# Supplementary Material (ESI) for Metallomics # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Metallomics _journal_coden_Cambridge 1400 _publ_contact_author_name 'John Spencer' _publ_contact_author_address ; Central Avenue Chatham Maritime ME4 4TB ; _publ_contact_author_email J.Spencer@gre.ac.uk _publ_author_name 'John Spencer' data_2008src1176p21c _database_code_depnum_ccdc_archive 'CCDC 770985' #TrackingRef '- Spencer_Dalton_all.cif' #structure (Z)-6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N O Ru' _chemical_formula_sum 'C19 H15 N O Ru' _chemical_formula_weight 374.39 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' Ru Ru -1.2594 0.8363 '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' 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 22.508(3) _cell_length_b 5.9232(7) _cell_length_c 22.328(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.252(5) _cell_angle_gamma 90.00 _cell_volume 2919.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4721 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 1.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8819 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 14130 reflections reduced R(int) from 0.1082 to 0.0640 Ratio of minimum to maximum apparent transmission: 0.563037 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 66.065 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19866 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5072 _reflns_number_gt 3515 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Residual electron density peak seen at 0.3679, 1.4165, 0.3935. This is too close to N2 (1.45A) to be an atom and is most likely from a Ru atom in a much smaller secondary crystal attached to the main crystal. Very faint extra peaks in the precession images also support this. ; _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^)+(0.0898P)^2^+55.7238P] 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 5072 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_gt 0.0833 _refine_ls_wR_factor_ref 0.2236 _refine_ls_wR_factor_gt 0.1927 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.2605(5) 1.2254(19) 0.3637(4) 0.028(3) Uani 1 1 d . . . C2 C 0.2763(5) 1.0063(18) 0.3963(4) 0.023(2) Uani 1 1 d . . . C3 C 0.3417(5) 0.9803(18) 0.4019(4) 0.022(2) Uani 1 1 d . . . C4 C 0.3828(6) 0.817(2) 0.4260(5) 0.035(3) Uani 1 1 d . . . H4 H 0.3696 0.6836 0.4430 0.042 Uiso 1 1 calc R . . C5 C 0.4439(5) 0.849(2) 0.4255(5) 0.034(3) Uani 1 1 d . . . H5 H 0.4722 0.7355 0.4420 0.041 Uiso 1 1 calc R . . C6 C 0.4639(5) 1.041(2) 0.4013(6) 0.039(3) Uani 1 1 d . . . H6 H 0.5059 1.0586 0.4018 0.047 Uiso 1 1 calc R . . C7 C 0.4239(5) 1.212(2) 0.3762(5) 0.037(3) Uani 1 1 d . . . H7 H 0.4376 1.3435 0.3585 0.045 Uiso 1 1 calc R . . C8 C 0.3628(5) 1.180(2) 0.3785(5) 0.026(2) Uani 1 1 d . . . C9 C 0.2391(5) 0.8495(18) 0.4146(4) 0.024(2) Uani 1 1 d . . . H9 H 0.2601 0.7211 0.4335 0.029 Uiso 1 1 calc R . . C10 C 0.1733(5) 0.8384(19) 0.4110(5) 0.026(2) Uani 1 1 d . . . C11 C 0.1269(5) 1.002(2) 0.3928(5) 0.028(3) Uani 1 1 d . . . H11 H 0.1323 1.1526 0.3805 0.033 Uiso 1 1 calc R . . C12 C 0.0708(5) 0.896(2) 0.3966(5) 0.030(3) Uani 1 1 d . . . H12 H 0.0320 0.9650 0.3861 0.036 Uiso 1 1 calc R . . C13 C 0.0816(5) 0.677(2) 0.4182(5) 0.031(3) Uani 1 1 d . . . H13 H 0.0519 0.5714 0.4253 0.037 Uiso 1 1 calc R . . C14 C 0.1460(5) 0.6375(18) 0.4278(5) 0.027(2) Uani 1 1 d . . . H14 H 0.1664 0.5023 0.4426 0.032 Uiso 1 1 calc R . . C15 C 0.1845(6) 1.056(2) 0.5695(5) 0.043(3) Uani 1 1 d . . . H15 H 0.2262 1.0900 0.5726 0.051 Uiso 1 1 calc R . . C16 C 0.1356(6) 1.203(2) 0.5475(5) 0.038(3) Uani 1 1 d . . . H16 H 0.1388 1.3535 0.5337 0.046 Uiso 1 1 calc R . . C17 C 0.0810(6) 1.087(2) 0.5497(5) 0.037(3) Uani 1 1 d . . . H17 H 0.0412 1.1460 0.5376 0.044 Uiso 1 1 calc R . . C18 C 0.0963(6) 0.869(2) 0.5732(5) 0.037(3) Uani 1 1 d . . . H18 H 0.0686 0.7538 0.5795 0.044 Uiso 1 1 calc R . . C19 C 0.1610(6) 0.852(2) 0.5859(5) 0.037(3) Uani 1 1 d . . . H19 H 0.1839 0.7237 0.6025 0.044 Uiso 1 1 calc R . . N1 N 0.3140(4) 1.3209(16) 0.3562(4) 0.026(2) Uani 1 1 d . . . H1 H 0.3171 1.4539 0.3396 0.031 Uiso 1 1 calc R . . O1 O 0.2098(3) 1.3120(13) 0.3480(3) 0.0303(18) Uani 1 1 d . . . Ru1 Ru 0.12791(4) 0.90990(15) 0.48755(4) 0.0236(3) Uani 1 1 d . . . C21 C 0.2513(5) -0.2248(19) 0.2579(5) 0.025(2) Uani 1 1 d . . . C22 C 0.2311(5) -0.0099(18) 0.2246(4) 0.024(2) Uani 1 1 d . . . C23 C 0.1633(5) -0.0077(18) 0.2179(5) 0.025(2) Uani 1 1 d . . . C24 C 0.1202(5) 0.147(2) 0.1943(5) 0.030(3) Uani 1 1 d . . . H24 H 0.1315 0.2863 0.1784 0.036 Uiso 1 1 calc R . . C25 C 0.0596(5) 0.099(2) 0.1937(5) 0.035(3) Uani 1 1 d . . . H25 H 0.0292 0.2077 0.1789 0.042 Uiso 1 1 calc R . . C26 C 0.0436(5) -0.108(2) 0.2149(5) 0.035(3) Uani 1 1 d . . . H26 H 0.0019 -0.1431 0.2116 0.042 Uiso 1 1 calc R . . C27 C 0.0870(5) -0.2666(19) 0.2409(5) 0.030(3) Uani 1 1 d . . . H27 H 0.0761 -0.4072 0.2562 0.037 Uiso 1 1 calc R . . C28 C 0.1459(6) -0.2071(18) 0.2430(5) 0.031(3) Uani 1 1 d . . . C29 C 0.2641(5) 0.160(2) 0.2056(4) 0.026(2) Uani 1 1 d . . . H29 H 0.2403 0.2831 0.1874 0.032 Uiso 1 1 calc R . . C30 C 0.3289(5) 0.188(2) 0.2079(5) 0.031(3) Uani 1 1 d . . . C31 C 0.3525(6) 0.395(2) 0.1884(5) 0.034(3) Uani 1 1 d . . . H31 H 0.3291 0.5256 0.1747 0.040 Uiso 1 1 calc R . . C32 C 0.4149(6) 0.376(2) 0.1928(5) 0.039(3) Uani 1 1 d . . . H32 H 0.4413 0.4896 0.1831 0.047 Uiso 1 1 calc R . . C33 C 0.4320(6) 0.152(2) 0.2149(5) 0.044(3) Uani 1 1 d . . . H33 H 0.4718 0.0917 0.2220 0.053 Uiso 1 1 calc R . . C34 C 0.3793(6) 0.036(2) 0.2244(5) 0.035(3) Uani 1 1 d . . . H34 H 0.3776 -0.1143 0.2389 0.042 Uiso 1 1 calc R . . C35 C 0.3101(6) -0.042(2) 0.0515(5) 0.037(3) Uani 1 1 d . . . H35 H 0.2701 -0.0890 0.0527 0.045 Uiso 1 1 calc R . . C36 C 0.3271(6) 0.171(2) 0.0312(5) 0.035(3) Uani 1 1 d . . . H36 H 0.3002 0.2911 0.0168 0.042 Uiso 1 1 calc R . . C37 C 0.3899(6) 0.1749(19) 0.0356(5) 0.031(3) Uani 1 1 d . . . H37 H 0.4131 0.2969 0.0248 0.037 Uiso 1 1 calc R . . C38 C 0.4124(6) -0.037(2) 0.0592(5) 0.038(3) Uani 1 1 d . . . H38 H 0.4536 -0.0832 0.0671 0.045 Uiso 1 1 calc R . . C39 C 0.3621(6) -0.168(2) 0.0691(5) 0.036(3) Uani 1 1 d . . . H39 H 0.3640 -0.3172 0.0851 0.044 Uiso 1 1 calc R . . N21 N 0.1997(4) -0.3327(15) 0.2650(4) 0.026(2) Uani 1 1 d . . . H21 H 0.1996 -0.4674 0.2816 0.031 Uiso 1 1 calc R . . O21 O 0.3036(3) -0.2939(13) 0.2770(3) 0.0300(18) Uani 1 1 d . . . Ru2 Ru 0.36978(4) 0.12721(16) 0.12761(4) 0.0283(3) 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 0.040(7) 0.032(6) 0.010(5) -0.006(5) 0.002(4) 0.002(6) C2 0.027(6) 0.024(6) 0.021(5) 0.006(4) 0.013(4) -0.002(5) C3 0.026(6) 0.019(5) 0.020(5) 0.000(4) 0.001(4) 0.002(5) C4 0.046(8) 0.032(7) 0.030(6) -0.004(5) 0.014(5) 0.002(6) C5 0.027(6) 0.034(7) 0.041(7) -0.004(6) 0.003(5) 0.000(5) C6 0.019(6) 0.049(8) 0.053(8) -0.014(6) 0.017(5) 0.000(6) C7 0.031(7) 0.050(8) 0.030(6) 0.001(6) 0.006(5) -0.008(6) C8 0.026(6) 0.034(6) 0.022(5) 0.000(5) 0.014(4) 0.007(5) C9 0.037(6) 0.020(6) 0.018(5) -0.005(4) 0.010(4) 0.007(5) C10 0.029(6) 0.028(6) 0.023(5) -0.005(5) 0.010(4) -0.007(5) C11 0.031(6) 0.028(6) 0.024(6) -0.005(5) 0.008(5) -0.005(5) C12 0.030(6) 0.042(7) 0.018(5) -0.002(5) 0.003(4) 0.002(6) C13 0.026(6) 0.033(7) 0.039(7) -0.012(5) 0.015(5) -0.015(5) C14 0.029(6) 0.022(6) 0.031(6) -0.003(5) 0.014(5) 0.000(5) C15 0.042(8) 0.063(9) 0.022(6) -0.010(6) 0.005(5) -0.008(7) C16 0.077(10) 0.021(6) 0.022(6) -0.004(5) 0.019(6) -0.016(6) C17 0.037(7) 0.053(8) 0.023(6) -0.011(6) 0.011(5) 0.009(6) C18 0.048(8) 0.040(8) 0.026(6) -0.006(5) 0.017(5) -0.017(6) C19 0.065(9) 0.031(7) 0.015(5) -0.008(5) 0.012(5) -0.013(6) N1 0.024(5) 0.031(5) 0.023(5) 0.005(4) 0.004(4) 0.004(4) O1 0.030(4) 0.030(4) 0.036(4) 0.010(4) 0.018(3) 0.010(4) Ru1 0.0269(5) 0.0252(5) 0.0207(5) -0.0026(4) 0.0097(3) -0.0041(4) C21 0.024(6) 0.031(6) 0.025(5) 0.002(5) 0.017(4) -0.002(5) C22 0.032(6) 0.020(6) 0.019(5) 0.002(4) 0.000(4) 0.017(5) C23 0.035(7) 0.019(6) 0.024(5) 0.003(5) 0.015(5) 0.006(5) C24 0.032(6) 0.029(6) 0.030(6) -0.003(5) 0.009(5) 0.009(5) C25 0.033(7) 0.041(8) 0.030(6) 0.000(6) 0.005(5) 0.013(6) C26 0.021(6) 0.049(8) 0.035(6) -0.007(6) 0.004(5) 0.005(6) C27 0.040(7) 0.018(6) 0.038(6) 0.000(5) 0.017(5) -0.003(5) C28 0.049(8) 0.014(6) 0.023(6) 0.006(5) -0.012(5) -0.010(5) C29 0.031(6) 0.035(7) 0.016(5) -0.008(5) 0.009(4) 0.002(5) C30 0.036(7) 0.038(7) 0.023(5) -0.004(5) 0.017(5) -0.006(6) C31 0.040(7) 0.039(7) 0.021(5) -0.006(5) 0.006(5) -0.013(6) C32 0.048(8) 0.047(8) 0.028(6) -0.018(6) 0.020(5) -0.021(7) C33 0.048(8) 0.065(10) 0.020(6) -0.003(6) 0.010(5) -0.015(7) C34 0.045(8) 0.034(7) 0.026(6) -0.001(5) 0.009(5) -0.006(6) C35 0.035(7) 0.052(8) 0.028(6) -0.006(6) 0.012(5) -0.016(6) C36 0.050(8) 0.036(7) 0.019(5) 0.002(5) 0.006(5) 0.003(6) C37 0.052(8) 0.019(6) 0.024(6) 0.000(5) 0.014(5) 0.004(5) C38 0.043(8) 0.040(8) 0.031(6) -0.009(6) 0.011(5) 0.001(6) C39 0.050(8) 0.033(7) 0.031(6) -0.006(5) 0.019(6) -0.017(6) N21 0.035(5) 0.018(5) 0.025(5) 0.003(4) 0.008(4) 0.002(4) O21 0.034(5) 0.031(4) 0.027(4) 0.005(3) 0.011(3) 0.008(4) Ru2 0.0313(6) 0.0303(6) 0.0245(5) -0.0018(4) 0.0087(4) -0.0061(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.239(13) . ? C1 N1 1.368(14) . ? C1 C2 1.496(15) . ? C2 C9 1.366(15) . ? C2 C3 1.462(15) . ? C3 C4 1.373(16) . ? C3 C8 1.412(15) . ? C4 C5 1.390(16) . ? C4 H4 0.9500 . ? C5 C6 1.374(18) . ? C5 H5 0.9500 . ? C6 C7 1.397(18) . ? C6 H6 0.9500 . ? C7 C8 1.401(15) . ? C7 H7 0.9500 . ? C8 N1 1.391(14) . ? C9 C10 1.468(15) . ? C9 H9 0.9500 . ? C10 C14 1.423(15) . ? C10 C11 1.424(16) . ? C10 Ru1 2.197(10) . ? C11 C12 1.426(16) . ? C11 Ru1 2.179(11) . ? C11 H11 0.9500 . ? C12 C13 1.392(16) . ? C12 Ru1 2.182(10) . ? C12 H12 0.9500 . ? C13 C14 1.441(15) . ? C13 Ru1 2.182(11) . ? C13 H13 0.9500 . ? C14 Ru1 2.182(10) . ? C14 H14 0.9500 . ? C15 C19 1.398(18) . ? C15 C16 1.414(19) . ? C15 Ru1 2.192(12) . ? C15 H15 0.9500 . ? C16 C17 1.417(18) . ? C16 Ru1 2.179(11) . ? C16 H16 0.9500 . ? C17 C18 1.415(18) . ? C17 Ru1 2.172(11) . ? C17 H17 0.9500 . ? C18 C19 1.432(18) . ? C18 Ru1 2.181(11) . ? C18 H18 0.9500 . ? C19 Ru1 2.203(11) . ? C19 H19 0.9500 . ? N1 H1 0.8800 . ? C21 O21 1.240(13) . ? C21 N21 1.362(13) . ? C21 C22 1.499(15) . ? C22 C29 1.365(16) . ? C22 C23 1.504(15) . ? C23 C24 1.364(15) . ? C23 C28 1.397(15) . ? C24 C25 1.392(16) . ? C24 H24 0.9500 . ? C25 C26 1.388(17) . ? C25 H25 0.9500 . ? C26 C27 1.396(16) . ? C26 H26 0.9500 . ? C27 C28 1.364(16) . ? C27 H27 0.9500 . ? C28 N21 1.424(14) . ? C29 C30 1.459(15) . ? C29 H29 0.9500 . ? C30 C34 1.437(17) . ? C30 C31 1.441(16) . ? C30 Ru2 2.198(10) . ? C31 C32 1.394(17) . ? C31 Ru2 2.174(12) . ? C31 H31 0.9500 . ? C32 C33 1.442(19) . ? C32 Ru2 2.179(11) . ? C32 H32 0.9500 . ? C33 C34 1.422(17) . ? C33 Ru2 2.171(12) . ? C33 H33 0.9500 . ? C34 Ru2 2.196(11) . ? C34 H34 0.9500 . ? C35 C39 1.379(18) . ? C35 C36 1.415(17) . ? C35 Ru2 2.192(12) . ? C35 H35 0.9500 . ? C36 C37 1.397(17) . ? C36 Ru2 2.195(11) . ? C36 H36 0.9500 . ? C37 C38 1.415(17) . ? C37 Ru2 2.206(11) . ? C37 H37 0.9500 . ? C38 C39 1.427(17) . ? C38 Ru2 2.184(12) . ? C38 H38 0.9500 . ? C39 Ru2 2.170(12) . ? C39 H39 0.9500 . ? N21 H21 0.8800 . ? 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 O1 C1 N1 125.4(10) . . ? O1 C1 C2 127.9(11) . . ? N1 C1 C2 106.7(9) . . ? C9 C2 C3 124.7(10) . . ? C9 C2 C1 129.4(10) . . ? C3 C2 C1 105.8(9) . . ? C4 C3 C8 119.1(10) . . ? C4 C3 C2 134.3(10) . . ? C8 C3 C2 106.5(9) . . ? C3 C4 C5 119.6(12) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 121.0(12) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.6(11) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 C8 116.6(11) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? N1 C8 C7 128.2(11) . . ? N1 C8 C3 109.7(9) . . ? C7 C8 C3 122.0(11) . . ? C2 C9 C10 133.2(10) . . ? C2 C9 H9 113.4 . . ? C10 C9 H9 113.4 . . ? C14 C10 C11 108.2(10) . . ? C14 C10 C9 120.4(10) . . ? C11 C10 C9 131.4(10) . . ? C14 C10 Ru1 70.5(6) . . ? C11 C10 Ru1 70.3(6) . . ? C9 C10 Ru1 124.5(7) . . ? C10 C11 C12 107.1(10) . . ? C10 C11 Ru1 71.7(6) . . ? C12 C11 Ru1 71.0(6) . . ? C10 C11 H11 126.4 . . ? C12 C11 H11 126.4 . . ? Ru1 C11 H11 122.6 . . ? C13 C12 C11 109.4(10) . . ? C13 C12 Ru1 71.4(6) . . ? C11 C12 Ru1 70.8(6) . . ? C13 C12 H12 125.3 . . ? C11 C12 H12 125.3 . . ? Ru1 C12 H12 124.1 . . ? C12 C13 C14 107.8(10) . . ? C12 C13 Ru1 71.4(6) . . ? C14 C13 Ru1 70.7(6) . . ? C12 C13 H13 126.1 . . ? C14 C13 H13 126.1 . . ? Ru1 C13 H13 123.4 . . ? C10 C14 C13 107.5(10) . . ? C10 C14 Ru1 71.6(6) . . ? C13 C14 Ru1 70.7(6) . . ? C10 C14 H14 126.3 . . ? C13 C14 H14 126.3 . . ? Ru1 C14 H14 123.1 . . ? C19 C15 C16 108.5(12) . . ? C19 C15 Ru1 71.9(7) . . ? C16 C15 Ru1 70.6(7) . . ? C19 C15 H15 125.8 . . ? C16 C15 H15 125.8 . . ? Ru1 C15 H15 123.3 . . ? C15 C16 C17 108.1(11) . . ? C15 C16 Ru1 71.6(7) . . ? C17 C16 Ru1 70.7(6) . . ? C15 C16 H16 126.0 . . ? C17 C16 H16 126.0 . . ? Ru1 C16 H16 123.4 . . ? C18 C17 C16 107.8(11) . . ? C18 C17 Ru1 71.4(7) . . ? C16 C17 Ru1 71.3(7) . . ? C18 C17 H17 126.1 . . ? C16 C17 H17 126.1 . . ? Ru1 C17 H17 122.9 . . ? C17 C18 C19 107.6(11) . . ? C17 C18 Ru1 70.7(6) . . ? C19 C18 Ru1 71.8(6) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? Ru1 C18 H18 123.0 . . ? C15 C19 C18 108.0(12) . . ? C15 C19 Ru1 71.0(7) . . ? C18 C19 Ru1 70.1(6) . . ? C15 C19 H19 126.0 . . ? C18 C19 H19 126.0 . . ? Ru1 C19 H19 124.5 . . ? C1 N1 C8 111.1(9) . . ? C1 N1 H1 124.5 . . ? C8 N1 H1 124.5 . . ? C17 Ru1 C11 125.8(5) . . ? C17 Ru1 C16 38.0(5) . . ? C11 Ru1 C16 112.5(4) . . ? C17 Ru1 C18 37.9(5) . . ? C11 Ru1 C18 159.3(5) . . ? C16 Ru1 C18 63.3(4) . . ? C17 Ru1 C12 109.9(4) . . ? C11 Ru1 C12 38.2(4) . . ? C16 Ru1 C12 124.3(5) . . ? C18 Ru1 C12 125.3(4) . . ? C17 Ru1 C14 157.0(5) . . ? C11 Ru1 C14 63.8(4) . . ? C16 Ru1 C14 164.4(5) . . ? C18 Ru1 C14 125.8(4) . . ? C12 Ru1 C14 63.2(4) . . ? C17 Ru1 C13 122.4(4) . . ? C11 Ru1 C13 63.7(4) . . ? C16 Ru1 C13 155.6(5) . . ? C18 Ru1 C13 111.0(4) . . ? C12 Ru1 C13 37.2(4) . . ? C14 Ru1 C13 38.5(4) . . ? C17 Ru1 C15 63.4(5) . . ? C11 Ru1 C15 127.3(5) . . ? C16 Ru1 C15 37.7(5) . . ? C18 Ru1 C15 63.1(5) . . ? C12 Ru1 C15 158.7(5) . . ? C14 Ru1 C15 130.9(5) . . ? C13 Ru1 C15 163.9(5) . . ? C17 Ru1 C10 161.5(5) . . ? C11 Ru1 C10 38.0(4) . . ? C16 Ru1 C10 129.7(4) . . ? C18 Ru1 C10 160.3(5) . . ? C12 Ru1 C10 63.1(4) . . ? C14 Ru1 C10 37.9(4) . . ? C13 Ru1 C10 63.6(4) . . ? C15 Ru1 C10 116.3(4) . . ? C17 Ru1 C19 63.3(5) . . ? C11 Ru1 C19 160.7(4) . . ? C16 Ru1 C19 62.7(5) . . ? C18 Ru1 C19 38.1(5) . . ? C12 Ru1 C19 160.8(4) . . ? C14 Ru1 C19 115.2(4) . . ? C13 Ru1 C19 129.0(4) . . ? C15 Ru1 C19 37.1(5) . . ? C10 Ru1 C19 128.8(5) . . ? O21 C21 N21 125.3(10) . . ? O21 C21 C22 128.8(10) . . ? N21 C21 C22 105.9(9) . . ? C29 C22 C21 130.4(10) . . ? C29 C22 C23 124.5(9) . . ? C21 C22 C23 105.1(9) . . ? C24 C23 C28 119.4(11) . . ? C24 C23 C22 132.4(10) . . ? C28 C23 C22 108.2(10) . . ? C23 C24 C25 119.1(11) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C26 C25 C24 119.8(11) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C27 122.0(11) . . ? C25 C26 H26 119.0 . . ? C27 C26 H26 119.0 . . ? C28 C27 C26 115.9(10) . . ? C28 C27 H27 122.0 . . ? C26 C27 H27 122.0 . . ? C27 C28 C23 123.5(11) . . ? C27 C28 N21 129.3(10) . . ? C23 C28 N21 107.0(10) . . ? C22 C29 C30 132.4(11) . . ? C22 C29 H29 113.8 . . ? C30 C29 H29 113.8 . . ? C34 C30 C31 107.1(10) . . ? C34 C30 C29 132.1(11) . . ? C31 C30 C29 120.8(11) . . ? C34 C30 Ru2 70.9(6) . . ? C31 C30 Ru2 69.8(6) . . ? C29 C30 Ru2 121.8(7) . . ? C32 C31 C30 109.5(12) . . ? C32 C31 Ru2 71.5(7) . . ? C30 C31 Ru2 71.7(6) . . ? C32 C31 H31 125.2 . . ? C30 C31 H31 125.2 . . ? Ru2 C31 H31 123.2 . . ? C31 C32 C33 107.3(11) . . ? C31 C32 Ru2 71.1(7) . . ? C33 C32 Ru2 70.4(7) . . ? C31 C32 H32 126.3 . . ? C33 C32 H32 126.3 . . ? Ru2 C32 H32 123.8 . . ? C34 C33 C32 108.7(12) . . ? C34 C33 Ru2 72.0(7) . . ? C32 C33 Ru2 70.9(7) . . ? C34 C33 H33 125.6 . . ? C32 C33 H33 125.6 . . ? Ru2 C33 H33 123.1 . . ? C33 C34 C30 107.4(11) . . ? C33 C34 Ru2 70.0(7) . . ? C30 C34 Ru2 71.0(6) . . ? C33 C34 H34 126.3 . . ? C30 C34 H34 126.3 . . ? Ru2 C34 H34 124.3 . . ? C39 C35 C36 107.9(11) . . ? C39 C35 Ru2 70.7(7) . . ? C36 C35 Ru2 71.3(7) . . ? C39 C35 H35 126.1 . . ? C36 C35 H35 126.1 . . ? Ru2 C35 H35 123.6 . . ? C37 C36 C35 109.0(11) . . ? C37 C36 Ru2 71.9(6) . . ? C35 C36 Ru2 71.0(6) . . ? C37 C36 H36 125.5 . . ? C35 C36 H36 125.5 . . ? Ru2 C36 H36 123.2 . . ? C36 C37 C38 107.1(11) . . ? C36 C37 Ru2 71.1(6) . . ? C38 C37 Ru2 70.3(6) . . ? C36 C37 H37 126.4 . . ? C38 C37 H37 126.4 . . ? Ru2 C37 H37 123.8 . . ? C37 C38 C39 107.6(12) . . ? C37 C38 Ru2 72.0(7) . . ? C39 C38 Ru2 70.4(7) . . ? C37 C38 H38 126.2 . . ? C39 C38 H38 126.2 . . ? Ru2 C38 H38 123.1 . . ? C35 C39 C38 108.4(11) . . ? C35 C39 Ru2 72.4(7) . . ? C38 C39 Ru2 71.4(7) . . ? C35 C39 H39 125.8 . . ? C38 C39 H39 125.8 . . ? Ru2 C39 H39 122.1 . . ? C21 N21 C28 113.7(9) . . ? C21 N21 H21 123.1 . . ? C28 N21 H21 123.1 . . ? C39 Ru2 C33 123.8(5) . . ? C39 Ru2 C31 164.2(4) . . ? C33 Ru2 C31 63.4(5) . . ? C39 Ru2 C32 156.9(5) . . ? C33 Ru2 C32 38.7(5) . . ? C31 Ru2 C32 37.4(4) . . ? C39 Ru2 C38 38.3(4) . . ? C33 Ru2 C38 111.3(5) . . ? C31 Ru2 C38 156.7(5) . . ? C32 Ru2 C38 123.9(5) . . ? C39 Ru2 C35 36.9(5) . . ? C33 Ru2 C35 156.5(5) . . ? C31 Ru2 C35 131.4(5) . . ? C32 Ru2 C35 164.2(5) . . ? C38 Ru2 C35 62.7(5) . . ? C39 Ru2 C36 62.3(5) . . ? C33 Ru2 C36 162.7(5) . . ? C31 Ru2 C36 115.4(5) . . ? C32 Ru2 C36 129.3(5) . . ? C38 Ru2 C36 62.2(5) . . ? C35 Ru2 C36 37.6(5) . . ? C39 Ru2 C34 112.0(5) . . ? C33 Ru2 C34 38.0(4) . . ? C31 Ru2 C34 63.9(5) . . ? C32 Ru2 C34 64.3(5) . . ? C38 Ru2 C34 127.3(5) . . ? C35 Ru2 C34 125.3(5) . . ? C36 Ru2 C34 159.0(5) . . ? C39 Ru2 C30 128.7(4) . . ? C33 Ru2 C30 63.6(5) . . ? C31 Ru2 C30 38.5(4) . . ? C32 Ru2 C30 63.9(4) . . ? C38 Ru2 C30 162.5(5) . . ? C35 Ru2 C30 114.6(4) . . ? C36 Ru2 C30 127.5(5) . . ? C34 Ru2 C30 38.2(5) . . ? C39 Ru2 C37 63.2(4) . . ? C33 Ru2 C37 127.8(5) . . ? C31 Ru2 C37 125.6(4) . . ? C32 Ru2 C37 112.4(4) . . ? C38 Ru2 C37 37.6(4) . . ? C35 Ru2 C37 62.8(4) . . ? C36 Ru2 C37 37.0(4) . . ? C34 Ru2 C37 161.6(5) . . ? C30 Ru2 C37 158.9(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O21 0.88 2.03 2.869(12) 159.7 1_575 N21 H21 O1 0.88 1.96 2.785(11) 156.2 1_535 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 5.537 _refine_diff_density_min -1.022 _refine_diff_density_rms 0.201 data_2009src0154 _database_code_depnum_ccdc_archive 'CCDC 770986' #TrackingRef '- Spencer_Dalton_all.cif' #structure (E)-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 Fe N O' _chemical_formula_sum 'C20 H17 Fe N O' _chemical_formula_weight 343.20 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' Fe Fe 0.3463 0.8444 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4825(5) _cell_length_b 7.3420(2) _cell_length_c 23.1152(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2966.99(15) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21471 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7774 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 15900 reflections reduced R(int) from 0.1898 to 0.0863 Ratio of minimum to maximum apparent transmission: 0.859938 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 66.065 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22133 _diffrn_reflns_av_R_equivalents 0.1137 _diffrn_reflns_av_sigmaI/netI 0.0806 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3408 _reflns_number_gt 2262 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0000P)^2^+24.7014P] 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 3408 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1399 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1426 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 0.3682(3) 0.2336(8) 0.5562(2) 0.0161(11) Uani 1 1 d . . . C2 C 0.3303(3) 0.2864(7) 0.5005(2) 0.0136(11) Uani 1 1 d . . . C3 C 0.2475(3) 0.2646(8) 0.5103(2) 0.0146(11) Uani 1 1 d . . . C4 C 0.1827(3) 0.3122(8) 0.4797(3) 0.0179(12) Uani 1 1 d . . . H4 H 0.1872 0.3669 0.4426 0.021 Uiso 1 1 calc R . . C5 C 0.1102(3) 0.2797(8) 0.5035(2) 0.0211(13) Uani 1 1 d . . . H5 H 0.0655 0.3118 0.4825 0.025 Uiso 1 1 calc R . . C6 C 0.1035(3) 0.2004(8) 0.5579(2) 0.0195(12) Uani 1 1 d . . . H6 H 0.0542 0.1749 0.5731 0.023 Uiso 1 1 calc R . . C7 C 0.1682(3) 0.1579(8) 0.5905(2) 0.0186(12) Uani 1 1 d . . . H7 H 0.1636 0.1063 0.6280 0.022 Uiso 1 1 calc R . . C8 C 0.2392(3) 0.1926(7) 0.5668(2) 0.0137(11) Uani 1 1 d . . . C9 C 0.3741(3) 0.3423(7) 0.4565(2) 0.0159(12) Uani 1 1 d . . . H9 H 0.4270 0.3556 0.4650 0.019 Uiso 1 1 calc R . . C10 C 0.3520(3) 0.3852(7) 0.3976(2) 0.0133(11) Uani 1 1 d . . . C11 C 0.3933(3) 0.5094(7) 0.3597(2) 0.0178(12) Uani 1 1 d . . . H11 H 0.4377 0.5769 0.3698 0.021 Uiso 1 1 calc R . . C12 C 0.3561(3) 0.5125(8) 0.3053(3) 0.0204(13) Uani 1 1 d . . . H12 H 0.3703 0.5849 0.2730 0.024 Uiso 1 1 calc R . . C13 C 0.2941(3) 0.3890(8) 0.3076(2) 0.0177(12) Uani 1 1 d . . . H13 H 0.2598 0.3631 0.2768 0.021 Uiso 1 1 calc R . . C14 C 0.2918(3) 0.3096(8) 0.3639(2) 0.0148(11) Uani 1 1 d . . . H14 H 0.2560 0.2211 0.3768 0.018 Uiso 1 1 calc R . . C15 C 0.4695(3) 0.0570(8) 0.3501(3) 0.0182(12) Uani 1 1 d . . . H15 H 0.4859 0.0320 0.3885 0.022 Uiso 1 1 calc R . . C16 C 0.5050(3) 0.1794(8) 0.3105(2) 0.0180(12) Uani 1 1 d . . . H16 H 0.5491 0.2511 0.3180 0.022 Uiso 1 1 calc R . . C17 C 0.4630(3) 0.1759(8) 0.2579(2) 0.0180(12) Uani 1 1 d . . . H17 H 0.4741 0.2444 0.2241 0.022 Uiso 1 1 calc R . . C18 C 0.4012(3) 0.0513(8) 0.2648(2) 0.0187(12) Uani 1 1 d . . . H18 H 0.3641 0.0220 0.2363 0.022 Uiso 1 1 calc R . . C19 C 0.4047(3) -0.0214(7) 0.3216(3) 0.0173(12) Uani 1 1 d . . . H19 H 0.3702 -0.1071 0.3378 0.021 Uiso 1 1 calc R . . C20 C 0.3233(3) 0.1128(9) 0.6511(2) 0.0210(13) Uani 1 1 d . . . H20A H 0.3783 0.1013 0.6585 0.032 Uiso 1 1 calc R . . H20B H 0.2985 -0.0053 0.6572 0.032 Uiso 1 1 calc R . . H20C H 0.3014 0.2029 0.6776 0.032 Uiso 1 1 calc R . . Fe1 Fe 0.39369(4) 0.25555(11) 0.32464(3) 0.01278(19) Uani 1 1 d . . . N1 N 0.3113(3) 0.1711(7) 0.59216(19) 0.0160(10) Uani 1 1 d . . . O1 O 0.4362(2) 0.2381(6) 0.56874(17) 0.0204(9) 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 0.021(3) 0.011(3) 0.016(3) -0.001(2) -0.003(2) 0.005(2) C2 0.017(3) 0.010(3) 0.014(3) 0.001(2) 0.000(2) 0.002(2) C3 0.017(2) 0.012(3) 0.015(2) -0.001(2) 0.001(2) -0.002(2) C4 0.019(3) 0.016(3) 0.019(3) 0.002(2) 0.002(2) 0.005(2) C5 0.020(3) 0.027(3) 0.017(3) -0.004(2) -0.001(2) -0.001(3) C6 0.014(3) 0.023(3) 0.021(3) -0.004(2) 0.003(2) 0.000(2) C7 0.025(3) 0.015(3) 0.015(3) -0.001(2) 0.006(2) 0.003(2) C8 0.017(3) 0.012(3) 0.011(3) -0.002(2) 0.001(2) 0.002(2) C9 0.018(3) 0.012(3) 0.018(3) -0.005(2) -0.004(2) 0.001(2) C10 0.015(3) 0.012(3) 0.013(3) -0.005(2) 0.007(2) 0.002(2) C11 0.017(3) 0.016(3) 0.020(3) -0.003(2) 0.007(3) -0.001(2) C12 0.027(3) 0.016(3) 0.018(3) 0.002(2) 0.002(3) 0.007(3) C13 0.018(3) 0.022(3) 0.013(3) 0.000(2) 0.002(2) 0.011(2) C14 0.012(3) 0.016(3) 0.016(3) -0.001(2) 0.004(2) 0.001(2) C15 0.016(3) 0.020(3) 0.019(3) 0.001(2) -0.002(2) 0.007(2) C16 0.014(3) 0.017(3) 0.023(3) -0.004(2) 0.003(2) 0.004(2) C17 0.020(3) 0.018(3) 0.015(3) 0.000(2) 0.007(2) 0.004(2) C18 0.012(3) 0.023(3) 0.021(3) -0.010(2) 0.005(2) 0.001(2) C19 0.023(3) 0.008(2) 0.020(3) -0.001(2) 0.006(3) 0.002(2) C20 0.020(3) 0.028(3) 0.015(3) 0.004(2) -0.001(2) 0.001(3) Fe1 0.0128(3) 0.0125(3) 0.0131(3) -0.0001(3) 0.0018(3) 0.0009(4) N1 0.017(2) 0.021(3) 0.010(2) -0.0010(19) -0.0007(19) -0.002(2) O1 0.0148(18) 0.026(2) 0.020(2) -0.0004(19) -0.0032(16) 0.0076(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.224(6) . ? C1 N1 1.376(7) . ? C1 C2 1.499(7) . ? C2 C9 1.337(8) . ? C2 C3 1.474(7) . ? C3 C4 1.380(8) . ? C3 C8 1.416(7) . ? C4 C5 1.403(8) . ? C4 H4 0.9500 . ? C5 C6 1.390(8) . ? C5 H5 0.9500 . ? C6 C7 1.395(8) . ? C6 H6 0.9500 . ? C7 C8 1.380(8) . ? C7 H7 0.9500 . ? C8 N1 1.399(7) . ? C9 C10 1.450(8) . ? C9 H9 0.9500 . ? C10 C14 1.423(8) . ? C10 C11 1.456(7) . ? C10 Fe1 2.069(5) . ? C11 C12 1.417(8) . ? C11 Fe1 2.033(6) . ? C11 H11 0.9500 . ? C12 C13 1.414(8) . ? C12 Fe1 2.047(6) . ? C12 H12 0.9500 . ? C13 C14 1.426(8) . ? C13 Fe1 2.036(5) . ? C13 H13 0.9500 . ? C14 Fe1 2.039(5) . ? C14 H14 0.9500 . ? C15 C16 1.425(8) . ? C15 C19 1.432(8) . ? C15 Fe1 2.056(6) . ? C15 H15 0.9500 . ? C16 C17 1.421(8) . ? C16 Fe1 2.051(5) . ? C16 H16 0.9500 . ? C17 C18 1.424(8) . ? C17 Fe1 2.047(5) . ? C17 H17 0.9500 . ? C18 C19 1.418(8) . ? C18 Fe1 2.044(5) . ? C18 H18 0.9500 . ? C19 Fe1 2.044(5) . ? C19 H19 0.9500 . ? C20 N1 1.443(7) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 O1 C1 N1 124.6(5) . . ? O1 C1 C2 128.8(5) . . ? N1 C1 C2 106.6(4) . . ? C9 C2 C3 135.6(5) . . ? C9 C2 C1 118.6(5) . . ? C3 C2 C1 105.9(4) . . ? C4 C3 C8 118.9(5) . . ? C4 C3 C2 134.3(5) . . ? C8 C3 C2 106.5(5) . . ? C3 C4 C5 119.8(5) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.1(5) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.9(5) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 118.3(5) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 N1 128.5(5) . . ? C7 C8 C3 121.8(5) . . ? N1 C8 C3 109.7(5) . . ? C2 C9 C10 128.8(5) . . ? C2 C9 H9 115.6 . . ? C10 C9 H9 115.6 . . ? C14 C10 C9 128.8(5) . . ? C14 C10 C11 106.4(5) . . ? C9 C10 C11 124.7(5) . . ? C14 C10 Fe1 68.6(3) . . ? C9 C10 Fe1 124.9(4) . . ? C11 C10 Fe1 67.9(3) . . ? C12 C11 C10 108.5(5) . . ? C12 C11 Fe1 70.2(3) . . ? C10 C11 Fe1 70.6(3) . . ? C12 C11 H11 125.8 . . ? C10 C11 H11 125.8 . . ? Fe1 C11 H11 125.0 . . ? C13 C12 C11 107.9(5) . . ? C13 C12 Fe1 69.3(3) . . ? C11 C12 Fe1 69.1(3) . . ? C13 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? Fe1 C12 H12 127.1 . . ? C12 C13 C14 108.6(5) . . ? C12 C13 Fe1 70.2(3) . . ? C14 C13 Fe1 69.6(3) . . ? C12 C13 H13 125.7 . . ? C14 C13 H13 125.7 . . ? Fe1 C13 H13 126.1 . . ? C10 C14 C13 108.6(5) . . ? C10 C14 Fe1 70.9(3) . . ? C13 C14 Fe1 69.4(3) . . ? C10 C14 H14 125.7 . . ? C13 C14 H14 125.7 . . ? Fe1 C14 H14 125.6 . . ? C16 C15 C19 107.6(5) . . ? C16 C15 Fe1 69.5(3) . . ? C19 C15 Fe1 69.1(3) . . ? C16 C15 H15 126.2 . . ? C19 C15 H15 126.2 . . ? Fe1 C15 H15 126.8 . . ? C17 C16 C15 108.3(5) . . ? C17 C16 Fe1 69.6(3) . . ? C15 C16 Fe1 69.9(3) . . ? C17 C16 H16 125.9 . . ? C15 C16 H16 125.9 . . ? Fe1 C16 H16 126.2 . . ? C16 C17 C18 107.9(5) . . ? C16 C17 Fe1 69.8(3) . . ? C18 C17 Fe1 69.5(3) . . ? C16 C17 H17 126.0 . . ? C18 C17 H17 126.0 . . ? Fe1 C17 H17 126.2 . . ? C19 C18 C17 108.2(5) . . ? C19 C18 Fe1 69.7(3) . . ? C17 C18 Fe1 69.7(3) . . ? C19 C18 H18 125.9 . . ? C17 C18 H18 125.9 . . ? Fe1 C18 H18 126.3 . . ? C18 C19 C15 108.0(5) . . ? C18 C19 Fe1 69.7(3) . . ? C15 C19 Fe1 70.0(3) . . ? C18 C19 H19 126.0 . . ? C15 C19 H19 126.0 . . ? Fe1 C19 H19 125.8 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 Fe1 C13 68.5(2) . . ? C11 Fe1 C14 68.9(2) . . ? C13 Fe1 C14 41.0(2) . . ? C11 Fe1 C19 157.9(2) . . ? C13 Fe1 C19 123.6(2) . . ? C14 Fe1 C19 107.0(2) . . ? C11 Fe1 C18 160.5(2) . . ? C13 Fe1 C18 106.1(2) . . ? C14 Fe1 C18 120.0(2) . . ? C19 Fe1 C18 40.6(2) . . ? C11 Fe1 C12 40.6(2) . . ? C13 Fe1 C12 40.5(2) . . ? C14 Fe1 C12 68.7(2) . . ? C19 Fe1 C12 160.0(2) . . ? C18 Fe1 C12 123.3(2) . . ? C11 Fe1 C17 124.4(2) . . ? C13 Fe1 C17 119.9(2) . . ? C14 Fe1 C17 155.3(2) . . ? C19 Fe1 C17 68.5(2) . . ? C18 Fe1 C17 40.7(2) . . ? C12 Fe1 C17 106.8(2) . . ? C11 Fe1 C16 108.5(2) . . ? C13 Fe1 C16 155.7(2) . . ? C14 Fe1 C16 162.4(2) . . ? C19 Fe1 C16 68.5(2) . . ? C18 Fe1 C16 68.3(2) . . ? C12 Fe1 C16 121.4(2) . . ? C17 Fe1 C16 40.6(2) . . ? C11 Fe1 C15 122.5(2) . . ? C13 Fe1 C15 161.4(2) . . ? C14 Fe1 C15 125.0(2) . . ? C19 Fe1 C15 40.9(2) . . ? C18 Fe1 C15 68.4(2) . . ? C12 Fe1 C15 157.3(2) . . ? C17 Fe1 C15 68.4(2) . . ? C16 Fe1 C15 40.6(2) . . ? C11 Fe1 C10 41.6(2) . . ? C13 Fe1 C10 68.6(2) . . ? C14 Fe1 C10 40.5(2) . . ? C19 Fe1 C10 121.3(2) . . ? C18 Fe1 C10 155.7(2) . . ? C12 Fe1 C10 69.0(2) . . ? C17 Fe1 C10 162.6(2) . . ? C16 Fe1 C10 126.1(2) . . ? C15 Fe1 C10 108.6(2) . . ? C1 N1 C8 111.1(4) . . ? C1 N1 C20 124.3(5) . . ? C8 N1 C20 124.1(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.599 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.133 data_2010src0017a _database_code_depnum_ccdc_archive 'CCDC 805395' #TrackingRef '- Spencer_Dalton_all.cif' #striucture (E)-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C19 H14 Br Fe N O)(unknown solvent)' _chemical_formula_sum 'C19 H14 Br Fe N O' _chemical_formula_weight 408.07 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.9574(11) _cell_length_b 16.2570(4) _cell_length_c 7.4078(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.757(2) _cell_angle_gamma 90.00 _cell_volume 3649.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13116 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description lath _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 3.018 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4646 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 31396 reflections reduced R(int) from 0.1377 to 0.0686 Ratio of minimum to maximum apparent transmission: 0.817387 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 66.065 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19710 _diffrn_reflns_av_R_equivalents 0.0881 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.42 _reflns_number_total 4129 _reflns_number_gt 3218 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. Structure forms with two channels per unit cell occupied by disordered solvent. This could not be modelled and the PLATON SQUEEZE routine was applied to the data which reduced the R-factor from 0.910 to 0.645 (results appended to end of CIF). The resultant electron count indicates electron density approximataing to 2.5 molecules hexane per unit cell. ; _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^)+(0.0290P)^2^+39.2560P] 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 4129 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.54678(16) 0.9284(3) 0.6535(7) 0.0243(11) Uani 1 1 d . . . C2 C 0.58808(15) 0.8976(3) 0.7798(6) 0.0210(10) Uani 1 1 d . . . C3 C 0.61420(16) 0.9721(3) 0.8422(6) 0.0208(10) Uani 1 1 d . . . C4 C 0.65485(16) 0.9861(3) 0.9551(6) 0.0207(10) Uani 1 1 d . . . H4 H 0.6721 0.9419 1.0150 0.025 Uiso 1 1 calc R . . C5 C 0.66971(16) 1.0672(3) 0.9785(7) 0.0232(10) Uani 1 1 d . . . C6 C 0.64469(16) 1.1331(3) 0.8997(7) 0.0262(11) Uani 1 1 d . . . H6 H 0.6560 1.1874 0.9189 0.031 Uiso 1 1 calc R . . C7 C 0.60291(17) 1.1200(3) 0.7922(7) 0.0262(11) Uani 1 1 d . . . H7 H 0.5848 1.1647 0.7404 0.031 Uiso 1 1 calc R . . C8 C 0.58862(16) 1.0397(3) 0.7632(7) 0.0244(11) Uani 1 1 d . . . C9 C 0.59218(16) 0.8170(3) 0.8196(7) 0.0245(11) Uani 1 1 d . . . H9 H 0.5680 0.7838 0.7625 0.029 Uiso 1 1 calc R . . C10 C 0.62822(17) 0.7728(3) 0.9371(7) 0.0242(10) Uani 1 1 d . . . C11 C 0.67472(17) 0.7871(3) 0.9675(7) 0.0255(11) Uani 1 1 d . . . H11 H 0.6888 0.8286 0.9099 0.031 Uiso 1 1 calc R . . C12 C 0.69638(19) 0.7292(3) 1.0976(7) 0.0309(12) Uani 1 1 d . . . H12 H 0.7273 0.7259 1.1439 0.037 Uiso 1 1 calc R . . C13 C 0.66418(19) 0.6774(3) 1.1466(7) 0.0313(12) Uani 1 1 d . . . H13 H 0.6697 0.6329 1.2313 0.038 Uiso 1 1 calc R . . C14 C 0.62225(19) 0.7029(3) 1.0480(7) 0.0300(12) Uani 1 1 d . . . H14 H 0.5948 0.6780 1.0541 0.036 Uiso 1 1 calc R . . C15 C 0.6392(2) 0.6438(4) 0.5954(8) 0.0459(16) Uani 1 1 d . . . H15 H 0.6176 0.6730 0.5093 0.055 Uiso 1 1 calc R . . C16 C 0.6314(3) 0.5771(4) 0.7101(9) 0.0517(17) Uani 1 1 d . . . H16 H 0.6034 0.5540 0.7142 0.062 Uiso 1 1 calc R . . C17 C 0.6723(2) 0.5510(4) 0.8165(9) 0.0468(17) Uani 1 1 d . . . H17 H 0.6765 0.5077 0.9043 0.056 Uiso 1 1 calc R . . C18 C 0.7061(2) 0.6003(3) 0.7702(8) 0.0419(15) Uani 1 1 d . . . H18 H 0.7368 0.5957 0.8198 0.050 Uiso 1 1 calc R . . C19 C 0.6856(2) 0.6579(4) 0.6359(8) 0.0422(15) Uani 1 1 d . . . H19 H 0.7004 0.6993 0.5815 0.051 Uiso 1 1 calc R . . N1 N 0.54899(13) 1.0119(3) 0.6562(6) 0.0255(9) Uani 1 1 d . . . H1 H 0.5280 1.0444 0.5976 0.031 Uiso 1 1 calc R . . O1 O 0.51660(11) 0.8874(2) 0.5626(5) 0.0302(8) Uani 1 1 d . . . Fe1 Fe 0.66117(3) 0.67120(4) 0.86985(10) 0.0273(2) Uani 1 1 d . . . Br1 Br 0.726777(17) 1.08645(3) 1.12512(8) 0.03251(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 0.024(3) 0.028(3) 0.023(2) 0.010(2) 0.009(2) 0.004(2) C2 0.020(2) 0.025(2) 0.017(2) 0.0046(19) 0.0017(19) 0.0022(18) C3 0.023(2) 0.024(2) 0.017(2) -0.0022(19) 0.0070(19) 0.0025(19) C4 0.023(2) 0.020(2) 0.020(2) 0.0015(19) 0.008(2) 0.0032(18) C5 0.020(2) 0.027(2) 0.021(2) -0.005(2) 0.003(2) -0.0031(19) C6 0.026(3) 0.027(3) 0.028(3) 0.000(2) 0.010(2) 0.000(2) C7 0.029(3) 0.024(2) 0.027(3) 0.004(2) 0.011(2) 0.005(2) C8 0.020(2) 0.033(3) 0.022(2) 0.007(2) 0.007(2) 0.004(2) C9 0.020(2) 0.029(3) 0.023(3) -0.001(2) 0.003(2) -0.002(2) C10 0.032(3) 0.017(2) 0.022(2) -0.001(2) 0.004(2) 0.0037(19) C11 0.029(3) 0.021(2) 0.025(3) 0.000(2) 0.003(2) 0.006(2) C12 0.036(3) 0.029(3) 0.025(3) -0.002(2) -0.001(2) 0.013(2) C13 0.045(3) 0.023(3) 0.026(3) 0.007(2) 0.009(2) 0.010(2) C14 0.042(3) 0.024(3) 0.027(3) 0.001(2) 0.012(2) -0.001(2) C15 0.069(5) 0.042(3) 0.022(3) -0.007(3) 0.000(3) 0.011(3) C16 0.071(5) 0.044(4) 0.041(4) -0.020(3) 0.013(3) -0.008(3) C17 0.080(5) 0.024(3) 0.040(3) -0.003(3) 0.022(3) 0.010(3) C18 0.061(4) 0.031(3) 0.038(3) 0.002(3) 0.018(3) 0.014(3) C19 0.073(5) 0.035(3) 0.024(3) 0.002(3) 0.023(3) 0.013(3) N1 0.018(2) 0.028(2) 0.030(2) 0.0070(19) 0.0028(18) 0.0069(16) O1 0.0231(19) 0.0310(19) 0.034(2) 0.0023(16) 0.0006(16) 0.0004(15) Fe1 0.0404(5) 0.0197(4) 0.0222(4) 0.0014(3) 0.0078(3) 0.0067(3) Br1 0.0248(3) 0.0302(3) 0.0409(3) -0.0089(2) 0.0029(2) -0.0024(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.231(6) . ? C1 N1 1.359(6) . ? C1 C2 1.508(7) . ? C2 C9 1.344(7) . ? C2 C3 1.477(7) . ? C3 C4 1.381(7) . ? C3 C8 1.410(7) . ? C4 C5 1.397(6) . ? C4 H4 0.9500 . ? C5 C6 1.380(7) . ? C5 Br1 1.902(5) . ? C6 C7 1.390(7) . ? C6 H6 0.9500 . ? C7 C8 1.381(7) . ? C7 H7 0.9500 . ? C8 N1 1.393(6) . ? C9 C10 1.456(7) . ? C9 H9 0.9500 . ? C10 C11 1.430(7) . ? C10 C14 1.436(7) . ? C10 Fe1 2.055(5) . ? C11 C12 1.414(7) . ? C11 Fe1 2.031(5) . ? C11 H11 0.9500 . ? C12 C13 1.408(8) . ? C12 Fe1 2.043(5) . ? C12 H12 0.9500 . ? C13 C14 1.415(8) . ? C13 Fe1 2.035(5) . ? C13 H13 0.9500 . ? C14 Fe1 2.026(5) . ? C14 H14 0.9500 . ? C15 C19 1.426(10) . ? C15 C16 1.428(9) . ? C15 Fe1 2.057(6) . ? C15 H15 0.9500 . ? C16 C17 1.414(10) . ? C16 Fe1 2.037(6) . ? C16 H16 0.9500 . ? C17 C18 1.413(9) . ? C17 Fe1 2.037(6) . ? C17 H17 0.9500 . ? C18 C19 1.418(8) . ? C18 Fe1 2.056(6) . ? C18 H18 0.9500 . ? C19 Fe1 2.038(5) . ? C19 H19 0.9500 . ? N1 H1 0.8800 . ? 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 O1 C1 N1 125.5(5) . . ? O1 C1 C2 127.7(4) . . ? N1 C1 C2 106.8(4) . . ? C9 C2 C3 135.2(4) . . ? C9 C2 C1 119.4(4) . . ? C3 C2 C1 105.2(4) . . ? C4 C3 C8 119.3(4) . . ? C4 C3 C2 134.3(4) . . ? C8 C3 C2 106.5(4) . . ? C3 C4 C5 117.9(4) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? C6 C5 C4 122.6(5) . . ? C6 C5 Br1 119.4(4) . . ? C4 C5 Br1 118.0(4) . . ? C5 C6 C7 120.0(5) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 117.7(5) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C7 C8 N1 127.7(4) . . ? C7 C8 C3 122.5(5) . . ? N1 C8 C3 109.8(4) . . ? C2 C9 C10 129.7(5) . . ? C2 C9 H9 115.2 . . ? C10 C9 H9 115.2 . . ? C11 C10 C14 106.3(4) . . ? C11 C10 C9 129.6(4) . . ? C14 C10 C9 124.0(5) . . ? C11 C10 Fe1 68.6(3) . . ? C14 C10 Fe1 68.3(3) . . ? C9 C10 Fe1 127.5(4) . . ? C12 C11 C10 108.8(5) . . ? C12 C11 Fe1 70.1(3) . . ? C10 C11 Fe1 70.4(3) . . ? C12 C11 H11 125.6 . . ? C10 C11 H11 125.6 . . ? Fe1 C11 H11 125.4 . . ? C13 C12 C11 108.1(5) . . ? C13 C12 Fe1 69.5(3) . . ? C11 C12 Fe1 69.2(3) . . ? C13 C12 H12 125.9 . . ? C11 C12 H12 125.9 . . ? Fe1 C12 H12 126.9 . . ? C12 C13 C14 108.3(4) . . ? C12 C13 Fe1 70.1(3) . . ? C14 C13 Fe1 69.3(3) . . ? C12 C13 H13 125.8 . . ? C14 C13 H13 125.8 . . ? Fe1 C13 H13 126.4 . . ? C13 C14 C10 108.4(5) . . ? C13 C14 Fe1 69.9(3) . . ? C10 C14 Fe1 70.5(3) . . ? C13 C14 H14 125.8 . . ? C10 C14 H14 125.8 . . ? Fe1 C14 H14 125.4 . . ? C19 C15 C16 106.3(6) . . ? C19 C15 Fe1 68.9(3) . . ? C16 C15 Fe1 68.8(3) . . ? C19 C15 H15 126.8 . . ? C16 C15 H15 126.8 . . ? Fe1 C15 H15 127.0 . . ? C17 C16 C15 108.6(6) . . ? C17 C16 Fe1 69.7(4) . . ? C15 C16 Fe1 70.4(4) . . ? C17 C16 H16 125.7 . . ? C15 C16 H16 125.7 . . ? Fe1 C16 H16 125.8 . . ? C18 C17 C16 108.5(6) . . ? C18 C17 Fe1 70.5(3) . . ? C16 C17 Fe1 69.7(3) . . ? C18 C17 H17 125.7 . . ? C16 C17 H17 125.7 . . ? Fe1 C17 H17 125.7 . . ? C17 C18 C19 107.3(6) . . ? C17 C18 Fe1 69.1(3) . . ? C19 C18 Fe1 69.1(3) . . ? C17 C18 H18 126.4 . . ? C19 C18 H18 126.4 . . ? Fe1 C18 H18 127.0 . . ? C18 C19 C15 109.2(6) . . ? C18 C19 Fe1 70.4(3) . . ? C15 C19 Fe1 70.3(3) . . ? C18 C19 H19 125.4 . . ? C15 C19 H19 125.4 . . ? Fe1 C19 H19 125.5 . . ? C1 N1 C8 111.6(4) . . ? C1 N1 H1 124.2 . . ? C8 N1 H1 124.2 . . ? C14 Fe1 C11 68.9(2) . . ? C14 Fe1 C13 40.8(2) . . ? C11 Fe1 C13 68.4(2) . . ? C14 Fe1 C16 108.1(3) . . ? C11 Fe1 C16 160.1(3) . . ? C13 Fe1 C16 123.0(3) . . ? C14 Fe1 C17 121.1(2) . . ? C11 Fe1 C17 158.1(3) . . ? C13 Fe1 C17 105.6(2) . . ? C16 Fe1 C17 40.6(3) . . ? C14 Fe1 C19 162.4(2) . . ? C11 Fe1 C19 108.4(2) . . ? C13 Fe1 C19 155.9(3) . . ? C16 Fe1 C19 68.2(3) . . ? C17 Fe1 C19 68.0(2) . . ? C14 Fe1 C12 68.5(2) . . ? C11 Fe1 C12 40.61(19) . . ? C13 Fe1 C12 40.4(2) . . ? C16 Fe1 C12 158.3(3) . . ? C17 Fe1 C12 121.3(3) . . ? C19 Fe1 C12 121.6(3) . . ? C14 Fe1 C10 41.2(2) . . ? C11 Fe1 C10 41.0(2) . . ? C13 Fe1 C10 68.9(2) . . ? C16 Fe1 C10 123.8(3) . . ? C17 Fe1 C10 158.5(3) . . ? C19 Fe1 C10 125.4(2) . . ? C12 Fe1 C10 68.7(2) . . ? C14 Fe1 C18 155.8(2) . . ? C11 Fe1 C18 122.8(2) . . ? C13 Fe1 C18 119.6(2) . . ? C16 Fe1 C18 68.2(3) . . ? C17 Fe1 C18 40.4(3) . . ? C19 Fe1 C18 40.5(2) . . ? C12 Fe1 C18 105.6(2) . . ? C10 Fe1 C18 160.6(2) . . ? C14 Fe1 C15 125.3(3) . . ? C11 Fe1 C15 123.8(2) . . ? C13 Fe1 C15 160.7(3) . . ? C16 Fe1 C15 40.8(3) . . ? C17 Fe1 C15 68.6(3) . . ? C19 Fe1 C15 40.7(3) . . ? C12 Fe1 C15 158.4(3) . . ? C10 Fe1 C15 109.4(2) . . ? C18 Fe1 C15 68.6(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 1.97 2.844(5) 172.6 5_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.544 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.120 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.031 342 58 ' ' 2 0.500 0.500 0.016 342 58 ' ' _platon_squeeze_details ; ; data_2009src1151 _database_code_depnum_ccdc_archive 'CCDC 805396' #TrackingRef '- Spencer_Dalton_all.cif' #structure 5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 Fe N O' _chemical_formula_sum 'C19 H17 Fe N O' _chemical_formula_weight 331.19 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_space_group_name_Hall '-P 2ybc' 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 6.0028(2) _cell_length_b 21.5130(12) _cell_length_c 11.3488(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.010(3) _cell_angle_gamma 90.00 _cell_volume 1463.54(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 20833 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.031 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7406 _exptl_absorpt_correction_T_max 0.8607 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6308 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16999 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3347 _reflns_number_gt 2562 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0569P)^2^+1.6847P] 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 3347 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.2656(5) 0.48227(14) 0.1191(2) 0.0200(6) Uani 1 1 d . . . C2 C 0.0510(5) 0.46553(13) 0.1782(2) 0.0180(6) Uani 1 1 d . . . H2 H -0.0545 0.5013 0.1680 0.022 Uiso 1 1 calc R . . C3 C -0.0394(4) 0.41227(13) 0.1027(2) 0.0165(6) Uani 1 1 d . . . C4 C -0.2305(5) 0.37704(15) 0.1082(3) 0.0220(6) Uani 1 1 d . . . H4 H -0.3312 0.3838 0.1687 0.026 Uiso 1 1 calc R . . C5 C -0.2733(5) 0.33088(15) 0.0221(3) 0.0245(6) Uani 1 1 d . . . H5 H -0.4040 0.3061 0.0246 0.029 Uiso 1 1 calc R . . C6 C -0.1262(5) 0.32130(14) -0.0662(3) 0.0238(6) Uani 1 1 d . . . H6 H -0.1577 0.2898 -0.1234 0.029 Uiso 1 1 calc R . . C7 C 0.0673(5) 0.35685(13) -0.0729(2) 0.0206(6) Uani 1 1 d . . . H7 H 0.1684 0.3503 -0.1333 0.025 Uiso 1 1 calc R . . C8 C 0.1050(5) 0.40208(13) 0.0124(2) 0.0176(6) Uani 1 1 d . . . C9 C 0.0869(5) 0.45213(13) 0.3116(2) 0.0184(6) Uani 1 1 d . . . H9A H 0.1378 0.4907 0.3521 0.022 Uiso 1 1 calc R . . H9B H -0.0578 0.4403 0.3431 0.022 Uiso 1 1 calc R . . C10 C 0.2534(5) 0.40160(13) 0.3400(2) 0.0176(6) Uani 1 1 d . . . C11 C 0.2215(5) 0.33610(14) 0.3265(2) 0.0207(6) Uani 1 1 d . . . H11 H 0.0879 0.3163 0.2981 0.025 Uiso 1 1 calc R . . C12 C 0.4247(5) 0.30560(15) 0.3628(2) 0.0233(6) Uani 1 1 d . . . H12 H 0.4497 0.2620 0.3627 0.028 Uiso 1 1 calc R . . C13 C 0.5840(5) 0.35201(15) 0.3994(3) 0.0240(7) Uani 1 1 d . . . H13 H 0.7334 0.3449 0.4279 0.029 Uiso 1 1 calc R . . C14 C 0.4775(4) 0.41084(15) 0.3854(2) 0.0205(6) Uani 1 1 d . . . H14 H 0.5446 0.4499 0.4034 0.025 Uiso 1 1 calc R . . C15 C 0.0726(5) 0.38223(15) 0.6124(2) 0.0221(6) Uani 1 1 d . . . H15 H -0.0552 0.4069 0.5929 0.027 Uiso 1 1 calc R . . C16 C 0.0829(5) 0.31705(14) 0.6050(3) 0.0250(7) Uani 1 1 d . . . H16 H -0.0360 0.2902 0.5801 0.030 Uiso 1 1 calc R . . C17 C 0.3026(6) 0.29864(16) 0.6416(3) 0.0317(8) Uani 1 1 d . . . H17 H 0.3576 0.2572 0.6449 0.038 Uiso 1 1 calc R . . C18 C 0.4268(5) 0.35360(18) 0.6725(3) 0.0342(8) Uani 1 1 d . . . H18 H 0.5785 0.3551 0.7007 0.041 Uiso 1 1 calc R . . C19 C 0.2837(5) 0.40504(15) 0.6536(3) 0.0274(7) Uani 1 1 d . . . H19 H 0.3222 0.4474 0.6662 0.033 Uiso 1 1 calc R . . N1 N 0.2837(4) 0.44449(12) 0.0236(2) 0.0193(5) Uani 1 1 d . . . H1 H 0.3931 0.4464 -0.0250 0.023 Uiso 1 1 calc R . . O1 O 0.3998(3) 0.52297(10) 0.15104(18) 0.0253(5) Uani 1 1 d . . . Fe1 Fe 0.31143(6) 0.356408(19) 0.49934(3) 0.01664(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 0.0251(15) 0.0233(15) 0.0112(13) 0.0073(11) -0.0030(11) 0.0007(12) C2 0.0209(14) 0.0192(14) 0.0137(13) 0.0022(11) -0.0007(10) 0.0021(11) C3 0.0193(14) 0.0202(14) 0.0096(12) 0.0039(11) -0.0017(10) 0.0019(11) C4 0.0181(14) 0.0315(16) 0.0164(14) 0.0030(12) 0.0018(11) 0.0000(12) C5 0.0242(15) 0.0289(16) 0.0202(15) 0.0015(13) 0.0004(12) -0.0080(13) C6 0.0323(16) 0.0221(16) 0.0167(14) 0.0000(12) -0.0008(12) -0.0028(13) C7 0.0256(15) 0.0242(15) 0.0123(14) 0.0009(11) 0.0042(11) 0.0020(12) C8 0.0200(14) 0.0180(14) 0.0147(13) 0.0063(11) -0.0010(10) 0.0008(11) C9 0.0241(15) 0.0212(15) 0.0101(13) 0.0001(11) 0.0022(11) 0.0000(11) C10 0.0206(14) 0.0236(15) 0.0087(13) 0.0017(11) 0.0023(10) 0.0023(11) C11 0.0264(15) 0.0243(15) 0.0112(13) -0.0022(11) -0.0003(11) 0.0018(12) C12 0.0329(17) 0.0247(16) 0.0126(14) -0.0015(12) 0.0032(12) 0.0111(13) C13 0.0210(15) 0.0374(18) 0.0138(14) 0.0052(13) 0.0034(11) 0.0071(13) C14 0.0193(14) 0.0315(17) 0.0110(13) 0.0010(12) 0.0040(10) -0.0032(12) C15 0.0261(15) 0.0268(16) 0.0140(14) 0.0003(12) 0.0058(11) 0.0048(12) C16 0.0332(17) 0.0267(17) 0.0157(15) -0.0007(12) 0.0074(12) -0.0082(13) C17 0.052(2) 0.0300(18) 0.0139(15) 0.0116(13) 0.0120(14) 0.0160(15) C18 0.0243(16) 0.067(3) 0.0106(15) 0.0064(15) -0.0001(12) 0.0007(16) C19 0.0413(19) 0.0303(18) 0.0112(14) -0.0046(12) 0.0064(12) -0.0113(14) N1 0.0202(12) 0.0258(13) 0.0121(11) 0.0002(10) 0.0044(9) -0.0043(10) O1 0.0306(11) 0.0298(12) 0.0152(10) 0.0019(9) -0.0006(8) -0.0108(9) Fe1 0.0201(2) 0.0218(2) 0.0081(2) 0.00111(16) 0.00071(14) 0.00110(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.231(3) . ? C1 N1 1.364(4) . ? C1 C2 1.527(4) . ? C2 C3 1.514(4) . ? C2 C9 1.546(4) . ? C2 H2 1.0000 . ? C3 C4 1.379(4) . ? C3 C8 1.394(4) . ? C4 C5 1.407(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(4) . ? C5 H5 0.9500 . ? C6 C7 1.396(4) . ? C6 H6 0.9500 . ? C7 C8 1.383(4) . ? C7 H7 0.9500 . ? C8 N1 1.409(4) . ? C9 C10 1.500(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C14 1.429(4) . ? C10 C11 1.429(4) . ? C10 Fe1 2.066(3) . ? C11 C12 1.426(4) . ? C11 Fe1 2.054(3) . ? C11 H11 0.9500 . ? C12 C13 1.429(4) . ? C12 Fe1 2.042(3) . ? C12 H12 0.9500 . ? C13 C14 1.423(4) . ? C13 Fe1 2.041(3) . ? C13 H13 0.9500 . ? C14 Fe1 2.042(3) . ? C14 H14 0.9500 . ? C15 C16 1.406(4) . ? C15 C19 1.415(4) . ? C15 Fe1 2.050(3) . ? C15 H15 0.9500 . ? C16 C17 1.418(5) . ? C16 Fe1 2.052(3) . ? C16 H16 0.9500 . ? C17 C18 1.431(5) . ? C17 Fe1 2.040(3) . ? C17 H17 0.9500 . ? C18 C19 1.410(5) . ? C18 Fe1 2.050(3) . ? C18 H18 0.9500 . ? C19 Fe1 2.053(3) . ? C19 H19 0.9500 . ? N1 H1 0.8800 . ? 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 O1 C1 N1 125.4(3) . . ? O1 C1 C2 126.3(3) . . ? N1 C1 C2 108.2(2) . . ? C3 C2 C1 102.5(2) . . ? C3 C2 C9 116.1(2) . . ? C1 C2 C9 113.4(2) . . ? C3 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? C9 C2 H2 108.2 . . ? C4 C3 C8 119.8(3) . . ? C4 C3 C2 131.7(3) . . ? C8 C3 C2 108.5(2) . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.4(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 116.9(3) . . ? C8 C7 H7 121.5 . . ? C6 C7 H7 121.5 . . ? C7 C8 C3 122.7(3) . . ? C7 C8 N1 127.9(3) . . ? C3 C8 N1 109.4(2) . . ? C10 C9 C2 113.8(2) . . ? C10 C9 H9A 108.8 . . ? C2 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C2 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C14 C10 C11 107.1(2) . . ? C14 C10 C9 125.5(3) . . ? C11 C10 C9 127.4(3) . . ? C14 C10 Fe1 68.76(16) . . ? C11 C10 Fe1 69.26(15) . . ? C9 C10 Fe1 127.51(19) . . ? C12 C11 C10 108.4(3) . . ? C12 C11 Fe1 69.15(16) . . ? C10 C11 Fe1 70.15(15) . . ? C12 C11 H11 125.8 . . ? C10 C11 H11 125.8 . . ? Fe1 C11 H11 126.4 . . ? C11 C12 C13 108.1(3) . . ? C11 C12 Fe1 70.09(16) . . ? C13 C12 Fe1 69.48(17) . . ? C11 C12 H12 125.9 . . ? C13 C12 H12 125.9 . . ? Fe1 C12 H12 126.1 . . ? C14 C13 C12 107.4(3) . . ? C14 C13 Fe1 69.66(16) . . ? C12 C13 Fe1 69.54(17) . . ? C14 C13 H13 126.3 . . ? C12 C13 H13 126.3 . . ? Fe1 C13 H13 126.1 . . ? C13 C14 C10 109.0(3) . . ? C13 C14 Fe1 69.55(17) . . ? C10 C14 Fe1 70.54(16) . . ? C13 C14 H14 125.5 . . ? C10 C14 H14 125.5 . . ? Fe1 C14 H14 126.0 . . ? C16 C15 C19 108.9(3) . . ? C16 C15 Fe1 70.03(16) . . ? C19 C15 Fe1 69.95(17) . . ? C16 C15 H15 125.5 . . ? C19 C15 H15 125.5 . . ? Fe1 C15 H15 126.1 . . ? C15 C16 C17 107.7(3) . . ? C15 C16 Fe1 69.88(16) . . ? C17 C16 Fe1 69.27(17) . . ? C15 C16 H16 126.1 . . ? C17 C16 H16 126.1 . . ? Fe1 C16 H16 126.3 . . ? C16 C17 C18 107.8(3) . . ? C16 C17 Fe1 70.18(17) . . ? C18 C17 Fe1 69.88(18) . . ? C16 C17 H17 126.1 . . ? C18 C17 H17 126.1 . . ? Fe1 C17 H17 125.4 . . ? C19 C18 C17 107.8(3) . . ? C19 C18 Fe1 70.04(17) . . ? C17 C18 Fe1 69.15(17) . . ? C19 C18 H18 126.1 . . ? C17 C18 H18 126.1 . . ? Fe1 C18 H18 126.3 . . ? C18 C19 C15 107.8(3) . . ? C18 C19 Fe1 69.76(18) . . ? C15 C19 Fe1 69.70(17) . . ? C18 C19 H19 126.1 . . ? C15 C19 H19 126.1 . . ? Fe1 C19 H19 126.0 . . ? C1 N1 C8 111.4(2) . . ? C1 N1 H1 124.3 . . ? C8 N1 H1 124.3 . . ? C17 Fe1 C13 117.78(12) . . ? C17 Fe1 C12 107.32(13) . . ? C13 Fe1 C12 40.98(13) . . ? C17 Fe1 C14 152.11(13) . . ? C13 Fe1 C14 40.79(12) . . ? C12 Fe1 C14 68.50(13) . . ? C17 Fe1 C18 40.98(14) . . ? C13 Fe1 C18 106.91(13) . . ? C12 Fe1 C18 127.05(13) . . ? C14 Fe1 C18 118.17(13) . . ? C17 Fe1 C15 67.78(12) . . ? C13 Fe1 C15 165.34(13) . . ? C12 Fe1 C15 153.09(13) . . ? C14 Fe1 C15 128.42(12) . . ? C18 Fe1 C15 67.67(12) . . ? C17 Fe1 C19 68.25(14) . . ? C13 Fe1 C19 126.88(13) . . ? C12 Fe1 C19 164.75(13) . . ? C14 Fe1 C19 108.14(12) . . ? C18 Fe1 C19 40.21(13) . . ? C15 Fe1 C19 40.35(12) . . ? C17 Fe1 C16 40.55(13) . . ? C13 Fe1 C16 152.33(13) . . ? C12 Fe1 C16 118.83(13) . . ? C14 Fe1 C16 165.95(12) . . ? C18 Fe1 C16 68.28(13) . . ? C15 Fe1 C16 40.09(13) . . ? C19 Fe1 C16 68.00(12) . . ? C17 Fe1 C11 127.57(14) . . ? C13 Fe1 C11 68.76(12) . . ? C12 Fe1 C11 40.76(11) . . ? C14 Fe1 C11 68.28(12) . . ? C18 Fe1 C11 165.43(14) . . ? C15 Fe1 C11 119.88(12) . . ? C19 Fe1 C11 153.31(13) . . ? C16 Fe1 C11 108.69(12) . . ? C17 Fe1 C10 165.65(13) . . ? C13 Fe1 C10 68.84(11) . . ? C12 Fe1 C10 68.62(11) . . ? C14 Fe1 C10 40.70(11) . . ? C18 Fe1 C10 152.34(13) . . ? C15 Fe1 C10 109.20(11) . . ? C19 Fe1 C10 119.25(12) . . ? C16 Fe1 C10 128.21(12) . . ? C11 Fe1 C10 40.59(11) . . ? 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 O1 C1 C2 C3 -178.8(3) . . . . ? N1 C1 C2 C3 1.6(3) . . . . ? O1 C1 C2 C9 -52.9(4) . . . . ? N1 C1 C2 C9 127.5(2) . . . . ? C1 C2 C3 C4 -178.9(3) . . . . ? C9 C2 C3 C4 56.9(4) . . . . ? C1 C2 C3 C8 -1.1(3) . . . . ? C9 C2 C3 C8 -125.2(3) . . . . ? C8 C3 C4 C5 0.7(4) . . . . ? C2 C3 C4 C5 178.3(3) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C6 C7 C8 C3 0.7(4) . . . . ? C6 C7 C8 N1 -178.6(3) . . . . ? C4 C3 C8 C7 -1.0(4) . . . . ? C2 C3 C8 C7 -179.1(2) . . . . ? C4 C3 C8 N1 178.4(2) . . . . ? C2 C3 C8 N1 0.3(3) . . . . ? C3 C2 C9 C10 61.7(3) . . . . ? C1 C2 C9 C10 -56.6(3) . . . . ? C2 C9 C10 C14 103.5(3) . . . . ? C2 C9 C10 C11 -75.9(4) . . . . ? C2 C9 C10 Fe1 -167.3(2) . . . . ? C14 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C12 179.2(3) . . . . ? Fe1 C10 C11 C12 -58.77(19) . . . . ? C14 C10 C11 Fe1 58.54(19) . . . . ? C9 C10 C11 Fe1 -122.0(3) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? Fe1 C11 C12 C13 -59.3(2) . . . . ? C10 C11 C12 Fe1 59.39(19) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? Fe1 C12 C13 C14 -59.6(2) . . . . ? C11 C12 C13 Fe1 59.6(2) . . . . ? C12 C13 C14 C10 -0.2(3) . . . . ? Fe1 C13 C14 C10 -59.7(2) . . . . ? C12 C13 C14 Fe1 59.5(2) . . . . ? C11 C10 C14 C13 0.2(3) . . . . ? C9 C10 C14 C13 -179.2(2) . . . . ? Fe1 C10 C14 C13 59.1(2) . . . . ? C11 C10 C14 Fe1 -58.86(19) . . . . ? C9 C10 C14 Fe1 121.7(3) . . . . ? C19 C15 C16 C17 -0.2(3) . . . . ? Fe1 C15 C16 C17 59.2(2) . . . . ? C19 C15 C16 Fe1 -59.3(2) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? Fe1 C16 C17 C18 60.0(2) . . . . ? C15 C16 C17 Fe1 -59.54(19) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? Fe1 C17 C18 C19 59.6(2) . . . . ? C16 C17 C18 Fe1 -60.2(2) . . . . ? C17 C18 C19 C15 0.5(3) . . . . ? Fe1 C18 C19 C15 59.6(2) . . . . ? C17 C18 C19 Fe1 -59.0(2) . . . . ? C16 C15 C19 C18 -0.2(3) . . . . ? Fe1 C15 C19 C18 -59.6(2) . . . . ? C16 C15 C19 Fe1 59.37(19) . . . . ? O1 C1 N1 C8 178.9(3) . . . . ? C2 C1 N1 C8 -1.5(3) . . . . ? C7 C8 N1 C1 -179.9(3) . . . . ? C3 C8 N1 C1 0.8(3) . . . . ? C16 C17 Fe1 C13 -157.51(18) . . . . ? C18 C17 Fe1 C13 84.0(2) . . . . ? C16 C17 Fe1 C12 -114.36(19) . . . . ? C18 C17 Fe1 C12 127.11(19) . . . . ? C16 C17 Fe1 C14 169.0(2) . . . . ? C18 C17 Fe1 C14 50.5(3) . . . . ? C16 C17 Fe1 C18 118.5(3) . . . . ? C16 C17 Fe1 C15 37.48(18) . . . . ? C18 C17 Fe1 C15 -81.1(2) . . . . ? C16 C17 Fe1 C19 81.1(2) . . . . ? C18 C17 Fe1 C19 -37.39(19) . . . . ? C18 C17 Fe1 C16 -118.5(3) . . . . ? C16 C17 Fe1 C11 -73.9(2) . . . . ? C18 C17 Fe1 C11 167.56(18) . . . . ? C16 C17 Fe1 C10 -43.1(6) . . . . ? C18 C17 Fe1 C10 -161.6(4) . . . . ? C14 C13 Fe1 C17 -156.74(18) . . . . ? C12 C13 Fe1 C17 84.7(2) . . . . ? C14 C13 Fe1 C12 118.6(2) . . . . ? C12 C13 Fe1 C14 -118.6(2) . . . . ? C14 C13 Fe1 C18 -113.77(19) . . . . ? C12 C13 Fe1 C18 127.62(19) . . . . ? C14 C13 Fe1 C15 -47.8(5) . . . . ? C12 C13 Fe1 C15 -166.4(4) . . . . ? C14 C13 Fe1 C19 -74.1(2) . . . . ? C12 C13 Fe1 C19 167.27(18) . . . . ? C14 C13 Fe1 C16 170.9(2) . . . . ? C12 C13 Fe1 C16 52.3(3) . . . . ? C14 C13 Fe1 C11 80.95(18) . . . . ? C12 C13 Fe1 C11 -37.66(17) . . . . ? C14 C13 Fe1 C10 37.27(17) . . . . ? C12 C13 Fe1 C10 -81.34(18) . . . . ? C11 C12 Fe1 C17 128.05(19) . . . . ? C13 C12 Fe1 C17 -112.67(19) . . . . ? C11 C12 Fe1 C13 -119.3(3) . . . . ? C11 C12 Fe1 C14 -81.24(19) . . . . ? C13 C12 Fe1 C14 38.05(17) . . . . ? C11 C12 Fe1 C18 168.98(19) . . . . ? C13 C12 Fe1 C18 -71.7(2) . . . . ? C11 C12 Fe1 C15 53.2(3) . . . . ? C13 C12 Fe1 C15 172.4(2) . . . . ? C11 C12 Fe1 C19 -161.3(4) . . . . ? C13 C12 Fe1 C19 -42.0(5) . . . . ? C11 C12 Fe1 C16 85.5(2) . . . . ? C13 C12 Fe1 C16 -155.21(17) . . . . ? C13 C12 Fe1 C11 119.3(3) . . . . ? C11 C12 Fe1 C10 -37.36(17) . . . . ? C13 C12 Fe1 C10 81.93(18) . . . . ? C13 C14 Fe1 C17 48.3(3) . . . . ? C10 C14 Fe1 C17 168.3(2) . . . . ? C10 C14 Fe1 C13 120.0(2) . . . . ? C13 C14 Fe1 C12 -38.23(17) . . . . ? C10 C14 Fe1 C12 81.78(18) . . . . ? C13 C14 Fe1 C18 83.4(2) . . . . ? C10 C14 Fe1 C18 -156.64(18) . . . . ? C13 C14 Fe1 C15 166.16(17) . . . . ? C10 C14 Fe1 C15 -73.8(2) . . . . ? C13 C14 Fe1 C19 125.95(18) . . . . ? C10 C14 Fe1 C19 -114.05(18) . . . . ? C13 C14 Fe1 C16 -162.4(4) . . . . ? C10 C14 Fe1 C16 -42.4(5) . . . . ? C13 C14 Fe1 C11 -82.22(19) . . . . ? C10 C14 Fe1 C11 37.78(16) . . . . ? C13 C14 Fe1 C10 -120.0(2) . . . . ? C19 C18 Fe1 C17 -119.1(3) . . . . ? C19 C18 Fe1 C13 127.75(19) . . . . ? C17 C18 Fe1 C13 -113.14(19) . . . . ? C19 C18 Fe1 C12 168.36(18) . . . . ? C17 C18 Fe1 C12 -72.5(2) . . . . ? C19 C18 Fe1 C14 85.0(2) . . . . ? C17 C18 Fe1 C14 -155.84(18) . . . . ? C19 C18 Fe1 C15 -37.78(18) . . . . ? C17 C18 Fe1 C15 81.3(2) . . . . ? C17 C18 Fe1 C19 119.1(3) . . . . ? C19 C18 Fe1 C16 -81.18(19) . . . . ? C17 C18 Fe1 C16 37.94(19) . . . . ? C19 C18 Fe1 C11 -161.9(4) . . . . ? C17 C18 Fe1 C11 -42.8(6) . . . . ? C19 C18 Fe1 C10 51.2(3) . . . . ? C17 C18 Fe1 C10 170.3(2) . . . . ? C16 C15 Fe1 C17 -37.89(19) . . . . ? C19 C15 Fe1 C17 82.1(2) . . . . ? C16 C15 Fe1 C13 -153.2(4) . . . . ? C19 C15 Fe1 C13 -33.2(5) . . . . ? C16 C15 Fe1 C12 46.7(3) . . . . ? C19 C15 Fe1 C12 166.7(2) . . . . ? C16 C15 Fe1 C14 168.65(17) . . . . ? C19 C15 Fe1 C14 -71.4(2) . . . . ? C16 C15 Fe1 C18 -82.3(2) . . . . ? C19 C15 Fe1 C18 37.6(2) . . . . ? C16 C15 Fe1 C19 -120.0(3) . . . . ? C19 C15 Fe1 C16 120.0(3) . . . . ? C16 C15 Fe1 C11 83.8(2) . . . . ? C19 C15 Fe1 C11 -156.24(19) . . . . ? C16 C15 Fe1 C10 127.10(18) . . . . ? C19 C15 Fe1 C10 -112.91(19) . . . . ? C18 C19 Fe1 C17 38.1(2) . . . . ? C15 C19 Fe1 C17 -80.8(2) . . . . ? C18 C19 Fe1 C13 -71.1(2) . . . . ? C15 C19 Fe1 C13 170.01(17) . . . . ? C18 C19 Fe1 C12 -37.8(5) . . . . ? C15 C19 Fe1 C12 -156.7(4) . . . . ? C18 C19 Fe1 C14 -112.5(2) . . . . ? C15 C19 Fe1 C14 128.62(18) . . . . ? C15 C19 Fe1 C18 -118.9(3) . . . . ? C18 C19 Fe1 C15 118.9(3) . . . . ? C18 C19 Fe1 C16 81.9(2) . . . . ? C15 C19 Fe1 C16 -36.99(18) . . . . ? C18 C19 Fe1 C11 170.0(3) . . . . ? C15 C19 Fe1 C11 51.1(3) . . . . ? C18 C19 Fe1 C10 -155.49(18) . . . . ? C15 C19 Fe1 C10 85.6(2) . . . . ? C15 C16 Fe1 C17 119.0(3) . . . . ? C15 C16 Fe1 C13 165.8(2) . . . . ? C17 C16 Fe1 C13 46.8(3) . . . . ? C15 C16 Fe1 C12 -157.91(17) . . . . ? C17 C16 Fe1 C12 83.1(2) . . . . ? C15 C16 Fe1 C14 -39.4(5) . . . . ? C17 C16 Fe1 C14 -158.4(4) . . . . ? C15 C16 Fe1 C18 80.69(19) . . . . ? C17 C16 Fe1 C18 -38.3(2) . . . . ? C17 C16 Fe1 C15 -119.0(3) . . . . ? C15 C16 Fe1 C19 37.21(18) . . . . ? C17 C16 Fe1 C19 -81.8(2) . . . . ? C15 C16 Fe1 C11 -114.50(18) . . . . ? C17 C16 Fe1 C11 126.5(2) . . . . ? C15 C16 Fe1 C10 -73.4(2) . . . . ? C17 C16 Fe1 C10 167.55(19) . . . . ? C12 C11 Fe1 C17 -71.5(2) . . . . ? C10 C11 Fe1 C17 168.75(17) . . . . ? C12 C11 Fe1 C13 37.86(18) . . . . ? C10 C11 Fe1 C13 -81.87(18) . . . . ? C10 C11 Fe1 C12 -119.7(2) . . . . ? C12 C11 Fe1 C14 81.8(2) . . . . ? C10 C11 Fe1 C14 -37.88(16) . . . . ? C12 C11 Fe1 C18 -37.3(6) . . . . ? C10 C11 Fe1 C18 -157.1(4) . . . . ? C12 C11 Fe1 C15 -155.31(18) . . . . ? C10 C11 Fe1 C15 84.97(19) . . . . ? C12 C11 Fe1 C19 169.2(3) . . . . ? C10 C11 Fe1 C19 49.5(3) . . . . ? C12 C11 Fe1 C16 -112.78(19) . . . . ? C10 C11 Fe1 C16 127.49(17) . . . . ? C12 C11 Fe1 C10 119.7(2) . . . . ? C14 C10 Fe1 C17 -157.6(4) . . . . ? C11 C10 Fe1 C17 -38.6(5) . . . . ? C9 C10 Fe1 C17 83.3(5) . . . . ? C14 C10 Fe1 C13 -37.35(17) . . . . ? C11 C10 Fe1 C13 81.64(18) . . . . ? C9 C10 Fe1 C13 -156.5(3) . . . . ? C14 C10 Fe1 C12 -81.47(19) . . . . ? C11 C10 Fe1 C12 37.51(17) . . . . ? C9 C10 Fe1 C12 159.4(3) . . . . ? C11 C10 Fe1 C14 119.0(2) . . . . ? C9 C10 Fe1 C14 -119.1(3) . . . . ? C14 C10 Fe1 C18 48.8(3) . . . . ? C11 C10 Fe1 C18 167.8(2) . . . . ? C9 C10 Fe1 C18 -70.3(4) . . . . ? C14 C10 Fe1 C15 127.17(18) . . . . ? C11 C10 Fe1 C15 -113.85(18) . . . . ? C9 C10 Fe1 C15 8.0(3) . . . . ? C14 C10 Fe1 C19 84.0(2) . . . . ? C11 C10 Fe1 C19 -156.97(17) . . . . ? C9 C10 Fe1 C19 -35.1(3) . . . . ? C14 C10 Fe1 C16 167.99(17) . . . . ? C11 C10 Fe1 C16 -73.0(2) . . . . ? C9 C10 Fe1 C16 48.8(3) . . . . ? C14 C10 Fe1 C11 -119.0(2) . . . . ? C9 C10 Fe1 C11 121.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.624 _refine_diff_density_min -0.736 _refine_diff_density_rms 0.099