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#$Date: 2025-04-05 06:40:45 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298997 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063556.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.
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data_7063556
loop_
_publ_author_name
'Kuznetsova, Agata N.'
'Leonov, Nikita E.'
'Anikin, Oleg V.'
'Klenov, Michael S.'
'Churakov, Aleksandr M.'
'Strelenko, Yurii A.'
'Novikov, Roman A.'
'Fedyanin, Ivan V.'
'Pivkina, Alla N.'
'Kon’kova, Tatiana S.'
'Sinditskii, Valery P.'
'Smirnova, Anastasia D.'
'Tartakovsky, Vladimir A.'
_publ_section_title
;
 Parent 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole and its
 derivatives as precursors for the design of promising high energy density
 materials
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              311
_journal_page_last               320
_journal_paper_doi               10.1039/D4NJ04427D
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C3 H2 N6 O'
_chemical_formula_sum            'C3 H2 N6 O'
_chemical_formula_weight         138.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_method           'Modified SHELXL output'
_audit_update_record
;
2024-09-09 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.6557(5)
_cell_length_b                   10.3968(14)
_cell_length_c                   13.7717(18)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.45
_cell_volume                     523.43(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_type            'Bruker PHOTON II CPAD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_measurement_method       'ο scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6619
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.125
_diffrn_reflns_theta_min         2.455
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0312
_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)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1345
_reflns_number_total             1541
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04427d2.cif
_cod_data_source_block           a1667
_cod_depositor_comments
'Adding full bibliography for 7063553--7063561.cif.'
_cod_database_code               7063556
_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru
_shelx_shelxl_version_number     2018/3
_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   0.955
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O1 O 0.9642(4) 0.62441(11) 0.49166(8) 0.0156(3) Uani 1 1 d . . . . .
N1 N 0.5510(5) 0.40316(13) 0.27444(9) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.4438(5) 0.28684(13) 0.31017(10) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.4269(4) 0.28410(13) 0.40525(10) 0.0150(3) Uani 1 1 d . . . . .
N6 N 0.5069(4) 0.43562(12) 0.52891(10) 0.0127(3) Uani 1 1 d . . . . .
N7 N 0.4755(5) 0.45510(13) 0.60717(9) 0.0180(3) Uani 1 1 d . . . . .
N8 N 0.7151(4) 0.60627(13) 0.34151(11) 0.0138(3) Uani 1 1 d . . . . .
H8 H 0.667(8) 0.644(2) 0.2875(16) 0.031(7) Uiso 1 1 d . . . . .
C4 C 0.5286(5) 0.40464(14) 0.43329(11) 0.0120(3) Uani 1 1 d . . . . .
C5 C 0.6055(5) 0.47949(15) 0.35110(12) 0.0123(3) Uani 1 1 d . . . . .
C9 C 0.8919(5) 0.67088(15) 0.41301(12) 0.0132(3) Uani 1 1 d . . . . .
H9 H 0.948(7) 0.7594(17) 0.3925(12) 0.011(5) Uiso 1 1 d . . . . .
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
C5 N1 N2 106.54(13) . . ?
N3 N2 N1 113.16(13) . . ?
N2 N3 C4 104.48(13) . . ?
N7 N6 C4 175.95(17) . . ?
C9 N8 C5 122.72(14) . . ?
C9 N8 H8 120.0(16) . . ?
C5 N8 H8 117.3(16) . . ?
N6 C4 N3 118.48(14) . . ?
N6 C4 C5 131.52(14) . . ?
N3 C4 C5 109.65(13) . . ?
N1 C5 N8 122.25(15) . . ?
N1 C5 C4 106.17(14) . . ?
N8 C5 C4 131.58(15) . . ?
O1 C9 N8 123.65(15) . . ?
O1 C9 H9 125.6(11) . . ?
N8 C9 H9 110.8(11) . . ?
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
O1 C9 1.215(2) . ?
N1 C5 1.336(2) . ?
N1 N2 1.363(2) . ?
N2 N3 1.3111(18) . ?
N3 C4 1.363(2) . ?
N6 N7 1.1027(18) . ?
N6 C4 1.3580(19) . ?
N8 C9 1.356(2) . ?
N8 C5 1.384(2) . ?
N8 H8 0.86(2) . ?
C4 C5 1.402(2) . ?
C9 H9 0.984(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 N2 0.86(2) 2.04(2) 2.8681(19) 160(2) 3_655 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 -0.1(2) . . . . ?
N1 N2 N3 C4 -0.1(2) . . . . ?
N2 N3 C4 N6 174.22(16) . . . . ?
N2 N3 C4 C5 0.2(2) . . . . ?
N2 N1 C5 N8 -179.56(17) . . . . ?
N2 N1 C5 C4 0.20(19) . . . . ?
C9 N8 C5 N1 -156.22(17) . . . . ?
C9 N8 C5 C4 24.1(3) . . . . ?
N6 C4 C5 N1 -173.2(2) . . . . ?
N3 C4 C5 N1 -0.26(19) . . . . ?
N6 C4 C5 N8 6.5(3) . . . . ?
N3 C4 C5 N8 179.47(18) . . . . ?
C5 N8 C9 O1 -1.2(3) . . . . ?
