#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:40:48 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708624.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_7708624 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 'C17 H16 Fe O4 S' _chemical_formula_sum 'C17 H16 Fe O4 S' _chemical_formula_weight 372.21 _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 96.042(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.7313(11) _cell_length_b 7.4199(5) _cell_length_c 12.4538(8) _cell_measurement_reflns_used 5229 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.4758 _cell_measurement_theta_min 2.4482 _cell_measurement_wavelength 0.710730 _cell_volume 1537.48(18) _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 0.997 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'APEXII Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_orient_matrix_UB_11 0.0502593 _diffrn_orient_matrix_UB_12 -0.0958491 _diffrn_orient_matrix_UB_13 -0.0155920 _diffrn_orient_matrix_UB_21 -0.0103060 _diffrn_orient_matrix_UB_22 -0.0679436 _diffrn_orient_matrix_UB_23 0.0502429 _diffrn_orient_matrix_UB_31 -0.0623510 _diffrn_orient_matrix_UB_32 -0.0660308 _diffrn_orient_matrix_UB_33 -0.0290652 _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 0.0376 _diffrn_reflns_av_unetI/netI 0.0405 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 10192 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.482 _diffrn_reflns_theta_min 2.448 _exptl_absorpt_coefficient_mu 1.134 _exptl_absorpt_correction_T_max 0.628 _exptl_absorpt_correction_T_min 0.531 _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 1.608 _exptl_crystal_description prism _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.540 _exptl_crystal_size_mid 0.490 _exptl_crystal_size_min 0.410 _refine_diff_density_max 0.293 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.093 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3490 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0303 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.2797P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.0858 _reflns_number_gt 3115 _reflns_number_total 3490 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1dt03492h2.cif _cod_data_source_block WE14161 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7708624 _shelx_res_file ; TITL WE14161 [Space group= P2(1)/c] job.res created by SHELXL-2018/3 at 15:33:16 on 28-Apr-2021 REM Old TITL WE14161 REM SHELXT solution in P2(1)/c: R1 0.065, Rweak 0.002, Alpha 0.023 REM 0.519 for 249 systematic absences, Orientation a'=c, b'=-b, c'=a REM Formula found by SHELXT: C17 Fe O4 S CELL 0.71073 16.7313 7.4199 12.4538 90.000 96.042 90.000 ZERR 4.000 0.0011 0.0005 0.0008 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H FE O S UNIT 68 64 4 16 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.41 0.49 0.54 ACTA OMIT 1 0 0 BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.051800 0.279700 FVAR 0.58306 FE1 3 0.134248 0.325368 0.652490 11.00000 0.01290 0.00909 = 0.01228 -0.00004 0.00242 -0.00032 C1 1 0.087301 0.217809 0.783145 11.00000 0.02211 0.01643 = 0.01829 0.00275 0.00684 -0.00333 AFIX 43 H1 2 0.094678 0.262776 0.854928 11.00000 -1.20000 AFIX 0 C2 1 0.024463 0.266530 0.702771 11.00000 0.01459 0.01834 = 0.02852 0.00344 0.00658 -0.00003 AFIX 43 H2 2 -0.017548 0.349742 0.711352 11.00000 -1.20000 AFIX 0 C3 1 0.035421 0.169301 0.607597 11.00000 0.01918 0.02000 = 0.02479 0.00001 -0.00195 -0.00750 AFIX 43 H3 2 0.001842 0.175744 0.541272 11.00000 -1.20000 AFIX 0 C4 1 0.105288 0.060338 0.628248 11.00000 0.02734 0.00962 = 0.02580 -0.00270 0.00783 -0.00414 AFIX 43 H4 2 0.126701 -0.018016 0.578161 11.00000 -1.20000 AFIX 0 C5 1 0.137439 0.089528 0.737300 11.00000 0.02115 0.01315 = 0.02512 0.00746 0.00401 0.00088 AFIX 43 H5 2 0.183916 0.033650 0.773111 11.00000 -1.20000 AFIX 0 C6 1 0.206651 0.529569 0.702871 11.00000 0.01632 0.01252 = 0.01517 -0.00149 0.00425 -0.00330 C7 1 0.138854 0.597474 0.634966 11.00000 0.02282 0.00907 = 0.01855 0.00225 0.00253 -0.00092 AFIX 43 H7 2 0.100160 0.681724 0.654532 11.00000 -1.20000 AFIX 0 C8 1 0.140894 0.514352 0.533070 11.00000 0.03127 0.01642 = 0.01343 0.00267 0.00216 -0.00489 AFIX 43 H8 2 0.103150 0.533652 0.471662 11.00000 -1.20000 AFIX 0 C9 1 0.208357 0.397453 0.537200 11.00000 0.02567 0.02078 = 0.01684 -0.00403 0.01148 -0.00847 AFIX 43 H9 2 0.223288 0.326176 0.479164 11.00000 -1.20000 AFIX 0 C10 1 0.249661 0.405015 0.642472 11.00000 0.01625 0.01662 = 0.02078 -0.00411 0.00689 -0.00349 AFIX 43 H10 2 0.296776 0.340023 0.668038 11.00000 -1.20000 AFIX 0 S1 5 0.233252 0.587912 0.836303 11.00000 0.01539 0.01432 = 0.01350 -0.00179 0.00350 -0.00239 O11 4 0.282546 0.448376 0.887100 11.00000 0.02230 0.01913 = 0.02058 0.00387 -0.00013 -0.00031 O12 4 0.165825 0.652032 0.886152 11.00000 0.01992 0.02576 = 0.01901 -0.00639 0.00897 -0.00292 O13 4 0.287654 0.764874 0.827274 11.00000 0.01765 0.01398 = 0.01829 -0.00461 0.00480 -0.00395 C14 1 0.350025 0.756926 0.757489 11.00000 0.01588 0.01460 = 0.01646 -0.00379 0.00321 -0.00522 C15 1 0.417656 0.654368 0.783425 11.00000 0.02109 0.02070 = 0.01534 0.00416 0.00151 -0.00123 AFIX 43 H15 2 0.423948 0.586736 0.848538 11.00000 -1.20000 AFIX 0 C16 1 0.477017 0.651089 0.712568 11.00000 0.01551 0.02133 = 0.02324 0.00314 0.00166 0.00272 AFIX 43 H16 2 0.523508 0.578413 0.728424 11.00000 -1.20000 AFIX 0 C17 1 0.468135 0.753837 0.619100 11.00000 0.01819 0.01876 = 0.01726 -0.00268 0.00450 -0.00529 C18 1 0.399860 0.860862 0.595881 11.00000 0.02210 0.02294 = 0.01731 0.00494 0.00006 -0.00086 AFIX 43 H18 2 0.394322 0.933422 0.532685 11.00000 -1.20000 AFIX 0 C19 1 0.340272 0.861195 0.664949 11.00000 0.01793 0.01820 = 0.01945 0.00113 -0.00064 -0.00018 AFIX 43 H19 2 0.293251 0.932136 0.649024 11.00000 -1.20000 AFIX 0 O20 4 0.522594 0.759102 0.544480 11.00000 0.02417 0.02981 = 0.02298 0.00476 0.01072 0.00073 C21 1 0.588272 0.634763 0.558493 11.00000 0.02185 0.03263 = 0.03390 -0.00297 0.01190 -0.00041 AFIX 137 H21A 2 0.624338 0.668554 0.622460 11.00000 -1.50000 H21B 2 0.617855 0.637750 0.494654 11.00000 -1.50000 H21C 2 0.567592 0.512856 0.567960 11.00000 -1.50000 AFIX 0 HKLF 4 REM WE14161 [Space group= P2(1)/c] REM wR2 = 0.0858, GooF = S = 1.017, Restrained GooF = 1.017 for all data REM R1 = 0.0303 for 3115 Fo > 4sig(Fo) and 0.0347 for all 3490 data REM 209 parameters refined using 0 restraints END WGHT 0.0355 0.6159 REM Highest difference peak 0.293, deepest hole -0.466, 1-sigma level 0.093 Q1 1 0.4170 0.3392 0.6921 11.00000 0.05 0.29 Q2 1 0.0222 0.1801 0.6641 11.00000 0.05 0.28 Q3 1 0.3807 0.2298 0.6749 11.00000 0.05 0.28 Q4 1 -0.0427 0.1012 0.7075 11.00000 0.05 0.27 Q5 1 0.3410 0.3392 0.6843 11.00000 0.05 0.26 Q6 1 0.3166 0.7522 0.4946 11.00000 0.05 0.26 Q7 1 0.3450 0.6303 0.5275 11.00000 0.05 0.25 Q8 1 0.3390 0.1669 0.6964 11.00000 0.05 0.25 Q9 1 0.3264 0.6476 0.5349 11.00000 0.05 0.25 Q10 1 0.3251 0.3263 0.6987 11.00000 0.05 0.25 Q11 1 0.0815 0.6281 0.7138 11.00000 0.05 0.25 Q12 1 0.0887 0.6562 0.6889 11.00000 0.05 0.24 Q13 1 0.0716 0.6273 0.6824 11.00000 0.05 0.24 Q14 1 0.0693 0.1090 0.6204 11.00000 0.05 0.24 Q15 1 0.2249 0.7125 0.6316 11.00000 0.05 0.24 Q16 1 0.0848 0.6746 0.8289 11.00000 0.05 0.24 Q17 1 0.4017 0.3732 0.7530 11.00000 0.05 0.23 Q18 1 0.6468 0.8038 0.6353 11.00000 0.05 0.23 Q19 1 0.1924 0.5805 0.8776 11.00000 0.05 0.23 Q20 1 0.6767 0.4653 0.4996 11.00000 0.05 0.23 ; _shelx_res_checksum 13198 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 Fe1 Fe 0.13425(2) 0.32537(3) 0.65249(2) 0.01135(9) Uani 1 1 d . . . . . C1 C 0.08730(11) 0.2178(3) 0.78315(15) 0.0186(4) Uani 1 1 d . . . . . H1 H 0.094678 0.262776 0.854928 0.022 Uiso 1 1 calc R U . . . C2 C 0.02446(10) 0.2665(3) 0.70277(15) 0.0202(4) Uani 1 1 d . . . . . H2 H -0.017548 0.349742 0.711352 0.024 Uiso 1 1 calc R U . . . C3 C 0.03542(11) 0.1693(3) 0.60760(16) 0.0216(4) Uani 1 1 d . . . . . H3 H 0.001842 0.175744 0.541272 0.026 Uiso 1 1 calc R U . . . C4 C 0.10529(11) 0.0603(2) 0.62825(16) 0.0206(4) Uani 1 1 d . . . . . H4 H 0.126701 -0.018016 0.578161 0.025 Uiso 1 1 calc R U . . . C5 C 0.13744(11) 0.0895(2) 0.73730(15) 0.0197(4) Uani 1 1 d . . . . . H5 H 0.183916 0.033650 0.773111 0.024 Uiso 1 1 calc R U . . . C6 C 0.20665(10) 0.5296(2) 0.70287(14) 0.0145(3) Uani 1 1 d . . . . . C7 C 0.13885(10) 0.5975(2) 0.63497(14) 0.0168(4) Uani 1 1 d . . . . . H7 H 0.100160 0.681724 0.654532 0.020 Uiso 1 1 calc R U . . . C8 C 0.14089(12) 0.5144(3) 0.53307(15) 0.0204(4) Uani 1 1 d . . . . . H8 H 0.103150 0.533652 0.471662 0.024 Uiso 1 1 calc R U . . . C9 C 0.20836(11) 0.3975(3) 0.53720(15) 0.0204(4) Uani 1 1 d . . . . . H9 H 0.223288 0.326176 0.479164 0.025 Uiso 1 1 calc R U . . . C10 C 0.24966(10) 0.4050(3) 0.64247(14) 0.0175(4) Uani 1 1 d . . . . . H10 H 0.296776 0.340023 0.668038 0.021 Uiso 1 1 calc R U . . . S1 S 0.23325(2) 0.58791(6) 0.83630(3) 0.01426(11) Uani 1 1 d . . . . . O11 O 0.28255(7) 0.44838(18) 0.88710(10) 0.0208(3) Uani 1 1 d . . . . . O12 O 0.16582(7) 0.65203(18) 0.88615(10) 0.0211(3) Uani 1 1 d . . . . . O13 O 0.28765(7) 0.76487(17) 0.82727(10) 0.0164(3) Uani 1 1 d . . . . . C14 C 0.35002(10) 0.7569(2) 0.75749(14) 0.0155(3) Uani 1 1 d . . . . . C15 C 0.41766(11) 0.6544(3) 0.78343(15) 0.0191(4) Uani 1 1 d . . . . . H15 H 0.423948 0.586736 0.848538 0.023 Uiso 1 1 calc R U . . . C16 C 0.47702(10) 0.6511(3) 0.71257(15) 0.0201(4) Uani 1 1 d . . . . . H16 H 0.523508 0.578413 0.728424 0.024 Uiso 1 1 calc R U . . . C17 C 0.46814(10) 0.7538(3) 0.61910(14) 0.0179(4) Uani 1 1 d . . . . . C18 C 0.39986(11) 0.8609(3) 0.59588(15) 0.0209(4) Uani 1 1 d . . . . . H18 H 0.394322 0.933422 0.532685 0.025 Uiso 1 1 calc R U . . . C19 C 0.34027(11) 0.8612(3) 0.66495(15) 0.0187(4) Uani 1 1 d . . . . . H19 H 0.293251 0.932136 0.649024 0.022 Uiso 1 1 calc R U . . . O20 O 0.52259(8) 0.7591(2) 0.54448(10) 0.0251(3) Uani 1 1 d . . . . . C21 C 0.58827(11) 0.6348(3) 0.55849(18) 0.0288(5) Uani 1 1 d . . . . . H21A H 0.624338 0.668554 0.622460 0.043 Uiso 1 1 calc R U . . . H21B H 0.617855 0.637750 0.494654 0.043 Uiso 1 1 calc R U . . . H21C H 0.567592 0.512856 0.567960 0.043 Uiso 1 1 calc R U . . . 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 0.01290(14) 0.00909(14) 0.01228(15) -0.00004(9) 0.00242(9) -0.00032(8) C1 0.0221(9) 0.0164(9) 0.0183(9) 0.0027(7) 0.0068(7) -0.0033(7) C2 0.0146(8) 0.0183(9) 0.0285(10) 0.0034(8) 0.0066(7) 0.0000(7) C3 0.0192(8) 0.0200(10) 0.0248(10) 0.0000(8) -0.0019(7) -0.0075(7) C4 0.0273(9) 0.0096(8) 0.0258(10) -0.0027(7) 0.0078(8) -0.0041(7) C5 0.0212(8) 0.0131(9) 0.0251(10) 0.0075(8) 0.0040(7) 0.0009(7) C6 0.0163(8) 0.0125(8) 0.0152(8) -0.0015(7) 0.0042(6) -0.0033(7) C7 0.0228(9) 0.0091(8) 0.0185(9) 0.0023(7) 0.0025(7) -0.0009(7) C8 0.0313(10) 0.0164(9) 0.0134(9) 0.0027(7) 0.0022(7) -0.0049(8) C9 0.0257(9) 0.0208(10) 0.0168(9) -0.0040(8) 0.0115(7) -0.0085(8) C10 0.0162(8) 0.0166(9) 0.0208(9) -0.0041(7) 0.0069(7) -0.0035(7) S1 0.0154(2) 0.0143(2) 0.0135(2) -0.00179(17) 0.00350(15) -0.00239(16) O11 0.0223(6) 0.0191(7) 0.0206(7) 0.0039(6) -0.0001(5) -0.0003(5) O12 0.0199(6) 0.0258(7) 0.0190(7) -0.0064(6) 0.0090(5) -0.0029(5) O13 0.0176(6) 0.0140(6) 0.0183(6) -0.0046(5) 0.0048(5) -0.0039(5) C14 0.0159(7) 0.0146(9) 0.0165(9) -0.0038(7) 0.0032(6) -0.0052(7) C15 0.0211(9) 0.0207(10) 0.0153(9) 0.0042(7) 0.0015(7) -0.0012(7) C16 0.0155(8) 0.0213(10) 0.0232(10) 0.0031(8) 0.0017(7) 0.0027(7) C17 0.0182(8) 0.0188(9) 0.0173(9) -0.0027(8) 0.0045(7) -0.0053(7) C18 0.0221(9) 0.0229(10) 0.0173(9) 0.0049(8) 0.0001(7) -0.0009(8) C19 0.0179(8) 0.0182(9) 0.0194(9) 0.0011(8) -0.0006(7) -0.0002(7) O20 0.0242(7) 0.0298(8) 0.0230(7) 0.0048(6) 0.0107(5) 0.0007(6) C21 0.0219(9) 0.0326(11) 0.0339(12) -0.0030(10) 0.0119(8) -0.0004(9) 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' 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 C6 Fe1 C7 41.63(7) . . ? C6 Fe1 C10 41.57(7) . . ? C7 Fe1 C10 70.01(7) . . ? C6 Fe1 C4 154.63(8) . . ? C7 Fe1 C4 162.26(8) . . ? C10 Fe1 C4 118.87(8) . . ? C6 Fe1 C5 120.35(7) . . ? C7 Fe1 C5 155.15(7) . . ? C10 Fe1 C5 107.89(7) . . ? C4 Fe1 C5 40.83(8) . . ? C6 Fe1 C1 108.50(7) . . ? C7 Fe1 C1 119.72(7) . . ? C10 Fe1 C1 127.53(7) . . ? C4 Fe1 C1 68.65(8) . . ? C5 Fe1 C1 40.90(7) . . ? C6 Fe1 C3 163.64(7) . . ? C7 Fe1 C3 124.81(7) . . ? C10 Fe1 C3 153.04(8) . . ? C4 Fe1 C3 40.72(7) . . ? C5 Fe1 C3 68.47(8) . . ? C1 Fe1 C3 68.24(8) . . ? C6 Fe1 C2 126.77(7) . . ? C7 Fe1 C2 106.84(7) . . ? C10 Fe1 C2 165.27(8) . . ? C4 Fe1 C2 68.49(8) . . ? C5 Fe1 C2 68.58(7) . . ? C1 Fe1 C2 40.62(7) . . ? C3 Fe1 C2 40.44(8) . . ? C6 Fe1 C8 68.47(7) . . ? C7 Fe1 C8 40.48(7) . . ? C10 Fe1 C8 68.51(8) . . ? C4 Fe1 C8 125.49(8) . . ? C5 Fe1 C8 163.43(8) . . ? C1 Fe1 C8 153.86(8) . . ? C3 Fe1 C8 106.97(8) . . ? C2 Fe1 C8 119.01(8) . . ? C6 Fe1 C9 68.49(7) . . ? C7 Fe1 C9 68.63(7) . . ? C10 Fe1 C9 40.44(7) . . ? C4 Fe1 C9 107.31(7) . . ? C5 Fe1 C9 126.66(8) . . ? C1 Fe1 C9 164.83(8) . . ? C3 Fe1 C9 118.92(8) . . ? C2 Fe1 C9 153.04(8) . . ? C8 Fe1 C9 40.33(7) . . ? C2 C1 C5 108.09(17) . . ? C2 C1 Fe1 69.95(10) . . ? C5 C1 Fe1 69.53(10) . . ? C2 C1 H1 126.0 . . ? C5 C1 H1 126.0 . . ? Fe1 C1 H1 126.1 . . ? C3 C2 C1 107.99(16) . . ? C3 C2 Fe1 69.73(10) . . ? C1 C2 Fe1 69.43(10) . . ? C3 C2 H2 126.0 . . ? C1 C2 H2 126.0 . . ? Fe1 C2 H2 126.4 . . ? C2 C3 C4 108.34(16) . . ? C2 C3 Fe1 69.84(10) . . ? C4 C3 Fe1 69.35(10) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe1 C3 H3 126.6 . . ? C3 C4 C5 107.87(16) . . ? C3 C4 Fe1 69.92(10) . . ? C5 C4 Fe1 69.65(10) . . ? C3 C4 H4 126.1 . . ? C5 C4 H4 126.1 . . ? Fe1 C4 H4 125.9 . . ? C4 C5 C1 107.71(16) . . ? C4 C5 Fe1 69.53(10) . . ? C1 C5 Fe1 69.56(10) . . ? C4 C5 H5 126.1 . . ? C1 C5 H5 126.1 . . ? Fe1 C5 H5 126.3 . . ? C7 C6 C10 109.10(15) . . ? C7 C6 S1 125.92(13) . . ? C10 C6 S1 124.99(14) . . ? C7 C6 Fe1 70.45(10) . . ? C10 C6 Fe1 70.58(10) . . ? S1 C6 Fe1 125.27(9) . . ? C8 C7 C6 106.48(16) . . ? C8 C7 Fe1 70.61(11) . . ? C6 C7 Fe1 67.92(10) . . ? C8 C7 H7 126.8 . . ? C6 C7 H7 126.8 . . ? Fe1 C7 H7 126.3 . . ? C7 C8 C9 109.14(16) . . ? C7 C8 Fe1 68.91(10) . . ? C9 C8 Fe1 70.15(10) . . ? C7 C8 H8 125.4 . . ? C9 C8 H8 125.4 . . ? Fe1 C8 H8 127.1 . . ? C10 C9 C8 108.52(16) . . ? C10 C9 Fe1 68.71(10) . . ? C8 C9 Fe1 69.52(10) . . ? C10 C9 H9 125.7 . . ? C8 C9 H9 125.7 . . ? Fe1 C9 H9 127.6 . . ? C9 C10 C6 106.76(16) . . ? C9 C10 Fe1 70.85(10) . . ? C6 C10 Fe1 67.85(9) . . ? C9 C10 H10 126.6 . . ? C6 C10 H10 126.6 . . ? Fe1 C10 H10 126.2 . . ? O12 S1 O11 119.69(8) . . ? O12 S1 O13 103.75(7) . . ? O11 S1 O13 108.54(7) . . ? O12 S1 C6 111.50(8) . . ? O11 S1 C6 108.79(8) . . ? O13 S1 C6 103.15(7) . . ? C14 O13 S1 117.65(11) . . ? C15 C14 C19 121.85(16) . . ? C15 C14 O13 121.10(16) . . ? C19 C14 O13 117.02(16) . . ? C14 C15 C16 118.95(17) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 120.03(17) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? O20 C17 C16 124.44(17) . . ? O20 C17 C18 115.58(16) . . ? C16 C17 C18 119.98(16) . . ? C19 C18 C17 119.97(17) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C14 119.17(17) . . ? C18 C19 H19 120.4 . . ? C14 C19 H19 120.4 . . ? C17 O20 C21 117.14(15) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C6 1.9992(17) . ? Fe1 C7 2.0331(18) . ? Fe1 C10 2.0358(17) . ? Fe1 C4 2.0402(19) . ? Fe1 C5 2.0417(18) . ? Fe1 C1 2.0422(18) . ? Fe1 C3 2.0477(18) . ? Fe1 C2 2.0491(17) . ? Fe1 C8 2.0556(18) . ? Fe1 C9 2.0639(17) . ? C1 C2 1.420(3) . ? C1 C5 1.427(3) . ? C1 H1 0.9500 . ? C2 C3 1.416(3) . ? C2 H2 0.9500 . ? C3 C4 1.422(3) . ? C3 H3 0.9500 . ? C4 C5 1.424(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.433(2) . ? C6 C10 1.432(2) . ? C6 S1 1.7295(17) . ? C7 C8 1.415(3) . ? C7 H7 0.9500 . ? C8 C9 1.420(3) . ? C8 H8 0.9500 . ? C9 C10 1.417(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? S1 O12 1.4255(12) . ? S1 O11 1.4292(14) . ? S1 O13 1.6083(13) . ? O13 C14 1.4278(19) . ? C14 C15 1.374(3) . ? C14 C19 1.383(3) . ? C15 C16 1.397(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C17 O20 1.369(2) . ? C17 C18 1.396(3) . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O20 C21 1.431(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 59.27(13) . . . . ? C5 C1 C2 Fe1 -59.28(12) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? Fe1 C2 C3 C4 58.84(13) . . . . ? C1 C2 C3 Fe1 -59.08(13) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? Fe1 C3 C4 C5 59.54(12) . . . . ? C2 C3 C4 Fe1 -59.14(13) . . . . ? C3 C4 C5 C1 -0.4(2) . . . . ? Fe1 C4 C5 C1 59.31(12) . . . . ? C3 C4 C5 Fe1 -59.72(12) . . . . ? C2 C1 C5 C4 0.3(2) . . . . ? Fe1 C1 C5 C4 -59.28(12) . . . . ? C2 C1 C5 Fe1 59.54(13) . . . . ? C10 C6 C7 C8 -0.2(2) . . . . ? S1 C6 C7 C8 179.62(13) . . . . ? Fe1 C6 C7 C8 -60.42(12) . . . . ? C10 C6 C7 Fe1 60.25(12) . . . . ? S1 C6 C7 Fe1 -119.96(14) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? Fe1 C7 C8 C9 -58.73(13) . . . . ? C6 C7 C8 Fe1 58.69(12) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? Fe1 C8 C9 C10 -57.73(12) . . . . ? C7 C8 C9 Fe1 57.97(13) . . . . ? C8 C9 C10 C6 -0.3(2) . . . . ? Fe1 C9 C10 C6 -58.57(12) . . . . ? C8 C9 C10 Fe1 58.22(12) . . . . ? C7 C6 C10 C9 0.3(2) . . . . ? S1 C6 C10 C9 -179.47(13) . . . . ? Fe1 C6 C10 C9 60.49(12) . . . . ? C7 C6 C10 Fe1 -60.17(12) . . . . ? S1 C6 C10 Fe1 120.04(14) . . . . ? C7 C6 S1 O12 23.89(18) . . . . ? C10 C6 S1 O12 -156.35(14) . . . . ? Fe1 C6 S1 O12 -66.47(13) . . . . ? C7 C6 S1 O11 158.02(14) . . . . ? C10 C6 S1 O11 -22.21(17) . . . . ? Fe1 C6 S1 O11 67.67(12) . . . . ? C7 C6 S1 O13 -86.87(16) . . . . ? C10 C6 S1 O13 92.90(16) . . . . ? Fe1 C6 S1 O13 -177.23(10) . . . . ? O12 S1 O13 C14 -165.03(12) . . . . ? O11 S1 O13 C14 66.66(14) . . . . ? C6 S1 O13 C14 -48.63(14) . . . . ? S1 O13 C14 C15 -70.74(19) . . . . ? S1 O13 C14 C19 111.25(16) . . . . ? C19 C14 C15 C16 -2.0(3) . . . . ? O13 C14 C15 C16 -179.95(16) . . . . ? C14 C15 C16 C17 1.6(3) . . . . ? C15 C16 C17 O20 -179.66(17) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? O20 C17 C18 C19 178.33(17) . . . . ? C16 C17 C18 C19 -1.4(3) . . . . ? C17 C18 C19 C14 1.1(3) . . . . ? C15 C14 C19 C18 0.7(3) . . . . ? O13 C14 C19 C18 178.70(16) . . . . ? C16 C17 O20 C21 7.3(3) . . . . ? C18 C17 O20 C21 -172.46(17) . . . . ?