# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email janzak@uni.lodz.pl _publ_contact_author_name 'Janusz Zakrzewski' _publ_author_name 'J. Zakrzewski' data_2d _database_code_depnum_ccdc_archive 'CCDC 839178' #TrackingRef 'web_deposit_cif_file_0_KrzysztofWozniak_1313347883.CIF_sum.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 Fe O' _chemical_formula_weight 314.15 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 21.5703(8) _cell_length_b 5.9474(2) _cell_length_c 10.9774(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1408.26(9) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 510 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.50 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_monochromator 'mutli-layer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17233 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2754 _reflns_number_gt 2725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0075P)^2^+0.4556P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(10) _refine_ls_number_reflns 2754 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0179 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0415 _refine_ls_wR_factor_gt 0.0414 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.003 _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 0.806654(7) 0.45806(3) 0.50187(2) 0.01072(5) Uani 1 1 d . . . O1 O 0.85122(6) -0.00038(18) 0.27368(10) 0.0212(2) Uani 1 1 d . . . C1 C 0.78882(6) 0.3005(2) 0.34166(12) 0.0132(2) Uani 1 1 d . . . C2 C 0.76675(7) 0.5289(2) 0.33813(13) 0.0151(3) Uani 1 1 d . . . H2 H 0.7797 0.6432 0.2833 0.018 Uiso 1 1 calc R . . C3 C 0.72191(6) 0.5511(2) 0.43229(13) 0.0164(3) Uani 1 1 d . . . H3 H 0.6991 0.6836 0.4503 0.020 Uiso 1 1 calc R . . C4 C 0.71681(6) 0.3425(2) 0.49524(17) 0.0166(2) Uani 1 1 d . . . H4 H 0.6904 0.3128 0.5625 0.020 Uiso 1 1 calc R . . C5 C 0.75799(6) 0.1868(2) 0.44027(13) 0.0153(3) Uani 1 1 d . . . H5 H 0.7641 0.0349 0.4642 0.018 Uiso 1 1 calc R . . C6 C 0.90088(6) 0.4731(2) 0.52481(13) 0.0182(3) Uani 1 1 d . . . H6 H 0.9314 0.4221 0.4688 0.022 Uiso 1 1 calc R . . C7 C 0.87488(6) 0.6933(2) 0.52879(12) 0.0166(3) Uani 1 1 d . . . H7 H 0.8848 0.8146 0.4760 0.020 Uiso 1 1 calc R . . C8 C 0.83131(6) 0.6985(2) 0.62622(13) 0.0160(3) Uani 1 1 d . . . H8 H 0.8071 0.8245 0.6500 0.019 Uiso 1 1 calc R . . C9 C 0.83032(7) 0.4828(3) 0.68170(13) 0.0171(3) Uani 1 1 d . . . H9 H 0.8053 0.4392 0.7489 0.021 Uiso 1 1 calc R . . C10 C 0.87339(7) 0.3432(3) 0.61895(13) 0.0183(3) Uani 1 1 d . . . H10 H 0.8822 0.1903 0.6369 0.022 Uiso 1 1 calc R . . C11 C 0.83748(6) 0.1992(2) 0.26686(12) 0.0149(3) Uani 1 1 d . . . C12 C 0.86923(7) 0.3464(2) 0.18048(12) 0.0158(3) Uani 1 1 d . . . C13 C 0.89620(7) 0.4595(2) 0.10759(13) 0.0150(3) Uani 1 1 d . . . C14 C 0.92785(6) 0.6027(2) 0.02280(12) 0.0135(3) Uani 1 1 d . . . C15 C 0.93765(7) 0.5351(2) -0.09762(13) 0.0180(3) Uani 1 1 d . . . H15 H 0.9241 0.3912 -0.1241 0.022 Uiso 1 1 calc R . . C16 C 0.96726(7) 0.6794(3) -0.17860(14) 0.0233(3) Uani 1 1 d . . . H16 H 0.9737 0.6342 -0.2606 0.028 Uiso 1 1 calc R . . C17 C 0.98737(7) 0.8890(3) -0.13991(15) 0.0262(3) Uani 1 1 d . . . H17 H 1.0077 0.9868 -0.1954 0.031 Uiso 1 1 calc R . . C18 C 0.97782(7) 0.9567(2) -0.02011(16) 0.0246(4) Uani 1 1 d . . . H18 H 0.9922 1.0997 0.0063 0.030 Uiso 1 1 calc R . . C19 C 0.94751(7) 0.8163(3) 0.06066(14) 0.0187(3) Uani 1 1 d . . . H19 H 0.9400 0.8646 0.1418 0.022 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 0.01020(8) 0.01194(8) 0.01003(8) -0.00039(10) 0.00024(8) -0.00164(6) O1 0.0297(6) 0.0155(5) 0.0183(5) 0.0003(4) 0.0043(4) 0.0017(4) C1 0.0143(6) 0.0144(6) 0.0109(6) 0.0001(5) -0.0025(5) -0.0031(5) C2 0.0138(6) 0.0168(6) 0.0146(6) 0.0022(5) -0.0025(5) -0.0005(5) C3 0.0128(6) 0.0194(7) 0.0171(7) -0.0017(6) -0.0023(5) 0.0006(5) C4 0.0114(5) 0.0224(6) 0.0160(6) -0.0006(7) -0.0012(6) -0.0053(4) C5 0.0158(6) 0.0163(6) 0.0138(6) -0.0009(5) -0.0013(5) -0.0055(5) C6 0.0108(5) 0.0243(6) 0.0196(9) -0.0067(6) -0.0014(5) -0.0006(5) C7 0.0143(5) 0.0188(6) 0.0166(7) 0.0000(5) -0.0013(5) -0.0066(5) C8 0.0154(6) 0.0162(6) 0.0165(6) -0.0046(5) -0.0015(5) -0.0019(5) C9 0.0186(7) 0.0217(7) 0.0110(6) 0.0002(5) -0.0021(5) -0.0050(5) C10 0.0181(6) 0.0181(7) 0.0187(7) -0.0012(6) -0.0088(6) 0.0004(5) C11 0.0177(6) 0.0170(6) 0.0100(6) -0.0009(5) -0.0021(5) -0.0030(5) C12 0.0170(6) 0.0166(7) 0.0139(6) -0.0024(5) -0.0005(5) 0.0006(5) C13 0.0142(6) 0.0171(6) 0.0136(6) -0.0020(5) -0.0016(5) 0.0011(5) C14 0.0101(5) 0.0172(6) 0.0133(8) 0.0015(5) -0.0001(5) 0.0016(4) C15 0.0150(7) 0.0243(7) 0.0148(8) -0.0005(6) -0.0028(5) 0.0008(5) C16 0.0185(7) 0.0380(9) 0.0135(6) 0.0051(6) 0.0002(6) 0.0007(6) C17 0.0177(7) 0.0336(8) 0.0274(8) 0.0153(7) 0.0045(6) -0.0016(6) C18 0.0187(6) 0.0193(7) 0.0357(12) 0.0035(6) 0.0012(6) -0.0014(5) C19 0.0150(6) 0.0200(7) 0.0211(7) -0.0027(6) 0.0016(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 2.0295(13) . ? Fe1 C2 2.0370(14) . ? Fe1 C5 2.0403(13) . ? Fe1 C9 2.0442(15) . ? Fe1 C10 2.0471(14) . ? Fe1 C8 2.0472(14) . ? Fe1 C6 2.0499(13) . ? Fe1 C7 2.0518(13) . ? Fe1 C3 2.0571(14) . ? Fe1 C4 2.0575(12) . ? O1 C11 1.2260(18) . ? C1 C5 1.4393(19) . ? C1 C2 1.4399(19) . ? C1 C11 1.462(2) . ? C2 C3 1.422(2) . ? C3 C4 1.425(2) . ? C4 C5 1.418(2) . ? C6 C10 1.420(2) . ? C6 C7 1.425(2) . ? C7 C8 1.424(2) . ? C8 C9 1.421(2) . ? C9 C10 1.423(2) . ? C11 C12 1.4608(19) . ? C12 C13 1.196(2) . ? C13 C14 1.4344(19) . ? C14 C15 1.3977(19) . ? C14 C19 1.403(2) . ? C15 C16 1.391(2) . ? C16 C17 1.387(3) . ? C17 C18 1.391(2) . ? C18 C19 1.382(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 C1 Fe1 C2 41.48(5) . . ? C1 Fe1 C5 41.42(5) . . ? C2 Fe1 C5 69.74(6) . . ? C1 Fe1 C9 156.53(6) . . ? C2 Fe1 C9 160.52(6) . . ? C5 Fe1 C9 120.36(6) . . ? C1 Fe1 C10 121.55(6) . . ? C2 Fe1 C10 156.95(6) . . ? C5 Fe1 C10 107.83(6) . . ? C9 Fe1 C10 40.72(6) . . ? C1 Fe1 C8 161.72(6) . . ? C2 Fe1 C8 123.61(6) . . ? C5 Fe1 C8 155.11(6) . . ? C9 Fe1 C8 40.63(6) . . ? C10 Fe1 C8 68.39(6) . . ? C1 Fe1 C6 108.33(5) . . ? C2 Fe1 C6 121.21(6) . . ? C5 Fe1 C6 125.83(6) . . ? C9 Fe1 C6 68.32(6) . . ? C10 Fe1 C6 40.56(6) . . ? C8 Fe1 C6 68.28(5) . . ? C1 Fe1 C7 125.14(5) . . ? C2 Fe1 C7 106.80(5) . . ? C5 Fe1 C7 162.93(6) . . ? C9 Fe1 C7 68.46(6) . . ? C10 Fe1 C7 68.45(6) . . ? C8 Fe1 C7 40.66(5) . . ? C6 Fe1 C7 40.66(6) . . ? C1 Fe1 C3 68.53(6) . . ? C2 Fe1 C3 40.64(6) . . ? C5 Fe1 C3 68.44(6) . . ? C9 Fe1 C3 124.14(6) . . ? C10 Fe1 C3 161.41(6) . . ? C8 Fe1 C3 106.88(6) . . ? C6 Fe1 C3 156.19(6) . . ? C7 Fe1 C3 120.48(6) . . ? C1 Fe1 C4 68.69(6) . . ? C2 Fe1 C4 68.89(7) . . ? C5 Fe1 C4 40.49(6) . . ? C9 Fe1 C4 107.06(7) . . ? C10 Fe1 C4 124.97(6) . . ? C8 Fe1 C4 120.11(6) . . ? C6 Fe1 C4 162.33(6) . . ? C7 Fe1 C4 155.28(5) . . ? C3 Fe1 C4 40.52(6) . . ? C5 C1 C2 108.11(12) . . ? C5 C1 C11 124.08(12) . . ? C2 C1 C11 127.64(12) . . ? C5 C1 Fe1 69.69(8) . . ? C2 C1 Fe1 69.54(8) . . ? C11 C1 Fe1 122.73(9) . . ? C3 C2 C1 107.04(12) . . ? C3 C2 Fe1 70.44(8) . . ? C1 C2 Fe1 68.99(8) . . ? C2 C3 C4 108.91(13) . . ? C2 C3 Fe1 68.92(8) . . ? C4 C3 Fe1 69.76(7) . . ? C5 C4 C3 108.31(14) . . ? C5 C4 Fe1 69.10(7) . . ? C3 C4 Fe1 69.73(7) . . ? C4 C5 C1 107.61(12) . . ? C4 C5 Fe1 70.41(7) . . ? C1 C5 Fe1 68.89(7) . . ? C10 C6 C7 108.26(12) . . ? C10 C6 Fe1 69.61(8) . . ? C7 C6 Fe1 69.74(8) . . ? C8 C7 C6 107.63(12) . . ? C8 C7 Fe1 69.50(8) . . ? C6 C7 Fe1 69.60(7) . . ? C9 C8 C7 108.19(12) . . ? C9 C8 Fe1 69.57(8) . . ? C7 C8 Fe1 69.85(8) . . ? C8 C9 C10 108.02(13) . . ? C8 C9 Fe1 69.80(8) . . ? C10 C9 Fe1 69.75(8) . . ? C6 C10 C9 107.91(13) . . ? C6 C10 Fe1 69.83(8) . . ? C9 C10 Fe1 69.53(8) . . ? O1 C11 C12 120.42(13) . . ? O1 C11 C1 122.55(13) . . ? C12 C11 C1 117.02(12) . . ? C13 C12 C11 177.43(15) . . ? C12 C13 C14 177.81(15) . . ? C15 C14 C19 119.66(13) . . ? C15 C14 C13 121.01(12) . . ? C19 C14 C13 119.30(12) . . ? C16 C15 C14 119.78(14) . . ? C17 C16 C15 120.16(14) . . ? C16 C17 C18 120.24(14) . . ? C19 C18 C17 120.13(15) . . ? C18 C19 C14 120.01(14) . . ? 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 C5 -119.46(11) . . . . ? C9 Fe1 C1 C5 46.18(17) . . . . ? C10 Fe1 C1 C5 81.20(9) . . . . ? C8 Fe1 C1 C5 -160.04(16) . . . . ? C6 Fe1 C1 C5 123.83(8) . . . . ? C7 Fe1 C1 C5 165.75(8) . . . . ? C3 Fe1 C1 C5 -81.30(8) . . . . ? C4 Fe1 C1 C5 -37.65(8) . . . . ? C5 Fe1 C1 C2 119.46(11) . . . . ? C9 Fe1 C1 C2 165.64(13) . . . . ? C10 Fe1 C1 C2 -159.34(8) . . . . ? C8 Fe1 C1 C2 -40.6(2) . . . . ? C6 Fe1 C1 C2 -116.71(8) . . . . ? C7 Fe1 C1 C2 -74.79(10) . . . . ? C3 Fe1 C1 C2 38.16(8) . . . . ? C4 Fe1 C1 C2 81.82(9) . . . . ? C2 Fe1 C1 C11 122.34(14) . . . . ? C5 Fe1 C1 C11 -118.19(14) . . . . ? C9 Fe1 C1 C11 -72.02(19) . . . . ? C10 Fe1 C1 C11 -37.00(13) . . . . ? C8 Fe1 C1 C11 81.8(2) . . . . ? C6 Fe1 C1 C11 5.63(13) . . . . ? C7 Fe1 C1 C11 47.56(14) . . . . ? C3 Fe1 C1 C11 160.50(13) . . . . ? C4 Fe1 C1 C11 -155.84(13) . . . . ? C5 C1 C2 C3 -1.26(15) . . . . ? C11 C1 C2 C3 -176.64(13) . . . . ? Fe1 C1 C2 C3 -60.47(9) . . . . ? C5 C1 C2 Fe1 59.21(9) . . . . ? C11 C1 C2 Fe1 -116.17(14) . . . . ? C1 Fe1 C2 C3 118.01(11) . . . . ? C5 Fe1 C2 C3 80.13(9) . . . . ? C9 Fe1 C2 C3 -44.8(2) . . . . ? C10 Fe1 C2 C3 168.18(13) . . . . ? C8 Fe1 C2 C3 -76.17(10) . . . . ? C6 Fe1 C2 C3 -159.47(8) . . . . ? C7 Fe1 C2 C3 -117.51(8) . . . . ? C4 Fe1 C2 C3 36.73(8) . . . . ? C5 Fe1 C2 C1 -37.88(8) . . . . ? C9 Fe1 C2 C1 -162.77(15) . . . . ? C10 Fe1 C2 C1 50.16(18) . . . . ? C8 Fe1 C2 C1 165.82(8) . . . . ? C6 Fe1 C2 C1 82.52(9) . . . . ? C7 Fe1 C2 C1 124.48(8) . . . . ? C3 Fe1 C2 C1 -118.01(11) . . . . ? C4 Fe1 C2 C1 -81.29(8) . . . . ? C1 C2 C3 C4 1.14(15) . . . . ? Fe1 C2 C3 C4 -58.40(10) . . . . ? C1 C2 C3 Fe1 59.54(9) . . . . ? C1 Fe1 C3 C2 -38.92(8) . . . . ? C5 Fe1 C3 C2 -83.61(9) . . . . ? C9 Fe1 C3 C2 163.52(8) . . . . ? C10 Fe1 C3 C2 -165.42(16) . . . . ? C8 Fe1 C3 C2 122.32(8) . . . . ? C6 Fe1 C3 C2 47.98(17) . . . . ? C7 Fe1 C3 C2 80.16(9) . . . . ? C4 Fe1 C3 C2 -120.82(12) . . . . ? C1 Fe1 C3 C4 81.90(10) . . . . ? C2 Fe1 C3 C4 120.82(12) . . . . ? C5 Fe1 C3 C4 37.21(9) . . . . ? C9 Fe1 C3 C4 -75.66(11) . . . . ? C10 Fe1 C3 C4 -44.6(2) . . . . ? C8 Fe1 C3 C4 -116.86(10) . . . . ? C6 Fe1 C3 C4 168.81(13) . . . . ? C7 Fe1 C3 C4 -159.01(9) . . . . ? C2 C3 C4 C5 -0.59(16) . . . . ? Fe1 C3 C4 C5 -58.48(9) . . . . ? C2 C3 C4 Fe1 57.89(10) . . . . ? C1 Fe1 C4 C5 38.49(9) . . . . ? C2 Fe1 C4 C5 83.13(10) . . . . ? C9 Fe1 C4 C5 -117.05(9) . . . . ? C10 Fe1 C4 C5 -75.88(11) . . . . ? C8 Fe1 C4 C5 -159.34(9) . . . . ? C6 Fe1 C4 C5 -45.1(3) . . . . ? C7 Fe1 C4 C5 167.54(13) . . . . ? C3 Fe1 C4 C5 119.97(14) . . . . ? C1 Fe1 C4 C3 -81.48(10) . . . . ? C2 Fe1 C4 C3 -36.84(9) . . . . ? C5 Fe1 C4 C3 -119.97(14) . . . . ? C9 Fe1 C4 C3 122.99(9) . . . . ? C10 Fe1 C4 C3 164.15(9) . . . . ? C8 Fe1 C4 C3 80.69(11) . . . . ? C6 Fe1 C4 C3 -165.04(18) . . . . ? C7 Fe1 C4 C3 47.57(19) . . . . ? C3 C4 C5 C1 -0.20(15) . . . . ? Fe1 C4 C5 C1 -59.07(9) . . . . ? C3 C4 C5 Fe1 58.87(9) . . . . ? C2 C1 C5 C4 0.90(15) . . . . ? C11 C1 C5 C4 176.49(13) . . . . ? Fe1 C1 C5 C4 60.02(9) . . . . ? C2 C1 C5 Fe1 -59.12(9) . . . . ? C11 C1 C5 Fe1 116.47(13) . . . . ? C1 Fe1 C5 C4 -118.79(12) . . . . ? C2 Fe1 C5 C4 -80.86(10) . . . . ? C9 Fe1 C5 C4 80.66(11) . . . . ? C10 Fe1 C5 C4 123.41(10) . . . . ? C8 Fe1 C5 C4 46.47(17) . . . . ? C6 Fe1 C5 C4 164.63(10) . . . . ? C7 Fe1 C5 C4 -162.09(18) . . . . ? C3 Fe1 C5 C4 -37.24(10) . . . . ? C2 Fe1 C5 C1 37.93(8) . . . . ? C9 Fe1 C5 C1 -160.55(8) . . . . ? C10 Fe1 C5 C1 -117.80(8) . . . . ? C8 Fe1 C5 C1 165.26(13) . . . . ? C6 Fe1 C5 C1 -76.58(10) . . . . ? C7 Fe1 C5 C1 -43.3(2) . . . . ? C3 Fe1 C5 C1 81.55(8) . . . . ? C4 Fe1 C5 C1 118.79(12) . . . . ? C1 Fe1 C6 C10 -117.43(9) . . . . ? C2 Fe1 C6 C10 -161.20(8) . . . . ? C5 Fe1 C6 C10 -74.75(10) . . . . ? C9 Fe1 C6 C10 37.82(9) . . . . ? C8 Fe1 C6 C10 81.71(9) . . . . ? C7 Fe1 C6 C10 119.56(12) . . . . ? C3 Fe1 C6 C10 164.34(13) . . . . ? C4 Fe1 C6 C10 -40.2(2) . . . . ? C1 Fe1 C6 C7 123.01(8) . . . . ? C2 Fe1 C6 C7 79.24(9) . . . . ? C5 Fe1 C6 C7 165.69(8) . . . . ? C9 Fe1 C6 C7 -81.74(9) . . . . ? C10 Fe1 C6 C7 -119.56(12) . . . . ? C8 Fe1 C6 C7 -37.86(8) . . . . ? C3 Fe1 C6 C7 44.78(17) . . . . ? C4 Fe1 C6 C7 -159.77(19) . . . . ? C10 C6 C7 C8 0.16(15) . . . . ? Fe1 C6 C7 C8 59.32(9) . . . . ? C10 C6 C7 Fe1 -59.15(9) . . . . ? C1 Fe1 C7 C8 164.29(8) . . . . ? C2 Fe1 C7 C8 122.41(9) . . . . ? C5 Fe1 C7 C8 -162.01(18) . . . . ? C9 Fe1 C7 C8 -37.57(8) . . . . ? C10 Fe1 C7 C8 -81.50(9) . . . . ? C6 Fe1 C7 C8 -118.95(12) . . . . ? C3 Fe1 C7 C8 80.32(10) . . . . ? C4 Fe1 C7 C8 46.51(18) . . . . ? C1 Fe1 C7 C6 -76.76(10) . . . . ? C2 Fe1 C7 C6 -118.64(9) . . . . ? C5 Fe1 C7 C6 -43.1(2) . . . . ? C9 Fe1 C7 C6 81.38(9) . . . . ? C10 Fe1 C7 C6 37.45(8) . . . . ? C8 Fe1 C7 C6 118.95(12) . . . . ? C3 Fe1 C7 C6 -160.73(8) . . . . ? C4 Fe1 C7 C6 165.46(15) . . . . ? C6 C7 C8 C9 -0.17(15) . . . . ? Fe1 C7 C8 C9 59.21(9) . . . . ? C6 C7 C8 Fe1 -59.38(9) . . . . ? C1 Fe1 C8 C9 -164.33(16) . . . . ? C2 Fe1 C8 C9 164.52(8) . . . . ? C5 Fe1 C8 C9 48.12(17) . . . . ? C10 Fe1 C8 C9 -37.79(9) . . . . ? C6 Fe1 C8 C9 -81.58(9) . . . . ? C7 Fe1 C8 C9 -119.44(12) . . . . ? C3 Fe1 C8 C9 123.15(9) . . . . ? C4 Fe1 C8 C9 81.09(10) . . . . ? C1 Fe1 C8 C7 -44.9(2) . . . . ? C2 Fe1 C8 C7 -76.04(10) . . . . ? C5 Fe1 C8 C7 167.56(13) . . . . ? C9 Fe1 C8 C7 119.44(12) . . . . ? C10 Fe1 C8 C7 81.65(9) . . . . ? C6 Fe1 C8 C7 37.86(8) . . . . ? C3 Fe1 C8 C7 -117.41(9) . . . . ? C4 Fe1 C8 C7 -159.47(8) . . . . ? C7 C8 C9 C10 0.12(15) . . . . ? Fe1 C8 C9 C10 59.50(10) . . . . ? C7 C8 C9 Fe1 -59.38(9) . . . . ? C1 Fe1 C9 C8 167.71(12) . . . . ? C2 Fe1 C9 C8 -41.8(2) . . . . ? C5 Fe1 C9 C8 -158.70(8) . . . . ? C10 Fe1 C9 C8 119.15(12) . . . . ? C6 Fe1 C9 C8 81.48(9) . . . . ? C7 Fe1 C9 C8 37.59(8) . . . . ? C3 Fe1 C9 C8 -75.45(10) . . . . ? C4 Fe1 C9 C8 -116.62(8) . . . . ? C1 Fe1 C9 C10 48.56(17) . . . . ? C2 Fe1 C9 C10 -160.95(16) . . . . ? C5 Fe1 C9 C10 82.14(10) . . . . ? C8 Fe1 C9 C10 -119.15(12) . . . . ? C6 Fe1 C9 C10 -37.68(9) . . . . ? C7 Fe1 C9 C10 -81.56(9) . . . . ? C3 Fe1 C9 C10 165.40(8) . . . . ? C4 Fe1 C9 C10 124.22(9) . . . . ? C7 C6 C10 C9 -0.09(16) . . . . ? Fe1 C6 C10 C9 -59.32(10) . . . . ? C7 C6 C10 Fe1 59.23(9) . . . . ? C8 C9 C10 C6 -0.02(16) . . . . ? Fe1 C9 C10 C6 59.51(10) . . . . ? C8 C9 C10 Fe1 -59.53(10) . . . . ? C1 Fe1 C10 C6 81.38(9) . . . . ? C2 Fe1 C10 C6 44.74(18) . . . . ? C5 Fe1 C10 C6 124.76(8) . . . . ? C9 Fe1 C10 C6 -119.13(12) . . . . ? C8 Fe1 C10 C6 -81.42(9) . . . . ? C7 Fe1 C10 C6 -37.54(8) . . . . ? C3 Fe1 C10 C6 -160.01(16) . . . . ? C4 Fe1 C10 C6 166.16(8) . . . . ? C1 Fe1 C10 C9 -159.49(8) . . . . ? C2 Fe1 C10 C9 163.87(13) . . . . ? C5 Fe1 C10 C9 -116.12(9) . . . . ? C8 Fe1 C10 C9 37.71(8) . . . . ? C6 Fe1 C10 C9 119.13(12) . . . . ? C7 Fe1 C10 C9 81.59(9) . . . . ? C3 Fe1 C10 C9 -40.9(2) . . . . ? C4 Fe1 C10 C9 -74.71(10) . . . . ? C5 C1 C11 O1 8.3(2) . . . . ? C2 C1 C11 O1 -177.02(14) . . . . ? Fe1 C1 C11 O1 94.64(15) . . . . ? C5 C1 C11 C12 -172.65(12) . . . . ? C2 C1 C11 C12 2.1(2) . . . . ? Fe1 C1 C11 C12 -86.28(14) . . . . ? C19 C14 C15 C16 0.6(2) . . . . ? C13 C14 C15 C16 178.58(13) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? C15 C16 C17 C18 -0.3(2) . . . . ? C16 C17 C18 C19 -0.8(2) . . . . ? C17 C18 C19 C14 1.8(2) . . . . ? C15 C14 C19 C18 -1.6(2) . . . . ? C13 C14 C19 C18 -179.70(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.246 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.043 data_2a _database_code_depnum_ccdc_archive 'CCDC 839179' #TrackingRef 'web_deposit_cif_file_0_KrzysztofWozniak_1313347883.CIF_sum.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Fe O' _chemical_formula_weight 238.06 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 8.9366(9) _cell_length_b 9.5424(10) _cell_length_c 12.1196(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1033.52(19) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.28 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.424 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details 'Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_monochromator 'mutli-layer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2561 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2561 _reflns_number_gt 2479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0201P)^2^+0.1886P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(13) _refine_ls_number_reflns 2561 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0208 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0460 _refine_ls_wR_factor_gt 0.0456 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.736772(19) 0.844238(19) 0.312824(16) 0.01335(6) Uani 1 1 d . . . O1 O 0.83888(12) 0.56178(12) 0.10651(10) 0.0244(2) Uani 1 1 d . . . C1 C 0.88093(15) 0.68935(14) 0.27093(13) 0.0149(3) Uani 1 1 d . . . C2 C 0.76384(15) 0.63443(14) 0.33958(12) 0.0191(3) Uani 1 1 d . . . H2 H 0.6951 0.5626 0.3200 0.023 Uiso 1 1 calc R . . C3 C 0.76913(16) 0.70628(16) 0.44142(13) 0.0218(3) Uani 1 1 d . . . H3 H 0.7044 0.6907 0.5024 0.026 Uiso 1 1 calc R . . C4 C 0.88797(15) 0.80618(16) 0.43745(13) 0.0188(3) Uani 1 1 d . . . H4 H 0.9160 0.8680 0.4953 0.023 Uiso 1 1 calc R . . C5 C 0.95695(15) 0.79710(15) 0.33226(12) 0.0154(3) Uani 1 1 d . . . H5 H 1.0385 0.8522 0.3069 0.018 Uiso 1 1 calc R . . C6 C 0.64919(18) 0.93035(17) 0.17191(14) 0.0247(3) Uani 1 1 d . . . H6 H 0.6738 0.9048 0.0983 0.030 Uiso 1 1 calc R . . C7 C 0.53421(17) 0.87064(17) 0.23633(17) 0.0280(4) Uani 1 1 d . . . H7 H 0.4681 0.7980 0.2140 0.034 Uiso 1 1 calc R . . C8 C 0.53498(16) 0.93846(18) 0.34061(15) 0.0255(4) Uani 1 1 d . . . H8 H 0.4692 0.9194 0.4003 0.031 Uiso 1 1 calc R . . C9 C 0.65133(17) 1.03982(16) 0.33989(13) 0.0203(3) Uani 1 1 d . . . H9 H 0.6774 1.1004 0.3990 0.024 Uiso 1 1 calc R . . C10 C 0.72148(17) 1.03437(15) 0.23511(12) 0.0189(3) Uani 1 1 d . . . H10 H 0.8029 1.0909 0.2116 0.023 Uiso 1 1 calc R . . C11 C 0.90291(14) 0.65772(16) 0.15475(12) 0.0172(3) Uani 1 1 d . . . C12 C 1.00845(17) 0.74792(17) 0.09613(13) 0.0206(3) Uani 1 1 d . . . C13 C 1.09589(18) 0.82158(18) 0.05091(14) 0.0264(4) Uani 1 1 d . . . H13 H 1.1660 0.8806 0.0147 0.032 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 0.01156(8) 0.01290(9) 0.01559(10) 0.00135(8) -0.00042(7) 0.00076(7) O1 0.0266(5) 0.0182(5) 0.0285(6) -0.0063(5) -0.0104(5) 0.0037(5) C1 0.0140(6) 0.0123(6) 0.0185(7) 0.0010(5) -0.0029(5) 0.0021(5) C2 0.0158(6) 0.0153(6) 0.0262(7) 0.0060(5) -0.0020(5) 0.0012(5) C3 0.0187(6) 0.0252(7) 0.0216(7) 0.0097(6) 0.0032(6) 0.0047(6) C4 0.0186(6) 0.0233(8) 0.0145(7) -0.0003(6) -0.0028(5) 0.0053(5) C5 0.0129(6) 0.0151(6) 0.0181(8) 0.0006(6) -0.0021(5) 0.0015(5) C6 0.0326(8) 0.0221(7) 0.0193(8) -0.0010(7) -0.0084(7) 0.0115(6) C7 0.0187(7) 0.0169(8) 0.0486(11) 0.0008(8) -0.0147(7) 0.0004(5) C8 0.0162(6) 0.0232(8) 0.0372(10) 0.0093(7) 0.0068(6) 0.0065(6) C9 0.0237(7) 0.0161(7) 0.0212(8) -0.0018(6) -0.0030(6) 0.0049(6) C10 0.0186(6) 0.0158(6) 0.0225(7) 0.0053(6) -0.0010(6) 0.0015(6) C11 0.0173(6) 0.0137(6) 0.0205(7) -0.0005(6) -0.0042(5) 0.0050(6) C12 0.0259(7) 0.0210(7) 0.0147(7) -0.0039(6) -0.0005(6) 0.0066(6) C13 0.0328(8) 0.0245(9) 0.0219(8) -0.0001(7) 0.0058(7) 0.0037(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 C1 2.0253(14) . ? Fe1 C5 2.0321(13) . ? Fe1 C2 2.0425(13) . ? Fe1 C8 2.0430(15) . ? Fe1 C9 2.0430(15) . ? Fe1 C10 2.0488(14) . ? Fe1 C7 2.0493(15) . ? Fe1 C6 2.0505(16) . ? Fe1 C4 2.0589(15) . ? Fe1 C3 2.0605(14) . ? O1 C11 1.2277(18) . ? C1 C2 1.436(2) . ? C1 C5 1.439(2) . ? C1 C11 1.453(2) . ? C2 C3 1.413(2) . ? C3 C4 1.428(2) . ? C4 C5 1.419(2) . ? C6 C10 1.411(2) . ? C6 C7 1.411(3) . ? C7 C8 1.420(3) . ? C8 C9 1.420(2) . ? C9 C10 1.417(2) . ? C11 C12 1.461(2) . ? C12 C13 1.185(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 C1 Fe1 C5 41.55(6) . . ? C1 Fe1 C2 41.34(6) . . ? C5 Fe1 C2 69.51(6) . . ? C1 Fe1 C8 157.51(6) . . ? C5 Fe1 C8 158.91(7) . . ? C2 Fe1 C8 120.65(6) . . ? C1 Fe1 C9 160.85(6) . . ? C5 Fe1 C9 123.06(6) . . ? C2 Fe1 C9 156.09(6) . . ? C8 Fe1 C9 40.67(6) . . ? C1 Fe1 C10 124.99(6) . . ? C5 Fe1 C10 108.30(6) . . ? C2 Fe1 C10 161.60(6) . . ? C8 Fe1 C10 68.11(6) . . ? C9 Fe1 C10 40.53(6) . . ? C1 Fe1 C7 122.56(7) . . ? C5 Fe1 C7 159.22(7) . . ? C2 Fe1 C7 107.27(6) . . ? C8 Fe1 C7 40.60(7) . . ? C9 Fe1 C7 68.30(6) . . ? C10 Fe1 C7 67.93(6) . . ? C1 Fe1 C6 109.05(6) . . ? C5 Fe1 C6 123.70(6) . . ? C2 Fe1 C6 124.76(6) . . ? C8 Fe1 C6 67.91(7) . . ? C9 Fe1 C6 67.98(6) . . ? C10 Fe1 C6 40.25(6) . . ? C7 Fe1 C6 40.25(7) . . ? C1 Fe1 C4 68.76(6) . . ? C5 Fe1 C4 40.58(6) . . ? C2 Fe1 C4 68.46(6) . . ? C8 Fe1 C4 122.41(7) . . ? C9 Fe1 C4 106.78(6) . . ? C10 Fe1 C4 122.50(6) . . ? C7 Fe1 C4 158.95(7) . . ? C6 Fe1 C4 158.78(7) . . ? C1 Fe1 C3 68.54(6) . . ? C5 Fe1 C3 68.59(6) . . ? C2 Fe1 C3 40.28(6) . . ? C8 Fe1 C3 106.28(6) . . ? C9 Fe1 C3 120.97(6) . . ? C10 Fe1 C3 157.35(6) . . ? C7 Fe1 C3 123.00(7) . . ? C6 Fe1 C3 159.98(7) . . ? C4 Fe1 C3 40.56(6) . . ? C2 C1 C5 107.79(13) . . ? C2 C1 C11 125.73(13) . . ? C5 C1 C11 125.80(13) . . ? C2 C1 Fe1 69.97(8) . . ? C5 C1 Fe1 69.48(8) . . ? C11 C1 Fe1 118.71(10) . . ? C3 C2 C1 107.74(13) . . ? C3 C2 Fe1 70.55(8) . . ? C1 C2 Fe1 68.69(8) . . ? C2 C3 C4 108.62(13) . . ? C2 C3 Fe1 69.18(8) . . ? C4 C3 Fe1 69.66(8) . . ? C5 C4 C3 108.22(13) . . ? C5 C4 Fe1 68.70(8) . . ? C3 C4 Fe1 69.78(8) . . ? C4 C5 C1 107.62(13) . . ? C4 C5 Fe1 70.73(8) . . ? C1 C5 Fe1 68.98(7) . . ? C10 C6 C7 108.49(15) . . ? C10 C6 Fe1 69.81(9) . . ? C7 C6 Fe1 69.83(9) . . ? C6 C7 C8 107.76(14) . . ? C6 C7 Fe1 69.92(9) . . ? C8 C7 Fe1 69.46(9) . . ? C7 C8 C9 107.97(14) . . ? C7 C8 Fe1 69.94(8) . . ? C9 C8 Fe1 69.66(8) . . ? C10 C9 C8 107.72(14) . . ? C10 C9 Fe1 69.96(8) . . ? C8 C9 Fe1 69.66(9) . . ? C6 C10 C9 108.05(14) . . ? C6 C10 Fe1 69.94(9) . . ? C9 C10 Fe1 69.52(8) . . ? O1 C11 C1 123.59(14) . . ? O1 C11 C12 120.57(14) . . ? C1 C11 C12 115.84(13) . . ? C13 C12 C11 178.41(18) . . ? 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 C5 Fe1 C1 C2 118.93(12) . . . . ? C8 Fe1 C1 C2 -43.3(2) . . . . ? C9 Fe1 C1 C2 161.02(17) . . . . ? C10 Fe1 C1 C2 -163.32(9) . . . . ? C7 Fe1 C1 C2 -78.90(11) . . . . ? C6 Fe1 C1 C2 -121.38(9) . . . . ? C4 Fe1 C1 C2 81.12(9) . . . . ? C3 Fe1 C1 C2 37.42(9) . . . . ? C2 Fe1 C1 C5 -118.93(12) . . . . ? C8 Fe1 C1 C5 -162.18(16) . . . . ? C9 Fe1 C1 C5 42.1(2) . . . . ? C10 Fe1 C1 C5 77.75(10) . . . . ? C7 Fe1 C1 C5 162.17(9) . . . . ? C6 Fe1 C1 C5 119.69(9) . . . . ? C4 Fe1 C1 C5 -37.81(9) . . . . ? C3 Fe1 C1 C5 -81.51(9) . . . . ? C5 Fe1 C1 C11 -120.47(15) . . . . ? C2 Fe1 C1 C11 120.60(15) . . . . ? C8 Fe1 C1 C11 77.3(2) . . . . ? C9 Fe1 C1 C11 -78.4(2) . . . . ? C10 Fe1 C1 C11 -42.72(13) . . . . ? C7 Fe1 C1 C11 41.70(14) . . . . ? C6 Fe1 C1 C11 -0.78(13) . . . . ? C4 Fe1 C1 C11 -158.28(13) . . . . ? C3 Fe1 C1 C11 158.02(13) . . . . ? C5 C1 C2 C3 -0.58(15) . . . . ? C11 C1 C2 C3 -171.56(13) . . . . ? Fe1 C1 C2 C3 -59.99(10) . . . . ? C5 C1 C2 Fe1 59.41(9) . . . . ? C11 C1 C2 Fe1 -111.57(14) . . . . ? C1 Fe1 C2 C3 118.99(12) . . . . ? C5 Fe1 C2 C3 80.70(9) . . . . ? C8 Fe1 C2 C3 -78.74(10) . . . . ? C9 Fe1 C2 C3 -45.74(18) . . . . ? C10 Fe1 C2 C3 167.16(16) . . . . ? C7 Fe1 C2 C3 -121.02(10) . . . . ? C6 Fe1 C2 C3 -161.81(9) . . . . ? C4 Fe1 C2 C3 37.10(8) . . . . ? C5 Fe1 C2 C1 -38.30(8) . . . . ? C8 Fe1 C2 C1 162.26(9) . . . . ? C9 Fe1 C2 C1 -164.73(13) . . . . ? C10 Fe1 C2 C1 48.2(2) . . . . ? C7 Fe1 C2 C1 119.99(10) . . . . ? C6 Fe1 C2 C1 79.20(10) . . . . ? C4 Fe1 C2 C1 -81.89(9) . . . . ? C3 Fe1 C2 C1 -118.99(12) . . . . ? C1 C2 C3 C4 0.20(16) . . . . ? Fe1 C2 C3 C4 -58.62(10) . . . . ? C1 C2 C3 Fe1 58.82(9) . . . . ? C1 Fe1 C3 C2 -38.37(8) . . . . ? C5 Fe1 C3 C2 -83.17(9) . . . . ? C8 Fe1 C3 C2 118.48(9) . . . . ? C9 Fe1 C3 C2 160.21(8) . . . . ? C10 Fe1 C3 C2 -169.51(13) . . . . ? C7 Fe1 C3 C2 77.37(11) . . . . ? C6 Fe1 C3 C2 48.5(2) . . . . ? C4 Fe1 C3 C2 -120.36(12) . . . . ? C1 Fe1 C3 C4 81.99(9) . . . . ? C5 Fe1 C3 C4 37.19(9) . . . . ? C2 Fe1 C3 C4 120.36(12) . . . . ? C8 Fe1 C3 C4 -121.16(9) . . . . ? C9 Fe1 C3 C4 -79.43(10) . . . . ? C10 Fe1 C3 C4 -49.15(18) . . . . ? C7 Fe1 C3 C4 -162.28(9) . . . . ? C6 Fe1 C3 C4 168.87(16) . . . . ? C2 C3 C4 C5 0.26(16) . . . . ? Fe1 C3 C4 C5 -58.07(10) . . . . ? C2 C3 C4 Fe1 58.33(10) . . . . ? C1 Fe1 C4 C5 38.69(9) . . . . ? C2 Fe1 C4 C5 83.24(9) . . . . ? C8 Fe1 C4 C5 -163.27(9) . . . . ? C9 Fe1 C4 C5 -121.59(9) . . . . ? C10 Fe1 C4 C5 -80.12(10) . . . . ? C7 Fe1 C4 C5 165.38(16) . . . . ? C6 Fe1 C4 C5 -49.4(2) . . . . ? C3 Fe1 C4 C5 120.09(13) . . . . ? C1 Fe1 C4 C3 -81.40(9) . . . . ? C5 Fe1 C4 C3 -120.09(13) . . . . ? C2 Fe1 C4 C3 -36.85(9) . . . . ? C8 Fe1 C4 C3 76.64(11) . . . . ? C9 Fe1 C4 C3 118.32(9) . . . . ? C10 Fe1 C4 C3 159.79(9) . . . . ? C7 Fe1 C4 C3 45.3(2) . . . . ? C6 Fe1 C4 C3 -169.48(16) . . . . ? C3 C4 C5 C1 -0.61(16) . . . . ? Fe1 C4 C5 C1 -59.35(9) . . . . ? C3 C4 C5 Fe1 58.74(10) . . . . ? C2 C1 C5 C4 0.74(15) . . . . ? C11 C1 C5 C4 171.71(13) . . . . ? Fe1 C1 C5 C4 60.46(10) . . . . ? C2 C1 C5 Fe1 -59.73(9) . . . . ? C11 C1 C5 Fe1 111.25(14) . . . . ? C1 Fe1 C5 C4 -118.54(12) . . . . ? C2 Fe1 C5 C4 -80.44(9) . . . . ? C8 Fe1 C5 C4 42.5(2) . . . . ? C9 Fe1 C5 C4 76.67(10) . . . . ? C10 Fe1 C5 C4 118.94(9) . . . . ? C7 Fe1 C5 C4 -165.20(16) . . . . ? C6 Fe1 C5 C4 160.72(9) . . . . ? C3 Fe1 C5 C4 -37.18(9) . . . . ? C2 Fe1 C5 C1 38.11(9) . . . . ? C8 Fe1 C5 C1 161.02(16) . . . . ? C9 Fe1 C5 C1 -164.79(9) . . . . ? C10 Fe1 C5 C1 -122.52(9) . . . . ? C7 Fe1 C5 C1 -46.7(2) . . . . ? C6 Fe1 C5 C1 -80.74(10) . . . . ? C4 Fe1 C5 C1 118.54(12) . . . . ? C3 Fe1 C5 C1 81.36(9) . . . . ? C1 Fe1 C6 C10 -122.07(9) . . . . ? C5 Fe1 C6 C10 -78.24(11) . . . . ? C2 Fe1 C6 C10 -165.42(8) . . . . ? C8 Fe1 C6 C10 81.75(10) . . . . ? C9 Fe1 C6 C10 37.71(9) . . . . ? C7 Fe1 C6 C10 119.68(14) . . . . ? C4 Fe1 C6 C10 -41.8(2) . . . . ? C3 Fe1 C6 C10 158.46(16) . . . . ? C1 Fe1 C6 C7 118.25(10) . . . . ? C5 Fe1 C6 C7 162.08(9) . . . . ? C2 Fe1 C6 C7 74.90(11) . . . . ? C8 Fe1 C6 C7 -37.93(10) . . . . ? C9 Fe1 C6 C7 -81.98(10) . . . . ? C10 Fe1 C6 C7 -119.68(14) . . . . ? C4 Fe1 C6 C7 -161.51(16) . . . . ? C3 Fe1 C6 C7 38.8(2) . . . . ? C10 C6 C7 C8 0.08(17) . . . . ? Fe1 C6 C7 C8 59.38(11) . . . . ? C10 C6 C7 Fe1 -59.29(10) . . . . ? C1 Fe1 C7 C6 -81.09(11) . . . . ? C5 Fe1 C7 C6 -46.2(2) . . . . ? C2 Fe1 C7 C6 -123.84(10) . . . . ? C8 Fe1 C7 C6 118.93(13) . . . . ? C9 Fe1 C7 C6 81.11(10) . . . . ? C10 Fe1 C7 C6 37.28(9) . . . . ? C4 Fe1 C7 C6 161.37(16) . . . . ? C3 Fe1 C7 C6 -165.19(9) . . . . ? C1 Fe1 C7 C8 159.97(9) . . . . ? C5 Fe1 C7 C8 -165.12(15) . . . . ? C2 Fe1 C7 C8 117.23(9) . . . . ? C9 Fe1 C7 C8 -37.82(9) . . . . ? C10 Fe1 C7 C8 -81.65(10) . . . . ? C6 Fe1 C7 C8 -118.93(13) . . . . ? C4 Fe1 C7 C8 42.4(2) . . . . ? C3 Fe1 C7 C8 75.88(11) . . . . ? C6 C7 C8 C9 -0.16(17) . . . . ? Fe1 C7 C8 C9 59.51(10) . . . . ? C6 C7 C8 Fe1 -59.67(10) . . . . ? C1 Fe1 C8 C7 -49.0(2) . . . . ? C5 Fe1 C8 C7 165.33(16) . . . . ? C2 Fe1 C8 C7 -80.74(11) . . . . ? C9 Fe1 C8 C7 119.06(13) . . . . ? C10 Fe1 C8 C7 81.17(10) . . . . ? C6 Fe1 C8 C7 37.61(10) . . . . ? C4 Fe1 C8 C7 -163.31(9) . . . . ? C3 Fe1 C8 C7 -122.08(10) . . . . ? C1 Fe1 C8 C9 -168.06(14) . . . . ? C5 Fe1 C8 C9 46.3(2) . . . . ? C2 Fe1 C8 C9 160.20(9) . . . . ? C10 Fe1 C8 C9 -37.88(9) . . . . ? C7 Fe1 C8 C9 -119.06(13) . . . . ? C6 Fe1 C8 C9 -81.45(10) . . . . ? C4 Fe1 C8 C9 77.63(11) . . . . ? C3 Fe1 C8 C9 118.86(10) . . . . ? C7 C8 C9 C10 0.18(17) . . . . ? Fe1 C8 C9 C10 59.86(10) . . . . ? C7 C8 C9 Fe1 -59.68(10) . . . . ? C1 Fe1 C9 C10 47.3(2) . . . . ? C5 Fe1 C9 C10 79.34(10) . . . . ? C2 Fe1 C9 C10 -164.71(14) . . . . ? C8 Fe1 C9 C10 -118.74(13) . . . . ? C7 Fe1 C9 C10 -80.98(10) . . . . ? C6 Fe1 C9 C10 -37.46(9) . . . . ? C4 Fe1 C9 C10 120.72(9) . . . . ? C3 Fe1 C9 C10 162.61(8) . . . . ? C1 Fe1 C9 C8 166.04(17) . . . . ? C5 Fe1 C9 C8 -161.92(10) . . . . ? C2 Fe1 C9 C8 -45.97(19) . . . . ? C10 Fe1 C9 C8 118.74(13) . . . . ? C7 Fe1 C9 C8 37.76(10) . . . . ? C6 Fe1 C9 C8 81.28(11) . . . . ? C4 Fe1 C9 C8 -120.54(10) . . . . ? C3 Fe1 C9 C8 -78.65(11) . . . . ? C7 C6 C10 C9 0.03(17) . . . . ? Fe1 C6 C10 C9 -59.28(10) . . . . ? C7 C6 C10 Fe1 59.31(11) . . . . ? C8 C9 C10 C6 -0.13(17) . . . . ? Fe1 C9 C10 C6 59.54(10) . . . . ? C8 C9 C10 Fe1 -59.67(10) . . . . ? C1 Fe1 C10 C6 77.87(11) . . . . ? C5 Fe1 C10 C6 120.92(10) . . . . ? C2 Fe1 C10 C6 41.0(2) . . . . ? C8 Fe1 C10 C6 -81.23(11) . . . . ? C9 Fe1 C10 C6 -119.25(13) . . . . ? C7 Fe1 C10 C6 -37.28(10) . . . . ? C4 Fe1 C10 C6 163.37(9) . . . . ? C3 Fe1 C10 C6 -160.95(14) . . . . ? C1 Fe1 C10 C9 -162.88(8) . . . . ? C5 Fe1 C10 C9 -119.83(9) . . . . ? C2 Fe1 C10 C9 160.20(17) . . . . ? C8 Fe1 C10 C9 38.02(9) . . . . ? C7 Fe1 C10 C9 81.96(10) . . . . ? C6 Fe1 C10 C9 119.25(13) . . . . ? C4 Fe1 C10 C9 -77.38(10) . . . . ? C3 Fe1 C10 C9 -41.71(18) . . . . ? C2 C1 C11 O1 -13.0(2) . . . . ? C5 C1 C11 O1 177.65(13) . . . . ? Fe1 C1 C11 O1 -97.97(15) . . . . ? C2 C1 C11 C12 167.23(13) . . . . ? C5 C1 C11 C12 -2.2(2) . . . . ? Fe1 C1 C11 C12 82.22(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.045 data_2b _database_code_depnum_ccdc_archive 'CCDC 839180' #TrackingRef 'web_deposit_cif_file_0_KrzysztofWozniak_1313347883.CIF_sum.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Fe O' _chemical_formula_weight 252.09 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)/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 5.8159(4) _cell_length_b 18.8274(15) _cell_length_c 10.1737(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.450(2) _cell_angle_gamma 90.00 _cell_volume 1112.98(15) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 520 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.50 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.327 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.831 _exptl_absorpt_process_details 'Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_monochromator 'mutli-layer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13021 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2567 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0325P)^2^+0.5946P] 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 2567 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.71609(4) 0.169914(12) 0.36434(2) 0.01161(8) Uani 1 1 d . . . O1 O 0.2694(2) 0.11730(7) 0.09437(12) 0.0208(3) Uani 1 1 d . . . C1 C 0.5646(3) 0.19033(9) 0.18492(15) 0.0135(3) Uani 1 1 d . . . C2 C 0.4373(3) 0.22350(9) 0.28567(16) 0.0151(3) Uani 1 1 d . . . H2 H 0.2726 0.2143 0.3045 0.018 Uiso 1 1 calc R . . C3 C 0.5869(3) 0.27188(9) 0.35391(16) 0.0157(3) Uani 1 1 d . . . H3 H 0.5464 0.3020 0.4305 0.019 Uiso 1 1 calc R . . C4 C 0.8065(3) 0.26864(9) 0.29703(16) 0.0154(3) Uani 1 1 d . . . H4 H 0.9461 0.2962 0.3269 0.018 Uiso 1 1 calc R . . C5 C 0.7954(3) 0.21797(9) 0.19308(15) 0.0145(3) Uani 1 1 d . . . H5 H 0.9236 0.2046 0.1355 0.017 Uiso 1 1 calc R . . C6 C 0.7379(3) 0.06187(9) 0.38693(17) 0.0187(4) Uani 1 1 d . . . H6 H 0.6865 0.0256 0.3202 0.022 Uiso 1 1 calc R . . C7 C 0.6007(3) 0.09166(10) 0.48508(17) 0.0197(4) Uani 1 1 d . . . H7 H 0.4360 0.0800 0.4996 0.024 Uiso 1 1 calc R . . C8 C 0.7376(3) 0.14140(10) 0.55846(16) 0.0191(4) Uani 1 1 d . . . H8 H 0.6864 0.1707 0.6338 0.023 Uiso 1 1 calc R . . C9 C 0.9602(3) 0.14230(10) 0.50586(16) 0.0177(4) Uani 1 1 d . . . H9 H 1.0929 0.1724 0.5377 0.021 Uiso 1 1 calc R . . C10 C 0.9610(3) 0.09306(9) 0.39931(16) 0.0171(3) Uani 1 1 d . . . H10 H 1.0939 0.0824 0.3433 0.020 Uiso 1 1 calc R . . C11 C 0.4732(3) 0.13487(9) 0.09613(16) 0.0150(3) Uani 1 1 d . . . C12 C 0.6331(3) 0.10250(9) 0.00816(16) 0.0161(3) Uani 1 1 d . . . C13 C 0.7662(3) 0.07639(9) -0.06404(16) 0.0167(3) Uani 1 1 d . . . C14 C 0.9326(3) 0.04403(10) -0.14946(16) 0.0198(4) Uani 1 1 d . . . H14A H 1.0881 0.0596 -0.1222 0.030 Uiso 1 1 calc R . . H14B H 0.8981 0.0585 -0.2407 0.030 Uiso 1 1 calc R . . H14C H 0.9230 -0.0078 -0.1428 0.030 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 0.00956(13) 0.01340(13) 0.01190(12) 0.00010(8) 0.00093(8) 0.00075(9) O1 0.0132(6) 0.0243(7) 0.0249(6) -0.0010(5) -0.0017(5) -0.0028(5) C1 0.0115(8) 0.0154(8) 0.0134(7) 0.0032(6) -0.0002(6) 0.0003(6) C2 0.0124(8) 0.0170(8) 0.0160(7) 0.0030(6) 0.0022(6) 0.0033(7) C3 0.0175(8) 0.0144(8) 0.0152(7) 0.0014(6) 0.0035(6) 0.0038(7) C4 0.0153(8) 0.0152(8) 0.0158(7) 0.0016(6) 0.0016(6) -0.0013(7) C5 0.0129(8) 0.0165(8) 0.0143(7) 0.0017(6) 0.0014(6) -0.0004(7) C6 0.0191(9) 0.0143(8) 0.0221(8) 0.0020(6) -0.0034(7) 0.0003(7) C7 0.0156(9) 0.0206(9) 0.0231(8) 0.0093(7) 0.0027(7) 0.0005(7) C8 0.0217(9) 0.0222(9) 0.0137(8) 0.0038(6) 0.0020(6) 0.0054(8) C9 0.0159(9) 0.0187(9) 0.0179(8) 0.0003(6) -0.0041(6) 0.0031(7) C10 0.0140(8) 0.0174(9) 0.0197(8) -0.0001(6) -0.0012(6) 0.0046(7) C11 0.0139(8) 0.0163(9) 0.0147(7) 0.0041(6) -0.0015(6) 0.0000(7) C12 0.0158(8) 0.0159(8) 0.0164(7) 0.0010(6) -0.0039(6) -0.0019(7) C13 0.0196(9) 0.0144(8) 0.0158(7) 0.0015(6) -0.0027(6) -0.0014(7) C14 0.0236(9) 0.0183(9) 0.0178(8) -0.0013(7) 0.0037(7) 0.0028(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 C1 2.0293(15) . ? Fe1 C5 2.0336(16) . ? Fe1 C2 2.0437(16) . ? Fe1 C8 2.0453(16) . ? Fe1 C9 2.0456(16) . ? Fe1 C7 2.0495(17) . ? Fe1 C10 2.0506(17) . ? Fe1 C6 2.0505(18) . ? Fe1 C4 2.0570(17) . ? Fe1 C3 2.0628(17) . ? O1 C11 1.230(2) . ? C1 C2 1.433(2) . ? C1 C5 1.438(2) . ? C1 C11 1.466(2) . ? C2 C3 1.420(2) . ? C3 C4 1.426(2) . ? C4 C5 1.424(2) . ? C6 C7 1.420(3) . ? C6 C10 1.425(2) . ? C7 C8 1.420(3) . ? C8 C9 1.422(2) . ? C9 C10 1.427(2) . ? C11 C12 1.452(2) . ? C12 C13 1.196(2) . ? C13 C14 1.461(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 C1 Fe1 C5 41.47(6) . . ? C1 Fe1 C2 41.20(6) . . ? C5 Fe1 C2 69.51(7) . . ? C1 Fe1 C8 157.61(7) . . ? C5 Fe1 C8 159.60(7) . . ? C2 Fe1 C8 121.51(7) . . ? C1 Fe1 C9 160.53(7) . . ? C5 Fe1 C9 122.69(7) . . ? C2 Fe1 C9 156.39(7) . . ? C8 Fe1 C9 40.68(7) . . ? C1 Fe1 C7 122.32(7) . . ? C5 Fe1 C7 157.73(7) . . ? C2 Fe1 C7 108.36(7) . . ? C8 Fe1 C7 40.59(7) . . ? C9 Fe1 C7 68.32(7) . . ? C1 Fe1 C10 124.15(7) . . ? C5 Fe1 C10 106.34(7) . . ? C2 Fe1 C10 161.77(7) . . ? C8 Fe1 C10 68.52(7) . . ? C9 Fe1 C10 40.76(7) . . ? C7 Fe1 C10 68.38(7) . . ? C1 Fe1 C6 108.13(7) . . ? C5 Fe1 C6 121.48(7) . . ? C2 Fe1 C6 125.31(7) . . ? C8 Fe1 C6 68.31(7) . . ? C9 Fe1 C6 68.36(7) . . ? C7 Fe1 C6 40.53(7) . . ? C10 Fe1 C6 40.65(7) . . ? C1 Fe1 C4 68.69(7) . . ? C5 Fe1 C4 40.73(6) . . ? C2 Fe1 C4 68.49(7) . . ? C8 Fe1 C4 123.55(7) . . ? C9 Fe1 C4 106.52(7) . . ? C7 Fe1 C4 160.74(7) . . ? C10 Fe1 C4 120.66(7) . . ? C6 Fe1 C4 156.68(7) . . ? C1 Fe1 C3 68.54(7) . . ? C5 Fe1 C3 68.73(7) . . ? C2 Fe1 C3 40.46(7) . . ? C8 Fe1 C3 107.53(7) . . ? C9 Fe1 C3 120.87(7) . . ? C7 Fe1 C3 124.88(7) . . ? C10 Fe1 C3 156.13(7) . . ? C6 Fe1 C3 161.76(7) . . ? C4 Fe1 C3 40.50(7) . . ? C2 C1 C5 108.09(14) . . ? C2 C1 C11 124.50(15) . . ? C5 C1 C11 127.31(15) . . ? C2 C1 Fe1 69.94(9) . . ? C5 C1 Fe1 69.42(9) . . ? C11 C1 Fe1 123.47(12) . . ? C3 C2 C1 107.74(14) . . ? C3 C2 Fe1 70.49(9) . . ? C1 C2 Fe1 68.86(9) . . ? C2 C3 C4 108.34(14) . . ? C2 C3 Fe1 69.05(9) . . ? C4 C3 Fe1 69.53(9) . . ? C5 C4 C3 108.49(15) . . ? C5 C4 Fe1 68.75(9) . . ? C3 C4 Fe1 69.97(9) . . ? C4 C5 C1 107.33(15) . . ? C4 C5 Fe1 70.52(9) . . ? C1 C5 Fe1 69.11(9) . . ? C7 C6 C10 108.17(16) . . ? C7 C6 Fe1 69.69(10) . . ? C10 C6 Fe1 69.68(10) . . ? C8 C7 C6 108.10(16) . . ? C8 C7 Fe1 69.54(10) . . ? C6 C7 Fe1 69.77(10) . . ? C7 C8 C9 108.01(15) . . ? C7 C8 Fe1 69.86(9) . . ? C9 C8 Fe1 69.67(9) . . ? C8 C9 C10 108.09(15) . . ? C8 C9 Fe1 69.65(9) . . ? C10 C9 Fe1 69.81(9) . . ? C6 C10 C9 107.63(15) . . ? C6 C10 Fe1 69.67(10) . . ? C9 C10 Fe1 69.43(10) . . ? O1 C11 C12 121.34(15) . . ? O1 C11 C1 121.63(16) . . ? C12 C11 C1 117.01(15) . . ? C13 C12 C11 179.33(19) . . ? C12 C13 C14 178.60(18) . . ? 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 C5 Fe1 C1 C2 -119.35(14) . . . . ? C8 Fe1 C1 C2 46.4(2) . . . . ? C9 Fe1 C1 C2 -160.45(19) . . . . ? C7 Fe1 C1 C2 80.98(12) . . . . ? C10 Fe1 C1 C2 165.37(10) . . . . ? C6 Fe1 C1 C2 123.32(10) . . . . ? C4 Fe1 C1 C2 -81.25(11) . . . . ? C3 Fe1 C1 C2 -37.61(10) . . . . ? C2 Fe1 C1 C5 119.35(14) . . . . ? C8 Fe1 C1 C5 165.73(17) . . . . ? C9 Fe1 C1 C5 -41.1(2) . . . . ? C7 Fe1 C1 C5 -159.68(10) . . . . ? C10 Fe1 C1 C5 -75.29(12) . . . . ? C6 Fe1 C1 C5 -117.34(10) . . . . ? C4 Fe1 C1 C5 38.09(10) . . . . ? C3 Fe1 C1 C5 81.74(11) . . . . ? C5 Fe1 C1 C11 121.87(18) . . . . ? C2 Fe1 C1 C11 -118.78(18) . . . . ? C8 Fe1 C1 C11 -72.4(2) . . . . ? C9 Fe1 C1 C11 80.8(3) . . . . ? C7 Fe1 C1 C11 -37.81(17) . . . . ? C10 Fe1 C1 C11 46.59(17) . . . . ? C6 Fe1 C1 C11 4.53(16) . . . . ? C4 Fe1 C1 C11 159.96(16) . . . . ? C3 Fe1 C1 C11 -156.39(16) . . . . ? C5 C1 C2 C3 0.88(18) . . . . ? C11 C1 C2 C3 177.50(15) . . . . ? Fe1 C1 C2 C3 60.03(11) . . . . ? C5 C1 C2 Fe1 -59.15(11) . . . . ? C11 C1 C2 Fe1 117.48(16) . . . . ? C1 Fe1 C2 C3 -118.92(14) . . . . ? C5 Fe1 C2 C3 -80.88(10) . . . . ? C8 Fe1 C2 C3 79.96(12) . . . . ? C9 Fe1 C2 C3 44.9(2) . . . . ? C7 Fe1 C2 C3 122.65(10) . . . . ? C10 Fe1 C2 C3 -160.8(2) . . . . ? C6 Fe1 C2 C3 164.38(10) . . . . ? C4 Fe1 C2 C3 -37.12(9) . . . . ? C5 Fe1 C2 C1 38.04(10) . . . . ? C8 Fe1 C2 C1 -161.13(10) . . . . ? C9 Fe1 C2 C1 163.83(16) . . . . ? C7 Fe1 C2 C1 -118.43(10) . . . . ? C10 Fe1 C2 C1 -41.9(3) . . . . ? C6 Fe1 C2 C1 -76.70(12) . . . . ? C4 Fe1 C2 C1 81.80(10) . . . . ? C3 Fe1 C2 C1 118.92(14) . . . . ? C1 C2 C3 C4 -0.43(18) . . . . ? Fe1 C2 C3 C4 58.57(11) . . . . ? C1 C2 C3 Fe1 -59.00(11) . . . . ? C1 Fe1 C3 C2 38.28(9) . . . . ? C5 Fe1 C3 C2 82.96(10) . . . . ? C8 Fe1 C3 C2 -118.31(10) . . . . ? C9 Fe1 C3 C2 -160.77(10) . . . . ? C7 Fe1 C3 C2 -76.95(12) . . . . ? C10 Fe1 C3 C2 165.30(15) . . . . ? C6 Fe1 C3 C2 -44.6(2) . . . . ? C4 Fe1 C3 C2 120.18(13) . . . . ? C1 Fe1 C3 C4 -81.90(10) . . . . ? C5 Fe1 C3 C4 -37.21(9) . . . . ? C2 Fe1 C3 C4 -120.18(13) . . . . ? C8 Fe1 C3 C4 121.51(10) . . . . ? C9 Fe1 C3 C4 79.06(11) . . . . ? C7 Fe1 C3 C4 162.87(10) . . . . ? C10 Fe1 C3 C4 45.1(2) . . . . ? C6 Fe1 C3 C4 -164.75(19) . . . . ? C2 C3 C4 C5 -0.18(18) . . . . ? Fe1 C3 C4 C5 58.09(11) . . . . ? C2 C3 C4 Fe1 -58.27(11) . . . . ? C1 Fe1 C4 C5 -38.77(10) . . . . ? C2 Fe1 C4 C5 -83.17(11) . . . . ? C8 Fe1 C4 C5 162.46(10) . . . . ? C9 Fe1 C4 C5 121.27(10) . . . . ? C7 Fe1 C4 C5 -167.34(19) . . . . ? C10 Fe1 C4 C5 79.22(11) . . . . ? C6 Fe1 C4 C5 47.7(2) . . . . ? C3 Fe1 C4 C5 -120.26(14) . . . . ? C1 Fe1 C4 C3 81.49(10) . . . . ? C5 Fe1 C4 C3 120.26(14) . . . . ? C2 Fe1 C4 C3 37.08(9) . . . . ? C8 Fe1 C4 C3 -77.29(11) . . . . ? C9 Fe1 C4 C3 -118.48(10) . . . . ? C7 Fe1 C4 C3 -47.1(2) . . . . ? C10 Fe1 C4 C3 -160.53(9) . . . . ? C6 Fe1 C4 C3 168.00(15) . . . . ? C3 C4 C5 C1 0.72(18) . . . . ? Fe1 C4 C5 C1 59.56(11) . . . . ? C3 C4 C5 Fe1 -58.83(11) . . . . ? C2 C1 C5 C4 -0.99(18) . . . . ? C11 C1 C5 C4 -177.49(15) . . . . ? Fe1 C1 C5 C4 -60.46(11) . . . . ? C2 C1 C5 Fe1 59.47(11) . . . . ? C11 C1 C5 Fe1 -117.03(17) . . . . ? C1 Fe1 C5 C4 118.25(14) . . . . ? C2 Fe1 C5 C4 80.45(11) . . . . ? C8 Fe1 C5 C4 -46.1(2) . . . . ? C9 Fe1 C5 C4 -76.84(12) . . . . ? C7 Fe1 C5 C4 169.00(16) . . . . ? C10 Fe1 C5 C4 -118.28(10) . . . . ? C6 Fe1 C5 C4 -159.90(10) . . . . ? C3 Fe1 C5 C4 37.01(10) . . . . ? C2 Fe1 C5 C1 -37.80(10) . . . . ? C8 Fe1 C5 C1 -164.37(18) . . . . ? C9 Fe1 C5 C1 164.91(10) . . . . ? C7 Fe1 C5 C1 50.8(2) . . . . ? C10 Fe1 C5 C1 123.47(10) . . . . ? C6 Fe1 C5 C1 81.85(11) . . . . ? C4 Fe1 C5 C1 -118.25(14) . . . . ? C3 Fe1 C5 C1 -81.24(11) . . . . ? C1 Fe1 C6 C7 -118.86(11) . . . . ? C5 Fe1 C6 C7 -162.47(10) . . . . ? C2 Fe1 C6 C7 -76.45(12) . . . . ? C8 Fe1 C6 C7 37.60(10) . . . . ? C9 Fe1 C6 C7 81.52(11) . . . . ? C10 Fe1 C6 C7 119.45(14) . . . . ? C4 Fe1 C6 C7 163.04(15) . . . . ? C3 Fe1 C6 C7 -42.5(2) . . . . ? C1 Fe1 C6 C10 121.69(10) . . . . ? C5 Fe1 C6 C10 78.08(11) . . . . ? C2 Fe1 C6 C10 164.10(10) . . . . ? C8 Fe1 C6 C10 -81.85(11) . . . . ? C9 Fe1 C6 C10 -37.93(10) . . . . ? C7 Fe1 C6 C10 -119.45(14) . . . . ? C4 Fe1 C6 C10 43.6(2) . . . . ? C3 Fe1 C6 C10 -161.97(19) . . . . ? C10 C6 C7 C8 0.07(19) . . . . ? Fe1 C6 C7 C8 -59.19(12) . . . . ? C10 C6 C7 Fe1 59.25(12) . . . . ? C1 Fe1 C7 C8 -160.59(10) . . . . ? C5 Fe1 C7 C8 162.05(16) . . . . ? C2 Fe1 C7 C8 -117.32(11) . . . . ? C9 Fe1 C7 C8 37.77(10) . . . . ? C10 Fe1 C7 C8 81.79(11) . . . . ? C6 Fe1 C7 C8 119.39(15) . . . . ? C4 Fe1 C7 C8 -40.1(3) . . . . ? C3 Fe1 C7 C8 -75.55(12) . . . . ? C1 Fe1 C7 C6 80.03(12) . . . . ? C5 Fe1 C7 C6 42.7(2) . . . . ? C2 Fe1 C7 C6 123.29(10) . . . . ? C8 Fe1 C7 C6 -119.39(15) . . . . ? C9 Fe1 C7 C6 -81.61(11) . . . . ? C10 Fe1 C7 C6 -37.60(10) . . . . ? C4 Fe1 C7 C6 -159.50(19) . . . . ? C3 Fe1 C7 C6 165.06(10) . . . . ? C6 C7 C8 C9 -0.12(19) . . . . ? Fe1 C7 C8 C9 -59.45(12) . . . . ? C6 C7 C8 Fe1 59.33(12) . . . . ? C1 Fe1 C8 C7 47.5(2) . . . . ? C5 Fe1 C8 C7 -160.42(18) . . . . ? C2 Fe1 C8 C7 81.52(12) . . . . ? C9 Fe1 C8 C7 -119.15(15) . . . . ? C10 Fe1 C8 C7 -81.42(11) . . . . ? C6 Fe1 C8 C7 -37.55(10) . . . . ? C4 Fe1 C8 C7 165.22(10) . . . . ? C3 Fe1 C8 C7 123.59(11) . . . . ? C1 Fe1 C8 C9 166.65(16) . . . . ? C5 Fe1 C8 C9 -41.3(2) . . . . ? C2 Fe1 C8 C9 -159.34(10) . . . . ? C7 Fe1 C8 C9 119.15(15) . . . . ? C10 Fe1 C8 C9 37.73(10) . . . . ? C6 Fe1 C8 C9 81.60(11) . . . . ? C4 Fe1 C8 C9 -75.63(12) . . . . ? C3 Fe1 C8 C9 -117.27(11) . . . . ? C7 C8 C9 C10 0.13(19) . . . . ? Fe1 C8 C9 C10 -59.44(12) . . . . ? C7 C8 C9 Fe1 59.57(12) . . . . ? C1 Fe1 C9 C8 -164.70(19) . . . . ? C5 Fe1 C9 C8 164.15(10) . . . . ? C2 Fe1 C9 C8 48.7(2) . . . . ? C7 Fe1 C9 C8 -37.70(11) . . . . ? C10 Fe1 C9 C8 -119.29(15) . . . . ? C6 Fe1 C9 C8 -81.47(11) . . . . ? C4 Fe1 C9 C8 122.64(11) . . . . ? C3 Fe1 C9 C8 80.95(12) . . . . ? C1 Fe1 C9 C10 -45.4(3) . . . . ? C5 Fe1 C9 C10 -76.56(12) . . . . ? C2 Fe1 C9 C10 167.98(16) . . . . ? C8 Fe1 C9 C10 119.29(15) . . . . ? C7 Fe1 C9 C10 81.59(11) . . . . ? C6 Fe1 C9 C10 37.83(10) . . . . ? C4 Fe1 C9 C10 -118.07(11) . . . . ? C3 Fe1 C9 C10 -159.76(10) . . . . ? C7 C6 C10 C9 0.01(19) . . . . ? Fe1 C6 C10 C9 59.28(12) . . . . ? C7 C6 C10 Fe1 -59.26(12) . . . . ? C8 C9 C10 C6 -0.09(19) . . . . ? Fe1 C9 C10 C6 -59.43(12) . . . . ? C8 C9 C10 Fe1 59.34(12) . . . . ? C1 Fe1 C10 C6 -77.72(12) . . . . ? C5 Fe1 C10 C6 -119.59(10) . . . . ? C2 Fe1 C10 C6 -45.6(3) . . . . ? C8 Fe1 C10 C6 81.30(11) . . . . ? C9 Fe1 C10 C6 118.95(15) . . . . ? C7 Fe1 C10 C6 37.50(10) . . . . ? C4 Fe1 C10 C6 -161.50(10) . . . . ? C3 Fe1 C10 C6 166.15(15) . . . . ? C1 Fe1 C10 C9 163.33(10) . . . . ? C5 Fe1 C10 C9 121.46(11) . . . . ? C2 Fe1 C10 C9 -164.5(2) . . . . ? C8 Fe1 C10 C9 -37.65(11) . . . . ? C7 Fe1 C10 C9 -81.45(11) . . . . ? C6 Fe1 C10 C9 -118.95(15) . . . . ? C4 Fe1 C10 C9 79.55(12) . . . . ? C3 Fe1 C10 C9 47.2(2) . . . . ? C2 C1 C11 O1 6.9(3) . . . . ? C5 C1 C11 O1 -177.12(16) . . . . ? Fe1 C1 C11 O1 94.36(18) . . . . ? C2 C1 C11 C12 -174.34(15) . . . . ? C5 C1 C11 C12 1.6(2) . . . . ? Fe1 C1 C11 C12 -86.89(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.482 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.065 data_2c _database_code_depnum_ccdc_archive 'CCDC 839181' #TrackingRef 'web_deposit_cif_file_0_KrzysztofWozniak_1313347883.CIF_sum.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Fe O Si' _chemical_formula_weight 310.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Si Si 0.0817 0.0704 '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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 25.3890(9) _cell_length_b 10.1455(4) _cell_length_c 5.8173(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1498.44(9) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 28.37 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_monochromator 'mutli-layer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12979 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3660 _reflns_number_gt 3482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0422P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.185(14) _refine_ls_number_reflns 3660 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _refine_ls_shift/su_max 0.003 _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 0.693258(9) 0.27101(2) 0.74153(5) 0.01016(8) Uani 1 1 d . . . Si2 Si 0.55626(2) 0.73911(5) 0.47223(12) 0.01584(14) Uani 1 1 d . . . O1 O 0.65436(6) 0.54033(14) 1.1755(3) 0.0189(3) Uani 1 1 d . . . C1 C 0.70740(8) 0.44995(19) 0.8827(4) 0.0117(4) Uani 1 1 d . . . C2 C 0.72711(7) 0.44415(18) 0.6512(4) 0.0120(4) Uani 1 1 d . . . H2 H 0.7168 0.5012 0.5229 0.014 Uiso 1 1 calc R . . C3 C 0.76596(7) 0.34176(18) 0.6457(4) 0.0133(4) Uani 1 1 d . . . H3 H 0.7860 0.3140 0.5102 0.016 Uiso 1 1 calc R . . C4 C 0.76919(8) 0.28405(18) 0.8686(4) 0.0137(4) Uani 1 1 d . . . H4 H 0.7916 0.2094 0.9115 0.016 Uiso 1 1 calc R . . C5 C 0.73339(7) 0.34922(17) 1.0151(4) 0.0129(4) Uani 1 1 d . . . H5 H 0.7272 0.3292 1.1777 0.016 Uiso 1 1 calc R . . C6 C 0.61339(7) 0.24716(18) 0.7292(5) 0.0191(4) Uani 1 1 d . . . H6 H 0.5872 0.3104 0.7854 0.023 Uiso 1 1 calc R . . C7 C 0.63493(8) 0.24409(19) 0.5043(5) 0.0174(4) Uani 1 1 d . . . H7 H 0.6261 0.3037 0.3776 0.021 Uiso 1 1 calc R . . C8 C 0.67169(8) 0.1380(2) 0.4964(4) 0.0171(4) Uani 1 1 d . . . H8 H 0.6928 0.1121 0.3627 0.021 Uiso 1 1 calc R . . C9 C 0.67237(7) 0.07624(18) 0.7151(4) 0.0165(4) Uani 1 1 d . . . H9 H 0.6942 0.0008 0.7591 0.020 Uiso 1 1 calc R . . C10 C 0.63636(8) 0.1437(2) 0.8599(4) 0.0191(4) Uani 1 1 d . . . H10 H 0.6289 0.1231 1.0213 0.023 Uiso 1 1 calc R . . C11 C 0.66450(7) 0.53173(18) 0.9699(4) 0.0133(4) Uani 1 1 d . . . C12 C 0.63270(8) 0.60359(19) 0.8023(3) 0.0149(4) Uani 1 1 d . . . C13 C 0.60408(8) 0.6598(2) 0.6693(4) 0.0175(4) Uani 1 1 d . . . C14 C 0.59091(8) 0.8596(2) 0.2861(4) 0.0245(5) Uani 1 1 d . . . H14A H 0.6107 0.9196 0.3800 0.037 Uiso 1 1 calc R . . H14B H 0.5656 0.9080 0.1972 0.037 Uiso 1 1 calc R . . H14C H 0.6144 0.8136 0.1846 0.037 Uiso 1 1 calc R . . C15 C 0.52584(8) 0.6067(2) 0.2959(4) 0.0205(5) Uani 1 1 d . . . H15A H 0.5530 0.5556 0.2236 0.031 Uiso 1 1 calc R . . H15B H 0.5038 0.6454 0.1802 0.031 Uiso 1 1 calc R . . H15C H 0.5050 0.5506 0.3928 0.031 Uiso 1 1 calc R . . C16 C 0.50631(10) 0.8243(3) 0.6548(5) 0.0347(6) Uani 1 1 d . . . H16A H 0.4893 0.7611 0.7526 0.052 Uiso 1 1 calc R . . H16B H 0.4805 0.8658 0.5582 0.052 Uiso 1 1 calc R . . H16C H 0.5234 0.8899 0.7475 0.052 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 0.01092(13) 0.00956(12) 0.01000(13) 0.00066(15) -0.00107(13) 0.00002(8) Si2 0.0164(3) 0.0158(3) 0.0153(3) -0.0001(2) -0.0030(2) 0.0051(2) O1 0.0230(7) 0.0221(7) 0.0115(7) 0.0001(6) 0.0000(5) 0.0046(6) C1 0.0127(9) 0.0105(8) 0.0118(9) 0.0006(7) -0.0009(7) -0.0012(7) C2 0.0136(9) 0.0095(8) 0.0130(9) 0.0010(7) -0.0015(7) -0.0016(7) C3 0.0128(9) 0.0112(9) 0.0159(10) -0.0002(8) 0.0011(8) -0.0008(7) C4 0.0107(9) 0.0118(9) 0.0185(11) 0.0014(8) -0.0035(8) -0.0006(7) C5 0.0149(9) 0.0132(9) 0.0107(9) -0.0001(7) -0.0037(7) -0.0010(7) C6 0.0117(8) 0.0194(9) 0.0262(11) -0.0038(12) -0.0005(11) -0.0021(6) C7 0.0173(10) 0.0160(9) 0.0189(11) 0.0017(8) -0.0071(9) -0.0019(7) C8 0.0194(10) 0.0171(9) 0.0149(10) -0.0041(8) -0.0017(8) -0.0031(7) C9 0.0180(9) 0.0117(8) 0.0197(12) -0.0008(8) -0.0041(9) -0.0032(7) C10 0.0177(10) 0.0233(10) 0.0163(11) 0.0007(9) 0.0003(8) -0.0094(8) C11 0.0144(9) 0.0109(8) 0.0148(10) -0.0007(8) -0.0017(8) -0.0008(7) C12 0.0181(9) 0.0131(8) 0.0133(10) -0.0012(7) 0.0013(7) 0.0014(7) C13 0.0193(10) 0.0183(10) 0.0150(10) -0.0014(8) 0.0005(8) 0.0046(8) C14 0.0235(10) 0.0198(10) 0.0303(15) 0.0062(9) -0.0064(9) -0.0015(8) C15 0.0191(10) 0.0217(10) 0.0207(12) 0.0001(8) -0.0016(8) -0.0011(8) C16 0.0325(13) 0.0465(16) 0.0249(12) -0.0062(12) -0.0009(11) 0.0249(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 2.0247(19) . ? Fe1 C2 2.0250(19) . ? Fe1 C8 2.038(2) . ? Fe1 C7 2.043(2) . ? Fe1 C6 2.0434(19) . ? Fe1 C5 2.050(2) . ? Fe1 C9 2.0518(18) . ? Fe1 C10 2.057(2) . ? Fe1 C3 2.0575(19) . ? Fe1 C4 2.069(2) . ? Si2 C13 1.854(2) . ? Si2 C14 1.855(2) . ? Si2 C15 1.859(2) . ? Si2 C16 1.866(2) . ? O1 C11 1.226(3) . ? C1 C2 1.438(3) . ? C1 C5 1.440(3) . ? C1 C11 1.460(3) . ? C2 C3 1.433(3) . ? C3 C4 1.425(3) . ? C4 C5 1.411(3) . ? C6 C7 1.418(4) . ? C6 C10 1.421(3) . ? C7 C8 1.425(3) . ? C8 C9 1.418(3) . ? C9 C10 1.419(3) . ? C11 C12 1.461(3) . ? C12 C13 1.205(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 C2 41.60(8) . . ? C1 Fe1 C8 157.68(9) . . ? C2 Fe1 C8 120.44(9) . . ? C1 Fe1 C7 121.51(8) . . ? C2 Fe1 C7 104.38(8) . . ? C8 Fe1 C7 40.89(8) . . ? C1 Fe1 C6 107.24(8) . . ? C2 Fe1 C6 120.99(8) . . ? C8 Fe1 C6 68.32(9) . . ? C7 Fe1 C6 40.63(11) . . ? C1 Fe1 C5 41.38(7) . . ? C2 Fe1 C5 69.80(8) . . ? C8 Fe1 C5 158.94(8) . . ? C7 Fe1 C5 159.52(8) . . ? C6 Fe1 C5 124.50(10) . . ? C1 Fe1 C9 160.02(9) . . ? C2 Fe1 C9 157.77(9) . . ? C8 Fe1 C9 40.58(9) . . ? C7 Fe1 C9 68.48(8) . . ? C6 Fe1 C9 68.09(7) . . ? C5 Fe1 C9 124.03(8) . . ? C1 Fe1 C10 123.50(9) . . ? C2 Fe1 C10 158.42(8) . . ? C8 Fe1 C10 68.28(9) . . ? C7 Fe1 C10 68.47(9) . . ? C6 Fe1 C10 40.57(9) . . ? C5 Fe1 C10 109.40(9) . . ? C9 Fe1 C10 40.42(8) . . ? C1 Fe1 C3 68.77(8) . . ? C2 Fe1 C3 41.08(7) . . ? C8 Fe1 C3 106.40(8) . . ? C7 Fe1 C3 120.94(10) . . ? C6 Fe1 C3 157.24(10) . . ? C5 Fe1 C3 68.24(8) . . ? C9 Fe1 C3 123.20(8) . . ? C10 Fe1 C3 160.05(8) . . ? C1 Fe1 C4 68.44(8) . . ? C2 Fe1 C4 69.01(8) . . ? C8 Fe1 C4 122.86(8) . . ? C7 Fe1 C4 157.74(9) . . ? C6 Fe1 C4 160.87(10) . . ? C5 Fe1 C4 40.06(8) . . ? C9 Fe1 C4 109.22(7) . . ? C10 Fe1 C4 125.10(9) . . ? C3 Fe1 C4 40.40(8) . . ? C13 Si2 C14 109.67(10) . . ? C13 Si2 C15 107.43(10) . . ? C14 Si2 C15 110.56(11) . . ? C13 Si2 C16 107.10(12) . . ? C14 Si2 C16 110.45(12) . . ? C15 Si2 C16 111.51(12) . . ? C2 C1 C5 108.21(17) . . ? C2 C1 C11 127.46(18) . . ? C5 C1 C11 124.01(18) . . ? C2 C1 Fe1 69.21(11) . . ? C5 C1 Fe1 70.23(11) . . ? C11 C1 Fe1 121.21(13) . . ? C3 C2 C1 106.86(17) . . ? C3 C2 Fe1 70.67(11) . . ? C1 C2 Fe1 69.19(11) . . ? C4 C3 C2 108.50(18) . . ? C4 C3 Fe1 70.23(12) . . ? C2 C3 Fe1 68.24(11) . . ? C5 C4 C3 108.67(16) . . ? C5 C4 Fe1 69.23(11) . . ? C3 C4 Fe1 69.37(11) . . ? C4 C5 C1 107.74(18) . . ? C4 C5 Fe1 70.71(12) . . ? C1 C5 Fe1 68.38(11) . . ? C7 C6 C10 108.60(18) . . ? C7 C6 Fe1 69.65(12) . . ? C10 C6 Fe1 70.22(11) . . ? C6 C7 C8 107.4(2) . . ? C6 C7 Fe1 69.72(13) . . ? C8 C7 Fe1 69.39(12) . . ? C9 C8 C7 108.2(2) . . ? C9 C8 Fe1 70.22(12) . . ? C7 C8 Fe1 69.72(13) . . ? C8 C9 C10 108.16(18) . . ? C8 C9 Fe1 69.19(11) . . ? C10 C9 Fe1 69.98(11) . . ? C9 C10 C6 107.6(2) . . ? C9 C10 Fe1 69.60(11) . . ? C6 C10 Fe1 69.21(11) . . ? O1 C11 C1 122.39(18) . . ? O1 C11 C12 119.97(18) . . ? C1 C11 C12 117.63(18) . . ? C13 C12 C11 176.4(2) . . ? C12 C13 Si2 176.0(2) . . ? 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 C8 Fe1 C1 C2 -42.8(2) . . . . ? C7 Fe1 C1 C2 -75.43(13) . . . . ? C6 Fe1 C1 C2 -117.54(13) . . . . ? C5 Fe1 C1 C2 119.45(15) . . . . ? C9 Fe1 C1 C2 169.3(2) . . . . ? C10 Fe1 C1 C2 -159.09(11) . . . . ? C3 Fe1 C1 C2 38.70(11) . . . . ? C4 Fe1 C1 C2 82.24(11) . . . . ? C2 Fe1 C1 C5 -119.45(15) . . . . ? C8 Fe1 C1 C5 -162.2(2) . . . . ? C7 Fe1 C1 C5 165.12(12) . . . . ? C6 Fe1 C1 C5 123.01(13) . . . . ? C9 Fe1 C1 C5 49.9(3) . . . . ? C10 Fe1 C1 C5 81.46(14) . . . . ? C3 Fe1 C1 C5 -80.75(12) . . . . ? C4 Fe1 C1 C5 -37.21(12) . . . . ? C2 Fe1 C1 C11 122.0(2) . . . . ? C8 Fe1 C1 C11 79.3(3) . . . . ? C7 Fe1 C1 C11 46.6(2) . . . . ? C6 Fe1 C1 C11 4.5(2) . . . . ? C5 Fe1 C1 C11 -118.5(2) . . . . ? C9 Fe1 C1 C11 -68.6(3) . . . . ? C10 Fe1 C1 C11 -37.0(2) . . . . ? C3 Fe1 C1 C11 160.75(19) . . . . ? C4 Fe1 C1 C11 -155.72(19) . . . . ? C5 C1 C2 C3 -1.4(2) . . . . ? C11 C1 C2 C3 -175.02(18) . . . . ? Fe1 C1 C2 C3 -60.98(13) . . . . ? C5 C1 C2 Fe1 59.62(13) . . . . ? C11 C1 C2 Fe1 -114.0(2) . . . . ? C1 Fe1 C2 C3 117.52(16) . . . . ? C8 Fe1 C2 C3 -79.88(14) . . . . ? C7 Fe1 C2 C3 -120.90(13) . . . . ? C6 Fe1 C2 C3 -161.44(14) . . . . ? C5 Fe1 C2 C3 79.69(13) . . . . ? C9 Fe1 C2 C3 -52.8(3) . . . . ? C10 Fe1 C2 C3 171.5(2) . . . . ? C4 Fe1 C2 C3 36.77(12) . . . . ? C8 Fe1 C2 C1 162.60(11) . . . . ? C7 Fe1 C2 C1 121.58(12) . . . . ? C6 Fe1 C2 C1 81.04(15) . . . . ? C5 Fe1 C2 C1 -37.83(11) . . . . ? C9 Fe1 C2 C1 -170.35(19) . . . . ? C10 Fe1 C2 C1 54.0(3) . . . . ? C3 Fe1 C2 C1 -117.52(16) . . . . ? C4 Fe1 C2 C1 -80.75(12) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? Fe1 C2 C3 C4 -58.83(14) . . . . ? C1 C2 C3 Fe1 60.02(13) . . . . ? C1 Fe1 C3 C4 81.26(12) . . . . ? C2 Fe1 C3 C4 120.43(17) . . . . ? C8 Fe1 C3 C4 -121.79(12) . . . . ? C7 Fe1 C3 C4 -163.86(11) . . . . ? C6 Fe1 C3 C4 165.3(2) . . . . ? C5 Fe1 C3 C4 36.63(11) . . . . ? C9 Fe1 C3 C4 -80.69(14) . . . . ? C10 Fe1 C3 C4 -50.4(3) . . . . ? C1 Fe1 C3 C2 -39.17(12) . . . . ? C8 Fe1 C3 C2 117.78(13) . . . . ? C7 Fe1 C3 C2 75.71(14) . . . . ? C6 Fe1 C3 C2 44.9(3) . . . . ? C5 Fe1 C3 C2 -83.80(13) . . . . ? C9 Fe1 C3 C2 158.88(13) . . . . ? C10 Fe1 C3 C2 -170.9(2) . . . . ? C4 Fe1 C3 C2 -120.43(17) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? Fe1 C3 C4 C5 -58.18(13) . . . . ? C2 C3 C4 Fe1 57.62(13) . . . . ? C1 Fe1 C4 C5 38.41(11) . . . . ? C2 Fe1 C4 C5 83.21(12) . . . . ? C8 Fe1 C4 C5 -163.33(12) . . . . ? C7 Fe1 C4 C5 159.60(18) . . . . ? C6 Fe1 C4 C5 -42.0(3) . . . . ? C9 Fe1 C4 C5 -120.41(12) . . . . ? C10 Fe1 C4 C5 -78.18(14) . . . . ? C3 Fe1 C4 C5 120.57(15) . . . . ? C1 Fe1 C4 C3 -82.17(11) . . . . ? C2 Fe1 C4 C3 -37.37(11) . . . . ? C8 Fe1 C4 C3 76.10(13) . . . . ? C7 Fe1 C4 C3 39.0(2) . . . . ? C6 Fe1 C4 C3 -162.6(2) . . . . ? C5 Fe1 C4 C3 -120.57(15) . . . . ? C9 Fe1 C4 C3 119.02(12) . . . . ? C10 Fe1 C4 C3 161.25(11) . . . . ? C3 C4 C5 C1 -0.3(2) . . . . ? Fe1 C4 C5 C1 -58.55(13) . . . . ? C3 C4 C5 Fe1 58.27(14) . . . . ? C2 C1 C5 C4 1.0(2) . . . . ? C11 C1 C5 C4 174.95(17) . . . . ? Fe1 C1 C5 C4 60.01(13) . . . . ? C2 C1 C5 Fe1 -58.99(13) . . . . ? C11 C1 C5 Fe1 114.94(19) . . . . ? C1 Fe1 C5 C4 -119.07(16) . . . . ? C2 Fe1 C5 C4 -81.05(12) . . . . ? C8 Fe1 C5 C4 42.1(3) . . . . ? C7 Fe1 C5 C4 -157.8(2) . . . . ? C6 Fe1 C5 C4 164.57(11) . . . . ? C9 Fe1 C5 C4 79.29(13) . . . . ? C10 Fe1 C5 C4 121.89(12) . . . . ? C3 Fe1 C5 C4 -36.93(10) . . . . ? C2 Fe1 C5 C1 38.03(11) . . . . ? C8 Fe1 C5 C1 161.2(2) . . . . ? C7 Fe1 C5 C1 -38.8(3) . . . . ? C6 Fe1 C5 C1 -76.35(14) . . . . ? C9 Fe1 C5 C1 -161.63(11) . . . . ? C10 Fe1 C5 C1 -119.03(12) . . . . ? C3 Fe1 C5 C1 82.14(12) . . . . ? C4 Fe1 C5 C1 119.07(16) . . . . ? C1 Fe1 C6 C7 118.59(12) . . . . ? C2 Fe1 C6 C7 75.23(14) . . . . ? C8 Fe1 C6 C7 -38.18(12) . . . . ? C5 Fe1 C6 C7 160.86(11) . . . . ? C9 Fe1 C6 C7 -82.04(13) . . . . ? C10 Fe1 C6 C7 -119.67(18) . . . . ? C3 Fe1 C6 C7 42.5(3) . . . . ? C4 Fe1 C6 C7 -167.6(2) . . . . ? C1 Fe1 C6 C10 -121.74(13) . . . . ? C2 Fe1 C6 C10 -165.11(13) . . . . ? C8 Fe1 C6 C10 81.49(14) . . . . ? C7 Fe1 C6 C10 119.67(18) . . . . ? C5 Fe1 C6 C10 -79.47(15) . . . . ? C9 Fe1 C6 C10 37.63(14) . . . . ? C3 Fe1 C6 C10 162.16(19) . . . . ? C4 Fe1 C6 C10 -48.0(3) . . . . ? C10 C6 C7 C8 -0.2(2) . . . . ? Fe1 C6 C7 C8 59.40(14) . . . . ? C10 C6 C7 Fe1 -59.62(14) . . . . ? C1 Fe1 C7 C6 -79.60(13) . . . . ? C2 Fe1 C7 C6 -121.16(12) . . . . ? C8 Fe1 C7 C6 118.65(17) . . . . ? C5 Fe1 C7 C6 -50.6(3) . . . . ? C9 Fe1 C7 C6 81.01(12) . . . . ? C10 Fe1 C7 C6 37.41(11) . . . . ? C3 Fe1 C7 C6 -162.26(11) . . . . ? C4 Fe1 C7 C6 169.33(18) . . . . ? C1 Fe1 C7 C8 161.75(12) . . . . ? C2 Fe1 C7 C8 120.19(13) . . . . ? C6 Fe1 C7 C8 -118.65(17) . . . . ? C5 Fe1 C7 C8 -169.2(2) . . . . ? C9 Fe1 C7 C8 -37.65(13) . . . . ? C10 Fe1 C7 C8 -81.25(14) . . . . ? C3 Fe1 C7 C8 79.09(14) . . . . ? C4 Fe1 C7 C8 50.7(3) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? Fe1 C7 C8 C9 59.92(14) . . . . ? C6 C7 C8 Fe1 -59.61(14) . . . . ? C1 Fe1 C8 C9 -163.81(18) . . . . ? C2 Fe1 C8 C9 164.67(11) . . . . ? C7 Fe1 C8 C9 -119.14(18) . . . . ? C6 Fe1 C8 C9 -81.19(13) . . . . ? C5 Fe1 C8 C9 50.4(3) . . . . ? C10 Fe1 C8 C9 -37.38(12) . . . . ? C3 Fe1 C8 C9 122.26(12) . . . . ? C4 Fe1 C8 C9 81.28(14) . . . . ? C1 Fe1 C8 C7 -44.7(3) . . . . ? C2 Fe1 C8 C7 -76.20(15) . . . . ? C6 Fe1 C8 C7 37.94(14) . . . . ? C5 Fe1 C8 C7 169.5(2) . . . . ? C9 Fe1 C8 C7 119.14(18) . . . . ? C10 Fe1 C8 C7 81.76(14) . . . . ? C3 Fe1 C8 C7 -118.60(14) . . . . ? C4 Fe1 C8 C7 -159.59(13) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? Fe1 C8 C9 C10 59.33(13) . . . . ? C7 C8 C9 Fe1 -59.60(14) . . . . ? C1 Fe1 C9 C8 161.9(2) . . . . ? C2 Fe1 C9 C8 -37.1(3) . . . . ? C7 Fe1 C9 C8 37.92(13) . . . . ? C6 Fe1 C9 C8 81.80(14) . . . . ? C5 Fe1 C9 C8 -160.49(12) . . . . ? C10 Fe1 C9 C8 119.57(17) . . . . ? C3 Fe1 C9 C8 -75.81(14) . . . . ? C4 Fe1 C9 C8 -118.44(13) . . . . ? C1 Fe1 C9 C10 42.4(3) . . . . ? C2 Fe1 C9 C10 -156.63(19) . . . . ? C8 Fe1 C9 C10 -119.57(17) . . . . ? C7 Fe1 C9 C10 -81.64(14) . . . . ? C6 Fe1 C9 C10 -37.76(14) . . . . ? C5 Fe1 C9 C10 79.95(14) . . . . ? C3 Fe1 C9 C10 164.63(13) . . . . ? C4 Fe1 C9 C10 121.99(13) . . . . ? C8 C9 C10 C6 0.1(2) . . . . ? Fe1 C9 C10 C6 58.98(14) . . . . ? C8 C9 C10 Fe1 -58.84(13) . . . . ? C7 C6 C10 C9 0.1(2) . . . . ? Fe1 C6 C10 C9 -59.22(14) . . . . ? C7 C6 C10 Fe1 59.27(14) . . . . ? C1 Fe1 C10 C9 -163.97(12) . . . . ? C2 Fe1 C10 C9 155.9(2) . . . . ? C8 Fe1 C10 C9 37.52(13) . . . . ? C7 Fe1 C10 C9 81.66(14) . . . . ? C6 Fe1 C10 C9 119.1(2) . . . . ? C5 Fe1 C10 C9 -120.10(13) . . . . ? C3 Fe1 C10 C9 -40.6(3) . . . . ? C4 Fe1 C10 C9 -78.19(15) . . . . ? C1 Fe1 C10 C6 76.91(17) . . . . ? C2 Fe1 C10 C6 36.8(3) . . . . ? C8 Fe1 C10 C6 -81.60(15) . . . . ? C7 Fe1 C10 C6 -37.46(15) . . . . ? C5 Fe1 C10 C6 120.79(15) . . . . ? C9 Fe1 C10 C6 -119.1(2) . . . . ? C3 Fe1 C10 C6 -159.7(2) . . . . ? C4 Fe1 C10 C6 162.69(14) . . . . ? C2 C1 C11 O1 -171.81(19) . . . . ? C5 C1 C11 O1 15.5(3) . . . . ? Fe1 C1 C11 O1 101.5(2) . . . . ? C2 C1 C11 C12 9.0(3) . . . . ? C5 C1 C11 C12 -163.76(18) . . . . ? Fe1 C1 C11 C12 -77.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.416 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.136 #end