#------------------------------------------------------------------------------ #$Date: 2012-03-17 10:31:40 +0200 (Sat, 17 Mar 2012) $ #$Revision: 44785 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/32/57/4325712.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_4325712 loop_ _publ_author_name 'Austin B. Scharf' 'Theodore A. Betley' _publ_contact_author_address ; Department of Chemistry and Chemical Biology Harvard University 12 Oxford St Cambridge, MA 02138 (USA) ; _publ_contact_author_email contact-betley@chemistry.harvard.edu _publ_contact_author_name 'Prof. Theodore Betley' _publ_section_title ; Electronic Perturbations of Iron Dipyrrinato Complexes via Ligand \b-Halogenation and meso-Fluoroarylation ; _journal_name_full 'Inorganic Chemistry' _journal_page_first 6837 _journal_page_last 6845 _journal_volume 50 _journal_year 2011 _chemical_formula_sum 'C40 H34 Cl F6 Fe N3' _chemical_formula_weight 762.00 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 96.774(2) _cell_angle_beta 100.237(2) _cell_angle_gamma 93.746(2) _cell_formula_units_Z 2 _cell_length_a 8.0378(8) _cell_length_b 13.8834(13) _cell_length_c 16.5650(15) _cell_measurement_reflns_used 29233 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 14.572 _cell_measurement_theta_min 2.326 _cell_volume 1799.3(3) _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.942 _diffrn_measured_fraction_theta_max 0.942 _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker D8 goniometer with CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator 'diamond 1 1 1' _diffrn_radiation_source synchrotron _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.41328 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 29174 _diffrn_reflns_theta_full 14.59 _diffrn_reflns_theta_max 14.59 _diffrn_reflns_theta_min 0.86 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_correction_T_min 0.9654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.406 _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.508 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 466 _refine_ls_number_reflns 6421 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+2.1034P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1022 _refine_ls_wR_factor_ref 0.1097 _reflns_number_gt 5122 _reflns_number_total 6421 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ic2009539_si_002_1.cif _[local]_cod_data_source_block as1_0m _cod_database_code 4325712 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags Fe1 Fe 0.41298(5) 0.64695(3) 0.79543(2) 0.01639(12) Uani 1 1 d . Cl1 Cl 0.68387(9) 0.61373(6) 0.81672(5) 0.0331(2) Uani 1 1 d . F1 F -0.6097(2) 0.77115(19) 0.47260(12) 0.0553(6) Uani 1 1 d . F2 F -0.5532(2) 0.69700(16) 0.57850(15) 0.0536(6) Uani 1 1 d . F3 F -0.5342(2) 0.85115(14) 0.59263(12) 0.0391(5) Uani 1 1 d . F4 F -0.1652(2) 0.89011(13) 0.34084(11) 0.0349(5) Uani 1 1 d . F5 F 0.0451(2) 0.80338(13) 0.35648(11) 0.0365(5) Uani 1 1 d . F6 F 0.0655(2) 0.94601(13) 0.42355(11) 0.0362(5) Uani 1 1 d . N1 N 0.3340(3) 0.77810(15) 0.77160(14) 0.0154(5) Uani 1 1 d . N2 N 0.2323(3) 0.57685(15) 0.70182(14) 0.0167(5) Uani 1 1 d . N3 N 0.3100(3) 0.62480(15) 0.90032(14) 0.0180(5) Uani 1 1 d . C1 C 0.2028(3) 0.48082(19) 0.67748(17) 0.0182(6) Uani 1 1 d . C2 C 0.0556(4) 0.4596(2) 0.61602(18) 0.0227(6) Uani 1 1 d . H2 H 0.0073 0.3968 0.5903 0.027 Uiso 1 1 calc R C3 C -0.0046(4) 0.54655(19) 0.60036(17) 0.0204(6) Uani 1 1 d . H3 H -0.1016 0.5557 0.5609 0.024 Uiso 1 1 calc R C4 C 0.1044(3) 0.62037(19) 0.65393(17) 0.0168(6) Uani 1 1 d . C5 C 0.0960(3) 0.72071(19) 0.65658(16) 0.0147(6) Uani 1 1 d . C6 C 0.2007(3) 0.79439(19) 0.70982(16) 0.0155(6) Uani 1 1 d . C7 C 0.1892(3) 0.89584(19) 0.71254(17) 0.0183(6) Uani 1 1 d . H7 H 0.1090 0.9273 0.6777 0.022 Uiso 1 1 calc R C8 C 0.3159(3) 0.94021(19) 0.77512(17) 0.0192(6) Uani 1 1 d . H8 H 0.3411 1.0083 0.7914 0.023 Uiso 1 1 calc R C9 C 0.4013(3) 0.86576(19) 0.81047(17) 0.0165(6) Uani 1 1 d . C10 C 0.5413(3) 0.87356(18) 0.88297(17) 0.0157(6) Uani 1 1 d . C11 C 0.7541(4) 0.8817(3) 0.78800(19) 0.0310(7) Uani 1 1 d . H11A H 0.6993 0.8236 0.7511 0.046 Uiso 1 1 calc R H11B H 0.8774 0.8830 0.7922 0.046 Uiso 1 1 calc R H11C H 0.7139 0.9401 0.7656 0.046 Uiso 1 1 calc R C12 C 0.3249(3) 0.8695(2) 0.97678(18) 0.0207(6) Uani 1 1 d . H12A H 0.3078 0.9312 1.0083 0.031 Uiso 1 1 calc R H12B H 0.3043 0.8158 1.0082 0.031 Uiso 1 1 calc R H12C H 0.2459 0.8596 0.9236 0.031 Uiso 1 1 calc R C13 C 0.5039(3) 0.87230(18) 0.96191(17) 0.0157(6) Uani 1 1 d . C14 C 0.7108(3) 0.87941(19) 0.87236(18) 0.0197(6) Uani 1 1 d . C15 C 0.8383(3) 0.8819(2) 0.94107(18) 0.0211(6) Uani 1 1 d . H15 H 0.9531 0.8855 0.9338 0.025 Uiso 1 1 calc R C16 C 0.6362(3) 0.87543(18) 1.02882(17) 0.0177(6) Uani 1 1 d . H16 H 0.6106 0.8748 1.0826 0.021 Uiso 1 1 calc R C17 C 0.8047(3) 0.87939(19) 1.01987(18) 0.0202(6) Uani 1 1 d . C18 C 0.9458(4) 0.8809(2) 1.09270(19) 0.0283(7) Uani 1 1 d . H18A H 0.9951 0.8182 1.0900 0.042 Uiso 1 1 calc R H18B H 0.9011 0.8925 1.1440 0.042 Uiso 1 1 calc R H18C H 1.0334 0.9331 1.0917 0.042 Uiso 1 1 calc R C19 C 0.3206(3) 0.41059(19) 0.70885(17) 0.0186(6) Uani 1 1 d . C20 C 0.4688(4) 0.39957(19) 0.67700(17) 0.0197(6) Uani 1 1 d . C21 C 0.5146(4) 0.4609(2) 0.61371(19) 0.0286(7) Uani 1 1 d . H21A H 0.4155 0.4613 0.5697 0.043 Uiso 1 1 calc R H21B H 0.6074 0.4337 0.5899 0.043 Uiso 1 1 calc R H21C H 0.5507 0.5277 0.6403 0.043 Uiso 1 1 calc R C22 C 0.1257(4) 0.3654(2) 0.8051(2) 0.0263(7) Uani 1 1 d . H22A H 0.1345 0.4313 0.8350 0.039 Uiso 1 1 calc R H22B H 0.1172 0.3176 0.8435 0.039 Uiso 1 1 calc R H22C H 0.0243 0.3561 0.7613 0.039 Uiso 1 1 calc R C23 C 0.2807(3) 0.35192(19) 0.76720(17) 0.0185(6) Uani 1 1 d . C24 C 0.3879(4) 0.2820(2) 0.79061(18) 0.0213(6) Uani 1 1 d . H24 H 0.3601 0.2417 0.8297 0.026 Uiso 1 1 calc R C25 C 0.5736(4) 0.3291(2) 0.70301(18) 0.0211(6) Uani 1 1 d . H25 H 0.6751 0.3219 0.6818 0.025 Uiso 1 1 calc R C26 C 0.5334(4) 0.2690(2) 0.75919(18) 0.0223(6) Uani 1 1 d . C27 C 0.6465(4) 0.1911(2) 0.7843(2) 0.0324(8) Uani 1 1 d . H27A H 0.6741 0.1966 0.8448 0.049 Uiso 1 1 calc R H27B H 0.7514 0.1991 0.7624 0.049 Uiso 1 1 calc R H27C H 0.5877 0.1268 0.7620 0.049 Uiso 1 1 calc R C28 C -0.0350(3) 0.75310(18) 0.59244(16) 0.0148(6) Uani 1 1 d . C29 C -0.2065(3) 0.74353(19) 0.59581(17) 0.0184(6) Uani 1 1 d . H29 H -0.2438 0.7148 0.6395 0.022 Uiso 1 1 calc R C30 C -0.3222(3) 0.7759(2) 0.53557(18) 0.0205(6) Uani 1 1 d . C31 C -0.2735(3) 0.81586(19) 0.46994(17) 0.0199(6) Uani 1 1 d . H31 H -0.3550 0.8371 0.4284 0.024 Uiso 1 1 calc R C32 C -0.1028(3) 0.82412(18) 0.46642(17) 0.0166(6) Uani 1 1 d . C33 C 0.0155(3) 0.79443(18) 0.52766(17) 0.0167(6) Uani 1 1 d . H33 H 0.1327 0.8025 0.5253 0.020 Uiso 1 1 calc R C34 C -0.5043(4) 0.7727(2) 0.54447(19) 0.0285(7) Uani 1 1 d . C35 C -0.0409(4) 0.8659(2) 0.39700(18) 0.0223(6) Uani 1 1 d . C36 C 0.1436(3) 0.63088(19) 0.89865(18) 0.0217(6) Uani 1 1 d . H36 H 0.0742 0.6432 0.8489 0.026 Uiso 1 1 calc R C37 C 0.0694(4) 0.6200(2) 0.96613(19) 0.0260(7) Uani 1 1 d . H37 H -0.0486 0.6258 0.9633 0.031 Uiso 1 1 calc R C38 C 0.1694(4) 0.6006(2) 1.03797(19) 0.0267(7) Uani 1 1 d . H38 H 0.1210 0.5918 1.0852 0.032 Uiso 1 1 calc R C39 C 0.3405(4) 0.5940(2) 1.04040(18) 0.0251(7) Uani 1 1 d . H39 H 0.4120 0.5804 1.0892 0.030 Uiso 1 1 calc R C40 C 0.4059(4) 0.60732(19) 0.97081(17) 0.0203(6) Uani 1 1 d . H40 H 0.5242 0.6040 0.9729 0.024 Uiso 1 1 calc R 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 0.0153(2) 0.0164(2) 0.0171(2) 0.00311(16) 0.00149(15) 0.00154(15) Cl1 0.0174(4) 0.0376(4) 0.0409(5) -0.0030(4) 0.0003(3) 0.0064(3) F1 0.0164(10) 0.119(2) 0.0259(11) -0.0054(12) -0.0003(8) 0.0116(11) F2 0.0235(10) 0.0565(13) 0.0902(18) 0.0265(13) 0.0251(11) 0.0016(9) F3 0.0277(10) 0.0536(12) 0.0367(11) -0.0063(10) 0.0132(8) 0.0116(9) F4 0.0355(10) 0.0390(11) 0.0295(10) 0.0200(9) -0.0047(8) -0.0008(8) F5 0.0525(12) 0.0379(10) 0.0274(10) 0.0121(9) 0.0214(9) 0.0130(9) F6 0.0404(11) 0.0335(10) 0.0318(11) 0.0093(9) 0.0030(8) -0.0165(8) N1 0.0144(11) 0.0157(11) 0.0157(12) 0.0021(10) 0.0024(9) -0.0009(9) N2 0.0207(12) 0.0141(11) 0.0152(12) 0.0023(10) 0.0029(9) 0.0017(9) N3 0.0197(12) 0.0139(11) 0.0189(13) 0.0006(10) 0.0014(10) -0.0004(9) C1 0.0220(15) 0.0166(14) 0.0174(15) 0.0036(12) 0.0065(11) 0.0009(11) C2 0.0280(16) 0.0152(14) 0.0216(16) -0.0004(12) -0.0003(12) -0.0036(12) C3 0.0222(15) 0.0190(14) 0.0187(15) 0.0025(12) 0.0008(12) -0.0006(11) C4 0.0161(14) 0.0189(14) 0.0163(15) 0.0045(12) 0.0046(11) 0.0013(11) C5 0.0136(13) 0.0177(13) 0.0145(14) 0.0048(11) 0.0053(11) 0.0014(10) C6 0.0143(13) 0.0182(13) 0.0148(14) 0.0042(11) 0.0042(11) 0.0005(10) C7 0.0185(14) 0.0184(14) 0.0190(15) 0.0057(12) 0.0029(11) 0.0043(11) C8 0.0212(15) 0.0127(13) 0.0224(16) 0.0005(12) 0.0026(12) -0.0016(11) C9 0.0139(13) 0.0181(14) 0.0176(15) 0.0023(12) 0.0046(11) -0.0020(11) C10 0.0169(14) 0.0122(13) 0.0171(14) 0.0000(11) 0.0024(11) -0.0009(10) C11 0.0232(16) 0.048(2) 0.0211(17) -0.0021(15) 0.0089(13) -0.0010(14) C12 0.0186(14) 0.0207(14) 0.0238(16) 0.0054(12) 0.0054(12) 0.0004(11) C13 0.0167(14) 0.0114(12) 0.0189(15) 0.0022(11) 0.0027(11) 0.0002(10) C14 0.0195(15) 0.0183(14) 0.0206(15) -0.0013(12) 0.0054(12) -0.0016(11) C15 0.0143(14) 0.0215(14) 0.0269(17) 0.0000(13) 0.0045(12) 0.0013(11) C16 0.0221(15) 0.0149(13) 0.0167(15) 0.0030(11) 0.0048(11) 0.0002(11) C17 0.0189(15) 0.0147(13) 0.0248(16) 0.0040(12) -0.0027(12) 0.0007(11) C18 0.0229(16) 0.0310(17) 0.0295(18) 0.0104(14) -0.0024(13) 0.0004(13) C19 0.0232(15) 0.0137(13) 0.0173(15) 0.0016(11) 0.0009(11) -0.0014(11) C20 0.0255(16) 0.0161(14) 0.0168(15) -0.0001(12) 0.0047(12) -0.0020(11) C21 0.0363(18) 0.0278(16) 0.0271(18) 0.0108(14) 0.0141(14) 0.0065(13) C22 0.0272(16) 0.0236(15) 0.0314(18) 0.0098(14) 0.0109(13) 0.0020(12) C23 0.0217(15) 0.0157(13) 0.0168(15) -0.0004(12) 0.0032(11) -0.0015(11) C24 0.0248(16) 0.0199(14) 0.0193(15) 0.0067(12) 0.0031(12) -0.0016(12) C25 0.0209(15) 0.0205(14) 0.0221(16) 0.0006(12) 0.0064(12) 0.0011(11) C26 0.0227(15) 0.0204(14) 0.0218(16) 0.0045(12) -0.0018(12) -0.0001(12) C27 0.0324(18) 0.0294(17) 0.039(2) 0.0129(15) 0.0065(15) 0.0118(14) C28 0.0160(13) 0.0127(13) 0.0144(14) -0.0025(11) 0.0022(11) 0.0000(10) C29 0.0205(15) 0.0189(14) 0.0153(15) -0.0014(12) 0.0050(11) -0.0006(11) C30 0.0153(14) 0.0233(15) 0.0214(16) -0.0026(12) 0.0034(12) 0.0012(11) C31 0.0209(15) 0.0195(14) 0.0174(15) -0.0004(12) -0.0008(11) 0.0062(11) C32 0.0213(15) 0.0126(13) 0.0149(14) -0.0006(11) 0.0023(11) 0.0024(11) C33 0.0149(13) 0.0154(13) 0.0195(15) 0.0015(12) 0.0023(11) 0.0021(10) C34 0.0214(16) 0.0420(19) 0.0205(17) -0.0012(15) 0.0014(13) 0.0072(14) C35 0.0259(16) 0.0200(14) 0.0191(16) 0.0037(12) -0.0008(12) -0.0002(12) C36 0.0209(15) 0.0180(14) 0.0236(16) 0.0017(12) -0.0014(12) -0.0010(11) C37 0.0248(16) 0.0220(15) 0.0311(18) 0.0009(13) 0.0096(13) -0.0049(12) C38 0.0365(18) 0.0225(15) 0.0223(17) 0.0018(13) 0.0118(14) -0.0042(13) C39 0.0358(18) 0.0203(15) 0.0188(16) 0.0028(12) 0.0034(13) 0.0033(13) C40 0.0221(15) 0.0183(14) 0.0185(15) 0.0010(12) -0.0007(12) 0.0018(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.0550 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.1990 0.3060 '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 N1 Fe1 N2 91.32(9) N1 Fe1 N3 102.00(9) N2 Fe1 N3 102.36(9) N1 Fe1 Cl1 124.25(7) N2 Fe1 Cl1 123.80(7) N3 Fe1 Cl1 109.24(7) C9 N1 C6 106.7(2) C9 N1 Fe1 127.02(18) C6 N1 Fe1 126.30(18) C1 N2 C4 106.3(2) C1 N2 Fe1 127.79(18) C4 N2 Fe1 125.76(17) C40 N3 C36 117.9(2) C40 N3 Fe1 122.18(19) C36 N3 Fe1 119.86(18) N2 C1 C2 111.0(2) N2 C1 C19 122.3(2) C2 C1 C19 126.6(2) C3 C2 C1 106.9(2) C3 C2 H2 126.5 C1 C2 H2 126.5 C2 C3 C4 107.1(2) C2 C3 H3 126.5 C4 C3 H3 126.5 C5 C4 N2 124.3(2) C5 C4 C3 126.9(2) N2 C4 C3 108.7(2) C6 C5 C4 127.7(2) C6 C5 C28 116.1(2) C4 C5 C28 116.2(2) C5 C6 N1 124.2(2) C5 C6 C7 127.1(2) N1 C6 C7 108.7(2) C8 C7 C6 106.9(2) C8 C7 H7 126.6 C6 C7 H7 126.6 C7 C8 C9 106.9(2) C7 C8 H8 126.5 C9 C8 H8 126.5 N1 C9 C8 110.8(2) N1 C9 C10 120.1(2) C8 C9 C10 129.0(2) C13 C10 C14 120.0(2) C13 C10 C9 119.7(2) C14 C10 C9 120.4(2) C14 C11 H11A 109.5 C14 C11 H11B 109.5 H11A C11 H11B 109.5 C14 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C13 C12 H12A 109.5 C13 C12 H12B 109.5 H12A C12 H12B 109.5 C13 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C16 C13 C10 119.0(2) C16 C13 C12 119.1(2) C10 C13 C12 121.9(2) C15 C14 C10 118.8(3) C15 C14 C11 120.3(3) C10 C14 C11 120.9(3) C17 C15 C14 122.4(3) C17 C15 H15 118.8 C14 C15 H15 118.8 C17 C16 C13 122.2(3) C17 C16 H16 118.9 C13 C16 H16 118.9 C15 C17 C16 117.6(3) C15 C17 C18 121.0(3) C16 C17 C18 121.5(3) C17 C18 H18A 109.5 C17 C18 H18B 109.5 H18A C18 H18B 109.5 C17 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C20 C19 C23 119.9(2) C20 C19 C1 119.5(2) C23 C19 C1 120.5(3) C25 C20 C19 119.2(2) C25 C20 C21 119.6(3) C19 C20 C21 121.2(2) C20 C21 H21A 109.5 C20 C21 H21B 109.5 H21A C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C23 C22 H22A 109.5 C23 C22 H22B 109.5 H22A C22 H22B 109.5 C23 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C24 C23 C19 118.9(3) C24 C23 C22 120.3(2) C19 C23 C22 120.9(2) C26 C24 C23 122.2(3) C26 C24 H24 118.9 C23 C24 H24 118.9 C26 C25 C20 121.5(3) C26 C25 H25 119.3 C20 C25 H25 119.3 C24 C26 C25 118.3(3) C24 C26 C27 121.3(3) C25 C26 C27 120.4(3) C26 C27 H27A 109.5 C26 C27 H27B 109.5 H27A C27 H27B 109.5 C26 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C33 C28 C29 118.9(2) C33 C28 C5 119.1(2) C29 C28 C5 122.0(2) C30 C29 C28 119.7(3) C30 C29 H29 120.2 C28 C29 H29 120.2 C29 C30 C31 121.9(3) C29 C30 C34 118.6(3) C31 C30 C34 119.4(3) C30 C31 C32 118.1(2) C30 C31 H31 120.9 C32 C31 H31 120.9 C31 C32 C33 120.7(3) C31 C32 C35 121.1(2) C33 C32 C35 118.3(2) C32 C33 C28 120.7(2) C32 C33 H33 119.6 C28 C33 H33 119.6 F2 C34 F1 107.2(3) F2 C34 F3 105.9(3) F1 C34 F3 105.9(2) F2 C34 C30 113.3(2) F1 C34 C30 112.7(3) F3 C34 C30 111.3(2) F4 C35 F6 106.8(2) F4 C35 F5 106.4(2) F6 C35 F5 105.9(2) F4 C35 C32 113.3(2) F6 C35 C32 112.2(2) F5 C35 C32 111.8(2) N3 C36 C37 122.7(3) N3 C36 H36 118.7 C37 C36 H36 118.7 C36 C37 C38 118.7(3) C36 C37 H37 120.6 C38 C37 H37 120.6 C39 C38 C37 119.1(3) C39 C38 H38 120.4 C37 C38 H38 120.4 C40 C39 C38 118.7(3) C40 C39 H39 120.7 C38 C39 H39 120.7 N3 C40 C39 122.8(3) N3 C40 H40 118.6 C39 C40 H40 118.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Fe1 N1 2.026(2) Fe1 N2 2.030(2) Fe1 N3 2.098(2) Fe1 Cl1 2.2304(8) F1 C34 1.330(4) F2 C34 1.319(4) F3 C34 1.333(4) F4 C35 1.327(3) F5 C35 1.337(3) F6 C35 1.337(3) N1 C9 1.339(3) N1 C6 1.394(3) N2 C1 1.340(3) N2 C4 1.399(3) N3 C40 1.337(3) N3 C36 1.341(4) C1 C2 1.407(4) C1 C19 1.477(4) C2 C3 1.365(4) C2 H2 0.9500 C3 C4 1.413(4) C3 H3 0.9500 C4 C5 1.395(4) C5 C6 1.394(4) C5 C28 1.489(4) C6 C7 1.413(4) C7 C8 1.372(4) C7 H7 0.9500 C8 C9 1.405(4) C8 H8 0.9500 C9 C10 1.481(4) C10 C13 1.395(4) C10 C14 1.403(4) C11 C14 1.502(4) C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 C13 1.500(4) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C16 1.388(4) C14 C15 1.385(4) C15 C17 1.383(4) C15 H15 0.9500 C16 C17 1.386(4) C16 H16 0.9500 C17 C18 1.499(4) C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 C20 1.395(4) C19 C23 1.401(4) C20 C25 1.390(4) C20 C21 1.506(4) C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 C23 1.504(4) C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 C24 1.383(4) C24 C26 1.376(4) C24 H24 0.9500 C25 C26 1.386(4) C25 H25 0.9500 C26 C27 1.506(4) C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C28 C33 1.384(4) C28 C29 1.388(4) C29 C30 1.376(4) C29 H29 0.9500 C30 C31 1.381(4) C30 C34 1.496(4) C31 C32 1.381(4) C31 H31 0.9500 C32 C33 1.382(4) C32 C35 1.493(4) C33 H33 0.9500 C36 C37 1.376(4) C36 H36 0.9500 C37 C38 1.378(4) C37 H37 0.9500 C38 C39 1.378(4) C38 H38 0.9500 C39 C40 1.375(4) C39 H39 0.9500 C40 H40 0.9500