#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:40:45 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298997 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/35/7063555.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_7063555
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         'C4 H6 N6'
_chemical_formula_sum            'C4 H6 N6'
_chemical_formula_weight         138.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 98.274(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8790(3)
_cell_length_b                   6.2602(5)
_cell_length_c                   12.9022(11)
_cell_measurement_reflns_used    2927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.35
_cell_measurement_theta_min      5.79
_cell_volume                     310.05(4)
_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      100(2)
_diffrn_detector_type            'Bruker PHOTON III CPAD area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Quest diffractometer'
_diffrn_measurement_method       'ο scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4193
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        29.991
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_min         5.322
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       needle
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     48
_refine_ls_number_reflns         905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0379
_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)+(0.0440P)²+0.1220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                868
_reflns_number_total             905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04427d2.cif
_cod_data_source_block           eae0311
_cod_depositor_comments
'Adding full bibliography for 7063553--7063561.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063555
_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   0.969
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_file
;
TITL eae0311 in P2(1)/n
    eae0311.res
    created by SHELXL-2018/3 at 09:01:05 on 03-Sep-2024
CELL 0.71073   3.87900   6.26020  12.90220  90.0000  98.2739  90.0000
ZERR    2.00   0.00030   0.00050   0.00110   0.0000   0.0023   0.0000
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C H N
UNIT 8 12 12
TEMP -173.000
REM QUEST
REM COLORLESS NEEDLE
SIZE 0.29 0.12 0.07
L.S. 10
BOND $H
ACTA 60

CONF

FMAP 2
PLAN 20
WGHT    0.044000    0.122000
FVAR       0.96964   0.63678
N1    3    0.424989    0.434861    0.369336    11.00000    0.02032    0.01744 =
         0.01808    0.00147    0.00227    0.00343
N2    3    0.616473    0.268454    0.409939    11.00000    0.01720    0.01571 =
         0.01779    0.00083    0.00276    0.00133
N3    3    0.726927    0.263350    0.513191    11.00000    0.02097    0.01718 =
         0.01741    0.00077    0.00195    0.00207
C3A   1    0.590580    0.448436    0.543119    11.00000    0.01549    0.01563 =
         0.01688    0.00217    0.00223   -0.00001
C4    1    0.707435    0.097923    0.341695    11.00000    0.02212    0.01932 =
         0.02201   -0.00426    0.00382    0.00296
AFIX 137
PART 1
H4A   2    0.816366   -0.019956    0.384456    21.00000   -1.50000
H4B   2    0.870815    0.152766    0.296817    21.00000   -1.50000
H4C   2    0.496219    0.046420    0.297974    21.00000   -1.50000
AFIX 137
PART 2
H4E   2    0.781688    0.160289    0.278834   -21.00000   -1.50000
H4D   2    0.503916    0.006416    0.321416   -21.00000   -1.50000
H4F   2    0.897797    0.012525    0.378996   -21.00000   -1.50000
PART   0

AFIX   0
HKLF 4




REM  eae0311 in P2(1)/n
REM wR2 = 0.0984, GooF = S = 1.070, Restrained GooF = 1.070 for all data
REM R1 = 0.0379 for 868 Fo > 4sig(Fo) and 0.0392 for all 905 data
REM 48 parameters refined using 0 restraints

END

WGHT      0.0437      0.1078

REM Highest difference peak  0.524,  deepest hole -0.232,  1-sigma level  0.046
Q1    1   0.5000  0.5000  0.5000  10.50000  0.05    0.52
Q2    1   0.6765  0.2670  0.4632  11.00000  0.05    0.31
Q3    1   0.5962  0.4950  0.5859  11.00000  0.05    0.26
Q4    1   0.6714  0.1839  0.3772  11.00000  0.05    0.23
Q5    1   0.3995  0.4452  0.3042  11.00000  0.05    0.22
Q6    1   0.6753  0.3608  0.5368  11.00000  0.05    0.21
Q7    1   0.9155  0.2468  0.5251  11.00000  0.05    0.15
Q8    1   0.6211  0.1013  0.2771  11.00000  0.05    0.14
Q9    1   0.5837  0.3723  0.3847  11.00000  0.05    0.12
Q10   1   0.4134  0.3010  0.3921  11.00000  0.05    0.11
Q11   1   0.7274  0.1815  0.5564  11.00000  0.05    0.10
Q12   1   0.8612  0.2234  0.5749  11.00000  0.05    0.09
Q13   1   0.6391  0.3446  0.2779  11.00000  0.05    0.08
Q14   1   0.9003  0.0604  0.3637  11.00000  0.05    0.08
Q15   1   0.6794 -0.0091  0.4622  11.00000  0.05    0.07
Q16   1   1.0118  0.1710  0.4645  11.00000  0.05    0.07
Q17   1   1.0944  0.3453  0.4996  11.00000  0.05    0.07
Q18   1   0.8792  0.0068  0.4198  11.00000  0.05    0.07
Q19   1   0.9868  0.3569  0.5593  11.00000  0.05    0.07
Q20   1   0.6660  0.0747  0.2207  11.00000  0.05    0.06
;
_shelx_res_checksum              87720
loop_
_space_group_symop_operation_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_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
N1 N 0.4250(2) 0.43486(13) 0.36934(6) 0.0187(2) Uani 1 1 d . . . . .
N2 N 0.6165(2) 0.26845(13) 0.40994(6) 0.0169(2) Uani 1 1 d . . . . .
N3 N 0.7269(2) 0.26335(13) 0.51319(7) 0.0186(2) Uani 1 1 d . . . . .
C3A C 0.5906(2) 0.44844(15) 0.54312(7) 0.0160(2) Uani 1 1 d . . . . .
C4 C 0.7074(3) 0.09792(16) 0.34169(8) 0.0211(2) Uani 1 1 d . . . . .
H4A H 0.816366 -0.019956 0.384456 0.032 Uiso 0.64(14) 1 calc R U P A 1
H4B H 0.870815 0.152766 0.296817 0.032 Uiso 0.64(14) 1 calc R U P A 1
H4C H 0.496219 0.046420 0.297974 0.032 Uiso 0.64(14) 1 calc R U P A 1
H4E H 0.781688 0.160289 0.278834 0.032 Uiso 0.36(14) 1 calc R U P A 2
H4D H 0.503916 0.006416 0.321416 0.032 Uiso 0.36(14) 1 calc R U P A 2
H4F H 0.897797 0.012525 0.378996 0.032 Uiso 0.36(14) 1 calc R U P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0203(4) 0.0174(4) 0.0181(4) 0.0015(3) 0.0023(3) 0.0034(3)
N2 0.0172(4) 0.0157(4) 0.0178(4) 0.0008(3) 0.0028(3) 0.0013(3)
N3 0.0210(4) 0.0172(4) 0.0174(4) 0.0008(3) 0.0020(3) 0.0021(3)
C3A 0.0155(4) 0.0156(4) 0.0169(4) 0.0022(3) 0.0022(3) 0.0000(3)
C4 0.0221(5) 0.0193(5) 0.0220(5) -0.0043(3) 0.0038(3) 0.0030(3)
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'
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
N2 N1 C3A 100.48(8) . 3_666 ?
N3 N2 N1 119.12(8) . . ?
N3 N2 C4 120.80(8) . . ?
N1 N2 C4 120.06(8) . . ?
N2 N3 C3A 100.44(7) . . ?
N3 C3A N1 140.05(9) . 3_666 ?
N3 C3A C3A 110.09(10) . 3_666 ?
N1 C3A C3A 109.87(10) 3_666 3_666 ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C4 H4E 109.5 . . ?
N2 C4 H4D 109.5 . . ?
H4E C4 H4D 109.5 . . ?
N2 C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
H4D C4 H4F 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
N1 N2 1.3414(11) . ?
N1 C3A 1.3538(12) 3_666 ?
N2 N3 1.3398(11) . ?
N2 C4 1.4591(12) . ?
N3 C3A 1.3528(12) . ?
C3A C3A 1.3870(17) 3_666 ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 H4E 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4F 0.9800 . ?
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
C3A N1 N2 N3 -0.03(11) 3_666 . . . ?
C3A N1 N2 C4 -178.91(8) 3_666 . . . ?
N1 N2 N3 C3A 0.05(11) . . . . ?
C4 N2 N3 C3A 178.92(8) . . . . ?
N2 N3 C3A N1 180.00(12) . . . 3_666 ?
N2 N3 C3A C3A -0.05(12) . . . 3_666 ?
