############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[\m-N'-isobutyryl-1-oxidonaphthalene-2- carbohydrazidato(3-)]dipyridinetricopper(II) ; _chemical_name_common ? _chemical_formula_moiety 'C40 H36 Cu3 N6 O6' _chemical_formula_sum 'C40 H36 Cu3 N6 O6' _chemical_formula_iupac '[Cu3 (C15 H13 N2 O3)2 (C5 H5 N)2]' _chemical_formula_weight 887.37 _chemical_melting_point ? _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 23.661(2) _cell_length_b 13.0521(18) _cell_length_c 13.3142(15) _cell_angle_alpha 90.00 _cell_angle_beta 113.684(2) _cell_angle_gamma 90.00 _cell_volume 3765.5(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3140 _cell_measurement_theta_min 2.715 _cell_measurement_theta_max 26.323 _cell_measurement_temperature 298(2) _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.31 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_meas 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1812 _exptl_absorpt_coefficient_mu 1.735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Siemens, 1996)' _exptl_absorpt_correction_T_min 0.566 _exptl_absorpt_correction_T_max 0.615 _exptl_special_details ; ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9477 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _reflns_number_total 3310 _reflns_number_gt 2319 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.1354 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_number_reflns 3310 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.079P)^2^+4.0071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.822 _refine_diff_density_min -0.328 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu1 0.5000 0.86302(6) 0.2500 0.0410(2) Uani d S 1 . . Cu Cu2 0.68569(2) 0.80745(4) 0.23216(4) 0.0404(2) Uani d . 1 . . N N1 0.62147(15) 0.8496(3) 0.2723(3) 0.0401(8) Uani d . 1 . . N N2 0.56137(15) 0.8380(3) 0.1900(3) 0.0425(9) Uani d . 1 . . N N3 0.74587(15) 0.7504(3) 0.1787(3) 0.0386(8) Uani d . 1 . . O O1 0.57183(12) 0.8896(2) 0.3816(2) 0.0446(7) Uani d . 1 . . O O2 0.74777(12) 0.8431(2) 0.3698(2) 0.0442(7) Uani d . 1 . . O O3 0.61596(13) 0.7851(3) 0.0920(2) 0.0523(8) Uani d . 1 . . C C1 0.62281(18) 0.8758(3) 0.3692(3) 0.0363(9) Uani d . 1 . . C C2 0.73934(18) 0.8742(3) 0.4567(3) 0.0361(9) Uani d . 1 . . C C3 0.68203(18) 0.8912(3) 0.4623(3) 0.0341(9) Uani d . 1 . . C C4 0.68036(19) 0.9281(3) 0.5618(3) 0.0399(10) Uani d . 1 . . H H4 0.6421 0.9386 0.5645 0.048 Uiso calc R 1 . . C C5 0.7314(2) 0.9484(3) 0.6518(3) 0.0440(11) Uani d . 1 . . H H5 0.7278 0.9733 0.7144 0.053 Uiso calc R 1 . . C C6 0.7909(2) 0.9322(3) 0.6522(3) 0.0421(10) Uani d . 1 . . C C7 0.79500(19) 0.8936(3) 0.5546(3) 0.0398(10) Uani d . 1 . . C C8 0.85377(19) 0.8776(4) 0.5545(4) 0.0503(11) Uani d . 1 . . H H8 0.8570 0.8522 0.4919 0.060 Uiso calc R 1 . . C C9 0.9059(2) 0.8990(5) 0.6448(4) 0.0674(15) Uani d . 1 . . H H9 0.9443 0.8885 0.6426 0.081 Uiso calc R 1 . . C C10 0.9026(2) 0.9367(4) 0.7415(4) 0.0655(15) Uani d . 1 . . H H10 0.9385 0.9507 0.8029 0.079 Uiso calc R 1 . . C C11 0.8464(2) 0.9522(4) 0.7439(4) 0.0559(13) Uani d . 1 . . H H11 0.8443 0.9767 0.8080 0.067 Uiso calc R 1 . . C C12 0.56432(19) 0.8035(4) 0.0990(4) 0.0451(11) Uani d . 1 . . C C13 0.5056(2) 0.7872(4) -0.0027(4) 0.0548(13) Uani d . 1 . . H H13 0.4703 0.7944 0.0176 0.066 Uiso calc R 1 . . C C14 0.5046(3) 0.6793(5) -0.0479(5) 0.090(2) Uani d . 1 . . H H14A 0.5318 0.6765 -0.0854 0.135 Uiso calc R 1 . . H H14B 0.4634 0.6627 -0.0982 0.135 Uiso calc R 1 . . H H14C 0.5180 0.6310 0.0114 0.135 Uiso calc R 1 . . C C15 0.5004(3) 0.8681(5) -0.0879(5) 0.0862(19) Uani d . 1 . . H H15A 0.5084 0.9344 -0.0539 0.129 Uiso calc R 1 . . H H15B 0.4595 0.8668 -0.1449 0.129 Uiso calc R 1 . . H H15C 0.5299 0.8541 -0.1188 0.129 Uiso calc R 1 . . C C16 0.7284(2) 0.6777(3) 0.0995(3) 0.0414(10) Uani d . 1 . . H H16 0.6872 0.6577 0.0689 0.050 Uiso calc R 1 . . C C17 0.7684(2) 0.6324(3) 0.0624(4) 0.0468(11) Uani d . 1 . . H H17 0.7548 0.5822 0.0084 0.056 Uiso calc R 1 . . C C18 0.8288(2) 0.6624(4) 0.1064(4) 0.0585(13) Uani d . 1 . . H H18 0.8571 0.6324 0.0829 0.070 Uiso calc R 1 . . C C19 0.8476(2) 0.7379(5) 0.1861(4) 0.0604(13) Uani d . 1 . . H H19 0.8883 0.7605 0.2160 0.072 Uiso calc R 1 . . C C20 0.8046(2) 0.7787(4) 0.2200(4) 0.0489(11) Uani d . 1 . . H H20 0.8174 0.8285 0.2745 0.059 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0270(4) 0.0562(5) 0.0400(4) 0.000 0.0138(3) 0.000 Cu2 0.0282(3) 0.0537(4) 0.0391(3) -0.0004(2) 0.0133(2) -0.0070(2) N1 0.0243(17) 0.058(2) 0.0350(19) -0.0019(16) 0.0083(15) -0.0053(17) N2 0.0269(18) 0.062(2) 0.0371(19) -0.0036(17) 0.0110(16) -0.0097(18) N3 0.0349(19) 0.044(2) 0.0392(19) 0.0012(16) 0.0175(16) -0.0024(17) O1 0.0286(15) 0.0644(19) 0.0435(17) -0.0017(14) 0.0172(13) -0.0100(15) O2 0.0308(15) 0.0602(19) 0.0417(17) -0.0003(14) 0.0146(13) -0.0083(15) O3 0.0291(16) 0.088(2) 0.0386(17) 0.0002(16) 0.0123(13) -0.0135(16) C1 0.031(2) 0.039(2) 0.041(2) -0.0013(18) 0.0161(18) -0.0011(19) C2 0.034(2) 0.032(2) 0.040(2) -0.0022(17) 0.0121(18) 0.0006(18) C3 0.029(2) 0.034(2) 0.037(2) -0.0010(17) 0.0120(17) -0.0024(18) C4 0.039(2) 0.042(2) 0.040(2) -0.0004(19) 0.016(2) -0.0016(19) C5 0.057(3) 0.041(2) 0.034(2) -0.003(2) 0.017(2) -0.0002(19) C6 0.046(3) 0.032(2) 0.041(2) -0.0017(19) 0.011(2) 0.0039(19) C7 0.040(2) 0.032(2) 0.043(2) -0.0017(18) 0.013(2) 0.0008(19) C8 0.034(2) 0.059(3) 0.053(3) 0.002(2) 0.012(2) -0.008(2) C9 0.037(3) 0.089(4) 0.066(3) 0.001(3) 0.009(3) -0.006(3) C10 0.041(3) 0.072(4) 0.058(3) -0.002(3) -0.007(2) -0.004(3) C11 0.057(3) 0.054(3) 0.043(3) -0.003(2) 0.006(2) -0.002(2) C12 0.031(2) 0.064(3) 0.040(2) -0.001(2) 0.0130(19) -0.001(2) C13 0.031(2) 0.088(4) 0.038(2) 0.001(2) 0.008(2) -0.009(3) C14 0.078(4) 0.082(4) 0.070(4) -0.011(3) -0.012(3) -0.016(3) C15 0.074(4) 0.084(4) 0.064(4) -0.006(3) -0.009(3) 0.004(3) C16 0.042(2) 0.038(2) 0.044(2) -0.0023(19) 0.018(2) 0.001(2) C17 0.056(3) 0.040(3) 0.046(3) 0.004(2) 0.022(2) -0.002(2) C18 0.057(3) 0.070(3) 0.055(3) 0.024(3) 0.031(3) 0.002(3) C19 0.035(3) 0.089(4) 0.056(3) 0.005(3) 0.017(2) -0.003(3) C20 0.035(2) 0.062(3) 0.047(3) 0.000(2) 0.014(2) -0.008(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O1 . 1.920(3) y Cu1 O1 2_655 1.920(3) y Cu1 N2 . 1.946(3) y Cu1 N2 2_655 1.946(3) y Cu2 N1 . 1.884(3) y Cu2 O2 . 1.890(3) y Cu2 O3 . 1.953(3) y Cu2 N3 . 1.975(3) y N1 C1 . 1.323(5) ? N1 N2 . 1.412(5) ? N2 C12 . 1.320(5) ? N3 C20 . 1.326(5) ? N3 C16 . 1.354(5) ? O1 C1 . 1.294(5) ? O2 C2 . 1.315(5) ? O3 C12 . 1.285(5) ? C1 C3 . 1.465(5) ? C2 C3 . 1.405(5) ? C2 C7 . 1.455(6) ? C3 C4 . 1.425(6) ? C4 C5 . 1.342(6) ? C4 H4 . 0.9300 ? C5 C6 . 1.423(6) ? C5 H5 . 0.9300 ? C6 C11 . 1.412(6) ? C6 C7 . 1.433(6) ? C7 C8 . 1.406(6) ? C8 C9 . 1.361(6) ? C8 H8 . 0.9300 ? C9 C10 . 1.409(7) ? C9 H9 . 0.9300 ? C10 C11 . 1.360(7) ? C10 H10 . 0.9300 ? C11 H11 . 0.9300 ? C12 C13 . 1.516(6) ? C13 C15 . 1.518(8) ? C13 C14 . 1.529(8) ? C13 H13 . 0.9800 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? C15 H15A . 0.9600 ? C15 H15B . 0.9600 ? C15 H15C . 0.9600 ? C16 C17 . 1.365(6) ? C16 H16 . 0.9300 ? C17 C18 . 1.367(7) ? C17 H17 . 0.9300 ? C18 C19 . 1.384(7) ? C18 H18 . 0.9300 ? C19 C20 . 1.374(6) ? C19 H19 . 0.9300 ? C20 H20 . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Cu1 O1 . 2_655 159.21(19) n O1 Cu1 N2 . . 82.65(13) n O1 Cu1 N2 2_655 . 100.87(13) n O1 Cu1 N2 . 2_655 100.87(13) n O1 Cu1 N2 2_655 2_655 82.65(13) n N2 Cu1 N2 . 2_655 160.7(2) n N1 Cu2 O2 . . 93.11(13) n N1 Cu2 O3 . . 81.17(13) n O2 Cu2 O3 . . 173.00(13) n N1 Cu2 N3 . . 172.94(14) n O2 Cu2 N3 . . 92.88(13) n O3 Cu2 N3 . . 93.10(13) n C1 N1 N2 . . 114.0(3) ? C1 N1 Cu2 . . 130.2(3) ? N2 N1 Cu2 . . 115.1(3) ? C12 N2 N1 . . 109.9(3) ? C12 N2 Cu1 . . 139.2(3) ? N1 N2 Cu1 . . 110.4(2) ? C20 N3 C16 . . 117.3(4) ? C20 N3 Cu2 . . 122.2(3) ? C16 N3 Cu2 . . 120.4(3) ? C1 O1 Cu1 . . 112.8(3) ? C2 O2 Cu2 . . 126.6(3) ? C12 O3 Cu2 . . 111.4(3) ? O1 C1 N1 . . 120.1(4) ? O1 C1 C3 . . 119.8(4) ? N1 C1 C3 . . 120.1(3) ? O2 C2 C3 . . 125.9(4) ? O2 C2 C7 . . 116.0(4) ? C3 C2 C7 . . 118.1(4) ? C2 C3 C4 . . 119.4(4) ? C2 C3 C1 . . 123.3(4) ? C4 C3 C1 . . 117.3(3) ? C5 C4 C3 . . 123.1(4) ? C5 C4 H4 . . 118.5 ? C3 C4 H4 . . 118.5 ? C4 C5 C6 . . 120.6(4) ? C4 C5 H5 . . 119.7 ? C6 C5 H5 . . 119.7 ? C11 C6 C5 . . 123.4(4) ? C11 C6 C7 . . 118.2(4) ? C5 C6 C7 . . 118.4(4) ? C8 C7 C6 . . 118.6(4) ? C8 C7 C2 . . 120.9(4) ? C6 C7 C2 . . 120.5(4) ? C9 C8 C7 . . 121.0(5) ? C9 C8 H8 . . 119.5 ? C7 C8 H8 . . 119.5 ? C8 C9 C10 . . 121.0(5) ? C8 C9 H9 . . 119.5 ? C10 C9 H9 . . 119.5 ? C11 C10 C9 . . 119.2(4) ? C11 C10 H10 . . 120.4 ? C9 C10 H10 . . 120.4 ? C10 C11 C6 . . 122.0(5) ? C10 C11 H11 . . 119.0 ? C6 C11 H11 . . 119.0 ? O3 C12 N2 . . 122.2(4) ? O3 C12 C13 . . 117.8(4) ? N2 C12 C13 . . 120.0(4) ? C12 C13 C15 . . 109.9(4) ? C12 C13 C14 . . 110.1(4) ? C15 C13 C14 . . 111.2(5) ? C12 C13 H13 . . 108.5 ? C15 C13 H13 . . 108.5 ? C14 C13 H13 . . 108.5 ? C13 C14 H14A . . 109.5 ? C13 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C13 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? C13 C15 H15A . . 109.5 ? C13 C15 H15B . . 109.5 ? H15A C15 H15B . . 109.5 ? C13 C15 H15C . . 109.5 ? H15A C15 H15C . . 109.5 ? H15B C15 H15C . . 109.5 ? N3 C16 C17 . . 123.1(4) ? N3 C16 H16 . . 118.5 ? C17 C16 H16 . . 118.5 ? C16 C17 C18 . . 118.6(4) ? C16 C17 H17 . . 120.7 ? C18 C17 H17 . . 120.7 ? C17 C18 C19 . . 119.4(4) ? C17 C18 H18 . . 120.3 ? C19 C18 H18 . . 120.3 ? C20 C19 C18 . . 118.4(5) ? C20 C19 H19 . . 120.8 ? C18 C19 H19 . . 120.8 ? N3 C20 C19 . . 123.2(4) ? N3 C20 H20 . . 118.4 ? C19 C20 H20 . . 118.4 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 Cu2 N1 C1 . . . . -10.5(4) ? O3 Cu2 N1 C1 . . . . 173.6(4) ? O2 Cu2 N1 N2 . . . . 179.6(3) ? O3 Cu2 N1 N2 . . . . 3.6(3) ? C1 N1 N2 C12 . . . . -174.6(4) ? Cu2 N1 N2 C12 . . . . -3.0(5) ? C1 N1 N2 Cu1 . . . . -0.9(5) ? Cu2 N1 N2 Cu1 . . . . 170.69(17) ? O1 Cu1 N2 C12 . . . . 172.5(5) ? O1 Cu1 N2 C12 2_655 . . . -28.3(5) ? N2 Cu1 N2 C12 2_655 . . . 70.6(5) ? O1 Cu1 N2 N1 . . . . 1.6(3) ? O1 Cu1 N2 N1 2_655 . . . 160.8(3) ? N2 Cu1 N2 N1 2_655 . . . -100.4(3) ? O2 Cu2 N3 C20 . . . . -23.5(4) ? O3 Cu2 N3 C20 . . . . 152.8(4) ? O2 Cu2 N3 C16 . . . . 154.6(3) ? O3 Cu2 N3 C16 . . . . -29.1(3) ? O1 Cu1 O1 C1 2_655 . . . -103.3(3) ? N2 Cu1 O1 C1 . . . . -2.0(3) ? N2 Cu1 O1 C1 2_655 . . . 158.7(3) ? N1 Cu2 O2 C2 . . . . 6.4(3) ? N3 Cu2 O2 C2 . . . . -169.9(3) ? N1 Cu2 O3 C12 . . . . -3.6(3) ? N3 Cu2 O3 C12 . . . . 172.2(3) ? Cu1 O1 C1 N1 . . . . 2.2(5) ? Cu1 O1 C1 C3 . . . . -179.0(3) ? N2 N1 C1 O1 . . . . -0.8(6) ? Cu2 N1 C1 O1 . . . . -170.8(3) ? N2 N1 C1 C3 . . . . -179.6(3) ? Cu2 N1 C1 C3 . . . . 10.4(6) ? Cu2 O2 C2 C3 . . . . -3.0(6) ? Cu2 O2 C2 C7 . . . . 177.9(3) ? O2 C2 C3 C4 . . . . -178.1(4) ? C7 C2 C3 C4 . . . . 1.1(6) ? O2 C2 C3 C1 . . . . 0.1(7) ? C7 C2 C3 C1 . . . . 179.2(4) ? O1 C1 C3 C2 . . . . 177.6(4) ? N1 C1 C3 C2 . . . . -3.6(6) ? O1 C1 C3 C4 . . . . -4.3(6) ? N1 C1 C3 C4 . . . . 174.6(4) ? C2 C3 C4 C5 . . . . 0.4(6) ? C1 C3 C4 C5 . . . . -177.8(4) ? C3 C4 C5 C6 . . . . -0.9(7) ? C4 C5 C6 C11 . . . . 179.9(4) ? C4 C5 C6 C7 . . . . -0.1(6) ? C11 C6 C7 C8 . . . . -0.1(6) ? C5 C6 C7 C8 . . . . 179.8(4) ? C11 C6 C7 C2 . . . . -178.4(4) ? C5 C6 C7 C2 . . . . 1.6(6) ? O2 C2 C7 C8 . . . . -1.0(6) ? C3 C2 C7 C8 . . . . 179.8(4) ? O2 C2 C7 C6 . . . . 177.1(4) ? C3 C2 C7 C6 . . . . -2.1(6) ? C6 C7 C8 C9 . . . . -0.4(7) ? C2 C7 C8 C9 . . . . 177.8(5) ? C7 C8 C9 C10 . . . . 0.7(8) ? C8 C9 C10 C11 . . . . -0.3(9) ? C9 C10 C11 C6 . . . . -0.3(8) ? C5 C6 C11 C10 . . . . -179.4(5) ? C7 C6 C11 C10 . . . . 0.5(7) ? Cu2 O3 C12 N2 . . . . 3.1(6) ? Cu2 O3 C12 C13 . . . . -178.6(3) ? N1 N2 C12 O3 . . . . -0.2(6) ? Cu1 N2 C12 O3 . . . . -171.2(3) ? N1 N2 C12 C13 . . . . -178.4(4) ? Cu1 N2 C12 C13 . . . . 10.7(8) ? O3 C12 C13 C15 . . . . -69.6(6) ? N2 C12 C13 C15 . . . . 108.6(5) ? O3 C12 C13 C14 . . . . 53.2(6) ? N2 C12 C13 C14 . . . . -128.5(5) ? C20 N3 C16 C17 . . . . 0.9(6) ? Cu2 N3 C16 C17 . . . . -177.3(3) ? N3 C16 C17 C18 . . . . -0.7(7) ? C16 C17 C18 C19 . . . . -0.5(7) ? C17 C18 C19 C20 . . . . 1.4(8) ? C16 N3 C20 C19 . . . . 0.0(7) ? Cu2 N3 C20 C19 . . . . 178.2(4) ? C18 C19 C20 N3 . . . . -1.2(8) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C17 H17 Cg1 4_645 0.93 2.53 3.362(4) 150 data_global _journal_date_recd_electronic 2009-02-20 _journal_date_accepted 2009-03-11 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2009 _journal_volume 65 _journal_issue 4 _journal_page_first m435 _journal_page_last m435 _journal_paper_category QM _journal_coeditor_code HB2917 _publ_contact_author_name 'Prof. Dacheng Li' _publ_contact_author_address ; College of Chemistry and Chemical Engineering Liaocheng University Shandong 252059 People's Republic of China ; _publ_contact_author_email lidacheng@lcu.edu.cn _publ_contact_author_fax '86 635 8239121' _publ_contact_author_phone '86 635 8230664' _publ_section_title ;\ Bis[\m-N'-isobutyryl-1-oxidonaphthalene-2-carbohydrazidato(3-)]\ dipyridinetricopper(II) ; loop_ _publ_author_name _publ_author_address 'Xue-Feng Shi' ; College of Chemistry and Chemical Engineering Liaocheng University Shandong 252059 People's Republic of China ; 'Dacheng Li' ; College of Chemistry and Chemical Engineering Liaocheng University Shandong 252059 People's Republic of China ; 'Pi-Yong Li' ; College of Chemistry and Chemical Engineering Liaocheng University Shandong 252059 People's Republic of China ; 'Da-Qi Wang' ; College of Chemistry and Chemical Engineering Liaocheng University Shandong 252059 People's Republic of China ;