#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/84/2238415.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_2238415
loop_
_publ_author_name
'Essid, Manel'
'Marouani, Houda'
'Al-Deyab, Salem S.'
'Rzaigui, Mohamed'
_publ_section_title
;
 5-Amino-1H-1,2,4-triazol-4-ium hydrogen oxalate
;
_journal_coeditor_code           PV2640
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1279
_journal_paper_doi               10.1107/S1600536813019363
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C2 H5 N4 +, C2 H O4 -'
_chemical_formula_moiety         'C2 H5 N4 +, C2 H O4 -'
_chemical_formula_sum            'C4 H6 N4 O4'
_chemical_formula_weight         174.13
_chemical_name_systematic        ?
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   23.093(4)
_cell_length_b                   23.093(4)
_cell_length_c                   6.603(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     3049.5(16)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56080
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3909
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.415
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0604
_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)+(0.0979P)²+1.6007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1940
_reflns_number_gt                1929
_reflns_number_total             3313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2640.cif
_cod_data_source_block           I
_cod_original_cell_volume        3049.3(16)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2238415
_cod_database_fobs_code          2238415
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_symmetry_multiplicity
O O1 0.35441(6) -0.03841(6) 0.4263(2) 0.0279(3) Uani d . 1 1
O O4 0.50310(6) -0.02945(6) 0.2759(2) 0.0304(3) Uani d . 1 1
O O3 0.46709(6) 0.04345(6) 0.2350(2) 0.0268(3) Uani d . 1 1
O O2 0.37748(7) -0.12148(6) 0.4035(3) 0.0384(4) Uani d . 1 1
N N3 0.40979(7) -0.14645(7) -0.1112(2) 0.0282(3) Uani d . 1 1
H H5 0.4515 -0.1183 -0.1295 0.034 Uiso calc R 1 1
N N1 0.36951(8) -0.06980(8) -0.0972(3) 0.0310(3) Uani d . 1 1
N N2 0.30499(7) -0.18848(8) -0.0659(3) 0.0308(3) Uani d . 1 1
H H4 0.2661 -0.1927 -0.0501 0.037 Uiso calc R 1 1
C C3 0.36142(7) -0.13134(8) -0.0947(2) 0.0228(3) Uani d . 1 1
C C2 0.46067(7) -0.01195(7) 0.2875(2) 0.0205(3) Uani d . 1 1
C C4 0.31868(9) -0.23999(9) -0.0656(3) 0.0338(4) Uani d . 1 1
H H6 0.2877 -0.2851 -0.0480 0.041 Uiso calc R 1 1
C C1 0.39246(8) -0.06374(7) 0.3785(2) 0.0217(3) Uani d . 1 1
N N4 0.38176(9) -0.21484(9) -0.0939(3) 0.0429(4) Uani d . 1 1
H H1 0.3155(15) -0.0699(15) 0.467(4) 0.054(8) Uiso d . 1 1
H H3 0.4074(14) -0.0368(14) -0.142(4) 0.049(7) Uiso d . 1 1
H H2 0.3342(14) -0.0667(12) -0.113(4) 0.039(6) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 -13 2
-11 8 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 110.1(19)
C3 N3 N4 108.56(14)
C3 N3 H5 125.7
N4 N3 H5 125.7
C3 N1 H3 118.4(19)
C3 N1 H2 117.1(17)
H3 N1 H2 118(2)
C3 N2 C4 108.94(14)
C3 N2 H4 125.5
C4 N2 H4 125.5
N2 C3 N3 106.69(14)
N2 C3 N1 127.24(15)
N3 C3 N1 126.00(15)
O4 C2 O3 127.23(15)
O4 C2 C1 116.06(13)
O3 C2 C1 116.71(13)
N4 C4 N2 107.94(15)
N4 C4 H6 126.0
N2 C4 H6 126.0
O2 C1 O1 124.85(15)
O2 C1 C2 121.67(14)
O1 C1 C2 113.47(12)
C4 N4 N3 107.86(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3143(19)
O1 H1 0.87(3)
O4 C2 1.2351(19)
O3 C2 1.2607(18)
O2 C1 1.2099(19)
N3 C3 1.331(2)
N3 N4 1.380(2)
N3 H5 0.8600
N1 C3 1.338(2)
N1 H3 0.88(3)
N1 H2 0.86(3)
N2 C3 1.325(2)
N2 C4 1.375(2)
N2 H4 0.8600
C2 C1 1.546(2)
C4 N4 1.284(3)
C4 H6 0.9300
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 H1 O3 6 0.87(3) 1.72(3) 2.5845(17) 174(3)
N1 H2 O1 6_554 0.86(3) 2.29(3) 3.087(2) 155(2)
N1 H3 O4 10_655 0.88(3) 2.06(3) 2.925(2) 171(3)
N2 H4 O4 15_445 0.86 2.09 2.892(2) 154.4
N2 H4 O2 15_445 0.86 2.28 2.878(2) 126.7
N3 H5 O3 10_655 0.86 1.94 2.7652(18) 161.0
C4 H6 N4 2_545 0.93 2.41 3.313(3) 164.9
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
C4 N2 C3 N3 -0.3(2)
C4 N2 C3 N1 -177.35(19)
N4 N3 C3 N2 0.6(2)
N4 N3 C3 N1 177.71(18)
C3 N2 C4 N4 -0.1(2)
O4 C2 C1 O2 -12.5(2)
O3 C2 C1 O2 168.06(17)
O4 C2 C1 O1 166.66(15)
O3 C2 C1 O1 -12.8(2)
N2 C4 N4 N3 0.5(2)
C3 N3 N4 C4 -0.7(2)
