#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/11/7221189.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_7221189
loop_
_publ_author_name
'Yin, Xin'
'Wu, Jin-Ting'
'Jin, Xin'
'Xu, Cai-Xia'
'He, Piao'
'Li, Tong'
'Wang, Kun'
'Qin, Jian'
'Zhang, Jian-Guo'
_publ_section_title
;
 Nitrogen-rich salts of 1-aminotetrazol-5-one: oxygen-containing
 insensitive energetic materials with high thermal stability
;
_journal_issue                   74
_journal_name_full               'RSC Adv.'
_journal_page_first              60005
_journal_paper_doi               10.1039/C5RA07649H
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C2 H10 N10 O'
_chemical_formula_weight         190.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.964(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0441(5)
_cell_length_b                   12.0324(11)
_cell_length_c                   10.1093(8)
_cell_measurement_reflns_used    83.387
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.301
_cell_volume                     823.79(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4077
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0155P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                866
_reflns_number_total             1452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra07649h2.cif
_cod_data_source_block           140726b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7221189
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.4008(3) 0.27227(16) 0.5936(2) 0.0383(5) Uani 1 1 d .
N2 N 0.4068(3) 0.38413(17) 0.5821(2) 0.0483(6) Uani 1 1 d .
N3 N 0.2308(3) 0.41322(17) 0.5116(2) 0.0540(7) Uani 1 1 d .
N4 N 0.1095(3) 0.32254(17) 0.4759(2) 0.0467(6) Uani 1 1 d .
N5 N 0.5691(3) 0.21366(16) 0.6645(2) 0.0482(6) Uani 1 1 d .
H5B H 0.5967 0.1629 0.6085 0.072 Uiso 1 1 d R
H5C H 0.5458 0.1800 0.7369 0.072 Uiso 1 1 d R
N6 N 0.2510(3) 0.39866(16) 0.9060(2) 0.0503(7) Uani 1 1 d .
H6A H 0.2113 0.4664 0.9035 0.060 Uiso 1 1 calc R
H6B H 0.3720 0.3825 0.9464 0.060 Uiso 1 1 calc R
N7 N -0.1272(3) 0.45305(17) 0.7801(2) 0.0615(8) Uani 1 1 d .
H7B H -0.2246 0.4568 0.8204 0.092 Uiso 1 1 d R
H7C H -0.1719 0.4743 0.6927 0.092 Uiso 1 1 d R
N8 N -0.0602(3) 0.34248(17) 0.7851(2) 0.0472(6) Uani 1 1 d .
H8 H -0.1403 0.2903 0.7476 0.057 Uiso 1 1 calc R
N9 N 0.1866(3) 0.21427(17) 0.8519(2) 0.0482(6) Uani 1 1 d .
H9 H 0.3081 0.1976 0.8897 0.058 Uiso 1 1 calc R
N10 N 0.0480(3) 0.13077(16) 0.7935(2) 0.0503(6) Uani 1 1 d .
H10B H 0.0519 0.0779 0.8559 0.075 Uiso 1 1 d R
H10C H 0.0783 0.1016 0.7210 0.075 Uiso 1 1 d R
O1 O 0.1690(2) 0.13119(14) 0.52029(19) 0.0491(5) Uani 1 1 d .
C1 C 0.2184(3) 0.2321(2) 0.5281(3) 0.0372(6) Uani 1 1 d .
C2 C 0.1259(3) 0.3192(2) 0.8475(3) 0.0367(6) 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
N1 0.0321(11) 0.0294(13) 0.0469(15) 0.0022(10) -0.0003(10) -0.0027(10)
N2 0.0456(13) 0.0334(15) 0.0585(17) -0.0006(11) 0.0018(12) -0.0035(11)
N3 0.0512(14) 0.0349(14) 0.0687(19) 0.0026(12) 0.0044(13) -0.0013(11)
N4 0.0403(12) 0.0343(13) 0.0588(17) 0.0019(12) 0.0023(11) -0.0004(11)
N5 0.0391(12) 0.0448(14) 0.0532(17) 0.0044(11) 0.0002(11) 0.0029(10)
N6 0.0358(11) 0.0353(14) 0.0696(18) -0.0021(11) -0.0030(11) 0.0031(10)
N7 0.0465(13) 0.0359(15) 0.088(2) 0.0101(12) -0.0048(13) 0.0058(11)
N8 0.0343(12) 0.0310(13) 0.0675(19) 0.0017(11) -0.0008(11) -0.0003(10)
N9 0.0363(12) 0.0360(14) 0.0641(18) -0.0018(11) 0.0002(11) 0.0028(11)
N10 0.0494(13) 0.0346(14) 0.0627(18) -0.0006(11) 0.0083(12) -0.0066(10)
O1 0.0386(10) 0.0322(11) 0.0674(15) 0.0008(9) -0.0008(9) -0.0063(8)
C1 0.0337(14) 0.0374(17) 0.0385(18) -0.0031(13) 0.0065(12) -0.0049(13)
C2 0.0338(14) 0.0352(17) 0.0390(18) 0.0047(12) 0.0064(12) 0.0014(13)
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
N2 N1 C1 111.0(2)
N2 N1 N5 120.30(19)
C1 N1 N5 128.7(2)
N3 N2 N1 105.56(19)
N2 N3 N4 111.24(19)
C1 N4 N3 106.95(18)
N1 N5 H5B 108.8
N1 N5 H5C 109.2
H5B N5 H5C 109.5
C2 N6 H6A 120.0
C2 N6 H6B 120.0
H6A N6 H6B 120.0
N8 N7 H7B 108.9
N8 N7 H7C 109.3
H7B N7 H7C 109.5
C2 N8 N7 119.8(2)
C2 N8 H8 120.1
N7 N8 H8 120.1
C2 N9 N10 118.87(19)
C2 N9 H9 120.6
N10 N9 H9 120.6
N9 N10 H10B 109.2
N9 N10 H10C 109.3
H10B N10 H10C 109.5
O1 C1 N4 129.3(2)
O1 C1 N1 125.5(2)
N4 C1 N1 105.2(2)
N8 C2 N6 120.8(2)
N8 C2 N9 119.0(2)
N6 C2 N9 120.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.353(2)
N1 C1 1.362(3)
N1 N5 1.397(2)
N2 N3 1.296(2)
N3 N4 1.372(2)
N4 C1 1.353(3)
N5 H5B 0.8900
N5 H5C 0.8900
N6 C2 1.324(3)
N6 H6A 0.8600
N6 H6B 0.8600
N7 N8 1.408(3)
N7 H7B 0.8900
N7 H7C 0.8900
N8 C2 1.319(3)
N8 H8 0.8600
N9 C2 1.330(3)
N9 N10 1.412(2)
N9 H9 0.8600
N10 H10B 0.8900
N10 H10C 0.8900
O1 C1 1.259(3)
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
C1 N1 N2 N3 0.5(3)
N5 N1 N2 N3 179.9(2)
N1 N2 N3 N4 -0.3(3)
N2 N3 N4 C1 0.1(3)
N3 N4 C1 O1 -179.6(3)
N3 N4 C1 N1 0.2(3)
N2 N1 C1 O1 179.4(2)
N5 N1 C1 O1 0.0(4)
N2 N1 C1 N4 -0.4(3)
N5 N1 C1 N4 -179.8(2)
N7 N8 C2 N6 0.1(4)
N7 N8 C2 N9 179.7(2)
N10 N9 C2 N8 -2.1(3)
N10 N9 C2 N6 177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200548
