#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:40:07 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573393.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573393
loop_
_publ_author_name
'Cai, Ziwu'
'Shi, Junhao'
'Yu, Qian'
'Jiang, Tianyu'
'Zhang, Wenquan'
_publ_section_title
;
 4-Amino-1,2,3-triazine 2-oxide: a promising structural unit for the
 design and synthesis of novel energetic materials with good thermal
 stability and low impact sensitivity
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              302
_journal_page_last               310
_journal_paper_doi               10.1039/D4NJ04219K
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C7 H4 N6 O5, C2 H3 N'
_chemical_formula_sum            'C9 H7 N7 O5'
_chemical_formula_weight         293.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-14 deposited with the CCDC.	2024-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.049(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.556(2)
_cell_length_b                   5.7279(12)
_cell_length_c                   21.606(5)
_cell_measurement_reflns_used    1960
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.494
_cell_measurement_theta_min      3.801
_cell_volume                     1296.5(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9440
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.682
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4918
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0645P)²+0.1915P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1490
_reflns_number_total             2627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04219k2.cif
_cod_data_source_block           mo_20231842_0m
_cod_depositor_comments
'Adding full bibliography for 1573393--1573394.cif.'
_cod_database_code               1573393
_shelxl_version_number           2013-2
_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_max   0.999
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N1(H1a,H1b)
2.c Idealised Me refined as rotating group:
 C00L(H00a,H00b,H00c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.21108(17) 1.1057(3) 0.44405(8) 0.0635(5) Uani 1 1 d . . . . .
O1 O 0.5474(2) -0.0301(3) 0.31647(10) 0.0738(6) Uani 1 1 d . . . . .
N4 N 0.19609(18) 0.7952(4) 0.38412(9) 0.0504(5) Uani 1 1 d . . . . .
N3 N 0.2635(2) 0.9276(4) 0.42529(9) 0.0495(5) Uani 1 1 d . . . . .
N2 N 0.38662(19) 0.8992(4) 0.44984(9) 0.0514(5) Uani 1 1 d . . . . .
O4 O -0.01485(19) 0.5174(4) 0.33383(11) 0.0829(7) Uani 1 1 d . . . . .
N1 N 0.56966(19) 0.6945(4) 0.45581(9) 0.0562(6) Uani 1 1 d . . . . .
H1A H 0.6024 0.7964 0.4823 0.067 Uiso 1 1 calc R . . . .
H1B H 0.6151 0.5795 0.4455 0.067 Uiso 1 1 calc R . . . .
O3 O 0.0331(2) 0.5209(4) 0.23942(11) 0.0902(7) Uani 1 1 d . . . . .
N6 N 0.4407(3) 0.0243(4) 0.29249(11) 0.0598(6) Uani 1 1 d . . . . .
N5 N 0.0606(2) 0.5047(4) 0.29594(13) 0.0640(6) Uani 1 1 d . . . . .
O2 O 0.3804(2) -0.0837(4) 0.25032(11) 0.0886(7) Uani 1 1 d . . . . .
C3 C 0.2598(2) 0.6061(4) 0.36466(10) 0.0436(6) Uani 1 1 d . . . . .
C2 C 0.3884(2) 0.5546(4) 0.38581(10) 0.0431(6) Uani 1 1 d . . . . .
C1 C 0.4496(2) 0.7144(4) 0.43092(10) 0.0462(6) Uani 1 1 d . . . . .
C7 C 0.4472(2) 0.3611(4) 0.36186(11) 0.0472(6) Uani 1 1 d . . . . .
H7 H 0.5313 0.3236 0.3764 0.057 Uiso 1 1 calc R . . . .
C5 C 0.2536(2) 0.2765(4) 0.29400(11) 0.0513(6) Uani 1 1 d . . . . .
H5 H 0.2103 0.1857 0.2625 0.062 Uiso 1 1 calc R . . . .
C4 C 0.1952(2) 0.4599(4) 0.31882(11) 0.0479(6) Uani 1 1 d . . . . .
C6 C 0.3798(2) 0.2287(4) 0.31705(11) 0.0470(6) Uani 1 1 d . . . . .
N00J N 0.2458(3) 0.6810(6) 0.56454(14) 0.0985(10) Uani 1 1 d . . . . .
C00K C 0.1874(3) 0.8333(7) 0.57661(15) 0.0771(9) Uani 1 1 d . . . . .
C00L C 0.1153(3) 1.0345(7) 0.59189(19) 0.1084(13) Uani 1 1 d . . . . .
H00A H 0.1268 1.1588 0.5633 0.163 Uiso 1 1 calc GR . . . .
H00B H 0.1446 1.0840 0.6336 0.163 Uiso 1 1 calc GR . . . .
H00C H 0.0264 0.9945 0.5889 0.163 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N4 C3 114.82(19) . . ?
O5 N3 N4 117.8(2) . . ?
O5 N3 N2 114.4(2) . . ?
N4 N3 N2 127.8(2) . . ?
C1 N2 N3 117.7(2) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O1 N6 C6 118.2(2) . . ?
O2 N6 O1 124.0(2) . . ?
O2 N6 C6 117.7(3) . . ?
O4 N5 O3 125.1(3) . . ?
O4 N5 C4 118.1(2) . . ?
O3 N5 C4 116.7(2) . . ?
N4 C3 C2 123.8(2) . . ?
N4 C3 C4 118.2(2) . . ?
C4 C3 C2 117.9(2) . . ?
C3 C2 C1 115.1(2) . . ?
C7 C2 C3 119.9(2) . . ?
C7 C2 C1 125.0(2) . . ?
N2 C1 C2 120.8(2) . . ?
N1 C1 N2 115.6(2) . . ?
N1 C1 C2 123.6(2) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 C2 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.1(2) . . ?
C6 C5 H5 121.0 . . ?
C3 C4 N5 119.9(2) . . ?
C5 C4 N5 117.9(2) . . ?
C5 C4 C3 122.2(2) . . ?
C7 C6 N6 119.3(2) . . ?
C7 C6 C5 122.6(2) . . ?
C5 C6 N6 118.1(2) . . ?
N00J C00K C00L 178.3(4) . . ?
C00K C00L H00A 109.5 . . ?
C00K C00L H00B 109.5 . . ?
C00K C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N3 1.252(2) . ?
O1 N6 1.221(3) . ?
N4 N3 1.311(3) . ?
N4 C3 1.368(3) . ?
N3 N2 1.352(3) . ?
N2 C1 1.341(3) . ?
O4 N5 1.212(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.319(3) . ?
O3 N5 1.224(3) . ?
N6 O2 1.215(3) . ?
N6 C6 1.466(3) . ?
N5 C4 1.469(3) . ?
C3 C2 1.409(3) . ?
C3 C4 1.408(3) . ?
C2 C1 1.432(3) . ?
C2 C7 1.400(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.360(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.361(3) . ?
C5 C6 1.391(3) . ?
N00J C00K 1.117(4) . ?
C00K C00L 1.442(5) . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00C 0.9600 . ?
