data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'David P. Goldberg' _publ_contact_author_address ;Department of Chemistry Johns Hopkins University Baltimore, Maryland, 21218 United States ; _publ_contact_author_email dpg@jhu.edu _publ_contact_author_phone 410.516.6658 loop_ _publ_author_name _publ_author_address 'McQuilken, Alison C.' ;Department of Chemistry Johns Hopkins University Baltimore, Maryland, 21218 United States ; 'Jiang, Yunbo' ;Department of Chemistry Johns Hopkins University Baltimore, Maryland, 21218 United States ; 'Siegler, Maxime A.' ;Department of Chemistry Johns Hopkins University Baltimore, Maryland, 21218 United States ; 'Goldberg, David P.' ;Department of Chemistry Johns Hopkins University Baltimore, Maryland, 21218 United States ; data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 Fe N5 O2 S2' _chemical_formula_sum 'C25 H21 Fe N5 O2 S2' _chemical_formula_weight 543.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.3797(3) _cell_length_b 18.0863(5) _cell_length_c 15.6327(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.970(2) _cell_angle_gamma 90.00 _cell_volume 2637.61(13) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4972 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 25.13 _exptl_crystal_description 'irregular lath' _exptl_crystal_colour 'orange-red' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.761 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 15.989 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17987 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4646 _reflns_number_gt 3549 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)' _computing_publication_material 'SHELXTL v6.10 (Sheldrick, 2008)' _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^)+(0.0754P)^2^+0.3562P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4646 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1220 _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 Fe1 Fe 0.37059(5) 0.26258(2) 0.15448(3) 0.01609(16) Uani 1 1 d . . . S1 S 0.32949(9) 0.23304(5) 0.28495(5) 0.0203(2) Uani 1 1 d . . . S2 S 0.78621(10) 0.12679(5) 0.13575(6) 0.0326(3) Uani 1 1 d . . . C1 C 0.3378(4) 0.10012(18) 0.1163(2) 0.0217(8) Uani 1 1 d . . . H1 H 0.4131 0.0905 0.1604 0.026 Uiso 1 1 calc R . . C2 C 0.2752(4) 0.0414(2) 0.0698(2) 0.0273(8) Uani 1 1 d . . . H2 H 0.3083 -0.0077 0.0808 0.033 Uiso 1 1 calc R . . C3 C 0.1633(4) 0.0556(2) 0.0069(2) 0.0283(9) Uani 1 1 d . . . H3 H 0.1192 0.0161 -0.0261 0.034 Uiso 1 1 calc R . . C4 C 0.1158(4) 0.12729(19) -0.0078(2) 0.0231(8) Uani 1 1 d . . . H4 H 0.0379 0.1379 -0.0498 0.028 Uiso 1 1 calc R . . C5 C 0.1849(4) 0.18303(18) 0.0405(2) 0.0192(7) Uani 1 1 d . . . C6 C 0.1564(4) 0.26464(18) 0.0278(2) 0.0174(7) Uani 1 1 d . . . H6 H 0.0604 0.2749 -0.0041 0.021 Uiso 1 1 calc R . . C7 C 0.2780(4) 0.29380(18) -0.0178(2) 0.0183(7) Uani 1 1 d . . . C8 C 0.2719(4) 0.31386(18) -0.1025(2) 0.0227(8) Uani 1 1 d . . . H8 H 0.1846 0.3106 -0.1390 0.027 Uiso 1 1 calc R . . C9 C 0.3963(4) 0.3390(2) -0.1338(2) 0.0289(9) Uani 1 1 d . . . H9 H 0.3958 0.3529 -0.1924 0.035 Uiso 1 1 calc R . . C10 C 0.5210(4) 0.3436(2) -0.0785(2) 0.0286(9) Uani 1 1 d . . . H10 H 0.6066 0.3620 -0.0982 0.034 Uiso 1 1 calc R . . C11 C 0.5193(4) 0.32114(18) 0.0056(2) 0.0227(8) Uani 1 1 d . . . H11 H 0.6055 0.3235 0.0432 0.027 Uiso 1 1 calc R . . C12 C 0.1750(3) 0.38177(17) 0.1142(2) 0.0173(7) Uani 1 1 d . . . H12A H 0.0838 0.4011 0.1319 0.021 Uiso 1 1 calc R . . H12B H 0.1835 0.3987 0.0547 0.021 Uiso 1 1 calc R . . C13 C 0.2996(3) 0.41176(18) 0.17380(19) 0.0169(7) Uani 1 1 d . . . C14 C 0.3039(4) 0.48404(18) 0.2009(2) 0.0211(8) Uani 1 1 d . . . H14 H 0.2254 0.5164 0.1862 0.025 Uiso 1 1 calc R . . C15 C 0.4263(4) 0.50845(19) 0.2503(2) 0.0240(8) Uani 1 1 d . . . H15 H 0.4333 0.5583 0.2692 0.029 Uiso 1 1 calc R . . C16 C 0.5378(4) 0.45984(19) 0.2717(2) 0.0246(8) Uani 1 1 d . . . H16 H 0.6227 0.4760 0.3050 0.030 Uiso 1 1 calc R . . C17 C 0.5244(4) 0.38837(19) 0.24451(19) 0.0196(7) Uani 1 1 d . . . H17 H 0.6004 0.3548 0.2608 0.023 Uiso 1 1 calc R . . C18 C 0.0540(4) 0.27155(19) 0.1645(2) 0.0201(8) Uani 1 1 d . . . H18A H 0.0568 0.2169 0.1669 0.024 Uiso 1 1 calc R . . H18B H -0.0387 0.2863 0.1330 0.024 Uiso 1 1 calc R . . C19 C 0.0627(4) 0.30172(18) 0.2545(2) 0.0213(8) Uani 1 1 d . . . C20 C -0.0514(4) 0.3420(2) 0.2805(2) 0.0281(9) Uani 1 1 d . . . H20 H -0.1323 0.3516 0.2403 0.034 Uiso 1 1 calc R . . C21 C -0.0495(4) 0.3686(2) 0.3643(2) 0.0287(9) Uani 1 1 d . . . H21 H -0.1289 0.3956 0.3812 0.034 Uiso 1 1 calc R . . C22 C 0.0688(4) 0.35551(19) 0.4223(2) 0.0262(8) Uani 1 1 d . . . H22 H 0.0704 0.3732 0.4797 0.031 Uiso 1 1 calc R . . C23 C 0.1847(4) 0.31692(19) 0.3979(2) 0.0244(8) Uani 1 1 d . . . H23 H 0.2671 0.3094 0.4376 0.029 Uiso 1 1 calc R . . C24 C 0.1803(4) 0.28903(18) 0.3144(2) 0.0194(7) Uani 1 1 d . . . C25 C 0.6580(4) 0.18365(19) 0.1573(2) 0.0215(8) Uani 1 1 d . . . N1 N 0.2957(3) 0.17040(14) 0.10136(16) 0.0178(6) Uani 1 1 d . . . N2 N 0.4011(3) 0.29626(15) 0.03581(16) 0.0179(6) Uani 1 1 d . . . N3 N 0.1732(3) 0.29851(15) 0.11662(15) 0.0159(6) Uani 1 1 d . . . N4 N 0.4078(3) 0.36340(14) 0.19545(16) 0.0155(6) Uani 1 1 d . . . N5 N 0.5638(3) 0.22278(15) 0.17043(17) 0.0208(6) Uani 1 1 d . . . O1 O 0.2782(3) 0.15619(13) 0.29645(15) 0.0283(6) Uani 1 1 d . . . O2 O 0.4474(3) 0.25265(13) 0.35102(15) 0.0271(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0204(3) 0.0158(3) 0.0122(3) 0.00056(19) 0.00232(19) 0.0009(2) S1 0.0243(5) 0.0211(4) 0.0154(4) 0.0021(3) 0.0015(3) 0.0030(4) S2 0.0269(5) 0.0333(5) 0.0355(6) -0.0081(4) -0.0071(4) 0.0114(4) C1 0.0252(19) 0.0177(17) 0.0232(18) 0.0016(14) 0.0080(15) 0.0006(15) C2 0.035(2) 0.0212(19) 0.027(2) 0.0007(15) 0.0114(17) 0.0000(16) C3 0.036(2) 0.025(2) 0.026(2) -0.0089(16) 0.0139(17) -0.0109(17) C4 0.024(2) 0.027(2) 0.0178(17) -0.0031(14) 0.0034(15) -0.0075(15) C5 0.0234(19) 0.0208(17) 0.0145(17) -0.0019(14) 0.0065(14) -0.0036(14) C6 0.0195(18) 0.0206(17) 0.0115(16) -0.0013(13) -0.0017(13) -0.0020(14) C7 0.0247(19) 0.0177(16) 0.0124(16) -0.0038(13) 0.0014(14) 0.0011(14) C8 0.030(2) 0.0240(18) 0.0131(17) -0.0011(14) -0.0024(15) -0.0003(15) C9 0.044(2) 0.030(2) 0.0133(18) 0.0034(15) 0.0054(17) 0.0040(18) C10 0.027(2) 0.034(2) 0.027(2) 0.0053(16) 0.0152(17) -0.0001(17) C11 0.026(2) 0.0215(18) 0.0213(18) -0.0006(14) 0.0054(15) 0.0023(15) C12 0.0172(18) 0.0164(17) 0.0180(17) 0.0030(13) -0.0001(14) 0.0037(13) C13 0.0192(18) 0.0193(17) 0.0121(16) 0.0032(13) 0.0012(13) -0.0012(14) C14 0.030(2) 0.0165(17) 0.0164(17) 0.0030(14) 0.0027(15) 0.0024(15) C15 0.031(2) 0.0220(18) 0.0187(18) 0.0001(14) 0.0030(15) -0.0072(16) C16 0.025(2) 0.030(2) 0.0184(18) -0.0014(15) -0.0033(15) -0.0071(16) C17 0.0192(18) 0.0258(18) 0.0135(16) 0.0027(14) 0.0009(14) -0.0003(15) C18 0.0156(18) 0.0241(19) 0.0207(18) -0.0008(14) 0.0024(14) -0.0038(14) C19 0.026(2) 0.0207(18) 0.0176(17) 0.0014(14) 0.0050(15) -0.0036(15) C20 0.023(2) 0.034(2) 0.028(2) -0.0008(16) 0.0054(16) -0.0002(16) C21 0.027(2) 0.035(2) 0.026(2) -0.0043(16) 0.0127(17) 0.0050(17) C22 0.036(2) 0.027(2) 0.0173(18) -0.0025(15) 0.0101(16) -0.0028(17) C23 0.030(2) 0.0230(18) 0.0194(18) 0.0045(15) 0.0009(15) -0.0028(16) C24 0.0198(19) 0.0162(16) 0.0229(18) 0.0006(14) 0.0052(15) -0.0048(14) C25 0.023(2) 0.0225(18) 0.0179(18) 0.0042(14) -0.0051(15) -0.0031(16) N1 0.0201(16) 0.0187(15) 0.0151(14) 0.0007(11) 0.0048(12) -0.0019(12) N2 0.0194(15) 0.0186(15) 0.0156(14) -0.0016(11) 0.0016(12) 0.0041(12) N3 0.0202(15) 0.0169(14) 0.0104(13) -0.0017(11) 0.0008(11) -0.0014(12) N4 0.0167(15) 0.0181(14) 0.0117(13) 0.0025(11) 0.0021(11) -0.0016(12) N5 0.0239(17) 0.0219(16) 0.0166(15) -0.0024(12) 0.0009(12) 0.0004(13) O1 0.0402(16) 0.0220(13) 0.0239(13) 0.0064(10) 0.0092(11) 0.0029(11) O2 0.0252(14) 0.0374(15) 0.0175(12) 0.0016(10) -0.0034(10) 0.0083(11) _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 Fe1 N5 1.941(3) . ? Fe1 N4 1.952(3) . ? Fe1 N1 1.960(3) . ? Fe1 N3 1.993(3) . ? Fe1 N2 2.001(3) . ? Fe1 S1 2.1812(9) . ? S1 O2 1.476(2) . ? S1 O1 1.488(2) . ? S1 C24 1.825(4) . ? S2 C25 1.643(4) . ? C1 N1 1.344(4) . ? C1 C2 1.383(5) . ? C1 H1 0.9500 . ? C2 C3 1.386(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 C5 1.380(5) . ? C4 H4 0.9500 . ? C5 N1 1.353(4) . ? C5 C6 1.510(5) . ? C6 C7 1.503(5) . ? C6 N3 1.511(4) . ? C6 H6 1.0000 . ? C7 N2 1.355(4) . ? C7 C8 1.368(4) . ? C8 C9 1.388(5) . ? C8 H8 0.9500 . ? C9 C10 1.383(5) . ? C9 H9 0.9500 . ? C10 C11 1.378(5) . ? C10 H10 0.9500 . ? C11 N2 1.328(4) . ? C11 H11 0.9500 . ? C12 N3 1.506(4) . ? C12 C13 1.517(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.356(4) . ? C13 C14 1.373(4) . ? C14 C15 1.387(5) . ? C14 H14 0.9500 . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 C17 1.362(5) . ? C16 H16 0.9500 . ? C17 N4 1.347(4) . ? C17 H17 0.9500 . ? C18 N3 1.490(4) . ? C18 C19 1.504(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.390(5) . ? C19 C20 1.390(5) . ? C20 C21 1.394(5) . ? C20 H20 0.9500 . ? C21 C22 1.379(5) . ? C21 H21 0.9500 . ? C22 C23 1.379(5) . ? C22 H22 0.9500 . ? C23 C24 1.395(5) . ? C23 H23 0.9500 . ? C25 N5 1.167(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Fe1 N4 99.87(11) . . ? N5 Fe1 N1 91.59(11) . . ? N4 Fe1 N1 167.85(11) . . ? N5 Fe1 N3 169.97(11) . . ? N4 Fe1 N3 85.52(11) . . ? N1 Fe1 N3 82.56(11) . . ? N5 Fe1 N2 90.60(11) . . ? N4 Fe1 N2 88.96(11) . . ? N1 Fe1 N2 86.89(11) . . ? N3 Fe1 N2 80.99(11) . . ? N5 Fe1 S1 92.43(8) . . ? N4 Fe1 S1 88.00(8) . . ? N1 Fe1 S1 95.59(8) . . ? N3 Fe1 S1 96.23(8) . . ? N2 Fe1 S1 176.03(8) . . ? O2 S1 O1 111.61(14) . . ? O2 S1 C24 103.21(15) . . ? O1 S1 C24 102.80(15) . . ? O2 S1 Fe1 113.77(11) . . ? O1 S1 Fe1 115.64(10) . . ? C24 S1 Fe1 108.35(11) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 122.9(3) . . ? N1 C5 C6 111.7(3) . . ? C4 C5 C6 125.2(3) . . ? C7 C6 C5 105.8(3) . . ? C7 C6 N3 106.4(2) . . ? C5 C6 N3 106.0(2) . . ? C7 C6 H6 112.7 . . ? C5 C6 H6 112.7 . . ? N3 C6 H6 112.7 . . ? N2 C7 C8 122.5(3) . . ? N2 C7 C6 111.0(3) . . ? C8 C7 C6 126.5(3) . . ? C7 C8 C9 118.4(3) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 119.1(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N2 C11 C10 122.1(3) . . ? N2 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? N3 C12 C13 110.6(2) . . ? N3 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N4 C13 C14 122.7(3) . . ? N4 C13 C12 115.6(3) . . ? C14 C13 C12 121.7(3) . . ? C13 C14 C15 118.1(3) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 119.0(3) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? N4 C17 C16 122.6(3) . . ? N4 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? N3 C18 C19 112.4(3) . . ? N3 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? N3 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C24 C19 C20 118.1(3) . . ? C24 C19 C18 122.2(3) . . ? C20 C19 C18 119.7(3) . . ? C19 C20 C21 121.4(3) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C22 C21 C20 119.3(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C19 C24 C23 121.0(3) . . ? C19 C24 S1 119.8(3) . . ? C23 C24 S1 119.2(3) . . ? N5 C25 S2 177.6(3) . . ? C1 N1 C5 118.2(3) . . ? C1 N1 Fe1 130.1(2) . . ? C5 N1 Fe1 111.7(2) . . ? C11 N2 C7 118.7(3) . . ? C11 N2 Fe1 129.6(2) . . ? C7 N2 Fe1 111.7(2) . . ? C18 N3 C12 110.5(2) . . ? C18 N3 C6 108.5(2) . . ? C12 N3 C6 112.5(2) . . ? C18 N3 Fe1 117.8(2) . . ? C12 N3 Fe1 108.72(19) . . ? C6 N3 Fe1 98.38(19) . . ? C17 N4 C13 117.9(3) . . ? C17 N4 Fe1 127.4(2) . . ? C13 N4 Fe1 114.6(2) . . ? C25 N5 Fe1 156.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Fe1 S1 O2 45.64(14) . . . . ? N4 Fe1 S1 O2 -54.16(14) . . . . ? N1 Fe1 S1 O2 137.48(14) . . . . ? N3 Fe1 S1 O2 -139.43(13) . . . . ? N5 Fe1 S1 O1 -85.49(14) . . . . ? N4 Fe1 S1 O1 174.70(14) . . . . ? N1 Fe1 S1 O1 6.34(14) . . . . ? N3 Fe1 S1 O1 89.44(14) . . . . ? N5 Fe1 S1 C24 159.79(14) . . . . ? N4 Fe1 S1 C24 59.99(14) . . . . ? N1 Fe1 S1 C24 -108.38(14) . . . . ? N3 Fe1 S1 C24 -25.28(14) . . . . ? N1 C1 C2 C3 -1.4(5) . . . . ? C1 C2 C3 C4 -0.4(5) . . . . ? C2 C3 C4 C5 1.3(5) . . . . ? C3 C4 C5 N1 -0.4(5) . . . . ? C3 C4 C5 C6 174.3(3) . . . . ? N1 C5 C6 C7 72.2(3) . . . . ? C4 C5 C6 C7 -103.0(4) . . . . ? N1 C5 C6 N3 -40.5(3) . . . . ? C4 C5 C6 N3 144.3(3) . . . . ? C5 C6 C7 N2 -72.2(3) . . . . ? N3 C6 C7 N2 40.2(3) . . . . ? C5 C6 C7 C8 106.0(4) . . . . ? N3 C6 C7 C8 -141.5(3) . . . . ? N2 C7 C8 C9 -1.3(5) . . . . ? C6 C7 C8 C9 -179.3(3) . . . . ? C7 C8 C9 C10 -0.6(5) . . . . ? C8 C9 C10 C11 1.8(5) . . . . ? C9 C10 C11 N2 -1.1(5) . . . . ? N3 C12 C13 N4 20.1(4) . . . . ? N3 C12 C13 C14 -162.4(3) . . . . ? N4 C13 C14 C15 1.9(5) . . . . ? C12 C13 C14 C15 -175.4(3) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C15 C16 C17 N4 1.7(5) . . . . ? N3 C18 C19 C24 -59.7(4) . . . . ? N3 C18 C19 C20 122.1(3) . . . . ? C24 C19 C20 C21 -0.5(5) . . . . ? C18 C19 C20 C21 177.7(3) . . . . ? C19 C20 C21 C22 0.8(6) . . . . ? C20 C21 C22 C23 0.5(6) . . . . ? C21 C22 C23 C24 -2.0(5) . . . . ? C20 C19 C24 C23 -1.0(5) . . . . ? C18 C19 C24 C23 -179.2(3) . . . . ? C20 C19 C24 S1 177.3(3) . . . . ? C18 C19 C24 S1 -0.9(5) . . . . ? C22 C23 C24 C19 2.2(5) . . . . ? C22 C23 C24 S1 -176.1(3) . . . . ? O2 S1 C24 C19 161.9(3) . . . . ? O1 S1 C24 C19 -81.9(3) . . . . ? Fe1 S1 C24 C19 40.9(3) . . . . ? O2 S1 C24 C23 -19.8(3) . . . . ? O1 S1 C24 C23 96.4(3) . . . . ? Fe1 S1 C24 C23 -140.7(2) . . . . ? C2 C1 N1 C5 2.3(5) . . . . ? C2 C1 N1 Fe1 -177.4(2) . . . . ? C4 C5 N1 C1 -1.4(5) . . . . ? C6 C5 N1 C1 -176.7(3) . . . . ? C4 C5 N1 Fe1 178.4(3) . . . . ? C6 C5 N1 Fe1 3.1(3) . . . . ? N5 Fe1 N1 C1 32.6(3) . . . . ? N4 Fe1 N1 C1 -166.7(4) . . . . ? N3 Fe1 N1 C1 -155.6(3) . . . . ? N2 Fe1 N1 C1 123.1(3) . . . . ? S1 Fe1 N1 C1 -60.0(3) . . . . ? N5 Fe1 N1 C5 -147.2(2) . . . . ? N4 Fe1 N1 C5 13.5(6) . . . . ? N3 Fe1 N1 C5 24.6(2) . . . . ? N2 Fe1 N1 C5 -56.7(2) . . . . ? S1 Fe1 N1 C5 120.2(2) . . . . ? C10 C11 N2 C7 -0.8(5) . . . . ? C10 C11 N2 Fe1 -178.7(3) . . . . ? C8 C7 N2 C11 2.0(5) . . . . ? C6 C7 N2 C11 -179.7(3) . . . . ? C8 C7 N2 Fe1 -179.7(3) . . . . ? C6 C7 N2 Fe1 -1.4(3) . . . . ? N5 Fe1 N2 C11 -34.1(3) . . . . ? N4 Fe1 N2 C11 65.8(3) . . . . ? N1 Fe1 N2 C11 -125.6(3) . . . . ? N3 Fe1 N2 C11 151.4(3) . . . . ? N5 Fe1 N2 C7 147.9(2) . . . . ? N4 Fe1 N2 C7 -112.3(2) . . . . ? N1 Fe1 N2 C7 56.3(2) . . . . ? N3 Fe1 N2 C7 -26.6(2) . . . . ? C19 C18 N3 C12 -57.0(3) . . . . ? C19 C18 N3 C6 179.3(3) . . . . ? C19 C18 N3 Fe1 68.8(3) . . . . ? C13 C12 N3 C18 106.9(3) . . . . ? C13 C12 N3 C6 -131.7(3) . . . . ? C13 C12 N3 Fe1 -23.8(3) . . . . ? C7 C6 N3 C18 179.7(3) . . . . ? C5 C6 N3 C18 -68.0(3) . . . . ? C7 C6 N3 C12 57.1(3) . . . . ? C5 C6 N3 C12 169.4(3) . . . . ? C7 C6 N3 Fe1 -57.2(2) . . . . ? C5 C6 N3 Fe1 55.1(2) . . . . ? N5 Fe1 N3 C18 127.5(6) . . . . ? N4 Fe1 N3 C18 -109.6(2) . . . . ? N1 Fe1 N3 C18 72.8(2) . . . . ? N2 Fe1 N3 C18 160.8(2) . . . . ? S1 Fe1 N3 C18 -22.1(2) . . . . ? N5 Fe1 N3 C12 -105.9(7) . . . . ? N4 Fe1 N3 C12 17.09(19) . . . . ? N1 Fe1 N3 C12 -160.6(2) . . . . ? N2 Fe1 N3 C12 -72.56(19) . . . . ? S1 Fe1 N3 C12 104.58(18) . . . . ? N5 Fe1 N3 C6 11.4(7) . . . . ? N4 Fe1 N3 C6 134.37(19) . . . . ? N1 Fe1 N3 C6 -43.30(18) . . . . ? N2 Fe1 N3 C6 44.71(18) . . . . ? S1 Fe1 N3 C6 -138.14(17) . . . . ? C16 C17 N4 C13 -0.9(5) . . . . ? C16 C17 N4 Fe1 -178.0(2) . . . . ? C14 C13 N4 C17 -1.0(5) . . . . ? C12 C13 N4 C17 176.5(3) . . . . ? C14 C13 N4 Fe1 176.5(2) . . . . ? C12 C13 N4 Fe1 -6.0(3) . . . . ? N5 Fe1 N4 C17 -18.0(3) . . . . ? N1 Fe1 N4 C17 -178.4(4) . . . . ? N3 Fe1 N4 C17 170.5(3) . . . . ? N2 Fe1 N4 C17 -108.4(3) . . . . ? S1 Fe1 N4 C17 74.1(3) . . . . ? N5 Fe1 N4 C13 164.8(2) . . . . ? N1 Fe1 N4 C13 4.4(6) . . . . ? N3 Fe1 N4 C13 -6.7(2) . . . . ? N2 Fe1 N4 C13 74.4(2) . . . . ? S1 Fe1 N4 C13 -103.1(2) . . . . ? N4 Fe1 N5 C25 -153.7(7) . . . . ? N1 Fe1 N5 C25 22.3(7) . . . . ? N3 Fe1 N5 C25 -31.8(11) . . . . ? N2 Fe1 N5 C25 -64.6(7) . . . . ? S1 Fe1 N5 C25 117.9(7) . . . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.011 0.500 0.000 219 97 ' ' 2 -0.030 1.000 0.500 219 97 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.645 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.087 _iucr_refine_instructions_details ; TITL x0809a - SHELXL CELL 0.71073 9.3797 18.0863 15.6327 90.000 95.970 90.000 ZERR 4 0.0003 0.0005 0.0004 0.000 0.002 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 + Y , 0.50000 - Z SFAC C H FE N O S UNIT 100 84 4 20 8 8 TEMP -163 ACTA HTAB BOND BOND $H CONF WPDB L.S. 6 FMAP 2 PLAN 10 OMIT -2 50 OMIT 0 1 1 OMIT 0 2 0 OMIT 0 4 0 OMIT -1 2 1 OMIT 0 3 1 WGHT 0.075400 0.356200 FVAR 4.86644 FE1 3 0.370591 0.262581 0.154482 11.00000 0.02038 0.01580 = 0.01222 0.00056 0.00232 0.00086 S1 6 0.329494 0.233038 0.284950 11.00000 0.02428 0.02109 = 0.01540 0.00211 0.00146 0.00296 S2 6 0.786206 0.126790 0.135753 11.00000 0.02688 0.03327 = 0.03551 -0.00814 -0.00708 0.01142 C1 1 0.337764 0.100116 0.116348 11.00000 0.02524 0.01767 = 0.02322 0.00157 0.00805 0.00060 AFIX 43 H1 2 0.413059 0.090461 0.160409 11.00000 -1.20000 AFIX 0 C2 1 0.275221 0.041395 0.069827 11.00000 0.03505 0.02117 = 0.02729 0.00068 0.01141 -0.00001 AFIX 43 H2 2 0.308305 -0.007686 0.080764 11.00000 -1.20000 AFIX 0 C3 1 0.163268 0.055615 0.006912 11.00000 0.03613 0.02502 = 0.02592 -0.00888 0.01390 -0.01094 AFIX 43 H3 2 0.119205 0.016134 -0.026088 11.00000 -1.20000 AFIX 0 C4 1 0.115814 0.127295 -0.007761 11.00000 0.02423 0.02746 = 0.01779 -0.00311 0.00342 -0.00749 AFIX 43 H4 2 0.037939 0.137871 -0.049818 11.00000 -1.20000 AFIX 0 C5 1 0.184912 0.183032 0.040493 11.00000 0.02341 0.02076 = 0.01453 -0.00188 0.00654 -0.00361 C6 1 0.156360 0.264642 0.027798 11.00000 0.01948 0.02055 = 0.01148 -0.00135 -0.00168 -0.00202 AFIX 13 H6 2 0.060437 0.274943 -0.004136 11.00000 -1.20000 AFIX 0 C7 1 0.278035 0.293802 -0.017829 11.00000 0.02469 0.01769 = 0.01242 -0.00385 0.00144 0.00108 C8 1 0.271893 0.313862 -0.102509 11.00000 0.02996 0.02398 = 0.01312 -0.00107 -0.00235 -0.00029 AFIX 43 H8 2 0.184589 0.310646 -0.139020 11.00000 -1.20000 AFIX 0 C9 1 0.396291 0.339027 -0.133797 11.00000 0.04362 0.03017 = 0.01328 0.00342 0.00536 0.00396 AFIX 43 H9 2 0.395779 0.352914 -0.192436 11.00000 -1.20000 AFIX 0 C10 1 0.520971 0.343616 -0.078482 11.00000 0.02718 0.03401 = 0.02723 0.00525 0.01519 -0.00009 AFIX 43 H10 2 0.606607 0.362017 -0.098202 11.00000 -1.20000 AFIX 0 C11 1 0.519332 0.321138 0.005634 11.00000 0.02582 0.02152 = 0.02128 -0.00057 0.00536 0.00230 AFIX 43 H11 2 0.605541 0.323509 0.043244 11.00000 -1.20000 AFIX 0 C12 1 0.174985 0.381766 0.114202 11.00000 0.01719 0.01636 = 0.01800 0.00304 -0.00013 0.00368 AFIX 23 H12A 2 0.083811 0.401122 0.131938 11.00000 -1.20000 H12B 2 0.183507 0.398657 0.054711 11.00000 -1.20000 AFIX 0 C13 1 0.299582 0.411759 0.173801 11.00000 0.01917 0.01933 = 0.01213 0.00317 0.00121 -0.00122 C14 1 0.303901 0.484038 0.200873 11.00000 0.03033 0.01652 = 0.01643 0.00299 0.00266 0.00237 AFIX 43 H14 2 0.225355 0.516384 0.186195 11.00000 -1.20000 AFIX 0 C15 1 0.426270 0.508448 0.250269 11.00000 0.03131 0.02204 = 0.01870 0.00006 0.00301 -0.00719 AFIX 43 H15 2 0.433295 0.558339 0.269245 11.00000 -1.20000 AFIX 0 C16 1 0.537839 0.459838 0.271720 11.00000 0.02458 0.02963 = 0.01842 -0.00135 -0.00327 -0.00714 AFIX 43 H16 2 0.622673 0.475994 0.304956 11.00000 -1.20000 AFIX 0 C17 1 0.524434 0.388372 0.244507 11.00000 0.01921 0.02580 = 0.01348 0.00271 0.00093 -0.00028 AFIX 43 H17 2 0.600360 0.354819 0.260784 11.00000 -1.20000 AFIX 0 C18 1 0.054009 0.271551 0.164483 11.00000 0.01560 0.02411 = 0.02070 -0.00080 0.00243 -0.00376 AFIX 23 H18A 2 0.056847 0.216868 0.166930 11.00000 -1.20000 H18B 2 -0.038654 0.286275 0.132959 11.00000 -1.20000 AFIX 0 C19 1 0.062703 0.301716 0.254518 11.00000 0.02612 0.02068 = 0.01761 0.00140 0.00498 -0.00361 C20 1 -0.051375 0.342011 0.280493 11.00000 0.02327 0.03370 = 0.02790 -0.00078 0.00535 -0.00017 AFIX 43 H20 2 -0.132344 0.351607 0.240296 11.00000 -1.20000 AFIX 0 C21 1 -0.049516 0.368644 0.364265 11.00000 0.02730 0.03476 = 0.02613 -0.00426 0.01270 0.00502 AFIX 43 H21 2 -0.128902 0.395567 0.381185 11.00000 -1.20000 AFIX 0 C22 1 0.068767 0.355508 0.422337 11.00000 0.03572 0.02702 = 0.01727 -0.00245 0.01007 -0.00283 AFIX 43 H22 2 0.070415 0.373189 0.479655 11.00000 -1.20000 AFIX 0 C23 1 0.184668 0.316915 0.397876 11.00000 0.03046 0.02301 = 0.01945 0.00454 0.00089 -0.00277 AFIX 43 H23 2 0.267063 0.309352 0.437642 11.00000 -1.20000 AFIX 0 C24 1 0.180306 0.289030 0.314420 11.00000 0.01984 0.01618 = 0.02290 0.00057 0.00524 -0.00483 C25 1 0.658010 0.183645 0.157285 11.00000 0.02256 0.02246 = 0.01790 0.00419 -0.00510 -0.00308 N1 4 0.295670 0.170401 0.101363 11.00000 0.02014 0.01871 = 0.01509 0.00066 0.00478 -0.00188 N2 4 0.401075 0.296262 0.035808 11.00000 0.01942 0.01864 = 0.01561 -0.00155 0.00164 0.00409 N3 4 0.173198 0.298509 0.116622 11.00000 0.02024 0.01692 = 0.01044 -0.00171 0.00079 -0.00137 N4 4 0.407822 0.363404 0.195449 11.00000 0.01673 0.01813 = 0.01169 0.00254 0.00214 -0.00160 N5 4 0.563765 0.222783 0.170428 11.00000 0.02385 0.02185 = 0.01655 -0.00238 0.00089 0.00040 O1 5 0.278160 0.156191 0.296453 11.00000 0.04015 0.02199 = 0.02392 0.00638 0.00916 0.00295 O2 5 0.447412 0.252652 0.351015 11.00000 0.02516 0.03744 = 0.01751 0.00164 -0.00336 0.00832 HKLF 4 REM x0809a - SHELXL REM R1 = 0.0488 for 3549 Fo > 4sig(Fo) and 0.0673 for all 4646 data REM 316 parameters refined using 0 restraints END WGHT 0.0752 0.3729 REM Highest difference peak 0.645, deepest hole -0.522, 1-sigma level 0.087 Q1 1 0.2799 0.2092 0.3373 11.00000 0.05 0.65 Q2 1 0.4552 0.2523 0.1831 11.00000 0.05 0.51 Q3 1 0.4506 0.2580 0.1234 11.00000 0.05 0.46 Q4 1 0.8483 0.1069 0.1018 11.00000 0.05 0.42 Q5 1 0.3383 0.1954 0.4188 11.00000 0.05 0.40 Q6 1 0.7070 0.1242 0.1754 11.00000 0.05 0.40 Q7 1 0.6572 0.2356 0.1607 11.00000 0.05 0.38 Q8 1 0.3273 0.4542 0.1641 11.00000 0.05 0.33 Q9 1 0.2942 0.2504 0.1988 11.00000 0.05 0.33 Q10 1 0.2048 0.1506 0.2651 11.00000 0.05 0.32 ;