#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/24/2232462.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232462
loop_
_publ_author_name
'Caballero, Ana B.'
'Castillo, Óscar'
'Rodríguez-Diéguez, Antonio'
'Salas, Juan M.'
_publ_section_title
;
 Bis(7-amino-1,2,4-triazolo[1,5-a]pyrimidin-4-ium)
 bis(oxalato-κ²O¹,O²)cuprate(II) dihydrate
;
_journal_coeditor_code           SU2318
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1531
_journal_page_last               m1532
_journal_paper_doi               10.1107/S1600536811040724
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '(C5 H6 N5)2 [Cu (C2 O4)2], 2H2 O'
_chemical_formula_moiety         '2(C5 H6 N5 +), C4 Cu O8 2-, 2(H2 O)'
_chemical_formula_sum            'C14 H16 Cu N10 O10'
_chemical_formula_weight         547.91
_chemical_name_systematic
;
Bis(7-amino-1,2,4-triazolo[1,5-a]pyrimidin-4-ium)
bis(oxalato-κ²O¹,O²)cuprate(II) dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.344(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.6599(2)
_cell_length_b                   24.1977(10)
_cell_length_c                   11.1963(5)
_cell_measurement_reflns_used    8945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.11
_cell_volume                     990.73(8)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8945
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             558
_exptl_crystal_size_max          0.5896
_exptl_crystal_size_mid          0.0724
_exptl_crystal_size_min          0.0515
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.424
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0369
_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)+(0.0552P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                1476
_reflns_number_total             2170
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2318.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232462
_cod_database_fobs_code          2232462
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cu Cu1 0.50000 0.00000 1.00000 0.0235(2) Uani d S 1.000
O O1 0.8421(5) 0.03719(7) 1.10908(16) 0.0295(6) Uani d . 1.000
O O2 1.0514(6) 0.12235(8) 1.14517(17) 0.0308(7) Uani d . 1.000
O O3 0.6886(6) 0.15536(7) 0.93468(16) 0.0305(7) Uani d . 1.000
O O4 0.4741(5) 0.06976(7) 0.91704(15) 0.0238(6) Uani d . 1.000
C C1 0.8723(7) 0.08907(11) 1.0863(2) 0.0203(8) Uani d . 1.000
C C2 0.6629(8) 0.10777(10) 0.9703(2) 0.0209(8) Uani d . 1.000
N N1A 0.7487(7) 0.11549(9) 0.4729(2) 0.0255(7) Uani d . 1.000
N N3A 0.6315(6) 0.20038(10) 0.39005(19) 0.0259(7) Uani d . 1.000
N N4A 0.9285(6) 0.25338(9) 0.5496(2) 0.0230(7) Uani d . 1.000
N N7A 1.1147(7) 0.10032(9) 0.6956(2) 0.0297(8) Uani d . 1.000
N N8A 0.8882(6) 0.15695(8) 0.54508(18) 0.0193(7) Uani d . 1.000
C C2A 0.6026(8) 0.14399(12) 0.3835(2) 0.0264(9) Uani d . 1.000
C C3A 0.8143(8) 0.20707(10) 0.4929(2) 0.0203(8) Uani d . 1.000
C C5A 1.1084(8) 0.24886(11) 0.6569(2) 0.0250(9) Uani d . 1.000
C C6A 1.1821(8) 0.19969(11) 0.7099(2) 0.0238(8) Uani d . 1.000
C C7A 1.0687(7) 0.15005(11) 0.6543(2) 0.0215(8) Uani d . 1.000
O O1W 0.9004(13) -0.00801(11) 0.6425(3) 0.1037(16) Uani d . 1.000
H H2A 0.48460 0.12670 0.31850 0.0320 Uiso c R 1.000
H H4A 0.88760 0.28530 0.51800 0.0280 Uiso c R 1.000
H H5A 1.18500 0.28100 0.69600 0.0300 Uiso c R 1.000
H H6A 1.30870 0.19870 0.78360 0.0290 Uiso c R 1.000
H H71A 1.22680 0.09520 0.76370 0.0360 Uiso c R 1.000
H H72A 1.03300 0.07250 0.65480 0.0360 Uiso c R 1.000
H H11W 1.00140 -0.03050 0.59390 0.1560 Uiso d . 1.000
H H12W 0.95310 -0.02300 0.71050 0.1560 Uiso d . 1.000
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 Cu1 O4 . . 85.10(7) no
O1 Cu1 O1 . 1_455 96.74(6) no
O1 Cu1 O1 . 3_657 180.00 no
O1 Cu1 O4 . 3_657 94.90(7) no
O1 Cu1 O1 . 3_757 83.26(6) no
O1 Cu1 O4 1_455 . 84.58(6) no
O1 Cu1 O4 3_657 . 94.90(7) no
O4 Cu1 O4 . 3_657 180.00 no
O1 Cu1 O4 3_757 . 95.43(6) no
O1 Cu1 O1 1_455 3_657 83.26(6) no
O1 Cu1 O4 1_455 3_657 95.43(6) no
O1 Cu1 O1 1_455 3_757 180.00 no
O1 Cu1 O4 3_657 3_657 85.10(7) no
O1 Cu1 O1 3_657 3_757 96.74(6) no
O1 Cu1 O4 3_757 3_657 84.58(6) no
Cu1 O1 C1 . . 112.79(15) no
Cu1 O1 Cu1 . 1_655 96.74(7) no
Cu1 O1 C1 1_655 . 98.07(15) no
Cu1 O4 C2 . . 112.90(15) no
H11W O1W H12W . . 102.00 no
N8A N1A C2A . . 101.3(2) no
C2A N3A C3A . . 101.8(2) no
C3A N4A C5A . . 118.9(2) no
C3A N8A C7A . . 124.5(2) no
N1A N8A C3A . . 109.5(2) no
N1A N8A C7A . . 126.0(2) no
C3A N4A H4A . . 121.00 no
C5A N4A H4A . . 121.00 no
H71A N7A H72A . . 120.00 no
C7A N7A H72A . . 120.00 no
C7A N7A H71A . . 120.00 no
O1 C1 O2 . . 126.0(2) no
O2 C1 C2 . . 119.9(2) no
O1 C1 C2 . . 114.1(2) no
O3 C2 C1 . . 120.4(2) no
O4 C2 C1 . . 114.8(2) no
O3 C2 O4 . . 124.8(2) no
N1A C2A N3A . . 117.0(2) no
N3A C3A N4A . . 130.6(2) no
N4A C3A N8A . . 119.0(2) no
N3A C3A N8A . . 110.4(2) no
N4A C5A C6A . . 122.9(2) no
C5A C6A C7A . . 120.5(2) no
N8A C7A C6A . . 114.3(2) no
N7A C7A C6A . . 127.0(2) no
N7A C7A N8A . . 118.7(2) no
N3A C2A H2A . . 121.00 no
N1A C2A H2A . . 121.00 no
N4A C5A H5A . . 119.00 no
C6A C5A H5A . . 119.00 no
C5A C6A H6A . . 120.00 no
C7A C6A H6A . . 120.00 no
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 . 1.9349(18) no
Cu1 O4 . 1.9272(17) no
Cu1 O1 1_455 2.8879(18) no
Cu1 O1 3_657 1.9349(18) no
Cu1 O4 3_657 1.9272(17) no
Cu1 O1 3_757 2.8879(18) no
O1 C1 . 1.287(3) no
O2 C1 . 1.215(3) no
O3 C2 . 1.224(3) no
O4 C2 . 1.283(3) no
O1W H11W . 0.8600 no
O1W H12W . 0.8600 no
N1A C2A . 1.311(3) no
N1A N8A . 1.374(3) no
N3A C3A . 1.318(3) no
N3A C2A . 1.370(4) no
N4A C5A . 1.351(3) no
N4A C3A . 1.346(3) no
N7A C7A . 1.298(3) no
N8A C3A . 1.368(3) no
N8A C7A . 1.376(3) no
N4A H4A . 0.8600 no
N7A H72A . 0.8600 no
N7A H71A . 0.8600 no
C1 C2 . 1.548(3) no
C5A C6A . 1.352(4) no
C6A C7A . 1.408(4) no
C2A H2A . 0.9300 no
C5A H5A . 0.9300 no
C6A H6A . 0.9300 no
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
N4A H4A O3 4_554 0.86 1.85 2.685(3) 165 yes
O1W H11W N1A 3_756 0.86 2.38 3.197(4) 157 yes
O1W H12W O1 3_757 0.86 2.15 2.985(4) 163 yes
N7A H71A O4 1_655 0.86 2.00 2.856(3) 170 yes
N7A H72A O1W . 0.86 2.01 2.793(4) 151 yes
N7A H72A N1A . 0.86 2.48 2.806(3) 103 no
C2A H2A O2 1_454 0.93 2.46 3.320(3) 154 yes
C5A H5A O2 4_554 0.93 2.45 3.126(3) 129 yes
C6A H6A O3 1_655 0.93 2.39 3.246(3) 153 yes
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_4
_geom_torsion
_geom_torsion_publ_flag
O4 Cu1 O1 C1 . . 5.64(17) no
O4 Cu1 O1 Cu1 . 1_655 -96.07(7) no
O1 Cu1 O1 C1 1_455 . -78.29(17) no
O4 Cu1 O1 C1 3_657 . -174.36(17) no
O1 Cu1 O1 C1 3_757 . 101.71(17) no
O1 Cu1 O4 C2 . . -3.55(18) no
O1 Cu1 O4 C2 1_455 . 93.71(18) no
O1 Cu1 O4 C2 3_657 . 176.45(18) no
O1 Cu1 O4 C2 3_757 . -86.29(18) no
Cu1 O1 C1 O2 . . 175.4(2) no
Cu1 O1 C1 C2 . . -6.3(3) no
Cu1 O1 C1 O2 1_655 . -83.8(3) no
Cu1 O1 C1 C2 1_655 . 94.6(2) no
Cu1 O4 C2 O3 . . 180.0(2) no
Cu1 O4 C2 C1 . . 1.1(3) no
N8A N1A C2A N3A . . -0.2(3) no
C2A N1A N8A C3A . . 0.0(3) no
C2A N1A N8A C7A . . 178.8(2) no
C3A N3A C2A N1A . . 0.4(3) no
C2A N3A C3A N4A . . 180.0(3) no
C2A N3A C3A N8A . . -0.3(3) no
C5A N4A C3A N3A . . 178.9(3) no
C3A N4A C5A C6A . . 0.5(4) no
C5A N4A C3A N8A . . -0.8(4) no
C7A N8A C3A N4A . . 1.2(4) no
C3A N8A C7A C6A . . -1.1(4) no
C7A N8A C3A N3A . . -178.6(2) no
N1A N8A C3A N3A . . 0.3(3) no
N1A N8A C3A N4A . . 180.0(2) no
N1A N8A C7A C6A . . -179.7(2) no
N1A N8A C7A N7A . . -0.3(4) no
C3A N8A C7A N7A . . 178.4(3) no
O2 C1 C2 O4 . . -178.0(2) no
O2 C1 C2 O3 . . 3.1(4) no
O1 C1 C2 O3 . . -175.4(2) no
O1 C1 C2 O4 . . 3.6(3) no
N4A C5A C6A C7A . . -0.5(4) no
C5A C6A C7A N7A . . -178.7(3) no
C5A C6A C7A N8A . . 0.8(4) no
