#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:40:45 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298997 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/35/7063561.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_7063561
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         'C2 H3 N6, Cl'
_chemical_formula_sum            'C2 H3 Cl N6'
_chemical_formula_weight         146.55
_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                 114.532(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5074(3)
_cell_length_b                   13.0530(6)
_cell_length_c                   7.7581(4)
_cell_measurement_reflns_used    3846
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      3.12
_cell_volume                     599.49(5)
_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 II CPAD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         3.121
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0263
_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)+(0.0368P)²+0.0531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1483
_reflns_number_total             1749
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04427d2.cif
_cod_data_source_block           a1799
_cod_depositor_comments
'Adding full bibliography for 7063553--7063561.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063561
_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   0.862
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_file
;
TITL a1799 in P2(1)/n
    a1799.res
    created by SHELXL-2018/3 at 13:10:13 on 03-Dec-2023

CELL  0.71073   6.5074  13.0530   7.7581   90.000  114.532   90.000
ZERR    4.000   0.0003   0.0006   0.0004    0.000    0.002    0.000
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C H N CL
UNIT 8 12 24 4
TEMP -173
L.S. 10
BOND
SIZE 0.28 0.1 0.1
ACTA

CONF
BOND $H
HTAB
REM Instructions for potential hydrogen bonds
HTAB N3 Cl1
EQIV $1 x, y, z+1
HTAB N4 Cl1_$1
EQIV $2 -x+2, -y+1, -z+1
HTAB N4 Cl1_$2

FMAP 2
PLAN 20

WGHT    0.036800    0.053100
FVAR       0.27192
CL1   4    0.809931    0.554233    0.232101    11.00000    0.02250    0.02111 =
         0.01733    0.00103    0.01207    0.00384
N1    3    0.317877    0.714508    0.501592    11.00000    0.02036    0.01825 =
         0.01473    0.00007    0.00534    0.00151
N2    3    0.412023    0.686343    0.392635    11.00000    0.02679    0.02054 =
         0.01484    0.00154    0.00790    0.00204
N3    3    0.590491    0.621883    0.492264    11.00000    0.02176    0.01691 =
         0.01507   -0.00068    0.01053    0.00015
H3    2    0.673803    0.597270    0.429943    11.00000    0.03664
N4    3    0.767246    0.551102    0.802756    11.00000    0.02119    0.02587 =
         0.01538    0.00121    0.00886    0.00875
H4A   2    0.775664    0.550425    0.915005    11.00000    0.03751
H4B   2    0.875451    0.518750    0.781724    11.00000    0.03894
N5    3    0.377530    0.680497    0.819892    11.00000    0.01589    0.01586 =
         0.01699   -0.00016    0.00612    0.00268
N6    3    0.331832    0.688158    0.941553    11.00000    0.02813    0.02764 =
         0.02225    0.00159    0.01487    0.00683
C4    1    0.614928    0.608238    0.671896    11.00000    0.01528    0.01391 =
         0.01394   -0.00295    0.00688   -0.00241
C5    1    0.436156    0.668398    0.674639    11.00000    0.01565    0.01461 =
         0.01342   -0.00093    0.00643    0.00092
HKLF 4




REM  a1799 in P2(1)/n
REM wR2 = 0.0734, GooF = S = 1.151, Restrained GooF = 1.151 for all data
REM R1 = 0.0263 for 1483 Fo > 4sig(Fo) and 0.0323 for all 1749 data
REM 94 parameters refined using 0 restraints

END

WGHT      0.0360      0.0605

REM Instructions for potential hydrogen bonds
HTAB N3 Cl1
HTAB N4 Cl1_$1
HTAB N4 Cl1_$2

REM Highest difference peak  0.412,  deepest hole -0.315,  1-sigma level  0.068
Q1    1   0.5225  0.6363  0.6847  11.00000  0.05    0.41
Q2    1   0.5958  0.6114  0.5837  11.00000  0.05    0.26
Q3    1   0.6791  0.4597  0.7431  11.00000  0.05    0.23
Q4    1   0.3859  0.6879  0.5987  11.00000  0.05    0.23
Q5    1   0.5263  0.6507  0.4516  11.00000  0.05    0.22
Q6    1   0.7243  0.4598  0.1357  11.00000  0.05    0.19
Q7    1   0.8316  0.6623  0.5603  11.00000  0.05    0.19
Q8    1   0.7469  0.6860  0.5740  11.00000  0.05    0.18
Q9    1   0.6804  0.4313  0.9210  11.00000  0.05    0.18
Q10   1   0.2163  0.7520  0.4744  11.00000  0.05    0.18
Q11   1   0.6301  0.4665  0.2277  11.00000  0.05    0.17
Q12   1   0.7433  0.6981  0.7737  11.00000  0.05    0.17
Q13   1   0.8400  0.6443  0.2032  11.00000  0.05    0.17
Q14   1   0.2616  0.5688  0.9400  11.00000  0.05    0.17
Q15   1   0.7849  0.4490  0.2608  11.00000  0.05    0.16
Q16   1   0.9078  0.6672  0.6597  11.00000  0.05    0.16
Q17   1   0.6801  0.6672  0.0867  11.00000  0.05    0.16
Q18   1   0.7457  0.4427  0.5552  11.00000  0.05    0.16
Q19   1   0.3512  0.7947  0.9149  11.00000  0.05    0.16
Q20   1   0.6681  0.6802  0.1571  11.00000  0.05    0.15
;
_shelx_res_checksum              30554
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
Cl1 Cl 0.80993(5) 0.55423(2) 0.23210(4) 0.01904(10) Uani 1 1 d . . . . .
N1 N 0.31788(17) 0.71451(8) 0.50159(14) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.41202(18) 0.68634(8) 0.39264(14) 0.0210(2) Uani 1 1 d . . . . .
N3 N 0.59049(17) 0.62188(7) 0.49226(14) 0.0169(2) Uani 1 1 d . . . . .
H3 H 0.674(3) 0.5973(12) 0.430(2) 0.037(4) Uiso 1 1 d . . . . .
N4 N 0.76725(19) 0.55110(8) 0.80276(15) 0.0204(2) Uani 1 1 d . . . . .
H4A H 0.776(3) 0.5504(11) 0.915(3) 0.038(5) Uiso 1 1 d . . . . .
H4B H 0.875(3) 0.5187(14) 0.782(2) 0.039(5) Uiso 1 1 d . . . . .
N5 N 0.37753(16) 0.68050(7) 0.81989(14) 0.0165(2) Uani 1 1 d . . . . .
N6 N 0.33183(19) 0.68816(8) 0.94155(15) 0.0245(2) Uani 1 1 d . . . . .
C4 C 0.61493(18) 0.60824(8) 0.67190(15) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.43616(18) 0.66840(8) 0.67464(15) 0.0144(2) Uani 1 1 d . . . . .
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
Cl1 0.02250(16) 0.02111(16) 0.01733(15) 0.00103(10) 0.01207(12) 0.00384(10)
N1 0.0204(5) 0.0183(5) 0.0147(4) 0.0001(4) 0.0053(4) 0.0015(4)
N2 0.0268(5) 0.0205(5) 0.0148(5) 0.0015(4) 0.0079(4) 0.0020(4)
N3 0.0218(5) 0.0169(5) 0.0151(4) -0.0007(4) 0.0105(4) 0.0002(4)
N4 0.0212(5) 0.0259(5) 0.0154(5) 0.0012(4) 0.0089(4) 0.0088(4)
N5 0.0159(5) 0.0159(4) 0.0170(5) -0.0002(3) 0.0061(4) 0.0027(3)
N6 0.0281(6) 0.0276(6) 0.0223(5) 0.0016(4) 0.0149(5) 0.0068(4)
C4 0.0153(5) 0.0139(5) 0.0139(5) -0.0029(4) 0.0069(4) -0.0024(4)
C5 0.0156(5) 0.0146(5) 0.0134(5) -0.0009(4) 0.0064(4) 0.0009(4)
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'
Cl Cl 0.1484 0.1585 '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 C5 106.83(10) . . ?
N1 N2 N3 108.99(9) . . ?
C4 N3 N2 111.71(9) . . ?
C4 N3 H3 130.9(11) . . ?
N2 N3 H3 117.4(10) . . ?
C4 N4 H4A 120.2(12) . . ?
C4 N4 H4B 121.7(11) . . ?
H4A N4 H4B 117.6(16) . . ?
N6 N5 C5 178.19(12) . . ?
N4 C4 N3 126.88(10) . . ?
N4 C4 C5 131.68(11) . . ?
N3 C4 C5 101.42(9) . . ?
N5 C5 N1 121.92(10) . . ?
N5 C5 C4 127.04(10) . . ?
N1 C5 C4 111.03(10) . . ?
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 1.2865(14) . ?
N1 C5 1.3780(14) . ?
N2 N3 1.3816(14) . ?
N3 C4 1.3473(14) . ?
N3 H3 0.921(16) . ?
N4 C4 1.3167(15) . ?
N4 H4A 0.85(2) . ?
N4 H4B 0.892(17) . ?
N5 N6 1.1056(14) . ?
N5 C5 1.3407(14) . ?
C4 C5 1.4110(15) . ?
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
N3 H3 Cl1 0.921(16) 2.141(17) 3.0473(10) 167.6(15) . yes
N4 H4A Cl1 0.85(2) 2.38(2) 3.2257(11) 177.6(16) 1_556 yes
N4 H4B Cl1 0.892(17) 2.301(17) 3.1862(11) 171.7(15) 3_766 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 0.21(12) . . . . ?
N1 N2 N3 C4 -0.56(13) . . . . ?
N2 N3 C4 N4 179.56(11) . . . . ?
N2 N3 C4 C5 0.61(12) . . . . ?
N2 N1 C5 N5 -178.57(10) . . . . ?
N2 N1 C5 C4 0.17(13) . . . . ?
N4 C4 C5 N5 -0.7(2) . . . . ?
N3 C4 C5 N5 178.18(11) . . . . ?
N4 C4 C5 N1 -179.35(12) . . . . ?
N3 C4 C5 N1 -0.48(12) . . . . ?
