#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/43/2234363.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_2234363
loop_
_publ_author_name
'Berrah, Fadila'
'Bouchene, Rafika'
'Bouacida, Sofiane'
'Roisnel, Thierry'
_publ_section_title
;
 5-Amino-3-carboxy-1H-1,2,4-triazol-4-ium nitrate monohydrate
;
_journal_coeditor_code           PV2522
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1116
_journal_paper_doi               10.1107/S1600536812011154
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C3 H5 N4 O2 +, N O3 -, H2 O'
_chemical_formula_moiety         'C3 H5 N4 O2 +, N O3 -, H2 O'
_chemical_formula_structural     'C3 H5 N4 O2 +, N O3 -, H2 O'
_chemical_formula_sum            'C3 H7 N5 O6'
_chemical_formula_weight         209.14
_chemical_name_systematic
;
5-Amino-3-carboxy-1H-1,2,4-triazol-4-ium nitrate monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.572(12)
_cell_angle_beta                 100.524(13)
_cell_angle_gamma                98.933(13)
_cell_formula_units_Z            2
_cell_length_a                   4.9934(13)
_cell_length_b                   6.7454(17)
_cell_length_c                   12.446(3)
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      3.38
_cell_volume                     401.59(18)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4012
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.1
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.0973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                1563
_reflns_number_total             1821
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2522.cif
_cod_data_source_block           I
_cod_original_cell_volume        401.60(18)
_cod_database_code               2234363
_cod_database_fobs_code          2234363
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 -0.1877(2) -0.15602(16) 0.31865(9) 0.0218(3) Uani d . 1 1
N N3 -0.0716(3) 0.32704(19) 0.20042(11) 0.0174(3) Uani d . 1 1
O O4 0.2001(2) 0.80430(17) 0.13489(10) 0.0241(3) Uani d . 1 1
O O5 -0.2192(2) 0.59982(18) 0.06811(10) 0.0234(3) Uani d . 1 1
H H5 -0.2505 0.6888 0.0311 0.035 Uiso calc R 1 1
O O1W -0.3752(3) 0.82557(19) -0.06786(10) 0.0272(3) Uani d . 1 1
H H2W -0.319(5) 0.946(4) -0.0762(18) 0.041 Uiso d . 1 1
H H1W -0.544(5) 0.791(3) -0.1043(19) 0.041 Uiso d . 1 1
N N5 0.5272(3) 0.2985(2) 0.39298(11) 0.0219(3) Uani d . 1 1
H H5A 0.4999 0.185 0.4172 0.026 Uiso calc R 1 1
H H5B 0.6829 0.3811 0.4162 0.026 Uiso calc R 1 1
O O2 -0.0623(2) -0.34292(17) 0.44188(10) 0.0284(3) Uani d . 1 1
O O3 0.2143(2) -0.06970(17) 0.43144(10) 0.0262(3) Uani d . 1 1
N N2 0.3435(2) 0.51522(18) 0.27273(10) 0.0158(3) Uani d . 1 1
H H2 0.4806 0.6154 0.2854 0.019 Uiso calc R 1 1
N N4 0.0781(3) 0.23345(19) 0.27646(10) 0.0167(3) Uani d . 1 1
H H4 0.0176 0.1178 0.2937 0.02 Uiso calc R 1 1
N N1 -0.0104(3) -0.18948(19) 0.39831(10) 0.0171(3) Uani d . 1 1
C C3 0.3308(3) 0.3458(2) 0.32034(12) 0.0155(3) Uani d . 1 1
C C2 0.0952(3) 0.4958(2) 0.20038(12) 0.0165(3) Uani d . 1 1
C C1 0.0296(3) 0.6523(2) 0.12995(13) 0.0175(3) Uani 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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
C2 N3 N4 103.98(12)
C1 O5 H5 109.5
H2W O1W H1W 107(2)
C3 N5 H5A 120
C3 N5 H5B 120
H5A N5 H5B 120
C3 N2 C2 106.57(12)
C3 N2 H2 126.7
C2 N2 H2 126.7
C3 N4 N3 111.38(12)
C3 N4 H4 124.3
N3 N4 H4 124.3
O3 N1 O2 120.44(13)
O3 N1 O1 119.79(12)
O2 N1 O1 119.77(12)
N5 C3 N4 126.95(13)
N5 C3 N2 127.13(13)
N4 C3 N2 105.91(12)
N3 C2 N2 112.16(13)
N3 C2 C1 124.96(14)
N2 C2 C1 122.89(13)
O4 C1 O5 128.33(15)
O4 C1 C2 120.16(14)
O5 C1 C2 111.50(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2720(16)
N3 C2 1.3023(19)
N3 N4 1.3779(18)
O4 C1 1.2139(18)
O5 C1 1.3051(19)
O5 H5 0.82
O1W H2W 0.84(3)
O1W H1W 0.86(2)
N5 C3 1.3155(19)
N5 H5A 0.86
N5 H5B 0.86
O2 N1 1.2443(16)
O3 N1 1.2426(16)
N2 C3 1.3529(19)
N2 C2 1.3698(19)
N2 H2 0.86
N4 C3 1.3443(18)
N4 H4 0.86
C2 C1 1.495(2)
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
O5 H5 O1W . 0.82 1.72 2.5210(17) 165.6 yes
O1W H2W O4 2_575 0.84(3) 1.97(3) 2.7985(18) 166(2) yes
O1W H1W N3 2_465 0.86(2) 2.05(3) 2.9011(19) 172(2) yes
N5 H5A O3 . 0.86 2.1 2.8672(18) 147.5 ?
N5 H5A O3 2_656 0.86 2.44 3.0498(19) 128.8 ?
N5 H5B O2 1_665 0.86 2.04 2.8352(18) 154.3 yes
N5 H5B O2 2_656 0.86 2.41 3.0060(18) 126.6 ?
N2 H2 O1 1_665 0.86 2.02 2.8790(17) 177.7 yes
N4 H4 O1 . 0.86 2.06 2.9112(18) 170.7 yes
N4 H4 O3 . 0.86 2.42 3.0590(18) 131.7 ?
N4 H4 N1 . 0.86 2.59 3.4099(19) 160.1 ?
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
C2 N3 N4 C3 -0.23(16)
N3 N4 C3 N5 -178.18(15)
N3 N4 C3 N2 0.55(16)
C2 N2 C3 N5 178.10(15)
C2 N2 C3 N4 -0.62(15)
N4 N3 C2 N2 -0.18(16)
N4 N3 C2 C1 179.43(14)
C3 N2 C2 N3 0.52(17)
C3 N2 C2 C1 -179.10(13)
N3 C2 C1 O4 -179.23(15)
N2 C2 C1 O4 0.3(2)
N3 C2 C1 O5 0.5(2)
N2 C2 C1 O5 -179.93(13)
