# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zdenek.travnicek@upol.c _publ_contact_author_name 'Zdenek Travnicek' loop_ _publ_author_name R.Herchel L.Pavelek Z.Travnicek data_r1 _database_code_depnum_ccdc_archive 'CCDC 830415' #TrackingRef 'dt-art-06-2011-011127-File009-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C102 H84 Fe4 N24 O15' _chemical_formula_weight 2109.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 28.6227(9) _cell_length_b 21.7750(7) _cell_length_c 8.2850(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5163.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11382 _cell_measurement_theta_min 2.9811 _cell_measurement_theta_max 33.3910 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.625 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8594 _exptl_absorpt_correction_T_max 0.9401 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32754 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4535 _reflns_number_gt 3396 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1087P)^2^+2.9037P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4535 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1611 _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 0.533259(18) 0.38316(2) 0.33334(6) 0.01103(19) Uani 1 1 d . . . O2 O 0.49033(9) 0.38907(11) 0.5121(3) 0.0150(6) Uani 1 1 d . . . O1 O 0.57667(9) 0.45012(11) 0.3651(3) 0.0150(6) Uani 1 1 d . . . O3 O 0.57137(8) 0.32173(11) 0.4412(3) 0.0131(6) Uani 1 1 d . . . N2 N 0.49127(11) 0.31298(14) 0.2368(4) 0.0142(7) Uani 1 1 d . . . N1 N 0.56759(11) 0.36455(14) 0.1143(4) 0.0138(7) Uani 1 1 d . . . N3 N 0.48469(11) 0.44598(14) 0.2106(4) 0.0150(7) Uani 1 1 d . . . N4 N 0.46910(12) 0.44184(16) 0.0518(4) 0.0227(8) Uani 1 1 d . . . N5 N 0.42859(11) 0.51204(14) 0.1808(4) 0.0138(7) Uani 1 1 d . . . N6 N 0.39146(11) 0.55291(14) 0.2139(4) 0.0147(7) Uani 1 1 d . . . C1 C 0.44854(13) 0.36538(17) 0.5339(5) 0.0154(8) Uani 1 1 d . . . C2 C 0.42441(14) 0.37900(18) 0.6773(5) 0.0205(9) Uani 1 1 d . . . H2A H 0.4388 0.4045 0.7558 0.025 Uiso 1 1 calc R . . C3 C 0.38006(15) 0.3561(2) 0.7067(5) 0.0268(10) Uani 1 1 d . . . H3A H 0.3645 0.3661 0.8045 0.032 Uiso 1 1 calc R . . C4 C 0.35825(15) 0.3187(2) 0.5948(6) 0.0295(10) Uani 1 1 d . . . H4A H 0.3276 0.3038 0.6148 0.035 Uiso 1 1 calc R . . C5 C 0.38091(14) 0.3034(2) 0.4547(5) 0.0250(10) Uani 1 1 d . . . H5A H 0.3658 0.2776 0.3784 0.030 Uiso 1 1 calc R . . C6 C 0.42639(13) 0.32530(17) 0.4220(4) 0.0165(8) Uani 1 1 d . . . C7 C 0.44959(13) 0.30018(17) 0.2804(5) 0.0163(8) Uani 1 1 d . . . H7A H 0.4324 0.2721 0.2155 0.020 Uiso 1 1 calc R . . C8 C 0.51368(14) 0.27951(18) 0.1032(5) 0.0190(8) Uani 1 1 d . . . H8A H 0.4896 0.2599 0.0347 0.023 Uiso 1 1 calc R . . H8B H 0.5342 0.2469 0.1467 0.023 Uiso 1 1 calc R . . C9 C 0.54228(13) 0.32459(18) 0.0031(5) 0.0171(8) Uani 1 1 d . . . H9A H 0.5645 0.3021 -0.0666 0.020 Uiso 1 1 calc R . . H9B H 0.5214 0.3493 -0.0668 0.020 Uiso 1 1 calc R . . C11 C 0.62111(13) 0.45251(17) 0.3195(5) 0.0143(8) Uani 1 1 d . . . C12 C 0.65124(14) 0.49357(18) 0.3977(5) 0.0196(9) Uani 1 1 d . . . H12A H 0.6393 0.5195 0.4803 0.023 Uiso 1 1 calc R . . C13 C 0.69803(15) 0.4971(2) 0.3566(5) 0.0261(10) Uani 1 1 d . . . H13A H 0.7178 0.5248 0.4127 0.031 Uiso 1 1 calc R . . C14 C 0.71653(15) 0.4605(2) 0.2342(5) 0.0267(10) Uani 1 1 d . . . H14A H 0.7487 0.4630 0.2066 0.032 Uiso 1 1 calc R . . C15 C 0.68712(14) 0.4205(2) 0.1540(5) 0.0225(9) Uani 1 1 d . . . H15A H 0.6995 0.3958 0.0698 0.027 Uiso 1 1 calc R . . C16 C 0.63964(13) 0.41539(17) 0.1930(4) 0.0158(8) Uani 1 1 d . . . C17 C 0.61150(13) 0.37444(16) 0.0951(5) 0.0150(8) Uani 1 1 d . . . H17A H 0.6268 0.3532 0.0099 0.018 Uiso 1 1 calc R . . C18 C 0.43522(15) 0.48176(19) 0.0384(5) 0.0230(9) Uani 1 1 d . . . H18A H 0.4177 0.4887 -0.0572 0.028 Uiso 1 1 calc R . . C19 C 0.45975(13) 0.48756(17) 0.2847(5) 0.0144(8) Uani 1 1 d . . . H19A H 0.4630 0.4988 0.3949 0.017 Uiso 1 1 calc R . . C20 C 0.61383(12) 0.32029(16) 0.5003(4) 0.0116(8) Uani 1 1 d . . . C21 C 0.64661(12) 0.27790(16) 0.4370(5) 0.0139(8) Uani 1 1 d . . . H21A H 0.6377 0.2513 0.3515 0.017 Uiso 1 1 calc R . . C22 C 0.69145(13) 0.27492(17) 0.4989(5) 0.0167(8) Uani 1 1 d . . . H22A H 0.7126 0.2454 0.4570 0.020 Uiso 1 1 calc R . . C23 C 0.70627(13) 0.31439(17) 0.6215(5) 0.0166(8) Uani 1 1 d . . . H23A H 0.7373 0.3122 0.6618 0.020 Uiso 1 1 calc R . . C24 C 0.67511(13) 0.35644(17) 0.6830(4) 0.0140(8) Uani 1 1 d . . . H24A H 0.6851 0.3841 0.7646 0.017 Uiso 1 1 calc R . . C25 C 0.62869(13) 0.35930(16) 0.6274(4) 0.0127(8) Uani 1 1 d . . . C26 C 0.40450(13) 0.59669(16) 0.3102(4) 0.0125(8) Uani 1 1 d . . . H26A H 0.4380 0.6020 0.3413 0.050 Uiso 1 1 d . . . O4 O 0.8215(6) 0.5750(9) 0.369(2) 0.156(6) Uiso 0.50 1 d P . . C27 C 0.7870(6) 0.6267(8) 0.386(2) 0.090(5) Uiso 0.50 1 d P . . O5 O 0.7581(6) 0.6833(8) 0.6439(19) 0.058(4) Uiso 0.25 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0122(3) 0.0096(3) 0.0113(3) -0.0007(2) -0.0005(2) 0.0023(2) O2 0.0121(14) 0.0188(14) 0.0140(13) -0.0026(11) 0.0004(11) 0.0022(10) O1 0.0147(14) 0.0127(13) 0.0175(14) 0.0000(11) 0.0000(11) 0.0004(10) O3 0.0120(14) 0.0107(13) 0.0167(13) 0.0010(11) -0.0015(10) 0.0014(10) N2 0.0158(17) 0.0131(16) 0.0138(16) -0.0016(13) 0.0004(13) 0.0021(12) N1 0.0180(18) 0.0108(15) 0.0124(15) 0.0011(13) 0.0003(13) 0.0015(12) N3 0.0188(17) 0.0122(16) 0.0140(16) -0.0009(13) -0.0013(13) 0.0029(13) N4 0.032(2) 0.0239(19) 0.0119(17) -0.0027(14) -0.0052(15) 0.0138(15) N5 0.0147(17) 0.0125(16) 0.0141(16) -0.0014(13) -0.0021(13) 0.0069(12) N6 0.0159(17) 0.0120(16) 0.0161(17) -0.0024(13) -0.0009(13) 0.0052(12) C1 0.0137(19) 0.0157(19) 0.017(2) 0.0035(16) -0.0007(16) 0.0071(15) C2 0.024(2) 0.019(2) 0.018(2) -0.0004(17) 0.0026(17) 0.0049(16) C3 0.025(2) 0.029(2) 0.026(2) 0.0009(19) 0.0116(19) 0.0076(19) C4 0.017(2) 0.036(3) 0.036(3) 0.003(2) 0.0093(19) 0.0006(18) C5 0.017(2) 0.030(2) 0.028(2) 0.0000(19) -0.0006(18) 0.0005(17) C6 0.014(2) 0.020(2) 0.016(2) 0.0014(16) -0.0007(16) 0.0025(15) C7 0.016(2) 0.017(2) 0.016(2) -0.0024(16) -0.0031(16) -0.0005(15) C8 0.022(2) 0.017(2) 0.018(2) -0.0068(17) 0.0034(17) 0.0001(16) C9 0.021(2) 0.017(2) 0.0128(19) -0.0022(16) -0.0018(16) 0.0022(15) C11 0.016(2) 0.0124(19) 0.0144(19) 0.0072(15) -0.0033(15) 0.0023(15) C12 0.022(2) 0.016(2) 0.021(2) 0.0023(17) -0.0015(17) -0.0007(15) C13 0.023(2) 0.026(2) 0.030(2) 0.0018(19) -0.0049(19) -0.0048(18) C14 0.015(2) 0.034(3) 0.031(2) 0.006(2) 0.0014(19) -0.0019(18) C15 0.019(2) 0.026(2) 0.023(2) 0.0052(18) 0.0018(17) 0.0043(17) C16 0.017(2) 0.015(2) 0.0151(19) 0.0066(16) -0.0013(16) 0.0046(15) C17 0.019(2) 0.0123(19) 0.014(2) 0.0032(15) 0.0028(16) 0.0059(14) C18 0.032(2) 0.022(2) 0.015(2) -0.0055(17) -0.0073(18) 0.0114(18) C19 0.016(2) 0.0140(19) 0.0126(19) -0.0023(15) -0.0029(15) 0.0025(15) C20 0.0105(18) 0.0088(17) 0.0156(19) 0.0041(14) 0.0015(15) 0.0005(13) C21 0.0137(19) 0.0103(18) 0.018(2) -0.0003(15) 0.0030(15) 0.0001(14) C22 0.0143(19) 0.0128(19) 0.023(2) -0.0002(16) 0.0031(16) 0.0042(14) C23 0.0121(19) 0.017(2) 0.020(2) 0.0027(16) -0.0004(16) 0.0012(15) C24 0.016(2) 0.0123(18) 0.0133(18) 0.0016(15) -0.0023(15) -0.0007(15) C25 0.0151(19) 0.0104(18) 0.0124(19) 0.0043(15) 0.0035(15) 0.0014(14) C26 0.016(2) 0.0107(18) 0.0110(18) 0.0050(15) 0.0007(15) 0.0016(15) _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 1.928(3) . ? Fe1 O1 1.934(3) . ? Fe1 O3 1.944(2) . ? Fe1 N2 2.102(3) . ? Fe1 N1 2.103(3) . ? Fe1 N3 2.200(3) . ? O2 C1 1.315(5) . ? O1 C11 1.328(4) . ? O3 C20 1.311(4) . ? N2 C7 1.277(5) . ? N2 C8 1.472(5) . ? N1 C17 1.285(5) . ? N1 C9 1.460(5) . ? N3 C19 1.306(5) . ? N3 N4 1.392(4) . ? N4 C18 1.307(5) . ? N5 C19 1.349(5) . ? N5 C18 1.365(5) . ? N5 N6 1.413(4) . ? N6 C26 1.298(5) . ? C1 C2 1.406(6) . ? C1 C6 1.422(5) . ? C2 C3 1.386(6) . ? C2 H2A 0.9500 . ? C3 C4 1.382(6) . ? C3 H3A 0.9500 . ? C4 C5 1.371(6) . ? C4 H4A 0.9500 . ? C5 C6 1.413(5) . ? C5 H5A 0.9500 . ? C6 C7 1.455(5) . ? C7 H7A 0.9500 . ? C8 C9 1.524(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 C12 1.401(5) . ? C11 C16 1.426(5) . ? C12 C13 1.384(6) . ? C12 H12A 0.9500 . ? C13 C14 1.394(6) . ? C13 H13A 0.9500 . ? C14 C15 1.381(6) . ? C14 H14A 0.9500 . ? C15 C16 1.401(5) . ? C15 H15A 0.9500 . ? C16 C17 1.450(5) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.416(5) . ? C20 C25 1.418(5) . ? C21 C22 1.383(5) . ? C21 H21A 0.9500 . ? C22 C23 1.397(5) . ? C22 H22A 0.9500 . ? C23 C24 1.376(5) . ? C23 H23A 0.9500 . ? C24 C25 1.408(5) . ? C24 H24A 0.9500 . ? C25 C26 1.445(5) 5_666 ? C26 C25 1.445(5) 5_666 ? C26 H26A 0.9995 . ? O4 C27 1.50(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Fe1 O1 104.74(11) . . ? O2 Fe1 O3 92.89(11) . . ? O1 Fe1 O3 95.49(11) . . ? O2 Fe1 N2 88.64(11) . . ? O1 Fe1 N2 165.31(12) . . ? O3 Fe1 N2 89.74(11) . . ? O2 Fe1 N1 166.68(12) . . ? O1 Fe1 N1 87.86(11) . . ? O3 Fe1 N1 90.11(11) . . ? N2 Fe1 N1 78.39(12) . . ? O2 Fe1 N3 84.89(11) . . ? O1 Fe1 N3 90.01(11) . . ? O3 Fe1 N3 174.43(11) . . ? N2 Fe1 N3 85.11(12) . . ? N1 Fe1 N3 90.92(12) . . ? C1 O2 Fe1 131.2(2) . . ? C11 O1 Fe1 127.3(2) . . ? C20 O3 Fe1 135.1(2) . . ? C7 N2 C8 120.8(3) . . ? C7 N2 Fe1 125.8(3) . . ? C8 N2 Fe1 113.4(2) . . ? C17 N1 C9 120.5(3) . . ? C17 N1 Fe1 122.1(3) . . ? C9 N1 Fe1 115.3(2) . . ? C19 N3 N4 108.3(3) . . ? C19 N3 Fe1 124.0(2) . . ? N4 N3 Fe1 126.8(2) . . ? C18 N4 N3 106.0(3) . . ? C19 N5 C18 105.6(3) . . ? C19 N5 N6 128.5(3) . . ? C18 N5 N6 125.2(3) . . ? C26 N6 N5 111.4(3) . . ? O2 C1 C2 118.7(4) . . ? O2 C1 C6 123.8(3) . . ? C2 C1 C6 117.5(4) . . ? C3 C2 C1 121.5(4) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 119.6(4) . . ? C5 C6 C7 116.6(3) . . ? C1 C6 C7 123.6(3) . . ? N2 C7 C6 124.9(4) . . ? N2 C7 H7A 117.5 . . ? C6 C7 H7A 117.5 . . ? N2 C8 C9 108.9(3) . . ? N2 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? N2 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? N1 C9 C8 107.9(3) . . ? N1 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N1 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O1 C11 C12 118.9(3) . . ? O1 C11 C16 122.9(3) . . ? C12 C11 C16 118.2(3) . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C15 C14 C13 118.6(4) . . ? C15 C14 H14A 120.7 . . ? C13 C14 H14A 120.7 . . ? C14 C15 C16 122.0(4) . . ? C14 C15 H15A 119.0 . . ? C16 C15 H15A 119.0 . . ? C15 C16 C11 119.0(4) . . ? C15 C16 C17 117.3(4) . . ? C11 C16 C17 123.6(3) . . ? N1 C17 C16 125.3(3) . . ? N1 C17 H17A 117.4 . . ? C16 C17 H17A 117.4 . . ? N4 C18 N5 110.5(3) . . ? N4 C18 H18A 124.7 . . ? N5 C18 H18A 124.7 . . ? N3 C19 N5 109.6(3) . . ? N3 C19 H19A 125.2 . . ? N5 C19 H19A 125.2 . . ? O3 C20 C21 119.4(3) . . ? O3 C20 C25 122.8(3) . . ? C21 C20 C25 117.8(3) . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C21 C22 C23 121.5(3) . . ? C21 C22 H22A 119.3 . . ? C23 C22 H22A 119.3 . . ? C24 C23 C22 118.8(4) . . ? C24 C23 H23A 120.6 . . ? C22 C23 H23A 120.6 . . ? C23 C24 C25 121.3(3) . . ? C23 C24 H24A 119.3 . . ? C25 C24 H24A 119.3 . . ? C24 C25 C20 120.0(3) . . ? C24 C25 C26 122.2(3) . 5_666 ? C20 C25 C26 117.8(3) . 5_666 ? N6 C26 C25 121.2(3) . 5_666 ? N6 C26 H26A 121.3 . . ? C25 C26 H26A 117.5 5_666 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.959 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.099 # Attachment 'dt-art-06-2011-011127-File010-v1-0.cif' data_r2 _database_code_depnum_ccdc_archive 'CCDC 830416' #TrackingRef 'dt-art-06-2011-011127-File010-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H46 Fe2 N12 O6' _chemical_formula_weight 1046.71 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 8.1712(3) _cell_length_b 11.4950(3) _cell_length_c 13.7935(4) _cell_angle_alpha 101.421(2) _cell_angle_beta 106.585(3) _cell_angle_gamma 104.783(3) _cell_volume 1148.17(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9125 _cell_measurement_theta_min 2.9923 _cell_measurement_theta_max 33.2742 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7917 _exptl_absorpt_correction_T_max 0.8727 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10611 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4050 _reflns_number_gt 3421 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+1.4322P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4050 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.25470(5) 0.22606(4) -0.14726(3) 0.01822(16) Uani 1 1 d . . . O1 O 0.2673(3) 0.30223(18) -0.00604(16) 0.0185(4) Uani 1 1 d . . . O2 O 0.2996(3) 0.3642(2) -0.20677(16) 0.0235(5) Uani 1 1 d . . . O3 O -0.0082(3) 0.17948(18) -0.20560(17) 0.0222(5) Uani 1 1 d . . . N1 N 0.2232(4) 0.0522(2) -0.1142(2) 0.0329(7) Uani 1 1 d . . . N2 N 0.2649(4) 0.1117(3) -0.2833(2) 0.0390(8) Uani 1 1 d . . . N3 N 0.4493(3) 0.7236(2) 0.0699(2) 0.0217(6) Uani 1 1 d . . . N4 N 0.3392(3) 0.7862(2) 0.0991(2) 0.0218(6) Uani 1 1 d . . . N5 N 0.1742(3) 0.6263(2) -0.0422(2) 0.0193(5) Uani 1 1 d . . . N6 N 0.0268(3) 0.5518(2) -0.1353(2) 0.0224(6) Uani 1 1 d . . . C1 C -0.1169(4) 0.2174(3) -0.2740(2) 0.0203(6) Uani 1 1 d . . . C2 C -0.2395(4) 0.1316(3) -0.3704(3) 0.0283(7) Uani 1 1 d . . . H2A H -0.2439 0.0463 -0.3858 0.034 Uiso 1 1 calc R . . C3 C -0.3539(5) 0.1682(3) -0.4434(3) 0.0358(8) Uani 1 1 d . . . H3A H -0.4355 0.1081 -0.5084 0.043 Uiso 1 1 calc R . . C4 C -0.3513(4) 0.2923(3) -0.4230(3) 0.0325(8) Uani 1 1 d . . . H4A H -0.4299 0.3173 -0.4738 0.039 Uiso 1 1 calc R . . C5 C -0.2335(4) 0.3782(3) -0.3286(3) 0.0253(7) Uani 1 1 d . . . H5A H -0.2320 0.4628 -0.3144 0.030 Uiso 1 1 calc R . . C6 C -0.1156(4) 0.3434(3) -0.2528(2) 0.0194(6) Uani 1 1 d . . . C7 C 0.0123(4) 0.4347(3) -0.1551(2) 0.0186(6) Uani 1 1 d . . . H7A H 0.0874 0.4076 -0.1043 0.022 Uiso 1 1 calc R . . C8 C 0.1767(4) 0.7267(3) 0.0303(2) 0.0202(6) Uani 1 1 d . . . H8A H 0.0735 0.7501 0.0307 0.024 Uiso 1 1 calc R . . C9 C 0.3474(4) 0.6282(3) -0.0150(2) 0.0206(6) Uani 1 1 d . . . H9A H 0.3893 0.5698 -0.0514 0.025 Uiso 1 1 calc R . . C10 C 0.2874(4) 0.2600(3) 0.0773(2) 0.0190(6) Uani 1 1 d . . . C11 C 0.3334(4) 0.3454(3) 0.1764(2) 0.0239(7) Uani 1 1 d . . . H11A H 0.3524 0.4319 0.1822 0.029 Uiso 1 1 calc R . . C12 C 0.3517(5) 0.3057(4) 0.2659(3) 0.0342(8) Uani 1 1 d . . . H12A H 0.3846 0.3651 0.3326 0.041 Uiso 1 1 calc R . . C13 C 0.3222(6) 0.1787(4) 0.2588(3) 0.0413(9) Uani 1 1 d . . . H13A H 0.3331 0.1517 0.3204 0.050 Uiso 1 1 calc R . . C14 C 0.2779(5) 0.0939(3) 0.1636(3) 0.0384(9) Uani 1 1 d . . . H14A H 0.2566 0.0075 0.1595 0.046 Uiso 1 1 calc R . . C15 C 0.2626(4) 0.1312(3) 0.0710(3) 0.0279(7) Uani 1 1 d . . . C16 C 0.2270(5) 0.0353(3) -0.0253(3) 0.0367(9) Uani 1 1 d . . . H16A H 0.2040 -0.0487 -0.0217 0.044 Uiso 1 1 calc R . . C17 C 0.1772(7) -0.0548(4) -0.2095(4) 0.0621(13) Uani 1 1 d . . . H17A H 0.0465 -0.0752 -0.2521 0.074 Uiso 1 1 calc R . . C18 C 0.2822(8) -0.0093(4) -0.2736(4) 0.0693(15) Uani 1 1 d . . . H18A H 0.4111 0.0006 -0.2392 0.083 Uiso 1 1 calc R . . H18B H 0.2360 -0.0708 -0.3446 0.083 Uiso 1 1 calc R . . C19 C 0.2019(8) -0.1736(4) -0.1940(4) 0.0632(13) Uani 1 1 d . . . H19A H 0.1307 -0.2048 -0.1525 0.095 Uiso 1 1 calc R . . H19B H 0.3302 -0.1586 -0.1563 0.095 Uiso 1 1 calc R . . H19C H 0.1611 -0.2363 -0.2630 0.095 Uiso 1 1 calc R . . C20 C 0.2389(5) 0.1391(4) -0.3721(3) 0.0470(11) Uani 1 1 d . . . H20A H 0.2281 0.0757 -0.4317 0.056 Uiso 1 1 calc R . . C21 C 0.2250(5) 0.2549(4) -0.3890(3) 0.0386(9) Uani 1 1 d . . . C22 C 0.1788(6) 0.2629(5) -0.4958(3) 0.0585(14) Uani 1 1 d . . . H22A H 0.1575 0.1912 -0.5517 0.070 Uiso 1 1 calc R . . C23 C 0.1648(6) 0.3707(6) -0.5186(4) 0.0601(14) Uani 1 1 d . . . H23A H 0.1340 0.3741 -0.5896 0.072 Uiso 1 1 calc R . . C24 C 0.1954(5) 0.4736(5) -0.4387(3) 0.0515(12) Uani 1 1 d . . . H24A H 0.1866 0.5492 -0.4541 0.062 Uiso 1 1 calc R . . C25 C 0.2391(4) 0.4696(4) -0.3357(3) 0.0384(9) Uani 1 1 d . . . H25A H 0.2588 0.5427 -0.2816 0.046 Uiso 1 1 calc R . . C26 C 0.2554(4) 0.3613(3) -0.3078(3) 0.0299(8) 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 0.0160(2) 0.0173(2) 0.0196(3) 0.00162(17) 0.00555(18) 0.00637(17) O1 0.0202(10) 0.0171(10) 0.0198(11) 0.0050(8) 0.0071(9) 0.0091(8) O2 0.0195(11) 0.0308(12) 0.0192(11) 0.0084(9) 0.0072(9) 0.0054(9) O3 0.0168(10) 0.0185(10) 0.0284(12) 0.0052(9) 0.0057(9) 0.0050(8) N1 0.0401(17) 0.0199(14) 0.0374(17) 0.0068(12) 0.0094(14) 0.0138(12) N2 0.0379(18) 0.0332(16) 0.0385(18) -0.0065(13) 0.0159(15) 0.0100(14) N3 0.0180(13) 0.0200(12) 0.0286(14) 0.0049(11) 0.0096(11) 0.0089(10) N4 0.0214(13) 0.0190(12) 0.0294(14) 0.0059(11) 0.0134(12) 0.0100(10) N5 0.0152(12) 0.0149(12) 0.0266(14) 0.0056(10) 0.0056(11) 0.0052(10) N6 0.0160(12) 0.0207(13) 0.0268(14) 0.0063(11) 0.0033(11) 0.0056(10) C1 0.0126(14) 0.0245(15) 0.0243(16) 0.0080(13) 0.0079(12) 0.0045(12) C2 0.0230(16) 0.0237(16) 0.0294(18) 0.0028(14) 0.0045(14) 0.0022(13) C3 0.0240(18) 0.0335(19) 0.0322(19) 0.0055(15) -0.0030(15) -0.0017(14) C4 0.0222(17) 0.0350(18) 0.0329(19) 0.0155(15) 0.0002(15) 0.0041(14) C5 0.0204(16) 0.0258(16) 0.0314(18) 0.0131(14) 0.0086(14) 0.0075(13) C6 0.0138(14) 0.0210(15) 0.0241(16) 0.0078(12) 0.0086(12) 0.0040(11) C7 0.0150(14) 0.0227(15) 0.0225(16) 0.0097(12) 0.0096(12) 0.0077(12) C8 0.0204(15) 0.0175(14) 0.0292(17) 0.0092(12) 0.0137(13) 0.0096(12) C9 0.0168(15) 0.0178(14) 0.0273(16) 0.0040(12) 0.0078(13) 0.0079(12) C10 0.0126(14) 0.0250(15) 0.0229(16) 0.0105(12) 0.0067(12) 0.0089(12) C11 0.0217(16) 0.0271(16) 0.0272(17) 0.0119(13) 0.0101(14) 0.0102(13) C12 0.037(2) 0.049(2) 0.0217(17) 0.0131(15) 0.0125(15) 0.0178(17) C13 0.050(2) 0.050(2) 0.038(2) 0.0312(19) 0.0191(19) 0.0210(19) C14 0.044(2) 0.0328(19) 0.046(2) 0.0240(17) 0.0165(19) 0.0159(17) C15 0.0257(17) 0.0246(16) 0.0347(19) 0.0142(14) 0.0085(15) 0.0087(14) C16 0.045(2) 0.0174(16) 0.049(2) 0.0127(16) 0.0147(18) 0.0122(15) C17 0.081(3) 0.029(2) 0.069(3) -0.001(2) 0.021(3) 0.023(2) C18 0.098(4) 0.038(2) 0.072(3) -0.007(2) 0.046(3) 0.023(3) C19 0.089(4) 0.044(2) 0.054(3) 0.012(2) 0.023(3) 0.023(2) C20 0.040(2) 0.066(3) 0.0225(19) -0.0097(18) 0.0157(17) 0.009(2) C21 0.0248(18) 0.063(3) 0.0256(18) 0.0081(17) 0.0111(15) 0.0111(17) C22 0.036(2) 0.105(4) 0.024(2) 0.000(2) 0.0148(18) 0.015(2) C23 0.041(2) 0.115(4) 0.043(3) 0.048(3) 0.019(2) 0.031(3) C24 0.030(2) 0.096(4) 0.042(2) 0.041(3) 0.0173(19) 0.020(2) C25 0.0197(17) 0.065(3) 0.039(2) 0.0332(19) 0.0128(16) 0.0117(17) C26 0.0122(15) 0.054(2) 0.0227(17) 0.0126(15) 0.0084(13) 0.0060(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 Fe1 O2 1.929(2) . ? Fe1 O1 1.933(2) . ? Fe1 O3 1.951(2) . ? Fe1 N2 2.104(3) . ? Fe1 N1 2.105(3) . ? Fe1 N3 2.211(2) 2_665 ? O1 C10 1.318(4) . ? O2 C26 1.327(4) . ? O3 C1 1.323(4) . ? N1 C16 1.272(5) . ? N1 C17 1.491(5) . ? N2 C20 1.297(5) . ? N2 C18 1.461(6) . ? N3 C9 1.317(4) . ? N3 N4 1.384(3) . ? N3 Fe1 2.211(2) 2_665 ? N4 C8 1.300(4) . ? N5 C9 1.350(4) . ? N5 C8 1.360(4) . ? N5 N6 1.410(3) . ? N6 C7 1.287(4) . ? C1 C2 1.401(4) . ? C1 C6 1.416(4) . ? C2 C3 1.377(5) . ? C2 H2A 0.9500 . ? C3 C4 1.392(5) . ? C3 H3A 0.9500 . ? C4 C5 1.374(5) . ? C4 H4A 0.9500 . ? C5 C6 1.403(4) . ? C5 H5A 0.9500 . ? C6 C7 1.444(4) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.399(4) . ? C10 C15 1.424(4) . ? C11 C12 1.381(5) . ? C11 H11A 0.9500 . ? C12 C13 1.395(5) . ? C12 H12A 0.9500 . ? C13 C14 1.359(5) . ? C13 H13A 0.9500 . ? C14 C15 1.410(5) . ? C14 H14A 0.9500 . ? C15 C16 1.449(5) . ? C16 H16A 0.9500 . ? C17 C18 1.476(7) . ? C17 C19 1.477(6) . ? C17 H17A 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.422(6) . ? C20 H20A 0.9500 . ? C21 C26 1.399(5) . ? C21 C22 1.441(6) . ? C22 C23 1.362(7) . ? C22 H22A 0.9500 . ? C23 C24 1.361(7) . ? C23 H23A 0.9500 . ? C24 C25 1.376(5) . ? C24 H24A 0.9500 . ? C25 C26 1.400(5) . ? C25 H25A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Fe1 O1 104.68(9) . . ? O2 Fe1 O3 94.73(9) . . ? O1 Fe1 O3 93.04(9) . . ? O2 Fe1 N2 87.67(11) . . ? O1 Fe1 N2 165.75(11) . . ? O3 Fe1 N2 92.99(11) . . ? O2 Fe1 N1 165.21(11) . . ? O1 Fe1 N1 89.40(10) . . ? O3 Fe1 N1 88.94(10) . . ? N2 Fe1 N1 77.82(12) . . ? O2 Fe1 N3 88.53(9) . 2_665 ? O1 Fe1 N3 83.33(9) . 2_665 ? O3 Fe1 N3 175.65(9) . 2_665 ? N2 Fe1 N3 90.01(11) . 2_665 ? N1 Fe1 N3 88.62(10) . 2_665 ? C10 O1 Fe1 130.99(18) . . ? C26 O2 Fe1 128.7(2) . . ? C1 O3 Fe1 132.33(18) . . ? C16 N1 C17 121.9(3) . . ? C16 N1 Fe1 124.8(2) . . ? C17 N1 Fe1 113.0(3) . . ? C20 N2 C18 122.1(3) . . ? C20 N2 Fe1 123.4(3) . . ? C18 N2 Fe1 114.1(3) . . ? C9 N3 N4 107.9(2) . . ? C9 N3 Fe1 125.0(2) . 2_665 ? N4 N3 Fe1 127.03(18) . 2_665 ? C8 N4 N3 106.3(2) . . ? C9 N5 C8 105.3(2) . . ? C9 N5 N6 128.0(2) . . ? C8 N5 N6 125.9(2) . . ? C7 N6 N5 112.1(2) . . ? O3 C1 C2 119.9(3) . . ? O3 C1 C6 122.1(3) . . ? C2 C1 C6 117.9(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 119.5(3) . . ? C5 C6 C7 121.3(3) . . ? C1 C6 C7 119.2(3) . . ? N6 C7 C6 121.5(3) . . ? N6 C7 H7A 119.2 . . ? C6 C7 H7A 119.2 . . ? N4 C8 N5 111.0(3) . . ? N4 C8 H8A 124.5 . . ? N5 C8 H8A 124.5 . . ? N3 C9 N5 109.5(3) . . ? N3 C9 H9A 125.2 . . ? N5 C9 H9A 125.2 . . ? O1 C10 C11 118.6(3) . . ? O1 C10 C15 122.9(3) . . ? C11 C10 C15 118.5(3) . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C11 C12 C13 120.4(3) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 121.4(3) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? C14 C15 C10 118.8(3) . . ? C14 C15 C16 117.4(3) . . ? C10 C15 C16 123.8(3) . . ? N1 C16 C15 126.7(3) . . ? N1 C16 H16A 116.7 . . ? C15 C16 H16A 116.7 . . ? C18 C17 C19 109.3(4) . . ? C18 C17 N1 107.5(4) . . ? C19 C17 N1 118.5(4) . . ? C18 C17 H17A 107.0 . . ? C19 C17 H17A 107.0 . . ? N1 C17 H17A 107.0 . . ? N2 C18 C17 108.8(4) . . ? N2 C18 H18A 109.9 . . ? C17 C18 H18A 109.9 . . ? N2 C18 H18B 109.9 . . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 C21 126.3(3) . . ? N2 C20 H20A 116.8 . . ? C21 C20 H20A 116.8 . . ? C26 C21 C20 123.7(3) . . ? C26 C21 C22 118.4(4) . . ? C20 C21 C22 117.9(4) . . ? C23 C22 C21 121.6(4) . . ? C23 C22 H22A 119.2 . . ? C21 C22 H22A 119.2 . . ? C24 C23 C22 119.3(4) . . ? C24 C23 H23A 120.4 . . ? C22 C23 H23A 120.4 . . ? C23 C24 C25 120.9(5) . . ? C23 C24 H24A 119.6 . . ? C25 C24 H24A 119.6 . . ? C24 C25 C26 122.2(4) . . ? C24 C25 H25A 118.9 . . ? C26 C25 H25A 118.9 . . ? O2 C26 C25 119.1(3) . . ? O2 C26 C21 123.2(3) . . ? C25 C26 C21 117.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.309 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.081 # Attachment 'dt-art-06-2011-011127-File011-v1-0.cif' data_l _database_code_depnum_ccdc_archive 'CCDC 830417' #TrackingRef 'dt-art-06-2011-011127-File011-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H31 Fe N6 O4' _chemical_formula_weight 595.46 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4571(2) _cell_length_b 16.3096(4) _cell_length_c 17.6369(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.704(3) _cell_angle_gamma 90.00 _cell_volume 2642.89(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16036 _cell_measurement_theta_min 3.0125 _cell_measurement_theta_max 33.2975 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 0.621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7893 _exptl_absorpt_correction_T_max 0.8859 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24639 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4649 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.7348P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4649 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.44837(3) 0.746850(17) 0.601694(17) 0.01424(11) Uani 1 1 d . . . C1 C 0.5866(2) 0.61531(13) 0.52338(12) 0.0159(5) Uani 1 1 d . . . N6 N 0.6652(2) 0.44504(11) 0.65977(10) 0.0208(4) Uani 1 1 d . . . N5 N 0.63145(18) 0.43043(11) 0.73266(10) 0.0173(4) Uani 1 1 d . . . N4 N 0.62408(19) 0.44000(11) 0.85561(10) 0.0196(4) Uani 1 1 d . . . N3 N 0.58829(19) 0.36063(11) 0.82972(10) 0.0179(4) Uani 1 1 d . . . N1 N 0.22243(19) 0.75679(10) 0.55329(10) 0.0159(4) Uani 1 1 d . . . N2 N 0.44032(18) 0.83004(10) 0.50937(9) 0.0146(4) Uani 1 1 d . . . O1 O 0.40618(15) 0.68646(9) 0.68784(8) 0.0189(3) Uani 1 1 d . . . O2 O 0.65428(15) 0.76870(9) 0.63771(8) 0.0169(3) Uani 1 1 d . . . O3 O 0.47768(15) 0.64955(9) 0.54755(8) 0.0180(3) Uani 1 1 d . . . C2 C 0.6384(2) 0.64909(14) 0.46189(13) 0.0205(5) Uani 1 1 d . . . H2A H 0.6032 0.7008 0.4408 0.025 Uiso 1 1 calc R . . C3 C 0.7398(2) 0.60783(14) 0.43192(13) 0.0225(5) Uani 1 1 d . . . H3A H 0.7722 0.6311 0.3896 0.027 Uiso 1 1 calc R . . C4 C 0.7959(2) 0.53269(14) 0.46245(13) 0.0224(5) Uani 1 1 d . . . H4A H 0.8633 0.5038 0.4401 0.027 Uiso 1 1 calc R . . O4 O 0.7502(2) 0.66090(11) 0.76879(11) 0.0421(5) Uani 1 1 d . . . C5 C 0.7524(2) 0.50086(13) 0.52539(13) 0.0202(5) Uani 1 1 d . . . H5A H 0.7922 0.4503 0.5474 0.024 Uiso 1 1 calc R . . C6 C 0.6500(2) 0.54192(12) 0.55755(12) 0.0158(5) Uani 1 1 d . . . C7 C 0.6124(2) 0.51258(13) 0.62760(12) 0.0166(5) Uani 1 1 d . . . H7A H 0.5478 0.5437 0.6501 0.020 Uiso 1 1 calc R . . C8 C 0.6503(2) 0.47988(13) 0.79595(12) 0.0203(5) Uani 1 1 d . . . H8A H 0.6787 0.5358 0.7969 0.024 Uiso 1 1 calc R . . C9 C 0.5957(2) 0.35698(13) 0.75686(13) 0.0209(5) Uani 1 1 d . . . H9A H 0.5783 0.3091 0.7254 0.025 Uiso 1 1 calc R . . C10 C 0.2906(2) 0.64130(13) 0.68952(12) 0.0176(5) Uani 1 1 d . . . C11 C 0.3033(2) 0.57839(14) 0.74474(13) 0.0228(5) Uani 1 1 d . . . H11A H 0.3957 0.5672 0.7783 0.027 Uiso 1 1 calc R . . C12 C 0.1846(3) 0.53218(14) 0.75157(14) 0.0279(6) Uani 1 1 d . . . H12A H 0.1966 0.4891 0.7888 0.034 Uiso 1 1 calc R . . C13 C 0.0472(3) 0.54842(15) 0.70411(14) 0.0277(6) Uani 1 1 d . . . H13A H -0.0351 0.5178 0.7098 0.033 Uiso 1 1 calc R . . C14 C 0.0324(2) 0.60916(14) 0.64909(13) 0.0227(5) Uani 1 1 d . . . H14A H -0.0614 0.6205 0.6170 0.027 Uiso 1 1 calc R . . C15 C 0.1521(2) 0.65511(13) 0.63882(12) 0.0179(5) Uani 1 1 d . . . C16 C 0.1250(2) 0.71498(13) 0.57677(12) 0.0182(5) Uani 1 1 d . . . H16A H 0.0263 0.7245 0.5508 0.022 Uiso 1 1 calc R . . C17 C 0.1780(2) 0.82188(13) 0.49304(12) 0.0171(5) Uani 1 1 d . . . H17A H 0.1714 0.8746 0.5210 0.020 Uiso 1 1 calc R . . C18 C 0.3011(2) 0.83119(13) 0.45044(12) 0.0175(5) Uani 1 1 d . . . H18A H 0.2903 0.8849 0.4223 0.021 Uiso 1 1 calc R . . C19 C 0.3014(2) 0.76225(13) 0.39230(13) 0.0200(5) Uani 1 1 d . . . H19A H 0.3747 0.7745 0.3620 0.024 Uiso 1 1 calc R . . H19B H 0.3304 0.7105 0.4212 0.024 Uiso 1 1 calc R . . C20 C 0.1535(2) 0.75047(14) 0.33615(13) 0.0210(5) Uani 1 1 d . . . H20A H 0.1291 0.7996 0.3026 0.025 Uiso 1 1 calc R . . H20B H 0.1573 0.7027 0.3020 0.025 Uiso 1 1 calc R . . C21 C 0.0367(2) 0.73669(14) 0.38092(13) 0.0220(5) Uani 1 1 d . . . H21A H -0.0592 0.7305 0.3438 0.026 Uiso 1 1 calc R . . H21B H 0.0577 0.6857 0.4120 0.026 Uiso 1 1 calc R . . C22 C 0.0328(2) 0.80900(14) 0.43468(12) 0.0213(5) Uani 1 1 d . . . H22A H -0.0439 0.7996 0.4634 0.026 Uiso 1 1 calc R . . H22B H 0.0073 0.8593 0.4029 0.026 Uiso 1 1 calc R . . C23 C 0.5423(2) 0.87928(13) 0.50295(12) 0.0161(5) Uani 1 1 d . . . H23A H 0.5211 0.9180 0.4615 0.019 Uiso 1 1 calc R . . C24 C 0.6876(2) 0.88088(13) 0.55368(12) 0.0159(5) Uani 1 1 d . . . C25 C 0.7850(2) 0.93952(13) 0.53667(12) 0.0188(5) Uani 1 1 d . . . H25A H 0.7516 0.9770 0.4951 0.023 Uiso 1 1 calc R . . C26 C 0.9272(2) 0.94389(14) 0.57862(13) 0.0211(5) Uani 1 1 d . . . H26A H 0.9910 0.9843 0.5666 0.025 Uiso 1 1 calc R . . C27 C 0.9765(2) 0.88809(14) 0.63900(12) 0.0202(5) Uani 1 1 d . . . H27A H 1.0751 0.8900 0.6678 0.024 Uiso 1 1 calc R . . C28 C 0.8840(2) 0.83025(13) 0.65737(12) 0.0173(5) Uani 1 1 d . . . H28A H 0.9201 0.7928 0.6987 0.021 Uiso 1 1 calc R . . C29 C 0.7375(2) 0.82523(12) 0.61648(11) 0.0149(4) Uani 1 1 d . . . C30 C 0.6790(3) 0.69249(18) 0.82181(17) 0.0432(7) Uani 1 1 d . . . H30C H 0.5771 0.6749 0.8081 0.065 Uiso 1 1 calc R . . H30B H 0.6836 0.7525 0.8210 0.065 Uiso 1 1 calc R . . H30A H 0.7257 0.6726 0.8742 0.065 Uiso 1 1 calc R . . H4W H 0.7210 0.6964 0.7183 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.01331(17) 0.01609(18) 0.01392(17) 0.00228(12) 0.00442(12) 0.00153(12) C1 0.0133(11) 0.0158(11) 0.0175(11) -0.0046(9) 0.0016(9) -0.0032(9) N6 0.0262(10) 0.0197(10) 0.0197(10) 0.0019(8) 0.0119(8) -0.0006(8) N5 0.0193(9) 0.0172(9) 0.0161(9) 0.0014(8) 0.0054(7) 0.0009(8) N4 0.0213(10) 0.0175(10) 0.0195(10) -0.0004(8) 0.0039(8) 0.0011(8) N3 0.0181(10) 0.0190(9) 0.0167(9) -0.0014(8) 0.0042(8) -0.0018(8) N1 0.0170(9) 0.0185(9) 0.0130(9) -0.0010(7) 0.0052(7) 0.0015(8) N2 0.0144(9) 0.0168(9) 0.0124(9) 0.0008(7) 0.0031(7) 0.0042(8) O1 0.0174(8) 0.0216(8) 0.0190(8) 0.0049(7) 0.0067(6) -0.0012(7) O2 0.0142(7) 0.0188(8) 0.0170(8) 0.0029(6) 0.0025(6) 0.0001(6) O3 0.0158(8) 0.0170(8) 0.0226(8) -0.0013(6) 0.0070(6) 0.0016(6) C2 0.0193(11) 0.0198(11) 0.0216(12) 0.0037(9) 0.0034(9) 0.0022(9) C3 0.0230(12) 0.0263(12) 0.0199(12) 0.0010(10) 0.0087(9) -0.0042(10) C4 0.0219(12) 0.0217(12) 0.0266(13) -0.0033(10) 0.0117(10) 0.0015(10) O4 0.0514(12) 0.0350(10) 0.0359(11) 0.0015(9) 0.0024(9) -0.0027(9) C5 0.0210(12) 0.0149(11) 0.0248(12) -0.0007(9) 0.0059(10) 0.0005(9) C6 0.0150(11) 0.0158(11) 0.0164(11) -0.0022(9) 0.0034(9) -0.0040(9) C7 0.0131(10) 0.0170(11) 0.0190(11) -0.0040(9) 0.0028(9) -0.0026(9) C8 0.0211(12) 0.0161(11) 0.0223(12) 0.0001(10) 0.0021(9) 0.0019(9) C9 0.0269(12) 0.0183(11) 0.0188(12) -0.0024(9) 0.0078(10) -0.0053(10) C10 0.0204(12) 0.0177(11) 0.0186(11) -0.0021(9) 0.0125(9) 0.0004(9) C11 0.0246(12) 0.0228(12) 0.0236(12) 0.0036(10) 0.0106(10) 0.0044(10) C12 0.0367(14) 0.0235(13) 0.0287(13) 0.0047(11) 0.0178(11) -0.0009(11) C13 0.0262(13) 0.0285(13) 0.0316(14) -0.0008(11) 0.0130(11) -0.0086(11) C14 0.0215(12) 0.0259(12) 0.0224(12) -0.0052(10) 0.0087(10) -0.0044(10) C15 0.0215(12) 0.0182(11) 0.0168(11) -0.0039(9) 0.0104(9) 0.0007(9) C16 0.0165(11) 0.0225(11) 0.0159(11) -0.0046(9) 0.0044(9) 0.0011(9) C17 0.0182(11) 0.0185(11) 0.0147(11) 0.0001(9) 0.0041(9) 0.0035(9) C18 0.0168(11) 0.0207(11) 0.0138(11) 0.0043(9) 0.0013(9) 0.0019(9) C19 0.0178(11) 0.0243(12) 0.0183(11) 0.0005(9) 0.0056(9) 0.0009(9) C20 0.0226(12) 0.0224(12) 0.0170(11) -0.0030(10) 0.0026(9) -0.0010(10) C21 0.0193(12) 0.0244(12) 0.0210(12) -0.0007(10) 0.0022(9) -0.0033(10) C22 0.0195(12) 0.0254(12) 0.0194(12) 0.0025(10) 0.0052(9) 0.0034(10) C23 0.0198(12) 0.0174(11) 0.0129(10) 0.0019(9) 0.0075(9) 0.0033(9) C24 0.0156(11) 0.0193(11) 0.0138(11) -0.0027(9) 0.0053(8) 0.0020(9) C25 0.0252(12) 0.0173(11) 0.0159(11) 0.0006(9) 0.0086(9) 0.0012(10) C26 0.0210(12) 0.0221(12) 0.0233(12) -0.0039(10) 0.0113(9) -0.0052(10) C27 0.0160(11) 0.0257(12) 0.0193(12) -0.0063(10) 0.0051(9) -0.0008(10) C28 0.0174(11) 0.0185(11) 0.0161(11) -0.0013(9) 0.0040(9) 0.0030(9) C29 0.0173(11) 0.0148(11) 0.0145(11) -0.0026(9) 0.0075(9) 0.0015(9) C30 0.0327(15) 0.0450(17) 0.0504(18) 0.0038(14) 0.0069(13) 0.0032(13) _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 1.9059(14) . ? Fe1 O1 1.9300(14) . ? Fe1 O2 1.9330(14) . ? Fe1 N2 2.1070(17) . ? Fe1 N1 2.1110(18) . ? Fe1 N3 2.2860(17) 2_656 ? C1 O3 1.327(2) . ? C1 C2 1.404(3) . ? C1 C6 1.409(3) . ? N6 C7 1.285(3) . ? N6 N5 1.416(2) . ? N5 C9 1.342(3) . ? N5 C8 1.354(3) . ? N4 C8 1.310(3) . ? N4 N3 1.388(2) . ? N3 C9 1.305(3) . ? N3 Fe1 2.2860(17) 2_646 ? N1 C16 1.291(3) . ? N1 C17 1.490(3) . ? N2 C23 1.280(3) . ? N2 C18 1.472(3) . ? O1 C10 1.324(3) . ? O2 C29 1.322(2) . ? C2 C3 1.376(3) . ? C2 H2A 0.9500 . ? C3 C4 1.392(3) . ? C3 H3A 0.9500 . ? C4 C5 1.374(3) . ? C4 H4A 0.9500 . ? O4 C30 1.375(3) . ? O4 H4W 1.0430 . ? C5 C6 1.403(3) . ? C5 H5A 0.9500 . ? C6 C7 1.446(3) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.400(3) . ? C10 C15 1.418(3) . ? C11 C12 1.381(3) . ? C11 H11A 0.9500 . ? C12 C13 1.394(3) . ? C12 H12A 0.9500 . ? C13 C14 1.370(3) . ? C13 H13A 0.9500 . ? C14 C15 1.405(3) . ? C14 H14A 0.9500 . ? C15 C16 1.443(3) . ? C16 H16A 0.9500 . ? C17 C22 1.523(3) . ? C17 C18 1.535(3) . ? C17 H17A 1.0000 . ? C18 C19 1.522(3) . ? C18 H18A 1.0000 . ? C19 C20 1.522(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.519(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.519(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.452(3) . ? C23 H23A 0.9500 . ? C24 C25 1.409(3) . ? C24 C29 1.423(3) . ? C25 C26 1.375(3) . ? C25 H25A 0.9500 . ? C26 C27 1.394(3) . ? C26 H26A 0.9500 . ? C27 C28 1.377(3) . ? C27 H27A 0.9500 . ? C28 C29 1.404(3) . ? C28 H28A 0.9500 . ? C30 H30C 0.9800 . ? C30 H30B 0.9800 . ? C30 H30A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Fe1 O1 92.94(6) . . ? O3 Fe1 O2 93.64(6) . . ? O1 Fe1 O2 102.44(6) . . ? O3 Fe1 N2 97.58(6) . . ? O1 Fe1 N2 163.87(6) . . ? O2 Fe1 N2 89.11(6) . . ? O3 Fe1 N1 96.59(6) . . ? O1 Fe1 N1 88.81(6) . . ? O2 Fe1 N1 164.38(6) . . ? N2 Fe1 N1 77.89(7) . . ? O3 Fe1 N3 177.90(6) . 2_656 ? O1 Fe1 N3 84.96(6) . 2_656 ? O2 Fe1 N3 86.77(6) . 2_656 ? N2 Fe1 N3 84.49(6) . 2_656 ? N1 Fe1 N3 83.44(6) . 2_656 ? O3 C1 C2 121.49(19) . . ? O3 C1 C6 120.28(18) . . ? C2 C1 C6 118.20(19) . . ? C7 N6 N5 113.44(17) . . ? C9 N5 C8 105.28(17) . . ? C9 N5 N6 124.54(17) . . ? C8 N5 N6 129.35(18) . . ? C8 N4 N3 106.06(17) . . ? C9 N3 N4 107.51(17) . . ? C9 N3 Fe1 122.30(14) . 2_646 ? N4 N3 Fe1 129.71(13) . 2_646 ? C16 N1 C17 120.20(18) . . ? C16 N1 Fe1 124.11(15) . . ? C17 N1 Fe1 115.48(13) . . ? C23 N2 C18 119.75(17) . . ? C23 N2 Fe1 125.60(14) . . ? C18 N2 Fe1 114.61(13) . . ? C10 O1 Fe1 128.84(13) . . ? C29 O2 Fe1 131.01(13) . . ? C1 O3 Fe1 136.65(13) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 119.0(2) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C30 O4 H4W 107.4 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 119.82(19) . . ? C5 C6 C7 121.38(19) . . ? C1 C6 C7 118.73(18) . . ? N6 C7 C6 120.84(19) . . ? N6 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? N4 C8 N5 110.70(19) . . ? N4 C8 H8A 124.7 . . ? N5 C8 H8A 124.7 . . ? N3 C9 N5 110.42(19) . . ? N3 C9 H9A 124.8 . . ? N5 C9 H9A 124.8 . . ? O1 C10 C11 119.2(2) . . ? O1 C10 C15 122.78(19) . . ? C11 C10 C15 118.0(2) . . ? C12 C11 C10 121.6(2) . . ? C12 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 119.1(2) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C15 121.8(2) . . ? C13 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? C14 C15 C10 119.1(2) . . ? C14 C15 C16 117.0(2) . . ? C10 C15 C16 123.89(19) . . ? N1 C16 C15 126.0(2) . . ? N1 C16 H16A 117.0 . . ? C15 C16 H16A 117.0 . . ? N1 C17 C22 116.12(18) . . ? N1 C17 C18 107.54(16) . . ? C22 C17 C18 110.45(17) . . ? N1 C17 H17A 107.5 . . ? C22 C17 H17A 107.5 . . ? C18 C17 H17A 107.5 . . ? N2 C18 C19 108.77(16) . . ? N2 C18 C17 107.95(16) . . ? C19 C18 C17 112.31(18) . . ? N2 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C20 C19 C18 112.52(18) . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19B 109.1 . . ? C18 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 110.47(18) . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 109.73(18) . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 C17 112.20(18) . . ? C21 C22 H22A 109.2 . . ? C17 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C17 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? N2 C23 C24 125.42(19) . . ? N2 C23 H23A 117.3 . . ? C24 C23 H23A 117.3 . . ? C25 C24 C29 119.05(19) . . ? C25 C24 C23 116.90(19) . . ? C29 C24 C23 124.00(19) . . ? C26 C25 C24 121.8(2) . . ? C26 C25 H25A 119.1 . . ? C24 C25 H25A 119.1 . . ? C25 C26 C27 119.0(2) . . ? C25 C26 H26A 120.5 . . ? C27 C26 H26A 120.5 . . ? C28 C27 C26 120.7(2) . . ? C28 C27 H27A 119.6 . . ? C26 C27 H27A 119.6 . . ? C27 C28 C29 121.6(2) . . ? C27 C28 H28A 119.2 . . ? C29 C28 H28A 119.2 . . ? O2 C29 C28 118.43(18) . . ? O2 C29 C24 123.71(19) . . ? C28 C29 C24 117.86(18) . . ? O4 C30 H30C 109.5 . . ? O4 C30 H30B 109.5 . . ? H30C C30 H30B 109.5 . . ? O4 C30 H30A 109.5 . . ? H30C C30 H30A 109.5 . . ? H30B C30 H30A 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4W O2 1.04 1.84 2.875(2) 171.3 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.311 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.059 # Attachment 'dt-art-06-2011-011127-File012-v1-0.cif' data_r3 _database_code_depnum_ccdc_archive 'CCDC 830418' #TrackingRef 'dt-art-06-2011-011127-File012-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H25 Fe N6 O4' _chemical_formula_weight 589.41 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1674(4) _cell_length_b 15.1874(5) _cell_length_c 16.4075(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.390(4) _cell_angle_gamma 90.00 _cell_volume 2682.97(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12032 _cell_measurement_theta_min 2.8792 _cell_measurement_theta_max 33.3986 _exptl_crystal_description plate-like _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8876 _exptl_absorpt_correction_T_max 0.9527 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24981 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4720 _reflns_number_gt 3526 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4720 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.38966(3) 0.62617(2) 0.305083(19) 0.01367(11) Uani 1 1 d . . . O3 O 0.38711(13) 0.52210(9) 0.37490(9) 0.0143(3) Uani 1 1 d . . . O2 O 0.42808(14) 0.56321(10) 0.21239(9) 0.0174(4) Uani 1 1 d . . . O1 O 0.21366(13) 0.63912(9) 0.26398(9) 0.0164(4) Uani 1 1 d . . . O4 O 0.25293(15) 0.59980(11) 0.06191(10) 0.0285(4) Uani 1 1 d . . . H4W H 0.3056 0.5905 0.1177 0.050 Uiso 1 1 d . . . N6 N 0.27150(17) 0.59916(12) 0.57698(11) 0.0162(4) Uani 1 1 d . . . N5 N 0.35302(16) 0.64946(11) 0.63973(11) 0.0142(4) Uani 1 1 d . . . N3 N 0.40342(17) 0.75290(12) 0.73394(11) 0.0164(4) Uani 1 1 d . . . N4 N 0.51101(17) 0.70632(12) 0.73413(11) 0.0172(4) Uani 1 1 d . . . N2 N 0.57925(16) 0.64195(11) 0.36346(11) 0.0128(4) Uani 1 1 d . . . N1 N 0.38730(16) 0.71178(11) 0.40644(11) 0.0135(4) Uani 1 1 d . . . C1 C 0.2807(2) 0.48958(14) 0.38441(14) 0.0138(5) Uani 1 1 d . . . C2 C 0.2018(2) 0.43905(14) 0.31989(14) 0.0166(5) Uani 1 1 d . . . H2A H 0.2268 0.4256 0.2703 0.020 Uiso 1 1 calc R . . C3 C 0.0898(2) 0.40908(15) 0.32785(14) 0.0194(5) Uani 1 1 d . . . H3A H 0.0374 0.3760 0.2833 0.023 Uiso 1 1 calc R . . C4 C 0.0519(2) 0.42640(15) 0.40030(14) 0.0190(5) Uani 1 1 d . . . H4A H -0.0258 0.4054 0.4054 0.023 Uiso 1 1 calc R . . C5 C 0.1283(2) 0.47434(14) 0.46454(15) 0.0179(5) Uani 1 1 d . . . H5A H 0.1029 0.4857 0.5144 0.021 Uiso 1 1 calc R . . C6 C 0.2423(2) 0.50668(14) 0.45794(14) 0.0129(5) Uani 1 1 d . . . C7 C 0.3209(2) 0.56009(14) 0.52484(13) 0.0134(5) Uani 1 1 d . . . H7A H 0.4072 0.5658 0.5297 0.016 Uiso 1 1 calc R . . C8 C 0.3113(2) 0.71664(14) 0.67752(14) 0.0159(5) Uani 1 1 d . . . H8A H 0.2272 0.7352 0.6652 0.019 Uiso 1 1 calc R . . C9 C 0.4774(2) 0.64454(15) 0.67773(14) 0.0175(5) Uani 1 1 d . . . H9A H 0.5319 0.6019 0.6648 0.021 Uiso 1 1 calc R . . C10 C 0.5347(2) 0.53286(14) 0.20349(14) 0.0149(5) Uani 1 1 d . . . C11 C 0.5356(2) 0.48475(15) 0.13077(14) 0.0199(5) Uani 1 1 d . . . H11A H 0.4596 0.4739 0.0895 0.024 Uiso 1 1 calc R . . C12 C 0.6446(2) 0.45303(15) 0.11814(15) 0.0217(6) Uani 1 1 d . . . H12A H 0.6428 0.4219 0.0676 0.026 Uiso 1 1 calc R . . C13 C 0.7572(2) 0.46576(15) 0.17815(15) 0.0219(6) Uani 1 1 d . . . H13A H 0.8318 0.4421 0.1697 0.026 Uiso 1 1 calc R . . C14 C 0.7591(2) 0.51292(15) 0.24951(15) 0.0189(5) Uani 1 1 d . . . H14A H 0.8361 0.5219 0.2905 0.023 Uiso 1 1 calc R . . C15 C 0.6496(2) 0.54874(14) 0.26403(13) 0.0147(5) Uani 1 1 d . . . C16 C 0.6655(2) 0.60230(14) 0.33816(13) 0.0146(5) Uani 1 1 d . . . H16A H 0.7482 0.6094 0.3723 0.018 Uiso 1 1 calc R . . C17 C 0.6083(2) 0.69732(14) 0.43555(13) 0.0133(5) Uani 1 1 d . . . C18 C 0.7277(2) 0.71827(14) 0.48239(14) 0.0176(5) Uani 1 1 d . . . H18A H 0.7968 0.6945 0.4664 0.021 Uiso 1 1 calc R . . C19 C 0.7478(2) 0.77289(15) 0.55152(14) 0.0204(5) Uani 1 1 d . . . H19A H 0.8302 0.7864 0.5829 0.024 Uiso 1 1 calc R . . C20 C 0.6480(2) 0.80822(15) 0.57544(15) 0.0216(6) Uani 1 1 d . . . H20A H 0.6619 0.8456 0.6234 0.026 Uiso 1 1 calc R . . C21 C 0.5282(2) 0.78894(14) 0.52937(14) 0.0185(5) Uani 1 1 d . . . H21A H 0.4599 0.8137 0.5457 0.022 Uiso 1 1 calc R . . C22 C 0.5067(2) 0.73389(14) 0.45964(13) 0.0148(5) Uani 1 1 d . . . C23 C 0.2869(2) 0.74169(14) 0.42219(14) 0.0168(5) Uani 1 1 d . . . H23A H 0.2968 0.7765 0.4716 0.020 Uiso 1 1 calc R . . C24 C 0.1624(2) 0.72695(14) 0.37166(14) 0.0170(5) Uani 1 1 d . . . C25 C 0.1304(2) 0.67743(14) 0.29572(14) 0.0167(5) Uani 1 1 d . . . C26 C 0.0046(2) 0.67038(15) 0.25250(15) 0.0204(5) Uani 1 1 d . . . H26A H -0.0189 0.6363 0.2022 0.025 Uiso 1 1 calc R . . C27 C -0.0860(2) 0.71200(16) 0.28147(16) 0.0241(6) Uani 1 1 d . . . H27A H -0.1706 0.7068 0.2505 0.029 Uiso 1 1 calc R . . C28 C -0.0552(2) 0.76125(16) 0.35517(15) 0.0229(6) Uani 1 1 d . . . H28A H -0.1180 0.7901 0.3745 0.027 Uiso 1 1 calc R . . C29 C 0.0669(2) 0.76785(16) 0.39989(15) 0.0224(6) Uani 1 1 d . . . H29A H 0.0879 0.8006 0.4510 0.027 Uiso 1 1 calc R . . C30 C 0.1668(3) 0.5298(2) 0.0509(2) 0.0548(9) Uani 1 1 d . . . H30A H 0.1048 0.5363 -0.0037 0.066 Uiso 1 1 calc R . . H30B H 0.1253 0.5309 0.0965 0.066 Uiso 1 1 calc R . . H30C H 0.2105 0.4737 0.0521 0.066 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 0.01278(18) 0.01573(18) 0.01309(18) 0.00032(14) 0.00449(13) -0.00072(14) O3 0.0121(8) 0.0149(8) 0.0174(8) 0.0015(7) 0.0068(7) -0.0003(6) O2 0.0148(9) 0.0248(9) 0.0137(8) -0.0026(7) 0.0056(7) -0.0011(7) O1 0.0145(9) 0.0176(8) 0.0171(8) -0.0007(7) 0.0039(7) 0.0000(7) O4 0.0255(10) 0.0376(10) 0.0201(9) 0.0032(8) 0.0018(8) -0.0061(8) N6 0.0170(11) 0.0170(10) 0.0143(10) -0.0027(8) 0.0039(8) -0.0023(8) N5 0.0139(10) 0.0145(10) 0.0156(10) -0.0021(8) 0.0062(8) -0.0001(8) N3 0.0156(11) 0.0174(10) 0.0172(10) -0.0025(9) 0.0063(8) 0.0014(8) N4 0.0166(11) 0.0185(10) 0.0164(10) -0.0019(9) 0.0041(8) 0.0031(8) N2 0.0133(10) 0.0139(10) 0.0117(9) 0.0033(8) 0.0041(8) -0.0010(8) N1 0.0135(10) 0.0137(10) 0.0135(10) 0.0019(8) 0.0038(8) -0.0004(8) C1 0.0135(12) 0.0108(11) 0.0165(12) 0.0041(10) 0.0032(10) 0.0036(9) C2 0.0201(14) 0.0153(12) 0.0152(12) -0.0025(10) 0.0064(10) 0.0015(10) C3 0.0167(13) 0.0174(12) 0.0211(13) -0.0052(10) -0.0005(10) -0.0007(10) C4 0.0104(12) 0.0210(13) 0.0259(13) -0.0007(11) 0.0055(10) -0.0013(10) C5 0.0161(13) 0.0180(13) 0.0222(13) -0.0015(10) 0.0098(10) 0.0025(10) C6 0.0117(12) 0.0105(11) 0.0165(12) 0.0002(9) 0.0038(9) 0.0026(9) C7 0.0131(12) 0.0135(12) 0.0139(12) 0.0022(10) 0.0040(9) 0.0008(9) C8 0.0156(13) 0.0171(12) 0.0178(12) -0.0022(10) 0.0090(10) 0.0011(10) C9 0.0170(13) 0.0185(13) 0.0175(12) -0.0001(10) 0.0055(10) 0.0030(10) C10 0.0174(13) 0.0121(11) 0.0164(12) 0.0035(10) 0.0069(10) 0.0004(10) C11 0.0213(14) 0.0202(13) 0.0176(13) -0.0011(11) 0.0041(10) -0.0025(10) C12 0.0296(15) 0.0191(13) 0.0193(13) -0.0035(11) 0.0116(11) -0.0004(11) C13 0.0233(14) 0.0189(13) 0.0262(14) -0.0030(11) 0.0112(11) 0.0054(10) C14 0.0183(13) 0.0172(13) 0.0211(13) 0.0035(11) 0.0051(10) 0.0010(10) C15 0.0192(13) 0.0126(11) 0.0141(12) 0.0037(10) 0.0074(10) -0.0003(10) C16 0.0143(13) 0.0153(12) 0.0131(12) 0.0052(9) 0.0018(10) -0.0015(9) C17 0.0172(13) 0.0115(11) 0.0117(11) 0.0030(9) 0.0049(9) -0.0003(9) C18 0.0153(13) 0.0182(12) 0.0193(12) 0.0012(10) 0.0043(10) 0.0017(10) C19 0.0173(13) 0.0210(13) 0.0196(13) -0.0017(11) -0.0007(10) -0.0016(10) C20 0.0259(15) 0.0192(13) 0.0180(13) -0.0038(10) 0.0028(11) 0.0011(11) C21 0.0196(13) 0.0188(13) 0.0176(12) -0.0002(10) 0.0055(10) 0.0032(10) C22 0.0158(13) 0.0138(12) 0.0139(12) 0.0033(10) 0.0026(10) -0.0004(9) C23 0.0212(14) 0.0148(12) 0.0164(12) 0.0020(10) 0.0085(10) 0.0007(10) C24 0.0161(13) 0.0181(12) 0.0182(12) 0.0042(10) 0.0072(10) -0.0019(10) C25 0.0166(13) 0.0162(12) 0.0188(13) 0.0112(10) 0.0072(10) 0.0009(10) C26 0.0193(14) 0.0188(13) 0.0228(13) 0.0041(11) 0.0049(11) -0.0032(10) C27 0.0144(13) 0.0270(14) 0.0310(14) 0.0105(12) 0.0061(11) -0.0034(11) C28 0.0141(13) 0.0272(14) 0.0306(15) 0.0062(12) 0.0119(11) 0.0028(11) C29 0.0243(15) 0.0254(14) 0.0213(13) 0.0018(11) 0.0125(11) 0.0000(11) C30 0.0394(19) 0.069(2) 0.0468(19) 0.0109(17) -0.0051(15) -0.0238(17) _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 O1 1.9112(15) . ? Fe1 O2 1.9384(14) . ? Fe1 O3 1.9566(14) . ? Fe1 N2 2.0931(18) . ? Fe1 N1 2.1166(18) . ? Fe1 N3 2.2033(18) 4_575 ? O3 C1 1.334(3) . ? O2 C10 1.320(3) . ? O1 C25 1.316(3) . ? O4 C30 1.412(3) . ? O4 H4W 0.9582 . ? N6 C7 1.280(3) . ? N6 N5 1.405(3) . ? N5 C8 1.340(3) . ? N5 C9 1.366(3) . ? N3 C8 1.309(3) . ? N3 N4 1.394(2) . ? N3 Fe1 2.2033(18) 4_576 ? N4 C9 1.301(3) . ? N2 C16 1.294(3) . ? N2 C17 1.417(3) . ? N1 C23 1.297(3) . ? N1 C22 1.426(3) . ? C1 C6 1.407(3) . ? C1 C2 1.411(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.9500 . ? C3 C4 1.388(3) . ? C3 H3A 0.9500 . ? C4 C5 1.375(3) . ? C4 H4A 0.9500 . ? C5 C6 1.395(3) . ? C5 H5A 0.9500 . ? C6 C7 1.457(3) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.402(3) . ? C10 C15 1.420(3) . ? C11 C12 1.374(3) . ? C11 H11A 0.9500 . ? C12 C13 1.390(3) . ? C12 H12A 0.9500 . ? C13 C14 1.368(3) . ? C13 H13A 0.9500 . ? C14 C15 1.415(3) . ? C14 H14A 0.9500 . ? C15 C16 1.434(3) . ? C16 H16A 0.9500 . ? C17 C18 1.388(3) . ? C17 C22 1.411(3) . ? C18 C19 1.375(3) . ? C18 H18A 0.9500 . ? C19 C20 1.384(3) . ? C19 H19A 0.9500 . ? C20 C21 1.382(3) . ? C20 H20A 0.9500 . ? C21 C22 1.386(3) . ? C21 H21A 0.9500 . ? C23 C24 1.435(3) . ? C23 H23A 0.9500 . ? C24 C29 1.415(3) . ? C24 C25 1.418(3) . ? C25 C26 1.399(3) . ? C26 C27 1.380(3) . ? C26 H26A 0.9500 . ? C27 C28 1.385(3) . ? C27 H27A 0.9500 . ? C28 C29 1.370(3) . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe1 O2 101.24(6) . . ? O1 Fe1 O3 96.68(6) . . ? O2 Fe1 O3 95.83(6) . . ? O1 Fe1 N2 166.00(7) . . ? O2 Fe1 N2 90.45(7) . . ? O3 Fe1 N2 89.70(6) . . ? O1 Fe1 N1 89.31(7) . . ? O2 Fe1 N1 166.14(7) . . ? O3 Fe1 N1 91.78(6) . . ? N2 Fe1 N1 78.00(7) . . ? O1 Fe1 N3 86.39(7) . 4_575 ? O2 Fe1 N3 86.24(6) . 4_575 ? O3 Fe1 N3 175.87(7) . 4_575 ? N2 Fe1 N3 86.71(7) . 4_575 ? N1 Fe1 N3 85.49(7) . 4_575 ? C1 O3 Fe1 121.28(13) . . ? C10 O2 Fe1 130.76(14) . . ? C25 O1 Fe1 132.42(14) . . ? C30 O4 H4W 103.7 . . ? C7 N6 N5 115.56(18) . . ? C8 N5 C9 105.48(18) . . ? C8 N5 N6 121.05(18) . . ? C9 N5 N6 133.44(18) . . ? C8 N3 N4 107.65(17) . . ? C8 N3 Fe1 124.98(15) . 4_576 ? N4 N3 Fe1 127.11(14) . 4_576 ? C9 N4 N3 106.20(18) . . ? C16 N2 C17 121.26(19) . . ? C16 N2 Fe1 123.28(15) . . ? C17 N2 Fe1 115.43(13) . . ? C23 N1 C22 120.82(19) . . ? C23 N1 Fe1 124.27(16) . . ? C22 N1 Fe1 114.89(14) . . ? O3 C1 C6 121.02(19) . . ? O3 C1 C2 120.78(19) . . ? C6 C1 C2 118.2(2) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 119.3(2) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C5 C6 C1 119.5(2) . . ? C5 C6 C7 121.13(19) . . ? C1 C6 C7 119.29(19) . . ? N6 C7 C6 118.8(2) . . ? N6 C7 H7A 120.6 . . ? C6 C7 H7A 120.6 . . ? N3 C8 N5 110.1(2) . . ? N3 C8 H8A 125.0 . . ? N5 C8 H8A 125.0 . . ? N4 C9 N5 110.58(19) . . ? N4 C9 H9A 124.7 . . ? N5 C9 H9A 124.7 . . ? O2 C10 C11 119.1(2) . . ? O2 C10 C15 122.5(2) . . ? C11 C10 C15 118.3(2) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C11 C12 C13 121.0(2) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C14 C13 C12 119.0(2) . . ? C14 C13 H13A 120.5 . . ? C12 C13 H13A 120.5 . . ? C13 C14 C15 121.9(2) . . ? C13 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? C14 C15 C10 118.6(2) . . ? C14 C15 C16 116.3(2) . . ? C10 C15 C16 125.1(2) . . ? N2 C16 C15 126.9(2) . . ? N2 C16 H16A 116.6 . . ? C15 C16 H16A 116.6 . . ? C18 C17 C22 118.7(2) . . ? C18 C17 N2 124.9(2) . . ? C22 C17 N2 116.41(19) . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C21 C20 C19 119.9(2) . . ? C21 C20 H20A 120.1 . . ? C19 C20 H20A 120.1 . . ? C20 C21 C22 120.7(2) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C21 C22 C17 119.5(2) . . ? C21 C22 N1 125.2(2) . . ? C17 C22 N1 115.24(19) . . ? N1 C23 C24 125.9(2) . . ? N1 C23 H23A 117.1 . . ? C24 C23 H23A 117.1 . . ? C29 C24 C25 119.0(2) . . ? C29 C24 C23 116.2(2) . . ? C25 C24 C23 124.8(2) . . ? O1 C25 C26 119.0(2) . . ? O1 C25 C24 122.8(2) . . ? C26 C25 C24 118.1(2) . . ? C27 C26 C25 121.3(2) . . ? C27 C26 H26A 119.4 . . ? C25 C26 H26A 119.4 . . ? C26 C27 C28 120.9(2) . . ? C26 C27 H27A 119.6 . . ? C28 C27 H27A 119.6 . . ? C29 C28 C27 119.2(2) . . ? C29 C28 H28A 120.4 . . ? C27 C28 H28A 120.4 . . ? C28 C29 C24 121.5(2) . . ? C28 C29 H29A 119.3 . . ? C24 C29 H29A 119.3 . . ? O4 C30 H30A 109.5 . . ? O4 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O4 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4W O2 0.96 1.82 2.769(2) 168.1 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.523 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.063