Supplementary Material (ESI) for Chemical Science This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _publ_contact_author_name 'Prof. Dr. Ulrich Siemeling' _publ_contact_author_address ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; _publ_contact_author_phone '+0049 561 804 4576' _publ_contact_author_fax '+0049 561 804 4777' _publ_contact_author_email siemeling@uni-kassl.de _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #===================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #===================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; N-heterocyclic carbenes which readily add ammonia, carbon monoxide and other small molecules ; loop_ _publ_author_name _publ_author_footnote _publ_author_address U.Siemeling ? ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; C.Farber ? ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; C.Bruhn ? ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; M.Leibold ? ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; D.Selent ? ; Leibniz Institute for Catalysis at the University of Rostock Albert-Einstein-Str. 29a D-18059 Rostock Germany ; W.Baumann ? ; Leibniz Institute for Catalysis at the University of Rostock Albert-Einstein-Str. 29a D-18059 Rostock Germany ; ; M.von Hopffgarten ; ? ; Department of Chemistry Phillips-University Marburg Hans-Meerwein-Str. D-35032 Marburg Germany ; C.Goedecke ? ; Department of Chemistry Phillips-University Marburg Hans-Meerwein-Str. D-35032 Marburg Germany ; G.Frenking ? ; Department of Chemistry Phillips-University Marburg Hans-Meerwein-Str. D-35032 Marburg Germany ; #============================================================================ data_i0605 _database_code_depnum_ccdc_archive 'CCDC 782899' #TrackingRef 'i0605_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H60 Fe2 N4 O' _chemical_formula_sum 'C43 H60 Fe2 N4 O' _chemical_formula_weight 760.65 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3194(13) _cell_length_b 10.7454(5) _cell_length_c 22.9601(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.397(6) _cell_angle_gamma 90.00 _cell_volume 3992.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14444 _cell_measurement_theta_min 1.78 _cell_measurement_theta_max 24.76 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 0.764 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7638 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 180 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 25199 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7035 _reflns_number_gt 4350 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. While the data/parameter ratio is ok, the size and form of the ellipsoids of the t-Bu groups as well as the negative volume for C39, in case of anisotropic refinement, may indicate slight packing disorder. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7035 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.3049 _refine_ls_wR_factor_gt 0.2727 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7909(3) 0.4945(5) 0.3651(3) 0.0494(13) Uani 1 1 d . . . C2 C 0.7175(4) 0.4624(7) 0.3314(3) 0.0632(16) Uani 1 1 d . . . C3 C 0.6991(4) 0.3316(7) 0.3063(3) 0.0627(17) Uani 1 1 d . . . C4 C 0.9397(4) 0.4623(5) 0.3617(3) 0.0584(15) Uani 1 1 d . . . C5 C 0.9638(4) 0.4829(6) 0.3042(4) 0.0681(18) Uani 1 1 d . . . H5A H 0.9321 0.4615 0.2679 0.082 Uiso 1 1 calc R . . C6 C 1.0442(5) 0.5415(6) 0.3110(5) 0.082(2) Uani 1 1 d . . . H6A H 1.0745 0.5668 0.2803 0.098 Uiso 1 1 calc R . . C7 C 1.0695(5) 0.5542(6) 0.3723(5) 0.091(3) Uani 1 1 d . . . H7A H 1.1207 0.5878 0.3898 0.109 Uiso 1 1 calc R . . C8 C 1.0052(4) 0.5081(6) 0.4033(4) 0.0720(19) Uani 1 1 d . . . H8A H 1.0059 0.5080 0.4447 0.086 Uiso 1 1 calc R . . C9 C 0.8487(4) 0.7020(5) 0.3731(3) 0.0644(18) Uani 1 1 d . . . C10 C 0.8517(5) 0.7290(6) 0.3121(4) 0.079(2) Uani 1 1 d . . . H10A H 0.8147 0.6984 0.2800 0.095 Uiso 1 1 calc R . . C11 C 0.9207(6) 0.8102(7) 0.3083(5) 0.096(3) Uani 1 1 d . . . H11A H 0.9369 0.8427 0.2731 0.115 Uiso 1 1 calc R . . C12 C 0.9611(6) 0.8342(6) 0.3664(6) 0.099(4) Uani 1 1 d . . . H12A H 1.0089 0.8840 0.3764 0.119 Uiso 1 1 calc R . . C13 C 0.9155(5) 0.7690(6) 0.4066(4) 0.074(2) Uani 1 1 d . . . H13A H 0.9275 0.7699 0.4482 0.088 Uiso 1 1 calc R . . C14 C 0.8698(4) 0.3336(5) 0.4270(3) 0.0565(15) Uani 1 1 d . . . H14B H 0.8144 0.3222 0.4394 0.068 Uiso 1 1 calc R . . H14A H 0.9042 0.3792 0.4587 0.068 Uiso 1 1 calc R . . C15 C 0.9090(4) 0.2032(6) 0.4201(4) 0.0671(18) Uani 1 1 d . . . C16 C 1.0029(4) 0.2078(6) 0.4154(4) 0.079(2) Uani 1 1 d . . . H16A H 1.0302 0.2630 0.4459 0.095 Uiso 1 1 calc R . . H16B H 1.0115 0.2393 0.3766 0.095 Uiso 1 1 calc R . . H16C H 1.0262 0.1239 0.4208 0.095 Uiso 1 1 calc R . . C17 C 0.8641(5) 0.1380(7) 0.3662(5) 0.095(3) Uani 1 1 d . . . H17A H 0.8748 0.1824 0.3306 0.115 Uiso 1 1 calc R . . H17B H 0.8045 0.1375 0.3685 0.115 Uiso 1 1 calc R . . H17C H 0.8840 0.0522 0.3647 0.115 Uiso 1 1 calc R . . C18 C 0.8959(5) 0.1288(7) 0.4755(5) 0.089(3) Uani 1 1 d . . . H18A H 0.8367 0.1150 0.4762 0.107 Uiso 1 1 calc R . . H18B H 0.9186 0.1755 0.5105 0.107 Uiso 1 1 calc R . . H18C H 0.9241 0.0483 0.4750 0.107 Uiso 1 1 calc R . . C19 C 0.7871(4) 0.6139(5) 0.4573(3) 0.0591(16) Uani 1 1 d . . . H19B H 0.8426 0.6303 0.4789 0.071 Uiso 1 1 calc R . . H19A H 0.7703 0.5296 0.4685 0.071 Uiso 1 1 calc R . . C20 C 0.7257(4) 0.7096(6) 0.4779(3) 0.0666(18) Uani 1 1 d . . . C21 C 0.6404(5) 0.6973(8) 0.4416(4) 0.087(2) Uani 1 1 d . . . H21A H 0.6176 0.6147 0.4479 0.105 Uiso 1 1 calc R . . H21B H 0.6458 0.7080 0.3999 0.105 Uiso 1 1 calc R . . H21C H 0.6034 0.7612 0.4538 0.105 Uiso 1 1 calc R . . C22 C 0.7212(6) 0.6798(7) 0.5436(4) 0.094(3) Uani 1 1 d . . . H22A H 0.7761 0.6895 0.5660 0.113 Uiso 1 1 calc R . . H22B H 0.7022 0.5940 0.5473 0.113 Uiso 1 1 calc R . . H22C H 0.6824 0.7370 0.5589 0.113 Uiso 1 1 calc R . . C23 C 0.7584(5) 0.8440(6) 0.4747(4) 0.082(2) Uani 1 1 d . . . H23A H 0.7598 0.8670 0.4335 0.099 Uiso 1 1 calc R . . H23B H 0.8142 0.8491 0.4961 0.099 Uiso 1 1 calc R . . H23C H 0.7218 0.9011 0.4924 0.099 Uiso 1 1 calc R . . C24 C 0.6918(5) 0.2018(10) 0.2168(3) 0.085(2) Uani 1 1 d . . . C25 C 0.7361(6) 0.0865(11) 0.2144(4) 0.102(3) Uani 1 1 d . . . H25A H 0.7881 0.0682 0.2364 0.122 Uiso 1 1 calc R . . C26 C 0.6909(9) 0.0049(14) 0.1746(5) 0.130(5) Uani 1 1 d . . . H26A H 0.7058 -0.0780 0.1661 0.156 Uiso 1 1 calc R . . C27 C 0.6188(8) 0.0692(18) 0.1492(4) 0.155(7) Uani 1 1 d . . . H27A H 0.5778 0.0369 0.1200 0.186 Uiso 1 1 calc R . . C28 C 0.6183(6) 0.1906(16) 0.1750(4) 0.127(5) Uani 1 1 d . . . H28A H 0.5769 0.2524 0.1661 0.152 Uiso 1 1 calc R . . C29 C 0.6139(5) 0.1403(11) 0.3158(3) 0.093(3) Uani 1 1 d . . . C30 C 0.6471(7) 0.0197(11) 0.3265(4) 0.102(3) Uani 1 1 d . . . H30A H 0.6990 0.0003 0.3483 0.122 Uiso 1 1 calc R . . C31 C 0.5889(8) -0.0674(12) 0.2988(5) 0.120(4) Uani 1 1 d . . . H31A H 0.5964 -0.1551 0.2988 0.144 Uiso 1 1 calc R . . C32 C 0.5218(8) -0.0073(15) 0.2725(4) 0.133(5) Uani 1 1 d . . . H32A H 0.4750 -0.0457 0.2508 0.159 Uiso 1 1 calc R . . C33 C 0.5321(5) 0.1258(12) 0.2825(4) 0.107(4) Uani 1 1 d . . . H33A H 0.4937 0.1899 0.2701 0.128 Uiso 1 1 calc R . . C34 C 0.7821(4) 0.3841(7) 0.2272(3) 0.0674(18) Uani 1 1 d . . . H34A H 0.8311 0.3310 0.2247 0.081 Uiso 1 1 calc R . . H34B H 0.7992 0.4508 0.2560 0.081 Uiso 1 1 calc R . . C35 C 0.7579(5) 0.4463(10) 0.1661(3) 0.096(3) Uani 1 1 d . . . C36 C 0.7600(8) 0.3530(13) 0.1148(4) 0.125(4) Uani 1 1 d . . . H36A H 0.7086 0.3049 0.1094 0.150 Uiso 1 1 calc R . . H36B H 0.8070 0.2963 0.1239 0.150 Uiso 1 1 calc R . . H36C H 0.7659 0.3987 0.0786 0.150 Uiso 1 1 calc R . . C37 C 0.8271(6) 0.5427(10) 0.1608(4) 0.106(3) Uani 1 1 d . . . H37A H 0.8808 0.5004 0.1652 0.127 Uiso 1 1 calc R . . H37B H 0.8268 0.6057 0.1916 0.127 Uiso 1 1 calc R . . H37C H 0.8176 0.5828 0.1222 0.127 Uiso 1 1 calc R . . C38 C 0.6745(7) 0.5130(16) 0.1628(5) 0.158(7) Uani 1 1 d . . . H38A H 0.6796 0.5848 0.1893 0.189 Uiso 1 1 calc R . . H38B H 0.6329 0.4554 0.1744 0.189 Uiso 1 1 calc R . . H38C H 0.6576 0.5413 0.1224 0.189 Uiso 1 1 calc R . . C39 C 0.6554(7) 0.2590(10) 0.4019(5) 0.105(3) Uiso 1 1 d . . . H39B H 0.6864 0.3347 0.4160 0.127 Uiso 1 1 calc R . . H39A H 0.6890 0.1868 0.4175 0.127 Uiso 1 1 calc R . . C40 C 0.5773(4) 0.2572(5) 0.4305(3) 0.0547(14) Uani 1 1 d . . . C41 C 0.5256(8) 0.1454(12) 0.4270(5) 0.148(6) Uani 1 1 d . . . H41A H 0.5335 0.0982 0.3916 0.178 Uiso 1 1 calc R . . H41B H 0.4674 0.1696 0.4252 0.178 Uiso 1 1 calc R . . H41C H 0.5413 0.0937 0.4618 0.178 Uiso 1 1 calc R . . C42 C 0.5760(7) 0.3333(11) 0.4839(4) 0.117(4) Uani 1 1 d . . . H42A H 0.6050 0.4119 0.4795 0.140 Uiso 1 1 calc R . . H42B H 0.6034 0.2879 0.5179 0.140 Uiso 1 1 calc R . . H42C H 0.5186 0.3506 0.4896 0.140 Uiso 1 1 calc R . . C43 C 0.5096(8) 0.3366(15) 0.3876(6) 0.151(6) Uani 1 1 d . . . H43C H 0.4681 0.3704 0.4104 0.181 Uiso 1 1 calc R . . H43B H 0.4827 0.2822 0.3566 0.181 Uiso 1 1 calc R . . H43A H 0.5373 0.4051 0.3698 0.181 Uiso 1 1 calc R . . N1 N 0.8617(3) 0.4099(4) 0.3734(2) 0.0495(11) Uani 1 1 d . . . N2 N 0.7938(3) 0.6141(4) 0.3932(2) 0.0561(13) Uani 1 1 d . . . N3 N 0.7174(3) 0.3059(6) 0.2514(2) 0.0639(14) Uani 1 1 d . . . N4 N 0.6521(4) 0.2564(7) 0.3364(2) 0.0747(18) Uani 1 1 d . . . Fe1 Fe 0.95945(6) 0.64631(7) 0.34982(5) 0.0679(4) Uani 1 1 d . . . Fe2 Fe 0.62421(8) 0.06435(17) 0.23971(5) 0.1039(6) Uani 1 1 d . . . O1 O 0.6513(3) 0.5289(7) 0.3173(3) 0.0918(17) 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 C1 0.050(3) 0.043(3) 0.058(3) 0.006(3) 0.016(3) 0.004(2) C2 0.060(4) 0.079(4) 0.055(4) 0.001(3) 0.025(3) 0.002(3) C3 0.048(3) 0.096(5) 0.045(3) 0.002(3) 0.007(3) -0.004(3) C4 0.058(3) 0.037(3) 0.083(5) -0.004(3) 0.018(3) -0.003(2) C5 0.060(4) 0.053(3) 0.098(5) -0.005(3) 0.036(4) 0.004(3) C6 0.069(4) 0.052(4) 0.134(8) -0.014(4) 0.048(5) -0.008(3) C7 0.057(4) 0.047(4) 0.170(10) -0.017(5) 0.023(5) -0.005(3) C8 0.062(4) 0.047(3) 0.105(6) -0.014(3) 0.003(4) -0.007(3) C9 0.081(4) 0.033(3) 0.088(5) 0.006(3) 0.042(4) 0.002(3) C10 0.093(5) 0.049(3) 0.108(6) 0.021(4) 0.057(5) 0.019(3) C11 0.120(7) 0.051(4) 0.135(8) 0.033(5) 0.089(7) 0.019(4) C12 0.112(7) 0.043(4) 0.162(10) 0.002(5) 0.086(7) -0.002(4) C13 0.082(5) 0.041(3) 0.107(6) -0.005(3) 0.047(4) -0.006(3) C14 0.068(4) 0.038(3) 0.062(4) 0.002(3) 0.004(3) -0.003(2) C15 0.062(4) 0.039(3) 0.099(5) 0.005(3) 0.006(4) 0.000(3) C16 0.067(4) 0.051(4) 0.121(7) 0.003(4) 0.015(4) 0.009(3) C17 0.079(5) 0.047(4) 0.153(9) -0.034(4) -0.013(5) 0.008(3) C18 0.073(5) 0.055(4) 0.138(8) 0.038(4) 0.011(5) 0.013(3) C19 0.075(4) 0.041(3) 0.067(4) 0.003(3) 0.030(3) 0.001(3) C20 0.075(4) 0.045(3) 0.087(5) 0.001(3) 0.038(4) -0.002(3) C21 0.079(5) 0.069(4) 0.123(7) -0.004(5) 0.050(5) 0.005(4) C22 0.137(7) 0.056(4) 0.105(7) -0.012(4) 0.074(6) -0.017(4) C23 0.103(6) 0.041(3) 0.113(7) -0.006(4) 0.054(5) 0.002(3) C24 0.070(4) 0.146(8) 0.040(4) -0.018(4) 0.015(3) -0.013(5) C25 0.085(6) 0.135(8) 0.090(6) -0.050(6) 0.028(5) -0.028(6) C26 0.138(10) 0.162(11) 0.100(8) -0.066(8) 0.056(7) -0.058(9) C27 0.120(10) 0.30(2) 0.054(6) -0.057(9) 0.026(6) -0.077(11) C28 0.079(6) 0.262(15) 0.039(4) -0.022(7) 0.006(4) -0.028(7) C29 0.080(5) 0.155(9) 0.042(4) -0.010(5) 0.009(3) -0.061(6) C30 0.109(7) 0.127(8) 0.067(5) -0.007(5) 0.001(5) -0.061(6) C31 0.130(9) 0.138(9) 0.088(7) -0.030(6) -0.004(6) -0.078(8) C32 0.119(9) 0.215(14) 0.063(5) -0.033(7) 0.010(6) -0.101(10) C33 0.073(5) 0.188(11) 0.059(5) -0.014(6) 0.006(4) -0.056(6) C34 0.059(4) 0.089(5) 0.059(4) 0.016(3) 0.022(3) 0.009(3) C35 0.086(5) 0.152(9) 0.055(4) 0.039(5) 0.031(4) 0.037(5) C36 0.128(8) 0.202(13) 0.053(5) 0.020(6) 0.033(5) 0.006(8) C37 0.117(7) 0.133(8) 0.080(6) 0.058(6) 0.058(5) 0.044(6) C38 0.116(8) 0.252(16) 0.115(8) 0.108(10) 0.054(7) 0.098(10) C40 0.060(3) 0.048(3) 0.060(4) 0.007(3) 0.021(3) 0.005(2) C41 0.176(11) 0.181(12) 0.105(7) -0.074(8) 0.088(8) -0.129(10) C42 0.151(9) 0.146(9) 0.062(5) -0.031(5) 0.047(5) -0.085(8) C43 0.137(10) 0.190(14) 0.132(10) 0.025(9) 0.045(8) 0.073(10) N1 0.055(3) 0.033(2) 0.061(3) -0.001(2) 0.011(2) -0.0061(19) N2 0.065(3) 0.040(2) 0.068(3) 0.007(2) 0.029(3) 0.004(2) N3 0.056(3) 0.103(4) 0.035(3) 0.004(3) 0.016(2) 0.001(3) N4 0.066(3) 0.127(5) 0.033(3) -0.009(3) 0.011(2) -0.038(3) Fe1 0.0700(6) 0.0370(5) 0.1054(9) 0.0007(5) 0.0447(6) -0.0008(4) Fe2 0.0859(8) 0.1710(15) 0.0560(7) -0.0374(8) 0.0141(6) -0.0560(9) O1 0.059(3) 0.136(5) 0.082(4) -0.012(3) 0.014(3) 0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.384(9) . ? C1 N2 1.436(8) . ? C1 N1 1.463(7) . ? C2 O1 1.301(8) . ? C2 C3 1.534(10) . ? C3 N3 1.361(8) . ? C3 N4 1.362(9) . ? C4 C8 1.425(10) . ? C4 C5 1.442(10) . ? C4 N1 1.449(7) . ? C4 Fe1 2.027(6) . ? C5 C6 1.447(10) . ? C5 Fe1 2.051(7) . ? C5 H5A 0.9500 . ? C6 C7 1.422(14) . ? C6 Fe1 2.073(7) . ? C6 H6A 0.9500 . ? C7 C8 1.431(11) . ? C7 Fe1 2.057(8) . ? C7 H7A 0.9500 . ? C8 Fe1 2.008(8) . ? C8 H8A 0.9500 . ? C9 N2 1.420(8) . ? C9 C10 1.437(11) . ? C9 C13 1.444(11) . ? C9 Fe1 2.040(6) . ? C10 C11 1.435(12) . ? C10 Fe1 2.059(8) . ? C10 H10A 0.9500 . ? C11 C12 1.431(15) . ? C11 Fe1 2.062(8) . ? C11 H11A 0.9500 . ? C12 C13 1.440(10) . ? C12 Fe1 2.054(7) . ? C12 H12A 0.9500 . ? C13 Fe1 2.048(7) . ? C13 H13A 0.9500 . ? C14 N1 1.471(8) . ? C14 C15 1.556(8) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? C15 C17 1.525(11) . ? C15 C18 1.541(11) . ? C15 C16 1.550(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N2 1.489(8) . ? C19 C20 1.552(8) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C20 C21 1.532(12) . ? C20 C23 1.545(9) . ? C20 C22 1.553(11) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 N3 1.404(11) . ? C24 C25 1.439(15) . ? C24 C28 1.442(12) . ? C24 Fe2 1.956(9) . ? C25 C26 1.405(14) . ? C25 Fe2 2.001(9) . ? C25 H25A 0.9500 . ? C26 C27 1.42(2) . ? C26 Fe2 2.062(10) . ? C26 H26A 0.9500 . ? C27 C28 1.43(2) . ? C27 Fe2 2.069(10) . ? C27 H27A 0.9500 . ? C28 Fe2 2.005(13) . ? C28 H28A 0.9500 . ? C29 C30 1.413(15) . ? C29 N4 1.446(11) . ? C29 C33 1.458(12) . ? C29 Fe2 1.955(8) . ? C30 C31 1.424(12) . ? C30 Fe2 2.037(10) . ? C30 H30A 0.9500 . ? C31 C32 1.346(19) . ? C31 Fe2 2.092(12) . ? C31 H31A 0.9500 . ? C32 C33 1.456(18) . ? C32 Fe2 2.068(10) . ? C32 H32A 0.9500 . ? C33 Fe2 2.011(10) . ? C33 H33A 0.9500 . ? C34 N3 1.510(8) . ? C34 C35 1.558(10) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C38 1.532(12) . ? C35 C37 1.548(14) . ? C35 C36 1.552(15) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 N4 1.499(12) . ? C39 C40 1.506(12) . ? C39 H39B 0.9900 . ? C39 H39A 0.9900 . ? C40 C41 1.464(10) . ? C40 C42 1.477(10) . ? C40 C43 1.623(14) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43C 0.9800 . ? C43 H43B 0.9800 . ? C43 H43A 0.9800 . ? 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 C2 C1 N2 116.8(5) . . ? C2 C1 N1 122.0(5) . . ? N2 C1 N1 121.2(5) . . ? O1 C2 C1 129.3(7) . . ? O1 C2 C3 107.0(6) . . ? C1 C2 C3 123.6(6) . . ? N3 C3 N4 123.7(6) . . ? N3 C3 C2 118.5(6) . . ? N4 C3 C2 116.7(6) . . ? C8 C4 C5 107.0(6) . . ? C8 C4 N1 127.6(6) . . ? C5 C4 N1 125.4(6) . . ? C8 C4 Fe1 68.6(4) . . ? C5 C4 Fe1 70.2(3) . . ? N1 C4 Fe1 124.2(4) . . ? C4 C5 C6 108.5(8) . . ? C4 C5 Fe1 68.4(4) . . ? C6 C5 Fe1 70.3(4) . . ? C4 C5 H5A 125.7 . . ? C6 C5 H5A 125.7 . . ? Fe1 C5 H5A 127.2 . . ? C7 C6 C5 107.0(7) . . ? C7 C6 Fe1 69.3(4) . . ? C5 C6 Fe1 68.6(4) . . ? C7 C6 H6A 126.5 . . ? C5 C6 H6A 126.5 . . ? Fe1 C6 H6A 127.1 . . ? C6 C7 C8 108.7(7) . . ? C6 C7 Fe1 70.4(5) . . ? C8 C7 Fe1 67.6(4) . . ? C6 C7 H7A 125.6 . . ? C8 C7 H7A 125.6 . . ? Fe1 C7 H7A 128.0 . . ? C4 C8 C7 108.7(8) . . ? C4 C8 Fe1 70.0(4) . . ? C7 C8 Fe1 71.3(5) . . ? C4 C8 H8A 125.6 . . ? C7 C8 H8A 125.6 . . ? Fe1 C8 H8A 124.7 . . ? N2 C9 C10 123.6(7) . . ? N2 C9 C13 128.6(7) . . ? C10 C9 C13 107.5(6) . . ? N2 C9 Fe1 120.5(4) . . ? C10 C9 Fe1 70.2(4) . . ? C13 C9 Fe1 69.6(4) . . ? C11 C10 C9 107.8(9) . . ? C11 C10 Fe1 69.7(5) . . ? C9 C10 Fe1 68.8(4) . . ? C11 C10 H10A 126.1 . . ? C9 C10 H10A 126.1 . . ? Fe1 C10 H10A 127.0 . . ? C12 C11 C10 108.9(7) . . ? C12 C11 Fe1 69.4(5) . . ? C10 C11 Fe1 69.5(4) . . ? C12 C11 H11A 125.5 . . ? C10 C11 H11A 125.5 . . ? Fe1 C11 H11A 127.2 . . ? C11 C12 C13 107.2(8) . . ? C11 C12 Fe1 69.9(5) . . ? C13 C12 Fe1 69.2(4) . . ? C11 C12 H12A 126.4 . . ? C13 C12 H12A 126.4 . . ? Fe1 C12 H12A 126.0 . . ? C12 C13 C9 108.5(9) . . ? C12 C13 Fe1 69.7(4) . . ? C9 C13 Fe1 69.0(4) . . ? C12 C13 H13A 125.7 . . ? C9 C13 H13A 125.7 . . ? Fe1 C13 H13A 127.1 . . ? N1 C14 C15 114.2(6) . . ? N1 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? N1 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? H14B C14 H14A 107.6 . . ? C17 C15 C18 109.2(7) . . ? C17 C15 C16 109.5(7) . . ? C18 C15 C16 108.5(6) . . ? C17 C15 C14 109.6(6) . . ? C18 C15 C14 106.3(6) . . ? C16 C15 C14 113.6(5) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 115.6(5) . . ? N2 C19 H19B 108.4 . . ? C20 C19 H19B 108.4 . . ? N2 C19 H19A 108.4 . . ? C20 C19 H19A 108.4 . . ? H19B C19 H19A 107.5 . . ? C21 C20 C23 110.5(7) . . ? C21 C20 C19 110.8(6) . . ? C23 C20 C19 111.4(5) . . ? C21 C20 C22 111.0(6) . . ? C23 C20 C22 107.4(6) . . ? C19 C20 C22 105.8(6) . . ? 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 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C25 126.4(7) . . ? N3 C24 C28 127.2(10) . . ? C25 C24 C28 106.4(10) . . ? N3 C24 Fe2 125.9(5) . . ? C25 C24 Fe2 70.4(6) . . ? C28 C24 Fe2 70.5(7) . . ? C26 C25 C24 109.7(11) . . ? C26 C25 Fe2 72.1(6) . . ? C24 C25 Fe2 67.0(5) . . ? C26 C25 H25A 125.1 . . ? C24 C25 H25A 125.1 . . ? Fe2 C25 H25A 127.3 . . ? C25 C26 C27 107.5(12) . . ? C25 C26 Fe2 67.5(5) . . ? C27 C26 Fe2 70.1(6) . . ? C25 C26 H26A 126.3 . . ? C27 C26 H26A 126.3 . . ? Fe2 C26 H26A 127.7 . . ? C26 C27 C28 108.8(9) . . ? C26 C27 Fe2 69.6(6) . . ? C28 C27 Fe2 67.1(6) . . ? C26 C27 H27A 125.6 . . ? C28 C27 H27A 125.6 . . ? Fe2 C27 H27A 129.4 . . ? C27 C28 C24 107.5(12) . . ? C27 C28 Fe2 71.8(8) . . ? C24 C28 Fe2 66.8(6) . . ? C27 C28 H28A 126.2 . . ? C24 C28 H28A 126.2 . . ? Fe2 C28 H28A 126.7 . . ? C30 C29 N4 126.5(8) . . ? C30 C29 C33 107.3(9) . . ? N4 C29 C33 126.2(11) . . ? C30 C29 Fe2 72.4(6) . . ? N4 C29 Fe2 124.7(5) . . ? C33 C29 Fe2 70.5(5) . . ? C29 C30 C31 107.8(10) . . ? C29 C30 Fe2 66.2(5) . . ? C31 C30 Fe2 71.9(6) . . ? C29 C30 H30A 126.1 . . ? C31 C30 H30A 126.1 . . ? Fe2 C30 H30A 127.3 . . ? C32 C31 C30 110.1(12) . . ? C32 C31 Fe2 70.2(7) . . ? C30 C31 Fe2 67.8(6) . . ? C32 C31 H31A 125.0 . . ? C30 C31 H31A 125.0 . . ? Fe2 C31 H31A 128.7 . . ? C31 C32 C33 109.2(9) . . ? C31 C32 Fe2 72.1(7) . . ? C33 C32 Fe2 67.0(5) . . ? C31 C32 H32A 125.4 . . ? C33 C32 H32A 125.4 . . ? Fe2 C32 H32A 127.1 . . ? C32 C33 C29 105.5(11) . . ? C32 C33 Fe2 71.2(7) . . ? C29 C33 Fe2 66.4(5) . . ? C32 C33 H33A 127.2 . . ? C29 C33 H33A 127.2 . . ? Fe2 C33 H33A 126.6 . . ? N3 C34 C35 117.5(6) . . ? N3 C34 H34A 107.9 . . ? C35 C34 H34A 107.9 . . ? N3 C34 H34B 107.9 . . ? C35 C34 H34B 107.9 . . ? H34A C34 H34B 107.2 . . ? C38 C35 C37 109.6(10) . . ? C38 C35 C36 111.7(10) . . ? C37 C35 C36 106.5(7) . . ? C38 C35 C34 111.5(6) . . ? C37 C35 C34 104.8(7) . . ? C36 C35 C34 112.3(8) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N4 C39 C40 120.9(8) . . ? N4 C39 H39B 107.1 . . ? C40 C39 H39B 107.1 . . ? N4 C39 H39A 107.1 . . ? C40 C39 H39A 107.1 . . ? H39B C39 H39A 106.8 . . ? C41 C40 C42 115.5(6) . . ? C41 C40 C39 120.0(8) . . ? C42 C40 C39 117.2(7) . . ? C41 C40 C43 93.2(10) . . ? C42 C40 C43 97.6(8) . . ? C39 C40 C43 106.1(7) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C40 C42 H42A 109.5 . . ? C40 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C40 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C40 C43 H43C 109.5 . . ? C40 C43 H43B 109.5 . . ? H43C C43 H43B 109.5 . . ? C40 C43 H43A 109.5 . . ? H43C C43 H43A 109.5 . . ? H43B C43 H43A 109.5 . . ? C4 N1 C1 115.6(4) . . ? C4 N1 C14 112.7(5) . . ? C1 N1 C14 116.1(5) . . ? C9 N2 C1 115.7(5) . . ? C9 N2 C19 116.9(5) . . ? C1 N2 C19 116.1(4) . . ? C3 N3 C24 126.9(6) . . ? C3 N3 C34 118.3(6) . . ? C24 N3 C34 114.0(5) . . ? C3 N4 C29 126.3(6) . . ? C3 N4 C39 123.3(6) . . ? C29 N4 C39 107.6(6) . . ? C8 Fe1 C4 41.4(3) . . ? C8 Fe1 C9 109.2(3) . . ? C4 Fe1 C9 95.2(2) . . ? C8 Fe1 C13 102.7(3) . . ? C4 Fe1 C13 117.9(3) . . ? C9 Fe1 C13 41.4(3) . . ? C8 Fe1 C5 69.2(3) . . ? C4 Fe1 C5 41.4(3) . . ? C9 Fe1 C5 118.4(3) . . ? C13 Fe1 C5 156.2(2) . . ? C8 Fe1 C12 128.3(4) . . ? C4 Fe1 C12 158.8(3) . . ? C9 Fe1 C12 69.7(3) . . ? C13 Fe1 C12 41.1(3) . . ? C5 Fe1 C12 159.3(4) . . ? C8 Fe1 C7 41.2(3) . . ? C4 Fe1 C7 69.3(3) . . ? C9 Fe1 C7 148.2(4) . . ? C13 Fe1 C7 121.1(4) . . ? C5 Fe1 C7 68.3(3) . . ? C12 Fe1 C7 115.9(4) . . ? C8 Fe1 C10 143.7(3) . . ? C4 Fe1 C10 109.6(3) . . ? C9 Fe1 C10 41.1(3) . . ? C13 Fe1 C10 68.9(4) . . ? C5 Fe1 C10 103.8(3) . . ? C12 Fe1 C10 69.1(4) . . ? C7 Fe1 C10 169.6(4) . . ? C8 Fe1 C11 168.9(4) . . ? C4 Fe1 C11 148.2(4) . . ? C9 Fe1 C11 68.9(3) . . ? C13 Fe1 C11 68.4(4) . . ? C5 Fe1 C11 121.6(4) . . ? C12 Fe1 C11 40.7(4) . . ? C7 Fe1 C11 137.1(3) . . ? C10 Fe1 C11 40.8(3) . . ? C8 Fe1 C6 69.2(4) . . ? C4 Fe1 C6 69.8(3) . . ? C9 Fe1 C6 159.3(3) . . ? C13 Fe1 C6 158.7(4) . . ? C5 Fe1 C6 41.1(3) . . ? C12 Fe1 C6 128.3(3) . . ? C7 Fe1 C6 40.3(4) . . ? C10 Fe1 C6 129.4(4) . . ? C11 Fe1 C6 116.6(3) . . ? C29 Fe2 C24 92.4(3) . . ? C29 Fe2 C25 113.4(3) . . ? C24 Fe2 C25 42.6(4) . . ? C29 Fe2 C28 112.3(5) . . ? C24 Fe2 C28 42.7(4) . . ? C25 Fe2 C28 70.3(5) . . ? C29 Fe2 C33 43.1(3) . . ? C24 Fe2 C33 111.5(4) . . ? C25 Fe2 C33 150.6(4) . . ? C28 Fe2 C33 99.9(5) . . ? C29 Fe2 C30 41.4(4) . . ? C24 Fe2 C30 113.7(3) . . ? C25 Fe2 C30 104.7(4) . . ? C28 Fe2 C30 150.4(5) . . ? C33 Fe2 C30 69.7(5) . . ? C29 Fe2 C26 153.1(4) . . ? C24 Fe2 C26 70.7(4) . . ? C25 Fe2 C26 40.4(4) . . ? C28 Fe2 C26 69.6(6) . . ? C33 Fe2 C26 162.7(5) . . ? C30 Fe2 C26 126.1(6) . . ? C29 Fe2 C32 70.3(4) . . ? C24 Fe2 C32 152.8(5) . . ? C25 Fe2 C32 163.9(6) . . ? C28 Fe2 C32 123.9(5) . . ? C33 Fe2 C32 41.8(5) . . ? C30 Fe2 C32 67.1(4) . . ? C26 Fe2 C32 132.5(5) . . ? C29 Fe2 C27 152.8(7) . . ? C24 Fe2 C27 70.3(4) . . ? C25 Fe2 C27 68.1(5) . . ? C28 Fe2 C27 41.1(6) . . ? C33 Fe2 C27 123.0(6) . . ? C30 Fe2 C27 165.3(7) . . ? C26 Fe2 C27 40.3(6) . . ? C32 Fe2 C27 116.3(4) . . ? C29 Fe2 C31 68.9(4) . . ? C24 Fe2 C31 153.8(4) . . ? C25 Fe2 C31 127.3(5) . . ? C28 Fe2 C31 161.3(5) . . ? C33 Fe2 C31 67.7(5) . . ? C30 Fe2 C31 40.3(3) . . ? C26 Fe2 C31 118.4(6) . . ? C32 Fe2 C31 37.8(5) . . ? C27 Fe2 C31 133.5(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.219 _refine_diff_density_min -0.850 _refine_diff_density_rms 0.106 #===================================================================== # Attachment 'i0739a.cif' data_i0739a _database_code_depnum_ccdc_archive 'CCDC 782900' #TrackingRef 'i0739a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H39 Fe N3' _chemical_formula_sum 'C26 H39 Fe N3' _chemical_formula_weight 449.45 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 15.253(2) _cell_length_b 9.8425(17) _cell_length_c 16.706(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.195(11) _cell_angle_gamma 90.00 _cell_volume 2497.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4591 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 25.10 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.147 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8729 _exptl_absorpt_correction_T_max 0.9758 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 117 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 13276 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.1209 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4397 _reflns_number_gt 2277 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4397 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1205 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 0.828 _refine_ls_restrained_S_all 0.828 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0371(2) 0.1204(4) 0.7338(2) 0.0392(9) Uani 1 1 d . . . C2 C -0.0783(3) 0.0028(4) 0.7347(2) 0.0443(9) Uani 1 1 d . . . C3 C -0.0939(2) -0.2374(4) 0.7184(2) 0.0488(10) Uani 1 1 d . . . C4 C 0.0033(3) -0.2532(5) 0.7454(3) 0.0798(14) Uani 1 1 d . . . H4A H 0.0372 -0.1912 0.7152 0.096 Uiso 1 1 calc R . . H4B H 0.0215 -0.3459 0.7359 0.096 Uiso 1 1 calc R . . H4C H 0.0134 -0.2327 0.8022 0.096 Uiso 1 1 calc R . . C5 C -0.1091(3) -0.2558(5) 0.6277(2) 0.0714(13) Uani 1 1 d . . . H5A H -0.0906 -0.3462 0.6134 0.086 Uiso 1 1 calc R . . H5B H -0.0752 -0.1887 0.6012 0.086 Uiso 1 1 calc R . . H5C H -0.1711 -0.2442 0.6108 0.086 Uiso 1 1 calc R . . C6 C -0.1479(4) -0.3376(5) 0.7616(3) 0.0890(18) Uani 1 1 d . . . H6A H -0.1389 -0.3216 0.8191 0.107 Uiso 1 1 calc R . . H6B H -0.1296 -0.4294 0.7499 0.107 Uiso 1 1 calc R . . H6C H -0.2097 -0.3262 0.7436 0.107 Uiso 1 1 calc R . . C7 C 0.0487(2) 0.2102(4) 0.63080(18) 0.0405(8) Uani 1 1 d . . . C8 C 0.0939(3) 0.3355(4) 0.6223(2) 0.0502(11) Uani 1 1 d . . . H8A H 0.0711 0.4228 0.6301 0.060 Uiso 1 1 calc R . . C9 C 0.1794(3) 0.3052(5) 0.5998(2) 0.0541(12) Uani 1 1 d . . . H9A H 0.2230 0.3687 0.5896 0.065 Uiso 1 1 calc R . . C10 C 0.1868(3) 0.1639(5) 0.5957(3) 0.0542(12) Uani 1 1 d . . . H10A H 0.2371 0.1162 0.5830 0.065 Uiso 1 1 calc R . . C11 C 0.1068(3) 0.1041(4) 0.6138(2) 0.0456(10) Uani 1 1 d . . . H11A H 0.0943 0.0106 0.6143 0.055 Uiso 1 1 calc R . . C12 C 0.0969(2) 0.1954(4) 0.8095(2) 0.0403(10) Uani 1 1 d . . . C13 C 0.1445(3) 0.3195(4) 0.8122(2) 0.0492(11) Uani 1 1 d . . . H13A H 0.1205 0.4068 0.8170 0.059 Uiso 1 1 calc R . . C14 C 0.2352(3) 0.2882(6) 0.8065(2) 0.0553(11) Uani 1 1 d . . . H14A H 0.2816 0.3511 0.8068 0.066 Uiso 1 1 calc R . . C15 C 0.2424(3) 0.1471(5) 0.8004(2) 0.0542(12) Uani 1 1 d . . . H15A H 0.2948 0.0988 0.7954 0.065 Uiso 1 1 calc R . . C16 C 0.1573(3) 0.0884(4) 0.8031(2) 0.0486(11) Uani 1 1 d . . . H16A H 0.1439 -0.0049 0.8011 0.058 Uiso 1 1 calc R . . C17 C -0.1039(2) 0.2915(4) 0.6378(2) 0.0450(9) Uani 1 1 d . . . H17A H -0.0761 0.3814 0.6399 0.054 Uiso 1 1 calc R . . H17B H -0.1464 0.2897 0.6784 0.054 Uiso 1 1 calc R . . C18 C -0.1538(2) 0.2718(4) 0.5541(2) 0.0432(9) Uani 1 1 d . . . C19 C -0.0916(3) 0.2895(6) 0.4875(2) 0.0685(12) Uani 1 1 d . . . H19A H -0.0474 0.2183 0.4919 0.082 Uiso 1 1 calc R . . H19B H -0.0629 0.3774 0.4932 0.082 Uiso 1 1 calc R . . H19C H -0.1251 0.2840 0.4354 0.082 Uiso 1 1 calc R . . C20 C -0.2246(3) 0.3822(4) 0.5450(3) 0.0653(13) Uani 1 1 d . . . H20A H -0.1968 0.4709 0.5468 0.078 Uiso 1 1 calc R . . H20B H -0.2624 0.3746 0.5885 0.078 Uiso 1 1 calc R . . H20C H -0.2596 0.3710 0.4940 0.078 Uiso 1 1 calc R . . C21 C -0.1970(3) 0.1348(4) 0.5475(3) 0.0576(12) Uani 1 1 d . . . H21A H -0.2352 0.1240 0.5904 0.069 Uiso 1 1 calc R . . H21B H -0.1522 0.0646 0.5518 0.069 Uiso 1 1 calc R . . H21C H -0.2315 0.1273 0.4960 0.069 Uiso 1 1 calc R . . C22 C -0.0460(2) 0.2817(5) 0.8466(2) 0.0591(10) Uani 1 1 d . . . H22A H -0.1044 0.2907 0.8174 0.071 Uiso 1 1 calc R . . H22B H -0.0158 0.3691 0.8430 0.071 Uiso 1 1 calc R . . C23 C -0.0574(2) 0.2522(4) 0.9348(2) 0.0455(10) Uani 1 1 d . . . C24 C -0.1082(4) 0.3730(6) 0.9645(4) 0.0953(18) Uani 1 1 d . . . H24A H -0.1633 0.3831 0.9313 0.114 Uiso 1 1 calc R . . H24B H -0.0734 0.4550 0.9612 0.114 Uiso 1 1 calc R . . H24C H -0.1201 0.3577 1.0198 0.114 Uiso 1 1 calc R . . C25 C -0.1094(4) 0.1241(5) 0.9427(4) 0.0930(18) Uani 1 1 d . . . H25A H -0.0794 0.0488 0.9196 0.112 Uiso 1 1 calc R . . H25B H -0.1675 0.1347 0.9146 0.112 Uiso 1 1 calc R . . H25C H -0.1150 0.1061 0.9991 0.112 Uiso 1 1 calc R . . C26 C 0.0322(3) 0.2447(5) 0.9837(2) 0.0712(14) Uani 1 1 d . . . H26A H 0.0645 0.3281 0.9766 0.085 Uiso 1 1 calc R . . H26B H 0.0652 0.1683 0.9654 0.085 Uiso 1 1 calc R . . H26C H 0.0237 0.2330 1.0401 0.085 Uiso 1 1 calc R . . N1 N -0.1260(2) -0.0982(3) 0.7350(2) 0.0506(9) Uani 1 1 d . . . N2 N -0.03671(18) 0.1892(3) 0.65808(17) 0.0426(8) Uani 1 1 d . . . N3 N 0.00306(19) 0.1787(3) 0.80718(17) 0.0410(8) Uani 1 1 d . . . Fe1 Fe 0.15793(3) 0.21966(6) 0.70830(3) 0.04084(15) 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 C1 0.036(2) 0.041(2) 0.041(2) 0.0008(19) 0.0054(17) 0.0000(18) C2 0.044(2) 0.044(3) 0.045(2) -0.0020(19) 0.0076(18) 0.007(2) C3 0.055(2) 0.035(3) 0.058(2) -0.001(2) 0.0132(19) -0.007(2) C4 0.074(3) 0.062(4) 0.102(3) -0.007(3) 0.003(3) 0.009(2) C5 0.084(3) 0.066(4) 0.065(3) -0.011(3) 0.014(2) -0.001(3) C6 0.110(5) 0.065(3) 0.098(4) 0.016(3) 0.040(4) -0.015(3) C7 0.042(2) 0.049(2) 0.0301(18) 0.002(2) -0.0011(15) -0.005(2) C8 0.046(3) 0.058(3) 0.046(2) 0.002(2) 0.000(2) 0.006(2) C9 0.053(3) 0.070(4) 0.039(2) 0.010(2) 0.0008(19) -0.012(2) C10 0.037(2) 0.074(3) 0.052(3) -0.004(2) 0.0074(19) -0.004(2) C11 0.044(2) 0.048(3) 0.043(2) -0.007(2) 0.0009(19) 0.001(2) C12 0.043(2) 0.045(3) 0.0321(19) 0.0010(19) -0.0027(16) -0.006(2) C13 0.056(3) 0.049(3) 0.042(2) -0.006(2) 0.001(2) 0.003(2) C14 0.047(2) 0.070(3) 0.046(2) -0.004(3) -0.0053(18) -0.014(3) C15 0.036(2) 0.078(4) 0.047(3) 0.006(3) -0.0042(19) 0.001(2) C16 0.044(3) 0.058(3) 0.043(2) 0.005(2) -0.0006(19) 0.004(2) C17 0.0386(19) 0.050(2) 0.045(2) -0.002(2) -0.0015(15) 0.005(2) C18 0.0351(18) 0.048(2) 0.045(2) -0.002(2) -0.0044(15) 0.004(2) C19 0.054(2) 0.106(4) 0.043(2) 0.014(3) -0.0079(18) -0.004(3) C20 0.052(3) 0.063(3) 0.078(3) 0.004(3) -0.009(2) 0.006(2) C21 0.056(3) 0.054(3) 0.061(3) -0.009(2) -0.005(2) -0.001(2) C22 0.049(2) 0.063(3) 0.065(3) 0.001(3) 0.0033(19) 0.007(2) C23 0.045(2) 0.046(3) 0.047(2) -0.0050(19) 0.0126(16) -0.0012(17) C24 0.064(4) 0.095(4) 0.128(5) -0.027(4) 0.012(3) 0.008(3) C25 0.087(4) 0.080(4) 0.114(5) 0.023(3) 0.023(4) -0.013(3) C26 0.064(3) 0.101(4) 0.049(2) -0.010(3) 0.007(2) 0.003(3) N1 0.051(2) 0.047(2) 0.055(2) -0.0065(18) 0.0107(17) -0.0077(18) N2 0.0366(16) 0.050(2) 0.0408(17) 0.0056(15) 0.0003(13) 0.0032(14) N3 0.0395(17) 0.045(2) 0.0392(17) -0.0055(15) 0.0053(14) -0.0007(14) Fe1 0.0332(3) 0.0520(3) 0.0369(3) 0.0010(4) 0.00062(19) -0.0019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.318(5) . ? C1 N2 1.435(4) . ? C1 N3 1.439(4) . ? C2 N1 1.232(5) . ? C3 N1 1.490(5) . ? C3 C6 1.510(5) . ? C3 C4 1.518(5) . ? C3 C5 1.523(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 H4C 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 C11 1.415(5) . ? C7 C8 1.427(5) . ? C7 N2 1.433(4) . ? C7 Fe1 2.018(3) . ? C8 C9 1.421(5) . ? C8 Fe1 2.016(4) . ? C8 H8A 0.9400 . ? C9 C10 1.398(6) . ? C9 Fe1 2.051(4) . ? C9 H9A 0.9400 . ? C10 C11 1.412(5) . ? C10 Fe1 2.045(4) . ? C10 H10A 0.9400 . ? C11 Fe1 2.043(4) . ? C11 H11A 0.9400 . ? C12 C16 1.410(5) . ? C12 C13 1.419(5) . ? C12 N3 1.439(4) . ? C12 Fe1 2.016(3) . ? C13 C14 1.429(5) . ? C13 Fe1 2.022(4) . ? C13 H13A 0.9400 . ? C14 C15 1.398(6) . ? C14 Fe1 2.046(4) . ? C14 H14A 0.9400 . ? C15 C16 1.425(6) . ? C15 Fe1 2.044(4) . ? C15 H15A 0.9400 . ? C16 Fe1 2.045(4) . ? C16 H16A 0.9400 . ? C17 N2 1.455(4) . ? C17 C18 1.543(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C21 1.501(5) . ? C18 C20 1.530(5) . ? C18 C19 1.536(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 N3 1.453(5) . ? C22 C23 1.527(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C25 1.502(6) . ? C23 C24 1.526(6) . ? C23 C26 1.529(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 H25C 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? 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 C2 C1 N2 117.6(3) . . ? C2 C1 N3 120.5(3) . . ? N2 C1 N3 121.9(3) . . ? N1 C2 C1 172.3(4) . . ? N1 C3 C6 108.0(3) . . ? N1 C3 C4 111.6(3) . . ? C6 C3 C4 110.6(4) . . ? N1 C3 C5 105.8(3) . . ? C6 C3 C5 110.9(4) . . ? C4 C3 C5 109.9(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C11 C7 C8 107.5(3) . . ? C11 C7 N2 124.1(4) . . ? C8 C7 N2 128.2(4) . . ? C11 C7 Fe1 70.6(2) . . ? C8 C7 Fe1 69.2(2) . . ? N2 C7 Fe1 121.6(2) . . ? C9 C8 C7 108.0(4) . . ? C9 C8 Fe1 70.9(2) . . ? C7 C8 Fe1 69.3(2) . . ? C9 C8 H8A 126.0 . . ? C7 C8 H8A 126.0 . . ? Fe1 C8 H8A 125.3 . . ? C10 C9 C8 107.6(4) . . ? C10 C9 Fe1 69.8(3) . . ? C8 C9 Fe1 68.2(2) . . ? C10 C9 H9A 126.2 . . ? C8 C9 H9A 126.2 . . ? Fe1 C9 H9A 127.3 . . ? C9 C10 C11 109.2(4) . . ? C9 C10 Fe1 70.3(3) . . ? C11 C10 Fe1 69.7(2) . . ? C9 C10 H10A 125.4 . . ? C11 C10 H10A 125.4 . . ? Fe1 C10 H10A 126.2 . . ? C10 C11 C7 107.8(4) . . ? C10 C11 Fe1 69.9(2) . . ? C7 C11 Fe1 68.7(2) . . ? C10 C11 H11A 126.1 . . ? C7 C11 H11A 126.1 . . ? Fe1 C11 H11A 126.9 . . ? C16 C12 C13 108.1(3) . . ? C16 C12 N3 124.6(3) . . ? C13 C12 N3 127.2(3) . . ? C16 C12 Fe1 70.8(2) . . ? C13 C12 Fe1 69.6(2) . . ? N3 C12 Fe1 121.7(2) . . ? C12 C13 C14 107.9(4) . . ? C12 C13 Fe1 69.2(2) . . ? C14 C13 Fe1 70.3(2) . . ? C12 C13 H13A 126.0 . . ? C14 C13 H13A 126.0 . . ? Fe1 C13 H13A 126.0 . . ? C15 C14 C13 107.6(4) . . ? C15 C14 Fe1 70.0(3) . . ? C13 C14 Fe1 68.5(2) . . ? C15 C14 H14A 126.2 . . ? C13 C14 H14A 126.2 . . ? Fe1 C14 H14A 126.8 . . ? C14 C15 C16 108.8(4) . . ? C14 C15 Fe1 70.1(3) . . ? C16 C15 Fe1 69.6(2) . . ? C14 C15 H15A 125.6 . . ? C16 C15 H15A 125.6 . . ? Fe1 C15 H15A 126.3 . . ? C12 C16 C15 107.6(4) . . ? C12 C16 Fe1 68.6(2) . . ? C15 C16 Fe1 69.6(2) . . ? C12 C16 H16A 126.2 . . ? C15 C16 H16A 126.2 . . ? Fe1 C16 H16A 127.2 . . ? N2 C17 C18 113.8(3) . . ? N2 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N2 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C21 C18 C20 109.2(3) . . ? C21 C18 C19 110.2(4) . . ? C20 C18 C19 109.0(4) . . ? C21 C18 C17 110.9(3) . . ? C20 C18 C17 106.6(3) . . ? C19 C18 C17 110.8(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 C23 114.3(3) . . ? N3 C22 H22A 108.7 . . ? C23 C22 H22A 108.7 . . ? N3 C22 H22B 108.7 . . ? C23 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C25 C23 C24 109.7(4) . . ? C25 C23 C22 110.6(4) . . ? C24 C23 C22 105.7(4) . . ? C25 C23 C26 111.5(4) . . ? C24 C23 C26 108.6(4) . . ? C22 C23 C26 110.5(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C2 N1 C3 122.4(3) . . ? C7 N2 C1 115.1(3) . . ? C7 N2 C17 117.9(3) . . ? C1 N2 C17 118.2(3) . . ? C12 N3 C1 114.5(3) . . ? C12 N3 C22 117.4(3) . . ? C1 N3 C22 117.8(3) . . ? C12 Fe1 C8 115.72(16) . . ? C12 Fe1 C7 96.64(13) . . ? C8 Fe1 C7 41.42(15) . . ? C12 Fe1 C13 41.14(15) . . ? C8 Fe1 C13 104.89(17) . . ? C7 Fe1 C13 115.55(16) . . ? C12 Fe1 C11 114.17(16) . . ? C8 Fe1 C11 68.74(16) . . ? C7 Fe1 C11 40.79(15) . . ? C13 Fe1 C11 150.83(17) . . ? C12 Fe1 C15 68.56(15) . . ? C8 Fe1 C15 164.96(19) . . ? C7 Fe1 C15 153.43(18) . . ? C13 Fe1 C15 68.24(18) . . ? C11 Fe1 C15 123.92(19) . . ? C12 Fe1 C16 40.62(15) . . ? C8 Fe1 C16 150.88(17) . . ? C7 Fe1 C16 113.98(16) . . ? C13 Fe1 C16 68.52(16) . . ? C11 Fe1 C16 102.64(17) . . ? C15 Fe1 C16 40.78(16) . . ? C12 Fe1 C10 153.32(16) . . ? C8 Fe1 C10 68.12(17) . . ? C7 Fe1 C10 68.40(15) . . ? C13 Fe1 C10 165.32(18) . . ? C11 Fe1 C10 40.42(15) . . ? C15 Fe1 C10 115.15(19) . . ? C16 Fe1 C10 124.00(19) . . ? C12 Fe1 C14 69.05(15) . . ? C8 Fe1 C14 126.3(2) . . ? C7 Fe1 C14 155.78(18) . . ? C13 Fe1 C14 41.13(16) . . ? C11 Fe1 C14 162.9(2) . . ? C15 Fe1 C14 39.97(16) . . ? C16 Fe1 C14 68.28(19) . . ? C10 Fe1 C14 132.03(16) . . ? C12 Fe1 C9 155.77(17) . . ? C8 Fe1 C9 40.88(16) . . ? C7 Fe1 C9 68.94(15) . . ? C13 Fe1 C9 126.58(17) . . ? C11 Fe1 C9 68.03(17) . . ? C15 Fe1 C9 131.96(17) . . ? C16 Fe1 C9 162.95(18) . . ? C10 Fe1 C9 39.91(15) . . ? C14 Fe1 C9 116.53(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.352 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.049 # Attachment 'i0765.cif' data_i0765 _database_code_depnum_ccdc_archive 'CCDC 782901' #TrackingRef 'i0765.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H36 Fe N2 O2' _chemical_formula_sum 'C25 H36 Fe N2 O2' _chemical_formula_weight 452.41 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1007(16) _cell_length_b 17.090(2) _cell_length_c 11.5086(13) _cell_angle_alpha 90.00 _cell_angle_beta 97.616(10) _cell_angle_gamma 90.00 _cell_volume 2359.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 6211 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 24.96 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8764 _exptl_absorpt_correction_T_max 0.9616 _exptl_absorpt_process_details 'X-red ver. 1.31 (stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 92 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 11142 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4155 _reflns_number_gt 2151 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0189P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4155 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1129 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2270(2) 0.12544(18) 0.1970(3) 0.0439(8) Uani 1 1 d . . . C2 C 0.1112(3) 0.16346(19) 0.1770(3) 0.0513(9) Uani 1 1 d . . . H2A H 0.0508 0.1297 0.1383 0.062 Uiso 1 1 calc R . . C3 C 0.2010(3) 0.18469(19) 0.1022(3) 0.0517(8) Uani 1 1 d . . . H3B H 0.1918 0.1661 0.0210 0.062 Uiso 1 1 calc R . . H3A H 0.2360 0.2363 0.1141 0.062 Uiso 1 1 calc R . . C4 C 0.0757(3) 0.2239(2) 0.2571(3) 0.0540(9) Uani 1 1 d . . . C5 C -0.0699(3) 0.2574(3) 0.3679(4) 0.0840(13) Uani 1 1 d . . . H5A H -0.0786 0.3082 0.3302 0.101 Uiso 1 1 calc R . . H5B H -0.0201 0.2620 0.4409 0.101 Uiso 1 1 calc R . . H5C H -0.1421 0.2388 0.3841 0.101 Uiso 1 1 calc R . . C6 C 0.2957(3) 0.11257(18) 0.4058(3) 0.0465(8) Uani 1 1 d . . . C7 C 0.3747(3) 0.0619(2) 0.4718(3) 0.0525(9) Uani 1 1 d . . . H7A H 0.4455 0.0492 0.4523 0.063 Uiso 1 1 calc R . . C8 C 0.3292(3) 0.0341(2) 0.5714(3) 0.0605(10) Uani 1 1 d . . . H8A H 0.3642 -0.0001 0.6288 0.073 Uiso 1 1 calc R . . C9 C 0.2226(3) 0.0665(2) 0.5690(3) 0.0609(10) Uani 1 1 d . . . H9A H 0.1734 0.0575 0.6244 0.073 Uiso 1 1 calc R . . C10 C 0.2014(3) 0.1154(2) 0.4686(3) 0.0544(9) Uani 1 1 d . . . H10A H 0.1362 0.1448 0.4471 0.065 Uiso 1 1 calc R . . C11 C 0.2010(2) -0.0131(2) 0.2434(3) 0.0492(8) Uani 1 1 d . . . C12 C 0.2714(3) -0.07317(19) 0.2970(3) 0.0569(9) Uani 1 1 d . . . H12A H 0.3434 -0.0849 0.2799 0.068 Uiso 1 1 calc R . . C13 C 0.2150(4) -0.1124(2) 0.3804(3) 0.0679(11) Uani 1 1 d . . . H13A H 0.2434 -0.1540 0.4288 0.082 Uiso 1 1 calc R . . C14 C 0.1098(3) -0.0784(2) 0.3781(3) 0.0691(11) Uani 1 1 d . . . H14A H 0.0552 -0.0937 0.4244 0.083 Uiso 1 1 calc R . . C15 C 0.0990(3) -0.0169(2) 0.2946(3) 0.0598(10) Uani 1 1 d . . . H15A H 0.0363 0.0154 0.2760 0.072 Uiso 1 1 calc R . . C16 C 0.4206(2) 0.16147(18) 0.2705(3) 0.0451(8) Uani 1 1 d . . . H16B H 0.4186 0.1654 0.1853 0.054 Uiso 1 1 calc R . . H16A H 0.4639 0.1147 0.2962 0.054 Uiso 1 1 calc R . . C17 C 0.4826(3) 0.23336(19) 0.3269(3) 0.0476(8) Uani 1 1 d . . . C18 C 0.4239(3) 0.3084(2) 0.2787(3) 0.0630(10) Uani 1 1 d . . . H18A H 0.3477 0.3085 0.2963 0.076 Uiso 1 1 calc R . . H18B H 0.4238 0.3106 0.1944 0.076 Uiso 1 1 calc R . . H18C H 0.4631 0.3536 0.3148 0.076 Uiso 1 1 calc R . . C19 C 0.6006(3) 0.2307(2) 0.2941(3) 0.0606(10) Uani 1 1 d . . . H19A H 0.5972 0.2290 0.2094 0.073 Uiso 1 1 calc R . . H19B H 0.6384 0.1843 0.3279 0.073 Uiso 1 1 calc R . . H19C H 0.6411 0.2769 0.3241 0.073 Uiso 1 1 calc R . . C20 C 0.4889(3) 0.2342(2) 0.4610(3) 0.0671(11) Uani 1 1 d . . . H20A H 0.5251 0.1867 0.4930 0.081 Uiso 1 1 calc R . . H20B H 0.4142 0.2369 0.4825 0.081 Uiso 1 1 calc R . . H20C H 0.5315 0.2793 0.4923 0.081 Uiso 1 1 calc R . . C21 C 0.3091(2) 0.02161(17) 0.0821(3) 0.0454(8) Uani 1 1 d . . . H21B H 0.3668 -0.0101 0.1276 0.054 Uiso 1 1 calc R . . H21A H 0.3449 0.0692 0.0578 0.054 Uiso 1 1 calc R . . C22 C 0.2625(3) -0.02445(17) -0.0285(3) 0.0456(8) Uani 1 1 d . . . C23 C 0.3612(3) -0.0413(2) -0.0964(3) 0.0664(10) Uani 1 1 d . . . H23A H 0.4160 -0.0729 -0.0484 0.080 Uiso 1 1 calc R . . H23B H 0.3949 0.0077 -0.1157 0.080 Uiso 1 1 calc R . . H23C H 0.3347 -0.0693 -0.1681 0.080 Uiso 1 1 calc R . . C24 C 0.2082(3) -0.10089(19) -0.0004(3) 0.0628(10) Uani 1 1 d . . . H24A H 0.1433 -0.0901 0.0382 0.075 Uiso 1 1 calc R . . H24B H 0.2610 -0.1320 0.0511 0.075 Uiso 1 1 calc R . . H24C H 0.1857 -0.1295 -0.0724 0.075 Uiso 1 1 calc R . . C25 C 0.1774(3) 0.0252(2) -0.1062(3) 0.0652(11) Uani 1 1 d . . . H25C H 0.1503 -0.0038 -0.1767 0.078 Uiso 1 1 calc R . . H25B H 0.2124 0.0732 -0.1272 0.078 Uiso 1 1 calc R . . H25A H 0.1154 0.0375 -0.0639 0.078 Uiso 1 1 calc R . . N1 N 0.30560(19) 0.15032(14) 0.2968(2) 0.0429(6) Uani 1 1 d . . . N2 N 0.22588(19) 0.04414(15) 0.1591(2) 0.0446(6) Uani 1 1 d . . . O1 O 0.1228(2) 0.28355(14) 0.2886(2) 0.0696(7) Uani 1 1 d . . . O2 O -0.02380(19) 0.20264(14) 0.2913(2) 0.0670(7) Uani 1 1 d . . . Fe1 Fe 0.23177(4) 0.00407(3) 0.41830(4) 0.05064(14) 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 C1 0.0501(18) 0.045(2) 0.036(2) 0.0025(16) 0.0062(15) 0.0054(15) C2 0.055(2) 0.050(2) 0.047(2) -0.0023(17) 0.0007(16) 0.0067(16) C3 0.058(2) 0.052(2) 0.045(2) 0.0033(18) 0.0081(16) 0.0048(16) C4 0.054(2) 0.058(2) 0.049(2) 0.003(2) 0.0013(18) 0.0127(19) C5 0.067(3) 0.103(3) 0.086(3) -0.016(3) 0.022(2) 0.025(2) C6 0.050(2) 0.047(2) 0.042(2) 0.0000(17) 0.0073(17) 0.0029(16) C7 0.055(2) 0.058(2) 0.045(2) 0.0092(18) 0.0091(17) 0.0058(17) C8 0.071(2) 0.064(2) 0.047(2) 0.0142(19) 0.0071(18) 0.0005(19) C9 0.073(2) 0.067(2) 0.046(2) 0.004(2) 0.021(2) 0.000(2) C10 0.061(2) 0.058(2) 0.045(2) 0.0056(19) 0.0127(18) 0.0033(18) C11 0.0550(18) 0.047(2) 0.045(2) 0.0001(18) 0.0048(15) -0.0044(17) C12 0.071(2) 0.050(2) 0.052(2) 0.0046(19) 0.0121(19) 0.0007(18) C13 0.087(3) 0.067(3) 0.049(3) 0.015(2) 0.007(2) -0.008(2) C14 0.075(3) 0.083(3) 0.050(3) 0.009(2) 0.012(2) -0.026(2) C15 0.0559(19) 0.068(3) 0.054(2) 0.006(2) 0.0049(16) -0.0058(18) C16 0.0497(19) 0.0466(19) 0.039(2) -0.0004(15) 0.0058(15) 0.0011(15) C17 0.058(2) 0.049(2) 0.037(2) -0.0047(17) 0.0085(16) -0.0061(16) C18 0.077(2) 0.054(2) 0.060(3) -0.006(2) 0.015(2) -0.0035(19) C19 0.064(2) 0.064(2) 0.054(3) -0.009(2) 0.0074(19) -0.0174(19) C20 0.086(3) 0.068(2) 0.047(3) -0.0098(19) 0.009(2) -0.020(2) C21 0.0513(17) 0.048(2) 0.0383(19) 0.0015(15) 0.0117(15) -0.0003(13) C22 0.0554(19) 0.040(2) 0.041(2) -0.0044(15) 0.0048(15) -0.0058(14) C23 0.081(3) 0.064(2) 0.059(3) -0.012(2) 0.023(2) -0.003(2) C24 0.083(3) 0.053(2) 0.053(3) -0.0034(19) 0.0105(19) -0.0147(19) C25 0.076(2) 0.070(3) 0.049(2) -0.0020(19) 0.0020(18) 0.0008(19) N1 0.0463(15) 0.0480(16) 0.0347(17) 0.0012(13) 0.0061(12) 0.0004(12) N2 0.0513(15) 0.0443(15) 0.0393(17) 0.0006(14) 0.0104(13) 0.0017(13) O1 0.0773(17) 0.0555(16) 0.076(2) -0.0119(14) 0.0115(14) 0.0017(14) O2 0.0518(14) 0.0748(18) 0.0755(19) -0.0153(14) 0.0131(13) 0.0105(13) Fe1 0.0557(2) 0.0548(3) 0.0429(3) 0.0063(3) 0.01188(18) -0.0014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.454(4) . ? C1 N2 1.456(4) . ? C1 C3 1.491(4) . ? C1 C2 1.534(4) . ? C2 C4 1.486(5) . ? C2 C3 1.517(5) . ? C2 H2A 0.9900 . ? C3 H3B 0.9800 . ? C3 H3A 0.9800 . ? C4 O1 1.200(4) . ? C4 O2 1.365(4) . ? C5 O2 1.448(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 N1 1.429(4) . ? C6 C10 1.430(4) . ? C6 C7 1.432(4) . ? C6 Fe1 2.021(3) . ? C7 C8 1.418(5) . ? C7 Fe1 2.016(3) . ? C7 H7A 0.9400 . ? C8 C9 1.401(4) . ? C8 Fe1 2.051(4) . ? C8 H8A 0.9400 . ? C9 C10 1.422(5) . ? C9 Fe1 2.052(4) . ? C9 H9A 0.9400 . ? C10 Fe1 2.037(4) . ? C10 H10A 0.9400 . ? C11 C12 1.422(4) . ? C11 N2 1.436(4) . ? C11 C15 1.439(4) . ? C11 Fe1 2.020(3) . ? C12 C13 1.418(5) . ? C12 Fe1 2.025(4) . ? C12 H12A 0.9400 . ? C13 C14 1.396(5) . ? C13 Fe1 2.042(4) . ? C13 H13A 0.9400 . ? C14 C15 1.417(5) . ? C14 Fe1 2.048(4) . ? C14 H14A 0.9400 . ? C15 Fe1 2.033(3) . ? C15 H15A 0.9400 . ? C16 N1 1.476(4) . ? C16 C17 1.538(4) . ? C16 H16B 0.9800 . ? C16 H16A 0.9800 . ? C17 C19 1.524(4) . ? C17 C18 1.534(4) . ? C17 C20 1.535(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? C21 N2 1.478(4) . ? C21 C22 1.538(4) . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? C22 C24 1.516(4) . ? C22 C25 1.528(4) . ? C22 C23 1.538(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 H25C 0.9700 . ? C25 H25B 0.9700 . ? C25 H25A 0.9700 . ? 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 N1 C1 N2 119.6(2) . . ? N1 C1 C3 115.6(3) . . ? N2 C1 C3 115.9(3) . . ? N1 C1 C2 118.9(3) . . ? N2 C1 C2 112.8(3) . . ? C3 C1 C2 60.2(2) . . ? C4 C2 C3 118.3(3) . . ? C4 C2 C1 122.4(3) . . ? C3 C2 C1 58.5(2) . . ? C4 C2 H2A 115.3 . . ? C3 C2 H2A 115.3 . . ? C1 C2 H2A 115.3 . . ? C1 C3 C2 61.3(2) . . ? C1 C3 H3B 117.6 . . ? C2 C3 H3B 117.6 . . ? C1 C3 H3A 117.6 . . ? C2 C3 H3A 117.6 . . ? H3B C3 H3A 114.7 . . ? O1 C4 O2 122.8(3) . . ? O1 C4 C2 127.8(3) . . ? O2 C4 C2 109.4(3) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C10 126.4(3) . . ? N1 C6 C7 127.7(3) . . ? C10 C6 C7 105.9(3) . . ? N1 C6 Fe1 123.7(2) . . ? C10 C6 Fe1 69.9(2) . . ? C7 C6 Fe1 69.04(19) . . ? C8 C7 C6 109.2(3) . . ? C8 C7 Fe1 70.9(2) . . ? C6 C7 Fe1 69.43(18) . . ? C8 C7 H7A 125.4 . . ? C6 C7 H7A 125.4 . . ? Fe1 C7 H7A 125.8 . . ? C9 C8 C7 107.9(3) . . ? C9 C8 Fe1 70.1(2) . . ? C7 C8 Fe1 68.3(2) . . ? C9 C8 H8A 126.1 . . ? C7 C8 H8A 126.1 . . ? Fe1 C8 H8A 127.1 . . ? C8 C9 C10 108.3(3) . . ? C8 C9 Fe1 70.0(2) . . ? C10 C9 Fe1 69.1(2) . . ? C8 C9 H9A 125.8 . . ? C10 C9 H9A 125.8 . . ? Fe1 C9 H9A 126.7 . . ? C9 C10 C6 108.7(3) . . ? C9 C10 Fe1 70.3(2) . . ? C6 C10 Fe1 68.8(2) . . ? C9 C10 H10A 125.6 . . ? C6 C10 H10A 125.6 . . ? Fe1 C10 H10A 126.9 . . ? C12 C11 N2 128.1(3) . . ? C12 C11 C15 106.6(3) . . ? N2 C11 C15 125.2(3) . . ? C12 C11 Fe1 69.61(19) . . ? N2 C11 Fe1 123.1(2) . . ? C15 C11 Fe1 69.69(19) . . ? C13 C12 C11 108.7(3) . . ? C13 C12 Fe1 70.3(2) . . ? C11 C12 Fe1 69.23(19) . . ? C13 C12 H12A 125.6 . . ? C11 C12 H12A 125.6 . . ? Fe1 C12 H12A 126.5 . . ? C14 C13 C12 108.0(3) . . ? C14 C13 Fe1 70.3(2) . . ? C12 C13 Fe1 68.9(2) . . ? C14 C13 H13A 126.0 . . ? C12 C13 H13A 126.0 . . ? Fe1 C13 H13A 126.4 . . ? C13 C14 C15 108.9(3) . . ? C13 C14 Fe1 69.8(2) . . ? C15 C14 Fe1 69.1(2) . . ? C13 C14 H14A 125.5 . . ? C15 C14 H14A 125.5 . . ? Fe1 C14 H14A 127.1 . . ? C14 C15 C11 107.7(3) . . ? C14 C15 Fe1 70.3(2) . . ? C11 C15 Fe1 68.72(18) . . ? C14 C15 H15A 126.1 . . ? C11 C15 H15A 126.1 . . ? Fe1 C15 H15A 126.4 . . ? N1 C16 C17 115.9(2) . . ? N1 C16 H16B 108.3 . . ? C17 C16 H16B 108.3 . . ? N1 C16 H16A 108.3 . . ? C17 C16 H16A 108.3 . . ? H16B C16 H16A 107.4 . . ? C19 C17 C18 109.9(3) . . ? C19 C17 C20 109.0(3) . . ? C18 C17 C20 108.4(3) . . ? C19 C17 C16 107.0(3) . . ? C18 C17 C16 109.8(3) . . ? C20 C17 C16 112.8(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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 C22 115.2(2) . . ? N2 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? N2 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? H21B C21 H21A 107.5 . . ? C24 C22 C25 109.0(3) . . ? C24 C22 C21 112.7(3) . . ? C25 C22 C21 110.2(2) . . ? C24 C22 C23 109.5(3) . . ? C25 C22 C23 108.4(3) . . ? C21 C22 C23 107.0(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25C 109.5 . . ? C22 C25 H25B 109.5 . . ? H25C C25 H25B 109.5 . . ? C22 C25 H25A 109.5 . . ? H25C C25 H25A 109.5 . . ? H25B C25 H25A 109.5 . . ? C6 N1 C1 116.0(2) . . ? C6 N1 C16 115.4(2) . . ? C1 N1 C16 114.3(2) . . ? C11 N2 C1 116.3(2) . . ? C11 N2 C21 116.6(2) . . ? C1 N2 C21 116.6(2) . . ? C4 O2 C5 115.4(3) . . ? C7 Fe1 C11 114.40(13) . . ? C7 Fe1 C6 41.53(12) . . ? C11 Fe1 C6 94.80(14) . . ? C7 Fe1 C12 104.99(14) . . ? C11 Fe1 C12 41.16(12) . . ? C6 Fe1 C12 114.90(14) . . ? C7 Fe1 C15 150.13(14) . . ? C11 Fe1 C15 41.59(12) . . ? C6 Fe1 C15 112.73(14) . . ? C12 Fe1 C15 68.86(14) . . ? C7 Fe1 C10 68.57(13) . . ? C11 Fe1 C10 113.74(14) . . ? C6 Fe1 C10 41.26(12) . . ? C12 Fe1 C10 150.85(14) . . ? C15 Fe1 C10 102.03(14) . . ? C7 Fe1 C13 126.89(15) . . ? C11 Fe1 C13 69.25(14) . . ? C6 Fe1 C13 155.10(15) . . ? C12 Fe1 C13 40.82(14) . . ? C15 Fe1 C13 68.36(15) . . ? C10 Fe1 C13 162.73(15) . . ? C7 Fe1 C14 165.78(16) . . ? C11 Fe1 C14 69.08(14) . . ? C6 Fe1 C14 152.33(15) . . ? C12 Fe1 C14 67.98(15) . . ? C15 Fe1 C14 40.64(13) . . ? C10 Fe1 C14 123.73(16) . . ? C13 Fe1 C14 39.91(15) . . ? C7 Fe1 C8 40.79(13) . . ? C11 Fe1 C8 154.38(13) . . ? C6 Fe1 C8 69.54(14) . . ? C12 Fe1 C8 126.43(14) . . ? C15 Fe1 C8 163.10(13) . . ? C10 Fe1 C8 68.10(14) . . ? C13 Fe1 C8 117.17(15) . . ? C14 Fe1 C8 132.91(15) . . ? C7 Fe1 C9 68.10(14) . . ? C11 Fe1 C9 153.45(14) . . ? C6 Fe1 C9 69.35(14) . . ? C12 Fe1 C9 165.09(15) . . ? C15 Fe1 C9 123.87(14) . . ? C10 Fe1 C9 40.69(13) . . ? C13 Fe1 C9 132.26(15) . . ? C14 Fe1 C9 115.51(15) . . ? C8 Fe1 C9 39.93(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.398 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.041