180(4) Uani 1 1 d . . . C3 C 0.4212(3) 0.76053(13) 0.24763(14) 0.0159(4) Uani 1 1 d . . . H3 H 0.4745 0.8099 0.2013 0.019 Uiso 1 1 calc R . . C4 C 0.5049(3) 0.65875(13) 0.27617(13) 0.0153(4) Uani 1 1 d . . . C5 C 0.3803(3) 0.61315(13) 0.34050(13) 0.0167(4) Uani 1 1 d . . . H5 H 0.3997 0.5420 0.3711 0.020 Uiso 1 1 calc R . . C6 C 0.2236(3) 0.68611(13) 0.35300(13) 0.0178(4) Uani 1 1 d . . . H6 H 0.1122 0.6755 0.3940 0.021 Uiso 1 1 calc R . . C7 C 0.2484(3) 0.77699(14) 0.29452(13) 0.0171(4) Uani 1 1 d . . . H7 H 0.1576 0.8406 0.2880 0.021 Uiso 1 1 calc R . . C8 C 0.6815(3) 0.60404(13) 0.24254(13) 0.0171(4) Uani 1 1 d . . . C9 C 0.9316(3) 0.61219(15) 0.13775(14) 0.0216(4) Uani 1 1 d . . . H9A H 1.0350 0.5833 0.1874 0.032 Uiso 1 1 calc R . . H9B H 0.9967 0.6630 0.0988 0.032 Uiso 1 1 calc R . . H9C H 0.8707 0.5547 0.0969 0.032 Uiso 1 1 calc R . . C10 C 0.6468(3) 0.66902(13) 0.50085(12) 0.0153(4) Uani 1 1 d . . . C11 C 0.9630(3) 0.60170(15) 0.58247(14) 0.0239(4) Uani 1 1 d . . . H11A H 0.9259 0.6275 0.6435 0.036 Uiso 1 1 calc R . . H11B H 1.1116 0.6086 0.5825 0.036 Uiso 1 1 calc R . . H11C H 0.9235 0.5273 0.5741 0.036 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 0.01189(15) 0.01202(15) 0.01462(17) 0.00149(9) 0.00382(10) 0.00042(8) O1 0.0278(7) 0.0264(7) 0.0287(8) -0.0064(6) 0.0104(6) 0.0054(6) O2 0.0232(7) 0.0231(7) 0.0410(9) -0.0010(6) 0.0132(6) -0.0071(6) O3 0.0176(6) 0.0156(6) 0.0242(7) 0.0014(5) 0.0087(5) 0.0049(5) O4 0.0329(8) 0.0161(6) 0.0280(8) 0.0031(6) 0.0090(6) 0.0070(5) O5 0.0147(6) 0.0225(6) 0.0207(7) 0.0035(5) 0.0007(5) 0.0014(5) O6 0.0224(7) 0.0187(6) 0.0196(7) 0.0032(5) 0.0069(5) 0.0007(5) C1 0.0145(8) 0.0181(8) 0.0212(10) 0.0040(7) 0.0031(7) 0.0003(7) C2 0.0213(9) 0.0154(8) 0.0182(9) 0.0000(7) 0.0055(7) 0.0023(7) C3 0.0157(9) 0.0157(8) 0.0164(10) 0.0022(7) 0.0029(7) 0.0005(6) C4 0.0163(8) 0.0153(8) 0.0142(9) 0.0008(7) 0.0012(7) 0.0011(6) C5 0.0182(9) 0.0150(8) 0.0166(9) -0.0006(7) 0.0004(7) -0.0046(6) C6 0.0132(8) 0.0197(9) 0.0205(10) 0.0017(7) 0.0019(7) -0.0027(7) C7 0.0143(8) 0.0205(8) 0.0162(9) 0.0016(7) 0.0010(7) 0.0004(7) C8 0.0196(9) 0.0167(8) 0.0143(9) -0.0022(7) 0.0000(7) -0.0006(7) C9 0.0186(9) 0.0226(9) 0.0249(10) -0.0017(8) 0.0079(8) 0.0055(7) C10 0.0174(9) 0.0139(8) 0.0145(9) -0.0022(7) 0.0014(7) 0.0007(6) C11 0.0218(10) 0.0233(10) 0.0250(11) 0.0057(8) -0.0025(8) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C2 1.7662(18) . ? Fe1 C1 1.7689(19) . ? Fe1 C10 1.9593(17) . ? Fe1 C4 2.0939(18) . ? Fe1 C3 2.1028(19) . ? Fe1 C6 2.1052(17) . ? Fe1 C7 2.1111(18) . ? Fe1 C5 2.1150(17) . ? O1 C1 1.141(2) . ? O2 C2 1.141(2) . ? O3 C8 1.343(2) . ? O3 C9 1.451(2) . ? O4 C8 1.202(2) . ? O5 C10 1.372(2) . ? O5 C11 1.457(2) . ? O6 C10 1.206(2) . ? C3 C7 1.402(2) . ? C3 C4 1.438(2) . ? C4 C5 1.422(2) . ? C4 C8 1.482(2) . ? C5 C6 1.412(2) . ? C6 C7 1.437(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 C2 Fe1 C1 93.18(8) . . ? C2 Fe1 C10 93.33(8) . . ? C1 Fe1 C10 89.11(8) . . ? C2 Fe1 C4 101.55(7) . . ? C1 Fe1 C4 159.90(8) . . ? C10 Fe1 C4 103.45(7) . . ? C2 Fe1 C3 92.85(8) . . ? C1 Fe1 C3 126.44(7) . . ? C10 Fe1 C3 143.44(7) . . ? C4 Fe1 C3 40.08(6) . . ? C2 Fe1 C6 158.53(8) . . ? C1 Fe1 C6 95.57(7) . . ? C10 Fe1 C6 106.35(7) . . ? C4 Fe1 C6 66.06(7) . . ? C3 Fe1 C6 66.25(7) . . ? C2 Fe1 C7 119.88(8) . . ? C1 Fe1 C7 94.69(8) . . ? C10 Fe1 C7 146.20(7) . . ? C4 Fe1 C7 66.15(7) . . ? C3 Fe1 C7 38.88(7) . . ? C6 Fe1 C7 39.87(7) . . ? C2 Fe1 C5 138.12(8) . . ? C1 Fe1 C5 128.58(8) . . ? C10 Fe1 C5 85.28(7) . . ? C4 Fe1 C5 39.49(7) . . ? C3 Fe1 C5 66.60(7) . . ? C6 Fe1 C5 39.09(7) . . ? C7 Fe1 C5 66.23(7) . . ? C8 O3 C9 114.63(13) . . ? C10 O5 C11 115.71(13) . . ? O1 C1 Fe1 178.70(17) . . ? O2 C2 Fe1 178.33(17) . . ? C7 C3 C4 107.77(16) . . ? C7 C3 Fe1 70.88(11) . . ? C4 C3 Fe1 69.62(10) . . ? C5 C4 C3 108.13(15) . . ? C5 C4 C8 123.71(15) . . ? C3 C4 C8 128.07(16) . . ? C5 C4 Fe1 71.05(10) . . ? C3 C4 Fe1 70.29(10) . . ? C8 C4 Fe1 127.05(12) . . ? C6 C5 C4 107.73(15) . . ? C6 C5 Fe1 70.08(10) . . ? C4 C5 Fe1 69.46(10) . . ? C5 C6 C7 108.23(16) . . ? C5 C6 Fe1 70.83(10) . . ? C7 C6 Fe1 70.29(10) . . ? C3 C7 C6 108.13(16) . . ? C3 C7 Fe1 70.24(11) . . ? C6 C7 Fe1 69.85(10) . . ? O4 C8 O3 124.32(16) . . ? O4 C8 C4 124.14(16) . . ? O3 C8 C4 111.51(14) . . ? O6 C10 O5 120.43(15) . . ? O6 C10 Fe1 125.46(13) . . ? O5 C10 Fe1 114.11(11) . . ? 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 C2 Fe1 C1 O1 82(7) . . . . ? C10 Fe1 C1 O1 175(100) . . . . ? C4 Fe1 C1 O1 -56(7) . . . . ? C3 Fe1 C1 O1 -14(7) . . . . ? C6 Fe1 C1 O1 -79(7) . . . . ? C7 Fe1 C1 O1 -39(7) . . . . ? C5 Fe1 C1 O1 -102(7) . . . . ? C1 Fe1 C2 O2 -81(6) . . . . ? C10 Fe1 C2 O2 -170(6) . . . . ? C4 Fe1 C2 O2 86(6) . . . . ? C3 Fe1 C2 O2 46(6) . . . . ? C6 Fe1 C2 O2 33(6) . . . . ? C7 Fe1 C2 O2 17(6) . . . . ? C5 Fe1 C2 O2 103(6) . . . . ? C2 Fe1 C3 C7 -137.14(11) . . . . ? C1 Fe1 C3 C7 -41.07(13) . . . . ? C10 Fe1 C3 C7 123.38(13) . . . . ? C4 Fe1 C3 C7 118.25(15) . . . . ? C6 Fe1 C3 C7 37.79(10) . . . . ? C5 Fe1 C3 C7 80.61(11) . . . . ? C2 Fe1 C3 C4 104.61(11) . . . . ? C1 Fe1 C3 C4 -159.32(10) . . . . ? C10 Fe1 C3 C4 5.13(17) . . . . ? C6 Fe1 C3 C4 -80.46(11) . . . . ? C7 Fe1 C3 C4 -118.25(15) . . . . ? C5 Fe1 C3 C4 -37.64(10) . . . . ? C7 C3 C4 C5 0.4(2) . . . . ? Fe1 C3 C4 C5 61.31(12) . . . . ? C7 C3 C4 C8 176.91(17) . . . . ? Fe1 C3 C4 C8 -122.16(18) . . . . ? C7 C3 C4 Fe1 -60.93(13) . . . . ? C2 Fe1 C4 C5 161.26(11) . . . . ? C1 Fe1 C4 C5 -62.4(2) . . . . ? C10 Fe1 C4 C5 64.95(11) . . . . ? C3 Fe1 C4 C5 -118.19(14) . . . . ? C6 Fe1 C4 C5 -37.20(10) . . . . ? C7 Fe1 C4 C5 -80.99(11) . . . . ? C2 Fe1 C4 C3 -80.56(11) . . . . ? C1 Fe1 C4 C3 55.7(2) . . . . ? C10 Fe1 C4 C3 -176.86(10) . . . . ? C6 Fe1 C4 C3 80.98(11) . . . . ? C7 Fe1 C4 C3 37.20(10) . . . . ? C5 Fe1 C4 C3 118.19(14) . . . . ? C2 Fe1 C4 C8 42.83(16) . . . . ? C1 Fe1 C4 C8 179.13(18) . . . . ? C10 Fe1 C4 C8 -53.48(16) . . . . ? C3 Fe1 C4 C8 123.38(19) . . . . ? C6 Fe1 C4 C8 -155.63(17) . . . . ? C7 Fe1 C4 C8 160.58(17) . . . . ? C5 Fe1 C4 C8 -118.43(19) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C8 C4 C5 C6 -177.66(16) . . . . ? Fe1 C4 C5 C6 59.88(12) . . . . ? C3 C4 C5 Fe1 -60.82(12) . . . . ? C8 C4 C5 Fe1 122.46(17) . . . . ? C2 Fe1 C5 C6 -146.93(13) . . . . ? C1 Fe1 C5 C6 38.27(14) . . . . ? C10 Fe1 C5 C6 123.35(11) . . . . ? C4 Fe1 C5 C6 -118.79(15) . . . . ? C3 Fe1 C5 C6 -80.60(11) . . . . ? C7 Fe1 C5 C6 -38.01(11) . . . . ? C2 Fe1 C5 C4 -28.14(16) . . . . ? C1 Fe1 C5 C4 157.06(11) . . . . ? C10 Fe1 C5 C4 -117.86(11) . . . . ? C3 Fe1 C5 C4 38.20(10) . . . . ? C6 Fe1 C5 C4 118.79(15) . . . . ? C7 Fe1 C5 C4 80.78(11) . . . . ? C4 C5 C6 C7 1.1(2) . . . . ? Fe1 C5 C6 C7 60.63(12) . . . . ? C4 C5 C6 Fe1 -59.49(12) . . . . ? C2 Fe1 C6 C5 95.5(2) . . . . ? C1 Fe1 C6 C5 -150.89(11) . . . . ? C10 Fe1 C6 C5 -60.18(12) . . . . ? C4 Fe1 C6 C5 37.57(10) . . . . ? C3 Fe1 C6 C5 81.58(11) . . . . ? C7 Fe1 C6 C5 118.45(16) . . . . ? C2 Fe1 C6 C7 -22.9(2) . . . . ? C1 Fe1 C6 C7 90.65(12) . . . . ? C10 Fe1 C6 C7 -178.64(10) . . . . ? C4 Fe1 C6 C7 -80.88(11) . . . . ? C3 Fe1 C6 C7 -36.87(10) . . . . ? C5 Fe1 C6 C7 -118.45(16) . . . . ? C4 C3 C7 C6 0.3(2) . . . . ? Fe1 C3 C7 C6 -59.81(13) . . . . ? C4 C3 C7 Fe1 60.13(13) . . . . ? C5 C6 C7 C3 -0.9(2) . . . . ? Fe1 C6 C7 C3 60.06(13) . . . . ? C5 C6 C7 Fe1 -60.97(12) . . . . ? C2 Fe1 C7 C3 51.58(13) . . . . ? C1 Fe1 C7 C3 147.97(11) . . . . ? C10 Fe1 C7 C3 -116.60(13) . . . . ? C4 Fe1 C7 C3 -38.33(10) . . . . ? C6 Fe1 C7 C3 -118.95(15) . . . . ? C5 Fe1 C7 C3 -81.67(11) . . . . ? C2 Fe1 C7 C6 170.54(11) . . . . ? C1 Fe1 C7 C6 -93.08(11) . . . . ? C10 Fe1 C7 C6 2.35(18) . . . . ? C4 Fe1 C7 C6 80.63(11) . . . . ? C3 Fe1 C7 C6 118.95(15) . . . . ? C5 Fe1 C7 C6 37.29(10) . . . . ? C9 O3 C8 O4 5.0(2) . . . . ? C9 O3 C8 C4 -173.17(15) . . . . ? C5 C4 C8 O4 1.8(3) . . . . ? C3 C4 C8 O4 -174.22(18) . . . . ? Fe1 C4 C8 O4 92.6(2) . . . . ? C5 C4 C8 O3 -179.99(15) . . . . ? C3 C4 C8 O3 4.0(3) . . . . ? Fe1 C4 C8 O3 -89.15(17) . . . . ? C11 O5 C10 O6 -2.4(2) . . . . ? C11 O5 C10 Fe1 178.41(12) . . . . ? C2 Fe1 C10 O6 156.21(16) . . . . ? C1 Fe1 C10 O6 63.08(16) . . . . ? C4 Fe1 C10 O6 -101.08(16) . . . . ? C3 Fe1 C10 O6 -104.47(17) . . . . ? C6 Fe1 C10 O6 -32.47(17) . . . . ? C7 Fe1 C10 O6 -34.0(2) . . . . ? C5 Fe1 C10 O6 -65.76(16) . . . . ? C2 Fe1 C10 O5 -24.68(13) . . . . ? C1 Fe1 C10 O5 -117.81(12) . . . . ? C4 Fe1 C10 O5 78.04(12) . . . . ? C3 Fe1 C10 O5 74.64(17) . . . . ? C6 Fe1 C10 O5 146.65(11) . . . . ? C7 Fe1 C10 O5 145.07(12) . . . . ? C5 Fe1 C10 O5 113.35(12) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.669 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.084 data_ime114 _database_code_depnum_ccdc_archive 'CCDC 640144' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Cl4 Fe2 O5' _chemical_formula_weight 460.66 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.0283(6) _cell_length_b 23.800(2) _cell_length_c 9.6737(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.931(4) _cell_angle_gamma 90.00 _cell_volume 1617.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7004 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.85 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 2.466 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5891 _exptl_absorpt_correction_T_max 0.7086 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 31667 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3830 _reflns_number_gt 3667 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.7489P] 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 3830 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0203 _refine_ls_R_factor_gt 0.0192 _refine_ls_wR_factor_ref 0.0534 _refine_ls_wR_factor_gt 0.0528 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.70696(2) 0.155788(7) 0.785738(18) 0.01464(6) Uani 1 1 d . . . Fe2 Fe 0.29351(3) 0.118218(8) 0.23533(2) 0.01961(6) Uani 1 1 d . . . Cl1 Cl 0.36144(5) 0.047680(14) 0.37184(4) 0.02830(8) Uani 1 1 d . . . Cl3 Cl 0.16169(6) 0.089848(19) 0.04157(4) 0.03675(10) Uani 1 1 d . . . Cl2 Cl 0.09832(6) 0.174543(17) 0.34291(4) 0.03740(10) Uani 1 1 d . . . Cl4 Cl 0.55375(6) 0.166616(19) 0.19455(4) 0.03760(10) Uani 1 1 d . . . O1 O 0.34062(14) 0.20705(4) 0.85777(11) 0.0268(2) Uani 1 1 d . . . O2 O 0.6444(2) 0.05089(5) 0.94072(13) 0.0396(3) Uani 1 1 d . . . O3 O 0.90748(16) 0.21773(5) 1.00598(12) 0.0350(3) Uani 1 1 d . . . O4 O 1.23601(14) 0.10436(4) 0.69505(11) 0.0246(2) Uani 1 1 d . . . O5 O 1.01974(14) 0.03446(4) 0.69369(12) 0.0291(2) Uani 1 1 d . . . C1 C 0.47980(19) 0.18650(5) 0.83220(14) 0.0193(2) Uani 1 1 d . . . C2 C 0.6685(2) 0.09135(6) 0.88350(15) 0.0242(3) Uani 1 1 d . . . C3 C 0.83121(19) 0.19253(6) 0.92370(14) 0.0222(3) Uani 1 1 d . . . C4 C 0.72335(19) 0.10849(6) 0.60317(14) 0.0206(3) Uani 1 1 d . . . H4A H 0.6764 0.0692 0.5896 0.025 Uiso 1 1 calc R . . C5 C 0.91063(18) 0.12461(5) 0.64999(13) 0.0180(2) Uani 1 1 d . . . C6 C 0.91913(18) 0.18422(6) 0.65069(13) 0.0189(2) Uani 1 1 d . . . H6A H 1.0326 0.2074 0.6774 0.023 Uiso 1 1 calc R . . C7 C 0.73867(19) 0.20530(6) 0.60837(14) 0.0215(3) Uani 1 1 d . . . H7A H 0.7030 0.2458 0.5986 0.026 Uiso 1 1 calc R . . C8 C 0.6190(2) 0.15815(6) 0.57686(14) 0.0219(3) Uani 1 1 d . . . H8A H 0.4843 0.1601 0.5422 0.026 Uiso 1 1 calc R . . C9 C 1.07561(19) 0.08725(6) 0.68284(13) 0.0192(2) Uani 1 1 d . . . C10 C 1.1696(2) -0.00613(7) 0.7215(2) 0.0359(4) Uani 1 1 d . . . H10A H 1.1142 -0.0438 0.7276 0.054 Uiso 1 1 calc R . . H10B H 1.2340 0.0032 0.8091 0.054 Uiso 1 1 calc R . . H10C H 1.2616 -0.0052 0.6465 0.054 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 0.01309(9) 0.01639(9) 0.01444(9) -0.00034(6) 0.00017(7) -0.00119(6) Fe2 0.02273(10) 0.01954(10) 0.01663(10) 0.00056(7) 0.00266(7) 0.00140(7) Cl1 0.03243(18) 0.02132(16) 0.03092(18) 0.00470(13) -0.00662(14) 0.00094(13) Cl3 0.0425(2) 0.0454(2) 0.02203(17) -0.00318(15) -0.00694(15) 0.00063(17) Cl2 0.0491(2) 0.03045(19) 0.0332(2) 0.00339(15) 0.01830(18) 0.01478(16) Cl4 0.0349(2) 0.0412(2) 0.0369(2) 0.00252(17) 0.00861(16) -0.01290(16) O1 0.0193(5) 0.0279(5) 0.0335(6) -0.0068(4) 0.0028(4) 0.0021(4) O2 0.0521(7) 0.0261(6) 0.0410(7) 0.0109(5) 0.0131(6) 0.0011(5) O3 0.0299(5) 0.0461(7) 0.0287(6) -0.0073(5) -0.0062(5) -0.0122(5) O4 0.0174(4) 0.0272(5) 0.0292(5) -0.0033(4) 0.0004(4) -0.0013(4) O5 0.0204(5) 0.0192(5) 0.0479(7) 0.0023(5) 0.0040(5) 0.0009(4) C1 0.0199(6) 0.0199(6) 0.0182(6) -0.0022(5) -0.0006(5) -0.0041(5) C2 0.0249(7) 0.0244(7) 0.0233(7) -0.0003(5) 0.0046(5) 0.0018(5) C3 0.0171(6) 0.0278(7) 0.0219(6) 0.0010(5) 0.0007(5) -0.0027(5) C4 0.0203(6) 0.0246(6) 0.0169(6) -0.0049(5) 0.0006(5) -0.0028(5) C5 0.0175(6) 0.0207(6) 0.0159(6) -0.0015(5) 0.0031(5) -0.0010(5) C6 0.0178(6) 0.0210(6) 0.0181(6) 0.0022(5) 0.0042(5) -0.0022(5) C7 0.0235(6) 0.0240(6) 0.0171(6) 0.0048(5) 0.0014(5) 0.0006(5) C8 0.0199(6) 0.0313(7) 0.0144(6) -0.0001(5) -0.0016(5) 0.0001(5) C9 0.0188(6) 0.0209(6) 0.0179(6) -0.0024(5) 0.0041(5) 0.0000(5) C10 0.0296(8) 0.0245(7) 0.0538(10) 0.0056(7) 0.0057(7) 0.0090(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C3 1.8085(14) . ? Fe1 C1 1.8189(14) . ? Fe1 C2 1.8242(15) . ? Fe1 C5 2.0941(13) . ? Fe1 C7 2.0963(13) . ? Fe1 C4 2.0991(13) . ? Fe1 C8 2.1042(13) . ? Fe1 C6 2.1099(13) . ? Fe2 Cl1 2.1839(4) . ? Fe2 Cl3 2.1843(4) . ? Fe2 Cl2 2.1928(4) . ? Fe2 Cl4 2.2026(4) . ? O1 C1 1.1249(17) . ? O2 C2 1.1248(19) . ? O3 C3 1.1255(18) . ? O4 C9 1.2026(17) . ? O5 C9 1.3212(17) . ? O5 C10 1.4508(18) . ? C4 C8 1.412(2) . ? C4 C5 1.4372(18) . ? C4 H4A 1.0000 . ? C5 C6 1.4201(18) . ? C5 C9 1.4913(18) . ? C6 C7 1.4181(19) . ? C6 H6A 1.0000 . ? C7 C8 1.432(2) . ? C7 H7A 1.0000 . ? C8 H8A 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Fe1 C1 92.21(6) . . ? C3 Fe1 C2 95.61(7) . . ? C1 Fe1 C2 94.10(6) . . ? C3 Fe1 C5 107.90(6) . . ? C1 Fe1 C5 155.37(6) . . ? C2 Fe1 C5 97.81(6) . . ? C3 Fe1 C7 106.01(6) . . ? C1 Fe1 C7 94.69(6) . . ? C2 Fe1 C7 156.28(6) . . ? C5 Fe1 C7 66.62(5) . . ? C3 Fe1 C4 147.97(6) . . ? C1 Fe1 C4 118.93(6) . . ? C2 Fe1 C4 89.77(6) . . ? C5 Fe1 C4 40.09(5) . . ? C7 Fe1 C4 66.72(6) . . ? C3 Fe1 C8 145.75(6) . . ? C1 Fe1 C8 88.92(6) . . ? C2 Fe1 C8 118.46(6) . . ? C5 Fe1 C8 66.45(5) . . ? C7 Fe1 C8 39.87(5) . . ? C4 Fe1 C8 39.25(5) . . ? C3 Fe1 C6 87.95(6) . . ? C1 Fe1 C6 131.01(6) . . ? C2 Fe1 C6 134.66(6) . . ? C5 Fe1 C6 39.48(5) . . ? C7 Fe1 C6 39.40(5) . . ? C4 Fe1 C6 66.55(5) . . ? C8 Fe1 C6 66.20(5) . . ? Cl1 Fe2 Cl3 111.516(18) . . ? Cl1 Fe2 Cl2 108.378(18) . . ? Cl3 Fe2 Cl2 109.65(2) . . ? Cl1 Fe2 Cl4 109.651(18) . . ? Cl3 Fe2 Cl4 110.478(19) . . ? Cl2 Fe2 Cl4 107.04(2) . . ? C9 O5 C10 115.61(12) . . ? O1 C1 Fe1 177.49(13) . . ? O2 C2 Fe1 178.25(14) . . ? O3 C3 Fe1 176.64(14) . . ? C8 C4 C5 107.68(12) . . ? C8 C4 Fe1 70.57(8) . . ? C5 C4 Fe1 69.77(7) . . ? C8 C4 H4A 126.2 . . ? C5 C4 H4A 126.2 . . ? Fe1 C4 H4A 126.2 . . ? C6 C5 C4 107.85(12) . . ? C6 C5 C9 124.20(12) . . ? C4 C5 C9 127.80(12) . . ? C6 C5 Fe1 70.86(7) . . ? C4 C5 Fe1 70.14(7) . . ? C9 C5 Fe1 127.93(9) . . ? C7 C6 C5 108.34(12) . . ? C7 C6 Fe1 69.78(7) . . ? C5 C6 Fe1 69.66(7) . . ? C7 C6 H6A 125.8 . . ? C5 C6 H6A 125.8 . . ? Fe1 C6 H6A 125.8 . . ? C6 C7 C8 107.68(12) . . ? C6 C7 Fe1 70.82(7) . . ? C8 C7 Fe1 70.36(8) . . ? C6 C7 H7A 126.1 . . ? C8 C7 H7A 126.1 . . ? Fe1 C7 H7A 126.1 . . ? C4 C8 C7 108.42(12) . . ? C4 C8 Fe1 70.18(8) . . ? C7 C8 Fe1 69.77(8) . . ? C4 C8 H8A 125.8 . . ? C7 C8 H8A 125.8 . . ? Fe1 C8 H8A 125.8 . . ? O4 C9 O5 126.41(13) . . ? O4 C9 C5 122.92(12) . . ? O5 C9 C5 110.66(11) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.548 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.080 data_ime75m _database_code_depnum_ccdc_archive 'CCDC 640137' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Fe2 O8' _chemical_formula_weight 469.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.525(3) _cell_length_b 6.757(3) _cell_length_c 10.099(5) _cell_angle_alpha 87.774(8) _cell_angle_beta 86.467(8) _cell_angle_gamma 73.748(7) _cell_volume 426.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1330 _cell_measurement_theta_min 6.282 _cell_measurement_theta_max 52.558 _exptl_crystal_description PLATE _exptl_crystal_colour RED _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 1.748 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6047 _exptl_absorpt_correction_T_max 0.9334 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3012 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1472 _reflns_number_gt 1255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+5.2504P] 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 1472 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1893 _refine_ls_wR_factor_gt 0.1856 _refine_ls_goodness_of_fit_ref 1.296 _refine_ls_restrained_S_all 1.296 _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 0.00366(19) -0.01197(18) 0.37540(12) 0.0144(4) Uani 1 1 d . . . O1 O -0.3094(11) 0.3821(10) 0.3337(7) 0.0340(17) Uani 1 1 d . . . O2 O 0.2991(9) 0.1930(9) 0.4752(6) 0.0235(14) Uani 1 1 d . . . O3 O 0.1923(10) 0.2497(9) 0.0837(6) 0.0242(14) Uani 1 1 d . . . O4 O 0.5123(10) 0.0712(11) 0.1574(7) 0.0308(16) Uani 1 1 d . . . C1 C -0.1895(14) 0.2264(14) 0.3529(9) 0.021(2) Uani 1 1 d . . . C2 C 0.1659(13) 0.1048(12) 0.4868(8) 0.0165(18) Uani 1 1 d . . . C3 C 0.2130(13) -0.0566(13) 0.2048(8) 0.0184(18) Uani 1 1 d . . . C4 C 0.2995(14) -0.2132(13) 0.2996(9) 0.024(2) Uani 1 1 d . . . H4A H 0.4416 -0.2392 0.3392 0.029 Uiso 1 1 calc R . . C5 C 0.1496(15) -0.3281(14) 0.3270(9) 0.026(2) Uani 1 1 d . . . H5A H 0.1677 -0.4487 0.3902 0.031 Uiso 1 1 calc R . . C6 C -0.0287(15) -0.2457(14) 0.2483(9) 0.024(2) Uani 1 1 d . . . H6A H -0.1567 -0.2989 0.2454 0.029 Uiso 1 1 calc R . . C7 C 0.0063(13) -0.0752(13) 0.1755(8) 0.0178(18) Uani 1 1 d . . . H7A H -0.0902 0.0106 0.1091 0.021 Uiso 1 1 calc R . . C8 C 0.3225(15) 0.0926(15) 0.1489(9) 0.024(2) Uani 1 1 d . . . C9 C 0.2948(16) 0.3948(15) 0.0212(10) 0.033(2) Uani 1 1 d . . . H9A H 0.1886 0.5042 -0.0239 0.049 Uiso 1 1 calc R . . H9B H 0.4064 0.3236 -0.0437 0.049 Uiso 1 1 calc R . . H9C H 0.3590 0.4553 0.0887 0.049 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 0.0154(6) 0.0132(6) 0.0140(7) -0.0039(4) 0.0039(4) -0.0035(4) O1 0.030(4) 0.019(4) 0.050(5) 0.000(3) -0.003(3) -0.001(3) O2 0.021(3) 0.020(3) 0.032(4) -0.006(3) 0.002(3) -0.010(3) O3 0.023(3) 0.024(3) 0.030(4) 0.000(3) 0.006(3) -0.015(3) O4 0.016(3) 0.047(4) 0.033(4) -0.008(3) 0.006(3) -0.016(3) C1 0.024(5) 0.022(5) 0.020(5) -0.009(4) 0.003(4) -0.013(4) C2 0.015(4) 0.015(4) 0.019(4) -0.010(3) 0.000(3) -0.003(3) C3 0.013(4) 0.022(5) 0.021(5) -0.008(4) 0.006(3) -0.006(4) C4 0.018(4) 0.020(5) 0.025(5) -0.013(4) 0.005(4) 0.008(4) C5 0.038(6) 0.016(5) 0.020(5) -0.008(4) 0.011(4) -0.003(4) C6 0.031(5) 0.026(5) 0.020(5) -0.016(4) 0.010(4) -0.015(4) C7 0.022(5) 0.023(5) 0.011(4) -0.008(3) 0.004(3) -0.012(4) C8 0.027(5) 0.030(5) 0.017(5) -0.011(4) 0.006(4) -0.013(4) C9 0.036(6) 0.029(5) 0.036(6) -0.004(4) 0.013(5) -0.016(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 1.762(10) . ? Fe1 C2 1.920(8) 2_556 ? Fe1 C2 1.921(8) . ? Fe1 C7 2.077(8) . ? Fe1 C3 2.108(8) . ? Fe1 C6 2.136(8) . ? Fe1 C4 2.143(8) . ? Fe1 C5 2.143(9) . ? Fe1 Fe1 2.525(3) 2_556 ? O1 C1 1.140(11) . ? O2 C2 1.182(10) . ? O3 C8 1.339(12) . ? O3 C9 1.440(10) . ? O4 C8 1.214(11) . ? C2 Fe1 1.920(8) 2_556 ? C3 C4 1.417(13) . ? C3 C7 1.439(11) . ? C3 C8 1.467(12) . ? C4 C5 1.418(13) . ? C4 H4A 1.0000 . ? C5 C6 1.418(14) . ? C5 H5A 1.0000 . ? C6 C7 1.407(12) . ? C6 H6A 1.0000 . ? C7 H7A 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 C2 93.6(4) . 2_556 ? C1 Fe1 C2 92.7(4) . . ? C2 Fe1 C2 97.8(3) 2_556 . ? C1 Fe1 C7 90.9(4) . . ? C2 Fe1 C7 124.6(3) 2_556 . ? C2 Fe1 C7 137.1(3) . . ? C1 Fe1 C3 107.0(4) . . ? C2 Fe1 C3 153.0(3) 2_556 . ? C2 Fe1 C3 98.5(3) . . ? C7 Fe1 C3 40.2(3) . . ? C1 Fe1 C6 113.3(4) . . ? C2 Fe1 C6 90.3(3) 2_556 . ? C2 Fe1 C6 152.3(4) . . ? C7 Fe1 C6 39.0(3) . . ? C3 Fe1 C6 65.8(3) . . ? C1 Fe1 C4 145.3(4) . . ? C2 Fe1 C4 120.8(4) 2_556 . ? C2 Fe1 C4 88.1(3) . . ? C7 Fe1 C4 66.1(3) . . ? C3 Fe1 C4 38.9(3) . . ? C6 Fe1 C4 65.2(4) . . ? C1 Fe1 C5 152.0(4) . . ? C2 Fe1 C5 88.4(3) 2_556 . ? C2 Fe1 C5 114.7(4) . . ? C7 Fe1 C5 65.5(4) . . ? C3 Fe1 C5 65.2(3) . . ? C6 Fe1 C5 38.7(4) . . ? C4 Fe1 C5 38.6(3) . . ? C1 Fe1 Fe1 94.8(3) . 2_556 ? C2 Fe1 Fe1 48.9(2) 2_556 2_556 ? C2 Fe1 Fe1 48.9(3) . 2_556 ? C7 Fe1 Fe1 171.6(2) . 2_556 ? C3 Fe1 Fe1 142.2(2) . 2_556 ? C6 Fe1 Fe1 132.7(3) . 2_556 ? C4 Fe1 Fe1 111.3(3) . 2_556 ? C5 Fe1 Fe1 107.3(3) . 2_556 ? C8 O3 C9 114.8(7) . . ? O1 C1 Fe1 177.1(8) . . ? O2 C2 Fe1 139.2(7) . 2_556 ? O2 C2 Fe1 138.6(7) . . ? Fe1 C2 Fe1 82.2(3) 2_556 . ? C4 C3 C7 107.5(7) . . ? C4 C3 C8 124.3(8) . . ? C7 C3 C8 128.1(8) . . ? C4 C3 Fe1 71.8(5) . . ? C7 C3 Fe1 68.7(4) . . ? C8 C3 Fe1 125.2(6) . . ? C3 C4 C5 107.8(8) . . ? C3 C4 Fe1 69.2(5) . . ? C5 C4 Fe1 70.7(5) . . ? C3 C4 H4A 126.1 . . ? C5 C4 H4A 126.1 . . ? Fe1 C4 H4A 126.1 . . ? C4 C5 C6 108.7(8) . . ? C4 C5 Fe1 70.7(5) . . ? C6 C5 Fe1 70.4(5) . . ? C4 C5 H5A 125.7 . . ? C6 C5 H5A 125.7 . . ? Fe1 C5 H5A 125.7 . . ? C7 C6 C5 107.8(8) . . ? C7 C6 Fe1 68.2(5) . . ? C5 C6 Fe1 70.9(5) . . ? C7 C6 H6A 126.1 . . ? C5 C6 H6A 126.1 . . ? Fe1 C6 H6A 126.1 . . ? C6 C7 C3 108.2(8) . . ? C6 C7 Fe1 72.8(5) . . ? C3 C7 Fe1 71.1(5) . . ? C6 C7 H7A 125.8 . . ? C3 C7 H7A 125.8 . . ? Fe1 C7 H7A 125.8 . . ? O4 C8 O3 123.9(8) . . ? O4 C8 C3 123.3(9) . . ? O3 C8 C3 112.7(8) . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 C2 Fe1 C1 O1 -171(16) 2_556 . . . ? C2 Fe1 C1 O1 91(16) . . . . ? C7 Fe1 C1 O1 -46(16) . . . . ? C3 Fe1 C1 O1 -9(16) . . . . ? C6 Fe1 C1 O1 -79(16) . . . . ? C4 Fe1 C1 O1 0(16) . . . . ? C5 Fe1 C1 O1 -78(16) . . . . ? Fe1 Fe1 C1 O1 140(16) 2_556 . . . ? C1 Fe1 C2 O2 -84.6(10) . . . . ? C2 Fe1 C2 O2 -178.5(12) 2_556 . . . ? C7 Fe1 C2 O2 9.7(13) . . . . ? C3 Fe1 C2 O2 23.0(10) . . . . ? C6 Fe1 C2 O2 75.7(13) . . . . ? C4 Fe1 C2 O2 60.7(10) . . . . ? C5 Fe1 C2 O2 89.6(10) . . . . ? Fe1 Fe1 C2 O2 -178.5(12) 2_556 . . . ? C1 Fe1 C2 Fe1 94.0(4) . . . 2_556 ? C2 Fe1 C2 Fe1 0.0 2_556 . . 2_556 ? C7 Fe1 C2 Fe1 -171.8(4) . . . 2_556 ? C3 Fe1 C2 Fe1 -158.4(3) . . . 2_556 ? C6 Fe1 C2 Fe1 -105.8(7) . . . 2_556 ? C4 Fe1 C2 Fe1 -120.8(3) . . . 2_556 ? C5 Fe1 C2 Fe1 -91.9(4) . . . 2_556 ? C1 Fe1 C3 C4 171.7(5) . . . . ? C2 Fe1 C3 C4 -50.4(10) 2_556 . . . ? C2 Fe1 C3 C4 76.2(6) . . . . ? C7 Fe1 C3 C4 -117.9(7) . . . . ? C6 Fe1 C3 C4 -79.9(6) . . . . ? C5 Fe1 C3 C4 -37.1(5) . . . . ? Fe1 Fe1 C3 C4 49.4(7) 2_556 . . . ? C1 Fe1 C3 C7 -70.4(6) . . . . ? C2 Fe1 C3 C7 67.5(9) 2_556 . . . ? C2 Fe1 C3 C7 -165.9(5) . . . . ? C6 Fe1 C3 C7 38.0(5) . . . . ? C4 Fe1 C3 C7 117.9(7) . . . . ? C5 Fe1 C3 C7 80.7(6) . . . . ? Fe1 Fe1 C3 C7 167.2(4) 2_556 . . . ? C1 Fe1 C3 C8 52.0(9) . . . . ? C2 Fe1 C3 C8 -170.1(7) 2_556 . . . ? C2 Fe1 C3 C8 -43.4(8) . . . . ? C7 Fe1 C3 C8 122.5(10) . . . . ? C6 Fe1 C3 C8 160.5(9) . . . . ? C4 Fe1 C3 C8 -119.7(10) . . . . ? C5 Fe1 C3 C8 -156.8(9) . . . . ? Fe1 Fe1 C3 C8 -70.3(9) 2_556 . . . ? C7 C3 C4 C5 0.7(9) . . . . ? C8 C3 C4 C5 -178.8(8) . . . . ? Fe1 C3 C4 C5 60.5(6) . . . . ? C7 C3 C4 Fe1 -59.8(5) . . . . ? C8 C3 C4 Fe1 120.8(8) . . . . ? C1 Fe1 C4 C3 -14.0(9) . . . . ? C2 Fe1 C4 C3 156.0(5) 2_556 . . . ? C2 Fe1 C4 C3 -106.0(5) . . . . ? C7 Fe1 C4 C3 38.6(5) . . . . ? C6 Fe1 C4 C3 81.6(5) . . . . ? C5 Fe1 C4 C3 118.6(8) . . . . ? Fe1 Fe1 C4 C3 -150.1(4) 2_556 . . . ? C1 Fe1 C4 C5 -132.6(7) . . . . ? C2 Fe1 C4 C5 37.4(7) 2_556 . . . ? C2 Fe1 C4 C5 135.3(6) . . . . ? C7 Fe1 C4 C5 -80.0(6) . . . . ? C3 Fe1 C4 C5 -118.6(8) . . . . ? C6 Fe1 C4 C5 -37.0(5) . . . . ? Fe1 Fe1 C4 C5 91.3(5) 2_556 . . . ? C3 C4 C5 C6 0.8(9) . . . . ? Fe1 C4 C5 C6 60.4(6) . . . . ? C3 C4 C5 Fe1 -59.5(6) . . . . ? C1 Fe1 C5 C4 116.8(8) . . . . ? C2 Fe1 C5 C4 -148.5(6) 2_556 . . . ? C2 Fe1 C5 C4 -50.7(6) . . . . ? C7 Fe1 C5 C4 81.9(6) . . . . ? C3 Fe1 C5 C4 37.4(5) . . . . ? C6 Fe1 C5 C4 119.0(8) . . . . ? Fe1 Fe1 C5 C4 -102.7(5) 2_556 . . . ? C1 Fe1 C5 C6 -2.2(10) . . . . ? C2 Fe1 C5 C6 92.4(5) 2_556 . . . ? C2 Fe1 C5 C6 -169.7(5) . . . . ? C7 Fe1 C5 C6 -37.2(5) . . . . ? C3 Fe1 C5 C6 -81.6(5) . . . . ? C4 Fe1 C5 C6 -119.0(8) . . . . ? Fe1 Fe1 C5 C6 138.2(5) 2_556 . . . ? C4 C5 C6 C7 -2.1(9) . . . . ? Fe1 C5 C6 C7 58.5(6) . . . . ? C4 C5 C6 Fe1 -60.5(6) . . . . ? C1 Fe1 C6 C7 59.7(6) . . . . ? C2 Fe1 C6 C7 153.7(6) 2_556 . . . ? C2 Fe1 C6 C7 -98.7(9) . . . . ? C3 Fe1 C6 C7 -39.2(5) . . . . ? C4 Fe1 C6 C7 -82.1(6) . . . . ? C5 Fe1 C6 C7 -119.1(7) . . . . ? Fe1 Fe1 C6 C7 -179.0(4) 2_556 . . . ? C1 Fe1 C6 C5 178.9(5) . . . . ? C2 Fe1 C6 C5 -87.1(5) 2_556 . . . ? C2 Fe1 C6 C5 20.4(10) . . . . ? C7 Fe1 C6 C5 119.1(7) . . . . ? C3 Fe1 C6 C5 80.0(6) . . . . ? C4 Fe1 C6 C5 37.0(5) . . . . ? Fe1 Fe1 C6 C5 -59.9(6) 2_556 . . . ? C5 C6 C7 C3 2.5(9) . . . . ? Fe1 C6 C7 C3 62.6(5) . . . . ? C5 C6 C7 Fe1 -60.1(6) . . . . ? C4 C3 C7 C6 -2.0(9) . . . . ? C8 C3 C7 C6 177.5(8) . . . . ? Fe1 C3 C7 C6 -63.7(6) . . . . ? C4 C3 C7 Fe1 61.7(6) . . . . ? C8 C3 C7 Fe1 -118.8(8) . . . . ? C1 Fe1 C7 C6 -127.5(6) . . . . ? C2 Fe1 C7 C6 -32.5(7) 2_556 . . . ? C2 Fe1 C7 C6 137.6(6) . . . . ? C3 Fe1 C7 C6 116.8(7) . . . . ? C4 Fe1 C7 C6 79.4(6) . . . . ? C5 Fe1 C7 C6 36.9(5) . . . . ? Fe1 Fe1 C7 C6 5(2) 2_556 . . . ? C1 Fe1 C7 C3 115.7(5) . . . . ? C2 Fe1 C7 C3 -149.4(5) 2_556 . . . ? C2 Fe1 C7 C3 20.7(8) . . . . ? C6 Fe1 C7 C3 -116.8(7) . . . . ? C4 Fe1 C7 C3 -37.4(5) . . . . ? C5 Fe1 C7 C3 -79.9(5) . . . . ? Fe1 Fe1 C7 C3 -111.7(17) 2_556 . . . ? C9 O3 C8 O4 0.6(12) . . . . ? C9 O3 C8 C3 -177.0(7) . . . . ? C4 C3 C8 O4 15.5(13) . . . . ? C7 C3 C8 O4 -163.9(8) . . . . ? Fe1 C3 C8 O4 106.7(9) . . . . ? C4 C3 C8 O3 -166.9(8) . . . . ? C7 C3 C8 O3 13.8(12) . . . . ? Fe1 C3 C8 O3 -75.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.280 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.162 data_ime112 _database_code_depnum_ccdc_archive 'CCDC 640138' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Fe2 O10' _chemical_formula_weight 530.04 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.283(4) _cell_length_b 8.083(4) _cell_length_c 17.632(8) _cell_angle_alpha 103.139(5) _cell_angle_beta 97.091(5) _cell_angle_gamma 98.965(5) _cell_volume 984.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6976 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.88 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 1.533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7391 _exptl_absorpt_correction_T_max 0.8872 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9874 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3875 _reflns_number_gt 3633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.7338P] 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 3875 _refine_ls_number_parameters 308 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 0.14895(3) 0.61124(3) 0.379554(13) 0.01322(7) Uani 1 1 d . . . Fe2 Fe -0.01560(3) 0.47027(3) 0.239980(13) 0.01271(7) Uani 1 1 d . . . O1 O 0.2604(2) 0.31817(18) 0.43030(8) 0.0301(3) Uani 1 1 d . . . O2 O -0.01283(19) 0.10839(16) 0.23452(8) 0.0264(3) Uani 1 1 d . . . O3 O -0.24439(17) 0.44393(16) 0.36251(7) 0.0212(3) Uani 1 1 d . . . O4 O 0.39307(17) 0.54154(17) 0.26191(7) 0.0224(3) Uani 1 1 d . . . O5 O 0.62433(18) 0.89710(17) 0.36800(8) 0.0246(3) Uani 1 1 d . . . O6 O 0.38824(17) 0.96880(16) 0.29426(7) 0.0200(3) Uani 1 1 d . . . O8 O 0.30858(18) 0.62359(16) 0.09543(8) 0.0228(3) Uani 1 1 d . . . O9 O 0.14889(18) 0.35192(16) 0.04415(7) 0.0223(3) Uani 1 1 d . . . C1 C 0.2149(3) 0.4320(2) 0.40943(10) 0.0197(4) Uani 1 1 d . . . C2 C -0.0104(2) 0.2516(2) 0.23634(10) 0.0181(4) Uani 1 1 d . . . C3 C -0.1044(2) 0.4871(2) 0.33987(10) 0.0159(3) Uani 1 1 d . . . C4 C 0.2469(2) 0.5385(2) 0.28349(10) 0.0158(3) Uani 1 1 d . . . C5 C 0.1223(2) 0.8750(2) 0.38778(10) 0.0169(3) Uani 1 1 d . . . H5A H 0.0595 0.9200 0.3451 0.020 Uiso 1 1 calc R . . C6 C 0.0354(3) 0.8158(2) 0.44655(10) 0.0194(4) Uani 1 1 d . . . H6A H -0.0999 0.8115 0.4526 0.023 Uiso 1 1 calc R . . C7 C 0.1722(3) 0.7635(2) 0.49512(10) 0.0221(4) Uani 1 1 d . . . H7A H 0.1518 0.7194 0.5426 0.026 Uiso 1 1 calc R . . C8 C 0.3474(3) 0.7926(2) 0.46693(10) 0.0213(4) Uani 1 1 d . . . H8A H 0.4711 0.7735 0.4914 0.026 Uiso 1 1 calc R . . C9 C 0.3166(2) 0.8631(2) 0.40127(10) 0.0173(3) Uani 1 1 d . . . C10 C -0.1552(2) 0.4079(2) 0.12321(10) 0.0185(4) Uani 1 1 d . . . H10A H -0.1869 0.2901 0.0860 0.022 Uiso 1 1 calc R . . C11 C -0.2735(3) 0.4843(2) 0.17352(10) 0.0204(4) Uani 1 1 d . . . H11A H -0.4020 0.4282 0.1790 0.024 Uiso 1 1 calc R . . C12 C -0.1797(2) 0.6526(2) 0.21394(10) 0.0184(4) Uani 1 1 d . . . H12A H -0.2299 0.7363 0.2534 0.022 Uiso 1 1 calc R . . C13 C -0.0034(2) 0.6845(2) 0.18875(10) 0.0165(3) Uani 1 1 d . . . H13A H 0.0920 0.7947 0.2067 0.020 Uiso 1 1 calc R . . C14 C 0.0115(2) 0.5335(2) 0.13148(10) 0.0164(3) Uani 1 1 d . . . C15 C 0.4618(2) 0.9097(2) 0.35433(10) 0.0187(4) Uani 1 1 d . . . C16 C 0.5178(3) 1.0116(3) 0.24257(12) 0.0284(4) Uani 1 1 d . A . H16A H 0.5612 0.9066 0.2159 0.034 Uiso 1 1 calc R . . H16B H 0.6293 1.0974 0.2734 0.034 Uiso 1 1 calc R . . C17 C 0.4168(3) 1.0844(3) 0.18319(13) 0.0354(5) Uani 1 1 d D . . H17A H 0.3541 1.1748 0.2111 0.042 Uiso 0.584(4) 1 calc PR A 1 H17B H 0.5105 1.1409 0.1563 0.042 Uiso 0.584(4) 1 calc PR A 1 H17C H 0.2902 1.0108 0.1639 0.042 Uiso 0.416(4) 1 calc PR A 2 H17D H 0.3985 1.2006 0.2104 0.042 Uiso 0.416(4) 1 calc PR A 2 C18 C 0.1728(2) 0.5121(2) 0.08997(10) 0.0170(3) Uani 1 1 d . . . C19 C 0.3004(3) 0.3112(2) 0.00182(11) 0.0237(4) Uani 1 1 d . B . H19A H 0.4141 0.3123 0.0392 0.028 Uiso 1 1 calc R . . H19B H 0.3326 0.3974 -0.0287 0.028 Uiso 1 1 calc R . . C20 C 0.2327(2) 0.13375(19) -0.05293(9) 0.0297(4) Uani 1 1 d D . . H20A H 0.1032 0.1254 -0.0804 0.036 Uiso 0.510(14) 1 calc PR B 1 H20B H 0.3155 0.1144 -0.0933 0.036 Uiso 0.510(14) 1 calc PR B 1 H20C H 0.1422 0.1427 -0.0979 0.036 Uiso 0.490(14) 1 calc PR B 2 H20D H 0.3415 0.0928 -0.0744 0.036 Uiso 0.490(14) 1 calc PR B 2 O7A O 0.2903(2) 0.97032(19) 0.12967(9) 0.0298(7) Uani 0.584(4) 1 d PRD A 1 H7A1 H 0.3098 0.8704 0.1292 0.045 Uiso 0.584(4) 1 calc PR A 1 O7B O 0.4956(4) 1.0994(4) 0.12181(17) 0.0246(9) Uani 0.416(4) 1 d PD A 2 H7B H 0.4161 1.0563 0.0805 0.037 Uiso 0.416(4) 1 calc PR A 2 O10A O 0.2337(17) 0.0036(6) -0.0095(3) 0.0500(16) Uani 0.510(14) 1 d PDU B 1 H10C H 0.3165 0.0403 0.0311 0.075 Uiso 0.510(14) 1 calc PR B 1 O10B O 0.1430(12) 0.0060(5) -0.0169(3) 0.0365(12) Uani 0.490(14) 1 d PDU B 2 H10B H 0.0351 0.0243 -0.0100 0.055 Uiso 0.490(14) 1 calc PR B 2 _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 0.01582(13) 0.01233(13) 0.01150(13) 0.00277(9) 0.00171(9) 0.00339(9) Fe2 0.01465(13) 0.01095(12) 0.01184(13) 0.00191(9) 0.00230(9) 0.00173(9) O1 0.0360(8) 0.0263(7) 0.0330(8) 0.0149(6) 0.0024(6) 0.0122(6) O2 0.0285(7) 0.0139(7) 0.0360(8) 0.0044(6) 0.0046(6) 0.0052(5) O3 0.0192(6) 0.0255(7) 0.0206(6) 0.0086(5) 0.0066(5) 0.0028(5) O4 0.0175(6) 0.0271(7) 0.0216(7) 0.0017(5) 0.0060(5) 0.0057(5) O5 0.0182(7) 0.0270(7) 0.0258(7) 0.0045(6) 0.0016(5) 0.0011(5) O6 0.0197(6) 0.0211(6) 0.0204(6) 0.0068(5) 0.0060(5) 0.0025(5) O8 0.0227(7) 0.0181(6) 0.0252(7) 0.0025(5) 0.0084(5) -0.0020(5) O9 0.0265(7) 0.0175(6) 0.0202(6) -0.0007(5) 0.0101(5) -0.0007(5) C1 0.0201(9) 0.0204(9) 0.0174(9) 0.0040(7) 0.0019(7) 0.0026(7) C2 0.0150(8) 0.0198(9) 0.0177(9) 0.0011(7) 0.0036(7) 0.0024(7) C3 0.0207(9) 0.0138(8) 0.0145(8) 0.0047(6) 0.0027(7) 0.0060(7) C4 0.0192(9) 0.0125(8) 0.0150(8) 0.0025(6) 0.0013(7) 0.0036(6) C5 0.0229(9) 0.0108(8) 0.0156(8) -0.0003(6) 0.0031(7) 0.0039(7) C6 0.0260(9) 0.0141(8) 0.0170(8) -0.0010(7) 0.0072(7) 0.0046(7) C7 0.0331(10) 0.0193(9) 0.0110(8) -0.0003(7) 0.0040(7) 0.0022(8) C8 0.0242(9) 0.0189(9) 0.0159(9) -0.0005(7) -0.0024(7) 0.0010(7) C9 0.0206(9) 0.0127(8) 0.0151(8) -0.0008(6) 0.0013(7) 0.0005(7) C10 0.0195(9) 0.0219(9) 0.0119(8) 0.0039(7) 0.0002(7) -0.0003(7) C11 0.0170(8) 0.0292(10) 0.0149(8) 0.0073(7) 0.0002(7) 0.0039(7) C12 0.0206(9) 0.0226(9) 0.0146(8) 0.0071(7) 0.0012(7) 0.0096(7) C13 0.0219(9) 0.0152(8) 0.0138(8) 0.0062(6) 0.0014(7) 0.0048(7) C14 0.0188(9) 0.0175(8) 0.0125(8) 0.0046(7) 0.0012(6) 0.0019(7) C15 0.0207(9) 0.0133(8) 0.0177(9) -0.0012(7) -0.0002(7) 0.0000(7) C16 0.0290(10) 0.0314(11) 0.0306(11) 0.0125(9) 0.0159(8) 0.0076(8) C17 0.0576(15) 0.0221(10) 0.0300(11) 0.0084(9) 0.0142(10) 0.0105(10) C18 0.0216(9) 0.0177(8) 0.0115(8) 0.0041(6) 0.0021(6) 0.0031(7) C19 0.0250(10) 0.0242(9) 0.0211(9) 0.0012(8) 0.0056(7) 0.0071(8) C20 0.0489(13) 0.0225(10) 0.0179(9) 0.0030(8) 0.0058(9) 0.0098(9) O7A 0.0395(15) 0.0201(12) 0.0301(14) 0.0095(10) 0.0045(11) 0.0028(10) O7B 0.0235(17) 0.0296(19) 0.0235(18) 0.0119(14) 0.0089(13) 0.0017(14) O10A 0.090(5) 0.0209(16) 0.033(2) 0.0068(13) -0.024(3) 0.020(2) O10B 0.068(3) 0.0195(16) 0.0208(18) 0.0077(12) -0.013(2) 0.017(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. ; _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 1.7633(19) . ? Fe1 C3 1.920(2) . ? Fe1 C4 1.9234(18) . ? Fe1 C8 2.0915(19) . ? Fe1 C7 2.0988(19) . ? Fe1 C9 2.1302(19) . ? Fe1 C6 2.1434(18) . ? Fe1 C5 2.145(2) . ? Fe1 Fe2 2.5224(10) . ? Fe2 C2 1.760(2) . ? Fe2 C4 1.914(2) . ? Fe2 C3 1.9335(18) . ? Fe2 C10 2.0927(19) . ? Fe2 C14 2.1135(19) . ? Fe2 C11 2.121(2) . ? Fe2 C13 2.1228(18) . ? Fe2 C12 2.1292(19) . ? O1 C1 1.145(2) . ? O2 C2 1.148(2) . ? O3 C3 1.172(2) . ? O4 C4 1.173(2) . ? O5 C15 1.203(2) . ? O6 C15 1.344(2) . ? O6 C16 1.447(2) . ? O8 C18 1.207(2) . ? O9 C18 1.334(2) . ? O9 C19 1.445(2) . ? C5 C6 1.413(3) . ? C5 C9 1.428(3) . ? C5 H5A 1.0000 . ? C6 C7 1.411(3) . ? C6 H6A 1.0000 . ? C7 C8 1.431(3) . ? C7 H7A 1.0000 . ? C8 C9 1.411(3) . ? C8 H8A 1.0000 . ? C9 C15 1.476(3) . ? C10 C11 1.420(3) . ? C10 C14 1.425(2) . ? C10 H10A 1.0000 . ? C11 C12 1.405(3) . ? C11 H11A 1.0000 . ? C12 C13 1.416(3) . ? C12 H12A 1.0000 . ? C13 C14 1.424(2) . ? C13 H13A 1.0000 . ? C14 C18 1.471(2) . ? C16 C17 1.486(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O7B 1.306(3) . ? C17 O7A 1.310(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 H17C 0.9900 . ? C17 H17D 0.9900 . ? C19 C20 1.505(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O10A 1.435(3) . ? C20 O10B 1.445(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? O7A H7A1 0.8400 . ? O7B H7B 0.8400 . ? O10A H10C 0.8400 . ? O10B H10B 0.8400 . ? _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe1 C3 91.53(8) . . ? C1 Fe1 C4 88.75(8) . . ? C3 Fe1 C4 96.25(8) . . ? C1 Fe1 C8 93.96(8) . . ? C3 Fe1 C8 150.88(7) . . ? C4 Fe1 C8 112.42(8) . . ? C1 Fe1 C7 94.50(8) . . ? C3 Fe1 C7 111.14(8) . . ? C4 Fe1 C7 152.28(8) . . ? C8 Fe1 C7 39.93(8) . . ? C1 Fe1 C9 126.96(8) . . ? C3 Fe1 C9 141.12(7) . . ? C4 Fe1 C9 90.46(7) . . ? C8 Fe1 C9 39.05(7) . . ? C7 Fe1 C9 65.71(7) . . ? C1 Fe1 C6 127.61(8) . . ? C3 Fe1 C6 88.37(8) . . ? C4 Fe1 C6 143.30(7) . . ? C8 Fe1 C6 65.80(8) . . ? C7 Fe1 C6 38.84(7) . . ? C9 Fe1 C6 65.04(8) . . ? C1 Fe1 C5 158.27(8) . . ? C3 Fe1 C5 102.79(7) . . ? C4 Fe1 C5 105.56(7) . . ? C8 Fe1 C5 65.68(7) . . ? C7 Fe1 C5 65.24(7) . . ? C9 Fe1 C5 39.02(7) . . ? C6 Fe1 C5 38.48(7) . . ? C1 Fe1 Fe2 101.10(6) . . ? C3 Fe1 Fe2 49.35(5) . . ? C4 Fe1 Fe2 48.74(6) . . ? C8 Fe1 Fe2 154.90(5) . . ? C7 Fe1 Fe2 154.81(6) . . ? C9 Fe1 Fe2 117.28(5) . . ? C6 Fe1 Fe2 117.35(6) . . ? C5 Fe1 Fe2 100.62(5) . . ? C2 Fe2 C4 91.70(8) . . ? C2 Fe2 C3 87.65(7) . . ? C4 Fe2 C3 96.11(8) . . ? C2 Fe2 C10 91.96(8) . . ? C4 Fe2 C10 131.15(7) . . ? C3 Fe2 C10 132.70(8) . . ? C2 Fe2 C14 113.32(7) . . ? C4 Fe2 C14 95.60(7) . . ? C3 Fe2 C14 155.59(7) . . ? C10 Fe2 C14 39.61(7) . . ? C2 Fe2 C11 108.62(8) . . ? C4 Fe2 C11 156.35(7) . . ? C3 Fe2 C11 96.67(8) . . ? C10 Fe2 C11 39.37(7) . . ? C14 Fe2 C11 65.68(7) . . ? C2 Fe2 C13 152.60(8) . . ? C4 Fe2 C13 91.07(7) . . ? C3 Fe2 C13 119.12(7) . . ? C10 Fe2 C13 66.17(7) . . ? C14 Fe2 C13 39.29(6) . . ? C11 Fe2 C13 65.31(7) . . ? C2 Fe2 C12 146.59(8) . . ? C4 Fe2 C12 121.66(7) . . ? C3 Fe2 C12 90.19(7) . . ? C10 Fe2 C12 65.69(7) . . ? C14 Fe2 C12 65.45(7) . . ? C11 Fe2 C12 38.62(7) . . ? C13 Fe2 C12 38.89(7) . . ? C2 Fe2 Fe1 100.38(6) . . ? C4 Fe2 Fe1 49.07(5) . . ? C3 Fe2 Fe1 48.89(6) . . ? C10 Fe2 Fe1 167.66(5) . . ? C14 Fe2 Fe1 132.29(5) . . ? C11 Fe2 Fe1 133.90(5) . . ? C13 Fe2 Fe1 101.97(5) . . ? C12 Fe2 Fe1 103.14(5) . . ? C15 O6 C16 115.22(15) . . ? C18 O9 C19 116.65(14) . . ? O1 C1 Fe1 178.41(17) . . ? O2 C2 Fe2 177.79(16) . . ? O3 C3 Fe1 140.27(14) . . ? O3 C3 Fe2 137.95(14) . . ? Fe1 C3 Fe2 81.77(7) . . ? O4 C4 Fe2 138.87(14) . . ? O4 C4 Fe1 138.86(14) . . ? Fe2 C4 Fe1 82.19(7) . . ? C6 C5 C9 107.95(16) . . ? C6 C5 Fe1 70.72(10) . . ? C9 C5 Fe1 69.95(9) . . ? C6 C5 H5A 126.0 . . ? C9 C5 H5A 126.0 . . ? Fe1 C5 H5A 126.0 . . ? C7 C6 C5 108.23(17) . . ? C7 C6 Fe1 68.88(10) . . ? C5 C6 Fe1 70.81(10) . . ? C7 C6 H6A 125.9 . . ? C5 C6 H6A 125.9 . . ? Fe1 C6 H6A 125.9 . . ? C6 C7 C8 108.10(16) . . ? C6 C7 Fe1 72.29(10) . . ? C8 C7 Fe1 69.76(10) . . ? C6 C7 H7A 125.9 . . ? C8 C7 H7A 125.9 . . ? Fe1 C7 H7A 125.9 . . ? C9 C8 C7 107.66(16) . . ? C9 C8 Fe1 71.96(10) . . ? C7 C8 Fe1 70.31(10) . . ? C9 C8 H8A 126.1 . . ? C7 C8 H8A 126.1 . . ? Fe1 C8 H8A 126.1 . . ? C8 C9 C5 108.04(16) . . ? C8 C9 C15 124.81(17) . . ? C5 C9 C15 127.12(16) . . ? C8 C9 Fe1 68.99(10) . . ? C5 C9 Fe1 71.03(10) . . ? C15 C9 Fe1 124.01(12) . . ? C11 C10 C14 107.64(16) . . ? C11 C10 Fe2 71.38(10) . . ? C14 C10 Fe2 70.98(10) . . ? C11 C10 H10A 126.1 . . ? C14 C10 H10A 126.1 . . ? Fe2 C10 H10A 126.1 . . ? C12 C11 C10 108.32(16) . . ? C12 C11 Fe2 71.01(10) . . ? C10 C11 Fe2 69.24(10) . . ? C12 C11 H11A 125.8 . . ? C10 C11 H11A 125.8 . . ? Fe2 C11 H11A 125.8 . . ? C11 C12 C13 108.52(16) . . ? C11 C12 Fe2 70.37(11) . . ? C13 C12 Fe2 70.31(10) . . ? C11 C12 H12A 125.7 . . ? C13 C12 H12A 125.7 . . ? Fe2 C12 H12A 125.7 . . ? C12 C13 C14 107.75(15) . . ? C12 C13 Fe2 70.80(10) . . ? C14 C13 Fe2 70.00(10) . . ? C12 C13 H13A 126.1 . . ? C14 C13 H13A 126.1 . . ? Fe2 C13 H13A 126.1 . . ? C13 C14 C10 107.74(15) . . ? C13 C14 C18 125.51(15) . . ? C10 C14 C18 126.74(16) . . ? C13 C14 Fe2 70.71(10) . . ? C10 C14 Fe2 69.41(9) . . ? C18 C14 Fe2 124.48(12) . . ? O5 C15 O6 124.42(17) . . ? O5 C15 C9 124.70(17) . . ? O6 C15 C9 110.87(15) . . ? O6 C16 C17 107.88(16) . . ? O6 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? O6 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? O7B C17 O7A 82.5(2) . . ? O7B C17 C16 117.4(2) . . ? O7A C17 C16 114.38(18) . . ? O7B C17 H17A 122.3 . . ? O7A C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? O7B C17 H17B 26.6 . . ? O7A C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? O7B C17 H17C 108.0 . . ? O7A C17 H17C 26.8 . . ? C16 C17 H17C 108.0 . . ? H17A C17 H17C 87.6 . . ? H17B C17 H17C 132.7 . . ? O7B C17 H17D 108.0 . . ? O7A C17 H17D 124.8 . . ? C16 C17 H17D 108.0 . . ? H17A C17 H17D 20.9 . . ? H17B C17 H17D 88.7 . . ? H17C C17 H17D 107.2 . . ? O8 C18 O9 123.90(16) . . ? O8 C18 C14 125.29(16) . . ? O9 C18 C14 110.81(15) . . ? O9 C19 C20 107.11(15) . . ? O9 C19 H19A 110.3 . . ? C20 C19 H19A 110.3 . . ? O9 C19 H19B 110.3 . . ? C20 C19 H19B 110.3 . . ? H19A C19 H19B 108.5 . . ? O10A C20 O10B 26.6(2) . . ? O10A C20 C19 110.4(3) . . ? O10B C20 C19 114.6(2) . . ? O10A C20 H20A 109.6 . . ? O10B C20 H20A 84.0 . . ? C19 C20 H20A 109.6 . . ? O10A C20 H20B 109.6 . . ? O10B C20 H20B 126.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? O10A C20 H20C 131.2 . . ? O10B C20 H20C 108.6 . . ? C19 C20 H20C 108.6 . . ? H20A C20 H20C 27.7 . . ? H20B C20 H20C 83.1 . . ? O10A C20 H20D 86.5 . . ? O10B C20 H20D 108.6 . . ? C19 C20 H20D 108.6 . . ? H20A C20 H20D 129.3 . . ? H20B C20 H20D 26.0 . . ? H20C C20 H20D 107.6 . . ? C17 O7A H7A1 109.5 . . ? C17 O7B H7B 109.5 . . ? C20 O10A H10C 109.5 . . ? C20 O10B H10B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.593 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.059 data_ime116m _database_code_depnum_ccdc_archive 'CCDC 640139' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 Cl Fe O4' _chemical_formula_weight 270.45 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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6386(8) _cell_length_b 12.6126(16) _cell_length_c 13.5047(17) _cell_angle_alpha 67.996(2) _cell_angle_beta 83.392(2) _cell_angle_gamma 77.062(2) _cell_volume 1021.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6291 _cell_measurement_theta_min 5.611 _cell_measurement_theta_max 55.010 _exptl_crystal_description BLOCK _exptl_crystal_colour RED _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.726 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4791 _exptl_absorpt_correction_T_max 0.8463 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11391 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.55 _reflns_number_total 4526 _reflns_number_gt 3814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.0477P] 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 4526 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Fe1A Fe 0.24473(4) 0.79616(2) 1.00184(2) 0.02225(8) Uani 1 1 d . . . Cl1A Cl -0.09129(7) 0.80886(5) 1.06557(4) 0.03151(12) Uani 1 1 d . . . O1A O 0.3399(3) 0.91081(14) 1.13839(14) 0.0460(4) Uani 1 1 d . . . O2A O 0.3537(2) 0.55857(14) 1.15535(13) 0.0433(4) Uani 1 1 d . . . O3A O -0.0689(2) 0.70459(14) 0.82927(13) 0.0394(4) Uani 1 1 d . . . O4A O 0.2265(2) 0.57318(12) 0.88525(12) 0.0329(3) Uani 1 1 d . . . C1A C 0.3024(3) 0.86585(18) 1.08606(17) 0.0309(5) Uani 1 1 d . . . C2A C 0.3118(3) 0.65141(19) 1.09722(17) 0.0289(4) Uani 1 1 d . . . C3A C 0.4363(3) 0.74454(18) 0.88809(15) 0.0263(4) Uani 1 1 d . . . H3AA H 0.5384 0.6694 0.9023 0.032 Uiso 1 1 calc R . . C4A C 0.4770(3) 0.84984(19) 0.88721(17) 0.0310(5) Uani 1 1 d . . . H4AA H 0.6130 0.8623 0.9012 0.037 Uiso 1 1 calc R . . C5A C 0.2910(3) 0.93720(19) 0.85905(16) 0.0316(5) Uani 1 1 d . . . H5AA H 0.2739 1.0206 0.8518 0.038 Uiso 1 1 calc R . . C6A C 0.1376(3) 0.88495(18) 0.84425(15) 0.0280(4) Uani 1 1 d . . . H6AA H -0.0082 0.9249 0.8248 0.034 Uiso 1 1 calc R . . C7A C 0.2227(3) 0.76452(17) 0.86315(15) 0.0244(4) Uani 1 1 d . . . C8A C 0.1081(3) 0.68032(18) 0.85631(15) 0.0271(4) Uani 1 1 d . . . C9A C 0.1349(4) 0.4818(2) 0.8787(2) 0.0402(5) Uani 1 1 d . . . H9AA H 0.2092 0.4056 0.9243 0.060 Uiso 1 1 calc R . . H9AB H 0.1444 0.4855 0.8045 0.060 Uiso 1 1 calc R . . H9AC H -0.0107 0.4926 0.9028 0.060 Uiso 1 1 calc R . . Fe1B Fe 0.49656(4) 0.20427(2) 0.52575(2) 0.02362(9) Uani 1 1 d . . . Cl1B Cl 0.20493(7) 0.12674(4) 0.58352(4) 0.03076(12) Uani 1 1 d . . . O1B O 0.4200(3) 0.31277(15) 0.68765(13) 0.0450(4) Uani 1 1 d . . . O2B O 0.7559(3) -0.01183(14) 0.65952(14) 0.0461(4) Uani 1 1 d . . . O3B O 0.0487(2) 0.42909(13) 0.36184(12) 0.0361(4) Uani 1 1 d . . . O4B O 0.2590(2) 0.53193(12) 0.38980(12) 0.0322(3) Uani 1 1 d . . . C1B C 0.4501(3) 0.27017(18) 0.62567(17) 0.0304(5) Uani 1 1 d . . . C2B C 0.6539(3) 0.07249(19) 0.60894(17) 0.0314(5) Uani 1 1 d . . . C3B C 0.6093(3) 0.34640(18) 0.41473(16) 0.0277(4) Uani 1 1 d . . . H3BA H 0.6521 0.4093 0.4306 0.033 Uiso 1 1 calc R . . C4B C 0.7383(3) 0.24204(18) 0.41336(17) 0.0311(5) Uani 1 1 d . . . H4BA H 0.8891 0.2177 0.4285 0.037 Uiso 1 1 calc R . . C5B C 0.6183(3) 0.17796(19) 0.38340(16) 0.0317(5) Uani 1 1 d . . . H5BA H 0.6700 0.1009 0.3750 0.038 Uiso 1 1 calc R . . C6B C 0.4153(3) 0.24384(18) 0.36658(15) 0.0286(4) Uani 1 1 d . . . H6BA H 0.2972 0.2209 0.3451 0.034 Uiso 1 1 calc R . . C7B C 0.4062(3) 0.34765(17) 0.38697(15) 0.0244(4) Uani 1 1 d . . . C8B C 0.2175(3) 0.43840(18) 0.37821(15) 0.0269(4) Uani 1 1 d . . . C9B C 0.0868(3) 0.6309(2) 0.3723(2) 0.0407(6) Uani 1 1 d . . . H9BA H 0.1300 0.6934 0.3860 0.061 Uiso 1 1 calc R . . H9BB H -0.0295 0.6066 0.4210 0.061 Uiso 1 1 calc R . . H9BC H 0.0441 0.6594 0.2983 0.061 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 Fe1A 0.02351(14) 0.02164(15) 0.02183(15) -0.00793(11) -0.00341(11) -0.00337(11) Cl1A 0.0265(2) 0.0339(3) 0.0345(3) -0.0148(2) 0.0022(2) -0.0040(2) O1A 0.0609(11) 0.0410(10) 0.0458(10) -0.0231(8) -0.0171(8) -0.0086(8) O2A 0.0461(9) 0.0315(9) 0.0369(9) -0.0001(7) -0.0012(7) 0.0010(7) O3A 0.0283(8) 0.0463(9) 0.0494(10) -0.0236(8) -0.0131(7) -0.0014(7) O4A 0.0304(7) 0.0278(8) 0.0457(9) -0.0173(7) -0.0102(6) -0.0041(6) C1A 0.0335(11) 0.0277(11) 0.0298(11) -0.0074(9) -0.0066(9) -0.0052(9) C2A 0.0246(10) 0.0332(12) 0.0273(11) -0.0109(9) -0.0006(8) -0.0025(8) C3A 0.0225(9) 0.0303(11) 0.0256(10) -0.0106(8) 0.0005(8) -0.0037(8) C4A 0.0298(10) 0.0350(12) 0.0293(11) -0.0111(9) 0.0033(8) -0.0115(9) C5A 0.0407(12) 0.0271(11) 0.0245(11) -0.0055(9) 0.0013(9) -0.0097(9) C6A 0.0322(10) 0.0282(11) 0.0204(10) -0.0068(8) -0.0044(8) -0.0011(8) C7A 0.0253(9) 0.0280(10) 0.0195(9) -0.0095(8) -0.0007(7) -0.0030(8) C8A 0.0279(10) 0.0324(11) 0.0229(10) -0.0126(8) -0.0022(8) -0.0047(8) C9A 0.0436(13) 0.0357(13) 0.0499(14) -0.0204(11) -0.0107(11) -0.0116(10) Fe1B 0.02478(15) 0.02174(15) 0.02216(15) -0.00552(11) -0.00431(11) -0.00268(11) Cl1B 0.0287(2) 0.0257(3) 0.0342(3) -0.0064(2) -0.0002(2) -0.00628(19) O1B 0.0510(10) 0.0509(11) 0.0415(10) -0.0263(9) -0.0016(8) -0.0100(8) O2B 0.0485(10) 0.0327(9) 0.0462(10) -0.0028(8) -0.0194(8) 0.0022(8) O3B 0.0282(8) 0.0385(9) 0.0381(9) -0.0075(7) -0.0067(6) -0.0075(6) O4B 0.0287(7) 0.0282(8) 0.0399(9) -0.0154(7) -0.0081(6) 0.0026(6) C1B 0.0303(10) 0.0292(11) 0.0295(11) -0.0070(9) -0.0046(8) -0.0061(9) C2B 0.0319(10) 0.0313(11) 0.0301(11) -0.0085(9) -0.0056(9) -0.0065(9) C3B 0.0263(10) 0.0274(10) 0.0273(10) -0.0058(8) -0.0017(8) -0.0077(8) C4B 0.0263(10) 0.0304(11) 0.0303(11) -0.0059(9) 0.0033(8) -0.0040(8) C5B 0.0383(11) 0.0273(11) 0.0261(11) -0.0094(9) 0.0033(9) -0.0023(9) C6B 0.0354(11) 0.0304(11) 0.0193(10) -0.0076(8) -0.0019(8) -0.0070(9) C7B 0.0254(9) 0.0247(10) 0.0195(9) -0.0036(8) -0.0016(7) -0.0052(8) C8B 0.0270(10) 0.0285(11) 0.0195(10) -0.0025(8) -0.0008(8) -0.0046(8) C9B 0.0364(12) 0.0354(12) 0.0458(14) -0.0168(11) -0.0073(10) 0.0085(10) _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 Fe1A C2A 1.788(2) . ? Fe1A C1A 1.792(2) . ? Fe1A C3A 2.081(2) . ? Fe1A C7A 2.0829(19) . ? Fe1A C4A 2.090(2) . ? Fe1A C6A 2.1201(19) . ? Fe1A C5A 2.125(2) . ? Fe1A Cl1A 2.2899(6) . ? O1A C1A 1.134(3) . ? O2A C2A 1.131(2) . ? O3A C8A 1.209(2) . ? O4A C8A 1.340(2) . ? O4A C9A 1.452(3) . ? C3A C4A 1.409(3) . ? C3A C7A 1.440(3) . ? C3A H3AA 1.0000 . ? C4A C5A 1.439(3) . ? C4A H4AA 1.0000 . ? C5A C6A 1.399(3) . ? C5A H5AA 1.0000 . ? C6A C7A 1.432(3) . ? C6A H6AA 1.0000 . ? C7A C8A 1.472(3) . ? C9A H9AA 0.9800 . ? C9A H9AB 0.9800 . ? C9A H9AC 0.9800 . ? Fe1B C2B 1.791(2) . ? Fe1B C1B 1.799(2) . ? Fe1B C4B 2.085(2) . ? Fe1B C3B 2.086(2) . ? Fe1B C7B 2.0919(18) . ? Fe1B C5B 2.112(2) . ? Fe1B C6B 2.122(2) . ? Fe1B Cl1B 2.2894(6) . ? O1B C1B 1.131(3) . ? O2B C2B 1.138(2) . ? O3B C8B 1.206(2) . ? O4B C8B 1.336(3) . ? O4B C9B 1.457(2) . ? C3B C4B 1.406(3) . ? C3B C7B 1.436(3) . ? C3B H3BA 1.0000 . ? C4B C5B 1.435(3) . ? C4B H4BA 1.0000 . ? C5B C6B 1.409(3) . ? C5B H5BA 1.0000 . ? C6B C7B 1.423(3) . ? C6B H6BA 1.0000 . ? C7B C8B 1.478(3) . ? C9B H9BA 0.9800 . ? C9B H9BB 0.9800 . ? C9B H9BC 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 C2A Fe1A C1A 94.95(9) . . ? C2A Fe1A C3A 89.42(9) . . ? C1A Fe1A C3A 128.52(9) . . ? C2A Fe1A C7A 101.75(9) . . ? C1A Fe1A C7A 159.14(9) . . ? C3A Fe1A C7A 40.47(7) . . ? C2A Fe1A C4A 114.87(9) . . ? C1A Fe1A C4A 94.62(9) . . ? C3A Fe1A C4A 39.50(8) . . ? C7A Fe1A C4A 67.09(8) . . ? C2A Fe1A C6A 140.36(9) . . ? C1A Fe1A C6A 124.69(9) . . ? C3A Fe1A C6A 66.66(8) . . ? C7A Fe1A C6A 39.82(8) . . ? C4A Fe1A C6A 66.10(8) . . ? C2A Fe1A C5A 154.15(9) . . ? C1A Fe1A C5A 93.33(9) . . ? C3A Fe1A C5A 66.45(8) . . ? C7A Fe1A C5A 66.32(8) . . ? C4A Fe1A C5A 39.91(8) . . ? C6A Fe1A C5A 38.47(8) . . ? C2A Fe1A Cl1A 90.67(7) . . ? C1A Fe1A Cl1A 90.86(7) . . ? C3A Fe1A Cl1A 140.45(6) . . ? C7A Fe1A Cl1A 101.25(5) . . ? C4A Fe1A Cl1A 153.21(6) . . ? C6A Fe1A Cl1A 89.31(6) . . ? C5A Fe1A Cl1A 113.67(6) . . ? C8A O4A C9A 116.44(16) . . ? O1A C1A Fe1A 179.2(2) . . ? O2A C2A Fe1A 178.0(2) . . ? C4A C3A C7A 108.05(17) . . ? C4A C3A Fe1A 70.58(12) . . ? C7A C3A Fe1A 69.84(11) . . ? C4A C3A H3AA 126.0 . . ? C7A C3A H3AA 126.0 . . ? Fe1A C3A H3AA 126.0 . . ? C3A C4A C5A 108.07(18) . . ? C3A C4A Fe1A 69.92(12) . . ? C5A C4A Fe1A 71.37(12) . . ? C3A C4A H4AA 125.9 . . ? C5A C4A H4AA 125.9 . . ? Fe1A C4A H4AA 125.9 . . ? C6A C5A C4A 108.03(19) . . ? C6A C5A Fe1A 70.58(12) . . ? C4A C5A Fe1A 68.72(11) . . ? C6A C5A H5AA 126.0 . . ? C4A C5A H5AA 126.0 . . ? Fe1A C5A H5AA 126.0 . . ? C5A C6A C7A 108.81(17) . . ? C5A C6A Fe1A 70.95(11) . . ? C7A C6A Fe1A 68.69(11) . . ? C5A C6A H6AA 125.6 . . ? C7A C6A H6AA 125.6 . . ? Fe1A C6A H6AA 125.6 . . ? C6A C7A C3A 107.01(17) . . ? C6A C7A C8A 124.94(17) . . ? C3A C7A C8A 128.05(18) . . ? C6A C7A Fe1A 71.49(11) . . ? C3A C7A Fe1A 69.69(11) . . ? C8A C7A Fe1A 124.47(14) . . ? O3A C8A O4A 124.9(2) . . ? O3A C8A C7A 124.54(19) . . ? O4A C8A C7A 110.56(16) . . ? O4A C9A H9AA 109.5 . . ? O4A C9A H9AB 109.5 . . ? H9AA C9A H9AB 109.5 . . ? O4A C9A H9AC 109.5 . . ? H9AA C9A H9AC 109.5 . . ? H9AB C9A H9AC 109.5 . . ? C2B Fe1B C1B 94.39(10) . . ? C2B Fe1B C4B 92.08(9) . . ? C1B Fe1B C4B 118.86(9) . . ? C2B Fe1B C3B 124.87(9) . . ? C1B Fe1B C3B 92.14(9) . . ? C4B Fe1B C3B 39.40(8) . . ? C2B Fe1B C7B 157.67(9) . . ? C1B Fe1B C7B 101.86(9) . . ? C4B Fe1B C7B 66.71(7) . . ? C3B Fe1B C7B 40.21(7) . . ? C2B Fe1B C5B 93.20(9) . . ? C1B Fe1B C5B 157.84(9) . . ? C4B Fe1B C5B 39.98(8) . . ? C3B Fe1B C5B 66.57(8) . . ? C7B Fe1B C5B 66.26(8) . . ? C2B Fe1B C6B 126.66(9) . . ? C1B Fe1B C6B 138.95(8) . . ? C4B Fe1B C6B 66.19(8) . . ? C3B Fe1B C6B 66.50(8) . . ? C7B Fe1B C6B 39.46(8) . . ? C5B Fe1B C6B 38.89(8) . . ? C2B Fe1B Cl1B 91.16(7) . . ? C1B Fe1B Cl1B 90.49(7) . . ? C4B Fe1B Cl1B 150.09(6) . . ? C3B Fe1B Cl1B 143.50(5) . . ? C7B Fe1B Cl1B 103.80(5) . . ? C5B Fe1B Cl1B 110.15(6) . . ? C6B Fe1B Cl1B 88.29(6) . . ? C8B O4B C9B 115.46(16) . . ? O1B C1B Fe1B 179.2(2) . . ? O2B C2B Fe1B 178.2(2) . . ? C4B C3B C7B 107.82(18) . . ? C4B C3B Fe1B 70.27(12) . . ? C7B C3B Fe1B 70.13(11) . . ? C4B C3B H3BA 126.1 . . ? C7B C3B H3BA 126.1 . . ? Fe1B C3B H3BA 126.1 . . ? C3B C4B C5B 108.37(18) . . ? C3B C4B Fe1B 70.34(11) . . ? C5B C4B Fe1B 71.02(12) . . ? C3B C4B H4BA 125.8 . . ? C5B C4B H4BA 125.8 . . ? Fe1B C4B H4BA 125.8 . . ? C6B C5B C4B 107.74(18) . . ? C6B C5B Fe1B 70.95(11) . . ? C4B C5B Fe1B 69.00(12) . . ? C6B C5B H5BA 126.1 . . ? C4B C5B H5BA 126.1 . . ? Fe1B C5B H5BA 126.1 . . ? C5B C6B C7B 108.43(18) . . ? C5B C6B Fe1B 70.16(11) . . ? C7B C6B Fe1B 69.13(11) . . ? C5B C6B H6BA 125.8 . . ? C7B C6B H6BA 125.8 . . ? Fe1B C6B H6BA 125.8 . . ? C6B C7B C3B 107.62(17) . . ? C6B C7B C8B 124.16(17) . . ? C3B C7B C8B 128.22(18) . . ? C6B C7B Fe1B 71.41(11) . . ? C3B C7B Fe1B 69.67(11) . . ? C8B C7B Fe1B 125.09(13) . . ? O3B C8B O4B 124.69(18) . . ? O3B C8B C7B 124.1(2) . . ? O4B C8B C7B 111.22(16) . . ? O4B C9B H9BA 109.5 . . ? O4B C9B H9BB 109.5 . . ? H9BA C9B H9BB 109.5 . . ? O4B C9B H9BC 109.5 . . ? H9BA C9B H9BC 109.5 . . ? H9BB C9B H9BC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.439 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.061 data_ime124m _database_code_depnum_ccdc_archive 'CCDC 640140' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 Br Fe O4' _chemical_formula_weight 314.91 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' Br Br -0.2901 2.4595 '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)/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 6.8607(8) _cell_length_b 18.920(2) _cell_length_c 8.0278(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.881(7) _cell_angle_gamma 90.00 _cell_volume 1041.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2027 _cell_measurement_theta_min 6.340 _cell_measurement_theta_max 54.164 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 5.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2330 _exptl_absorpt_correction_T_max 0.4505 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11597 _diffrn_reflns_av_R_equivalents 0.1916 _diffrn_reflns_av_sigmaI/netI 0.1234 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2361 _reflns_number_gt 1455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2361 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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 0.09447(12) 0.14441(5) 0.24518(11) 0.0160(3) Uani 1 1 d . . . Br1 Br 0.40024(9) 0.20865(3) 0.24242(8) 0.0227(2) Uani 1 1 d . . . O1 O 0.1436(6) 0.1186(2) 0.6031(5) 0.0250(11) Uani 1 1 d . . . O2 O -0.1222(7) 0.2766(3) 0.2866(6) 0.0303(11) Uani 1 1 d . . . O3 O 0.4816(6) -0.0026(2) 0.2001(6) 0.0277(11) Uani 1 1 d . . . O4 O 0.2361(6) -0.0458(2) 0.3551(6) 0.0249(11) Uani 1 1 d . . . C1 C 0.1231(8) 0.1296(3) 0.4643(8) 0.0200(14) Uani 1 1 d . . . C2 C -0.0358(9) 0.2251(4) 0.2707(7) 0.0209(14) Uani 1 1 d . . . C3 C -0.0440(9) 0.0481(3) 0.2112(8) 0.0191(14) Uani 1 1 d . . . H3A H -0.1092 0.0198 0.2995 0.023 Uiso 1 1 calc R . . C4 C -0.1331(9) 0.0982(3) 0.1085(7) 0.0203(14) Uani 1 1 d . . . H4A H -0.2733 0.1126 0.1120 0.024 Uiso 1 1 calc R . . C5 C 0.0090(9) 0.1252(3) -0.0042(8) 0.0208(14) Uani 1 1 d . . . H5A H -0.0148 0.1621 -0.0915 0.025 Uiso 1 1 calc R . . C6 C 0.1873(9) 0.0902(3) 0.0273(8) 0.0212(14) Uani 1 1 d . . . H6A H 0.3121 0.0981 -0.0325 0.025 Uiso 1 1 calc R . . C7 C 0.1579(8) 0.0421(3) 0.1626(7) 0.0147(13) Uani 1 1 d . . . C8 C 0.3120(9) -0.0031(3) 0.2366(7) 0.0185(14) Uani 1 1 d . . . C9 C 0.3683(10) -0.0955(4) 0.4328(9) 0.0298(17) Uani 1 1 d . . . H9A H 0.2947 -0.1361 0.4741 0.045 Uiso 1 1 calc R . . H9B H 0.4369 -0.0725 0.5260 0.045 Uiso 1 1 calc R . . H9C H 0.4631 -0.1116 0.3510 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0151(5) 0.0146(5) 0.0181(5) -0.0010(4) 0.0006(3) -0.0004(4) Br1 0.0179(3) 0.0210(4) 0.0292(4) -0.0021(3) 0.0012(3) -0.0048(3) O1 0.029(2) 0.029(3) 0.017(2) -0.001(2) 0.0015(19) -0.006(2) O2 0.033(3) 0.025(3) 0.033(3) -0.001(2) 0.004(2) 0.008(2) O3 0.017(2) 0.029(3) 0.038(3) 0.006(2) 0.009(2) 0.004(2) O4 0.016(2) 0.024(3) 0.034(3) 0.011(2) -0.0011(19) 0.0045(19) C1 0.010(3) 0.017(3) 0.033(4) -0.003(3) 0.002(3) 0.000(3) C2 0.020(3) 0.022(4) 0.021(3) 0.006(3) 0.000(3) 0.001(3) C3 0.021(3) 0.013(3) 0.023(3) -0.007(3) 0.000(3) 0.002(3) C4 0.015(3) 0.024(4) 0.022(3) 0.003(3) -0.007(3) 0.002(3) C5 0.024(3) 0.015(3) 0.023(4) 0.001(3) 0.002(3) -0.006(3) C6 0.024(3) 0.016(4) 0.023(3) -0.008(3) 0.002(3) 0.000(3) C7 0.017(3) 0.014(3) 0.013(3) -0.001(2) 0.000(2) 0.001(2) C8 0.024(3) 0.010(3) 0.022(3) -0.005(3) -0.006(3) 0.002(3) C9 0.028(4) 0.024(4) 0.037(4) 0.003(3) -0.002(3) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C2 1.783(7) . ? Fe1 C1 1.789(7) . ? Fe1 C3 2.071(6) . ? Fe1 C4 2.086(6) . ? Fe1 C7 2.094(6) . ? Fe1 C5 2.109(6) . ? Fe1 C6 2.133(6) . ? Fe1 Br1 2.4248(10) . ? O1 C1 1.140(7) . ? O2 C2 1.148(8) . ? O3 C8 1.204(7) . ? O4 C8 1.358(7) . ? O4 C9 1.441(7) . ? C3 C4 1.391(8) . ? C3 C7 1.449(8) . ? C3 H3A 1.0000 . ? C4 C5 1.435(9) . ? C4 H4A 1.0000 . ? C5 C6 1.410(9) . ? C5 H5A 1.0000 . ? C6 C7 1.434(9) . ? C6 H6A 1.0000 . ? C7 C8 1.477(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Fe1 C1 93.9(3) . . ? C2 Fe1 C3 122.6(3) . . ? C1 Fe1 C3 92.0(3) . . ? C2 Fe1 C4 92.7(3) . . ? C1 Fe1 C4 121.4(3) . . ? C3 Fe1 C4 39.1(2) . . ? C2 Fe1 C7 159.3(3) . . ? C1 Fe1 C7 98.4(3) . . ? C3 Fe1 C7 40.7(2) . . ? C4 Fe1 C7 66.7(2) . . ? C2 Fe1 C5 97.1(3) . . ? C1 Fe1 C5 158.6(3) . . ? C3 Fe1 C5 66.6(2) . . ? C4 Fe1 C5 40.0(2) . . ? C7 Fe1 C5 66.2(2) . . ? C2 Fe1 C6 131.5(3) . . ? C1 Fe1 C6 134.6(3) . . ? C3 Fe1 C6 67.1(2) . . ? C4 Fe1 C6 66.3(2) . . ? C7 Fe1 C6 39.7(2) . . ? C5 Fe1 C6 38.8(2) . . ? C2 Fe1 Br1 90.4(2) . . ? C1 Fe1 Br1 90.31(19) . . ? C3 Fe1 Br1 146.61(17) . . ? C4 Fe1 Br1 147.76(18) . . ? C7 Fe1 Br1 106.05(16) . . ? C5 Fe1 Br1 107.79(17) . . ? C6 Fe1 Br1 87.95(18) . . ? C8 O4 C9 116.5(5) . . ? O1 C1 Fe1 178.2(6) . . ? O2 C2 Fe1 179.0(6) . . ? C4 C3 C7 107.9(5) . . ? C4 C3 Fe1 71.1(4) . . ? C7 C3 Fe1 70.5(3) . . ? C4 C3 H3A 126.0 . . ? C7 C3 H3A 126.0 . . ? Fe1 C3 H3A 126.0 . . ? C3 C4 C5 108.6(5) . . ? C3 C4 Fe1 69.8(3) . . ? C5 C4 Fe1 70.8(3) . . ? C3 C4 H4A 125.7 . . ? C5 C4 H4A 125.7 . . ? Fe1 C4 H4A 125.7 . . ? C6 C5 C4 108.4(6) . . ? C6 C5 Fe1 71.5(4) . . ? C4 C5 Fe1 69.2(3) . . ? C6 C5 H5A 125.8 . . ? C4 C5 H5A 125.8 . . ? Fe1 C5 H5A 125.8 . . ? C5 C6 C7 107.6(6) . . ? C5 C6 Fe1 69.7(4) . . ? C7 C6 Fe1 68.7(3) . . ? C5 C6 H6A 126.2 . . ? C7 C6 H6A 126.2 . . ? Fe1 C6 H6A 126.2 . . ? C6 C7 C3 107.4(5) . . ? C6 C7 C8 124.3(5) . . ? C3 C7 C8 128.2(6) . . ? C6 C7 Fe1 71.6(3) . . ? C3 C7 Fe1 68.8(3) . . ? C8 C7 Fe1 123.9(4) . . ? O3 C8 O4 123.9(6) . . ? O3 C8 C7 125.9(6) . . ? O4 C8 C7 110.3(5) . . ? O4 C9 H9A 109.5 . . ? O4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.189 _refine_diff_density_min -0.863 _refine_diff_density_rms 0.194