#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:40:48 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708626.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_7708626 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 'C12 H9 F Fe O2 S' _chemical_formula_sum 'C12 H9 F Fe O2 S' _chemical_formula_weight 292.10 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 81.337(6) _cell_angle_beta 74.314(6) _cell_angle_gamma 84.801(6) _cell_formula_units_Z 2 _cell_length_a 6.9415(12) _cell_length_b 9.1569(18) _cell_length_c 9.4381(18) _cell_measurement_reflns_used 5096 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4940 _cell_measurement_theta_min 2.2529 _cell_measurement_wavelength 0.710730 _cell_volume 570.19(19) _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, ver. 2021)' _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 0.999 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'APEXII Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_orient_matrix_UB_11 0.0608765 _diffrn_orient_matrix_UB_12 -0.0776709 _diffrn_orient_matrix_UB_13 -0.0652122 _diffrn_orient_matrix_UB_21 0.0512060 _diffrn_orient_matrix_UB_22 0.0787527 _diffrn_orient_matrix_UB_23 -0.0842916 _diffrn_orient_matrix_UB_31 0.1269790 _diffrn_orient_matrix_UB_32 -0.0013626 _diffrn_orient_matrix_UB_33 0.0310972 _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 0.0268 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9163 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.568 _diffrn_reflns_theta_min 2.975 _exptl_absorpt_coefficient_mu 1.502 _exptl_absorpt_correction_T_max 0.775 _exptl_absorpt_correction_T_min 0.676 _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 1.701 _exptl_crystal_description prism _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.330 _exptl_crystal_size_min 0.170 _refine_diff_density_max 0.940 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2602 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0264 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.2906P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0701 _reflns_number_gt 2386 _reflns_number_total 2602 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1dt03492h2.cif _cod_data_source_block WE13761 _cod_database_code 7708626 _shelx_res_file ; TITL WE13761 [Space group= P-1] job.res created by SHELXL-2018/3 at 14:06:15 on 28-Apr-2021 REM Old TITL WE13761 REM SHELXT solution in P-1: R1 0.084, Rweak 0.007, Alpha 0.029 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C11 F Fe O3 S CELL 0.71073 6.9415 9.1569 9.4381 81.337 74.314 84.801 ZERR 2.000 0.0012 0.0018 0.0018 0.006 0.006 0.006 LATT 1 SFAC C H F FE O S UNIT 24.00 18.00 2.00 2.00 4.00 2.00 MERG 2 FMAP 2 PLAN 20 SIZE 0.17 0.33 0.39 OMIT 0 1 0 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.035900 0.290600 FVAR 0.80270 C1 1 0.885788 0.755431 0.455716 11.00000 0.02724 0.07774 = 0.03391 -0.00898 -0.01943 0.00708 AFIX 43 H1 2 0.823822 0.742419 0.559344 11.00000 -1.20000 AFIX 0 C2 1 0.940700 0.642267 0.363830 11.00000 0.03368 0.02806 = 0.08114 0.00217 -0.03869 0.00201 AFIX 43 H2 2 0.922498 0.539598 0.394088 11.00000 -1.20000 AFIX 0 C3 1 1.027415 0.709784 0.219082 11.00000 0.02066 0.05477 = 0.05264 -0.02788 -0.01541 0.01106 AFIX 43 H3 2 1.078614 0.660211 0.134065 11.00000 -1.20000 AFIX 0 C4 1 1.025473 0.862498 0.221554 11.00000 0.02118 0.04661 = 0.05551 0.00246 -0.01451 -0.00914 AFIX 43 H4 2 1.074530 0.934413 0.138711 11.00000 -1.20000 AFIX 0 C5 1 0.938682 0.890342 0.367311 11.00000 0.03122 0.03777 = 0.07088 -0.02437 -0.03176 0.00491 AFIX 43 H5 2 0.918877 0.984685 0.400819 11.00000 -1.20000 AFIX 0 C6 1 0.574616 0.919596 0.167433 11.00000 0.02135 0.02166 = 0.02906 -0.00042 -0.01119 -0.00004 AFIX 43 H6 2 0.619974 1.000255 0.093198 11.00000 -1.20000 AFIX 0 C7 1 0.481801 0.927081 0.319473 11.00000 0.01988 0.02103 = 0.03080 -0.00537 -0.01065 0.00333 AFIX 43 H7 2 0.453221 1.014788 0.365478 11.00000 -1.20000 AFIX 0 C8 1 0.437831 0.779767 0.392932 11.00000 0.01735 0.02517 = 0.02481 -0.00389 -0.00826 -0.00038 C9 1 0.503595 0.679363 0.285683 11.00000 0.01840 0.02185 = 0.02541 -0.00282 -0.00828 -0.00326 AFIX 43 H9 2 0.493851 0.575042 0.303039 11.00000 -1.20000 AFIX 0 C10 1 0.587000 0.766243 0.147030 11.00000 0.01879 0.02290 = 0.02243 -0.00366 -0.00796 -0.00120 C11 1 0.348740 0.739530 0.547834 11.00000 0.02107 0.02601 = 0.02920 -0.00593 -0.00730 -0.00057 C12 1 0.273278 0.704896 0.675950 11.00000 0.03089 0.03980 = 0.02913 -0.00552 -0.00566 -0.00206 AFIX 163 H12 2 0.212886 0.677178 0.778479 11.00000 -1.20000 AFIX 0 O13 5 0.838768 0.795856 -0.112541 11.00000 0.04998 0.04636 = 0.03322 -0.00659 0.00843 -0.01480 O14 5 0.751668 0.544598 0.009814 11.00000 0.05611 0.02993 = 0.03560 -0.01148 -0.00776 0.00568 F15 3 0.520985 0.709284 -0.088683 11.00000 0.05683 0.05479 = 0.03655 -0.01178 -0.02767 -0.00374 FE1 4 0.739924 0.792065 0.292183 11.00000 0.01591 0.01891 = 0.02506 -0.00414 -0.00866 -0.00025 S1 6 0.700941 0.697475 -0.015970 11.00000 0.03138 0.02802 = 0.02346 -0.00570 -0.00562 -0.00299 HKLF 4 REM WE13761 [Space group= P-1] REM wR2 = 0.0701, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0264 for 2386 Fo > 4sig(Fo) and 0.0295 for all 2602 data REM 154 parameters refined using 0 restraints END WGHT 0.0345 0.2799 REM Highest difference peak 0.940, deepest hole -0.302, 1-sigma level 0.061 Q1 1 0.7452 0.6971 0.2991 11.00000 0.05 0.94 Q2 1 0.6377 0.7351 0.0745 11.00000 0.05 0.37 Q3 1 0.4521 0.7297 0.3493 11.00000 0.05 0.36 Q4 1 1.0002 0.8660 0.2995 11.00000 0.05 0.35 Q5 1 0.4370 0.8534 0.3585 11.00000 0.05 0.34 Q6 1 0.7489 0.7695 -0.0856 11.00000 0.05 0.34 Q7 1 1.0393 0.7847 0.2246 11.00000 0.05 0.31 Q8 1 0.5631 0.8440 0.1364 11.00000 0.05 0.30 Q9 1 0.7554 0.6149 -0.0059 11.00000 0.05 0.29 Q10 1 0.2522 0.7753 0.6241 11.00000 0.05 0.28 Q11 1 0.8767 0.8289 0.4042 11.00000 0.05 0.28 Q12 1 0.5628 0.6275 -0.0952 11.00000 0.05 0.27 Q13 1 0.9507 0.6669 0.2787 11.00000 0.05 0.26 Q14 1 0.4925 0.9425 0.2378 11.00000 0.05 0.26 Q15 1 0.8723 0.7630 0.4900 11.00000 0.05 0.25 Q16 1 0.4224 0.7368 0.4818 11.00000 0.05 0.23 Q17 1 0.5877 0.7134 0.2027 11.00000 0.05 0.23 Q18 1 0.2838 0.6946 0.5790 11.00000 0.05 0.23 Q19 1 0.6803 0.7537 0.3810 11.00000 0.05 0.22 Q20 1 0.3740 0.6976 0.6216 11.00000 0.05 0.22 ; _shelx_res_checksum 93719 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.8858(3) 0.7554(3) 0.4557(3) 0.0445(6) Uani 1 1 d . . . . . H1 H 0.823822 0.742419 0.559344 0.053 Uiso 1 1 calc R U . . . C2 C 0.9407(3) 0.6423(2) 0.3638(3) 0.0442(6) Uani 1 1 d . . . . . H2 H 0.922498 0.539598 0.394088 0.053 Uiso 1 1 calc R U . . . C3 C 1.0274(3) 0.7098(3) 0.2191(3) 0.0402(5) Uani 1 1 d . . . . . H3 H 1.078614 0.660211 0.134065 0.048 Uiso 1 1 calc R U . . . C4 C 1.0255(3) 0.8625(3) 0.2216(3) 0.0407(5) Uani 1 1 d . . . . . H4 H 1.074530 0.934413 0.138711 0.049 Uiso 1 1 calc R U . . . C5 C 0.9387(3) 0.8903(2) 0.3673(3) 0.0416(6) Uani 1 1 d . . . . . H5 H 0.918877 0.984685 0.400819 0.050 Uiso 1 1 calc R U . . . C6 C 0.5746(3) 0.91960(19) 0.1674(2) 0.0235(4) Uani 1 1 d . . . . . H6 H 0.619974 1.000255 0.093198 0.028 Uiso 1 1 calc R U . . . C7 C 0.4818(3) 0.92708(19) 0.3195(2) 0.0232(4) Uani 1 1 d . . . . . H7 H 0.453221 1.014788 0.365478 0.028 Uiso 1 1 calc R U . . . C8 C 0.4378(2) 0.77977(19) 0.3929(2) 0.0219(3) Uani 1 1 d . . . . . C9 C 0.5036(2) 0.67936(19) 0.28568(19) 0.0213(3) Uani 1 1 d . . . . . H9 H 0.493851 0.575042 0.303039 0.026 Uiso 1 1 calc R U . . . C10 C 0.5870(3) 0.76624(19) 0.14703(19) 0.0208(3) Uani 1 1 d . . . . . C11 C 0.3487(3) 0.7395(2) 0.5478(2) 0.0251(4) Uani 1 1 d . . . . . C12 C 0.2733(3) 0.7049(2) 0.6759(2) 0.0336(4) Uani 1 1 d . . . . . H12 H 0.212886 0.677178 0.778479 0.040 Uiso 1 1 calc R U . . . O13 O 0.8388(3) 0.79586(18) -0.11254(17) 0.0460(4) Uani 1 1 d . . . . . O14 O 0.7517(3) 0.54460(16) 0.00981(17) 0.0411(4) Uani 1 1 d . . . . . F15 F 0.5210(2) 0.70928(15) -0.08868(14) 0.0457(3) Uani 1 1 d . . . . . Fe1 Fe 0.73992(3) 0.79207(3) 0.29218(3) 0.01922(9) Uani 1 1 d . . . . . S1 S 0.70094(7) 0.69747(5) -0.01597(5) 0.02758(12) 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 C1 0.0272(11) 0.0777(18) 0.0339(11) -0.0090(11) -0.0194(9) 0.0071(11) C2 0.0337(11) 0.0281(10) 0.0811(18) 0.0022(11) -0.0387(12) 0.0020(9) C3 0.0207(9) 0.0548(14) 0.0526(14) -0.0279(11) -0.0154(9) 0.0111(9) C4 0.0212(10) 0.0466(13) 0.0555(14) 0.0025(11) -0.0145(9) -0.0091(9) C5 0.0312(11) 0.0378(12) 0.0709(16) -0.0244(11) -0.0318(11) 0.0049(9) C6 0.0213(8) 0.0217(8) 0.0291(9) -0.0004(7) -0.0112(7) 0.0000(7) C7 0.0199(8) 0.0210(8) 0.0308(9) -0.0054(7) -0.0106(7) 0.0033(6) C8 0.0173(8) 0.0252(9) 0.0248(9) -0.0039(7) -0.0083(7) -0.0004(6) C9 0.0184(8) 0.0219(8) 0.0254(9) -0.0028(7) -0.0083(7) -0.0033(6) C10 0.0188(8) 0.0229(8) 0.0224(8) -0.0037(6) -0.0080(6) -0.0012(6) C11 0.0211(8) 0.0260(9) 0.0292(10) -0.0059(7) -0.0073(7) -0.0006(7) C12 0.0309(10) 0.0398(11) 0.0291(10) -0.0055(8) -0.0057(8) -0.0021(9) O13 0.0500(10) 0.0464(9) 0.0332(8) -0.0066(7) 0.0084(7) -0.0148(8) O14 0.0561(10) 0.0299(8) 0.0356(8) -0.0115(6) -0.0078(7) 0.0057(7) F15 0.0568(8) 0.0548(8) 0.0366(7) -0.0118(6) -0.0277(6) -0.0037(6) Fe1 0.01591(13) 0.01891(14) 0.02506(15) -0.00414(9) -0.00866(10) -0.00025(9) S1 0.0314(3) 0.0280(2) 0.0235(2) -0.00570(18) -0.00562(18) -0.00299(19) 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 C5 C1 C2 108.0(2) . . ? C5 C1 Fe1 70.04(12) . . ? C2 C1 Fe1 69.91(12) . . ? C5 C1 H1 126.0 . . ? C2 C1 H1 126.0 . . ? Fe1 C1 H1 125.6 . . ? C3 C2 C1 107.3(2) . . ? C3 C2 Fe1 69.85(12) . . ? C1 C2 Fe1 69.59(12) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? Fe1 C2 H2 125.8 . . ? C4 C3 C2 108.4(2) . . ? C4 C3 Fe1 70.05(12) . . ? C2 C3 Fe1 69.83(12) . . ? C4 C3 H3 125.8 . . ? C2 C3 H3 125.8 . . ? Fe1 C3 H3 125.9 . . ? C5 C4 C3 107.9(2) . . ? C5 C4 Fe1 69.87(12) . . ? C3 C4 Fe1 69.84(12) . . ? C5 C4 H4 126.0 . . ? C3 C4 H4 126.0 . . ? Fe1 C4 H4 125.8 . . ? C4 C5 C1 108.4(2) . . ? C4 C5 Fe1 70.14(12) . . ? C1 C5 Fe1 69.76(12) . . ? C4 C5 H5 125.8 . . ? C1 C5 H5 125.8 . . ? Fe1 C5 H5 125.9 . . ? C7 C6 C10 106.69(15) . . ? C7 C6 Fe1 70.82(10) . . ? C10 C6 Fe1 67.72(9) . . ? C7 C6 H6 126.7 . . ? C10 C6 H6 126.7 . . ? Fe1 C6 H6 126.3 . . ? C6 C7 C8 108.69(15) . . ? C6 C7 Fe1 68.78(10) . . ? C8 C7 Fe1 69.53(10) . . ? C6 C7 H7 125.7 . . ? C8 C7 H7 125.7 . . ? Fe1 C7 H7 127.6 . . ? C9 C8 C11 125.49(16) . . ? C9 C8 C7 108.39(15) . . ? C11 C8 C7 126.10(16) . . ? C9 C8 Fe1 68.65(10) . . ? C11 C8 Fe1 126.17(12) . . ? C7 C8 Fe1 69.60(10) . . ? C8 C9 C10 106.61(15) . . ? C8 C9 Fe1 70.61(10) . . ? C10 C9 Fe1 67.85(9) . . ? C8 C9 H9 126.7 . . ? C10 C9 H9 126.7 . . ? Fe1 C9 H9 126.4 . . ? C9 C10 C6 109.62(15) . . ? C9 C10 S1 125.29(13) . . ? C6 C10 S1 124.93(14) . . ? C9 C10 Fe1 70.66(10) . . ? C6 C10 Fe1 70.51(10) . . ? S1 C10 Fe1 121.63(9) . . ? C12 C11 C8 179.1(2) . . ? C11 C12 H12 180.0 . . ? C10 Fe1 C6 41.77(7) . . ? C10 Fe1 C9 41.49(7) . . ? C6 Fe1 C9 70.29(7) . . ? C10 Fe1 C1 163.66(9) . . ? C6 Fe1 C1 153.21(9) . . ? C9 Fe1 C1 125.27(9) . . ? C10 Fe1 C5 154.91(9) . . ? C6 Fe1 C5 118.94(8) . . ? C9 Fe1 C5 162.28(9) . . ? C1 Fe1 C5 40.20(10) . . ? C10 Fe1 C2 126.61(9) . . ? C6 Fe1 C2 164.34(10) . . ? C9 Fe1 C2 107.58(8) . . ? C1 Fe1 C2 40.50(10) . . ? C5 Fe1 C2 67.78(9) . . ? C10 Fe1 C3 108.99(8) . . ? C6 Fe1 C3 126.61(9) . . ? C9 Fe1 C3 121.04(8) . . ? C1 Fe1 C3 67.63(9) . . ? C5 Fe1 C3 67.32(9) . . ? C2 Fe1 C3 40.32(10) . . ? C10 Fe1 C4 120.96(9) . . ? C6 Fe1 C4 107.49(8) . . ? C9 Fe1 C4 155.94(9) . . ? C1 Fe1 C4 67.56(10) . . ? C5 Fe1 C4 39.99(10) . . ? C2 Fe1 C4 67.79(9) . . ? C3 Fe1 C4 40.11(9) . . ? C10 Fe1 C8 68.64(7) . . ? C6 Fe1 C8 68.97(7) . . ? C9 Fe1 C8 40.74(7) . . ? C1 Fe1 C8 107.38(8) . . ? C5 Fe1 C8 125.41(9) . . ? C2 Fe1 C8 120.14(9) . . ? C3 Fe1 C8 155.43(9) . . ? C4 Fe1 C8 162.41(9) . . ? C10 Fe1 C7 68.61(7) . . ? C6 Fe1 C7 40.39(7) . . ? C9 Fe1 C7 69.11(7) . . ? C1 Fe1 C7 119.48(9) . . ? C5 Fe1 C7 107.27(8) . . ? C2 Fe1 C7 154.51(10) . . ? C3 Fe1 C7 162.98(9) . . ? C4 Fe1 C7 125.50(8) . . ? C8 Fe1 C7 40.87(7) . . ? O13 S1 O14 121.31(10) . . ? O13 S1 F15 104.17(10) . . ? O14 S1 F15 105.58(9) . . ? O13 S1 C10 111.50(9) . . ? O14 S1 C10 111.12(9) . . ? F15 S1 C10 100.55(8) . . ? 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 C1 C5 1.401(4) . ? C1 C2 1.411(3) . ? C1 Fe1 2.037(2) . ? C1 H1 0.9500 . ? C2 C3 1.407(4) . ? C2 Fe1 2.041(2) . ? C2 H2 0.9500 . ? C3 C4 1.401(3) . ? C3 Fe1 2.041(2) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 Fe1 2.044(2) . ? C4 H4 0.9500 . ? C5 Fe1 2.040(2) . ? C5 H5 0.9500 . ? C6 C7 1.414(3) . ? C6 C10 1.438(2) . ? C6 Fe1 2.0348(17) . ? C6 H6 0.9500 . ? C7 C8 1.439(2) . ? C7 Fe1 2.0616(17) . ? C7 H7 0.9500 . ? C8 C9 1.426(2) . ? C8 C11 1.430(3) . ? C8 Fe1 2.0607(17) . ? C9 C10 1.429(2) . ? C9 Fe1 2.0348(17) . ? C9 H9 0.9500 . ? C10 S1 1.7124(18) . ? C10 Fe1 1.9972(17) . ? C11 C12 1.187(3) . ? C12 H12 0.9500 . ? O13 S1 1.4124(16) . ? O14 S1 1.4132(15) . ? F15 S1 1.5684(13) . ? 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 0.0(2) . . . . ? Fe1 C1 C2 C3 59.96(14) . . . . ? C5 C1 C2 Fe1 -59.92(14) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? Fe1 C2 C3 C4 59.63(14) . . . . ? C1 C2 C3 Fe1 -59.80(14) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? Fe1 C3 C4 C5 59.73(14) . . . . ? C2 C3 C4 Fe1 -59.49(14) . . . . ? C3 C4 C5 C1 -0.2(2) . . . . ? Fe1 C4 C5 C1 59.50(14) . . . . ? C3 C4 C5 Fe1 -59.71(14) . . . . ? C2 C1 C5 C4 0.1(2) . . . . ? Fe1 C1 C5 C4 -59.74(14) . . . . ? C2 C1 C5 Fe1 59.84(14) . . . . ? C10 C6 C7 C8 0.27(18) . . . . ? Fe1 C6 C7 C8 -58.17(12) . . . . ? C10 C6 C7 Fe1 58.44(11) . . . . ? C6 C7 C8 C9 -0.07(19) . . . . ? Fe1 C7 C8 C9 -57.79(12) . . . . ? C6 C7 C8 C11 178.25(16) . . . . ? Fe1 C7 C8 C11 120.53(17) . . . . ? C6 C7 C8 Fe1 57.72(12) . . . . ? C11 C8 C9 C10 -178.49(16) . . . . ? C7 C8 C9 C10 -0.15(18) . . . . ? Fe1 C8 C9 C10 -58.52(11) . . . . ? C11 C8 C9 Fe1 -119.97(17) . . . . ? C7 C8 C9 Fe1 58.37(12) . . . . ? C8 C9 C10 C6 0.32(19) . . . . ? Fe1 C9 C10 C6 -59.97(12) . . . . ? C8 C9 C10 S1 175.93(13) . . . . ? Fe1 C9 C10 S1 115.63(14) . . . . ? C8 C9 C10 Fe1 60.30(11) . . . . ? C7 C6 C10 C9 -0.37(19) . . . . ? Fe1 C6 C10 C9 60.06(12) . . . . ? C7 C6 C10 S1 -175.99(13) . . . . ? Fe1 C6 C10 S1 -115.56(14) . . . . ? C7 C6 C10 Fe1 -60.43(11) . . . . ? C9 C10 S1 O13 -154.62(15) . . . . ? C6 C10 S1 O13 20.33(18) . . . . ? Fe1 C10 S1 O13 -66.93(14) . . . . ? C9 C10 S1 O14 -15.95(18) . . . . ? C6 C10 S1 O14 159.00(15) . . . . ? Fe1 C10 S1 O14 71.74(13) . . . . ? C9 C10 S1 F15 95.44(16) . . . . ? C6 C10 S1 F15 -89.61(15) . . . . ? Fe1 C10 S1 F15 -176.87(10) . . . . ?