# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/188 #=============================================================================== data_global #=============================================================================== _audit_creation_date 11-12-98 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; ; _publ_contact_author_address # Address of author for correspondance ; ; _publ_contact_author_phone 'xxxxxxxxxx' _publ_contact_author_fax 'xxxxxxxxxx' _publ_contact_author_email xxx@xx.xx.xx _publ_requested_journal 'Acta Crystallographica C' _publ_contact_letter ; Please consider this CIF submission for publication as a new structure paper in Acta Crystallographica Section C. The figures, chemical structure diagram (scheme), Transfert of Copyright Agreement form and structure factors will be sent on receipt of your acknowledgement letter ; _publ_requested_category FM #=============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Dupont Karl' #<--'Last name, first name' ; Research School of Chemistry National Laboratory Ouchnock Islandia ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. data_st273 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C32 H34 Fe2 N4 O8' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C32 H34 Fe2 N4 O8' _chemical_formula_weight 714.34 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Fe ? 0.301 0.845 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 7.6960(1) _cell_length_b 7.7810(4) _cell_length_c 25.554(1) _cell_angle_alpha 90 _cell_angle_beta 90.239(1) _cell_angle_gamma 90 _cell_volume 1530.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.55 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 180 frames, 25 sec/frame, delta phi = 1.0 deg. Each frame measured 2 times. Detector to crystal distance 31 mm. ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7860 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.48 _reflns_number_total 4249 _reflns_number_gt 2456 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2456 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.046 _refine_ls_wR_factor_all 0.106 _refine_ls_wR_factor_ref 0.076 _refine_ls_goodness_of_fit_all 1.953 _refine_ls_goodness_of_fit_ref 1.458 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.583 _refine_diff_density_min -0.546 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 0.8107(4) 0.3899(4) -0.0340(1) 0.042(1) Uani ? ? C N1 0.7681(3) 0.2394(3) -0.0150(1) 0.048(1) Uani ? ? N C2 0.5814(4) 0.2083(5) -0.0241(1) 0.058(2) Uani ? ? C C3 0.5267(5) 0.3592(5) -0.0591(1) 0.060(2) Uani ? ? C N2 0.6823(4) 0.4665(4) -0.0580(1) 0.055(2) Uani ? ? N C4 0.9883(4) 0.4621(4) -0.0278(1) 0.047(2) Uani ? ? C FE 0.97129(5) 0.02090(6) 0.18025(2) 0.0437(2) Uani ? ? Fe C5 1.0908(4) -0.0271(4) 0.1113(1) 0.043(1) Uani ? ? C C6 1.1799(4) -0.1129(4) 0.1536(1) 0.050(2) Uani ? ? C C7 1.0569(5) -0.2267(5) 0.1772(1) 0.058(2) Uani ? ? C C8 0.8997(4) -0.2152(5) 0.1508(1) 0.056(2) Uani ? ? C C9 0.9170(4) -0.0905(4) 0.1101(1) 0.050(2) Uani ? ? C C10 1.1579(4) 0.1114(4) 0.0770(1) 0.044(1) Uani ? ? C O1 1.2936(3) 0.1906(3) 0.09028(9) 0.059(1) Uani ? ? O O2 1.0805(4) 0.1422(3) 0.03589(9) 0.068(1) Uani ? ? O C11 0.7952(4) 0.2099(5) 0.1907(1) 0.054(2) Uani ? ? C C12 0.9636(4) 0.2827(5) 0.1863(1) 0.058(2) Uani ? ? C C13 1.0667(5) 0.2129(6) 0.2271(1) 0.071(2) Uani ? ? C C14 0.9631(5) 0.0994(7) 0.2570(1) 0.067(2) Uani ? ? C C15 0.7940(5) 0.0935(6) 0.2345(1) 0.063(2) Uani ? ? C C16 0.6519(5) 0.2432(5) 0.1537(1) 0.060(2) Uani ? ? C O3 0.6621(4) 0.3412(4) 0.1170(1) 0.084(2) Uani ? ? O O4 0.5130(3) 0.1523(4) 0.1642(1) 0.073(2) Uani ? ? O H1 0.8455 0.1622 0.0020 0.0624 Uiso calc N1 H H2 0.5191 0.2094 0.0079 0.0764 Uiso calc C2 H H3 0.5632 0.1016 -0.0413 0.0764 Uiso calc C2 H H4 0.4293 0.4182 -0.0452 0.0791 Uiso calc C3 H H5 0.5006 0.3218 -0.0937 0.0791 Uiso calc C3 H H6 0.6891 0.5782 -0.0728 0.0733 Uiso calc N2 H H7 1.0054 0.5503 -0.0529 0.0614 Uiso calc C4 H H8 1.0713 0.3735 -0.0330 0.0614 Uiso calc C4 H H9 1.2746 -0.1852 0.1629 0.0660 Uiso calc C6 H H10 1.0795 -0.2989 0.2064 0.0765 Uiso calc C7 H H11 0.7978 -0.2792 0.1585 0.0733 Uiso calc C8 H H12 0.8312 -0.1477 0.0897 0.0648 Uiso calc C9 H H13 1.0297 0.3858 0.1862 0.0759 Uiso calc C12 H H14 1.1857 0.2381 0.2334 0.0933 Uiso calc C13 H H15 1.0005 0.0375 0.2871 0.0940 Uiso calc C14 H H16 0.7433 0.0676 0.2674 0.0853 Uiso calc C15 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.052(2) 0.036(2) 0.040(1) -0.001(1) 0.009(1) -0.002(1) C N1 0.050(1) 0.040(1) 0.054(1) -0.004(1) -0.001(1) 0.008(1) N C2 0.057(2) 0.047(2) 0.073(2) -0.010(1) 0.010(2) -0.001(2) C C3 0.054(2) 0.058(2) 0.071(2) 0.001(2) 0.002(2) 0.007(2) C N2 0.058(2) 0.042(1) 0.070(2) 0.002(1) 0.000(1) 0.015(1) N C4 0.057(2) 0.043(2) 0.042(1) -0.006(1) 0.008(1) -0.001(1) C FE 0.0425(3) 0.0495(2) 0.0396(2) -0.0037(2) -0.0051(2) -0.0010(2) Fe C5 0.049(2) 0.036(1) 0.044(1) 0.002(1) 0.001(1) -0.003(1) C C6 0.051(2) 0.042(2) 0.059(2) 0.007(1) -0.004(1) 0.007(2) C C7 0.071(2) 0.047(2) 0.059(2) -0.003(2) -0.008(2) 0.011(2) C C8 0.061(2) 0.054(2) 0.054(2) -0.012(2) -0.001(1) 0.003(2) C C9 0.055(2) 0.048(2) 0.047(1) -0.007(1) -0.010(1) -0.005(2) C C10 0.055(2) 0.035(2) 0.044(1) 0.010(1) 0.002(1) 0.000(1) C O1 0.055(1) 0.051(1) 0.073(1) -0.006(1) -0.009(1) 0.022(1) O O2 0.100(2) 0.055(1) 0.058(1) -0.008(1) -0.024(1) 0.011(1) O C11 0.058(2) 0.050(2) 0.055(2) 0.005(1) 0.003(1) -0.001(2) C C12 0.064(2) 0.048(2) 0.064(2) -0.010(1) -0.001(2) -0.022(2) C C13 0.064(2) 0.083(3) 0.068(2) -0.005(2) -0.013(2) -0.029(2) C C14 0.066(2) 0.107(3) 0.043(2) -0.000(2) -0.008(2) -0.009(2) C C15 0.073(2) 0.083(3) 0.040(2) 0.012(2) 0.007(1) 0.001(2) C C16 0.056(2) 0.054(2) 0.073(2) 0.001(2) -0.002(2) 0.004(2) C O3 0.078(2) 0.074(2) 0.103(2) -0.007(1) -0.013(1) 0.041(1) O O4 0.050(1) 0.094(2) 0.085(2) -0.014(1) -0.006(1) 0.026(1) O # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.310(4) . . ? C1 N2 1.304(4) . . ? C1 C4 1.486(5) . . ? N1 C2 1.474(5) . . ? N1 N2 2.181(4) . . ? C2 C3 1.535(6) . . ? C3 N2 1.460(5) . . ? FE C5 2.026(3) . . ? FE C6 2.034(4) . . ? FE C7 2.038(4) . . ? FE C8 2.059(4) . . ? FE C9 2.034(3) . . ? FE C11 2.018(4) . . ? FE C12 2.043(4) . . ? FE C13 2.048(4) . . ? FE C14 2.055(4) . . ? FE C15 2.030(4) . . ? C5 C6 1.441(5) . . ? C5 C9 1.426(5) . . ? C5 C10 1.483(5) . . ? C6 C7 1.431(5) . . ? C7 C8 1.385(5) . . ? C8 C9 1.430(5) . . ? C10 O1 1.258(4) . . ? C10 O2 1.229(4) . . ? O1 O2 2.178(3) . . ? C11 C12 1.419(5) . . ? C11 C15 1.441(5) . . ? C11 C16 1.472(5) . . ? C12 C13 1.416(6) . . ? C13 C14 1.415(7) . . ? C14 C15 1.421(6) . . ? C16 O3 1.212(5) . . ? C16 O4 1.311(5) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 113.1(3) . . . ? N1 C1 C4 122.0(3) . . . ? N2 C1 C4 125.0(3) . . . ? C1 N1 C2 109.5(3) . . . ? C1 N1 N2 33.4(2) . . . ? C2 N1 N2 76.2(2) . . . ? N1 C2 C3 103.4(3) . . . ? C2 C3 N2 101.7(3) . . . ? C1 N2 N1 33.5(2) . . . ? C1 N2 C3 111.6(3) . . . ? N1 N2 C3 78.1(2) . . . ? C5 FE C6 41.6(1) . . . ? C5 FE C7 69.2(1) . . . ? C5 FE C8 68.9(1) . . . ? C5 FE C9 41.1(1) . . . ? C5 FE C11 123.8(1) . . . ? C5 FE C12 105.2(1) . . . ? C5 FE C13 118.7(2) . . . ? C5 FE C14 154.2(2) . . . ? C5 FE C15 162.7(2) . . . ? C6 FE C7 41.2(2) . . . ? C6 FE C8 68.4(2) . . . ? C6 FE C9 69.3(1) . . . ? C6 FE C11 161.6(2) . . . ? C6 FE C12 124.0(1) . . . ? C6 FE C13 106.7(2) . . . ? C6 FE C14 120.0(2) . . . ? C6 FE C15 154.9(2) . . . ? C7 FE C8 39.5(2) . . . ? C7 FE C9 68.2(1) . . . ? C7 FE C11 155.7(2) . . . ? C7 FE C12 162.7(2) . . . ? C7 FE C13 126.6(2) . . . ? C7 FE C14 109.2(2) . . . ? C7 FE C15 120.5(2) . . . ? C8 FE C9 40.9(1) . . . ? C8 FE C11 121.3(2) . . . ? C8 FE C12 155.4(1) . . . ? C8 FE C13 163.5(2) . . . ? C8 FE C14 127.2(2) . . . ? C8 FE C15 108.6(2) . . . ? C9 FE C11 106.9(1) . . . ? C9 FE C12 119.0(2) . . . ? C9 FE C13 153.9(2) . . . ? C9 FE C14 164.0(2) . . . ? C9 FE C15 125.8(2) . . . ? C11 FE C12 40.9(1) . . . ? C11 FE C13 68.3(2) . . . ? C11 FE C14 68.6(2) . . . ? C11 FE C15 41.7(2) . . . ? C12 FE C13 40.5(2) . . . ? C12 FE C14 68.3(2) . . . ? C12 FE C15 69.6(2) . . . ? C13 FE C14 40.4(2) . . . ? C13 FE C15 68.8(2) . . . ? C14 FE C15 40.7(2) . . . ? FE C5 C6 69.5(2) . . . ? FE C5 C9 69.7(2) . . . ? FE C5 C10 122.7(2) . . . ? C6 C5 C9 107.4(3) . . . ? C6 C5 C10 127.9(3) . . . ? C9 C5 C10 124.6(3) . . . ? FE C6 C5 68.9(2) . . . ? FE C6 C7 69.6(2) . . . ? C5 C6 C7 106.8(3) . . . ? FE C7 C6 69.3(2) . . . ? FE C7 C8 71.1(2) . . . ? C6 C7 C8 109.4(3) . . . ? FE C8 C7 69.4(2) . . . ? FE C8 C9 68.6(2) . . . ? C7 C8 C9 108.3(3) . . . ? FE C9 C5 69.1(2) . . . ? FE C9 C8 70.5(2) . . . ? C5 C9 C8 108.0(3) . . . ? C5 C10 O1 119.2(3) . . . ? C5 C10 O2 118.5(3) . . . ? O1 C10 O2 122.2(3) . . . ? C10 O1 O2 28.5(2) . . . ? C10 O2 O1 29.2(2) . . . ? FE C11 C12 70.5(2) . . . ? FE C11 C15 69.6(2) . . . ? FE C11 C16 123.0(3) . . . ? C12 C11 C15 108.7(3) . . . ? C12 C11 C16 124.1(3) . . . ? C15 C11 C16 127.0(4) . . . ? FE C12 C11 68.6(2) . . . ? FE C12 C13 69.9(2) . . . ? C11 C12 C13 107.3(4) . . . ? FE C13 C12 69.6(2) . . . ? FE C13 C14 70.1(2) . . . ? C12 C13 C14 108.8(4) . . . ? FE C14 C13 69.6(2) . . . ? FE C14 C15 68.7(2) . . . ? C13 C14 C15 108.6(4) . . . ? FE C15 C11 68.7(2) . . . ? FE C15 C14 70.6(2) . . . ? C11 C15 C14 106.5(4) . . . ? C11 C16 O3 123.8(4) . . . ? C11 C16 O4 112.5(3) . . . ? O3 C16 O4 123.6(4) . . . ? data_st266 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C24 H36 Fe N4 O6' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H36 Fe N4 O6' _chemical_formula_weight 532.42 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Fe ? 0.301 0.845 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,1/2-y,1/2+z -x,+y,1/2-z 1/2+x,1/2-y,-z -x,-y,-z 1/2+x,1/2+y,1/2-z +x,-y,1/2+z 1/2-x,1/2+y,+z _cell_length_a 17.3450(4) _cell_length_b 13.8160(3) _cell_length_c 10.5130(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2519.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.40 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 180 frames, 30 sec/frame, delta phi = 1.0 deg. Each frame measured 2 times. Detector to crystal distance 29 mm. ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18527 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 28.54 _reflns_number_total 3199 _reflns_number_gt 2156 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^)+0.0004 Fo^4^)+1.0' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2156 _refine_ls_number_parameters 168 _refine_ls_number_restraints 4 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.063 _refine_ls_R_factor_gt 0.048 _refine_ls_wR_factor_all 0.067 _refine_ls_wR_factor_ref 0.063 _refine_ls_goodness_of_fit_all 1.365 _refine_ls_goodness_of_fit_ref 1.400 _refine_ls_shift/su_max 0.022 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.633 _refine_diff_density_min -0.435 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 0.1014(2) 0.4864(2) 0.5715(3) 0.034(1) 1.000 Uani ? ? C N1 0.1401(1) 0.4277(2) 0.6466(2) 0.036(1) 1.000 Uani ? ? N C2 0.2231(2) 0.4477(3) 0.6400(3) 0.043(2) 1.000 Uani ? ? C C3 0.2271(2) 0.5309(3) 0.5439(3) 0.049(2) 1.000 Uani ? ? C N2 0.1463(1) 0.5444(2) 0.5078(3) 0.044(1) 1.000 Uani ? ? N C4 0.0154(2) 0.4861(2) 0.5646(3) 0.039(2) 1.000 Uani ? ? C FE 0.0000 0.90982(4) 0.2500 0.0255(2) 0.500 Uani ? ? Fe C5 0.0644(2) 0.9173(2) 0.0861(3) 0.036(1) 1.000 Uani ? ? C C6 0.0864(2) 0.9928(2) 0.1701(3) 0.036(1) 1.000 Uani ? ? C C7 0.1112(2) 0.9500(2) 0.2858(3) 0.033(1) 1.000 Uani ? ? C C8 0.1049(1) 0.8469(2) 0.2742(3) 0.028(1) 1.000 Uani ? ? C C9 0.0757(2) 0.8275(2) 0.1494(3) 0.030(1) 1.000 Uani ? ? C C10 0.1173(2) 0.7751(2) 0.3774(3) 0.032(1) 1.000 Uani ? ? C O1 0.1380(2) 0.8041(2) 0.4835(2) 0.051(1) 1.000 Uani ? ? O O2 0.1048(1) 0.6862(1) 0.3489(2) 0.0336(9) 1.000 Uani ? ? O C11 0.1831(4) 0.2741(6) 0.3456(7) 0.124(5) 1.000 Uani ? ? C C12 0.1076(4) 0.2601(5) 0.3016(5) 0.104(4) 1.000 Uani ? ? C O3 0.0691(9) 0.3414(8) 0.337(1) 0.20(1) 0.500 Uani ? ? O O3a 0.0881(4) 0.3055(5) 0.1881(5) 0.078(4) 0.500 Uani ? ? O H1 0.1174 0.3790 0.6982 0.0486 1.000 Uiso calc N1 H H2 0.2508 0.3928 0.6104 0.0595 1.000 Uiso calc C2 H H3 0.2427 0.4669 0.7205 0.0595 1.000 Uiso calc C2 H H4 0.2576 0.5137 0.4723 0.0695 1.000 Uiso calc C3 H H5 0.2474 0.5878 0.5820 0.0695 1.000 Uiso calc C3 H H6 0.1289 0.5896 0.4461 0.0603 1.000 Uiso calc N2 H H7 -0.0038 0.5306 0.6256 0.0526 1.000 Uiso calc C4 H H8 -0.0024 0.4228 0.5844 0.0526 1.000 Uiso calc C4 H H9 0.0454 0.9253 0.0020 0.0469 1.000 Uiso calc C5 H H10 0.0847 1.0602 0.1521 0.0495 1.000 Uiso calc C6 H H11 0.1290 0.9839 0.3587 0.0456 1.000 Uiso calc C7 H H12 0.0655 0.7652 0.1149 0.0387 1.000 Uiso calc C9 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.027(1) 0.041(1) 0.035(1) -0.001(1) -0.003(1) 0.008(1) C N1 0.026(1) 0.042(1) 0.044(1) -0.002(1) -0.007(1) 0.015(1) N C2 0.027(1) 0.060(2) 0.050(2) -0.001(1) -0.008(1) 0.017(2) C C3 0.027(1) 0.076(2) 0.058(2) -0.005(1) -0.007(1) 0.029(2) C N2 0.027(1) 0.061(1) 0.051(1) -0.003(1) -0.004(1) 0.028(1) N C4 0.026(1) 0.056(2) 0.040(2) -0.002(1) -0.004(1) 0.013(1) C FE 0.0218(2) 0.0225(2) 0.0337(2) 0.0000 0.0012(2) 0.0000 Fe C5 0.033(1) 0.039(1) 0.036(1) 0.006(1) 0.008(1) 0.011(1) C C6 0.028(1) 0.028(1) 0.059(2) -0.001(1) 0.008(1) 0.010(1) C C7 0.022(1) 0.030(1) 0.053(2) -0.002(1) -0.000(1) -0.005(1) C C8 0.023(1) 0.028(1) 0.035(1) 0.003(1) 0.000(1) -0.001(1) C C9 0.029(1) 0.028(1) 0.033(1) 0.005(1) 0.003(1) 0.000(1) C C10 0.030(1) 0.036(1) 0.031(1) 0.006(1) -0.004(1) -0.003(1) C O1 0.076(2) 0.048(1) 0.037(1) 0.011(1) -0.021(1) -0.009(1) O O2 0.042(1) 0.0291(9) 0.0310(9) 0.0040(8) -0.0030(9) 0.0010(8) O C11 0.066(3) 0.211(7) 0.138(5) 0.005(4) -0.001(4) -0.038(5) C C12 0.154(6) 0.099(4) 0.074(3) 0.013(4) 0.014(4) -0.004(3) C O3 0.33(2) 0.136(6) 0.187(9) 0.089(8) 0.02(1) -0.070(6) O O3a 0.118(5) 0.119(5) 0.033(3) 0.016(4) -0.002(3) 0.014(3) O # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.316(4) . . yes C1 N2 1.303(4) . . yes C1 C4 1.493(4) . . yes N1 C2 1.467(4) . . yes N1 N2 2.177(3) . . yes C2 C3 1.532(5) . . yes C3 N2 1.464(4) . . yes C4 C4 1.510(6) . 5_566 yes FE C5 2.056(3) . . yes FE C5 2.056(3) . 3_555 yes FE C6 2.065(3) . . yes FE C6 2.065(3) . 3_555 yes FE C7 2.042(3) . . yes FE C7 2.042(3) . 3_555 yes FE C8 2.032(3) . . yes FE C8 2.032(3) . 3_555 yes FE C9 2.033(3) . . yes FE C9 2.033(3) . 3_555 yes C5 C6 1.419(5) . . yes C5 C9 1.421(4) . . yes C6 C7 1.420(4) . . yes C7 C8 1.433(4) . . yes C8 C9 1.431(4) . . yes C8 C10 1.487(4) . . yes C10 O1 1.238(3) . . yes C10 O2 1.283(3) . . yes C11 C12 1.401(9) . . yes C11 O3 2.19(2) . . yes C12 O3 1.36(1) . . yes C12 O3a 1.390(8) . . yes O3 O3a 1.68(1) . . yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 112.5(3) . . . yes N1 C1 C4 122.5(3) . . . yes N2 C1 C4 125.0(3) . . . yes C1 N1 C2 110.9(2) . . . yes C1 N1 N2 33.6(2) . . . yes C2 N1 N2 77.4(2) . . . yes N1 C2 C3 102.5(2) . . . yes C2 C3 N2 103.0(3) . . . yes C1 N2 N1 33.9(2) . . . yes C1 N2 C3 111.1(3) . . . yes N1 N2 C3 77.2(2) . . . yes C1 C4 C4 113.4(3) . . 5_566 yes C5 FE C5 174.3(2) . . 3_555 yes C5 FE C6 40.3(1) . . . yes C5 FE C6 135.0(1) . . 3_555 yes C5 FE C7 68.1(1) . . . yes C5 FE C7 110.2(1) . . 3_555 yes C5 FE C8 68.9(1) . . . yes C5 FE C8 113.8(1) . . 3_555 yes C5 FE C9 40.7(1) . . . yes C5 FE C9 144.5(1) . . 3_555 yes C5 FE C6 135.0(1) . 3_555 . yes C5 FE C6 40.3(1) . 3_555 3_555 yes C5 FE C7 110.2(1) . 3_555 . yes C5 FE C7 68.1(1) . 3_555 3_555 yes C5 FE C8 113.8(1) . 3_555 . yes C5 FE C8 68.9(1) . 3_555 3_555 yes C5 FE C9 144.5(1) . 3_555 . yes C5 FE C9 40.7(1) . 3_555 3_555 yes C6 FE C6 112.5(2) . . 3_555 yes C6 FE C7 40.4(1) . . . yes C6 FE C7 117.3(1) . . 3_555 yes C6 FE C8 68.8(1) . . . yes C6 FE C8 146.7(1) . . 3_555 yes C6 FE C9 68.3(1) . . . yes C6 FE C9 172.1(1) . . 3_555 yes C6 FE C7 117.3(1) . 3_555 . yes C6 FE C7 40.4(1) . 3_555 3_555 yes C6 FE C8 146.7(1) . 3_555 . yes C6 FE C8 68.8(1) . 3_555 3_555 yes C6 FE C9 172.1(1) . 3_555 . yes C6 FE C9 68.3(1) . 3_555 3_555 yes C7 FE C7 148.5(2) . . 3_555 yes C7 FE C8 41.2(1) . . . yes C7 FE C8 170.0(1) . . 3_555 yes C7 FE C9 68.8(1) . . . yes C7 FE C9 131.7(1) . . 3_555 yes C7 FE C8 170.0(1) . 3_555 . yes C7 FE C8 41.2(1) . 3_555 3_555 yes C7 FE C9 131.7(1) . 3_555 . yes C7 FE C9 68.8(1) . 3_555 3_555 yes C8 FE C8 129.4(2) . . 3_555 yes C8 FE C9 41.2(1) . . . yes C8 FE C9 105.9(1) . . 3_555 yes C8 FE C9 105.9(1) . 3_555 . yes C8 FE C9 41.2(1) . 3_555 3_555 yes C9 FE C9 112.0(2) . . 3_555 yes FE C5 C6 70.2(2) . . . yes FE C5 C9 68.8(2) . . . yes C6 C5 C9 108.3(3) . . . yes FE C6 C5 69.5(2) . . . yes FE C6 C7 68.9(2) . . . yes C5 C6 C7 107.9(3) . . . yes FE C7 C6 70.7(2) . . . yes FE C7 C8 69.1(2) . . . yes C6 C7 C8 108.6(3) . . . yes FE C8 C7 69.8(2) . . . yes FE C8 C9 69.4(1) . . . yes FE C8 C10 120.4(2) . . . yes C7 C8 C9 107.0(2) . . . yes C7 C8 C10 126.2(3) . . . yes C9 C8 C10 126.5(2) . . . yes FE C9 C5 70.5(2) . . . yes FE C9 C8 69.4(1) . . . yes C5 C9 C8 108.3(2) . . . yes C8 C10 O1 118.9(3) . . . yes C8 C10 O2 116.4(2) . . . yes O1 C10 O2 124.8(3) . . . yes C12 C11 O3 37.0(5) . . . yes C11 C12 O3 104(1) . . . yes C11 C12 O3a 116.7(7) . . . yes O3 C12 O3a 75.1(8) . . . yes C11 O3 C12 38.3(6) . . . yes C11 O3 O3a 74.6(6) . . . yes C12 O3 O3a 53.2(5) . . . yes C12 O3a O3 51.6(5) . . . yes data_bad23fe _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 Fe1 N4 O7' _chemical_formula_weight 518.34 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' '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' _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 5.799(8) _cell_length_b 9.962(7) _cell_length_c 11.54(2) _cell_angle_alpha 102.12(8) _cell_angle_beta 104.00(10) _cell_angle_gamma 103.66(8) _cell_volume 602.8(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.675 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2347 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.1063 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2026 _reflns_number_gt 1302 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1713P)^2^+0.6139P] 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 2026 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1453 _refine_ls_R_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.2708 _refine_ls_wR_factor_gt 0.2325 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.0000 0.0000 0.0000 0.0229(5) Uani 1 2 d S . . C1 C -0.3361(14) -0.1532(8) -0.0762(7) 0.0307(17) Uani 1 1 d . . . H1 H -0.4796 -0.1432 -0.1260 0.037 Uiso 1 1 d R . . O1 O -0.3105(11) -0.2311(8) -0.3341(5) 0.0450(16) Uani 1 1 d . . . N1 N -0.3430(12) -0.3527(7) -0.5780(6) 0.0333(16) Uani 1 1 d . . . H1A H -0.3299 -0.3165 -0.4929 0.087 Uiso 1 1 d R . . C2 C -0.2628(16) -0.1230(9) 0.0547(7) 0.0344(18) Uani 1 1 d . . . H2 H -0.3512 -0.0904 0.1060 0.041 Uiso 1 1 d R . . O2 O 0.0543(10) -0.2650(6) -0.2625(5) 0.0391(15) Uani 1 1 d . . . N2 N -0.2707(12) -0.5161(7) -0.7264(5) 0.0290(15) Uani 1 1 d . . . H2A H -0.1986 -0.5914 -0.7440 0.970 Uiso 1 1 d R . . C3 C -0.0324(16) -0.1507(9) 0.0947(7) 0.0342(18) Uani 1 1 d . . . H3 H 0.0574 -0.1390 0.1766 0.041 Uiso 1 1 d R . . C4 C 0.0358(15) -0.1996(8) -0.0125(7) 0.0299(17) Uani 1 1 d . . . H4 H 0.1792 -0.2258 -0.0131 0.036 Uiso 1 1 d R . . C5 C -0.1496(13) -0.2014(8) -0.1182(6) 0.0251(16) Uani 1 1 d . . . C6 C -0.1289(14) -0.2322(8) -0.2461(7) 0.0289(17) Uani 1 1 d . . . C7 C -0.458(2) -0.2863(10) -0.6688(8) 0.045(2) Uani 1 1 d . . . H7A H -0.3327 -0.2059 -0.6742 0.054 Uiso 1 1 d R . . H7B H -0.5840 -0.2503 -0.6427 0.054 Uiso 1 1 d R . . C9 C -0.2584(13) -0.4598(8) -0.6105(6) 0.0247(16) Uani 1 1 d . . . C11 C -0.3911(17) -0.4670(9) -0.8293(7) 0.0363(19) Uani 1 1 d . . . H11A H -0.4757 -0.5484 -0.9029 0.044 Uiso 1 1 d R . . H11B H -0.2662 -0.3989 -0.8483 0.044 Uiso 1 1 d R . . C12 C -0.5742(18) -0.3967(10) -0.7936(8) 0.045(2) Uani 1 1 d . . . H12A H -0.7158 -0.4694 -0.7908 0.054 Uiso 1 1 d R . . H12B H -0.6344 -0.3508 -0.8559 0.054 Uiso 1 1 d R . . C13 C -0.1403(13) -0.5224(8) -0.5136(6) 0.0262(16) Uani 1 1 d . . . H13A H -0.2062 -0.6267 -0.5424 0.031 Uiso 1 1 d R . . H13B H -0.1807 -0.4898 -0.4378 0.031 Uiso 1 1 d R . . O3 O 0.342(2) -0.0688(11) -0.3515(9) 0.098(3) Uani 1 1 d . . . O4 O -0.155(3) 0.0709(18) -0.4041(12) 0.068(4) Uani 0.50 1 d P . . 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 0.0212(8) 0.0275(9) 0.0170(8) 0.0015(6) 0.0026(6) 0.0097(6) C1 0.020(4) 0.037(4) 0.029(4) 0.004(3) 0.005(3) 0.007(3) O1 0.035(3) 0.074(5) 0.024(3) 0.001(3) 0.005(3) 0.030(3) N1 0.036(4) 0.039(4) 0.027(3) 0.007(3) 0.006(3) 0.020(3) C2 0.038(5) 0.033(4) 0.034(4) 0.007(3) 0.020(4) 0.008(4) O2 0.034(3) 0.049(4) 0.037(3) 0.000(3) 0.014(3) 0.025(3) N2 0.035(4) 0.037(4) 0.017(3) 0.007(3) 0.005(3) 0.018(3) C3 0.038(5) 0.036(4) 0.023(4) 0.010(3) 0.002(3) 0.008(4) C4 0.030(4) 0.031(4) 0.029(4) 0.012(3) 0.004(3) 0.013(3) C5 0.021(4) 0.027(4) 0.020(3) -0.004(3) 0.001(3) 0.008(3) C6 0.021(4) 0.033(4) 0.024(4) -0.003(3) 0.001(3) 0.006(3) C7 0.065(6) 0.042(5) 0.040(5) 0.019(4) 0.016(4) 0.035(5) C9 0.018(3) 0.032(4) 0.020(3) 0.004(3) -0.001(3) 0.010(3) C11 0.050(5) 0.036(5) 0.023(4) 0.015(3) 0.001(3) 0.018(4) C12 0.049(5) 0.051(5) 0.037(5) 0.024(4) 0.001(4) 0.025(5) C13 0.023(4) 0.035(4) 0.020(3) 0.006(3) 0.003(3) 0.014(3) O3 0.143(10) 0.089(7) 0.092(7) 0.041(6) 0.052(7) 0.061(7) O4 0.109(13) 0.082(11) 0.029(7) 0.024(7) 0.018(7) 0.052(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 Fe1 C5 2.023(7) . ? Fe1 C5 2.023(7) 2 ? Fe1 C1 2.025(8) . ? Fe1 C1 2.025(8) 2 ? Fe1 C4 2.026(8) 2 ? Fe1 C4 2.026(8) . ? Fe1 C2 2.032(8) 2 ? Fe1 C2 2.032(8) . ? Fe1 C3 2.035(8) 2 ? Fe1 C3 2.035(8) . ? C1 C2 1.410(11) . ? C1 C5 1.427(10) . ? C1 H1 0.9300 . ? O1 C6 1.278(9) . ? N1 C9 1.299(9) . ? N1 C7 1.463(10) . ? N1 H1A 0.9500 . ? C2 C3 1.416(12) . ? C2 H2 0.9299 . ? O2 C6 1.227(9) . ? N2 C9 1.315(9) . ? N2 C11 1.462(9) . ? N2 H2A 0.9500 . ? C3 C4 1.413(11) . ? C3 H3 0.9300 . ? C4 C5 1.411(10) . ? C4 H4 0.9300 . ? C5 C6 1.484(10) . ? C7 C12 1.500(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C13 1.495(10) . ? C11 C12 1.493(13) . ? C11 H11A 0.9700 . ? C11 H11B 0.9699 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C13 1.515(14) 2_544 ? C13 H13A 0.9700 . ? C13 H13B 0.9699 . ? 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 Fe1 C5 180.0(5) . 2 ? C5 Fe1 C1 41.3(3) . . ? C5 Fe1 C1 138.7(3) 2 . ? C5 Fe1 C1 138.7(3) . 2 ? C5 Fe1 C1 41.3(3) 2 2 ? C1 Fe1 C1 180.0(4) . 2 ? C5 Fe1 C4 139.2(3) . 2 ? C5 Fe1 C4 40.8(3) 2 2 ? C1 Fe1 C4 111.1(3) . 2 ? C1 Fe1 C4 68.9(3) 2 2 ? C5 Fe1 C4 40.8(3) . . ? C5 Fe1 C4 139.2(3) 2 . ? C1 Fe1 C4 68.9(3) . . ? C1 Fe1 C4 111.1(3) 2 . ? C4 Fe1 C4 180.0(4) 2 . ? C5 Fe1 C2 111.3(3) . 2 ? C5 Fe1 C2 68.7(3) 2 2 ? C1 Fe1 C2 139.3(3) . 2 ? C1 Fe1 C2 40.7(3) 2 2 ? C4 Fe1 C2 68.4(3) 2 2 ? C4 Fe1 C2 111.6(3) . 2 ? C5 Fe1 C2 68.7(3) . . ? C5 Fe1 C2 111.3(3) 2 . ? C1 Fe1 C2 40.7(3) . . ? C1 Fe1 C2 139.3(3) 2 . ? C4 Fe1 C2 111.6(3) 2 . ? C4 Fe1 C2 68.4(3) . . ? C2 Fe1 C2 180.0(5) 2 . ? C5 Fe1 C3 111.2(3) . 2 ? C5 Fe1 C3 68.8(3) 2 2 ? C1 Fe1 C3 111.1(3) . 2 ? C1 Fe1 C3 68.9(3) 2 2 ? C4 Fe1 C3 40.7(3) 2 2 ? C4 Fe1 C3 139.3(3) . 2 ? C2 Fe1 C3 40.7(4) 2 2 ? C2 Fe1 C3 139.3(4) . 2 ? C5 Fe1 C3 68.8(3) . . ? C5 Fe1 C3 111.2(3) 2 . ? C1 Fe1 C3 68.9(3) . . ? C1 Fe1 C3 111.1(3) 2 . ? C4 Fe1 C3 139.3(3) 2 . ? C4 Fe1 C3 40.7(3) . . ? C2 Fe1 C3 139.3(4) 2 . ? C2 Fe1 C3 40.7(4) . . ? C3 Fe1 C3 180.0(4) 2 . ? C2 C1 C5 107.6(7) . . ? C2 C1 Fe1 69.9(5) . . ? C5 C1 Fe1 69.3(4) . . ? C2 C1 H1 126.2 . . ? C5 C1 H1 126.2 . . ? Fe1 C1 H1 126.0 . . ? C9 N1 C7 121.8(6) . . ? C9 N1 H1A 119.1 . . ? C7 N1 H1A 119.1 . . ? C1 C2 C3 108.7(7) . . ? C1 C2 Fe1 69.4(5) . . ? C3 C2 Fe1 69.7(5) . . ? C1 C2 H2 125.6 . . ? C3 C2 H2 125.7 . . ? Fe1 C2 H2 126.8 . . ? C9 N2 C11 122.4(6) . . ? C9 N2 H2A 118.8 . . ? C11 N2 H2A 118.8 . . ? C4 C3 C2 107.5(7) . . ? C4 C3 Fe1 69.3(5) . . ? C2 C3 Fe1 69.5(5) . . ? C4 C3 H3 126.3 . . ? C2 C3 H3 126.2 . . ? Fe1 C3 H3 126.5 . . ? C5 C4 C3 108.6(7) . . ? C5 C4 Fe1 69.5(4) . . ? C3 C4 Fe1 70.0(5) . . ? C5 C4 H4 125.7 . . ? C3 C4 H4 125.7 . . ? Fe1 C4 H4 126.2 . . ? C4 C5 C1 107.7(6) . . ? C4 C5 C6 123.9(6) . . ? C1 C5 C6 128.1(7) . . ? C4 C5 Fe1 69.7(4) . . ? C1 C5 Fe1 69.4(4) . . ? C6 C5 Fe1 120.9(6) . . ? O2 C6 O1 123.7(7) . . ? O2 C6 C5 118.3(7) . . ? O1 C6 C5 117.8(6) . . ? N1 C7 C12 109.1(7) . . ? N1 C7 H7A 109.9 . . ? C12 C7 H7A 109.9 . . ? N1 C7 H7B 109.8 . . ? C12 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N1 C9 N2 122.6(7) . . ? N1 C9 C13 119.5(6) . . ? N2 C9 C13 117.8(6) . . ? N2 C11 C12 109.5(7) . . ? N2 C11 H11A 109.7 . . ? C12 C11 H11A 109.9 . . ? N2 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.3 . . ? C11 C12 C7 111.1(7) . . ? C11 C12 H12A 109.3 . . ? C7 C12 H12A 109.4 . . ? C11 C12 H12B 109.5 . . ? C7 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C9 C13 C13 110.6(8) . 2_544 ? C9 C13 H13A 109.5 . . ? C13 C13 H13A 109.5 2_544 . ? C9 C13 H13B 109.5 . . ? C13 C13 H13B 109.6 2_544 . ? H13A C13 H13B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 1.174 _refine_diff_density_min -1.017 _refine_diff_density_rms 0.158 data_bad23fe2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H38 Fe2 N4 O8' _chemical_formula_weight 742.38 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.91(1) _cell_length_b 10.623(5) _cell_length_c 13.516(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.96(8) _cell_angle_gamma 90.00 _cell_volume 1626.7(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.951 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2972 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2845 _reflns_number_gt 1806 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.3909P] 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 2845 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.25531(4) 0.08921(5) 0.87155(4) 0.03069(18) Uani 1 1 d . . . C1 C 0.12886(15) 0.0136(2) 0.9278(2) 0.0347(9) Uani 1 1 d G . . H1 H 0.0481 0.0291 0.9040 0.042 Uiso 1 1 calc R . . C2 C 0.1889(2) -0.0841(2) 0.89308(19) 0.0406(9) Uani 1 1 d G . . H2 H 0.1544 -0.1437 0.8425 0.049 Uiso 1 1 calc R . . C3 C 0.3109(2) -0.0747(2) 0.9492(2) 0.0381(9) Uani 1 1 d G . . H3 H 0.3704 -0.1271 0.9417 0.046 Uiso 1 1 calc R . . C4 C 0.32625(16) 0.0288(2) 1.01857(19) 0.0338(9) Uani 1 1 d G . . H4 H 0.3975 0.0560 1.0646 0.041 Uiso 1 1 calc R . . C5 C 0.2137(2) 0.0833(2) 1.00540(19) 0.0283(7) Uani 1 1 d G . . C6 C 0.1870(3) 0.1987(3) 1.0566(3) 0.0316(8) Uani 1 1 d . . . O1 O 0.0844(2) 0.2157(3) 1.0561(2) 0.0440(7) Uani 1 1 d . . . O2 O 0.2707(2) 0.2719(2) 1.0986(2) 0.0411(7) Uani 1 1 d . . . C7 C 0.2322(2) 0.1179(2) 0.71750(19) 0.0449(10) Uani 1 1 d G . . H7 H 0.1934 0.0648 0.6630 0.054 Uiso 1 1 calc R . . C8 C 0.3543(2) 0.1144(3) 0.7742(2) 0.0511(12) Uani 1 1 d G . . H8 H 0.4095 0.0587 0.7633 0.061 Uiso 1 1 calc R . . C9 C 0.37730(17) 0.2110(3) 0.8504(2) 0.0510(12) Uani 1 1 d G . . H9 H 0.4502 0.2297 0.8982 0.061 Uiso 1 1 calc R . . C10 C 0.2694(2) 0.2742(2) 0.8409(2) 0.0396(10) Uani 1 1 d G . . H10 H 0.2593 0.3415 0.8813 0.048 Uiso 1 1 calc R . . C11 C 0.17971(16) 0.2167(2) 0.7587(2) 0.0337(9) Uani 1 1 d G . . C12 C 0.0561(3) 0.2564(3) 0.7262(3) 0.0341(9) Uani 1 1 d . . . O3 O -0.0078(2) 0.1952(3) 0.6436(2) 0.0494(7) Uani 1 1 d . . . H300 H -0.0836 0.2329 0.6388 0.050 Uiso 1 1 d . . . O4 O 0.0182(2) 0.3380(3) 0.7686(2) 0.0472(7) Uani 1 1 d . . . C13 C 0.0507(3) 0.5186(4) 0.9798(3) 0.0336(9) Uani 1 1 d . . . H13 H 0.021(3) 0.571(4) 0.925(3) 0.035(11) Uiso 1 1 d . . . H14 H 0.080(3) 0.444(4) 0.957(3) 0.039(11) Uiso 1 1 d . . . C14 C 0.1431(3) 0.5876(4) 1.0598(3) 0.0323(8) Uani 1 1 d . . . N1 N 0.1309(3) 0.7089(3) 1.0699(3) 0.0317(7) Uani 1 1 d . . . H15 H 0.069(3) 0.739(4) 1.035(3) 0.035(12) Uiso 1 1 d . . . N2 N 0.2318(3) 0.5254(3) 1.1206(3) 0.0401(8) Uani 1 1 d . . . H16 H 0.233(3) 0.445(4) 1.110(3) 0.033(11) Uiso 1 1 d . . . C15 C 0.3229(4) 0.5841(4) 1.2045(4) 0.0524(11) Uani 1 1 d . . . H17 H 0.309(4) 0.576(4) 1.271(4) 0.057(14) Uiso 1 1 d . . . H18 H 0.402(4) 0.543(5) 1.214(4) 0.075(15) Uiso 1 1 d . . . C16 C 0.3319(4) 0.7219(4) 1.1807(4) 0.0457(11) Uani 1 1 d . . . H19 H 0.385(4) 0.758(4) 1.245(4) 0.058(13) Uiso 1 1 d . . . H20 H 0.361(3) 0.734(4) 1.131(3) 0.042(12) Uiso 1 1 d . . . C17 C 0.2121(4) 0.7811(4) 1.1516(3) 0.0377(9) Uani 1 1 d . . . H21 H 0.182(3) 0.779(4) 1.210(3) 0.042(11) Uiso 1 1 d . . . H22 H 0.213(3) 0.863(4) 1.127(3) 0.047(12) 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 0.0325(3) 0.0284(3) 0.0324(3) 0.0054(3) 0.0118(2) 0.0022(2) C1 0.036(2) 0.033(2) 0.035(2) 0.0039(18) 0.0116(18) -0.0070(17) C2 0.060(3) 0.0279(19) 0.037(2) -0.0072(19) 0.020(2) -0.0061(19) C3 0.049(2) 0.030(2) 0.037(2) 0.0049(18) 0.0152(19) 0.0091(18) C4 0.037(2) 0.030(2) 0.032(2) 0.0057(17) 0.0073(18) 0.0076(17) C5 0.0323(18) 0.0245(17) 0.0277(19) 0.0018(16) 0.0084(16) 0.0009(16) C6 0.035(2) 0.031(2) 0.026(2) 0.0056(17) 0.0050(18) 0.0055(17) O1 0.0342(15) 0.0517(17) 0.0451(17) -0.0008(14) 0.0109(13) 0.0144(13) O2 0.0357(14) 0.0347(15) 0.0450(17) -0.0089(13) 0.0007(13) 0.0037(12) C7 0.058(3) 0.049(3) 0.035(2) 0.011(2) 0.025(2) 0.011(2) C8 0.050(3) 0.060(3) 0.056(3) 0.024(2) 0.034(2) 0.020(2) C9 0.032(2) 0.060(3) 0.061(3) 0.026(3) 0.015(2) -0.003(2) C10 0.040(2) 0.034(2) 0.046(3) 0.0128(19) 0.015(2) -0.0038(18) C11 0.038(2) 0.030(2) 0.034(2) 0.0097(17) 0.0137(18) 0.0029(17) C12 0.037(2) 0.030(2) 0.036(2) 0.0021(18) 0.0133(19) -0.0015(17) O3 0.0412(16) 0.0505(17) 0.0499(19) -0.0100(15) 0.0043(15) 0.0064(13) O4 0.0420(16) 0.0440(17) 0.056(2) -0.0081(15) 0.0160(15) 0.0059(13) C13 0.037(2) 0.031(2) 0.031(2) -0.0033(19) 0.0062(19) -0.0011(17) C14 0.0328(19) 0.0313(19) 0.035(2) -0.0069(19) 0.0141(17) -0.0059(18) N1 0.0288(18) 0.0280(17) 0.038(2) 0.0000(15) 0.0090(16) 0.0004(14) N2 0.042(2) 0.0262(18) 0.043(2) -0.0061(17) -0.0002(17) 0.0054(16) C15 0.051(3) 0.043(2) 0.047(3) -0.010(2) -0.009(2) 0.000(2) C16 0.040(2) 0.044(3) 0.047(3) -0.004(2) 0.004(2) -0.010(2) C17 0.048(2) 0.027(2) 0.036(2) -0.0036(18) 0.010(2) -0.0093(18) _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 C4 2.010(3) . yes Fe1 C5 2.019(3) . yes Fe1 C10 2.026(3) . yes Fe1 C11 2.030(3) . yes Fe1 C9 2.031(3) . yes Fe1 C7 2.037(3) . yes Fe1 C3 2.035(3) . yes Fe1 C8 2.037(3) . yes Fe1 C1 2.049(3) . yes Fe1 C2 2.059(3) . yes C1 C2 1.4200 . yes C1 C5 1.4200 . yes C1 H1 0.9300 . yes C2 C3 1.4200 . yes C2 H2 0.9300 . yes C3 C4 1.4200 . yes C3 H3 0.9300 . yes C4 C5 1.4200 . yes C4 H4 0.9300 . yes C5 C6 1.489(4) . yes C6 O1 1.234(4) . yes C6 O2 1.254(4) . yes C7 C8 1.4200 . yes C7 C11 1.4200 . yes C7 H7 0.9300 . yes C8 C9 1.4200 . yes C8 H8 0.9300 . yes C9 C10 1.4200 . yes C9 H9 0.9300 . yes C10 C11 1.4200 . yes C10 H10 0.9300 . yes C11 C12 1.463(4) . yes C12 O4 1.201(4) . yes C12 O3 1.313(5) . yes O3 H300 0.9708 . yes C13 C14 1.478(5) . yes C13 C13 1.524(7) 3_567 yes C13 H13 0.90(4) . yes C13 H14 0.95(4) . yes C14 N2 1.301(5) . yes C14 N1 1.309(5) . yes N1 C17 1.444(5) . yes N1 H15 0.81(4) . yes N2 C15 1.447(5) . yes N2 H16 0.86(4) . yes C15 C16 1.509(6) . yes C15 H17 0.97(5) . yes C15 H18 1.02(5) . yes C16 C17 1.497(6) . yes C16 H19 0.98(5) . yes C16 H20 0.85(4) . yes C17 H21 0.97(4) . yes C17 H22 0.93(4) . yes 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 C4 Fe1 C5 41.3 . . yes C4 Fe1 C10 118.43(10) . . yes C5 Fe1 C10 105.79(9) . . yes C4 Fe1 C11 155.43(11) . . yes C5 Fe1 C11 121.28(10) . . yes C10 Fe1 C11 41.0 . . yes C4 Fe1 C9 103.99(11) . . yes C5 Fe1 C9 121.98(12) . . yes C10 Fe1 C9 41.0 . . yes C11 Fe1 C9 68.91(8) . . yes C4 Fe1 C7 160.29(10) . . yes C5 Fe1 C7 158.03(11) . . yes C10 Fe1 C7 68.86(6) . . yes C11 Fe1 C7 40.9 . . yes C9 Fe1 C7 68.78(8) . . yes C4 Fe1 C3 41.1 . . yes C5 Fe1 C3 69.05(7) . . yes C10 Fe1 C3 154.28(11) . . yes C11 Fe1 C3 162.95(11) . . yes C9 Fe1 C3 118.98(11) . . yes C7 Fe1 C3 125.07(10) . . yes C4 Fe1 C8 122.01(12) . . yes C5 Fe1 C8 159.03(12) . . yes C10 Fe1 C8 68.86(6) . . yes C11 Fe1 C8 68.78(7) . . yes C9 Fe1 C8 40.9 . . yes C7 Fe1 C8 40.8 . . yes C3 Fe1 C8 106.51(9) . . yes C4 Fe1 C1 68.94(9) . . yes C5 Fe1 C1 40.9 . . yes C10 Fe1 C1 124.96(10) . . yes C11 Fe1 C1 109.51(10) . . yes C9 Fe1 C1 160.35(12) . . yes C7 Fe1 C1 123.70(12) . . yes C3 Fe1 C1 68.46(7) . . yes C8 Fe1 C1 158.33(12) . . yes C4 Fe1 C2 68.74(7) . . yes C5 Fe1 C2 68.58(6) . . yes C10 Fe1 C2 162.88(11) . . yes C11 Fe1 C2 126.98(11) . . yes C9 Fe1 C2 155.80(11) . . yes C7 Fe1 C2 109.96(10) . . yes C3 Fe1 C2 40.6 . . yes C8 Fe1 C2 122.18(11) . . yes C1 Fe1 C2 40.4 . . yes C2 C1 C5 108.0 . . yes C2 C1 Fe1 70.17(10) . . yes C5 C1 Fe1 68.41(11) . . yes C2 C1 H1 126.0 . . yes C5 C1 H1 126.0 . . yes Fe1 C1 H1 127.0 . . yes C3 C2 C1 108.0 . . yes C3 C2 Fe1 68.80(10) . . yes C1 C2 Fe1 69.40(10) . . yes C3 C2 H2 126.0 . . yes C1 C2 H2 126.0 . . yes Fe1 C2 H2 127.4 . . yes C4 C3 C2 108.0 . . yes C4 C3 Fe1 68.49(11) . . yes C2 C3 Fe1 70.63(10) . . yes C4 C3 H3 126.0 . . yes C2 C3 H3 126.0 . . yes Fe1 C3 H3 126.4 . . yes C3 C4 C5 108.0 . . yes C3 C4 Fe1 70.41(10) . . yes C5 C4 Fe1 69.69(11) . . yes C3 C4 H4 126.0 . . yes C5 C4 H4 126.0 . . yes Fe1 C4 H4 125.5 . . yes C4 C5 C1 108.0 . . yes C4 C5 C6 127.3(2) . . yes C1 C5 C6 124.5(2) . . yes C4 C5 Fe1 69.03(12) . . yes C1 C5 Fe1 70.73(11) . . yes C6 C5 Fe1 122.5(2) . . yes O1 C6 O2 124.0(4) . . yes O1 C6 C5 118.2(3) . . yes O2 C6 C5 117.8(3) . . yes C8 C7 C11 108.0 . . yes C8 C7 Fe1 69.61(12) . . yes C11 C7 Fe1 69.31(10) . . yes C8 C7 H7 126.0 . . yes C11 C7 H7 126.0 . . yes Fe1 C7 H7 126.7 . . yes C9 C8 C7 108.0 . . yes C9 C8 Fe1 69.32(11) . . yes C7 C8 Fe1 69.60(12) . . yes C9 C8 H8 126.0 . . yes C7 C8 H8 126.0 . . yes Fe1 C8 H8 126.7 . . yes C10 C9 C8 108.0 . . yes C10 C9 Fe1 69.35(11) . . yes C8 C9 Fe1 69.82(11) . . yes C10 C9 H9 126.0 . . yes C8 C9 H9 126.0 . . yes Fe1 C9 H9 126.4 . . yes C11 C10 C9 108.0 . . yes C11 C10 Fe1 69.67(11) . . yes C9 C10 Fe1 69.67(10) . . yes C11 C10 H10 126.0 . . yes C9 C10 H10 126.0 . . yes Fe1 C10 H10 126.2 . . yes C10 C11 C7 108.0 . . yes C10 C11 C12 123.7(2) . . yes C7 C11 C12 128.3(2) . . yes C10 C11 Fe1 69.36(12) . . yes C7 C11 Fe1 69.83(11) . . yes C12 C11 Fe1 126.2(2) . . yes O4 C12 O3 123.9(4) . . yes O4 C12 C11 123.8(4) . . yes O3 C12 C11 112.2(3) . . yes C12 O3 H300 97.8 . . yes C14 C13 C13 111.1(4) . 3_567 yes C14 C13 H13 108(2) . . yes C13 C13 H13 107(2) 3_567 . yes C14 C13 H14 113(2) . . yes C13 C13 H14 108(2) 3_567 . yes H13 C13 H14 109(3) . . yes N2 C14 N1 121.9(4) . . yes N2 C14 C13 119.1(4) . . yes N1 C14 C13 118.9(4) . . yes C14 N1 C17 122.2(4) . . yes C14 N1 H15 116(3) . . yes C17 N1 H15 121(3) . . yes C14 N2 C15 122.9(4) . . yes C14 N2 H16 117(3) . . yes C15 N2 H16 121(3) . . yes N2 C15 C16 109.6(4) . . yes N2 C15 H17 113(3) . . yes C16 C15 H17 109(3) . . yes N2 C15 H18 111(3) . . yes C16 C15 H18 109(3) . . yes H17 C15 H18 106(4) . . yes C17 C16 C15 109.8(4) . . yes C17 C16 H19 112(2) . . yes C15 C16 H19 105(3) . . yes C17 C16 H20 109(3) . . yes C15 C16 H20 113(3) . . yes H19 C16 H20 109(4) . . yes N1 C17 C16 109.7(3) . . yes N1 C17 H21 106(2) . . yes C16 C17 H21 110(2) . . yes N1 C17 H22 108(3) . . yes C16 C17 H22 112(2) . . yes H21 C17 H22 111(3) . . yes _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.621 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.075 data_st288 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C22 H36 Fe N4 O10' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H36 Fe N4 O10' _chemical_formula_weight 572.40 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Fe ? 0.301 0.845 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,-y,-z _cell_length_a 5.7680(6) _cell_length_b 10.553(1) _cell_length_c 11.536(1) _cell_angle_alpha 109.374(1) _cell_angle_beta 94.184(1) _cell_angle_gamma 90.998(1) _cell_volume 660.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.44 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 302 _exptl_absorpt_coefficient_mu 0.632 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 91 frames,180 sec/frame, delta phi = 2.0 deg. Each frame measured 2 times. Detector to crystal distance 29 mm. ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5265 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 34.27 _reflns_number_total 4093 _reflns_number_gt 3223 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3223 _refine_ls_number_parameters 169 _refine_ls_number_restraints 3 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.060 _refine_ls_R_factor_gt 0.046 _refine_ls_wR_factor_all 0.074 _refine_ls_wR_factor_ref 0.074 _refine_ls_goodness_of_fit_all 1.329 _refine_ls_goodness_of_fit_ref 1.325 _refine_ls_shift/su_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.586 _refine_diff_density_min -0.608 #=============================================================================== # 9. ATOMIC COORDINATES AND TH ERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 1.7225(3) 0.3721(2) 1.5102(2) 0.0249(7) 1.000 Uani ? ? C N1 1.6655(3) 0.2497(2) 1.4333(1) 0.0277(6) 1.000 Uani ? ? N C2 1.7424(4) 0.1298(2) 1.4586(2) 0.0321(8) 1.000 Uani ? ? C C3 1.7724(4) 0.1603(2) 1.5973(2) 0.0333(8) 1.000 Uani ? ? C C4 1.9372(3) 0.2834(2) 1.6540(2) 0.0342(8) 1.000 Uani ? ? C N2 1.8564(3) 0.3937(1) 1.6128(1) 0.0276(6) 1.000 Uani ? ? N O1 1.5494(3) 0.1805(1) 1.6403(1) 0.0381(7) 1.000 Uani ? ? O C5 1.6250(3) 0.4897(2) 1.4810(2) 0.0257(7) 1.000 Uani ? ? C FE 2.0000 1.0000 2.0000 0.0218(1) 0.500 Uani ? ? Fe C6 1.9824(3) 0.8863(2) 1.8183(2) 0.0236(7) 1.000 Uani ? ? C C7 2.2190(3) 0.9296(2) 1.8630(2) 0.0256(7) 1.000 Uani ? ? C C8 2.2328(3) 1.0725(2) 1.9081(2) 0.0293(8) 1.000 Uani ? ? C C9 1.9942(4) 0.8807(2) 2.1091(2) 0.0306(8) 1.000 Uani ? ? C C10 2.1478(3) 0.9943(2) 2.1642(2) 0.0282(7) 1.000 Uani ? ? C C11 1.8808(3) 0.7465(2) 1.7726(2) 0.0249(7) 1.000 Uani ? ? C O2 2.0141(2) 0.6505(1) 1.7609(1) 0.0318(6) 1.000 Uani ? ? O O3 1.6634(2) 0.7312(1) 1.7473(1) 0.0296(6) 1.000 Uani ? ? O O4 1.4169(3) 0.6092(1) 1.8771(1) 0.0403(7) 1.000 Uani ? ? O O5 1.5546(4) 0.3539(2) 1.8713(2) 0.054(1) 1.000 Uani ? ? O H1 1.5716 0.2395 1.3593 0.0379 1.000 Uiso calc N1 H H2 1.8866 0.1047 1.4245 0.0441 1.000 Uiso calc C2 H H3 1.6294 0.0582 1.4228 0.0441 1.000 Uiso calc C2 H H4 1.8389 0.0891 1.6197 0.0449 1.000 Uiso calc C3 H H5 2.0889 0.2616 1.6289 0.0443 1.000 Uiso calc C4 H H6 1.9412 0.3106 1.7413 0.0443 1.000 Uiso calc C4 H H7 1.9022 0.4836 1.6617 0.0374 1.000 Uiso calc N2 H H8 1.6247 0.4734 1.3949 0.0340 1.000 Uiso calc C5 H H9 1.7189 0.5683 1.5247 0.0340 1.000 Uiso calc C5 H H10 2.3449 0.8726 1.8625 0.0351 1.000 Uiso calc C7 H H11 2.3692 1.1275 1.9436 0.0400 1.000 Uiso calc C8 H H12 2.0347 0.7893 2.0874 0.0406 1.000 Uiso calc C9 H H13 2.3094 0.9923 2.1860 0.0372 1.000 Uiso calc C10 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.0252(7) 0.0247(7) 0.0247(7) 0.0021(6) 0.0031(6) 0.0050(6) C N1 0.0358(7) 0.0240(6) 0.0248(6) 0.0025(5) -0.0008(6) 0.0048(6) N C2 0.049(1) 0.0232(7) 0.0291(8) 0.0089(7) 0.0073(7) 0.0070(7) C C3 0.045(1) 0.0274(8) 0.0299(8) 0.0057(7) 0.0028(7) 0.0079(7) C C4 0.0334(8) 0.0359(8) 0.0335(8) 0.0053(7) -0.0049(7) 0.0137(7) C N2 0.0277(6) 0.0261(6) 0.0290(7) 0.0009(5) -0.0039(5) 0.0060(6) N O1 0.0433(7) 0.0359(6) 0.0356(7) -0.0034(6) 0.0073(6) 0.0075(6) O C5 0.0281(7) 0.0241(7) 0.0251(7) 0.0005(6) 0.0005(6) 0.0069(6) C FE 0.0245(1) 0.0216(1) 0.0196(1) -0.0000(1) 0.0014(1) 0.0039(1) Fe C6 0.0259(7) 0.0273(7) 0.0186(6) -0.0004(6) 0.0004(5) 0.0030(6) C C7 0.0244(7) 0.0287(7) 0.0240(7) -0.0005(6) 0.0026(6) 0.0036(6) C C8 0.0310(8) 0.0303(8) 0.0269(7) -0.0069(6) 0.0040(6) 0.0042(7) C C9 0.0400(9) 0.0263(7) 0.0273(7) 0.0019(7) 0.0040(7) 0.0087(7) C C10 0.0319(8) 0.0322(8) 0.0218(7) 0.0032(6) 0.0000(6) 0.0097(6) C C11 0.0266(7) 0.0290(7) 0.0201(7) -0.0011(6) -0.0004(6) 0.0037(6) C O2 0.0311(6) 0.0261(5) 0.0396(7) -0.0008(5) -0.0046(5) 0.0016(6) O O3 0.0246(5) 0.0352(6) 0.0298(6) -0.0033(5) -0.0039(5) 0.0058(5) O O4 0.0379(7) 0.0433(7) 0.0399(7) 0.0038(6) 0.0011(6) 0.0193(6) O O5 0.110(1) 0.0417(8) 0.0337(8) 0.0192(9) 0.0152(9) 0.0069(7) O # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.321(2) . . ? C1 N2 1.315(2) . . ? C1 C5 1.498(3) . . ? N1 C2 1.459(3) . . ? C2 C3 1.520(3) . . ? C3 C4 1.524(3) . . ? C3 O1 1.406(3) . . ? C4 N2 1.467(3) . . ? C5 C5 1.536(4) . 2_868 ? FE C6 2.034(2) . . ? FE C7 2.047(2) . . ? FE C8 2.055(2) . . ? FE C9 2.056(2) . . ? FE C10 2.040(2) . . ? C6 C7 1.434(2) . . ? C6 C11 1.485(3) . . ? C7 C8 1.422(3) . . ? C9 C10 1.415(3) . . ? C11 O2 1.261(2) . . ? C11 O3 1.261(2) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 122.2(2) . . . ? N1 C1 C5 118.6(2) . . . ? N2 C1 C5 119.1(2) . . . ? C1 N1 C2 122.0(2) . . . ? N1 C2 C3 109.0(2) . . . ? C2 C3 C4 108.6(2) . . . ? C2 C3 O1 106.9(2) . . . ? C4 C3 O1 112.7(2) . . . ? C3 C4 N2 109.8(2) . . . ? C1 N2 C4 122.1(2) . . . ? C1 C5 C5 110.2(2) . . 2_868 ? C6 FE C7 41.14(7) . . . ? C6 FE C8 68.93(7) . . . ? C6 FE C9 110.97(8) . . . ? C6 FE C10 138.55(8) . . . ? C7 FE C8 40.55(8) . . . ? C7 FE C9 111.45(8) . . . ? C7 FE C10 111.07(8) . . . ? C8 FE C9 139.25(8) . . . ? C8 FE C10 111.56(8) . . . ? C9 FE C10 40.41(8) . . . ? FE C6 C7 69.9(1) . . . ? FE C6 C11 121.8(1) . . . ? C7 C6 C11 127.6(2) . . . ? FE C7 C6 68.9(1) . . . ? FE C7 C8 70.0(1) . . . ? C6 C7 C8 108.2(2) . . . ? FE C8 C7 69.4(1) . . . ? FE C9 C10 69.2(1) . . . ? FE C10 C9 70.4(1) . . . ? C6 C11 O2 118.9(2) . . . ? C6 C11 O3 117.4(2) . . . ? O2 C11 O3 123.7(2) . . . ?