#------------------------------------------------------------------------------
#$Date: 2025-07-06 17:05:59 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300706 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/01/7250106.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_7250106
loop_
_publ_author_name
'Yang, Feng'
'Jiang, Shuaijie'
'Xu, Yuangang'
'Wang, Quan'
'He, Zhiwei'
'Lu, Ming'
_publ_section_title
;
 Constructing an energetic hydroxytetrazole with high thermal stability by
 linking aminotriazole to 1-hydroxytetrazole
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2570
_journal_page_last               2576
_journal_paper_doi               10.1039/D5CE00030K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C3 H4 N8 O, H4 N2'
_chemical_formula_sum            'C3 H8 N10 O'
_chemical_formula_weight         200.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-06 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.5314(4)
_cell_length_b                   25.0039(17)
_cell_length_c                   9.2895(6)
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.73
_cell_volume                     1517.07(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            724
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         2.732
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0743
_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)+(0.0248P)²+20.9846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                664
_reflns_number_total             724
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00030k2.cif
_cod_data_source_block           YF_110
_cod_depositor_comments
'Adding full bibliography for 7250102--7250107.cif.'
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7250106
_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   0.972
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, -z'
'-x+1/2, y, -z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x+1, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, z'
'x-1/2, -y, z-1/2'
'x-1/2, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z-1/2'
'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
C1 C 0.500000 0.3644(2) 0.6761(6) 0.0211(14) Uani 1 2 d S T P . .
C2 C 0.500000 0.3363(2) 0.5394(6) 0.0222(14) Uani 1 2 d S T P . .
C3 C 0.500000 0.3189(2) 0.3188(7) 0.0324(17) Uani 1 2 d S T P . .
N1 N 0.500000 0.41776(19) 0.6949(5) 0.0206(12) Uani 1 2 d S T P . .
N2 N 0.500000 0.4286(2) 0.8363(5) 0.0274(13) Uani 1 2 d S T P . .
N3 N 0.500000 0.3820(2) 0.9029(5) 0.0269(13) Uani 1 2 d S T P . .
N4 N 0.500000 0.3417(2) 0.8064(5) 0.0223(12) Uani 1 2 d S T P . .
N5 N 0.500000 0.36073(19) 0.4081(6) 0.0350(16) Uani 1 2 d S T P . .
N6 N 0.500000 0.28376(19) 0.5363(5) 0.0272(13) Uani 1 2 d S T P . .
N7 N 0.500000 0.27314(19) 0.3908(5) 0.0281(14) Uani 1 2 d S T P . .
H7 H 0.500000 0.241787 0.352753 0.034 Uiso 1 2 calc R U P . .
N8 N 0.500000 0.3208(2) 0.1747(6) 0.062(3) Uani 1 2 d S T P . .
H8A H 0.500000 0.291582 0.125656 0.075 Uiso 1 2 calc R U P . .
H8B H 0.500000 0.351120 0.131163 0.075 Uiso 1 2 calc R U P . .
N9 N 0.7289(7) 0.54432(14) 0.8269(4) 0.0364(11) Uani 1 1 d . . . . .
H9A H 0.784625 0.515350 0.866437 0.055 Uiso 1 1 d R U . . .
H9B H 0.783488 0.573475 0.866287 0.055 Uiso 1 1 d R U . . .
O1 O 0.500000 0.45605(16) 0.5974(5) 0.0282(12) Uani 1 2 d S T P . .
H1 H 0.582786 0.479175 0.620383 0.042 Uiso 0.5 1 calc R U P . .
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
N4 C1 N1 107.7(5) . . ?
N4 C1 C2 126.0(5) . . ?
N1 C1 C2 126.4(5) . . ?
N6 C2 N5 115.3(5) . . ?
N6 C2 C1 120.2(5) . . ?
N5 C2 C1 124.5(5) . . ?
N7 C3 N5 111.3(5) . . ?
N7 C3 N8 122.3(6) . . ?
N5 C3 N8 126.4(6) . . ?
O1 N1 N2 121.7(5) . . ?
O1 N1 C1 129.1(5) . . ?
N2 N1 C1 109.2(5) . . ?
N3 N2 N1 106.2(5) . . ?
N2 N3 N4 110.4(5) . . ?
C1 N4 N3 106.5(5) . . ?
C3 N5 C2 101.8(5) . . ?
C2 N6 N7 102.4(5) . . ?
C3 N7 N6 109.2(5) . . ?
C3 N7 H7 125.4 . . ?
N6 N7 H7 125.4 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
N9 N9 H9A 109.1 3_656 . ?
N9 N9 H9B 109.1 3_656 . ?
H9A N9 H9B 109.5 . . ?
N1 O1 H1 109.5 . . ?
N1 O1 H1 109(2) . 10_655 ?
H1 O1 H1 82.5 . 10_655 ?
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
C1 N4 1.337(7) . ?
C1 N1 1.346(7) . ?
C1 C2 1.450(8) . ?
C2 N6 1.315(8) . ?
C2 N5 1.364(8) . ?
C3 N7 1.326(8) . ?
C3 N5 1.334(8) . ?
C3 N8 1.340(8) . ?
N1 O1 1.318(6) . ?
N1 N2 1.341(7) . ?
N2 N3 1.321(7) . ?
N3 N4 1.348(7) . ?
N6 N7 1.377(7) . ?
N7 H7 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 N9 1.455(7) 3_656 ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
O1 H1 0.8200 . ?
O1 H1 0.82(9) 10_655 ?
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
N7 H7 N4 0.86 2.13 2.976(7) 167.4 15 yes
N8 H8A N6 0.86 2.06 2.912(8) 171.8 15 yes
N8 H8B N3 0.86 2.26 2.952(8) 138.0 1_554 yes
N9 H9A O1 0.89 2.07 2.916(5) 158.0 3_656 yes
N9 H9B N5 0.89 2.20 3.056(5) 160.2 11_666 yes
O1 H1 N9 0.82 2.69 3.414(5) 147.8 . yes
O1 H1 N9 0.82 2.10 2.916(5) 173.9 3_656 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
N4 C1 C2 N6 0.000(3) . . . . ?
N1 C1 C2 N6 180.000(2) . . . . ?
N4 C1 C2 N5 180.000(2) . . . . ?
N1 C1 C2 N5 0.000(3) . . . . ?
N4 C1 N1 O1 180.000(2) . . . . ?
C2 C1 N1 O1 0.000(3) . . . . ?
N4 C1 N1 N2 0.000(2) . . . . ?
C2 C1 N1 N2 180.000(2) . . . . ?
O1 N1 N2 N3 180.000(2) . . . . ?
C1 N1 N2 N3 0.000(2) . . . . ?
N1 N2 N3 N4 0.000(2) . . . . ?
N1 C1 N4 N3 0.000(2) . . . . ?
C2 C1 N4 N3 180.000(2) . . . . ?
N2 N3 N4 C1 0.000(2) . . . . ?
N7 C3 N5 C2 0.000(2) . . . . ?
N8 C3 N5 C2 180.000(2) . . . . ?
N6 C2 N5 C3 0.000(2) . . . . ?
C1 C2 N5 C3 180.000(2) . . . . ?
N5 C2 N6 N7 0.000(2) . . . . ?
C1 C2 N6 N7 180.000(2) . . . . ?
N5 C3 N7 N6 0.000(2) . . . . ?
N8 C3 N7 N6 180.000(2) . . . . ?
C2 N6 N7 C3 0.000(2) . . . . ?
