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_7249655
_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 H4 N4 O3), C2 N6 O3'
_chemical_formula_sum            'C18 H8 N14 O9'
_chemical_formula_weight         564.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'Modified SHELXL output'
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                93.9700(10)
_cell_angle_beta                 92.7460(10)
_cell_angle_gamma                100.6530(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5638(2)
_cell_length_b                   9.2989(2)
_cell_length_c                   15.1960(4)
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.23
_cell_volume                     1045.86(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       '\o scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            127230
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         54.999
_diffrn_reflns_theta_min         2.236
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         26217
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16319
_reflns_number_total             26217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01081g2.cif
_cod_data_source_block           ftdo-cnldo
_cod_depositor_comments
'Adding full bibliography for 7249654--7249655.cif.'
_cod_database_code               7249655
_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              95975
_shelx_hkl_checksum              92529