# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Catalina Ruiz-Perez' 'M. Julve' 'Franceso Lloref' 'Alfredo Mederos' 'Yolanda Rodriguez-Martin' 'Joaquin Sanchiz' _publ_contact_author_name 'Prof Catalina Ruiz-Perez' _publ_contact_author_address ; Departamento de Fisica Fundamental II Universidad de La Laguna Avda. Astrofisico Francisco Sanchez 38204 La laguna Tenerife SPAIN ; _publ_contact_author_email 'CARUIZ@ULL.ES' _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Ferromagnetic Coupling in the Malonato-Bridged Copper (II) Chains {[Cu(2-MeIm)2(mal)]}n(H2mal - Malonic Acid, Iin = Imidazole and 2-Melm = 2-Methylimidazole) ; data_COMPOUND_1 _database_code_CSD 193604 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cu N4 O4' _chemical_formula_weight 301.75 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 ? _symmetry_space_group_name_H-M ? 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 7.791(2) _cell_length_b 7.634(2) _cell_length_c 19.364(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.42(3) _cell_angle_gamma 90.00 _cell_volume 1139.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.930 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3586 _diffrn_reflns_av_R_equivalents 0.0110 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 29.96 _reflns_number_total 3308 _reflns_number_gt 2491 _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^)+(0.0672P)^2^+0.4775P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3308 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 1.820 _refine_ls_shift/su_mean 0.067 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 Cu1 Cu 0.63062(4) 0.93870(4) 0.131969(16) 0.02935(12) Uani 1 1 d . . . O1 O 0.5736(2) 0.7489(3) 0.19308(10) 0.0350(4) Uani 1 1 d . . . O2 O 0.6632(3) 0.5644(3) 0.27784(11) 0.0439(5) Uani 1 1 d . . . O3 O 0.8194(3) 0.8066(3) 0.10311(11) 0.0422(5) Uani 1 1 d . . . O4 O 1.0174(4) 0.6012(4) 0.10833(17) 0.0784(11) Uani 1 1 d . . . C7 C 0.2739(4) 0.9881(4) 0.16521(16) 0.0359(6) Uani 1 1 d . . . C8 C 0.2399(4) 1.2682(5) 0.1796(2) 0.0501(8) Uani 1 1 d . . . C9 C 0.3989(5) 1.2375(4) 0.1631(2) 0.0510(8) Uani 1 1 d . . . C4 C 0.5525(4) 1.2232(4) 0.02006(16) 0.0390(6) Uani 1 1 d . . . C5 C 0.6342(5) 1.3158(4) -0.02437(17) 0.0445(7) Uani 1 1 d . . . C6 C 0.8195(4) 1.1475(4) 0.03856(16) 0.0380(6) Uani 1 1 d . . . C1 C 0.6768(3) 0.6337(4) 0.22034(13) 0.0292(5) Uani 1 1 d . . . C2 C 0.8141(7) 0.5622(6) 0.1812(3) 0.0660(14) Uani 1 1 d . . . C3 C 0.8887(3) 0.6655(3) 0.12756(14) 0.0312(5) Uani 1 1 d . . . N3 N 0.4206(3) 1.0607(3) 0.15376(13) 0.0353(5) Uani 1 1 d . . . N4 N 0.1619(3) 1.1096(4) 0.18022(14) 0.0407(6) Uani 1 1 d . . . N1 N 0.6701(3) 1.1167(3) 0.06025(12) 0.0314(4) Uani 1 1 d . . . N2 N 0.8031(4) 1.2665(4) -0.01222(14) 0.0419(6) Uani 1 1 d . . . H6 H 0.915(5) 1.091(5) 0.0556(18) 0.041(9) Uiso 1 1 d . . . H4 H 0.431(4) 1.230(5) 0.0233(16) 0.038(8) Uiso 1 1 d . . . H5 H 0.593(6) 1.391(6) -0.056(2) 0.067(13) Uiso 1 1 d . . . H4N H 0.071(6) 1.089(6) 0.191(3) 0.073(14) Uiso 1 1 d . . . H7 H 0.248(5) 0.868(5) 0.1596(19) 0.053(11) Uiso 1 1 d . . . H9 H 0.481(6) 1.309(6) 0.164(2) 0.076(14) Uiso 1 1 d . . . H2N H 0.882(6) 1.301(6) -0.024(2) 0.073(15) Uiso 1 1 d . . . H8 H 0.193(6) 1.366(6) 0.189(2) 0.074(13) Uiso 1 1 d . . . H2A H 0.896(8) 0.510(8) 0.208(3) 0.098(17) Uiso 1 1 d . . . H2B H 0.783(13) 0.474(13) 0.166(5) 0.18(5) 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 Cu1 0.02511(17) 0.02939(18) 0.03705(19) 0.00521(13) 0.01624(12) 0.00663(12) O1 0.0263(8) 0.0397(10) 0.0427(10) 0.0103(9) 0.0175(7) 0.0073(7) O2 0.0319(10) 0.0646(14) 0.0392(10) 0.0199(10) 0.0185(8) 0.0120(9) O3 0.0442(11) 0.0380(10) 0.0517(12) 0.0173(9) 0.0311(9) 0.0178(9) O4 0.0763(18) 0.0680(17) 0.109(2) 0.0544(17) 0.0753(18) 0.0484(15) C7 0.0285(12) 0.0382(14) 0.0444(15) 0.0026(12) 0.0166(11) 0.0036(11) C8 0.0471(17) 0.0424(16) 0.066(2) -0.0020(15) 0.0274(15) 0.0177(14) C9 0.0433(17) 0.0349(15) 0.082(2) -0.0047(16) 0.0339(17) 0.0012(13) C4 0.0343(13) 0.0385(14) 0.0443(15) 0.0053(12) 0.0066(11) 0.0062(11) C5 0.0548(18) 0.0386(15) 0.0416(15) 0.0128(13) 0.0121(13) 0.0121(13) C6 0.0324(13) 0.0433(16) 0.0406(14) 0.0111(12) 0.0130(11) 0.0067(11) C1 0.0238(11) 0.0347(13) 0.0314(11) 0.0015(10) 0.0117(9) 0.0002(9) C2 0.071(3) 0.065(2) 0.075(3) 0.041(2) 0.057(2) 0.041(2) C3 0.0284(11) 0.0308(12) 0.0382(13) 0.0051(10) 0.0177(10) 0.0064(9) N3 0.0284(10) 0.0311(11) 0.0507(13) 0.0014(10) 0.0204(9) 0.0038(9) N4 0.0252(11) 0.0551(15) 0.0453(13) 0.0013(11) 0.0171(10) 0.0083(11) N1 0.0281(10) 0.0311(10) 0.0369(11) 0.0045(9) 0.0111(8) 0.0049(9) N2 0.0478(14) 0.0405(13) 0.0419(13) 0.0101(11) 0.0221(11) 0.0026(11) _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 O3 1.9319(19) . ? Cu1 O1 1.9621(19) . ? Cu1 N3 1.981(2) . ? Cu1 N1 1.999(2) . ? Cu1 O2 2.394(2) 2_655 ? O1 C1 1.255(3) . ? O2 C1 1.251(3) . ? O2 Cu1 2.394(2) 2_645 ? O3 C3 1.266(3) . ? O4 C3 1.223(3) . ? C7 N3 1.318(3) . ? C7 N4 1.334(4) . ? C7 H7 0.94(4) . ? C8 C9 1.345(4) . ? C8 N4 1.355(5) . ? C8 H8 0.86(5) . ? C9 N3 1.376(4) . ? C9 H9 0.84(5) . ? C4 C5 1.344(4) . ? C4 N1 1.377(4) . ? C4 H4 0.96(3) . ? C5 N2 1.356(4) . ? C5 H5 0.87(4) . ? C6 N1 1.315(3) . ? C6 N2 1.331(4) . ? C6 H6 0.88(4) . ? C1 C2 1.502(4) . ? C2 C3 1.488(4) . ? C2 H2A 0.86(6) . ? C2 H2B 0.76(10) . ? N4 H4N 0.78(5) . ? N2 H2N 0.73(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 O3 Cu1 O1 92.20(8) . . ? O3 Cu1 N3 173.92(10) . . ? O1 Cu1 N3 87.22(9) . . ? O3 Cu1 N1 87.29(9) . . ? O1 Cu1 N1 172.95(9) . . ? N3 Cu1 N1 92.54(9) . . ? O3 Cu1 O2 87.84(9) . 2_655 ? O1 Cu1 O2 92.47(8) . 2_655 ? N3 Cu1 O2 98.23(9) . 2_655 ? N1 Cu1 O2 94.54(9) . 2_655 ? C1 O1 Cu1 125.70(16) . . ? C1 O2 Cu1 133.11(17) . 2_645 ? C3 O3 Cu1 129.59(16) . . ? N3 C7 N4 110.8(3) . . ? N3 C7 H7 125(2) . . ? N4 C7 H7 124(2) . . ? C9 C8 N4 106.1(3) . . ? C9 C8 H8 129(3) . . ? N4 C8 H8 125(3) . . ? C8 C9 N3 109.7(3) . . ? C8 C9 H9 127(3) . . ? N3 C9 H9 122(3) . . ? C5 C4 N1 109.5(3) . . ? C5 C4 H4 125(2) . . ? N1 C4 H4 125(2) . . ? C4 C5 N2 106.4(3) . . ? C4 C5 H5 130(3) . . ? N2 C5 H5 124(3) . . ? N1 C6 N2 111.3(3) . . ? N1 C6 H6 122(2) . . ? N2 C6 H6 126(2) . . ? O2 C1 O1 122.6(2) . . ? O2 C1 C2 117.1(2) . . ? O1 C1 C2 120.2(2) . . ? C3 C2 C1 122.6(3) . . ? C3 C2 H2A 110(4) . . ? C1 C2 H2A 112(4) . . ? C3 C2 H2B 110(7) . . ? C1 C2 H2B 108(7) . . ? H2A C2 H2B 89(7) . . ? O4 C3 O3 123.5(2) . . ? O4 C3 C2 114.9(2) . . ? O3 C3 C2 121.6(2) . . ? C7 N3 C9 105.3(2) . . ? C7 N3 Cu1 127.0(2) . . ? C9 N3 Cu1 127.6(2) . . ? C7 N4 C8 108.1(2) . . ? C7 N4 H4N 125(3) . . ? C8 N4 H4N 127(3) . . ? C6 N1 C4 105.1(2) . . ? C6 N1 Cu1 125.21(19) . . ? C4 N1 Cu1 129.53(19) . . ? C6 N2 C5 107.7(3) . . ? C6 N2 H2N 119(4) . . ? C5 N2 H2N 133(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.855 _refine_diff_density_min -1.053 _refine_diff_density_rms 0.101 #===END data_COMPOUND_2 _database_code_CSD 193605 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cu N4 O4' _chemical_formula_weight 329.80 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.036(2) _cell_length_b 8.230(2) _cell_length_c 22.932(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1327.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 1.664 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2277 _diffrn_reflns_av_R_equivalents 0.0027 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 29.97 _reflns_number_total 2230 _reflns_number_gt 1810 _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^)+(0.0609P)^2^+1.4324P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 2230 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cu1 Cu 0.91589(8) 0.15261(6) 0.89714(2) 0.01894(14) Uani 1 1 d . . . O1 O 1.0833(5) 0.1132(4) 0.96403(13) 0.0236(7) Uani 1 1 d . . . O2 O 1.2148(5) 0.2041(4) 1.04503(15) 0.0266(8) Uani 1 1 d . . . O3 O 1.0883(6) 0.3265(4) 0.87050(14) 0.0316(8) Uani 1 1 d . . . O4 O 1.2972(6) 0.5227(5) 0.88277(15) 0.0317(9) Uani 1 1 d . . . N1 N 0.7799(6) 0.1789(5) 0.82156(16) 0.0231(8) Uani 1 1 d . . . N2 N 0.5799(11) 0.2435(9) 0.7516(3) 0.0639(18) Uani 1 1 d . . . H2 H 0.4880 0.2871 0.7324 0.060(8) Uiso 1 1 calc R . . N3 N 0.8031(6) -0.0716(5) 0.90796(18) 0.0223(8) Uani 1 1 d . . . N4 N 0.7934(10) -0.3354(8) 0.9204(4) 0.088(3) Uani 1 1 d . . . H4 H 0.8251 -0.4348 0.9266 0.060(8) Uiso 1 1 calc R . . C1 C 1.1601(7) 0.2257(6) 0.9939(2) 0.0195(9) Uani 1 1 d . . . C2 C 1.1826(8) 0.3953(6) 0.9680(2) 0.0242(10) Uani 1 1 d . . . H2A H 1.0775 0.4610 0.9819 0.060(8) Uiso 1 1 calc R . . H2B H 1.2980 0.4421 0.9840 0.060(8) Uiso 1 1 calc R . . C3 C 1.1911(6) 0.4129(6) 0.9025(2) 0.0208(8) Uani 1 1 d . . . C4 C 0.6243(8) 0.2729(8) 0.8084(2) 0.0344(13) Uani 1 1 d . . . H4A H 0.5613 0.3433 0.8336 0.060(8) Uiso 1 1 calc R . . C5 C 0.7055(7) 0.1337(7) 0.73060(18) 0.0245(10) Uani 1 1 d . . . H5 H 0.7083 0.0909 0.6931 0.060(8) Uiso 1 1 calc R . . C6 C 0.8230(8) 0.0991(7) 0.7735(2) 0.0284(11) Uani 1 1 d . . . C7 C 0.9138(10) -0.2070(7) 0.9191(3) 0.0466(16) Uani 1 1 d . . . H7 H 1.0448 -0.2094 0.9246 0.060(8) Uiso 1 1 calc R . . C9 C 0.6250(7) -0.1223(6) 0.9030(2) 0.0262(10) Uani 1 1 d . . . C8 C 0.6176(7) -0.2819(6) 0.9103(2) 0.0280(11) Uani 1 1 d . . . H8 H 0.5086 -0.3457 0.9086 0.060(8) Uiso 1 1 calc R . . C10 C 0.4534(7) -0.0235(8) 0.8934(4) 0.0475(16) Uani 1 1 d . . . H10A H 0.4818 0.0887 0.9008 0.111(16) Uiso 1 1 calc R . . H10B H 0.3545 -0.0590 0.9193 0.111(16) Uiso 1 1 calc R . . H10C H 0.4120 -0.0358 0.8537 0.111(16) Uiso 1 1 calc R . . C11 C 0.9892(13) -0.0142(12) 0.7666(3) 0.069(3) Uani 1 1 d . . . H11A H 1.1053 0.0446 0.7730 0.111(16) Uiso 1 1 calc R . . H11B H 0.9891 -0.0586 0.7279 0.111(16) Uiso 1 1 calc R . . H11C H 0.9794 -0.1007 0.7945 0.111(16) 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 Cu1 0.0218(2) 0.0175(2) 0.0175(2) -0.0015(2) -0.0015(2) -0.0045(2) O1 0.0283(16) 0.0179(14) 0.0245(14) -0.0001(12) -0.0056(16) -0.0063(16) O2 0.0359(19) 0.0216(16) 0.0223(15) 0.0036(14) -0.0089(15) -0.0048(16) O3 0.0395(19) 0.036(2) 0.0196(14) 0.0045(14) -0.0044(16) -0.017(2) O4 0.0347(19) 0.038(2) 0.0225(16) 0.0074(15) -0.0041(15) -0.0194(18) N1 0.0262(19) 0.023(2) 0.0202(17) -0.0018(15) -0.0027(16) -0.0008(17) N2 0.066(4) 0.083(5) 0.042(3) 0.012(3) -0.016(4) 0.001(5) N3 0.0207(18) 0.0170(17) 0.029(2) -0.0012(15) -0.0025(16) -0.0035(15) N4 0.065(4) 0.027(3) 0.172(9) 0.024(4) -0.036(5) -0.015(3) C1 0.018(2) 0.020(2) 0.020(2) -0.0007(19) 0.0006(17) 0.0034(19) C2 0.034(3) 0.018(2) 0.020(2) -0.0007(17) -0.005(2) -0.002(2) C3 0.0215(19) 0.0223(19) 0.019(2) 0.0021(18) -0.0023(19) -0.0026(17) C4 0.038(3) 0.037(3) 0.028(2) 0.000(2) -0.001(2) 0.007(3) C5 0.030(2) 0.030(3) 0.0137(17) -0.0049(18) -0.0039(17) 0.001(2) C6 0.030(3) 0.029(2) 0.026(2) -0.005(2) 0.000(2) -0.001(2) C7 0.028(3) 0.023(2) 0.089(5) 0.011(3) -0.013(3) -0.006(3) C9 0.027(2) 0.025(2) 0.026(2) -0.0054(19) 0.001(2) -0.0069(18) C8 0.022(2) 0.015(2) 0.047(3) 0.005(2) -0.005(2) -0.0107(18) C10 0.021(3) 0.046(3) 0.076(5) 0.002(4) -0.004(3) -0.002(2) C11 0.074(5) 0.090(7) 0.042(4) -0.024(4) -0.007(4) 0.051(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.961(3) . ? Cu1 O3 1.973(4) . ? Cu1 N1 1.992(4) . ? Cu1 N3 2.024(4) . ? Cu1 O2 2.270(4) 4_457 ? O1 C1 1.272(5) . ? O2 C1 1.246(6) . ? O2 Cu1 2.270(4) 4_557 ? O3 C3 1.251(6) . ? O4 C3 1.256(6) . ? N1 C6 1.318(6) . ? N1 C4 1.374(7) . ? N2 C5 1.353(9) . ? N2 C4 1.362(8) . ? N2 H2 0.8600 . ? N3 C9 1.325(6) . ? N3 C7 1.383(7) . ? N4 C8 1.333(9) . ? N4 C7 1.355(8) . ? N4 H4 0.8600 . ? C1 C2 1.525(7) . ? C2 C3 1.512(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 H4A 0.9300 . ? C5 C6 1.317(7) . ? C5 H5 0.9300 . ? C6 C11 1.504(9) . ? C7 H7 0.9300 . ? C9 C8 1.326(6) . ? C9 C10 1.473(8) . ? C8 H8 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 O1 Cu1 O3 89.59(15) . . ? O1 Cu1 N1 170.86(17) . . ? O3 Cu1 N1 86.97(15) . . ? O1 Cu1 N3 89.36(15) . . ? O3 Cu1 N3 160.11(17) . . ? N1 Cu1 N3 90.99(17) . . ? O1 Cu1 O2 90.20(14) . 4_457 ? O3 Cu1 O2 100.80(15) . 4_457 ? N1 Cu1 O2 98.76(15) . 4_457 ? N3 Cu1 O2 99.07(15) . 4_457 ? C1 O1 Cu1 123.8(3) . . ? C1 O2 Cu1 131.9(3) . 4_557 ? C3 O3 Cu1 125.9(3) . . ? C6 N1 C4 106.3(4) . . ? C6 N1 Cu1 124.2(4) . . ? C4 N1 Cu1 129.4(3) . . ? C5 N2 C4 108.0(6) . . ? C5 N2 H2 126.0 . . ? C4 N2 H2 126.0 . . ? C9 N3 C7 107.2(4) . . ? C9 N3 Cu1 130.3(3) . . ? C7 N3 Cu1 122.4(4) . . ? C8 N4 C7 108.6(6) . . ? C8 N4 H4 125.7 . . ? C7 N4 H4 125.7 . . ? O2 C1 O1 122.3(5) . . ? O2 C1 C2 117.7(4) . . ? O1 C1 C2 120.0(4) . . ? C3 C2 C1 118.6(4) . . ? C3 C2 H2A 107.7 . . ? C1 C2 H2A 107.7 . . ? C3 C2 H2B 107.7 . . ? C1 C2 H2B 107.7 . . ? H2A C2 H2B 107.1 . . ? O3 C3 O4 122.8(4) . . ? O3 C3 C2 120.4(4) . . ? O4 C3 C2 116.7(4) . . ? N2 C4 N1 107.0(5) . . ? N2 C4 H4A 126.5 . . ? N1 C4 H4A 126.5 . . ? C6 C5 N2 106.8(5) . . ? C6 C5 H5 126.6 . . ? N2 C5 H5 126.6 . . ? C5 C6 N1 111.9(5) . . ? C5 C6 C11 122.9(5) . . ? N1 C6 C11 125.2(5) . . ? N4 C7 N3 106.2(5) . . ? N4 C7 H7 126.9 . . ? N3 C7 H7 126.9 . . ? N3 C9 C8 109.8(5) . . ? N3 C9 C10 127.9(5) . . ? C8 C9 C10 122.3(5) . . ? C9 C8 N4 108.2(5) . . ? C9 C8 H8 125.9 . . ? N4 C8 H8 125.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.718 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.117