#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239953.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_2239953
loop_
_publ_author_name
'Laus, Gerhard'
'Kahlenberg, Volker'
'Schottenberger, Herwig'
_publ_section_title
;
 Crystal structure of 4-amino-1-benzyl-1,2,4-triazolin-5-one
;
_journal_coeditor_code           FJ2680
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1083
_journal_page_last               o1084
_journal_paper_doi               10.1107/S160053681401931X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H10 N4 O'
_chemical_formula_moiety         'C9 H10 N4 O'
_chemical_formula_sum            'C9 H10 N4 O'
_chemical_formula_weight         190.21
_chemical_name_systematic
;
4-Amino-1-benzyl-1,2,4-triazolin-5-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.003(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0861(8)
_cell_length_b                   4.1690(2)
_cell_length_c                   12.3694(6)
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.9272
_cell_measurement_theta_min      3.6797
_cell_volume                     904.95(8)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur (Ruby, Gemini ultra)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7377
_diffrn_reflns_theta_full        68.04
_diffrn_reflns_theta_max         68.04
_diffrn_reflns_theta_min         5.04
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.86705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.2066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                1448
_reflns_number_total             1613
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2680sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        904.95(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239953
_cod_database_fobs_code          2239953
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_symmetry_multiplicity
O O1 0.41353(5) -0.0910(2) 1.01696(7) 0.0378(3) Uani d . 1 1
N N3 0.47943(7) -0.4111(3) 0.84565(10) 0.0398(3) Uani d D 1 1
H H31 0.5197(9) -0.283(4) 0.8730(13) 0.048 Uiso d D 1 1
H H32 0.4789(10) -0.550(4) 0.9007(12) 0.048 Uiso d D 1 1
N N1 0.32531(6) 0.0899(3) 0.85723(8) 0.0315(3) Uani d . 1 1
N N4 0.41310(6) -0.2253(2) 0.83245(8) 0.0301(3) Uani d . 1 1
N N2 0.31212(6) 0.0442(3) 0.74333(9) 0.0376(3) Uani d . 1 1
C C1 0.38691(7) -0.0749(3) 0.91540(10) 0.0290(3) Uani d . 1 1
C C5 0.14844(8) 0.0222(3) 0.81353(11) 0.0368(3) Uani d . 1 1
H H5 0.1579 0.0711 0.743 0.044 Uiso calc R 1 1
C C4 0.20132(7) 0.1088(3) 0.91021(11) 0.0322(3) Uani d . 1 1
C C6 0.08204(8) -0.1351(4) 0.81894(12) 0.0404(3) Uani d . 1 1
H H6 0.0465 -0.1967 0.7523 0.049 Uiso calc R 1 1
C C7 0.06730(8) -0.2024(4) 0.92066(13) 0.0448(4) Uani d . 1 1
H H7 0.0215 -0.3082 0.9243 0.054 Uiso calc R 1 1
C C9 0.18659(8) 0.0385(4) 1.01228(12) 0.0417(3) Uani d . 1 1
H H9 0.2225 0.0957 1.0791 0.05 Uiso calc R 1 1
C C2 0.36666(7) -0.1467(3) 0.73250(10) 0.0349(3) Uani d . 1 1
H H2 0.3732 -0.2221 0.6629 0.042 Uiso calc R 1 1
C C3 0.27350(7) 0.2839(3) 0.90400(12) 0.0384(3) Uani d . 1 1
H H3A 0.2596 0.4788 0.8578 0.046 Uiso calc R 1 1
H H3B 0.3003 0.3534 0.9799 0.046 Uiso calc R 1 1
C C8 0.11940(9) -0.1154(4) 1.01708(13) 0.0492(4) Uani d . 1 1
H H8 0.1093 -0.161 1.0874 0.059 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N4 N3 H31 107.9(11)
N4 N3 H32 106.2(11)
H31 N3 H32 104.7(15)
C1 N1 N2 112.77(10)
C1 N1 C3 126.43(11)
N2 N1 C3 120.72(10)
C2 N4 C1 108.65(10)
C2 N4 N3 124.24(11)
C1 N4 N3 126.97(11)
C2 N2 N1 103.95(10)
O1 C1 N1 129.42(12)
O1 C1 N4 127.80(12)
N1 C1 N4 102.77(10)
C6 C5 C4 120.48(12)
C6 C5 H5 119.8
C4 C5 H5 119.8
C9 C4 C5 119.16(13)
C9 C4 C3 120.48(12)
C5 C4 C3 120.35(12)
C7 C6 C5 120.20(13)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 C8 119.63(13)
C6 C7 H7 120.2
C8 C7 H7 120.2
C4 C9 C8 120.05(13)
C4 C9 H9 120
C8 C9 H9 120
N2 C2 N4 111.85(11)
N2 C2 H2 124.1
N4 C2 H2 124.1
N1 C3 C4 113.40(11)
N1 C3 H3A 108.9
C4 C3 H3A 108.9
N1 C3 H3B 108.9
C4 C3 H3B 108.9
H3A C3 H3B 107.7
C7 C8 C9 120.47(13)
C7 C8 H8 119.8
C9 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2335(15)
N3 N4 1.4040(15)
N3 H31 0.900(14)
N3 H32 0.895(14)
N1 C1 1.3577(17)
N1 N2 1.3840(15)
N1 C3 1.4592(16)
N4 C2 1.3561(17)
N4 C1 1.3803(16)
N2 C2 1.2993(18)
C5 C6 1.384(2)
C5 C4 1.3861(19)
C5 H5 0.95
C4 C9 1.383(2)
C4 C3 1.5138(18)
C6 C7 1.377(2)
C6 H6 0.95
C7 C8 1.378(2)
C7 H7 0.95
C9 C8 1.388(2)
C9 H9 0.95
C2 H2 0.95
C3 H3A 0.99
C3 H3B 0.99
C8 H8 0.95
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
N3 H32 O1 3_647 0.895(14) 2.471(16) 3.0583(15) 123.6(13) y
N3 H31 O1 3_657 0.900(14) 2.224(15) 3.0701(16) 156.2(15) y
C2 H2 O1 4_555 0.950 2.244 3.181(2) 168.4 y
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
C1 N1 N2 C2 -0.71(14)
C3 N1 N2 C2 -177.58(11)
N2 N1 C1 O1 -178.86(12)
C3 N1 C1 O1 -2.2(2)
N2 N1 C1 N4 0.78(13)
C3 N1 C1 N4 177.44(11)
C2 N4 C1 O1 179.10(12)
N3 N4 C1 O1 -5.1(2)
C2 N4 C1 N1 -0.55(13)
N3 N4 C1 N1 175.21(11)
C6 C5 C4 C9 -0.6(2)
C6 C5 C4 C3 -179.35(12)
C4 C5 C6 C7 1.1(2)
C5 C6 C7 C8 -0.7(2)
C5 C4 C9 C8 -0.3(2)
C3 C4 C9 C8 178.48(13)
N1 N2 C2 N4 0.32(14)
C1 N4 C2 N2 0.15(15)
N3 N4 C2 N2 -175.76(12)
C1 N1 C3 C4 -97.82(15)
N2 N1 C3 C4 78.60(15)
C9 C4 C3 N1 114.42(14)
C5 C4 C3 N1 -66.81(16)
C6 C7 C8 C9 -0.2(2)
C4 C9 C8 C7 0.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 686827
