#------------------------------------------------------------------------------ #$Date: 2020-05-01 04:34:16 +0300 (Fri, 01 May 2020) $ #$Revision: 251350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240439.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_7240439 loop_ _publ_author_name 'Verpekin, Victor V.' 'Semeikin, Oleg V.' 'Vasiliev, Alexander D.' 'Kondrasenko, Alexander A.' 'Belousov, Yuri A.' 'Ustynyuk, Nikolai A.' _publ_section_title ; Catalyzed M--C coupling reactions in the synthesis of \s-(pyridylethynyl)dicarbonylcyclopentadienyliron complexes ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 17014 _journal_paper_doi 10.1039/D0RA02333G _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C15 H8 Fe N2 O2 S' _chemical_formula_sum 'C15 H8 Fe N2 O2 S' _chemical_formula_weight 336.14 _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-02-07 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.765(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.4302(5) _cell_length_b 11.8451(10) _cell_length_c 17.9823(15) _cell_measurement_reflns_used 2151 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.44 _cell_measurement_theta_min 2.27 _cell_volume 1366.69(19) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker PHOTON II' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL (Sheldrick 2015)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker PHOTON-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_unetI/netI 0.0467 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 14867 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.963 _diffrn_reflns_theta_min 2.060 _exptl_absorpt_coefficient_mu 1.260 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.6461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10. ; _exptl_crystal_colour dark-yellow _exptl_crystal_density_diffrn 1.634 _exptl_crystal_description prism _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.310 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.311 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2964 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0496 _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^)+(0.0442P)^2^+0.2917P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.1087 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2227 _reflns_number_total 2964 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02333g2.cif _cod_data_source_block Ant19 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240439 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.607 _shelx_estimated_absorpt_t_max 0.843 _shelx_res_file ; Ant19.res created by SHELXL-2014/7 TITL Ant19_0m_a_a.res in P2(1)/n REM Old TITL Ant19_0m_a.res in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.136, Rweak 0.014, Alpha 0.069, Orientation as input REM Formula found by SHELXT: C14 N3 O2 S Fe CELL 0.71073 6.4302 11.8451 17.9823 90.000 93.765 90.000 ZERR 4.000 0.0005 0.0010 0.0015 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O S FE UNIT 60 32 8 8 4 4 TEMP 23.000 SIZE 0.44 0.31 0.14 L.S. 10 acta BOND $H LIST 6 FMAP 2 PLAN 40 WGHT 0.044200 0.291700 FVAR 0.46066 FE 6 0.547703 0.273292 0.514517 11.00000 0.03324 0.03919 = 0.03351 0.00034 -0.00759 0.00237 S 5 -0.292362 0.278551 0.241461 11.00000 0.05068 0.10667 = 0.05743 -0.00297 -0.00307 -0.01626 O1 4 0.284087 0.074050 0.503125 11.00000 0.06456 0.04743 = 0.07291 -0.00675 -0.00263 -0.00934 O2 4 0.264657 0.408853 0.597149 11.00000 0.04821 0.06683 = 0.07165 -0.01338 0.00931 0.00492 N1 3 -0.080359 0.284273 0.294108 11.00000 0.04771 0.06150 = 0.03849 -0.00136 -0.00088 -0.00460 N2 3 -0.262005 0.382365 0.186508 11.00000 0.04824 0.10552 = 0.04995 -0.00029 -0.00842 0.00674 C1 1 0.388717 0.152174 0.508349 11.00000 0.04161 0.04435 = 0.04044 -0.00572 -0.00670 0.01002 C2 1 0.372925 0.354566 0.563909 11.00000 0.03469 0.04983 = 0.04404 0.00175 -0.00957 -0.00231 C3 1 0.412920 0.325172 0.422590 11.00000 0.03905 0.04126 = 0.04219 -0.00177 -0.00596 0.00207 C4 1 0.801485 0.378112 0.545960 11.00000 0.03762 0.04912 = 0.06041 -0.00602 -0.01065 -0.00463 AFIX 43 H4 2 0.790942 0.454759 0.556273 11.00000 -1.20000 AFIX 0 C5 1 0.833021 0.330179 0.476662 11.00000 0.03753 0.06681 = 0.04691 0.00238 0.00021 -0.00572 AFIX 43 H5 2 0.849455 0.369861 0.432810 11.00000 -1.20000 AFIX 0 C6 1 0.835842 0.211548 0.484146 11.00000 0.03913 0.06561 = 0.05809 -0.01483 -0.00612 0.01079 AFIX 43 H6 2 0.851780 0.159413 0.446272 11.00000 -1.20000 AFIX 0 C7 1 0.809887 0.186592 0.560079 11.00000 0.04164 0.05148 = 0.06437 0.00780 -0.01437 0.00642 AFIX 43 H7 2 0.807559 0.114878 0.581061 11.00000 -1.20000 AFIX 0 C8 1 0.788458 0.288342 0.597818 11.00000 0.04098 0.07229 = 0.04496 -0.00539 -0.01570 0.00711 AFIX 43 H8 2 0.768951 0.296108 0.648351 11.00000 -1.20000 AFIX 0 C9 1 0.325614 0.359421 0.365496 11.00000 0.04932 0.04245 = 0.03788 -0.00632 -0.00622 0.00763 C10 1 0.226293 0.410625 0.300157 11.00000 0.05199 0.04549 = 0.02992 -0.00747 -0.00371 0.01134 C11 1 0.309921 0.500977 0.263947 11.00000 0.05926 0.04711 = 0.04362 -0.00509 -0.00532 -0.00076 AFIX 43 H11 2 0.441827 0.525962 0.280780 11.00000 -1.20000 AFIX 0 C12 1 0.207546 0.558032 0.202785 11.00000 0.08553 0.04938 = 0.03879 -0.00127 -0.00183 0.00313 AFIX 43 H12 2 0.271375 0.619339 0.181367 11.00000 -1.20000 AFIX 0 C13 1 0.016066 0.523351 0.175303 11.00000 0.07877 0.06278 = 0.03853 0.00517 -0.00929 0.02045 AFIX 43 H13 2 -0.052747 0.560946 0.135496 11.00000 -1.20000 AFIX 0 C14 1 -0.075612 0.430118 0.207963 11.00000 0.04832 0.06692 = 0.02947 -0.00456 -0.00338 0.01703 C15 1 0.027736 0.372896 0.269911 11.00000 0.04759 0.04573 = 0.03058 -0.00834 0.00248 0.01051 HKLF 4 REM Ant19_0m_a_a.res in P2(1)/n REM R1 = 0.0496 for 2227 Fo > 4sig(Fo) and 0.0738 for all 2964 data REM 190 parameters refined using 0 restraints END WGHT 0.0378 0.3733 REM Highest difference peak 0.311, deepest hole -0.392, 1-sigma level 0.062 Q1 1 -0.2856 0.3648 0.2409 11.00000 0.05 0.31 Q2 1 0.4331 0.3335 0.4841 11.00000 0.05 0.28 Q3 1 -0.1739 0.2328 0.2468 11.00000 0.05 0.27 Q4 1 0.3124 0.3054 0.3803 11.00000 0.05 0.25 Q5 1 0.4772 0.2225 0.4865 11.00000 0.05 0.25 Q6 1 0.3437 0.4028 0.4017 11.00000 0.05 0.24 Q7 1 0.8160 0.1178 0.5624 11.00000 0.05 0.24 Q8 1 -0.2592 0.4130 0.1403 11.00000 0.05 0.24 Q9 1 0.5311 0.3651 0.5224 11.00000 0.05 0.24 Q10 1 0.7370 0.2773 0.4690 11.00000 0.05 0.23 Q11 1 0.5288 0.2085 0.5576 11.00000 0.05 0.22 Q12 1 0.2449 0.5963 0.1798 11.00000 0.05 0.21 Q13 1 0.4354 0.2607 0.4210 11.00000 0.05 0.20 Q14 1 0.5551 0.2829 0.5785 11.00000 0.05 0.20 Q15 1 0.4359 0.2774 0.5501 11.00000 0.05 0.20 Q16 1 0.5870 0.3487 0.4771 11.00000 0.05 0.20 Q17 1 -0.2043 0.1648 0.1997 11.00000 0.05 0.19 Q18 1 0.1420 0.3567 0.2969 11.00000 0.05 0.19 Q19 1 0.8520 0.2143 0.5245 11.00000 0.05 0.19 Q20 1 0.4397 0.2183 0.6042 11.00000 0.05 0.19 Q21 1 0.1970 0.5060 0.2608 11.00000 0.05 0.19 Q22 1 0.5371 0.4854 0.2405 11.00000 0.05 0.19 Q23 1 -0.0199 0.2174 0.3065 11.00000 0.05 0.19 Q24 1 -0.4183 0.2169 0.2566 11.00000 0.05 0.19 Q25 1 0.2711 0.5228 0.2134 11.00000 0.05 0.18 Q26 1 0.4358 0.3540 0.3588 11.00000 0.05 0.18 Q27 1 0.5790 0.1946 0.5216 11.00000 0.05 0.18 Q28 1 0.3117 0.6033 0.1628 11.00000 0.05 0.18 Q29 1 0.9099 0.2696 0.4780 11.00000 0.05 0.17 Q30 1 1.0290 0.2161 0.4454 11.00000 0.05 0.17 Q31 1 0.1755 0.5841 0.2219 11.00000 0.05 0.17 Q32 1 0.4820 0.4767 0.3059 11.00000 0.05 0.17 Q33 1 0.7865 0.2025 0.5938 11.00000 0.05 0.17 Q34 1 0.2657 0.3366 0.6355 11.00000 0.05 0.17 Q35 1 0.7231 0.3217 0.5203 11.00000 0.05 0.17 Q36 1 0.0838 0.5614 0.2027 11.00000 0.05 0.17 Q37 1 0.8439 0.2274 0.5967 11.00000 0.05 0.17 Q38 1 0.2069 0.4437 0.3056 11.00000 0.05 0.16 Q39 1 0.7196 0.2618 0.5769 11.00000 0.05 0.16 Q40 1 0.6833 0.3521 0.5553 11.00000 0.05 0.16 ; _shelx_res_checksum 67600 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 Fe Fe 0.54770(7) 0.27329(4) 0.51452(2) 0.03574(16) Uani 1 1 d . . . . . S S -0.29236(17) 0.27855(11) 0.24146(6) 0.0719(3) Uani 1 1 d . . . . . O1 O 0.2841(4) 0.0741(2) 0.50313(15) 0.0619(7) Uani 1 1 d . . . . . O2 O 0.2647(4) 0.4089(2) 0.59715(16) 0.0620(7) Uani 1 1 d . . . . . N1 N -0.0804(5) 0.2843(3) 0.29411(16) 0.0494(7) Uani 1 1 d . . . . . N2 N -0.2620(5) 0.3824(3) 0.18651(18) 0.0684(10) Uani 1 1 d . . . . . C1 C 0.3887(5) 0.1522(3) 0.50835(18) 0.0425(8) Uani 1 1 d . . . . . C2 C 0.3729(5) 0.3546(3) 0.56391(19) 0.0434(8) Uani 1 1 d . . . . . C3 C 0.4129(5) 0.3252(3) 0.42259(18) 0.0412(8) Uani 1 1 d . . . . . C4 C 0.8015(5) 0.3781(3) 0.5460(2) 0.0497(9) Uani 1 1 d . . . . . H4 H 0.7909 0.4548 0.5563 0.060 Uiso 1 1 calc R U . . . C5 C 0.8330(5) 0.3302(3) 0.4767(2) 0.0505(9) Uani 1 1 d . . . . . H5 H 0.8495 0.3699 0.4328 0.061 Uiso 1 1 calc R U . . . C6 C 0.8358(5) 0.2115(3) 0.4841(2) 0.0547(10) Uani 1 1 d . . . . . H6 H 0.8518 0.1594 0.4463 0.066 Uiso 1 1 calc R U . . . C7 C 0.8099(5) 0.1866(3) 0.5601(2) 0.0533(9) Uani 1 1 d . . . . . H7 H 0.8076 0.1149 0.5811 0.064 Uiso 1 1 calc R U . . . C8 C 0.7885(5) 0.2883(3) 0.5978(2) 0.0536(10) Uani 1 1 d . . . . . H8 H 0.7690 0.2961 0.6484 0.064 Uiso 1 1 calc R U . . . C9 C 0.3256(5) 0.3594(3) 0.36550(19) 0.0436(8) Uani 1 1 d . . . . . C10 C 0.2263(5) 0.4106(3) 0.30016(18) 0.0427(8) Uani 1 1 d . . . . . C11 C 0.3099(6) 0.5010(3) 0.26395(19) 0.0504(9) Uani 1 1 d . . . . . H11 H 0.4418 0.5260 0.2808 0.060 Uiso 1 1 calc R U . . . C12 C 0.2075(7) 0.5580(3) 0.2028(2) 0.0582(10) Uani 1 1 d . . . . . H12 H 0.2714 0.6193 0.1814 0.070 Uiso 1 1 calc R U . . . C13 C 0.0161(7) 0.5234(3) 0.1753(2) 0.0606(11) Uani 1 1 d . . . . . H13 H -0.0527 0.5609 0.1355 0.073 Uiso 1 1 calc R U . . . C14 C -0.0756(6) 0.4301(3) 0.20796(18) 0.0485(9) Uani 1 1 d . . . . . C15 C 0.0277(5) 0.3729(3) 0.26991(17) 0.0413(8) 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 Fe 0.0332(3) 0.0392(3) 0.0335(3) 0.0003(2) -0.00759(18) 0.0024(2) S 0.0507(6) 0.1067(9) 0.0574(7) -0.0030(6) -0.0031(5) -0.0163(6) O1 0.0646(18) 0.0474(16) 0.0729(19) -0.0068(13) -0.0026(14) -0.0093(13) O2 0.0482(15) 0.0668(18) 0.0717(19) -0.0134(15) 0.0093(14) 0.0049(13) N1 0.0477(17) 0.061(2) 0.0385(16) -0.0014(14) -0.0009(13) -0.0046(15) N2 0.048(2) 0.106(3) 0.050(2) -0.0003(19) -0.0084(16) 0.0067(19) C1 0.0416(19) 0.044(2) 0.0404(19) -0.0057(15) -0.0067(15) 0.0100(16) C2 0.0347(18) 0.050(2) 0.044(2) 0.0017(16) -0.0096(15) -0.0023(15) C3 0.0390(18) 0.0413(19) 0.0422(19) -0.0018(15) -0.0060(15) 0.0021(14) C4 0.0376(19) 0.049(2) 0.060(2) -0.0060(18) -0.0106(17) -0.0046(15) C5 0.038(2) 0.067(3) 0.047(2) 0.0024(19) 0.0002(16) -0.0057(17) C6 0.039(2) 0.066(3) 0.058(2) -0.015(2) -0.0061(17) 0.0108(18) C7 0.042(2) 0.051(2) 0.064(3) 0.0078(19) -0.0144(18) 0.0064(16) C8 0.041(2) 0.072(3) 0.045(2) -0.0054(19) -0.0157(16) 0.0071(18) C9 0.049(2) 0.0425(19) 0.0379(19) -0.0063(15) -0.0062(16) 0.0076(15) C10 0.052(2) 0.045(2) 0.0299(17) -0.0075(14) -0.0037(15) 0.0113(16) C11 0.059(2) 0.047(2) 0.044(2) -0.0051(16) -0.0053(17) -0.0008(17) C12 0.086(3) 0.049(2) 0.039(2) -0.0013(17) -0.002(2) 0.003(2) C13 0.079(3) 0.063(3) 0.039(2) 0.0052(19) -0.009(2) 0.020(2) C14 0.048(2) 0.067(2) 0.0295(18) -0.0046(16) -0.0034(15) 0.0170(18) C15 0.0476(19) 0.046(2) 0.0306(17) -0.0083(15) 0.0025(15) 0.0105(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' 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' Fe Fe 0.3463 0.8444 '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 C1 Fe C2 95.16(15) . . ? C1 Fe C3 88.80(15) . . ? C2 Fe C3 89.56(14) . . ? C1 Fe C8 120.95(15) . . ? C2 Fe C8 93.38(15) . . ? C3 Fe C8 149.61(15) . . ? C1 Fe C7 94.26(15) . . ? C2 Fe C7 126.43(16) . . ? C3 Fe C7 143.26(16) . . ? C8 Fe C7 38.93(14) . . ? C1 Fe C6 102.63(15) . . ? C2 Fe C6 157.61(15) . . ? C3 Fe C6 104.15(15) . . ? C8 Fe C6 65.85(15) . . ? C7 Fe C6 39.53(15) . . ? C1 Fe C4 159.56(15) . . ? C2 Fe C4 92.94(15) . . ? C3 Fe C4 110.02(15) . . ? C8 Fe C4 39.65(14) . . ? C7 Fe C4 65.98(15) . . ? C6 Fe C4 65.91(15) . . ? C1 Fe C5 138.92(16) . . ? C2 Fe C5 125.79(15) . . ? C3 Fe C5 88.44(14) . . ? C8 Fe C5 65.48(15) . . ? C7 Fe C5 65.67(15) . . ? C6 Fe C5 39.22(14) . . ? C4 Fe C5 38.76(14) . . ? N2 S N1 101.44(17) . . ? C15 N1 S 106.1(2) . . ? C14 N2 S 106.6(3) . . ? O1 C1 Fe 178.8(3) . . ? O2 C2 Fe 177.9(3) . . ? C9 C3 Fe 178.6(3) . . ? C5 C4 C8 107.4(3) . . ? C5 C4 Fe 71.0(2) . . ? C8 C4 Fe 69.85(19) . . ? C5 C4 H4 126.3 . . ? C8 C4 H4 126.3 . . ? Fe C4 H4 124.5 . . ? C4 C5 C6 108.7(3) . . ? C4 C5 Fe 70.2(2) . . ? C6 C5 Fe 70.0(2) . . ? C4 C5 H5 125.6 . . ? C6 C5 H5 125.6 . . ? Fe C5 H5 125.8 . . ? C5 C6 C7 107.3(3) . . ? C5 C6 Fe 70.8(2) . . ? C7 C6 Fe 70.1(2) . . ? C5 C6 H6 126.3 . . ? C7 C6 H6 126.3 . . ? Fe C6 H6 124.3 . . ? C8 C7 C6 108.1(3) . . ? C8 C7 Fe 70.36(19) . . ? C6 C7 Fe 70.3(2) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? Fe C7 H7 124.9 . . ? C7 C8 C4 108.4(3) . . ? C7 C8 Fe 70.71(19) . . ? C4 C8 Fe 70.50(19) . . ? C7 C8 H8 125.8 . . ? C4 C8 H8 125.8 . . ? Fe C8 H8 124.6 . . ? C3 C9 C10 174.6(4) . . ? C11 C10 C15 115.5(3) . . ? C11 C10 C9 123.2(3) . . ? C15 C10 C9 121.3(3) . . ? C10 C11 C12 124.1(4) . . ? C10 C11 H11 117.9 . . ? C12 C11 H11 117.9 . . ? C13 C12 C11 120.1(4) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 118.8(3) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? N2 C14 C13 126.7(3) . . ? N2 C14 C15 112.3(4) . . ? C13 C14 C15 120.9(3) . . ? N1 C15 C10 126.1(3) . . ? N1 C15 C14 113.4(3) . . ? C10 C15 C14 120.5(3) . . ? 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 Fe C1 1.761(4) . ? Fe C2 1.763(4) . ? Fe C3 1.917(3) . ? Fe C8 2.090(3) . ? Fe C7 2.094(3) . ? Fe C6 2.097(4) . ? Fe C4 2.098(3) . ? Fe C5 2.109(4) . ? S N2 1.598(4) . ? S N1 1.609(3) . ? O1 C1 1.144(4) . ? O2 C2 1.145(4) . ? N1 C15 1.347(4) . ? N2 C14 1.358(5) . ? C3 C9 1.208(4) . ? C4 C5 1.396(5) . ? C4 C8 1.420(5) . ? C4 H4 0.9300 . ? C5 C6 1.412(5) . ? C5 H5 0.9300 . ? C6 C7 1.418(5) . ? C6 H6 0.9300 . ? C7 C8 1.394(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.434(4) . ? C10 C11 1.380(5) . ? C10 C15 1.426(5) . ? C11 C12 1.416(5) . ? C11 H11 0.9300 . ? C12 C13 1.360(5) . ? C12 H12 0.9300 . ? C13 C14 1.399(5) . ? C13 H13 0.9300 . ? C14 C15 1.430(4) . ?