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_7247738
_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 H4 N4 O3'
_chemical_formula_sum            'C8 H4 N4 O3'
_chemical_formula_weight         204.15
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-01-30
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.09790(10)
_cell_length_b                   15.91000(10)
_cell_length_c                   18.71190(10)
_cell_measurement_reflns_used    24861
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      77.2940
_cell_measurement_theta_min      3.6320
_cell_volume                     2400.54(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_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 0.997
_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   -118.00 -73.00   0.50    0.15    --  -48.70-125.00 -90.00   90
  2  \w   -116.00 -78.00   0.50    0.15    --  -48.70-125.00   0.00   76
  3  \w   -158.00 -79.00   0.50    0.45    --  -86.25 -78.00 117.00  158
  4  \w   -121.00 -39.00   0.50    0.15    --  -48.70 -38.00 -60.00  164
  5  \w   -108.00 -14.00   0.50    0.45    --  -86.25  78.00-118.00  188
  6  \w    -71.00  24.00   0.50    0.15    --  -48.70  78.00-118.00  190
  7  \w     68.00 101.00   0.50    0.45    --  107.75 -95.00-150.00   66
  8  \w     74.00 107.00   0.50    0.45    --  107.75-110.00-172.60   66
  9  \w     63.00 127.00   0.50    0.45    --  107.75-147.00-163.59  128
 10  \w     76.00 103.00   0.50    0.45    --  107.75 -95.00 -90.00   54
 11  \w     40.00  65.00   0.50    0.45    --  107.75-125.00 -30.00   50
 12  \w     39.00  74.00   0.50    0.45    --  107.75-103.00 -55.62   70
 13  \w     56.00  82.00   0.50    0.45    --  107.75 -95.00   0.00   52
 14  \w     40.00 110.00   0.50    0.45    --  107.75-125.00  30.00  140
 15  \w     40.00 111.00   0.50    0.45    --  107.75-125.00  90.00  142
 16  \w     41.00 101.00   0.50    0.45    --  107.75 -95.00 120.00  120
 17  \w     36.00  66.00   0.50    0.45    --  107.75 -61.00  60.00   60
 18  \w     36.00 100.00   0.50    0.45    --  107.75 -78.00 117.00  128
 19  \w    -21.00  71.00   0.50    0.15    --   48.70 -78.00 117.00  184
 20  \w     36.00  64.00   0.50    0.45    --  107.75 -61.00 150.00   56
 21  \w     45.00  70.00   0.50    0.45    --  107.75 -61.00 -60.00   50
 22  \w     51.00  77.00   0.50    0.45    --  107.75 -77.00-120.00   52
 23  \w     37.00  71.00   0.50    0.45    --  107.75 -61.00-150.00   68
 24  \w     37.00  65.00   0.50    0.45    --  107.75 -77.00-180.00   56
 25  \w     56.00  82.00   0.50    0.45    --  107.75 -76.00-178.96   52
 26  \w     45.00  71.00   0.50    0.45    --  107.75 -61.00-180.00   52
 27  \w    101.00 174.00   0.50    0.45    --  107.75  78.00-118.00  146
 28  \w     86.00 154.00   0.50    0.45    --  107.75  77.00 -90.00  136
 29  \w    130.00 171.00   0.50    0.45    --  107.75  72.00 -19.10   82
 30  \w    109.00 172.00   0.50    0.45    --  107.75  72.00 -36.27  126
 31  \w     99.00 125.00   0.50    0.45    --  107.75  72.00 -19.10   52
 32  \w    114.00 151.00   0.50    0.45    --  107.75  77.00   0.00   74
 33  \w    103.00 136.00   0.50    0.45    --  107.75  45.00 150.00   66
 34  \w    151.00 177.00   0.50    0.45    --  107.75  15.00 120.00   52
 35  \w    120.00 147.00   0.50    0.45    --  107.75  30.00  60.00   54
 36  \w    122.00 148.00   0.50    0.45    --  107.75  15.00 120.00   52
 37  \w    108.00 155.00   0.50    0.45    --  107.75  45.00   0.00   94
 38  \w    146.00 176.00   0.50    0.45    --  107.75  15.00-150.00   60
 39  \w    150.00 176.00   0.50    0.45    --  107.75  45.00-180.00   52
 40  \w     99.00 125.00   0.50    0.45    --  107.75  45.00-180.00   52
 41  \w    119.00 176.00   0.50    0.45    --  107.75 125.00-180.00  114
 42  \w    111.00 170.00   0.50    0.45    --  107.75 125.00  60.00  118
 43  \w    122.00 154.00   0.50    0.45    --  107.75 125.00 120.00   64
;
_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      -0.0773423000
_diffrn_orient_matrix_UB_12      -0.0820853000
_diffrn_orient_matrix_UB_13      -0.0313091000
_diffrn_orient_matrix_UB_21      0.1220750000
_diffrn_orient_matrix_UB_22      0.0006123000
_diffrn_orient_matrix_UB_23      -0.0584484000
_diffrn_orient_matrix_UB_31      0.1250306000
_diffrn_orient_matrix_UB_32      -0.0513564000
_diffrn_orient_matrix_UB_33      0.0493710000
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32530
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.866
_diffrn_reflns_theta_min         3.653
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.8672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4842
_reflns_number_total             5114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           z0231
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247738
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H4N4O3
_chemical_oxdiff_usercomment     Z0231
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C2C(H2C), C3A(H3A), C3B(H3B), C3C(H3C), C4A(H4A),
 C4B(H4B), C4C(H4C), C5A(H5A), C5B(H5B), C5C(H5C)
;
_shelx_res_checksum              82144
_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 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.694