##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1407396'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
5-Amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C2 H5 N4 +, C5 H3 N2 O2 -'
_chemical_formula_sum     'C7 H8 N6 O2'
_chemical_formula_iupac     'C2 H5 N4 +, C5 H3 N2 O2 -'
_chemical_formula_weight     208.19
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.0599(5)
_cell_length_b     12.1868(8)
_cell_length_c     10.8385(6)
_cell_angle_alpha     90
_cell_angle_beta     103.593(4)
_cell_angle_gamma     90
_cell_volume     906.40(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1298
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     19.68
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.090
_exptl_crystal_size_mid     0.040
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.526
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     0.118
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1998)
;
_shelx_estimated_absorpt_T_min     0.989
_shelx_estimated_absorpt_T_max     0.996
_exptl_absorpt_correction_T_min     0.9894
_exptl_absorpt_correction_T_max     0.9965
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device_type     'Bruker X8 Kappa CCD APEXII'
_diffrn_measurement_method     'ω / φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12089
_diffrn_reflns_av_R_equivalents     0.0766
_diffrn_reflns_theta_min     2.556
_diffrn_reflns_theta_max     26.363
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     1858
_reflns_number_gt     1037
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1291
_refine_ls_R_factor_gt     0.0587
_refine_ls_wR_factor_gt     0.1100
_refine_ls_wR_factor_ref     0.1333
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     3.784
_refine_ls_number_reflns     1858
_refine_ls_number_parameters     148
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.188
_refine_diff_density_min     -0.196
_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'
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2005)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2005)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.2890(3) 0.79063(17) 0.49872(19) 0.0389(6) Uani d 1 . .
    N N2 0.0664(3) 0.79145(18) 0.2472(2) 0.0468(6) Uani d 1 . .
    C C1 0.2177(4) 0.8840(2) 0.4404(2) 0.0334(6) Uani d 1 . .
    C C2 0.1066(4) 0.8815(2) 0.3165(2) 0.0412(7) Uani d 1 . .
    H H2 0.0571 0.9476 0.2797 0.049 Uiso calc 1 . .
    C C3 0.1381(4) 0.6995(2) 0.3059(2) 0.0448(7) Uani d 1 . .
    H H3 0.1147 0.6334 0.2623 0.054 Uiso calc 1 . .
    C C4 0.2461(4) 0.6993(2) 0.4297(3) 0.0442(7) Uani d 1 . .
    H H4 0.2912 0.6326 0.4668 0.053 Uiso calc 1 . .
    C C5 0.2560(4) 0.9921(2) 0.5101(2) 0.0378(7) Uani d 1 . .
    O O1 0.1745(3) 1.07442(14) 0.45075(15) 0.0481(6) Uani d 1 . .
    O O2 0.3628(3) 0.99415(14) 0.61986(16) 0.0543(6) Uani d 1 . .
    N N3 0.7128(4) 0.94320(19) 0.8957(2) 0.0622(8) Uani d 1 . .
    N N4 0.6167(4) 0.88117(19) 0.7929(2) 0.0476(6) Uani d 1 . .
    H H4A 0.535(3) 0.912(2) 0.7253(18) 0.071 Uiso d 1 . .
    N N5 0.7480(3) 0.76575(18) 0.93596(19) 0.0417(6) Uani d 1 . .
    H H5 0.778(4) 0.6996(13) 0.972(2) 0.063 Uiso d 1 . .
    N N6 0.5628(4) 0.6942(2) 0.7405(2) 0.0540(7) Uani d 1 . .
    H H6A 0.473(3) 0.714(2) 0.6709(19) 0.081 Uiso d 1 . .
    H H6B 0.585(5) 0.6271(13) 0.775(3) 0.081 Uiso d 1 . .
    C C6 0.6369(4) 0.7751(2) 0.8181(2) 0.0365(7) Uani d 1 . .
    C C7 0.7892(5) 0.8695(2) 0.9782(3) 0.0553(8) Uani d 1 . .
    H H7 0.8649 0.8861 1.0584 0.066 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C4 . 1.335(3) ?
    N1 C1 . 1.341(3) ?
    N2 C2 . 1.323(3) ?
    N2 C3 . 1.328(3) ?
    C1 C2 . 1.387(3) ?
    C1 C5 . 1.512(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.379(4) ?
    C3 H3 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C5 O2 . 1.250(2) ?
    C5 O1 . 1.256(3) ?
    N3 C7 . 1.293(3) ?
    N3 N4 . 1.384(3) ?
    N4 C6 . 1.322(3) ?
    N4 H4A . 0.902(10) ?
    N5 C6 . 1.338(3) ?
    N5 C7 . 1.353(3) ?
    N5 H5 . 0.901(10) ?
    N6 C6 . 1.321(3) ?
    N6 H6A . 0.899(10) ?
    N6 H6B . 0.896(10) ?
    C7 H7 . 0.9300 ?
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
    C4 N1 C1 . . 115.6(2) ?
    C2 N2 C3 . . 114.9(2) ?
    N1 C1 C2 . . 120.2(2) ?
    N1 C1 C5 . . 120.1(2) ?
    C2 C1 C5 . . 119.8(2) ?
    N2 C2 C1 . . 124.4(2) ?
    N2 C2 H2 . . 117.8 ?
    C1 C2 H2 . . 117.8 ?
    N2 C3 C4 . . 122.0(2) ?
    N2 C3 H3 . . 119.0 ?
    C4 C3 H3 . . 119.0 ?
    N1 C4 C3 . . 123.0(2) ?
    N1 C4 H4 . . 118.5 ?
    C3 C4 H4 . . 118.5 ?
    O2 C5 O1 . . 125.0(2) ?
    O2 C5 C1 . . 119.3(2) ?
    O1 C5 C1 . . 115.7(2) ?
    C7 N3 N4 . . 102.9(2) ?
    C6 N4 N3 . . 111.1(2) ?
    C6 N4 H4A . . 126(2) ?
    N3 N4 H4A . . 121.7(19) ?
    C6 N5 C7 . . 105.9(2) ?
    C6 N5 H5 . . 121.3(18) ?
    C7 N5 H5 . . 132.7(18) ?
    C6 N6 H6A . . 115(2) ?
    C6 N6 H6B . . 115(2) ?
    H6A N6 H6B . . 128(3) ?
    N6 C6 N4 . . 126.2(2) ?
    N6 C6 N5 . . 126.9(2) ?
    N4 C6 N5 . . 106.9(2) ?
    N3 C7 N5 . . 113.2(2) ?
    N3 C7 H7 . . 123.4 ?
    N5 C7 H7 . . 123.4 ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 N1 C1 C2 . . . . 0.3(4) ?
    C4 N1 C1 C5 . . . . 179.5(2) ?
    C3 N2 C2 C1 . . . . 1.2(4) ?
    N1 C1 C2 N2 . . . . -1.4(4) ?
    C5 C1 C2 N2 . . . . 179.4(2) ?
    C2 N2 C3 C4 . . . . -0.1(4) ?
    C1 N1 C4 C3 . . . . 0.8(4) ?
    N2 C3 C4 N1 . . . . -1.0(4) ?
    N1 C1 C5 O2 . . . . 3.7(4) ?
    C2 C1 C5 O2 . . . . -177.1(2) ?
    N1 C1 C5 O1 . . . . -176.1(2) ?
    C2 C1 C5 O1 . . . . 3.1(4) ?
    C7 N3 N4 C6 . . . . 0.8(3) ?
    N3 N4 C6 N6 . . . . 179.8(3) ?
    N3 N4 C6 N5 . . . . -0.9(3) ?
    C7 N5 C6 N6 . . . . 179.9(3) ?
    C7 N5 C6 N4 . . . . 0.6(3) ?
    N4 N3 C7 N5 . . . . -0.4(4) ?
    C6 N5 C7 N3 . . . . -0.1(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
    N4 H4A O2 . 0.902(10) 1.769(12) 2.655(3) 166(3)
    N5 H5 O1 2_646 0.901(10) 1.733(11) 2.632(3) 176(3)
    N6 H6B O2 2_646 0.896(10) 1.968(12) 2.853(3) 169(3)
    N6 H6A N1 . 0.899(10) 2.212(12) 3.099(3) 169(3)
data_New_Global_Publ_Block
_journal_date_recd_electronic     2015-06-13
_journal_date_accepted     2015-06-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      7
_journal_page_first     840
_journal_page_last     843
_journal_paper_category     GO
_journal_paper_doi     10.1107/S205698901501172X
_journal_coeditor_code     HB7446
_publ_contact_author_name     'Filipe A. Almeida Paz'
_publ_contact_author_address
;
Department of Chemistry
CICECO -- Aveiro Institute of Materials
University of Aveiro
3810-193 Aveiro
Portugal
;
_publ_contact_author_email     'filipe.paz@ua.pt'
_publ_contact_author_fax     '(+351) 234 370 985'
_publ_contact_author_phone     '(+351) 234 370 200'
_publ_section_title
;
Crystal structure of
5-amino-4H-1,2,4-triazol-1-ium pyrazine-2-carboxylate: an unexpected salt
arising from the decarboxylation of both precursors
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fernandes, José A.' .
;
 Department of Chemistry
 CICECO -- Aveiro Institute of Materials
 University of Aveiro
 3810-193 Aveiro
 Portugal
;
    'Liu, Bing' .
;
 REQUIMTE / LAQV & Departamento de Química e Bioquímica
 Faculdade de Ciencias
 Universidade do Porto
 4169-007 Porto
 Portugal
;
    'Tomé, João P. C.' .
;
 Department of Chemistry
 QOPNA
 University of Aveiro
 3810-193 Aveiro
 Portugal
 Department of Organic and Macromolecular Chemistry
 Ghent University
 B-9000 Ghent
 Belgium
;
    'Cunha-Silva, Luís' .
;
 REQUIMTE / LAQV & Departamento de Química e Bioquímica
 Faculdade de Ciencias
 Universidade do Porto
 4169-007 Porto
 Portugal
;
    'Almeida Paz, Filipe A.' .
;
 Department of Chemistry
 CICECO -- Aveiro Institute of Materials
 University of Aveiro
 3810-193 Aveiro
 Portugal
;
_publ_section_synopsis
;
The salt 3-amino-2H,4H-1,2,4-triazolium pyrazine-2-carboxylate
was isolated by reacting 5-amino-1H-1,2,4-triazole-3-carboxylic acid
and pyrazine-2,3-dicarboxylic acid in the presence of silver nitrate and
1-butyl-3-methylimidazolium bromide in ionothermal conditions.
;
