# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/212 data_calcul _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common [Cu(CH3COO)2(NITpPy)]2 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Cu N3 O6' _chemical_formula_weight 415.91 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' '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 7.307(3) _cell_length_b 9.337(2) _cell_length_c 14.654(4) _cell_angle_alpha 101.79(2) _cell_angle_beta 97.75(2) _cell_angle_gamma 103.75(3) _cell_volume 932.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.312 _cell_measurement_theta_max 17.085 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 1.208 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_correction_T_min 0.930035 _exptl_absorpt_correction_T_max 0.999635 _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 'Nonius CAD4' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -2.0 _diffrn_reflns_number 4844 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.98 _reflns_number_total 4500 _reflns_number_gt 3165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius CAD4' _computing_cell_refinement MolEN _computing_data_reduction molEN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.4340P] 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 4500 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.62690(5) 0.54730(4) 0.57968(2) 0.03518(11) Uani 1 d . . . N1 N 0.8395(3) 0.6238(2) 0.71077(14) 0.0319(5) Uani 1 d . . . O6 O 1.5042(3) 0.7697(2) 0.93962(13) 0.0445(5) Uani 1 d . . . N4 N 1.1381(3) 0.7221(2) 1.06315(13) 0.0309(4) Uani 1 d . . . O2 O 0.7831(3) 0.6611(3) 0.50548(14) 0.0552(6) Uani 1 d . . . C16 C 0.2710(4) 0.3421(3) 0.57997(19) 0.0422(6) Uani 1 d . . . O4 O 0.4290(3) 0.4204(3) 0.63051(14) 0.0535(5) Uani 1 d . . . O5 O 0.9652(3) 0.6759(3) 1.07309(14) 0.0517(5) Uani 1 d . . . N3 N 1.3944(3) 0.7592(2) 0.99928(13) 0.0280(4) Uani 1 d . . . O1 O 0.5034(3) 0.7123(2) 0.60707(14) 0.0543(6) Uani 1 d . . . O3 O 0.7071(3) 0.3649(2) 0.52945(14) 0.0544(6) Uani 1 d . . . C6 C 1.2015(3) 0.7176(3) 0.98050(15) 0.0277(5) Uani 1 d . . . C8 C 1.4725(3) 0.7813(3) 1.10329(15) 0.0286(5) Uani 1 d . . . C4 C 0.8964(3) 0.7043(3) 0.87986(17) 0.0316(5) Uani 1 d . . . H4 H 0.8510 0.7385 0.9343 0.038 Uiso 1 calc R . . C12 C 1.6525(4) 0.9148(3) 1.1344(2) 0.0430(7) Uani 1 d . . . H12A H 1.7512 0.8902 1.1021 0.064 Uiso 1 calc R . . H12B H 1.6960 0.9351 1.2017 0.064 Uiso 1 calc R . . H12C H 1.6239 1.0031 1.1188 0.064 Uiso 1 calc R . . C10 C 1.2677(4) 0.7405(3) 1.23194(18) 0.0437(7) Uani 1 d . . . H10A H 1.1556 0.7604 1.2534 0.066 Uiso 1 calc R . . H10B H 1.3779 0.7871 1.2821 0.066 Uiso 1 calc R . . H10C H 1.2509 0.6327 1.2143 0.066 Uiso 1 calc R . . C2 C 1.1404(4) 0.6329(3) 0.80283(17) 0.0348(6) Uani 1 d . . . H2 H 1.2623 0.6185 0.8043 0.042 Uiso 1 calc R . . C7 C 1.2973(3) 0.8062(3) 1.14623(16) 0.0294(5) Uani 1 d . . . C1 C 1.0156(4) 0.6050(3) 0.71748(17) 0.0357(6) Uani 1 d . . . H1 H 1.0567 0.5713 0.6617 0.043 Uiso 1 calc R . . C5 C 0.7833(3) 0.6738(3) 0.79121(17) 0.0320(5) Uani 1 d . . . H5 H 0.6615 0.6890 0.7874 0.038 Uiso 1 calc R . . C11 C 1.5196(4) 0.6343(3) 1.11325(19) 0.0404(6) Uani 1 d . . . H11A H 1.4061 0.5507 1.0896 0.061 Uiso 1 calc R . . H11B H 1.5655 0.6413 1.1790 0.061 Uiso 1 calc R . . H11C H 1.6168 0.6181 1.0775 0.061 Uiso 1 calc R . . C9 C 1.2858(4) 0.9700(3) 1.1672(2) 0.0444(7) Uani 1 d . . . H9A H 1.3076 1.0111 1.1134 0.067 Uiso 1 calc R . . H9B H 1.3817 1.0294 1.2218 0.067 Uiso 1 calc R . . H9C H 1.1609 0.9729 1.1796 0.067 Uiso 1 calc R . . C3 C 1.0790(3) 0.6832(3) 0.88674(16) 0.0277(5) Uani 1 d . . . C13 C 0.6310(4) 0.2749(3) 0.4506(2) 0.0438(7) Uani 1 d . . . C14 C 0.7074(5) 0.1394(4) 0.4231(3) 0.0705(11) Uani 1 d . . . H14A H 0.6428 0.0815 0.3603 0.106 Uiso 1 calc R . . H14B H 0.6855 0.0768 0.4672 0.106 Uiso 1 calc R . . H14C H 0.8427 0.1734 0.4244 0.106 Uiso 1 calc R . . C15 C 0.1340(5) 0.2435(4) 0.6240(2) 0.0602(9) Uani 1 d . . . H15A H 0.1338 0.1393 0.6019 0.090 Uiso 1 calc R . . H15B H 0.0071 0.2536 0.6065 0.090 Uiso 1 calc R . . H15C H 0.1733 0.2743 0.6919 0.090 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 Cu1 0.03258(18) 0.0446(2) 0.02440(15) 0.00517(12) -0.00447(11) 0.01137(14) N1 0.0322(11) 0.0341(12) 0.0275(10) 0.0077(9) -0.0007(8) 0.0094(9) O6 0.0321(10) 0.0684(14) 0.0342(10) 0.0171(9) 0.0103(8) 0.0101(9) N4 0.0245(10) 0.0408(12) 0.0256(10) 0.0092(9) 0.0046(8) 0.0050(9) O2 0.0434(11) 0.0751(15) 0.0376(11) 0.0188(10) -0.0019(9) -0.0009(11) C16 0.0388(15) 0.0530(17) 0.0396(14) 0.0148(13) 0.0077(12) 0.0185(13) O4 0.0415(11) 0.0738(15) 0.0396(11) 0.0218(10) -0.0015(9) 0.0038(10) O5 0.0288(10) 0.0819(16) 0.0433(11) 0.0204(11) 0.0096(8) 0.0069(10) N3 0.0241(10) 0.0361(11) 0.0223(9) 0.0080(8) 0.0034(8) 0.0055(9) O1 0.0543(13) 0.0599(13) 0.0422(11) -0.0040(10) -0.0100(10) 0.0285(11) O3 0.0553(13) 0.0573(13) 0.0436(11) -0.0051(10) -0.0118(9) 0.0287(11) C6 0.0262(12) 0.0331(13) 0.0232(11) 0.0080(9) 0.0021(9) 0.0075(10) C8 0.0266(12) 0.0341(13) 0.0224(11) 0.0070(9) -0.0005(9) 0.0061(10) C4 0.0314(13) 0.0344(13) 0.0266(11) 0.0031(10) 0.0023(10) 0.0099(11) C12 0.0310(14) 0.0455(16) 0.0410(15) 0.0038(12) -0.0012(11) -0.0008(12) C10 0.0507(17) 0.0555(18) 0.0275(13) 0.0142(12) 0.0094(12) 0.0146(14) C2 0.0282(12) 0.0468(15) 0.0289(12) 0.0079(11) 0.0040(10) 0.0113(11) C7 0.0308(12) 0.0315(13) 0.0233(11) 0.0066(9) 0.0022(9) 0.0054(10) C1 0.0352(13) 0.0456(15) 0.0245(12) 0.0057(11) 0.0031(10) 0.0119(12) C5 0.0268(12) 0.0362(14) 0.0315(12) 0.0055(10) -0.0006(10) 0.0116(10) C11 0.0423(15) 0.0445(16) 0.0358(14) 0.0097(12) 0.0013(11) 0.0184(13) C9 0.0511(17) 0.0393(15) 0.0455(16) 0.0073(12) 0.0120(13) 0.0182(13) C3 0.0271(12) 0.0287(12) 0.0248(11) 0.0080(9) 0.0000(9) 0.0044(10) C13 0.0414(15) 0.0481(17) 0.0395(15) 0.0031(12) 0.0014(12) 0.0180(13) C14 0.074(2) 0.064(2) 0.067(2) -0.0073(18) -0.0102(19) 0.041(2) C15 0.054(2) 0.074(2) 0.0507(18) 0.0247(17) 0.0082(15) 0.0082(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.960(2) . ? Cu1 O1 1.964(2) . ? Cu1 O3 1.966(2) . ? Cu1 O4 1.971(2) . ? Cu1 N1 2.173(2) . ? Cu1 Cu1 2.6236(12) 2_666 ? N1 C5 1.332(3) . ? N1 C1 1.333(3) . ? O6 N3 1.266(3) . ? N4 O5 1.272(3) . ? N4 C6 1.351(3) . ? N4 C7 1.499(3) . ? O2 C16 1.253(3) 2_666 ? C16 O4 1.250(3) . ? C16 O2 1.253(3) 2_666 ? C16 C15 1.499(4) . ? N3 C6 1.343(3) . ? N3 C8 1.507(3) . ? O1 C13 1.251(3) 2_666 ? O3 C13 1.249(3) . ? C6 C3 1.464(3) . ? C8 C11 1.522(3) . ? C8 C12 1.523(4) . ? C8 C7 1.545(3) . ? C4 C5 1.378(3) . ? C4 C3 1.388(3) . ? C10 C7 1.525(3) . ? C2 C1 1.382(3) . ? C2 C3 1.395(3) . ? C7 C9 1.522(4) . ? C13 O1 1.251(3) 2_666 ? C13 C14 1.504(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 O2 Cu1 O1 89.38(10) . . ? O2 Cu1 O3 90.68(10) . . ? O1 Cu1 O3 168.20(8) . . ? O2 Cu1 O4 168.25(8) . . ? O1 Cu1 O4 88.74(10) . . ? O3 Cu1 O4 88.81(10) . . ? O2 Cu1 N1 96.33(9) . . ? O1 Cu1 N1 96.19(8) . . ? O3 Cu1 N1 95.54(8) . . ? O4 Cu1 N1 95.41(9) . . ? O2 Cu1 Cu1 83.41(7) . 2_666 ? O1 Cu1 Cu1 84.56(6) . 2_666 ? O3 Cu1 Cu1 83.72(6) . 2_666 ? O4 Cu1 Cu1 84.87(7) . 2_666 ? N1 Cu1 Cu1 179.21(6) . 2_666 ? C5 N1 C1 117.5(2) . . ? C5 N1 Cu1 118.07(16) . . ? C1 N1 Cu1 123.77(17) . . ? O5 N4 C6 126.8(2) . . ? O5 N4 C7 121.89(19) . . ? C6 N4 C7 110.96(19) . . ? C16 O2 Cu1 124.3(2) 2_666 . ? O4 C16 O2 125.2(3) . 2_666 ? O4 C16 C15 118.1(3) . . ? O2 C16 C15 116.7(3) 2_666 . ? C16 O4 Cu1 122.14(18) . . ? O6 N3 C6 126.88(19) . . ? O6 N3 C8 121.54(18) . . ? C6 N3 C8 111.39(19) . . ? C13 O1 Cu1 122.58(19) 2_666 . ? C13 O3 Cu1 123.52(18) . . ? N3 C6 N4 108.87(19) . . ? N3 C6 C3 125.9(2) . . ? N4 C6 C3 125.1(2) . . ? N3 C8 C11 106.30(19) . . ? N3 C8 C12 109.2(2) . . ? C11 C8 C12 110.7(2) . . ? N3 C8 C7 100.49(17) . . ? C11 C8 C7 113.5(2) . . ? C12 C8 C7 115.6(2) . . ? C5 C4 C3 119.0(2) . . ? C1 C2 C3 118.3(2) . . ? N4 C7 C9 105.4(2) . . ? N4 C7 C10 110.4(2) . . ? C9 C7 C10 110.1(2) . . ? N4 C7 C8 100.28(18) . . ? C9 C7 C8 114.5(2) . . ? C10 C7 C8 115.2(2) . . ? N1 C1 C2 123.6(2) . . ? N1 C5 C4 123.4(2) . . ? C4 C3 C2 118.1(2) . . ? C4 C3 C6 119.5(2) . . ? C2 C3 C6 122.4(2) . . ? O3 C13 O1 125.6(3) . 2_666 ? O3 C13 C14 116.9(3) . . ? O1 C13 C14 117.5(3) 2_666 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.283 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.073