# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Chi Ming Che.' 'Guo-Su Fang.' 'Ella Wong' 'Nianyong Zhu.' _publ_contact_author_name 'Chi-Ming Che' _publ_contact_author_address ; Department of Chemistry The University of Hong Kong Hong Kong nil HONG KONG ; _publ_contact_author_email CMCHE@HKU.HK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Highly Cytotoxic Iron(II) Complexes with Pentadentate Pyridyl Ligands as a New Class of Anti-tumor Agents ; data_Complex_1b _database_code_depnum_ccdc_archive 'CCDC 274157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H31 Cl2 Fe N7 O8' _chemical_formula_sum 'C41 H31 Cl2 Fe N7 O8' _chemical_formula_weight 876.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 '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 13.072(3) _cell_length_b 13.181(3) _cell_length_c 14.660(3) _cell_angle_alpha 76.69(3) _cell_angle_beta 67.58(3) _cell_angle_gamma 62.77(3) _cell_volume 2071.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.554 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearch IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2805 _diffrn_reflns_av_R_equivalents 0.0725 _diffrn_reflns_av_sigmaI/netI 0.2094 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 23.52 _reflns_number_total 2193 _reflns_number_gt 918 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2193 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1903 _refine_ls_R_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.3377 _refine_ls_wR_factor_gt 0.2941 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.907 _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 0.6103(3) 0.3171(3) 0.2624(3) 0.0654(13) Uani 1 1 d . . . N1 N 0.5159(15) 0.1897(15) 0.3334(14) 0.069(5) Uiso 1 1 d . . . N2 N 0.4420(14) 0.3970(14) 0.3834(13) 0.062(5) Uiso 1 1 d . . . N3 N 0.6127(15) 0.4685(14) 0.3071(14) 0.068(5) Uiso 1 1 d . . . N4 N 0.7852(14) 0.3359(14) 0.1679(13) 0.066(5) Uiso 1 1 d . . . N5 N 0.7009(15) 0.2109(15) 0.1244(14) 0.073(5) Uiso 1 1 d . . . N6 N 0.7393(16) 0.1872(16) 0.3486(13) 0.073(6) Uiso 1 1 d . . . N7 N 0.4797(16) 0.4412(16) 0.1744(14) 0.074(6) Uiso 1 1 d . . . C1 C 0.574(2) 0.081(2) 0.3090(18) 0.079(7) Uiso 1 1 d . . . C2 C 0.513(2) 0.007(2) 0.351(2) 0.100(9) Uiso 1 1 d . . . C3 C 0.389(2) 0.050(2) 0.4162(19) 0.087(8) Uiso 1 1 d . . . C4 C 0.331(2) 0.169(2) 0.446(2) 0.095(8) Uiso 1 1 d . . . C5 C 0.3979(19) 0.2388(19) 0.3986(17) 0.072(7) Uiso 1 1 d . . . C6 C 0.3526(17) 0.3567(18) 0.4189(16) 0.059(6) Uiso 1 1 d . . . C7 C 0.2340(18) 0.418(2) 0.4753(17) 0.071(7) Uiso 1 1 d . . . C8 C 0.2010(19) 0.531(2) 0.5019(18) 0.074(7) Uiso 1 1 d . . . C9 C 0.2895(19) 0.5762(19) 0.4679(18) 0.074(7) Uiso 1 1 d . . . C10 C 0.4052(18) 0.5082(19) 0.4059(17) 0.066(6) Uiso 1 1 d . . . C11 C 0.5107(19) 0.544(2) 0.3638(18) 0.074(7) Uiso 1 1 d . . . C12 C 0.5086(17) 0.6454(17) 0.3932(16) 0.060(6) Uiso 1 1 d . . . C13 C 0.6134(19) 0.6667(19) 0.3539(18) 0.076(7) Uiso 1 1 d . . . C14 C 0.7192(19) 0.589(2) 0.2801(19) 0.081(7) Uiso 1 1 d . . . C15 C 0.7129(19) 0.4874(19) 0.2668(18) 0.072(7) Uiso 1 1 d . . . C16 C 0.8141(19) 0.4072(19) 0.1948(17) 0.068(7) Uiso 1 1 d . . . C17 C 0.9372(17) 0.4023(17) 0.1560(16) 0.060(6) Uiso 1 1 d . . . C18 C 1.0238(18) 0.3220(18) 0.0863(17) 0.066(6) Uiso 1 1 d . . . C19 C 0.9917(18) 0.2468(19) 0.0526(18) 0.069(7) Uiso 1 1 d . . . C20 C 0.8671(19) 0.2571(18) 0.1011(17) 0.069(7) Uiso 1 1 d . . . C21 C 0.8149(18) 0.1925(18) 0.0701(18) 0.067(7) Uiso 1 1 d . . . C22 C 0.8790(19) 0.1311(19) -0.0152(18) 0.070(7) Uiso 1 1 d . . . C23 C 0.819(2) 0.083(2) -0.0498(19) 0.082(7) Uiso 1 1 d . . . C24 C 0.699(2) 0.107(2) 0.0064(19) 0.076(7) Uiso 1 1 d . . . C25 C 0.635(2) 0.171(2) 0.093(2) 0.087(8) Uiso 1 1 d . . . C26 C 0.074(2) 0.602(2) 0.5662(19) 0.079(7) Uiso 1 1 d . . . C27 C 0.003(2) 0.539(2) 0.633(2) 0.086(8) Uiso 1 1 d . . . C28 C -0.112(2) 0.608(2) 0.6976(18) 0.078(7) Uiso 1 1 d . . . C29 C -0.153(2) 0.734(2) 0.699(2) 0.089(8) Uiso 1 1 d . . . C30 C -0.086(2) 0.791(2) 0.6381(19) 0.081(7) Uiso 1 1 d . . . C31 C 0.030(2) 0.725(2) 0.559(2) 0.093(8) Uiso 1 1 d . . . C32 C 1.155(2) 0.312(2) 0.034(2) 0.087(8) Uiso 1 1 d . . . C33 C 1.1753(19) 0.4087(19) 0.0354(17) 0.073(7) Uiso 1 1 d . . . C34 C 1.298(2) 0.398(2) -0.015(2) 0.084(8) Uiso 1 1 d . . . C35 C 1.390(2) 0.302(3) -0.055(2) 0.112(10) Uiso 1 1 d . . . C36 C 1.370(3) 0.207(3) -0.056(3) 0.128(11) Uiso 1 1 d . . . C37 C 1.244(3) 0.209(3) -0.003(2) 0.126(10) Uiso 1 1 d . . . C38 C 0.815(2) 0.106(2) 0.3707(19) 0.074(7) Uiso 1 1 d . . . C39 C 0.916(2) 0.006(2) 0.398(2) 0.103(9) Uiso 1 1 d . . . C40 C 0.395(2) 0.514(2) 0.1587(18) 0.075(7) Uiso 1 1 d . . . C41 C 0.284(2) 0.618(2) 0.135(2) 0.108(9) Uiso 1 1 d . . . Cl1 Cl 1.2799(6) 0.8859(6) 0.2857(6) 0.089(2) Uani 1 1 d . . . Cl2 Cl 0.9027(7) 0.7819(7) 0.2471(6) 0.098(3) Uani 1 1 d . . . O1 O 1.3248(19) 0.776(2) 0.2460(18) 0.146(8) Uiso 1 1 d . . . O2 O 1.1962(18) 0.9771(18) 0.2371(16) 0.128(7) Uiso 1 1 d . . . O3 O 1.2255(18) 0.8813(17) 0.3891(19) 0.135(8) Uiso 1 1 d . . . O4 O 1.387(2) 0.908(2) 0.259(2) 0.199(11) Uiso 1 1 d . . . O5 O 0.9665(16) 0.6880(17) 0.1859(16) 0.121(6) Uiso 1 1 d . . . O6 O 0.8021(17) 0.7735(17) 0.3204(17) 0.129(7) Uiso 1 1 d . . . O7 O 0.875(2) 0.886(3) 0.202(3) 0.212(12) Uiso 1 1 d . . . O8 O 0.974(3) 0.764(3) 0.303(3) 0.264(16) Uiso 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 0.069(2) 0.057(2) 0.083(3) -0.0056(19) -0.0214(18) -0.0368(18) Cl1 0.076(4) 0.093(5) 0.107(7) -0.020(5) -0.026(4) -0.037(4) Cl2 0.099(5) 0.085(6) 0.113(7) -0.001(5) -0.017(5) -0.056(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 Fe1 N2 2.205(17) . ? Fe1 N3 2.256(17) . ? Fe1 N4 2.270(17) . ? Fe1 N6 2.314(19) . ? Fe1 N7 2.33(2) . ? Fe1 N5 2.327(19) . ? Fe1 N1 2.353(17) . ? N1 C1 1.34(3) . ? N1 C5 1.40(2) . ? N2 C6 1.38(2) . ? N2 C10 1.39(2) . ? N3 C15 1.33(2) . ? N3 C11 1.33(3) . ? N4 C16 1.34(2) . ? N4 C20 1.35(3) . ? N5 C21 1.33(2) . ? N5 C25 1.43(3) . ? N6 C38 1.16(2) . ? N7 C40 1.15(2) . ? C1 C2 1.42(3) . ? C2 C3 1.44(3) . ? C3 C4 1.49(3) . ? C4 C5 1.44(3) . ? C5 C6 1.45(3) . ? C6 C7 1.39(3) . ? C7 C8 1.45(3) . ? C8 C9 1.42(3) . ? C8 C26 1.52(3) . ? C9 C10 1.42(3) . ? C10 C11 1.52(3) . ? C11 C12 1.48(3) . ? C12 C13 1.40(3) . ? C13 C14 1.49(3) . ? C14 C15 1.44(3) . ? C15 C16 1.47(3) . ? C16 C17 1.46(3) . ? C17 C18 1.40(3) . ? C18 C19 1.47(3) . ? C18 C32 1.54(3) . ? C19 C20 1.46(3) . ? C20 C21 1.53(3) . ? C21 C22 1.40(3) . ? C22 C23 1.48(3) . ? C23 C24 1.38(3) . ? C24 C25 1.44(3) . ? C26 C31 1.44(3) . ? C26 C27 1.46(3) . ? C27 C28 1.43(3) . ? C28 C29 1.49(3) . ? C29 C30 1.34(3) . ? C30 C31 1.52(3) . ? C32 C37 1.38(3) . ? C32 C33 1.42(3) . ? C33 C34 1.44(3) . ? C34 C35 1.35(3) . ? C35 C36 1.39(4) . ? C36 C37 1.51(4) . ? C38 C39 1.49(3) . ? C40 C41 1.56(3) . ? Cl1 O3 1.41(2) . ? Cl1 O4 1.44(3) . ? Cl1 O1 1.46(2) . ? Cl1 O2 1.46(2) . ? Cl2 O7 1.32(3) . ? Cl2 O8 1.37(4) . ? Cl2 O6 1.38(2) . ? Cl2 O5 1.42(2) . ? 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 N2 Fe1 N3 70.7(6) . . ? N2 Fe1 N4 141.2(7) . . ? N3 Fe1 N4 70.6(6) . . ? N2 Fe1 N6 101.9(6) . . ? N3 Fe1 N6 92.9(6) . . ? N4 Fe1 N6 80.1(6) . . ? N2 Fe1 N7 78.7(6) . . ? N3 Fe1 N7 89.5(6) . . ? N4 Fe1 N7 101.0(6) . . ? N6 Fe1 N7 177.6(6) . . ? N2 Fe1 N5 146.0(6) . . ? N3 Fe1 N5 137.8(7) . . ? N4 Fe1 N5 70.3(6) . . ? N6 Fe1 N5 95.4(6) . . ? N7 Fe1 N5 82.9(6) . . ? N2 Fe1 N1 70.3(7) . . ? N3 Fe1 N1 137.8(7) . . ? N4 Fe1 N1 145.9(6) . . ? N6 Fe1 N1 79.9(6) . . ? N7 Fe1 N1 98.1(6) . . ? N5 Fe1 N1 84.4(6) . . ? C1 N1 C5 125(2) . . ? C1 N1 Fe1 120.5(15) . . ? C5 N1 Fe1 114.3(15) . . ? C6 N2 C10 115.3(17) . . ? C6 N2 Fe1 121.5(13) . . ? C10 N2 Fe1 120.4(14) . . ? C15 N3 C11 121(2) . . ? C15 N3 Fe1 118.6(15) . . ? C11 N3 Fe1 119.8(15) . . ? C16 N4 C20 122.1(19) . . ? C16 N4 Fe1 118.3(16) . . ? C20 N4 Fe1 117.9(14) . . ? C21 N5 C25 119(2) . . ? C21 N5 Fe1 118.8(16) . . ? C25 N5 Fe1 122.0(15) . . ? C38 N6 Fe1 162.1(17) . . ? C40 N7 Fe1 159.4(17) . . ? N1 C1 C2 119(2) . . ? C1 C2 C3 120(2) . . ? C2 C3 C4 119(2) . . ? C5 C4 C3 117(2) . . ? N1 C5 C4 119(2) . . ? N1 C5 C6 117(2) . . ? C4 C5 C6 123(2) . . ? N2 C6 C7 124(2) . . ? N2 C6 C5 112.6(18) . . ? C7 C6 C5 123(2) . . ? C6 C7 C8 119(2) . . ? C9 C8 C7 119(2) . . ? C9 C8 C26 119(2) . . ? C7 C8 C26 122(2) . . ? C10 C9 C8 116(2) . . ? N2 C10 C9 126(2) . . ? N2 C10 C11 111.0(18) . . ? C9 C10 C11 123(2) . . ? N3 C11 C12 121(2) . . ? N3 C11 C10 114(2) . . ? C12 C11 C10 124(2) . . ? C13 C12 C11 119.0(19) . . ? C12 C13 C14 117(2) . . ? C15 C14 C13 117(2) . . ? N3 C15 C14 123(2) . . ? N3 C15 C16 116(2) . . ? C14 C15 C16 120(2) . . ? N4 C16 C17 122(2) . . ? N4 C16 C15 114(2) . . ? C17 C16 C15 124(2) . . ? C18 C17 C16 117.3(19) . . ? C17 C18 C19 121(2) . . ? C17 C18 C32 123(2) . . ? C19 C18 C32 116(2) . . ? C20 C19 C18 115(2) . . ? N4 C20 C19 122(2) . . ? N4 C20 C21 115.0(19) . . ? C19 C20 C21 123(2) . . ? N5 C21 C22 124(2) . . ? N5 C21 C20 114(2) . . ? C22 C21 C20 122(2) . . ? C21 C22 C23 120(2) . . ? C24 C23 C22 114(2) . . ? C23 C24 C25 125(2) . . ? N5 C25 C24 117(2) . . ? C31 C26 C27 124(2) . . ? C31 C26 C8 120(2) . . ? C27 C26 C8 117(2) . . ? C28 C27 C26 115(2) . . ? C27 C28 C29 122(2) . . ? C30 C29 C28 123(2) . . ? C29 C30 C31 118(2) . . ? C26 C31 C30 118(2) . . ? C37 C32 C33 125(2) . . ? C37 C32 C18 119(2) . . ? C33 C32 C18 116(2) . . ? C32 C33 C34 115(2) . . ? C35 C34 C33 123(2) . . ? C34 C35 C36 121(3) . . ? C35 C36 C37 119(3) . . ? C32 C37 C36 116(3) . . ? N6 C38 C39 176(2) . . ? N7 C40 C41 176(2) . . ? O3 Cl1 O4 110.9(15) . . ? O3 Cl1 O1 111.6(14) . . ? O4 Cl1 O1 104.1(14) . . ? O3 Cl1 O2 111.2(12) . . ? O4 Cl1 O2 107.8(15) . . ? O1 Cl1 O2 110.8(13) . . ? O7 Cl2 O8 110(2) . . ? O7 Cl2 O6 111.0(16) . . ? O8 Cl2 O6 100.1(19) . . ? O7 Cl2 O5 117.1(17) . . ? O8 Cl2 O5 105.5(18) . . ? O6 Cl2 O5 111.3(13) . . ? _diffrn_measured_fraction_theta_max 0.356 _diffrn_reflns_theta_full 23.52 _diffrn_measured_fraction_theta_full 0.356 _refine_diff_density_max 0.469 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.119 data_Complex_1a _database_code_depnum_ccdc_archive 'CCDC 274158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H27.50 Cl2 Fe N8.50 O8' _chemical_formula_sum 'C32 H27.50 Cl2 Fe N8.50 O8' _chemical_formula_weight 785.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 '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 11.732(2) _cell_length_b 12.453(3) _cell_length_c 13.997(3) _cell_angle_alpha 94.77(3) _cell_angle_beta 113.14(3) _cell_angle_gamma 104.39(3) _cell_volume 1783.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 806 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Marresearch Imaging Plate mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4652 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.1367 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 23.85 _reflns_number_total 3030 _reflns_number_gt 1514 _reflns_threshold_expression >2sigma(I) _computing_data_collection MarControl _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1848P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3030 _refine_ls_number_parameters 419 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0941 _refine_ls_wR_factor_ref 0.2811 _refine_ls_wR_factor_gt 0.2494 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.956 _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 0.75393(16) 0.24645(15) 0.24676(12) 0.0737(8) Uani 1 1 d . . . N1 N 0.5309(10) 0.1642(8) 0.1993(10) 0.075(3) Uani 1 1 d . . . N2 N 0.6432(12) 0.1791(8) 0.0704(8) 0.071(3) Uani 1 1 d . . . N3 N 0.8912(11) 0.2345(8) 0.1729(12) 0.081(3) Uani 1 1 d . . . N4 N 0.9630(12) 0.3034(9) 0.3727(11) 0.089(3) Uani 1 1 d . . . N5 N 0.7608(14) 0.3405(9) 0.3971(9) 0.087(3) Uani 1 1 d . . . N6 N 0.7404(11) 0.4040(10) 0.1924(9) 0.088(4) Uani 1 1 d . . . N7 N 0.7632(10) 0.0934(10) 0.3111(9) 0.093(4) Uani 1 1 d . . . C1 C 0.4800(17) 0.1379(13) 0.2688(12) 0.096(4) Uani 1 1 d . . . H1 H 0.5364 0.1521 0.3405 0.115 Uiso 1 1 calc R . . C2 C 0.350(2) 0.0915(13) 0.2389(17) 0.106(5) Uani 1 1 d . . . H2 H 0.3182 0.0741 0.2887 0.127 Uiso 1 1 calc R . . C3 C 0.2687(16) 0.0712(13) 0.134(2) 0.116(6) Uani 1 1 d . . . H3 H 0.1793 0.0429 0.1120 0.139 Uiso 1 1 calc R . . C4 C 0.3161(16) 0.0919(13) 0.0596(13) 0.099(5) Uani 1 1 d . . . H4 H 0.2607 0.0748 -0.0125 0.119 Uiso 1 1 calc R . . C5 C 0.4504(15) 0.1394(11) 0.0961(13) 0.082(4) Uani 1 1 d . . . C6 C 0.5173(16) 0.1586(10) 0.0249(12) 0.079(4) Uani 1 1 d . . . C7 C 0.4439(16) 0.1557(13) -0.0834(14) 0.106(5) Uani 1 1 d . . . H7 H 0.3546 0.1445 -0.1120 0.128 Uiso 1 1 calc R . . C8 C 0.510(2) 0.1701(16) -0.1422(14) 0.131(7) Uani 1 1 d . . . H8 H 0.4668 0.1678 -0.2144 0.158 Uiso 1 1 calc R . . C9 C 0.641(2) 0.1879(14) -0.0980(16) 0.123(6) Uani 1 1 d . . . H9 H 0.6859 0.1959 -0.1401 0.147 Uiso 1 1 calc R . . C10 C 0.7072(17) 0.1943(11) 0.0099(14) 0.087(4) Uani 1 1 d . . . C11 C 0.8461(19) 0.2137(11) 0.0659(15) 0.096(4) Uani 1 1 d . . . C12 C 0.934(2) 0.2151(13) 0.0209(17) 0.129(6) Uani 1 1 d . . . H12 H 0.9062 0.1996 -0.0522 0.155 Uiso 1 1 calc R . . C13 C 1.067(3) 0.2415(18) 0.093(3) 0.156(9) Uani 1 1 d . . . H13 H 1.1279 0.2456 0.0656 0.187 Uiso 1 1 calc R . . C14 C 1.109(2) 0.2605(17) 0.197(2) 0.131(7) Uani 1 1 d . . . H14 H 1.1967 0.2756 0.2424 0.158 Uiso 1 1 calc R . . C15 C 1.0161(18) 0.2567(12) 0.2341(18) 0.095(4) Uani 1 1 d . . . C16 C 1.0538(14) 0.2838(12) 0.3466(18) 0.096(5) Uani 1 1 d . . . C17 C 1.170(2) 0.2889(16) 0.422(2) 0.144(8) Uani 1 1 d . . . H17 H 1.2344 0.2744 0.4047 0.172 Uiso 1 1 calc R . . C18 C 1.192(2) 0.3175(18) 0.531(3) 0.173(14) Uani 1 1 d . . . H18 H 1.2714 0.3194 0.5842 0.208 Uiso 1 1 calc R . . C19 C 1.102(2) 0.3414(16) 0.5568(15) 0.134(7) Uani 1 1 d . . . H19 H 1.1173 0.3628 0.6270 0.161 Uiso 1 1 calc R . . C20 C 0.9814(18) 0.3322(12) 0.4704(16) 0.097(5) Uani 1 1 d . . . C21 C 0.875(2) 0.3544(12) 0.4837(12) 0.096(5) Uani 1 1 d . . . C22 C 0.887(2) 0.3995(17) 0.5834(19) 0.144(8) Uani 1 1 d . . . H22 H 0.9612 0.4081 0.6449 0.173 Uiso 1 1 calc R . . C23 C 0.785(3) 0.4302(15) 0.5871(15) 0.137(8) Uani 1 1 d . . . H23 H 0.7937 0.4603 0.6536 0.165 Uiso 1 1 calc R . . C24 C 0.672(2) 0.4211(14) 0.5028(18) 0.117(5) Uani 1 1 d . . . H24 H 0.6042 0.4435 0.5075 0.141 Uiso 1 1 calc R . . C25 C 0.6704(17) 0.3727(11) 0.4055(12) 0.095(4) Uani 1 1 d . . . H25 H 0.5966 0.3641 0.3434 0.114 Uiso 1 1 calc R . . C26 C 0.7195(13) 0.4773(17) 0.1527(10) 0.093(5) Uani 1 1 d . . . C27 C 0.6954(16) 0.5792(13) 0.1039(11) 0.117(5) Uani 1 1 d . . . C28 C 0.7836(13) 0.0275(14) 0.3601(12) 0.087(4) Uani 1 1 d . . . C29 C 0.8137(18) -0.0630(15) 0.4259(12) 0.135(6) Uani 1 1 d . . . Cl1 Cl 0.9893(4) -0.1079(4) 0.2363(3) 0.1252(15) Uiso 1 1 d D . . Cl2 Cl 0.4128(4) 0.5173(5) 0.2269(4) 0.152(2) Uani 1 1 d D . . O1 O 0.8599(18) -0.1494(17) 0.2311(16) 0.137(7) Uiso 0.50 1 d PD A 1 O2 O 0.985(3) -0.038(2) 0.163(2) 0.216(12) Uiso 0.50 1 d PD A 1 O3 O 1.026(2) -0.2032(18) 0.2136(19) 0.182(10) Uiso 0.50 1 d PD A 1 O4 O 1.077(2) -0.049(3) 0.3411(18) 0.28(2) Uiso 0.50 1 d PD A 1 O1' O 0.993(3) -0.177(2) 0.309(2) 0.228(13) Uiso 0.50 1 d PD A 2 O2' O 1.063(2) 0.003(2) 0.294(2) 0.176(10) Uiso 0.50 1 d PD A 2 O3' O 1.052(3) -0.139(3) 0.179(2) 0.283(19) Uiso 0.50 1 d PD A 2 O4' O 0.867(3) -0.110(3) 0.173(2) 0.33(3) Uiso 0.50 1 d PD A 2 O5 O 0.4123(17) 0.4253(14) 0.1569(13) 0.297(10) Uiso 1 1 d D . . O6 O 0.3051(14) 0.5460(14) 0.1766(11) 0.239(7) Uiso 1 1 d D . . O7 O 0.4103(13) 0.4684(12) 0.3126(10) 0.207(6) Uiso 1 1 d D . . O8 O 0.5247(13) 0.5988(12) 0.2529(11) 0.227(7) Uiso 1 1 d D . . N8 N 0.005(4) 0.534(4) 0.141(3) 0.195(16) Uiso 0.50 1 d P . . C30 C -0.014(4) 0.519(3) 0.034(3) 0.093(13) Uiso 0.50 1 d P . . C31 C -0.004(5) 0.490(4) -0.073(4) 0.13(2) Uiso 0.50 1 d P . . N9 N 0.445(3) 0.153(3) 0.517(2) 0.307(13) Uiso 1 1 d . . . C32 C 0.544(3) 0.143(2) 0.576(2) 0.195(9) Uiso 1 1 d . . . C33 C 0.678(2) 0.164(2) 0.6292(17) 0.190(8) Uiso 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 0.0705(13) 0.0598(13) 0.0762(13) 0.0069(9) 0.0205(9) 0.0161(9) N1 0.076(7) 0.050(7) 0.096(9) 0.004(6) 0.040(8) 0.013(6) N2 0.067(8) 0.061(7) 0.073(7) 0.010(6) 0.022(7) 0.016(6) N3 0.058(8) 0.066(8) 0.123(10) 0.015(7) 0.041(7) 0.021(6) N4 0.084(9) 0.061(8) 0.081(9) 0.004(6) 0.008(8) 0.004(6) N5 0.121(10) 0.052(7) 0.072(8) 0.000(6) 0.034(9) 0.015(7) N6 0.100(9) 0.069(9) 0.072(8) 0.007(7) 0.019(7) 0.017(7) N7 0.083(8) 0.052(8) 0.124(10) 0.026(7) 0.031(7) 0.009(7) C1 0.094(13) 0.093(12) 0.107(11) 0.018(9) 0.047(10) 0.029(10) C2 0.104(14) 0.080(12) 0.151(17) 0.012(11) 0.078(13) 0.021(11) C3 0.074(11) 0.064(11) 0.180(19) 0.012(13) 0.030(14) 0.016(9) C4 0.077(13) 0.097(13) 0.104(12) 0.013(10) 0.023(10) 0.023(10) C5 0.069(11) 0.059(9) 0.085(11) -0.002(8) 0.003(10) 0.022(8) C6 0.085(11) 0.048(9) 0.088(12) 0.006(7) 0.024(10) 0.017(8) C7 0.105(12) 0.099(12) 0.084(12) -0.003(9) 0.018(11) 0.024(10) C8 0.140(18) 0.138(17) 0.079(12) 0.005(11) 0.012(13) 0.045(15) C9 0.18(2) 0.114(14) 0.093(14) 0.025(11) 0.079(14) 0.041(14) C10 0.097(12) 0.056(9) 0.098(13) 0.001(8) 0.041(12) 0.011(8) C11 0.132(16) 0.063(10) 0.108(13) 0.008(9) 0.072(13) 0.023(10) C12 0.175(19) 0.080(12) 0.187(18) 0.029(12) 0.125(19) 0.051(13) C13 0.17(2) 0.106(16) 0.29(3) 0.05(2) 0.16(3) 0.083(17) C14 0.102(15) 0.122(16) 0.167(19) 0.007(15) 0.060(17) 0.035(11) C15 0.081(13) 0.060(10) 0.141(16) 0.024(10) 0.043(15) 0.023(9) C16 0.033(9) 0.069(10) 0.151(18) 0.023(10) 0.005(11) 0.013(7) C17 0.087(16) 0.085(14) 0.23(2) 0.048(17) 0.035(18) 0.020(11) C18 0.094(17) 0.082(15) 0.23(3) 0.037(18) -0.04(2) 0.008(12) C19 0.122(17) 0.087(14) 0.111(14) 0.033(10) -0.013(15) -0.004(13) C20 0.098(14) 0.058(10) 0.100(15) 0.020(9) 0.017(14) 0.009(9) C21 0.142(17) 0.063(10) 0.041(9) -0.003(8) 0.022(11) -0.006(10) C22 0.152(19) 0.082(14) 0.15(2) 0.028(13) 0.029(16) 0.016(13) C23 0.24(3) 0.075(13) 0.075(13) 0.009(10) 0.061(17) 0.025(16) C24 0.176(19) 0.082(12) 0.139(15) 0.029(12) 0.110(16) 0.042(12) C25 0.123(13) 0.055(10) 0.104(13) 0.010(8) 0.049(11) 0.021(9) C26 0.079(10) 0.122(16) 0.050(9) -0.031(10) 0.026(8) 0.005(11) C27 0.190(16) 0.078(11) 0.115(11) 0.064(9) 0.073(11) 0.065(11) C28 0.081(10) 0.069(12) 0.107(11) 0.007(9) 0.043(9) 0.013(9) C29 0.189(17) 0.121(14) 0.137(13) 0.085(12) 0.083(13) 0.078(13) Cl2 0.102(3) 0.214(6) 0.130(4) 0.061(4) 0.039(3) 0.040(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 Fe1 N6 2.183(12) . ? Fe1 N7 2.184(12) . ? Fe1 N2 2.254(10) . ? Fe1 N3 2.255(10) . ? Fe1 N4 2.271(11) . ? Fe1 N5 2.284(11) . ? Fe1 N1 2.351(10) . ? N1 C5 1.335(14) . ? N1 C1 1.350(16) . ? N2 C6 1.304(14) . ? N2 C10 1.330(16) . ? N3 C15 1.316(17) . ? N3 C11 1.355(16) . ? N4 C20 1.300(18) . ? N4 C16 1.323(17) . ? N5 C25 1.265(16) . ? N5 C21 1.369(18) . ? N6 C26 1.135(18) . ? N7 C28 1.123(15) . ? C1 C2 1.360(18) . ? C2 C3 1.362(19) . ? C3 C4 1.37(2) . ? C4 C5 1.395(18) . ? C5 C6 1.493(18) . ? C6 C7 1.411(17) . ? C7 C8 1.33(2) . ? C8 C9 1.36(2) . ? C9 C10 1.385(19) . ? C10 C11 1.448(19) . ? C11 C12 1.40(2) . ? C12 C13 1.42(3) . ? C13 C14 1.31(2) . ? C14 C15 1.37(2) . ? C15 C16 1.44(2) . ? C16 C17 1.34(2) . ? C17 C18 1.43(3) . ? C18 C19 1.33(3) . ? C19 C20 1.43(2) . ? C20 C21 1.41(2) . ? C21 C22 1.40(2) . ? C22 C23 1.36(2) . ? C23 C24 1.35(2) . ? C24 C25 1.434(19) . ? C26 C27 1.53(2) . ? C28 C29 1.54(2) . ? Cl1 O4' 1.35(2) . ? Cl1 O3' 1.38(2) . ? Cl1 O1' 1.38(2) . ? Cl1 O2 1.39(2) . ? Cl1 O2' 1.40(2) . ? Cl1 O3 1.412(19) . ? Cl1 O4 1.42(2) . ? Cl1 O1 1.447(17) . ? Cl2 O6 1.337(13) . ? Cl2 O8 1.337(13) . ? Cl2 O7 1.396(12) . ? Cl2 O5 1.442(13) . ? N8 C31 0.97(5) 2_565 ? N8 C30 1.42(6) . ? C30 C31 0.54(7) 2_565 ? C30 C30 1.20(6) 2_565 ? C30 C31 1.56(5) . ? C31 C30 0.54(7) 2_565 ? C31 N8 0.97(5) 2_565 ? C31 C31 2.00(11) 2_565 ? N9 C32 1.18(3) . ? C32 C33 1.39(3) . ? 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 N6 Fe1 N7 175.4(4) . . ? N6 Fe1 N2 80.1(4) . . ? N7 Fe1 N2 103.2(4) . . ? N6 Fe1 N3 89.7(4) . . ? N7 Fe1 N3 94.5(4) . . ? N2 Fe1 N3 69.2(5) . . ? N6 Fe1 N4 100.6(4) . . ? N7 Fe1 N4 79.2(4) . . ? N2 Fe1 N4 138.7(5) . . ? N3 Fe1 N4 69.5(6) . . ? N6 Fe1 N5 83.3(4) . . ? N7 Fe1 N5 92.3(4) . . ? N2 Fe1 N5 147.6(5) . . ? N3 Fe1 N5 138.5(5) . . ? N4 Fe1 N5 71.7(5) . . ? N6 Fe1 N1 97.1(4) . . ? N7 Fe1 N1 81.2(4) . . ? N2 Fe1 N1 69.1(5) . . ? N3 Fe1 N1 135.8(4) . . ? N4 Fe1 N1 149.2(5) . . ? N5 Fe1 N1 85.7(5) . . ? C5 N1 C1 118.3(12) . . ? C5 N1 Fe1 117.2(10) . . ? C1 N1 Fe1 124.5(10) . . ? C6 N2 C10 118.0(12) . . ? C6 N2 Fe1 119.8(10) . . ? C10 N2 Fe1 118.9(10) . . ? C15 N3 C11 120.4(15) . . ? C15 N3 Fe1 119.6(13) . . ? C11 N3 Fe1 119.7(10) . . ? C20 N4 C16 123.2(16) . . ? C20 N4 Fe1 116.9(12) . . ? C16 N4 Fe1 118.4(11) . . ? C25 N5 C21 121.3(14) . . ? C25 N5 Fe1 126.7(11) . . ? C21 N5 Fe1 111.9(12) . . ? C26 N6 Fe1 171.0(13) . . ? C28 N7 Fe1 167.9(12) . . ? N1 C1 C2 123.0(14) . . ? C1 C2 C3 117.9(16) . . ? C2 C3 C4 121.2(16) . . ? C3 C4 C5 117.5(15) . . ? N1 C5 C4 121.8(15) . . ? N1 C5 C6 114.3(13) . . ? C4 C5 C6 123.7(15) . . ? N2 C6 C7 124.8(14) . . ? N2 C6 C5 115.6(13) . . ? C7 C6 C5 119.7(16) . . ? C8 C7 C6 115.9(16) . . ? C7 C8 C9 120.7(17) . . ? C8 C9 C10 120.1(17) . . ? N2 C10 C9 120.5(15) . . ? N2 C10 C11 114.6(15) . . ? C9 C10 C11 124.9(18) . . ? N3 C11 C12 119.4(17) . . ? N3 C11 C10 113.7(15) . . ? C12 C11 C10 126.9(19) . . ? C11 C12 C13 116.2(19) . . ? C14 C13 C12 124(2) . . ? C13 C14 C15 116(2) . . ? N3 C15 C14 124.2(19) . . ? N3 C15 C16 115.6(16) . . ? C14 C15 C16 120.1(19) . . ? N4 C16 C17 120(2) . . ? N4 C16 C15 114.9(14) . . ? C17 C16 C15 125(2) . . ? C16 C17 C18 118(2) . . ? C19 C18 C17 122(2) . . ? C18 C19 C20 116(2) . . ? N4 C20 C21 115.7(16) . . ? N4 C20 C19 121.0(19) . . ? C21 C20 C19 123(2) . . ? N5 C21 C22 117.7(19) . . ? N5 C21 C20 120.2(14) . . ? C22 C21 C20 122(2) . . ? C23 C22 C21 118(2) . . ? C24 C23 C22 126.0(19) . . ? C23 C24 C25 111.5(16) . . ? N5 C25 C24 125.5(16) . . ? N6 C26 C27 177.5(16) . . ? N7 C28 C29 178.6(15) . . ? O4' Cl1 O3' 112.0(12) . . ? O4' Cl1 O1' 112.5(12) . . ? O3' Cl1 O1' 108.5(11) . . ? O4' Cl1 O2 67.0(15) . . ? O3' Cl1 O2 72.1(14) . . ? O1' Cl1 O2 179.4(13) . . ? O4' Cl1 O2' 109.6(12) . . ? O3' Cl1 O2' 106.5(11) . . ? O1' Cl1 O2' 107.4(11) . . ? O2 Cl1 O2' 72.5(13) . . ? O4' Cl1 O3 116.2(17) . . ? O3' Cl1 O3 42.9(13) . . ? O1' Cl1 O3 67.9(13) . . ? O2 Cl1 O3 112.7(10) . . ? O2' Cl1 O3 131.9(14) . . ? O4' Cl1 O4 132.4(19) . . ? O3' Cl1 O4 112.3(18) . . ? O1' Cl1 O4 68.2(14) . . ? O2 Cl1 O4 111.9(11) . . ? O2' Cl1 O4 39.9(13) . . ? O3 Cl1 O4 107.9(10) . . ? O4' Cl1 O1 41.8(14) . . ? O3' Cl1 O1 135.1(15) . . ? O1' Cl1 O1 71.5(12) . . ? O2 Cl1 O1 108.0(10) . . ? O2' Cl1 O1 116.4(13) . . ? O3 Cl1 O1 107.3(10) . . ? O4 Cl1 O1 109.0(10) . . ? O6 Cl2 O8 115.0(9) . . ? O6 Cl2 O7 112.0(8) . . ? O8 Cl2 O7 112.4(8) . . ? O6 Cl2 O5 108.0(9) . . ? O8 Cl2 O5 105.9(8) . . ? O7 Cl2 O5 102.3(9) . . ? C31 N8 C30 14(4) 2_565 . ? C31 C30 C30 122(10) 2_565 2_565 ? C31 C30 N8 27(8) 2_565 . ? C30 C30 N8 149(5) 2_565 . ? C31 C30 C31 139(8) 2_565 . ? C30 C30 C31 17(3) 2_565 . ? N8 C30 C31 165(3) . . ? C30 C31 N8 139(10) 2_565 2_565 ? C30 C31 C30 41(8) 2_565 . ? N8 C31 C30 175(5) 2_565 . ? C30 C31 C31 31(6) 2_565 2_565 ? N8 C31 C31 168(7) 2_565 2_565 ? C30 C31 C31 10(2) . 2_565 ? N9 C32 C33 158(3) . . ? _diffrn_measured_fraction_theta_max 0.550 _diffrn_reflns_theta_full 23.85 _diffrn_measured_fraction_theta_full 0.550 _refine_diff_density_max 0.545 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.081 data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 274159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H25 Cl F3 Fe N5 O6 S' _chemical_formula_sum 'C29 H25 Cl F3 Fe N5 O6 S' _chemical_formula_weight 719.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' F F 0.0171 0.0103 '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' _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 8.570(2) _cell_length_b 12.315(3) _cell_length_c 15.762(3) _cell_angle_alpha 102.03(3) _cell_angle_beta 97.89(3) _cell_angle_gamma 108.04(3) _cell_volume 1510.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.728 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearach IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6218 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3711 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1039P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3711 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 Fe1 Fe 0.44392(11) 0.07912(8) 0.24182(6) 0.0302(3) Uani 1 1 d . . . Cl1 Cl 0.54676(19) -0.03239(15) 0.13476(11) 0.0403(5) Uani 1 1 d . . . O1 O 0.7293(5) 0.3672(4) 0.5069(3) 0.0401(11) Uani 1 1 d . . . H1 H 0.6888 0.3518 0.5491 0.060 Uiso 1 1 calc R . . O2 O -0.0938(5) 0.0784(4) 0.2444(3) 0.0459(12) Uani 1 1 d . . . H2 H -0.1640 0.0254 0.2040 0.069 Uiso 1 1 calc R . . O3 O 0.3641(6) 0.6400(5) 0.3342(3) 0.0569(14) Uani 1 1 d . . . O4 O 0.6370(6) 0.6176(6) 0.3345(3) 0.0738(18) Uani 1 1 d . . . O5 O 0.5156(6) 0.6929(4) 0.2219(3) 0.0585(15) Uani 1 1 d . . . O6 O 0.2657(9) 0.7371(7) -0.0002(4) 0.102(2) Uani 1 1 d . . . N1 N 0.5932(6) 0.0656(5) 0.3628(3) 0.0339(13) Uani 1 1 d . . . N2 N 0.6537(6) 0.2478(4) 0.2703(3) 0.0303(13) Uani 1 1 d . . . N3 N 0.3461(6) 0.1808(4) 0.3391(3) 0.0275(12) Uani 1 1 d . . . N4 N 0.2706(6) 0.1115(4) 0.1430(3) 0.0311(13) Uani 1 1 d . . . N5 N 0.2140(6) -0.0687(5) 0.2320(3) 0.0323(13) Uani 1 1 d . . . C1 C 0.6194(8) -0.0358(6) 0.3655(5) 0.0427(18) Uani 1 1 d . . . H1A H 0.5748 -0.0995 0.3150 0.051 Uiso 1 1 calc R . . C2 C 0.7101(9) -0.0500(7) 0.4400(5) 0.052(2) Uani 1 1 d . . . H2A H 0.7239 -0.1220 0.4400 0.062 Uiso 1 1 calc R . . C3 C 0.7792(10) 0.0462(8) 0.5142(5) 0.059(2) Uani 1 1 d . . . H3 H 0.8428 0.0403 0.5647 0.071 Uiso 1 1 calc R . . C4 C 0.7526(9) 0.1515(7) 0.5127(5) 0.0474(19) Uani 1 1 d . . . H4 H 0.7951 0.2160 0.5626 0.057 Uiso 1 1 calc R . . C5 C 0.6617(7) 0.1591(6) 0.4356(4) 0.0322(16) Uani 1 1 d . . . C6 C 0.6387(8) 0.2767(6) 0.4286(4) 0.0325(16) Uani 1 1 d . . . C7 C 0.7200(7) 0.3181(5) 0.3549(4) 0.0288(15) Uani 1 1 d . . . C8 C 0.8598(8) 0.4206(6) 0.3744(5) 0.0405(17) Uani 1 1 d . . . H8 H 0.9022 0.4682 0.4324 0.049 Uiso 1 1 calc R . . C9 C 0.9352(8) 0.4510(6) 0.3068(5) 0.0459(19) Uani 1 1 d . . . H9 H 1.0305 0.5185 0.3188 0.055 Uiso 1 1 calc R . . C10 C 0.8677(8) 0.3801(6) 0.2212(5) 0.0442(19) Uani 1 1 d . . . H10 H 0.9157 0.3998 0.1746 0.053 Uiso 1 1 calc R . . C11 C 0.7297(8) 0.2808(6) 0.2057(4) 0.0346(16) Uani 1 1 d . . . H11 H 0.6858 0.2334 0.1477 0.042 Uiso 1 1 calc R . . C12 C 0.4514(8) 0.2640(6) 0.4115(4) 0.0333(16) Uani 1 1 d . . . C13 C 0.3944(8) 0.3367(6) 0.4693(4) 0.0381(17) Uani 1 1 d . . . H13 H 0.4690 0.3965 0.5172 0.046 Uiso 1 1 calc R . . C14 C 0.2251(9) 0.3182(7) 0.4542(5) 0.050(2) Uani 1 1 d . . . H14 H 0.1836 0.3637 0.4936 0.060 Uiso 1 1 calc R . . C15 C 0.1187(8) 0.2340(6) 0.3823(5) 0.0422(18) Uani 1 1 d . . . H15 H 0.0042 0.2212 0.3719 0.051 Uiso 1 1 calc R . . C16 C 0.1830(7) 0.1670(5) 0.3242(4) 0.0292(15) Uani 1 1 d . . . C17 C 0.0657(7) 0.0753(6) 0.2393(4) 0.0355(16) Uani 1 1 d . . . C18 C 0.1192(8) 0.1107(5) 0.1564(4) 0.0322(16) Uani 1 1 d . . . C19 C 0.0127(8) 0.1411(6) 0.0982(5) 0.0421(18) Uani 1 1 d . . . H19 H -0.0911 0.1414 0.1092 0.051 Uiso 1 1 calc R . . C20 C 0.0631(9) 0.1709(6) 0.0236(5) 0.0470(19) Uani 1 1 d . . . H20 H -0.0058 0.1922 -0.0157 0.056 Uiso 1 1 calc R . . C21 C 0.2148(9) 0.1685(6) 0.0090(4) 0.0445(18) Uani 1 1 d . . . H21 H 0.2507 0.1870 -0.0410 0.053 Uiso 1 1 calc R . . C22 C 0.3144(9) 0.1383(6) 0.0695(4) 0.0401(17) Uani 1 1 d . . . H22 H 0.4177 0.1365 0.0587 0.048 Uiso 1 1 calc R . . C23 C 0.0676(8) -0.0517(6) 0.2350(4) 0.0366(17) Uani 1 1 d . . . C24 C -0.0765(8) -0.1422(6) 0.2333(5) 0.0451(19) Uani 1 1 d . . . H24 H -0.1760 -0.1280 0.2373 0.054 Uiso 1 1 calc R . . C25 C -0.0706(9) -0.2553(7) 0.2255(5) 0.054(2) Uani 1 1 d . . . H25 H -0.1661 -0.3180 0.2243 0.065 Uiso 1 1 calc R . . C26 C 0.0762(9) -0.2727(6) 0.2196(5) 0.0467(19) Uani 1 1 d . . . H26 H 0.0823 -0.3480 0.2127 0.056 Uiso 1 1 calc R . . C27 C 0.2170(9) -0.1773(6) 0.2238(4) 0.0420(18) Uani 1 1 d . . . H27 H 0.3180 -0.1897 0.2208 0.050 Uiso 1 1 calc R . . C28 C 0.3857(13) 0.4723(8) 0.2146(6) 0.069(2) Uani 1 1 d . . . C29 C 0.2927(15) 0.6308(11) 0.0105(7) 0.112(4) Uani 1 1 d . . . S1 S 0.4878(2) 0.62299(17) 0.28397(12) 0.0450(5) Uani 1 1 d . . . F1 F 0.3491(9) 0.3973(5) 0.2617(5) 0.143(3) Uani 1 1 d . . . F2 F 0.2419(7) 0.4628(5) 0.1629(4) 0.0972(18) Uani 1 1 d . . . F3 F 0.4814(8) 0.4441(5) 0.1615(4) 0.112(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 Fe1 0.0269(5) 0.0316(6) 0.0310(6) 0.0069(4) 0.0073(4) 0.0093(4) Cl1 0.0345(9) 0.0436(11) 0.0405(11) 0.0032(9) 0.0106(8) 0.0147(8) O1 0.038(3) 0.041(3) 0.030(3) 0.000(2) 0.005(2) 0.005(2) O2 0.031(3) 0.054(4) 0.053(4) 0.006(3) 0.010(2) 0.019(2) O3 0.055(3) 0.081(4) 0.041(3) 0.012(3) 0.020(3) 0.033(3) O4 0.050(3) 0.126(6) 0.051(4) 0.021(4) 0.006(3) 0.041(4) O5 0.068(4) 0.045(3) 0.069(4) 0.029(3) 0.030(3) 0.014(3) O6 0.096(5) 0.132(7) 0.055(4) 0.005(4) 0.005(4) 0.027(5) N1 0.035(3) 0.031(4) 0.035(4) 0.011(3) 0.008(3) 0.009(3) N2 0.030(3) 0.030(3) 0.036(3) 0.012(3) 0.010(3) 0.013(3) N3 0.028(3) 0.030(3) 0.025(3) 0.010(3) 0.007(2) 0.009(3) N4 0.032(3) 0.035(3) 0.028(3) 0.006(3) 0.008(2) 0.014(3) N5 0.024(3) 0.035(4) 0.039(4) 0.012(3) 0.009(2) 0.011(3) C1 0.042(4) 0.034(5) 0.046(5) 0.010(4) 0.009(3) 0.006(4) C2 0.069(5) 0.045(5) 0.051(5) 0.024(5) 0.009(4) 0.029(4) C3 0.074(6) 0.063(6) 0.049(5) 0.022(5) 0.008(4) 0.035(5) C4 0.060(5) 0.051(5) 0.029(4) 0.007(4) 0.002(4) 0.021(4) C5 0.028(3) 0.036(4) 0.033(4) 0.010(4) 0.010(3) 0.010(3) C6 0.034(4) 0.033(4) 0.029(4) 0.003(3) 0.008(3) 0.013(3) C7 0.027(3) 0.029(4) 0.025(4) 0.005(3) 0.000(3) 0.006(3) C8 0.033(4) 0.037(4) 0.040(4) 0.009(4) 0.000(3) 0.001(3) C9 0.038(4) 0.037(5) 0.056(5) 0.017(4) 0.009(4) 0.003(3) C10 0.037(4) 0.050(5) 0.047(5) 0.024(4) 0.016(4) 0.007(4) C11 0.037(4) 0.042(4) 0.025(4) 0.011(3) 0.010(3) 0.012(4) C12 0.037(4) 0.032(4) 0.027(4) 0.011(3) 0.001(3) 0.007(3) C13 0.037(4) 0.038(4) 0.036(4) -0.001(3) 0.007(3) 0.016(3) C14 0.056(5) 0.052(5) 0.041(5) 0.000(4) 0.009(4) 0.028(4) C15 0.037(4) 0.052(5) 0.047(5) 0.008(4) 0.014(4) 0.030(4) C16 0.024(4) 0.030(4) 0.034(4) 0.011(3) 0.006(3) 0.008(3) C17 0.023(3) 0.040(4) 0.044(4) 0.011(4) 0.009(3) 0.012(3) C18 0.039(4) 0.026(4) 0.032(4) 0.002(3) 0.007(3) 0.017(3) C19 0.037(4) 0.044(5) 0.050(5) 0.012(4) 0.006(3) 0.022(4) C20 0.059(5) 0.047(5) 0.038(5) 0.012(4) -0.004(4) 0.029(4) C21 0.054(5) 0.045(5) 0.035(5) 0.007(4) 0.009(4) 0.020(4) C22 0.042(4) 0.044(5) 0.035(4) 0.010(4) 0.008(3) 0.015(4) C23 0.035(4) 0.045(5) 0.025(4) 0.008(3) 0.005(3) 0.010(3) C24 0.027(4) 0.051(5) 0.059(5) 0.025(4) 0.017(3) 0.005(3) C25 0.047(5) 0.041(5) 0.069(6) 0.026(4) 0.015(4) -0.001(4) C26 0.040(4) 0.034(4) 0.066(5) 0.017(4) 0.014(4) 0.010(4) C27 0.043(4) 0.042(5) 0.044(5) 0.017(4) 0.009(3) 0.016(4) C28 0.081(7) 0.052(6) 0.077(7) 0.014(5) 0.021(6) 0.027(5) C29 0.142(11) 0.122(10) 0.087(8) 0.033(8) 0.001(7) 0.074(9) S1 0.0468(11) 0.0487(13) 0.0413(12) 0.0108(10) 0.0170(9) 0.0169(10) F1 0.202(8) 0.057(4) 0.179(7) 0.069(5) 0.061(6) 0.024(4) F2 0.080(4) 0.079(4) 0.093(4) -0.001(3) 0.008(3) -0.005(3) F3 0.124(5) 0.080(4) 0.128(5) -0.016(4) 0.046(4) 0.051(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 Fe1 N4 2.187(5) . ? Fe1 N5 2.191(5) . ? Fe1 N3 2.196(5) . ? Fe1 N2 2.197(5) . ? Fe1 N1 2.212(5) . ? Fe1 Cl1 2.3878(19) . ? O1 C6 1.413(7) . ? O2 C17 1.392(7) . ? O3 S1 1.447(5) . ? O4 S1 1.438(5) . ? O5 S1 1.429(5) . ? O6 C29 1.438(12) . ? N1 C1 1.344(8) . ? N1 C5 1.355(8) . ? N2 C11 1.347(7) . ? N2 C7 1.363(8) . ? N3 C16 1.336(7) . ? N3 C12 1.350(8) . ? N4 C22 1.339(8) . ? N4 C18 1.341(7) . ? N5 C27 1.325(8) . ? N5 C23 1.340(7) . ? C1 C2 1.391(9) . ? C2 C3 1.386(11) . ? C3 C4 1.389(10) . ? C4 C5 1.387(9) . ? C5 C6 1.544(9) . ? C6 C7 1.532(8) . ? C6 C12 1.543(8) . ? C7 C8 1.387(9) . ? C8 C9 1.377(9) . ? C9 C10 1.378(9) . ? C10 C11 1.361(9) . ? C12 C13 1.386(8) . ? C13 C14 1.376(9) . ? C14 C15 1.354(10) . ? C15 C16 1.388(8) . ? C16 C17 1.541(9) . ? C17 C18 1.544(9) . ? C17 C23 1.556(9) . ? C18 C19 1.393(9) . ? C19 C20 1.387(9) . ? C20 C21 1.359(9) . ? C21 C22 1.378(9) . ? C23 C24 1.376(9) . ? C24 C25 1.389(10) . ? C25 C26 1.352(9) . ? C26 C27 1.382(9) . ? C28 F1 1.294(10) . ? C28 F3 1.318(10) . ? C28 F2 1.339(10) . ? C28 S1 1.814(9) . ? 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 N4 Fe1 N5 80.17(19) . . ? N4 Fe1 N3 84.65(18) . . ? N5 Fe1 N3 84.69(19) . . ? N4 Fe1 N2 98.31(19) . . ? N5 Fe1 N2 168.54(19) . . ? N3 Fe1 N2 83.86(19) . . ? N4 Fe1 N1 167.39(19) . . ? N5 Fe1 N1 97.51(19) . . ? N3 Fe1 N1 82.80(19) . . ? N2 Fe1 N1 81.48(19) . . ? N4 Fe1 Cl1 94.72(14) . . ? N5 Fe1 Cl1 94.81(15) . . ? N3 Fe1 Cl1 179.26(15) . . ? N2 Fe1 Cl1 96.64(14) . . ? N1 Fe1 Cl1 97.82(14) . . ? C1 N1 C5 118.2(6) . . ? C1 N1 Fe1 120.6(5) . . ? C5 N1 Fe1 121.2(4) . . ? C11 N2 C7 117.6(5) . . ? C11 N2 Fe1 121.1(4) . . ? C7 N2 Fe1 121.1(4) . . ? C16 N3 C12 119.0(5) . . ? C16 N3 Fe1 120.3(4) . . ? C12 N3 Fe1 120.6(4) . . ? C22 N4 C18 117.7(5) . . ? C22 N4 Fe1 121.5(4) . . ? C18 N4 Fe1 120.7(4) . . ? C27 N5 C23 118.4(6) . . ? C27 N5 Fe1 120.5(4) . . ? C23 N5 Fe1 121.1(4) . . ? N1 C1 C2 123.2(7) . . ? C3 C2 C1 118.0(7) . . ? C2 C3 C4 119.5(7) . . ? C5 C4 C3 119.1(7) . . ? N1 C5 C4 121.9(6) . . ? N1 C5 C6 117.1(5) . . ? C4 C5 C6 121.0(6) . . ? O1 C6 C7 104.5(5) . . ? O1 C6 C12 110.4(5) . . ? C7 C6 C12 110.7(5) . . ? O1 C6 C5 109.9(5) . . ? C7 C6 C5 109.5(5) . . ? C12 C6 C5 111.6(5) . . ? N2 C7 C8 121.5(6) . . ? N2 C7 C6 117.3(5) . . ? C8 C7 C6 121.1(6) . . ? C9 C8 C7 119.2(6) . . ? C8 C9 C10 119.1(6) . . ? C11 C10 C9 119.2(6) . . ? N2 C11 C10 123.2(6) . . ? N3 C12 C13 121.5(6) . . ? N3 C12 C6 118.2(6) . . ? C13 C12 C6 120.3(6) . . ? C14 C13 C12 118.5(7) . . ? C15 C14 C13 120.2(7) . . ? C14 C15 C16 119.1(6) . . ? N3 C16 C15 121.7(6) . . ? N3 C16 C17 118.3(5) . . ? C15 C16 C17 120.0(5) . . ? O2 C17 C16 104.7(5) . . ? O2 C17 C18 111.3(5) . . ? C16 C17 C18 109.9(5) . . ? O2 C17 C23 109.9(5) . . ? C16 C17 C23 112.1(5) . . ? C18 C17 C23 108.9(5) . . ? N4 C18 C19 121.6(6) . . ? N4 C18 C17 117.8(5) . . ? C19 C18 C17 120.6(6) . . ? C20 C19 C18 119.3(6) . . ? C21 C20 C19 118.9(6) . . ? C20 C21 C22 118.9(6) . . ? N4 C22 C21 123.6(6) . . ? N5 C23 C24 121.9(6) . . ? N5 C23 C17 117.2(5) . . ? C24 C23 C17 120.8(6) . . ? C23 C24 C25 118.8(7) . . ? C26 C25 C24 118.9(7) . . ? C25 C26 C27 119.2(7) . . ? N5 C27 C26 122.6(7) . . ? F1 C28 F3 110.1(8) . . ? F1 C28 F2 107.6(8) . . ? F3 C28 F2 107.1(8) . . ? F1 C28 S1 111.7(7) . . ? F3 C28 S1 110.5(7) . . ? F2 C28 S1 109.7(6) . . ? O5 S1 O4 115.3(3) . . ? O5 S1 O3 114.2(3) . . ? O4 S1 O3 115.3(3) . . ? O5 S1 C28 104.1(4) . . ? O4 S1 C28 102.6(4) . . ? O3 S1 C28 103.0(4) . . ? _diffrn_measured_fraction_theta_max 0.671 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.671 _refine_diff_density_max 0.539 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.126