# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_jt170 _database_code_depnum_ccdc_archive 'CCDC 922133' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Fe N2 O2, 0.50 (H2 O)' _chemical_formula_sum 'C18 H17 Fe N2 O2.5' _chemical_formula_weight 357.19 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 C2/c 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 12.0028(4) _cell_length_b 13.0095(5) _cell_length_c 20.3429(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.2160(10) _cell_angle_gamma 90.00 _cell_volume 3135.55(19) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9901 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.977 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 26062 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3619 _reflns_number_gt 3045 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0390P)^2^+5.3024P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3619 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Fe Fe 0.21873(2) 0.249243(19) 0.314073(11) 0.01699(9) Uani 1 1 d . . . O1 O 0.33478(11) 0.17129(10) 0.16512(6) 0.0228(3) Uani 1 1 d . . . N1 N 0.16921(13) 0.24710(11) 0.11732(7) 0.0179(3) Uani 1 1 d . . . H1N H 0.1279 0.3015 0.1187 0.018(5) Uiso 1 1 d R . . N2 N 0.04769(13) 0.40240(12) -0.05590(7) 0.0205(3) Uani 1 1 d . . . H2N H 0.0230 0.4656 -0.0566 0.030(6) Uiso 1 1 d R . . H3N H 0.0803 0.3777 -0.0891 0.020(5) Uiso 1 1 d R . . O2 O 0.02872(11) 0.38786(10) 0.05227(6) 0.0222(3) Uani 1 1 d . . . O1W O 0.5000 0.0586(2) 0.2500 0.0669(8) Uani 1 2 d S . . H1W H 0.4413 0.1118 0.2333 0.080 Uiso 1 1 d R . . C1 C 0.25606(14) 0.30028(13) 0.22559(8) 0.0179(3) Uani 1 1 d . . . C2 C 0.35016(15) 0.31436(14) 0.27770(9) 0.0216(4) Uani 1 1 d . . . H2 H 0.4231 0.2851 0.2794 0.026 Uiso 1 1 calc R . . C3 C 0.31519(16) 0.37964(15) 0.32625(10) 0.0267(4) Uani 1 1 d . . . H3 H 0.3609 0.4021 0.3662 0.032 Uiso 1 1 calc R . . C4 C 0.19974(17) 0.40593(14) 0.30500(10) 0.0257(4) Uani 1 1 d . . . H4 H 0.1552 0.4486 0.3284 0.031 Uiso 1 1 calc R . . C5 C 0.16272(15) 0.35755(13) 0.24302(9) 0.0206(4) Uani 1 1 d . . . H5 H 0.0893 0.3621 0.2175 0.025 Uiso 1 1 calc R . . C6 C 0.16659(17) 0.09881(15) 0.30431(10) 0.0283(4) Uani 1 1 d . . . H6 H 0.1532 0.0603 0.2641 0.034 Uiso 1 1 calc R . . C7 C 0.27113(17) 0.10632(16) 0.34836(10) 0.0303(4) Uani 1 1 d . . . H7 H 0.3398 0.0736 0.3428 0.036 Uiso 1 1 calc R . . C8 C 0.25464(18) 0.17131(18) 0.40189(10) 0.0329(5) Uani 1 1 d . . . H8 H 0.3104 0.1899 0.4385 0.039 Uiso 1 1 calc R . . C9 C 0.13989(17) 0.20395(18) 0.39126(10) 0.0303(4) Uani 1 1 d . . . H9 H 0.1057 0.2480 0.4195 0.036 Uiso 1 1 calc R . . C10 C 0.08572(17) 0.15900(16) 0.33101(10) 0.0279(4) Uani 1 1 d . . . H10 H 0.0088 0.1676 0.3118 0.033 Uiso 1 1 calc R . . C11 C 0.25769(15) 0.23329(13) 0.16740(8) 0.0173(3) Uani 1 1 d . . . C21 C 0.14738(14) 0.19145(13) 0.05725(8) 0.0170(3) Uani 1 1 d . . . C22 C 0.09204(14) 0.24013(13) -0.00054(8) 0.0159(3) Uani 1 1 d . . . C23 C 0.06895(15) 0.18317(14) -0.05931(9) 0.0214(4) Uani 1 1 d . . . H23 H 0.0310 0.2153 -0.0985 0.026 Uiso 1 1 calc R . . C24 C 0.10007(17) 0.08098(15) -0.06175(10) 0.0271(4) Uani 1 1 d . . . H24 H 0.0847 0.0436 -0.1023 0.033 Uiso 1 1 calc R . . C25 C 0.15388(17) 0.03419(14) -0.00439(10) 0.0282(4) Uani 1 1 d . . . H25 H 0.1752 -0.0360 -0.0056 0.034 Uiso 1 1 calc R . . C26 C 0.17711(16) 0.08814(14) 0.05473(9) 0.0236(4) Uani 1 1 d . . . H26 H 0.2135 0.0547 0.0938 0.028 Uiso 1 1 calc R . . C27 C 0.05491(13) 0.34974(13) 0.00057(8) 0.0164(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 Fe 0.01770(14) 0.02070(14) 0.01274(13) -0.00015(9) 0.00296(9) 0.00431(9) O1 0.0242(6) 0.0293(7) 0.0149(6) 0.0020(5) 0.0032(5) 0.0104(5) N1 0.0211(7) 0.0177(7) 0.0145(7) 0.0007(5) 0.0016(5) 0.0051(6) N2 0.0264(8) 0.0203(7) 0.0152(7) 0.0015(6) 0.0043(6) 0.0080(6) O2 0.0301(7) 0.0215(6) 0.0158(6) 0.0013(5) 0.0063(5) 0.0091(5) O1W 0.0510(16) 0.0443(15) 0.096(2) 0.000 -0.0165(15) 0.000 C1 0.0199(8) 0.0179(8) 0.0158(8) 0.0029(6) 0.0025(6) 0.0011(7) C2 0.0195(8) 0.0234(9) 0.0218(9) 0.0004(7) 0.0025(7) -0.0012(7) C3 0.0276(10) 0.0251(9) 0.0255(9) -0.0067(8) -0.0017(8) -0.0007(8) C4 0.0304(10) 0.0192(9) 0.0268(10) -0.0063(7) 0.0025(8) 0.0046(7) C5 0.0217(8) 0.0188(8) 0.0204(8) 0.0010(7) 0.0010(7) 0.0041(7) C6 0.0348(11) 0.0208(9) 0.0311(10) 0.0051(8) 0.0103(8) 0.0011(8) C7 0.0283(10) 0.0298(10) 0.0344(11) 0.0137(8) 0.0098(8) 0.0096(8) C8 0.0300(10) 0.0481(13) 0.0203(9) 0.0132(9) 0.0034(8) 0.0044(9) C9 0.0304(10) 0.0428(12) 0.0205(9) 0.0055(8) 0.0125(8) 0.0050(9) C10 0.0239(9) 0.0319(10) 0.0289(10) 0.0082(8) 0.0074(8) 0.0004(8) C11 0.0205(8) 0.0180(8) 0.0142(8) 0.0040(6) 0.0047(6) 0.0006(6) C21 0.0175(8) 0.0179(8) 0.0163(8) 0.0001(6) 0.0046(6) 0.0002(6) C22 0.0150(7) 0.0169(8) 0.0163(8) 0.0003(6) 0.0041(6) -0.0001(6) C23 0.0230(9) 0.0228(9) 0.0179(8) -0.0013(7) 0.0021(7) -0.0011(7) C24 0.0318(10) 0.0232(9) 0.0263(10) -0.0099(8) 0.0044(8) -0.0032(8) C25 0.0330(10) 0.0157(8) 0.0356(11) -0.0039(8) 0.0043(8) 0.0015(8) C26 0.0259(9) 0.0184(9) 0.0254(9) 0.0030(7) 0.0010(7) 0.0021(7) C27 0.0131(7) 0.0191(8) 0.0164(8) 0.0007(6) 0.0004(6) 0.0016(6) _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 Fe C2 2.0317(18) . ? Fe C1 2.0347(17) . ? Fe C8 2.0393(19) . ? Fe C9 2.0455(19) . ? Fe C3 2.046(2) . ? Fe C7 2.049(2) . ? Fe C5 2.0532(17) . ? Fe C6 2.055(2) . ? Fe C10 2.0547(19) . ? Fe C4 2.0561(19) . ? O1 C11 1.234(2) . ? N1 C11 1.361(2) . ? N1 C21 1.408(2) . ? N1 H1N 0.8674 . ? N2 C27 1.328(2) . ? N2 H2N 0.8739 . ? N2 H3N 0.8928 . ? O2 C27 1.248(2) . ? O1W H1W 1.0073 . ? C1 C2 1.431(2) . ? C1 C5 1.436(2) . ? C1 C11 1.473(2) . ? C2 C3 1.416(3) . ? C2 H2 0.9500 . ? C3 C4 1.426(3) . ? C3 H3 0.9500 . ? C4 C5 1.416(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.421(3) . ? C6 C7 1.424(3) . ? C6 H6 0.9500 . ? C7 C8 1.417(3) . ? C7 H7 0.9500 . ? C8 C9 1.424(3) . ? C8 H8 0.9500 . ? C9 C10 1.418(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C21 C26 1.394(2) . ? C21 C22 1.405(2) . ? C22 C23 1.396(2) . ? C22 C27 1.495(2) . ? C23 C24 1.384(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(3) . ? C24 H24 0.9500 . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 Fe C1 41.22(7) . . ? C2 Fe C8 117.31(8) . . ? C1 Fe C8 153.08(8) . . ? C2 Fe C9 151.81(8) . . ? C1 Fe C9 165.37(8) . . ? C8 Fe C9 40.81(8) . . ? C2 Fe C3 40.64(7) . . ? C1 Fe C3 68.66(7) . . ? C8 Fe C3 105.66(9) . . ? C9 Fe C3 117.92(9) . . ? C2 Fe C7 106.76(8) . . ? C1 Fe C7 119.88(7) . . ? C8 Fe C7 40.57(9) . . ? C9 Fe C7 68.40(8) . . ? C3 Fe C7 125.04(8) . . ? C2 Fe C5 69.10(7) . . ? C1 Fe C5 41.14(7) . . ? C8 Fe C5 163.22(8) . . ? C9 Fe C5 126.77(8) . . ? C3 Fe C5 68.37(7) . . ? C7 Fe C5 155.56(8) . . ? C2 Fe C6 127.17(8) . . ? C1 Fe C6 109.40(8) . . ? C8 Fe C6 68.25(9) . . ? C9 Fe C6 68.20(9) . . ? C3 Fe C6 163.53(8) . . ? C7 Fe C6 40.60(9) . . ? C5 Fe C6 121.69(8) . . ? C2 Fe C10 165.64(8) . . ? C1 Fe C10 128.46(8) . . ? C8 Fe C10 68.28(8) . . ? C9 Fe C10 40.47(8) . . ? C3 Fe C10 153.27(8) . . ? C7 Fe C10 68.21(8) . . ? C5 Fe C10 109.55(8) . . ? C6 Fe C10 40.46(8) . . ? C2 Fe C4 68.61(8) . . ? C1 Fe C4 68.53(7) . . ? C8 Fe C4 125.19(9) . . ? C9 Fe C4 107.23(8) . . ? C3 Fe C4 40.67(8) . . ? C7 Fe C4 162.50(8) . . ? C5 Fe C4 40.31(7) . . ? C6 Fe C4 155.23(8) . . ? C10 Fe C4 120.24(8) . . ? C11 N1 C21 126.60(14) . . ? C11 N1 H1N 117.7 . . ? C21 N1 H1N 114.8 . . ? C27 N2 H2N 118.4 . . ? C27 N2 H3N 119.6 . . ? H2N N2 H3N 121.0 . . ? C2 C1 C5 107.76(15) . . ? C2 C1 C11 124.09(15) . . ? C5 C1 C11 128.07(16) . . ? C2 C1 Fe 69.28(10) . . ? C5 C1 Fe 70.12(10) . . ? C11 C1 Fe 123.45(12) . . ? C3 C2 C1 107.84(16) . . ? C3 C2 Fe 70.24(11) . . ? C1 C2 Fe 69.50(10) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 125.8 . . ? C2 C3 C4 108.34(16) . . ? C2 C3 Fe 69.12(11) . . ? C4 C3 Fe 70.03(11) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe C3 H3 126.6 . . ? C5 C4 C3 108.34(16) . . ? C5 C4 Fe 69.74(10) . . ? C3 C4 Fe 69.30(11) . . ? C5 C4 H4 125.8 . . ? C3 C4 H4 125.8 . . ? Fe C4 H4 126.7 . . ? C4 C5 C1 107.72(16) . . ? C4 C5 Fe 69.96(11) . . ? C1 C5 Fe 68.74(10) . . ? C4 C5 H5 126.1 . . ? C1 C5 H5 126.1 . . ? Fe C5 H5 126.7 . . ? C10 C6 C7 107.99(18) . . ? C10 C6 Fe 69.78(11) . . ? C7 C6 Fe 69.49(12) . . ? C10 C6 H6 126.0 . . ? C7 C6 H6 126.0 . . ? Fe C6 H6 126.3 . . ? C8 C7 C6 107.88(17) . . ? C8 C7 Fe 69.34(11) . . ? C6 C7 Fe 69.91(11) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? Fe C7 H7 126.3 . . ? C7 C8 C9 108.16(19) . . ? C7 C8 Fe 70.09(11) . . ? C9 C8 Fe 69.83(11) . . ? C7 C8 H8 125.9 . . ? C9 C8 H8 125.9 . . ? Fe C8 H8 125.8 . . ? C10 C9 C8 107.86(18) . . ? C10 C9 Fe 70.11(11) . . ? C8 C9 Fe 69.36(11) . . ? C10 C9 H9 126.1 . . ? C8 C9 H9 126.1 . . ? Fe C9 H9 126.0 . . ? C9 C10 C6 108.10(18) . . ? C9 C10 Fe 69.41(11) . . ? C6 C10 Fe 69.76(11) . . ? C9 C10 H10 125.9 . . ? C6 C10 H10 125.9 . . ? Fe C10 H10 126.5 . . ? O1 C11 N1 123.92(16) . . ? O1 C11 C1 121.58(16) . . ? N1 C11 C1 114.49(15) . . ? C26 C21 C22 119.57(16) . . ? C26 C21 N1 120.96(16) . . ? C22 C21 N1 119.45(15) . . ? C23 C22 C21 118.66(15) . . ? C23 C22 C27 120.02(15) . . ? C21 C22 C27 121.29(15) . . ? C24 C23 C22 121.53(17) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C25 C24 C23 119.04(17) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.89(17) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 120.30(17) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? O2 C27 N2 122.25(16) . . ? O2 C27 C22 120.51(15) . . ? N2 C27 C22 117.20(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.344 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.058 data_jt175 _database_code_depnum_ccdc_archive 'CCDC 922134' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 Fe N2 O' _chemical_formula_sum 'C18 H14 Fe N2 O' _chemical_formula_weight 330.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c 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 13.2738(4) _cell_length_b 8.4806(2) _cell_length_c 14.0205(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.8590(10) _cell_angle_gamma 90.00 _cell_volume 1432.05(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9915 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.055 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.565 _exptl_absorpt_correction_T_max 0.684 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 23072 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3275 _reflns_number_gt 2992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0339P)^2^+0.9066P] 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 3275 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.003 _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 Fe Fe 0.289056(17) 0.13587(2) 1.092050(15) 0.01868(7) Uani 1 1 d . . . O O 0.43956(8) 0.63975(12) 0.90617(9) 0.0261(2) Uani 1 1 d . . . N11 N 0.16017(9) 0.53227(13) 0.94728(9) 0.0167(2) Uani 1 1 d . . . N13 N 0.35240(9) 0.51400(13) 0.99325(9) 0.0178(2) Uani 1 1 d . . . H1N H 0.4165 0.4633 1.0293 0.021 Uiso 1 1 d R . . C1 C 0.27042(11) 0.37323(15) 1.09445(10) 0.0175(3) Uani 1 1 d . . . C2 C 0.18015(12) 0.29488(17) 1.10480(11) 0.0210(3) Uani 1 1 d . . . H2 H 0.1037 0.3051 1.0587 0.025 Uiso 1 1 calc R . . C3 C 0.22516(13) 0.19879(18) 1.19638(12) 0.0255(3) Uani 1 1 d . . . H3 H 0.1839 0.1335 1.2221 0.031 Uiso 1 1 calc R . . C4 C 0.34233(13) 0.21723(19) 1.24275(11) 0.0262(3) Uani 1 1 d . . . H4 H 0.3928 0.1666 1.3050 0.031 Uiso 1 1 calc R . . C5 C 0.37156(12) 0.32449(18) 1.18025(11) 0.0228(3) Uani 1 1 d . . . H5 H 0.4445 0.3576 1.1930 0.027 Uiso 1 1 calc R . . C6 C 0.2125(2) 0.0199(2) 0.95279(13) 0.0476(5) Uani 1 1 d . . . H6 H 0.1427 0.0467 0.8979 0.057 Uiso 1 1 calc R . . C7 C 0.23050(15) -0.08391(19) 1.03709(13) 0.0317(3) Uani 1 1 d . . . H7 H 0.1748 -0.1396 1.0491 0.038 Uiso 1 1 calc R . . C8 C 0.34525(14) -0.09040(19) 1.10004(13) 0.0316(3) Uani 1 1 d . . . H8 H 0.3803 -0.1518 1.1620 0.038 Uiso 1 1 calc R . . C9 C 0.39988(18) 0.0086(2) 1.05661(18) 0.0448(5) Uani 1 1 d . . . H9 H 0.4777 0.0262 1.0838 0.054 Uiso 1 1 calc R . . C10 C 0.3181(2) 0.0770(2) 0.96520(17) 0.0567(7) Uani 1 1 d . . . H10 H 0.3313 0.1488 0.9197 0.068 Uiso 1 1 calc R . . C12 C 0.25799(10) 0.47825(15) 1.00734(10) 0.0157(2) Uani 1 1 d . . . C14 C 0.35284(11) 0.61325(15) 0.91620(11) 0.0181(3) Uani 1 1 d . . . C15 C 0.24481(11) 0.67645(15) 0.84772(10) 0.0164(2) Uani 1 1 d . . . C16 C 0.15214(11) 0.62921(14) 0.86466(10) 0.0162(2) Uani 1 1 d . . . C17 C 0.23219(12) 0.77872(16) 0.76480(11) 0.0208(3) Uani 1 1 d . . . H17 H 0.2955 0.8128 0.7553 0.025 Uiso 1 1 calc R . . C18 C 0.12814(13) 0.82953(17) 0.69736(11) 0.0236(3) Uani 1 1 d . . . H18 H 0.1193 0.8979 0.6407 0.028 Uiso 1 1 calc R . . C19 C 0.03505(12) 0.78006(17) 0.71248(12) 0.0240(3) Uani 1 1 d . . . H19 H -0.0368 0.8142 0.6651 0.029 Uiso 1 1 calc R . . C20 C 0.04645(11) 0.68264(16) 0.79509(11) 0.0205(3) Uani 1 1 d . . . H20 H -0.0173 0.6516 0.8050 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.02615(12) 0.01630(11) 0.01707(11) 0.00131(7) 0.01250(9) 0.00341(7) O 0.0158(5) 0.0284(6) 0.0369(6) 0.0094(4) 0.0136(4) 0.0028(4) N11 0.0147(5) 0.0154(5) 0.0201(5) -0.0011(4) 0.0074(4) -0.0010(4) N13 0.0122(5) 0.0182(5) 0.0213(5) 0.0020(4) 0.0055(4) 0.0015(4) C1 0.0197(6) 0.0160(6) 0.0174(6) -0.0019(5) 0.0082(5) 0.0010(5) C2 0.0228(7) 0.0203(7) 0.0239(7) 0.0005(5) 0.0138(6) 0.0023(5) C3 0.0357(8) 0.0244(7) 0.0257(7) 0.0033(6) 0.0220(6) 0.0043(6) C4 0.0345(8) 0.0300(8) 0.0153(6) 0.0019(6) 0.0116(6) 0.0060(6) C5 0.0233(7) 0.0263(7) 0.0162(6) -0.0009(5) 0.0058(5) 0.0009(6) C6 0.0784(15) 0.0295(9) 0.0187(7) -0.0060(7) 0.0045(8) 0.0183(9) C7 0.0420(9) 0.0200(7) 0.0301(8) -0.0054(6) 0.0123(7) -0.0003(6) C8 0.0395(9) 0.0213(7) 0.0356(9) 0.0015(6) 0.0173(7) 0.0092(6) C9 0.0564(12) 0.0347(9) 0.0653(13) -0.0077(9) 0.0469(11) 0.0046(8) C10 0.129(2) 0.0241(9) 0.0511(12) -0.0021(8) 0.0714(15) 0.0026(11) C12 0.0160(6) 0.0132(6) 0.0178(6) -0.0041(5) 0.0071(5) -0.0021(4) C14 0.0165(6) 0.0156(6) 0.0227(6) -0.0009(5) 0.0088(5) -0.0002(5) C15 0.0161(6) 0.0138(6) 0.0196(6) -0.0024(5) 0.0078(5) 0.0002(5) C16 0.0160(6) 0.0129(6) 0.0193(6) -0.0020(5) 0.0070(5) -0.0003(4) C17 0.0231(7) 0.0180(6) 0.0246(7) 0.0002(5) 0.0133(6) 0.0007(5) C18 0.0298(7) 0.0182(6) 0.0229(7) 0.0038(5) 0.0113(6) 0.0036(5) C19 0.0205(7) 0.0199(7) 0.0257(7) 0.0023(5) 0.0040(6) 0.0047(5) C20 0.0147(6) 0.0183(6) 0.0267(7) 0.0007(5) 0.0069(5) 0.0005(5) _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 Fe C1 2.0301(13) . ? Fe C10 2.0343(16) . ? Fe C6 2.0358(17) . ? Fe C5 2.0369(15) . ? Fe C2 2.0390(14) . ? Fe C7 2.0416(16) . ? Fe C8 2.0448(16) . ? Fe C4 2.0456(14) . ? Fe C3 2.0462(14) . ? Fe C9 2.0472(17) . ? O C14 1.2375(16) . ? N11 C12 1.2984(17) . ? N11 C16 1.3874(17) . ? N13 C14 1.3714(18) . ? N13 C12 1.3819(16) . ? N13 H1N 0.8960 . ? C1 C2 1.4297(19) . ? C1 C5 1.4361(19) . ? C1 C12 1.4638(18) . ? C2 C3 1.423(2) . ? C2 H2 0.9500 . ? C3 C4 1.420(2) . ? C3 H3 0.9500 . ? C4 C5 1.425(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.411(3) . ? C6 C10 1.423(4) . ? C6 H6 0.9500 . ? C7 C8 1.404(2) . ? C7 H7 0.9500 . ? C8 C9 1.404(3) . ? C8 H8 0.9500 . ? C9 C10 1.410(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C14 C15 1.4518(18) . ? C15 C17 1.4029(19) . ? C15 C16 1.4056(18) . ? C16 C20 1.4052(18) . ? C17 C18 1.375(2) . ? C17 H17 0.9500 . ? C18 C19 1.403(2) . ? C18 H18 0.9500 . ? C19 C20 1.378(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C10 109.10(7) . . ? C1 Fe C6 118.68(6) . . ? C10 Fe C6 40.93(10) . . ? C1 Fe C5 41.36(5) . . ? C10 Fe C5 118.19(8) . . ? C6 Fe C5 152.37(8) . . ? C1 Fe C2 41.14(5) . . ? C10 Fe C2 129.87(8) . . ? C6 Fe C2 108.49(7) . . ? C5 Fe C2 69.36(6) . . ? C1 Fe C7 151.85(6) . . ? C10 Fe C7 68.15(8) . . ? C6 Fe C7 40.49(7) . . ? C5 Fe C7 165.54(6) . . ? C2 Fe C7 117.74(7) . . ? C1 Fe C8 166.86(6) . . ? C10 Fe C8 67.58(7) . . ? C6 Fe C8 67.82(7) . . ? C5 Fe C8 127.81(6) . . ? C2 Fe C8 150.65(6) . . ? C7 Fe C8 40.20(7) . . ? C1 Fe C4 68.90(6) . . ? C10 Fe C4 151.12(10) . . ? C6 Fe C4 165.95(8) . . ? C5 Fe C4 40.87(6) . . ? C2 Fe C4 68.68(6) . . ? C7 Fe C4 127.54(7) . . ? C8 Fe C4 107.47(7) . . ? C1 Fe C3 68.87(6) . . ? C10 Fe C3 167.68(10) . . ? C6 Fe C3 128.45(9) . . ? C5 Fe C3 68.89(6) . . ? C2 Fe C3 40.77(6) . . ? C7 Fe C3 107.54(7) . . ? C8 Fe C3 117.19(7) . . ? C4 Fe C3 40.61(6) . . ? C1 Fe C9 129.19(7) . . ? C10 Fe C9 40.41(10) . . ? C6 Fe C9 68.43(9) . . ? C5 Fe C9 107.68(8) . . ? C2 Fe C9 168.05(7) . . ? C7 Fe C9 68.00(8) . . ? C8 Fe C9 40.14(7) . . ? C4 Fe C9 117.19(8) . . ? C3 Fe C9 150.13(8) . . ? C12 N11 C16 117.09(11) . . ? C14 N13 C12 123.48(11) . . ? C14 N13 H1N 114.9 . . ? C12 N13 H1N 121.2 . . ? C2 C1 C5 108.03(12) . . ? C2 C1 C12 124.20(12) . . ? C5 C1 C12 127.71(12) . . ? C2 C1 Fe 69.76(8) . . ? C5 C1 Fe 69.57(8) . . ? C12 C1 Fe 124.14(9) . . ? C3 C2 C1 107.81(13) . . ? C3 C2 Fe 69.89(8) . . ? C1 C2 Fe 69.10(8) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 126.5 . . ? C4 C3 C2 108.28(13) . . ? C4 C3 Fe 69.67(8) . . ? C2 C3 Fe 69.34(8) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? Fe C3 H3 126.7 . . ? C3 C4 C5 108.52(13) . . ? C3 C4 Fe 69.72(8) . . ? C5 C4 Fe 69.24(8) . . ? C3 C4 H4 125.7 . . ? C5 C4 H4 125.7 . . ? Fe C4 H4 126.9 . . ? C4 C5 C1 107.36(13) . . ? C4 C5 Fe 69.89(9) . . ? C1 C5 Fe 69.07(8) . . ? C4 C5 H5 126.3 . . ? C1 C5 H5 126.3 . . ? Fe C5 H5 126.3 . . ? C7 C6 C10 107.37(18) . . ? C7 C6 Fe 69.98(9) . . ? C10 C6 Fe 69.48(11) . . ? C7 C6 H6 126.3 . . ? C10 C6 H6 126.3 . . ? Fe C6 H6 125.8 . . ? C8 C7 C6 107.94(17) . . ? C8 C7 Fe 70.02(9) . . ? C6 C7 Fe 69.53(10) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? Fe C7 H7 126.0 . . ? C7 C8 C9 108.99(16) . . ? C7 C8 Fe 69.78(9) . . ? C9 C8 Fe 70.02(10) . . ? C7 C8 H8 125.5 . . ? C9 C8 H8 125.5 . . ? Fe C8 H8 126.3 . . ? C8 C9 C10 107.43(19) . . ? C8 C9 Fe 69.83(9) . . ? C10 C9 Fe 69.30(11) . . ? C8 C9 H9 126.3 . . ? C10 C9 H9 126.3 . . ? Fe C9 H9 126.1 . . ? C9 C10 C6 108.27(16) . . ? C9 C10 Fe 70.29(10) . . ? C6 C10 Fe 69.59(10) . . ? C9 C10 H10 125.9 . . ? C6 C10 H10 125.9 . . ? Fe C10 H10 125.8 . . ? N11 C12 N13 123.34(12) . . ? N11 C12 C1 119.15(11) . . ? N13 C12 C1 117.51(11) . . ? O C14 N13 120.87(12) . . ? O C14 C15 124.42(13) . . ? N13 C14 C15 114.67(11) . . ? C17 C15 C16 120.54(12) . . ? C17 C15 C14 121.12(12) . . ? C16 C15 C14 118.31(12) . . ? N11 C16 C20 118.33(12) . . ? N11 C16 C15 122.99(12) . . ? C20 C16 C15 118.69(12) . . ? C18 C17 C15 119.95(13) . . ? C18 C17 H17 120.0 . . ? C15 C17 H17 120.0 . . ? C17 C18 C19 119.76(13) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 120.92(13) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C16 120.10(13) . . ? C19 C20 H20 120.0 . . ? C16 C20 H20 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.388 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.061 data_kh5 _database_code_depnum_ccdc_archive 'CCDC 922135' #TrackingRef 'CCDC_922135.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 Fe N2 S' _chemical_formula_sum 'C18 H14 Fe N2 S' _chemical_formula_weight 346.22 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 14.1216(4) _cell_length_b 8.5142(2) _cell_length_c 13.7245(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.6260(10) _cell_angle_gamma 90.00 _cell_volume 1487.84(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9857 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5339 _exptl_absorpt_correction_T_max 0.6251 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 24353 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0091 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3412 _reflns_number_gt 3171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SIR (Spek, 2003)' _computing_publication_material 'SIR (Spek, 2003)' _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^)+(0.0263P)^2^+0.9697P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3412 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Fe Fe 0.285608(15) 0.35981(2) 1.101462(14) 0.01721(6) Uani 1 1 d . . . S S 0.44510(2) -0.19494(4) 0.91397(3) 0.02089(8) Uani 1 1 d . . . N11 N 0.15781(8) -0.03337(12) 0.95112(9) 0.0169(2) Uani 1 1 d . . . N13 N 0.33892(8) -0.03174(12) 0.99763(8) 0.0161(2) Uani 1 1 d . . . H1N H 0.3971 0.0153 1.0352 0.019 Uiso 1 1 d R . . C1 C 0.26912(10) 0.12163(15) 1.10218(10) 0.0168(2) Uani 1 1 d . . . C2 C 0.18531(11) 0.19904(16) 1.11578(11) 0.0204(3) Uani 1 1 d . . . H2 H 0.1125 0.1896 1.0695 0.024 Uiso 1 1 calc R . . C3 C 0.23092(12) 0.29249(16) 1.21098(11) 0.0243(3) Uani 1 1 d . . . H3 H 0.1936 0.3561 1.2395 0.029 Uiso 1 1 calc R . . C4 C 0.34186(12) 0.27453(17) 1.25621(11) 0.0239(3) Uani 1 1 d . . . H4 H 0.3912 0.3243 1.3200 0.029 Uiso 1 1 calc R . . C5 C 0.36655(10) 0.16935(16) 1.18976(10) 0.0197(3) Uani 1 1 d . . . H5 H 0.4349 0.1367 1.2012 0.024 Uiso 1 1 calc R . . C6 C 0.20870(15) 0.47447(18) 0.95789(12) 0.0368(4) Uani 1 1 d . . . H6 H 0.1443 0.4425 0.9005 0.044 Uiso 1 1 calc R . . C7 C 0.22005(12) 0.57463(17) 1.04543(12) 0.0273(3) Uani 1 1 d . . . H7 H 0.1648 0.6213 1.0572 0.033 Uiso 1 1 calc R . . C8 C 0.32915(12) 0.59171(16) 1.11172(11) 0.0238(3) Uani 1 1 d . . . H8 H 0.3598 0.6526 1.1759 0.029 Uiso 1 1 calc R . . C9 C 0.38465(13) 0.50288(17) 1.06629(13) 0.0292(3) Uani 1 1 d . . . H9 H 0.4588 0.4935 1.0947 0.035 Uiso 1 1 calc R . . C10 C 0.31077(16) 0.43079(18) 0.97163(13) 0.0371(4) Uani 1 1 d . . . H10 H 0.3265 0.3644 0.9250 0.045 Uiso 1 1 calc R . . C12 C 0.25248(9) 0.01528(14) 1.01266(10) 0.0153(2) Uani 1 1 d . . . C14 C 0.33523(9) -0.13575(14) 0.92075(10) 0.0153(2) Uani 1 1 d . . . C15 C 0.23079(9) -0.18849(14) 0.84871(10) 0.0154(2) Uani 1 1 d . . . C16 C 0.14561(9) -0.13239(14) 0.86672(10) 0.0161(2) Uani 1 1 d . . . C17 C 0.21229(10) -0.29140(15) 0.76208(11) 0.0192(2) Uani 1 1 d . . . H17 H 0.2697 -0.3318 0.7512 0.023 Uiso 1 1 calc R . . C18 C 0.11112(11) -0.33369(16) 0.69301(11) 0.0224(3) Uani 1 1 d . . . H18 H 0.0987 -0.4007 0.6334 0.027 Uiso 1 1 calc R . . C19 C 0.02640(10) -0.27778(16) 0.71071(11) 0.0237(3) Uani 1 1 d . . . H19 H -0.0432 -0.3078 0.6631 0.028 Uiso 1 1 calc R . . C20 C 0.04299(10) -0.17998(16) 0.79627(11) 0.0213(3) Uani 1 1 d . . . H20 H -0.0150 -0.1443 0.8080 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.02598(11) 0.01344(10) 0.01384(9) -0.00009(6) 0.01014(8) -0.00159(7) S 0.01554(14) 0.02066(16) 0.02880(17) -0.00304(13) 0.01178(13) -0.00054(11) N11 0.0161(5) 0.0144(5) 0.0200(5) 0.0007(4) 0.0076(4) 0.0009(4) N13 0.0125(4) 0.0160(5) 0.0188(5) -0.0010(4) 0.0059(4) -0.0021(4) C1 0.0202(6) 0.0142(6) 0.0169(6) 0.0024(4) 0.0088(5) -0.0010(5) C2 0.0231(6) 0.0188(6) 0.0230(6) -0.0002(5) 0.0135(5) -0.0009(5) C3 0.0361(7) 0.0220(7) 0.0225(6) -0.0007(5) 0.0199(6) -0.0020(6) C4 0.0346(7) 0.0238(7) 0.0145(6) 0.0003(5) 0.0117(5) -0.0055(6) C5 0.0222(6) 0.0202(6) 0.0154(6) 0.0033(5) 0.0069(5) -0.0013(5) C6 0.0561(10) 0.0236(7) 0.0166(6) 0.0060(6) 0.0023(7) -0.0084(7) C7 0.0331(7) 0.0180(6) 0.0287(7) 0.0063(6) 0.0114(6) 0.0042(6) C8 0.0338(7) 0.0143(6) 0.0254(7) -0.0010(5) 0.0148(6) -0.0024(5) C9 0.0419(8) 0.0181(6) 0.0398(8) 0.0057(6) 0.0293(7) 0.0006(6) C10 0.0782(13) 0.0187(7) 0.0290(8) 0.0024(6) 0.0370(8) -0.0011(7) C12 0.0170(5) 0.0117(5) 0.0177(5) 0.0038(4) 0.0081(4) 0.0010(4) C14 0.0159(5) 0.0126(5) 0.0183(6) 0.0034(4) 0.0082(5) 0.0002(4) C15 0.0164(5) 0.0118(5) 0.0178(6) 0.0021(4) 0.0072(5) -0.0008(4) C16 0.0165(6) 0.0121(5) 0.0189(6) 0.0021(4) 0.0068(5) 0.0004(4) C17 0.0223(6) 0.0157(6) 0.0223(6) -0.0001(5) 0.0122(5) -0.0015(5) C18 0.0266(7) 0.0174(6) 0.0216(6) -0.0033(5) 0.0090(5) -0.0040(5) C19 0.0188(6) 0.0191(6) 0.0266(7) -0.0025(5) 0.0036(5) -0.0032(5) C20 0.0151(6) 0.0187(6) 0.0276(7) -0.0011(5) 0.0070(5) 0.0001(5) _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 Fe C2 2.0393(13) . ? Fe C6 2.0406(14) . ? Fe C1 2.0417(13) . ? Fe C7 2.0440(14) . ? Fe C3 2.0466(13) . ? Fe C5 2.0509(13) . ? Fe C4 2.0517(13) . ? Fe C10 2.0529(14) . ? Fe C8 2.0546(14) . ? Fe C9 2.0632(14) . ? S C14 1.6717(12) . ? N11 C12 1.3021(16) . ? N11 C16 1.3819(16) . ? N13 C14 1.3611(16) . ? N13 C12 1.3822(15) . ? N13 H1N 0.8566 . ? C1 C2 1.4357(18) . ? C1 C5 1.4396(17) . ? C1 C12 1.4611(17) . ? C2 C3 1.4237(19) . ? C2 H2 0.9500 . ? C3 C4 1.422(2) . ? C3 H3 0.9500 . ? C4 C5 1.4249(19) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.420(3) . ? C6 C7 1.425(2) . ? C6 H6 0.9500 . ? C7 C8 1.418(2) . ? C7 H7 0.9500 . ? C8 C9 1.413(2) . ? C8 H8 0.9500 . ? C9 C10 1.407(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C14 C15 1.4467(16) . ? C15 C17 1.4075(18) . ? C15 C16 1.4119(17) . ? C16 C20 1.4096(17) . ? C17 C18 1.3776(19) . ? C17 H17 0.9500 . ? C18 C19 1.403(2) . ? C18 H18 0.9500 . ? C19 C20 1.374(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 Fe C6 108.20(6) . . ? C2 Fe C1 41.19(5) . . ? C6 Fe C1 117.75(6) . . ? C2 Fe C7 114.61(6) . . ? C6 Fe C7 40.83(6) . . ? C1 Fe C7 148.93(6) . . ? C2 Fe C3 40.78(5) . . ? C6 Fe C3 129.11(7) . . ? C1 Fe C3 68.79(5) . . ? C7 Fe C3 105.88(6) . . ? C2 Fe C5 69.22(5) . . ? C6 Fe C5 151.24(6) . . ? C1 Fe C5 41.19(5) . . ? C7 Fe C5 167.36(6) . . ? C3 Fe C5 68.62(6) . . ? C2 Fe C4 68.71(6) . . ? C6 Fe C4 167.15(7) . . ? C1 Fe C4 68.74(5) . . ? C7 Fe C4 128.00(6) . . ? C3 Fe C4 40.60(6) . . ? C5 Fe C4 40.64(5) . . ? C2 Fe C10 132.02(6) . . ? C6 Fe C10 40.59(8) . . ? C1 Fe C10 111.07(6) . . ? C7 Fe C10 68.30(6) . . ? C3 Fe C10 169.09(7) . . ? C5 Fe C10 118.96(6) . . ? C4 Fe C10 150.21(7) . . ? C2 Fe C8 146.94(6) . . ? C6 Fe C8 67.97(6) . . ? C1 Fe C8 170.24(6) . . ? C7 Fe C8 40.47(6) . . ? C3 Fe C8 114.56(6) . . ? C5 Fe C8 130.20(6) . . ? C4 Fe C8 107.38(6) . . ? C10 Fe C8 67.52(6) . . ? C2 Fe C9 171.16(6) . . ? C6 Fe C9 67.86(7) . . ? C1 Fe C9 132.67(5) . . ? C7 Fe C9 68.05(6) . . ? C3 Fe C9 147.83(6) . . ? C5 Fe C9 110.13(6) . . ? C4 Fe C9 116.93(6) . . ? C10 Fe C9 39.98(7) . . ? C8 Fe C9 40.15(6) . . ? C12 N11 C16 117.30(11) . . ? C14 N13 C12 124.33(10) . . ? C14 N13 H1N 118.4 . . ? C12 N13 H1N 116.9 . . ? C2 C1 C5 107.80(11) . . ? C2 C1 C12 123.51(11) . . ? C5 C1 C12 128.69(12) . . ? C2 C1 Fe 69.32(7) . . ? C5 C1 Fe 69.75(7) . . ? C12 C1 Fe 126.07(9) . . ? C3 C2 C1 107.74(12) . . ? C3 C2 Fe 69.88(8) . . ? C1 C2 Fe 69.49(7) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 126.1 . . ? C4 C3 C2 108.44(12) . . ? C4 C3 Fe 69.89(8) . . ? C2 C3 Fe 69.34(7) . . ? C4 C3 H3 125.8 . . ? C2 C3 H3 125.8 . . ? Fe C3 H3 126.6 . . ? C3 C4 C5 108.45(12) . . ? C3 C4 Fe 69.50(8) . . ? C5 C4 Fe 69.65(7) . . ? C3 C4 H4 125.8 . . ? C5 C4 H4 125.8 . . ? Fe C4 H4 126.7 . . ? C4 C5 C1 107.57(12) . . ? C4 C5 Fe 69.71(8) . . ? C1 C5 Fe 69.06(7) . . ? C4 C5 H5 126.2 . . ? C1 C5 H5 126.2 . . ? Fe C5 H5 126.6 . . ? C10 C6 C7 107.89(14) . . ? C10 C6 Fe 70.17(9) . . ? C7 C6 Fe 69.71(8) . . ? C10 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe C6 H6 125.6 . . ? C8 C7 C6 107.30(14) . . ? C8 C7 Fe 70.17(8) . . ? C6 C7 Fe 69.46(8) . . ? C8 C7 H7 126.4 . . ? C6 C7 H7 126.4 . . ? Fe C7 H7 125.6 . . ? C9 C8 C7 108.54(13) . . ? C9 C8 Fe 70.25(8) . . ? C7 C8 Fe 69.36(8) . . ? C9 C8 H8 125.7 . . ? C7 C8 H8 125.7 . . ? Fe C8 H8 126.2 . . ? C10 C9 C8 108.03(14) . . ? C10 C9 Fe 69.61(9) . . ? C8 C9 Fe 69.60(8) . . ? C10 C9 H9 126.0 . . ? C8 C9 H9 126.0 . . ? Fe C9 H9 126.4 . . ? C9 C10 C6 108.24(13) . . ? C9 C10 Fe 70.40(8) . . ? C6 C10 Fe 69.24(8) . . ? C9 C10 H10 125.9 . . ? C6 C10 H10 125.9 . . ? Fe C10 H10 126.1 . . ? N11 C12 N13 122.43(11) . . ? N11 C12 C1 119.28(11) . . ? N13 C12 C1 118.28(11) . . ? N13 C14 C15 114.68(10) . . ? N13 C14 S 120.93(9) . . ? C15 C14 S 124.39(10) . . ? C17 C15 C16 119.84(11) . . ? C17 C15 C14 122.17(11) . . ? C16 C15 C14 117.99(11) . . ? N11 C16 C20 117.96(11) . . ? N11 C16 C15 123.11(11) . . ? C20 C16 C15 118.92(12) . . ? C18 C17 C15 120.15(12) . . ? C18 C17 H17 119.9 . . ? C15 C17 H17 119.9 . . ? C17 C18 C19 120.03(12) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 120.69(12) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C16 120.33(12) . . ? C19 C20 H20 119.8 . . ? C16 C20 H20 119.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.052 data_jt195 _database_code_depnum_ccdc_archive 'CCDC 922136' #TrackingRef 'CCDC_922136.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Fe N O2' _chemical_formula_sum 'C18 H13 Fe N O2' _chemical_formula_weight 331.14 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 P21/c 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 10.3361(3) _cell_length_b 7.9197(2) _cell_length_c 17.1157(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.9840(10) _cell_angle_gamma 90.00 _cell_volume 1383.88(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9983 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.50 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.618 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23033 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3187 _reflns_number_gt 2855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon (Spek, 2003)' _computing_publication_material 'Platon (Spek, 2003)' _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^)+(0.0235P)^2^+0.9979P] 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 3187 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 Fe Fe 0.25634(2) 0.64391(3) 0.027354(12) 0.01529(7) Uani 1 1 d . . . C1 C 0.25010(14) 0.89988(18) 0.03499(9) 0.0172(3) Uani 1 1 d . . . C2 C 0.13183(15) 0.83658(19) -0.01086(9) 0.0192(3) Uani 1 1 d . . . H2 H 0.0456 0.8506 0.0008 0.023 Uiso 1 1 calc R . . C3 C 0.16709(16) 0.7491(2) -0.07692(9) 0.0228(3) Uani 1 1 d . . . H3 H 0.1081 0.6951 -0.1174 0.027 Uiso 1 1 calc R . . C4 C 0.30547(17) 0.7562(2) -0.07233(9) 0.0240(3) Uani 1 1 d . . . H4 H 0.3546 0.7075 -0.1091 0.029 Uiso 1 1 calc R . . C5 C 0.35781(15) 0.84834(19) -0.00345(9) 0.0195(3) Uani 1 1 d . . . H5 H 0.4478 0.8718 0.0141 0.023 Uiso 1 1 calc R . . C6 C 0.27200(17) 0.5497(2) 0.13989(10) 0.0251(3) Uani 1 1 d . . . H6 H 0.2736 0.6135 0.1870 0.030 Uiso 1 1 calc R . . C7 C 0.15849(16) 0.4842(2) 0.09188(10) 0.0243(3) Uani 1 1 d . . . H7 H 0.0708 0.4966 0.1014 0.029 Uiso 1 1 calc R . . C8 C 0.19872(17) 0.39703(19) 0.02736(10) 0.0252(3) Uani 1 1 d . . . H8 H 0.1429 0.3410 -0.0140 0.030 Uiso 1 1 calc R . . C9 C 0.33764(17) 0.4083(2) 0.03547(11) 0.0261(3) Uani 1 1 d . . . H9 H 0.3909 0.3611 0.0006 0.031 Uiso 1 1 calc R . . C10 C 0.38248(16) 0.5028(2) 0.10494(10) 0.0263(4) Uani 1 1 d . . . H10 H 0.4711 0.5299 0.1246 0.032 Uiso 1 1 calc R . . N11 N 0.15901(12) 1.02047(16) 0.14306(8) 0.0186(3) Uani 1 1 d . . . C12 C 0.25839(14) 0.99242(18) 0.10878(9) 0.0168(3) Uani 1 1 d . . . O13 O 0.38422(10) 1.04769(14) 0.13492(6) 0.0195(2) Uani 1 1 d . . . C14 C 0.41250(15) 1.1486(2) 0.20187(9) 0.0199(3) Uani 1 1 d . . . O O 0.52318(11) 1.19638(17) 0.21962(7) 0.0284(3) Uani 1 1 d . . . C15 C 0.30161(15) 1.18389(19) 0.24275(9) 0.0188(3) Uani 1 1 d . . . C16 C 0.17881(15) 1.11650(18) 0.21222(9) 0.0176(3) Uani 1 1 d . . . C17 C 0.31776(17) 1.2881(2) 0.30950(10) 0.0241(3) Uani 1 1 d . . . H17 H 0.4014 1.3338 0.3295 0.029 Uiso 1 1 calc R . . C18 C 0.21106(18) 1.3239(2) 0.34597(10) 0.0269(4) Uani 1 1 d . . . H18 H 0.2207 1.3957 0.3910 0.032 Uiso 1 1 calc R . . C19 C 0.08862(17) 1.2545(2) 0.31674(10) 0.0255(3) Uani 1 1 d . . . H19 H 0.0158 1.2787 0.3426 0.031 Uiso 1 1 calc R . . C20 C 0.07199(16) 1.1515(2) 0.25090(10) 0.0224(3) Uani 1 1 d . . . H20 H -0.0116 1.1046 0.2319 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.01713(11) 0.01240(11) 0.01649(11) 0.00182(8) 0.00310(8) 0.00049(8) C1 0.0193(7) 0.0127(6) 0.0203(7) 0.0046(5) 0.0055(6) 0.0005(5) C2 0.0198(7) 0.0161(7) 0.0212(7) 0.0048(6) 0.0012(6) 0.0029(6) C3 0.0307(8) 0.0190(7) 0.0177(7) 0.0044(6) 0.0006(6) 0.0005(6) C4 0.0335(9) 0.0199(7) 0.0209(8) 0.0039(6) 0.0118(7) 0.0013(7) C5 0.0207(7) 0.0161(7) 0.0234(7) 0.0038(6) 0.0084(6) -0.0010(6) C6 0.0368(9) 0.0193(8) 0.0184(7) 0.0059(6) 0.0022(7) -0.0009(7) C7 0.0266(8) 0.0193(7) 0.0283(8) 0.0082(6) 0.0082(7) -0.0026(6) C8 0.0316(9) 0.0135(7) 0.0291(9) 0.0014(6) 0.0006(7) -0.0037(6) C9 0.0297(9) 0.0156(7) 0.0337(9) 0.0027(7) 0.0072(7) 0.0067(6) C10 0.0246(8) 0.0194(8) 0.0324(9) 0.0082(7) -0.0034(7) 0.0013(6) N11 0.0177(6) 0.0172(6) 0.0214(6) -0.0002(5) 0.0044(5) 0.0003(5) C12 0.0160(7) 0.0128(6) 0.0212(7) 0.0047(6) 0.0017(5) 0.0002(5) O13 0.0154(5) 0.0217(5) 0.0217(5) 0.0007(4) 0.0037(4) -0.0003(4) C14 0.0207(7) 0.0199(7) 0.0184(7) 0.0052(6) 0.0006(6) -0.0006(6) O 0.0199(6) 0.0398(7) 0.0245(6) 0.0016(5) 0.0003(5) -0.0067(5) C15 0.0216(7) 0.0160(7) 0.0184(7) 0.0041(6) 0.0024(6) 0.0004(6) C16 0.0200(7) 0.0134(7) 0.0193(7) 0.0029(5) 0.0031(6) 0.0021(5) C17 0.0289(8) 0.0208(8) 0.0217(8) 0.0014(6) 0.0012(6) -0.0043(6) C18 0.0412(10) 0.0182(8) 0.0218(8) -0.0013(6) 0.0066(7) 0.0008(7) C19 0.0314(9) 0.0224(8) 0.0247(8) 0.0024(6) 0.0111(7) 0.0069(7) C20 0.0213(7) 0.0219(7) 0.0249(8) 0.0014(6) 0.0060(6) 0.0023(6) _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 Fe C1 2.0331(15) . ? Fe C2 2.0370(15) . ? Fe C9 2.0419(16) . ? Fe C10 2.0423(16) . ? Fe C5 2.0425(15) . ? Fe C8 2.0439(16) . ? Fe C7 2.0474(15) . ? Fe C6 2.0483(16) . ? Fe C3 2.0535(16) . ? Fe C4 2.0567(15) . ? C1 C2 1.436(2) . ? C1 C5 1.438(2) . ? C1 C12 1.451(2) . ? C2 C3 1.421(2) . ? C2 H2 0.9500 . ? C3 C4 1.421(2) . ? C3 H3 0.9500 . ? C4 C5 1.420(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.419(2) . ? C6 C7 1.421(2) . ? C6 H6 0.9500 . ? C7 C8 1.419(2) . ? C7 H7 0.9500 . ? C8 C9 1.424(2) . ? C8 H8 0.9500 . ? C9 C10 1.420(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N11 C12 1.2793(19) . ? N11 C16 1.395(2) . ? C12 O13 1.3789(17) . ? O13 C14 1.3900(19) . ? C14 O 1.1984(19) . ? C14 C15 1.460(2) . ? C15 C17 1.398(2) . ? C15 C16 1.401(2) . ? C16 C20 1.401(2) . ? C17 C18 1.379(2) . ? C17 H17 0.9500 . ? C18 C19 1.399(3) . ? C18 H18 0.9500 . ? C19 C20 1.380(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C2 41.32(6) . . ? C1 Fe C9 157.44(7) . . ? C2 Fe C9 159.87(7) . . ? C1 Fe C10 121.81(7) . . ? C2 Fe C10 157.78(7) . . ? C9 Fe C10 40.69(7) . . ? C1 Fe C5 41.32(6) . . ? C2 Fe C5 69.36(6) . . ? C9 Fe C5 121.29(7) . . ? C10 Fe C5 107.47(7) . . ? C1 Fe C8 160.33(7) . . ? C2 Fe C8 123.17(7) . . ? C9 Fe C8 40.78(7) . . ? C10 Fe C8 68.47(7) . . ? C5 Fe C8 156.87(7) . . ? C1 Fe C7 123.92(6) . . ? C2 Fe C7 107.19(6) . . ? C9 Fe C7 68.38(7) . . ? C10 Fe C7 68.29(7) . . ? C5 Fe C7 161.05(7) . . ? C8 Fe C7 40.57(7) . . ? C1 Fe C6 107.54(6) . . ? C2 Fe C6 121.87(7) . . ? C9 Fe C6 68.40(7) . . ? C10 Fe C6 40.58(7) . . ? C5 Fe C6 124.27(7) . . ? C8 Fe C6 68.39(7) . . ? C7 Fe C6 40.61(7) . . ? C1 Fe C3 68.70(6) . . ? C2 Fe C3 40.66(6) . . ? C9 Fe C3 123.66(7) . . ? C10 Fe C3 160.34(7) . . ? C5 Fe C3 68.47(6) . . ? C8 Fe C3 107.27(7) . . ? C7 Fe C3 121.80(7) . . ? C6 Fe C3 157.51(7) . . ? C1 Fe C4 68.70(6) . . ? C2 Fe C4 68.61(6) . . ? C9 Fe C4 107.40(7) . . ? C10 Fe C4 124.10(7) . . ? C5 Fe C4 40.53(6) . . ? C8 Fe C4 121.55(7) . . ? C7 Fe C4 157.12(7) . . ? C6 Fe C4 160.75(7) . . ? C3 Fe C4 40.46(7) . . ? C2 C1 C5 107.73(13) . . ? C2 C1 C12 125.56(13) . . ? C5 C1 C12 126.65(14) . . ? C2 C1 Fe 69.49(8) . . ? C5 C1 Fe 69.69(8) . . ? C12 C1 Fe 124.15(10) . . ? C3 C2 C1 107.63(13) . . ? C3 C2 Fe 70.29(9) . . ? C1 C2 Fe 69.20(8) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? Fe C2 H2 125.9 . . ? C2 C3 C4 108.53(14) . . ? C2 C3 Fe 69.05(9) . . ? C4 C3 Fe 69.89(9) . . ? C2 C3 H3 125.7 . . ? C4 C3 H3 125.7 . . ? Fe C3 H3 126.9 . . ? C5 C4 C3 108.40(14) . . ? C5 C4 Fe 69.20(9) . . ? C3 C4 Fe 69.65(9) . . ? C5 C4 H4 125.8 . . ? C3 C4 H4 125.8 . . ? Fe C4 H4 126.9 . . ? C4 C5 C1 107.70(14) . . ? C4 C5 Fe 70.27(9) . . ? C1 C5 Fe 68.99(8) . . ? C4 C5 H5 126.2 . . ? C1 C5 H5 126.2 . . ? Fe C5 H5 126.2 . . ? C10 C6 C7 107.87(15) . . ? C10 C6 Fe 69.48(9) . . ? C7 C6 Fe 69.66(9) . . ? C10 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe C6 H6 126.4 . . ? C8 C7 C6 108.17(15) . . ? C8 C7 Fe 69.58(9) . . ? C6 C7 Fe 69.73(9) . . ? C8 C7 H7 125.9 . . ? C6 C7 H7 125.9 . . ? Fe C7 H7 126.4 . . ? C7 C8 C9 107.89(15) . . ? C7 C8 Fe 69.85(9) . . ? C9 C8 Fe 69.53(9) . . ? C7 C8 H8 126.1 . . ? C9 C8 H8 126.1 . . ? Fe C8 H8 126.1 . . ? C10 C9 C8 107.89(15) . . ? C10 C9 Fe 69.67(9) . . ? C8 C9 Fe 69.68(9) . . ? C10 C9 H9 126.1 . . ? C8 C9 H9 126.1 . . ? Fe C9 H9 126.2 . . ? C6 C10 C9 108.18(15) . . ? C6 C10 Fe 69.93(9) . . ? C9 C10 Fe 69.64(9) . . ? C6 C10 H10 125.9 . . ? C9 C10 H10 125.9 . . ? Fe C10 H10 126.1 . . ? C12 N11 C16 117.51(13) . . ? N11 C12 O13 125.47(14) . . ? N11 C12 C1 122.97(14) . . ? O13 C12 C1 111.54(12) . . ? C12 O13 C14 121.07(12) . . ? O C14 O13 117.40(14) . . ? O C14 C15 127.42(15) . . ? O13 C14 C15 115.18(13) . . ? C17 C15 C16 121.03(14) . . ? C17 C15 C14 120.15(14) . . ? C16 C15 C14 118.78(14) . . ? N11 C16 C15 121.92(14) . . ? N11 C16 C20 119.15(14) . . ? C15 C16 C20 118.90(14) . . ? C18 C17 C15 119.30(15) . . ? C18 C17 H17 120.4 . . ? C15 C17 H17 120.4 . . ? C17 C18 C19 120.02(15) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 120.98(15) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C16 119.74(15) . . ? C19 C20 H20 120.1 . . ? C16 C20 H20 120.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.052 data_kh8a _database_code_depnum_ccdc_archive 'CCDC 922137' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Fe N S2' _chemical_formula_sum 'C18 H13 Fe N S2' _chemical_formula_weight 363.26 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3774(3) _cell_length_b 9.9499(4) _cell_length_c 10.5660(4) _cell_angle_alpha 87.4510(10) _cell_angle_beta 79.7700(10) _cell_angle_gamma 74.6700(10) _cell_volume 736.10(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4498 _cell_measurement_theta_min 5.81 _cell_measurement_theta_max 55.12 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 1.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9376 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3375 _reflns_number_gt 2944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0424P)^2^+0.3148P] 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 3375 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Fe Fe 0.45556(4) 0.34639(3) 0.25077(2) 0.01371(9) Uani 1 1 d . . . S13 S 0.29308(8) 0.32986(6) 0.62899(5) 0.02499(13) Uani 1 1 d . . . S S 0.27877(9) 0.24750(6) 0.89268(5) 0.02942(14) Uani 1 1 d . . . N11 N 0.0460(2) 0.24351(16) 0.50941(15) 0.0177(3) Uani 1 1 d . . . C1 C 0.2156(3) 0.39321(19) 0.38861(18) 0.0163(4) Uani 1 1 d . . . C2 C 0.1672(3) 0.3777(2) 0.26561(18) 0.0185(4) Uani 1 1 d . . . H2 H 0.1038 0.3124 0.2443 0.022 Uiso 1 1 calc R . . C3 C 0.2306(3) 0.4774(2) 0.18112(19) 0.0211(4) Uani 1 1 d . . . H3 H 0.2158 0.4908 0.0936 0.025 Uiso 1 1 calc R . . C4 C 0.3200(3) 0.5537(2) 0.24976(19) 0.0204(4) Uani 1 1 d . . . H4 H 0.3754 0.6265 0.2158 0.024 Uiso 1 1 calc R . . C5 C 0.3123(3) 0.50252(19) 0.37789(18) 0.0179(4) Uani 1 1 d . . . H5 H 0.3619 0.5346 0.4444 0.022 Uiso 1 1 calc R . . C6 C 0.6321(3) 0.1575(2) 0.2871(2) 0.0217(4) Uani 1 1 d . . . H6 H 0.6057 0.0958 0.3549 0.026 Uiso 1 1 calc R . . C7 C 0.5868(3) 0.1581(2) 0.1615(2) 0.0232(4) Uani 1 1 d . . . H7 H 0.5259 0.0964 0.1304 0.028 Uiso 1 1 calc R . . C8 C 0.6486(3) 0.2672(2) 0.09105(19) 0.0234(4) Uani 1 1 d . . . H8 H 0.6356 0.2917 0.0046 0.028 Uiso 1 1 calc R . . C9 C 0.7333(3) 0.3334(2) 0.1718(2) 0.0224(4) Uani 1 1 d . . . H9 H 0.7871 0.4098 0.1488 0.027 Uiso 1 1 calc R . . C10 C 0.7238(3) 0.2657(2) 0.2932(2) 0.0213(4) Uani 1 1 d . . . H10 H 0.7704 0.2885 0.3655 0.026 Uiso 1 1 calc R . . C12 C 0.1706(3) 0.31413(19) 0.50397(18) 0.0163(4) Uani 1 1 d . . . C14 C 0.1961(3) 0.2416(2) 0.75789(19) 0.0186(4) Uani 1 1 d . . . C15 C 0.0547(3) 0.17010(18) 0.73857(18) 0.0165(4) Uani 1 1 d . . . C16 C -0.0087(3) 0.17227(19) 0.62003(18) 0.0164(4) Uani 1 1 d . . . C17 C -0.0220(3) 0.0961(2) 0.84209(19) 0.0202(4) Uani 1 1 d . . . H17 H 0.0188 0.0950 0.9226 0.024 Uiso 1 1 calc R . . C18 C -0.1545(3) 0.0253(2) 0.8290(2) 0.0237(4) Uani 1 1 d . . . H18 H -0.2040 -0.0246 0.8996 0.028 Uiso 1 1 calc R . . C19 C -0.2157(3) 0.0275(2) 0.7109(2) 0.0255(4) Uani 1 1 d . . . H19 H -0.3063 -0.0220 0.7010 0.031 Uiso 1 1 calc R . . C20 C -0.1460(3) 0.1004(2) 0.60937(19) 0.0214(4) Uani 1 1 d . . . H20 H -0.1911 0.1026 0.5303 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.01325(14) 0.01537(15) 0.01300(15) 0.00161(10) -0.00251(10) -0.00468(10) S13 0.0287(3) 0.0357(3) 0.0190(3) 0.0087(2) -0.0088(2) -0.0213(2) S 0.0412(3) 0.0370(3) 0.0201(3) 0.0082(2) -0.0138(2) -0.0233(3) N11 0.0189(8) 0.0193(8) 0.0158(8) 0.0019(6) -0.0025(6) -0.0070(7) C1 0.0132(9) 0.0177(9) 0.0165(9) -0.0008(7) -0.0005(7) -0.0026(7) C2 0.0118(9) 0.0229(10) 0.0206(10) 0.0019(8) -0.0039(7) -0.0036(7) C3 0.0187(10) 0.0239(10) 0.0189(10) 0.0061(8) -0.0055(8) -0.0022(8) C4 0.0217(10) 0.0164(9) 0.0210(10) 0.0038(7) -0.0020(8) -0.0030(8) C5 0.0211(9) 0.0152(9) 0.0167(9) -0.0002(7) -0.0008(7) -0.0050(8) C6 0.0171(9) 0.0185(10) 0.0261(11) 0.0036(8) -0.0020(8) -0.0005(8) C7 0.0217(10) 0.0213(10) 0.0258(11) -0.0062(8) -0.0013(8) -0.0051(8) C8 0.0217(10) 0.0309(11) 0.0148(9) -0.0018(8) 0.0019(8) -0.0050(9) C9 0.0151(9) 0.0272(11) 0.0247(11) 0.0024(8) 0.0006(8) -0.0082(8) C10 0.0148(9) 0.0259(10) 0.0228(10) 0.0011(8) -0.0054(8) -0.0037(8) C12 0.0152(9) 0.0169(9) 0.0161(9) -0.0006(7) -0.0024(7) -0.0029(7) C14 0.0205(10) 0.0173(9) 0.0176(9) 0.0023(7) -0.0033(8) -0.0047(8) C15 0.0160(9) 0.0137(9) 0.0179(9) -0.0012(7) -0.0008(7) -0.0021(7) C16 0.0159(9) 0.0149(9) 0.0170(9) -0.0004(7) 0.0000(7) -0.0033(7) C17 0.0209(10) 0.0207(10) 0.0186(10) 0.0035(8) -0.0041(8) -0.0048(8) C18 0.0259(11) 0.0254(11) 0.0203(10) 0.0065(8) 0.0004(8) -0.0117(9) C19 0.0253(11) 0.0268(11) 0.0275(11) 0.0007(9) -0.0025(9) -0.0140(9) C20 0.0236(10) 0.0245(10) 0.0186(10) 0.0000(8) -0.0032(8) -0.0106(8) _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 Fe C5 2.0366(19) . ? Fe C4 2.0412(19) . ? Fe C8 2.042(2) . ? Fe C9 2.0432(19) . ? Fe C1 2.0446(18) . ? Fe C2 2.0454(18) . ? Fe C6 2.0479(19) . ? Fe C3 2.0492(18) . ? Fe C10 2.0509(19) . ? Fe C7 2.052(2) . ? S13 C14 1.737(2) . ? S13 C12 1.7614(19) . ? S C14 1.655(2) . ? N11 C12 1.289(2) . ? N11 C16 1.393(2) . ? C1 C2 1.433(3) . ? C1 C5 1.441(3) . ? C1 C12 1.457(3) . ? C2 C3 1.421(3) . ? C2 H2 0.9500 . ? C3 C4 1.421(3) . ? C3 H3 0.9500 . ? C4 C5 1.422(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.424(3) . ? C6 C7 1.425(3) . ? C6 H6 0.9500 . ? C7 C8 1.418(3) . ? C7 H7 0.9500 . ? C8 C9 1.418(3) . ? C8 H8 0.9500 . ? C9 C10 1.422(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C14 C15 1.455(3) . ? C15 C17 1.410(3) . ? C15 C16 1.410(3) . ? C16 C20 1.407(3) . ? C17 C18 1.375(3) . ? C17 H17 0.9500 . ? C18 C19 1.398(3) . ? C18 H18 0.9500 . ? C19 C20 1.369(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 C5 Fe C4 40.82(8) . . ? C5 Fe C8 152.80(8) . . ? C4 Fe C8 117.19(8) . . ? C5 Fe C9 119.19(8) . . ? C4 Fe C9 105.12(8) . . ? C8 Fe C9 40.61(8) . . ? C5 Fe C1 41.34(7) . . ? C4 Fe C1 68.85(8) . . ? C8 Fe C1 162.86(8) . . ? C9 Fe C1 156.24(8) . . ? C5 Fe C2 69.26(8) . . ? C4 Fe C2 68.69(8) . . ? C8 Fe C2 123.94(8) . . ? C9 Fe C2 160.10(8) . . ? C1 Fe C2 41.01(7) . . ? C5 Fe C6 127.99(8) . . ? C4 Fe C6 163.61(8) . . ? C8 Fe C6 68.34(8) . . ? C9 Fe C6 68.37(8) . . ? C1 Fe C6 110.69(8) . . ? C2 Fe C6 122.47(8) . . ? C5 Fe C3 68.73(8) . . ? C4 Fe C3 40.66(8) . . ? C8 Fe C3 104.87(8) . . ? C9 Fe C3 122.63(8) . . ? C1 Fe C3 68.58(8) . . ? C2 Fe C3 40.61(8) . . ? C6 Fe C3 155.53(9) . . ? C5 Fe C10 108.55(8) . . ? C4 Fe C10 124.84(8) . . ? C8 Fe C10 68.34(8) . . ? C9 Fe C10 40.64(8) . . ? C1 Fe C10 122.89(8) . . ? C2 Fe C10 158.01(8) . . ? C6 Fe C10 40.65(8) . . ? C3 Fe C10 160.66(8) . . ? C5 Fe C7 165.64(8) . . ? C4 Fe C7 152.62(8) . . ? C8 Fe C7 40.52(8) . . ? C9 Fe C7 68.27(8) . . ? C1 Fe C7 127.57(8) . . ? C2 Fe C7 108.05(8) . . ? C6 Fe C7 40.66(8) . . ? C3 Fe C7 119.03(8) . . ? C10 Fe C7 68.34(8) . . ? C14 S13 C12 104.85(9) . . ? C12 N11 C16 121.94(16) . . ? C2 C1 C5 107.68(16) . . ? C2 C1 C12 125.76(17) . . ? C5 C1 C12 126.55(17) . . ? C2 C1 Fe 69.53(10) . . ? C5 C1 Fe 69.03(11) . . ? C12 C1 Fe 127.85(13) . . ? C3 C2 C1 107.87(17) . . ? C3 C2 Fe 69.84(11) . . ? C1 C2 Fe 69.47(10) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 126.2 . . ? C2 C3 C4 108.44(17) . . ? C2 C3 Fe 69.55(10) . . ? C4 C3 Fe 69.37(11) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe C3 H3 126.9 . . ? C3 C4 C5 108.41(18) . . ? C3 C4 Fe 69.97(11) . . ? C5 C4 Fe 69.42(11) . . ? C3 C4 H4 125.8 . . ? C5 C4 H4 125.8 . . ? Fe C4 H4 126.4 . . ? C4 C5 C1 107.59(17) . . ? C4 C5 Fe 69.76(11) . . ? C1 C5 Fe 69.63(10) . . ? C4 C5 H5 126.2 . . ? C1 C5 H5 126.2 . . ? Fe C5 H5 126.0 . . ? C10 C6 C7 108.02(18) . . ? C10 C6 Fe 69.79(11) . . ? C7 C6 Fe 69.83(11) . . ? C10 C6 H6 126.0 . . ? C7 C6 H6 126.0 . . ? Fe C6 H6 126.0 . . ? C8 C7 C6 107.82(18) . . ? C8 C7 Fe 69.35(11) . . ? C6 C7 Fe 69.51(11) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? Fe C7 H7 126.6 . . ? C9 C8 C7 108.29(18) . . ? C9 C8 Fe 69.75(11) . . ? C7 C8 Fe 70.13(12) . . ? C9 C8 H8 125.9 . . ? C7 C8 H8 125.9 . . ? Fe C8 H8 125.8 . . ? C8 C9 C10 108.11(18) . . ? C8 C9 Fe 69.64(11) . . ? C10 C9 Fe 69.97(11) . . ? C8 C9 H9 125.9 . . ? C10 C9 H9 125.9 . . ? Fe C9 H9 126.0 . . ? C9 C10 C6 107.77(18) . . ? C9 C10 Fe 69.39(11) . . ? C6 C10 Fe 69.56(11) . . ? C9 C10 H10 126.1 . . ? C6 C10 H10 126.1 . . ? Fe C10 H10 126.5 . . ? N11 C12 C1 119.96(17) . . ? N11 C12 S13 125.48(15) . . ? C1 C12 S13 114.53(14) . . ? C15 C14 S 126.46(15) . . ? C15 C14 S13 118.57(14) . . ? S C14 S13 114.97(11) . . ? C17 C15 C16 118.74(18) . . ? C17 C15 C14 118.88(17) . . ? C16 C15 C14 122.39(17) . . ? N11 C16 C20 114.53(17) . . ? N11 C16 C15 126.60(17) . . ? C20 C16 C15 118.83(17) . . ? C18 C17 C15 121.40(18) . . ? C18 C17 H17 119.3 . . ? C15 C17 H17 119.3 . . ? C17 C18 C19 119.43(19) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 120.41(19) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C16 121.18(19) . . ? C19 C20 H20 119.4 . . ? C16 C20 H20 119.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.517 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.073 data_kh8b _database_code_depnum_ccdc_archive 'CCDC 922138' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Fe N O S' _chemical_formula_sum 'C18 H13 Fe N O S' _chemical_formula_weight 347.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 13.1577(14) _cell_length_b 8.6907(9) _cell_length_c 13.8343(16) _cell_angle_alpha 90.00 _cell_angle_beta 114.783(3) _cell_angle_gamma 90.00 _cell_volume 1436.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6592 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.35 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 1.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_T_max 0.777 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12897 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3127 _reflns_number_gt 2630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0767P)^2^+0.9225P] 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 3127 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 Fe Fe 0.36201(3) 0.62944(4) 0.11026(3) 0.02235(15) Uani 1 1 d . . . S13 S 0.19970(6) 1.02353(9) 0.10151(6) 0.0324(2) Uani 1 1 d . . . O O 0.02934(18) 1.2026(3) 0.01875(19) 0.0438(6) Uani 1 1 d . . . N11 N 0.29472(17) 1.0107(3) -0.03991(17) 0.0243(5) Uani 1 1 d . . . C1 C 0.3816(2) 0.8611(3) 0.1179(2) 0.0243(5) Uani 1 1 d . . . C2 C 0.4639(2) 0.7904(3) 0.0898(2) 0.0268(6) Uani 1 1 d . . . H2 H 0.4741 0.8085 0.0267 0.032 Uiso 1 1 calc R . . C3 C 0.5278(2) 0.6882(3) 0.1738(2) 0.0320(6) Uani 1 1 d . . . H3 H 0.5878 0.6253 0.1760 0.038 Uiso 1 1 calc R . . C4 C 0.4868(2) 0.6957(3) 0.2536(2) 0.0308(6) Uani 1 1 d . . . H4 H 0.5153 0.6401 0.3187 0.037 Uiso 1 1 calc R . . C5 C 0.3959(2) 0.8009(3) 0.2193(2) 0.0283(6) Uani 1 1 d . . . H5 H 0.3522 0.8269 0.2569 0.034 Uiso 1 1 calc R . . C6 C 0.2048(2) 0.5799(4) -0.0039(3) 0.0380(7) Uani 1 1 d . . . H6 H 0.1502 0.6515 -0.0473 0.046 Uiso 1 1 calc R . . C7 C 0.2887(3) 0.5084(4) -0.0287(2) 0.0381(7) Uani 1 1 d . . . H7 H 0.3002 0.5244 -0.0913 0.046 Uiso 1 1 calc R . . C8 C 0.3517(2) 0.4093(3) 0.0567(2) 0.0330(6) Uani 1 1 d . . . H8 H 0.4129 0.3470 0.0613 0.040 Uiso 1 1 calc R . . C9 C 0.3079(2) 0.4189(3) 0.1341(2) 0.0330(6) Uani 1 1 d . . . H9 H 0.3340 0.3642 0.1995 0.040 Uiso 1 1 calc R . . C10 C 0.2177(2) 0.5253(4) 0.0962(3) 0.0383(7) Uani 1 1 d . . . H10 H 0.1734 0.5546 0.1325 0.046 Uiso 1 1 calc R . . C12 C 0.2951(2) 0.9675(3) 0.0485(2) 0.0232(5) Uani 1 1 d . . . C14 C 0.1059(2) 1.1484(3) 0.0022(2) 0.0315(6) Uani 1 1 d . . . C15 C 0.1263(2) 1.1801(3) -0.0914(2) 0.0272(6) Uani 1 1 d . . . C16 C 0.2157(2) 1.1131(3) -0.1081(2) 0.0235(5) Uani 1 1 d . . . C17 C 0.0563(2) 1.2859(3) -0.1659(2) 0.0337(6) Uani 1 1 d . . . H17 H -0.0037 1.3312 -0.1548 0.040 Uiso 1 1 calc R . . C18 C 0.0724(2) 1.3259(4) -0.2546(2) 0.0351(7) Uani 1 1 d . . . H18 H 0.0245 1.3989 -0.3037 0.042 Uiso 1 1 calc R . . C19 C 0.1595(2) 1.2587(3) -0.2723(2) 0.0321(6) Uani 1 1 d . . . H19 H 0.1709 1.2856 -0.3336 0.038 Uiso 1 1 calc R . . C20 C 0.2287(2) 1.1530(3) -0.2005(2) 0.0273(6) Uani 1 1 d . . . H20 H 0.2868 1.1061 -0.2139 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.0147(2) 0.0222(2) 0.0262(2) -0.00073(14) 0.00468(16) -0.00082(13) S13 0.0267(4) 0.0377(4) 0.0367(4) 0.0020(3) 0.0172(3) 0.0038(3) O 0.0280(11) 0.0531(14) 0.0547(14) -0.0013(12) 0.0216(10) 0.0093(10) N11 0.0156(9) 0.0245(11) 0.0294(11) -0.0020(9) 0.0061(8) -0.0005(8) C1 0.0185(11) 0.0181(13) 0.0334(14) -0.0022(10) 0.0081(10) -0.0023(9) C2 0.0145(11) 0.0292(14) 0.0332(14) -0.0008(11) 0.0065(10) -0.0028(10) C3 0.0163(12) 0.0306(15) 0.0411(16) 0.0020(12) 0.0043(11) 0.0003(11) C4 0.0246(13) 0.0298(15) 0.0269(13) -0.0012(11) -0.0003(10) -0.0026(11) C5 0.0271(13) 0.0268(14) 0.0267(13) -0.0065(11) 0.0070(11) -0.0035(11) C6 0.0203(13) 0.0273(15) 0.0463(17) 0.0008(13) -0.0056(12) -0.0037(11) C7 0.0433(17) 0.0340(16) 0.0292(14) -0.0073(12) 0.0074(12) -0.0125(13) C8 0.0271(14) 0.0245(14) 0.0417(16) -0.0063(12) 0.0088(12) -0.0006(11) C9 0.0272(14) 0.0243(14) 0.0413(16) 0.0034(12) 0.0083(12) -0.0039(11) C10 0.0208(13) 0.0368(17) 0.0565(19) -0.0015(14) 0.0153(13) -0.0061(12) C12 0.0151(11) 0.0213(13) 0.0300(13) -0.0044(10) 0.0062(10) -0.0029(9) C14 0.0181(12) 0.0315(15) 0.0414(16) -0.0057(12) 0.0090(11) -0.0016(11) C15 0.0143(11) 0.0258(14) 0.0354(14) -0.0053(11) 0.0043(10) -0.0021(10) C16 0.0148(11) 0.0205(12) 0.0293(13) -0.0038(10) 0.0035(10) -0.0031(9) C17 0.0170(12) 0.0315(15) 0.0430(16) -0.0043(13) 0.0031(11) 0.0022(11) C18 0.0241(14) 0.0281(15) 0.0364(15) 0.0006(12) -0.0036(11) 0.0026(11) C19 0.0290(14) 0.0284(15) 0.0292(14) -0.0001(11) 0.0028(11) -0.0031(12) C20 0.0219(12) 0.0258(14) 0.0294(13) -0.0016(11) 0.0061(10) -0.0018(10) _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 Fe C1 2.027(3) . ? Fe C5 2.032(3) . ? Fe C8 2.035(3) . ? Fe C10 2.038(3) . ? Fe C2 2.038(3) . ? Fe C9 2.040(3) . ? Fe C7 2.044(3) . ? Fe C3 2.045(3) . ? Fe C6 2.054(3) . ? Fe C4 2.057(3) . ? S13 C12 1.767(3) . ? S13 C14 1.779(3) . ? O C14 1.218(4) . ? N11 C12 1.277(3) . ? N11 C16 1.393(3) . ? C1 C5 1.433(4) . ? C1 C2 1.435(4) . ? C1 C12 1.468(4) . ? C2 C3 1.424(4) . ? C2 H2 0.9500 . ? C3 C4 1.419(4) . ? C3 H3 0.9500 . ? C4 C5 1.420(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.406(5) . ? C6 C7 1.428(5) . ? C6 H6 0.9500 . ? C7 C8 1.415(4) . ? C7 H7 0.9500 . ? C8 C9 1.416(4) . ? C8 H8 0.9500 . ? C9 C10 1.419(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C14 C15 1.455(4) . ? C15 C17 1.399(4) . ? C15 C16 1.416(4) . ? C16 C20 1.402(4) . ? C17 C18 1.375(5) . ? C17 H17 0.9500 . ? C18 C19 1.396(4) . ? C18 H18 0.9500 . ? C19 C20 1.379(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C5 41.34(11) . . ? C1 Fe C8 160.11(12) . . ? C5 Fe C8 156.89(12) . . ? C1 Fe C10 122.61(12) . . ? C5 Fe C10 107.59(12) . . ? C8 Fe C10 68.32(12) . . ? C1 Fe C2 41.33(10) . . ? C5 Fe C2 69.36(11) . . ? C8 Fe C2 122.81(12) . . ? C10 Fe C2 158.86(12) . . ? C1 Fe C9 158.08(12) . . ? C5 Fe C9 121.36(12) . . ? C8 Fe C9 40.66(13) . . ? C10 Fe C9 40.74(12) . . ? C2 Fe C9 158.89(12) . . ? C1 Fe C7 124.06(12) . . ? C5 Fe C7 161.01(13) . . ? C8 Fe C7 40.60(12) . . ? C10 Fe C7 68.18(14) . . ? C2 Fe C7 107.52(12) . . ? C9 Fe C7 68.37(13) . . ? C1 Fe C3 68.94(11) . . ? C5 Fe C3 68.63(12) . . ? C8 Fe C3 106.69(12) . . ? C10 Fe C3 159.23(13) . . ? C2 Fe C3 40.81(11) . . ? C9 Fe C3 122.43(12) . . ? C7 Fe C3 122.02(13) . . ? C1 Fe C6 108.26(12) . . ? C5 Fe C6 124.15(13) . . ? C8 Fe C6 68.34(12) . . ? C10 Fe C6 40.18(13) . . ? C2 Fe C6 123.10(12) . . ? C9 Fe C6 68.22(12) . . ? C7 Fe C6 40.78(13) . . ? C3 Fe C6 158.65(14) . . ? C1 Fe C4 68.82(11) . . ? C5 Fe C4 40.63(11) . . ? C8 Fe C4 121.24(12) . . ? C10 Fe C4 123.49(13) . . ? C2 Fe C4 68.64(11) . . ? C9 Fe C4 106.69(12) . . ? C7 Fe C4 157.23(13) . . ? C3 Fe C4 40.47(12) . . ? C6 Fe C4 160.01(13) . . ? C12 S13 C14 103.35(13) . . ? C12 N11 C16 122.6(2) . . ? C5 C1 C2 107.8(2) . . ? C5 C1 C12 128.2(2) . . ? C2 C1 C12 123.9(2) . . ? C5 C1 Fe 69.55(15) . . ? C2 C1 Fe 69.77(15) . . ? C12 C1 Fe 123.01(18) . . ? C3 C2 C1 107.5(2) . . ? C3 C2 Fe 69.85(15) . . ? C1 C2 Fe 68.89(14) . . ? C3 C2 H2 126.3 . . ? C1 C2 H2 126.3 . . ? Fe C2 H2 126.5 . . ? C4 C3 C2 108.7(2) . . ? C4 C3 Fe 70.21(15) . . ? C2 C3 Fe 69.34(14) . . ? C4 C3 H3 125.7 . . ? C2 C3 H3 125.7 . . ? Fe C3 H3 126.4 . . ? C3 C4 C5 108.1(2) . . ? C3 C4 Fe 69.32(16) . . ? C5 C4 Fe 68.76(15) . . ? C3 C4 H4 125.9 . . ? C5 C4 H4 125.9 . . ? Fe C4 H4 127.6 . . ? C4 C5 C1 108.0(2) . . ? C4 C5 Fe 70.61(16) . . ? C1 C5 Fe 69.11(15) . . ? C4 C5 H5 126.0 . . ? C1 C5 H5 126.0 . . ? Fe C5 H5 125.9 . . ? C10 C6 C7 107.7(3) . . ? C10 C6 Fe 69.31(16) . . ? C7 C6 Fe 69.26(16) . . ? C10 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe C6 H6 126.8 . . ? C8 C7 C6 107.8(3) . . ? C8 C7 Fe 69.36(17) . . ? C6 C7 Fe 69.96(17) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? Fe C7 H7 126.1 . . ? C7 C8 C9 108.3(3) . . ? C7 C8 Fe 70.04(17) . . ? C9 C8 Fe 69.83(17) . . ? C7 C8 H8 125.9 . . ? C9 C8 H8 125.9 . . ? Fe C8 H8 125.9 . . ? C8 C9 C10 107.6(3) . . ? C8 C9 Fe 69.51(17) . . ? C10 C9 Fe 69.58(17) . . ? C8 C9 H9 126.2 . . ? C10 C9 H9 126.2 . . ? Fe C9 H9 126.3 . . ? C6 C10 C9 108.7(3) . . ? C6 C10 Fe 70.50(16) . . ? C9 C10 Fe 69.68(16) . . ? C6 C10 H10 125.7 . . ? C9 C10 H10 125.7 . . ? Fe C10 H10 125.7 . . ? N11 C12 C1 120.2(2) . . ? N11 C12 S13 126.7(2) . . ? C1 C12 S13 113.09(19) . . ? O C14 C15 124.7(3) . . ? O C14 S13 116.8(2) . . ? C15 C14 S13 118.4(2) . . ? C17 C15 C16 119.1(3) . . ? C17 C15 C14 118.0(3) . . ? C16 C15 C14 122.9(3) . . ? N11 C16 C20 115.7(2) . . ? N11 C16 C15 126.0(2) . . ? C20 C16 C15 118.3(2) . . ? C18 C17 C15 121.5(3) . . ? C18 C17 H17 119.2 . . ? C15 C17 H17 119.2 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 119.7(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C16 121.7(3) . . ? C19 C20 H20 119.2 . . ? C16 C20 H20 119.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.922 _refine_diff_density_min -1.184 _refine_diff_density_rms 0.111 data_kh6 _database_code_depnum_ccdc_archive 'CCDC 922139' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Fe N3 O2' _chemical_formula_sum 'C18 H17 Fe N3 O2' _chemical_formula_weight 363.20 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' 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 C2/c 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 16.2896(4) _cell_length_b 12.4546(3) _cell_length_c 16.4543(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.7190(10) _cell_angle_gamma 90.00 _cell_volume 3101.27(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9960 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.997 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6721 _exptl_absorpt_correction_T_max 0.7973 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25230 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3570 _reflns_number_gt 3316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0323P)^2^+2.7854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3570 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Fe Fe 0.146050(11) -0.054473(13) 0.216147(11) 0.01660(6) Uani 1 1 d . . . O1 O 0.39628(6) -0.11744(8) 0.29084(6) 0.0267(2) Uani 1 1 d . . . O2 O 0.31895(6) 0.17240(8) 0.45782(6) 0.0266(2) Uani 1 1 d . . . N1 N 0.37225(6) 0.02178(9) 0.37039(7) 0.0197(2) Uani 1 1 d . . . H1N H 0.3348 0.0509 0.3883 0.024 Uiso 1 1 d R . . N2 N 0.42827(7) 0.21334(9) 0.58509(7) 0.0216(2) Uani 1 1 d . . . H2N H 0.4838 0.2088 0.6191 0.026 Uiso 1 1 d R . . N3 N 0.37077(7) 0.24964(10) 0.62604(7) 0.0247(2) Uani 1 1 d . . . H3N H 0.3158 0.2589 0.5798 0.030 Uiso 1 1 d R . . H4N H 0.3650 0.1962 0.6593 0.030 Uiso 1 1 d R . . C1 C 0.25903(8) -0.10892(10) 0.30895(8) 0.0191(2) Uani 1 1 d . . . C2 C 0.21550(8) -0.19393(10) 0.24977(8) 0.0213(2) Uani 1 1 d . . . H2 H 0.2394 -0.2337 0.2144 0.026 Uiso 1 1 calc R . . C3 C 0.13055(8) -0.20797(10) 0.25342(8) 0.0227(3) Uani 1 1 d . . . H3 H 0.0876 -0.2589 0.2207 0.027 Uiso 1 1 calc R . . C4 C 0.12063(8) -0.13299(10) 0.31424(8) 0.0220(2) Uani 1 1 d . . . H4 H 0.0700 -0.1256 0.3293 0.026 Uiso 1 1 calc R . . C5 C 0.19918(8) -0.07099(10) 0.34876(8) 0.0203(2) Uani 1 1 d . . . H5 H 0.2102 -0.0148 0.3905 0.024 Uiso 1 1 calc R . . C6 C 0.17996(9) 0.06833(11) 0.15239(10) 0.0287(3) Uani 1 1 d . . . H6 H 0.2376 0.0967 0.1658 0.034 Uiso 1 1 calc R . . C7 C 0.14141(12) -0.01805(13) 0.09405(9) 0.0363(3) Uani 1 1 d . . . H7 H 0.1687 -0.0574 0.0614 0.044 Uiso 1 1 calc R . . C8 C 0.05508(11) -0.03495(12) 0.09338(10) 0.0369(4) Uani 1 1 d . . . H8 H 0.0146 -0.0881 0.0604 0.044 Uiso 1 1 calc R . . C9 C 0.03964(9) 0.04087(11) 0.15015(10) 0.0307(3) Uani 1 1 d . . . H9 H -0.0131 0.0480 0.1616 0.037 Uiso 1 1 calc R . . C10 C 0.11708(8) 0.10448(10) 0.18694(9) 0.0250(3) Uani 1 1 d . . . H10 H 0.1253 0.1614 0.2276 0.030 Uiso 1 1 calc R . . C11 C 0.34820(8) -0.06904(10) 0.32159(8) 0.0191(2) Uani 1 1 d . . . C21 C 0.45468(8) 0.07358(10) 0.40214(8) 0.0180(2) Uani 1 1 d . . . C22 C 0.46937(7) 0.15249(10) 0.46748(8) 0.0178(2) Uani 1 1 d . . . C23 C 0.55052(8) 0.20616(11) 0.49922(8) 0.0235(3) Uani 1 1 d . . . H23 H 0.5602 0.2605 0.5423 0.028 Uiso 1 1 calc R . . C24 C 0.61699(9) 0.18140(12) 0.46899(10) 0.0302(3) Uani 1 1 d . . . H24 H 0.6720 0.2181 0.4913 0.036 Uiso 1 1 calc R . . C25 C 0.60247(9) 0.10275(12) 0.40597(10) 0.0307(3) Uani 1 1 d . . . H25 H 0.6483 0.0850 0.3856 0.037 Uiso 1 1 calc R . . C26 C 0.52230(9) 0.04932(11) 0.37193(9) 0.0240(3) Uani 1 1 d . . . H26 H 0.5133 -0.0038 0.3280 0.029 Uiso 1 1 calc R . . C27 C 0.39924(8) 0.17946(9) 0.50280(8) 0.0181(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.01642(9) 0.01387(9) 0.01550(10) -0.00024(6) 0.00124(7) 0.00143(6) O1 0.0218(4) 0.0319(5) 0.0261(5) -0.0078(4) 0.0086(4) 0.0052(4) O2 0.0158(4) 0.0343(5) 0.0255(5) -0.0087(4) 0.0027(3) 0.0052(4) N1 0.0161(4) 0.0218(5) 0.0210(5) -0.0027(4) 0.0066(4) 0.0035(4) N2 0.0169(5) 0.0260(5) 0.0199(5) -0.0021(4) 0.0045(4) 0.0026(4) N3 0.0234(5) 0.0297(6) 0.0216(5) -0.0029(4) 0.0089(4) 0.0040(4) C1 0.0181(5) 0.0196(6) 0.0163(5) 0.0004(4) 0.0024(4) 0.0057(4) C2 0.0236(6) 0.0161(5) 0.0214(6) -0.0001(5) 0.0050(5) 0.0060(4) C3 0.0250(6) 0.0157(6) 0.0237(6) 0.0019(5) 0.0046(5) 0.0009(4) C4 0.0213(6) 0.0219(6) 0.0217(6) 0.0024(5) 0.0066(5) 0.0022(5) C5 0.0196(6) 0.0234(6) 0.0154(5) -0.0009(5) 0.0037(4) 0.0038(5) C6 0.0277(7) 0.0272(7) 0.0319(7) 0.0087(6) 0.0120(6) 0.0015(5) C7 0.0563(9) 0.0319(8) 0.0197(7) 0.0054(6) 0.0129(6) 0.0078(7) C8 0.0422(8) 0.0274(7) 0.0217(7) 0.0071(6) -0.0109(6) -0.0053(6) C9 0.0184(6) 0.0243(7) 0.0403(8) 0.0146(6) 0.0001(5) 0.0027(5) C10 0.0243(6) 0.0149(6) 0.0333(7) 0.0051(5) 0.0077(5) 0.0020(5) C11 0.0182(5) 0.0217(6) 0.0144(5) 0.0011(4) 0.0024(4) 0.0062(4) C21 0.0169(5) 0.0184(5) 0.0178(5) 0.0066(4) 0.0055(4) 0.0042(4) C22 0.0166(5) 0.0178(5) 0.0176(5) 0.0054(4) 0.0047(4) 0.0028(4) C23 0.0222(6) 0.0233(6) 0.0224(6) 0.0055(5) 0.0050(5) -0.0022(5) C24 0.0204(6) 0.0360(8) 0.0345(7) 0.0098(6) 0.0104(5) -0.0054(5) C25 0.0248(6) 0.0368(8) 0.0372(8) 0.0106(6) 0.0196(6) 0.0033(6) C26 0.0260(6) 0.0260(6) 0.0241(6) 0.0064(5) 0.0139(5) 0.0049(5) C27 0.0179(5) 0.0144(5) 0.0205(6) 0.0010(4) 0.0052(4) 0.0023(4) _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 Fe C1 2.0245(11) . ? Fe C8 2.0299(13) . ? Fe C7 2.0336(14) . ? Fe C2 2.0346(12) . ? Fe C5 2.0383(12) . ? Fe C6 2.0431(14) . ? Fe C9 2.0496(13) . ? Fe C10 2.0506(13) . ? Fe C3 2.0517(12) . ? Fe C4 2.0561(13) . ? O1 C11 1.2354(15) . ? O2 C27 1.2449(15) . ? N1 C11 1.3582(16) . ? N1 C21 1.4045(16) . ? N1 H1N 0.8518 . ? N2 C27 1.3270(16) . ? N2 N3 1.4154(14) . ? N2 H2N 0.8715 . ? N3 H3N 0.9434 . ? N3 H4N 0.8884 . ? C1 C2 1.4355(17) . ? C1 C5 1.4406(16) . ? C1 C11 1.4753(17) . ? C2 C3 1.4180(18) . ? C2 H2 0.9500 . ? C3 C4 1.4210(18) . ? C3 H3 0.9500 . ? C4 C5 1.4206(17) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.4163(19) . ? C6 C7 1.424(2) . ? C6 H6 0.9500 . ? C7 C8 1.418(2) . ? C7 H7 0.9500 . ? C8 C9 1.415(2) . ? C8 H8 0.9500 . ? C9 C10 1.4214(18) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C21 C26 1.3990(17) . ? C21 C22 1.4102(17) . ? C22 C23 1.3986(17) . ? C22 C27 1.4990(16) . ? C23 C24 1.3833(19) . ? C23 H23 0.9500 . ? C24 C25 1.382(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe C8 156.33(6) . . ? C1 Fe C7 120.73(6) . . ? C8 Fe C7 40.85(7) . . ? C1 Fe C2 41.42(5) . . ? C8 Fe C2 120.04(6) . . ? C7 Fe C2 105.83(6) . . ? C1 Fe C5 41.53(5) . . ? C8 Fe C5 160.36(7) . . ? C7 Fe C5 157.81(6) . . ? C2 Fe C5 69.49(5) . . ? C1 Fe C6 107.16(5) . . ? C8 Fe C6 68.64(6) . . ? C7 Fe C6 40.88(6) . . ? C2 Fe C6 123.36(5) . . ? C5 Fe C6 122.47(6) . . ? C1 Fe C9 161.48(6) . . ? C8 Fe C9 40.58(7) . . ? C7 Fe C9 68.43(7) . . ? C2 Fe C9 156.18(5) . . ? C5 Fe C9 124.50(6) . . ? C6 Fe C9 68.32(6) . . ? C1 Fe C10 124.49(5) . . ? C8 Fe C10 68.36(6) . . ? C7 Fe C10 68.40(6) . . ? C2 Fe C10 160.82(5) . . ? C5 Fe C10 108.54(5) . . ? C6 Fe C10 40.48(5) . . ? C9 Fe C10 40.57(5) . . ? C1 Fe C3 68.93(5) . . ? C8 Fe C3 106.49(6) . . ? C7 Fe C3 122.65(6) . . ? C2 Fe C3 40.61(5) . . ? C5 Fe C3 68.68(5) . . ? C6 Fe C3 159.66(6) . . ? C9 Fe C3 121.65(5) . . ? C10 Fe C3 157.90(5) . . ? C1 Fe C4 68.87(5) . . ? C8 Fe C4 123.59(6) . . ? C7 Fe C4 159.55(6) . . ? C2 Fe C4 68.51(5) . . ? C5 Fe C4 40.60(5) . . ? C6 Fe C4 158.50(6) . . ? C9 Fe C4 108.36(6) . . ? C10 Fe C4 123.19(5) . . ? C3 Fe C4 40.48(5) . . ? C11 N1 C21 129.01(10) . . ? C11 N1 H1N 118.2 . . ? C21 N1 H1N 112.6 . . ? C27 N2 N3 122.59(10) . . ? C27 N2 H2N 121.8 . . ? N3 N2 H2N 115.3 . . ? N2 N3 H3N 104.7 . . ? N2 N3 H4N 107.1 . . ? H3N N3 H4N 107.6 . . ? C2 C1 C5 107.62(11) . . ? C2 C1 C11 123.88(11) . . ? C5 C1 C11 128.47(11) . . ? C2 C1 Fe 69.67(7) . . ? C5 C1 Fe 69.75(7) . . ? C11 C1 Fe 124.50(9) . . ? C3 C2 C1 107.88(11) . . ? C3 C2 Fe 70.34(7) . . ? C1 C2 Fe 68.91(7) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 126.3 . . ? C2 C3 C4 108.41(11) . . ? C2 C3 Fe 69.05(7) . . ? C4 C3 Fe 69.93(7) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe C3 H3 126.8 . . ? C5 C4 C3 108.58(11) . . ? C5 C4 Fe 69.03(7) . . ? C3 C4 Fe 69.60(7) . . ? C5 C4 H4 125.7 . . ? C3 C4 H4 125.7 . . ? Fe C4 H4 127.2 . . ? C4 C5 C1 107.51(11) . . ? C4 C5 Fe 70.37(7) . . ? C1 C5 Fe 68.72(7) . . ? C4 C5 H5 126.2 . . ? C1 C5 H5 126.2 . . ? Fe C5 H5 126.2 . . ? C10 C6 C7 107.87(13) . . ? C10 C6 Fe 70.04(8) . . ? C7 C6 Fe 69.20(8) . . ? C10 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe C6 H6 126.3 . . ? C8 C7 C6 107.82(14) . . ? C8 C7 Fe 69.44(8) . . ? C6 C7 Fe 69.92(8) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? Fe C7 H7 126.1 . . ? C9 C8 C7 108.30(13) . . ? C9 C8 Fe 70.46(8) . . ? C7 C8 Fe 69.72(8) . . ? C9 C8 H8 125.8 . . ? C7 C8 H8 125.8 . . ? Fe C8 H8 125.6 . . ? C8 C9 C10 107.85(13) . . ? C8 C9 Fe 68.96(8) . . ? C10 C9 Fe 69.75(7) . . ? C8 C9 H9 126.1 . . ? C10 C9 H9 126.1 . . ? Fe C9 H9 126.8 . . ? C6 C10 C9 108.16(13) . . ? C6 C10 Fe 69.47(8) . . ? C9 C10 Fe 69.68(7) . . ? C6 C10 H10 125.9 . . ? C9 C10 H10 125.9 . . ? Fe C10 H10 126.5 . . ? O1 C11 N1 124.09(12) . . ? O1 C11 C1 121.22(11) . . ? N1 C11 C1 114.67(10) . . ? C26 C21 N1 122.59(12) . . ? C26 C21 C22 119.18(11) . . ? N1 C21 C22 118.22(10) . . ? C23 C22 C21 119.21(11) . . ? C23 C22 C27 119.92(11) . . ? C21 C22 C27 120.87(10) . . ? C24 C23 C22 121.11(13) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C25 C24 C23 119.24(12) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 121.19(12) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C25 C26 C21 120.05(13) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? O2 C27 N2 121.90(11) . . ? O2 C27 C22 122.50(11) . . ? N2 C27 C22 115.59(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.340 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.048 data_jt204_2 _database_code_depnum_ccdc_archive 'CCDC 922140' #TrackingRef 'cif_files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 Fe N5 O2' _chemical_formula_sum 'C23 H25 Fe N5 O2' _chemical_formula_weight 459.33 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 P21/c 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 11.9743(3) _cell_length_b 12.3974(3) _cell_length_c 14.2253(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.7130(10) _cell_angle_gamma 90.00 _cell_volume 2109.38(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8433 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details SADABS _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16290 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4844 _reflns_number_gt 4113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon (Spek, 2003)' _computing_publication_material 'Platon (Spek, 2003)' _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^)+(0.0372P)^2^+0.9854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4844 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Fe Fe 0.495044(17) 0.316933(17) 0.879194(15) 0.02163(7) Uani 1 1 d . . . O1 O 0.37232(9) 0.22494(10) 0.64632(8) 0.0326(3) Uani 1 1 d . . . O2 O 0.10407(9) 0.20322(9) 0.88881(8) 0.0298(3) Uani 1 1 d . . . N1 N 0.22713(10) 0.20878(10) 0.74465(9) 0.0226(3) Uani 1 1 d . . . H1N H 0.1998 0.2302 0.7983 0.027 Uiso 1 1 d R . . N2 N -0.04229(11) 0.08386(11) 0.88466(9) 0.0273(3) Uani 1 1 d . . . N3 N -0.06032(11) 0.13303(11) 0.97141(9) 0.0266(3) Uani 1 1 d . . . H3N H -0.0104 0.1791 0.9906 0.032 Uiso 1 1 d R . . N4 N -0.22021(11) 0.03098(11) 1.00984(9) 0.0273(3) Uani 1 1 d . . . N5 N -0.15138(11) 0.15132(12) 1.11062(10) 0.0315(3) Uani 1 1 d . . . C1 C 0.36927(12) 0.33865(12) 0.77982(10) 0.0220(3) Uani 1 1 d . . . C2 C 0.33344(12) 0.37023(12) 0.87072(11) 0.0238(3) Uani 1 1 d . . . H2 H 0.2726 0.3403 0.9024 0.029 Uiso 1 1 calc R . . C3 C 0.40520(13) 0.45420(13) 0.90469(12) 0.0287(3) Uani 1 1 d . . . H3 H 0.4005 0.4903 0.9633 0.034 Uiso 1 1 calc R . . C4 C 0.48523(13) 0.47507(13) 0.83619(12) 0.0307(4) Uani 1 1 d . . . H4 H 0.5430 0.5276 0.8410 0.037 Uiso 1 1 calc R . . C5 C 0.46378(13) 0.40355(13) 0.75936(11) 0.0273(3) Uani 1 1 d . . . H5 H 0.5050 0.3996 0.7040 0.033 Uiso 1 1 calc R . . C6 C 0.53235(15) 0.15636(13) 0.88124(12) 0.0298(3) Uani 1 1 d . . . H6 H 0.4970 0.1025 0.8428 0.036 Uiso 1 1 calc R . . C7 C 0.49878(14) 0.19026(12) 0.97064(11) 0.0261(3) Uani 1 1 d . . . H7 H 0.4371 0.1625 1.0027 0.031 Uiso 1 1 calc R . . C8 C 0.57216(15) 0.27205(14) 1.00423(12) 0.0335(4) Uani 1 1 d . . . H8 H 0.5685 0.3093 1.0623 0.040 Uiso 1 1 calc R . . C9 C 0.65210(14) 0.28842(15) 0.93581(16) 0.0439(5) Uani 1 1 d . . . H9 H 0.7120 0.3387 0.9401 0.053 Uiso 1 1 calc R . . C10 C 0.62772(15) 0.21682(16) 0.85928(15) 0.0421(5) Uani 1 1 d . . . H10 H 0.6682 0.2108 0.8037 0.051 Uiso 1 1 calc R . . C11 C 0.32442(12) 0.25201(12) 0.71708(10) 0.0220(3) Uani 1 1 d . . . C21 C 0.16464(12) 0.12299(12) 0.70461(10) 0.0209(3) Uani 1 1 d . . . C22 C 0.07565(12) 0.08217(12) 0.75540(10) 0.0208(3) Uani 1 1 d . . . C23 C 0.01320(13) -0.00356(13) 0.71643(11) 0.0273(3) Uani 1 1 d . . . H23 H -0.0465 -0.0324 0.7503 0.033 Uiso 1 1 calc R . . C24 C 0.03583(14) -0.04758(14) 0.63007(12) 0.0317(4) Uani 1 1 d . . . H24 H -0.0069 -0.1066 0.6054 0.038 Uiso 1 1 calc R . . C25 C 0.12176(14) -0.00432(14) 0.57995(11) 0.0313(4) Uani 1 1 d . . . H25 H 0.1366 -0.0331 0.5199 0.038 Uiso 1 1 calc R . . C26 C 0.18615(13) 0.07989(13) 0.61592(11) 0.0269(3) Uani 1 1 d . . . H26 H 0.2448 0.1086 0.5808 0.032 Uiso 1 1 calc R . . C27 C 0.04612(12) 0.12786(12) 0.84895(10) 0.0208(3) Uani 1 1 d . . . C28 C -0.14059(12) 0.10423(12) 1.02643(10) 0.0218(3) Uani 1 1 d . . . C29 C -0.29235(12) 0.02358(13) 1.08939(11) 0.0243(3) Uani 1 1 d . . . H29A H -0.2830 -0.0467 1.1218 0.029 Uiso 1 1 calc R . . H29B H -0.3719 0.0328 1.0687 0.029 Uiso 1 1 calc R . . C30 C -0.25258(12) 0.11649(13) 1.15376(11) 0.0249(3) Uani 1 1 d . . . H30A H -0.3086 0.1752 1.1541 0.030 Uiso 1 1 calc R . . H30B H -0.2366 0.0912 1.2190 0.030 Uiso 1 1 calc R . . C31 C -0.23469(15) -0.04791(15) 0.93437(12) 0.0351(4) Uani 1 1 d . . . H31A H -0.1801 -0.0340 0.8866 0.053 Uiso 1 1 calc R . . H31B H -0.3105 -0.0421 0.9057 0.053 Uiso 1 1 calc R . . H31C H -0.2232 -0.1206 0.9600 0.053 Uiso 1 1 calc R . . C32 C -0.08788(17) 0.24305(16) 1.14550(13) 0.0410(4) Uani 1 1 d . . . H32A H -0.0085 0.2318 1.1347 0.061 Uiso 1 1 calc R . . H32B H -0.0979 0.2514 1.2131 0.061 Uiso 1 1 calc R . . H32C H -0.1141 0.3083 1.1124 0.061 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe 0.02079(11) 0.01872(11) 0.02548(12) 0.00490(9) 0.00205(8) -0.00189(8) O1 0.0338(6) 0.0392(7) 0.0259(6) -0.0019(5) 0.0125(5) -0.0007(5) O2 0.0311(6) 0.0329(6) 0.0262(6) -0.0093(5) 0.0097(5) -0.0134(5) N1 0.0240(6) 0.0258(6) 0.0183(6) -0.0022(5) 0.0042(5) -0.0009(5) N2 0.0293(6) 0.0302(7) 0.0227(6) -0.0043(6) 0.0045(5) -0.0081(6) N3 0.0275(6) 0.0293(7) 0.0234(6) -0.0054(5) 0.0047(5) -0.0120(6) N4 0.0272(6) 0.0285(7) 0.0266(7) -0.0055(6) 0.0060(5) -0.0110(6) N5 0.0304(7) 0.0372(8) 0.0274(7) -0.0094(6) 0.0072(6) -0.0146(6) C1 0.0212(6) 0.0214(7) 0.0236(7) 0.0055(6) 0.0025(6) 0.0013(6) C2 0.0222(7) 0.0232(7) 0.0263(8) 0.0005(6) 0.0029(6) 0.0004(6) C3 0.0304(8) 0.0202(7) 0.0351(9) -0.0011(7) -0.0022(7) 0.0005(6) C4 0.0291(8) 0.0207(8) 0.0419(10) 0.0098(7) -0.0026(7) -0.0040(6) C5 0.0261(7) 0.0262(8) 0.0297(8) 0.0111(7) 0.0036(6) -0.0006(6) C6 0.0380(8) 0.0213(7) 0.0303(8) -0.0001(6) 0.0028(7) 0.0054(7) C7 0.0332(8) 0.0191(7) 0.0263(8) 0.0058(6) 0.0035(6) 0.0007(6) C8 0.0426(9) 0.0227(8) 0.0339(9) 0.0036(7) -0.0129(7) 0.0027(7) C9 0.0244(8) 0.0326(9) 0.0733(14) 0.0184(10) -0.0118(9) -0.0026(7) C10 0.0360(9) 0.0427(10) 0.0492(11) 0.0205(9) 0.0184(8) 0.0171(8) C11 0.0234(7) 0.0236(7) 0.0191(7) 0.0068(6) 0.0023(6) 0.0048(6) C21 0.0218(7) 0.0215(7) 0.0189(7) 0.0002(6) -0.0031(5) 0.0048(6) C22 0.0231(7) 0.0193(7) 0.0196(7) 0.0009(6) -0.0039(5) 0.0030(6) C23 0.0292(7) 0.0235(8) 0.0288(8) 0.0000(6) -0.0044(6) -0.0001(6) C24 0.0353(8) 0.0265(8) 0.0321(9) -0.0077(7) -0.0108(7) 0.0024(7) C25 0.0348(8) 0.0349(9) 0.0235(8) -0.0099(7) -0.0065(6) 0.0117(7) C26 0.0274(7) 0.0328(8) 0.0203(7) -0.0019(6) -0.0005(6) 0.0073(7) C27 0.0215(6) 0.0200(7) 0.0209(7) 0.0023(6) -0.0007(6) 0.0004(6) C28 0.0218(6) 0.0219(7) 0.0216(7) 0.0017(6) -0.0006(5) -0.0025(6) C29 0.0205(7) 0.0262(8) 0.0263(8) 0.0044(6) 0.0023(6) -0.0022(6) C30 0.0244(7) 0.0270(8) 0.0236(7) 0.0028(6) 0.0037(6) 0.0002(6) C31 0.0364(9) 0.0352(9) 0.0341(9) -0.0115(8) 0.0058(7) -0.0157(7) C32 0.0513(11) 0.0400(10) 0.0319(9) -0.0108(8) 0.0054(8) -0.0208(9) _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 Fe C1 2.0340(15) . ? Fe C5 2.0344(15) . ? Fe C7 2.0384(15) . ? Fe C6 2.0401(16) . ? Fe C9 2.0413(17) . ? Fe C8 2.0422(16) . ? Fe C2 2.0430(15) . ? Fe C10 2.0464(17) . ? Fe C3 2.0547(16) . ? Fe C4 2.0554(16) . ? O1 C11 1.2285(18) . ? O2 C27 1.2801(18) . ? N1 C11 1.3571(19) . ? N1 C21 1.4053(19) . ? N1 H1N 0.8855 . ? N2 C27 1.3143(19) . ? N2 N3 1.4023(18) . ? N3 C28 1.3173(19) . ? N3 H3N 0.8624 . ? N4 C28 1.3297(19) . ? N4 C31 1.457(2) . ? N4 C29 1.4585(19) . ? N5 C28 1.344(2) . ? N5 C32 1.443(2) . ? N5 C30 1.4498(19) . ? C1 C5 1.430(2) . ? C1 C2 1.436(2) . ? C1 C11 1.481(2) . ? C2 C3 1.420(2) . ? C2 H2 0.9500 . ? C3 C4 1.422(2) . ? C3 H3 0.9500 . ? C4 C5 1.421(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.413(3) . ? C6 C7 1.416(2) . ? C6 H6 0.9500 . ? C7 C8 1.410(2) . ? C7 H7 0.9500 . ? C8 C9 1.412(3) . ? C8 H8 0.9500 . ? C9 C10 1.424(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C21 C26 1.405(2) . ? C21 C22 1.409(2) . ? C22 C23 1.399(2) . ? C22 C27 1.504(2) . ? C23 C24 1.383(2) . ? C23 H23 0.9500 . ? C24 C25 1.387(3) . ? C24 H24 0.9500 . ? C25 C26 1.382(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C29 C30 1.533(2) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 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 C1 Fe C5 41.14(6) . . ? C1 Fe C7 122.60(6) . . ? C5 Fe C7 159.89(7) . . ? C1 Fe C6 107.07(7) . . ? C5 Fe C6 123.95(7) . . ? C7 Fe C6 40.62(6) . . ? C1 Fe C9 159.24(8) . . ? C5 Fe C9 123.47(7) . . ? C7 Fe C9 67.84(7) . . ? C6 Fe C9 68.18(7) . . ? C1 Fe C8 158.55(7) . . ? C5 Fe C8 158.64(7) . . ? C7 Fe C8 40.44(7) . . ? C6 Fe C8 68.41(7) . . ? C9 Fe C8 40.45(8) . . ? C1 Fe C2 41.24(6) . . ? C5 Fe C2 69.12(6) . . ? C7 Fe C2 106.20(6) . . ? C6 Fe C2 121.51(7) . . ? C9 Fe C2 158.70(8) . . ? C8 Fe C2 121.84(7) . . ? C1 Fe C10 122.56(8) . . ? C5 Fe C10 108.51(7) . . ? C7 Fe C10 68.12(7) . . ? C6 Fe C10 40.47(7) . . ? C9 Fe C10 40.78(9) . . ? C8 Fe C10 68.49(8) . . ? C2 Fe C10 158.04(8) . . ? C1 Fe C3 68.68(6) . . ? C5 Fe C3 68.51(7) . . ? C7 Fe C3 121.42(7) . . ? C6 Fe C3 157.19(7) . . ? C9 Fe C3 123.65(8) . . ? C8 Fe C3 106.91(7) . . ? C2 Fe C3 40.55(6) . . ? C10 Fe C3 160.60(8) . . ? C1 Fe C4 68.71(6) . . ? C5 Fe C4 40.67(7) . . ? C7 Fe C4 157.52(7) . . ? C6 Fe C4 160.79(7) . . ? C9 Fe C4 108.74(7) . . ? C8 Fe C4 122.43(7) . . ? C2 Fe C4 68.49(6) . . ? C10 Fe C4 124.83(7) . . ? C3 Fe C4 40.50(7) . . ? C11 N1 C21 129.02(13) . . ? C11 N1 H1N 119.2 . . ? C21 N1 H1N 111.4 . . ? C27 N2 N3 108.66(12) . . ? C28 N3 N2 123.51(13) . . ? C28 N3 H3N 120.4 . . ? N2 N3 H3N 115.7 . . ? C28 N4 C31 130.44(13) . . ? C28 N4 C29 110.56(12) . . ? C31 N4 C29 118.39(12) . . ? C28 N5 C32 125.27(14) . . ? C28 N5 C30 111.43(13) . . ? C32 N5 C30 121.77(14) . . ? C5 C1 C2 107.64(13) . . ? C5 C1 C11 123.60(13) . . ? C2 C1 C11 128.69(13) . . ? C5 C1 Fe 69.44(9) . . ? C2 C1 Fe 69.71(8) . . ? C11 C1 Fe 123.93(10) . . ? C3 C2 C1 107.73(13) . . ? C3 C2 Fe 70.17(9) . . ? C1 C2 Fe 69.04(8) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? Fe C2 H2 126.2 . . ? C2 C3 C4 108.46(15) . . ? C2 C3 Fe 69.28(9) . . ? C4 C3 Fe 69.78(9) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? Fe C3 H3 126.7 . . ? C5 C4 C3 108.07(14) . . ? C5 C4 Fe 68.87(9) . . ? C3 C4 Fe 69.73(9) . . ? C5 C4 H4 126.0 . . ? C3 C4 H4 126.0 . . ? Fe C4 H4 127.0 . . ? C4 C5 C1 108.09(14) . . ? C4 C5 Fe 70.46(9) . . ? C1 C5 Fe 69.41(8) . . ? C4 C5 H5 126.0 . . ? C1 C5 H5 126.0 . . ? Fe C5 H5 125.8 . . ? C10 C6 C7 107.93(16) . . ? C10 C6 Fe 70.00(10) . . ? C7 C6 Fe 69.62(9) . . ? C10 C6 H6 126.0 . . ? C7 C6 H6 126.0 . . ? Fe C6 H6 125.9 . . ? C8 C7 C6 108.60(15) . . ? C8 C7 Fe 69.93(9) . . ? C6 C7 Fe 69.76(9) . . ? C8 C7 H7 125.7 . . ? C6 C7 H7 125.7 . . ? Fe C7 H7 126.2 . . ? C7 C8 C9 107.56(16) . . ? C7 C8 Fe 69.64(9) . . ? C9 C8 Fe 69.74(10) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? Fe C8 H8 126.0 . . ? C8 C9 C10 108.44(16) . . ? C8 C9 Fe 69.81(10) . . ? C10 C9 Fe 69.80(10) . . ? C8 C9 H9 125.8 . . ? C10 C9 H9 125.8 . . ? Fe C9 H9 126.2 . . ? C6 C10 C9 107.46(16) . . ? C6 C10 Fe 69.53(10) . . ? C9 C10 Fe 69.42(10) . . ? C6 C10 H10 126.3 . . ? C9 C10 H10 126.3 . . ? Fe C10 H10 126.3 . . ? O1 C11 N1 124.70(15) . . ? O1 C11 C1 121.46(14) . . ? N1 C11 C1 113.83(13) . . ? C26 C21 N1 122.34(14) . . ? C26 C21 C22 119.93(14) . . ? N1 C21 C22 117.70(13) . . ? C23 C22 C21 118.21(14) . . ? C23 C22 C27 119.55(13) . . ? C21 C22 C27 122.25(13) . . ? C24 C23 C22 121.89(15) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C25 119.04(15) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C26 C25 C24 121.08(15) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C21 119.81(15) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? O2 C27 N2 124.16(14) . . ? O2 C27 C22 121.44(13) . . ? N2 C27 C22 114.40(13) . . ? N3 C28 N4 128.09(14) . . ? N3 C28 N5 121.02(13) . . ? N4 C28 N5 110.88(13) . . ? N4 C29 C30 103.74(12) . . ? N4 C29 H29A 111.0 . . ? C30 C29 H29A 111.0 . . ? N4 C29 H29B 111.0 . . ? C30 C29 H29B 111.0 . . ? H29A C29 H29B 109.0 . . ? N5 C30 C29 102.31(12) . . ? N5 C30 H30A 111.3 . . ? C29 C30 H30A 111.3 . . ? N5 C30 H30B 111.3 . . ? C29 C30 H30B 111.3 . . ? H30A C30 H30B 109.2 . . ? N4 C31 H31A 109.5 . . ? N4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N5 C32 H32A 109.5 . . ? N5 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N5 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.289 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.050 #===END