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_7247739
_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 H2 N6 O6'
_chemical_formula_sum            'C8 H2 N6 O6'
_chemical_formula_weight         278.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2023-09-19 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                   12.53304(19)
_cell_length_b                   8.30693(13)
_cell_length_c                   9.61288(13)
_cell_measurement_reflns_used    9012
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      78.3880
_cell_measurement_theta_min      3.5270
_cell_volume                     1000.81(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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(5)
_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    -38.00  28.00   0.50    1.50    --  -46.94  33.00  74.00  132
  2  \w   -121.00 -32.00   0.50    1.50    --  -46.94 -33.00 -84.00  178
  3  \w      8.00  82.00   0.50    1.50    --   46.94-102.00  75.00  148
  4  \w   -166.00 -77.00   0.50    6.00    --  -91.75 -33.00 -84.00  178
  5  \w    -80.00 -21.00   0.50    6.00    --  -91.75 101.00 -85.00  118
  6  \w   -163.00 -85.00   0.50    6.00    --  -91.75-102.00  75.00  156
  7  \w     42.00 106.00   0.50    6.00    --  113.25-102.00  75.00  128
  8  \w    107.00 178.00   0.50    6.00    --  113.25 101.00 -85.00  142
  9  \w    106.00 178.00   0.50    6.00    --  113.25 102.00 178.00  144
 10  \w     42.00 106.00   0.50    6.00    --  113.25-101.00 170.00  128
 11  \w     99.00 178.00   0.50    6.00    --  113.25  33.00  74.00  158
 12  \w    -81.00  14.00   0.50    1.50    --  -46.94 102.00 178.00  190
 13  \w    -26.00  25.00   0.50    1.50    --   46.94 -19.00 150.00  102
 14  \w    137.00 163.00   0.50    6.00    --  113.25  77.00-120.00   52
 15  \w     96.00 141.00   0.50    6.00    --  113.25 125.00-120.00   90
 16  \w     43.00  79.00   0.50    6.00    --  113.25-125.00  60.00   72
 17  \w     83.00 109.00   0.50    6.00    --  113.25-125.00  60.00   52
 18  \w     81.00 106.00   0.50    6.00    --  113.25 -95.00  90.00   50
 19  \w     41.00  67.00   0.50    6.00    --  113.25 -61.00  30.00   52
 20  \w     43.00  97.00   0.50    6.00    --  113.25 -77.00 -60.00  108
 21  \w     42.00  89.00   0.50    6.00    --  113.25 -77.00 -30.00   94
 22  \w     78.00 111.00   0.50    6.00    --  113.25-125.00-150.00   66
 23  \w    140.00 166.00   0.50    6.00    --  113.25  15.00-180.00   52
 24  \w     43.00  69.00   0.50    6.00    --  113.25 -77.00-180.00   52
 25  \w     65.00 103.00   0.50    6.00    --  113.25 -77.00-120.00   76
 26  \w     41.00  69.00   0.50    6.00    --  113.25 -95.00  90.00   56
 27  \w     41.00  68.00   0.50    6.00    --  113.25 -61.00 150.00   54
 28  \w     42.00  71.00   0.50    6.00    --  113.25 -61.00  90.00   58
 29  \w     70.00 106.00   0.50    6.00    --  113.25-125.00-120.00   72
 30  \w     74.00 108.00   0.50    6.00    --  113.25-125.00  30.00   68
 31  \w    107.00 133.00   0.50    6.00    --  113.25  45.00-150.00   52
 32  \w     49.00  75.00   0.50    6.00    --  113.25 -77.00-150.00   52
 33  \w     62.00 103.00   0.50    6.00    --  113.25 -77.00 -90.00   82
 34  \w     49.00 100.00   0.50    6.00    --  113.25 -77.00  90.00  102
 35  \w     91.00 138.00   0.50    6.00    --  113.25   0.00-180.00   94
 36  \w    151.00 177.00   0.50    6.00    --  113.25  90.00 -43.37   52
 37  \w    105.00 175.00   0.50    6.00    --  113.25  45.00-120.00  140
 38  \w    104.00 174.00   0.50    6.00    --  113.25  45.00-153.54  140
 39  \w     93.00 175.00   0.50    6.00    --  113.25  77.00 120.00  164
 40  \w     68.00 111.00   0.50    6.00    --  113.25 -82.00-162.92   86
 41  \w     42.00  71.00   0.50    6.00    --  113.25 -61.00-150.00   58
;
_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      -0.0865604000
_diffrn_orient_matrix_UB_12      -0.1065404000
_diffrn_orient_matrix_UB_13      0.0668261000
_diffrn_orient_matrix_UB_21      -0.0794001000
_diffrn_orient_matrix_UB_22      0.1414677000
_diffrn_orient_matrix_UB_23      -0.0062789000
_diffrn_orient_matrix_UB_31      -0.0362754000
_diffrn_orient_matrix_UB_32      -0.0549599000
_diffrn_orient_matrix_UB_33      -0.1455292000
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.794
_diffrn_reflns_theta_min         5.325
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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            yellow
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_coef       0.0032(7)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0485P)^2^+0.4434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.728
_reflns_number_gt                1884
_reflns_number_total             1908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00964e2.cif
_cod_data_source_block           Z461504
_cod_depositor_comments
'Adding full bibliography for 7247734--7247739.cif.'
_cod_database_code               7247739
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H2N6O6
_chemical_oxdiff_usercomment     Z461504
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.783
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12)
;
_shelx_res_checksum              16697
_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.865