# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Enrique Colacio' 'Jean-Pierre Costes' 'Jose M. Dominguez-Vera' 'Ikram Ben Maimoun' 'Jose Suarez-Varela' _publ_contact_author_name 'Prof Enrique Colacio' _publ_contact_author_address ; Departmento de Quimica Inorganica Universidad de Granada Granada 18071 SPAIN ; _publ_contact_author_email ECOLACIO@UGR.ES _publ_requested_journal 'Chemical Communications' _publ_section_title ; Rational design of azide-bridged bimetallic complexes. Crystal Structure and magnetic properties of FeIIIMFeIII (M=NiII and CuII) trinuclear species ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 249654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H44 Cl4 Fe2 N24 Ni O4' _chemical_formula_weight 1309.26 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' 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' Ni Ni 0.3393 1.1124 '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 9.787(3) _cell_length_b 13.274(4) _cell_length_c 20.682(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.242(7) _cell_angle_gamma 90.00 _cell_volume 2675.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1058 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 17 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 1.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction. (1996) Bruker-AXS within SAINT+package, v.6.22. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 63 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 16760 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_sigmaI/netI 0.1274 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6070 _reflns_number_gt 3245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'WINGX V.1.64' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6070 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1528 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.004 _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 Ni Ni 0.5000 0.0000 0.5000 0.0406(3) Uani 1 2 d S . . Fe Fe 0.72460(7) 0.16098(5) 0.28142(3) 0.0366(2) Uani 1 1 d . . . Cl1 Cl 1.00083(15) 0.40624(11) 0.56028(7) 0.0544(4) Uani 1 1 d . . . Cl2 Cl 0.69847(15) 0.49418(11) 0.53991(7) 0.0597(4) Uani 1 1 d . . . N7 N 0.4880(5) 0.0149(4) 0.3928(3) 0.0639(14) Uani 1 1 d . . . O1 O 1.1041(4) 0.1633(3) 0.3896(2) 0.0694(13) Uani 1 1 d . . . O2 O 0.4355(4) 0.3632(3) 0.3418(2) 0.0637(12) Uani 1 1 d . . . N6 N 0.5750(4) 0.0215(3) 0.3575(2) 0.0389(11) Uani 1 1 d . . . N3 N 0.6313(4) 0.2646(3) 0.33691(19) 0.0345(10) Uani 1 1 d . . . N2 N 0.8789(4) 0.1982(3) 0.35075(19) 0.0355(10) Uani 1 1 d . . . N1 N 0.8909(4) 0.0650(3) 0.2589(2) 0.0424(11) Uani 1 1 d . . . C10 C 0.8885(5) 0.3687(4) 0.4946(2) 0.0378(12) Uani 1 1 d . . . N4 N 0.5158(4) 0.1636(3) 0.2390(2) 0.0400(10) Uani 1 1 d . . . C12 C 0.6689(5) 0.3748(4) 0.4346(2) 0.0360(12) Uani 1 1 d . . . H12 H 0.5801 0.4004 0.4294 0.043 Uiso 1 1 calc R . . C8 C 0.8474(5) 0.2671(4) 0.3988(2) 0.0348(12) Uani 1 1 d . . . C13 C 0.7106(5) 0.3056(4) 0.3904(2) 0.0336(12) Uani 1 1 d . . . C2 C 1.0079(6) 0.0793(4) 0.2958(3) 0.0445(14) Uani 1 1 d . . . N11 N 0.8586(5) 0.2659(4) 0.1810(2) 0.0531(13) Uani 1 1 d . . . N9 N 0.5722(5) 0.1446(4) 0.5108(3) 0.0521(13) Uani 1 1 d . . . N5 N 0.6612(5) 0.0257(3) 0.3230(2) 0.0487(12) Uani 1 1 d . . . N8 N 0.7033(5) -0.0416(4) 0.5111(3) 0.0536(14) Uani 1 1 d . . . N10 N 0.7572(5) 0.2391(4) 0.2023(2) 0.0519(13) Uani 1 1 d . . . C19 C 0.4637(6) 0.1055(4) 0.1889(3) 0.0477(14) Uani 1 1 d . . . H19 H 0.5166 0.0530 0.1748 0.057 Uiso 1 1 calc R . . C9 C 0.9339(5) 0.3011(4) 0.4510(2) 0.0360(12) Uani 1 1 d . . . H9 H 1.0238 0.2779 0.4567 0.043 Uiso 1 1 calc R . . C7 C 1.0027(6) 0.1526(4) 0.3513(3) 0.0439(14) Uani 1 1 d . . . C11 C 0.7569(5) 0.4062(4) 0.4861(2) 0.0373(12) Uani 1 1 d . . . C18 C 0.3352(6) 0.1215(4) 0.1582(3) 0.0552(16) Uani 1 1 d . . . H18 H 0.3011 0.0806 0.1240 0.066 Uiso 1 1 calc R . . C23 C 0.3381(7) 0.2190(5) 0.5172(3) 0.0698(19) Uani 1 1 d . . . H23A H 0.2933 0.2765 0.5351 0.084 Uiso 1 1 calc R . . H23B H 0.3370 0.2296 0.4708 0.084 Uiso 1 1 calc R . . C14 C 0.5016(5) 0.2956(4) 0.3178(3) 0.0412(13) Uani 1 1 d . . . C22 C 0.4862(7) 0.2164(5) 0.5461(3) 0.0674(19) Uani 1 1 d . . . H22A H 0.5249 0.2836 0.5445 0.081 Uiso 1 1 calc R . . H22B H 0.4890 0.1966 0.5914 0.081 Uiso 1 1 calc R . . C20 C 0.7845(6) 0.0516(5) 0.5059(3) 0.0644(18) Uani 1 1 d . . . H20A H 0.7901 0.0687 0.4606 0.077 Uiso 1 1 calc R . . H20B H 0.8768 0.0422 0.5263 0.077 Uiso 1 1 calc R . . C6 C 0.8870(6) -0.0021(4) 0.2100(3) 0.0574(16) Uani 1 1 d . . . H6 H 0.8046 -0.0124 0.1847 0.069 Uiso 1 1 calc R . . C3 C 1.1263(6) 0.0276(4) 0.2843(3) 0.0575(16) Uani 1 1 d . . . H3 H 1.2075 0.0383 0.3105 0.069 Uiso 1 1 calc R . . C4 C 1.1219(7) -0.0399(5) 0.2336(3) 0.0676(19) Uani 1 1 d . . . H4 H 1.2006 -0.0746 0.2247 0.081 Uiso 1 1 calc R . . C17 C 0.2579(6) 0.1994(5) 0.1792(3) 0.0617(17) Uani 1 1 d . . . H17 H 0.1712 0.2124 0.1587 0.074 Uiso 1 1 calc R . . C15 C 0.4385(5) 0.2376(4) 0.2597(3) 0.0398(13) Uani 1 1 d . . . C21 C 0.7128(6) 0.1344(5) 0.5397(3) 0.0653(18) Uani 1 1 d . . . H21A H 0.7130 0.1188 0.5855 0.078 Uiso 1 1 calc R . . H21B H 0.7614 0.1975 0.5356 0.078 Uiso 1 1 calc R . . C16 C 0.3095(6) 0.2583(4) 0.2310(3) 0.0544(16) Uani 1 1 d . . . H16 H 0.2580 0.3108 0.2460 0.065 Uiso 1 1 calc R . . C5 C 1.0008(7) -0.0557(5) 0.1962(3) 0.0649(19) Uani 1 1 d . . . H5 H 0.9958 -0.1018 0.1622 0.078 Uiso 1 1 calc R . . N12 N 0.9549(6) 0.2965(5) 0.1590(3) 0.088(2) Uani 1 1 d . . . C24 C 0.7444(6) -0.1264(5) 0.4714(3) 0.0647(18) Uani 1 1 d . . . H24A H 0.8410 -0.1406 0.4820 0.078 Uiso 1 1 calc R . . H24B H 0.7312 -0.1081 0.4258 0.078 Uiso 1 1 calc R . . H8 H 0.716(4) -0.061(3) 0.546(2) 0.022(14) Uiso 1 1 d . . . H91 H 0.573(6) 0.172(4) 0.470(3) 0.08(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0426(6) 0.0403(6) 0.0389(6) 0.0029(5) 0.0041(4) -0.0056(5) Fe 0.0422(5) 0.0353(4) 0.0316(4) -0.0014(4) -0.0009(3) 0.0053(4) Cl1 0.0647(10) 0.0534(9) 0.0407(8) -0.0032(7) -0.0186(7) -0.0024(7) Cl2 0.0685(10) 0.0583(10) 0.0505(9) -0.0229(8) -0.0037(7) 0.0115(8) N7 0.063(3) 0.071(4) 0.059(4) 0.009(3) 0.012(3) -0.002(3) O1 0.047(3) 0.094(3) 0.064(3) -0.022(3) -0.015(2) 0.029(2) O2 0.043(2) 0.065(3) 0.081(3) -0.033(2) -0.009(2) 0.020(2) N6 0.043(3) 0.033(3) 0.040(3) 0.006(2) 0.000(2) -0.002(2) N3 0.031(2) 0.035(2) 0.036(3) -0.005(2) -0.0055(19) 0.0012(19) N2 0.031(2) 0.040(3) 0.035(2) -0.003(2) 0.0015(19) 0.0058(19) N1 0.056(3) 0.037(3) 0.035(3) 0.002(2) 0.008(2) 0.013(2) C10 0.046(3) 0.033(3) 0.033(3) 0.007(2) -0.004(2) -0.012(2) N4 0.040(3) 0.039(3) 0.040(3) 0.000(2) -0.004(2) 0.003(2) C12 0.037(3) 0.036(3) 0.034(3) -0.003(2) 0.001(2) 0.005(2) C8 0.042(3) 0.030(3) 0.032(3) 0.005(2) 0.001(2) -0.001(2) C13 0.038(3) 0.032(3) 0.032(3) 0.001(2) 0.006(2) 0.000(2) C2 0.050(4) 0.046(4) 0.038(3) 0.013(3) 0.011(3) 0.009(3) N11 0.055(3) 0.056(3) 0.047(3) 0.000(3) -0.003(3) 0.018(3) N9 0.060(3) 0.052(3) 0.042(3) 0.008(3) -0.008(3) -0.017(3) N5 0.058(3) 0.040(3) 0.048(3) 0.009(2) 0.008(2) 0.004(2) N8 0.058(3) 0.060(4) 0.043(3) 0.009(3) 0.005(3) 0.004(3) N10 0.049(3) 0.060(3) 0.045(3) 0.019(2) 0.000(2) 0.006(3) C19 0.059(4) 0.039(3) 0.044(4) -0.011(3) 0.000(3) -0.003(3) C9 0.032(3) 0.037(3) 0.039(3) 0.005(2) 0.002(2) -0.001(2) C7 0.046(4) 0.048(3) 0.038(3) -0.004(3) 0.003(3) 0.003(3) C11 0.048(3) 0.029(3) 0.034(3) -0.003(2) -0.001(2) -0.003(2) C18 0.056(4) 0.057(4) 0.051(4) -0.014(3) -0.007(3) -0.013(3) C23 0.084(5) 0.060(5) 0.064(5) -0.002(4) 0.001(4) 0.015(4) C14 0.040(3) 0.041(3) 0.042(3) -0.004(3) -0.004(3) -0.003(3) C22 0.095(5) 0.052(4) 0.057(4) -0.016(3) 0.017(4) -0.013(4) C20 0.040(4) 0.085(5) 0.066(5) 0.018(4) -0.002(3) -0.019(3) C6 0.083(5) 0.052(4) 0.037(3) 0.002(3) 0.008(3) 0.018(3) C3 0.057(4) 0.057(4) 0.059(4) 0.003(3) 0.012(3) 0.018(3) C4 0.081(5) 0.061(4) 0.066(5) 0.014(4) 0.034(4) 0.026(4) C17 0.045(4) 0.079(5) 0.057(4) -0.013(4) -0.018(3) 0.004(3) C15 0.031(3) 0.043(3) 0.044(3) -0.002(3) -0.004(2) 0.003(3) C21 0.071(5) 0.065(4) 0.059(4) 0.001(3) 0.003(4) -0.024(4) C16 0.047(4) 0.055(4) 0.058(4) -0.010(3) -0.010(3) 0.011(3) C5 0.095(6) 0.052(4) 0.050(4) -0.002(3) 0.023(4) 0.019(4) N12 0.064(4) 0.089(5) 0.115(6) -0.007(4) 0.035(4) 0.010(3) C24 0.061(4) 0.073(5) 0.059(4) 0.011(4) 0.002(3) 0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni N9 2.050(5) . ? Ni N9 2.050(5) 3_656 ? Ni N8 2.057(5) 3_656 ? Ni N8 2.057(5) . ? Ni N7 2.218(5) 3_656 ? Ni N7 2.218(5) . ? Fe N10 1.988(4) . ? Fe N2 2.046(4) . ? Fe N3 2.057(4) . ? Fe N5 2.109(4) . ? Fe N4 2.149(4) . ? Fe N1 2.152(4) . ? Cl1 C10 1.741(5) . ? Cl2 C11 1.745(5) . ? N7 N6 1.175(6) . ? O1 C7 1.220(6) . ? O2 C14 1.236(6) . ? N6 N5 1.154(5) . ? N3 C14 1.359(6) . ? N3 C13 1.402(6) . ? N2 C7 1.353(6) . ? N2 C8 1.406(6) . ? N1 C2 1.331(6) . ? N1 C6 1.344(7) . ? C10 C9 1.373(7) . ? C10 C11 1.377(7) . ? N4 C15 1.334(6) . ? N4 C19 1.354(6) . ? C12 C11 1.371(6) . ? C12 C13 1.384(6) . ? C12 H12 0.9300 . ? C8 C9 1.385(7) . ? C8 C13 1.429(6) . ? C2 C3 1.386(7) . ? C2 C7 1.508(7) . ? N11 N12 1.157(6) . ? N11 N10 1.177(6) . ? N9 C21 1.455(7) . ? N9 C22 1.505(7) . ? N9 H91 0.93(6) . ? N8 C24 1.471(7) . ? N8 C20 1.479(7) . ? N8 H8 0.77(4) . ? C19 C18 1.372(7) . ? C19 H19 0.9300 . ? C9 H9 0.9300 . ? C18 C17 1.374(7) . ? C18 H18 0.9300 . ? C23 C24 1.501(8) 3_656 ? C23 C22 1.517(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C14 C15 1.511(7) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C20 C21 1.510(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C6 C5 1.374(7) . ? C6 H6 0.9300 . ? C3 C4 1.378(8) . ? C3 H3 0.9300 . ? C4 C5 1.370(8) . ? C4 H4 0.9300 . ? C17 C16 1.384(7) . ? C17 H17 0.9300 . ? C15 C16 1.373(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C16 H16 0.9300 . ? C5 H5 0.9300 . ? C24 C23 1.501(8) 3_656 ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 N9 Ni N9 180.000(1) . 3_656 ? N9 Ni N8 94.6(2) . 3_656 ? N9 Ni N8 85.4(2) 3_656 3_656 ? N9 Ni N8 85.4(2) . . ? N9 Ni N8 94.6(2) 3_656 . ? N8 Ni N8 180.000(1) 3_656 . ? N9 Ni N7 89.3(2) . 3_656 ? N9 Ni N7 90.7(2) 3_656 3_656 ? N8 Ni N7 95.6(2) 3_656 3_656 ? N8 Ni N7 84.4(2) . 3_656 ? N9 Ni N7 90.7(2) . . ? N9 Ni N7 89.3(2) 3_656 . ? N8 Ni N7 84.4(2) 3_656 . ? N8 Ni N7 95.6(2) . . ? N7 Ni N7 180.0 3_656 . ? N10 Fe N2 106.71(18) . . ? N10 Fe N3 102.94(18) . . ? N2 Fe N3 77.55(15) . . ? N10 Fe N5 148.79(19) . . ? N2 Fe N5 98.38(17) . . ? N3 Fe N5 100.32(16) . . ? N10 Fe N4 82.73(17) . . ? N2 Fe N4 153.61(16) . . ? N3 Fe N4 76.31(16) . . ? N5 Fe N4 82.87(17) . . ? N10 Fe N1 87.05(17) . . ? N2 Fe N1 76.73(17) . . ? N3 Fe N1 154.14(17) . . ? N5 Fe N1 80.85(16) . . ? N4 Fe N1 129.10(17) . . ? N6 N7 Ni 130.8(4) . . ? N5 N6 N7 178.4(6) . . ? C14 N3 C13 123.2(4) . . ? C14 N3 Fe 119.4(3) . . ? C13 N3 Fe 117.3(3) . . ? C7 N2 C8 122.6(4) . . ? C7 N2 Fe 120.0(4) . . ? C8 N2 Fe 117.2(3) . . ? C2 N1 C6 119.4(5) . . ? C2 N1 Fe 114.8(3) . . ? C6 N1 Fe 125.8(4) . . ? C9 C10 C11 120.5(5) . . ? C9 C10 Cl1 118.7(4) . . ? C11 C10 Cl1 120.8(4) . . ? C15 N4 C19 118.7(5) . . ? C15 N4 Fe 115.2(3) . . ? C19 N4 Fe 125.5(4) . . ? C11 C12 C13 120.9(5) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C9 C8 N2 127.3(5) . . ? C9 C8 C13 118.5(5) . . ? N2 C8 C13 114.2(4) . . ? C12 C13 N3 127.2(4) . . ? C12 C13 C8 119.1(5) . . ? N3 C13 C8 113.7(4) . . ? N1 C2 C3 121.3(5) . . ? N1 C2 C7 116.2(5) . . ? C3 C2 C7 122.5(6) . . ? N12 N11 N10 176.6(6) . . ? C21 N9 C22 114.2(5) . . ? C21 N9 Ni 105.2(4) . . ? C22 N9 Ni 116.4(4) . . ? C21 N9 H91 109(4) . . ? C22 N9 H91 105(4) . . ? Ni N9 H91 107(4) . . ? N6 N5 Fe 123.5(4) . . ? C24 N8 C20 115.0(5) . . ? C24 N8 Ni 117.0(4) . . ? C20 N8 Ni 106.7(4) . . ? C24 N8 H8 104(4) . . ? C20 N8 H8 108(4) . . ? Ni N8 H8 105(3) . . ? N11 N10 Fe 132.1(4) . . ? N4 C19 C18 122.0(5) . . ? N4 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C10 C9 C8 120.8(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? O1 C7 N2 128.8(5) . . ? O1 C7 C2 119.1(5) . . ? N2 C7 C2 112.0(5) . . ? C12 C11 C10 120.2(5) . . ? C12 C11 Cl2 118.6(4) . . ? C10 C11 Cl2 121.2(4) . . ? C19 C18 C17 118.6(5) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C24 C23 C22 115.3(5) 3_656 . ? C24 C23 H23A 108.4 3_656 . ? C22 C23 H23A 108.4 . . ? C24 C23 H23B 108.4 3_656 . ? C22 C23 H23B 108.4 . . ? H23A C23 H23B 107.5 . . ? O2 C14 N3 127.8(5) . . ? O2 C14 C15 119.9(5) . . ? N3 C14 C15 112.3(4) . . ? N9 C22 C23 112.3(5) . . ? N9 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N9 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? N8 C20 C21 107.4(4) . . ? N8 C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? N8 C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? N1 C6 C5 122.0(6) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C4 C3 C2 119.0(6) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 119.6(6) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C18 C17 C16 119.8(5) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N4 C15 C16 122.3(5) . . ? N4 C15 C14 115.4(4) . . ? C16 C15 C14 122.3(5) . . ? N9 C21 C20 109.8(5) . . ? N9 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? N9 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C15 C16 C17 118.5(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C4 C5 C6 118.7(6) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? N8 C24 C23 111.2(5) . 3_656 ? N8 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 3_656 . ? N8 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 3_656 . ? H24A C24 H24B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.471 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.084 #===END data_compond_2 _database_code_depnum_ccdc_archive 'CCDC 249655' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 Cl2 Cu0.50 Fe N12 O2' _chemical_formula_weight 657.05 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' 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' Cu Cu 0.3201 1.2651 '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 9.8154(9) _cell_length_b 13.1970(12) _cell_length_c 20.7739(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.782(2) _cell_angle_gamma 90.00 _cell_volume 2677.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5967 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1338 _exptl_absorpt_coefficient_mu 1.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ;SADABS: Area-Detector absorption Correction. (1996) Bruker-AXS within SAINT+package, v.6.22 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 APEX CCD system' _diffrn_measurement_method '\w rotations with narrow frames' _diffrn_detector_area_resol_mean 66.06 _diffrn_standards_number 413 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 16700 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.25 _reflns_number_total 6108 _reflns_number_gt 5080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'WINGX V.1.64' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0524P)^2^+0.7926P] 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 6108 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.0000 0.0000 0.0000 0.04065(11) Uani 1 2 d S . . Fe Fe 0.77419(3) 0.16082(2) 0.218796(14) 0.03388(10) Uani 1 1 d . . . Cl2 Cl 0.49677(7) 0.40615(5) -0.06045(3) 0.05197(16) Uani 1 1 d . . . Cl1 Cl 0.79894(7) 0.49426(5) -0.03965(3) 0.05761(18) Uani 1 1 d . . . N3 N 0.61900(17) 0.19812(13) 0.14897(8) 0.0343(4) Uani 1 1 d . . . O1 O 1.06280(18) 0.36233(14) 0.15799(9) 0.0627(5) Uani 1 1 d . . . O2 O 0.39668(18) 0.15850(16) 0.10740(10) 0.0684(6) Uani 1 1 d . . . N2 N 0.86685(17) 0.26489(13) 0.16364(8) 0.0350(4) Uani 1 1 d . . . N6 N 0.9351(2) 0.02128(14) 0.15090(9) 0.0439(4) Uani 1 1 d . . . C9 C 0.8298(2) 0.37510(16) 0.06596(10) 0.0364(4) Uani 1 1 d . . . H9 H 0.9184 0.4008 0.0716 0.044 Uiso 1 1 calc R . . N4 N 0.60758(19) 0.06527(14) 0.24158(9) 0.0404(4) Uani 1 1 d . . . C11 C 0.6089(2) 0.36916(15) 0.00514(10) 0.0365(5) Uani 1 1 d . . . N1 N 0.98413(19) 0.16432(13) 0.26211(9) 0.0390(4) Uani 1 1 d . . . C15 C 0.4911(2) 0.07847(17) 0.20339(11) 0.0409(5) Uani 1 1 d . . . N8 N -0.0696(2) 0.14390(16) -0.00883(11) 0.0511(5) Uani 1 1 d . . . C5 C 1.1662(3) 0.12338(19) 0.34137(12) 0.0512(6) Uani 1 1 d . . . H5 H 1.2016 0.0820 0.3753 0.061 Uiso 1 1 calc R . . N9 N -0.1995(2) -0.04176(17) -0.01002(11) 0.0493(5) Uani 1 1 d . . . N5 N 0.8362(2) 0.02595(15) 0.17860(10) 0.0485(5) Uani 1 1 d . . . C12 C 0.5640(2) 0.30050(16) 0.04831(10) 0.0360(4) Uani 1 1 d . . . H12 H 0.4746 0.2763 0.0421 0.043 Uiso 1 1 calc R . . N10 N 0.7431(2) 0.23873(16) 0.29800(10) 0.0516(5) Uani 1 1 d . . . N11 N 0.6418(2) 0.26595(16) 0.32008(10) 0.0530(5) Uani 1 1 d . . . C8 C 0.7872(2) 0.30512(15) 0.11008(10) 0.0329(4) Uani 1 1 d . . . C13 C 0.6508(2) 0.26680(15) 0.10125(10) 0.0323(4) Uani 1 1 d . . . C7 C 0.9969(2) 0.29612(17) 0.18223(11) 0.0406(5) Uani 1 1 d . . . N7 N 1.0310(3) 0.0148(2) 0.12291(13) 0.0704(7) Uani 1 1 d . . . C2 C 1.0599(2) 0.23809(16) 0.24009(11) 0.0391(5) Uani 1 1 d . . . C10 C 0.7404(2) 0.40650(15) 0.01366(10) 0.0383(5) Uani 1 1 d . . . C24 C -0.1616(3) -0.2199(2) 0.01694(15) 0.0647(7) Uani 1 1 d . . . H24A H -0.1665 -0.2310 -0.0294 0.078 Uiso 1 1 calc R . . H24B H -0.2050 -0.2773 0.0357 0.078 Uiso 1 1 calc R . . C14 C 0.4970(2) 0.15045(18) 0.14750(11) 0.0426(5) Uani 1 1 d . . . C6 C 1.0367(3) 0.10729(18) 0.31180(11) 0.0470(5) Uani 1 1 d . . . H6 H 0.9841 0.0553 0.3267 0.056 Uiso 1 1 calc R . . C3 C 1.1900(2) 0.2596(2) 0.26867(13) 0.0538(6) Uani 1 1 d . . . H3 H 1.2410 0.3123 0.2535 0.065 Uiso 1 1 calc R . . C16 C 0.3720(3) 0.0276(2) 0.21408(13) 0.0550(6) Uani 1 1 d . . . H16 H 0.2913 0.0382 0.1874 0.066 Uiso 1 1 calc R . . C19 C 0.6111(3) -0.00084(19) 0.29044(12) 0.0534(6) Uani 1 1 d . . . H19 H 0.6930 -0.0108 0.3163 0.064 Uiso 1 1 calc R . . C18 C 0.4977(3) -0.0543(2) 0.30347(13) 0.0612(7) Uani 1 1 d . . . H18 H 0.5026 -0.1003 0.3376 0.073 Uiso 1 1 calc R . . N12 N 0.5484(3) 0.2971(2) 0.34269(15) 0.0868(9) Uani 1 1 d . . . C25 C -0.2405(3) -0.1266(2) 0.02924(13) 0.0596(7) Uani 1 1 d . . . H25A H -0.3376 -0.1397 0.0191 0.072 Uiso 1 1 calc R . . H25B H -0.2250 -0.1089 0.0747 0.072 Uiso 1 1 calc R . . C21 C -0.2803(3) 0.0529(2) -0.00415(15) 0.0612(7) Uani 1 1 d . . . H21A H -0.3730 0.0436 -0.0243 0.073 Uiso 1 1 calc R . . H21B H -0.2849 0.0691 0.0411 0.073 Uiso 1 1 calc R . . C4 C 1.2424(3) 0.2007(2) 0.32045(13) 0.0580(7) Uani 1 1 d . . . H4 H 1.3293 0.2139 0.3409 0.070 Uiso 1 1 calc R . . C23 C 0.0119(3) 0.2169(2) -0.04389(15) 0.0631(7) Uani 1 1 d . . . H23A H -0.0271 0.2841 -0.0411 0.076 Uiso 1 1 calc R . . H23B H 0.0058 0.1981 -0.0892 0.076 Uiso 1 1 calc R . . C22 C -0.2129(3) 0.1369(2) -0.03648(14) 0.0606(7) Uani 1 1 d . . . H22A H -0.2171 0.1240 -0.0826 0.073 Uiso 1 1 calc R . . H22B H -0.2598 0.2002 -0.0300 0.073 Uiso 1 1 calc R . . C17 C 0.3760(3) -0.0393(2) 0.26539(14) 0.0630(8) Uani 1 1 d . . . H17 H 0.2973 -0.0738 0.2742 0.076 Uiso 1 1 calc R . . H7 H -0.211(3) -0.062(2) -0.0488(15) 0.068(9) Uiso 1 1 d . . . H8 H -0.075(3) 0.164(2) 0.0323(14) 0.067(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0376(2) 0.0372(2) 0.0472(2) -0.00104(16) 0.00459(17) 0.00649(15) Fe 0.03463(16) 0.03444(17) 0.03162(16) 0.00138(12) -0.00137(12) -0.00472(11) Cl2 0.0605(4) 0.0497(3) 0.0412(3) 0.0024(2) -0.0169(3) 0.0048(3) Cl1 0.0672(4) 0.0550(4) 0.0489(3) 0.0203(3) -0.0026(3) -0.0100(3) N3 0.0326(9) 0.0369(9) 0.0328(8) 0.0004(7) 0.0001(7) -0.0023(7) O1 0.0453(10) 0.0666(12) 0.0722(12) 0.0310(10) -0.0144(9) -0.0212(8) O2 0.0431(10) 0.0915(15) 0.0664(12) 0.0233(11) -0.0147(9) -0.0233(9) N2 0.0323(9) 0.0352(9) 0.0360(9) 0.0057(7) -0.0036(7) -0.0021(7) N6 0.0483(11) 0.0412(10) 0.0413(10) -0.0072(8) 0.0002(9) -0.0011(8) C9 0.0364(11) 0.0347(11) 0.0374(11) -0.0009(9) -0.0002(9) -0.0011(8) N4 0.0481(11) 0.0392(10) 0.0345(9) -0.0021(8) 0.0071(8) -0.0086(8) C11 0.0445(12) 0.0316(10) 0.0312(10) -0.0015(8) -0.0071(9) 0.0074(9) N1 0.0403(10) 0.0357(9) 0.0390(10) 0.0030(8) -0.0054(8) -0.0016(7) C15 0.0448(12) 0.0394(12) 0.0396(11) -0.0071(9) 0.0093(10) -0.0092(9) N8 0.0604(13) 0.0445(12) 0.0479(12) -0.0035(9) 0.0035(10) 0.0122(9) C5 0.0502(14) 0.0522(14) 0.0479(13) 0.0075(11) -0.0115(11) 0.0056(11) N9 0.0466(11) 0.0564(13) 0.0444(12) -0.0091(10) 0.0014(9) -0.0022(9) N5 0.0498(12) 0.0429(11) 0.0534(12) -0.0084(9) 0.0079(10) -0.0044(9) C12 0.0338(10) 0.0366(11) 0.0366(11) -0.0059(9) -0.0021(8) 0.0016(8) N10 0.0519(12) 0.0561(13) 0.0465(11) -0.0129(10) 0.0036(10) -0.0062(10) N11 0.0544(13) 0.0562(13) 0.0482(12) -0.0018(10) 0.0041(10) -0.0146(10) C8 0.0351(10) 0.0307(10) 0.0321(10) -0.0029(8) -0.0001(8) 0.0016(8) C13 0.0330(10) 0.0312(10) 0.0324(10) -0.0038(8) 0.0029(8) 0.0026(8) C7 0.0362(11) 0.0396(12) 0.0444(12) 0.0044(10) -0.0035(9) -0.0046(9) N7 0.0560(14) 0.0871(19) 0.0704(16) -0.0186(13) 0.0183(12) -0.0005(13) C2 0.0350(11) 0.0381(11) 0.0425(12) 0.0021(9) -0.0048(9) -0.0017(9) C10 0.0503(12) 0.0303(10) 0.0341(11) 0.0031(8) 0.0033(9) 0.0005(9) C24 0.079(2) 0.0526(16) 0.0617(17) 0.0009(13) 0.0029(15) -0.0153(14) C14 0.0363(11) 0.0490(13) 0.0424(12) -0.0007(10) 0.0026(10) -0.0055(9) C6 0.0514(13) 0.0424(13) 0.0453(12) 0.0086(10) -0.0049(11) -0.0021(10) C3 0.0392(12) 0.0569(15) 0.0623(16) 0.0135(12) -0.0098(11) -0.0099(11) C16 0.0480(14) 0.0588(15) 0.0598(16) -0.0081(13) 0.0135(12) -0.0166(12) C19 0.0710(17) 0.0509(15) 0.0386(12) 0.0032(10) 0.0075(12) -0.0143(12) C18 0.087(2) 0.0529(16) 0.0458(14) -0.0001(12) 0.0187(14) -0.0238(14) N12 0.0673(17) 0.093(2) 0.105(2) 0.0012(18) 0.0337(16) -0.0101(15) C25 0.0593(16) 0.0654(17) 0.0536(15) -0.0091(13) 0.0035(13) -0.0172(13) C21 0.0398(13) 0.0743(19) 0.0694(18) -0.0161(15) 0.0044(12) 0.0157(13) C4 0.0392(13) 0.0676(17) 0.0629(16) 0.0108(14) -0.0164(12) -0.0034(12) C23 0.083(2) 0.0439(15) 0.0638(17) 0.0079(13) 0.0120(15) 0.0094(13) C22 0.0585(16) 0.0573(16) 0.0648(17) -0.0037(13) 0.0006(13) 0.0254(13) C17 0.0749(19) 0.0549(16) 0.0637(17) -0.0095(13) 0.0293(15) -0.0294(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 Cu N8 2.020(2) . ? Cu N8 2.020(2) 3 ? Cu N9 2.025(2) 3 ? Cu N9 2.025(2) . ? Fe N10 1.990(2) . ? Fe N3 2.0547(16) . ? Fe N2 2.0583(17) . ? Fe N5 2.083(2) . ? Fe N4 2.1551(18) . ? Fe N1 2.1643(18) . ? Cl2 C11 1.733(2) . ? Cl1 C10 1.740(2) . ? N3 C14 1.350(3) . ? N3 C13 1.401(3) . ? O1 C7 1.225(3) . ? O2 C14 1.228(3) . ? N2 C7 1.360(3) . ? N2 C8 1.398(2) . ? N6 N7 1.158(3) . ? N6 N5 1.179(3) . ? C9 C10 1.389(3) . ? C9 C8 1.395(3) . ? N4 C15 1.336(3) . ? N4 C19 1.336(3) . ? C11 C10 1.376(3) . ? C11 C12 1.378(3) . ? N1 C2 1.334(3) . ? N1 C6 1.338(3) . ? C15 C16 1.385(3) . ? C15 C14 1.506(3) . ? N8 C22 1.468(3) . ? N8 C23 1.488(4) . ? C5 C4 1.362(4) . ? C5 C6 1.371(3) . ? N9 C25 1.466(3) . ? N9 C21 1.492(3) . ? C12 C13 1.395(3) . ? N10 N11 1.192(3) . ? N11 N12 1.147(3) . ? C8 C13 1.426(3) . ? C7 C2 1.505(3) . ? C2 C3 1.382(3) . ? C24 C25 1.490(4) . ? C24 C23 1.519(4) 3 ? C3 C4 1.383(3) . ? C16 C17 1.381(4) . ? C19 C18 1.368(4) . ? C18 C17 1.379(4) . ? C21 C22 1.485(4) . ? C23 C24 1.519(4) 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 N8 Cu N8 180.00(12) . 3 ? N8 Cu N9 93.90(9) . 3 ? N8 Cu N9 86.10(9) 3 3 ? N8 Cu N9 86.10(9) . . ? N8 Cu N9 93.90(9) 3 . ? N9 Cu N9 180.00(12) 3 . ? N10 Fe N3 107.18(8) . . ? N10 Fe N2 103.23(8) . . ? N3 Fe N2 77.57(7) . . ? N10 Fe N5 148.05(9) . . ? N3 Fe N5 98.49(8) . . ? N2 Fe N5 100.58(8) . . ? N10 Fe N4 86.42(8) . . ? N3 Fe N4 76.72(7) . . ? N2 Fe N4 154.20(7) . . ? N5 Fe N4 81.20(8) . . ? N10 Fe N1 82.20(8) . . ? N3 Fe N1 153.56(7) . . ? N2 Fe N1 76.20(7) . . ? N5 Fe N1 83.13(7) . . ? N4 Fe N1 129.27(7) . . ? C14 N3 C13 123.05(17) . . ? C14 N3 Fe 119.81(15) . . ? C13 N3 Fe 116.90(13) . . ? C7 N2 C8 122.98(18) . . ? C7 N2 Fe 119.93(14) . . ? C8 N2 Fe 116.96(13) . . ? N7 N6 N5 178.4(3) . . ? C10 C9 C8 120.25(19) . . ? C15 N4 C19 119.5(2) . . ? C15 N4 Fe 114.60(14) . . ? C19 N4 Fe 125.91(17) . . ? C10 C11 C12 120.60(19) . . ? C10 C11 Cl2 120.88(17) . . ? C12 C11 Cl2 118.52(17) . . ? C2 N1 C6 119.32(19) . . ? C2 N1 Fe 114.44(13) . . ? C6 N1 Fe 125.86(16) . . ? N4 C15 C16 121.8(2) . . ? N4 C15 C14 116.30(19) . . ? C16 C15 C14 121.9(2) . . ? C22 N8 C23 113.0(2) . . ? C22 N8 Cu 106.13(16) . . ? C23 N8 Cu 117.35(17) . . ? C4 C5 C6 119.1(2) . . ? C25 N9 C21 114.6(2) . . ? C25 N9 Cu 117.88(17) . . ? C21 N9 Cu 106.28(16) . . ? N6 N5 Fe 121.91(16) . . ? C11 C12 C13 120.85(19) . . ? N11 N10 Fe 132.66(18) . . ? N12 N11 N10 176.0(3) . . ? C9 C8 N2 126.42(18) . . ? C9 C8 C13 119.36(18) . . ? N2 C8 C13 114.21(18) . . ? C12 C13 N3 127.04(18) . . ? C12 C13 C8 118.66(19) . . ? N3 C13 C8 114.30(17) . . ? O1 C7 N2 128.2(2) . . ? O1 C7 C2 120.00(19) . . ? N2 C7 C2 111.78(18) . . ? N1 C2 C3 121.7(2) . . ? N1 C2 C7 116.54(18) . . ? C3 C2 C7 121.7(2) . . ? C11 C10 C9 120.29(19) . . ? C11 C10 Cl1 121.47(16) . . ? C9 C10 Cl1 118.24(17) . . ? C25 C24 C23 114.5(2) . 3 ? O2 C14 N3 128.6(2) . . ? O2 C14 C15 119.1(2) . . ? N3 C14 C15 112.30(19) . . ? N1 C6 C5 121.8(2) . . ? C2 C3 C4 118.2(2) . . ? C17 C16 C15 118.3(3) . . ? N4 C19 C18 121.8(3) . . ? C19 C18 C17 119.2(3) . . ? N9 C25 C24 111.1(2) . . ? C22 C21 N9 108.8(2) . . ? C5 C4 C3 119.8(2) . . ? N8 C23 C24 112.6(2) . 3 ? N8 C22 C21 108.9(2) . . ? C18 C17 C16 119.4(2) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.379 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.060