Cocrystals of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides and 1,5-dioxides: step-by-step development of crystal engineering of energetic materials
Baraboshkin, N. M.; Zelenov, V. P.; Fedyanin, I. V.; Samigullina, A. I.; Klenov, M. S.; CrystEngComm 27 (2025) 386–399; doi:10.1039/D4CE01081G

data_7249654
_publ_section_title
;
 Cocrystals of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxides and
 1,5-dioxides: step-by-step development of crystal engineering of
 energetic materials
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              386
_journal_page_last               399
_journal_paper_doi               10.1039/D4CE01081G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C8 H3 N5 O5), C6 N6 O6'
_chemical_formula_sum            'C22 H6 N16 O16'
_chemical_formula_weight         750.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           'Modified SHELXL output'
_audit_update_record
;
2024-11-25 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.843(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.51400(10)
_cell_length_b                   32.5430(8)
_cell_length_c                   12.9337(3)
_cell_measurement_reflns_used    5068
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.1240
_cell_measurement_theta_min      5.4120
_cell_volume                     2738.38(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.103a 64-bit (release 20-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -74.00  30.00   0.50    1.40    --  -44.13  84.00  25.00  208
  2  \w    -16.00  20.00   0.50    1.40    --   44.13 -84.00 -94.00   72
  3  \w    -98.00 -73.00   0.50    6.00    --  -96.00  84.00  25.00   50
  4  \w     61.00  89.00   0.50    6.00    --  117.50 -84.00 -94.00   56
  5  \w    137.00 176.00   0.50    6.00    --  117.50  84.00  25.00   78
  6  \w    103.00 130.00   0.50    6.00    --  117.50  84.00  25.00   54
  7  \w    -42.00  18.00   0.50    1.40    --  -44.13  38.00 150.00  120
  8  \w    -32.00  27.00   0.50    1.40    --   44.13 -19.00 -90.00  118
  9  \w     17.00 113.00   0.50    1.40    --   44.13  77.00   0.00  192
 10  \w   -141.00 -82.00   0.50    6.00    --  -96.00 -84.00 -94.00  118
 11  \w     72.00  98.00   0.50    6.00    --  117.50 -95.00 -30.00   52
 12  \w    111.00 139.00   0.50    6.00    --  117.50  30.00 -60.00   56
 13  \w     45.00  70.00   0.50    6.00    --  117.50 -77.00  60.00   50
 14  \w    139.00 178.00   0.50    6.00    --  117.50  15.00 -90.00   78
 15  \w     47.00  91.00   0.50    6.00    --  117.50 -77.00  30.00   88
 16  \w     45.00  70.00   0.50    6.00    --  117.50 -61.00 -30.00   50
 17  \w     97.00 145.00   0.50    6.00    --  117.50  61.00 -30.00   96
 18  \w     46.00  88.00   0.50    6.00    --  117.50 -77.00 -30.00   84
 19  \w     87.00 130.00   0.50    6.00    --  117.50  15.00-150.00   86
 20  \w    141.00 177.00   0.50    6.00    --  117.50  15.00-150.00   72
 21  \w    122.00 148.00   0.50    6.00    --  117.50  30.00 120.00   52
 22  \w     94.00 121.00   0.50    6.00    --  117.50  15.00 -90.00   54
 23  \w     98.00 152.00   0.50    6.00    --  117.50  45.00 -30.00  108
 24  \w    128.00 154.00   0.50    6.00    --  117.50 125.00 120.00   52
 25  \w     98.00 144.00   0.50    6.00    --  117.50  45.00 -90.00   92
 26  \w     88.00 114.00   0.50    6.00    --  117.50  15.00   0.00   52
 27  \w    146.00 178.00   0.50    6.00    --  117.50  15.00   0.00   64
 28  \w     46.00  90.00   0.50    6.00    --  117.50 -77.00-150.00   88
 29  \w     99.00 173.00   0.50    6.00    --  117.50  45.00-180.00  148
 30  \w     74.00 105.00   0.50    6.00    --  117.50 -77.00 -90.00   62
 31  \w     61.00  93.00   0.50    6.00    --  117.50-125.00   0.00   64
 32  \w     45.00  70.00   0.50    6.00    --  117.50 -61.00  30.00   50
 33  \w     46.00  83.00   0.50    6.00    --  117.50 -77.00-180.00   74
 34  \w     47.00 111.00   0.50    6.00    --  117.50-125.00 150.00  128
 35  \w     70.00  96.00   0.50    6.00    --  117.50 -81.00 171.11   52
 36  \w    103.00 146.00   0.50    6.00    --  117.50 -81.00 171.11   86
 37  \w     69.00 109.00   0.50    6.00    --  117.50-125.00-150.00   80
 38  \w     45.00 147.00   0.50    6.00    --  117.50 -83.00 134.53  204
 39  \w     59.00  99.00   0.50    6.00    --  117.50 -95.00-180.00   80
 40  \w     48.00  75.00   0.50    6.00    --  117.50-125.00 -30.00   54
 41  \w     50.00  76.00   0.50    6.00    --  117.50-125.00  30.00   52
 42  \w    105.00 131.00   0.50    6.00    --  117.50  45.00-150.00   52
 43  \w    125.00 163.00   0.50    6.00    --  117.50  30.00-150.00   76
 44  \w     97.00 124.00   0.50    6.00    --  117.50  61.00 150.00   54
 45  \w    136.00 176.00   0.50    6.00    --  117.50  61.00 150.00   80
 46  \w    119.00 145.00   0.50    6.00    --  117.50  77.00 -60.00   52
 47  \w     81.00 107.00   0.50    6.00    --  117.50 -82.00 -15.10   52
 48  \w     89.00 115.00   0.50    6.00    --  117.50 -84.00-152.74   52
 49  \w     77.00 103.00   0.50    6.00    --  117.50   8.00  99.67   52
 50  \w    108.00 147.00   0.50    6.00    --  117.50 -84.00 -94.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0678983000
_diffrn_orient_matrix_UB_12      0.0342481000
_diffrn_orient_matrix_UB_13      -0.0765163000
_diffrn_orient_matrix_UB_21      0.0972122000
_diffrn_orient_matrix_UB_22      -0.0236141000
_diffrn_orient_matrix_UB_23      -0.0884653000
_diffrn_orient_matrix_UB_31      -0.2048956000
_diffrn_orient_matrix_UB_32      -0.0225881000
_diffrn_orient_matrix_UB_33      -0.0234659000
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30352
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.811
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (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    1.820
_exptl_crystal_description       prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.985
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     814
_refine_ls_number_reflns         5983
_refine_ls_number_restraints     649
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0935
_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^)+(0.1100P)^2^+6.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2444
_refine_ls_wR_factor_ref         0.2462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5635
_reflns_number_total             5983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01081g2.cif
_cod_data_source_block           z482101_g
_cod_depositor_comments
'Adding full bibliography for 7249654--7249655.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249654
_publ_contact_name               'Aida I. Samigullina'
_publ_contact_email              s_aida_88@mail.ru
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.695
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              15301
_shelx_hkl_checksum              17580