#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:40:48 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708628.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_7708628 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 'C16 H12 F2 Fe O2 S' _chemical_formula_sum 'C16 H12 F2 Fe O2 S' _chemical_formula_weight 362.17 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 90.465(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.9437(7) _cell_length_b 7.5335(4) _cell_length_c 15.7854(7) _cell_measurement_reflns_used 8111 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4583 _cell_measurement_theta_min 2.5815 _cell_measurement_wavelength 0.710730 _cell_volume 1420.29(13) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'Bruker APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics ; 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)' ; _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2021)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_detector '(CMOS) PHOTON 100' _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 0.0271702 _diffrn_orient_matrix_UB_12 0.0907929 _diffrn_orient_matrix_UB_13 -0.0412220 _diffrn_orient_matrix_UB_21 -0.0295416 _diffrn_orient_matrix_UB_22 0.0966013 _diffrn_orient_matrix_UB_23 0.0370686 _diffrn_orient_matrix_UB_31 0.0734181 _diffrn_orient_matrix_UB_32 0.0052697 _diffrn_orient_matrix_UB_33 0.0307019 _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_unetI/netI 0.0622 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 7384 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.474 _diffrn_reflns_theta_min 2.996 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 1.234 _exptl_absorpt_correction_T_max 0.811 _exptl_absorpt_correction_T_min 0.475 _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 1.694 _exptl_crystal_description prism _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.170 _refine_diff_density_max 1.411 _refine_diff_density_min -1.545 _refine_diff_density_rms 0.153 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3196 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0634 _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^)+(0.1066P)^2^+2.6328P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1594 _refine_ls_wR_factor_ref 0.1733 _reflns_number_gt 2725 _reflns_number_total 3196 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1dt03492h2.cif _cod_data_source_block WE13081 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7708628 _shelx_res_file ; TITL WE13081 [Space group= P2(1)/c] job.res created by SHELXL-2018/3 at 10:10:25 on 05-Feb-2021 CELL 0.71073 11.9437 7.5335 15.7854 90.000 90.465 90.000 ZERR 4.00 0.0007 0.0004 0.0007 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H F FE O S UNIT 64 48 8 4 8 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.17 0.38 0.48 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.106600 2.632800 FVAR 0.61340 C1 1 0.180520 0.233883 0.726020 11.00000 0.01902 0.03491 = 0.01872 0.00985 0.00448 0.00092 AFIX 43 H1 2 0.249672 0.204140 0.752577 11.00000 -1.20000 AFIX 0 C2 1 0.117744 0.392154 0.739646 11.00000 0.03066 0.04654 = 0.01358 0.00219 0.00944 0.00477 AFIX 43 H2 2 0.137698 0.486969 0.776461 11.00000 -1.20000 AFIX 0 C3 1 0.018951 0.382038 0.687600 11.00000 0.01911 0.06255 = 0.02663 0.01382 0.01228 0.00985 AFIX 43 H3 2 -0.038514 0.468988 0.684157 11.00000 -1.20000 AFIX 0 C4 1 0.021930 0.220159 0.642295 11.00000 0.02043 0.05877 = 0.02503 0.01631 0.00092 -0.01375 AFIX 43 H4 2 -0.033005 0.179554 0.602986 11.00000 -1.20000 AFIX 0 C5 1 0.121805 0.128674 0.665971 11.00000 0.02574 0.03193 = 0.02750 0.01033 0.00598 -0.00770 AFIX 43 H5 2 0.145038 0.016411 0.645080 11.00000 -1.20000 AFIX 0 C6 1 0.161070 0.415878 0.486863 11.00000 0.01771 0.03961 = 0.01677 0.01162 -0.00125 -0.00191 AFIX 43 H6 2 0.107836 0.373257 0.446712 11.00000 -1.20000 AFIX 0 C7 1 0.157536 0.580811 0.531250 11.00000 0.01859 0.03092 = 0.02938 0.01433 0.00424 0.00457 AFIX 43 H7 2 0.100634 0.668250 0.525701 11.00000 -1.20000 AFIX 0 C8 1 0.252493 0.592606 0.584742 11.00000 0.02061 0.02147 = 0.02555 0.00604 0.00534 0.00384 AFIX 43 H8 2 0.269103 0.689802 0.621069 11.00000 -1.20000 AFIX 0 C9 1 0.320404 0.436283 0.576287 11.00000 0.01544 0.02161 = 0.01604 0.00433 0.00476 -0.00015 C10 1 0.261600 0.326728 0.515108 11.00000 0.01482 0.02772 = 0.01512 0.00369 0.00037 -0.00029 C11 1 0.428103 0.405648 0.619407 11.00000 0.01632 0.01810 = 0.01527 0.00108 0.00116 -0.00195 C12 1 0.442496 0.458408 0.703890 11.00000 0.02357 0.02185 = 0.01831 -0.00348 0.00051 0.00160 AFIX 43 H12 2 0.380938 0.507511 0.733569 11.00000 -1.20000 AFIX 0 C13 1 0.545094 0.440289 0.745106 11.00000 0.02546 0.02616 = 0.01958 -0.00235 -0.00320 -0.00634 AFIX 43 H13 2 0.555048 0.476815 0.802275 11.00000 -1.20000 AFIX 0 C14 1 0.632215 0.366969 0.699640 11.00000 0.01639 0.02306 = 0.02591 0.00477 -0.00358 -0.00353 C15 1 0.622522 0.314245 0.616370 11.00000 0.01498 0.02229 = 0.02538 0.00379 0.00455 0.00019 AFIX 43 H15 2 0.684577 0.265287 0.587230 11.00000 -1.20000 AFIX 0 C16 1 0.519108 0.334755 0.576082 11.00000 0.01722 0.02424 = 0.01586 0.00024 0.00095 -0.00274 AFIX 43 H16 2 0.510476 0.300119 0.518531 11.00000 -1.20000 AFIX 0 F17 3 0.733511 0.344420 0.738683 11.00000 0.02086 0.04044 = 0.03425 0.00209 -0.01215 -0.00196 O18 5 0.193383 0.032520 0.447899 11.00000 0.03491 0.04457 = 0.03305 -0.01451 -0.00873 -0.00651 O19 5 0.355522 0.018427 0.544864 11.00000 0.02834 0.02718 = 0.02704 -0.00419 -0.00376 0.00265 F20 3 0.371087 0.146280 0.408404 11.00000 0.03919 0.05268 = 0.02051 -0.00664 0.01162 0.00044 FE1 4 0.161293 0.369669 0.614372 11.00000 0.01242 0.02626 = 0.01550 0.00405 0.00318 0.00145 S1 6 0.290088 0.112159 0.484681 11.00000 0.02208 0.02948 = 0.01539 -0.00542 0.00082 -0.00308 HKLF 4 REM WE13081 [Space group= P2(1)/c] REM wR2 = 0.1733, GooF = S = 1.029, Restrained GooF = 1.029 for all data REM R1 = 0.0634 for 2725 Fo > 4sig(Fo) and 0.0724 for all 3196 data REM 199 parameters refined using 0 restraints END WGHT 0.1004 2.5427 REM Highest difference peak 1.411, deepest hole -1.545, 1-sigma level 0.153 Q1 1 0.1599 0.5023 0.6151 11.00000 0.05 1.41 Q2 1 0.1581 0.2332 0.6080 11.00000 0.05 1.27 Q3 1 0.2824 0.2380 0.4949 11.00000 0.05 0.85 Q4 1 0.2905 -0.0266 0.4950 11.00000 0.05 0.61 Q5 1 0.1173 0.2994 0.5785 11.00000 0.05 0.55 Q6 1 0.2948 -0.1541 0.5014 11.00000 0.05 0.49 Q7 1 0.7378 0.1957 0.7508 11.00000 0.05 0.47 Q8 1 0.3583 0.1348 0.5289 11.00000 0.05 0.46 Q9 1 0.1158 0.4453 0.5803 11.00000 0.05 0.45 Q10 1 0.2478 0.5028 0.6042 11.00000 0.05 0.43 Q11 1 0.1016 -0.0105 0.6235 11.00000 0.05 0.43 Q12 1 0.2034 0.1717 0.4516 11.00000 0.05 0.43 Q13 1 0.2184 0.1365 0.4418 11.00000 0.05 0.42 Q14 1 0.2450 0.8014 0.5596 11.00000 0.05 0.41 Q15 1 0.2207 0.6676 0.5468 11.00000 0.05 0.40 Q16 1 0.1577 0.4797 0.5241 11.00000 0.05 0.39 Q17 1 0.3663 0.2833 0.3927 11.00000 0.05 0.38 Q18 1 0.2274 0.8250 0.5965 11.00000 0.05 0.37 Q19 1 0.0870 0.7258 0.6400 11.00000 0.05 0.36 Q20 1 0.2019 -0.0781 0.4534 11.00000 0.05 0.35 ; _shelx_res_checksum 4286 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.1805(3) 0.2339(5) 0.7260(2) 0.0242(7) Uani 1 1 d . . . . . H1 H 0.249672 0.204140 0.752577 0.029 Uiso 1 1 calc R U . . . C2 C 0.1177(3) 0.3922(5) 0.7396(2) 0.0302(8) Uani 1 1 d . . . . . H2 H 0.137698 0.486969 0.776461 0.036 Uiso 1 1 calc R U . . . C3 C 0.0190(3) 0.3820(6) 0.6876(3) 0.0360(10) Uani 1 1 d . . . . . H3 H -0.038514 0.468988 0.684157 0.043 Uiso 1 1 calc R U . . . C4 C 0.0219(3) 0.2202(6) 0.6423(2) 0.0347(9) Uani 1 1 d . . . . . H4 H -0.033005 0.179554 0.602986 0.042 Uiso 1 1 calc R U . . . C5 C 0.1218(3) 0.1287(5) 0.6660(2) 0.0284(8) Uani 1 1 d . . . . . H5 H 0.145038 0.016411 0.645080 0.034 Uiso 1 1 calc R U . . . C6 C 0.1611(3) 0.4159(5) 0.4869(2) 0.0247(7) Uani 1 1 d . . . . . H6 H 0.107836 0.373257 0.446712 0.030 Uiso 1 1 calc R U . . . C7 C 0.1575(3) 0.5808(5) 0.5313(2) 0.0263(7) Uani 1 1 d . . . . . H7 H 0.100634 0.668250 0.525701 0.032 Uiso 1 1 calc R U . . . C8 C 0.2525(3) 0.5926(4) 0.5847(2) 0.0225(7) Uani 1 1 d . . . . . H8 H 0.269103 0.689802 0.621069 0.027 Uiso 1 1 calc R U . . . C9 C 0.3204(3) 0.4363(4) 0.57629(19) 0.0177(6) Uani 1 1 d . . . . . C10 C 0.2616(3) 0.3267(5) 0.5151(2) 0.0192(6) Uani 1 1 d . . . . . C11 C 0.4281(3) 0.4056(4) 0.61941(19) 0.0166(6) Uani 1 1 d . . . . . C12 C 0.4425(3) 0.4584(4) 0.7039(2) 0.0212(6) Uani 1 1 d . . . . . H12 H 0.380938 0.507511 0.733569 0.025 Uiso 1 1 calc R U . . . C13 C 0.5451(3) 0.4403(5) 0.7451(2) 0.0238(7) Uani 1 1 d . . . . . H13 H 0.555048 0.476815 0.802275 0.029 Uiso 1 1 calc R U . . . C14 C 0.6322(3) 0.3670(4) 0.6996(2) 0.0218(7) Uani 1 1 d . . . . . C15 C 0.6225(3) 0.3142(4) 0.6164(2) 0.0209(6) Uani 1 1 d . . . . . H15 H 0.684577 0.265287 0.587230 0.025 Uiso 1 1 calc R U . . . C16 C 0.5191(3) 0.3348(4) 0.5761(2) 0.0191(6) Uani 1 1 d . . . . . H16 H 0.510476 0.300119 0.518531 0.023 Uiso 1 1 calc R U . . . F17 F 0.73351(18) 0.3444(3) 0.73868(15) 0.0319(5) Uani 1 1 d . . . . . O18 O 0.1934(3) 0.0325(4) 0.44790(18) 0.0376(7) Uani 1 1 d . . . . . O19 O 0.3555(2) 0.0184(3) 0.54486(16) 0.0275(5) Uani 1 1 d . . . . . F20 F 0.3711(2) 0.1463(3) 0.40840(15) 0.0374(6) Uani 1 1 d . . . . . Fe1 Fe 0.16129(4) 0.36967(6) 0.61437(3) 0.01804(19) Uani 1 1 d . . . . . S1 S 0.29009(7) 0.11216(11) 0.48468(5) 0.0223(2) 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 0.0190(15) 0.0349(18) 0.0187(14) 0.0098(13) 0.0045(12) 0.0009(13) C2 0.0307(19) 0.047(2) 0.0136(15) 0.0022(13) 0.0094(14) 0.0048(16) C3 0.0191(17) 0.063(3) 0.0266(19) 0.0138(17) 0.0123(15) 0.0098(16) C4 0.0204(17) 0.059(3) 0.0250(17) 0.0163(17) 0.0009(14) -0.0137(17) C5 0.0257(18) 0.0319(19) 0.0275(18) 0.0103(14) 0.0060(15) -0.0077(14) C6 0.0177(15) 0.0396(18) 0.0168(15) 0.0116(13) -0.0012(12) -0.0019(14) C7 0.0186(16) 0.0309(17) 0.0294(17) 0.0143(14) 0.0042(13) 0.0046(13) C8 0.0206(16) 0.0215(15) 0.0256(16) 0.0060(12) 0.0053(13) 0.0038(12) C9 0.0154(14) 0.0216(15) 0.0160(13) 0.0043(11) 0.0048(11) -0.0002(11) C10 0.0148(14) 0.0277(16) 0.0151(13) 0.0037(12) 0.0004(11) -0.0003(12) C11 0.0163(14) 0.0181(13) 0.0153(14) 0.0011(11) 0.0012(11) -0.0020(11) C12 0.0236(16) 0.0219(15) 0.0183(14) -0.0035(12) 0.0005(12) 0.0016(12) C13 0.0255(17) 0.0262(16) 0.0196(15) -0.0023(12) -0.0032(13) -0.0063(13) C14 0.0164(15) 0.0231(16) 0.0259(16) 0.0048(12) -0.0036(13) -0.0035(11) C15 0.0150(15) 0.0223(15) 0.0254(16) 0.0038(12) 0.0046(12) 0.0002(12) C16 0.0172(15) 0.0242(15) 0.0159(14) 0.0002(11) 0.0009(12) -0.0027(12) F17 0.0209(11) 0.0404(12) 0.0343(12) 0.0021(9) -0.0121(9) -0.0020(9) O18 0.0349(15) 0.0446(16) 0.0331(14) -0.0145(12) -0.0087(12) -0.0065(13) O19 0.0283(13) 0.0272(12) 0.0270(12) -0.0042(10) -0.0038(10) 0.0026(10) F20 0.0392(14) 0.0527(15) 0.0205(10) -0.0066(9) 0.0116(10) 0.0004(11) Fe1 0.0124(3) 0.0263(3) 0.0155(3) 0.00405(15) 0.00318(19) 0.00145(16) S1 0.0221(4) 0.0295(5) 0.0154(4) -0.0054(3) 0.0008(3) -0.0031(3) 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 108.1(3) . . ? C5 C1 Fe1 69.66(19) . . ? C2 C1 Fe1 69.93(19) . . ? C5 C1 H1 125.9 . . ? C2 C1 H1 125.9 . . ? Fe1 C1 H1 126.0 . . ? C1 C2 C3 107.5(4) . . ? C1 C2 Fe1 69.42(19) . . ? C3 C2 Fe1 70.0(2) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? Fe1 C2 H2 125.9 . . ? C4 C3 C2 108.1(3) . . ? C4 C3 Fe1 69.8(2) . . ? C2 C3 Fe1 69.3(2) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? Fe1 C3 H3 126.6 . . ? C3 C4 C5 108.0(4) . . ? C3 C4 Fe1 70.2(2) . . ? C5 C4 Fe1 69.2(2) . . ? C3 C4 H4 126.0 . . ? C5 C4 H4 126.0 . . ? Fe1 C4 H4 126.2 . . ? C1 C5 C4 108.3(3) . . ? C1 C5 Fe1 69.86(19) . . ? C4 C5 Fe1 70.2(2) . . ? C1 C5 H5 125.9 . . ? C4 C5 H5 125.9 . . ? Fe1 C5 H5 125.6 . . ? C7 C6 C10 106.3(3) . . ? C7 C6 Fe1 70.39(19) . . ? C10 C6 Fe1 67.78(17) . . ? C7 C6 H6 126.8 . . ? C10 C6 H6 126.8 . . ? Fe1 C6 H6 126.5 . . ? C8 C7 C6 108.8(3) . . ? C8 C7 Fe1 69.80(19) . . ? C6 C7 Fe1 68.92(19) . . ? C8 C7 H7 125.6 . . ? C6 C7 H7 125.6 . . ? Fe1 C7 H7 127.3 . . ? C7 C8 C9 110.1(3) . . ? C7 C8 Fe1 70.1(2) . . ? C9 C8 Fe1 69.66(18) . . ? C7 C8 H8 124.9 . . ? C9 C8 H8 124.9 . . ? Fe1 C8 H8 126.9 . . ? C8 C9 C10 105.0(3) . . ? C8 C9 C11 125.4(3) . . ? C10 C9 C11 129.6(3) . . ? C8 C9 Fe1 69.50(18) . . ? C10 C9 Fe1 67.18(17) . . ? C11 C9 Fe1 129.3(2) . . ? C6 C10 C9 109.8(3) . . ? C6 C10 S1 121.1(3) . . ? C9 C10 S1 128.7(2) . . ? C6 C10 Fe1 70.47(18) . . ? C9 C10 Fe1 71.14(18) . . ? S1 C10 Fe1 119.34(17) . . ? C16 C11 C12 119.0(3) . . ? C16 C11 C9 121.1(3) . . ? C12 C11 C9 119.8(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 117.4(3) . . ? C14 C13 H13 121.3 . . ? C12 C13 H13 121.3 . . ? F17 C14 C15 117.6(3) . . ? F17 C14 C13 118.9(3) . . ? C15 C14 C13 123.5(3) . . ? C14 C15 C16 118.1(3) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C15 C16 C11 120.7(3) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C10 Fe1 C6 41.75(13) . . ? C10 Fe1 C5 107.99(15) . . ? C6 Fe1 C5 123.02(16) . . ? C10 Fe1 C1 121.85(14) . . ? C6 Fe1 C1 158.73(15) . . ? C5 Fe1 C1 40.48(15) . . ? C10 Fe1 C2 157.19(15) . . ? C6 Fe1 C2 159.31(16) . . ? C5 Fe1 C2 68.24(16) . . ? C1 Fe1 C2 40.65(15) . . ? C10 Fe1 C8 68.50(14) . . ? C6 Fe1 C8 68.49(15) . . ? C5 Fe1 C8 159.83(15) . . ? C1 Fe1 C8 123.17(14) . . ? C2 Fe1 C8 106.85(16) . . ? C10 Fe1 C9 41.69(13) . . ? C6 Fe1 C9 70.41(13) . . ? C5 Fe1 C9 123.26(14) . . ? C1 Fe1 C9 105.99(13) . . ? C2 Fe1 C9 120.12(15) . . ? C8 Fe1 C9 40.84(12) . . ? C10 Fe1 C4 124.57(16) . . ? C6 Fe1 C4 108.02(15) . . ? C5 Fe1 C4 40.60(16) . . ? C1 Fe1 C4 68.17(14) . . ? C2 Fe1 C4 68.17(17) . . ? C8 Fe1 C4 157.64(16) . . ? C9 Fe1 C4 160.80(16) . . ? C10 Fe1 C7 68.75(14) . . ? C6 Fe1 C7 40.69(15) . . ? C5 Fe1 C7 159.00(16) . . ? C1 Fe1 C7 159.07(16) . . ? C2 Fe1 C7 122.96(16) . . ? C8 Fe1 C7 40.06(14) . . ? C9 Fe1 C7 69.01(13) . . ? C4 Fe1 C7 122.98(15) . . ? C10 Fe1 C3 160.67(17) . . ? C6 Fe1 C3 123.31(15) . . ? C5 Fe1 C3 67.91(16) . . ? C1 Fe1 C3 68.17(15) . . ? C2 Fe1 C3 40.73(17) . . ? C8 Fe1 C3 122.00(16) . . ? C9 Fe1 C3 156.60(17) . . ? C4 Fe1 C3 40.09(18) . . ? C7 Fe1 C3 107.91(15) . . ? O19 S1 O18 120.43(18) . . ? O19 S1 F20 104.84(16) . . ? O18 S1 F20 105.03(17) . . ? O19 S1 C10 113.01(15) . . ? O18 S1 C10 110.40(17) . . ? F20 S1 C10 100.63(14) . . ? 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 1.417(5) . ? C1 C2 1.426(5) . ? C1 Fe1 2.049(3) . ? C1 H1 0.9500 . ? C2 C3 1.434(6) . ? C2 Fe1 2.056(3) . ? C2 H2 0.9500 . ? C3 C4 1.414(6) . ? C3 Fe1 2.066(4) . ? C3 H3 0.9500 . ? C4 C5 1.425(6) . ? C4 Fe1 2.060(4) . ? C4 H4 0.9500 . ? C5 Fe1 2.047(3) . ? C5 H5 0.9500 . ? C6 C7 1.427(6) . ? C6 C10 1.443(5) . ? C6 Fe1 2.043(3) . ? C6 H6 0.9500 . ? C7 C8 1.411(5) . ? C7 Fe1 2.062(3) . ? C7 H7 0.9500 . ? C8 C9 1.437(4) . ? C8 Fe1 2.058(3) . ? C8 H8 0.9500 . ? C9 C10 1.448(5) . ? C9 C11 1.469(4) . ? C9 Fe1 2.060(3) . ? C10 S1 1.721(4) . ? C10 Fe1 2.006(3) . ? C11 C16 1.395(4) . ? C11 C12 1.401(4) . ? C12 C13 1.389(5) . ? C12 H12 0.9500 . ? C13 C14 1.384(5) . ? C13 H13 0.9500 . ? C14 F17 1.364(4) . ? C14 C15 1.377(5) . ? C15 C16 1.393(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? O18 S1 1.421(3) . ? O19 S1 1.414(3) . ? F20 S1 1.572(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 C5 C1 C2 C3 0.5(4) . . . . ? Fe1 C1 C2 C3 59.9(2) . . . . ? C5 C1 C2 Fe1 -59.4(2) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? Fe1 C2 C3 C4 59.1(3) . . . . ? C1 C2 C3 Fe1 -59.6(2) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? Fe1 C3 C4 C5 59.0(2) . . . . ? C2 C3 C4 Fe1 -58.8(3) . . . . ? C2 C1 C5 C4 -0.4(4) . . . . ? Fe1 C1 C5 C4 -60.0(2) . . . . ? C2 C1 C5 Fe1 59.6(2) . . . . ? C3 C4 C5 C1 0.1(4) . . . . ? Fe1 C4 C5 C1 59.7(2) . . . . ? C3 C4 C5 Fe1 -59.6(3) . . . . ? C10 C6 C7 C8 0.1(4) . . . . ? Fe1 C6 C7 C8 58.5(2) . . . . ? C10 C6 C7 Fe1 -58.5(2) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? Fe1 C7 C8 C9 58.3(2) . . . . ? C6 C7 C8 Fe1 -58.0(2) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? Fe1 C8 C9 C10 58.1(2) . . . . ? C7 C8 C9 C11 177.2(3) . . . . ? Fe1 C8 C9 C11 -124.3(3) . . . . ? C7 C8 C9 Fe1 -58.5(2) . . . . ? C7 C6 C10 C9 -0.3(4) . . . . ? Fe1 C6 C10 C9 -60.5(2) . . . . ? C7 C6 C10 S1 173.3(2) . . . . ? Fe1 C6 C10 S1 113.2(2) . . . . ? C7 C6 C10 Fe1 60.2(2) . . . . ? C8 C9 C10 C6 0.5(3) . . . . ? C11 C9 C10 C6 -177.0(3) . . . . ? Fe1 C9 C10 C6 60.1(2) . . . . ? C8 C9 C10 S1 -172.6(2) . . . . ? C11 C9 C10 S1 10.0(5) . . . . ? Fe1 C9 C10 S1 -112.9(3) . . . . ? C8 C9 C10 Fe1 -59.6(2) . . . . ? C11 C9 C10 Fe1 122.9(3) . . . . ? C8 C9 C11 C16 -136.1(3) . . . . ? C10 C9 C11 C16 40.9(5) . . . . ? Fe1 C9 C11 C16 132.4(3) . . . . ? C8 C9 C11 C12 39.8(5) . . . . ? C10 C9 C11 C12 -143.2(3) . . . . ? Fe1 C9 C11 C12 -51.6(4) . . . . ? C16 C11 C12 C13 -0.4(5) . . . . ? C9 C11 C12 C13 -176.4(3) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 F17 -178.9(3) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? F17 C14 C15 C16 179.3(3) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C11 -0.4(5) . . . . ? C12 C11 C16 C15 0.9(5) . . . . ? C9 C11 C16 C15 176.8(3) . . . . ? C6 C10 S1 O19 -151.4(3) . . . . ? C9 C10 S1 O19 21.0(3) . . . . ? Fe1 C10 S1 O19 -67.6(2) . . . . ? C6 C10 S1 O18 -13.2(3) . . . . ? C9 C10 S1 O18 159.1(3) . . . . ? Fe1 C10 S1 O18 70.5(2) . . . . ? C6 C10 S1 F20 97.3(3) . . . . ? C9 C10 S1 F20 -90.3(3) . . . . ? Fe1 C10 S1 F20 -178.89(18) . . . . ?