#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218368.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_2218368
loop_
_publ_author_name
'Xie, Qing-Ruo'
_publ_section_title
;
 1H-1,2,4-Triazole-3-carboxamide
;
_journal_coeditor_code           CS2075
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1110
_journal_paper_doi               10.1107/S1600536808014013
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C3 H4 N4 O'
_chemical_formula_moiety         'C3 H4 N4 O'
_chemical_formula_sum            'C3 H4 N4 O'
_chemical_formula_weight         112.10
_chemical_name_systematic
;
1H-1,2,4-Triazole-3-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.4670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.6944(4)
_cell_length_b                   17.527(3)
_cell_length_c                   7.0520(17)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.324
_cell_volume                     455.24(14)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2199
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0347
_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)+(0.0653P)²+0.058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                657
_reflns_number_total             807
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs2075.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218368
_cod_database_fobs_code          2218368
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N N1 0.2702(4) 0.99272(7) 0.7168(2) 0.0381(4) Uani d . 1
H H1A 0.3404 1.0240 0.6332 0.046 Uiso calc R 1
H H1B 0.1763 1.0098 0.8163 0.046 Uiso calc R 1
N N2 0.0498(4) 0.77481(8) 1.00884(19) 0.0330(4) Uani d . 1
H H2 0.0162 0.7288 1.0460 0.040 Uiso calc R 1
N N3 0.1784(4) 0.79443(7) 0.84073(18) 0.0329(4) Uani d . 1
N N4 0.0595(4) 0.89955(8) 1.01228(18) 0.0349(4) Uani d . 1
O O1 0.4402(3) 0.88844(6) 0.55202(16) 0.0386(4) Uani d . 1
C C1 0.3067(4) 0.91813(8) 0.6923(2) 0.0289(4) Uani d . 1
C C2 0.1793(4) 0.87021(8) 0.8491(2) 0.0271(4) Uani d . 1
C C3 -0.0168(5) 0.83716(9) 1.1079(2) 0.0360(4) Uani d . 1
H H3 -0.1048 0.8370 1.2279 0.043 Uiso calc R 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
N1 0.0594(10) 0.0241(8) 0.0333(8) 0.0011(6) 0.0202(7) 0.0017(5)
N2 0.0449(9) 0.0220(7) 0.0331(8) -0.0010(5) 0.0098(6) 0.0056(5)
N3 0.0434(8) 0.0250(8) 0.0314(7) -0.0006(5) 0.0093(6) 0.0010(5)
N4 0.0494(9) 0.0259(8) 0.0310(8) 0.0004(6) 0.0145(6) 0.0004(5)
O1 0.0566(8) 0.0267(6) 0.0347(7) 0.0030(5) 0.0176(5) -0.0001(5)
C1 0.0339(9) 0.0259(9) 0.0274(8) 0.0006(6) 0.0055(6) -0.0007(6)
C2 0.0307(8) 0.0243(8) 0.0268(8) 0.0016(6) 0.0052(6) -0.0009(6)
C3 0.0495(10) 0.0292(9) 0.0308(8) -0.0012(7) 0.0131(7) 0.0013(7)
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
C1 N1 H1A 120.0
C1 N1 H1B 120.0
H1A N1 H1B 120.0
C3 N2 N3 110.03(13)
C3 N2 H2 125.0
N3 N2 H2 125.0
C2 N3 N2 102.40(13)
C3 N4 C2 102.33(13)
O1 C1 N1 124.23(15)
O1 C1 C2 121.15(14)
N1 C1 C2 114.62(14)
N3 C2 N4 114.43(13)
N3 C2 C1 121.94(13)
N4 C2 C1 123.62(14)
N4 C3 N2 110.81(15)
N4 C3 H3 124.6
N2 C3 H3 124.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3270(19)
N1 H1A 0.8600
N1 H1B 0.8600
N2 C3 1.330(2)
N2 N3 1.3553(19)
N2 H2 0.8600
N3 C2 1.3294(19)
N4 C3 1.326(2)
N4 C2 1.366(2)
O1 C1 1.2524(18)
C1 C2 1.493(2)
C3 H3 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
N1 H1A O1 3_676 0.86 2.21 3.065(2) 173
N1 H1B N4 3_577 0.86 2.22 3.010(2) 154
N2 H2 O1 4_576 0.86 2.07 2.909(2) 163
N2 H2 N3 4_576 0.86 2.54 3.055(2) 120
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
C3 N2 N3 C2 -0.33(17)
N2 N3 C2 N4 0.05(17)
N2 N3 C2 C1 179.30(13)
C3 N4 C2 N3 0.23(18)
C3 N4 C2 C1 -179.00(14)
O1 C1 C2 N3 -4.7(2)
N1 C1 C2 N3 176.10(15)
O1 C1 C2 N4 174.46(15)
N1 C1 C2 N4 -4.7(2)
C2 N4 C3 N2 -0.43(18)
N3 N2 C3 N4 0.50(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 58634
