Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name V.Niel A.Galet A.B.Gaspar M.C.Munoz J.A.Real data_compound1 _database_code_CSD 203741 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Cu Fe0.50 N4' _chemical_formula_weight 223.60 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' 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8020(4) _cell_length_b 8.0470(3) _cell_length_c 8.0650(4) _cell_angle_alpha 110.214(2) _cell_angle_beta 99.134(2) _cell_angle_gamma 108.733(2) _cell_volume 373.81(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 20 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 3.785 _exptl_absorpt_correction_type phi-scan _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_process_details ? _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 ?-2? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4004 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.38 _reflns_number_total 1692 _reflns_number_gt 1190 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.1876P] 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 1692 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 0.0000 0.0000 0.0000 0.0266(2) Uani 1 2 d S . . Cu1 Cu 0.48467(8) 0.84812(7) 0.36978(8) 0.0332(2) Uani 1 1 d . . . N4 N 0.1780(6) 0.6286(5) 0.2882(5) 0.0329(9) Uani 1 1 d . . . C6 C 0.6420(7) 0.9087(6) 0.6296(7) 0.0312(10) Uani 1 1 d . . . C5 C 0.6484(7) 0.8451(6) 0.1916(7) 0.0304(10) Uani 1 1 d . . . N1 N -0.0227(6) 0.2870(5) 0.1392(5) 0.0322(9) Uani 1 1 d . . . N3 N 0.2538(6) 0.0788(5) 0.2495(7) 0.0391(10) Uani 1 1 d . . . N2 N 0.2404(6) 0.1266(5) -0.1096(6) 0.0361(9) Uani 1 1 d . . . C4 C 0.1534(7) 0.4468(6) 0.1908(6) 0.0350(11) Uani 1 1 d . . . H4 H 0.2726 0.4315 0.1558 0.037(6) Uiso 1 1 calc R . . C1 C -0.1946(7) 0.3098(6) 0.1857(7) 0.0387(11) Uani 1 1 d . . . H1 H -0.3227 0.2010 0.1501 0.037(6) Uiso 1 1 calc R . . C2 C -0.1873(8) 0.4905(7) 0.2852(9) 0.0481(14) Uani 1 1 d . . . H2 H -0.3076 0.5058 0.3181 0.037(6) Uiso 1 1 calc R . . C3 C 0.0044(7) 0.6471(6) 0.3340(7) 0.0417(12) Uani 1 1 d . . . H3 H 0.0132 0.7706 0.4015 0.037(6) 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 0.0255(4) 0.0272(4) 0.0251(5) 0.0110(4) 0.0068(4) 0.0087(3) Cu1 0.0323(3) 0.0333(3) 0.0295(4) 0.0101(2) 0.0096(3) 0.0114(2) N4 0.030(2) 0.0254(18) 0.034(2) 0.0070(16) 0.0058(17) 0.0083(15) C6 0.025(2) 0.035(2) 0.022(3) 0.0054(19) 0.006(2) 0.0054(18) C5 0.029(2) 0.025(2) 0.033(3) 0.0115(19) 0.005(2) 0.0096(18) N1 0.0269(19) 0.0288(19) 0.037(2) 0.0096(16) 0.0087(17) 0.0110(15) N3 0.042(2) 0.037(2) 0.048(3) 0.021(2) 0.020(2) 0.0207(19) N2 0.041(2) 0.034(2) 0.036(2) 0.0151(18) 0.014(2) 0.0178(18) C4 0.030(2) 0.034(2) 0.036(3) 0.010(2) 0.010(2) 0.0115(19) C1 0.028(2) 0.031(2) 0.050(3) 0.017(2) 0.008(2) 0.0055(19) C2 0.032(3) 0.041(3) 0.077(4) 0.025(3) 0.021(3) 0.019(2) C3 0.035(3) 0.030(2) 0.055(3) 0.014(2) 0.011(2) 0.013(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 Fe1 N2 2.123(4) . ? Fe1 N2 2.123(4) 2 ? Fe1 N3 2.178(5) 2 ? Fe1 N3 2.178(5) . ? Fe1 N1 2.261(3) 2 ? Fe1 N1 2.261(3) . ? Cu1 C5 1.951(5) . ? Cu1 C6 2.005(5) . ? Cu1 N4 2.074(3) . ? Cu1 C6 2.377(5) 2_676 ? Cu1 Cu1 2.5329(11) 2_676 ? N4 C3 1.329(6) . ? N4 C4 1.339(5) . ? C6 N3 1.063(6) 2_666 ? C6 Cu1 2.377(5) 2_676 ? C5 N2 1.101(6) 2_665 ? N1 C4 1.321(5) . ? N1 C1 1.331(6) . ? N3 C6 1.063(6) 2_666 ? N2 C5 1.101(6) 2_665 ? C4 H4 0.9300 . ? C1 C2 1.377(7) . ? C1 H1 0.9300 . ? C2 C3 1.372(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? 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 N2 Fe1 N2 180.0(2) . 2 ? N2 Fe1 N3 89.97(15) . 2 ? N2 Fe1 N3 90.03(15) 2 2 ? N2 Fe1 N3 90.03(15) . . ? N2 Fe1 N3 89.97(15) 2 . ? N3 Fe1 N3 180.0(2) 2 . ? N2 Fe1 N1 89.32(13) . 2 ? N2 Fe1 N1 90.68(13) 2 2 ? N3 Fe1 N1 88.86(13) 2 2 ? N3 Fe1 N1 91.14(13) . 2 ? N2 Fe1 N1 90.68(13) . . ? N2 Fe1 N1 89.32(13) 2 . ? N3 Fe1 N1 91.14(13) 2 . ? N3 Fe1 N1 88.86(13) . . ? N1 Fe1 N1 180.0(2) 2 . ? C5 Cu1 C6 118.46(18) . . ? C5 Cu1 N4 118.99(17) . . ? C6 Cu1 N4 108.84(17) . . ? C5 Cu1 C6 101.77(16) . 2_676 ? C6 Cu1 C6 109.97(15) . 2_676 ? N4 Cu1 C6 95.60(14) . 2_676 ? C5 Cu1 Cu1 124.66(12) . 2_676 ? C6 Cu1 Cu1 61.88(13) . 2_676 ? N4 Cu1 Cu1 110.33(11) . 2_676 ? C6 Cu1 Cu1 48.09(12) 2_676 2_676 ? C3 N4 C4 115.6(4) . . ? C3 N4 Cu1 126.7(3) . . ? C4 N4 Cu1 117.6(3) . . ? N3 C6 Cu1 165.8(4) 2_666 . ? N3 C6 Cu1 122.4(4) 2_666 2_676 ? Cu1 C6 Cu1 70.03(15) . 2_676 ? N2 C5 Cu1 168.8(4) 2_665 . ? C4 N1 C1 116.5(4) . . ? C4 N1 Fe1 117.8(3) . . ? C1 N1 Fe1 125.5(3) . . ? C6 N3 Fe1 168.9(4) 2_666 . ? C5 N2 Fe1 165.8(4) 2_665 . ? N1 C4 N4 126.7(4) . . ? N1 C4 H4 116.7 . . ? N4 C4 H4 116.7 . . ? N1 C1 C2 121.6(4) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C3 C2 C1 117.3(4) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? N4 C3 C2 122.3(4) . . ? N4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.541 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.113