# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_FeCID-1 _database_code_depnum_ccdc_archive 'CCDC 901080' #TrackingRef 'web_deposit_cif_file_0_SatoshiHorike_1347458117.FeCID-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Fe N2 O4' _chemical_formula_weight 376.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0217(19) _cell_length_b 10.100(2) _cell_length_c 10.108(2) _cell_angle_alpha 78.436(9) _cell_angle_beta 73.667(7) _cell_angle_gamma 79.609(9) _cell_volume 858.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8401 _exptl_absorpt_correction_T_max 0.8401 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6872 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3737 _reflns_number_gt 3189 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.1159P)^2^+0.1423P] 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 3737 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 -0.06638(4) 0.37352(4) -0.10412(4) 0.01801(18) Uani 1 1 d . . . O2 O -0.0545(3) 1.1591(2) -0.0997(2) 0.0260(5) Uani 1 1 d . . . O3 O -0.0842(3) 0.6610(2) -0.0216(2) 0.0266(5) Uani 1 1 d . . . O4 O -0.1892(3) 1.2940(2) -0.2355(2) 0.0291(5) Uani 1 1 d . . . O5 O -0.1395(3) 0.5710(2) -0.1822(2) 0.0227(5) Uani 1 1 d . . . C1 C -0.1211(3) 0.6719(3) -0.1336(3) 0.0203(6) Uani 1 1 d . . . N7 N -0.2613(3) 0.3678(2) 0.0832(3) 0.0221(5) Uani 1 1 d . . . C8 C -0.4914(3) 0.3700(3) 0.3386(3) 0.0214(6) Uani 1 1 d . . . C9 C 0.1411(4) 0.4732(3) -0.3968(3) 0.0295(7) Uani 1 1 d . . . H1 H 0.0569 0.5436 -0.3931 0.035 Uiso 1 1 calc R . . N1 N 0.1394(3) 0.3775(2) -0.2838(2) 0.0217(5) Uani 1 1 d . . . C11 C -0.1300(3) 0.9251(3) -0.1657(3) 0.0218(6) Uani 1 1 d . . . H2 H -0.1009 0.9145 -0.0815 0.026 Uiso 1 1 calc R . . C12 C 0.3853(3) 0.3733(3) -0.5286(3) 0.0215(6) Uani 1 1 d . . . C13 C -0.3708(4) 0.4745(3) 0.1074(3) 0.0312(7) Uani 1 1 d . . . H3 H -0.3704 0.5502 0.0360 0.037 Uiso 1 1 calc R . . C14 C -0.1553(4) 1.0550(3) -0.2416(3) 0.0239(6) Uani 1 1 d . . . C15 C -0.1326(4) 1.1775(3) -0.1891(3) 0.0225(6) Uani 1 1 d . . . C16 C 0.2589(4) 0.4748(3) -0.5182(3) 0.0297(7) Uani 1 1 d . . . H4 H 0.2534 0.5450 -0.5940 0.036 Uiso 1 1 calc R . . C17 C -0.1479(4) 0.8111(3) -0.2150(3) 0.0232(6) Uani 1 1 d . . . C18 C -0.4850(4) 0.4801(3) 0.2313(3) 0.0311(7) Uani 1 1 d . . . H5 H -0.5582 0.5586 0.2427 0.037 Uiso 1 1 calc R . . C19 C -0.1864(5) 0.8279(3) -0.3418(4) 0.0357(8) Uani 1 1 d . . . H6 H -0.1963 0.7511 -0.3764 0.043 Uiso 1 1 calc R . . C20 C -0.1969(5) 1.0715(3) -0.3668(4) 0.0381(8) Uani 1 1 d . . . H7 H -0.2159 1.1591 -0.4169 0.046 Uiso 1 1 calc R . . C21 C 0.2628(4) 0.2809(4) -0.2926(3) 0.0340(8) Uani 1 1 d . . . H8 H 0.2662 0.2132 -0.2144 0.041 Uiso 1 1 calc R . . C22 C 0.3863(4) 0.2750(4) -0.4108(3) 0.0339(8) Uani 1 1 d . . . H9 H 0.4704 0.2048 -0.4111 0.041 Uiso 1 1 calc R . . C23 C -0.3799(4) 0.2582(4) 0.3129(4) 0.0371(8) Uani 1 1 d . . . H10 H -0.3793 0.1804 0.3819 0.045 Uiso 1 1 calc R . . C24 C -0.2695(4) 0.2604(4) 0.1861(4) 0.0381(9) Uani 1 1 d . . . H11 H -0.1962 0.1824 0.1713 0.046 Uiso 1 1 calc R . . C25 C -0.2103(6) 0.9568(4) -0.4175(4) 0.0470(11) Uani 1 1 d . . . H12 H -0.2356 0.9669 -0.5034 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0240(3) 0.0117(3) 0.0168(3) -0.00192(16) -0.00310(17) -0.00214(17) O2 0.0384(12) 0.0160(11) 0.0268(11) -0.0035(8) -0.0139(10) -0.0027(9) O3 0.0357(12) 0.0201(11) 0.0254(11) 0.0017(8) -0.0132(9) -0.0046(9) O4 0.0407(13) 0.0126(11) 0.0356(12) -0.0017(9) -0.0166(10) 0.0008(9) O5 0.0322(11) 0.0123(10) 0.0233(10) -0.0044(8) -0.0054(9) -0.0031(8) C1 0.0214(13) 0.0178(14) 0.0205(13) -0.0023(11) -0.0041(11) -0.0021(11) N7 0.0257(12) 0.0159(12) 0.0230(12) 0.0002(9) -0.0065(10) -0.0017(9) C8 0.0223(14) 0.0194(15) 0.0220(13) -0.0021(11) -0.0061(11) -0.0018(11) C9 0.0289(16) 0.0284(17) 0.0219(15) 0.0028(12) -0.0014(12) 0.0047(13) N1 0.0267(13) 0.0174(12) 0.0175(11) 0.0006(9) -0.0040(10) -0.0002(10) C11 0.0261(14) 0.0183(15) 0.0236(14) -0.0050(11) -0.0095(11) -0.0027(11) C12 0.0236(14) 0.0195(15) 0.0213(14) -0.0041(11) -0.0056(11) -0.0017(11) C13 0.0315(17) 0.0247(17) 0.0266(16) 0.0048(13) 0.0015(13) -0.0001(13) C14 0.0333(16) 0.0126(14) 0.0287(15) -0.0025(11) -0.0127(13) -0.0033(11) C15 0.0275(15) 0.0163(14) 0.0243(14) -0.0046(11) -0.0051(11) -0.0050(11) C16 0.0317(17) 0.0278(17) 0.0193(14) 0.0027(12) -0.0011(12) 0.0061(13) C17 0.0309(15) 0.0138(14) 0.0266(15) -0.0017(11) -0.0111(12) -0.0030(11) C18 0.0297(16) 0.0225(17) 0.0280(16) 0.0019(13) 0.0045(13) 0.0045(13) C19 0.063(2) 0.0158(16) 0.0408(19) -0.0050(13) -0.0322(18) -0.0053(15) C20 0.061(2) 0.0167(16) 0.045(2) 0.0013(14) -0.0316(18) -0.0021(15) C21 0.0343(18) 0.0340(19) 0.0202(14) 0.0060(13) 0.0016(13) 0.0049(14) C22 0.0284(17) 0.0346(19) 0.0262(16) 0.0046(14) -0.0001(13) 0.0065(14) C23 0.0374(19) 0.0282(18) 0.0276(16) 0.0073(14) 0.0045(14) 0.0086(14) C24 0.039(2) 0.0278(18) 0.0308(18) 0.0028(14) 0.0049(15) 0.0069(14) C25 0.088(3) 0.0265(19) 0.041(2) 0.0013(15) -0.044(2) -0.0095(19) _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 O3 2.051(2) 2_565 ? Fe1 O5 2.055(2) . ? Fe1 O2 2.140(2) 1_545 ? Fe1 N7 2.191(3) . ? Fe1 N1 2.202(3) . ? Fe1 O4 2.283(2) 1_545 ? O2 C15 1.262(4) . ? O2 Fe1 2.141(2) 1_565 ? O3 C1 1.246(3) . ? O3 Fe1 2.051(2) 2_565 ? O4 C15 1.250(4) . ? O4 Fe1 2.283(2) 1_565 ? O5 C1 1.270(3) . ? C1 C17 1.497(4) . ? N7 C13 1.335(4) . ? N7 C24 1.341(4) . ? C8 C23 1.384(4) . ? C8 C18 1.385(4) . ? C8 C12 1.485(4) 1_456 ? C9 N1 1.338(4) . ? C9 C16 1.378(4) . ? C9 H1 0.9400 . ? N1 C21 1.337(4) . ? C11 C17 1.393(4) . ? C11 C14 1.396(4) . ? C11 H2 0.9400 . ? C12 C16 1.385(4) . ? C12 C22 1.390(4) . ? C12 C8 1.485(4) 1_654 ? C13 C18 1.384(4) . ? C13 H3 0.9400 . ? C14 C20 1.390(4) . ? C14 C15 1.506(4) . ? C16 H4 0.9400 . ? C17 C19 1.391(4) . ? C18 H5 0.9400 . ? C19 C25 1.385(5) . ? C19 H6 0.9400 . ? C20 C25 1.393(5) . ? C20 H7 0.9400 . ? C21 C22 1.388(4) . ? C21 H8 0.9400 . ? C22 H9 0.9400 . ? C23 C24 1.384(5) . ? C23 H10 0.9400 . ? C24 H11 0.9400 . ? C25 H12 0.9400 . ? 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 O3 Fe1 O5 118.93(8) 2_565 . ? O3 Fe1 O2 91.02(8) 2_565 1_545 ? O5 Fe1 O2 149.77(9) . 1_545 ? O3 Fe1 N7 88.96(9) 2_565 . ? O5 Fe1 N7 93.44(9) . . ? O2 Fe1 N7 90.98(9) 1_545 . ? O3 Fe1 N1 87.48(9) 2_565 . ? O5 Fe1 N1 88.16(9) . . ? O2 Fe1 N1 89.24(9) 1_545 . ? N7 Fe1 N1 176.43(8) . . ? O3 Fe1 O4 150.01(8) 2_565 1_545 ? O5 Fe1 O4 90.46(8) . 1_545 ? O2 Fe1 O4 59.33(8) 1_545 1_545 ? N7 Fe1 O4 95.46(9) . 1_545 ? N1 Fe1 O4 87.72(9) . 1_545 ? C15 O2 Fe1 92.52(17) . 1_565 ? C1 O3 Fe1 155.5(2) . 2_565 ? C15 O4 Fe1 86.35(18) . 1_565 ? C1 O5 Fe1 121.95(19) . . ? O3 C1 O5 123.6(3) . . ? O3 C1 C17 118.6(3) . . ? O5 C1 C17 117.8(3) . . ? C13 N7 C24 116.1(3) . . ? C13 N7 Fe1 122.3(2) . . ? C24 N7 Fe1 121.3(2) . . ? C23 C8 C18 116.3(3) . . ? C23 C8 C12 122.9(3) . 1_456 ? C18 C8 C12 120.8(3) . 1_456 ? N1 C9 C16 124.0(3) . . ? N1 C9 H1 118.0 . . ? C16 C9 H1 118.0 . . ? C21 N1 C9 116.0(3) . . ? C21 N1 Fe1 123.15(19) . . ? C9 N1 Fe1 120.6(2) . . ? C17 C11 C14 119.9(3) . . ? C17 C11 H2 120.0 . . ? C14 C11 H2 120.0 . . ? C16 C12 C22 116.3(3) . . ? C16 C12 C8 120.5(3) . 1_654 ? C22 C12 C8 123.1(3) . 1_654 ? N7 C13 C18 123.8(3) . . ? N7 C13 H3 118.1 . . ? C18 C13 H3 118.1 . . ? C20 C14 C11 120.4(3) . . ? C20 C14 C15 120.0(3) . . ? C11 C14 C15 119.6(3) . . ? O4 C15 O2 121.7(3) . . ? O4 C15 C14 119.8(3) . . ? O2 C15 C14 118.5(3) . . ? C9 C16 C12 120.1(3) . . ? C9 C16 H4 119.9 . . ? C12 C16 H4 119.9 . . ? C19 C17 C11 119.4(3) . . ? C19 C17 C1 120.6(3) . . ? C11 C17 C1 119.9(3) . . ? C8 C18 C13 120.0(3) . . ? C8 C18 H5 120.0 . . ? C13 C18 H5 120.0 . . ? C25 C19 C17 120.6(3) . . ? C25 C19 H6 119.7 . . ? C17 C19 H6 119.7 . . ? C14 C20 C25 119.4(3) . . ? C14 C20 H7 120.3 . . ? C25 C20 H7 120.3 . . ? N1 C21 C22 123.7(3) . . ? N1 C21 H8 118.2 . . ? C22 C21 H8 118.2 . . ? C12 C22 C21 119.8(3) . . ? C12 C22 H9 120.1 . . ? C21 C22 H9 120.1 . . ? C8 C23 C24 120.2(3) . . ? C8 C23 H10 119.9 . . ? C24 C23 H10 119.9 . . ? N7 C24 C23 123.5(3) . . ? N7 C24 H11 118.3 . . ? C23 C24 H11 118.3 . . ? C19 C25 C20 120.2(3) . . ? C19 C25 H12 119.9 . . ? C20 C25 H12 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Fe1 O5 C1 -14.7(2) 2_565 . . . ? O2 Fe1 O5 C1 173.9(2) 1_545 . . . ? N7 Fe1 O5 C1 76.0(2) . . . . ? N1 Fe1 O5 C1 -100.8(2) . . . . ? O4 Fe1 O5 C1 171.5(2) 1_545 . . . ? Fe1 O3 C1 O5 83.1(5) 2_565 . . . ? Fe1 O3 C1 C17 -97.9(5) 2_565 . . . ? Fe1 O5 C1 O3 -13.1(4) . . . . ? Fe1 O5 C1 C17 167.80(19) . . . . ? O3 Fe1 N7 C13 118.7(3) 2_565 . . . ? O5 Fe1 N7 C13 -0.2(3) . . . . ? O2 Fe1 N7 C13 -150.3(3) 1_545 . . . ? N1 Fe1 N7 C13 116.2(13) . . . . ? O4 Fe1 N7 C13 -91.0(3) 1_545 . . . ? O3 Fe1 N7 C24 -55.3(3) 2_565 . . . ? O5 Fe1 N7 C24 -174.3(3) . . . . ? O2 Fe1 N7 C24 35.7(3) 1_545 . . . ? N1 Fe1 N7 C24 -57.8(14) . . . . ? O4 Fe1 N7 C24 94.9(3) 1_545 . . . ? C16 C9 N1 C21 1.3(5) . . . . ? C16 C9 N1 Fe1 -173.5(3) . . . . ? O3 Fe1 N1 C21 49.6(3) 2_565 . . . ? O5 Fe1 N1 C21 168.6(3) . . . . ? O2 Fe1 N1 C21 -41.5(3) 1_545 . . . ? N7 Fe1 N1 C21 52.0(14) . . . . ? O4 Fe1 N1 C21 -100.8(3) 1_545 . . . ? O3 Fe1 N1 C9 -136.0(3) 2_565 . . . ? O5 Fe1 N1 C9 -16.9(2) . . . . ? O2 Fe1 N1 C9 133.0(2) 1_545 . . . ? N7 Fe1 N1 C9 -133.5(13) . . . . ? O4 Fe1 N1 C9 73.6(2) 1_545 . . . ? C24 N7 C13 C18 2.1(5) . . . . ? Fe1 N7 C13 C18 -172.2(3) . . . . ? C17 C11 C14 C20 -0.6(5) . . . . ? C17 C11 C14 C15 -178.8(3) . . . . ? Fe1 O4 C15 O2 3.7(3) 1_565 . . . ? Fe1 O4 C15 C14 -175.4(3) 1_565 . . . ? Fe1 O2 C15 O4 -3.9(3) 1_565 . . . ? Fe1 O2 C15 C14 175.2(2) 1_565 . . . ? C20 C14 C15 O4 18.8(5) . . . . ? C11 C14 C15 O4 -162.9(3) . . . . ? C20 C14 C15 O2 -160.3(3) . . . . ? C11 C14 C15 O2 17.9(5) . . . . ? N1 C9 C16 C12 0.0(6) . . . . ? C22 C12 C16 C9 -1.4(5) . . . . ? C8 C12 C16 C9 176.8(3) 1_654 . . . ? C14 C11 C17 C19 1.9(5) . . . . ? C14 C11 C17 C1 -179.9(3) . . . . ? O3 C1 C17 C19 178.8(3) . . . . ? O5 C1 C17 C19 -2.1(5) . . . . ? O3 C1 C17 C11 0.6(4) . . . . ? O5 C1 C17 C11 179.7(3) . . . . ? C23 C8 C18 C13 -0.5(5) . . . . ? C12 C8 C18 C13 -178.9(3) 1_456 . . . ? N7 C13 C18 C8 -0.9(6) . . . . ? C11 C17 C19 C25 -1.4(6) . . . . ? C1 C17 C19 C25 -179.6(4) . . . . ? C11 C14 C20 C25 -1.2(6) . . . . ? C15 C14 C20 C25 176.9(4) . . . . ? C9 N1 C21 C22 -1.2(5) . . . . ? Fe1 N1 C21 C22 173.4(3) . . . . ? C16 C12 C22 C21 1.4(5) . . . . ? C8 C12 C22 C21 -176.7(3) 1_654 . . . ? N1 C21 C22 C12 -0.1(6) . . . . ? C18 C8 C23 C24 0.5(6) . . . . ? C12 C8 C23 C24 178.9(3) 1_456 . . . ? C13 N7 C24 C23 -2.1(6) . . . . ? Fe1 N7 C24 C23 172.3(3) . . . . ? C8 C23 C24 N7 0.9(6) . . . . ? C17 C19 C25 C20 -0.4(7) . . . . ? C14 C20 C25 C19 1.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.482 _refine_diff_density_min -0.897 _refine_diff_density_rms 0.241 data_FeCID-1_DMF _database_code_depnum_ccdc_archive 'CCDC 901081' #TrackingRef 'web_deposit_cif_file_1_SatoshiHorike_1347458117.FeCID-1_DMF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Fe N2 O4' _chemical_formula_weight 376.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.064(3) _cell_length_b 11.475(3) _cell_length_c 15.916(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.182(5) _cell_angle_gamma 90.00 _cell_volume 1789.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.866 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8459 _exptl_absorpt_correction_T_max 0.8459 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13949 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4020 _reflns_number_gt 3504 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.1497P)^2^+11.5383P] 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 4020 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1087 _refine_ls_R_factor_gt 0.0987 _refine_ls_wR_factor_ref 0.3074 _refine_ls_wR_factor_gt 0.2965 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _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 0.12205(8) 0.26978(7) 0.66430(5) 0.0217(3) Uani 1 1 d . . . O2 O -0.6612(4) 0.2781(4) 0.6727(3) 0.0287(10) Uani 1 1 d . . . O3 O -0.0740(4) 0.2744(4) 0.5884(3) 0.0277(9) Uani 1 1 d . . . C4 C -0.1720(6) 0.2774(5) 0.6253(4) 0.0212(11) Uani 1 1 d . . . O5 O -0.1586(5) 0.2594(4) 0.7036(3) 0.0325(10) Uani 1 1 d . . . O6 O -0.7949(5) 0.2871(5) 0.5437(3) 0.0379(12) Uani 1 1 d . . . C28 C -0.4257(6) 0.2884(5) 0.6065(4) 0.0227(11) Uani 1 1 d . . . H1 H -0.4148 0.2668 0.6647 0.027 Uiso 1 1 calc R . . C8 C -0.3121(6) 0.3015(5) 0.5713(4) 0.0221(11) Uani 1 1 d . . . N8 N 0.1246(5) 0.0796(5) 0.6615(3) 0.0298(11) Uani 1 1 d . . . C10 C 0.0242(7) 0.5232(6) 0.6185(4) 0.0315(14) Uani 1 1 d . . . H2 H -0.0451 0.4827 0.5800 0.038 Uiso 1 1 calc R . . C11 C -0.5554(6) 0.3073(6) 0.5552(4) 0.0260(12) Uani 1 1 d . . . C12 C 0.1254(6) -0.1656(6) 0.6682(4) 0.0282(13) Uani 1 1 d . . . C13 C 0.0226(7) 0.6427(6) 0.6162(4) 0.0323(14) Uani 1 1 d . . . H3 H -0.0468 0.6819 0.5768 0.039 Uiso 1 1 calc R . . C14 C -0.3279(6) 0.3393(7) 0.4862(4) 0.0330(14) Uani 1 1 d . . . H4 H -0.2511 0.3495 0.4627 0.040 Uiso 1 1 calc R . . C15 C 0.2229(8) 0.6437(6) 0.7285(5) 0.0382(16) Uani 1 1 d . . . H5 H 0.2941 0.6824 0.7669 0.046 Uiso 1 1 calc R . . C16 C 0.2150(8) 0.5212(6) 0.7271(5) 0.0391(16) Uani 1 1 d . . . H6 H 0.2812 0.4792 0.7669 0.047 Uiso 1 1 calc R . . C17 C -0.6785(6) 0.2898(5) 0.5925(4) 0.0257(12) Uani 1 1 d . . . C18 C 0.1230(6) 0.7057(5) 0.6718(4) 0.0244(12) Uani 1 1 d . . . C19 C -0.5709(7) 0.3443(7) 0.4699(4) 0.0381(16) Uani 1 1 d . . . H7 H -0.6588 0.3572 0.4354 0.046 Uiso 1 1 calc R . . N9 N 0.1194(5) 0.4617(5) 0.6727(3) 0.0261(11) Uani 1 1 d . . . C29 C -0.4590(7) 0.3619(8) 0.4362(5) 0.046(2) Uani 1 1 d . . . H8 H -0.4701 0.3893 0.3793 0.055 Uiso 1 1 calc R . . C23 C 0.0365(14) 0.0189(12) 0.6031(9) 0.031(3) Uiso 0.50 1 d P . . H9 H -0.0263 0.0589 0.5600 0.037 Uiso 0.50 1 calc PR . . C25 C 0.0346(15) -0.1056(12) 0.6041(10) 0.034(3) Uiso 0.50 1 d P . . H10 H -0.0279 -0.1466 0.5614 0.041 Uiso 0.50 1 calc PR . . C26 C 0.2202(14) -0.0963(12) 0.7262(10) 0.031(3) Uiso 0.50 1 d P . . H11 H 0.2877 -0.1326 0.7688 0.037 Uiso 0.50 1 calc PR . . C27 C 0.2157(15) 0.0232(12) 0.7215(10) 0.032(3) Uiso 0.50 1 d P . . H12 H 0.2790 0.0667 0.7620 0.038 Uiso 0.50 1 calc PR . . C30 C 0.0034(17) -0.1070(14) 0.6398(11) 0.042(3) Uiso 0.50 1 d P . . H13 H -0.0790 -0.1483 0.6229 0.051 Uiso 0.50 1 calc PR . . C31 C 0.0047(18) 0.0143(15) 0.6368(11) 0.045(4) Uiso 0.50 1 d P . . H14 H -0.0784 0.0539 0.6173 0.054 Uiso 0.50 1 calc PR . . C32 C 0.2339(15) 0.0210(12) 0.6899(10) 0.033(3) Uiso 0.50 1 d P . . H15 H 0.3154 0.0628 0.7096 0.040 Uiso 0.50 1 calc PR . . C33 C 0.2409(17) -0.1023(14) 0.6939(11) 0.039(3) Uiso 0.50 1 d P . . H16 H 0.3251 -0.1398 0.7142 0.047 Uiso 0.50 1 calc PR . . 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 0.0130(5) 0.0256(5) 0.0262(5) 0.0002(3) 0.0041(3) 0.0009(3) O2 0.016(2) 0.043(3) 0.027(2) 0.0027(18) 0.0055(16) 0.0005(17) O3 0.013(2) 0.036(2) 0.034(2) 0.0025(18) 0.0067(17) 0.0010(16) C4 0.016(3) 0.018(2) 0.029(3) -0.001(2) 0.004(2) -0.0020(19) O5 0.023(2) 0.049(3) 0.024(2) -0.0004(19) 0.0007(17) 0.0039(19) O6 0.013(2) 0.066(4) 0.033(2) 0.004(2) 0.0027(18) 0.001(2) C28 0.018(3) 0.026(3) 0.023(3) 0.000(2) 0.004(2) 0.001(2) C8 0.015(3) 0.026(3) 0.024(3) -0.001(2) 0.003(2) 0.002(2) N8 0.029(3) 0.025(3) 0.033(3) -0.002(2) 0.004(2) 0.003(2) C10 0.028(3) 0.022(3) 0.040(4) 0.001(2) -0.002(3) -0.001(2) C11 0.019(3) 0.031(3) 0.029(3) -0.004(2) 0.008(2) 0.000(2) C12 0.029(3) 0.025(3) 0.030(3) -0.002(2) 0.006(2) 0.005(2) C13 0.025(3) 0.028(3) 0.038(3) 0.005(3) -0.004(3) 0.001(2) C14 0.021(3) 0.054(4) 0.026(3) 0.006(3) 0.009(2) 0.000(3) C15 0.041(4) 0.028(3) 0.037(4) -0.003(3) -0.009(3) -0.002(3) C16 0.043(4) 0.029(3) 0.038(4) 0.008(3) -0.007(3) -0.001(3) C17 0.017(3) 0.030(3) 0.029(3) 0.002(2) 0.005(2) 0.001(2) C18 0.025(3) 0.023(3) 0.025(3) 0.002(2) 0.006(2) 0.004(2) C19 0.021(3) 0.062(5) 0.031(3) 0.009(3) 0.004(3) 0.007(3) N9 0.021(3) 0.027(3) 0.030(3) 0.004(2) 0.004(2) 0.0022(19) C29 0.025(4) 0.085(6) 0.028(3) 0.017(4) 0.005(3) 0.003(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 O5 2.054(5) 2_556 ? Fe1 O3 2.066(4) . ? Fe1 O2 2.157(4) 1_655 ? Fe1 N8 2.184(6) . ? Fe1 N9 2.207(5) . ? Fe1 O6 2.270(5) 1_655 ? O2 C17 1.256(8) . ? O2 Fe1 2.157(4) 1_455 ? O3 C4 1.258(7) . ? C4 O5 1.240(7) . ? C4 C8 1.500(8) . ? O5 Fe1 2.054(5) 2_556 ? O6 C17 1.250(8) . ? O6 Fe1 2.270(5) 1_455 ? C28 C11 1.390(9) . ? C28 C8 1.390(8) . ? C28 H1 0.9400 . ? C8 C14 1.397(8) . ? N8 C32 1.280(15) . ? N8 C23 1.326(15) . ? N8 C27 1.330(15) . ? N8 C31 1.398(18) . ? C10 N9 1.336(8) . ? C10 C13 1.371(9) . ? C10 H2 0.9400 . ? C11 C19 1.396(9) . ? C11 C17 1.505(8) . ? C12 C33 1.353(17) . ? C12 C30 1.382(17) . ? C12 C25 1.388(15) . ? C12 C26 1.413(15) . ? C12 C18 1.478(9) 1_545 ? C13 C18 1.386(9) . ? C13 H3 0.9400 . ? C14 C29 1.401(9) . ? C14 H4 0.9400 . ? C15 C18 1.385(9) . ? C15 C16 1.408(10) . ? C15 H5 0.9400 . ? C16 N9 1.328(9) . ? C16 H6 0.9400 . ? C18 C12 1.478(9) 1_565 ? C19 C29 1.369(9) . ? C19 H7 0.9400 . ? C29 H8 0.9400 . ? C23 C25 1.429(19) . ? C23 H9 0.9400 . ? C25 H10 0.9400 . ? C26 C27 1.37(2) . ? C26 H11 0.9400 . ? C27 H12 0.9400 . ? C30 C31 1.39(2) . ? C30 H13 0.9400 . ? C31 H14 0.9400 . ? C32 C33 1.42(2) . ? C32 H15 0.9400 . ? C33 H16 0.9400 . ? 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 O5 Fe1 O3 121.64(18) 2_556 . ? O5 Fe1 O2 89.79(18) 2_556 1_655 ? O3 Fe1 O2 148.50(18) . 1_655 ? O5 Fe1 N8 87.9(2) 2_556 . ? O3 Fe1 N8 91.60(19) . . ? O2 Fe1 N8 91.66(19) 1_655 . ? O5 Fe1 N9 89.88(19) 2_556 . ? O3 Fe1 N9 89.23(18) . . ? O2 Fe1 N9 88.75(18) 1_655 . ? N8 Fe1 N9 177.69(19) . . ? O5 Fe1 O6 148.90(18) 2_556 1_655 ? O3 Fe1 O6 89.41(17) . 1_655 ? O2 Fe1 O6 59.12(16) 1_655 1_655 ? N8 Fe1 O6 93.5(2) . 1_655 ? N9 Fe1 O6 88.6(2) . 1_655 ? C17 O2 Fe1 92.1(4) . 1_455 ? C4 O3 Fe1 118.2(4) . . ? O5 C4 O3 123.2(6) . . ? O5 C4 C8 118.6(5) . . ? O3 C4 C8 118.2(5) . . ? C4 O5 Fe1 166.5(5) . 2_556 ? C17 O6 Fe1 87.1(4) . 1_455 ? C11 C28 C8 119.6(5) . . ? C11 C28 H1 120.2 . . ? C8 C28 H1 120.2 . . ? C28 C8 C14 120.1(5) . . ? C28 C8 C4 120.1(5) . . ? C14 C8 C4 119.8(5) . . ? C32 N8 C23 110.8(10) . . ? C32 N8 C27 25.3(7) . . ? C23 N8 C27 119.3(10) . . ? C32 N8 C31 115.8(11) . . ? C23 N8 C31 29.0(7) . . ? C27 N8 C31 110.5(10) . . ? C32 N8 Fe1 122.0(7) . . ? C23 N8 Fe1 122.0(7) . . ? C27 N8 Fe1 118.7(7) . . ? C31 N8 Fe1 121.9(8) . . ? N9 C10 C13 123.2(6) . . ? N9 C10 H2 118.4 . . ? C13 C10 H2 118.4 . . ? C28 C11 C19 120.1(6) . . ? C28 C11 C17 119.6(5) . . ? C19 C11 C17 120.3(6) . . ? C33 C12 C30 118.4(11) . . ? C33 C12 C25 109.4(10) . . ? C30 C12 C25 29.7(7) . . ? C33 C12 C26 25.0(7) . . ? C30 C12 C26 110.9(10) . . ? C25 C12 C26 115.7(10) . . ? C33 C12 C18 123.0(8) . 1_545 ? C30 C12 C18 118.6(9) . 1_545 ? C25 C12 C18 120.8(8) . 1_545 ? C26 C12 C18 123.5(7) . 1_545 ? C10 C13 C18 120.1(6) . . ? C10 C13 H3 119.9 . . ? C18 C13 H3 119.9 . . ? C8 C14 C29 119.5(6) . . ? C8 C14 H4 120.2 . . ? C29 C14 H4 120.2 . . ? C18 C15 C16 118.2(6) . . ? C18 C15 H5 120.9 . . ? C16 C15 H5 120.9 . . ? N9 C16 C15 123.6(6) . . ? N9 C16 H6 118.2 . . ? C15 C16 H6 118.2 . . ? O6 C17 O2 121.5(6) . . ? O6 C17 C11 119.8(6) . . ? O2 C17 C11 118.7(5) . . ? C15 C18 C13 117.7(6) . . ? C15 C18 C12 121.5(6) . 1_565 ? C13 C18 C12 120.8(5) . 1_565 ? C29 C19 C11 120.4(6) . . ? C29 C19 H7 119.8 . . ? C11 C19 H7 119.8 . . ? C16 N9 C10 117.1(6) . . ? C16 N9 Fe1 122.4(4) . . ? C10 N9 Fe1 120.3(4) . . ? C19 C29 C14 120.1(6) . . ? C19 C29 H8 119.9 . . ? C14 C29 H8 119.9 . . ? N8 C23 C25 121.7(12) . . ? N8 C23 H9 119.1 . . ? C25 C23 H9 119.1 . . ? C12 C25 C23 119.8(12) . . ? C12 C25 H10 120.1 . . ? C23 C25 H10 120.1 . . ? C27 C26 C12 121.1(12) . . ? C27 C26 H11 119.4 . . ? C12 C26 H11 119.4 . . ? N8 C27 C26 122.3(13) . . ? N8 C27 H12 118.9 . . ? C26 C27 H12 118.9 . . ? C12 C30 C31 118.9(15) . . ? C12 C30 H13 120.6 . . ? C31 C30 H13 120.6 . . ? C30 C31 N8 122.7(15) . . ? C30 C31 H14 118.7 . . ? N8 C31 H14 118.7 . . ? N8 C32 C33 124.7(13) . . ? N8 C32 H15 117.7 . . ? C33 C32 H15 117.7 . . ? C12 C33 C32 119.5(13) . . ? C12 C33 H16 120.3 . . ? C32 C33 H16 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Fe1 O3 C4 4.0(5) 2_556 . . . ? O2 Fe1 O3 C4 -171.7(4) 1_655 . . . ? N8 Fe1 O3 C4 92.5(4) . . . . ? N9 Fe1 O3 C4 -85.4(4) . . . . ? O6 Fe1 O3 C4 -174.0(4) 1_655 . . . ? Fe1 O3 C4 O5 -11.8(8) . . . . ? Fe1 O3 C4 C8 169.6(4) . . . . ? O3 C4 O5 Fe1 81(2) . . . 2_556 ? C8 C4 O5 Fe1 -99.9(18) . . . 2_556 ? C11 C28 C8 C14 3.3(9) . . . . ? C11 C28 C8 C4 -178.0(5) . . . . ? O5 C4 C8 C28 -8.4(8) . . . . ? O3 C4 C8 C28 170.3(5) . . . . ? O5 C4 C8 C14 170.4(6) . . . . ? O3 C4 C8 C14 -10.9(9) . . . . ? O5 Fe1 N8 C32 -68.4(10) 2_556 . . . ? O3 Fe1 N8 C32 170.0(10) . . . . ? O2 Fe1 N8 C32 21.3(10) 1_655 . . . ? N9 Fe1 N8 C32 -79(5) . . . . ? O6 Fe1 N8 C32 80.5(10) 1_655 . . . ? O5 Fe1 N8 C23 139.2(9) 2_556 . . . ? O3 Fe1 N8 C23 17.6(9) . . . . ? O2 Fe1 N8 C23 -131.0(8) 1_655 . . . ? N9 Fe1 N8 C23 129(5) . . . . ? O6 Fe1 N8 C23 -71.9(8) 1_655 . . . ? O5 Fe1 N8 C27 -39.3(9) 2_556 . . . ? O3 Fe1 N8 C27 -160.9(9) . . . . ? O2 Fe1 N8 C27 50.4(9) 1_655 . . . ? N9 Fe1 N8 C27 -50(5) . . . . ? O6 Fe1 N8 C27 109.6(9) 1_655 . . . ? O5 Fe1 N8 C31 104.9(10) 2_556 . . . ? O3 Fe1 N8 C31 -16.7(10) . . . . ? O2 Fe1 N8 C31 -165.4(10) 1_655 . . . ? N9 Fe1 N8 C31 94(5) . . . . ? O6 Fe1 N8 C31 -106.2(10) 1_655 . . . ? C8 C28 C11 C19 -2.8(10) . . . . ? C8 C28 C11 C17 178.3(5) . . . . ? N9 C10 C13 C18 0.1(11) . . . . ? C28 C8 C14 C29 -1.1(11) . . . . ? C4 C8 C14 C29 -179.8(7) . . . . ? C18 C15 C16 N9 2.0(12) . . . . ? Fe1 O6 C17 O2 3.0(6) 1_455 . . . ? Fe1 O6 C17 C11 -177.1(5) 1_455 . . . ? Fe1 O2 C17 O6 -3.2(7) 1_455 . . . ? Fe1 O2 C17 C11 176.9(5) 1_455 . . . ? C28 C11 C17 O6 -167.8(6) . . . . ? C19 C11 C17 O6 13.3(10) . . . . ? C28 C11 C17 O2 12.1(9) . . . . ? C19 C11 C17 O2 -166.8(7) . . . . ? C16 C15 C18 C13 -1.0(10) . . . . ? C16 C15 C18 C12 -178.9(6) . . . 1_565 ? C10 C13 C18 C15 0.0(10) . . . . ? C10 C13 C18 C12 178.0(6) . . . 1_565 ? C28 C11 C19 C29 0.1(12) . . . . ? C17 C11 C19 C29 179.0(7) . . . . ? C15 C16 N9 C10 -1.9(11) . . . . ? C15 C16 N9 Fe1 174.0(6) . . . . ? C13 C10 N9 C16 0.9(10) . . . . ? C13 C10 N9 Fe1 -175.2(5) . . . . ? O5 Fe1 N9 C16 47.5(6) 2_556 . . . ? O3 Fe1 N9 C16 169.1(6) . . . . ? O2 Fe1 N9 C16 -42.3(6) 1_655 . . . ? N8 Fe1 N9 C16 58(5) . . . . ? O6 Fe1 N9 C16 -101.5(6) 1_655 . . . ? O5 Fe1 N9 C10 -136.7(5) 2_556 . . . ? O3 Fe1 N9 C10 -15.1(5) . . . . ? O2 Fe1 N9 C10 133.5(5) 1_655 . . . ? N8 Fe1 N9 C10 -126(5) . . . . ? O6 Fe1 N9 C10 74.4(5) 1_655 . . . ? C11 C19 C29 C14 2.1(14) . . . . ? C8 C14 C29 C19 -1.6(13) . . . . ? C32 N8 C23 C25 27.9(18) . . . . ? C27 N8 C23 C25 1.5(19) . . . . ? C31 N8 C23 C25 -78(2) . . . . ? Fe1 N8 C23 C25 -177.0(10) . . . . ? C33 C12 C25 C23 -29.7(17) . . . . ? C30 C12 C25 C23 84(2) . . . . ? C26 C12 C25 C23 -3.5(17) . . . . ? C18 C12 C25 C23 178.5(10) 1_545 . . . ? N8 C23 C25 C12 1(2) . . . . ? C33 C12 C26 C27 84(3) . . . . ? C30 C12 C26 C27 -28.2(18) . . . . ? C25 C12 C26 C27 3.8(18) . . . . ? C18 C12 C26 C27 -178.2(11) 1_545 . . . ? C32 N8 C27 C26 -78(3) . . . . ? C23 N8 C27 C26 -1(2) . . . . ? C31 N8 C27 C26 29.3(19) . . . . ? Fe1 N8 C27 C26 177.3(11) . . . . ? C12 C26 C27 N8 -1(2) . . . . ? C33 C12 C30 C31 2(2) . . . . ? C25 C12 C30 C31 -78(2) . . . . ? C26 C12 C30 C31 28.0(19) . . . . ? C18 C12 C30 C31 179.6(12) 1_545 . . . ? C12 C30 C31 N8 0(2) . . . . ? C32 N8 C31 C30 -2(2) . . . . ? C23 N8 C31 C30 85(2) . . . . ? C27 N8 C31 C30 -29(2) . . . . ? Fe1 N8 C31 C30 -175.8(13) . . . . ? C23 N8 C32 C33 -28(2) . . . . ? C27 N8 C32 C33 87(3) . . . . ? C31 N8 C32 C33 3(2) . . . . ? Fe1 N8 C32 C33 176.7(12) . . . . ? C30 C12 C33 C32 -1(2) . . . . ? C25 C12 C33 C32 30.2(18) . . . . ? C26 C12 C33 C32 -79(3) . . . . ? C18 C12 C33 C32 -178.7(11) 1_545 . . . ? N8 C32 C33 C12 -2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 3.659 _refine_diff_density_min -0.864 _refine_diff_density_rms 0.262 data_FeCID-1_Iodine _database_code_depnum_ccdc_archive 'CCDC 901082' #TrackingRef 'web_deposit_cif_file_2_SatoshiHorike_1347458117.FeCID-1_Iodine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Fe I2.50 N2 O4' _chemical_formula_weight 693.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.230(14) _cell_length_b 11.580(15) _cell_length_c 17.68(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.09(2) _cell_angle_gamma 90.00 _cell_volume 2074(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1298 _exptl_absorpt_coefficient_mu 4.474 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4681 _exptl_absorpt_correction_T_max 0.4681 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15213 _diffrn_reflns_av_R_equivalents 0.1219 _diffrn_reflns_av_sigmaI/netI 0.1256 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4720 _reflns_number_gt 2005 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.2000P)^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 4720 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2631 _refine_ls_R_factor_gt 0.1548 _refine_ls_wR_factor_ref 0.4283 _refine_ls_wR_factor_gt 0.3527 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.218 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0847(13) 0.8980(10) 0.7534(5) 0.055(5) Uani 1 1 d G . . H1 H -0.0904 0.9383 0.7069 0.066 Uiso 1 1 calc R . . C2 C -0.0897(14) 0.7780(10) 0.7535(5) 0.061(5) Uani 1 1 d G . . H2 H -0.0989 0.7373 0.7070 0.074 Uiso 1 1 calc R . . C3 C -0.0812(13) 0.7183(7) 0.8222(7) 0.045(4) Uani 1 1 d G . . C4 C -0.0676(12) 0.7786(9) 0.8908(5) 0.058(5) Uani 1 1 d G . . H3 H -0.0618 0.7382 0.9373 0.069 Uiso 1 1 calc R . . C5 C -0.0626(12) 0.8985(9) 0.8907(5) 0.047(4) Uani 1 1 d G . . H4 H -0.0534 0.9393 0.9372 0.056 Uiso 1 1 calc R . . N1 N -0.0711(11) 0.9582(7) 0.8220(6) 0.056(4) Uani 1 1 d G . . N2 N -0.0841(10) 0.3406(7) 0.8262(6) 0.054(4) Uani 1 1 d G . . C8 C -0.1276(12) 0.4010(10) 0.8858(6) 0.055(5) Uani 1 1 d G . . H5 H -0.1559 0.3606 0.9267 0.067 Uiso 1 1 calc R . . C9 C -0.1293(13) 0.5210(9) 0.8850(6) 0.067(6) Uani 1 1 d G . . H6 H -0.1588 0.5618 0.9254 0.080 Uiso 1 1 calc R . . C10 C -0.0875(12) 0.5807(7) 0.8246(7) 0.050(4) Uani 1 1 d G . . C11 C -0.0440(12) 0.5203(9) 0.7649(6) 0.047(4) Uani 1 1 d G . . H7 H -0.0157 0.5607 0.7240 0.056 Uiso 1 1 calc R . . C12 C -0.0423(11) 0.4003(9) 0.7657(6) 0.070(6) Uani 1 1 d G . . H8 H -0.0129 0.3595 0.7253 0.083 Uiso 1 1 calc R . . I1 I 1.0000 0.5000 0.5000 0.0784(13) Uani 0.80 2 d SP . . Fe1 Fe -0.0659(2) 0.1492(2) 0.82785(14) 0.0459(8) Uani 1 1 d . . . I2 I 0.7500 0.0896(8) 0.2500 0.052(6) Uani 0.20 2 d SP . . I3 I 0.7612(3) 0.3034(3) 0.31164(19) 0.0788(11) Uani 0.50 1 d P . . I4 I 0.763(2) 0.5381(18) 0.400(2) 0.094(7) Uani 0.25 1 d P . . O1 O 0.0758(10) 0.1471(11) 0.9328(6) 0.052(3) Uani 1 1 d . . . C13 C 0.3156(17) 0.1545(16) 0.9253(11) 0.051(5) Uani 1 1 d . . . O2 O 0.1428(11) 0.1606(11) 0.8190(7) 0.057(3) Uani 1 1 d . . . C14 C 0.3509(19) 0.1502(18) 1.0056(11) 0.065(6) Uani 1 1 d . . . H9 H 0.2848 0.1494 1.0376 0.078 Uiso 1 1 calc R . . C15 C 0.4152(17) 0.1548(15) 0.8748(9) 0.045(4) Uani 1 1 d . . . H10 H 0.3915 0.1591 0.8215 0.054 Uiso 1 1 calc R . . C16 C 0.1717(16) 0.1533(16) 0.8895(11) 0.051(4) Uani 1 1 d . . . O3 O 0.6213(12) 0.1542(10) 0.7836(7) 0.050(3) Uani 1 1 d . . . C17 C 0.6572(15) 0.1516(13) 0.8584(10) 0.041(4) Uani 1 1 d . . . C18 C 0.5842(19) 0.1483(16) 0.9902(10) 0.055(5) Uani 1 1 d . . . H11 H 0.6739 0.1490 1.0112 0.065 Uiso 1 1 calc R . . C19 C 0.5476(14) 0.1485(14) 0.9073(11) 0.045(4) Uani 1 1 d . . . C20 C 0.488(2) 0.147(2) 1.0384(13) 0.077(7) Uani 1 1 d . . . H12 H 0.5117 0.1441 1.0917 0.092 Uiso 1 1 calc R . . O4 O 0.7764(11) 0.1432(10) 0.8891(6) 0.049(3) Uani 1 1 d . . . I5 I 0.752(2) 0.0959(7) 0.2304(14) 0.135(6) Uani 0.40 1 d P . . I6 I 0.7552(16) 0.476(2) 0.4008(13) 0.181(11) Uani 0.30 1 d P . . I7 I 0.7503(17) 0.5212(16) 0.3893(14) 0.120(6) Uani 0.45 1 d P . . I8 I 0.998(3) 0.4562(19) 0.5013(16) 0.069(8) Uiso 0.10 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 C1 0.058(12) 0.047(11) 0.054(12) -0.007(9) -0.009(9) 0.002(9) C2 0.067(14) 0.081(16) 0.037(11) -0.012(10) 0.014(8) -0.004(11) C3 0.032(8) 0.053(10) 0.054(11) -0.008(9) 0.022(7) 0.011(7) C4 0.038(9) 0.082(15) 0.059(12) -0.021(10) 0.030(8) -0.012(9) C5 0.060(12) 0.053(11) 0.032(10) 0.016(8) 0.022(8) 0.005(9) N1 0.031(7) 0.051(9) 0.092(12) 0.002(9) 0.024(7) -0.004(7) N2 0.028(7) 0.058(10) 0.074(10) 0.002(8) 0.005(7) 0.002(7) C8 0.062(12) 0.059(12) 0.051(11) -0.019(9) 0.027(9) 0.007(9) C9 0.051(12) 0.064(14) 0.094(15) -0.016(11) 0.034(11) 0.004(9) C10 0.036(9) 0.075(13) 0.043(10) -0.011(9) 0.023(7) 0.008(8) C11 0.042(9) 0.023(8) 0.076(12) 0.017(8) 0.011(8) -0.007(6) C12 0.044(11) 0.079(15) 0.093(15) -0.018(12) 0.034(10) 0.012(10) I1 0.0558(19) 0.051(3) 0.133(4) 0.008(3) 0.0272(16) 0.007(2) Fe1 0.0270(12) 0.0493(15) 0.0658(18) -0.0003(12) 0.0219(11) -0.0019(10) I2 0.012(5) 0.000(3) 0.141(18) 0.000 0.005(7) 0.000 I3 0.0428(15) 0.082(2) 0.116(3) 0.0091(17) 0.0274(15) 0.0035(13) I4 0.060(9) 0.062(7) 0.157(18) -0.049(9) 0.007(9) -0.006(6) O1 0.027(6) 0.070(8) 0.065(7) -0.015(6) 0.029(5) -0.009(6) C13 0.035(9) 0.054(11) 0.069(13) -0.006(9) 0.022(8) -0.017(8) O2 0.033(6) 0.071(9) 0.071(9) 0.015(7) 0.027(6) -0.008(6) C14 0.048(11) 0.087(15) 0.065(14) -0.036(11) 0.030(9) -0.035(11) C15 0.047(10) 0.060(11) 0.033(9) -0.009(8) 0.023(7) 0.009(8) C16 0.028(8) 0.068(12) 0.061(12) 0.013(10) 0.016(8) -0.003(8) O3 0.046(7) 0.049(7) 0.061(8) 0.011(6) 0.028(6) -0.013(5) C17 0.030(8) 0.028(8) 0.069(12) 0.006(8) 0.016(8) -0.001(6) C18 0.046(10) 0.070(13) 0.054(12) -0.002(9) 0.028(8) 0.011(9) C19 0.018(7) 0.037(9) 0.082(13) 0.006(8) 0.008(7) 0.006(6) C20 0.046(11) 0.102(17) 0.083(15) -0.056(13) 0.013(10) -0.009(11) O4 0.038(6) 0.046(7) 0.065(8) -0.001(6) 0.013(5) -0.004(5) I5 0.078(5) 0.138(6) 0.201(18) -0.037(7) 0.065(9) -0.018(5) I6 0.052(6) 0.39(3) 0.088(7) 0.034(15) -0.029(5) -0.073(11) I7 0.067(6) 0.147(12) 0.134(10) -0.019(10) -0.023(5) 0.045(7) _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 C1 C2 1.3900 . ? C1 N1 1.3900 . ? C1 H1 0.9400 . ? C2 C3 1.3900 . ? C2 H2 0.9400 . ? C3 C4 1.3900 . ? C3 C10 1.596(11) . ? C4 C5 1.3900 . ? C4 H3 0.9400 . ? C5 N1 1.3900 . ? C5 H4 0.9400 . ? N1 Fe1 2.215(9) 1_565 ? N2 C8 1.3900 . ? N2 C12 1.3900 . ? N2 Fe1 2.224(9) . ? C8 C9 1.3900 . ? C8 H5 0.9400 . ? C9 C10 1.3900 . ? C9 H6 0.9400 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C11 H7 0.9400 . ? C12 H8 0.9400 . ? I1 I8 0.51(2) . ? I1 I8 0.51(2) 3_766 ? I1 I4 2.83(3) 3_766 ? I1 I4 2.83(3) . ? I1 I6 2.862(17) . ? I1 I6 2.862(17) 3_766 ? I1 I7 3.002(16) . ? I1 I7 3.002(16) 3_766 ? Fe1 O3 1.974(13) 2_556 ? Fe1 O4 2.067(12) 1_455 ? Fe1 O2 2.167(12) . ? Fe1 O1 2.189(12) . ? Fe1 N1 2.214(9) 1_545 ? I2 I5 0.36(2) 2_655 ? I2 I3 2.702(9) 2_655 ? I2 I3 2.702(9) . ? I3 I3 2.160(7) 2_655 ? I3 I5 2.513(11) 2_655 ? I3 I6 2.55(3) . ? I3 I5 2.795(15) . ? I3 I7 2.88(2) . ? I3 I4 3.13(2) . ? I4 I6 0.72(3) . ? I4 I8 2.80(4) 3_766 ? I4 I8 2.94(4) . ? O1 C16 1.330(19) . ? C13 C14 1.42(3) . ? C13 C15 1.45(2) . ? C13 C16 1.52(2) . ? O2 C16 1.24(2) . ? C14 C20 1.44(3) . ? C14 H9 0.9400 . ? C15 C19 1.40(2) . ? C15 H10 0.9400 . ? O3 C17 1.321(19) . ? O3 Fe1 1.974(13) 2_556 ? C17 O4 1.267(18) . ? C17 C19 1.51(2) . ? C18 C20 1.39(3) . ? C18 C19 1.46(2) . ? C18 H11 0.9400 . ? C20 H12 0.9400 . ? O4 Fe1 2.067(12) 1_655 ? I5 I5 0.70(5) 2_655 ? I5 I3 2.513(11) 2_655 ? I6 I7 0.56(3) . ? I6 I8 2.85(3) . ? I6 I8 2.96(3) 3_766 ? I7 I8 3.01(3) 3_766 ? I7 I8 3.08(3) . ? I8 I8 1.02(5) 3_766 ? I8 I4 2.80(4) 3_766 ? I8 I6 2.96(3) 3_766 ? I8 I7 3.01(3) 3_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 120.0 . . ? C2 C1 H1 120.0 . . ? N1 C1 H1 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 C10 121.5(8) . . ? C4 C3 C10 118.5(8) . . ? C3 C4 C5 120.0 . . ? C3 C4 H3 120.0 . . ? C5 C4 H3 120.0 . . ? C4 C5 N1 120.0 . . ? C4 C5 H4 120.0 . . ? N1 C5 H4 120.0 . . ? C5 N1 C1 120.0 . . ? C5 N1 Fe1 117.3(6) . 1_565 ? C1 N1 Fe1 122.7(6) . 1_565 ? C8 N2 C12 120.0 . . ? C8 N2 Fe1 121.7(6) . . ? C12 N2 Fe1 118.1(6) . . ? C9 C8 N2 120.0 . . ? C9 C8 H5 120.0 . . ? N2 C8 H5 120.0 . . ? C8 C9 C10 120.0 . . ? C8 C9 H6 120.0 . . ? C10 C9 H6 120.0 . . ? C11 C10 C9 120.0 . . ? C11 C10 C3 117.6(8) . . ? C9 C10 C3 122.3(8) . . ? C10 C11 C12 120.0 . . ? C10 C11 H7 120.0 . . ? C12 C11 H7 120.0 . . ? C11 C12 N2 120.0 . . ? C11 C12 H8 120.0 . . ? N2 C12 H8 120.0 . . ? I8 I1 I8 180(7) . 3_766 ? I8 I1 I4 82(3) . 3_766 ? I8 I1 I4 98(3) 3_766 3_766 ? I8 I1 I4 98(3) . . ? I8 I1 I4 82(3) 3_766 . ? I4 I1 I4 180.0(8) 3_766 . ? I8 I1 I6 83(3) . . ? I8 I1 I6 97(3) 3_766 . ? I4 I1 I6 165.4(6) 3_766 . ? I4 I1 I6 14.6(6) . . ? I8 I1 I6 97(3) . 3_766 ? I8 I1 I6 83(3) 3_766 3_766 ? I4 I1 I6 14.6(6) 3_766 3_766 ? I4 I1 I6 165.4(6) . 3_766 ? I6 I1 I6 179.999(2) . 3_766 ? I8 I1 I7 94(3) . . ? I8 I1 I7 86(3) 3_766 . ? I4 I1 I7 175.4(7) 3_766 . ? I4 I1 I7 4.6(7) . . ? I6 I1 I7 10.7(7) . . ? I6 I1 I7 169.3(7) 3_766 . ? I8 I1 I7 86(3) . 3_766 ? I8 I1 I7 94(3) 3_766 3_766 ? I4 I1 I7 4.6(7) 3_766 3_766 ? I4 I1 I7 175.4(7) . 3_766 ? I6 I1 I7 169.3(7) . 3_766 ? I6 I1 I7 10.7(7) 3_766 3_766 ? I7 I1 I7 179.999(3) . 3_766 ? O3 Fe1 O4 112.9(5) 2_556 1_455 ? O3 Fe1 O2 94.2(5) 2_556 . ? O4 Fe1 O2 152.8(5) 1_455 . ? O3 Fe1 O1 155.5(4) 2_556 . ? O4 Fe1 O1 91.6(4) 1_455 . ? O2 Fe1 O1 61.3(4) . . ? O3 Fe1 N1 88.9(17) 2_556 1_545 ? O4 Fe1 N1 88.6(17) 1_455 1_545 ? O2 Fe1 N1 94.3(18) . 1_545 ? O1 Fe1 N1 92.1(18) . 1_545 ? O3 Fe1 N2 86.9(4) 2_556 . ? O4 Fe1 N2 88.3(4) 1_455 . ? O2 Fe1 N2 91.2(4) . . ? O1 Fe1 N2 93.8(4) . . ? N1 Fe1 N2 173.4(18) 1_545 . ? I5 I2 I3 102(3) 2_655 2_655 ? I5 I2 I3 55(3) 2_655 . ? I3 I2 I3 47.1(2) 2_655 . ? I3 I3 I5 73.0(5) 2_655 2_655 ? I3 I3 I6 128.0(5) 2_655 . ? I5 I3 I6 157.9(7) 2_655 . ? I3 I3 I2 66.44(11) 2_655 . ? I5 I3 I2 6.7(5) 2_655 . ? I6 I3 I2 164.5(5) . . ? I3 I3 I5 59.3(4) 2_655 . ? I5 I3 I5 13.9(9) 2_655 . ? I6 I3 I5 171.5(6) . . ? I2 I3 I5 7.2(4) . . ? I3 I3 I7 118.4(5) 2_655 . ? I5 I3 I7 166.9(7) 2_655 . ? I6 I3 I7 9.6(8) . . ? I2 I3 I7 172.9(5) . . ? I5 I3 I7 175.5(6) . . ? I3 I3 I4 119.8(6) 2_655 . ? I5 I3 I4 166.6(8) 2_655 . ? I6 I3 I4 8.7(8) . . ? I2 I3 I4 173.2(7) . . ? I5 I3 I4 178.2(7) . . ? I7 I3 I4 2.7(7) . . ? I6 I4 I8 96(3) . 3_766 ? I6 I4 I1 85(3) . . ? I8 I4 I1 10.4(5) 3_766 . ? I6 I4 I8 76(3) . . ? I8 I4 I8 20.2(9) 3_766 . ? I1 I4 I8 9.9(5) . . ? I6 I4 I3 32(3) . . ? I8 I4 I3 105.9(9) 3_766 . ? I1 I4 I3 96.9(7) . . ? I8 I4 I3 88.3(8) . . ? C16 O1 Fe1 88.0(10) . . ? C14 C13 C15 121.2(16) . . ? C14 C13 C16 120.9(15) . . ? C15 C13 C16 117.9(16) . . ? C16 O2 Fe1 91.2(10) . . ? C13 C14 C20 120.1(17) . . ? C13 C14 H9 120.0 . . ? C20 C14 H9 120.0 . . ? C19 C15 C13 118.2(16) . . ? C19 C15 H10 120.9 . . ? C13 C15 H10 120.9 . . ? O2 C16 O1 119.4(15) . . ? O2 C16 C13 119.9(15) . . ? O1 C16 C13 120.7(17) . . ? C17 O3 Fe1 177.0(10) . 2_556 ? O4 C17 O3 123.1(15) . . ? O4 C17 C19 120.0(16) . . ? O3 C17 C19 116.7(14) . . ? C20 C18 C19 120.7(18) . . ? C20 C18 H11 119.6 . . ? C19 C18 H11 119.6 . . ? C15 C19 C18 120.6(15) . . ? C15 C19 C17 121.2(16) . . ? C18 C19 C17 118.0(14) . . ? C18 C20 C14 119(2) . . ? C18 C20 H12 120.4 . . ? C14 C20 H12 120.4 . . ? C17 O4 Fe1 123.2(11) . 1_655 ? I5 I5 I3 106.6(5) 2_655 2_655 ? I5 I5 I3 59.5(6) 2_655 . ? I3 I5 I3 47.6(2) 2_655 . ? I7 I6 I4 22(5) . . ? I7 I6 I3 121(5) . . ? I4 I6 I3 139(4) . . ? I7 I6 I8 109(3) . . ? I4 I6 I8 90(2) . . ? I3 I6 I8 103.2(8) . . ? I7 I6 I1 99(3) . . ? I4 I6 I1 80(2) . . ? I3 I6 I1 111.1(7) . . ? I8 I6 I1 10.2(5) . . ? I7 I6 I8 89(3) . 3_766 ? I4 I6 I8 70(2) . 3_766 ? I3 I6 I8 118.4(9) . 3_766 ? I8 I6 I8 20.1(9) . 3_766 ? I1 I6 I8 9.8(4) . 3_766 ? I6 I7 I3 49(4) . . ? I6 I7 I1 70(3) . . ? I3 I7 I1 98.8(4) . . ? I6 I7 I8 80(3) . 3_766 ? I3 I7 I8 107.2(7) . 3_766 ? I1 I7 I8 9.7(4) . 3_766 ? I6 I7 I8 61(3) . . ? I3 I7 I8 90.5(6) . . ? I1 I7 I8 9.5(4) . . ? I8 I7 I8 19.2(8) 3_766 . ? I1 I8 I8 0.001(10) . 3_766 ? I1 I8 I4 88(3) . 3_766 ? I8 I8 I4 88(3) 3_766 3_766 ? I1 I8 I6 86(3) . . ? I8 I8 I6 86(3) 3_766 . ? I4 I8 I6 174.0(11) 3_766 . ? I1 I8 I4 72(3) . . ? I8 I8 I4 72(3) 3_766 . ? I4 I8 I4 159.8(9) 3_766 . ? I6 I8 I4 14.3(6) . . ? I1 I8 I6 74(3) . 3_766 ? I8 I8 I6 74(3) 3_766 3_766 ? I4 I8 I6 14.1(7) 3_766 3_766 ? I6 I8 I6 159.9(9) . 3_766 ? I4 I8 I6 145.7(10) . 3_766 ? I1 I8 I7 84(3) . 3_766 ? I8 I8 I7 84(3) 3_766 3_766 ? I4 I8 I7 4.0(8) 3_766 3_766 ? I6 I8 I7 170.3(11) . 3_766 ? I4 I8 I7 156.2(10) . 3_766 ? I6 I8 I7 10.8(7) 3_766 3_766 ? I1 I8 I7 77(3) . . ? I8 I8 I7 77(3) 3_766 . ? I4 I8 I7 164.2(12) 3_766 . ? I6 I8 I7 9.9(7) . . ? I4 I8 I7 4.9(7) . . ? I6 I8 I7 150.2(11) 3_766 . ? I7 I8 I7 160.8(8) 3_766 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C10 179.6(10) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C10 C3 C4 C5 -179.6(10) . . . . ? C3 C4 C5 N1 0.0 . . . . ? C4 C5 N1 C1 0.0 . . . . ? C4 C5 N1 Fe1 178.9(7) . . . 1_565 ? C2 C1 N1 C5 0.0 . . . . ? C2 C1 N1 Fe1 -178.8(7) . . . 1_565 ? C12 N2 C8 C9 0.0 . . . . ? Fe1 N2 C8 C9 175.7(7) . . . . ? N2 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C11 0.0 . . . . ? C8 C9 C10 C3 -177.2(11) . . . . ? C2 C3 C10 C11 27.9(11) . . . . ? C4 C3 C10 C11 -152.5(7) . . . . ? C2 C3 C10 C9 -154.8(7) . . . . ? C4 C3 C10 C9 24.8(12) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C3 C10 C11 C12 177.4(10) . . . . ? C10 C11 C12 N2 0.0 . . . . ? C8 N2 C12 C11 0.0 . . . . ? Fe1 N2 C12 C11 -175.9(7) . . . . ? C8 N2 Fe1 O3 144.8(7) . . . 2_556 ? C12 N2 Fe1 O3 -39.4(6) . . . 2_556 ? C8 N2 Fe1 O4 31.8(7) . . . 1_455 ? C12 N2 Fe1 O4 -152.4(6) . . . 1_455 ? C8 N2 Fe1 O2 -121.0(7) . . . . ? C12 N2 Fe1 O2 54.8(6) . . . . ? C8 N2 Fe1 O1 -59.7(7) . . . . ? C12 N2 Fe1 O1 116.1(6) . . . . ? C8 N2 Fe1 N1 94(14) . . . 1_545 ? C12 N2 Fe1 N1 -90(14) . . . 1_545 ? I5 I2 I3 I3 -170(5) 2_655 . . 2_655 ? I3 I2 I3 I5 170(5) 2_655 . . 2_655 ? I5 I2 I3 I6 -9(5) 2_655 . . . ? I3 I2 I3 I6 160.6(14) 2_655 . . . ? I5 I2 I3 I5 -178.3(9) 2_655 . . . ? I3 I2 I3 I5 -9(4) 2_655 . . . ? I5 I2 I3 I7 -35(5) 2_655 . . . ? I3 I2 I3 I7 134(3) 2_655 . . . ? I5 I2 I3 I4 -13(6) 2_655 . . . ? I3 I2 I3 I4 157(4) 2_655 . . . ? I8 I1 I4 I6 1(5) . . . . ? I8 I1 I4 I6 -179(5) 3_766 . . . ? I4 I1 I4 I6 79(15) 3_766 . . . ? I6 I1 I4 I6 180.004(10) 3_766 . . . ? I7 I1 I4 I6 25(13) . . . . ? I7 I1 I4 I6 -155(13) 3_766 . . . ? I8 I1 I4 I8 180.000(13) . . . 3_766 ? I4 I1 I4 I8 -102(18) 3_766 . . 3_766 ? I6 I1 I4 I8 179(5) . . . 3_766 ? I6 I1 I4 I8 -1(5) 3_766 . . 3_766 ? I7 I1 I4 I8 -155(15) . . . 3_766 ? I7 I1 I4 I8 25(15) 3_766 . . 3_766 ? I8 I1 I4 I8 180.000(12) 3_766 . . . ? I4 I1 I4 I8 78(18) 3_766 . . . ? I6 I1 I4 I8 -1(5) . . . . ? I6 I1 I4 I8 179(5) 3_766 . . . ? I7 I1 I4 I8 25(15) . . . . ? I7 I1 I4 I8 -155(15) 3_766 . . . ? I8 I1 I4 I3 -29(3) . . . . ? I8 I1 I4 I3 151(3) 3_766 . . . ? I4 I1 I4 I3 48(6) 3_766 . . . ? I6 I1 I4 I3 -30(3) . . . . ? I6 I1 I4 I3 150(3) 3_766 . . . ? I7 I1 I4 I3 -5(14) . . . . ? I7 I1 I4 I3 175(14) 3_766 . . . ? I3 I3 I4 I6 162(4) 2_655 . . . ? I5 I3 I4 I6 0(6) 2_655 . . . ? I2 I3 I4 I6 7(7) . . . . ? I5 I3 I4 I6 103(23) . . . . ? I7 I3 I4 I6 102(24) . . . . ? I3 I3 I4 I8 -122.7(10) 2_655 . . 3_766 ? I5 I3 I4 I8 76(3) 2_655 . . 3_766 ? I6 I3 I4 I8 75(4) . . . 3_766 ? I2 I3 I4 I8 82(4) . . . 3_766 ? I5 I3 I4 I8 178(100) . . . 3_766 ? I7 I3 I4 I8 177(24) . . . 3_766 ? I3 I3 I4 I1 -128.0(7) 2_655 . . . ? I5 I3 I4 I1 70(3) 2_655 . . . ? I6 I3 I4 I1 70(4) . . . . ? I2 I3 I4 I1 77(4) . . . . ? I5 I3 I4 I1 173(23) . . . . ? I7 I3 I4 I1 171(24) . . . . ? I3 I3 I4 I8 -132.8(8) 2_655 . . . ? I5 I3 I4 I8 65(3) 2_655 . . . ? I6 I3 I4 I8 65(4) . . . . ? I2 I3 I4 I8 72(4) . . . . ? I5 I3 I4 I8 168(23) . . . . ? I7 I3 I4 I8 167(24) . . . . ? O3 Fe1 O1 C16 0.5(17) 2_556 . . . ? O4 Fe1 O1 C16 -178.9(10) 1_455 . . . ? O2 Fe1 O1 C16 -1.3(10) . . . . ? N1 Fe1 O1 C16 92.5(19) 1_545 . . . ? N2 Fe1 O1 C16 -90.5(10) . . . . ? O3 Fe1 O2 C16 -177.9(11) 2_556 . . . ? O4 Fe1 O2 C16 6.5(17) 1_455 . . . ? O1 Fe1 O2 C16 1.4(10) . . . . ? N1 Fe1 O2 C16 -88.7(19) 1_545 . . . ? N2 Fe1 O2 C16 95.1(11) . . . . ? C15 C13 C14 C20 1(3) . . . . ? C16 C13 C14 C20 177.7(19) . . . . ? C14 C13 C15 C19 1(3) . . . . ? C16 C13 C15 C19 -176.0(15) . . . . ? Fe1 O2 C16 O1 -2.3(17) . . . . ? Fe1 O2 C16 C13 179.3(15) . . . . ? Fe1 O1 C16 O2 2.2(17) . . . . ? Fe1 O1 C16 C13 -179.3(16) . . . . ? C14 C13 C16 O2 177.8(18) . . . . ? C15 C13 C16 O2 -5(3) . . . . ? C14 C13 C16 O1 -1(3) . . . . ? C15 C13 C16 O1 176.6(16) . . . . ? Fe1 O3 C17 O4 97(20) 2_556 . . . ? Fe1 O3 C17 C19 -78(21) 2_556 . . . ? C13 C15 C19 C18 -3(3) . . . . ? C13 C15 C19 C17 -178.3(15) . . . . ? C20 C18 C19 C15 4(3) . . . . ? C20 C18 C19 C17 179.1(17) . . . . ? O4 C17 C19 C15 -178.5(15) . . . . ? O3 C17 C19 C15 -4(2) . . . . ? O4 C17 C19 C18 7(2) . . . . ? O3 C17 C19 C18 -178.6(14) . . . . ? C19 C18 C20 C14 -2(3) . . . . ? C13 C14 C20 C18 0(3) . . . . ? O3 C17 O4 Fe1 7(2) . . . 1_655 ? C19 C17 O4 Fe1 -178.9(10) . . . 1_655 ? I3 I3 I5 I5 -170(4) 2_655 . . 2_655 ? I6 I3 I5 I5 -19(8) . . . 2_655 ? I2 I3 I5 I5 0.8(4) . . . 2_655 ? I7 I3 I5 I5 -109(9) . . . 2_655 ? I4 I3 I5 I5 -110(24) . . . 2_655 ? I5 I3 I5 I3 170(4) 2_655 . . 2_655 ? I6 I3 I5 I3 151(4) . . . 2_655 ? I2 I3 I5 I3 171(4) . . . 2_655 ? I7 I3 I5 I3 61(8) . . . 2_655 ? I4 I3 I5 I3 60(23) . . . 2_655 ? I8 I4 I6 I7 -151(13) 3_766 . . . ? I1 I4 I6 I7 -151(13) . . . . ? I8 I4 I6 I7 -151(12) . . . . ? I3 I4 I6 I7 -40(14) . . . . ? I8 I4 I6 I3 -111(3) 3_766 . . . ? I1 I4 I6 I3 -111(3) . . . . ? I8 I4 I6 I3 -111(3) . . . . ? I8 I4 I6 I8 -0.2(17) 3_766 . . . ? I1 I4 I6 I8 -0.1(8) . . . . ? I3 I4 I6 I8 111(3) . . . . ? I8 I4 I6 I1 -0.1(9) 3_766 . . . ? I8 I4 I6 I1 0.1(8) . . . . ? I3 I4 I6 I1 111(3) . . . . ? I1 I4 I6 I8 0.1(9) . . . 3_766 ? I8 I4 I6 I8 0.2(17) . . . 3_766 ? I3 I4 I6 I8 111(3) . . . 3_766 ? I3 I3 I6 I7 -4(4) 2_655 . . . ? I5 I3 I6 I7 -164(4) 2_655 . . . ? I2 I3 I6 I7 -161(3) . . . . ? I5 I3 I6 I7 -152(5) . . . . ? I4 I3 I6 I7 16(5) . . . . ? I3 I3 I6 I4 -20(4) 2_655 . . . ? I5 I3 I6 I4 -180(4) 2_655 . . . ? I2 I3 I6 I4 -177(3) . . . . ? I5 I3 I6 I4 -168(5) . . . . ? I7 I3 I6 I4 -16(5) . . . . ? I3 I3 I6 I8 -125.7(7) 2_655 . . . ? I5 I3 I6 I8 74(2) 2_655 . . . ? I2 I3 I6 I8 77.0(17) . . . . ? I5 I3 I6 I8 86(4) . . . . ? I7 I3 I6 I8 -122(4) . . . . ? I4 I3 I6 I8 -106(4) . . . . ? I3 I3 I6 I1 -119.0(6) 2_655 . . . ? I5 I3 I6 I1 81.0(19) 2_655 . . . ? I2 I3 I6 I1 83.8(16) . . . . ? I5 I3 I6 I1 93(4) . . . . ? I7 I3 I6 I1 -115(4) . . . . ? I4 I3 I6 I1 -99(4) . . . . ? I3 I3 I6 I8 -111.8(9) 2_655 . . 3_766 ? I5 I3 I6 I8 88(2) 2_655 . . 3_766 ? I2 I3 I6 I8 91.0(17) . . . 3_766 ? I5 I3 I6 I8 100(4) . . . 3_766 ? I7 I3 I6 I8 -108(4) . . . 3_766 ? I4 I3 I6 I8 -92(4) . . . 3_766 ? I8 I1 I6 I7 -169(6) . . . . ? I8 I1 I6 I7 11(6) 3_766 . . . ? I4 I1 I6 I7 -169(5) 3_766 . . . ? I4 I1 I6 I7 11(5) . . . . ? I6 I1 I6 I7 150(10) 3_766 . . . ? I7 I1 I6 I7 180.003(8) 3_766 . . . ? I8 I1 I6 I4 -179(5) . . . . ? I8 I1 I6 I4 1(5) 3_766 . . . ? I4 I1 I6 I4 180.004(9) 3_766 . . . ? I6 I1 I6 I4 139(10) 3_766 . . . ? I7 I1 I6 I4 -11(5) . . . . ? I7 I1 I6 I4 169(5) 3_766 . . . ? I8 I1 I6 I3 -40(3) . . . . ? I8 I1 I6 I3 140(3) 3_766 . . . ? I4 I1 I6 I3 -41(4) 3_766 . . . ? I4 I1 I6 I3 139(4) . . . . ? I6 I1 I6 I3 -82(7) 3_766 . . . ? I7 I1 I6 I3 128(5) . . . . ? I7 I1 I6 I3 -52(5) 3_766 . . . ? I8 I1 I6 I8 180.000(13) 3_766 . . . ? I4 I1 I6 I8 -1(5) 3_766 . . . ? I4 I1 I6 I8 179(5) . . . . ? I6 I1 I6 I8 -41(11) 3_766 . . . ? I7 I1 I6 I8 169(6) . . . . ? I7 I1 I6 I8 -11(6) 3_766 . . . ? I8 I1 I6 I8 180.000(15) . . . 3_766 ? I4 I1 I6 I8 179(5) 3_766 . . 3_766 ? I4 I1 I6 I8 -1(5) . . . 3_766 ? I6 I1 I6 I8 139(11) 3_766 . . 3_766 ? I7 I1 I6 I8 -11(6) . . . 3_766 ? I7 I1 I6 I8 169(6) 3_766 . . 3_766 ? I4 I6 I7 I3 151(11) . . . . ? I8 I6 I7 I3 119(4) . . . . ? I1 I6 I7 I3 121(3) . . . . ? I8 I6 I7 I3 123(2) 3_766 . . . ? I4 I6 I7 I1 29(13) . . . . ? I3 I6 I7 I1 -121(3) . . . . ? I8 I6 I7 I1 -2.1(10) . . . . ? I8 I6 I7 I1 1.9(9) 3_766 . . . ? I4 I6 I7 I8 27(12) . . . 3_766 ? I3 I6 I7 I8 -123(2) . . . 3_766 ? I8 I6 I7 I8 -4(2) . . . 3_766 ? I1 I6 I7 I8 -1.9(9) . . . 3_766 ? I4 I6 I7 I8 31(13) . . . . ? I3 I6 I7 I8 -119(4) . . . . ? I1 I6 I7 I8 2.1(10) . . . . ? I8 I6 I7 I8 4(2) 3_766 . . . ? I3 I3 I7 I6 177(4) 2_655 . . . ? I5 I3 I7 I6 28(5) 2_655 . . . ? I2 I3 I7 I6 45(5) . . . . ? I5 I3 I7 I6 118(7) . . . . ? I4 I3 I7 I6 -62(22) . . . . ? I3 I3 I7 I1 -128.8(5) 2_655 . . . ? I5 I3 I7 I1 82(3) 2_655 . . . ? I6 I3 I7 I1 54(3) . . . . ? I2 I3 I7 I1 100(3) . . . . ? I5 I3 I7 I1 172(8) . . . . ? I4 I3 I7 I1 -8(23) . . . . ? I3 I3 I7 I8 -123.8(8) 2_655 . . 3_766 ? I5 I3 I7 I8 87(3) 2_655 . . 3_766 ? I6 I3 I7 I8 59(3) . . . 3_766 ? I2 I3 I7 I8 105(3) . . . 3_766 ? I5 I3 I7 I8 177(8) . . . 3_766 ? I4 I3 I7 I8 -3(23) . . . 3_766 ? I3 I3 I7 I8 -133.5(7) 2_655 . . . ? I5 I3 I7 I8 78(3) 2_655 . . . ? I6 I3 I7 I8 50(3) . . . . ? I2 I3 I7 I8 95(3) . . . . ? I5 I3 I7 I8 168(8) . . . . ? I4 I3 I7 I8 -13(23) . . . . ? I8 I1 I7 I6 11(6) . . . . ? I8 I1 I7 I6 -169(6) 3_766 . . . ? I4 I1 I7 I6 36(18) 3_766 . . . ? I4 I1 I7 I6 -144(18) . . . . ? I6 I1 I7 I6 180.004(6) 3_766 . . . ? I7 I1 I7 I6 124(10) 3_766 . . . ? I8 I1 I7 I3 -30(3) . . . . ? I8 I1 I7 I3 150(3) 3_766 . . . ? I4 I1 I7 I3 -5(15) 3_766 . . . ? I4 I1 I7 I3 175(15) . . . . ? I6 I1 I7 I3 -41(4) . . . . ? I6 I1 I7 I3 139(4) 3_766 . . . ? I7 I1 I7 I3 83(9) 3_766 . . . ? I8 I1 I7 I8 180.000(14) . . . 3_766 ? I4 I1 I7 I8 -156(15) 3_766 . . 3_766 ? I4 I1 I7 I8 24(15) . . . 3_766 ? I6 I1 I7 I8 169(6) . . . 3_766 ? I6 I1 I7 I8 -11(6) 3_766 . . 3_766 ? I7 I1 I7 I8 -67(9) 3_766 . . 3_766 ? I8 I1 I7 I8 180.000(14) 3_766 . . . ? I4 I1 I7 I8 24(15) 3_766 . . . ? I4 I1 I7 I8 -156(15) . . . . ? I6 I1 I7 I8 -11(6) . . . . ? I6 I1 I7 I8 169(6) 3_766 . . . ? I7 I1 I7 I8 113(9) 3_766 . . . ? I4 I1 I8 I8 -169(38) 3_766 . . 3_766 ? I4 I1 I8 I8 11(37) . . . 3_766 ? I6 I1 I8 I8 11(37) . . . 3_766 ? I6 I1 I8 I8 -169(38) 3_766 . . 3_766 ? I7 I1 I8 I8 9(37) . . . 3_766 ? I7 I1 I8 I8 -171(38) 3_766 . . 3_766 ? I8 I1 I8 I4 169(48) 3_766 . . 3_766 ? I4 I1 I8 I4 179.999(4) . . . 3_766 ? I6 I1 I8 I4 -179.8(12) . . . 3_766 ? I6 I1 I8 I4 0.2(12) 3_766 . . 3_766 ? I7 I1 I8 I4 178.1(12) . . . 3_766 ? I7 I1 I8 I4 -1.9(12) 3_766 . . 3_766 ? I8 I1 I8 I6 -11(46) 3_766 . . . ? I4 I1 I8 I6 179.8(12) 3_766 . . . ? I4 I1 I8 I6 -0.2(12) . . . . ? I6 I1 I8 I6 179.999(2) 3_766 . . . ? I7 I1 I8 I6 -2.1(10) . . . . ? I7 I1 I8 I6 177.9(10) 3_766 . . . ? I8 I1 I8 I4 -11(49) 3_766 . . . ? I4 I1 I8 I4 180.001(3) 3_766 . . . ? I6 I1 I8 I4 0.2(12) . . . . ? I6 I1 I8 I4 -179.8(12) 3_766 . . . ? I7 I1 I8 I4 -1.9(12) . . . . ? I7 I1 I8 I4 178.1(12) 3_766 . . . ? I8 I1 I8 I6 169(45) 3_766 . . 3_766 ? I4 I1 I8 I6 -0.2(12) 3_766 . . 3_766 ? I4 I1 I8 I6 179.8(12) . . . 3_766 ? I6 I1 I8 I6 180.001(2) . . . 3_766 ? I7 I1 I8 I6 177.9(10) . . . 3_766 ? I7 I1 I8 I6 -2.1(10) 3_766 . . 3_766 ? I8 I1 I8 I7 171(43) 3_766 . . 3_766 ? I4 I1 I8 I7 1.9(12) 3_766 . . 3_766 ? I4 I1 I8 I7 -178.1(12) . . . 3_766 ? I6 I1 I8 I7 -177.9(10) . . . 3_766 ? I6 I1 I8 I7 2.1(10) 3_766 . . 3_766 ? I7 I1 I8 I7 179.999(2) . . . 3_766 ? I8 I1 I8 I7 -9(44) 3_766 . . . ? I4 I1 I8 I7 -178.1(12) 3_766 . . . ? I4 I1 I8 I7 1.9(12) . . . . ? I6 I1 I8 I7 2.1(10) . . . . ? I6 I1 I8 I7 -177.9(10) 3_766 . . . ? I7 I1 I8 I7 180.001(2) 3_766 . . . ? I7 I6 I8 I1 12(6) . . . . ? I4 I6 I8 I1 1(5) . . . . ? I3 I6 I8 I1 142(3) . . . . ? I8 I6 I8 I1 0.000(7) 3_766 . . . ? I7 I6 I8 I8 12(6) . . . 3_766 ? I4 I6 I8 I8 1(5) . . . 3_766 ? I3 I6 I8 I8 142(3) . . . 3_766 ? I1 I6 I8 I8 0.000(10) . . . 3_766 ? I7 I6 I8 I4 13(15) . . . 3_766 ? I4 I6 I8 I4 2(16) . . . 3_766 ? I3 I6 I8 I4 143(14) . . . 3_766 ? I1 I6 I8 I4 2(12) . . . 3_766 ? I8 I6 I8 I4 2(12) 3_766 . . 3_766 ? I7 I6 I8 I4 11(6) . . . . ? I3 I6 I8 I4 141(4) . . . . ? I1 I6 I8 I4 -1(5) . . . . ? I8 I6 I8 I4 -1(5) 3_766 . . . ? I7 I6 I8 I6 12(6) . . . 3_766 ? I4 I6 I8 I6 1(5) . . . 3_766 ? I3 I6 I8 I6 142(3) . . . 3_766 ? I1 I6 I8 I6 0.003(7) . . . 3_766 ? I8 I6 I8 I6 0.003(2) 3_766 . . 3_766 ? I7 I6 I8 I7 24(12) . . . 3_766 ? I4 I6 I8 I7 13(9) . . . 3_766 ? I3 I6 I8 I7 154(8) . . . 3_766 ? I1 I6 I8 I7 12(6) . . . 3_766 ? I8 I6 I8 I7 12(6) 3_766 . . 3_766 ? I4 I6 I8 I7 -11(6) . . . . ? I3 I6 I8 I7 130(5) . . . . ? I1 I6 I8 I7 -12(6) . . . . ? I8 I6 I8 I7 -12(6) 3_766 . . . ? I6 I4 I8 I1 -179(5) . . . . ? I8 I4 I8 I1 0.000(6) 3_766 . . . ? I3 I4 I8 I1 151(3) . . . . ? I6 I4 I8 I8 -179(5) . . . 3_766 ? I1 I4 I8 I8 0.000(11) . . . 3_766 ? I3 I4 I8 I8 151(3) . . . 3_766 ? I6 I4 I8 I4 -179(5) . . . 3_766 ? I8 I4 I8 I4 -0.002(2) 3_766 . . 3_766 ? I1 I4 I8 I4 -0.003(8) . . . 3_766 ? I3 I4 I8 I4 151(3) . . . 3_766 ? I8 I4 I8 I6 179(5) 3_766 . . . ? I1 I4 I8 I6 179(5) . . . . ? I3 I4 I8 I6 -30(3) . . . . ? I6 I4 I8 I6 -180(3) . . . 3_766 ? I8 I4 I8 I6 0(2) 3_766 . . 3_766 ? I1 I4 I8 I6 0(2) . . . 3_766 ? I3 I4 I8 I6 150(2) . . . 3_766 ? I6 I4 I8 I7 -175(4) . . . 3_766 ? I8 I4 I8 I7 5(3) 3_766 . . 3_766 ? I1 I4 I8 I7 5(3) . . . 3_766 ? I3 I4 I8 I7 155(3) . . . 3_766 ? I6 I4 I8 I7 23(11) . . . . ? I8 I4 I8 I7 -158(14) 3_766 . . . ? I1 I4 I8 I7 -158(14) . . . . ? I3 I4 I8 I7 -7(13) . . . . ? I6 I7 I8 I1 -168(6) . . . . ? I3 I7 I8 I1 151(3) . . . . ? I8 I7 I8 I1 0.000(6) 3_766 . . . ? I6 I7 I8 I8 -168(6) . . . 3_766 ? I3 I7 I8 I8 151(3) . . . 3_766 ? I1 I7 I8 I8 0.000(12) . . . 3_766 ? I6 I7 I8 I4 -175(6) . . . 3_766 ? I3 I7 I8 I4 144(6) . . . 3_766 ? I1 I7 I8 I4 -7(4) . . . 3_766 ? I8 I7 I8 I4 -7(4) 3_766 . . 3_766 ? I3 I7 I8 I6 -41(4) . . . . ? I1 I7 I8 I6 168(6) . . . . ? I8 I7 I8 I6 168(6) 3_766 . . . ? I6 I7 I8 I4 -146(16) . . . . ? I3 I7 I8 I4 172(14) . . . . ? I1 I7 I8 I4 22(13) . . . . ? I8 I7 I8 I4 22(13) 3_766 . . . ? I6 I7 I8 I6 -172(4) . . . 3_766 ? I3 I7 I8 I6 147(2) . . . 3_766 ? I1 I7 I8 I6 -4(2) . . . 3_766 ? I8 I7 I8 I6 -4(2) 3_766 . . 3_766 ? I6 I7 I8 I7 -168(6) . . . 3_766 ? I3 I7 I8 I7 151(3) . . . 3_766 ? I1 I7 I8 I7 -0.002(8) . . . 3_766 ? I8 I7 I8 I7 -0.002(2) 3_766 . . 3_766 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 4.228 _refine_diff_density_min -1.381 _refine_diff_density_rms 0.323 data_FeCID2_DMF _database_code_depnum_ccdc_archive 'CCDC 901083' #TrackingRef 'web_deposit_cif_file_3_SatoshiHorike_1347458117.FeCID-2_DMF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H29 Fe2 N7 O9' _chemical_formula_weight 827.37 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.110(3) _cell_length_b 11.484(4) _cell_length_c 15.735(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.542(4) _cell_angle_gamma 90.00 _cell_volume 1760.0(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.892 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8417 _exptl_absorpt_correction_T_max 0.8417 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13269 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6199 _reflns_number_gt 5950 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.13(3) _refine_ls_number_reflns 6199 _refine_ls_number_parameters 498 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2659 _refine_ls_wR_factor_gt 0.2583 _refine_ls_goodness_of_fit_ref 1.887 _refine_ls_restrained_S_all 1.887 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.005 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 Fe3 Fe -0.06644(8) 0.27013(8) 0.71162(6) 0.0232(3) Uani 1 1 d . . . Fe1 Fe 0.18036(9) 0.26115(9) 0.53582(6) 0.0230(3) Uani 1 1 d . . . O3 O -0.2793(6) 0.2781(5) 0.7028(4) 0.0258(13) Uani 1 1 d . . . O4 O -0.8631(6) 0.2772(5) 0.7880(4) 0.0296(13) Uani 1 1 d . . . O8 O -0.7850(8) 0.2502(5) 0.6700(4) 0.0324(15) Uani 1 1 d . . . C104 C -0.7688(8) 0.2765(6) 0.7519(6) 0.0232(16) Uani 1 1 d . . . C1 C -0.1846(9) 0.6409(8) 0.6468(5) 0.0303(17) Uani 1 1 d . . . H4 H -0.2610 0.6778 0.6107 0.036 Uiso 1 1 calc R . . N15 N -0.0731(10) 1.0775(5) 0.7133(7) 0.0340(15) Uani 1 1 d . . . C100 C 0.1993(9) -0.1741(7) 0.5432(6) 0.0295(17) Uani 1 1 d . . . C102 C -0.5192(9) 0.2890(8) 0.7650(5) 0.0299(17) Uani 1 1 d . . . H1 H -0.5345 0.2655 0.7066 0.036 Uiso 1 1 calc R . . O10 O -0.1440(6) 0.2917(7) 0.8353(4) 0.0380(15) Uani 1 1 d . . . C99 C -0.1773(10) 0.5210(8) 0.6461(6) 0.0361(19) Uani 1 1 d . . . H5 H -0.2466 0.4795 0.6070 0.043 Uiso 1 1 calc R . . C103 C -0.6226(7) 0.3016(8) 0.8013(5) 0.0291(16) Uani 1 1 d . . . N1 N -0.0715(8) 0.4614(5) 0.7009(5) 0.0262(13) Uani 1 1 d . . . C22 C 0.0266(9) 0.6452(7) 0.7514(6) 0.0361(19) Uani 1 1 d . . . H6 H 0.1001 0.6862 0.7871 0.043 Uiso 1 1 calc R . . C23 C 0.0309(10) 0.5245(7) 0.7528(7) 0.038(2) Uani 1 1 d . . . H7 H 0.1056 0.4867 0.7901 0.046 Uiso 1 1 calc R . . N21 N 0.1866(8) -0.5487(5) 0.5457(5) 0.0276(13) Uani 1 1 d . . . C26 C 0.1935(9) -0.3028(7) 0.5482(6) 0.0273(17) Uani 1 1 d . . . N22 N 0.1888(7) 0.0713(6) 0.5343(5) 0.0268(13) Uani 1 1 d . . . C28 C 0.1051(8) -0.1158(7) 0.4753(5) 0.0350(17) Uani 1 1 d . . . H8 H 0.0433 -0.1583 0.4320 0.042 Uiso 1 1 calc R . . C30 C 0.0799(10) -0.4838(8) 0.5033(7) 0.039(2) Uani 1 1 d . . . H9 H 0.0012 -0.5231 0.4726 0.047 Uiso 1 1 calc R . . C31 C -0.0822(10) 0.7069(7) 0.6994(6) 0.0302(18) Uani 1 1 d . . . C32 C -0.2630(8) 0.2933(8) 0.7822(5) 0.0263(15) Uani 1 1 d . . . C33 C -0.5986(9) 0.3391(10) 0.8895(6) 0.044(2) Uani 1 1 d . . . H2 H -0.6741 0.3478 0.9121 0.053 Uiso 1 1 calc R . . C35 C -0.0770(10) 0.8357(6) 0.7061(6) 0.0297(16) Uani 1 1 d . . . C36 C 0.0756(10) -0.3640(8) 0.5006(7) 0.0382(19) Uani 1 1 d . . . H10 H -0.0022 -0.3246 0.4686 0.046 Uiso 1 1 calc R . . C39 C -0.3842(8) 0.3125(7) 0.8181(5) 0.0286(16) Uani 1 1 d . . . C40 C -0.3718(9) 0.3511(9) 0.9035(6) 0.043(2) Uani 1 1 d . . . H3 H -0.2840 0.3705 0.9370 0.051 Uiso 1 1 calc R . . C41 C 0.2891(8) -0.1073(7) 0.6042(6) 0.0337(16) Uani 1 1 d . . . H11 H 0.3535 -0.1422 0.6508 0.040 Uiso 1 1 calc R . . C42 C 0.1031(8) 0.0052(8) 0.4719(6) 0.0398(18) Uani 1 1 d . . . H12 H 0.0410 0.0420 0.4252 0.048 Uiso 1 1 calc R . . N23 N -0.4743(8) 0.3632(11) 0.9430(5) 0.059(3) Uani 1 1 d . . . C44 C 0.0418(9) 0.8948(8) 0.7221(8) 0.049(2) Uani 1 1 d . . . H13 H 0.1243 0.8548 0.7306 0.059 Uiso 1 1 calc R . . C45 C -0.1891(9) 1.0206(8) 0.7012(6) 0.0391(18) Uani 1 1 d . . . H14 H -0.2690 1.0626 0.6977 0.047 Uiso 1 1 calc R . . C46 C 0.3054(9) -0.3682(8) 0.5949(6) 0.0315(18) Uani 1 1 d . . . H15 H 0.3848 -0.3317 0.6277 0.038 Uiso 1 1 calc R . . C48 C 0.2835(8) 0.0137(7) 0.5961(6) 0.0337(17) Uani 1 1 d . . . H16 H 0.3495 0.0571 0.6360 0.040 Uiso 1 1 calc R . . C49 C 0.0416(9) 1.0158(7) 0.7260(8) 0.051(3) Uani 1 1 d . . . H17 H 0.1251 1.0551 0.7378 0.061 Uiso 1 1 calc R . . C50 C -0.1980(8) 0.8999(7) 0.6933(6) 0.0388(18) Uani 1 1 d . . . H18 H -0.2828 0.8628 0.6797 0.047 Uiso 1 1 calc R . . C55 C 0.2962(8) -0.4884(7) 0.5916(5) 0.0257(15) Uani 1 1 d . . . H19 H 0.3717 -0.5306 0.6237 0.031 Uiso 1 1 calc R . . O9 O -0.0215(7) 0.2635(5) 0.4589(4) 0.0316(15) Uani 1 1 d . . . C108 C -0.3686(8) 0.2755(7) 0.4803(6) 0.0259(17) Uani 1 1 d . . . H27 H -0.3520 0.2636 0.5407 0.031 Uiso 1 1 calc R . . C114 C -0.5003(8) 0.2847(8) 0.4274(5) 0.0302(17) Uani 1 1 d . . . C105 C -0.1154(10) 0.2659(6) 0.4980(6) 0.0249(17) Uani 1 1 d . . . O1 O -0.0947(7) 0.2543(6) 0.5777(5) 0.0367(16) Uani 1 1 d . . . C106 C -0.2587(9) 0.2844(8) 0.4409(5) 0.0310(17) Uani 1 1 d . . . C109 C -0.5209(8) 0.3088(10) 0.3375(5) 0.040(2) Uani 1 1 d . . . H28 H -0.6103 0.3147 0.3018 0.049 Uiso 1 1 calc R . . N26 N -0.4158(8) 0.3238(11) 0.3011(5) 0.062(3) Uani 1 1 d . . . C107 C -0.2875(8) 0.3075(11) 0.3528(6) 0.043(2) Uani 1 1 d . . . H29 H -0.2148 0.3123 0.3271 0.051 Uiso 1 1 calc R . . O13 O -0.6033(7) 0.2634(5) 0.5472(4) 0.0291(14) Uani 1 1 d . . . O12 O -0.7413(7) 0.2729(7) 0.4143(5) 0.0428(18) Uani 1 1 d . . . C115 C -0.6230(10) 0.2731(7) 0.4637(6) 0.0315(19) Uani 1 1 d . . . N27 N -0.4203(10) -0.0218(9) 0.4134(6) 0.057(2) Uani 1 1 d . . . O14 O -0.4598(12) 0.0182(11) 0.2691(8) 0.105(4) Uani 1 1 d . . . C116 C -0.511(5) -0.0007(18) 0.3331(14) 0.31(3) Uani 1 1 d . . . H26 H -0.6052 -0.0003 0.3258 0.374 Uiso 1 1 calc R . . C117 C -0.2690(13) -0.0306(16) 0.4420(12) 0.104(6) Uani 1 1 d . . . H20 H -0.2327 -0.0196 0.3921 0.156 Uiso 1 1 calc R . . H21 H -0.2430 -0.1060 0.4672 0.156 Uiso 1 1 calc R . . H22 H -0.2330 0.0283 0.4853 0.156 Uiso 1 1 calc R . . C118 C -0.482(2) -0.0365(17) 0.4867(11) 0.116(7) Uani 1 1 d . . . H23 H -0.4833 0.0370 0.5157 0.173 Uiso 1 1 calc R . . H24 H -0.4299 -0.0918 0.5280 0.173 Uiso 1 1 calc R . . H25 H -0.5748 -0.0643 0.4646 0.173 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe3 0.0156(5) 0.0271(5) 0.0260(5) -0.0006(5) 0.0039(4) -0.0009(4) Fe1 0.0129(5) 0.0281(5) 0.0290(6) -0.0011(5) 0.0072(4) -0.0002(4) O3 0.023(3) 0.032(3) 0.028(3) 0.000(2) 0.016(3) 0.003(2) O4 0.019(3) 0.035(3) 0.036(3) -0.002(2) 0.010(3) 0.000(2) O8 0.027(4) 0.046(3) 0.020(3) 0.000(2) -0.001(3) 0.002(2) C104 0.003(3) 0.030(4) 0.035(4) 0.006(3) 0.001(3) 0.000(2) C1 0.027(4) 0.039(4) 0.022(3) -0.004(3) 0.001(3) 0.005(3) N15 0.044(4) 0.014(2) 0.051(4) -0.002(3) 0.024(3) 0.000(3) C100 0.030(4) 0.030(4) 0.025(3) 0.003(3) 0.001(3) 0.011(4) C102 0.033(4) 0.031(4) 0.022(4) -0.005(3) 0.000(3) -0.001(3) O10 0.015(3) 0.066(4) 0.027(3) 0.001(3) -0.006(2) -0.008(3) C99 0.036(4) 0.031(4) 0.036(4) 0.003(3) 0.001(3) 0.002(3) C103 0.010(3) 0.037(4) 0.033(4) 0.001(3) -0.008(3) -0.006(3) N1 0.021(3) 0.024(3) 0.034(3) 0.002(3) 0.008(3) -0.004(3) C22 0.027(4) 0.027(4) 0.043(4) -0.004(4) -0.010(3) -0.002(3) C23 0.029(4) 0.017(4) 0.060(5) -0.009(4) -0.001(4) -0.001(3) N21 0.023(3) 0.026(3) 0.030(3) 0.002(3) -0.001(2) -0.003(3) C26 0.023(4) 0.026(3) 0.031(4) 0.000(3) 0.005(3) 0.001(4) N22 0.014(3) 0.033(3) 0.030(3) -0.003(3) 0.001(2) 0.001(3) C28 0.026(4) 0.033(4) 0.036(4) -0.008(3) -0.007(3) 0.000(3) C30 0.028(4) 0.036(5) 0.045(5) -0.007(4) -0.003(3) -0.005(4) C31 0.031(5) 0.032(4) 0.029(5) 0.003(4) 0.010(4) 0.003(4) C32 0.009(3) 0.038(4) 0.035(4) 0.002(3) 0.010(3) 0.004(3) C33 0.029(4) 0.078(7) 0.032(4) -0.011(4) 0.022(3) -0.008(4) C35 0.026(4) 0.031(4) 0.036(4) 0.012(4) 0.016(3) 0.006(4) C36 0.031(4) 0.032(4) 0.045(5) -0.003(4) 0.000(4) 0.000(4) C39 0.019(3) 0.035(4) 0.037(4) -0.002(3) 0.017(3) -0.002(3) C40 0.023(3) 0.069(6) 0.034(4) -0.002(4) 0.003(3) 0.005(4) C41 0.034(4) 0.028(4) 0.035(4) 0.002(3) 0.001(3) 0.006(3) C42 0.029(4) 0.039(4) 0.050(5) -0.001(4) 0.009(3) 0.006(3) N23 0.022(3) 0.120(9) 0.036(4) -0.021(5) 0.009(3) -0.016(4) C44 0.032(4) 0.032(4) 0.094(8) -0.004(5) 0.034(5) -0.003(3) C45 0.037(4) 0.036(4) 0.046(5) -0.008(4) 0.015(4) -0.001(3) C46 0.024(4) 0.031(4) 0.042(4) -0.002(3) 0.013(3) -0.001(3) C48 0.021(3) 0.022(3) 0.051(5) -0.003(3) -0.002(3) -0.001(3) C49 0.030(4) 0.027(4) 0.102(9) -0.008(5) 0.028(5) -0.002(3) C50 0.031(4) 0.026(4) 0.057(5) -0.004(4) 0.008(4) -0.007(3) C55 0.014(3) 0.027(4) 0.035(4) -0.002(3) 0.004(3) 0.006(3) O9 0.015(3) 0.044(4) 0.034(4) -0.002(2) 0.004(3) -0.001(2) C108 0.011(3) 0.041(4) 0.026(4) -0.005(3) 0.005(3) -0.005(3) C114 0.009(3) 0.053(5) 0.026(4) -0.004(3) -0.002(3) -0.002(3) C105 0.026(5) 0.025(4) 0.025(4) 0.002(2) 0.008(3) -0.001(2) O1 0.018(4) 0.069(4) 0.023(4) 0.000(2) 0.004(3) 0.009(2) C106 0.024(4) 0.047(5) 0.026(4) 0.001(3) 0.013(3) 0.005(3) C109 0.015(3) 0.081(7) 0.025(3) 0.003(4) 0.007(3) 0.002(4) N26 0.022(3) 0.133(10) 0.031(4) 0.029(5) 0.007(3) 0.003(5) C107 0.015(3) 0.082(7) 0.029(4) 0.005(4) 0.003(3) 0.008(4) O13 0.022(3) 0.038(3) 0.025(3) 0.003(2) 0.004(3) 0.000(2) O12 0.023(4) 0.073(5) 0.036(4) 0.000(3) 0.015(3) -0.009(3) C115 0.023(4) 0.038(4) 0.031(4) 0.006(3) 0.002(3) 0.002(3) N27 0.058(5) 0.067(6) 0.049(5) -0.014(4) 0.018(4) -0.009(4) O14 0.089(8) 0.125(10) 0.095(8) 0.004(7) 0.017(6) 0.001(7) C116 0.84(9) 0.054(11) 0.086(14) -0.008(10) 0.19(3) 0.02(2) C117 0.047(7) 0.090(11) 0.166(18) -0.006(11) 0.013(9) 0.002(7) C118 0.157(18) 0.120(16) 0.085(11) 0.024(10) 0.060(12) 0.037(14) _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 Fe3 O1 2.058(7) . ? Fe3 O4 2.086(7) 1_655 ? Fe3 O3 2.120(6) . ? Fe3 N1 2.202(6) . ? Fe3 N15 2.214(6) 1_545 ? Fe3 O10 2.298(7) . ? Fe1 O8 2.050(7) 1_655 ? Fe1 O9 2.076(6) . ? Fe1 O13 2.146(7) 1_655 ? Fe1 N22 2.182(6) . ? Fe1 N21 2.189(6) 1_565 ? Fe1 O12 2.261(7) 1_655 ? O3 C32 1.229(10) . ? O4 C104 1.234(11) . ? O4 Fe3 2.086(6) 1_455 ? O8 C104 1.291(12) . ? O8 Fe1 2.050(7) 1_455 ? C104 C103 1.502(10) . ? C1 C31 1.368(13) . ? C1 C99 1.379(13) . ? C1 H4 0.9300 . ? N15 C45 1.311(12) . ? N15 C49 1.328(12) . ? N15 Fe3 2.214(6) 1_565 ? C100 C41 1.367(12) . ? C100 C28 1.396(11) . ? C100 C26 1.482(12) . ? C102 C103 1.327(12) . ? C102 C39 1.423(11) . ? C102 H1 0.9300 . ? O10 C32 1.268(10) . ? C99 N1 1.365(11) . ? C99 H5 0.9300 . ? C103 C33 1.411(12) . ? N1 C23 1.346(11) . ? C22 C31 1.378(12) . ? C22 C23 1.387(11) . ? C22 H6 0.9300 . ? C23 H7 0.9300 . ? N21 C30 1.334(12) . ? N21 C55 1.342(11) . ? N21 Fe1 2.189(6) 1_545 ? C26 C46 1.391(12) . ? C26 C36 1.413(12) . ? N22 C48 1.342(11) . ? N22 C42 1.355(11) . ? C28 C42 1.392(12) . ? C28 H8 0.9300 . ? C30 C36 1.378(13) . ? C30 H9 0.9300 . ? C31 C35 1.482(12) . ? C32 C39 1.496(10) . ? C33 N23 1.340(11) . ? C33 H2 0.9300 . ? C35 C44 1.344(12) . ? C35 C50 1.396(11) . ? C36 H10 0.9300 . ? C39 C40 1.388(12) . ? C40 N23 1.351(11) . ? C40 H3 0.9300 . ? C41 C48 1.395(11) . ? C41 H11 0.9300 . ? C42 H12 0.9300 . ? C44 C49 1.391(12) . ? C44 H13 0.9300 . ? C45 C50 1.392(11) . ? C45 H14 0.9300 . ? C46 C55 1.385(12) . ? C46 H15 0.9300 . ? C48 H16 0.9300 . ? C49 H17 0.9300 . ? C50 H18 0.9300 . ? C55 H19 0.9300 . ? O9 C105 1.262(12) . ? C108 C114 1.372(11) . ? C108 C106 1.414(11) . ? C108 H27 0.9300 . ? C114 C109 1.400(12) . ? C114 C115 1.505(12) . ? C105 O1 1.221(12) . ? C105 C106 1.502(13) . ? C106 C107 1.364(12) . ? C109 N26 1.347(10) . ? C109 H28 0.9300 . ? N26 C107 1.347(10) . ? C107 H29 0.9300 . ? O13 C115 1.281(12) . ? O13 Fe1 2.146(7) 1_455 ? O12 C115 1.239(12) . ? O12 Fe1 2.261(7) 1_455 ? N27 C116 1.37(3) . ? N27 C118 1.465(18) . ? N27 C117 1.477(14) . ? O14 C116 1.27(3) . ? C116 H26 0.9300 . ? C117 H20 0.9600 . ? C117 H21 0.9600 . ? C117 H22 0.9600 . ? C118 H23 0.9600 . ? C118 H24 0.9600 . ? C118 H25 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe3 O4 116.0(3) . 1_655 ? O1 Fe3 O3 94.4(3) . . ? O4 Fe3 O3 149.5(2) 1_655 . ? O1 Fe3 N1 90.9(3) . . ? O4 Fe3 N1 90.2(3) 1_655 . ? O3 Fe3 N1 87.1(2) . . ? O1 Fe3 N15 85.9(3) . 1_545 ? O4 Fe3 N15 93.5(3) 1_655 1_545 ? O3 Fe3 N15 90.6(3) . 1_545 ? N1 Fe3 N15 175.9(4) . 1_545 ? O1 Fe3 O10 153.1(3) . . ? O4 Fe3 O10 90.9(2) 1_655 . ? O3 Fe3 O10 58.7(2) . . ? N1 Fe3 O10 87.2(3) . . ? N15 Fe3 O10 94.5(3) 1_545 . ? O8 Fe1 O9 118.1(3) 1_655 . ? O8 Fe1 O13 91.5(3) 1_655 1_655 ? O9 Fe1 O13 150.4(3) . 1_655 ? O8 Fe1 N22 87.3(3) 1_655 . ? O9 Fe1 N22 92.4(2) . . ? O13 Fe1 N22 88.4(2) 1_655 . ? O8 Fe1 N21 89.7(3) 1_655 1_565 ? O9 Fe1 N21 91.9(3) . 1_565 ? O13 Fe1 N21 88.4(3) 1_655 1_565 ? N22 Fe1 N21 175.5(3) . 1_565 ? O8 Fe1 O12 150.8(3) 1_655 1_655 ? O9 Fe1 O12 91.1(3) . 1_655 ? O13 Fe1 O12 59.3(3) 1_655 1_655 ? N22 Fe1 O12 91.6(3) . 1_655 ? N21 Fe1 O12 89.5(3) 1_565 1_655 ? C32 O3 Fe3 94.8(5) . . ? C104 O4 Fe3 119.9(6) . 1_455 ? C104 O8 Fe1 162.8(5) . 1_455 ? O4 C104 O8 123.6(8) . . ? O4 C104 C103 122.4(8) . . ? O8 C104 C103 113.9(7) . . ? C31 C1 C99 121.7(8) . . ? C31 C1 H4 119.2 . . ? C99 C1 H4 119.2 . . ? C45 N15 C49 117.9(7) . . ? C45 N15 Fe3 121.7(6) . 1_565 ? C49 N15 Fe3 120.4(6) . 1_565 ? C41 C100 C28 117.2(7) . . ? C41 C100 C26 123.4(7) . . ? C28 C100 C26 119.4(7) . . ? C103 C102 C39 117.9(7) . . ? C103 C102 H1 121.0 . . ? C39 C102 H1 121.0 . . ? C32 O10 Fe3 85.6(5) . . ? N1 C99 C1 122.0(8) . . ? N1 C99 H5 119.0 . . ? C1 C99 H5 119.0 . . ? C102 C103 C33 120.6(7) . . ? C102 C103 C104 122.4(8) . . ? C33 C103 C104 117.0(8) . . ? C23 N1 C99 117.3(7) . . ? C23 N1 Fe3 119.5(6) . . ? C99 N1 Fe3 123.1(6) . . ? C31 C22 C23 122.7(8) . . ? C31 C22 H6 118.6 . . ? C23 C22 H6 118.6 . . ? N1 C23 C22 120.9(8) . . ? N1 C23 H7 119.6 . . ? C22 C23 H7 119.6 . . ? C30 N21 C55 114.9(7) . . ? C30 N21 Fe1 121.2(6) . 1_545 ? C55 N21 Fe1 123.8(5) . 1_545 ? C46 C26 C36 117.6(8) . . ? C46 C26 C100 121.8(7) . . ? C36 C26 C100 120.5(7) . . ? C48 N22 C42 116.2(7) . . ? C48 N22 Fe1 120.5(5) . . ? C42 N22 Fe1 123.3(6) . . ? C42 C28 C100 120.6(7) . . ? C42 C28 H8 119.7 . . ? C100 C28 H8 119.7 . . ? N21 C30 C36 126.1(9) . . ? N21 C30 H9 117.0 . . ? C36 C30 H9 117.0 . . ? C1 C31 C22 115.3(8) . . ? C1 C31 C35 127.0(8) . . ? C22 C31 C35 117.6(7) . . ? O3 C32 O10 120.8(7) . . ? O3 C32 C39 120.3(7) . . ? O10 C32 C39 118.8(7) . . ? N23 C33 C103 124.5(8) . . ? N23 C33 H2 117.7 . . ? C103 C33 H2 117.7 . . ? C44 C35 C50 117.7(7) . . ? C44 C35 C31 122.0(8) . . ? C50 C35 C31 120.3(7) . . ? C30 C36 C26 117.7(9) . . ? C30 C36 H10 121.1 . . ? C26 C36 H10 121.1 . . ? C40 C39 C102 117.0(7) . . ? C40 C39 C32 122.8(7) . . ? C102 C39 C32 120.2(7) . . ? N23 C40 C39 126.7(8) . . ? N23 C40 H3 116.7 . . ? C39 C40 H3 116.7 . . ? C100 C41 C48 119.4(7) . . ? C100 C41 H11 120.3 . . ? C48 C41 H11 120.3 . . ? N22 C42 C28 122.1(8) . . ? N22 C42 H12 118.9 . . ? C28 C42 H12 118.9 . . ? C33 N23 C40 113.3(8) . . ? C35 C44 C49 120.1(8) . . ? C35 C44 H13 119.9 . . ? C49 C44 H13 119.9 . . ? N15 C45 C50 122.9(8) . . ? N15 C45 H14 118.6 . . ? C50 C45 H14 118.6 . . ? C55 C46 C26 118.8(8) . . ? C55 C46 H15 120.6 . . ? C26 C46 H15 120.6 . . ? N22 C48 C41 124.2(7) . . ? N22 C48 H16 117.9 . . ? C41 C48 H16 117.9 . . ? N15 C49 C44 122.5(8) . . ? N15 C49 H17 118.7 . . ? C44 C49 H17 118.7 . . ? C45 C50 C35 118.7(7) . . ? C45 C50 H18 120.7 . . ? C35 C50 H18 120.6 . . ? N21 C55 C46 124.9(8) . . ? N21 C55 H19 117.6 . . ? C46 C55 H19 117.6 . . ? C105 O9 Fe1 117.8(6) . . ? C114 C108 C106 118.4(8) . . ? C114 C108 H27 120.8 . . ? C106 C108 H27 120.8 . . ? C108 C114 C109 119.1(8) . . ? C108 C114 C115 121.9(8) . . ? C109 C114 C115 119.1(7) . . ? O1 C105 O9 123.6(9) . . ? O1 C105 C106 120.2(8) . . ? O9 C105 C106 116.2(8) . . ? C105 O1 Fe3 168.5(6) . . ? C107 C106 C108 118.8(8) . . ? C107 C106 C105 123.0(7) . . ? C108 C106 C105 118.2(7) . . ? N26 C109 C114 122.3(7) . . ? N26 C109 H28 118.9 . . ? C114 C109 H28 118.9 . . ? C109 N26 C107 117.9(8) . . ? N26 C107 C106 123.3(8) . . ? N26 C107 H29 118.4 . . ? C106 C107 H29 118.4 . . ? C115 O13 Fe1 92.3(6) . 1_455 ? C115 O12 Fe1 88.2(6) . 1_455 ? O12 C115 O13 120.1(9) . . ? O12 C115 C114 121.2(8) . . ? O13 C115 C114 118.7(8) . . ? C116 N27 C118 115.2(19) . . ? C116 N27 C117 132.5(19) . . ? C118 N27 C117 112.3(12) . . ? O14 C116 N27 117(4) . . ? O14 C116 H26 121.6 . . ? N27 C116 H26 121.7 . . ? N27 C117 H20 109.5 . . ? N27 C117 H21 109.5 . . ? H20 C117 H21 109.5 . . ? N27 C117 H22 109.5 . . ? H20 C117 H22 109.5 . . ? H21 C117 H22 109.5 . . ? N27 C118 H23 109.5 . . ? N27 C118 H24 109.5 . . ? H23 C118 H24 109.5 . . ? N27 C118 H25 109.5 . . ? H23 C118 H25 109.5 . . ? H24 C118 H25 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Fe3 O3 C32 -176.9(5) . . . . ? O4 Fe3 O3 C32 -0.7(7) 1_655 . . . ? N1 Fe3 O3 C32 -86.2(5) . . . . ? N15 Fe3 O3 C32 97.2(6) 1_545 . . . ? O10 Fe3 O3 C32 2.3(5) . . . . ? Fe3 O4 C104 O8 -13.3(10) 1_455 . . . ? Fe3 O4 C104 C103 169.4(5) 1_455 . . . ? Fe1 O8 C104 O4 91(2) 1_455 . . . ? Fe1 O8 C104 C103 -91(2) 1_455 . . . ? O1 Fe3 O10 C32 -0.3(9) . . . . ? O4 Fe3 O10 C32 176.3(5) 1_655 . . . ? O3 Fe3 O10 C32 -2.2(5) . . . . ? N1 Fe3 O10 C32 86.1(5) . . . . ? N15 Fe3 O10 C32 -90.1(6) 1_545 . . . ? C31 C1 C99 N1 3.5(15) . . . . ? C39 C102 C103 C33 1.1(14) . . . . ? C39 C102 C103 C104 -178.6(7) . . . . ? O4 C104 C103 C102 172.8(8) . . . . ? O8 C104 C103 C102 -4.8(12) . . . . ? O4 C104 C103 C33 -6.9(12) . . . . ? O8 C104 C103 C33 175.6(8) . . . . ? C1 C99 N1 C23 -3.8(15) . . . . ? C1 C99 N1 Fe3 173.5(7) . . . . ? O1 Fe3 N1 C23 -127.9(8) . . . . ? O4 Fe3 N1 C23 -11.9(8) 1_655 . . . ? O3 Fe3 N1 C23 137.8(8) . . . . ? N15 Fe3 N1 C23 -166(5) 1_545 . . . ? O10 Fe3 N1 C23 79.0(8) . . . . ? O1 Fe3 N1 C99 54.9(8) . . . . ? O4 Fe3 N1 C99 170.9(8) 1_655 . . . ? O3 Fe3 N1 C99 -39.5(8) . . . . ? N15 Fe3 N1 C99 17(5) 1_545 . . . ? O10 Fe3 N1 C99 -98.3(8) . . . . ? C99 N1 C23 C22 1.4(15) . . . . ? Fe3 N1 C23 C22 -176.1(8) . . . . ? C31 C22 C23 N1 1.5(17) . . . . ? C41 C100 C26 C46 -23.2(12) . . . . ? C28 C100 C26 C46 159.7(10) . . . . ? C41 C100 C26 C36 160.8(11) . . . . ? C28 C100 C26 C36 -16.2(12) . . . . ? O8 Fe1 N22 C48 -41.5(7) 1_655 . . . ? O9 Fe1 N22 C48 -159.6(7) . . . . ? O13 Fe1 N22 C48 50.0(7) 1_655 . . . ? N21 Fe1 N22 C48 6(5) 1_565 . . . ? O12 Fe1 N22 C48 109.3(7) 1_655 . . . ? O8 Fe1 N22 C42 139.8(8) 1_655 . . . ? O9 Fe1 N22 C42 21.7(7) . . . . ? O13 Fe1 N22 C42 -128.7(7) 1_655 . . . ? N21 Fe1 N22 C42 -173(4) 1_565 . . . ? O12 Fe1 N22 C42 -69.4(7) 1_655 . . . ? C41 C100 C28 C42 -1.0(14) . . . . ? C26 C100 C28 C42 176.3(8) . . . . ? C55 N21 C30 C36 2.2(16) . . . . ? Fe1 N21 C30 C36 -175.9(8) 1_545 . . . ? C99 C1 C31 C22 -0.6(15) . . . . ? C99 C1 C31 C35 179.7(9) . . . . ? C23 C22 C31 C1 -1.8(16) . . . . ? C23 C22 C31 C35 177.8(10) . . . . ? Fe3 O3 C32 O10 -4.1(9) . . . . ? Fe3 O3 C32 C39 176.7(7) . . . . ? Fe3 O10 C32 O3 3.8(8) . . . . ? Fe3 O10 C32 C39 -177.0(7) . . . . ? C102 C103 C33 N23 -0.8(17) . . . . ? C104 C103 C33 N23 178.8(11) . . . . ? C1 C31 C35 C44 -147.0(12) . . . . ? C22 C31 C35 C44 33.4(13) . . . . ? C1 C31 C35 C50 31.1(13) . . . . ? C22 C31 C35 C50 -148.5(10) . . . . ? N21 C30 C36 C26 -1.1(17) . . . . ? C46 C26 C36 C30 -0.4(15) . . . . ? C100 C26 C36 C30 175.7(8) . . . . ? C103 C102 C39 C40 -2.2(13) . . . . ? C103 C102 C39 C32 176.5(8) . . . . ? O3 C32 C39 C40 -167.9(9) . . . . ? O10 C32 C39 C40 12.9(14) . . . . ? O3 C32 C39 C102 13.5(13) . . . . ? O10 C32 C39 C102 -165.7(8) . . . . ? C102 C39 C40 N23 3.5(16) . . . . ? C32 C39 C40 N23 -175.2(10) . . . . ? C28 C100 C41 C48 -0.3(14) . . . . ? C26 C100 C41 C48 -177.4(8) . . . . ? C48 N22 C42 C28 5.2(13) . . . . ? Fe1 N22 C42 C28 -176.1(7) . . . . ? C100 C28 C42 N22 -1.6(14) . . . . ? C103 C33 N23 C40 1.7(18) . . . . ? C39 C40 N23 C33 -3.1(18) . . . . ? C50 C35 C44 C49 0.4(17) . . . . ? C31 C35 C44 C49 178.6(10) . . . . ? C49 N15 C45 C50 -5.8(16) . . . . ? Fe3 N15 C45 C50 173.5(7) 1_565 . . . ? C36 C26 C46 C55 0.6(14) . . . . ? C100 C26 C46 C55 -175.4(7) . . . . ? C42 N22 C48 C41 -6.6(14) . . . . ? Fe1 N22 C48 C41 174.6(7) . . . . ? C100 C41 C48 N22 4.3(14) . . . . ? C45 N15 C49 C44 3.4(18) . . . . ? Fe3 N15 C49 C44 -175.9(9) 1_565 . . . ? C35 C44 C49 N15 -0.8(18) . . . . ? N15 C45 C50 C35 5.5(15) . . . . ? C44 C35 C50 C45 -2.6(15) . . . . ? C31 C35 C50 C45 179.2(8) . . . . ? C30 N21 C55 C46 -1.9(14) . . . . ? Fe1 N21 C55 C46 176.2(6) 1_545 . . . ? C26 C46 C55 N21 0.5(14) . . . . ? O8 Fe1 O9 C105 4.7(6) 1_655 . . . ? O13 Fe1 O9 C105 -176.2(5) 1_655 . . . ? N22 Fe1 O9 C105 92.9(6) . . . . ? N21 Fe1 O9 C105 -86.0(6) 1_565 . . . ? O12 Fe1 O9 C105 -175.5(5) 1_655 . . . ? C106 C108 C114 C109 -3.4(14) . . . . ? C106 C108 C114 C115 178.4(8) . . . . ? Fe1 O9 C105 O1 -8.2(10) . . . . ? Fe1 O9 C105 C106 171.7(5) . . . . ? O9 C105 O1 Fe3 105(3) . . . . ? C106 C105 O1 Fe3 -75(4) . . . . ? O4 Fe3 O1 C105 -99(4) 1_655 . . . ? O3 Fe3 O1 C105 79(4) . . . . ? N1 Fe3 O1 C105 -9(4) . . . . ? N15 Fe3 O1 C105 169(4) 1_545 . . . ? O10 Fe3 O1 C105 77(4) . . . . ? C114 C108 C106 C107 3.2(14) . . . . ? C114 C108 C106 C105 -175.8(7) . . . . ? O1 C105 C106 C107 174.4(10) . . . . ? O9 C105 C106 C107 -5.5(13) . . . . ? O1 C105 C106 C108 -6.7(12) . . . . ? O9 C105 C106 C108 173.4(7) . . . . ? C108 C114 C109 N26 -0.3(17) . . . . ? C115 C114 C109 N26 178.0(10) . . . . ? C114 C109 N26 C107 4.2(19) . . . . ? C109 N26 C107 C106 -4(2) . . . . ? C108 C106 C107 N26 0.8(18) . . . . ? C105 C106 C107 N26 179.7(11) . . . . ? Fe1 O12 C115 O13 2.4(8) 1_455 . . . ? Fe1 O12 C115 C114 -177.6(7) 1_455 . . . ? Fe1 O13 C115 O12 -2.5(8) 1_455 . . . ? Fe1 O13 C115 C114 177.4(7) 1_455 . . . ? C108 C114 C115 O12 -174.5(8) . . . . ? C109 C114 C115 O12 7.3(14) . . . . ? C108 C114 C115 O13 5.5(13) . . . . ? C109 C114 C115 O13 -172.7(9) . . . . ? C118 N27 C116 O14 176.6(17) . . . . ? C117 N27 C116 O14 -2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.062 _refine_diff_density_min -1.523 _refine_diff_density_rms 0.251 data_FeCID-5_DMF _database_code_depnum_ccdc_archive 'CCDC 901084' #TrackingRef 'web_deposit_cif_file_4_SatoshiHorike_1347458117.FeCID-5_DMF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 Fe N4 O6' _chemical_formula_weight 400.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.187(11) _cell_length_b 10.273(10) _cell_length_c 10.759(9) _cell_angle_alpha 66.69(3) _cell_angle_beta 77.57(4) _cell_angle_gamma 81.17(4) _cell_volume 1006.8(16) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.783 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8591 _exptl_absorpt_correction_T_max 0.8591 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7708 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4336 _reflns_number_gt 3530 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.1975P)^2^+3.5715P] 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 4336 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.3096 _refine_ls_wR_factor_gt 0.2804 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.38392(7) 0.43143(8) 0.40771(7) 0.0224(3) Uani 1 1 d . . . O2 O 0.4205(4) 0.6263(4) 0.6663(4) 0.0267(8) Uani 1 1 d . . . N2 N 0.4037(5) 0.6271(5) 0.2190(5) 0.0249(10) Uani 1 1 d . . . O4 O -0.1712(4) 0.5632(5) 0.5826(4) 0.0301(9) Uani 1 1 d . . . O5 O -0.2983(4) 0.6641(5) 0.7195(4) 0.0321(9) Uani 1 1 d . . . O6 O 0.3385(4) 0.5513(5) 0.5309(4) 0.0338(10) Uani 1 1 d . . . C32 C 0.0704(5) 0.6052(6) 0.6535(6) 0.0248(11) Uani 1 1 d . . . H1 H 0.0812 0.5762 0.5790 0.030 Uiso 1 1 calc R . . C1 C 0.3253(5) 0.5968(6) 0.6256(5) 0.0246(11) Uani 1 1 d . . . C29 C 0.1841(5) 0.6213(6) 0.6979(6) 0.0249(11) Uani 1 1 d . . . C30 C -0.1852(5) 0.6200(6) 0.6701(6) 0.0283(12) Uani 1 1 d . . . C31 C -0.0601(5) 0.6322(6) 0.7193(6) 0.0272(12) Uani 1 1 d . . . N3 N 0.3872(5) 1.2285(5) -0.4117(5) 0.0276(10) Uani 1 1 d . . . C13 C 0.4033(6) 0.8641(6) -0.0337(6) 0.0280(12) Uani 1 1 d . . . C14 C 0.3364(7) 0.8696(6) 0.0927(6) 0.0358(14) Uani 1 1 d . . . H2 H 0.2887 0.9548 0.0950 0.043 Uiso 1 1 calc R . . C15 C 0.3388(7) 0.7534(6) 0.2133(6) 0.0340(13) Uani 1 1 d . . . H3 H 0.2930 0.7624 0.2955 0.041 Uiso 1 1 calc R . . C16 C 0.1691(6) 0.6588(7) 0.8119(6) 0.0329(13) Uani 1 1 d . . . H4 H 0.2446 0.6711 0.8422 0.040 Uiso 1 1 calc R . . C17 C 0.4740(7) 0.7335(7) -0.0266(6) 0.0363(14) Uani 1 1 d . . . H5 H 0.5235 0.7228 -0.1069 0.044 Uiso 1 1 calc R . . C18 C 0.4815(7) 1.1200(6) -0.4040(6) 0.0343(14) Uani 1 1 d . . . H6 H 0.5456 1.1262 -0.4829 0.041 Uiso 1 1 calc R . . C19 C -0.0751(6) 0.6660(7) 0.8364(7) 0.0346(14) Uani 1 1 d . . . H7 H -0.1614 0.6805 0.8841 0.041 Uiso 1 1 calc R . . O1 O -0.0900(6) 0.7081(8) 1.0734(6) 0.0677(19) Uani 1 1 d . . . C21 C 0.4894(7) 0.9980(7) -0.2844(6) 0.0397(16) Uani 1 1 d . . . H8 H 0.5566 0.9243 -0.2847 0.048 Uiso 1 1 calc R . . C22 C 0.4710(7) 0.6206(7) 0.0982(6) 0.0352(14) Uani 1 1 d . . . H9 H 0.5185 0.5343 0.0994 0.042 Uiso 1 1 calc R . . C23 C 0.0381(6) 0.6775(8) 0.8797(6) 0.0338(14) Uani 1 1 d . . . N1 N 0.0232(6) 0.7112(9) 1.0033(7) 0.059(2) Uani 1 1 d . . . C25 C 0.3973(6) 0.9869(6) -0.1656(6) 0.0290(12) Uani 1 1 d . . . O8 O 0.1215(7) 0.7227(14) 1.0424(10) 0.134(5) Uani 1 1 d . . . C27 C 0.2993(8) 1.2159(8) -0.2993(7) 0.059(3) Uani 1 1 d . . . H10 H 0.2324 1.2906 -0.3020 0.071 Uiso 1 1 calc R . . C28 C 0.2994(9) 1.0973(9) -0.1750(8) 0.067(3) Uani 1 1 d . . . H11 H 0.2327 1.0935 -0.0985 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0123(4) 0.0295(5) 0.0218(5) -0.0075(3) -0.0016(3) 0.0010(3) O2 0.0131(17) 0.039(2) 0.0279(19) -0.0134(16) -0.0036(14) 0.0003(15) N2 0.025(2) 0.025(2) 0.022(2) -0.0068(17) -0.0036(18) 0.0004(18) O4 0.0162(18) 0.049(2) 0.034(2) -0.0245(19) -0.0046(16) -0.0025(17) O5 0.0120(17) 0.048(2) 0.038(2) -0.0197(19) -0.0031(16) 0.0004(16) O6 0.024(2) 0.051(3) 0.033(2) -0.026(2) 0.0002(17) -0.0002(18) C32 0.013(2) 0.036(3) 0.026(2) -0.014(2) 0.0012(19) -0.001(2) C1 0.016(2) 0.029(3) 0.023(2) -0.006(2) -0.0012(19) 0.0008(19) C29 0.014(2) 0.032(3) 0.027(3) -0.012(2) 0.0007(19) 0.000(2) C30 0.015(2) 0.033(3) 0.033(3) -0.008(2) -0.005(2) -0.001(2) C31 0.013(2) 0.042(3) 0.029(3) -0.018(2) 0.002(2) -0.003(2) N3 0.027(2) 0.027(2) 0.020(2) -0.0007(17) -0.0020(18) -0.0024(18) C13 0.027(3) 0.026(3) 0.026(3) -0.005(2) -0.004(2) 0.000(2) C14 0.045(4) 0.028(3) 0.031(3) -0.012(2) -0.005(3) 0.007(3) C15 0.038(3) 0.032(3) 0.027(3) -0.010(2) -0.001(2) 0.006(2) C16 0.016(3) 0.058(4) 0.032(3) -0.025(3) -0.004(2) -0.002(2) C17 0.038(3) 0.036(3) 0.025(3) -0.009(2) 0.003(2) 0.005(3) C18 0.039(3) 0.028(3) 0.024(3) -0.003(2) 0.003(2) 0.003(2) C19 0.019(3) 0.051(4) 0.037(3) -0.024(3) 0.000(2) 0.000(2) O1 0.043(3) 0.117(6) 0.055(3) -0.057(4) 0.008(3) 0.006(3) C21 0.045(4) 0.033(3) 0.026(3) -0.003(2) 0.005(3) 0.006(3) C22 0.041(3) 0.031(3) 0.024(3) -0.005(2) -0.002(2) 0.006(3) C23 0.021(3) 0.059(4) 0.028(3) -0.026(3) 0.002(2) 0.000(3) N1 0.033(3) 0.111(6) 0.054(4) -0.060(4) -0.001(3) 0.002(3) C25 0.030(3) 0.026(3) 0.026(3) -0.007(2) 0.000(2) -0.001(2) O8 0.049(4) 0.319(15) 0.123(7) -0.179(10) 0.016(4) -0.056(6) C27 0.050(4) 0.045(4) 0.036(4) 0.014(3) 0.017(3) 0.019(3) C28 0.057(5) 0.058(5) 0.035(4) 0.009(3) 0.021(3) 0.031(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 O2 2.070(4) 2_666 ? Fe1 O6 2.083(4) . ? Fe1 O4 2.140(4) 2_566 ? Fe1 N2 2.219(5) . ? Fe1 N3 2.219(5) 1_546 ? Fe1 O5 2.332(5) 2_566 ? O2 C1 1.266(7) . ? O2 Fe1 2.070(4) 2_666 ? N2 C15 1.347(7) . ? N2 C22 1.354(7) . ? O4 C30 1.264(7) . ? O4 Fe1 2.140(4) 2_566 ? O5 C30 1.258(7) . ? O5 Fe1 2.332(5) 2_566 ? O6 C1 1.254(7) . ? C32 C29 1.399(8) . ? C32 C31 1.408(7) . ? C32 H1 0.9400 . ? C1 C29 1.516(7) . ? C29 C16 1.397(8) . ? C30 C31 1.521(8) . ? C31 C19 1.407(8) . ? N3 C27 1.314(8) . ? N3 C18 1.343(8) . ? N3 Fe1 2.219(5) 1_564 ? C13 C14 1.403(8) . ? C13 C17 1.404(8) . ? C13 C25 1.485(8) . ? C14 C15 1.374(8) . ? C14 H2 0.9400 . ? C15 H3 0.9400 . ? C16 C23 1.401(8) . ? C16 H4 0.9400 . ? C17 C22 1.382(8) . ? C17 H5 0.9400 . ? C18 C21 1.404(8) . ? C18 H6 0.9400 . ? C19 C23 1.370(9) . ? C19 H7 0.9400 . ? O1 N1 1.231(8) . ? C21 C25 1.389(8) . ? C21 H8 0.9400 . ? C22 H9 0.9400 . ? C23 N1 1.474(8) . ? N1 O8 1.205(9) . ? C25 C28 1.376(9) . ? C27 C28 1.409(9) . ? C27 H10 0.9400 . ? C28 H11 0.9400 . ? 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 O2 Fe1 O6 122.87(17) 2_666 . ? O2 Fe1 O4 150.22(17) 2_666 2_566 ? O6 Fe1 O4 86.85(16) . 2_566 ? O2 Fe1 N2 85.50(17) 2_666 . ? O6 Fe1 N2 91.09(19) . . ? O4 Fe1 N2 92.59(18) 2_566 . ? O2 Fe1 N3 88.21(18) 2_666 1_546 ? O6 Fe1 N3 92.3(2) . 1_546 ? O4 Fe1 N3 92.89(18) 2_566 1_546 ? N2 Fe1 N3 173.71(17) . 1_546 ? O2 Fe1 O5 91.11(16) 2_666 2_566 ? O6 Fe1 O5 145.61(16) . 2_566 ? O4 Fe1 O5 59.11(15) 2_566 2_566 ? N2 Fe1 O5 86.08(18) . 2_566 ? N3 Fe1 O5 94.08(19) 1_546 2_566 ? C1 O2 Fe1 118.0(4) . 2_666 ? C15 N2 C22 116.2(5) . . ? C15 N2 Fe1 123.1(4) . . ? C22 N2 Fe1 120.3(4) . . ? C30 O4 Fe1 93.3(3) . 2_566 ? C30 O5 Fe1 84.8(4) . 2_566 ? C1 O6 Fe1 165.6(4) . . ? C29 C32 C31 120.5(5) . . ? C29 C32 H1 119.7 . . ? C31 C32 H1 119.7 . . ? O2 C1 O6 125.6(5) . . ? O2 C1 C29 116.0(5) . . ? O6 C1 C29 118.4(5) . . ? C32 C29 C16 120.1(5) . . ? C32 C29 C1 121.2(5) . . ? C16 C29 C1 118.7(5) . . ? O5 C30 O4 122.7(5) . . ? O5 C30 C31 119.0(5) . . ? O4 C30 C31 118.3(5) . . ? C19 C31 C32 119.2(5) . . ? C19 C31 C30 119.2(5) . . ? C32 C31 C30 121.5(5) . . ? C27 N3 C18 116.4(5) . . ? C27 N3 Fe1 119.0(4) . 1_564 ? C18 N3 Fe1 124.3(4) . 1_564 ? C14 C13 C17 115.1(5) . . ? C14 C13 C25 122.2(5) . . ? C17 C13 C25 122.6(5) . . ? C15 C14 C13 121.5(6) . . ? C15 C14 H2 119.2 . . ? C13 C14 H2 119.2 . . ? N2 C15 C14 123.0(5) . . ? N2 C15 H3 118.5 . . ? C14 C15 H3 118.5 . . ? C29 C16 C23 118.0(5) . . ? C29 C16 H4 121.0 . . ? C23 C16 H4 121.0 . . ? C22 C17 C13 120.1(5) . . ? C22 C17 H5 119.9 . . ? C13 C17 H5 119.9 . . ? N3 C18 C21 123.5(5) . . ? N3 C18 H6 118.2 . . ? C21 C18 H6 118.2 . . ? C23 C19 C31 118.8(5) . . ? C23 C19 H7 120.6 . . ? C31 C19 H7 120.6 . . ? C25 C21 C18 119.5(6) . . ? C25 C21 H8 120.2 . . ? C18 C21 H8 120.2 . . ? N2 C22 C17 123.9(6) . . ? N2 C22 H9 118.1 . . ? C17 C22 H9 118.1 . . ? C19 C23 C16 123.1(6) . . ? C19 C23 N1 119.2(5) . . ? C16 C23 N1 117.7(6) . . ? O8 N1 O1 121.7(6) . . ? O8 N1 C23 120.1(6) . . ? O1 N1 C23 117.5(6) . . ? C28 C25 C21 116.6(5) . . ? C28 C25 C13 121.0(5) . . ? C21 C25 C13 122.5(5) . . ? N3 C27 C28 123.9(6) . . ? N3 C27 H10 118.1 . . ? C28 C27 H10 118.1 . . ? C25 C28 C27 120.0(6) . . ? C25 C28 H11 120.0 . . ? C27 C28 H11 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 N2 C15 -149.5(5) 2_666 . . . ? O6 Fe1 N2 C15 -26.7(5) . . . . ? O4 Fe1 N2 C15 60.2(5) 2_566 . . . ? N3 Fe1 N2 C15 -149.2(15) 1_546 . . . ? O5 Fe1 N2 C15 119.0(5) 2_566 . . . ? O2 Fe1 N2 C22 38.1(5) 2_666 . . . ? O6 Fe1 N2 C22 161.0(5) . . . . ? O4 Fe1 N2 C22 -112.1(5) 2_566 . . . ? N3 Fe1 N2 C22 38.5(18) 1_546 . . . ? O5 Fe1 N2 C22 -53.3(5) 2_566 . . . ? O2 Fe1 O6 C1 -64.1(16) 2_666 . . . ? O4 Fe1 O6 C1 118.0(16) 2_566 . . . ? N2 Fe1 O6 C1 -149.4(16) . . . . ? N3 Fe1 O6 C1 25.3(16) 1_546 . . . ? O5 Fe1 O6 C1 125.9(15) 2_566 . . . ? Fe1 O2 C1 O6 -9.5(7) 2_666 . . . ? Fe1 O2 C1 C29 171.3(3) 2_666 . . . ? Fe1 O6 C1 O2 66.3(18) . . . . ? Fe1 O6 C1 C29 -114.5(15) . . . . ? C31 C32 C29 C16 2.6(9) . . . . ? C31 C32 C29 C1 -178.2(5) . . . . ? O2 C1 C29 C32 174.0(5) . . . . ? O6 C1 C29 C32 -5.2(8) . . . . ? O2 C1 C29 C16 -6.8(8) . . . . ? O6 C1 C29 C16 174.0(5) . . . . ? Fe1 O5 C30 O4 4.3(6) 2_566 . . . ? Fe1 O5 C30 C31 -174.3(5) 2_566 . . . ? Fe1 O4 C30 O5 -4.6(6) 2_566 . . . ? Fe1 O4 C30 C31 174.0(5) 2_566 . . . ? C29 C32 C31 C19 -4.4(9) . . . . ? C29 C32 C31 C30 178.0(5) . . . . ? O5 C30 C31 C19 12.2(9) . . . . ? O4 C30 C31 C19 -166.4(6) . . . . ? O5 C30 C31 C32 -170.2(5) . . . . ? O4 C30 C31 C32 11.2(9) . . . . ? C17 C13 C14 C15 -1.3(10) . . . . ? C25 C13 C14 C15 177.5(6) . . . . ? C22 N2 C15 C14 1.7(10) . . . . ? Fe1 N2 C15 C14 -170.9(5) . . . . ? C13 C14 C15 N2 -0.5(11) . . . . ? C32 C29 C16 C23 0.8(9) . . . . ? C1 C29 C16 C23 -178.4(6) . . . . ? C14 C13 C17 C22 1.8(10) . . . . ? C25 C13 C17 C22 -176.9(6) . . . . ? C27 N3 C18 C21 0.0(11) . . . . ? Fe1 N3 C18 C21 173.7(5) 1_564 . . . ? C32 C31 C19 C23 2.7(10) . . . . ? C30 C31 C19 C23 -179.7(6) . . . . ? N3 C18 C21 C25 -1.0(11) . . . . ? C15 N2 C22 C17 -1.0(10) . . . . ? Fe1 N2 C22 C17 171.8(6) . . . . ? C13 C17 C22 N2 -0.7(11) . . . . ? C31 C19 C23 C16 0.8(11) . . . . ? C31 C19 C23 N1 -179.3(7) . . . . ? C29 C16 C23 C19 -2.6(11) . . . . ? C29 C16 C23 N1 177.5(6) . . . . ? C19 C23 N1 O8 -179.5(10) . . . . ? C16 C23 N1 O8 0.4(14) . . . . ? C19 C23 N1 O1 10.0(12) . . . . ? C16 C23 N1 O1 -170.1(8) . . . . ? C18 C21 C25 C28 2.1(11) . . . . ? C18 C21 C25 C13 -177.2(6) . . . . ? C14 C13 C25 C28 -17.1(11) . . . . ? C17 C13 C25 C28 161.6(8) . . . . ? C14 C13 C25 C21 162.1(7) . . . . ? C17 C13 C25 C21 -19.2(10) . . . . ? C18 N3 C27 C28 -0.2(14) . . . . ? Fe1 N3 C27 C28 -174.2(8) 1_564 . . . ? C21 C25 C28 C27 -2.3(14) . . . . ? C13 C25 C28 C27 177.0(9) . . . . ? N3 C27 C28 C25 1.4(17) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 2.820 _refine_diff_density_min -1.730 _refine_diff_density_rms 0.316 data_FeCID-6_DMF _database_code_depnum_ccdc_archive 'CCDC 901085' #TrackingRef 'web_deposit_cif_file_5_SatoshiHorike_1347458117.FeCID-6_DMF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 Fe N2 O6' _chemical_formula_weight 435.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.034(3) _cell_length_b 10.250(3) _cell_length_c 10.487(3) _cell_angle_alpha 67.006(17) _cell_angle_beta 75.61(2) _cell_angle_gamma 77.56(2) _cell_volume 953.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8513 _exptl_absorpt_correction_T_max 0.8513 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7777 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4201 _reflns_number_gt 3524 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction yadokari _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^)+(0.1337P)^2^+4.6295P] 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 4201 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.2596 _refine_ls_wR_factor_gt 0.2482 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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 0.60916(7) 0.06749(8) 0.58865(7) 0.0130(3) Uani 1 1 d . . . O2 O 1.3411(4) 0.0541(4) 0.5373(4) 0.0218(8) Uani 1 1 d . . . N10 N 0.5926(5) 0.8726(5) -0.2248(5) 0.0189(9) Uani 1 1 d . . . O4 O 1.4081(4) 0.1391(4) 0.6721(4) 0.0194(8) Uani 1 1 d . . . O5 O 0.8278(4) 0.0497(5) 0.5875(5) 0.0246(9) Uani 1 1 d . . . C6 C 0.5977(6) 0.6310(6) 0.0254(6) 0.0183(11) Uani 1 1 d . . . O7 O 0.6830(4) 0.1652(5) 0.7143(4) 0.0235(9) Uani 1 1 d . . . C28 C 0.6051(6) 0.5047(6) 0.1562(6) 0.0191(11) Uani 1 1 d . . . N9 N 0.6130(5) 0.2624(5) 0.4044(5) 0.0192(9) Uani 1 1 d . . . C10 C 0.5268(7) 0.8792(6) -0.0991(6) 0.0260(13) Uani 1 1 d . . . H1 H 0.4770 0.9672 -0.0961 0.031 Uiso 1 1 calc R . . C11 C 1.1675(5) 0.1275(6) 0.7060(5) 0.0154(10) Uani 1 1 d . . . C12 C 0.5256(6) 0.3820(6) 0.4023(6) 0.0248(12) Uani 1 1 d . . . H2 H 0.4656 0.3828 0.4866 0.030 Uiso 1 1 calc R . . C13 C 1.3152(5) 0.1049(6) 0.6338(5) 0.0166(10) Uani 1 1 d . . . C14 C 0.8049(6) 0.1156(6) 0.6713(6) 0.0180(10) Uani 1 1 d . . . C15 C 0.6975(6) 0.3818(7) 0.1593(6) 0.0281(13) Uani 1 1 d . . . H3 H 0.7592 0.3777 0.0768 0.034 Uiso 1 1 calc R . . C16 C 0.8971(6) 0.1736(7) 0.8409(6) 0.0263(13) Uani 1 1 d . . . H4 H 0.8051 0.1903 0.8859 0.032 Uiso 1 1 calc R . . C17 C 1.0601(6) 0.1060(6) 0.6578(6) 0.0180(10) Uani 1 1 d . . . H5 H 1.0787 0.0739 0.5818 0.022 Uiso 1 1 calc R . . O8 O 0.9664(5) 0.2279(7) 1.0085(6) 0.0485(16) Uani 1 1 d . . . C19 C 0.9235(6) 0.1329(6) 0.7246(6) 0.0206(11) Uani 1 1 d . . . C20 C 0.5185(7) 0.5033(6) 0.2847(6) 0.0246(12) Uani 1 1 d . . . H6 H 0.4563 0.5847 0.2899 0.029 Uiso 1 1 calc R . . C21 C 0.6987(6) 0.2655(6) 0.2835(6) 0.0268(13) Uani 1 1 d . . . H7 H 0.7631 0.1841 0.2830 0.032 Uiso 1 1 calc R . . C22 C 0.6625(7) 0.6228(6) -0.1054(6) 0.0242(12) Uani 1 1 d . . . H8 H 0.7087 0.5350 -0.1122 0.029 Uiso 1 1 calc R . . C23 C 0.5278(7) 0.7646(6) 0.0260(6) 0.0254(13) Uani 1 1 d . . . H9 H 0.4817 0.7761 0.1114 0.030 Uiso 1 1 calc R . . C24 C 0.6587(6) 0.7447(6) -0.2258(6) 0.0224(12) Uani 1 1 d . . . H10 H 0.7051 0.7370 -0.3127 0.027 Uiso 1 1 calc R . . C25 C 1.0049(6) 0.1899(8) 0.8912(7) 0.0276(14) Uani 1 1 d . . . C26 C 1.1412(6) 0.1695(7) 0.8230(6) 0.0243(12) Uani 1 1 d . . . H11 H 1.2146 0.1838 0.8549 0.029 Uiso 1 1 calc R . . C27 C 1.0731(8) 0.2559(11) 1.0586(9) 0.048(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 0.0104(4) 0.0164(4) 0.0116(4) -0.0056(3) -0.0004(3) -0.0014(3) O2 0.019(2) 0.030(2) 0.0197(19) -0.0167(17) 0.0032(15) -0.0013(16) N10 0.023(2) 0.018(2) 0.016(2) -0.0053(17) -0.0043(18) -0.0016(18) O4 0.0099(17) 0.028(2) 0.0209(19) -0.0118(16) 0.0002(14) -0.0026(15) O5 0.0155(19) 0.038(2) 0.030(2) -0.0232(19) -0.0047(16) -0.0006(17) C6 0.017(3) 0.020(3) 0.017(2) -0.006(2) -0.001(2) -0.004(2) O7 0.0134(19) 0.034(2) 0.028(2) -0.0184(18) -0.0040(16) 0.0013(16) C28 0.016(3) 0.020(3) 0.017(2) -0.004(2) 0.001(2) -0.003(2) N9 0.020(2) 0.018(2) 0.017(2) -0.0018(17) -0.0027(18) -0.0047(18) C10 0.035(3) 0.022(3) 0.017(3) -0.008(2) -0.002(2) 0.002(2) C11 0.009(2) 0.021(2) 0.016(2) -0.009(2) -0.0002(18) -0.0003(19) C12 0.028(3) 0.024(3) 0.018(3) -0.007(2) 0.000(2) -0.001(2) C13 0.014(2) 0.019(2) 0.014(2) -0.0047(19) -0.0023(19) -0.0011(19) C14 0.016(3) 0.021(3) 0.018(2) -0.007(2) -0.003(2) -0.003(2) C15 0.025(3) 0.025(3) 0.022(3) -0.005(2) 0.005(2) 0.003(2) C16 0.014(3) 0.045(4) 0.027(3) -0.024(3) 0.001(2) -0.001(2) C17 0.015(2) 0.024(3) 0.016(2) -0.010(2) -0.0022(19) 0.000(2) O8 0.017(2) 0.107(5) 0.050(3) -0.064(3) 0.002(2) -0.007(3) C19 0.013(2) 0.027(3) 0.024(3) -0.012(2) -0.003(2) -0.002(2) C20 0.031(3) 0.019(3) 0.017(3) -0.007(2) 0.002(2) 0.001(2) C21 0.023(3) 0.021(3) 0.022(3) -0.001(2) 0.005(2) 0.002(2) C22 0.031(3) 0.021(3) 0.017(3) -0.007(2) -0.003(2) 0.001(2) C23 0.031(3) 0.025(3) 0.012(2) -0.006(2) 0.001(2) 0.004(2) C24 0.026(3) 0.023(3) 0.015(2) -0.007(2) -0.002(2) 0.003(2) C25 0.015(3) 0.050(4) 0.030(3) -0.032(3) 0.000(2) -0.002(3) C26 0.017(3) 0.040(3) 0.024(3) -0.019(3) -0.006(2) -0.003(2) C27 0.029(4) 0.094(7) 0.051(5) -0.059(5) -0.006(3) -0.007(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 O2 2.059(4) 2_756 ? Fe1 O4 2.089(4) 1_455 ? Fe1 O5 2.159(4) . ? Fe1 N9 2.169(5) . ? Fe1 N10 2.185(5) 1_546 ? Fe1 O7 2.264(4) . ? O2 C13 1.259(6) . ? O2 Fe1 2.059(4) 2_756 ? N10 C10 1.340(7) . ? N10 C24 1.338(7) . ? N10 Fe1 2.185(5) 1_564 ? O4 C13 1.260(7) . ? O4 Fe1 2.089(4) 1_655 ? O5 C14 1.255(7) . ? C6 C22 1.391(7) . ? C6 C23 1.399(8) . ? C6 C28 1.478(7) . ? O7 C14 1.263(7) . ? C28 C15 1.389(8) . ? C28 C20 1.407(7) . ? N9 C21 1.337(7) . ? N9 C12 1.341(7) . ? C10 C23 1.378(8) . ? C10 H1 0.9400 . ? C11 C17 1.388(8) . ? C11 C26 1.402(7) . ? C11 C13 1.502(7) . ? C12 C20 1.371(8) . ? C12 H2 0.9400 . ? C14 C19 1.504(8) . ? C15 C21 1.381(8) . ? C15 H3 0.9400 . ? C16 C19 1.386(8) . ? C16 C25 1.380(9) . ? C16 H4 0.9400 . ? C17 C19 1.398(7) . ? C17 H5 0.9400 . ? O8 C25 1.373(7) . ? O8 C27 1.426(8) . ? C20 H6 0.9400 . ? C21 H7 0.9400 . ? C22 C24 1.389(8) . ? C22 H8 0.9400 . ? C23 H9 0.9400 . ? C24 H10 0.9400 . ? C25 C26 1.390(8) . ? C26 H11 0.9400 . ? 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 O2 Fe1 O4 125.41(16) 2_756 1_455 ? O2 Fe1 O5 88.63(16) 2_756 . ? O4 Fe1 O5 145.73(16) 1_455 . ? O2 Fe1 N9 90.72(18) 2_756 . ? O4 Fe1 N9 90.74(17) 1_455 . ? O5 Fe1 N9 92.92(18) . . ? O2 Fe1 N10 89.63(17) 2_756 1_546 ? O4 Fe1 N10 86.44(17) 1_455 1_546 ? O5 Fe1 N10 90.30(18) . 1_546 ? N9 Fe1 N10 176.77(18) . 1_546 ? O2 Fe1 O7 147.92(16) 2_756 . ? O4 Fe1 O7 86.41(15) 1_455 . ? O5 Fe1 O7 59.37(14) . . ? N9 Fe1 O7 93.03(17) . . ? N10 Fe1 O7 88.36(17) 1_546 . ? C13 O2 Fe1 168.5(4) . 2_756 ? C10 N10 C24 116.5(5) . . ? C10 N10 Fe1 120.4(4) . 1_564 ? C24 N10 Fe1 122.7(4) . 1_564 ? C13 O4 Fe1 113.3(3) . 1_655 ? C14 O5 Fe1 92.2(3) . . ? C22 C6 C23 116.5(5) . . ? C22 C6 C28 121.1(5) . . ? C23 C6 C28 122.4(5) . . ? C14 O7 Fe1 87.3(3) . . ? C15 C28 C20 116.5(5) . . ? C15 C28 C6 122.1(5) . . ? C20 C28 C6 121.4(5) . . ? C21 N9 C12 116.6(5) . . ? C21 N9 Fe1 120.7(4) . . ? C12 N9 Fe1 122.7(4) . . ? N10 C10 C23 123.8(5) . . ? N10 C10 H1 118.1 . . ? C23 C10 H1 118.1 . . ? C17 C11 C26 121.1(5) . . ? C17 C11 C13 120.4(5) . . ? C26 C11 C13 118.5(5) . . ? N9 C12 C20 124.0(5) . . ? N9 C12 H2 118.0 . . ? C20 C12 H2 118.0 . . ? O2 C13 O4 122.9(5) . . ? O2 C13 C11 118.9(5) . . ? O4 C13 C11 118.2(5) . . ? O5 C14 O7 121.1(5) . . ? O5 C14 C19 119.8(5) . . ? O7 C14 C19 119.1(5) . . ? C28 C15 C21 120.0(5) . . ? C28 C15 H3 120.0 . . ? C21 C15 H3 120.0 . . ? C19 C16 C25 120.6(5) . . ? C19 C16 H4 119.7 . . ? C25 C16 H4 119.7 . . ? C11 C17 C19 118.7(5) . . ? C11 C17 H5 120.6 . . ? C19 C17 H5 120.6 . . ? C25 O8 C27 117.5(5) . . ? C16 C19 C17 120.3(5) . . ? C16 C19 C14 119.9(5) . . ? C17 C19 C14 119.8(5) . . ? C12 C20 C28 119.4(5) . . ? C12 C20 H6 120.3 . . ? C28 C20 H6 120.3 . . ? N9 C21 C15 123.5(5) . . ? N9 C21 H7 118.2 . . ? C15 C21 H7 118.2 . . ? C6 C22 C24 119.8(5) . . ? C6 C22 H8 120.1 . . ? C24 C22 H8 120.1 . . ? C10 C23 C6 119.8(5) . . ? C10 C23 H9 120.1 . . ? C6 C23 H9 120.1 . . ? N10 C24 C22 123.5(5) . . ? N10 C24 H10 118.2 . . ? C22 C24 H10 118.2 . . ? O8 C25 C16 115.4(5) . . ? O8 C25 C26 124.4(5) . . ? C16 C25 C26 120.2(5) . . ? C25 C26 C11 119.1(5) . . ? C25 C26 H11 120.5 . . ? C11 C26 H11 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 O5 C14 -176.2(4) 2_756 . . . ? O4 Fe1 O5 C14 -2.4(5) 1_455 . . . ? N9 Fe1 O5 C14 93.2(4) . . . . ? N10 Fe1 O5 C14 -86.5(4) 1_546 . . . ? O7 Fe1 O5 C14 1.4(3) . . . . ? O2 Fe1 O7 C14 3.2(5) 2_756 . . . ? O4 Fe1 O7 C14 176.5(3) 1_455 . . . ? O5 Fe1 O7 C14 -1.4(3) . . . . ? N9 Fe1 O7 C14 -93.0(3) . . . . ? N10 Fe1 O7 C14 89.9(3) 1_546 . . . ? C22 C6 C28 C15 13.0(9) . . . . ? C23 C6 C28 C15 -166.0(6) . . . . ? C22 C6 C28 C20 -167.2(6) . . . . ? C23 C6 C28 C20 13.8(9) . . . . ? O2 Fe1 N9 C21 -31.5(5) 2_756 . . . ? O4 Fe1 N9 C21 -157.0(5) 1_455 . . . ? O5 Fe1 N9 C21 57.1(5) . . . . ? N10 Fe1 N9 C21 -128(3) 1_546 . . . ? O7 Fe1 N9 C21 116.6(5) . . . . ? O2 Fe1 N9 C12 144.3(5) 2_756 . . . ? O4 Fe1 N9 C12 18.9(5) 1_455 . . . ? O5 Fe1 N9 C12 -127.0(5) . . . . ? N10 Fe1 N9 C12 48(3) 1_546 . . . ? O7 Fe1 N9 C12 -67.6(5) . . . . ? C24 N10 C10 C23 2.1(9) . . . . ? Fe1 N10 C10 C23 -171.0(5) 1_564 . . . ? C21 N9 C12 C20 1.1(9) . . . . ? Fe1 N9 C12 C20 -174.9(5) . . . . ? Fe1 O2 C13 O4 86(2) 2_756 . . . ? Fe1 O2 C13 C11 -94.8(19) 2_756 . . . ? Fe1 O4 C13 O2 -11.1(7) 1_655 . . . ? Fe1 O4 C13 C11 169.5(4) 1_655 . . . ? C17 C11 C13 O2 -6.3(8) . . . . ? C26 C11 C13 O2 173.3(5) . . . . ? C17 C11 C13 O4 173.1(5) . . . . ? C26 C11 C13 O4 -7.3(8) . . . . ? Fe1 O5 C14 O7 -2.5(6) . . . . ? Fe1 O5 C14 C19 176.0(4) . . . . ? Fe1 O7 C14 O5 2.4(5) . . . . ? Fe1 O7 C14 C19 -176.1(5) . . . . ? C20 C28 C15 C21 1.4(9) . . . . ? C6 C28 C15 C21 -178.8(6) . . . . ? C26 C11 C17 C19 2.7(8) . . . . ? C13 C11 C17 C19 -177.7(5) . . . . ? C25 C16 C19 C17 0.8(10) . . . . ? C25 C16 C19 C14 179.9(6) . . . . ? C11 C17 C19 C16 -3.1(9) . . . . ? C11 C17 C19 C14 177.8(5) . . . . ? O5 C14 C19 C16 -164.4(6) . . . . ? O7 C14 C19 C16 14.1(8) . . . . ? O5 C14 C19 C17 14.7(8) . . . . ? O7 C14 C19 C17 -166.8(5) . . . . ? N9 C12 C20 C28 1.2(10) . . . . ? C15 C28 C20 C12 -2.4(9) . . . . ? C6 C28 C20 C12 177.8(6) . . . . ? C12 N9 C21 C15 -2.1(10) . . . . ? Fe1 N9 C21 C15 173.9(5) . . . . ? C28 C15 C21 N9 0.9(11) . . . . ? C23 C6 C22 C24 1.8(9) . . . . ? C28 C6 C22 C24 -177.3(5) . . . . ? N10 C10 C23 C6 -1.7(10) . . . . ? C22 C6 C23 C10 -0.4(9) . . . . ? C28 C6 C23 C10 178.7(6) . . . . ? C10 N10 C24 C22 -0.5(9) . . . . ? Fe1 N10 C24 C22 172.4(5) 1_564 . . . ? C6 C22 C24 N10 -1.5(10) . . . . ? C27 O8 C25 C16 -175.6(7) . . . . ? C27 O8 C25 C26 3.6(12) . . . . ? C19 C16 C25 O8 -178.8(6) . . . . ? C19 C16 C25 C26 1.9(11) . . . . ? O8 C25 C26 C11 178.5(7) . . . . ? C16 C25 C26 C11 -2.3(10) . . . . ? C17 C11 C26 C25 0.0(9) . . . . ? C13 C11 C26 C25 -179.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 3.036 _refine_diff_density_min -0.529 _refine_diff_density_rms 0.186