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#$Date: 2023-05-23 11:51:32 +0300 (Tue, 23 May 2023) $
#$Revision: 283961 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107254.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_8107254
loop_
_publ_author_name
'Huipeng, Zhao'
'Pengbao, Lian'
'Yumin, Yan'
'Lizhen, Chen'
'Jianlong, Wang'
_publ_section_title
;
 The crystal structure of 3-amino-1,2,4-triazolium
 2,4,5-trinitroimidazolate, C5H5O6N9
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              927
_journal_page_last               928
_journal_paper_doi               10.1515/ncrs-2022-0321
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration .
_chemical_formula_moiety         'C3 N5 O6, C2 H5 N4'
_chemical_formula_sum            'C5 H5 N9 O6'
_chemical_formula_weight         287.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6068(2)
_cell_length_b                   10.0191(4)
_cell_length_c                   18.3799(8)
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    140
_cell_measurement_theta_max      26.021
_cell_measurement_theta_min      2.315
_cell_volume                     1032.49(7)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.315
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) 
was 0.1127 before and 0.0543 after correction. The Ratio of minimum to 
maximum transmission is 0.9082. The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1.6(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0340
_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)+(0.0333P)²+0.2231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1876
_reflns_number_total             2104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0321_suppl.cif
_cod_data_source_block           5
_cod_database_code               8107254
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2.6(19)
 -1.6(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N6-H6A = N6-H6B
 0.87 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.1581(4) 0.3467(2) 0.40202(11) 0.0289(5) Uani 1 1 d . . . . .
O2 O 0.1356(4) 0.33102(19) 0.51979(11) 0.0236(5) Uani 1 1 d . . . . .
O3 O 0.8714(4) 0.6139(2) 0.32868(10) 0.0260(5) Uani 1 1 d . . . . .
O4 O 1.0630(5) 0.6970(2) 0.41970(12) 0.0440(7) Uani 1 1 d . . . . .
O5 O 1.0795(4) 0.6398(2) 0.56244(11) 0.0327(5) Uani 1 1 d . . . . .
O6 O 0.8268(4) 0.5552(2) 0.63872(10) 0.0277(5) Uani 1 1 d . . . . .
N1 N 0.2340(4) 0.3684(2) 0.46367(13) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.5578(4) 0.4958(2) 0.41201(12) 0.0172(5) Uani 1 1 d . . . . .
N3 N 0.5467(4) 0.4683(2) 0.53523(12) 0.0169(5) Uani 1 1 d . . . . .
N4 N 0.9062(4) 0.6282(2) 0.39414(13) 0.0206(5) Uani 1 1 d . . . . .
N5 N 0.8926(4) 0.5829(2) 0.57685(12) 0.0199(5) Uani 1 1 d . . . . .
C1 C 0.7446(5) 0.5586(3) 0.44219(14) 0.0167(6) Uani 1 1 d . . . . .
C2 C 0.7374(5) 0.5419(3) 0.51797(14) 0.0165(6) Uani 1 1 d . . . . .
C3 C 0.4495(5) 0.4454(3) 0.47035(14) 0.0162(6) Uani 1 1 d . . . . .
N6 N 0.3564(5) 0.6117(2) 0.72791(14) 0.0221(6) Uani 1 1 d D . . . .
H6A H 0.250(6) 0.668(3) 0.7452(18) 0.036(10) Uiso 1 1 d D . . . .
H6B H 0.469(5) 0.633(3) 0.6983(16) 0.038(10) Uiso 1 1 d D . . . .
N7 N 0.3411(5) 0.3964(2) 0.67237(13) 0.0198(5) Uani 1 1 d . . . . .
H7 H 0.433(6) 0.410(3) 0.6372(17) 0.026(9) Uiso 1 1 d . . . . .
N8 N 0.1117(4) 0.4287(2) 0.76341(13) 0.0192(5) Uani 1 1 d . . . . .
H8 H 0.037(7) 0.458(3) 0.8021(18) 0.035(10) Uiso 1 1 d . . . . .
N9 N 0.0681(5) 0.2991(2) 0.74079(13) 0.0235(6) Uani 1 1 d . . . . .
C4 C 0.2739(5) 0.4878(3) 0.72159(14) 0.0175(6) Uani 1 1 d . . . . .
C5 C 0.2107(6) 0.2843(3) 0.68597(16) 0.0234(6) Uani 1 1 d . . . . .
H5 H 0.223127 0.204449 0.658366 0.028 Uiso 1 1 calc R . . . .
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
O1 N1 C3 117.7(2) . .
O2 N1 O1 124.3(2) . .
O2 N1 C3 118.0(2) . .
C3 N2 C1 101.6(2) . .
C3 N3 C2 102.1(2) . .
O3 N4 C1 116.3(2) . .
O4 N4 O3 124.2(2) . .
O4 N4 C1 119.5(2) . .
O5 N5 O6 124.3(2) . .
O5 N5 C2 119.1(2) . .
O6 N5 C2 116.6(2) . .
N2 C1 N4 117.6(2) . .
N2 C1 C2 109.4(2) . .
C2 C1 N4 133.0(3) . .
N3 C2 N5 117.4(2) . .
N3 C2 C1 108.9(2) . .
C1 C2 N5 133.7(3) . .
N2 C3 N1 121.2(2) . .
N3 C3 N1 120.9(2) . .
N3 C3 N2 118.0(2) . .
H6A N6 H6B 124(3) . .
C4 N6 H6A 113(2) . .
C4 N6 H6B 116(2) . .
C4 N7 H7 125(2) . .
C4 N7 C5 106.8(2) . .
C5 N7 H7 127(2) . .
N9 N8 H8 119(2) . .
C4 N8 H8 130(2) . .
C4 N8 N9 111.4(2) . .
C5 N9 N8 103.4(2) . .
N6 C4 N7 126.8(3) . .
N8 C4 N6 127.1(3) . .
N8 C4 N7 106.2(2) . .
N7 C5 H5 123.8 . .
N9 C5 N7 112.3(2) . .
N9 C5 H5 123.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.230(3) .
O2 N1 1.228(3) .
O3 N4 1.227(3) .
O4 N4 1.212(3) .
O5 N5 1.222(3) .
O6 N5 1.227(3) .
N1 C3 1.439(4) .
N2 C1 1.342(4) .
N2 C3 1.332(3) .
N3 C2 1.337(3) .
N3 C3 1.331(3) .
N4 C1 1.445(3) .
N5 C2 1.448(3) .
C1 C2 1.403(4) .
N6 H6A 0.88(2) .
N6 H6B 0.86(2) .
N6 C4 1.330(4) .
N7 H7 0.84(3) .
N7 C4 1.341(3) .
N7 C5 1.363(4) .
N8 H8 0.88(3) .
N8 N9 1.386(3) .
N8 C4 1.329(4) .
N9 C5 1.295(4) .
C5 H5 0.9500 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2.6(19)
2 -1.6(19)
