# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year 2011 _journal_volume 47 _journal_page_first 7239 _publ_contact_author_name 'Lentz, Dieter' _publ_contact_author_email lentz@chemie.fu-berlin.de _publ_section_title ; Autocatalytic Formation of Fluorinated Ferrocenophanes from 1,1'-Bis(trifluorovinyl)ferrocene ; loop_ _publ_author_name M.Roemer D.Lentz data_max2b _database_code_depnum_ccdc_archive 'CCDC 788090' #TrackingRef '3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-(1,1'-ferrocenediyl)2,2,3,3,4-Pentafluorobutan-1-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H9 F5 Fe O' _chemical_formula_weight 344.06 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' F F 0.0171 0.0103 '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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.437(2) _cell_length_b 16.168(5) _cell_length_c 20.250(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2434.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 976 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 30.5 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (BRUKER_AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26148 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.56 _reflns_number_total 3721 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-AXS)' _computing_cell_refinement 'SAINT (BRUKER-AXS)' _computing_data_reduction 'SAINT (BRUKER-AXS)' _computing_structure_solution 'SHELXS (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0782P)^2^+1.6550P] 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 3721 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.07234(4) 0.599486(17) 0.379971(13) 0.01836(11) Uani 1 1 d . . . C1 C -0.0888(3) 0.64706(13) 0.30979(9) 0.0203(4) Uani 1 1 d . . . C2 C 0.0127(3) 0.57940(14) 0.28197(10) 0.0251(4) Uani 1 1 d . . . H2 H 0.0991 0.5831 0.2442 0.030 Uiso 1 1 calc R . . C3 C -0.0305(3) 0.50666(14) 0.31831(11) 0.0286(4) Uani 1 1 d . . . H3 H 0.0230 0.4506 0.3114 0.034 Uiso 1 1 calc R . . C4 C -0.1582(3) 0.52854(14) 0.36807(11) 0.0261(4) Uani 1 1 d . . . H4 H -0.2093 0.4899 0.4018 0.031 Uiso 1 1 calc R . . C5 C -0.1954(3) 0.61429(14) 0.36380(10) 0.0230(4) Uani 1 1 d . . . H5 H -0.2811 0.6461 0.3921 0.028 Uiso 1 1 calc R . . C6 C 0.3048(3) 0.66693(14) 0.38946(10) 0.0231(4) Uani 1 1 d . . . H6 H 0.3595 0.7033 0.3549 0.028 Uiso 1 1 calc R . . C7 C 0.3431(3) 0.58173(14) 0.39971(12) 0.0270(4) Uani 1 1 d . . . H7 H 0.4279 0.5474 0.3729 0.032 Uiso 1 1 calc R . . C8 C 0.2375(3) 0.55306(14) 0.45403(10) 0.0266(4) Uani 1 1 d . . . H8 H 0.2355 0.4952 0.4715 0.032 Uiso 1 1 calc R . . C9 C 0.1311(3) 0.62001(14) 0.47766(10) 0.0233(4) Uani 1 1 d . . . H9 H 0.0441 0.6180 0.5153 0.028 Uiso 1 1 calc R . . C10 C 0.1707(3) 0.69118(12) 0.43710(10) 0.0209(4) Uani 1 1 d . . . C11 C 0.0883(3) 0.77390(13) 0.44895(10) 0.0220(4) Uani 1 1 d . . . H11 H -0.0275 0.7662 0.4733 0.026 Uiso 1 1 calc R . . C12 C 0.0545(3) 0.83011(13) 0.38895(11) 0.0235(4) Uani 1 1 d . . . C13 C -0.0965(3) 0.80502(13) 0.33974(11) 0.0239(4) Uani 1 1 d . . . C14 C -0.0480(3) 0.73266(13) 0.29177(10) 0.0226(4) Uani 1 1 d . . . F1 F 0.2075(2) 0.82063(9) 0.48907(7) 0.0350(3) Uani 1 1 d . . . F2 F 0.20816(19) 0.84282(9) 0.35418(7) 0.0338(3) Uani 1 1 d . . . F3 F 0.0030(2) 0.90523(8) 0.41380(8) 0.0343(3) Uani 1 1 d . . . F4 F -0.1327(2) 0.87241(9) 0.30250(7) 0.0383(4) Uani 1 1 d . . . F5 F -0.24584(18) 0.78897(9) 0.37663(6) 0.0288(3) Uani 1 1 d . . . O1 O 0.0324(2) 0.75218(11) 0.24189(8) 0.0338(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01465(17) 0.02077(17) 0.01965(17) -0.00018(9) 0.00073(8) -0.00143(9) C1 0.0158(8) 0.0269(10) 0.0183(8) -0.0022(7) -0.0014(6) -0.0013(7) C2 0.0241(9) 0.0297(10) 0.0216(9) -0.0058(8) 0.0025(7) -0.0016(8) C3 0.0296(10) 0.0248(10) 0.0315(10) -0.0069(8) -0.0020(8) -0.0026(8) C4 0.0227(10) 0.0276(10) 0.0279(9) -0.0004(8) -0.0002(7) -0.0089(8) C5 0.0176(9) 0.0302(10) 0.0211(8) -0.0030(7) -0.0003(7) -0.0048(7) C6 0.0155(8) 0.0273(10) 0.0267(9) 0.0016(7) 0.0003(7) -0.0027(7) C7 0.0173(9) 0.0292(10) 0.0346(11) 0.0015(8) 0.0000(7) 0.0034(8) C8 0.0243(10) 0.0269(10) 0.0285(10) 0.0052(8) -0.0031(7) 0.0027(8) C9 0.0206(9) 0.0281(10) 0.0211(9) 0.0021(7) -0.0018(7) -0.0007(7) C10 0.0170(8) 0.0237(9) 0.0220(8) -0.0011(7) -0.0035(6) -0.0020(7) C11 0.0200(8) 0.0239(9) 0.0222(9) -0.0044(7) -0.0038(6) -0.0026(7) C12 0.0217(9) 0.0194(9) 0.0295(10) -0.0009(7) -0.0010(7) -0.0020(7) C13 0.0228(9) 0.0239(10) 0.0251(9) 0.0017(7) -0.0018(7) 0.0020(7) C14 0.0210(9) 0.0269(10) 0.0198(8) -0.0004(7) -0.0035(6) -0.0004(7) F1 0.0359(8) 0.0336(7) 0.0353(7) -0.0097(6) -0.0149(6) -0.0028(6) F2 0.0262(7) 0.0346(7) 0.0406(8) 0.0072(6) 0.0031(6) -0.0085(5) F3 0.0392(8) 0.0205(6) 0.0432(8) -0.0068(5) -0.0074(6) 0.0018(5) F4 0.0519(9) 0.0280(7) 0.0349(7) 0.0062(6) -0.0092(7) 0.0087(6) F5 0.0189(6) 0.0363(7) 0.0313(7) -0.0073(5) -0.0002(5) 0.0027(5) O1 0.0420(9) 0.0369(9) 0.0226(7) 0.0030(7) 0.0054(6) -0.0071(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 2.012(2) . ? Fe1 C10 2.018(2) . ? Fe1 C5 2.032(2) . ? Fe1 C6 2.053(2) . ? Fe1 C9 2.053(2) . ? Fe1 C2 2.059(2) . ? Fe1 C7 2.073(2) . ? Fe1 C4 2.077(2) . ? Fe1 C8 2.079(2) . ? Fe1 C3 2.097(2) . ? C1 C2 1.444(3) . ? C1 C5 1.451(3) . ? C1 C14 1.463(3) . ? C2 C3 1.424(3) . ? C3 C4 1.430(3) . ? C4 C5 1.416(3) . ? C6 C7 1.422(3) . ? C6 C10 1.442(3) . ? C7 C8 1.429(3) . ? C8 C9 1.424(3) . ? C9 C10 1.444(3) . ? C10 C11 1.490(3) . ? C11 F1 1.420(2) . ? C11 C12 1.538(3) . ? C12 F2 1.358(3) . ? C12 F3 1.369(2) . ? C12 C13 1.555(3) . ? C13 F4 1.352(2) . ? C13 F5 1.363(2) . ? C13 C14 1.563(3) . ? C14 O1 1.216(3) . ? 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 C10 109.88(8) . . ? C1 Fe1 C5 42.05(8) . . ? C10 Fe1 C5 111.16(8) . . ? C1 Fe1 C6 111.38(8) . . ? C10 Fe1 C6 41.48(8) . . ? C5 Fe1 C6 141.04(9) . . ? C1 Fe1 C9 138.22(8) . . ? C10 Fe1 C9 41.55(8) . . ? C5 Fe1 C9 110.17(8) . . ? C6 Fe1 C9 69.19(8) . . ? C1 Fe1 C2 41.52(8) . . ? C10 Fe1 C2 138.29(9) . . ? C5 Fe1 C2 69.65(8) . . ? C6 Fe1 C2 110.81(8) . . ? C9 Fe1 C2 179.74(9) . . ? C1 Fe1 C7 140.15(9) . . ? C10 Fe1 C7 68.84(9) . . ? C5 Fe1 C7 177.78(9) . . ? C6 Fe1 C7 40.32(9) . . ? C9 Fe1 C7 68.28(9) . . ? C2 Fe1 C7 111.91(9) . . ? C1 Fe1 C4 68.75(9) . . ? C10 Fe1 C4 140.49(9) . . ? C5 Fe1 C4 40.31(9) . . ? C6 Fe1 C4 178.00(9) . . ? C9 Fe1 C4 112.13(9) . . ? C2 Fe1 C4 67.88(8) . . ? C7 Fe1 C4 138.41(9) . . ? C1 Fe1 C8 178.48(9) . . ? C10 Fe1 C8 68.75(9) . . ? C5 Fe1 C8 137.54(9) . . ? C6 Fe1 C8 68.09(9) . . ? C9 Fe1 C8 40.31(8) . . ? C2 Fe1 C8 139.95(9) . . ? C7 Fe1 C8 40.27(9) . . ? C4 Fe1 C8 111.84(9) . . ? C1 Fe1 C3 68.64(9) . . ? C10 Fe1 C3 178.33(9) . . ? C5 Fe1 C3 68.35(9) . . ? C6 Fe1 C3 137.99(9) . . ? C9 Fe1 C3 140.10(9) . . ? C2 Fe1 C3 40.06(9) . . ? C7 Fe1 C3 111.71(9) . . ? C4 Fe1 C3 40.06(9) . . ? C8 Fe1 C3 112.74(9) . . ? C2 C1 C5 107.64(19) . . ? C2 C1 C14 120.75(18) . . ? C5 C1 C14 130.29(18) . . ? C2 C1 Fe1 71.00(12) . . ? C5 C1 Fe1 69.71(12) . . ? C14 C1 Fe1 114.50(13) . . ? C3 C2 C1 107.83(18) . . ? C3 C2 Fe1 71.38(13) . . ? C1 C2 Fe1 67.48(11) . . ? C2 C3 C4 108.1(2) . . ? C2 C3 Fe1 68.56(12) . . ? C4 C3 Fe1 69.24(12) . . ? C5 C4 C3 109.19(19) . . ? C5 C4 Fe1 68.13(12) . . ? C3 C4 Fe1 70.71(12) . . ? C4 C5 C1 107.29(18) . . ? C4 C5 Fe1 71.57(12) . . ? C1 C5 Fe1 68.24(11) . . ? C7 C6 C10 107.72(18) . . ? C7 C6 Fe1 70.61(12) . . ? C10 C6 Fe1 67.95(11) . . ? C6 C7 C8 108.45(19) . . ? C6 C7 Fe1 69.08(12) . . ? C8 C7 Fe1 70.08(12) . . ? C9 C8 C7 108.52(19) . . ? C9 C8 Fe1 68.87(12) . . ? C7 C8 Fe1 69.65(12) . . ? C8 C9 C10 107.54(18) . . ? C8 C9 Fe1 70.82(12) . . ? C10 C9 Fe1 67.92(11) . . ? C6 C10 C9 107.76(18) . . ? C6 C10 C11 129.48(18) . . ? C9 C10 C11 122.67(18) . . ? C6 C10 Fe1 70.56(12) . . ? C9 C10 Fe1 70.54(12) . . ? C11 C10 Fe1 127.07(13) . . ? F1 C11 C10 108.25(16) . . ? F1 C11 C12 103.87(16) . . ? C10 C11 C12 118.04(17) . . ? F2 C12 F3 106.96(17) . . ? F2 C12 C11 111.19(17) . . ? F3 C12 C11 106.23(17) . . ? F2 C12 C13 108.36(18) . . ? F3 C12 C13 105.35(17) . . ? C11 C12 C13 118.05(17) . . ? F4 C13 F5 107.26(17) . . ? F4 C13 C12 106.91(17) . . ? F5 C13 C12 106.67(17) . . ? F4 C13 C14 107.61(17) . . ? F5 C13 C14 112.70(17) . . ? C12 C13 C14 115.28(16) . . ? O1 C14 C1 123.7(2) . . ? O1 C14 C13 115.8(2) . . ? C1 C14 C13 120.35(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.621 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.134 # Attachment '4.cif' data_max4 _database_code_depnum_ccdc_archive 'CCDC 788091' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-(1,1'-ferrocenediyl)2,2,3,3-Tetrafluorobutan-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 F4 Fe O2' _chemical_formula_weight 340.05 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.6994(18) _cell_length_b 11.6626(17) _cell_length_c 15.498(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2295.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 902 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 26.6 _exptl_crystal_description platelett _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (BRUKER_AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19876 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.43 _reflns_number_total 2359 _reflns_number_gt 1707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER-AXS)' _computing_cell_refinement 'SAINT (BRUKER-AXS)' _computing_data_reduction 'SAINT (BRUKER-AXS)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0298P)^2^+4.1315P] 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 2359 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.56334(3) 0.87369(3) 0.34752(2) 0.01792(13) Uani 1 1 d . . . C1 C 0.4361(2) 0.8697(2) 0.27058(18) 0.0203(6) Uani 1 1 d . . . C2 C 0.4169(2) 0.7988(3) 0.34479(19) 0.0238(6) Uani 1 1 d . . . H2 H 0.4019 0.7190 0.3442 0.029 Uiso 1 1 calc R . . C3 C 0.4243(2) 0.8694(3) 0.4189(2) 0.0262(7) Uani 1 1 d . . . H3 H 0.4154 0.8450 0.4769 0.031 Uiso 1 1 calc R . . C4 C 0.4473(2) 0.9828(3) 0.3916(2) 0.0264(7) Uani 1 1 d . . . H4 H 0.4560 1.0471 0.4286 0.032 Uiso 1 1 calc R . . C5 C 0.4551(2) 0.9852(3) 0.3010(2) 0.0227(6) Uani 1 1 d . . . H5 H 0.4701 1.0503 0.2663 0.027 Uiso 1 1 calc R . . C6 C 0.6776(2) 0.7708(3) 0.29794(19) 0.0223(6) Uani 1 1 d . . . H6 H 0.6671 0.7102 0.2579 0.027 Uiso 1 1 calc R . . C7 C 0.6789(2) 0.7611(3) 0.38881(19) 0.0259(7) Uani 1 1 d . . . H7 H 0.6690 0.6922 0.4204 0.031 Uiso 1 1 calc R . . C8 C 0.6974(2) 0.8709(3) 0.42518(18) 0.0270(7) Uani 1 1 d . . . H8 H 0.7022 0.8876 0.4850 0.032 Uiso 1 1 calc R . . C9 C 0.7075(2) 0.9506(3) 0.35780(19) 0.0236(6) Uani 1 1 d . . . H9 H 0.7202 1.0304 0.3642 0.028 Uiso 1 1 calc R . . C10 C 0.6951(2) 0.8900(2) 0.27708(18) 0.0199(6) Uani 1 1 d . . . C11 C 0.6838(2) 0.9509(2) 0.19486(19) 0.0212(6) Uani 1 1 d . . . C12 C 0.6307(2) 0.8906(2) 0.11728(19) 0.0236(6) Uani 1 1 d . . . C13 C 0.5092(2) 0.8951(3) 0.11470(19) 0.0246(7) Uani 1 1 d . . . C14 C 0.4530(2) 0.8217(3) 0.18455(19) 0.0226(6) Uani 1 1 d . . . F2 F 0.65931(14) 0.77806(15) 0.11271(11) 0.0291(4) Uani 1 1 d . . . F3 F 0.66632(15) 0.94124(16) 0.04422(11) 0.0346(5) Uani 1 1 d . . . F4 F 0.47880(15) 0.85663(16) 0.03647(11) 0.0345(5) Uani 1 1 d . . . F5 F 0.48013(14) 1.00684(15) 0.11977(12) 0.0298(4) Uani 1 1 d . . . O1 O 0.42954(17) 0.72449(18) 0.16440(14) 0.0292(5) Uani 1 1 d . . . O2 O 0.71035(17) 1.04940(18) 0.18452(14) 0.0292(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0144(2) 0.0192(2) 0.0202(2) -0.00112(17) 0.00047(17) 0.00099(17) C1 0.0139(14) 0.0220(14) 0.0249(14) -0.0007(12) -0.0008(12) 0.0011(12) C2 0.0167(15) 0.0263(15) 0.0282(15) 0.0013(13) 0.0023(12) -0.0023(12) C3 0.0169(15) 0.0344(17) 0.0275(15) 0.0006(14) 0.0055(12) 0.0024(14) C4 0.0198(16) 0.0294(16) 0.0300(16) -0.0061(13) 0.0008(13) 0.0057(13) C5 0.0184(15) 0.0208(15) 0.0288(16) -0.0007(12) -0.0020(12) 0.0026(12) C6 0.0183(15) 0.0225(15) 0.0260(15) -0.0006(12) 0.0006(12) 0.0038(12) C7 0.0204(15) 0.0297(17) 0.0275(16) 0.0067(13) 0.0014(13) 0.0082(13) C8 0.0203(16) 0.0401(19) 0.0206(14) -0.0032(14) -0.0050(12) 0.0009(14) C9 0.0138(15) 0.0276(16) 0.0293(16) -0.0066(13) -0.0008(12) -0.0023(12) C10 0.0121(14) 0.0267(15) 0.0209(13) -0.0033(12) 0.0017(11) 0.0000(12) C11 0.0150(14) 0.0233(15) 0.0254(14) -0.0016(12) 0.0034(12) 0.0012(12) C12 0.0278(17) 0.0221(16) 0.0209(14) 0.0017(12) 0.0033(13) -0.0016(13) C13 0.0297(17) 0.0229(16) 0.0213(14) -0.0014(12) -0.0061(13) 0.0020(13) C14 0.0174(15) 0.0237(16) 0.0267(15) 0.0012(12) -0.0052(12) 0.0024(12) F2 0.0318(10) 0.0257(9) 0.0299(9) -0.0076(8) 0.0014(8) 0.0044(8) F3 0.0388(11) 0.0427(11) 0.0225(9) 0.0042(8) 0.0053(8) -0.0074(9) F4 0.0389(11) 0.0438(12) 0.0209(9) -0.0037(8) -0.0091(8) -0.0035(9) F5 0.0326(10) 0.0239(9) 0.0330(10) 0.0069(8) -0.0023(8) 0.0052(8) O1 0.0302(12) 0.0218(11) 0.0355(12) -0.0044(9) -0.0033(10) -0.0032(9) O2 0.0277(12) 0.0228(11) 0.0369(12) 0.0027(10) 0.0016(10) -0.0028(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C10 2.007(3) . ? Fe1 C1 2.009(3) . ? Fe1 C5 2.025(3) . ? Fe1 C6 2.033(3) . ? Fe1 C9 2.045(3) . ? Fe1 C2 2.056(3) . ? Fe1 C4 2.064(3) . ? Fe1 C7 2.071(3) . ? Fe1 C3 2.085(3) . ? Fe1 C8 2.086(3) . ? C1 C2 1.437(4) . ? C1 C5 1.448(4) . ? C1 C14 1.462(4) . ? C2 C3 1.416(4) . ? C2 H2 0.9500 . ? C3 C4 1.420(4) . ? C3 H3 0.9500 . ? C4 C5 1.408(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.413(4) . ? C6 C10 1.444(4) . ? C6 H6 0.9500 . ? C7 C8 1.418(4) . ? C7 H7 0.9500 . ? C8 C9 1.404(4) . ? C8 H8 0.9500 . ? C9 C10 1.445(4) . ? C9 H9 0.9500 . ? C10 C11 1.466(4) . ? C11 O2 1.208(3) . ? C11 C12 1.547(4) . ? C12 F3 1.355(3) . ? C12 F2 1.364(3) . ? C12 C13 1.544(4) . ? C13 F4 1.349(3) . ? C13 F5 1.357(3) . ? C13 C14 1.554(4) . ? C14 O1 1.213(4) . ? 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 C10 Fe1 C1 110.49(11) . . ? C10 Fe1 C5 108.14(12) . . ? C1 Fe1 C5 42.06(11) . . ? C10 Fe1 C6 41.87(11) . . ? C1 Fe1 C6 109.63(12) . . ? C5 Fe1 C6 136.76(12) . . ? C10 Fe1 C9 41.78(11) . . ? C1 Fe1 C9 140.96(12) . . ? C5 Fe1 C9 110.72(12) . . ? C6 Fe1 C9 69.47(12) . . ? C10 Fe1 C2 141.59(12) . . ? C1 Fe1 C2 41.40(11) . . ? C5 Fe1 C2 69.60(12) . . ? C6 Fe1 C2 112.78(12) . . ? C9 Fe1 C2 176.58(12) . . ? C10 Fe1 C4 135.81(12) . . ? C1 Fe1 C4 68.67(12) . . ? C5 Fe1 C4 40.27(12) . . ? C6 Fe1 C4 176.89(12) . . ? C9 Fe1 C4 110.07(12) . . ? C2 Fe1 C4 67.83(12) . . ? C10 Fe1 C7 68.73(12) . . ? C1 Fe1 C7 137.63(12) . . ? C5 Fe1 C7 176.76(12) . . ? C6 Fe1 C7 40.27(11) . . ? C9 Fe1 C7 67.64(12) . . ? C2 Fe1 C7 112.23(12) . . ? C4 Fe1 C7 142.67(12) . . ? C10 Fe1 C3 175.82(12) . . ? C1 Fe1 C3 68.47(11) . . ? C5 Fe1 C3 68.26(12) . . ? C6 Fe1 C3 142.26(12) . . ? C9 Fe1 C3 136.70(12) . . ? C2 Fe1 C3 40.00(12) . . ? C4 Fe1 C3 40.03(12) . . ? C7 Fe1 C3 114.90(12) . . ? C10 Fe1 C8 68.56(11) . . ? C1 Fe1 C8 177.46(12) . . ? C5 Fe1 C8 140.36(12) . . ? C6 Fe1 C8 68.04(12) . . ? C9 Fe1 C8 39.73(12) . . ? C2 Fe1 C8 138.08(12) . . ? C4 Fe1 C8 113.71(12) . . ? C7 Fe1 C8 39.90(12) . . ? C3 Fe1 C8 112.65(12) . . ? C2 C1 C5 107.7(2) . . ? C2 C1 C14 122.3(3) . . ? C5 C1 C14 128.9(3) . . ? C2 C1 Fe1 71.04(16) . . ? C5 C1 Fe1 69.57(16) . . ? C14 C1 Fe1 115.6(2) . . ? C3 C2 C1 107.7(3) . . ? C3 C2 Fe1 71.11(17) . . ? C1 C2 Fe1 67.56(16) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? Fe1 C2 H2 126.7 . . ? C2 C3 C4 108.3(3) . . ? C2 C3 Fe1 68.89(16) . . ? C4 C3 Fe1 69.20(17) . . ? C2 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? Fe1 C3 H3 127.6 . . ? C5 C4 C3 109.3(3) . . ? C5 C4 Fe1 68.38(17) . . ? C3 C4 Fe1 70.77(17) . . ? C5 C4 H4 125.4 . . ? C3 C4 H4 125.4 . . ? Fe1 C4 H4 127.1 . . ? C4 C5 C1 107.1(3) . . ? C4 C5 Fe1 71.35(18) . . ? C1 C5 Fe1 68.38(16) . . ? C4 C5 H5 126.4 . . ? C1 C5 H5 126.4 . . ? Fe1 C5 H5 125.4 . . ? C7 C6 C10 107.4(3) . . ? C7 C6 Fe1 71.29(17) . . ? C10 C6 Fe1 68.10(16) . . ? C7 C6 H6 126.3 . . ? C10 C6 H6 126.3 . . ? Fe1 C6 H6 125.9 . . ? C6 C7 C8 109.0(3) . . ? C6 C7 Fe1 68.44(16) . . ? C8 C7 Fe1 70.62(17) . . ? C6 C7 H7 125.5 . . ? C8 C7 H7 125.5 . . ? Fe1 C7 H7 127.0 . . ? C9 C8 C7 108.5(3) . . ? C9 C8 Fe1 68.57(16) . . ? C7 C8 Fe1 69.48(16) . . ? C9 C8 H8 125.7 . . ? C7 C8 H8 125.7 . . ? Fe1 C8 H8 127.8 . . ? C8 C9 C10 108.0(3) . . ? C8 C9 Fe1 71.69(17) . . ? C10 C9 Fe1 67.71(16) . . ? C8 C9 H9 126.0 . . ? C10 C9 H9 126.0 . . ? Fe1 C9 H9 126.2 . . ? C6 C10 C9 107.1(2) . . ? C6 C10 C11 130.2(3) . . ? C9 C10 C11 121.8(3) . . ? C6 C10 Fe1 70.03(16) . . ? C9 C10 Fe1 70.51(16) . . ? C11 C10 Fe1 115.9(2) . . ? O2 C11 C10 123.3(3) . . ? O2 C11 C12 116.8(3) . . ? C10 C11 C12 119.9(2) . . ? F3 C12 F2 106.7(2) . . ? F3 C12 C13 107.3(2) . . ? F2 C12 C13 107.3(2) . . ? F3 C12 C11 107.8(2) . . ? F2 C12 C11 111.2(2) . . ? C13 C12 C11 116.1(2) . . ? F4 C13 F5 107.1(2) . . ? F4 C13 C12 107.4(2) . . ? F5 C13 C12 107.6(2) . . ? F4 C13 C14 108.1(2) . . ? F5 C13 C14 111.3(2) . . ? C12 C13 C14 115.0(2) . . ? O1 C14 C1 123.8(3) . . ? O1 C14 C13 116.6(3) . . ? C1 C14 C13 119.5(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.413 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.080 # Attachment '3.cif' data_maufoa _database_code_depnum_ccdc_archive 'CCDC 819731' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 F6 Fe' _chemical_formula_weight 346.05 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' F F 0.0171 0.0103 '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' H H 0.0000 0.0000 '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 7.3340(16) _cell_length_b 15.551(3) _cell_length_c 10.017(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.958(5) _cell_angle_gamma 90.00 _cell_volume 1141.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 961 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.1 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.013 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6580 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD Bruker-AXS' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12787 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 30.56 _reflns_number_total 3488 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker-AXS)' _computing_cell_refinement 'SAINT (Bruker-AXS)' _computing_data_reduction 'SAINT (Bruker-AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0459P)^2^+0.5334P] 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 3488 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.94088(4) 0.855239(17) 0.86829(3) 0.01470(9) Uani 1 1 d . . . C1 C 0.9507(3) 0.83782(14) 0.6684(2) 0.0232(4) Uani 1 1 d . . . H1 H 0.8435 0.8355 0.6041 0.028 Uiso 1 1 calc R . . C2 C 1.0537(3) 0.91226(15) 0.7035(2) 0.0277(5) Uani 1 1 d . . . H2 H 1.0282 0.9719 0.6707 0.033 Uiso 1 1 calc R . . C3 C 1.1931(3) 0.88841(14) 0.7985(2) 0.0257(5) Uani 1 1 d . . . H3 H 1.2827 0.9284 0.8434 0.031 Uiso 1 1 calc R . . C4 C 1.1789(3) 0.79816(13) 0.8225(2) 0.0203(4) Uani 1 1 d . . . H4 H 1.2593 0.7634 0.8845 0.024 Uiso 1 1 calc R . . C5 C 1.0264(3) 0.76654(13) 0.74298(19) 0.0167(4) Uani 1 1 d . . . C6 C 0.9230(3) 0.68403(13) 0.75944(19) 0.0162(4) Uani 1 1 d . . . C7 C 1.0225(3) 0.60520(13) 0.8246(2) 0.0189(4) Uani 1 1 d . . . C8 C 0.8999(3) 0.60976(13) 0.9467(2) 0.0189(4) Uani 1 1 d . . . C9 C 0.7883(3) 0.68530(13) 0.88156(19) 0.0160(4) Uani 1 1 d . . . C10 C 0.7775(3) 0.77099(12) 0.95074(18) 0.0158(4) Uani 1 1 d . . . C11 C 0.6714(3) 0.84082(14) 0.8947(2) 0.0207(4) Uani 1 1 d . . . H11 H 0.5744 0.8362 0.8225 0.025 Uiso 1 1 calc R . . C12 C 0.7300(3) 0.91776(14) 0.9601(2) 0.0225(4) Uani 1 1 d . . . H12 H 0.6850 0.9770 0.9385 0.027 Uiso 1 1 calc R . . C13 C 0.8700(3) 0.89685(14) 1.0561(2) 0.0224(4) Uani 1 1 d . . . H13 H 0.9402 0.9388 1.1134 0.027 Uiso 1 1 calc R . . C14 C 0.8988(3) 0.80627(13) 1.05277(19) 0.0182(4) Uani 1 1 d . . . H14 H 0.9893 0.7733 1.1094 0.022 Uiso 1 1 calc R . . F1 F 0.83552(18) 0.66034(9) 0.64139(12) 0.0244(3) Uani 1 1 d . . . F2 F 0.9968(2) 0.53239(8) 0.75426(13) 0.0296(3) Uani 1 1 d . . . F3 F 1.20217(17) 0.61340(9) 0.85290(14) 0.0286(3) Uani 1 1 d . . . F4 F 0.8026(2) 0.53827(8) 0.96576(14) 0.0310(3) Uani 1 1 d . . . F5 F 0.9930(2) 0.62842(9) 1.06173(12) 0.0282(3) Uani 1 1 d . . . F6 F 0.61700(17) 0.65597(8) 0.84370(13) 0.0245(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01386(14) 0.01648(14) 0.01390(14) 0.00132(10) 0.00262(9) 0.00134(11) C1 0.0273(11) 0.0283(11) 0.0143(9) 0.0052(8) 0.0062(8) 0.0059(8) C2 0.0345(13) 0.0239(10) 0.0257(11) 0.0062(9) 0.0152(9) 0.0018(9) C3 0.0195(10) 0.0222(10) 0.0361(12) -0.0020(9) 0.0128(9) -0.0039(8) C4 0.0141(9) 0.0224(10) 0.0246(10) -0.0020(8) 0.0043(8) -0.0005(7) C5 0.0156(9) 0.0218(9) 0.0129(8) 0.0001(7) 0.0042(7) 0.0002(7) C6 0.0157(9) 0.0211(9) 0.0118(8) -0.0031(7) 0.0004(7) -0.0001(7) C7 0.0191(10) 0.0172(9) 0.0206(9) -0.0022(7) 0.0017(7) 0.0000(7) C8 0.0230(10) 0.0181(9) 0.0159(9) -0.0005(7) 0.0023(7) -0.0007(8) C9 0.0129(9) 0.0197(9) 0.0152(9) -0.0011(7) 0.0002(7) -0.0022(7) C10 0.0147(9) 0.0201(9) 0.0129(8) -0.0003(7) 0.0038(7) -0.0004(7) C11 0.0130(9) 0.0280(11) 0.0214(10) 0.0009(8) 0.0036(7) 0.0034(8) C12 0.0233(11) 0.0217(10) 0.0231(10) -0.0004(8) 0.0080(8) 0.0060(8) C13 0.0278(11) 0.0207(10) 0.0190(10) -0.0019(8) 0.0032(8) 0.0008(8) C14 0.0219(10) 0.0187(9) 0.0140(9) -0.0007(7) 0.0007(7) -0.0008(7) F1 0.0240(6) 0.0348(7) 0.0142(6) -0.0061(5) -0.0033(5) -0.0020(5) F2 0.0459(9) 0.0189(6) 0.0243(7) -0.0080(5) 0.0066(6) 0.0028(6) F3 0.0164(6) 0.0319(7) 0.0375(8) 0.0119(6) 0.0017(5) 0.0041(5) F4 0.0352(8) 0.0186(6) 0.0402(8) 0.0038(6) 0.0162(6) -0.0034(5) F5 0.0398(8) 0.0284(7) 0.0159(6) -0.0023(5) -0.0066(5) 0.0123(6) F6 0.0148(6) 0.0331(7) 0.0257(6) -0.0049(5) -0.0003(5) -0.0070(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 C10 1.9755(19) . ? Fe1 C5 1.981(2) . ? Fe1 C11 2.015(2) . ? Fe1 C1 2.024(2) . ? Fe1 C4 2.025(2) . ? Fe1 C14 2.032(2) . ? Fe1 C3 2.065(2) . ? Fe1 C12 2.069(2) . ? Fe1 C2 2.071(2) . ? Fe1 C13 2.072(2) . ? C1 C2 1.420(3) . ? C1 C5 1.438(3) . ? C1 H1 1.0000 . ? C2 C3 1.422(4) . ? C2 H2 1.0000 . ? C3 C4 1.428(3) . ? C3 H3 1.0000 . ? C4 C5 1.437(3) . ? C4 H4 1.0000 . ? C5 C6 1.502(3) . ? C6 F1 1.376(2) . ? C6 C7 1.558(3) . ? C6 C9 1.599(3) . ? C7 F2 1.343(2) . ? C7 F3 1.345(2) . ? C7 C8 1.544(3) . ? C8 F4 1.338(2) . ? C8 F5 1.351(2) . ? C8 C9 1.562(3) . ? C9 F6 1.377(2) . ? C9 C10 1.505(3) . ? C10 C11 1.438(3) . ? C10 C14 1.441(3) . ? C11 C12 1.423(3) . ? C11 H11 1.0000 . ? C12 C13 1.420(3) . ? C12 H12 1.0000 . ? C13 C14 1.425(3) . ? C13 H13 1.0000 . ? C14 H14 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Fe1 C5 90.74(8) . . ? C10 Fe1 C11 42.24(8) . . ? C5 Fe1 C11 109.81(9) . . ? C10 Fe1 C1 111.55(9) . . ? C5 Fe1 C1 42.05(8) . . ? C11 Fe1 C1 100.56(9) . . ? C10 Fe1 C4 110.13(8) . . ? C5 Fe1 C4 42.03(8) . . ? C11 Fe1 C4 146.91(9) . . ? C1 Fe1 C4 69.95(9) . . ? C10 Fe1 C14 42.11(8) . . ? C5 Fe1 C14 112.11(8) . . ? C11 Fe1 C14 70.04(9) . . ? C1 Fe1 C14 149.43(9) . . ? C4 Fe1 C14 101.58(9) . . ? C10 Fe1 C3 150.51(9) . . ? C5 Fe1 C3 69.68(9) . . ? C11 Fe1 C3 165.00(9) . . ? C1 Fe1 C3 68.66(10) . . ? C4 Fe1 C3 40.86(9) . . ? C14 Fe1 C3 124.55(9) . . ? C10 Fe1 C12 69.66(9) . . ? C5 Fe1 C12 150.05(9) . . ? C11 Fe1 C12 40.76(9) . . ? C1 Fe1 C12 123.70(9) . . ? C4 Fe1 C12 165.95(9) . . ? C14 Fe1 C12 68.46(8) . . ? C3 Fe1 C12 136.46(9) . . ? C10 Fe1 C2 151.85(9) . . ? C5 Fe1 C2 69.47(9) . . ? C11 Fe1 C2 124.94(9) . . ? C1 Fe1 C2 40.55(9) . . ? C4 Fe1 C2 68.65(9) . . ? C14 Fe1 C2 164.27(10) . . ? C3 Fe1 C2 40.21(10) . . ? C12 Fe1 C2 118.57(9) . . ? C10 Fe1 C13 69.70(8) . . ? C5 Fe1 C13 152.52(8) . . ? C11 Fe1 C13 68.77(9) . . ? C1 Fe1 C13 163.37(9) . . ? C4 Fe1 C13 125.98(9) . . ? C14 Fe1 C13 40.62(8) . . ? C3 Fe1 C13 118.99(9) . . ? C12 Fe1 C13 40.12(9) . . ? C2 Fe1 C13 135.18(9) . . ? C2 C1 C5 107.9(2) . . ? C2 C1 Fe1 71.51(13) . . ? C5 C1 Fe1 67.38(11) . . ? C2 C1 H1 126.1 . . ? C5 C1 H1 126.1 . . ? Fe1 C1 H1 126.1 . . ? C1 C2 C3 108.5(2) . . ? C1 C2 Fe1 67.94(12) . . ? C3 C2 Fe1 69.66(12) . . ? C1 C2 H2 125.7 . . ? C3 C2 H2 125.7 . . ? Fe1 C2 H2 125.7 . . ? C2 C3 C4 108.3(2) . . ? C2 C3 Fe1 70.13(13) . . ? C4 C3 Fe1 68.08(12) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe1 C3 H3 125.8 . . ? C3 C4 C5 107.61(19) . . ? C3 C4 Fe1 71.06(12) . . ? C5 C4 Fe1 67.35(11) . . ? C3 C4 H4 126.2 . . ? C5 C4 H4 126.2 . . ? Fe1 C4 H4 126.2 . . ? C4 C5 C1 107.67(18) . . ? C4 C5 C6 128.13(18) . . ? C1 C5 C6 121.88(18) . . ? C4 C5 Fe1 70.62(11) . . ? C1 C5 Fe1 70.57(12) . . ? C6 C5 Fe1 110.69(13) . . ? F1 C6 C5 110.89(16) . . ? F1 C6 C7 110.30(16) . . ? C5 C6 C7 119.16(17) . . ? F1 C6 C9 112.23(15) . . ? C5 C6 C9 113.63(16) . . ? C7 C6 C9 88.98(14) . . ? F2 C7 F3 108.04(17) . . ? F2 C7 C8 112.27(17) . . ? F3 C7 C8 114.91(17) . . ? F2 C7 C6 112.86(17) . . ? F3 C7 C6 117.07(17) . . ? C8 C7 C6 91.07(15) . . ? F4 C8 F5 108.24(16) . . ? F4 C8 C7 113.74(16) . . ? F5 C8 C7 113.27(18) . . ? F4 C8 C9 114.20(17) . . ? F5 C8 C9 115.92(16) . . ? C7 C8 C9 90.84(15) . . ? F6 C9 C10 110.97(16) . . ? F6 C9 C8 109.03(16) . . ? C10 C9 C8 120.58(16) . . ? F6 C9 C6 111.54(15) . . ? C10 C9 C6 114.01(16) . . ? C8 C9 C6 88.93(14) . . ? C11 C10 C14 107.56(17) . . ? C11 C10 C9 121.68(17) . . ? C14 C10 C9 128.51(18) . . ? C11 C10 Fe1 70.36(12) . . ? C14 C10 Fe1 71.04(11) . . ? C9 C10 Fe1 110.63(13) . . ? C12 C11 C10 107.75(18) . . ? C12 C11 Fe1 71.65(12) . . ? C10 C11 Fe1 67.41(11) . . ? C12 C11 H11 126.1 . . ? C10 C11 H11 126.1 . . ? Fe1 C11 H11 126.1 . . ? C13 C12 C11 108.58(19) . . ? C13 C12 Fe1 70.05(12) . . ? C11 C12 Fe1 67.59(12) . . ? C13 C12 H12 125.7 . . ? C11 C12 H12 125.7 . . ? Fe1 C12 H12 125.7 . . ? C12 C13 C14 108.36(19) . . ? C12 C13 Fe1 69.83(12) . . ? C14 C13 Fe1 68.18(11) . . ? C12 C13 H13 125.8 . . ? C14 C13 H13 125.8 . . ? Fe1 C13 H13 125.8 . . ? C13 C14 C10 107.73(18) . . ? C13 C14 Fe1 71.20(12) . . ? C10 C14 Fe1 66.85(11) . . ? C13 C14 H14 126.1 . . ? C10 C14 H14 126.1 . . ? Fe1 C14 H14 126.1 . . ? 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 C6 C7 C8 C9 3.26(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.767 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.104