#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:40:48 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708618.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7708618 loop_ _publ_author_name 'Erb, William' 'Roisnel, Thierry' _publ_section_title ; The chemistry of ferrocenesulfonyl fluoride revealed ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D1DT03492H _journal_year 2021 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C10 H9 F Fe O2 S' _chemical_formula_sum 'C10 H9 F Fe O2 S' _chemical_formula_weight 268.08 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_update_record ; 2021-10-12 deposited with the CCDC. 2021-10-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.978(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6335(6) _cell_length_b 10.0261(10) _cell_length_c 13.0870(11) _cell_measurement_reflns_used 3168 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.2871 _cell_measurement_theta_min 2.5684 _cell_measurement_wavelength 0.710730 _cell_volume 991.91(15) _computing_cell_refinement 'Bruker APEX2 (Bruker, 2014)' _computing_data_collection 'Bruker APEX2 (Bruker, 2014)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2020)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'APEXII Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_orient_matrix_UB_11 0.0871409 _diffrn_orient_matrix_UB_12 -0.0302006 _diffrn_orient_matrix_UB_13 0.0596828 _diffrn_orient_matrix_UB_21 -0.0200056 _diffrn_orient_matrix_UB_22 -0.0947574 _diffrn_orient_matrix_UB_23 -0.0224818 _diffrn_orient_matrix_UB_31 0.0974929 _diffrn_orient_matrix_UB_32 0.0075496 _diffrn_orient_matrix_UB_33 -0.0434279 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0324 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6671 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.479 _diffrn_reflns_theta_min 2.568 _exptl_absorpt_coefficient_mu 1.718 _exptl_absorpt_correction_T_max 0.512 _exptl_absorpt_correction_T_min 0.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.795 _exptl_crystal_description prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.580 _exptl_crystal_size_mid 0.560 _exptl_crystal_size_min 0.390 _refine_diff_density_max 0.440 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef 0.0179(10) _refine_ls_extinction_method 'SHELXL-2018_3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 2254 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0265 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.3447P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.0654 _reflns_number_gt 1990 _reflns_number_total 2254 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1dt03492h2.cif _cod_data_source_block WE12701_2 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7708618 _shelx_res_file ; TITL WE12701 [Space group= P2(1)/n] job.res created by SHELXL-2018/3 at 15:09:36 on 12-Jan-2021 CELL 0.71073 7.6335 10.0261 13.0870 90.000 97.978 90.000 ZERR 4.00 0.0006 0.0010 0.0011 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H F FE O S UNIT 40 36 4 4 8 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.39 0.56 0.58 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.028100 0.344700 EXTI 0.017887 FVAR 0.60838 FE1 4 0.486763 0.296709 0.711538 11.00000 0.01220 0.01294 = 0.01363 -0.00090 0.00160 0.00059 S1 6 0.714555 0.197051 0.533949 11.00000 0.01923 0.02809 = 0.01736 0.00186 0.00539 0.00738 C1 1 0.357558 0.409426 0.593614 11.00000 0.02053 0.02391 = 0.02091 0.00489 0.00106 0.00625 AFIX 43 H1 2 0.384247 0.413612 0.524912 11.00000 -1.20000 AFIX 0 C2 1 0.429777 0.492338 0.676434 11.00000 0.02321 0.01421 = 0.03474 0.00283 0.00262 0.00485 AFIX 43 H2 2 0.513093 0.561994 0.672907 11.00000 -1.20000 AFIX 0 C3 1 0.356037 0.453308 0.765759 11.00000 0.02407 0.02294 = 0.02539 -0.00657 0.00348 0.01056 AFIX 43 H3 2 0.381115 0.492276 0.832353 11.00000 -1.20000 AFIX 0 C4 1 0.238211 0.345704 0.737761 11.00000 0.01377 0.03006 = 0.02621 0.00121 0.00648 0.00525 AFIX 43 H4 2 0.171041 0.299647 0.782512 11.00000 -1.20000 AFIX 0 C5 1 0.238245 0.318875 0.631073 11.00000 0.01334 0.02583 = 0.02577 0.00014 -0.00322 0.00168 AFIX 43 H5 2 0.170564 0.252287 0.591850 11.00000 -1.20000 AFIX 0 C6 1 0.554704 0.102351 0.699651 11.00000 0.01934 0.01331 = 0.02335 0.00107 0.00286 0.00261 AFIX 43 H6 2 0.484507 0.035326 0.662526 11.00000 -1.20000 AFIX 0 C7 1 0.558687 0.135728 0.805666 11.00000 0.02493 0.02043 = 0.01851 0.00661 0.00496 0.00602 AFIX 43 H7 2 0.491363 0.093810 0.852425 11.00000 -1.20000 AFIX 0 C8 1 0.679719 0.241809 0.829775 11.00000 0.02349 0.02608 = 0.01710 -0.00292 -0.00464 0.00852 AFIX 43 H8 2 0.706845 0.282656 0.895568 11.00000 -1.20000 AFIX 0 C9 1 0.753989 0.277401 0.740208 11.00000 0.01305 0.01819 = 0.02471 -0.00438 -0.00224 0.00079 AFIX 43 H9 2 0.838040 0.345931 0.734531 11.00000 -1.20000 AFIX 0 C10 1 0.677395 0.189760 0.660062 11.00000 0.01348 0.01753 = 0.01577 0.00051 0.00099 0.00386 O11 5 0.565885 0.154771 0.464586 11.00000 0.03266 0.04004 = 0.01908 -0.00586 0.00081 0.00189 O12 5 0.808401 0.314183 0.515625 11.00000 0.03292 0.04970 = 0.03196 0.01266 0.00954 -0.00910 F13 3 0.853172 0.080886 0.532221 11.00000 0.05068 0.05973 = 0.03171 0.00250 0.01577 0.03877 HKLF 4 REM WE12701 [Space group= P2(1)/n] REM wR2 = 0.0654, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0265 for 1990 Fo > 4sig(Fo) and 0.0317 for all 2254 data REM 137 parameters refined using 0 restraints END WGHT 0.0257 0.3854 REM Highest difference peak 0.440, deepest hole -0.311, 1-sigma level 0.064 Q1 1 0.6894 0.2006 0.6072 11.00000 0.05 0.44 Q2 1 0.4530 0.2956 0.7772 11.00000 0.05 0.37 Q3 1 0.6305 0.1403 0.6823 11.00000 0.05 0.33 Q4 1 0.8392 0.2489 0.5060 11.00000 0.05 0.31 Q5 1 0.7391 0.2255 0.6983 11.00000 0.05 0.31 Q6 1 0.4986 0.2876 0.6411 11.00000 0.05 0.29 Q7 1 0.5692 0.1082 0.7562 11.00000 0.05 0.28 Q8 1 0.3864 0.4788 0.7223 11.00000 0.05 0.28 Q9 1 0.2956 0.4002 0.7428 11.00000 0.05 0.27 Q10 1 0.3951 0.4451 0.6381 11.00000 0.05 0.27 Q11 1 0.7558 0.0600 0.5350 11.00000 0.05 0.27 Q12 1 0.2561 0.3163 0.6842 11.00000 0.05 0.26 Q13 1 0.5658 0.3644 0.7281 11.00000 0.05 0.26 Q14 1 0.7568 0.2393 0.7979 11.00000 0.05 0.26 Q15 1 0.2890 0.3762 0.6103 11.00000 0.05 0.25 Q16 1 0.4079 0.2380 0.6664 11.00000 0.05 0.24 Q17 1 0.5418 0.3181 0.6568 11.00000 0.05 0.24 Q18 1 0.6226 0.1366 0.5000 11.00000 0.05 0.23 Q19 1 0.7610 0.3145 0.4811 11.00000 0.05 0.23 Q20 1 0.8303 0.3454 0.4931 11.00000 0.05 0.22 ; _shelx_res_checksum 28966 loop_ _space_group_symop_operation_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' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.48676(3) 0.29671(2) 0.71154(2) 0.01294(10) Uani 1 1 d . . . . . S1 S 0.71455(6) 0.19705(5) 0.53395(4) 0.02129(13) Uani 1 1 d . . . . . C1 C 0.3576(2) 0.4094(2) 0.59361(15) 0.0220(4) Uani 1 1 d . . . . . H1 H 0.384247 0.413612 0.524912 0.026 Uiso 1 1 calc R U . . . C2 C 0.4298(3) 0.49234(19) 0.67643(16) 0.0242(4) Uani 1 1 d . . . . . H2 H 0.513093 0.561994 0.672907 0.029 Uiso 1 1 calc R U . . . C3 C 0.3560(2) 0.4533(2) 0.76576(15) 0.0241(4) Uani 1 1 d . . . . . H3 H 0.381115 0.492276 0.832353 0.029 Uiso 1 1 calc R U . . . C4 C 0.2382(2) 0.3457(2) 0.73776(15) 0.0230(4) Uani 1 1 d . . . . . H4 H 0.171041 0.299647 0.782512 0.028 Uiso 1 1 calc R U . . . C5 C 0.2382(2) 0.3189(2) 0.63107(15) 0.0222(4) Uani 1 1 d . . . . . H5 H 0.170564 0.252287 0.591850 0.027 Uiso 1 1 calc R U . . . C6 C 0.5547(2) 0.10235(18) 0.69965(14) 0.0187(4) Uani 1 1 d . . . . . H6 H 0.484507 0.035326 0.662526 0.022 Uiso 1 1 calc R U . . . C7 C 0.5587(2) 0.13573(19) 0.80567(14) 0.0211(4) Uani 1 1 d . . . . . H7 H 0.491363 0.093810 0.852425 0.025 Uiso 1 1 calc R U . . . C8 C 0.6797(2) 0.2418(2) 0.82977(15) 0.0229(4) Uani 1 1 d . . . . . H8 H 0.706845 0.282656 0.895568 0.028 Uiso 1 1 calc R U . . . C9 C 0.7540(2) 0.27740(19) 0.74021(15) 0.0191(4) Uani 1 1 d . . . . . H9 H 0.838040 0.345931 0.734531 0.023 Uiso 1 1 calc R U . . . C10 C 0.6774(2) 0.18976(18) 0.66006(14) 0.0157(4) Uani 1 1 d . . . . . O11 O 0.56589(19) 0.15477(16) 0.46459(10) 0.0309(4) Uani 1 1 d . . . . . O12 O 0.8084(2) 0.31418(17) 0.51562(12) 0.0377(4) Uani 1 1 d . . . . . F13 F 0.85317(18) 0.08089(15) 0.53222(10) 0.0464(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 0.01220(15) 0.01294(15) 0.01363(15) -0.00090(10) 0.00160(9) 0.00059(10) S1 0.0192(2) 0.0281(3) 0.0174(2) 0.00186(19) 0.00539(18) 0.0074(2) C1 0.0205(9) 0.0239(10) 0.0209(9) 0.0049(8) 0.0011(7) 0.0063(8) C2 0.0232(10) 0.0142(10) 0.0347(11) 0.0028(8) 0.0026(8) 0.0049(8) C3 0.0241(10) 0.0229(10) 0.0254(10) -0.0066(8) 0.0035(8) 0.0106(8) C4 0.0138(9) 0.0301(11) 0.0262(10) 0.0012(9) 0.0065(7) 0.0053(8) C5 0.0133(9) 0.0258(11) 0.0258(10) 0.0001(8) -0.0032(7) 0.0017(8) C6 0.0193(9) 0.0133(9) 0.0233(9) 0.0011(8) 0.0029(7) 0.0026(8) C7 0.0249(10) 0.0204(10) 0.0185(9) 0.0066(8) 0.0050(7) 0.0060(8) C8 0.0235(10) 0.0261(11) 0.0171(9) -0.0029(8) -0.0046(7) 0.0085(9) C9 0.0130(8) 0.0182(10) 0.0247(10) -0.0044(8) -0.0022(7) 0.0008(7) C10 0.0135(8) 0.0175(10) 0.0158(8) 0.0005(7) 0.0010(6) 0.0039(7) O11 0.0327(8) 0.0400(9) 0.0191(7) -0.0059(7) 0.0008(6) 0.0019(7) O12 0.0329(9) 0.0497(11) 0.0320(9) 0.0127(8) 0.0095(7) -0.0091(8) F13 0.0507(8) 0.0597(10) 0.0317(7) 0.0025(7) 0.0158(6) 0.0388(8) 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C6 41.63(7) . . ? C10 Fe1 C9 41.55(7) . . ? C6 Fe1 C9 70.23(7) . . ? C10 Fe1 C4 157.84(8) . . ? C6 Fe1 C4 119.95(8) . . ? C9 Fe1 C4 158.10(8) . . ? C10 Fe1 C3 160.83(8) . . ? C6 Fe1 C3 155.36(8) . . ? C9 Fe1 C3 122.43(8) . . ? C4 Fe1 C3 40.78(8) . . ? C10 Fe1 C2 125.48(8) . . ? C6 Fe1 C2 162.16(8) . . ? C9 Fe1 C2 108.02(8) . . ? C4 Fe1 C2 68.44(8) . . ? C3 Fe1 C2 40.69(8) . . ? C10 Fe1 C5 123.38(8) . . ? C6 Fe1 C5 107.04(8) . . ? C9 Fe1 C5 159.90(8) . . ? C4 Fe1 C5 40.74(8) . . ? C3 Fe1 C5 68.45(8) . . ? C2 Fe1 C5 68.18(8) . . ? C10 Fe1 C1 109.79(7) . . ? C6 Fe1 C1 124.96(8) . . ? C9 Fe1 C1 123.85(8) . . ? C4 Fe1 C1 68.39(8) . . ? C3 Fe1 C1 68.31(8) . . ? C2 Fe1 C1 40.41(8) . . ? C5 Fe1 C1 40.53(8) . . ? C10 Fe1 C8 68.36(7) . . ? C6 Fe1 C8 68.70(8) . . ? C9 Fe1 C8 40.54(8) . . ? C4 Fe1 C8 121.65(8) . . ? C3 Fe1 C8 106.14(8) . . ? C2 Fe1 C8 122.18(8) . . ? C5 Fe1 C8 158.44(8) . . ? C1 Fe1 C8 158.78(8) . . ? C10 Fe1 C7 68.58(7) . . ? C6 Fe1 C7 40.76(7) . . ? C9 Fe1 C7 68.72(8) . . ? C4 Fe1 C7 105.42(8) . . ? C3 Fe1 C7 119.88(8) . . ? C2 Fe1 C7 156.39(8) . . ? C5 Fe1 C7 122.92(8) . . ? C1 Fe1 C7 160.50(8) . . ? C8 Fe1 C7 40.23(8) . . ? O12 S1 O11 121.33(10) . . ? O12 S1 F13 104.75(10) . . ? O11 S1 F13 104.45(9) . . ? O12 S1 C10 110.75(9) . . ? O11 S1 C10 112.29(9) . . ? F13 S1 C10 100.57(8) . . ? C2 C1 C5 108.14(17) . . ? C2 C1 Fe1 69.64(11) . . ? C5 C1 Fe1 69.68(11) . . ? C2 C1 H1 125.9 . . ? C5 C1 H1 125.9 . . ? Fe1 C1 H1 126.3 . . ? C1 C2 C3 108.15(17) . . ? C1 C2 Fe1 69.96(11) . . ? C3 C2 Fe1 69.37(11) . . ? C1 C2 H2 125.9 . . ? C3 C2 H2 125.9 . . ? Fe1 C2 H2 126.3 . . ? C4 C3 C2 107.82(17) . . ? C4 C3 Fe1 69.41(11) . . ? C2 C3 Fe1 69.94(11) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.1 . . ? Fe1 C3 H3 126.1 . . ? C3 C4 C5 108.10(17) . . ? C3 C4 Fe1 69.81(10) . . ? C5 C4 Fe1 70.21(11) . . ? C3 C4 H4 125.9 . . ? C5 C4 H4 125.9 . . ? Fe1 C4 H4 125.6 . . ? C1 C5 C4 107.79(18) . . ? C1 C5 Fe1 69.80(11) . . ? C4 C5 Fe1 69.05(11) . . ? C1 C5 H5 126.1 . . ? C4 C5 H5 126.1 . . ? Fe1 C5 H5 126.6 . . ? C7 C6 C10 106.40(17) . . ? C7 C6 Fe1 70.76(11) . . ? C10 C6 Fe1 68.07(10) . . ? C7 C6 H6 126.8 . . ? C10 C6 H6 126.8 . . ? Fe1 C6 H6 125.9 . . ? C8 C7 C6 108.60(17) . . ? C8 C7 Fe1 69.87(11) . . ? C6 C7 Fe1 68.48(10) . . ? C8 C7 H7 125.7 . . ? C6 C7 H7 125.7 . . ? Fe1 C7 H7 127.5 . . ? C7 C8 C9 109.18(17) . . ? C7 C8 Fe1 69.90(11) . . ? C9 C8 Fe1 68.74(11) . . ? C7 C8 H8 125.4 . . ? C9 C8 H8 125.4 . . ? Fe1 C8 H8 127.6 . . ? C8 C9 C10 106.40(16) . . ? C8 C9 Fe1 70.73(11) . . ? C10 C9 Fe1 67.98(10) . . ? C8 C9 H9 126.8 . . ? C10 C9 H9 126.8 . . ? Fe1 C9 H9 126.0 . . ? C9 C10 C6 109.41(16) . . ? C9 C10 S1 125.07(14) . . ? C6 C10 S1 125.35(14) . . ? C9 C10 Fe1 70.47(10) . . ? C6 C10 Fe1 70.29(10) . . ? S1 C10 Fe1 121.81(10) . . ? 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 1.9983(17) . ? Fe1 C6 2.0280(19) . ? Fe1 C9 2.0315(18) . ? Fe1 C4 2.0346(18) . ? Fe1 C3 2.0399(18) . ? Fe1 C2 2.0474(19) . ? Fe1 C5 2.0500(19) . ? Fe1 C1 2.0516(19) . ? Fe1 C8 2.0577(19) . ? Fe1 C7 2.0582(19) . ? S1 O12 1.4133(16) . ? S1 O11 1.4162(15) . ? S1 F13 1.5759(13) . ? S1 C10 1.7146(18) . ? C1 C2 1.416(3) . ? C1 C5 1.421(3) . ? C1 H1 0.9500 . ? C2 C3 1.421(3) . ? C2 H2 0.9500 . ? C3 C4 1.420(3) . ? C3 H3 0.9500 . ? C4 C5 1.422(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.423(3) . ? C6 C10 1.431(2) . ? C6 H6 0.9500 . ? C7 C8 1.415(3) . ? C7 H7 0.9500 . ? C8 C9 1.417(3) . ? C8 H8 0.9500 . ? C9 C10 1.430(3) . ? C9 H9 0.9500 . ? 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 C1 C2 C3 0.2(2) . . . . ? Fe1 C1 C2 C3 -59.05(13) . . . . ? C5 C1 C2 Fe1 59.24(13) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? Fe1 C2 C3 C4 -59.29(13) . . . . ? C1 C2 C3 Fe1 59.42(13) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? Fe1 C3 C4 C5 -60.02(13) . . . . ? C2 C3 C4 Fe1 59.63(13) . . . . ? C2 C1 C5 C4 -0.4(2) . . . . ? Fe1 C1 C5 C4 58.79(13) . . . . ? C2 C1 C5 Fe1 -59.22(13) . . . . ? C3 C4 C5 C1 0.5(2) . . . . ? Fe1 C4 C5 C1 -59.25(13) . . . . ? C3 C4 C5 Fe1 59.76(13) . . . . ? C10 C6 C7 C8 0.5(2) . . . . ? Fe1 C6 C7 C8 -58.46(13) . . . . ? C10 C6 C7 Fe1 59.00(12) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? Fe1 C7 C8 C9 -57.58(13) . . . . ? C6 C7 C8 Fe1 57.62(13) . . . . ? C7 C8 C9 C10 -0.6(2) . . . . ? Fe1 C8 C9 C10 -58.88(12) . . . . ? C7 C8 C9 Fe1 58.28(13) . . . . ? C8 C9 C10 C6 0.9(2) . . . . ? Fe1 C9 C10 C6 -59.71(12) . . . . ? C8 C9 C10 S1 176.40(14) . . . . ? Fe1 C9 C10 S1 115.74(14) . . . . ? C8 C9 C10 Fe1 60.65(12) . . . . ? C7 C6 C10 C9 -0.9(2) . . . . ? Fe1 C6 C10 C9 59.82(12) . . . . ? C7 C6 C10 S1 -176.36(13) . . . . ? Fe1 C6 C10 S1 -115.62(14) . . . . ? C7 C6 C10 Fe1 -60.74(12) . . . . ? O12 S1 C10 C9 -9.42(19) . . . . ? O11 S1 C10 C9 -148.55(16) . . . . ? F13 S1 C10 C9 100.91(16) . . . . ? O12 S1 C10 C6 165.32(15) . . . . ? O11 S1 C10 C6 26.20(19) . . . . ? F13 S1 C10 C6 -84.34(17) . . . . ? O12 S1 C10 Fe1 77.99(13) . . . . ? O11 S1 C10 Fe1 -61.14(14) . . . . ? F13 S1 C10 Fe1 -171.68(11) . . . . ?