#------------------------------------------------------------------------------
#$Date: 2022-06-16 01:56:21 +0300 (Thu, 16 Jun 2022) $
#$Revision: 276055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/04/7710484.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_7710484
loop_
_publ_author_name
'Yang, Feng'
'Qin, Yaqi'
'Wang, Pengcheng'
'Lin, Qiuhan'
'Xu, Yuangang'
'Lu, Ming'
_publ_section_title
;
 Nitrogen-rich ion salts of 1-hydroxytetrazole-5-hydrazide: a new series
 of high energy compounds that combine good stability and high energy
 performance
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01173E
_journal_year                    2022
_chemical_formula_moiety         'C2 H3 N6 O2, C H9 N6, H2 O'
_chemical_formula_sum            'C3 H14 N12 O3'
_chemical_formula_weight         266.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-02 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                99.301(2)
_cell_angle_beta                 99.086(2)
_cell_angle_gamma                113.948(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2673(5)
_cell_length_b                   7.5778(5)
_cell_length_c                   11.4906(7)
_cell_measurement_reflns_used    5505
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      3.04
_cell_volume                     552.91(6)
_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 0.988
_diffrn_measured_fraction_theta_max 0.989
_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_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8535
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         3.038
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0389
_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)+(0.0611P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2144
_reflns_number_total             2530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01173e2.cif
_cod_data_source_block           YF_078_a
_cod_database_code               7710484
_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   0.971
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 1.06481(19) 0.77352(18) 0.68141(11) 0.0258(3) Uani 1 1 d . . . . .
C2 C 1.04087(19) 0.79343(18) 0.55474(11) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.32084(19) 0.11528(19) 0.21755(11) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.94673(16) 0.61774(15) 0.72108(9) 0.0272(2) Uani 1 1 d . . . . .
N2 N 1.01945(19) 0.65606(18) 0.84112(10) 0.0356(3) Uani 1 1 d . . . . .
N3 N 1.1786(2) 0.83442(19) 0.87291(11) 0.0398(3) Uani 1 1 d . . . . .
N4 N 1.20938(18) 0.90998(17) 0.77636(10) 0.0347(3) Uani 1 1 d . . . . .
N5 N 0.86853(17) 0.65231(16) 0.47639(9) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.782095 0.560800 0.502580 0.035 Uiso 1 1 calc R U . . .
N6 N 0.8230(2) 0.64790(19) 0.35183(10) 0.0339(3) Uani 1 1 d . . . . .
H6A H 0.938(3) 0.671(3) 0.3305(17) 0.047(5) Uiso 1 1 d . . . . .
H6B H 0.801(3) 0.760(3) 0.3502(18) 0.065(6) Uiso 1 1 d . . . . .
N7 N 0.45796(18) 0.27951(17) 0.19855(9) 0.0315(3) Uani 1 1 d . . . . .
H7 H 0.558123 0.368341 0.257370 0.038 Uiso 1 1 calc R U . . .
N8 N 0.4360(2) 0.3056(2) 0.07900(10) 0.0364(3) Uani 1 1 d . . . . .
H8A H 0.448(3) 0.427(3) 0.0869(17) 0.049(5) Uiso 1 1 d . . . . .
H8B H 0.544(3) 0.297(3) 0.0512(18) 0.050(5) Uiso 1 1 d . . . . .
N9 N 0.17018(19) -0.02155(17) 0.12470(10) 0.0344(3) Uani 1 1 d . . . . .
H9 H 0.155268 -0.000250 0.053307 0.041 Uiso 1 1 calc R U . . .
N10 N 0.0352(2) -0.20240(19) 0.14558(12) 0.0392(3) Uani 1 1 d . . . . .
H10B H -0.084(3) -0.231(3) 0.105(2) 0.062(6) Uiso 1 1 d . . . . .
H10A H 0.076(3) -0.298(3) 0.117(2) 0.068(6) Uiso 1 1 d . . . . .
N11 N 0.33173(18) 0.08686(18) 0.32927(10) 0.0337(3) Uani 1 1 d . . . . .
H11 H 0.240295 -0.018664 0.342013 0.040 Uiso 1 1 calc R U . . .
N12 N 0.49444(18) 0.23134(19) 0.42620(10) 0.0325(3) Uani 1 1 d . . . . .
H12B H 0.575(3) 0.172(3) 0.4540(17) 0.050(5) Uiso 1 1 d . . . . .
H12A H 0.436(3) 0.251(3) 0.4848(18) 0.052(5) Uiso 1 1 d . . . . .
O1 O 0.78870(15) 0.44956(14) 0.65837(9) 0.0386(3) Uani 1 1 d . . . . .
O2 O 1.17377(14) 0.93270(14) 0.52791(9) 0.0338(2) Uani 1 1 d . . . . .
O3 O 0.5711(2) 0.30141(19) 0.83869(11) 0.0493(3) Uani 1 1 d . . . . .
H3A H 0.622(4) 0.337(4) 0.781(2) 0.071(7) Uiso 1 1 d . . . . .
H3B H 0.475(4) 0.190(4) 0.806(2) 0.069(7) 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
N4 C1 N1 108.20(11) . . ?
N4 C1 C2 124.83(11) . . ?
N1 C1 C2 126.97(11) . . ?
O2 C2 N5 124.57(11) . . ?
O2 C2 C1 120.57(12) . . ?
N5 C2 C1 114.86(10) . . ?
N7 C3 N9 119.70(11) . . ?
N7 C3 N11 120.37(12) . . ?
N9 C3 N11 119.93(12) . . ?
O1 N1 N2 122.28(10) . . ?
O1 N1 C1 128.95(10) . . ?
N2 N1 C1 108.74(11) . . ?
N3 N2 N1 105.85(10) . . ?
N2 N3 N4 111.09(11) . . ?
C1 N4 N3 106.11(11) . . ?
C2 N5 N6 122.11(10) . . ?
C2 N5 H5 118.9 . . ?
N6 N5 H5 118.9 . . ?
N5 N6 H6A 105.1(12) . . ?
N5 N6 H6B 104.3(13) . . ?
H6A N6 H6B 106.4(18) . . ?
C3 N7 N8 118.24(11) . . ?
C3 N7 H7 120.9 . . ?
N8 N7 H7 120.9 . . ?
N7 N8 H8A 104.9(12) . . ?
N7 N8 H8B 107.7(12) . . ?
H8A N8 H8B 109.8(17) . . ?
C3 N9 N10 118.63(11) . . ?
C3 N9 H9 120.7 . . ?
N10 N9 H9 120.7 . . ?
N9 N10 H10B 106.2(15) . . ?
N9 N10 H10A 107.6(14) . . ?
H10B N10 H10A 110(2) . . ?
C3 N11 N12 119.23(11) . . ?
C3 N11 H11 120.4 . . ?
N12 N11 H11 120.4 . . ?
N11 N12 H12B 106.7(12) . . ?
N11 N12 H12A 105.6(13) . . ?
H12B N12 H12A 105.3(17) . . ?
H3A O3 H3B 104(2) . . ?
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 1.3247(17) . ?
C1 N1 1.3464(16) . ?
C1 C2 1.4777(17) . ?
C2 O2 1.2302(15) . ?
C2 N5 1.3297(16) . ?
C3 N7 1.3188(17) . ?
C3 N9 1.3282(17) . ?
C3 N11 1.3311(15) . ?
N1 O1 1.3100(14) . ?
N1 N2 1.3349(15) . ?
N2 N3 1.3176(17) . ?
N3 N4 1.3373(16) . ?
N5 N6 1.4089(14) . ?
N5 H5 0.8600 . ?
N6 H6A 0.87(2) . ?
N6 H6B 0.93(2) . ?
N7 N8 1.4128(14) . ?
N7 H7 0.8600 . ?
N8 H8A 0.88(2) . ?
N8 H8B 0.91(2) . ?
N9 N10 1.4096(16) . ?
N9 H9 0.8600 . ?
N10 H10B 0.84(2) . ?
N10 H10A 0.92(2) . ?
N11 N12 1.4058(15) . ?
N11 H11 0.8600 . ?
N12 H12B 0.919(19) . ?
N12 H12A 0.88(2) . ?
O3 H3A 0.84(2) . ?
O3 H3B 0.82(2) . ?
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
O3 H3A O1 0.84(2) 2.07(2) 2.8983(16) 171(2) . yes
N5 H5 N12 0.86 2.42 3.1256(16) 139.9 . yes
N5 H5 O1 0.86 2.10 2.7870(14) 136.4 . yes
N7 H7 N6 0.86 2.16 2.9758(16) 158.7 . yes
N9 H9 N3 0.86 2.31 2.9419(17) 130.4 1_444 yes
N11 H11 O2 0.86 2.32 2.9143(14) 126.8 1_445 yes
N6 H6A N1 0.87(2) 2.658(19) 3.1918(18) 120.9(15) 2_766 yes
N6 H6A N10 0.87(2) 2.552(19) 3.1442(17) 126.3(15) 1_665 yes
N6 H6A O1 0.87(2) 2.494(19) 3.2081(18) 140.0(16) 2_766 yes
N8 H8A O3 0.88(2) 2.16(2) 2.9988(19) 159.1(17) 2_666 yes
N12 H12B O2 0.919(19) 2.26(2) 3.1434(16) 160.0(16) 2_766 yes
N6 H6B O2 0.93(2) 2.44(2) 3.2434(17) 145.4(17) 2_776 yes
N8 H8B N3 0.91(2) 2.679(18) 3.375(2) 133.6(15) 2_766 yes
N8 H8B O3 0.91(2) 2.48(2) 3.0730(17) 122.4(14) 1_554 yes
N10 H10A N2 0.92(2) 2.66(2) 3.3285(18) 130.0(17) 2_656 yes
N10 H10A O3 0.92(2) 2.55(2) 3.225(2) 130.7(17) 2_656 yes
N12 H12A O2 0.88(2) 2.58(2) 3.0581(14) 115.4(15) 1_445 yes
O3 H3B N4 0.82(2) 2.14(2) 2.9343(17) 163(2) 1_445 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 O2 9.0(2) . . . . ?
N1 C1 C2 O2 -171.21(12) . . . . ?
N4 C1 C2 N5 -170.82(12) . . . . ?
N1 C1 C2 N5 9.02(19) . . . . ?
N4 C1 N1 O1 -178.92(12) . . . . ?
C2 C1 N1 O1 1.2(2) . . . . ?
N4 C1 N1 N2 -0.75(15) . . . . ?
C2 C1 N1 N2 179.40(12) . . . . ?
O1 N1 N2 N3 178.91(12) . . . . ?
C1 N1 N2 N3 0.60(15) . . . . ?
N1 N2 N3 N4 -0.24(16) . . . . ?
N1 C1 N4 N3 0.58(15) . . . . ?
C2 C1 N4 N3 -179.56(12) . . . . ?
N2 N3 N4 C1 -0.21(16) . . . . ?
O2 C2 N5 N6 1.0(2) . . . . ?
C1 C2 N5 N6 -179.24(11) . . . . ?
N9 C3 N7 N8 1.43(19) . . . . ?
N11 C3 N7 N8 -178.02(12) . . . . ?
N7 C3 N9 N10 175.17(13) . . . . ?
N11 C3 N9 N10 -5.4(2) . . . . ?
N7 C3 N11 N12 -1.75(19) . . . . ?
N9 C3 N11 N12 178.80(12) . . . . ?
