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_7247734
_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 O2'
_chemical_formula_sum            'C8 H4 N4 O2'
_chemical_formula_weight         188.15
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-02-15
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3886(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.74397(15)
_cell_length_b                   5.37413(10)
_cell_length_c                   18.7390(3)
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      76.5310
_cell_measurement_theta_min      5.7650
_cell_volume                     769.42(2)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      99.97(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 0.996
_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     40.00  79.00   0.50    0.25    --  107.75-125.00   0.00   78
  2  \w     39.00 111.00   0.50    0.25    --  107.75-125.00-120.00  144
  3  \w    -62.00  24.00   0.50    0.08    --  -48.68  55.00   0.00  172
  4  \w    -51.00 -14.00   0.50    0.25    --  -86.25  45.00-180.00   74
  5  \w    -63.00 -14.00   0.50    0.25    --  -86.25  55.00   0.00   98
  6  \w     61.00  87.00   0.50    0.25    --  107.75-125.00  90.00   52
  7  \w     45.00  77.00   0.50    0.25    --  107.75-125.00 120.00   64
  8  \w     82.00 109.00   0.50    0.25    --  107.75-125.00 120.00   54
  9  \w     36.00 105.00   0.50    0.25    --  107.75 -95.00 -60.00  138
 10  \w     69.00  94.00   0.50    0.25    --  107.75 -95.00-120.00   50
 11  \w     42.00  67.00   0.50    0.25    --  107.75-125.00-180.00   50
 12  \w     36.00  62.00   0.50    0.25    --  107.75 -95.00-120.00   52
 13  \w     40.00  66.00   0.50    0.25    --  107.75 -83.00 -27.90   52
 14  \w    106.00 132.00   0.50    0.25    --  107.75 -83.00 -27.90   52
 15  \w     51.00  90.00   0.50    0.25    --  107.75 -77.00  30.00   78
 16  \w     38.00  64.00   0.50    0.25    --  107.75 -61.00 150.00   52
 17  \w     36.00  71.00   0.50    0.25    --  107.75 -61.00   0.00   70
 18  \w     40.00  71.00   0.50    0.25    --  107.75 -61.00-120.00   62
 19  \w     36.00  63.00   0.50    0.25    --  107.75 -55.00-142.00   54
 20  \w     36.00 166.00   0.50    0.25    --  107.75   0.00   0.00  260
 21  \w     97.00 178.00   0.50    0.25    --  107.75  45.00 -60.00  162
 22  \w     86.00 133.00   0.50    0.25    --  107.75  77.00   0.00   94
 23  \w     95.00 178.00   0.50    0.25    --  107.75  55.00   0.00  166
 24  \w    120.00 146.00   0.50    0.25    --  107.75  30.00 -30.00   52
 25  \w    110.00 136.00   0.50    0.25    --  107.75  30.00  90.00   52
 26  \w     97.00 146.00   0.50    0.25    --  107.75  45.00 120.00   98
 27  \w     36.00 120.00   0.50    0.08    --   48.68  55.00   0.00  168
 28  \w     96.00 128.00   0.50    0.25    --  107.75 125.00-120.00   64
 29  \w    -22.00  62.00   0.50    0.08    --   48.68 -55.00-142.00  168
 30  \w    137.00 176.00   0.50    0.25    --  107.75 125.00-120.00   78
 31  \w    -25.00  26.00   0.50    0.08    --   48.68 -19.00  30.00  102
 32  \w   -120.00 -35.00   0.50    0.08    --  -48.68 -55.00-142.00  170
 33  \w   -158.00 -73.00   0.50    0.25    --  -86.25 -55.00-142.00  170
 34  \w   -118.00 -73.00   0.50    0.08    --  -48.68-125.00-180.00   90
;
_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      -0.0134039000
_diffrn_orient_matrix_UB_12      0.0603290000
_diffrn_orient_matrix_UB_13      -0.0810875000
_diffrn_orient_matrix_UB_21      0.1525398000
_diffrn_orient_matrix_UB_22      -0.1796052000
_diffrn_orient_matrix_UB_23      -0.0051457000
_diffrn_orient_matrix_UB_31      -0.1311815000
_diffrn_orient_matrix_UB_32      -0.2150304000
_diffrn_orient_matrix_UB_33      -0.0185772000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8675
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.623
_diffrn_reflns_theta_min         4.784
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0603P)^2^+0.2643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1531
_reflns_number_total             1627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           Z-458101
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247734
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H4N4O2
_chemical_oxdiff_usercomment     Z458101
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.655
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C10(H10), C9(H9)
;
_shelx_res_checksum              3329
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.871