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#$Date: 2024-04-05 02:12:11 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/81/7248194.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_7248194
loop_
_publ_author_name
'Zhao, Pinxu'
'Lin, Qiuhan'
'Huang, Haifeng'
'Li, Xiaoqiang'
'Yang, Jun'
_publ_section_title
;
 Synthesis of energetic salts based on
 4-nitro-5-dinitromethyl-1,2,3-1H-triazole
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1730
_journal_page_last               1737
_journal_paper_doi               10.1039/D3CE01184D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C5 H14 N14 O6'
_chemical_formula_weight         366.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-04-17 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.543(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.215(2)
_cell_length_b                   6.5819(7)
_cell_length_c                   13.6351(18)
_cell_measurement_reflns_used    7091
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.750
_cell_measurement_theta_min      4.963
_cell_volume                     1473.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19333
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.003
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0513P)²+0.7444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2343
_reflns_number_total             2886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01184d2.cif
_cod_data_source_block           d8v22495
_cod_depositor_comments
'Adding full bibliography for 7248192--7248195.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248194
_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   0.974
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
O1 O 0.28164(9) 0.0401(2) 0.21319(12) 0.0445(4) Uani 1 1 d . . . . .
O2 O 0.18396(8) 0.1695(2) 0.26281(12) 0.0448(4) Uani 1 1 d . . . . .
O3 O 0.26131(9) 0.7044(2) 0.35578(14) 0.0501(4) Uani 1 1 d . . . . .
O4 O 0.15609(10) 0.7475(2) 0.40823(16) 0.0598(5) Uani 1 1 d . . . . .
O5 O 0.10855(8) 0.4330(2) 0.48536(12) 0.0424(4) Uani 1 1 d . . . . .
O6 O 0.19391(9) 0.1802(2) 0.52185(12) 0.0431(4) Uani 1 1 d . . . . .
N1 N 0.37368(10) 0.3599(3) 0.51137(12) 0.0348(4) Uani 1 1 d . . . . .
N2 N 0.42734(10) 0.2390(3) 0.48416(13) 0.0365(4) Uani 1 1 d . . . . .
N3 N 0.39159(9) 0.1434(2) 0.39654(12) 0.0313(4) Uani 1 1 d . . . . .
N4 N 0.25659(10) 0.1328(2) 0.27553(13) 0.0321(4) Uani 1 1 d . . . . .
N5 N 0.21340(10) 0.6396(3) 0.40097(14) 0.0364(4) Uani 1 1 d . . . . .
N6 N 0.17509(10) 0.3545(2) 0.48522(13) 0.0326(4) Uani 1 1 d . . . . .
C1 C 0.31368(10) 0.2040(3) 0.36846(14) 0.0268(4) Uani 1 1 d . . . . .
C2 C 0.30142(11) 0.3389(3) 0.43945(14) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.22880(11) 0.4488(3) 0.44394(14) 0.0289(4) Uani 1 1 d . . . . .
N7 N 0.46095(10) 0.4277(2) 0.72610(13) 0.0341(4) Uani 1 1 d . . . . .
H7A H 0.4303 0.4197 0.6625 0.041 Uiso 1 1 calc R U . . .
H7B H 0.4391 0.4504 0.7749 0.041 Uiso 1 1 calc R U . . .
N8 N 0.57493(10) 0.3709(3) 0.67608(13) 0.0356(4) Uani 1 1 d . . . . .
H8A H 0.5452 0.3625 0.6121 0.043 Uiso 1 1 calc R U . . .
H8B H 0.6275 0.3565 0.6922 0.043 Uiso 1 1 calc DR U . . .
N9 N 0.58561(11) 0.4198(3) 0.84637(14) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.5630 0.4423 0.8944 0.050 Uiso 1 1 calc R U . . .
N10 N 0.67006(13) 0.3983(4) 0.87064(19) 0.0715(7) Uani 1 1 d . . . . .
H10A H 0.6928 0.4287 0.9349 0.086 Uiso 1 1 d R U . . .
H10B H 0.6819 0.2736 0.8602 0.086 Uiso 1 1 d DR U . . .
C4 C 0.54039(11) 0.4054(3) 0.74851(15) 0.0285(4) Uani 1 1 d . . . . .
N11 N -0.10782(11) 1.2498(3) 0.34682(16) 0.0459(5) Uani 1 1 d . . . . .
H11A H -0.1525 1.2660 0.2967 0.055 Uiso 1 1 d R U . . .
H11B H -0.1116 1.3180 0.3996 0.055 Uiso 1 1 d R U . . .
N12 N -0.09499(10) 1.0436(2) 0.37241(14) 0.0366(4) Uani 1 1 d . . . . .
H12 H -0.1313 0.9740 0.3908 0.044 Uiso 1 1 calc R U . . .
N13 N 0.02476(11) 1.0590(3) 0.33305(16) 0.0478(5) Uani 1 1 d . . . . .
H13A H 0.0692 1.0014 0.3291 0.057 Uiso 1 1 calc R U . . .
H13B H 0.0144 1.1846 0.3137 0.057 Uiso 1 1 calc R U . . .
N14 N -0.01254(10) 0.7659(3) 0.39791(15) 0.0414(5) Uani 1 1 d . . . . .
H14A H 0.0316 0.7056 0.3946 0.050 Uiso 1 1 calc R U . . .
H14B H -0.0473 0.7003 0.4209 0.050 Uiso 1 1 calc R U . . .
C5 C -0.02665(11) 0.9563(3) 0.36813(14) 0.0299(4) Uani 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
N5 O4 H14A 136.6 . . ?
C2 N1 N2 107.39(15) . . ?
C2 N1 H7A 144.8 . . ?
N2 N1 H7A 103.5 . . ?
N3 N2 N1 110.87(15) . . ?
N2 N3 C1 105.58(15) . . ?
O1 N4 O2 123.62(17) . . ?
O1 N4 C1 119.13(16) . . ?
O2 N4 C1 117.25(16) . . ?
O4 N5 O3 120.29(17) . . ?
O4 N5 C3 122.85(16) . . ?
O3 N5 C3 116.83(15) . . ?
O6 N6 O5 120.11(15) . . ?
O6 N6 C3 116.97(15) . . ?
O5 N6 C3 122.90(16) . . ?
N3 C1 C2 110.11(16) . . ?
N3 C1 N4 121.17(16) . . ?
C2 C1 N4 128.71(16) . . ?
N1 C2 C1 106.03(15) . . ?
N1 C2 C3 122.40(17) . . ?
C1 C2 C3 131.56(17) . . ?
N6 C3 N5 121.44(16) . . ?
N6 C3 C2 119.05(16) . . ?
N5 C3 C2 119.39(16) . . ?
C4 N7 H7A 120.0 . . ?
C4 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N9 N10 118.88(19) . . ?
C4 N9 H9 120.6 . . ?
N10 N9 H9 120.6 . . ?
N9 N10 H10A 109.7 . . ?
N9 N10 H10B 109.6 . . ?
H10A N10 H10B 109.1 . . ?
N7 C4 N8 121.15(18) . . ?
N7 C4 N9 118.55(18) . . ?
N8 C4 N9 120.29(18) . . ?
N12 N11 H11A 110.5 . . ?
N12 N11 H11B 109.9 . . ?
H11A N11 H11B 108.6 . . ?
C5 N12 N11 118.93(16) . . ?
C5 N12 H12 120.5 . . ?
N11 N12 H12 120.5 . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N13 C5 N14 121.36(18) . . ?
N13 C5 N12 119.81(18) . . ?
N14 C5 N12 118.83(17) . . ?
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
O1 N4 1.226(2) . ?
O2 N4 1.233(2) . ?
O3 N5 1.244(2) . ?
O4 N5 1.243(2) . ?
O5 N6 1.257(2) . ?
O6 N6 1.254(2) . ?
N1 C2 1.339(2) . ?
N1 N2 1.353(2) . ?
N2 N3 1.327(2) . ?
N3 C1 1.340(2) . ?
N4 C1 1.428(2) . ?
N5 C3 1.378(2) . ?
N6 C3 1.368(2) . ?
C1 C2 1.376(3) . ?
C2 C3 1.461(2) . ?
N7 C4 1.316(2) . ?
N7 H7A 0.8700 . ?
N7 H7B 0.8700 . ?
N8 C4 1.317(2) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N9 C4 1.330(3) . ?
N9 N10 1.397(3) . ?
N9 H9 0.8700 . ?
N10 H10A 0.8685 . ?
N10 H10B 0.8678 . ?
N11 N12 1.402(2) . ?
N11 H11A 0.8678 . ?
N11 H11B 0.8673 . ?
N12 C5 1.326(2) . ?
N12 H12 0.8700 . ?
N13 C5 1.313(3) . ?
N13 H13A 0.8700 . ?
N13 H13B 0.8700 . ?
N14 C5 1.317(3) . ?
N14 H14A 0.8700 . ?
N14 H14B 0.8700 . ?
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
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N10 H10B O1 0.87 2.46 3.301(3) 164.4 3_656
N10 H10A O6 0.87 2.49 3.001(3) 118.4 2_656
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N10 H10B O1 0.87 2.46 3.301(3) 164.4 3_656
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N7 H7A N1 0.87 2.04 2.894(2) 169.2 .
N7 H7A N2 0.87 2.69 3.407(2) 140.1 .
N7 H7B O1 0.87 2.59 3.046(2) 114.1 4_566
N7 H7B N3 0.87 2.15 2.953(2) 153.3 4_566
N8 H8A N2 0.87 2.38 3.170(2) 150.4 .
N8 H8B O3 0.87 2.24 3.020(2) 149.6 3_666
N9 H9 N2 0.87 2.53 3.180(2) 131.8 2_656
N11 H11A O3 0.87 2.38 3.210(3) 161.0 2
N11 H11B O5 0.87 2.26 3.100(3) 163.9 3_576
N12 H12 O6 0.87 2.09 2.937(2) 163.0 3_566
N13 H13A O2 0.87 2.65 3.247(2) 126.8 1_565
N13 H13A O4 0.87 2.28 2.995(2) 138.8 .
N14 H14A O4 0.87 2.11 2.866(2) 144.5 .
N14 H14A O5 0.87 2.35 3.011(2) 133.1 .
N14 H14B O5 0.87 2.08 2.926(2) 164.3 3_566
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
C2 N1 N2 N3 0.6(2) . . . . ?
H7A N1 N2 N3 163.6 . . . . ?
N1 N2 N3 C1 -0.5(2) . . . . ?
H14A O4 N5 O3 138.0 . . . . ?
H14A O4 N5 C3 -44.0 . . . . ?
N2 N3 C1 C2 0.2(2) . . . . ?
N2 N3 C1 N4 179.07(16) . . . . ?
O1 N4 C1 N3 -11.1(3) . . . . ?
O2 N4 C1 N3 168.96(16) . . . . ?
O1 N4 C1 C2 167.55(18) . . . . ?
O2 N4 C1 C2 -12.4(3) . . . . ?
N2 N1 C2 C1 -0.5(2) . . . . ?
H7A N1 C2 C1 -150.8 . . . . ?
N2 N1 C2 C3 -179.77(16) . . . . ?
H7A N1 C2 C3 29.9 . . . . ?
N3 C1 C2 N1 0.2(2) . . . . ?
N4 C1 C2 N1 -178.59(17) . . . . ?
N3 C1 C2 C3 179.39(18) . . . . ?
N4 C1 C2 C3 0.6(3) . . . . ?
O6 N6 C3 N5 179.43(18) . . . . ?
O5 N6 C3 N5 1.1(3) . . . . ?
O6 N6 C3 C2 3.5(3) . . . . ?
O5 N6 C3 C2 -174.88(17) . . . . ?
O4 N5 C3 N6 9.3(3) . . . . ?
O3 N5 C3 N6 -172.64(18) . . . . ?
O4 N5 C3 C2 -174.8(2) . . . . ?
O3 N5 C3 C2 3.3(3) . . . . ?
N1 C2 C3 N6 -96.2(2) . . . . ?
C1 C2 C3 N6 84.8(3) . . . . ?
N1 C2 C3 N5 87.8(2) . . . . ?
C1 C2 C3 N5 -91.3(3) . . . . ?
N10 N9 C4 N7 -179.38(19) . . . . ?
N10 N9 C4 N8 0.2(3) . . . . ?
N11 N12 C5 N13 -5.0(3) . . . . ?
N11 N12 C5 N14 176.09(19) . . . . ?
