##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.1
_journal_date_recd_electronic     2004-04-20
_journal_date_accepted     2004-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      6
_journal_page_first     m720
_journal_page_last     m722
_journal_paper_category     EM
_publ_contact_author_name     'Luque, Antonio'
_publ_contact_author_address
;
Departamento de Química Inorgánica. Facultad de Ciencia y Tecnología
 Universidad del País Vasco, Apdo. 644, E-48080 Bilbao, Spain
;
_publ_contact_author_email     qipluara@lg.ehu.es
_publ_contact_author_fax     '+34-944-648 500'
_publ_contact_author_phone     '+34-946-012 701'
_publ_section_title
;
trans-Bis[4-amino-3,5-bis(2-pyridyl)-4H-1,2,4-triazole-
κ²N¹,N⁵]bis(nitrato-\kO)copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'García-Couceiro, Urko'
;
Departamento de Química Inorgánica
Facultad de Ciencia y Tecnología
Universidad del País Vasco
Apdo. 644
E-48080 Bilbao
Spain
;
    'Castillo, Oscar'
;
Departamento de Química Inorgánica
Facultad de Ciencia y Tecnología
Universidad del País Vasco
Apdo. 644
E-48080 Bilbao
Spain
;
    'Luque, Antonio'
;
Departamento de Química Inorgánica
Facultad de Ciencia y Tecnología
Universidad del País Vasco
Apdo. 644
E-48080 Bilbao
Spain
;
    'Beobide, Garikoitz'
;
Departamento de Química Inorgánica
Facultad de Ciencia y Tecnología
Universidad del País Vasco
Apdo. 644
E-48080 Bilbao
Spain
;
    'Román, Pascual'
;
Departamento de Química Inorgánica
Facultad de Ciencia y Tecnología
Universidad del País Vasco
Apdo. 644
E-48080 Bilbao
Spain
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
trans-bis[4-amino-3,5-bis(2-pyridyl)-4H-1,2,4-triazole-
κ²N¹,N⁵]bis(nitrato-\kO)copper(II)
;
_chemical_formula_moiety     'C24 H20 Cu N14 O6'
_chemical_formula_sum     'C24 H20 Cu N14 O6'
_chemical_formula_iupac     '[Cu (N O3)2 (C12 H10 N6)2]'
_chemical_formula_weight     664.09
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9400(10)
_cell_length_b     9.319(2)
_cell_length_c     10.765(2)
_cell_angle_alpha     99.360(10)
_cell_angle_beta     94.86(2)
_cell_angle_gamma     106.27(2)
_cell_volume     653.2(2)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     6086
_cell_measurement_theta_min     3.26
_cell_measurement_theta_max     29.99
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'light blue'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.688
_exptl_crystal_density_meas     1.690(10)
_exptl_crystal_density_method
                  'flotation in a mixture of carbon tetrachloride and bromoform'
_exptl_crystal_F_000     339
_exptl_absorpt_coefficient_mu     0.909
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     'CrysAlis RED (Oxford Diffraction, 2003)'
_exptl_absorpt_correction_T_min     0.884
_exptl_absorpt_correction_T_max     0.973
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device_type     'Xcalibur'
_diffrn_measurement_method     ω
_diffrn_reflns_number     5600
_diffrn_reflns_av_R_equivalents     0.0510
_diffrn_reflns_av_sigmaI/netI     0.2211
_diffrn_reflns_theta_min     3.26
_diffrn_reflns_theta_max     28.00
_diffrn_reflns_theta_full     28.00
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3102
_reflns_number_gt     1192
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1526
_refine_ls_R_factor_gt     0.0462
_refine_ls_wR_factor_gt     0.0642
_refine_ls_wR_factor_ref     0.0781
_refine_ls_goodness_of_fit_ref     0.812
_refine_ls_restrained_S_all     0.812
_refine_ls_number_reflns     3102
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0159P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap (N-H) and geom (C-H)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.339
_refine_diff_density_min     -0.323
_refine_ls_extinction_method     none
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 0 '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'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_cell_refinement     'CrysAlis CCD'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    Cu1 0.0000 0.0000 0.0000 0.0423(3) Uani d S 1 . . Cu
    N1 -0.1024(4) 0.0832(3) 0.1437(2) 0.0360(10)
                                               Uani d . 1 . . N
    N2 -0.2734(4) 0.0481(3) 0.2027(3) 0.0390(10)
                                               Uani d . 1 . . N
    C3 -0.2518(5) 0.1579(4) 0.2860(3) 0.0370(10)
                                               Uani d . 1 . . C
    N4 -0.0695(4) 0.2626(3) 0.2821(3) 0.0400(10)
                                               Uani d . 1 . . N
    C5 0.0215(5) 0.2117(4) 0.1902(3) 0.0350(10)
                                              Uani d . 1 . . C
    N6 0.0179(4) 0.3967(3) 0.3563(3) 0.0570(10)
                                              Uani d . 1 . . N
    C7 0.2178(5) 0.2691(4) 0.1469(3) 0.0380(10)
                                              Uani d . 1 . . C
    N8 0.2453(4) 0.1783(3) 0.0538(2) 0.0360(10)
                                              Uani d . 1 . . N
    C9 0.4247(5) 0.2128(4) 0.0084(3) 0.0410(10)
                                              Uani d . 1 . . C
    H9 0.4398 0.1438 -0.0601 0.049 Uiso calc R 1 . . H
    C10 0.5811(5) 0.3353(4) 0.0521(4) 0.0490(10)
                                               Uani d . 1 . . C
    H10 0.7024 0.3540 0.0180 0.059 Uiso calc R 1 . . H
    C11 0.5503(5) 0.4249(4) 0.1447(4) 0.0500(10)
                                               Uani d . 1 . . C
    H11 0.6524 0.5145 0.1806 0.060 Uiso calc R 1 . . H
    C12 0.3660(5) 0.3924(4) 0.1945(3) 0.0470(10)
                                               Uani d . 1 . . C
    H12 0.3492 0.4605 0.2631 0.057 Uiso calc R 1 . . H
    C13 -0.4060(6) 0.1657(4) 0.3679(3) 0.0410(10)
                                                Uani d . 1 . . C
    N14 -0.3536(5) 0.2743(3) 0.4589(3) 0.0640(10)
                                                Uani d . 1 . . N
    C15 -0.4938(7) 0.2817(5) 0.5327(4) 0.087(2) Uani d . 1 . . C
    H15 -0.4565 0.3628 0.6017 0.104 Uiso calc R 1 . . H
    C16 -0.6859(7) 0.1868(5) 0.5217(4) 0.077(2) Uani d . 1 . . C
    H16 -0.7760 0.2039 0.5776 0.092 Uiso calc R 1 . . H
    C17 -0.7331(6) 0.0748(5) 0.4310(4) 0.0570(10)
                                                Uani d . 1 . . C
    H17 -0.8594 0.0019 0.4184 0.069 Uiso calc R 1 . . H
    C18 -0.5925(5) 0.0636(4) 0.3512(3) 0.0420(10)
                                                Uani d . 1 . . C
    H18 -0.6266 -0.0178 0.2826 0.050 Uiso calc R 1 . . H
    N20 -0.0574(5) 0.2724(5) -0.1798(4) 0.0610(10)
                                                 Uani d . 1 . . N
    H61 -0.0743 0.4030 0.4181 0.073 Uiso d . 1 . . H
    H62 -0.0026 0.4610 0.2979 0.073 Uiso d . 1 . . H
    O21 -0.0486(6) 0.3979(4) -0.1450(4) 0.128(2) Uani d . 1 . . O
    O22 0.0354(6) 0.2619(4) -0.2639(3) 0.137(2) Uani d . 1 . . O
    O23 -0.1483(4) 0.1648(3) -0.1218(3) 0.0650(10)
                                                 Uani d . 1 . . O
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 0.0363(5) 0.0375(5) 0.0420(5) 0.0018(4) 0.0114(4) -0.0104(4)
    N1 0.033(2) 0.036(2) 0.033(2) 0.007(2) 0.011(2) -0.005(2)
    N2 0.038(2) 0.033(2) 0.036(2) 0.003(2) 0.009(2) -0.014(2)
    C3 0.038(2) 0.031(2) 0.037(2) 0.006(2) 0.007(2) 0.002(2)
    N4 0.041(2) 0.031(2) 0.041(2) 0.004(2) 0.010(2) -0.008(2)
    C5 0.034(2) 0.031(2) 0.033(2) 0.005(2) 0.004(2) -0.004(2)
    N6 0.057(2) 0.038(2) 0.058(2) -0.001(2) 0.010(2) -0.023(2)
    C7 0.034(2) 0.035(2) 0.037(2) 0.008(2) 0.002(2) -0.007(2)
    N8 0.033(2) 0.030(2) 0.035(2) 0.002(2) 0.006(2) -0.006(2)
    C9 0.036(2) 0.037(2) 0.046(3) 0.011(2) 0.009(2) -0.004(2)
    C10 0.034(2) 0.043(3) 0.063(3) 0.004(2) 0.012(2) -0.001(2)
    C11 0.045(3) 0.032(2) 0.060(3) 0.002(2) -0.001(2) -0.007(2)
    C12 0.035(3) 0.038(2) 0.054(3) 0.001(2) 0.009(2) -0.014(2)
    C13 0.046(3) 0.038(2) 0.036(2) 0.011(2) 0.015(2) -0.004(2)
    N14 0.060(2) 0.060(2) 0.051(2) 0.002(2) 0.026(2) -0.025(2)
    C15 0.085(4) 0.069(3) 0.073(3) -0.007(3) 0.041(3) -0.039(3)
    C16 0.079(4) 0.075(3) 0.076(3) 0.031(3) 0.040(3) -0.017(3)
    C17 0.048(3) 0.061(3) 0.058(3) 0.011(2) 0.018(2) 0.001(2)
    C18 0.041(2) 0.048(3) 0.032(2) 0.011(2) 0.010(2) -0.004(2)
    N20 0.053(3) 0.050(3) 0.067(3) 0.006(2) 0.018(2) -0.012(2)
    O21 0.143(3) 0.058(2) 0.185(4) 0.023(2) 0.104(3) 0.001(2)
    O22 0.143(3) 0.113(3) 0.119(3) -0.005(3) 0.089(3) -0.042(2)
    O23 0.052(2) 0.050(2) 0.080(2) -0.002(2) 0.005(2) 0.006(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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cu1 N1 . 1.899(3) yes
    Cu1 N1 2 1.899(3) ?
    Cu1 N8 . 1.983(3) yes
    Cu1 N8 2 1.983(3) ?
    Cu1 O23 . 2.541(3) yes
    Cu1 O23 2 2.541(3) ?
    N1 C5 . 1.256(4) ?
    N1 N2 . 1.377(3) ?
    N2 C3 . 1.211(4) ?
    C3 N4 . 1.373(4) ?
    C3 C13 . 1.452(4) ?
    N4 C5 . 1.313(4) ?
    N4 N6 . 1.318(3) ?
    C5 C7 . 1.462(5) ?
    N6 H62 . 0.96 ?
    N6 H61 . 0.97 ?
    C7 N8 . 1.267(3) ?
    C7 C12 . 1.303(4) ?
    N8 C9 . 1.350(4) ?
    C9 C10 . 1.322(4) ?
    C9 H9 . 0.93 ?
    C10 C11 . 1.266(4) ?
    C10 H10 . 0.93 ?
    C11 C12 . 1.402(4) ?
    C11 H11 . 0.93 ?
    C12 H12 . 0.93 ?
    C13 N14 . 1.236(4) ?
    C13 C18 . 1.352(5) ?
    N14 C15 . 1.317(4) ?
    C15 C16 . 1.361(5) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.254(4) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.368(4) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
    N20 O21 . 1.151(4) ?
    N20 O22 . 1.162(4) ?
    N20 O23 . 1.307(4) ?
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
    N1 Cu1 N1 . 2 180.0 yes
    N1 Cu1 N8 . . 86.10(10)
                          yes
    N1 Cu1 N8 . 2 93.90(10)
                          yes
    N1 Cu1 N8 2 . 93.90(10)
                          ?
    N1 Cu1 N8 2 2 86.10(10)
                          ?
    N1 Cu1 O23 . . 87.00(10)
                           yes
    N1 Cu1 O23 . 2 93.10(10)
                           yes
    N1 Cu1 O23 2 . 93.10(10)
                           ?
    N1 Cu1 O23 2 2 87.00(10)
                           ?
    N8 Cu1 N8 . 2 180.0 yes
    N8 Cu1 O23 . . 87.40(10)
                           yes
    N8 Cu1 O23 . 2 92.60(10)
                           yes
    N8 Cu1 O23 2 . 92.60(10)
                           ?
    N8 Cu1 O23 2 2 87.40(10)
                           ?
    O23 Cu1 O23 . 2 180.0 yes
    C5 N1 N2 . . 114.3(3) ?
    C5 N1 Cu1 . . 106.9(2) ?
    N2 N1 Cu1 . . 138.6(2) ?
    C3 N2 N1 . . 105.1(3) ?
    N2 C3 N4 . . 108.1(3) ?
    N2 C3 C13 . . 121.6(4) ?
    N4 C3 C13 . . 130.4(3) ?
    C5 N4 N6 . . 120.2(3) ?
    C5 N4 C3 . . 110.7(3) ?
    N6 N4 C3 . . 129.2(3) ?
    N1 C5 N4 . . 101.9(3) ?
    N1 C5 C7 . . 123.6(3) ?
    N4 C5 C7 . . 134.4(3) ?
    N4 N6 H62 . . 99 ?
    N4 N6 H61 . . 104 ?
    H62 N6 H61 . . 107 ?
    N8 C7 C12 . . 117.8(3) ?
    N8 C7 C5 . . 112.7(3) ?
    C12 C7 C5 . . 129.4(3) ?
    C7 N8 C9 . . 119.1(3) ?
    C7 N8 Cu1 . . 110.1(2) ?
    C9 N8 Cu1 . . 130.8(2) ?
    C10 C9 N8 . . 126.2(3) ?
    C10 C9 H9 . . 117 ?
    N8 C9 H9 . . 117 ?
    C11 C10 C9 . . 113.7(4) ?
    C11 C10 H10 . . 123 ?
    C9 C10 H10 . . 123 ?
    C10 C11 C12 . . 121.6(4) ?
    C10 C11 H11 . . 119 ?
    C12 C11 H11 . . 119 ?
    C7 C12 C11 . . 121.6(3) ?
    C7 C12 H12 . . 119 ?
    C11 C12 H12 . . 119 ?
    N14 C13 C18 . . 120.6(4) ?
    N14 C13 C3 . . 114.6(4) ?
    C18 C13 C3 . . 124.7(3) ?
    C13 N14 C15 . . 114.6(4) ?
    N14 C15 C16 . . 128.8(4) ?
    N14 C15 H15 . . 116 ?
    C16 C15 H15 . . 116 ?
    C17 C16 C15 . . 115.3(4) ?
    C17 C16 H16 . . 122 ?
    C15 C16 H16 . . 122 ?
    C16 C17 C18 . . 117.8(4) ?
    C16 C17 H17 . . 121 ?
    C18 C17 H17 . . 121 ?
    C13 C18 C17 . . 122.8(3) ?
    C13 C18 H18 . . 119 ?
    C17 C18 H18 . . 119 ?
    O21 N20 O22 . . 110.1(5) ?
    O21 N20 O23 . . 121.9(4) ?
    O22 N20 O23 . . 127.8(4) ?
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
    _geom_hbond_publ_flag
    N6 H61 N14 . 0.97 2.10 2.901(4) 139 yes
    C9 H9 N2 2_555 0.93 2.13 2.923(4) 143 yes
    N6 H62 O21 2_565 0.96 2.26 3.186(5) 161 yes
    C10 H10 O21 1_655 0.93 2.57 3.454(6) 160 yes
    C16 H16 O22 1_456 0.93 2.32 3.247(5) 173 yes
    C18 H18 O23 2_455 0.93 2.21 3.043(4) 149 yes
    C11 H11 O22 2_665 0.93 2.52 3.447(5) 172 yes
