3-(3,5-Dinitrophenyl)-5-amino-1,2,4-oxadiazole: synthesis, structure and properties of a novel insensitive energetic material
Zhao, Binshan; Kuang, Baolong; Sun, Mou; Wang, Tingwei; Zhang, Chao; Xu, Meiqi; Li, Cong; Lu, Zujia; Zhang, Jian-guo; CrystEngComm 26 (2024) 2491–2497; doi:10.1039/D4CE00201F

data_7248377
_publ_section_title
;
 3-(3,5-Dinitrophenyl)-5-amino-1,2,4-oxadiazole: synthesis, structure and
 properties of a novel insensitive energetic material
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2491
_journal_page_last               2497
_journal_paper_doi               10.1039/D4CE00201F
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H3 Cl3 N4 O5'
_chemical_formula_sum            'C9 H3 Cl3 N4 O5'
_chemical_formula_weight         353.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-06-05
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2024-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4240(8)
_cell_length_b                   10.6544(14)
_cell_length_c                   11.243(7)
_cell_measurement_reflns_used    1505
_cell_measurement_temperature    120.1(2)
_cell_measurement_theta_max      26.1440
_cell_measurement_theta_min      4.1510
_cell_volume                     636.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8181
_diffrn_measurement_details
;
  1 omega    1.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000   30.0000 86

  2 omega  -51.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289    0.0000    0.0000 100

  3 omega  -23.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7727   37.0000  -60.0000 51

  4 omega    1.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000 -180.0000 36

  5 omega   32.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289 -178.0000   60.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0826593000
_diffrn_orient_matrix_UB_12      -0.0084591000
_diffrn_orient_matrix_UB_13      0.0567322000
_diffrn_orient_matrix_UB_21      -0.0818254000
_diffrn_orient_matrix_UB_22      0.0361222000
_diffrn_orient_matrix_UB_23      0.0286077000
_diffrn_orient_matrix_UB_31      -0.0659232000
_diffrn_orient_matrix_UB_32      -0.0554426000
_diffrn_orient_matrix_UB_33      0.0099941000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4110
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.70
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0189P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                2202
_reflns_number_total             2421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ce00201f2.cif
_cod_data_source_block           exp_8578
_cod_depositor_comments
'Adding full bibliography for 7248377--7248378.cif.'
_cod_database_code               7248377
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07