#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:28:44 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284276 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246616.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_7246616
loop_
_publ_author_name
'Zhang, Jinhao'
'Jin, Zhiyuan'
'Xia, Yunlong'
'Li, Ying'
'Hao, Wenjia'
'Guo, Zhicheng'
'Wang, Ying'
'Peng, Rufang'
'Jin, Bo'
_publ_section_title
;
 A π-stacking highly stable insensitive energetic inner salt and its
 insensitive energetic salts
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3181
_journal_page_last               3188
_journal_paper_doi               10.1039/D3CE00209H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C3 H6 N8 O'
_chemical_formula_weight         170.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-12 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.280(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.6672(3)
_cell_length_b                   24.648(2)
_cell_length_c                   7.3252(7)
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      3.31
_cell_volume                     655.22(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3026
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.762
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.807
_diffrn_reflns_theta_min         3.306
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1192
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0386
_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)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.764
_reflns_Friedel_fraction_max     0.618
_reflns_number_gt                1039
_reflns_number_total             1192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00209h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7246615--7246618.cif.'
_cod_original_cell_volume        655.21(10)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7246616
_shelx_shelxl_version_number     2014/7
_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   0.973
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_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 0.3182(8) 0.36763(12) 0.5723(4) 0.0246(7) Uani 1 1 d . . . . .
C2 C 0.4185(8) 0.33502(12) 0.4219(4) 0.0249(7) Uani 1 1 d . . . . .
C3 C 0.5782(10) 0.31112(13) 0.1722(5) 0.0330(9) Uani 1 1 d . . . . .
H3 H 0.6500 0.3106 0.0555 0.040 Uiso 1 1 calc R U . . .
N1 N 0.3344(7) 0.42160(10) 0.5865(4) 0.0279(7) Uani 1 1 d . . . . .
N2 N 0.2248(8) 0.43586(12) 0.7478(4) 0.0368(8) Uani 1 1 d . . . . .
N3 N 0.1460(9) 0.39079(11) 0.8278(4) 0.0409(8) Uani 1 1 d . . . . .
N4 N 0.1991(8) 0.34766(11) 0.7230(4) 0.0319(7) Uani 1 1 d . . . . .
N5 N 0.5050(8) 0.35555(11) 0.2613(4) 0.0331(7) Uani 1 1 d . . . . .
N6 N 0.4312(8) 0.28187(11) 0.4347(4) 0.0313(7) Uani 1 1 d . . . . .
N7 N 0.5359(8) 0.26807(11) 0.2707(4) 0.0332(7) Uani 1 1 d . . . . .
H7 H 0.5698 0.2353 0.2363 0.040 Uiso 1 1 calc R U . . .
N8 N 0.8560(8) 0.54643(10) 0.6477(4) 0.0298(7) Uani 1 1 d D . . . .
H8D H 1.033(7) 0.5354(10) 0.735(3) 0.036 Uiso 1 1 d D U . . .
H8A H 0.731(7) 0.5166(9) 0.598(4) 0.036 Uiso 1 1 d D U . . .
H8B H 0.706(7) 0.5692(10) 0.687(4) 0.036 Uiso 1 1 d D U . . .
H8C H 0.963(8) 0.5618(11) 0.554(3) 0.036 Uiso 1 1 d D U . . .
O1 O 0.4296(7) 0.45808(8) 0.4725(3) 0.0383(7) 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
N1 C1 N4 108.5(3) . . ?
N1 C1 C2 126.7(3) . . ?
N4 C1 C2 124.8(3) . . ?
N6 C2 N5 115.0(3) . . ?
N6 C2 C1 120.5(3) . . ?
N5 C2 C1 124.5(3) . . ?
N7 C3 N5 110.6(3) . . ?
N7 C3 H3 124.7 . . ?
N5 C3 H3 124.7 . . ?
O1 N1 C1 130.4(3) . . ?
O1 N1 N2 121.4(3) . . ?
C1 N1 N2 108.2(3) . . ?
N3 N2 N1 106.5(3) . . ?
N2 N3 N4 111.0(3) . . ?
C1 N4 N3 105.8(3) . . ?
C3 N5 C2 102.0(3) . . ?
C2 N6 N7 101.5(3) . . ?
C3 N7 N6 110.9(3) . . ?
C3 N7 H7 124.5 . . ?
N6 N7 H7 124.5 . . ?
H8D N8 H8A 108.4(17) . . ?
H8D N8 H8B 113(2) . . ?
H8A N8 H8B 110(2) . . ?
H8D N8 H8C 109(2) . . ?
H8A N8 H8C 106.0(18) . . ?
H8B N8 H8C 110.1(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
C1 N1 1.335(4) . ?
C1 N4 1.338(4) . ?
C1 C2 1.453(4) . ?
C2 N6 1.314(4) . ?
C2 N5 1.360(4) . ?
C3 N7 1.305(4) . ?
C3 N5 1.322(4) . ?
C3 H3 0.9300 . ?
N1 O1 1.309(3) . ?
N1 N2 1.348(4) . ?
N2 N3 1.307(4) . ?
N3 N4 1.342(4) . ?
N6 N7 1.356(4) . ?
N7 H7 0.8600 . ?
N8 H8D 0.89(2) . ?
N8 H8A 0.92(2) . ?
N8 H8B 0.87(2) . ?
N8 H8C 0.92(2) . ?
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
N1 C1 C2 N6 171.9(3) . . . . ?
N4 C1 C2 N6 -6.7(5) . . . . ?
N1 C1 C2 N5 -8.0(5) . . . . ?
N4 C1 C2 N5 173.3(3) . . . . ?
N4 C1 N1 O1 -179.0(3) . . . . ?
C2 C1 N1 O1 2.2(5) . . . . ?
N4 C1 N1 N2 0.1(3) . . . . ?
C2 C1 N1 N2 -178.8(3) . . . . ?
O1 N1 N2 N3 179.3(3) . . . . ?
C1 N1 N2 N3 0.2(3) . . . . ?
N1 N2 N3 N4 -0.3(4) . . . . ?
N1 C1 N4 N3 -0.3(3) . . . . ?
C2 C1 N4 N3 178.6(3) . . . . ?
N2 N3 N4 C1 0.4(4) . . . . ?
N7 C3 N5 C2 0.5(4) . . . . ?
N6 C2 N5 C3 -0.6(4) . . . . ?
C1 C2 N5 C3 179.3(3) . . . . ?
N5 C2 N6 N7 0.5(4) . . . . ?
C1 C2 N6 N7 -179.5(3) . . . . ?
N5 C3 N7 N6 -0.2(4) . . . . ?
C2 N6 N7 C3 -0.1(4) . . . . ?
