#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:40:48 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270122 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708621.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_7708621 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 'C15 H11 F Fe I N O2 S' _chemical_formula_sum 'C15 H11 F Fe I N O2 S' _chemical_formula_weight 471.06 _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 92.999(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.0556(16) _cell_length_b 6.8264(7) _cell_length_c 15.1425(14) _cell_measurement_reflns_used 9588 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5016 _cell_measurement_theta_min 2.7095 _cell_measurement_wavelength 0.710730 _cell_volume 1554.1(3) _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 2018_2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector '(CMOS) PHOTON 100' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_orient_matrix_UB_11 0.0199892 _diffrn_orient_matrix_UB_12 -0.1015034 _diffrn_orient_matrix_UB_13 0.0443228 _diffrn_orient_matrix_UB_21 0.0633461 _diffrn_orient_matrix_UB_22 0.0373167 _diffrn_orient_matrix_UB_23 -0.0077605 _diffrn_orient_matrix_UB_31 -0.0033892 _diffrn_orient_matrix_UB_32 0.0988122 _diffrn_orient_matrix_UB_33 0.0484607 _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 0.0380 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14099 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.529 _diffrn_reflns_theta_min 2.694 _diffrn_source_current 1.00 _diffrn_source_power 50.0 _diffrn_source_voltage 50.00 _exptl_absorpt_coefficient_mu 3.106 _exptl_absorpt_correction_T_max 0.805 _exptl_absorpt_correction_T_min 0.616 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.013 _exptl_crystal_description plate _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.070 _refine_diff_density_max 3.385 _refine_diff_density_min -3.565 _refine_diff_density_rms 0.950 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3722 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0168P)^2^+6.9064P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.0787 _reflns_number_gt 3246 _reflns_number_total 3722 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1dt03492h2.cif _cod_data_source_block WE13091 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7708621 _shelx_res_file ; TITL WE13091 [Space group= P2(1)/c] job.res created by SHELXL-2018/3 at 15:17:42 on 05-Feb-2021 REM Old TITL WE13091 REM SHELXT solution in P2(1)/c: R1 0.176, Rweak 0.008, Alpha 0.024 REM 0.728 for 271 systematic absences, Orientation as input REM Formula found by SHELXT: C16 F3 Fe I N CELL 0.71073 15.0556 6.8264 15.1425 90.000 92.999 90.000 ZERR 4.000 0.0016 0.0007 0.0014 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H F FE I N O S UNIT 60 44 4 4 4 4 8 4 MERG 2 TWIN 0.006 0. -0.994 0 -1 0 -1.006 0 -0.006 FMAP 2 PLAN 20 SIZE 0.07 0.18 0.29 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.016800 6.906400 BASF 0.00040 FVAR 0.33180 FE1 4 0.211119 0.373177 0.416490 11.00000 0.01411 0.00933 = 0.01411 -0.00006 0.00010 -0.00087 C1 1 0.251147 0.625996 0.480118 11.00000 0.03026 0.01366 = 0.03752 -0.00850 -0.00827 -0.00116 AFIX 43 H1 2 0.292358 0.634614 0.529659 11.00000 -1.20000 AFIX 0 C2 1 0.272024 0.633019 0.390334 11.00000 0.02705 0.01057 = 0.05209 0.00460 0.00682 -0.00487 AFIX 43 H2 2 0.329881 0.647201 0.368950 11.00000 -1.20000 AFIX 0 C3 1 0.191833 0.615276 0.337599 11.00000 0.04734 0.01559 = 0.02949 0.00892 -0.00512 0.00211 AFIX 43 H3 2 0.186380 0.615745 0.274812 11.00000 -1.20000 AFIX 0 C4 1 0.121384 0.596744 0.395288 11.00000 0.02268 0.01558 = 0.04595 0.00130 -0.00731 0.00457 AFIX 43 H4 2 0.060180 0.582086 0.377982 11.00000 -1.20000 AFIX 0 C5 1 0.157870 0.603826 0.483147 11.00000 0.03211 0.01873 = 0.03365 -0.01016 0.00234 0.00897 AFIX 43 H5 2 0.125447 0.595210 0.535168 11.00000 -1.20000 AFIX 0 I1 5 0.013163 0.070855 0.348581 11.00000 0.01199 0.02899 = 0.02406 0.00122 0.00083 -0.00488 C6 1 0.144722 0.121223 0.391289 11.00000 0.00983 0.01255 = 0.01333 0.00183 0.00144 -0.00220 C7 1 0.174392 0.124419 0.481888 11.00000 0.01794 0.01436 = 0.01187 0.00167 0.00426 -0.00161 AFIX 43 H7 2 0.137369 0.115282 0.530634 11.00000 -1.20000 AFIX 0 C8 1 0.268315 0.143480 0.487670 11.00000 0.01876 0.01250 = 0.01018 0.00207 -0.00204 0.00258 AFIX 43 H8 2 0.304084 0.150588 0.541149 11.00000 -1.20000 AFIX 0 C9 1 0.300940 0.150363 0.400806 11.00000 0.01336 0.01145 = 0.01265 0.00083 -0.00015 0.00022 C10 1 0.223140 0.136989 0.340151 11.00000 0.01321 0.00975 = 0.00989 -0.00087 0.00073 -0.00044 S1 8 0.223203 0.166900 0.227306 11.00000 0.01459 0.02123 = 0.00922 0.00166 0.00163 -0.00040 O11 7 0.138730 0.219947 0.189965 11.00000 0.02004 0.04920 = 0.01521 0.00526 -0.00136 0.00534 O12 7 0.300925 0.266031 0.202821 11.00000 0.02226 0.04420 = 0.01666 0.00953 0.00339 -0.00987 F13 3 0.236963 -0.050614 0.196683 11.00000 0.04365 0.02640 = 0.01756 -0.00827 0.00248 0.00215 C14 1 0.396361 0.154057 0.382203 11.00000 0.01358 0.01725 = 0.01485 0.00318 0.00180 0.00158 C15 1 0.431833 0.026914 0.321689 11.00000 0.01771 0.01745 = 0.01920 -0.00127 0.00014 0.00013 AFIX 43 H15 2 0.394031 -0.059496 0.287946 11.00000 -1.20000 AFIX 0 C16 1 0.522387 0.026767 0.310826 11.00000 0.01673 0.02210 = 0.02657 -0.00114 0.00324 0.00449 AFIX 43 H16 2 0.547743 -0.059398 0.269798 11.00000 -1.20000 AFIX 0 C17 1 0.575553 0.155472 0.361250 11.00000 0.01332 0.02602 = 0.03289 0.00222 0.00246 0.00009 AFIX 43 H17 2 0.637768 0.155097 0.353530 11.00000 -1.20000 AFIX 0 N18 6 0.543708 0.279777 0.420053 11.00000 0.01587 0.03000 = 0.03245 -0.00691 -0.00483 -0.00196 C19 1 0.455547 0.278196 0.429361 11.00000 0.01576 0.02630 = 0.02397 -0.00596 -0.00200 0.00092 AFIX 43 H19 2 0.431927 0.366754 0.470466 11.00000 -1.20000 AFIX 0 HKLF 4 REM WE13091 [Space group= P2(1)/c] REM wR2 = 0.0787, GooF = S = 1.071, Restrained GooF = 1.071 for all data REM R1 = 0.0337 for 3246 Fo > 4sig(Fo) and 0.0405 for all 3722 data REM 200 parameters refined using 0 restraints END WGHT 0.0177 6.5890 REM Highest difference peak 3.385, deepest hole -3.565, 1-sigma level 0.950 Q1 1 0.1001 0.7332 0.2973 11.00000 0.05 3.39 Q2 1 0.0996 0.8441 0.2965 11.00000 0.05 3.36 Q3 1 0.0997 0.5981 0.2964 11.00000 0.05 3.30 Q4 1 0.1012 0.2492 0.2957 11.00000 0.05 3.28 Q5 1 0.1011 0.4607 0.2957 11.00000 0.05 3.27 Q6 1 0.1010 0.0975 0.2966 11.00000 0.05 3.26 Q7 1 0.1004 0.3427 0.2966 11.00000 0.05 3.25 Q8 1 0.0992 -0.0009 0.2973 11.00000 0.05 3.19 Q9 1 0.4806 0.4143 0.3648 11.00000 0.05 3.16 Q10 1 0.4800 -0.0850 0.3657 11.00000 0.05 3.15 Q11 1 0.0031 0.1954 0.3450 11.00000 0.05 3.14 Q12 1 0.4800 0.6446 0.3655 11.00000 0.05 3.13 Q13 1 0.4802 -0.2073 0.3651 11.00000 0.05 3.13 Q14 1 0.4810 0.2250 0.3643 11.00000 0.05 2.80 Q15 1 0.4799 0.1426 0.1827 11.00000 0.05 2.61 Q16 1 0.4798 0.0152 0.1831 11.00000 0.05 2.59 Q17 1 0.5198 -0.0501 0.3171 11.00000 0.05 2.56 Q18 1 0.1515 0.1226 0.1414 11.00000 0.05 2.56 Q19 1 0.0981 -0.1020 0.4197 11.00000 0.05 2.55 Q20 1 0.5196 -0.2338 0.3162 11.00000 0.05 2.50 ; _shelx_res_checksum 38290 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 0.21112(3) 0.37318(7) 0.41649(3) 0.01254(12) Uani 1 1 d . . . . . C1 C 0.2511(3) 0.6260(6) 0.4801(3) 0.0275(9) Uani 1 1 d . . . . . H1 H 0.292358 0.634614 0.529659 0.033 Uiso 1 1 calc R U . . . C2 C 0.2720(3) 0.6330(6) 0.3903(3) 0.0297(10) Uani 1 1 d . . . . . H2 H 0.329881 0.647201 0.368950 0.036 Uiso 1 1 calc R U . . . C3 C 0.1918(3) 0.6153(6) 0.3376(3) 0.0311(10) Uani 1 1 d . . . . . H3 H 0.186380 0.615745 0.274812 0.037 Uiso 1 1 calc R U . . . C4 C 0.1214(3) 0.5967(6) 0.3953(3) 0.0284(9) Uani 1 1 d . . . . . H4 H 0.060180 0.582086 0.377982 0.034 Uiso 1 1 calc R U . . . C5 C 0.1579(3) 0.6038(6) 0.4831(3) 0.0281(9) Uani 1 1 d . . . . . H5 H 0.125447 0.595210 0.535168 0.034 Uiso 1 1 calc R U . . . I1 I 0.01316(2) 0.07086(4) 0.34858(2) 0.02169(8) Uani 1 1 d . . . . . C6 C 0.1447(2) 0.1212(5) 0.3913(2) 0.0119(6) Uani 1 1 d . . . . . C7 C 0.1744(2) 0.1244(5) 0.4819(2) 0.0146(7) Uani 1 1 d . . . . . H7 H 0.137369 0.115282 0.530634 0.018 Uiso 1 1 calc R U . . . C8 C 0.2683(2) 0.1435(5) 0.4877(2) 0.0139(7) Uani 1 1 d . . . . . H8 H 0.304084 0.150588 0.541149 0.017 Uiso 1 1 calc R U . . . C9 C 0.3009(2) 0.1504(5) 0.4008(2) 0.0125(6) Uani 1 1 d . . . . . C10 C 0.2231(2) 0.1370(5) 0.3402(2) 0.0109(6) Uani 1 1 d . . . . . S1 S 0.22320(6) 0.16690(14) 0.22731(5) 0.01498(18) Uani 1 1 d . . . . . O11 O 0.13873(19) 0.2199(5) 0.18997(17) 0.0282(7) Uani 1 1 d . . . . . O12 O 0.30092(19) 0.2660(5) 0.20282(17) 0.0276(7) Uani 1 1 d . . . . . F13 F 0.23696(18) -0.0506(4) 0.19668(15) 0.0292(6) Uani 1 1 d . . . . . C14 C 0.3964(2) 0.1541(6) 0.3822(2) 0.0152(7) Uani 1 1 d . . . . . C15 C 0.4318(2) 0.0269(6) 0.3217(2) 0.0181(7) Uani 1 1 d . . . . . H15 H 0.394031 -0.059496 0.287946 0.022 Uiso 1 1 calc R U . . . C16 C 0.5224(3) 0.0268(6) 0.3108(3) 0.0217(8) Uani 1 1 d . . . . . H16 H 0.547743 -0.059398 0.269798 0.026 Uiso 1 1 calc R U . . . C17 C 0.5756(3) 0.1555(6) 0.3613(3) 0.0240(8) Uani 1 1 d . . . . . H17 H 0.637768 0.155097 0.353530 0.029 Uiso 1 1 calc R U . . . N18 N 0.5437(2) 0.2798(6) 0.4201(2) 0.0263(8) Uani 1 1 d . . . . . C19 C 0.4555(3) 0.2782(6) 0.4294(3) 0.0221(8) Uani 1 1 d . . . . . H19 H 0.431927 0.366754 0.470466 0.027 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 0.0141(2) 0.0093(2) 0.0141(2) -0.00006(18) 0.00010(18) -0.00087(18) C1 0.030(2) 0.0137(19) 0.038(2) -0.0085(17) -0.0083(18) -0.0012(16) C2 0.027(2) 0.0106(18) 0.052(3) 0.0046(18) 0.007(2) -0.0049(16) C3 0.047(3) 0.016(2) 0.029(2) 0.0089(16) -0.0051(19) 0.0021(18) C4 0.023(2) 0.016(2) 0.046(3) 0.0013(18) -0.0073(18) 0.0046(16) C5 0.032(2) 0.019(2) 0.034(2) -0.0102(17) 0.0023(18) 0.0090(17) I1 0.01199(12) 0.02899(15) 0.02406(14) 0.00122(10) 0.00083(9) -0.00488(10) C6 0.0098(15) 0.0125(16) 0.0133(15) 0.0018(12) 0.0014(12) -0.0022(12) C7 0.0179(17) 0.0144(17) 0.0119(15) 0.0017(13) 0.0043(13) -0.0016(13) C8 0.0188(17) 0.0125(16) 0.0102(15) 0.0021(12) -0.0020(13) 0.0026(13) C9 0.0134(16) 0.0114(16) 0.0127(15) 0.0008(12) -0.0002(12) 0.0002(13) C10 0.0132(16) 0.0098(16) 0.0099(14) -0.0009(12) 0.0007(12) -0.0004(12) S1 0.0146(4) 0.0212(5) 0.0092(4) 0.0017(3) 0.0016(3) -0.0004(3) O11 0.0200(14) 0.049(2) 0.0152(13) 0.0053(13) -0.0014(10) 0.0053(14) O12 0.0223(14) 0.0442(19) 0.0167(13) 0.0095(13) 0.0034(11) -0.0099(13) F13 0.0437(15) 0.0264(13) 0.0176(11) -0.0083(10) 0.0025(10) 0.0022(11) C14 0.0136(17) 0.0173(18) 0.0149(16) 0.0032(13) 0.0018(13) 0.0016(13) C15 0.0177(18) 0.0175(19) 0.0192(17) -0.0013(14) 0.0001(14) 0.0001(14) C16 0.0167(18) 0.022(2) 0.027(2) -0.0011(16) 0.0032(15) 0.0045(15) C17 0.0133(18) 0.026(2) 0.033(2) 0.0022(17) 0.0025(15) 0.0001(15) N18 0.0159(16) 0.030(2) 0.0325(18) -0.0069(15) -0.0048(13) -0.0020(14) C19 0.0158(18) 0.026(2) 0.0240(19) -0.0060(16) -0.0020(14) 0.0009(16) 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 42.34(13) . . ? C10 Fe1 C2 122.20(17) . . ? C6 Fe1 C2 157.88(17) . . ? C10 Fe1 C3 109.13(16) . . ? C6 Fe1 C3 121.57(17) . . ? C2 Fe1 C3 40.49(19) . . ? C10 Fe1 C1 156.55(16) . . ? C6 Fe1 C1 159.59(17) . . ? C2 Fe1 C1 40.33(19) . . ? C3 Fe1 C1 67.97(18) . . ? C10 Fe1 C4 126.05(16) . . ? C6 Fe1 C4 106.80(16) . . ? C2 Fe1 C4 67.84(18) . . ? C3 Fe1 C4 40.33(19) . . ? C1 Fe1 C4 67.83(17) . . ? C10 Fe1 C5 162.15(16) . . ? C6 Fe1 C5 122.97(17) . . ? C2 Fe1 C5 67.73(19) . . ? C3 Fe1 C5 67.78(19) . . ? C1 Fe1 C5 40.32(18) . . ? C4 Fe1 C5 40.25(18) . . ? C10 Fe1 C7 69.32(14) . . ? C6 Fe1 C7 40.82(13) . . ? C2 Fe1 C7 160.78(17) . . ? C3 Fe1 C7 155.87(18) . . ? C1 Fe1 C7 123.25(17) . . ? C4 Fe1 C7 119.87(17) . . ? C5 Fe1 C7 105.93(17) . . ? C10 Fe1 C9 41.97(13) . . ? C6 Fe1 C9 70.72(14) . . ? C2 Fe1 C9 108.35(16) . . ? C3 Fe1 C9 127.04(17) . . ? C1 Fe1 C9 119.83(16) . . ? C4 Fe1 C9 164.38(17) . . ? C5 Fe1 C9 153.98(16) . . ? C7 Fe1 C9 68.90(14) . . ? C10 Fe1 C8 68.98(13) . . ? C6 Fe1 C8 68.90(14) . . ? C2 Fe1 C8 125.50(17) . . ? C3 Fe1 C8 163.39(18) . . ? C1 Fe1 C8 106.82(16) . . ? C4 Fe1 C8 154.07(17) . . ? C5 Fe1 C8 119.21(16) . . ? C7 Fe1 C8 40.26(14) . . ? C9 Fe1 C8 40.56(13) . . ? C2 C1 C5 107.8(4) . . ? C2 C1 Fe1 69.6(2) . . ? C5 C1 Fe1 70.0(2) . . ? C2 C1 H1 126.1 . . ? C5 C1 H1 126.1 . . ? Fe1 C1 H1 125.9 . . ? C1 C2 C3 108.3(4) . . ? C1 C2 Fe1 70.1(2) . . ? C3 C2 Fe1 70.0(2) . . ? C1 C2 H2 125.9 . . ? C3 C2 H2 125.9 . . ? Fe1 C2 H2 125.6 . . ? C4 C3 C2 107.7(4) . . ? C4 C3 Fe1 69.9(2) . . ? C2 C3 Fe1 69.5(2) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? Fe1 C3 H3 126.0 . . ? C5 C4 C3 108.1(4) . . ? C5 C4 Fe1 70.0(2) . . ? C3 C4 Fe1 69.8(2) . . ? C5 C4 H4 125.9 . . ? C3 C4 H4 125.9 . . ? Fe1 C4 H4 125.9 . . ? C4 C5 C1 108.1(4) . . ? C4 C5 Fe1 69.8(2) . . ? C1 C5 Fe1 69.7(2) . . ? C4 C5 H5 126.0 . . ? C1 C5 H5 126.0 . . ? Fe1 C5 H5 126.2 . . ? C7 C6 C10 106.9(3) . . ? C7 C6 Fe1 71.1(2) . . ? C10 C6 Fe1 68.16(19) . . ? C7 C6 I1 123.3(2) . . ? C10 C6 I1 129.4(2) . . ? Fe1 C6 I1 130.90(18) . . ? C8 C7 C6 108.9(3) . . ? C8 C7 Fe1 70.2(2) . . ? C6 C7 Fe1 68.07(19) . . ? C8 C7 H7 125.6 . . ? C6 C7 H7 125.6 . . ? Fe1 C7 H7 127.7 . . ? C7 C8 C9 109.6(3) . . ? C7 C8 Fe1 69.5(2) . . ? C9 C8 Fe1 69.43(19) . . ? C7 C8 H8 125.2 . . ? C9 C8 H8 125.2 . . ? Fe1 C8 H8 127.5 . . ? C8 C9 C10 106.0(3) . . ? C8 C9 C14 124.1(3) . . ? C10 C9 C14 129.8(3) . . ? C8 C9 Fe1 70.0(2) . . ? C10 C9 Fe1 66.82(19) . . ? C14 C9 Fe1 131.3(3) . . ? C6 C10 C9 108.6(3) . . ? C6 C10 S1 125.6(3) . . ? C9 C10 S1 125.3(3) . . ? C6 C10 Fe1 69.50(19) . . ? C9 C10 Fe1 71.21(19) . . ? S1 C10 Fe1 118.92(18) . . ? O11 S1 O12 120.76(19) . . ? O11 S1 F13 104.71(18) . . ? O12 S1 F13 104.50(18) . . ? O11 S1 C10 112.39(17) . . ? O12 S1 C10 111.08(17) . . ? F13 S1 C10 100.82(15) . . ? C15 C14 C19 117.3(3) . . ? C15 C14 C9 121.7(3) . . ? C19 C14 C9 120.8(3) . . ? C16 C15 C14 119.7(4) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 118.5(4) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? N18 C17 C16 123.4(4) . . ? N18 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C17 N18 C19 117.1(3) . . ? N18 C19 C14 124.0(4) . . ? N18 C19 H19 118.0 . . ? C14 C19 H19 118.0 . . ? 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 1.998(3) . ? Fe1 C6 2.016(3) . ? Fe1 C2 2.045(4) . ? Fe1 C3 2.051(4) . ? Fe1 C1 2.052(4) . ? Fe1 C4 2.052(4) . ? Fe1 C5 2.056(4) . ? Fe1 C7 2.056(4) . ? Fe1 C9 2.057(4) . ? Fe1 C8 2.065(3) . ? C1 C2 1.412(7) . ? C1 C5 1.416(6) . ? C1 H1 0.9500 . ? C2 C3 1.417(7) . ? C2 H2 0.9500 . ? C3 C4 1.415(7) . ? C3 H3 0.9500 . ? C4 C5 1.413(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? I1 C6 2.080(3) . ? C6 C7 1.421(5) . ? C6 C10 1.449(5) . ? C7 C8 1.418(5) . ? C7 H7 0.9500 . ? C8 C9 1.429(5) . ? C8 H8 0.9500 . ? C9 C10 1.453(5) . ? C9 C14 1.479(5) . ? C10 S1 1.721(3) . ? S1 O11 1.412(3) . ? S1 O12 1.418(3) . ? S1 F13 1.572(3) . ? C14 C15 1.389(5) . ? C14 C19 1.398(5) . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 C17 1.390(6) . ? C16 H16 0.9500 . ? C17 N18 1.337(5) . ? C17 H17 0.9500 . ? N18 C19 1.342(5) . ? C19 H19 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 0.0(5) . . . . ? Fe1 C1 C2 C3 59.8(3) . . . . ? C5 C1 C2 Fe1 -59.8(3) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? Fe1 C2 C3 C4 59.7(3) . . . . ? C1 C2 C3 Fe1 -59.9(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? Fe1 C3 C4 C5 59.7(3) . . . . ? C2 C3 C4 Fe1 -59.5(3) . . . . ? C3 C4 C5 C1 -0.2(5) . . . . ? Fe1 C4 C5 C1 59.4(3) . . . . ? C3 C4 C5 Fe1 -59.6(3) . . . . ? C2 C1 C5 C4 0.1(5) . . . . ? Fe1 C1 C5 C4 -59.4(3) . . . . ? C2 C1 C5 Fe1 59.5(3) . . . . ? C10 C6 C7 C8 0.5(4) . . . . ? Fe1 C6 C7 C8 -58.5(3) . . . . ? I1 C6 C7 C8 174.4(2) . . . . ? C10 C6 C7 Fe1 59.0(2) . . . . ? I1 C6 C7 Fe1 -127.1(3) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? Fe1 C7 C8 C9 -57.9(2) . . . . ? C6 C7 C8 Fe1 57.2(2) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? Fe1 C8 C9 C10 -57.3(2) . . . . ? C7 C8 C9 C14 -175.0(3) . . . . ? Fe1 C8 C9 C14 127.1(3) . . . . ? C7 C8 C9 Fe1 58.0(3) . . . . ? C7 C6 C10 C9 -0.2(4) . . . . ? Fe1 C6 C10 C9 60.7(2) . . . . ? I1 C6 C10 C9 -173.5(3) . . . . ? C7 C6 C10 S1 -172.4(3) . . . . ? Fe1 C6 C10 S1 -111.5(3) . . . . ? I1 C6 C10 S1 14.2(5) . . . . ? C7 C6 C10 Fe1 -60.9(2) . . . . ? I1 C6 C10 Fe1 125.7(3) . . . . ? C8 C9 C10 C6 -0.3(4) . . . . ? C14 C9 C10 C6 175.0(3) . . . . ? Fe1 C9 C10 C6 -59.7(2) . . . . ? C8 C9 C10 S1 172.0(3) . . . . ? C14 C9 C10 S1 -12.7(6) . . . . ? Fe1 C9 C10 S1 112.6(3) . . . . ? C8 C9 C10 Fe1 59.4(2) . . . . ? C14 C9 C10 Fe1 -125.3(4) . . . . ? C6 C10 S1 O11 13.7(4) . . . . ? C9 C10 S1 O11 -157.4(3) . . . . ? Fe1 C10 S1 O11 -70.8(3) . . . . ? C6 C10 S1 O12 152.4(3) . . . . ? C9 C10 S1 O12 -18.6(4) . . . . ? Fe1 C10 S1 O12 67.9(3) . . . . ? C6 C10 S1 F13 -97.3(3) . . . . ? C9 C10 S1 F13 91.6(3) . . . . ? Fe1 C10 S1 F13 178.22(18) . . . . ? C8 C9 C14 C15 130.2(4) . . . . ? C10 C9 C14 C15 -44.3(6) . . . . ? Fe1 C9 C14 C15 -137.2(3) . . . . ? C8 C9 C14 C19 -45.7(5) . . . . ? C10 C9 C14 C19 139.8(4) . . . . ? Fe1 C9 C14 C19 46.9(5) . . . . ? C19 C14 C15 C16 0.4(5) . . . . ? C9 C14 C15 C16 -175.7(3) . . . . ? C14 C15 C16 C17 -0.1(6) . . . . ? C15 C16 C17 N18 0.1(6) . . . . ? C16 C17 N18 C19 -0.4(6) . . . . ? C17 N18 C19 C14 0.7(6) . . . . ? C15 C14 C19 N18 -0.7(6) . . . . ? C9 C14 C19 N18 175.4(4) . . . . ?