# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1599 data_1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H16 Fe N2 O2' _chemical_formula_weight 324.16 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' '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(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8871(12) _cell_length_b 11.597(2) _cell_length_c 20.262(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.02(3) _cell_angle_gamma 90.00 _cell_volume 1383.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 4748 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 28.20 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method ? _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8316 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.42 _reflns_number_total 3172 _reflns_number_observed 2320 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.6699P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom and located' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3172 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_obs 0.0422 _refine_ls_wR_factor_all 0.0933 _refine_ls_wR_factor_obs 0.0840 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.107 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.107 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe1 Fe -0.59046(6) 0.02934(3) 0.184558(17) 0.02065(12) Uani 1 d . . O2 O -0.8984(4) -0.02609(18) 0.41762(9) 0.0357(5) Uani 1 d . . O4 O -0.6529(4) 0.23063(18) 0.57237(10) 0.0410(6) Uani 1 d . . N1 N -0.5574(4) 0.06231(18) 0.40188(10) 0.0235(5) Uani 1 d . . N3 N -0.7676(4) 0.1024(2) 0.49438(11) 0.0289(6) Uani 1 d . . H3 H -0.884(6) 0.087(3) 0.5184(17) 0.055(11) Uiso 1 d . . C2 C -0.7508(5) 0.0417(2) 0.43652(13) 0.0263(6) Uani 1 d . . C4 C -0.6148(5) 0.1828(2) 0.51951(13) 0.0277(6) Uani 1 d . . C5 C -0.4181(5) 0.2025(2) 0.47981(13) 0.0267(6) Uani 1 d . . C6 C -0.3982(5) 0.1417(2) 0.42359(13) 0.0268(6) Uani 1 d . . H6 H -0.2707 0.1539 0.3981 0.032 Uiso 1 calc R . C7 C -0.2434(6) 0.2863(3) 0.50408(15) 0.0374(7) Uani 1 d . . H7A H -0.3099 0.3617 0.5068 0.056 Uiso 1 calc R . H7B H -0.1191 0.2880 0.4741 0.056 Uiso 1 calc R . H7C H -0.1889 0.2632 0.5470 0.056 Uiso 1 calc R . C8 C -0.5245(5) 0.0018(2) 0.33815(12) 0.0261(6) Uani 1 d . . H8A H -0.6088 -0.0700 0.3381 0.031 Uiso 1 calc R . H8B H -0.3648 -0.0165 0.3334 0.031 Uiso 1 calc R . C9 C -0.6022(4) 0.0738(2) 0.28111(12) 0.0216(6) Uani 1 d . . C10 C -0.4661(5) 0.1535(2) 0.24598(13) 0.0265(6) Uani 1 d . . H10 H -0.3137 0.1696 0.2546 0.032 Uiso 1 calc R . C11 C -0.6042(5) 0.2045(2) 0.19521(13) 0.0307(7) Uani 1 d . . H11 H -0.5573 0.2594 0.1649 0.037 Uiso 1 calc R . C12 C -0.8245(5) 0.1570(2) 0.19897(13) 0.0294(7) Uani 1 d . . H12 H -0.9477 0.1748 0.1715 0.035 Uiso 1 calc R . C13 C -0.8249(5) 0.0770(2) 0.25221(13) 0.0267(6) Uani 1 d . . H13 H -0.9491 0.0341 0.2658 0.032 Uiso 1 calc R . C14 C -0.4442(6) -0.1294(2) 0.18041(15) 0.0365(8) Uani 1 d . . H14 H -0.3926 -0.1723 0.2165 0.044 Uiso 1 calc R . C15 C -0.3153(5) -0.0487(2) 0.14463(14) 0.0338(7) Uani 1 d . . H15 H -0.1639 -0.0297 0.1528 0.041 Uiso 1 calc R . C16 C -0.4567(5) -0.0018(2) 0.09431(13) 0.0292(7) Uani 1 d . . H16 H -0.4154 0.0539 0.0638 0.035 Uiso 1 calc R . C17 C -0.6724(5) -0.0548(2) 0.09868(13) 0.0303(7) Uani 1 d . . H17 H -0.7977 -0.0403 0.0713 0.036 Uiso 1 calc R . C18 C -0.6644(6) -0.1338(2) 0.15206(14) 0.0352(7) Uani 1 d . . H18 H -0.7831 -0.1803 0.1659 0.042 Uiso 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 0.0252(2) 0.0217(2) 0.01504(19) -0.00122(16) 0.00184(14) 0.00172(17) O2 0.0376(12) 0.0482(13) 0.0214(10) -0.0080(9) 0.0055(9) -0.0154(10) O4 0.0467(14) 0.0487(14) 0.0278(12) -0.0137(10) 0.0049(10) -0.0050(11) N1 0.0279(13) 0.0299(13) 0.0129(10) -0.0020(9) 0.0014(9) -0.0028(10) N3 0.0304(14) 0.0362(14) 0.0203(12) -0.0032(10) 0.0047(11) -0.0050(11) C2 0.0306(15) 0.0313(16) 0.0170(13) 0.0007(11) 0.0009(11) -0.0011(13) C4 0.0331(16) 0.0281(15) 0.0218(14) 0.0009(12) -0.0029(12) -0.0007(13) C5 0.0322(16) 0.0283(15) 0.0194(13) 0.0038(11) -0.0036(12) -0.0015(12) C6 0.0309(16) 0.0290(15) 0.0203(14) 0.0060(11) -0.0005(12) -0.0031(12) C7 0.0443(19) 0.0367(18) 0.0310(17) -0.0036(13) -0.0034(14) -0.0129(15) C8 0.0295(16) 0.0312(16) 0.0177(13) -0.0016(11) 0.0027(11) 0.0009(11) C9 0.0273(15) 0.0237(13) 0.0139(12) -0.0033(10) 0.0035(11) 0.0018(11) C10 0.0301(16) 0.0272(15) 0.0224(14) -0.0054(11) 0.0019(12) -0.0045(12) C11 0.0482(19) 0.0231(14) 0.0210(15) -0.0004(11) 0.0055(13) 0.0015(13) C12 0.0342(17) 0.0328(16) 0.0213(15) -0.0046(12) -0.0016(12) 0.0104(13) C13 0.0273(15) 0.0320(15) 0.0210(14) -0.0031(12) 0.0044(12) 0.0046(12) C14 0.055(2) 0.0278(16) 0.0271(15) -0.0009(13) 0.0010(15) 0.0181(14) C15 0.0263(16) 0.0428(19) 0.0324(16) -0.0132(14) 0.0021(13) 0.0075(13) C16 0.0374(17) 0.0315(16) 0.0191(14) -0.0040(11) 0.0084(12) 0.0023(12) C17 0.0337(16) 0.0356(17) 0.0215(14) -0.0068(12) -0.0033(12) 0.0022(13) C18 0.051(2) 0.0253(16) 0.0292(16) -0.0050(13) 0.0080(15) -0.0044(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 C9 2.026(2) . ? Fe1 C10 2.031(3) . ? Fe1 C14 2.035(3) . ? Fe1 C15 2.036(3) . ? Fe1 C16 2.036(3) . ? Fe1 C13 2.039(3) . ? Fe1 C11 2.044(3) . ? Fe1 C17 2.045(3) . ? Fe1 C12 2.047(3) . ? Fe1 C18 2.048(3) . ? O2 C2 1.228(3) . ? O4 C4 1.230(3) . ? N1 C2 1.369(3) . ? N1 C6 1.380(3) . ? N1 C8 1.485(3) . ? N3 H3 0.87(4) . ? N3 C2 1.373(3) . ? N3 C4 1.386(4) . ? C4 C5 1.440(4) . ? C5 C6 1.346(4) . ? C5 C7 1.492(4) . ? C8 C9 1.491(4) . ? C9 C10 1.422(4) . ? C9 C13 1.427(4) . ? C10 C11 1.428(4) . ? C11 C12 1.412(4) . ? C12 C13 1.423(4) . ? C14 C18 1.409(5) . ? C14 C15 1.414(4) . ? C15 C16 1.414(4) . ? C16 C17 1.415(4) . ? C17 C18 1.418(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Fe1 C10 41.04(10) . . ? C9 Fe1 C14 106.99(11) . . ? C10 Fe1 C14 121.24(13) . . ? C9 Fe1 C15 122.56(12) . . ? C10 Fe1 C15 106.14(12) . . ? C14 Fe1 C15 40.64(12) . . ? C9 Fe1 C16 158.91(11) . . ? C10 Fe1 C16 122.36(11) . . ? C14 Fe1 C16 68.39(12) . . ? C15 Fe1 C16 40.63(12) . . ? C9 Fe1 C13 41.09(10) . . ? C10 Fe1 C13 68.70(11) . . ? C14 Fe1 C13 124.40(12) . . ? C15 Fe1 C13 160.16(12) . . ? C16 Fe1 C13 158.31(12) . . ? C9 Fe1 C11 69.07(11) . . ? C10 Fe1 C11 41.02(11) . . ? C14 Fe1 C11 157.06(13) . . ? C15 Fe1 C11 121.12(12) . . ? C16 Fe1 C11 106.73(11) . . ? C13 Fe1 C11 68.36(11) . . ? C9 Fe1 C17 158.69(11) . . ? C10 Fe1 C17 159.48(11) . . ? C14 Fe1 C17 68.08(12) . . ? C15 Fe1 C17 68.11(12) . . ? C16 Fe1 C17 40.57(11) . . ? C13 Fe1 C17 123.30(12) . . ? C11 Fe1 C17 123.69(11) . . ? C9 Fe1 C12 69.09(11) . . ? C10 Fe1 C12 68.66(12) . . ? C14 Fe1 C12 161.19(13) . . ? C15 Fe1 C12 157.03(12) . . ? C16 Fe1 C12 121.91(11) . . ? C13 Fe1 C12 40.76(11) . . ? C11 Fe1 C12 40.40(12) . . ? C17 Fe1 C12 108.50(12) . . ? C9 Fe1 C18 122.36(11) . . ? C10 Fe1 C18 157.56(12) . . ? C14 Fe1 C18 40.37(13) . . ? C15 Fe1 C18 68.13(13) . . ? C16 Fe1 C18 68.32(11) . . ? C13 Fe1 C18 108.91(12) . . ? C11 Fe1 C18 160.65(13) . . ? C17 Fe1 C18 40.53(11) . . ? C12 Fe1 C18 125.06(13) . . ? C2 N1 C6 121.3(2) . . ? C2 N1 C8 119.1(2) . . ? C6 N1 C8 119.6(2) . . ? H3 N3 C2 116(2) . . ? H3 N3 C4 117(2) . . ? C2 N3 C4 127.1(3) . . ? O2 C2 N1 122.8(2) . . ? O2 C2 N3 122.2(3) . . ? N1 C2 N3 114.9(2) . . ? O4 C4 N3 119.7(3) . . ? O4 C4 C5 125.2(3) . . ? N3 C4 C5 115.1(2) . . ? C6 C5 C4 118.2(3) . . ? C6 C5 C7 123.4(3) . . ? C4 C5 C7 118.4(3) . . ? C5 C6 N1 123.4(3) . . ? N1 C8 C9 111.5(2) . . ? C10 C9 C13 107.5(2) . . ? C10 C9 C8 125.7(2) . . ? C13 C9 C8 126.8(2) . . ? C10 C9 Fe1 69.68(14) . . ? C13 C9 Fe1 69.95(14) . . ? C8 C9 Fe1 126.18(18) . . ? C9 C10 C11 108.1(3) . . ? C9 C10 Fe1 69.28(15) . . ? C11 C10 Fe1 69.98(16) . . ? C12 C11 C10 108.1(2) . . ? C12 C11 Fe1 69.89(16) . . ? C10 C11 Fe1 69.00(15) . . ? C11 C12 C13 108.0(3) . . ? C11 C12 Fe1 69.71(16) . . ? C13 C12 Fe1 69.33(15) . . ? C12 C13 C9 108.3(2) . . ? C12 C13 Fe1 69.91(15) . . ? C9 C13 Fe1 68.96(14) . . ? C18 C14 C15 108.3(3) . . ? C18 C14 Fe1 70.30(16) . . ? C15 C14 Fe1 69.71(16) . . ? C16 C15 C14 108.0(3) . . ? C16 C15 Fe1 69.69(15) . . ? C14 C15 Fe1 69.65(16) . . ? C15 C16 C17 107.8(3) . . ? C15 C16 Fe1 69.68(15) . . ? C17 C16 Fe1 70.06(15) . . ? C16 C17 C18 108.1(3) . . ? C16 C17 Fe1 69.37(15) . . ? C18 C17 Fe1 69.84(16) . . ? C14 C18 C17 107.8(3) . . ? C14 C18 Fe1 69.33(16) . . ? C17 C18 Fe1 69.63(16) . . ? _refine_diff_density_max 0.373 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.074 data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H15 Fe N3 O' _chemical_formula_weight 309.15 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' '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(1)/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 17.0466(19) _cell_length_b 7.3337(8) _cell_length_c 10.6368(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.972(3) _cell_angle_gamma 90.00 _cell_volume 1278.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3777 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.15 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method ? _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 1.177 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.676 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6972 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.43 _reflns_number_total 2864 _reflns_number_observed 2118 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.2615P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom and located' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2864 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_obs 0.0409 _refine_ls_wR_factor_all 0.0950 _refine_ls_wR_factor_obs 0.0848 _refine_ls_goodness_of_fit_all 1.017 _refine_ls_goodness_of_fit_obs 1.067 _refine_ls_restrained_S_all 1.017 _refine_ls_restrained_S_obs 1.067 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Fe1 Fe 0.34814(2) 0.48775(5) 0.55983(3) 0.02339(14) Uani 1 d . . O2 O 0.09696(12) 0.6240(3) 0.19863(18) 0.0338(5) Uani 1 d . . N1 N 0.13741(13) 0.8286(3) 0.3650(2) 0.0243(5) Uani 1 d . . N3 N 0.06326(13) 0.9220(3) 0.1517(2) 0.0274(5) Uani 1 d . . N4 N 0.03987(15) 1.2263(4) 0.1056(3) 0.0321(6) Uani 1 d . . H4A H 0.0446(17) 1.337(4) 0.134(3) 0.028(8) Uiso 1 d . . H4B H 0.0116(19) 1.196(5) 0.026(3) 0.044(10) Uiso 1 d . . C2 C 0.09798(16) 0.7856(4) 0.2345(3) 0.0268(6) Uani 1 d . . C4 C 0.06947(16) 1.0953(4) 0.1933(3) 0.0260(6) Uani 1 d . . C5 C 0.10702(17) 1.1416(4) 0.3262(3) 0.0298(6) Uani 1 d . . H5 H 0.1097 1.2642 0.3559 0.036 Uiso 1 calc R . C6 C 0.13849(15) 1.0041(4) 0.4075(3) 0.0281(6) Uani 1 d . . H6 H 0.1623 1.0298 0.4974 0.034 Uiso 1 calc R . C8 C 0.18018(16) 0.6861(4) 0.4554(2) 0.0270(6) Uani 1 d . . H8A H 0.1519 0.5681 0.4310 0.032 Uiso 1 calc R . H8B H 0.1786 0.7165 0.5453 0.032 Uiso 1 calc R . C9 C 0.26713(15) 0.6680(3) 0.4524(2) 0.0209(5) Uani 1 d . . C10 C 0.33549(17) 0.7606(3) 0.5359(2) 0.0282(6) Uani 1 d . . H10 H 0.3337 0.8467 0.6018 0.034 Uiso 1 calc R . C11 C 0.40667(17) 0.7009(4) 0.5029(3) 0.0303(6) Uani 1 d . . H11 H 0.4609 0.7400 0.5432 0.036 Uiso 1 calc R . C12 C 0.38282(18) 0.5736(4) 0.4001(3) 0.0307(6) Uani 1 d . . H12 H 0.4182 0.5120 0.3592 0.037 Uiso 1 calc R . C13 C 0.29706(17) 0.5537(4) 0.3683(2) 0.0258(6) Uani 1 d . . H13 H 0.2650 0.4769 0.3020 0.031 Uiso 1 calc R . C14 C 0.2845(2) 0.3290(4) 0.6529(3) 0.0421(8) Uani 1 d . . H14 H 0.2273 0.3338 0.6411 0.050 Uiso 1 calc R . C15 C 0.3437(4) 0.4297(5) 0.7437(3) 0.0730(15) Uani 1 d . . H15 H 0.3337 0.5147 0.8049 0.088 Uiso 1 calc R . C16 C 0.4203(3) 0.3827(6) 0.7284(4) 0.0791(17) Uani 1 d . . H16 H 0.4714 0.4304 0.7772 0.095 Uiso 1 calc R . C17 C 0.4080(2) 0.2538(5) 0.6288(4) 0.0552(11) Uani 1 d . . H17 H 0.4495 0.1982 0.5977 0.066 Uiso 1 calc R . C18 C 0.3250(2) 0.2204(4) 0.5829(3) 0.0363(7) Uani 1 d . . H18 H 0.2999 0.1376 0.5151 0.044 Uiso 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 0.0316(2) 0.0173(2) 0.0189(2) 0.00322(16) 0.00314(14) -0.00076(17) O2 0.0376(12) 0.0288(11) 0.0351(11) -0.0041(9) 0.0104(9) 0.0014(9) N1 0.0230(12) 0.0279(12) 0.0226(11) 0.0020(10) 0.0071(9) 0.0026(9) N3 0.0251(12) 0.0343(13) 0.0234(11) 0.0011(10) 0.0075(10) 0.0047(10) N4 0.0356(15) 0.0335(15) 0.0261(14) 0.0041(12) 0.0067(12) 0.0067(11) C2 0.0221(14) 0.0360(16) 0.0251(14) -0.0007(12) 0.0110(11) 0.0020(12) C4 0.0217(14) 0.0316(15) 0.0282(14) 0.0018(13) 0.0126(11) 0.0042(11) C5 0.0303(16) 0.0275(15) 0.0306(15) -0.0050(12) 0.0068(12) 0.0019(12) C6 0.0243(13) 0.0332(15) 0.0257(13) -0.0031(13) 0.0048(10) -0.0007(13) C8 0.0308(15) 0.0287(14) 0.0219(13) 0.0056(11) 0.0079(11) 0.0014(12) C9 0.0260(14) 0.0176(12) 0.0190(12) 0.0035(10) 0.0061(10) 0.0017(10) C10 0.0445(18) 0.0156(12) 0.0227(13) 0.0025(11) 0.0060(12) -0.0015(12) C11 0.0248(15) 0.0299(14) 0.0333(15) 0.0127(13) 0.0030(12) -0.0020(12) C12 0.0361(16) 0.0319(15) 0.0276(14) 0.0102(12) 0.0149(12) 0.0107(12) C13 0.0376(16) 0.0251(14) 0.0145(12) 0.0018(10) 0.0069(11) 0.0035(11) C14 0.052(2) 0.0367(17) 0.0458(18) 0.0240(16) 0.0270(16) 0.0098(15) C15 0.169(5) 0.0298(18) 0.0211(16) 0.0087(14) 0.027(3) -0.009(3) C16 0.079(3) 0.066(3) 0.057(2) 0.043(2) -0.042(2) -0.036(2) C17 0.039(2) 0.0414(19) 0.087(3) 0.042(2) 0.0195(19) 0.0142(16) C18 0.052(2) 0.0179(13) 0.0393(17) 0.0053(13) 0.0127(14) -0.0030(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 C10 2.021(3) . ? Fe1 C9 2.023(2) . ? Fe1 C15 2.024(3) . ? Fe1 C14 2.026(3) . ? Fe1 C16 2.026(3) . ? Fe1 C17 2.028(3) . ? Fe1 C18 2.028(3) . ? Fe1 C11 2.034(3) . ? Fe1 C13 2.041(2) . ? Fe1 C12 2.046(3) . ? O2 C2 1.244(3) . ? N1 C6 1.363(3) . ? N1 C2 1.402(3) . ? N1 C8 1.471(3) . ? N3 C4 1.341(4) . ? N3 C2 1.357(3) . ? N4 C4 1.338(4) . ? C4 C5 1.423(4) . ? C5 C6 1.340(4) . ? C8 C9 1.497(4) . ? C9 C13 1.419(3) . ? C9 C10 1.428(4) . ? C10 C11 1.422(4) . ? C11 C12 1.410(4) . ? C12 C13 1.414(4) . ? C14 C18 1.396(4) . ? C14 C15 1.399(5) . ? C15 C16 1.403(7) . ? C16 C17 1.392(6) . ? C17 C18 1.386(5) . ? 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 C10 Fe1 C9 41.35(10) . . ? C10 Fe1 C15 107.40(14) . . ? C9 Fe1 C15 118.83(18) . . ? C10 Fe1 C14 125.28(12) . . ? C9 Fe1 C14 106.12(11) . . ? C15 Fe1 C14 40.44(16) . . ? C10 Fe1 C16 120.37(16) . . ? C9 Fe1 C16 154.42(19) . . ? C15 Fe1 C16 40.53(19) . . ? C14 Fe1 C16 68.00(16) . . ? C10 Fe1 C17 155.35(14) . . ? C9 Fe1 C17 162.70(14) . . ? C15 Fe1 C17 67.75(17) . . ? C14 Fe1 C17 67.72(13) . . ? C16 Fe1 C17 40.16(18) . . ? C10 Fe1 C18 162.70(13) . . ? C9 Fe1 C18 125.08(12) . . ? C15 Fe1 C18 67.63(14) . . ? C14 Fe1 C18 40.30(12) . . ? C16 Fe1 C18 67.45(14) . . ? C17 Fe1 C18 39.97(13) . . ? C10 Fe1 C11 41.04(11) . . ? C9 Fe1 C11 69.16(10) . . ? C15 Fe1 C11 126.97(15) . . ? C14 Fe1 C11 163.64(12) . . ? C16 Fe1 C11 109.11(14) . . ? C17 Fe1 C11 121.24(13) . . ? C18 Fe1 C11 155.03(13) . . ? C10 Fe1 C13 68.78(10) . . ? C9 Fe1 C13 40.86(10) . . ? C15 Fe1 C13 153.56(19) . . ? C14 Fe1 C13 119.04(13) . . ? C16 Fe1 C13 164.0(2) . . ? C17 Fe1 C13 126.56(15) . . ? C18 Fe1 C13 107.82(12) . . ? C11 Fe1 C13 68.30(11) . . ? C10 Fe1 C12 68.64(11) . . ? C9 Fe1 C12 68.77(11) . . ? C15 Fe1 C12 164.55(18) . . ? C14 Fe1 C12 154.00(14) . . ? C16 Fe1 C12 127.45(18) . . ? C17 Fe1 C12 109.22(14) . . ? C18 Fe1 C12 120.54(12) . . ? C11 Fe1 C12 40.44(12) . . ? C13 Fe1 C12 40.49(11) . . ? C6 N1 C2 120.0(2) . . ? C6 N1 C8 119.7(2) . . ? C2 N1 C8 120.2(2) . . ? C4 N3 C2 120.3(2) . . ? O2 C2 N3 122.5(2) . . ? O2 C2 N1 118.7(2) . . ? N3 C2 N1 118.8(2) . . ? N4 C4 N3 118.0(2) . . ? N4 C4 C5 120.1(3) . . ? N3 C4 C5 121.8(2) . . ? C6 C5 C4 116.9(3) . . ? C5 C6 N1 122.0(2) . . ? N1 C8 C9 111.4(2) . . ? C13 C9 C10 107.4(2) . . ? C13 C9 C8 126.6(2) . . ? C10 C9 C8 126.0(2) . . ? C13 C9 Fe1 70.26(14) . . ? C10 C9 Fe1 69.25(14) . . ? C8 C9 Fe1 124.87(17) . . ? C11 C10 C9 107.8(2) . . ? C11 C10 Fe1 69.99(15) . . ? C9 C10 Fe1 69.40(14) . . ? C12 C11 C10 108.1(2) . . ? C12 C11 Fe1 70.23(16) . . ? C10 C11 Fe1 68.97(15) . . ? C11 C12 C13 108.2(2) . . ? C11 C12 Fe1 69.33(15) . . ? C13 C12 Fe1 69.56(15) . . ? C12 C13 C9 108.4(2) . . ? C12 C13 Fe1 69.95(15) . . ? C9 C13 Fe1 68.88(14) . . ? C18 C14 C15 107.5(3) . . ? C18 C14 Fe1 69.95(17) . . ? C15 C14 Fe1 69.7(2) . . ? C14 C15 C16 107.9(4) . . ? C14 C15 Fe1 69.86(18) . . ? C16 C15 Fe1 69.8(2) . . ? C17 C16 C15 107.8(3) . . ? C17 C16 Fe1 69.98(19) . . ? C15 C16 Fe1 69.6(2) . . ? C18 C17 C16 108.3(4) . . ? C18 C17 Fe1 70.02(17) . . ? C16 C17 Fe1 69.9(2) . . ? C17 C18 C14 108.5(3) . . ? C17 C18 Fe1 70.01(18) . . ? C14 C18 Fe1 69.76(16) . . ? _refine_diff_density_max 0.363 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.069 data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl Fe N5' _chemical_formula_weight 367.62 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' 'Cl' 'Cl' 0.1484 0.1585 '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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 7.912(3) _cell_length_b 9.803(3) _cell_length_c 38.335(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.622(8) _cell_angle_gamma 90.00 _cell_volume 2970.3(17) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 2536 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 1.201 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.518 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6990 _diffrn_reflns_av_R_equivalents 0.1035 _diffrn_reflns_av_sigmaI/netI 0.1381 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2593 _reflns_number_gt 1494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0822P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2593 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1502 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.1806 _refine_ls_wR_factor_gt 0.1510 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.10384(13) 0.24065(10) 0.43452(3) 0.0207(4) Uani 1 1 d . . . N1 N 0.2475(8) 0.6153(6) 0.34235(17) 0.0279(16) Uani 1 1 d . . . C2 C 0.2804(9) 0.4801(7) 0.33371(18) 0.0204(17) Uani 1 1 d . . . N3 N 0.3531(7) 0.4343(6) 0.30579(15) 0.0233(15) Uani 1 1 d . . . C4 C 0.4077(10) 0.5338(7) 0.28518(19) 0.0230(18) Uani 1 1 d . . . C5 C 0.3895(9) 0.6757(6) 0.29133(19) 0.0224(18) Uani 1 1 d . . . C6 C 0.3038(9) 0.7087(7) 0.3206(2) 0.0249(18) Uani 1 1 d . . . Cl6 Cl 0.2648(3) 0.87900(18) 0.33086(5) 0.0372(6) Uani 1 1 d . . . N7 N 0.4626(8) 0.7497(6) 0.26536(15) 0.0279(15) Uani 1 1 d . . . C8 C 0.5222(10) 0.6538(7) 0.24441(19) 0.0266(19) Uani 1 1 d . . . H8 H 0.5814 0.6737 0.2240 0.032 Uiso 1 1 calc R . . N9 N 0.4892(8) 0.5237(5) 0.25538(15) 0.0264(16) Uani 1 1 d . . . H9 H 0.5166 0.4476 0.2448 0.032 Uiso 1 1 calc R . . N2 N 0.2287(8) 0.3918(6) 0.35825(15) 0.0289(17) Uani 1 1 d . . . H2 H 0.1780 0.4261 0.3762 0.035 Uiso 1 1 calc R . . C10 C 0.2508(10) 0.2442(7) 0.35706(19) 0.0300(18) Uani 1 1 d . . . H10A H 0.3602 0.2225 0.3468 0.036 Uiso 1 1 calc R . . H10B H 0.1593 0.2033 0.3420 0.036 Uiso 1 1 calc R . . C11 C 0.2474(9) 0.1847(7) 0.3930(2) 0.0247(18) Uani 1 1 d . . . C12 C 0.3513(9) 0.2190(7) 0.42237(19) 0.0203(17) Uani 1 1 d . . . H12 H 0.4345 0.2889 0.4231 0.024 Uiso 1 1 calc R . . C13 C 0.3132(10) 0.1334(7) 0.4507(2) 0.0287(19) Uani 1 1 d . . . H13 H 0.3653 0.1358 0.4735 0.034 Uiso 1 1 calc R . . C14 C 0.1831(10) 0.0436(7) 0.4387(2) 0.028(2) Uani 1 1 d . . . H14 H 0.1336 -0.0260 0.4521 0.034 Uiso 1 1 calc R . . C15 C 0.1388(9) 0.0750(7) 0.4033(2) 0.0235(18) Uani 1 1 d . . . H15 H 0.0534 0.0317 0.3890 0.028 Uiso 1 1 calc R . . C16 C -0.0518(9) 0.4026(7) 0.4211(2) 0.028(2) Uani 1 1 d . . . H16 H -0.0611 0.4481 0.3992 0.034 Uiso 1 1 calc R . . C17 C 0.0583(10) 0.4378(7) 0.4500(2) 0.0284(19) Uani 1 1 d . . . H17 H 0.1380 0.5103 0.4507 0.034 Uiso 1 1 calc R . . C18 C 0.0286(10) 0.3460(7) 0.4774(2) 0.0276(19) Uani 1 1 d . . . H18 H 0.0845 0.3463 0.4999 0.033 Uiso 1 1 calc R . . C19 C -0.0981(10) 0.2543(7) 0.4657(2) 0.0316(19) Uani 1 1 d . . . H19 H -0.1436 0.1827 0.4790 0.038 Uiso 1 1 calc R . . C20 C -0.1459(10) 0.2857(7) 0.4313(2) 0.031(2) Uani 1 1 d . . . H20 H -0.2272 0.2378 0.4170 0.038 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 0.0347(6) 0.0048(5) 0.0231(6) -0.0007(5) 0.0070(4) 0.0021(5) N1 0.043(4) 0.013(3) 0.028(4) 0.002(3) 0.009(3) -0.001(3) C2 0.034(4) 0.010(4) 0.017(4) -0.003(3) 0.003(4) 0.002(3) N3 0.040(4) 0.010(3) 0.021(4) 0.001(3) 0.006(3) -0.001(3) C4 0.044(5) 0.011(4) 0.014(4) -0.002(3) 0.001(4) -0.002(4) C5 0.045(5) 0.002(3) 0.020(4) 0.001(3) -0.001(4) 0.003(3) C6 0.038(4) 0.005(4) 0.031(5) 0.003(3) -0.004(4) 0.007(3) Cl6 0.0683(15) 0.0081(10) 0.0356(13) -0.0042(9) 0.0091(11) 0.0093(9) N7 0.050(4) 0.011(3) 0.023(4) 0.006(3) 0.006(3) 0.000(3) C8 0.044(5) 0.021(4) 0.015(4) -0.001(3) 0.006(4) -0.004(4) N9 0.052(4) 0.004(3) 0.024(4) -0.002(3) 0.011(3) 0.001(3) N2 0.065(5) 0.010(3) 0.014(3) 0.000(3) 0.020(3) 0.003(3) C10 0.054(5) 0.009(4) 0.028(4) -0.001(4) 0.011(4) 0.006(4) C11 0.037(4) 0.011(4) 0.026(5) -0.001(3) 0.006(4) 0.010(3) C12 0.028(4) 0.008(4) 0.026(5) 0.004(3) 0.009(3) 0.002(3) C13 0.039(5) 0.017(4) 0.030(5) -0.003(4) 0.001(4) 0.006(4) C14 0.038(5) 0.007(4) 0.041(5) 0.001(3) 0.010(4) 0.005(3) C15 0.031(4) 0.012(4) 0.028(5) 0.000(3) 0.003(4) 0.003(3) C16 0.041(5) 0.014(4) 0.032(5) 0.001(4) 0.014(4) 0.009(4) C17 0.036(5) 0.014(4) 0.036(5) -0.002(4) 0.011(4) 0.004(4) C18 0.035(5) 0.023(4) 0.025(5) -0.014(4) 0.003(4) 0.007(4) C19 0.051(5) 0.010(4) 0.035(5) 0.001(4) 0.021(4) 0.006(4) C20 0.030(4) 0.014(4) 0.050(6) -0.010(4) 0.007(4) 0.008(3) _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 C20 2.023(8) . ? Fe1 C13 2.035(8) . ? Fe1 C14 2.035(7) . ? Fe1 C19 2.042(7) . ? Fe1 C12 2.044(7) . ? Fe1 C15 2.045(7) . ? Fe1 C18 2.052(7) . ? Fe1 C17 2.058(7) . ? Fe1 C16 2.060(7) . ? Fe1 C11 2.071(7) . ? N1 C6 1.329(9) . ? N1 C2 1.394(8) . ? C2 N3 1.317(8) . ? C2 N2 1.355(8) . ? N3 C4 1.339(8) . ? C4 N9 1.341(8) . ? C4 C5 1.420(9) . ? C5 C6 1.376(10) . ? C5 N7 1.380(8) . ? C6 Cl6 1.745(7) . ? N7 C8 1.337(9) . ? C8 N9 1.372(9) . ? N2 C10 1.458(8) . ? C10 C11 1.498(10) . ? C11 C12 1.404(10) . ? C11 C15 1.443(10) . ? C12 C13 1.416(10) . ? C13 C14 1.415(10) . ? C14 C15 1.422(10) . ? C16 C17 1.419(11) . ? C16 C20 1.430(10) . ? C17 C18 1.411(10) . ? C18 C19 1.405(10) . ? C19 C20 1.390(11) . ? 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 C20 Fe1 C13 155.6(3) . . ? C20 Fe1 C14 120.6(3) . . ? C13 Fe1 C14 40.7(3) . . ? C20 Fe1 C19 40.0(3) . . ? C13 Fe1 C19 120.2(3) . . ? C14 Fe1 C19 105.2(3) . . ? C20 Fe1 C12 162.1(3) . . ? C13 Fe1 C12 40.6(3) . . ? C14 Fe1 C12 67.9(3) . . ? C19 Fe1 C12 157.4(3) . . ? C20 Fe1 C15 107.2(3) . . ? C13 Fe1 C15 68.8(3) . . ? C14 Fe1 C15 40.8(3) . . ? C19 Fe1 C15 121.7(3) . . ? C12 Fe1 C15 68.1(3) . . ? C20 Fe1 C18 67.7(3) . . ? C13 Fe1 C18 106.1(3) . . ? C14 Fe1 C18 120.9(3) . . ? C19 Fe1 C18 40.1(3) . . ? C12 Fe1 C18 123.4(3) . . ? C15 Fe1 C18 157.1(3) . . ? C20 Fe1 C17 68.2(3) . . ? C13 Fe1 C17 123.2(3) . . ? C14 Fe1 C17 157.8(3) . . ? C19 Fe1 C17 67.5(3) . . ? C12 Fe1 C17 110.2(3) . . ? C15 Fe1 C17 160.9(3) . . ? C18 Fe1 C17 40.2(3) . . ? C20 Fe1 C16 41.0(3) . . ? C13 Fe1 C16 160.6(3) . . ? C14 Fe1 C16 158.4(3) . . ? C19 Fe1 C16 67.7(3) . . ? C12 Fe1 C16 126.2(3) . . ? C15 Fe1 C16 124.1(3) . . ? C18 Fe1 C16 67.7(3) . . ? C17 Fe1 C16 40.3(3) . . ? C20 Fe1 C11 125.4(3) . . ? C13 Fe1 C11 68.3(3) . . ? C14 Fe1 C11 68.4(3) . . ? C19 Fe1 C11 159.7(3) . . ? C12 Fe1 C11 39.9(3) . . ? C15 Fe1 C11 41.0(3) . . ? C18 Fe1 C11 159.7(3) . . ? C17 Fe1 C11 125.4(3) . . ? C16 Fe1 C11 110.8(3) . . ? C6 N1 C2 115.7(6) . . ? N3 C2 N2 120.2(6) . . ? N3 C2 N1 127.7(6) . . ? N2 C2 N1 112.1(6) . . ? C2 N3 C4 113.3(6) . . ? N3 C4 N9 129.0(6) . . ? N3 C4 C5 125.3(7) . . ? N9 C4 C5 105.7(6) . . ? C6 C5 N7 134.7(6) . . ? C6 C5 C4 115.0(6) . . ? N7 C5 C4 110.3(6) . . ? N1 C6 C5 122.8(6) . . ? N1 C6 Cl6 116.7(6) . . ? C5 C6 Cl6 120.5(6) . . ? C8 N7 C5 103.6(6) . . ? N7 C8 N9 113.1(6) . . ? C4 N9 C8 107.3(6) . . ? C2 N2 C10 124.8(6) . . ? N2 C10 C11 110.5(6) . . ? C12 C11 C15 107.1(7) . . ? C12 C11 C10 127.6(7) . . ? C15 C11 C10 125.3(7) . . ? C12 C11 Fe1 69.0(4) . . ? C15 C11 Fe1 68.5(4) . . ? C10 C11 Fe1 129.6(5) . . ? C11 C12 C13 109.6(7) . . ? C11 C12 Fe1 71.1(4) . . ? C13 C12 Fe1 69.3(4) . . ? C14 C13 C12 107.3(7) . . ? C14 C13 Fe1 69.6(4) . . ? C12 C13 Fe1 70.1(4) . . ? C13 C14 C15 108.7(7) . . ? C13 C14 Fe1 69.6(4) . . ? C15 C14 Fe1 70.0(4) . . ? C14 C15 C11 107.3(7) . . ? C14 C15 Fe1 69.2(4) . . ? C11 C15 Fe1 70.5(4) . . ? C17 C16 C20 106.9(7) . . ? C17 C16 Fe1 69.8(4) . . ? C20 C16 Fe1 68.1(4) . . ? C18 C17 C16 108.0(7) . . ? C18 C17 Fe1 69.7(4) . . ? C16 C17 Fe1 69.9(4) . . ? C19 C18 C17 108.1(7) . . ? C19 C18 Fe1 69.5(4) . . ? C17 C18 Fe1 70.1(4) . . ? C20 C19 C18 108.7(7) . . ? C20 C19 Fe1 69.3(4) . . ? C18 C19 Fe1 70.3(4) . . ? C19 C20 C16 108.2(7) . . ? C19 C20 Fe1 70.7(5) . . ? C16 C20 Fe1 70.9(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.867 _refine_diff_density_min -0.809 _refine_diff_density_rms 0.133 data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H24 Cl Fe2 N5' _chemical_formula_weight 565.66 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' 'Cl' 'Cl' 0.1484 0.1585 '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 7.4437(7) _cell_length_b 11.2087(10) _cell_length_c 14.7197(14) _cell_angle_alpha 101.704(2) _cell_angle_beta 95.290(2) _cell_angle_gamma 96.077(3) _cell_volume 1187.66(19) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 5557 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 26.68 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 1.361 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.491 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8808 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5235 _reflns_number_gt 4022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0465P)^2^+3.8169P] 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 5235 _refine_ls_number_parameters 334 _refine_ls_number_restraints 263 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.238 _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 Cl1 Cl 0.51177(18) 0.62996(13) 0.43454(10) 0.0375(3) Uani 1 1 d . . . Fe1 Fe 1.54045(10) 0.83838(8) 0.83202(5) 0.0307(2) Uani 1 1 d . . . Fe2 Fe 1.01885(10) 1.33604(7) 0.82911(5) 0.0293(2) Uani 1 1 d . . . C13 C 1.3353(7) 0.8442(6) 0.7321(4) 0.0369(13) Uani 1 1 d . . . C14 C 1.4404(8) 0.9609(6) 0.7625(4) 0.0424(15) Uani 1 1 d . . . H14 H 1.5049 1.0051 0.7244 0.051 Uiso 1 1 calc R . . C15 C 1.4328(8) 0.9993(6) 0.8576(5) 0.0462(16) Uani 1 1 d . . . H15 H 1.4915 1.0746 0.8956 0.055 Uiso 1 1 calc R . . C16 C 1.3243(8) 0.9090(6) 0.8887(4) 0.0426(15) Uani 1 1 d . . . H16 H 1.2967 0.9126 0.9509 0.051 Uiso 1 1 calc R . . C17 C 1.2632(7) 0.8115(6) 0.8108(4) 0.0352(13) Uani 1 1 d . . . H17 H 1.1877 0.7378 0.8112 0.042 Uiso 1 1 calc R . . C18 C 1.6984(9) 0.7126(7) 0.7737(5) 0.0526(18) Uani 1 1 d . . . H18 H 1.6802 0.6668 0.7110 0.063 Uiso 1 1 calc R . . C19 C 1.8038(8) 0.8271(7) 0.8061(5) 0.0507(17) Uani 1 1 d . . . H19 H 1.8699 0.8723 0.7692 0.061 Uiso 1 1 calc R . . C20 C 1.7952(8) 0.8632(6) 0.9010(5) 0.0456(16) Uani 1 1 d . . . H20 H 1.8538 0.9380 0.9398 0.055 Uiso 1 1 calc R . . C21 C 1.6871(8) 0.7725(7) 0.9307(5) 0.0475(16) Uani 1 1 d . . . H21 H 1.6607 0.7741 0.9929 0.057 Uiso 1 1 calc R . . C22 C 1.6236(9) 0.6771(7) 0.8511(6) 0.057(2) Uani 1 1 d . . . H22 H 1.5460 0.6036 0.8498 0.068 Uiso 1 1 calc R . . C23 C 0.8964(8) 1.1833(5) 0.7387(4) 0.0375(13) Uani 1 1 d . . . C24 C 0.9892(8) 1.1502(5) 0.8164(5) 0.0393(14) Uani 1 1 d . . . H24 H 1.0834 1.0991 0.8146 0.047 Uiso 1 1 calc R . . C25 C 0.9163(8) 1.2070(6) 0.8971(4) 0.0417(15) Uani 1 1 d . . . H25 H 0.9544 1.2006 0.9591 0.050 Uiso 1 1 calc R . . C26 C 0.7797(7) 1.2742(5) 0.8715(4) 0.0350(13) Uani 1 1 d . . . H26 H 0.7106 1.3218 0.9127 0.042 Uiso 1 1 calc R . . C27 C 0.7625(8) 1.2583(5) 0.7726(4) 0.0365(13) Uani 1 1 d . . . H27 H 0.6775 1.2916 0.7357 0.044 Uiso 1 1 calc R . . C28 C 1.2865(9) 1.3933(6) 0.8312(6) 0.061(2) Uani 1 1 d . . . H28 H 1.3802 1.3418 0.8274 0.073 Uiso 1 1 calc R . . C29 C 1.1859(10) 1.4236(7) 0.7557(5) 0.056(2) Uani 1 1 d . . . H29 H 1.2008 1.3964 0.6917 0.068 Uiso 1 1 calc R . . C30 C 1.0616(10) 1.4993(6) 0.7894(5) 0.0501(17) Uani 1 1 d . . . H30 H 0.9754 1.5321 0.7529 0.060 Uiso 1 1 calc R . . C31 C 1.0852(10) 1.5195(5) 0.8882(5) 0.0495(18) Uani 1 1 d . . . H31 H 1.0186 1.5692 0.9295 0.059 Uiso 1 1 calc R . . C32 C 1.2225(9) 1.4540(6) 0.9146(5) 0.0492(17) Uani 1 1 d . . . H32 H 1.2657 1.4504 0.9767 0.059 Uiso 1 1 calc R . . N1 N 0.9933(7) 0.8876(5) 0.6004(3) 0.0602(16) Uani 1 1 d DU . . C2 C 0.9896(8) 0.7693(6) 0.5758(4) 0.0506(15) Uani 1 1 d DU . . N3 N 0.8500(6) 0.6811(5) 0.5264(3) 0.0384(11) Uani 0.50 1 d PDU . . C4 C 0.6973(7) 0.7291(5) 0.4987(4) 0.0312(11) Uani 1 1 d DU . . C5 C 0.6842(7) 0.8510(4) 0.5181(3) 0.0379(11) Uani 0.50 1 d PDU . . C6 C 0.8409(8) 0.9227(5) 0.5701(4) 0.0521(15) Uani 1 1 d DU . . N7 N 0.5761(10) 0.9315(7) 0.5029(7) 0.045(2) Uani 0.50 1 d PDU . . C8 C 0.6579(15) 1.0420(7) 0.5463(8) 0.046(3) Uani 0.50 1 d PDU . . H8 H 0.6051 1.1156 0.5467 0.055 Uiso 0.50 1 calc PR . . N9 N 0.8065(9) 1.0388(5) 0.5852(4) 0.0648(17) Uani 1 1 d DU . . N10 N 1.1291(6) 0.7081(6) 0.5956(4) 0.0652(18) Uani 1 1 d DU . . C11 C 1.3168(8) 0.7650(8) 0.6339(4) 0.060(2) Uani 1 1 d U . . H11A H 1.3630 0.8163 0.5916 0.071 Uiso 1 1 calc R . . H11B H 1.3950 0.6989 0.6340 0.071 Uiso 1 1 calc R . . C12 C 0.9311(12) 1.1476(6) 0.6380(5) 0.067(2) Uani 1 1 d U . . H12A H 0.9164 1.2177 0.6077 0.080 Uiso 1 1 calc R . . H12B H 1.0582 1.1297 0.6356 0.080 Uiso 1 1 calc R . . N3A N 0.6842(7) 0.8510(4) 0.5181(3) 0.0379(11) Uani 0.50 1 d PU . . C5A C 0.8500(6) 0.6811(5) 0.5264(3) 0.0384(11) Uani 0.50 1 d PU . . N7A N 0.9173(11) 0.5767(7) 0.5151(6) 0.043(2) Uani 0.50 1 d PDU . . C8A C 1.0849(12) 0.5961(8) 0.5549(7) 0.046(3) Uani 0.50 1 d PDU . . H8A H 1.1635 0.5345 0.5536 0.055 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 Cl1 0.0297(7) 0.0384(8) 0.0354(7) -0.0037(6) -0.0043(5) -0.0068(6) Fe1 0.0240(4) 0.0398(5) 0.0277(4) 0.0107(3) -0.0008(3) -0.0027(3) Fe2 0.0326(4) 0.0229(4) 0.0306(4) 0.0046(3) 0.0068(3) -0.0051(3) C13 0.022(3) 0.058(4) 0.030(3) 0.012(3) -0.002(2) 0.000(2) C14 0.033(3) 0.051(4) 0.048(4) 0.030(3) -0.006(3) -0.002(3) C15 0.036(3) 0.034(3) 0.060(4) 0.000(3) -0.011(3) 0.000(3) C16 0.031(3) 0.065(4) 0.031(3) 0.007(3) 0.001(2) 0.010(3) C17 0.024(3) 0.044(3) 0.035(3) 0.009(3) 0.004(2) -0.005(2) C18 0.050(4) 0.058(4) 0.048(4) 0.004(3) 0.000(3) 0.019(3) C19 0.026(3) 0.075(5) 0.059(4) 0.029(4) 0.007(3) 0.011(3) C20 0.030(3) 0.055(4) 0.050(4) 0.017(3) -0.007(3) -0.003(3) C21 0.040(3) 0.067(5) 0.045(4) 0.030(3) 0.007(3) 0.017(3) C22 0.038(4) 0.043(4) 0.095(6) 0.035(4) -0.002(4) 0.000(3) C23 0.051(4) 0.024(3) 0.034(3) 0.005(2) 0.010(3) -0.012(2) C24 0.040(3) 0.022(3) 0.058(4) 0.014(3) 0.010(3) -0.001(2) C25 0.048(4) 0.036(3) 0.040(3) 0.019(3) -0.002(3) -0.013(3) C26 0.032(3) 0.036(3) 0.034(3) 0.001(2) 0.009(2) -0.003(2) C27 0.034(3) 0.035(3) 0.037(3) 0.010(3) -0.008(2) -0.004(2) C28 0.031(3) 0.037(4) 0.111(7) 0.009(4) 0.020(4) -0.010(3) C29 0.067(5) 0.049(4) 0.045(4) 0.000(3) 0.027(4) -0.026(4) C30 0.063(4) 0.031(3) 0.055(4) 0.018(3) 0.007(3) -0.013(3) C31 0.067(4) 0.019(3) 0.055(4) -0.005(3) 0.024(3) -0.013(3) C32 0.057(4) 0.032(3) 0.050(4) 0.007(3) -0.002(3) -0.022(3) N1 0.051(3) 0.088(4) 0.021(3) -0.015(3) 0.007(2) -0.035(3) C2 0.034(3) 0.090(4) 0.020(3) 0.001(3) 0.003(2) -0.006(3) N3 0.033(3) 0.053(3) 0.025(3) 0.003(2) 0.002(2) -0.001(2) C4 0.028(2) 0.034(3) 0.026(3) 0.001(2) 0.003(2) -0.008(2) C5 0.048(3) 0.038(3) 0.024(2) 0.000(2) 0.008(2) -0.003(2) C6 0.082(4) 0.038(3) 0.028(3) -0.001(3) 0.013(3) -0.022(3) N7 0.056(5) 0.034(5) 0.043(6) 0.005(4) 0.014(4) -0.004(4) C8 0.076(7) 0.034(5) 0.033(6) 0.013(5) 0.018(5) 0.003(5) N9 0.106(5) 0.042(3) 0.037(3) 0.000(2) 0.020(3) -0.028(3) N10 0.029(3) 0.126(5) 0.029(3) -0.008(3) -0.004(2) 0.010(3) C11 0.025(3) 0.110(6) 0.038(4) 0.006(4) -0.002(3) 0.006(3) C12 0.111(6) 0.034(4) 0.043(4) -0.007(3) 0.030(4) -0.033(4) N3A 0.048(3) 0.038(3) 0.024(2) 0.000(2) 0.008(2) -0.003(2) C5A 0.033(3) 0.053(3) 0.025(3) 0.003(2) 0.002(2) -0.001(2) N7A 0.036(5) 0.060(5) 0.033(5) 0.015(4) -0.003(4) 0.007(4) C8A 0.034(5) 0.078(7) 0.020(5) 0.001(6) -0.002(4) 0.005(5) _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 Cl1 C4 1.744(5) . ? Fe1 C20 2.031(6) . ? Fe1 C15 2.031(6) . ? Fe1 C14 2.033(6) . ? Fe1 C22 2.035(7) . ? Fe1 C13 2.035(5) . ? Fe1 C18 2.038(7) . ? Fe1 C17 2.040(5) . ? Fe1 C16 2.040(6) . ? Fe1 C21 2.040(6) . ? Fe1 C19 2.043(6) . ? Fe2 C23 2.014(5) . ? Fe2 C28 2.023(6) . ? Fe2 C29 2.024(6) . ? Fe2 C30 2.034(6) . ? Fe2 C27 2.038(5) . ? Fe2 C24 2.039(6) . ? Fe2 C26 2.040(6) . ? Fe2 C25 2.041(6) . ? Fe2 C32 2.045(6) . ? Fe2 C31 2.051(6) . ? C13 C14 1.416(9) . ? C13 C17 1.417(8) . ? C13 C11 1.521(9) . ? C14 C15 1.387(9) . ? C15 C16 1.403(9) . ? C16 C17 1.417(8) . ? C18 C19 1.399(10) . ? C18 C22 1.422(10) . ? C19 C20 1.382(9) . ? C20 C21 1.395(9) . ? C21 C22 1.423(10) . ? C23 C24 1.415(9) . ? C23 C27 1.432(8) . ? C23 C12 1.508(8) . ? C24 C25 1.413(9) . ? C25 C26 1.396(8) . ? C26 C27 1.422(8) . ? C28 C29 1.402(11) . ? C28 C32 1.427(10) . ? C29 C30 1.379(10) . ? C30 C31 1.417(9) . ? C31 C32 1.391(10) . ? N1 C2 1.298(7) . ? N1 C6 1.308(7) . ? C2 N10 1.345(7) . ? C2 N3 1.392(7) . ? N3 N7A 1.307(8) . ? N3 C4 1.371(6) . ? C4 C5 1.354(6) . ? C5 N7 1.309(8) . ? C5 C6 1.407(7) . ? C6 N9 1.331(7) . ? N7 C8 1.327(9) . ? N7 C8 1.900(14) 2_676 ? C8 N9 1.205(9) . ? C8 N7 1.900(14) 2_676 ? N9 C12 1.481(8) . ? N10 C8A 1.271(8) . ? N10 C11 1.482(7) . ? N7A C8A 1.305(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 Fe1 C15 109.2(3) . . ? C20 Fe1 C14 123.9(3) . . ? C15 Fe1 C14 39.9(3) . . ? C20 Fe1 C22 68.0(3) . . ? C15 Fe1 C22 160.2(3) . . ? C14 Fe1 C22 158.1(3) . . ? C20 Fe1 C13 159.4(3) . . ? C15 Fe1 C13 67.8(2) . . ? C14 Fe1 C13 40.7(2) . . ? C22 Fe1 C13 121.9(3) . . ? C20 Fe1 C18 67.3(3) . . ? C15 Fe1 C18 157.9(3) . . ? C14 Fe1 C18 122.3(3) . . ? C22 Fe1 C18 40.9(3) . . ? C13 Fe1 C18 107.3(3) . . ? C20 Fe1 C17 159.0(3) . . ? C15 Fe1 C17 68.1(2) . . ? C14 Fe1 C17 68.4(2) . . ? C22 Fe1 C17 107.1(3) . . ? C13 Fe1 C17 40.7(2) . . ? C18 Fe1 C17 123.2(3) . . ? C20 Fe1 C16 123.7(3) . . ? C15 Fe1 C16 40.3(3) . . ? C14 Fe1 C16 67.8(3) . . ? C22 Fe1 C16 123.6(3) . . ? C13 Fe1 C16 68.2(2) . . ? C18 Fe1 C16 159.9(3) . . ? C17 Fe1 C16 40.7(2) . . ? C20 Fe1 C21 40.1(3) . . ? C15 Fe1 C21 124.3(3) . . ? C14 Fe1 C21 159.6(3) . . ? C22 Fe1 C21 40.9(3) . . ? C13 Fe1 C21 158.5(3) . . ? C18 Fe1 C21 68.2(3) . . ? C17 Fe1 C21 122.9(3) . . ? C16 Fe1 C21 108.5(3) . . ? C20 Fe1 C19 39.7(3) . . ? C15 Fe1 C19 123.3(3) . . ? C14 Fe1 C19 108.2(3) . . ? C22 Fe1 C19 68.0(3) . . ? C13 Fe1 C19 123.5(3) . . ? C18 Fe1 C19 40.1(3) . . ? C17 Fe1 C19 159.4(3) . . ? C16 Fe1 C19 158.7(3) . . ? C21 Fe1 C19 67.4(3) . . ? C23 Fe2 C28 121.0(3) . . ? C23 Fe2 C29 105.7(3) . . ? C28 Fe2 C29 40.5(3) . . ? C23 Fe2 C30 121.4(3) . . ? C28 Fe2 C30 67.8(3) . . ? C29 Fe2 C30 39.7(3) . . ? C23 Fe2 C27 41.4(2) . . ? C28 Fe2 C27 157.2(3) . . ? C29 Fe2 C27 121.2(3) . . ? C30 Fe2 C27 106.7(3) . . ? C23 Fe2 C24 40.9(2) . . ? C28 Fe2 C24 107.7(3) . . ? C29 Fe2 C24 122.8(3) . . ? C30 Fe2 C24 157.9(3) . . ? C27 Fe2 C24 68.6(2) . . ? C23 Fe2 C26 69.3(2) . . ? C28 Fe2 C26 160.7(3) . . ? C29 Fe2 C26 157.6(3) . . ? C30 Fe2 C26 123.0(3) . . ? C27 Fe2 C26 40.8(2) . . ? C24 Fe2 C26 68.4(2) . . ? C23 Fe2 C25 68.4(2) . . ? C28 Fe2 C25 124.9(3) . . ? C29 Fe2 C25 160.1(3) . . ? C30 Fe2 C25 159.5(3) . . ? C27 Fe2 C25 67.8(2) . . ? C24 Fe2 C25 40.5(2) . . ? C26 Fe2 C25 40.0(2) . . ? C23 Fe2 C32 158.6(3) . . ? C28 Fe2 C32 41.1(3) . . ? C29 Fe2 C32 68.2(3) . . ? C30 Fe2 C32 67.9(3) . . ? C27 Fe2 C32 159.5(3) . . ? C24 Fe2 C32 123.9(3) . . ? C26 Fe2 C32 124.2(3) . . ? C25 Fe2 C32 109.9(3) . . ? C23 Fe2 C31 158.7(3) . . ? C28 Fe2 C31 67.7(3) . . ? C29 Fe2 C31 67.4(3) . . ? C30 Fe2 C31 40.6(3) . . ? C27 Fe2 C31 123.5(3) . . ? C24 Fe2 C31 159.8(3) . . ? C26 Fe2 C31 109.0(3) . . ? C25 Fe2 C31 124.7(3) . . ? C32 Fe2 C31 39.7(3) . . ? C14 C13 C17 107.8(5) . . ? C14 C13 C11 125.4(6) . . ? C17 C13 C11 126.6(6) . . ? C14 C13 Fe1 69.5(3) . . ? C17 C13 Fe1 69.8(3) . . ? C11 C13 Fe1 122.6(4) . . ? C15 C14 C13 108.0(5) . . ? C15 C14 Fe1 70.0(3) . . ? C13 C14 Fe1 69.7(3) . . ? C14 C15 C16 109.1(5) . . ? C14 C15 Fe1 70.1(4) . . ? C16 C15 Fe1 70.2(4) . . ? C15 C16 C17 107.7(5) . . ? C15 C16 Fe1 69.5(4) . . ? C17 C16 Fe1 69.6(3) . . ? C13 C17 C16 107.4(5) . . ? C13 C17 Fe1 69.5(3) . . ? C16 C17 Fe1 69.7(3) . . ? C19 C18 C22 107.9(6) . . ? C19 C18 Fe1 70.1(4) . . ? C22 C18 Fe1 69.4(4) . . ? C20 C19 C18 108.4(6) . . ? C20 C19 Fe1 69.7(4) . . ? C18 C19 Fe1 69.8(4) . . ? C19 C20 C21 109.3(6) . . ? C19 C20 Fe1 70.7(3) . . ? C21 C20 Fe1 70.3(3) . . ? C20 C21 C22 107.5(6) . . ? C20 C21 Fe1 69.6(3) . . ? C22 C21 Fe1 69.4(4) . . ? C18 C22 C21 106.9(6) . . ? C18 C22 Fe1 69.7(4) . . ? C21 C22 Fe1 69.8(4) . . ? C24 C23 C27 107.7(5) . . ? C24 C23 C12 126.9(6) . . ? C27 C23 C12 125.5(6) . . ? C24 C23 Fe2 70.5(3) . . ? C27 C23 Fe2 70.2(3) . . ? C12 C23 Fe2 124.4(4) . . ? C25 C24 C23 107.5(5) . . ? C25 C24 Fe2 69.8(3) . . ? C23 C24 Fe2 68.6(3) . . ? C26 C25 C24 109.4(5) . . ? C26 C25 Fe2 69.9(3) . . ? C24 C25 Fe2 69.7(3) . . ? C25 C26 C27 107.7(5) . . ? C25 C26 Fe2 70.1(3) . . ? C27 C26 Fe2 69.5(3) . . ? C26 C27 C23 107.6(5) . . ? C26 C27 Fe2 69.6(3) . . ? C23 C27 Fe2 68.4(3) . . ? C29 C28 C32 107.5(6) . . ? C29 C28 Fe2 69.8(4) . . ? C32 C28 Fe2 70.3(4) . . ? C30 C29 C28 108.9(6) . . ? C30 C29 Fe2 70.5(4) . . ? C28 C29 Fe2 69.7(4) . . ? C29 C30 C31 107.9(7) . . ? C29 C30 Fe2 69.8(4) . . ? C31 C30 Fe2 70.4(4) . . ? C32 C31 C30 108.4(6) . . ? C32 C31 Fe2 69.9(3) . . ? C30 C31 Fe2 69.0(3) . . ? C31 C32 C28 107.3(6) . . ? C31 C32 Fe2 70.4(4) . . ? C28 C32 Fe2 68.7(4) . . ? C2 N1 C6 111.3(5) . . ? N1 C2 N10 124.3(5) . . ? N1 C2 N3 129.5(5) . . ? N10 C2 N3 106.3(4) . . ? N7A N3 C4 140.2(5) . . ? N7A N3 C2 105.7(4) . . ? C4 N3 C2 113.7(5) . . ? C5 C4 N3 122.9(5) . . ? C5 C4 Cl1 118.1(4) . . ? N3 C4 Cl1 119.1(4) . . ? N7 C5 C4 142.3(5) . . ? N7 C5 C6 104.2(4) . . ? C4 C5 C6 113.5(5) . . ? N1 C6 N9 124.4(6) . . ? N1 C6 C5 129.1(5) . . ? N9 C6 C5 106.6(5) . . ? C5 N7 C8 107.8(5) . . ? C5 N7 C8 146.7(6) . 2_676 ? C8 N7 C8 105.1(7) . 2_676 ? N9 C8 N7 112.6(6) . . ? N9 C8 N7 171.9(8) . 2_676 ? N7 C8 N7 74.9(7) . 2_676 ? C8 N9 C6 108.7(5) . . ? C8 N9 C12 125.0(7) . . ? C6 N9 C12 126.2(7) . . ? C8A N10 C2 107.6(4) . . ? C8A N10 C11 124.8(7) . . ? C2 N10 C11 125.5(6) . . ? N10 C11 C13 114.9(5) . . ? N9 C12 C23 112.6(5) . . ? C8A N7A N3 109.0(5) . . ? N10 C8A N7A 111.2(6) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.709 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.097 data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl Fe N5' _chemical_formula_weight 367.62 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6304(10) _cell_length_b 11.3735(10) _cell_length_c 13.3561(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.155(2) _cell_angle_gamma 90.00 _cell_volume 1543.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 7568 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.58 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.156 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.642 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9574 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.62 _reflns_number_total 3627 _reflns_number_gt 3190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0323P)^2^+0.6874P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except H2A&B coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3627 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.61852(2) 0.343364(19) 0.180298(17) 0.01916(8) Uani 1 1 d . . . N1 N 0.59335(13) 0.86721(11) 0.53449(10) 0.0193(3) Uani 1 1 d . . . C2 C 0.51645(14) 0.81681(13) 0.44349(11) 0.0173(3) Uani 1 1 d . . . N2 N 0.42729(14) 0.88848(13) 0.38052(11) 0.0243(3) Uani 1 1 d . . . H2A H 0.4257(19) 0.9558(19) 0.3992(15) 0.029 Uiso 1 1 d . . . H2B H 0.3868(19) 0.8705(18) 0.3195(17) 0.029 Uiso 1 1 d . . . N3 N 0.52379(12) 0.70469(11) 0.41326(9) 0.0166(2) Uani 1 1 d . . . C4 C 0.61686(14) 0.64385(12) 0.48218(11) 0.0154(3) Uani 1 1 d . . . C5 C 0.70161(14) 0.68412(13) 0.57739(11) 0.0174(3) Uani 1 1 d . . . C6 C 0.68412(14) 0.80079(14) 0.59822(11) 0.0182(3) Uani 1 1 d . . . Cl6 Cl 0.78565(4) 0.86498(4) 0.71046(3) 0.02964(11) Uani 1 1 d . . . N7 N 0.78391(13) 0.59501(12) 0.63018(10) 0.0234(3) Uani 1 1 d . . . C8 C 0.74854(16) 0.50465(14) 0.56742(12) 0.0231(3) Uani 1 1 d . . . H8 H 0.7887 0.4295 0.5827 0.028 Uiso 1 1 calc R . . N9 N 0.64765(12) 0.52777(11) 0.47687(9) 0.0181(3) Uani 1 1 d . . . C10 C 0.58805(15) 0.44767(13) 0.38933(12) 0.0194(3) Uani 1 1 d . . . H10A H 0.5008 0.4786 0.3490 0.023 Uiso 1 1 calc R . . H10B H 0.5744 0.3698 0.4177 0.023 Uiso 1 1 calc R . . C11 C 0.67120(14) 0.43305(13) 0.31747(11) 0.0183(3) Uani 1 1 d . . . C12 C 0.76100(15) 0.33900(14) 0.32227(12) 0.0215(3) Uani 1 1 d . . . H12 H 0.7783 0.2763 0.3715 0.026 Uiso 1 1 calc R . . C13 C 0.82027(16) 0.35497(16) 0.24078(13) 0.0272(4) Uani 1 1 d . . . H13 H 0.8836 0.3046 0.2257 0.033 Uiso 1 1 calc R . . C14 C 0.76848(17) 0.45904(16) 0.18605(13) 0.0284(4) Uani 1 1 d . . . H14 H 0.7912 0.4907 0.1279 0.034 Uiso 1 1 calc R . . C15 C 0.67643(16) 0.50827(14) 0.23317(12) 0.0235(3) Uani 1 1 d . . . H15 H 0.6273 0.5785 0.2123 0.028 Uiso 1 1 calc R . . C16 C 0.42545(16) 0.29797(17) 0.15329(15) 0.0316(4) Uani 1 1 d . . . H16 H 0.3700 0.3211 0.1941 0.038 Uiso 1 1 calc R . . C17 C 0.50575(17) 0.19606(17) 0.16910(15) 0.0338(4) Uani 1 1 d . . . H17 H 0.5140 0.1390 0.2226 0.041 Uiso 1 1 calc R . . C18 C 0.57168(18) 0.19433(18) 0.09097(15) 0.0367(4) Uani 1 1 d . . . H18 H 0.6315 0.1357 0.0829 0.044 Uiso 1 1 calc R . . C19 C 0.53307(18) 0.2947(2) 0.02730(14) 0.0379(5) Uani 1 1 d . . . H19 H 0.5624 0.3155 -0.0310 0.045 Uiso 1 1 calc R . . C20 C 0.44247(18) 0.35925(17) 0.06585(15) 0.0346(4) Uani 1 1 d . . . H20 H 0.4007 0.4309 0.0379 0.042 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 0.01935(12) 0.02072(13) 0.01691(12) -0.00400(8) 0.00458(8) -0.00039(8) N1 0.0219(6) 0.0182(6) 0.0148(6) -0.0019(5) 0.0007(5) 0.0013(5) C2 0.0175(7) 0.0194(7) 0.0140(7) -0.0004(5) 0.0031(5) 0.0015(5) N2 0.0279(7) 0.0200(7) 0.0181(7) -0.0043(5) -0.0037(5) 0.0068(6) N3 0.0180(6) 0.0175(6) 0.0127(6) -0.0011(5) 0.0022(4) 0.0007(5) C4 0.0165(6) 0.0178(7) 0.0132(7) 0.0004(5) 0.0064(5) -0.0003(5) C5 0.0190(7) 0.0206(7) 0.0117(7) 0.0010(5) 0.0032(5) 0.0004(6) C6 0.0200(7) 0.0206(7) 0.0120(7) -0.0011(5) 0.0016(5) -0.0014(6) Cl6 0.0341(2) 0.0281(2) 0.01743(19) -0.00600(15) -0.00672(15) -0.00073(16) N7 0.0271(7) 0.0226(7) 0.0172(6) 0.0026(5) 0.0015(5) 0.0060(5) C8 0.0275(8) 0.0223(8) 0.0178(7) 0.0042(6) 0.0042(6) 0.0075(6) N9 0.0221(6) 0.0175(6) 0.0142(6) -0.0004(5) 0.0048(5) 0.0027(5) C10 0.0230(7) 0.0172(7) 0.0190(7) -0.0038(6) 0.0079(6) -0.0011(6) C11 0.0207(7) 0.0182(7) 0.0154(7) -0.0037(5) 0.0044(5) -0.0017(6) C12 0.0202(7) 0.0247(8) 0.0183(8) -0.0017(6) 0.0037(6) 0.0016(6) C13 0.0198(7) 0.0377(10) 0.0250(9) -0.0091(7) 0.0078(6) -0.0015(7) C14 0.0307(9) 0.0354(10) 0.0213(8) -0.0029(7) 0.0113(7) -0.0107(7) C15 0.0300(8) 0.0187(8) 0.0213(8) -0.0009(6) 0.0066(6) -0.0053(6) C16 0.0202(8) 0.0360(10) 0.0372(10) -0.0131(8) 0.0065(7) -0.0052(7) C17 0.0289(9) 0.0268(9) 0.0403(10) -0.0041(8) 0.0021(8) -0.0086(7) C18 0.0278(9) 0.0353(10) 0.0421(11) -0.0227(9) 0.0029(8) 0.0003(8) C19 0.0327(10) 0.0562(13) 0.0208(9) -0.0136(8) 0.0019(7) -0.0030(9) C20 0.0261(9) 0.0375(10) 0.0317(10) -0.0042(8) -0.0047(7) 0.0023(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 Fe1 C11 2.0261(15) . ? Fe1 C15 2.0344(16) . ? Fe1 C17 2.0398(18) . ? Fe1 C16 2.0426(17) . ? Fe1 C20 2.0455(17) . ? Fe1 C18 2.0479(17) . ? Fe1 C12 2.0488(15) . ? Fe1 C14 2.0507(17) . ? Fe1 C19 2.0524(17) . ? Fe1 C13 2.0609(16) . ? N1 C6 1.3198(19) . ? N1 C2 1.3740(18) . ? C2 N2 1.3416(19) . ? C2 N3 1.3469(19) . ? N3 C4 1.3296(18) . ? C4 N9 1.3671(19) . ? C4 C5 1.401(2) . ? C5 C6 1.380(2) . ? C5 N7 1.3877(19) . ? C6 Cl6 1.7294(15) . ? N7 C8 1.309(2) . ? C8 N9 1.3845(19) . ? N9 C10 1.4701(18) . ? C10 C11 1.494(2) . ? C11 C12 1.422(2) . ? C11 C15 1.428(2) . ? C12 C13 1.421(2) . ? C13 C14 1.415(3) . ? C14 C15 1.425(2) . ? C16 C20 1.417(3) . ? C16 C17 1.418(3) . ? C17 C18 1.418(3) . ? C18 C19 1.410(3) . ? C19 C20 1.423(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Fe1 C15 41.18(6) . . ? C11 Fe1 C17 118.65(7) . . ? C15 Fe1 C17 153.35(7) . . ? C11 Fe1 C16 106.39(7) . . ? C15 Fe1 C16 118.66(7) . . ? C17 Fe1 C16 40.65(8) . . ? C11 Fe1 C20 125.39(7) . . ? C15 Fe1 C20 107.12(7) . . ? C17 Fe1 C20 68.24(8) . . ? C16 Fe1 C20 40.55(8) . . ? C11 Fe1 C18 153.94(8) . . ? C15 Fe1 C18 164.14(8) . . ? C17 Fe1 C18 40.61(8) . . ? C16 Fe1 C18 68.22(7) . . ? C20 Fe1 C18 68.04(8) . . ? C11 Fe1 C12 40.86(6) . . ? C15 Fe1 C12 68.64(6) . . ? C17 Fe1 C12 107.82(7) . . ? C16 Fe1 C12 125.97(7) . . ? C20 Fe1 C12 163.21(7) . . ? C18 Fe1 C12 120.36(7) . . ? C11 Fe1 C14 68.82(6) . . ? C15 Fe1 C14 40.83(7) . . ? C17 Fe1 C14 164.41(8) . . ? C16 Fe1 C14 153.92(8) . . ? C20 Fe1 C14 120.07(8) . . ? C18 Fe1 C14 127.27(7) . . ? C12 Fe1 C14 68.07(7) . . ? C11 Fe1 C19 163.57(8) . . ? C15 Fe1 C19 126.44(8) . . ? C17 Fe1 C19 68.13(8) . . ? C16 Fe1 C19 68.25(8) . . ? C20 Fe1 C19 40.63(8) . . ? C18 Fe1 C19 40.23(8) . . ? C12 Fe1 C19 154.72(7) . . ? C14 Fe1 C19 108.74(8) . . ? C11 Fe1 C13 68.60(6) . . ? C15 Fe1 C13 68.38(7) . . ? C17 Fe1 C13 127.05(7) . . ? C16 Fe1 C13 163.87(8) . . ? C20 Fe1 C13 154.72(8) . . ? C18 Fe1 C13 109.12(7) . . ? C12 Fe1 C13 40.45(6) . . ? C14 Fe1 C13 40.24(7) . . ? C19 Fe1 C13 120.75(7) . . ? C6 N1 C2 117.56(13) . . ? N2 C2 N3 118.68(13) . . ? N2 C2 N1 115.28(13) . . ? N3 C2 N1 126.04(13) . . ? C4 N3 C2 112.47(12) . . ? N3 C4 N9 127.39(13) . . ? N3 C4 C5 127.32(13) . . ? N9 C4 C5 105.26(12) . . ? C6 C5 N7 134.61(14) . . ? C6 C5 C4 114.12(13) . . ? N7 C5 C4 111.26(13) . . ? N1 C6 C5 122.47(13) . . ? N1 C6 Cl6 117.91(12) . . ? C5 C6 Cl6 119.61(11) . . ? C8 N7 C5 103.24(12) . . ? N7 C8 N9 114.36(14) . . ? C4 N9 C8 105.88(12) . . ? C4 N9 C10 125.88(12) . . ? C8 N9 C10 128.18(13) . . ? N9 C10 C11 112.47(12) . . ? C12 C11 C15 107.72(14) . . ? C12 C11 C10 124.84(14) . . ? C15 C11 C10 127.44(14) . . ? C12 C11 Fe1 70.43(9) . . ? C15 C11 Fe1 69.72(9) . . ? C10 C11 Fe1 125.38(10) . . ? C13 C12 C11 108.22(14) . . ? C13 C12 Fe1 70.23(9) . . ? C11 C12 Fe1 68.72(8) . . ? C14 C13 C12 108.05(14) . . ? C14 C13 Fe1 69.49(9) . . ? C12 C13 Fe1 69.32(9) . . ? C13 C14 C15 108.29(14) . . ? C13 C14 Fe1 70.27(10) . . ? C15 C14 Fe1 68.97(9) . . ? C14 C15 C11 107.71(15) . . ? C14 C15 Fe1 70.20(9) . . ? C11 C15 Fe1 69.10(9) . . ? C20 C16 C17 107.90(17) . . ? C20 C16 Fe1 69.84(10) . . ? C17 C16 Fe1 69.57(10) . . ? C16 C17 C18 107.94(17) . . ? C16 C17 Fe1 69.78(10) . . ? C18 C17 Fe1 70.01(11) . . ? C19 C18 C17 108.26(16) . . ? C19 C18 Fe1 70.05(10) . . ? C17 C18 Fe1 69.39(10) . . ? C18 C19 C20 107.88(18) . . ? C18 C19 Fe1 69.71(10) . . ? C20 C19 Fe1 69.43(10) . . ? C16 C20 C19 108.01(17) . . ? C16 C20 Fe1 69.62(10) . . ? C19 C20 Fe1 69.94(10) . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.360 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.053 data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Fe N5 O2' _chemical_formula_weight 391.22 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(1)/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 10.2282(9) _cell_length_b 7.1859(6) _cell_length_c 22.3765(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.597(2) _cell_angle_gamma 90.00 _cell_volume 1605.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 7237 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.91 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11607 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.80 _reflns_number_total 3884 _reflns_number_gt 2981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0462P)^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 SHELXL _refine_ls_extinction_coef 0.0018(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3884 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _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 0.26164(2) 0.53763(3) 0.270839(11) 0.01560(8) Uani 1 1 d . . . N1 N -0.06983(14) -0.02799(19) 0.42439(6) 0.0175(3) Uani 1 1 d . . . H1 H -0.1566 -0.0094 0.4192 0.021 Uiso 1 1 calc R . . C2 C -0.02360(17) -0.2060(2) 0.43547(7) 0.0178(3) Uani 1 1 d . . . N3 N 0.10133(14) -0.25699(19) 0.44555(6) 0.0189(3) Uani 1 1 d . . . C4 C 0.18676(17) -0.1123(2) 0.44119(7) 0.0179(3) Uani 1 1 d . . . C5 C 0.14643(17) 0.0703(2) 0.42710(7) 0.0169(3) Uani 1 1 d . . . C6 C 0.01128(17) 0.1272(2) 0.42064(7) 0.0168(3) Uani 1 1 d . . . O6 O -0.03755(12) 0.28458(16) 0.41365(6) 0.0216(3) Uani 1 1 d . . . N7 N 0.26276(14) 0.16860(19) 0.42699(6) 0.0187(3) Uani 1 1 d . . . C8 C 0.36238(17) 0.0428(3) 0.44041(8) 0.0232(4) Uani 1 1 d . . . H8 H 0.4536 0.0740 0.4425 0.028 Uiso 1 1 calc R . . N9 N 0.32279(15) -0.1291(2) 0.45046(7) 0.0228(3) Uani 1 1 d . . . C10 C 0.27190(18) 0.3584(2) 0.40290(8) 0.0200(4) Uani 1 1 d . . . H10A H 0.3666 0.3995 0.4121 0.024 Uiso 1 1 calc R . . H10B H 0.2202 0.4457 0.4230 0.024 Uiso 1 1 calc R . . C11 C 0.21750(17) 0.3611(2) 0.33492(8) 0.0169(3) Uani 1 1 d . . . C12 C 0.27312(19) 0.2630(2) 0.29083(8) 0.0230(4) Uani 1 1 d . . . H12 H 0.3528 0.1908 0.2992 0.028 Uiso 1 1 calc R . . C13 C 0.1886(2) 0.2922(3) 0.23229(8) 0.0289(4) Uani 1 1 d . . . H13 H 0.2014 0.2419 0.1947 0.035 Uiso 1 1 calc R . . C14 C 0.08148(19) 0.4094(3) 0.23961(9) 0.0285(4) Uani 1 1 d . . . H14 H 0.0107 0.4525 0.2078 0.034 Uiso 1 1 calc R . . C15 C 0.09879(17) 0.4510(2) 0.30300(8) 0.0228(4) Uani 1 1 d . . . H15 H 0.0410 0.5258 0.3209 0.027 Uiso 1 1 calc R . . C16 C 0.40110(17) 0.7253(2) 0.31410(8) 0.0208(4) Uani 1 1 d . . . H16 H 0.4403 0.7309 0.3567 0.025 Uiso 1 1 calc R . . C17 C 0.45140(18) 0.6234(2) 0.26941(8) 0.0233(4) Uani 1 1 d . . . H17 H 0.5296 0.5480 0.2769 0.028 Uiso 1 1 calc R . . C18 C 0.36411(19) 0.6542(3) 0.21165(8) 0.0265(4) Uani 1 1 d . . . H18 H 0.3738 0.6034 0.1737 0.032 Uiso 1 1 calc R . . C19 C 0.25925(18) 0.7747(3) 0.22060(9) 0.0265(4) Uani 1 1 d . . . H19 H 0.1869 0.8188 0.1897 0.032 Uiso 1 1 calc R . . C20 C 0.28239(18) 0.8170(2) 0.28398(9) 0.0239(4) Uani 1 1 d . . . H20 H 0.2276 0.8937 0.3030 0.029 Uiso 1 1 calc R . . N21 N -0.11899(14) -0.34453(19) 0.43620(6) 0.0206(3) Uani 1 1 d . . . H21 H -0.0892 -0.4597 0.4406 0.025 Uiso 1 1 calc R . . O22 O -0.30806(12) -0.16759(17) 0.42446(6) 0.0257(3) Uani 1 1 d . . . C22 C -0.25430(18) -0.3204(2) 0.43084(8) 0.0211(4) Uani 1 1 d . . . C23 C -0.33065(19) -0.4979(3) 0.43331(9) 0.0291(4) Uani 1 1 d . . . H23A H -0.4109 -0.4718 0.4491 0.044 Uiso 1 1 calc R . . H23B H -0.2738 -0.5869 0.4604 0.044 Uiso 1 1 calc R . . H23C H -0.3571 -0.5507 0.3921 0.044 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 0.01654(13) 0.01378(12) 0.01709(13) 0.00223(10) 0.00501(9) -0.00198(10) N1 0.0165(7) 0.0166(7) 0.0198(7) 0.0001(6) 0.0048(5) -0.0005(6) C2 0.0229(9) 0.0177(8) 0.0133(8) -0.0001(6) 0.0054(6) -0.0035(7) N3 0.0193(7) 0.0179(7) 0.0201(7) 0.0025(6) 0.0059(6) -0.0006(6) C4 0.0200(8) 0.0201(8) 0.0137(8) 0.0018(7) 0.0043(6) 0.0002(7) C5 0.0191(8) 0.0179(8) 0.0138(8) 0.0021(6) 0.0041(6) -0.0031(6) C6 0.0227(9) 0.0177(8) 0.0105(8) 0.0008(6) 0.0044(6) -0.0024(7) O6 0.0249(7) 0.0162(6) 0.0239(6) 0.0004(5) 0.0055(5) 0.0010(5) N7 0.0166(7) 0.0220(7) 0.0167(7) 0.0041(6) 0.0022(5) -0.0039(6) C8 0.0183(8) 0.0293(10) 0.0218(9) 0.0060(8) 0.0039(7) -0.0010(8) N9 0.0190(8) 0.0261(8) 0.0236(8) 0.0066(6) 0.0051(6) 0.0011(6) C10 0.0225(9) 0.0169(8) 0.0206(9) 0.0020(7) 0.0046(7) -0.0045(7) C11 0.0191(8) 0.0128(8) 0.0197(8) 0.0022(6) 0.0059(6) -0.0036(6) C12 0.0310(10) 0.0142(8) 0.0266(9) 0.0009(7) 0.0124(8) -0.0026(7) C13 0.0436(12) 0.0225(10) 0.0221(10) -0.0027(8) 0.0101(8) -0.0111(9) C14 0.0250(10) 0.0342(10) 0.0239(10) 0.0072(8) 0.0002(8) -0.0137(8) C15 0.0177(8) 0.0245(9) 0.0271(9) 0.0060(8) 0.0072(7) -0.0029(7) C16 0.0191(9) 0.0189(8) 0.0240(9) 0.0014(7) 0.0037(7) -0.0053(7) C17 0.0191(9) 0.0224(9) 0.0300(10) 0.0041(8) 0.0087(7) -0.0013(7) C18 0.0320(10) 0.0285(10) 0.0215(9) 0.0028(8) 0.0114(8) -0.0103(8) C19 0.0232(9) 0.0217(9) 0.0321(11) 0.0132(8) 0.0005(8) -0.0049(7) C20 0.0240(9) 0.0138(8) 0.0342(11) 0.0017(7) 0.0071(8) -0.0018(7) N21 0.0219(8) 0.0161(7) 0.0237(8) 0.0018(6) 0.0044(6) -0.0018(6) O22 0.0206(6) 0.0265(7) 0.0300(7) 0.0024(6) 0.0051(5) -0.0011(5) C22 0.0235(9) 0.0258(9) 0.0139(8) 0.0021(7) 0.0037(7) -0.0048(7) C23 0.0256(10) 0.0292(10) 0.0307(11) 0.0071(8) 0.0020(8) -0.0094(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 Fe1 C12 2.0213(17) . ? Fe1 C13 2.0329(18) . ? Fe1 C20 2.0332(17) . ? Fe1 C11 2.0374(16) . ? Fe1 C19 2.0385(17) . ? Fe1 C18 2.0396(17) . ? Fe1 C14 2.0423(18) . ? Fe1 C17 2.0433(17) . ? Fe1 C16 2.0467(17) . ? Fe1 C15 2.0500(17) . ? N1 C2 1.368(2) . ? N1 C6 1.403(2) . ? C2 N3 1.301(2) . ? C2 N21 1.396(2) . ? N3 C4 1.375(2) . ? C4 N9 1.366(2) . ? C4 C5 1.391(2) . ? C5 N7 1.384(2) . ? C5 C6 1.418(2) . ? C6 O6 1.2323(19) . ? N7 C8 1.346(2) . ? N7 C10 1.477(2) . ? C8 N9 1.334(2) . ? C10 C11 1.502(2) . ? C11 C15 1.422(2) . ? C11 C12 1.428(2) . ? C12 C13 1.419(3) . ? C13 C14 1.419(3) . ? C14 C15 1.422(3) . ? C16 C20 1.416(2) . ? C16 C17 1.423(2) . ? C17 C18 1.419(3) . ? C18 C19 1.426(3) . ? C19 C20 1.419(3) . ? N21 C22 1.374(2) . ? O22 C22 1.222(2) . ? C22 C23 1.503(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 C12 Fe1 C13 40.97(8) . . ? C12 Fe1 C20 158.87(8) . . ? C13 Fe1 C20 159.25(8) . . ? C12 Fe1 C11 41.20(7) . . ? C13 Fe1 C11 68.97(7) . . ? C20 Fe1 C11 123.02(7) . . ? C12 Fe1 C19 158.63(8) . . ? C13 Fe1 C19 122.15(8) . . ? C20 Fe1 C19 40.79(7) . . ? C11 Fe1 C19 158.53(7) . . ? C12 Fe1 C18 122.10(7) . . ? C13 Fe1 C18 105.92(7) . . ? C20 Fe1 C18 68.67(7) . . ? C11 Fe1 C18 159.53(7) . . ? C19 Fe1 C18 40.94(8) . . ? C12 Fe1 C14 68.89(8) . . ? C13 Fe1 C14 40.77(8) . . ? C20 Fe1 C14 123.56(8) . . ? C11 Fe1 C14 68.78(7) . . ? C19 Fe1 C14 106.68(8) . . ? C18 Fe1 C14 121.08(8) . . ? C12 Fe1 C17 106.76(7) . . ? C13 Fe1 C17 121.17(8) . . ? C20 Fe1 C17 68.59(7) . . ? C11 Fe1 C17 123.77(7) . . ? C19 Fe1 C17 68.68(7) . . ? C18 Fe1 C17 40.67(7) . . ? C14 Fe1 C17 156.92(8) . . ? C12 Fe1 C16 122.54(7) . . ? C13 Fe1 C16 157.87(8) . . ? C20 Fe1 C16 40.62(7) . . ? C11 Fe1 C16 108.42(7) . . ? C19 Fe1 C16 68.49(8) . . ? C18 Fe1 C16 68.45(7) . . ? C14 Fe1 C16 160.54(8) . . ? C17 Fe1 C16 40.73(7) . . ? C12 Fe1 C15 68.79(7) . . ? C13 Fe1 C15 68.51(8) . . ? C20 Fe1 C15 108.44(7) . . ? C11 Fe1 C15 40.72(7) . . ? C19 Fe1 C15 122.32(7) . . ? C18 Fe1 C15 157.61(8) . . ? C14 Fe1 C15 40.67(7) . . ? C17 Fe1 C15 160.80(8) . . ? C16 Fe1 C15 124.75(7) . . ? C2 N1 C6 124.66(14) . . ? N3 C2 N1 125.62(15) . . ? N3 C2 N21 117.38(15) . . ? N1 C2 N21 117.00(15) . . ? C2 N3 C4 112.97(14) . . ? N9 C4 N3 124.35(15) . . ? N9 C4 C5 111.06(15) . . ? N3 C4 C5 124.59(15) . . ? N7 C5 C4 105.62(14) . . ? N7 C5 C6 132.19(15) . . ? C4 C5 C6 121.97(15) . . ? O6 C6 N1 120.56(15) . . ? O6 C6 C5 129.53(15) . . ? N1 C6 C5 109.90(14) . . ? C8 N7 C5 105.43(13) . . ? C8 N7 C10 126.60(14) . . ? C5 N7 C10 126.50(14) . . ? N9 C8 N7 114.61(15) . . ? C8 N9 C4 103.25(14) . . ? N7 C10 C11 110.05(13) . . ? C15 C11 C12 107.59(15) . . ? C15 C11 C10 127.01(16) . . ? C12 C11 C10 125.31(16) . . ? C15 C11 Fe1 70.12(9) . . ? C12 C11 Fe1 68.80(9) . . ? C10 C11 Fe1 129.13(11) . . ? C13 C12 C11 108.09(16) . . ? C13 C12 Fe1 69.95(10) . . ? C11 C12 Fe1 70.01(9) . . ? C12 C13 C14 108.14(16) . . ? C12 C13 Fe1 69.07(10) . . ? C14 C13 Fe1 69.97(11) . . ? C13 C14 C15 107.96(17) . . ? C13 C14 Fe1 69.26(11) . . ? C15 C14 Fe1 69.96(10) . . ? C14 C15 C11 108.22(16) . . ? C14 C15 Fe1 69.37(10) . . ? C11 C15 Fe1 69.16(9) . . ? C20 C16 C17 107.99(16) . . ? C20 C16 Fe1 69.18(10) . . ? C17 C16 Fe1 69.51(10) . . ? C18 C17 C16 107.92(16) . . ? C18 C17 Fe1 69.52(10) . . ? C16 C17 Fe1 69.76(10) . . ? C17 C18 C19 108.05(16) . . ? C17 C18 Fe1 69.80(10) . . ? C19 C18 Fe1 69.49(10) . . ? C20 C19 C18 107.68(16) . . ? C20 C19 Fe1 69.40(10) . . ? C18 C19 Fe1 69.57(10) . . ? C16 C20 C19 108.36(16) . . ? C16 C20 Fe1 70.21(10) . . ? C19 C20 Fe1 69.81(10) . . ? C22 N21 C2 127.02(15) . . ? O22 C22 N21 122.87(16) . . ? O22 C22 C23 122.86(17) . . ? N21 C22 C23 114.27(16) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.441 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.059 data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Fe N6 O3' _chemical_formula_weight 464.31 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 22.443(3) _cell_length_b 7.6933(11) _cell_length_c 23.913(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4128.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3526 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 24.15 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.768 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.608 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23293 _diffrn_reflns_av_R_equivalents 0.1032 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3636 _reflns_number_gt 2377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0375P)^2^+5.6258P] 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 SHELXL _refine_ls_extinction_coef 0.00067(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3636 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.12841(2) 0.83796(7) 0.20572(2) 0.01714(16) Uani 1 1 d . . . N1 N 0.25386(13) 1.0563(4) -0.09012(11) 0.0178(7) Uani 1 1 d . . . H1 H 0.2557 1.1059 -0.1232 0.021 Uiso 1 1 calc R . . C2 C 0.19854(15) 1.0311(5) -0.06783(15) 0.0157(8) Uani 1 1 d . . . N3 N 0.18812(12) 0.9555(4) -0.01970(12) 0.0146(7) Uani 1 1 d . . . C4 C 0.23984(15) 0.9095(5) 0.00625(13) 0.0157(8) Uani 1 1 d . . . C5 C 0.29797(15) 0.9354(5) -0.01126(14) 0.0155(8) Uani 1 1 d . . . O6 O 0.35536(10) 1.0354(3) -0.08966(10) 0.0240(6) Uani 1 1 d . . . C6 C 0.30873(16) 1.0098(5) -0.06466(15) 0.0183(8) Uani 1 1 d . . . N7 N 0.33805(13) 0.8710(4) 0.02772(12) 0.0197(7) Uani 1 1 d . . . C8 C 0.30384(16) 0.8070(5) 0.06726(15) 0.0196(9) Uani 1 1 d . . . H8 H 0.3191 0.7527 0.0999 0.024 Uiso 1 1 calc R . . N9 N 0.24377(12) 0.8262(4) 0.05689(11) 0.0153(6) Uani 1 1 d . . . C10 C 0.19554(15) 0.7587(5) 0.09257(14) 0.0172(8) Uani 1 1 d . . . H10A H 0.2104 0.6566 0.1136 0.021 Uiso 1 1 calc R . . H10B H 0.1622 0.7195 0.0685 0.021 Uiso 1 1 calc R . . C11 C 0.17266(15) 0.8919(5) 0.13337(14) 0.0158(8) Uani 1 1 d . . . C12 C 0.11598(15) 0.9731(5) 0.13349(14) 0.0195(9) Uani 1 1 d . . . H12 H 0.0851 0.9544 0.1070 0.023 Uiso 1 1 calc R . . C13 C 0.11339(17) 1.0873(5) 0.18011(15) 0.0235(9) Uani 1 1 d . . . H13 H 0.0805 1.1584 0.1902 0.028 Uiso 1 1 calc R . . C14 C 0.16869(17) 1.0766(5) 0.20914(16) 0.0260(9) Uani 1 1 d . . . H14 H 0.1793 1.1393 0.2419 0.031 Uiso 1 1 calc R . . C15 C 0.20489(16) 0.9554(5) 0.18022(15) 0.0205(9) Uani 1 1 d . . . H15 H 0.2442 0.9221 0.1905 0.025 Uiso 1 1 calc R . . C16 C 0.12250(18) 0.5747(5) 0.21149(17) 0.0317(10) Uani 1 1 d . . . H16 H 0.1382 0.4935 0.1854 0.038 Uiso 1 1 calc R . . C17 C 0.06477(17) 0.6494(5) 0.20974(17) 0.0304(9) Uani 1 1 d . . . H17 H 0.0350 0.6270 0.1824 0.036 Uiso 1 1 calc R . . C18 C 0.05941(18) 0.7632(6) 0.25593(17) 0.0313(10) Uani 1 1 d . . . H18 H 0.0254 0.8311 0.2650 0.038 Uiso 1 1 calc R . . C19 C 0.11376(18) 0.7582(6) 0.28635(16) 0.0332(10) Uani 1 1 d . . . H19 H 0.1224 0.8217 0.3194 0.040 Uiso 1 1 calc R . . C20 C 0.15277(18) 0.6420(5) 0.25866(16) 0.0315(10) Uani 1 1 d . . . H20 H 0.1923 0.6141 0.2698 0.038 Uiso 1 1 calc R . . N21 N 0.15022(12) 1.0884(4) -0.09823(12) 0.0174(7) Uani 1 1 d . . . H21 H 0.1148 1.0662 -0.0841 0.021 Uiso 1 1 calc R . . C22 C 0.15141(16) 1.1764(5) -0.14822(14) 0.0198(8) Uani 1 1 d . . . O22 O 0.19768(11) 1.2093(3) -0.17333(10) 0.0255(7) Uani 1 1 d . . . C23 C 0.09115(16) 1.2277(5) -0.16996(15) 0.0257(9) Uani 1 1 d . . . H23A H 0.0945 1.3370 -0.1908 0.039 Uiso 1 1 calc R . . H23B H 0.0637 1.2432 -0.1385 0.039 Uiso 1 1 calc R . . H23C H 0.0760 1.1364 -0.1948 0.039 Uiso 1 1 calc R . . C24 C 0.49859(19) 0.8131(6) 0.08027(16) 0.0374(11) Uani 1 1 d . . . H24A H 0.4570 0.8081 0.0925 0.056 Uiso 1 1 calc R . . H24B H 0.5140 0.9311 0.0858 0.056 Uiso 1 1 calc R . . H24C H 0.5224 0.7309 0.1022 0.056 Uiso 1 1 calc R . . N25 N 0.50220(13) 0.7674(4) 0.02124(12) 0.0214(7) Uani 1 1 d . . . C26 C 0.55795(16) 0.8028(5) -0.00783(17) 0.0287(10) Uani 1 1 d . . . H26A H 0.5877 0.7156 0.0028 0.043 Uiso 1 1 calc R . . H26B H 0.5723 0.9188 0.0024 0.043 Uiso 1 1 calc R . . H26C H 0.5513 0.7978 -0.0483 0.043 Uiso 1 1 calc R . . C27 C 0.45984(15) 0.6747(5) -0.00343(16) 0.0219(9) Uani 1 1 d . . . H27 H 0.4248 0.6513 0.0175 0.026 Uiso 1 1 calc R . . O28 O 0.46249(11) 0.6167(3) -0.05139(11) 0.0254(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0185(3) 0.0203(3) 0.0126(3) 0.0009(3) 0.0016(2) -0.0019(2) N1 0.0180(16) 0.0239(19) 0.0116(15) 0.0028(14) 0.0023(13) 0.0007(14) C2 0.0165(19) 0.015(2) 0.015(2) -0.0030(16) 0.0000(15) 0.0036(15) N3 0.0150(16) 0.0159(17) 0.0128(17) 0.0010(13) -0.0001(12) 0.0013(13) C4 0.023(2) 0.0140(19) 0.0104(17) -0.0024(16) 0.0027(15) 0.0030(16) C5 0.0165(19) 0.018(2) 0.0120(19) -0.0033(16) 0.0017(15) 0.0013(16) O6 0.0173(14) 0.0357(17) 0.0188(14) 0.0015(12) 0.0056(11) -0.0043(12) C6 0.020(2) 0.016(2) 0.019(2) -0.0057(16) -0.0005(17) 0.0005(16) N7 0.0193(17) 0.0217(19) 0.0180(17) -0.0011(14) 0.0003(13) 0.0024(14) C8 0.023(2) 0.018(2) 0.017(2) -0.0007(17) -0.0091(16) 0.0048(16) N9 0.0159(15) 0.0165(16) 0.0136(14) 0.0006(14) 0.0000(12) 0.0017(13) C10 0.0204(19) 0.019(2) 0.0123(19) 0.0036(16) 0.0012(15) -0.0026(17) C11 0.0200(19) 0.015(2) 0.0120(19) 0.0027(15) 0.0049(15) -0.0037(15) C12 0.024(2) 0.021(2) 0.0138(19) 0.0020(16) -0.0017(15) 0.0022(16) C13 0.028(2) 0.021(2) 0.022(2) 0.0026(18) 0.0078(17) 0.0049(17) C14 0.036(2) 0.023(2) 0.018(2) -0.0075(19) 0.0030(19) -0.0082(18) C15 0.021(2) 0.024(2) 0.017(2) 0.0013(18) 0.0017(16) -0.0064(17) C16 0.040(2) 0.021(2) 0.034(2) 0.004(2) 0.008(2) -0.0058(19) C17 0.027(2) 0.034(2) 0.030(2) 0.002(2) 0.0006(19) -0.0097(19) C18 0.025(2) 0.039(3) 0.030(2) 0.006(2) 0.0157(19) -0.006(2) C19 0.045(3) 0.039(3) 0.015(2) 0.005(2) 0.0092(19) -0.010(2) C20 0.030(2) 0.036(3) 0.028(2) 0.018(2) 0.0032(18) 0.003(2) N21 0.0125(15) 0.0270(18) 0.0126(16) 0.0035(14) 0.0021(12) 0.0002(13) C22 0.023(2) 0.023(2) 0.0135(18) -0.0012(18) 0.0004(15) 0.0031(17) O22 0.0223(14) 0.0372(18) 0.0170(14) 0.0068(13) 0.0022(12) 0.0028(12) C23 0.025(2) 0.034(2) 0.018(2) 0.0014(18) -0.0031(17) 0.0068(18) C24 0.041(3) 0.045(3) 0.027(2) -0.009(2) 0.003(2) -0.003(2) N25 0.0167(16) 0.0243(18) 0.0233(17) -0.0059(15) 0.0007(13) 0.0018(14) C26 0.021(2) 0.030(3) 0.035(2) -0.001(2) 0.0007(18) -0.0035(18) C27 0.0131(19) 0.023(2) 0.029(2) 0.0042(19) 0.0010(16) 0.0041(17) O28 0.0187(14) 0.0315(17) 0.0262(16) -0.0035(13) -0.0039(11) -0.0003(12) _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 C15 2.033(4) . ? Fe1 C16 2.034(4) . ? Fe1 C12 2.035(3) . ? Fe1 C11 2.038(3) . ? Fe1 C17 2.038(4) . ? Fe1 C13 2.042(4) . ? Fe1 C18 2.042(4) . ? Fe1 C20 2.043(4) . ? Fe1 C14 2.048(4) . ? Fe1 C19 2.050(4) . ? N1 C2 1.365(4) . ? N1 C6 1.419(4) . ? C2 N3 1.311(4) . ? C2 N21 1.378(4) . ? N3 C4 1.363(4) . ? C4 N9 1.373(4) . ? C4 C5 1.385(5) . ? C5 N7 1.387(4) . ? C5 C6 1.420(5) . ? O6 C6 1.221(4) . ? N7 C8 1.314(5) . ? C8 N9 1.379(4) . ? N9 C10 1.473(4) . ? C10 C11 1.505(5) . ? C11 C12 1.417(5) . ? C11 C15 1.420(5) . ? C12 C13 1.420(5) . ? C13 C14 1.424(5) . ? C14 C15 1.417(5) . ? C16 C20 1.415(6) . ? C16 C17 1.418(6) . ? C17 C18 1.415(6) . ? C18 C19 1.421(6) . ? C19 C20 1.416(6) . ? N21 C22 1.374(4) . ? C22 O22 1.226(4) . ? C22 C23 1.502(5) . ? C24 N25 1.457(5) . ? N25 C27 1.327(4) . ? N25 C26 1.457(5) . ? C27 O28 1.232(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 Fe1 C16 121.18(16) . . ? C15 Fe1 C12 68.55(14) . . ? C16 Fe1 C12 123.87(16) . . ? C15 Fe1 C11 40.83(13) . . ? C16 Fe1 C11 107.00(15) . . ? C12 Fe1 C11 40.73(13) . . ? C15 Fe1 C17 157.21(16) . . ? C16 Fe1 C17 40.75(16) . . ? C12 Fe1 C17 107.92(16) . . ? C11 Fe1 C17 121.78(15) . . ? C15 Fe1 C13 68.41(15) . . ? C16 Fe1 C13 160.91(16) . . ? C12 Fe1 C13 40.78(14) . . ? C11 Fe1 C13 68.55(14) . . ? C17 Fe1 C13 124.57(16) . . ? C15 Fe1 C18 160.32(16) . . ? C16 Fe1 C18 68.29(17) . . ? C12 Fe1 C18 122.62(16) . . ? C11 Fe1 C18 157.85(15) . . ? C17 Fe1 C18 40.57(16) . . ? C13 Fe1 C18 108.42(16) . . ? C15 Fe1 C20 106.72(16) . . ? C16 Fe1 C20 40.60(16) . . ? C12 Fe1 C20 159.96(16) . . ? C11 Fe1 C20 123.09(15) . . ? C17 Fe1 C20 68.46(17) . . ? C13 Fe1 C20 157.43(16) . . ? C18 Fe1 C20 68.33(16) . . ? C15 Fe1 C14 40.63(14) . . ? C16 Fe1 C14 156.71(16) . . ? C12 Fe1 C14 68.68(15) . . ? C11 Fe1 C14 68.66(14) . . ? C17 Fe1 C14 161.01(16) . . ? C13 Fe1 C14 40.76(15) . . ? C18 Fe1 C14 124.32(17) . . ? C20 Fe1 C14 121.25(17) . . ? C15 Fe1 C19 123.40(15) . . ? C16 Fe1 C19 68.14(17) . . ? C12 Fe1 C19 158.31(16) . . ? C11 Fe1 C19 159.68(16) . . ? C17 Fe1 C19 68.29(17) . . ? C13 Fe1 C19 122.48(16) . . ? C18 Fe1 C19 40.63(16) . . ? C20 Fe1 C19 40.47(16) . . ? C14 Fe1 C19 107.55(17) . . ? C2 N1 C6 125.9(3) . . ? N3 C2 N1 124.6(3) . . ? N3 C2 N21 117.7(3) . . ? N1 C2 N21 117.7(3) . . ? C2 N3 C4 111.3(3) . . ? N3 C4 N9 125.3(3) . . ? N3 C4 C5 128.9(3) . . ? N9 C4 C5 105.9(3) . . ? C4 C5 N7 110.9(3) . . ? C4 C5 C6 119.3(3) . . ? N7 C5 C6 129.7(3) . . ? O6 C6 N1 119.5(3) . . ? O6 C6 C5 130.6(3) . . ? N1 C6 C5 109.9(3) . . ? C8 N7 C5 103.8(3) . . ? N7 C8 N9 113.7(3) . . ? C4 N9 C8 105.7(3) . . ? C4 N9 C10 128.9(3) . . ? C8 N9 C10 125.2(3) . . ? N9 C10 C11 112.7(3) . . ? C12 C11 C15 107.7(3) . . ? C12 C11 C10 127.4(3) . . ? C15 C11 C10 124.9(3) . . ? C12 C11 Fe1 69.55(19) . . ? C15 C11 Fe1 69.42(19) . . ? C10 C11 Fe1 125.3(2) . . ? C11 C12 C13 108.1(3) . . ? C11 C12 Fe1 69.73(19) . . ? C13 C12 Fe1 69.9(2) . . ? C12 C13 C14 108.1(3) . . ? C12 C13 Fe1 69.4(2) . . ? C14 C13 Fe1 69.9(2) . . ? C15 C14 C13 107.4(3) . . ? C15 C14 Fe1 69.1(2) . . ? C13 C14 Fe1 69.4(2) . . ? C14 C15 C11 108.6(3) . . ? C14 C15 Fe1 70.2(2) . . ? C11 C15 Fe1 69.75(19) . . ? C20 C16 C17 108.3(4) . . ? C20 C16 Fe1 70.0(2) . . ? C17 C16 Fe1 69.8(2) . . ? C18 C17 C16 107.8(4) . . ? C18 C17 Fe1 69.9(2) . . ? C16 C17 Fe1 69.5(2) . . ? C17 C18 C19 108.1(4) . . ? C17 C18 Fe1 69.6(2) . . ? C19 C18 Fe1 70.0(2) . . ? C20 C19 C18 108.0(4) . . ? C20 C19 Fe1 69.5(2) . . ? C18 C19 Fe1 69.4(2) . . ? C16 C20 C19 107.9(4) . . ? C16 C20 Fe1 69.4(2) . . ? C19 C20 Fe1 70.0(2) . . ? C22 N21 C2 127.0(3) . . ? O22 C22 N21 123.0(3) . . ? O22 C22 C23 122.6(3) . . ? N21 C22 C23 114.4(3) . . ? C27 N25 C24 121.4(3) . . ? C27 N25 C26 120.2(3) . . ? C24 N25 C26 117.7(3) . . ? O28 C27 N25 125.0(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.426 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.081