#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:35:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022348.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_2022348
loop_
_publ_author_name
'Kumasaki, Mieko'
'Gontani, Saori'
'Mori, Kanae'
'Matsumoto, Shinya'
'Inoue, Kazuki'
_publ_section_title
;
 Crystallographic study of the energetic salt 1,2,4-triazolium perchlorate
;
_journal_coeditor_code           WP3012
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              197
_journal_page_last               201
_journal_paper_doi               10.1107/S2053229621003260
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C2 H4 N3 +, Cl O4 -'
_chemical_formula_moiety         'C2 H4 N3 +, Cl O4 -'
_chemical_formula_sum            'C2 H4 Cl N3 O4'
_chemical_formula_weight         169.53
_chemical_name_systematic        '1H-1,2,4-Triazolium perchlorate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 96.1530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.18590(10)
_cell_length_b                   11.84970(10)
_cell_length_c                   9.64610(10)
_cell_measurement_reflns_used    2328
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      73.0720
_cell_measurement_theta_min      4.6110
_cell_volume                     589.351(14)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
and OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      223(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC) Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3611
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.342
_diffrn_reflns_theta_min         4.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.753
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0362
_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
'w=1/[σ²(Fo²)+(0.0523P)²+0.1864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                1136
_reflns_number_total             1217
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3012sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022348.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2022348
_cod_database_fobs_code          2022348
_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.
;
_shelx_estimated_absorpt_t_min   0.072
_shelx_estimated_absorpt_t_max   0.287
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl10 0.85233(11) 0.750000 0.42804(6) 0.0232(2) Uani d 1 . .
O O11 0.8685(4) 0.750000 0.28056(18) 0.0319(5) Uani d 1 . .
O O12 0.5866(4) 0.750000 0.4563(2) 0.0416(5) Uani d 1 . .
O O13 0.9799(3) 0.65063(13) 0.48852(15) 0.0388(4) Uani d 1 . .
N N1 0.5121(3) 0.43779(14) 0.83520(17) 0.0277(4) Uani d 1 . .
H H1 0.477(5) 0.391(2) 0.888(3) 0.044(7) Uiso d 1 . .
N N2 0.3322(3) 0.51339(16) 0.7827(2) 0.0429(5) Uani d 1 . .
N N4 0.6962(3) 0.53346(15) 0.69127(17) 0.0297(4) Uani d 1 . .
H H4 0.808(6) 0.561(3) 0.648(3) 0.052(8) Uiso d 1 . .
C C3 0.4530(4) 0.57112(19) 0.6944(2) 0.0384(5) Uani d 1 . .
H H3 0.379350 0.631209 0.640211 0.046 Uiso calc 1 . .
C C5 0.7300(4) 0.44967(17) 0.7816(2) 0.0288(4) Uani d 1 . .
H H5 0.881871 0.406992 0.803017 0.035 Uiso calc 1 . .
Cl Cl6 1.03081(10) 0.250000 0.06220(5) 0.0209(2) Uani d 1 . .
O O7 0.7698(4) 0.250000 -0.0070(2) 0.0327(5) Uani d 1 . .
O O8 1.0241(4) 0.250000 0.21008(18) 0.0319(5) Uani d 1 . .
O O9 1.1632(3) 0.34949(12) 0.02056(13) 0.0313(3) Uani d 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 Cl10 O13 . . 109.15(8) ?
O11 Cl10 O13 . 4_575 109.15(8) ?
O12 Cl10 O11 . . 110.38(13) ?
O12 Cl10 O13 . . 109.38(8) ?
O12 Cl10 O13 . 4_575 109.38(8) ?
O13 Cl10 O13 . 4_575 109.40(14) ?
N2 N1 H1 . . 120(2) ?
C5 N1 H1 . . 127(2) ?
C5 N1 N2 . . 111.94(17) ?
C3 N2 N1 . . 103.41(17) ?
C3 N4 H4 . . 127(2) ?
C5 N4 H4 . . 126(2) ?
C5 N4 C3 . . 107.08(16) ?
N2 C3 N4 . . 111.04(19) ?
N2 C3 H3 . . 124.5 ?
N4 C3 H3 . . 124.5 ?
N1 C5 N4 . . 106.52(17) ?
N1 C5 H5 . . 126.7 ?
N4 C5 H5 . . 126.7 ?
O8 Cl6 O7 . . 109.84(12) ?
O8 Cl6 O9 . 4_565 109.92(7) ?
O8 Cl6 O9 . . 109.92(7) ?
O9 Cl6 O7 4_565 . 108.77(8) ?
O9 Cl6 O7 . . 108.77(7) ?
O9 Cl6 O9 4_565 . 109.60(12) ?
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
Cl10 O11 . 1.4341(18) ?
Cl10 O12 . 1.433(2) ?
Cl10 O13 4_575 1.4428(15) ?
Cl10 O13 . 1.4428(15) ?
N1 H1 . 0.78(3) ?
N1 N2 . 1.352(2) ?
N1 C5 . 1.299(2) ?
N2 C3 . 1.303(3) ?
N4 H4 . 0.82(3) ?
N4 C3 . 1.341(3) ?
N4 C5 . 1.321(3) ?
C3 H3 . 0.9400 ?
C5 H5 . 0.9400 ?
Cl6 O7 . 1.4438(19) ?
Cl6 O8 . 1.4305(18) ?
Cl6 O9 . 1.4428(14) ?
Cl6 O9 4_565 1.4427(14) ?
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
N4 H4 O13 . 0.818 2.141 2.921 159.61 yes
N1 H1 O9 . 0.787 2.230 2.874 139.46 yes
N H1 O7 . 0.787 2.407 2.936 125.59 yes
N4 H4 O8 . 0.818 2.719 3.049 106.14 yes
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
N1 N2 C3 N4 . . . . 0.2(3) ?
N2 N1 C5 N4 . . . . -0.5(2) ?
C3 N4 C5 N1 . . . . 0.6(2) ?
C5 N1 N2 C3 . . . . 0.2(3) ?
C5 N4 C3 N2 . . . . -0.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308334
