#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238014.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_2238014
loop_
_publ_author_name
'Bel Haj Salah, Souhir'
'Mrad, Mohamed Lahbib'
'Ferretti, Valeria'
'Lefebvre, Frederic'
'Ben Nasr, Cherif'
_publ_section_title
;
 3-Amino-5,6-dimethyl-1,2,4-triazin-2-ium nitrate
;
_journal_coeditor_code           RZ5062
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o844
_journal_paper_doi               10.1107/S1600536813012026
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H9 N4 +, N O3 -'
_chemical_formula_moiety         'C5 H9 N4 +, N O3 -'
_chemical_formula_sum            'C5 H9 N5 O3'
_chemical_formula_weight         187.17
_chemical_name_systematic
;
3-Amino-5,6-dimethyl-1,2,4-triazin-2-ium nitrate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.7213(2)
_cell_length_b                   6.4245(2)
_cell_length_c                   6.7197(6)
_cell_measurement_reflns_used    2321
_cell_measurement_temperature    295
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     851.38(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection
'KappaCCD Server Software  (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2321
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0487
_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)+(0.1038P)²+0.0610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                1031
_reflns_number_total             1326
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz5062.cif
_cod_data_source_block           I
_cod_database_code               2238014
_cod_database_fobs_code          2238014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 -0.07155(6) 0.2500 -0.1964(2) 0.0634(4) Uani d S 1 2
O O2 -0.15520(7) 0.2500 0.0121(2) 0.0705(5) Uani d S 1 2
O O3 -0.17374(7) 0.2500 -0.3030(2) 0.0767(5) Uani d S 1 2
N N1 0.04674(7) 0.2500 0.4549(2) 0.0477(4) Uani d S 1 2
N N2 0.08600(8) 0.2500 0.0580(2) 0.0520(4) Uani d S 1 2
N N3 0.02034(7) 0.2500 0.11531(19) 0.0478(4) Uani d S 1 2
N N4 -0.06438(7) 0.2500 0.3511(2) 0.0562(4) Uani d S 1 2
N N5 -0.13454(7) 0.2500 -0.1615(2) 0.0519(4) Uani d S 1 2
C C1 0.00063(7) 0.2500 0.3055(2) 0.0419(4) Uani d S 1 2
C C2 0.13126(8) 0.2500 0.1986(2) 0.0479(4) Uani d S 1 2
C C3 0.11066(8) 0.2500 0.4046(2) 0.0462(4) Uani d S 1 2
C C4 0.20428(9) 0.2500 0.1392(4) 0.0650(5) Uani d S 1 2
C C5 0.16177(11) 0.2500 0.5668(3) 0.0695(6) Uani d S 1 2
H H1N -0.1005(17) 0.2500 0.254(5) 0.100(9) Uiso d S 1 2
H H2N -0.0701(14) 0.2500 0.479(5) 0.083(8) Uiso d S 1 2
H H3N -0.0130(17) 0.2500 0.007(5) 0.086(7) Uiso d S 1 2
H H1 0.2269(9) 0.133(3) 0.203(3) 0.092(6) Uiso d . 1 1
H H2 0.206(3) 0.2500 0.019(9) 0.153(16) Uiso d S 1 2
H H3 0.1438(16) 0.2500 0.683(5) 0.102(10) Uiso d S 1 2
H H4 0.1920(13) 0.130(3) 0.544(4) 0.128(8) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0410(6) 0.1020(10) 0.0472(7) 0.000 0.0003(5) 0.000
O2 0.0505(7) 0.1173(12) 0.0438(7) 0.000 0.0051(6) 0.000
O3 0.0532(8) 0.1263(14) 0.0506(8) 0.000 -0.0160(6) 0.000
N1 0.0417(7) 0.0647(8) 0.0366(6) 0.000 -0.0006(5) 0.000
N2 0.0452(7) 0.0729(9) 0.0379(7) 0.000 0.0026(5) 0.000
N3 0.0419(7) 0.0646(8) 0.0369(6) 0.000 -0.0028(5) 0.000
N4 0.0405(7) 0.0801(10) 0.0480(8) 0.000 0.0019(6) 0.000
N5 0.0421(7) 0.0695(9) 0.0441(7) 0.000 -0.0033(5) 0.000
C1 0.0400(7) 0.0475(7) 0.0381(7) 0.000 -0.0010(6) 0.000
C2 0.0421(7) 0.0592(9) 0.0424(8) 0.000 0.0024(6) 0.000
C3 0.0412(7) 0.0583(8) 0.0390(7) 0.000 -0.0015(6) 0.000
C4 0.0416(8) 0.0970(15) 0.0564(11) 0.000 0.0075(8) 0.000
C5 0.0474(9) 0.1150(18) 0.0461(10) 0.000 -0.0072(8) 0.000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 C1 117.14(14)
C2 N2 N3 116.81(14)
C1 N3 N2 123.48(13)
C1 N3 H3N 121(2)
N2 N3 H3N 116(2)
C1 N4 H1N 124(2)
C1 N4 H2N 111.0(18)
H1N N4 H2N 125(2)
O3 N5 O2 121.64(15)
O3 N5 O1 118.39(16)
O2 N5 O1 119.97(15)
N4 C1 N3 120.37(14)
N4 C1 N1 118.70(15)
N3 C1 N1 120.93(14)
N2 C2 C3 120.27(15)
N2 C2 C4 117.90(16)
C3 C2 C4 121.83(15)
N1 C3 C2 121.37(14)
N1 C3 C5 117.75(16)
C2 C3 C5 120.88(15)
C2 C4 H1 108.9(11)
C2 C4 H2 108(4)
H1 C4 H2 115(2)
C3 C5 H3 113(2)
C3 C5 H4 107.1(15)
H3 C5 H4 113.1(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2642(18)
O2 N5 1.236(2)
O3 N5 1.2256(19)
N1 C3 1.305(2)
N1 C1 1.3547(19)
N2 C2 1.300(2)
N2 N3 1.3510(19)
N3 C1 1.3357(19)
N3 H3N 0.98(4)
N4 C1 1.3183(19)
N4 H1N 0.97(3)
N4 H2N 0.87(4)
C2 C3 1.443(2)
C2 C4 1.494(2)
C3 C5 1.485(2)
C4 H1 0.972(17)
C4 H2 0.81(6)
C5 H3 0.86(3)
C5 H4 0.99(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
N3 H3N O1 . 0.98(4) 1.79(4) 2.770(2) 178(3)
N4 H1N O2 . 0.97(3) 1.93(3) 2.898(2) 166(3)
N4 H2N O1 1_556 0.87(4) 2.18(4) 3.043(2) 173(3)
