##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-04-29
_journal_date_accepted     2007-05-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     m1598
_journal_page_last     m1598
_journal_paper_category     QM
_journal_coeditor_code     LH2382
_publ_contact_author_name     'Dr. Duane Choquesillo-Lazarte'
_publ_contact_author_address
;
Laboratorio de Estudios Cristalográficos,
IACT - CSIC,
P. T. Ciencias de la Salud, Granada 18100,
Spain
;
_publ_contact_author_email     duanec@ugr.es
_publ_contact_author_fax     '+34 958181632'
_publ_contact_author_phone     '+34 958181644'
_publ_section_title
;\
A redetermination of
(N⁹-adenine-κN)aqua[glycylglycinato(2-)-κ³N,\
N',O]copper(II)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Brandi-Blanco, María Pilar' .
;
Departamento de Química Inorgánica,
Facultad de Farmacia, Universidad de Granada
c/ Campus de Cartuja s/n, 18071 Granada, Spain
;
    'Dumet-Fernandes, Bruno' .
;
Departamento de Química Inorgánica,
Facultad de Farmacia, Universidad de Granada
c/ Campus de Cartuja s/n, 18071 Granada, Spain
;
    'González-Pérez, Josefa María' .
;
Departamento de Química Inorgánica,
Facultad de Farmacia, Universidad de Granada
c/ Campus de Cartuja s/n, 18071 Granada, Spain
;
    'Choquesillo-Lazarte, Duane' .
;
Laboratorio de Estudios Cristalográficos,
IACT--CSIC,
P. T. Ciencias de la Salud, Granada 18100,
Spain
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(N⁹-adenine-κN)aqua[glycylglycinato(2-)-\
κ³N,N',O]copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H13 Cu N7 O4'
_chemical_formula_sum     'C9 H13 Cu N7 O4'
_chemical_formula_iupac     '[Cu (C4 H6 N2 O3) (C5 H5 N5) (H2 O)]'
_chemical_formula_weight     346.80
_chemical_melting_point     ?
_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     6.919(3)
_cell_length_b     7.617(3)
_cell_length_c     12.060(5)
_cell_angle_alpha     93.213(7)
_cell_angle_beta     94.640(6)
_cell_angle_gamma     94.614(7)
_cell_volume     630.2(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     806
_cell_measurement_theta_min     2.69
_cell_measurement_theta_max     28.45
_cell_measurement_temperature     273(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.828
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     354
_exptl_absorpt_coefficient_mu     1.764
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.5937
_exptl_absorpt_correction_T_max     0.8718
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(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     'Bruker SMART 1000'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6720
_diffrn_reflns_av_R_equivalents     0.0676
_diffrn_reflns_av_sigmaI/netI     0.0940
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     15
_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     2566
_reflns_number_gt     1816
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0921
_refine_ls_R_factor_gt     0.0591
_refine_ls_wR_factor_gt     0.1459
_refine_ls_wR_factor_ref     0.1660
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     2566
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0870P)²+0.0000P] where P=(Fo²+2Fc²)/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     0.987
_refine_diff_density_min     -1.405
_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 (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'publCIF (Westrip, 2007)'
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 0.36815(9) 0.28116(9) 0.21733(5) 0.0320(3) Uani d . 1 . .
    N N1 -0.3262(6) 0.0393(6) 0.3990(3) 0.0308(10) Uani d . 1 . .
    C C2 -0.2523(8) 0.0108(8) 0.3017(4) 0.0337(13) Uani d . 1 . .
    H H2 -0.3304 -0.0627 0.2490 0.040 Uiso calc R 1 . .
    N N3 -0.0810(6) 0.0733(6) 0.2693(3) 0.0336(11) Uani d . 1 . .
    C C4 0.0252(7) 0.1750(7) 0.3516(4) 0.0244(10) Uani d . 1 . .
    C C5 -0.0351(7) 0.2129(7) 0.4549(4) 0.0255(11) Uani d . 1 . .
    C C6 -0.2217(7) 0.1437(7) 0.4798(4) 0.0282(11) Uani d . 1 . .
    N N6 -0.3000(7) 0.1763(7) 0.5760(4) 0.0415(12) Uani d . 1 . .
    H H6A -0.2466 0.2336 0.6363 0.050 Uiso d R 1 . .
    H H6B -0.3954 0.1102 0.5982 0.050 Uiso d R 1 . .
    N N7 0.1150(6) 0.3158(6) 0.5138(3) 0.0313(10) Uani d . 1 . .
    H H7 0.1034 0.3582 0.5842 0.038 Uiso d R 1 . .
    C C8 0.2554(8) 0.3370(7) 0.4460(4) 0.0345(13) Uani d . 1 . .
    H H8 0.3733 0.4029 0.4664 0.041 Uiso calc R 1 . .
    N N9 0.2114(6) 0.2550(6) 0.3458(3) 0.0295(10) Uani d . 1 . .
    N N11 0.5310(6) 0.2917(6) 0.0976(3) 0.0334(11) Uani d . 1 . .
    C C11 0.7143(8) 0.3996(7) 0.1182(4) 0.0324(12) Uani d . 1 . .
    H H11A 0.7187 0.4940 0.0675 0.039 Uiso calc R 1 . .
    H H11B 0.8218 0.3285 0.1064 0.039 Uiso calc R 1 . .
    C C12 0.7302(7) 0.4758(7) 0.2375(4) 0.0297(11) Uani d . 1 . .
    O O11 0.5924(5) 0.4369(5) 0.2984(3) 0.0368(9) Uani d . 1 . .
    O O12 0.8795(5) 0.5740(5) 0.2714(3) 0.0413(10) Uani d . 1 . .
    C C21 0.4650(8) 0.2204(7) -0.0009(4) 0.0335(13) Uani d . 1 . .
    O O13 0.5490(6) 0.2262(5) -0.0904(3) 0.0445(11) Uani d . 1 . .
    C C22 0.2650(8) 0.1224(8) -0.0016(4) 0.0400(14) Uani d . 1 . .
    H H22A 0.1673 0.1927 -0.0347 0.048 Uiso calc R 1 . .
    H H22B 0.2606 0.0119 -0.0462 0.048 Uiso calc R 1 . .
    N N12 0.2224(7) 0.0868(6) 0.1136(4) 0.0387(12) Uani d . 1 . .
    H H12A 0.0982 0.0717 0.1181 0.046 Uiso d R 1 . .
    H H12B 0.2639 -0.0105 0.1358 0.046 Uiso d R 1 . .
    O O1 0.1997(7) 0.5145(7) 0.1604(5) 0.0747(17) Uani d . 1 . .
    H H1A 0.1943 0.5830 0.2159 0.090 Uiso d R 1 . .
    H H1B 0.2392 0.5803 0.1138 0.090 Uiso d 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 0.0182(4) 0.0414(5) 0.0332(4) -0.0137(3) 0.0056(2) -0.0064(3)
    N1 0.018(2) 0.038(3) 0.034(2) -0.0133(19) 0.0031(17) 0.0008(19)
    C2 0.021(3) 0.045(3) 0.031(3) -0.014(2) -0.001(2) -0.004(2)
    N3 0.021(2) 0.045(3) 0.030(2) -0.018(2) 0.0017(17) -0.0037(19)
    C4 0.016(2) 0.026(3) 0.029(2) -0.008(2) -0.0010(18) 0.001(2)
    C5 0.014(2) 0.030(3) 0.031(3) -0.007(2) -0.0001(18) 0.003(2)
    C6 0.019(3) 0.037(3) 0.029(2) -0.004(2) 0.0048(19) 0.007(2)
    N6 0.030(3) 0.061(3) 0.030(2) -0.018(2) 0.0086(19) -0.005(2)
    N7 0.021(2) 0.037(3) 0.032(2) -0.015(2) -0.0001(17) -0.0038(18)
    C8 0.024(3) 0.041(3) 0.037(3) -0.011(2) 0.005(2) 0.001(2)
    N9 0.015(2) 0.038(3) 0.033(2) -0.0133(19) 0.0028(17) -0.0002(18)
    N11 0.022(2) 0.043(3) 0.032(2) -0.016(2) 0.0040(18) -0.0038(19)
    C11 0.021(3) 0.044(3) 0.030(3) -0.011(2) 0.005(2) -0.004(2)
    C12 0.019(3) 0.037(3) 0.032(3) -0.004(2) 0.004(2) -0.004(2)
    O11 0.0220(19) 0.054(3) 0.0317(19) -0.0125(17) 0.0090(15) -0.0059(17)
    O12 0.025(2) 0.055(3) 0.038(2) -0.0212(19) 0.0083(16) -0.0134(18)
    C21 0.025(3) 0.039(3) 0.033(3) -0.012(2) 0.001(2) -0.006(2)
    O13 0.038(2) 0.057(3) 0.034(2) -0.019(2) 0.0083(17) -0.0069(18)
    C22 0.024(3) 0.049(4) 0.041(3) -0.017(3) -0.001(2) -0.009(3)
    N12 0.025(2) 0.044(3) 0.044(3) -0.014(2) 0.010(2) -0.010(2)
    O1 0.043(3) 0.084(4) 0.107(4) 0.012(3) 0.033(3) 0.044(3)
_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 N11 . 1.903(4) ?
    Cu1 N9 . 1.972(4) ?
    Cu1 O11 . 2.024(4) ?
    Cu1 N12 . 2.030(4) ?
    Cu1 O1 . 2.309(5) ?
    N1 C2 . 1.331(6) ?
    N1 C6 . 1.346(7) ?
    C2 N3 . 1.337(6) ?
    C2 H2 . 0.9300 ?
    N3 C4 . 1.352(6) ?
    C4 C5 . 1.369(6) ?
    C4 N9 . 1.389(6) ?
    C5 N7 . 1.373(6) ?
    C5 C6 . 1.416(6) ?
    C6 N6 . 1.339(6) ?
    N6 H6A . 0.8669 ?
    N6 H6B . 0.8663 ?
    N7 C8 . 1.326(6) ?
    N7 H7 . 0.9031 ?
    C8 N9 . 1.330(7) ?
    C8 H8 . 0.9300 ?
    N11 C21 . 1.310(7) ?
    N11 C11 . 1.451(6) ?
    C11 C12 . 1.513(7) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 O12 . 1.252(6) ?
    C12 O11 . 1.276(6) ?
    C21 O13 . 1.268(6) ?
    C21 C22 . 1.518(7) ?
    C22 N12 . 1.479(7) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    N12 H12A . 0.8640 ?
    N12 H12B . 0.8644 ?
    O1 H1A . 0.8305 ?
    O1 H1B . 0.8219 ?
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
    N11 Cu1 N9 . . 175.42(19) ?
    N11 Cu1 O11 . . 82.58(16) ?
    N9 Cu1 O11 . . 96.86(15) ?
    N11 Cu1 N12 . . 81.47(18) ?
    N9 Cu1 N12 . . 98.07(17) ?
    O11 Cu1 N12 . . 159.99(17) ?
    N11 Cu1 O1 . . 93.39(19) ?
    N9 Cu1 O1 . . 91.19(17) ?
    O11 Cu1 O1 . . 94.36(19) ?
    N12 Cu1 O1 . . 98.6(2) ?
    C2 N1 C6 . . 119.2(4) ?
    N1 C2 N3 . . 128.9(5) ?
    N1 C2 H2 . . 115.6 ?
    N3 C2 H2 . . 115.6 ?
    C2 N3 C4 . . 111.7(4) ?
    N3 C4 C5 . . 124.6(4) ?
    N3 C4 N9 . . 126.0(4) ?
    C5 C4 N9 . . 109.4(4) ?
    C4 C5 N7 . . 106.5(4) ?
    C4 C5 C6 . . 119.2(5) ?
    N7 C5 C6 . . 134.3(5) ?
    N6 C6 N1 . . 118.7(5) ?
    N6 C6 C5 . . 124.9(5) ?
    N1 C6 C5 . . 116.4(4) ?
    C6 N6 H6A . . 128.6 ?
    C6 N6 H6B . . 123.3 ?
    H6A N6 H6B . . 104.3 ?
    C8 N7 C5 . . 106.7(4) ?
    C8 N7 H7 . . 132.5 ?
    C5 N7 H7 . . 120.8 ?
    N7 C8 N9 . . 113.5(5) ?
    N7 C8 H8 . . 123.3 ?
    N9 C8 H8 . . 123.3 ?
    C8 N9 C4 . . 104.0(4) ?
    C8 N9 Cu1 . . 125.0(3) ?
    C4 N9 Cu1 . . 130.4(3) ?
    C21 N11 C11 . . 123.2(4) ?
    C21 N11 Cu1 . . 119.5(4) ?
    C11 N11 Cu1 . . 116.8(3) ?
    N11 C11 C12 . . 108.1(4) ?
    N11 C11 H11A . . 110.1 ?
    C12 C11 H11A . . 110.1 ?
    N11 C11 H11B . . 110.1 ?
    C12 C11 H11B . . 110.1 ?
    H11A C11 H11B . . 108.4 ?
    O12 C12 O11 . . 123.4(5) ?
    O12 C12 C11 . . 117.8(4) ?
    O11 C12 C11 . . 118.8(5) ?
    C12 O11 Cu1 . . 113.6(3) ?
    O13 C21 N11 . . 127.3(5) ?
    O13 C21 C22 . . 119.7(5) ?
    N11 C21 C22 . . 113.0(4) ?
    N12 C22 C21 . . 109.9(4) ?
    N12 C22 H22A . . 109.7 ?
    C21 C22 H22A . . 109.7 ?
    N12 C22 H22B . . 109.7 ?
    C21 C22 H22B . . 109.7 ?
    H22A C22 H22B . . 108.2 ?
    C22 N12 Cu1 . . 107.8(3) ?
    C22 N12 H12A . . 110.4 ?
    Cu1 N12 H12A . . 116.1 ?
    C22 N12 H12B . . 113.6 ?
    Cu1 N12 H12B . . 105.5 ?
    H12A N12 H12B . . 103.5 ?
    Cu1 O1 H1A . . 107.6 ?
    Cu1 O1 H1B . . 121.9 ?
    H1A O1 H1B . . 103.0 ?
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
    O1 H1B O13 2_665 0.82 2.04 2.740(6) 142.6
    O1 H1A O12 1_455 0.83 2.33 2.735(6) 110.9
    N12 H12B O13 2_655 0.86 2.24 2.978(7) 142.9
    N12 H12A N3 . 0.86 2.29 2.927(6) 130.9
    N7 H7 O12 2_666 0.90 1.78 2.674(5) 169.8
    N6 H6B N1 2_456 0.87 2.16 2.996(6) 161.6
