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_7247737
_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_absolute_configuration unk
_chemical_formula_moiety         'C8 H3 N5 O5'
_chemical_formula_sum            'C8 H3 N5 O5'
_chemical_formula_weight         249.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.40027(12)
_cell_length_b                   10.46252(9)
_cell_length_c                   6.13809(5)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      77.0910
_cell_measurement_theta_min      5.2140
_cell_volume                     924.784(13)
_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      99.98(15)
_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 1.000
_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   -111.00 -14.00   0.50    0.36    --  -86.25  83.00  31.00  194
  2  \w    -44.00 -14.00   0.50    0.36    --  -86.25  39.00-117.00   60
  3  \w    -44.00  23.00   0.50    0.09    --  -48.70  39.00-117.00  134
  4  \w     68.00  94.00   0.50    0.36    --  107.75-153.00-136.00   52
  5  \w     82.00 107.00   0.50    0.36    --  107.75-125.00-120.00   50
  6  \w     39.00  72.00   0.50    0.36    --  107.75-108.00-105.53   66
  7  \w     39.00  72.00   0.50    0.36    --  107.75-125.00-120.00   66
  8  \w     82.00 107.00   0.50    0.36    --  107.75 -83.00 -89.00   50
  9  \w     79.00 104.00   0.50    0.36    --  107.75-108.00-105.53   50
 10  \w     46.00  89.00   0.50    0.36    --  107.75-125.00   0.00   86
 11  \w     50.00  75.00   0.50    0.36    --  107.75-121.00  23.00   50
 12  \w     56.00 103.00   0.50    0.36    --  107.75-107.00 169.67   94
 13  \w    -23.00  44.00   0.50    0.09    --   48.70 -39.00  88.00  134
 14  \w     43.00  76.00   0.50    0.36    --  107.75 -77.00 120.00   66
 15  \w     42.00  89.00   0.50    0.36    --  107.75 -77.00  30.00   94
 16  \w     45.00  83.00   0.50    0.36    --  107.75 -69.00 176.30   76
 17  \w     38.00  91.00   0.50    0.36    --  107.75 -77.00   0.00  106
 18  \w     49.00  82.00   0.50    0.36    --  107.75 -77.00 -30.00   66
 19  \w     43.00  71.00   0.50    0.36    --  107.75 -61.00  30.00   56
 20  \w     37.00  63.00   0.50    0.36    --  107.75 -61.00  90.00   52
 21  \w     36.00  69.00   0.50    0.36    --  107.75 -61.00 -30.00   66
 22  \w     36.00  70.00   0.50    0.36    --  107.75 -61.00 -60.00   68
 23  \w     36.00  61.00   0.50    0.36    --  107.75 -61.00-120.00   50
 24  \w     45.00  71.00   0.50    0.36    --  107.75 -77.00-180.00   52
 25  \w     38.00  71.00   0.50    0.36    --  107.75 -61.00  60.00   66
 26  \w    127.00 153.00   0.50    0.36    --  107.75  30.00   0.00   52
 27  \w    100.00 133.00   0.50    0.36    --  107.75  45.00 -60.00   66
 28  \w     97.00 178.00   0.50    0.36    --  107.75  39.00-117.00  162
 29  \w    153.00 178.00   0.50    0.36    --  107.75  45.00 -60.00   50
 30  \w    107.00 153.00   0.50    0.36    --  107.75  45.00  30.00   92
 31  \w     97.00 122.00   0.50    0.36    --  107.75  30.00 150.00   50
 32  \w    130.00 178.00   0.50    0.36    --  107.75  30.00 150.00   96
 33  \w    117.00 155.00   0.50    0.36    --  107.75  83.00  31.00   76
 34  \w    137.00 163.00   0.50    0.36    --  107.75 125.00 -60.00   52
 35  \w     76.00 158.00   0.50    0.36    --  107.75 153.00 -94.00  164
 36  \w     99.00 125.00   0.50    0.36    --  107.75 125.00 -60.00   52
 37  \w    124.00 149.00   0.50    0.36    --  107.75 121.00 105.00   50
 38  \w   -158.00 -75.00   0.50    0.36    --  -86.25 -39.00  88.00  166
 39  \w   -121.00 -39.00   0.50    0.09    --  -48.70 -39.00  88.00  164
 40  \w   -158.00 -79.00   0.50    0.36    --  -86.25 -83.00 -89.00  158
 41  \w   -120.00 -54.00   0.50    0.09    --  -48.70-153.00-136.00  132
 42  \w   -146.00 -54.00   0.50    0.36    --  -86.25-153.00-136.00  184
;
_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      0.0456779000
_diffrn_orient_matrix_UB_12      0.1128969000
_diffrn_orient_matrix_UB_13      -0.1201207000
_diffrn_orient_matrix_UB_21      0.0960193000
_diffrn_orient_matrix_UB_22      -0.0624762000
_diffrn_orient_matrix_UB_23      0.0305903000
_diffrn_orient_matrix_UB_31      -0.0117275000
_diffrn_orient_matrix_UB_32      -0.0709415000
_diffrn_orient_matrix_UB_33      -0.2182532000
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11803
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.688
_diffrn_reflns_theta_min         5.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72010
_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    1.790
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(14)
_refine_ls_extinction_coef       0.0069(12)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0584P)^2^+0.1363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_full    0.714
_reflns_Friedel_fraction_max     0.711
_reflns_number_gt                1703
_reflns_number_total             1716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           z456301
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_original_cell_volume        924.783(13)
_cod_database_code               7247737
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H3N5O5
_chemical_oxdiff_usercomment     Z456301
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
;
_shelx_res_checksum              3383
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.361