What are the prospects of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides, 1,5-dioxides and their nitro derivatives as high-energy-density materials? Synthesis, experimental and predicted crystal structures, and calculated explosive properties
Baraboshkin, Nikita M.; Zelenov, Victor P.; Fedyanin, Ivan V.; CrystEngComm 25 (2023) 6719–6739; doi:10.1039/D3CE00964E

data_7247736
_publ_section_title
;
 What are the prospects of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides,
 1,5-dioxides and their nitro derivatives as high-energy-density
 materials? Synthesis, experimental and predicted crystal structures, and
 calculated explosive properties
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6719
_journal_page_last               6739
_journal_paper_doi               10.1039/D3CE00964E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H3 N5 O4'
_chemical_formula_sum            'C8 H3 N5 O4'
_chemical_formula_weight         233.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6598(2)
_cell_length_b                   12.7026(3)
_cell_length_c                   15.5750(4)
_cell_measurement_reflns_used    7039
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      77.3860
_cell_measurement_theta_min      2.7580
_cell_volume                     1713.28(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -121.00 -53.00   0.50    1.50    --  -48.70 -36.00-102.00  136
  2  \w    -97.00 -53.00   0.50    1.50    --  -48.70-154.00-121.00   88
  3  \w    -65.00 -15.00   0.50    1.50    --  -48.70  86.00-129.00  100
  4  \w    133.00 159.00   0.50    6.00    --  107.75  36.00  53.00   52
  5  \w    105.00 130.00   0.50    6.00    --  107.75  86.00-129.00   50
  6  \w     49.00  98.00   0.50    6.00    --  107.75 -86.00 112.00   98
  7  \w     61.00 106.00   0.50    6.00    --  107.75-121.00  36.00   90
  8  \w     35.00  93.00   0.50    1.50    --   48.70-125.00 -60.00  116
  9  \w     42.00  68.00   0.50    6.00    --  107.75 -61.00 150.00   52
 10  \w     36.00  69.00   0.50    6.00    --  107.75 -61.00-120.00   66
 11  \w    100.00 127.00   0.50    6.00    --  107.75 125.00 150.00   54
 12  \w    146.00 172.00   0.50    6.00    --  107.75 125.00 150.00   52
 13  \w     37.00  80.00   0.50    6.00    --  107.75 -77.00-180.00   86
 14  \w     40.00  65.00   0.50    6.00    --  107.75 -61.00 -90.00   50
 15  \w     98.00 132.00   0.50    6.00    --  107.75  45.00 150.00   68
 16  \w    143.00 178.00   0.50    6.00    --  107.75  45.00 150.00   70
 17  \w     70.00 100.00   0.50    6.00    --  107.75 -95.00  30.00   60
 18  \w     87.00 122.00   0.50    6.00    --  107.75  77.00  60.00   70
 19  \w    144.00 175.00   0.50    6.00    --  107.75  77.00  60.00   62
 20  \w     57.00  83.00   0.50    6.00    --  107.75 -77.00 120.00   52
 21  \w     44.00  70.00   0.50    6.00    --  107.75 -77.00  90.00   52
 22  \w     36.00  61.00   0.50    6.00    --  107.75 -61.00 -30.00   50
 23  \w     40.00  65.00   0.50    6.00    --  107.75-125.00   0.00   50
 24  \w     62.00  88.00   0.50    6.00    --  107.75 -77.00 150.00   52
 25  \w     72.00 102.00   0.50    6.00    --  107.75 -95.00 -90.00   60
 26  \w     99.00 150.00   0.50    6.00    --  107.75  45.00  30.00  102
 27  \w     36.00  61.00   0.50    6.00    --  107.75 -95.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0753862000
_diffrn_orient_matrix_UB_12      0.1070162000
_diffrn_orient_matrix_UB_13      0.0201907000
_diffrn_orient_matrix_UB_21      0.0341470000
_diffrn_orient_matrix_UB_22      -0.0162046000
_diffrn_orient_matrix_UB_23      0.0961463000
_diffrn_orient_matrix_UB_31      0.1574432000
_diffrn_orient_matrix_UB_32      0.0547864000
_diffrn_orient_matrix_UB_33      -0.0114003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10416
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.670
_diffrn_reflns_theta_min         5.681
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0439
_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/[\s^2^(Fo^2^)+(0.0858P)^2^+0.6883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1680
_reflns_number_total             1824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           z461201
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247736
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C8 H3 N5 O4'
_chemical_oxdiff_usercomment     Z461201
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.727
_olex2_refinement_description
;
;
_shelx_res_checksum              75134
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.773
_oxdiff_exptl_absorpt_empirical_full_min 0.327