# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/2102 data_MM9902 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H16 N2 O2 Fe' _chemical_formula_weight 348.18 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1474(4) _cell_length_b 9.5438(10) _cell_length_c 10.7708(7) _cell_angle_alpha 116.293(6) _cell_angle_beta 93.363(5) _cell_angle_gamma 102.472(6) _cell_volume 721.66(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 31 _cell_measurement_theta_min 11.35 _cell_measurement_theta_max 36.74 _exptl_crystal_description prisms _exptl_crystal_colour Orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method ? _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 8.476 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2207 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.65 _diffrn_reflns_theta_max 59.93 _reflns_number_total 2038 _reflns_number_observed 1772 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 63 with very negative F^2^ or flagged by the user for potential systematic errors. 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^)+(0.0658P)^2^+0.2211P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1975 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_obs 0.0440 _refine_ls_wR_factor_all 0.1108 _refine_ls_wR_factor_obs 0.1048 _refine_ls_goodness_of_fit_all 1.065 _refine_ls_goodness_of_fit_obs 1.095 _refine_ls_restrained_S_all 1.072 _refine_ls_restrained_S_obs 1.095 _refine_ls_shift/esd_max 0.000 _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 Fe Fe 0.39306(7) 0.20116(7) 0.24578(6) 0.0352(2) Uani 1 d . . C1 C 0.5091(5) 0.0275(5) 0.2292(5) 0.0455(9) Uani 1 d . . H1A H 0.4758(5) -0.0808(5) 0.1609(5) 0.055 Uiso 1 calc R . C2 C 0.6274(5) 0.1548(6) 0.2221(5) 0.0517(10) Uani 1 d . . H2A H 0.6854(5) 0.1446(6) 0.1480(5) 0.062 Uiso 1 calc R . C3 C 0.6429(5) 0.3006(6) 0.3469(5) 0.0516(10) Uani 1 d . . H3A H 0.7124(5) 0.4023(6) 0.3685(5) 0.062 Uiso 1 calc R . C4 C 0.5343(5) 0.2651(5) 0.4334(4) 0.0422(9) Uani 1 d . . H4A H 0.5206(5) 0.3388(5) 0.5216(4) 0.051 Uiso 1 calc R . C5 C 0.4495(5) 0.0949(5) 0.3599(4) 0.0376(8) Uani 1 d . . C6 C 0.1789(5) 0.0791(5) 0.0974(4) 0.0453(9) Uani 1 d . . H6A H 0.1483(5) -0.0307(5) 0.0330(4) 0.054 Uiso 1 calc R . C7 C 0.2733(6) 0.2052(6) 0.0752(5) 0.0540(11) Uani 1 d . . H7A H 0.3160(6) 0.1934(6) -0.0060(5) 0.065 Uiso 1 calc R . C8 C 0.2918(6) 0.3527(6) 0.1976(5) 0.0541(11) Uani 1 d . . H8A H 0.3500(6) 0.4549(6) 0.2112(5) 0.065 Uiso 1 calc R . C9 C 0.2064(5) 0.3193(5) 0.2975(4) 0.0436(9) Uani 1 d . . H9A H 0.1973(5) 0.3952(5) 0.3865(4) 0.052 Uiso 1 calc R . C10 C 0.1379(5) 0.1480(5) 0.2354(4) 0.0406(8) Uani 1 d . . C11 C 0.3047(5) 0.0024(5) 0.3994(4) 0.0405(8) Uani 1 d . . H11A H 0.2621(5) -0.1072(5) 0.3227(4) 0.049 Uiso 1 calc R . H11B H 0.3489(5) -0.0050(5) 0.4813(4) 0.049 Uiso 1 calc R . C12 C 0.0532(5) 0.0507(5) 0.3047(4) 0.0428(9) Uani 1 d . . H12A H -0.0511(5) 0.0801(5) 0.3306(4) 0.051 Uiso 1 calc R . H12B H 0.0223(5) -0.0637(5) 0.2373(4) 0.051 Uiso 1 calc R . N13 N 0.1623(4) 0.0767(4) 0.4305(3) 0.0385(7) Uani 1 d . . C14 C 0.1672(4) 0.2012(4) 0.5623(4) 0.0355(8) Uani 1 d . . C15 C 0.2970(5) 0.2448(5) 0.6762(4) 0.0417(9) Uani 1 d . . H15A H 0.3804(5) 0.1889(5) 0.6618(4) 0.050 Uiso 1 calc R . C16 C 0.3023(5) 0.3682(5) 0.8080(4) 0.0427(9) Uani 1 d . . H16A H 0.3890(5) 0.3955(5) 0.8815(4) 0.051 Uiso 1 calc R . C17 C 0.1796(5) 0.4511(5) 0.8311(4) 0.0396(8) Uani 1 d . . C18 C 0.0482(5) 0.4109(5) 0.7235(5) 0.0443(9) Uani 1 d . . H18A H -0.0355(5) 0.4665(5) 0.7407(5) 0.053 Uiso 1 calc R . C19 C 0.0421(5) 0.2880(5) 0.5908(4) 0.0416(9) Uani 1 d . . H19A H -0.0459(5) 0.2618(5) 0.5187(4) 0.050 Uiso 1 calc R . N20 N 0.1898(5) 0.5858(4) 0.9694(4) 0.0489(8) Uani 1 d . . O21 O 0.3077(5) 0.6184(4) 1.0636(4) 0.0677(9) Uani 1 d . . O22 O 0.0819(5) 0.6614(4) 0.9870(4) 0.0686(9) Uani 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 Fe 0.0311(3) 0.0383(3) 0.0437(3) 0.0270(2) 0.0087(2) 0.0053(2) C1 0.042(2) 0.048(2) 0.058(2) 0.031(2) 0.017(2) 0.018(2) C2 0.035(2) 0.069(3) 0.065(3) 0.043(2) 0.020(2) 0.012(2) C3 0.033(2) 0.062(3) 0.060(2) 0.037(2) 0.007(2) -0.007(2) C4 0.034(2) 0.047(2) 0.049(2) 0.028(2) 0.007(2) 0.005(2) C5 0.030(2) 0.042(2) 0.050(2) 0.028(2) 0.0068(15) 0.012(2) C6 0.039(2) 0.056(2) 0.042(2) 0.025(2) 0.003(2) 0.013(2) C7 0.051(2) 0.078(3) 0.050(2) 0.043(2) 0.012(2) 0.020(2) C8 0.057(3) 0.058(3) 0.073(3) 0.051(2) 0.020(2) 0.017(2) C9 0.042(2) 0.048(2) 0.053(2) 0.032(2) 0.011(2) 0.015(2) C10 0.028(2) 0.052(2) 0.044(2) 0.024(2) 0.0030(14) 0.011(2) C11 0.042(2) 0.033(2) 0.056(2) 0.029(2) 0.014(2) 0.009(2) C12 0.029(2) 0.044(2) 0.055(2) 0.027(2) 0.005(2) 0.001(2) N13 0.0302(15) 0.043(2) 0.052(2) 0.0320(15) 0.0116(13) 0.0054(13) C14 0.028(2) 0.038(2) 0.051(2) 0.033(2) 0.0129(14) 0.0041(15) C15 0.035(2) 0.051(2) 0.056(2) 0.037(2) 0.013(2) 0.015(2) C16 0.036(2) 0.052(2) 0.050(2) 0.035(2) 0.007(2) 0.005(2) C17 0.036(2) 0.039(2) 0.052(2) 0.030(2) 0.013(2) 0.005(2) C18 0.039(2) 0.048(2) 0.060(2) 0.034(2) 0.015(2) 0.016(2) C19 0.031(2) 0.049(2) 0.055(2) 0.035(2) 0.008(2) 0.008(2) N20 0.053(2) 0.040(2) 0.059(2) 0.029(2) 0.013(2) 0.007(2) O21 0.071(2) 0.060(2) 0.062(2) 0.025(2) -0.002(2) 0.009(2) O22 0.077(2) 0.057(2) 0.075(2) 0.028(2) 0.022(2) 0.028(2) _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 Fe C5 1.998(4) . ? Fe C10 2.015(4) . ? Fe C6 2.025(4) . ? Fe C1 2.026(4) . ? Fe C4 2.028(4) . ? Fe C8 2.042(4) . ? Fe C9 2.044(4) . ? Fe C7 2.049(4) . ? Fe C3 2.054(4) . ? Fe C2 2.056(4) . ? C1 C2 1.413(6) . ? C1 C5 1.430(6) . ? C2 C3 1.416(7) . ? C3 C4 1.418(6) . ? C4 C5 1.434(6) . ? C5 C11 1.515(5) . ? C6 C7 1.404(7) . ? C6 C10 1.429(6) . ? C7 C8 1.408(7) . ? C8 C9 1.427(6) . ? C9 C10 1.423(6) . ? C10 C12 1.514(6) . ? C11 N13 1.467(5) . ? C12 N13 1.468(5) . ? N13 C14 1.381(5) . ? C14 C19 1.412(5) . ? C14 C15 1.415(5) . ? C15 C16 1.376(6) . ? C16 C17 1.372(6) . ? C17 C18 1.385(6) . ? C17 N20 1.457(5) . ? C18 C19 1.380(6) . ? N20 O22 1.225(5) . ? N20 O21 1.235(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 C5 Fe C10 98.6(2) . . ? C5 Fe C6 115.9(2) . . ? C10 Fe C6 41.4(2) . . ? C5 Fe C1 41.6(2) . . ? C10 Fe C1 117.5(2) . . ? C6 Fe C1 104.3(2) . . ? C5 Fe C4 41.7(2) . . ? C10 Fe C4 116.0(2) . . ? C6 Fe C4 152.4(2) . . ? C1 Fe C4 69.6(2) . . ? C5 Fe C8 157.0(2) . . ? C10 Fe C8 68.8(2) . . ? C6 Fe C8 68.0(2) . . ? C1 Fe C8 161.3(2) . . ? C4 Fe C8 125.2(2) . . ? C5 Fe C9 117.3(2) . . ? C10 Fe C9 41.1(2) . . ? C6 Fe C9 68.9(2) . . ? C1 Fe C9 154.2(2) . . ? C4 Fe C9 104.4(2) . . ? C8 Fe C9 40.9(2) . . ? C5 Fe C7 154.4(2) . . ? C10 Fe C7 68.9(2) . . ? C6 Fe C7 40.3(2) . . ? C1 Fe C7 123.1(2) . . ? C4 Fe C7 163.9(2) . . ? C8 Fe C7 40.3(2) . . ? C9 Fe C7 68.6(2) . . ? C5 Fe C3 69.1(2) . . ? C10 Fe C3 154.9(2) . . ? C6 Fe C3 163.6(2) . . ? C1 Fe C3 68.5(2) . . ? C4 Fe C3 40.7(2) . . ? C8 Fe C3 114.0(2) . . ? C9 Fe C3 124.0(2) . . ? C7 Fe C3 130.5(2) . . ? C5 Fe C2 69.0(2) . . ? C10 Fe C2 156.6(2) . . ? C6 Fe C2 125.0(2) . . ? C1 Fe C2 40.5(2) . . ? C4 Fe C2 68.5(2) . . ? C8 Fe C2 129.1(2) . . ? C9 Fe C2 162.3(2) . . ? C7 Fe C2 113.6(2) . . ? C3 Fe C2 40.3(2) . . ? C2 C1 C5 107.8(4) . . ? C2 C1 Fe 70.9(3) . . ? C5 C1 Fe 68.1(2) . . ? C1 C2 C3 108.5(4) . . ? C1 C2 Fe 68.6(2) . . ? C3 C2 Fe 69.8(2) . . ? C2 C3 C4 108.4(4) . . ? C2 C3 Fe 69.9(2) . . ? C4 C3 Fe 68.7(2) . . ? C3 C4 C5 107.5(4) . . ? C3 C4 Fe 70.7(2) . . ? C5 C4 Fe 68.0(2) . . ? C1 C5 C4 107.8(3) . . ? C1 C5 C11 124.1(4) . . ? C4 C5 C11 127.6(3) . . ? C1 C5 Fe 70.3(2) . . ? C4 C5 Fe 70.3(2) . . ? C11 C5 Fe 118.6(3) . . ? C7 C6 C10 108.5(4) . . ? C7 C6 Fe 70.7(2) . . ? C10 C6 Fe 68.9(2) . . ? C6 C7 C8 108.0(4) . . ? C6 C7 Fe 68.9(2) . . ? C8 C7 Fe 69.6(2) . . ? C7 C8 C9 108.8(4) . . ? C7 C8 Fe 70.1(3) . . ? C9 C8 Fe 69.6(2) . . ? C10 C9 C8 107.1(4) . . ? C10 C9 Fe 68.4(2) . . ? C8 C9 Fe 69.5(2) . . ? C9 C10 C6 107.6(4) . . ? C9 C10 C12 127.5(4) . . ? C6 C10 C12 124.7(4) . . ? C9 C10 Fe 70.6(2) . . ? C6 C10 Fe 69.7(2) . . ? C12 C10 Fe 120.3(3) . . ? N13 C11 C5 113.7(3) . . ? N13 C12 C10 113.2(3) . . ? C14 N13 C11 120.8(3) . . ? C14 N13 C12 122.1(3) . . ? C11 N13 C12 113.6(3) . . ? N13 C14 C19 122.0(3) . . ? N13 C14 C15 121.0(3) . . ? C19 C14 C15 117.0(4) . . ? C16 C15 C14 121.3(4) . . ? C17 C16 C15 120.0(4) . . ? C16 C17 C18 120.9(4) . . ? C16 C17 N20 119.7(4) . . ? C18 C17 N20 119.4(4) . . ? C19 C18 C17 119.6(4) . . ? C18 C19 C14 121.2(4) . . ? O22 N20 O21 123.1(4) . . ? O22 N20 C17 118.8(4) . . ? O21 N20 C17 118.1(4) . . ? _refine_diff_density_max 0.550 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.067 data_MM9824 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H24 N2 O Fe Br2' _chemical_formula_weight 548.10 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' -1.1336 3.1974 '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 7.0023(10) _cell_length_b 17.849(2) _cell_length_c 17.560(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.526(11) _cell_angle_gamma 90.00 _cell_volume 2193.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19 _cell_measurement_theta_min 11.20 _cell_measurement_theta_max 19.11 _exptl_crystal_description 'prismatic needles' _exptl_crystal_colour Orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method ? _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 9.890 _exptl_absorpt_correction_type Ellipsoidal _exptl_absorpt_correction_T_min 0.3546 _exptl_absorpt_correction_T_max 0.5144 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3559 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.1103 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 60.00 _reflns_number_total 3258 _reflns_number_observed 2063 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 338 with very negative F^2^ or flagged by the user for potential systematic errors. 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^)+(0.0353P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00009(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2920 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_obs 0.0581 _refine_ls_wR_factor_all 0.1321 _refine_ls_wR_factor_obs 0.1097 _refine_ls_goodness_of_fit_all 1.004 _refine_ls_goodness_of_fit_obs 1.097 _refine_ls_restrained_S_all 1.028 _refine_ls_restrained_S_obs 1.097 _refine_ls_shift/esd_max 0.000 _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 Fe Fe 0.2113(2) 0.78508(7) 0.19641(7) 0.0373(3) Uani 1 d . . N1 N 0.5696(9) 0.9872(4) 0.1814(4) 0.0386(14) Uani 1 d . . C2 C 0.6275(14) 1.0203(5) 0.2456(5) 0.050(2) Uani 1 d . . H2A H 0.5504(14) 1.0197(5) 0.2879(5) 0.060 Uiso 1 calc R . C3 C 0.8014(15) 1.0555(5) 0.2493(6) 0.056(2) Uani 1 d . . H3A H 0.8451(15) 1.0775(5) 0.2945(6) 0.067 Uiso 1 calc R . C4 C 0.9127(13) 1.0579(5) 0.1841(7) 0.058(3) Uani 1 d . . H4A H 1.0291(13) 1.0830(5) 0.1851(7) 0.070 Uiso 1 calc R . C5 C 0.8484(13) 1.0231(5) 0.1194(6) 0.054(2) Uani 1 d . . H5A H 0.9231(13) 1.0222(5) 0.0764(6) 0.064 Uiso 1 calc R . C6 C 0.6743(15) 0.9897(6) 0.1183(5) 0.053(2) Uani 1 d . . H6A H 0.6267(15) 0.9682(6) 0.0734(5) 0.064 Uiso 1 calc R . C7 C 0.3781(13) 0.9479(5) 0.1793(6) 0.051(2) Uani 1 d . . H7A H 0.3048(13) 0.9627(5) 0.2228(6) 0.061 Uiso 1 calc R . H7B H 0.3066(13) 0.9616(5) 0.1333(6) 0.061 Uiso 1 calc R . C8 C 0.4078(15) 0.8152(6) 0.1175(6) 0.060(3) Uani 1 d . . H8A H 0.3835(15) 0.8285(6) 0.0670(6) 0.072 Uiso 1 calc R . C9 C 0.4470(18) 0.7425(7) 0.1452(9) 0.081(4) Uani 1 d . . H9A H 0.4517(18) 0.6992(7) 0.1158(9) 0.097 Uiso 1 calc R . C10 C 0.4776(16) 0.7464(6) 0.2238(9) 0.070(3) Uani 1 d . . H10A H 0.5069(16) 0.7063(6) 0.2559(9) 0.084 Uiso 1 calc R . C11 C 0.4559(14) 0.8233(5) 0.2469(6) 0.052(2) Uani 1 d . . H11A H 0.4686(14) 0.8420(5) 0.2962(6) 0.063 Uiso 1 calc R . C12 C 0.4122(11) 0.8644(4) 0.1809(4) 0.036(2) Uani 1 d . . N13 N -0.1326(10) 0.8090(4) 0.4009(4) 0.0391(15) Uani 1 d . . C14 C -0.2092(15) 0.8768(6) 0.4189(5) 0.054(2) Uani 1 d . . H14A H -0.1430(15) 0.9207(6) 0.4089(5) 0.065 Uiso 1 calc R . C15 C -0.3862(17) 0.8797(8) 0.4522(6) 0.072(3) Uani 1 d . . H15A H -0.4406(17) 0.9255(8) 0.4646(6) 0.086 Uiso 1 calc R . C16 C -0.4807(16) 0.8134(8) 0.4667(6) 0.071(3) Uani 1 d . . H16A H -0.6008(16) 0.8148(8) 0.4881(6) 0.085 Uiso 1 calc R . C17 C -0.3983(16) 0.7446(7) 0.4498(6) 0.063(3) Uani 1 d . . H17A H -0.4586(16) 0.6998(7) 0.4616(6) 0.076 Uiso 1 calc R . C18 C -0.2239(14) 0.7453(5) 0.4149(5) 0.048(2) Uani 1 d . . H18A H -0.1689(14) 0.7001(5) 0.4008(5) 0.057 Uiso 1 calc R . C19 C 0.0537(12) 0.8059(5) 0.3606(5) 0.044(2) Uani 1 d . . H19A H 0.1175(12) 0.8540(5) 0.3644(5) 0.053 Uiso 1 calc R . H19B H 0.1362(12) 0.7684(5) 0.3842(5) 0.053 Uiso 1 calc R . C20 C 0.0277(13) 0.7134(5) 0.2470(5) 0.046(2) Uani 1 d . . H20A H 0.0592(13) 0.6699(5) 0.2737(5) 0.056 Uiso 1 calc R . C21 C -0.0164(15) 0.7177(6) 0.1678(6) 0.058(2) Uani 1 d . . H21A H -0.0160(15) 0.6782(6) 0.1333(6) 0.070 Uiso 1 calc R . C22 C -0.0613(14) 0.7936(7) 0.1510(5) 0.057(2) Uani 1 d . . H22A H -0.0976(14) 0.8121(7) 0.1032(5) 0.068 Uiso 1 calc R . C23 C -0.0424(13) 0.8361(5) 0.2175(5) 0.047(2) Uani 1 d . . H23A H -0.0635(13) 0.8874(5) 0.2215(5) 0.057 Uiso 1 calc R . C24 C 0.0157(12) 0.7866(5) 0.2790(5) 0.042(2) Uani 1 d . . Br1 Br 0.19039(15) 0.61455(5) 0.44166(6) 0.0507(3) Uani 1 d . . Br2 Br 0.2160(2) 1.01202(7) 0.37724(6) 0.0618(3) Uani 1 d . . O O -0.1724(15) 1.0822(6) 0.4594(6) 0.100(3) Uani 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 Fe 0.0363(7) 0.0339(6) 0.0419(6) 0.0010(5) 0.0080(5) -0.0042(6) N1 0.031(3) 0.030(3) 0.055(4) 0.005(3) 0.006(3) -0.008(3) C2 0.056(5) 0.043(4) 0.052(5) 0.001(4) 0.004(4) 0.004(4) C3 0.057(6) 0.041(4) 0.068(6) -0.014(4) -0.005(5) -0.008(4) C4 0.031(4) 0.041(5) 0.103(8) -0.001(5) 0.013(5) -0.007(4) C5 0.037(5) 0.056(5) 0.069(6) 0.002(4) 0.028(4) 0.008(4) C6 0.057(6) 0.059(5) 0.044(4) 0.001(4) 0.011(4) 0.005(5) C7 0.033(5) 0.041(5) 0.078(6) 0.008(4) 0.006(4) -0.013(4) C8 0.061(6) 0.065(6) 0.056(5) -0.017(5) 0.024(5) -0.024(5) C9 0.057(7) 0.054(6) 0.134(13) -0.023(7) 0.034(8) -0.007(5) C10 0.045(6) 0.036(5) 0.130(11) 0.015(6) 0.004(6) 0.005(4) C11 0.042(5) 0.053(5) 0.062(5) 0.010(4) 0.002(4) -0.008(4) C12 0.034(4) 0.034(4) 0.039(4) 0.004(3) 0.004(3) -0.001(3) N13 0.035(4) 0.047(4) 0.035(3) 0.000(3) 0.003(3) 0.002(3) C14 0.059(6) 0.050(5) 0.053(5) -0.015(4) -0.002(4) 0.001(5) C15 0.062(6) 0.092(8) 0.062(6) -0.037(6) 0.002(5) 0.025(7) C16 0.043(6) 0.127(11) 0.043(4) -0.017(6) 0.007(4) 0.012(6) C17 0.050(6) 0.089(8) 0.049(5) 0.014(5) 0.007(4) -0.016(6) C18 0.047(5) 0.050(5) 0.047(4) 0.010(4) 0.005(4) -0.007(4) C19 0.031(4) 0.055(5) 0.048(4) -0.010(4) 0.014(4) -0.005(4) C20 0.053(5) 0.037(4) 0.050(4) -0.007(4) 0.018(4) -0.011(4) C21 0.057(6) 0.066(6) 0.051(5) -0.004(5) 0.005(4) -0.027(5) C22 0.044(5) 0.085(7) 0.042(5) 0.007(5) 0.000(4) -0.017(5) C23 0.038(5) 0.053(5) 0.052(5) 0.007(4) 0.009(4) -0.008(4) C24 0.036(4) 0.049(4) 0.040(4) -0.002(4) 0.003(3) -0.013(4) Br1 0.0511(5) 0.0481(5) 0.0534(5) -0.0014(4) 0.0110(4) -0.0004(5) Br2 0.0584(6) 0.0676(6) 0.0600(6) -0.0068(5) 0.0149(5) -0.0041(5) O 0.092(7) 0.107(7) 0.101(7) 0.031(6) 0.026(6) 0.029(6) _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 Fe C12 2.019(8) . ? Fe C24 2.022(8) . ? Fe C11 2.026(10) . ? Fe C10 2.034(11) . ? Fe C20 2.035(8) . ? Fe C23 2.039(9) . ? Fe C9 2.047(11) . ? Fe C21 2.049(10) . ? Fe C8 2.050(9) . ? Fe C22 2.055(10) . ? N1 C2 1.328(12) . ? N1 C6 1.345(11) . ? N1 C7 1.512(10) . ? C2 C3 1.370(14) . ? C3 C4 1.402(15) . ? C4 C5 1.36(2) . ? C5 C6 1.357(14) . ? C7 C12 1.509(12) . ? C8 C9 1.41(2) . ? C8 C12 1.417(12) . ? C9 C10 1.39(2) . ? C10 C11 1.440(15) . ? C11 C12 1.399(12) . ? N13 C18 1.332(12) . ? N13 C14 1.363(12) . ? N13 C19 1.501(10) . ? C14 C15 1.39(2) . ? C15 C16 1.38(2) . ? C16 C17 1.39(2) . ? C17 C18 1.381(14) . ? C19 C24 1.490(12) . ? C20 C21 1.420(14) . ? C20 C24 1.426(12) . ? C21 C22 1.42(2) . ? C22 C23 1.397(14) . ? C23 C24 1.446(12) . ? 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 Fe C24 125.1(3) . . ? C12 Fe C11 40.5(3) . . ? C24 Fe C11 105.2(4) . . ? C12 Fe C10 68.5(4) . . ? C24 Fe C10 118.0(5) . . ? C11 Fe C10 41.6(4) . . ? C12 Fe C20 161.9(3) . . ? C24 Fe C20 41.2(3) . . ? C11 Fe C20 123.9(4) . . ? C10 Fe C20 105.6(4) . . ? C12 Fe C23 108.9(3) . . ? C24 Fe C23 41.7(4) . . ? C11 Fe C23 120.0(4) . . ? C10 Fe C23 155.0(5) . . ? C20 Fe C23 68.8(4) . . ? C12 Fe C9 68.2(4) . . ? C24 Fe C9 152.9(5) . . ? C11 Fe C9 68.6(5) . . ? C10 Fe C9 39.9(6) . . ? C20 Fe C9 119.0(4) . . ? C23 Fe C9 164.2(6) . . ? C12 Fe C21 156.7(4) . . ? C24 Fe C21 69.3(4) . . ? C11 Fe C21 161.5(4) . . ? C10 Fe C21 124.2(5) . . ? C20 Fe C21 40.7(4) . . ? C23 Fe C21 68.3(4) . . ? C9 Fe C21 107.8(5) . . ? C12 Fe C8 40.7(3) . . ? C24 Fe C8 163.9(4) . . ? C11 Fe C8 68.4(4) . . ? C10 Fe C8 67.8(5) . . ? C20 Fe C8 154.6(4) . . ? C23 Fe C8 127.5(4) . . ? C9 Fe C8 40.3(5) . . ? C21 Fe C8 121.3(4) . . ? C12 Fe C22 122.6(4) . . ? C24 Fe C22 68.8(4) . . ? C11 Fe C22 155.6(4) . . ? C10 Fe C22 162.4(5) . . ? C20 Fe C22 68.0(4) . . ? C23 Fe C22 39.9(4) . . ? C9 Fe C22 127.5(5) . . ? C21 Fe C22 40.5(4) . . ? C8 Fe C22 110.6(4) . . ? C2 N1 C6 121.6(8) . . ? C2 N1 C7 118.5(8) . . ? C6 N1 C7 119.8(8) . . ? N1 C2 C3 119.7(9) . . ? C2 C3 C4 119.3(9) . . ? C5 C4 C3 119.2(8) . . ? C6 C5 C4 119.3(8) . . ? N1 C6 C5 120.8(9) . . ? C12 C7 N1 108.5(7) . . ? C9 C8 C12 107.5(10) . . ? C9 C8 Fe 69.8(6) . . ? C12 C8 Fe 68.5(5) . . ? C10 C9 C8 108.5(10) . . ? C10 C9 Fe 69.5(7) . . ? C8 C9 Fe 70.0(6) . . ? C9 C10 C11 108.1(10) . . ? C9 C10 Fe 70.5(7) . . ? C11 C10 Fe 68.9(6) . . ? C12 C11 C10 106.9(10) . . ? C12 C11 Fe 69.5(5) . . ? C10 C11 Fe 69.5(6) . . ? C11 C12 C8 108.9(8) . . ? C11 C12 C7 124.4(8) . . ? C8 C12 C7 126.7(8) . . ? C11 C12 Fe 70.0(5) . . ? C8 C12 Fe 70.8(5) . . ? C7 C12 Fe 125.8(6) . . ? C18 N13 C14 121.4(8) . . ? C18 N13 C19 118.9(7) . . ? C14 N13 C19 119.7(8) . . ? N13 C14 C15 119.6(11) . . ? C16 C15 C14 118.8(11) . . ? C15 C16 C17 120.9(10) . . ? C18 C17 C16 117.6(11) . . ? N13 C18 C17 121.7(10) . . ? C24 C19 N13 109.1(7) . . ? C21 C20 C24 108.8(9) . . ? C21 C20 Fe 70.2(5) . . ? C24 C20 Fe 68.9(4) . . ? C22 C21 C20 107.3(9) . . ? C22 C21 Fe 70.0(5) . . ? C20 C21 Fe 69.1(5) . . ? C23 C22 C21 109.2(9) . . ? C23 C22 Fe 69.5(6) . . ? C21 C22 Fe 69.5(6) . . ? C22 C23 C24 108.2(8) . . ? C22 C23 Fe 70.7(6) . . ? C24 C23 Fe 68.5(5) . . ? C20 C24 C23 106.5(8) . . ? C20 C24 C19 125.4(8) . . ? C23 C24 C19 128.1(8) . . ? C20 C24 Fe 69.9(5) . . ? C23 C24 Fe 69.8(5) . . ? C19 C24 Fe 125.9(6) . . ? _refine_diff_density_max 0.428 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.100 data_MM9819 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H22 N4 O6 Fe' _chemical_formula_weight 422.23 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Fe' 'Fe' -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.6173(13) _cell_length_b 9.8859(12) _cell_length_c 13.1947(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.883(13) _cell_angle_gamma 90.00 _cell_volume 1774.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 6.72 _cell_measurement_theta_max 21.90 _exptl_crystal_description needles _exptl_crystal_colour Orange/yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method ? _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 7.208 _exptl_absorpt_correction_type Ellipsoidal _exptl_absorpt_correction_T_min 0.4066 _exptl_absorpt_correction_T_max 0.5175 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1386 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.53 _diffrn_reflns_theta_max 59.95 _reflns_number_total 1324 _reflns_number_observed 1082 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 45 with very negative F^2^ or flagged by the user for potential systematic errors. 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^)+(0.0577P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1279 _refine_ls_number_parameters 144 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_obs 0.0452 _refine_ls_wR_factor_all 0.1089 _refine_ls_wR_factor_obs 0.1004 _refine_ls_goodness_of_fit_all 1.058 _refine_ls_goodness_of_fit_obs 1.106 _refine_ls_restrained_S_all 1.069 _refine_ls_restrained_S_obs 1.103 _refine_ls_shift/esd_max 0.000 _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 Fe Fe 0.0000 0.35757(8) 0.2500 0.0274(3) Uani 1 d S . C1 C 0.0328(3) 0.4600(4) 0.1230(3) 0.0306(8) Uani 1 d . . C2 C -0.0714(3) 0.4484(4) 0.1283(3) 0.0346(9) Uani 1 d . . H2A H -0.1159(3) 0.5195(4) 0.1304(3) 0.042 Uiso 1 calc R . C3 C -0.0942(3) 0.3089(4) 0.1298(3) 0.0393(9) Uani 1 d . . H3A H -0.1570(3) 0.2726(4) 0.1332(3) 0.047 Uiso 1 calc R . C4 C -0.0063(4) 0.2337(4) 0.1253(3) 0.0432(10) Uani 1 d . . H4A H -0.0011(4) 0.1399(4) 0.1254(3) 0.052 Uiso 1 calc R . C5 C 0.0721(3) 0.3258(4) 0.1205(3) 0.0397(10) Uani 1 d . . H5A H 0.1381(3) 0.3034(4) 0.1164(3) 0.048 Uiso 1 calc R . C6 C 0.0915(3) 0.5856(4) 0.1209(3) 0.0306(8) Uani 1 d . . O6 O 0.1809(2) 0.5839(3) 0.1079(2) 0.0429(7) Uani 1 d . . N7 N 0.0427(3) 0.7007(3) 0.1328(2) 0.0354(8) Uani 1 d D . H7A H -0.0199(9) 0.6973(37) 0.1515(26) 0.017(9) Uiso 1 d D . C8 C 0.0921(4) 0.8293(4) 0.1265(3) 0.0449(11) Uani 1 d . . H8A H 0.0442(4) 0.8979(4) 0.1058(3) 0.054 Uiso 1 calc R . H8B H 0.1398(4) 0.8240(4) 0.0745(3) 0.054 Uiso 1 calc R . C9 C 0.1446(3) 0.8730(4) 0.2264(3) 0.0369(9) Uani 1 d . . O9 O 0.1420(3) 0.8045(4) 0.3043(2) 0.0597(10) Uani 1 d . . N10 N 0.1912(3) 0.9901(4) 0.2200(3) 0.0434(9) Uani 1 d D . H10B H 0.2283(29) 1.0184(48) 0.2742(22) 0.045(13) Uiso 1 d D . H10A H 0.1931(50) 1.0339(59) 0.1603(25) 0.083(21) Uiso 1 d D . O20 O 0.2977(3) 0.4175(4) -0.0082(3) 0.0705(12) Uani 1 d D . H20A H 0.2508(25) 0.4694(41) 0.0177(36) 0.047(13) Uiso 1 d D . H20B H 0.3323(51) 0.3751(72) 0.0424(42) 0.115(28) Uiso 1 d 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 Fe 0.0419(5) 0.0214(4) 0.0189(4) 0.000 -0.0011(3) 0.000 C1 0.044(2) 0.031(2) 0.016(2) -0.0044(14) -0.0027(15) 0.004(2) C2 0.044(2) 0.035(2) 0.024(2) 0.000(2) -0.004(2) 0.001(2) C3 0.051(2) 0.039(2) 0.027(2) -0.003(2) -0.005(2) -0.012(2) C4 0.072(3) 0.026(2) 0.031(2) -0.002(2) 0.004(2) 0.001(2) C5 0.054(2) 0.035(2) 0.031(2) -0.008(2) 0.007(2) 0.008(2) C6 0.044(2) 0.031(2) 0.016(2) 0.0029(14) -0.0044(15) 0.001(2) O6 0.048(2) 0.044(2) 0.037(2) 0.0061(13) 0.0020(13) 0.0012(13) N7 0.045(2) 0.030(2) 0.031(2) -0.0001(13) -0.0041(14) -0.0025(15) C8 0.070(3) 0.033(2) 0.030(2) 0.003(2) -0.007(2) -0.007(2) C9 0.045(2) 0.040(2) 0.027(2) -0.002(2) 0.001(2) -0.004(2) O9 0.083(2) 0.062(2) 0.033(2) 0.010(2) -0.010(2) -0.031(2) N10 0.052(2) 0.042(2) 0.036(2) 0.000(2) -0.002(2) -0.012(2) O20 0.098(3) 0.073(3) 0.042(2) 0.012(2) 0.021(2) 0.033(2) _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 Fe C1 2.027(4) 2 ? Fe C1 2.027(4) . ? Fe C5 2.037(4) 2 ? Fe C5 2.037(4) . ? Fe C2 2.042(4) 2 ? Fe C2 2.042(4) . ? Fe C3 2.047(4) . ? Fe C3 2.047(4) 2 ? Fe C4 2.050(4) 2 ? Fe C4 2.050(4) . ? C1 C2 1.428(6) . ? C1 C5 1.432(5) . ? C1 C6 1.478(5) . ? C2 C3 1.414(6) . ? C3 C4 1.414(7) . ? C4 C5 1.406(6) . ? C6 O6 1.238(5) . ? C6 N7 1.331(5) . ? N7 C8 1.443(5) . ? C8 C9 1.530(5) . ? C9 O9 1.233(5) . ? C9 N10 1.324(6) . ? 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 C1 Fe C1 120.0(2) 2 . ? C1 Fe C5 41.3(2) 2 2 ? C1 Fe C5 154.9(2) . 2 ? C1 Fe C5 154.9(2) 2 . ? C1 Fe C5 41.3(2) . . ? C5 Fe C5 162.3(2) 2 . ? C1 Fe C2 41.1(2) 2 2 ? C1 Fe C2 108.3(2) . 2 ? C5 Fe C2 68.8(2) 2 2 ? C5 Fe C2 119.8(2) . 2 ? C1 Fe C2 108.3(2) 2 . ? C1 Fe C2 41.1(2) . . ? C5 Fe C2 119.8(2) 2 . ? C5 Fe C2 68.8(2) . . ? C2 Fe C2 127.9(2) 2 . ? C1 Fe C3 127.0(2) 2 . ? C1 Fe C3 68.4(2) . . ? C5 Fe C3 107.7(2) 2 . ? C5 Fe C3 67.9(2) . . ? C2 Fe C3 165.3(2) 2 . ? C2 Fe C3 40.5(2) . . ? C1 Fe C3 68.4(2) 2 2 ? C1 Fe C3 127.0(2) . 2 ? C5 Fe C3 67.9(2) 2 2 ? C5 Fe C3 107.7(2) . 2 ? C2 Fe C3 40.5(2) 2 2 ? C2 Fe C3 165.3(2) . 2 ? C3 Fe C3 152.8(2) . 2 ? C1 Fe C4 68.7(2) 2 2 ? C1 Fe C4 163.8(2) . 2 ? C5 Fe C4 40.3(2) 2 2 ? C5 Fe C4 125.4(2) . 2 ? C2 Fe C4 68.4(2) 2 2 ? C2 Fe C4 153.2(2) . 2 ? C3 Fe C4 118.8(2) . 2 ? C3 Fe C4 40.4(2) 2 2 ? C1 Fe C4 163.8(2) 2 . ? C1 Fe C4 68.7(2) . . ? C5 Fe C4 125.4(2) 2 . ? C5 Fe C4 40.3(2) . . ? C2 Fe C4 153.2(2) 2 . ? C2 Fe C4 68.4(2) . . ? C3 Fe C4 40.4(2) . . ? C3 Fe C4 118.8(2) 2 . ? C4 Fe C4 106.6(2) 2 . ? C2 C1 C5 107.4(4) . . ? C2 C1 C6 127.5(3) . . ? C5 C1 C6 125.1(4) . . ? C2 C1 Fe 70.0(2) . . ? C5 C1 Fe 69.8(2) . . ? C6 C1 Fe 125.3(2) . . ? C3 C2 C1 107.4(4) . . ? C3 C2 Fe 69.9(2) . . ? C1 C2 Fe 68.9(2) . . ? C2 C3 C4 108.9(4) . . ? C2 C3 Fe 69.6(2) . . ? C4 C3 Fe 69.9(2) . . ? C5 C4 C3 107.9(4) . . ? C5 C4 Fe 69.4(2) . . ? C3 C4 Fe 69.7(2) . . ? C4 C5 C1 108.3(4) . . ? C4 C5 Fe 70.3(2) . . ? C1 C5 Fe 69.0(2) . . ? O6 C6 N7 121.9(4) . . ? O6 C6 C1 121.9(4) . . ? N7 C6 C1 116.3(3) . . ? C6 N7 C8 120.7(4) . . ? N7 C8 C9 113.5(3) . . ? O9 C9 N10 124.5(4) . . ? O9 C9 C8 122.1(4) . . ? N10 C9 C8 113.4(4) . . ? _refine_diff_density_max 0.300 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.062