#------------------------------------------------------------------------------ #$Date: 2021-10-16 02:57:36 +0300 (Sat, 16 Oct 2021) $ #$Revision: 269974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/37/7243743.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_7243743 loop_ _publ_author_name 'Krause, Bernhard Markus' 'Bauer, Britta' 'Neudoerfl, Joerg' 'Wieder, Thomas' 'Schmalz, Hans G\"unther' _publ_section_title ; ItaCORMs: Conjugation with a CO-releasing Unit greatly Enhances the Anti-inflammatory Activity of Itaconates ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D1MD00163A _journal_year 2021 _chemical_formula_moiety 'C15 H14 Fe O7' _chemical_formula_sum 'C15 H14 Fe O7' _chemical_formula_weight 362.11 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-04-14 deposited with the CCDC. 2021-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.110(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.1067(3) _cell_length_b 12.2043(5) _cell_length_c 9.3734(4) _cell_measurement_reflns_used 8640 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 71.74 _cell_measurement_theta_min 4.86 _cell_volume 788.45(6) _computing_cell_refinement 'Bruker APEX 3' _computing_data_collection 'Bruker APEX 3' _computing_data_reduction 'Bruker APEX 3' _computing_molecular_graphics 'SCHAKAL99 (E. Keller 1999)' _computing_publication_material 'PLATON (A. L. Spek 1980-2015)' _computing_structure_refinement ; SHELXL-2014/7 (Sheldrick, 2014) SHELXLE (C. B. Huebschle 2016)' ; _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_detector_type 'Bruker PhotonIII M14' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_unetI/netI 0.0432 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _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 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 14895 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 71.892 _diffrn_reflns_theta_min 4.865 _diffrn_source 'micro focus' _exptl_absorpt_coefficient_mu 7.987 _exptl_absorpt_correction_T_max 0.7535 _exptl_absorpt_correction_T_min 0.4517 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.525 _exptl_crystal_description 'Irregular block' _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.030 _refine_diff_density_max 1.104 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.069 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.467(8) _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 210 _refine_ls_number_reflns 3057 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0431 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.8031P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.1039 _reflns_Friedel_coverage 0.905 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 2880 _reflns_number_total 3057 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1md00163a2.cif _cod_data_source_block bhd_kse9_nm _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7243743 _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 0.380 _shelx_estimated_absorpt_t_max 0.796 _shelx_res_file ; bhd_kse9_nm_0m_b.res created by SHELXL-2014/7 TITL bhd_kse9_nm_0m_b.res in P2(1) CELL 1.54178 7.1067 12.2043 9.3734 90.000 104.110 90.000 ZERR 2.000 0.0003 0.0005 0.0004 0.000 0.002 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H FE O UNIT 30 28 2 14 TEMP -173.150 SIZE 0.03 0.10 0.15 L.S. 10 ACTA CONF BOND $H LIST 6 FMAP 2 PLAN 20 TWIN WGHT 0.046800 0.803100 BASF 0.46708 FVAR 0.27523 FE1 3 0.218752 0.477211 0.538509 11.00000 0.02322 0.03140 = 0.01955 -0.00266 0.00687 -0.00472 O1 4 0.256638 0.531698 0.227202 11.00000 0.02124 0.04791 = 0.01903 -0.00004 0.00701 0.00325 O2 4 0.574933 0.495693 0.318735 11.00000 0.02043 0.04985 = 0.02416 -0.00523 0.00689 -0.00157 O3 4 0.861049 0.542330 -0.005268 11.00000 0.02881 0.02788 = 0.02418 0.00205 0.00580 -0.00239 O4 4 0.578728 0.624723 -0.007280 11.00000 0.05111 0.03712 = 0.05152 0.00607 0.01867 0.01561 O5 4 0.212526 0.281042 0.356837 11.00000 0.05286 0.03901 = 0.04866 -0.01459 0.02004 -0.01074 O6 4 0.072628 0.360443 0.765541 11.00000 0.05078 0.06932 = 0.02917 0.00575 0.01491 -0.01877 O7 4 0.636496 0.496995 0.670924 11.00000 0.02510 0.06195 = 0.02317 -0.00066 0.00205 -0.00476 C1 1 0.230336 0.577670 0.361137 11.00000 0.02705 0.03670 = 0.02725 -0.00150 0.00912 -0.00028 C2 1 0.036892 0.561577 0.373026 11.00000 0.02219 0.03745 = 0.03297 0.00001 0.00886 0.00355 AFIX 13 H2 2 -0.064395 0.524896 0.294689 11.00000 -1.20000 AFIX 0 C3 1 0.004147 0.593566 0.509740 11.00000 0.02922 0.04107 = 0.03733 -0.00414 0.01490 0.00387 AFIX 13 H3 2 -0.121814 0.581468 0.537007 11.00000 -1.20000 AFIX 0 C4 1 0.173123 0.637523 0.609732 11.00000 0.03363 0.03530 = 0.03702 -0.01232 0.01911 -0.00374 AFIX 13 H4 2 0.165582 0.644396 0.714502 11.00000 -1.20000 AFIX 0 C5 1 0.304047 0.718117 0.559753 11.00000 0.04099 0.03655 = 0.05189 -0.01380 0.01964 -0.00646 AFIX 23 H5A 2 0.430441 0.721522 0.633095 11.00000 -1.20000 H5AB 2 0.244904 0.792010 0.551577 11.00000 -1.20000 AFIX 0 C6 1 0.336278 0.682465 0.407029 11.00000 0.03248 0.03115 = 0.04218 0.00470 0.01861 -0.00092 AFIX 23 H6A 2 0.287432 0.740069 0.332886 11.00000 -1.20000 H6AB 2 0.476524 0.672197 0.414454 11.00000 -1.20000 AFIX 0 C7 1 0.431405 0.490210 0.220542 11.00000 0.02327 0.04587 = 0.02157 -0.00106 0.00824 -0.00110 C8 1 0.415272 0.433028 0.074710 11.00000 0.02964 0.05494 = 0.02336 -0.00969 0.00906 -0.00399 AFIX 23 H8A 2 0.372940 0.356397 0.082091 11.00000 -1.20000 H8AB 2 0.315437 0.470203 -0.002254 11.00000 -1.20000 AFIX 0 C9 1 0.605170 0.433341 0.030537 11.00000 0.02931 0.03106 = 0.01981 -0.00282 0.00919 -0.00447 C10 1 0.693363 0.342209 0.008880 11.00000 0.04814 0.02530 = 0.06707 0.00025 0.02869 -0.00071 AFIX 93 H10A 2 0.807979 0.345313 -0.026085 11.00000 -1.20000 H10B 2 0.642389 0.273342 0.028217 11.00000 -1.20000 AFIX 0 C11 1 0.674851 0.543677 0.003195 11.00000 0.04099 0.03189 = 0.01510 0.00081 0.01325 0.00728 C12 1 0.940800 0.645842 -0.031250 11.00000 0.05011 0.03220 = 0.03500 0.00950 0.01557 -0.00442 AFIX 137 H12A 2 0.872732 0.673229 -0.128414 11.00000 -1.50000 H12B 2 1.078988 0.637107 -0.027550 11.00000 -1.50000 H12C 2 0.925351 0.698148 0.044405 11.00000 -1.50000 AFIX 0 C13 1 0.212817 0.357100 0.431108 11.00000 0.02886 0.03554 = 0.03880 0.00274 0.01251 -0.00878 C14 1 0.131157 0.407687 0.677438 11.00000 0.02758 0.04874 = 0.03335 -0.01029 0.00574 -0.00910 C15 1 0.473831 0.487639 0.619866 11.00000 0.03551 0.03939 = 0.01860 -0.00214 0.00783 -0.00364 HKLF 4 REM bhd_kse9_nm_0m_b.res in P2(1) REM R1 = 0.0431 for 2880 Fo > 4sig(Fo) and 0.0471 for all 3057 data REM 210 parameters refined using 1 restraints END WGHT 0.0468 0.8031 REM Highest difference peak 1.104, deepest hole -0.293, 1-sigma level 0.069 Q1 1 0.2585 0.5822 0.5213 11.00000 0.05 1.10 Q2 1 0.2552 0.3727 0.5299 11.00000 0.05 0.63 Q3 1 0.1805 0.4724 0.4187 11.00000 0.05 0.49 Q4 1 0.2558 0.4740 0.6538 11.00000 0.05 0.48 Q5 1 0.2458 0.4345 0.2532 11.00000 0.05 0.41 Q6 1 0.3165 0.5213 0.4695 11.00000 0.05 0.35 Q7 1 0.5390 0.5225 0.0595 11.00000 0.05 0.28 Q8 1 0.2047 0.5802 0.6195 11.00000 0.05 0.28 Q9 1 0.3396 0.7221 0.2995 11.00000 0.05 0.26 Q10 1 0.1106 0.4837 0.6268 11.00000 0.05 0.26 Q11 1 0.2162 0.7968 0.7371 11.00000 0.05 0.26 Q12 1 0.0322 0.4928 0.5076 11.00000 0.05 0.25 Q13 1 0.3125 0.4348 0.4690 11.00000 0.05 0.24 Q14 1 0.2765 0.3750 0.3852 11.00000 0.05 0.24 Q15 1 0.4027 0.4026 0.2162 11.00000 0.05 0.22 Q16 1 0.6223 0.6400 0.0790 11.00000 0.05 0.22 Q17 1 0.6612 0.4730 0.0320 11.00000 0.05 0.22 Q18 1 0.5728 0.4607 -0.0199 11.00000 0.05 0.22 Q19 1 0.7055 0.4406 -0.0348 11.00000 0.05 0.22 Q20 1 0.0325 0.2569 0.7852 11.00000 0.05 0.21 ; _shelx_res_checksum 9829 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 Fe1 Fe 0.21875(10) 0.47721(7) 0.53851(8) 0.0244(2) Uani 1 1 d . . . . . O1 O 0.2566(5) 0.5317(4) 0.2272(4) 0.0290(8) Uani 1 1 d . . . . . O2 O 0.5749(5) 0.4957(4) 0.3187(4) 0.0312(10) Uani 1 1 d . . . . . O3 O 0.8610(5) 0.5423(3) -0.0053(4) 0.0271(8) Uani 1 1 d . . . . . O4 O 0.5787(7) 0.6247(4) -0.0073(6) 0.0455(12) Uani 1 1 d . . . . . O5 O 0.2125(7) 0.2810(4) 0.3568(5) 0.0455(12) Uani 1 1 d . . . . . O6 O 0.0726(7) 0.3604(4) 0.7655(5) 0.0489(12) Uani 1 1 d . . . . . O7 O 0.6365(5) 0.4970(4) 0.6709(4) 0.0374(11) Uani 1 1 d . . . . . C1 C 0.2303(9) 0.5777(5) 0.3611(7) 0.0299(13) Uani 1 1 d . . . . . C2 C 0.0369(8) 0.5616(5) 0.3730(7) 0.0305(12) Uani 1 1 d . . . . . H2 H -0.0644 0.5249 0.2947 0.037 Uiso 1 1 calc R U . . . C3 C 0.0041(10) 0.5936(5) 0.5097(7) 0.0347(13) Uani 1 1 d . . . . . H3 H -0.1218 0.5815 0.5370 0.042 Uiso 1 1 calc R U . . . C4 C 0.1731(9) 0.6375(5) 0.6097(7) 0.0335(13) Uani 1 1 d . . . . . H4 H 0.1656 0.6444 0.7145 0.040 Uiso 1 1 calc R U . . . C5 C 0.3040(10) 0.7181(5) 0.5598(8) 0.0417(15) Uani 1 1 d . . . . . H5A H 0.4304 0.7215 0.6331 0.050 Uiso 1 1 calc R U . . . H5AB H 0.2449 0.7920 0.5516 0.050 Uiso 1 1 calc R U . . . C6 C 0.3363(9) 0.6825(5) 0.4070(7) 0.0336(13) Uani 1 1 d . . . . . H6A H 0.2874 0.7401 0.3329 0.040 Uiso 1 1 calc R U . . . H6AB H 0.4765 0.6722 0.4145 0.040 Uiso 1 1 calc R U . . . C7 C 0.4314(7) 0.4902(6) 0.2205(5) 0.0298(12) Uani 1 1 d . . . . . C8 C 0.4153(8) 0.4330(6) 0.0747(6) 0.0355(13) Uani 1 1 d . . . . . H8A H 0.3729 0.3564 0.0821 0.043 Uiso 1 1 calc R U . . . H8AB H 0.3154 0.4702 -0.0023 0.043 Uiso 1 1 calc R U . . . C9 C 0.6052(8) 0.4333(5) 0.0305(6) 0.0262(12) Uani 1 1 d . . . . . C10 C 0.6934(10) 0.3422(5) 0.0089(9) 0.0443(17) Uani 1 1 d . . . . . H10A H 0.8080 0.3453 -0.0261 0.053 Uiso 1 1 calc R U . . . H10B H 0.6424 0.2733 0.0282 0.053 Uiso 1 1 calc R U . . . C11 C 0.6749(9) 0.5437(5) 0.0032(6) 0.0282(12) Uani 1 1 d . . . . . C12 C 0.9408(10) 0.6458(5) -0.0312(7) 0.0382(14) Uani 1 1 d . . . . . H12A H 0.8727 0.6732 -0.1284 0.057 Uiso 1 1 calc R U . . . H12B H 1.0790 0.6371 -0.0276 0.057 Uiso 1 1 calc R U . . . H12C H 0.9254 0.6981 0.0444 0.057 Uiso 1 1 calc R U . . . C13 C 0.2128(9) 0.3571(5) 0.4311(7) 0.0337(13) Uani 1 1 d . . . . . C14 C 0.1312(9) 0.4077(6) 0.6774(7) 0.0368(14) Uani 1 1 d . . . . . C15 C 0.4738(8) 0.4876(6) 0.6199(5) 0.0310(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 Fe1 0.0232(4) 0.0314(4) 0.0195(3) -0.0027(4) 0.0069(3) -0.0047(4) O1 0.0212(18) 0.048(2) 0.0190(17) 0.0000(17) 0.0070(14) 0.0032(17) O2 0.0204(16) 0.050(3) 0.0242(17) -0.0052(18) 0.0069(13) -0.0016(17) O3 0.029(2) 0.028(2) 0.0242(19) 0.0020(15) 0.0058(15) -0.0024(16) O4 0.051(3) 0.037(3) 0.052(3) 0.006(2) 0.019(2) 0.016(2) O5 0.053(3) 0.039(3) 0.049(3) -0.015(2) 0.020(2) -0.011(2) O6 0.051(3) 0.069(3) 0.029(2) 0.006(2) 0.015(2) -0.019(3) O7 0.0251(19) 0.062(3) 0.0232(17) -0.0007(19) 0.0020(14) -0.0048(19) C1 0.027(3) 0.037(3) 0.027(3) -0.002(2) 0.009(2) 0.000(2) C2 0.022(3) 0.037(3) 0.033(3) 0.000(2) 0.009(2) 0.004(2) C3 0.029(3) 0.041(3) 0.037(3) -0.004(3) 0.015(3) 0.004(2) C4 0.034(3) 0.035(3) 0.037(3) -0.012(3) 0.019(3) -0.004(3) C5 0.041(4) 0.037(3) 0.052(4) -0.014(3) 0.020(3) -0.006(3) C6 0.032(3) 0.031(3) 0.042(4) 0.005(3) 0.019(3) -0.001(2) C7 0.023(2) 0.046(4) 0.022(2) -0.001(3) 0.0082(18) -0.001(3) C8 0.030(3) 0.055(4) 0.023(3) -0.010(2) 0.009(2) -0.004(3) C9 0.029(3) 0.031(3) 0.020(3) -0.003(2) 0.009(2) -0.004(2) C10 0.048(4) 0.025(3) 0.067(5) 0.000(3) 0.029(4) -0.001(3) C11 0.041(3) 0.032(3) 0.015(3) 0.001(2) 0.013(2) 0.007(3) C12 0.050(4) 0.032(3) 0.035(3) 0.009(3) 0.016(3) -0.004(3) C13 0.029(3) 0.036(3) 0.039(3) 0.003(3) 0.013(3) -0.009(3) C14 0.028(3) 0.049(4) 0.033(3) -0.010(3) 0.006(3) -0.009(3) C15 0.036(3) 0.039(3) 0.019(2) -0.002(3) 0.008(2) -0.004(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C13 Fe1 C14 93.3(3) . . ? C13 Fe1 C15 100.5(3) . . ? C14 Fe1 C15 102.7(3) . . ? C13 Fe1 C2 93.6(3) . . ? C14 Fe1 C2 121.7(3) . . ? C15 Fe1 C2 132.5(3) . . ? C13 Fe1 C3 125.7(3) . . ? C14 Fe1 C3 92.6(3) . . ? C15 Fe1 C3 130.5(3) . . ? C2 Fe1 C3 40.4(2) . . ? C13 Fe1 C1 91.9(3) . . ? C14 Fe1 C1 161.6(3) . . ? C15 Fe1 C1 93.7(3) . . ? C2 Fe1 C1 40.3(2) . . ? C3 Fe1 C1 70.2(2) . . ? C13 Fe1 C4 163.5(3) . . ? C14 Fe1 C4 95.8(3) . . ? C15 Fe1 C4 91.0(3) . . ? C2 Fe1 C4 69.9(3) . . ? C3 Fe1 C4 40.2(3) . . ? C1 Fe1 C4 75.3(2) . . ? C7 O1 C1 120.3(4) . . ? C11 O3 C12 115.8(5) . . ? C2 C1 O1 110.6(5) . . ? C2 C1 C6 121.7(5) . . ? O1 C1 C6 115.1(5) . . ? C2 C1 Fe1 68.2(3) . . ? O1 C1 Fe1 120.6(4) . . ? C6 C1 Fe1 112.9(4) . . ? C3 C2 C1 114.2(5) . . ? C3 C2 Fe1 70.3(4) . . ? C1 C2 Fe1 71.5(3) . . ? C3 C2 H2 122.8 . . ? C1 C2 H2 122.8 . . ? Fe1 C2 H2 122.8 . . ? C2 C3 C4 113.5(5) . . ? C2 C3 Fe1 69.3(3) . . ? C4 C3 Fe1 72.3(4) . . ? C2 C3 H3 123.2 . . ? C4 C3 H3 123.2 . . ? Fe1 C3 H3 123.2 . . ? C3 C4 C5 121.6(6) . . ? C3 C4 Fe1 67.5(3) . . ? C5 C4 Fe1 110.6(4) . . ? C3 C4 H4 115.9 . . ? C5 C4 H4 115.9 . . ? Fe1 C4 H4 115.9 . . ? C4 C5 C6 110.0(5) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5AB 109.7 . . ? C6 C5 H5AB 109.7 . . ? H5A C5 H5AB 108.2 . . ? C1 C6 C5 109.0(5) . . ? C1 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? C1 C6 H6AB 109.9 . . ? C5 C6 H6AB 109.9 . . ? H6A C6 H6AB 108.3 . . ? O2 C7 O1 124.2(5) . . ? O2 C7 C8 125.6(5) . . ? O1 C7 C8 110.2(4) . . ? C9 C8 C7 111.8(5) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8AB 109.3 . . ? C7 C8 H8AB 109.3 . . ? H8A C8 H8AB 107.9 . . ? C10 C9 C11 123.4(5) . . ? C10 C9 C8 122.2(6) . . ? C11 C9 C8 114.2(5) . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? O4 C11 O3 123.9(6) . . ? O4 C11 C9 124.1(6) . . ? O3 C11 C9 112.0(5) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 Fe1 177.1(6) . . ? O6 C14 Fe1 178.4(6) . . ? O7 C15 Fe1 178.3(7) . . ? 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 C13 1.773(6) . ? Fe1 C14 1.788(7) . ? Fe1 C15 1.792(5) . ? Fe1 C2 2.039(6) . ? Fe1 C3 2.053(6) . ? Fe1 C1 2.083(6) . ? Fe1 C4 2.118(6) . ? O1 C7 1.357(7) . ? O1 C1 1.428(7) . ? O2 C7 1.198(6) . ? O3 C11 1.345(7) . ? O3 C12 1.430(7) . ? O4 C11 1.192(7) . ? O5 C13 1.160(8) . ? O6 C14 1.164(8) . ? O7 C15 1.144(6) . ? C1 C2 1.420(8) . ? C1 C6 1.493(8) . ? C2 C3 1.412(8) . ? C2 H2 1.0000 . ? C3 C4 1.435(9) . ? C3 H3 1.0000 . ? C4 C5 1.505(9) . ? C4 H4 1.0000 . ? C5 C6 1.566(9) . ? C5 H5A 0.9900 . ? C5 H5AB 0.9900 . ? C6 H6A 0.9900 . ? C6 H6AB 0.9900 . ? C7 C8 1.514(8) . ? C8 C9 1.505(8) . ? C8 H8A 0.9900 . ? C8 H8AB 0.9900 . ? C9 C10 1.316(9) . ? C9 C11 1.479(8) . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C7 O1 C1 C2 -148.5(5) . . . . ? C7 O1 C1 C6 68.7(7) . . . . ? C7 O1 C1 Fe1 -72.4(6) . . . . ? O1 C1 C2 C3 173.2(5) . . . . ? C6 C1 C2 C3 -46.8(8) . . . . ? Fe1 C1 C2 C3 57.4(5) . . . . ? O1 C1 C2 Fe1 115.8(4) . . . . ? C6 C1 C2 Fe1 -104.2(6) . . . . ? C1 C2 C3 C4 0.7(8) . . . . ? Fe1 C2 C3 C4 58.8(5) . . . . ? C1 C2 C3 Fe1 -58.0(5) . . . . ? C2 C3 C4 C5 44.0(8) . . . . ? Fe1 C3 C4 C5 101.1(5) . . . . ? C2 C3 C4 Fe1 -57.1(5) . . . . ? C3 C4 C5 C6 -42.0(8) . . . . ? Fe1 C4 C5 C6 33.5(7) . . . . ? C2 C1 C6 C5 45.4(8) . . . . ? O1 C1 C6 C5 -176.3(5) . . . . ? Fe1 C1 C6 C5 -32.3(6) . . . . ? C4 C5 C6 C1 -1.5(8) . . . . ? C1 O1 C7 O2 -5.4(10) . . . . ? C1 O1 C7 C8 172.4(5) . . . . ? O2 C7 C8 C9 -29.3(10) . . . . ? O1 C7 C8 C9 152.9(5) . . . . ? C7 C8 C9 C10 120.3(7) . . . . ? C7 C8 C9 C11 -64.0(7) . . . . ? C12 O3 C11 O4 -1.2(8) . . . . ? C12 O3 C11 C9 -179.9(5) . . . . ? C10 C9 C11 O4 163.9(7) . . . . ? C8 C9 C11 O4 -11.7(8) . . . . ? C10 C9 C11 O3 -17.5(9) . . . . ? C8 C9 C11 O3 166.9(4) . . . . ?