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_7247735
_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           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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-11
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2846(2)
_cell_length_b                   9.99780(10)
_cell_length_c                   6.38630(10)
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.9440
_cell_measurement_theta_min      5.3760
_cell_volume                     912.06(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      99.9(3)
_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   -120.00 -64.00   0.50    1.00    --  -48.70-139.00  13.00  112
  2  \w   -122.00 -39.00   0.50    1.00    --  -48.70 -22.00  45.00  166
  3  \w    -28.00  26.00   0.50    1.00    --  -48.70  22.00-148.00  108
  4  \w   -156.00 -84.00   0.50    3.87    --  -86.25-103.00 -96.00  144
  5  \w    -90.00 -16.00   0.50    3.87    --  -86.25 131.00-100.00  148
  6  \w     38.00 116.00   0.50    3.87    --  107.75-131.00-171.00  156
  7  \w     97.00 178.00   0.50    3.87    --  107.75  22.00-148.00  162
  8  \w     46.00 121.00   0.50    3.87    --  107.75-139.00  13.00  150
  9  \w     71.00  97.00   0.50    3.87    --  107.75-103.00 -96.00   52
 10  \w    -22.00  25.00   0.50    1.00    --   48.70 -19.00 -90.00   94
 11  \w     37.00  71.00   0.50    3.87    --  107.75 -61.00  30.00   68
 12  \w     40.00  72.00   0.50    3.87    --  107.75-125.00 -30.00   64
 13  \w     49.00  75.00   0.50    3.87    --  107.75 -95.00  30.00   52
 14  \w     39.00  65.00   0.50    3.87    --  107.75-103.00 -34.16   52
 15  \w     36.00  69.00   0.50    3.87    --  107.75 -95.00  90.00   66
 16  \w    138.00 178.00   0.50    3.87    --  107.75  45.00 -60.00   80
 17  \w     83.00 109.00   0.50    3.87    --  107.75-125.00 -30.00   52
 18  \w     39.00  70.00   0.50    3.87    --  107.75 -61.00-150.00   62
 19  \w    147.00 177.00   0.50    3.87    --  107.75  30.00  90.00   60
 20  \w     41.00  69.00   0.50    3.87    --  107.75 -61.00 -30.00   56
 21  \w     69.00 106.00   0.50    3.87    --  107.75-103.00 -34.16   74
 22  \w     43.00  69.00   0.50    3.87    --  107.75-125.00   0.00   52
 23  \w     84.00 110.00   0.50    3.87    --  107.75-125.00  90.00   52
 24  \w    109.00 135.00   0.50    3.87    --  107.75  45.00  27.49   52
 25  \w     36.00  61.00   0.50    3.87    --  107.75 -61.00  60.00   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      -0.0776967000
_diffrn_orient_matrix_UB_12      0.1032424000
_diffrn_orient_matrix_UB_13      0.0430505000
_diffrn_orient_matrix_UB_21      -0.0747014000
_diffrn_orient_matrix_UB_22      -0.1056354000
_diffrn_orient_matrix_UB_23      -0.0537301000
_diffrn_orient_matrix_UB_31      -0.0030715000
_diffrn_orient_matrix_UB_32      -0.0438743000
_diffrn_orient_matrix_UB_33      0.2312489000
_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  0.0227
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6846
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.814
_diffrn_reflns_theta_min         5.401
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_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    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0316P)^2^+0.2094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.389
_reflns_Friedel_fraction_full    0.507
_reflns_Friedel_fraction_max     0.468
_reflns_number_gt                1441
_reflns_number_total             1472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           Z461401
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247735
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H3N5O4
_chemical_oxdiff_usercomment     Z461401
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 98.40
_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:
 C8(H8), C10(H10), C11(H11)
;
_shelx_res_checksum              8460
_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 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.793