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#$Date: 2025-08-20 22:19:29 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/79/4307957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4307957
loop_
_publ_author_name
'Juan P. García-Terán'
'Oscar Castillo'
'Antonio Luque'
'Urko García-Couceiro'
'Garikoitz Beobide'
'Pascual Román'
_publ_contact_author
;
 Oscar Castillo. Departamento de Quimica Inorganica. Facultad de Ciencias
 Universidad del Pais Vasco,  Apdo. 644, E-48080 Bilbao, Spain
;
_publ_contact_author_email       oscar.castillo@ehu.es
_publ_contact_author_fax         '+34-946 013 500'
_publ_contact_author_phone       '+34-946 015 991'
_publ_section_title
;
Molecular Recognition of Adeninium Cations on Anionic Metal-Oxalato
Frameworks: An Experimental and Theoretical Analysis
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3593
_journal_page_last               3602
_journal_paper_doi               10.1021/ic062448s
_journal_volume                  46
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C4 H2 Cu O9, 2(C5 H6 N5)'
_chemical_formula_structural     'C4 H2 Cu O9, 2(C5 H6 N5)'
_chemical_formula_sum            'C14 H14 Cu N10 O9'
_chemical_formula_weight         529.89
_chemical_name_systematic
;
adeninium aquabis(oxalato)cuprate(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                103.96(4)
_cell_angle_beta                 103.68(4)
_cell_angle_gamma                104.94(5)
_cell_formula_units_Z            2
_cell_length_a                   8.960(5)
_cell_length_b                   10.104(5)
_cell_length_c                   11.403(4)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.71
_cell_volume                     917.6(9)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir92 (Altamore et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.7733
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7974
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.273
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.170.32 (release 06.06.2003 CrysAlis170 VC++)
(compiled Jun  6 2003,13:53:32)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
;
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_meas      1.91(1)
_exptl_crystal_density_method    flotation
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4409
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.2686
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+11.2765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                888
_reflns_number_total             4409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062448ssi20061221_061210_1.cif
_cod_data_source_block           compound1
_cod_database_code               4307957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.09070(12) 0.35123(11) -0.01942(9) 0.0446(3) Uani 1 1 d . . .
O11 O 0.1146(5) 0.2611(5) 0.1106(4) 0.0340(13) Uani 1 1 d U . .
O12 O -0.1310(5) 0.2160(5) -0.0875(4) 0.0344(14) Uani 1 1 d U . .
O13 O -0.2856(5) 0.0305(5) -0.0460(4) 0.0382(13) Uani 1 1 d U . .
O14 O -0.0183(5) 0.0700(5) 0.1540(4) 0.0435(15) Uani 1 1 d U . .
C11 C -0.0125(8) 0.1512(7) 0.0891(6) 0.0249(19) Uani 1 1 d U . .
C12 C -0.1494(8) 0.1313(7) -0.0170(6) 0.0235(18) Uani 1 1 d U . .
O21 O 0.3014(4) 0.4968(4) 0.0600(3) 0.0347(13) Uani 1 1 d U . .
O22 O 0.0521(5) 0.4577(5) -0.1345(4) 0.0424(15) Uani 1 1 d U . .
O23 O 0.1925(5) 0.6403(5) -0.1853(4) 0.0446(14) Uani 1 1 d U . .
O24 O 0.4577(5) 0.6874(5) 0.0250(4) 0.0543(17) Uani 1 1 d U . .
C21 C 0.3332(8) 0.5898(7) 0.0011(6) 0.0246(19) Uani 1 1 d U . .
C22 C 0.1807(7) 0.5620(7) -0.1176(6) 0.0223(17) Uani 1 1 d U . .
O1W O 0.2056(5) 0.1930(4) -0.1343(4) 0.0551(15) Uani 1 1 d . . .
H11W H 0.1758 0.1031 -0.1415 0.083 Uiso 1 1 d . . .
H12W H 0.3035 0.1951 -0.1152 0.083 Uiso 1 1 d . . .
N1A N 0.5376(6) -0.0074(5) 0.2484(4) 0.0367(16) Uani 1 1 d U . .
H1A H 0.4576 -0.0331 0.1794 0.044 Uiso 1 1 calc R . .
C2A C 0.6661(7) 0.1043(7) 0.2684(6) 0.0347(19) Uani 1 1 d U . .
H2A H 0.6613 0.1501 0.2067 0.042 Uiso 1 1 calc R . .
N3A N 0.8015(6) 0.1582(6) 0.3671(5) 0.0384(16) Uani 1 1 d U . .
C4A C 0.7892(7) 0.0832(7) 0.4496(6) 0.0299(18) Uani 1 1 d U . .
C5A C 0.6627(8) -0.0357(7) 0.4383(6) 0.0264(17) Uani 1 1 d U . .
C6A C 0.5234(7) -0.0848(7) 0.3302(5) 0.0297(18) Uani 1 1 d U . .
N6A N 0.3932(6) -0.1952(5) 0.3055(4) 0.0359(16) Uani 1 1 d U . .
H62A H 0.3138 -0.2206 0.2361 0.043 Uiso 1 1 calc R . .
H61A H 0.3869 -0.2425 0.3585 0.043 Uiso 1 1 calc R . .
N7A N 0.6953(6) -0.0831(6) 0.5419(4) 0.0411(17) Uani 1 1 d U . .
C8A C 0.8409(8) 0.0091(7) 0.6107(6) 0.043(2) Uani 1 1 d U . .
H8A H 0.8963 0.0052 0.6891 0.052 Uiso 1 1 calc R . .
N9A N 0.9059(6) 0.1103(5) 0.5610(4) 0.0437(17) Uani 1 1 d U . .
H9A H 1.0000 0.1768 0.5930 0.052 Uiso 1 1 calc R . .
N1B N 1.4701(6) 0.5093(6) 0.7309(4) 0.0385(16) Uani 1 1 d U . .
H1B H 1.5526 0.5294 0.7969 0.046 Uiso 1 1 calc R . .
C2B C 1.3399(8) 0.3940(7) 0.7073(6) 0.0350(19) Uani 1 1 d U . .
H2B H 1.3465 0.3427 0.7649 0.042 Uiso 1 1 calc R . .
N3B N 1.2048(6) 0.3459(6) 0.6123(5) 0.0412(17) Uani 1 1 d U . .
C4B C 1.2166(7) 0.4295(7) 0.5358(6) 0.0292(18) Uani 1 1 d U . .
C5B C 1.3433(7) 0.5498(7) 0.5497(6) 0.0241(16) Uani 1 1 d U . .
C6B C 1.4803(8) 0.5977(7) 0.6563(6) 0.0315(19) Uani 1 1 d U . .
N6B N 1.6099(6) 0.7102(5) 0.6841(4) 0.0405(16) Uani 1 1 d U . .
H61B H 1.6918 0.7306 0.7506 0.049 Uiso 1 1 calc R . .
H62B H 1.6131 0.7638 0.6358 0.049 Uiso 1 1 calc R . .
N7B N 1.3089(6) 0.6059(5) 0.4505(4) 0.0328(16) Uani 1 1 d U . .
C8B C 1.1626(7) 0.5163(7) 0.3812(5) 0.0333(19) Uani 1 1 d U . .
H8B H 1.1045 0.5262 0.3065 0.040 Uiso 1 1 calc R . .
N9B N 1.1020(6) 0.4091(5) 0.4252(4) 0.0410(17) Uani 1 1 d U . .
H9B H 1.0091 0.3411 0.3903 0.049 Uiso 1 1 calc R . .
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
O22 Cu1 O21 86.27(17) . . ?
O22 Cu1 O11 171.4(3) . . ?
O21 Cu1 O11 94.13(18) . . ?
O22 Cu1 O12 93.82(18) . . ?
O21 Cu1 O12 174.0(3) . . ?
O11 Cu1 O12 84.89(17) . . ?
O22 Cu1 O1W 99.20(19) . . ?
O21 Cu1 O1W 90.34(18) . . ?
O11 Cu1 O1W 89.34(18) . . ?
O12 Cu1 O1W 95.59(18) . . ?
C11 O11 Cu1 112.6(4) . . ?
C12 O12 Cu1 109.0(3) . . ?
O14 C11 O11 123.5(6) . . ?
O14 C11 C12 121.9(6) . . ?
O11 C11 C12 114.6(6) . . ?
O13 C12 O12 120.1(5) . . ?
O13 C12 C11 121.4(6) . . ?
O12 C12 C11 118.5(6) . . ?
C21 O21 Cu1 114.2(3) . . ?
C22 O22 Cu1 111.9(4) . . ?
O24 C21 O21 128.8(5) . . ?
O24 C21 C22 120.0(6) . . ?
O21 C21 C22 111.2(6) . . ?
O23 C22 O22 125.0(5) . . ?
O23 C22 C21 119.1(6) . . ?
O22 C22 C21 115.9(6) . . ?
Cu1 O1W H11W 120.1 . . ?
Cu1 O1W H12W 127.8 . . ?
H11W O1W H12W 88.8 . . ?
C2A N1A C6A 124.1(5) . . ?
C2A N1A H1A 117.9 . . ?
C6A N1A H1A 117.9 . . ?
N1A C2A N3A 126.8(6) . . ?
N1A C2A H2A 116.6 . . ?
N3A C2A H2A 116.6 . . ?
C2A N3A C4A 109.8(5) . . ?
N3A C4A N9A 125.2(6) . . ?
N3A C4A C5A 128.5(5) . . ?
N9A C4A C5A 106.3(6) . . ?
N7A C5A C4A 111.5(5) . . ?
N7A C5A C6A 130.9(7) . . ?
C4A C5A C6A 117.5(6) . . ?
N6A C6A N1A 121.6(5) . . ?
N6A C6A C5A 125.2(6) . . ?
N1A C6A C5A 113.1(6) . . ?
C6A N6A H62A 120.0 . . ?
C6A N6A H61A 120.0 . . ?
H62A N6A H61A 120.0 . . ?
C8A N7A C5A 101.5(5) . . ?
N7A C8A N9A 116.2(5) . . ?
N7A C8A H8A 121.9 . . ?
N9A C8A H8A 121.9 . . ?
C8A N9A C4A 104.4(6) . . ?
C8A N9A H9A 127.8 . . ?
C4A N9A H9A 127.8 . . ?
C2B N1B C6B 124.2(5) . . ?
C2B N1B H1B 117.9 . . ?
C6B N1B H1B 117.9 . . ?
N3B C2B N1B 126.9(6) . . ?
N3B C2B H2B 116.6 . . ?
N1B C2B H2B 116.6 . . ?
C2B N3B C4B 109.2(6) . . ?
N9B C4B N3B 125.9(6) . . ?
N9B C4B C5B 104.9(6) . . ?
N3B C4B C5B 129.2(6) . . ?
C4B C5B C6B 118.1(6) . . ?
C4B C5B N7B 111.9(5) . . ?
C6B C5B N7B 130.0(6) . . ?
N6B C6B N1B 121.9(5) . . ?
N6B C6B C5B 125.7(6) . . ?
N1B C6B C5B 112.4(6) . . ?
C6B N6B H61B 120.0 . . ?
C6B N6B H62B 120.0 . . ?
H61B N6B H62B 120.0 . . ?
C8B N7B C5B 101.3(5) . . ?
N7B C8B N9B 115.6(5) . . ?
N7B C8B H8B 122.2 . . ?
N9B C8B H8B 122.2 . . ?
C8B N9B C4B 106.3(5) . . ?
C8B N9B H9B 126.9 . . ?
C4B N9B H9B 126.9 . . ?
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 O22 1.912(4) . ?
Cu1 O21 1.914(4) . ?
Cu1 O11 1.917(4) . ?
Cu1 O12 1.943(4) . ?
Cu1 O1W 2.411(5) . ?
O11 C11 1.294(7) . ?
O12 C12 1.314(6) . ?
O13 C12 1.281(6) . ?
O14 C11 1.229(6) . ?
C11 C12 1.436(7) . ?
O21 C21 1.294(6) . ?
O22 C22 1.283(7) . ?
O23 C22 1.235(6) . ?
O24 C21 1.205(6) . ?
C21 C22 1.588(8) . ?
O1W H11W 0.8557 . ?
O1W H12W 0.8458 . ?
N1A C2A 1.316(7) . ?
N1A C6A 1.362(6) . ?
N1A H1A 0.8600 . ?
C2A N3A 1.324(6) . ?
C2A H2A 0.9300 . ?
N3A C4A 1.350(7) . ?
C4A N9A 1.356(6) . ?
C4A C5A 1.378(8) . ?
C5A N7A 1.375(6) . ?
C5A C6A 1.408(7) . ?
C6A N6A 1.306(7) . ?
N6A H62A 0.8600 . ?
N6A H61A 0.8600 . ?
N7A C8A 1.312(6) . ?
C8A N9A 1.354(7) . ?
C8A H8A 0.9300 . ?
N9A H9A 0.8600 . ?
N1B C2B 1.338(7) . ?
N1B C6B 1.375(7) . ?
N1B H1B 0.8600 . ?
C2B N3B 1.303(7) . ?
C2B H2B 0.9300 . ?
N3B C4B 1.356(7) . ?
C4B N9B 1.356(6) . ?
C4B C5B 1.379(8) . ?
C5B C6B 1.387(7) . ?
C5B N7B 1.389(6) . ?
C6B N6B 1.309(7) . ?
N6B H61B 0.8600 . ?
N6B H62B 0.8600 . ?
N7B C8B 1.310(6) . ?
C8B N9B 1.345(6) . ?
C8B H8B 0.9300 . ?
N9B H9B 0.8600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H11W O14 0.86 1.89 2.677(6) 151.6 2
O1W H12W O24 0.85 2.03 2.780(6) 148.1 2_665
N1A H1A O13 0.86 1.90 2.736(6) 162.6 2
N6A H62A O12 0.86 2.08 2.911(6) 162.6 2
N6A H61A N7B 0.86 2.12 2.959(6) 164.2 1_445
N9A H9A N3B 0.86 2.09 2.913(7) 161.3 .
N1B H1B O21 0.86 1.95 2.776(6) 159.3 2_766
N6B H61B O11 0.86 2.02 2.869(6) 168.5 2_766
N6B H62B N7A 0.86 2.16 2.995(7) 163.5 1_665
N9B H9B N3A 0.86 2.17 2.990(7) 159.6 .
C8A H8A O14 0.93 2.26 3.168(8) 163.6 2_656
C2A H2A O23 0.93 2.29 3.037(9) 137.4 2_665
C8B H8B O22 0.93 2.19 3.121(7) 175.0 2_665
C2B H2B O1W 0.93 2.40 3.221(8) 147.6 1_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139129069
