R-Substituent vs. exocyclic oxygen: influence on synthesis and crystal packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides
Zelenov, Victor P.; Fedyanin, Ivan V.; Samigullina, Aida I.; Larin, Alexandr A.; Sheremetev, Aleksei B.; CrystEngComm 27 (2025) 372–385; doi:10.1039/D4CE01068J

data_7249666
_publ_section_title
;
 R-Substituent vs. exocyclic oxygen: influence on synthesis and crystal
 packing of R-[1,2,5]oxadiazolo[3,4-c]cinnoline mono- and dioxides
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              372
_journal_page_last               385
_journal_paper_doi               10.1039/D4CE01068J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C8 H3 Br N4 O3'
_chemical_formula_sum            'C8 H3 Br N4 O3'
_chemical_formula_weight         283.05
_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
;
2024-06-24 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.796(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6295(2)
_cell_length_b                   6.38437(16)
_cell_length_c                   16.6319(4)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.7830
_cell_measurement_theta_min      5.2990
_cell_volume                     915.87(4)
_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 (Sheldrick, 2015b)'
_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 0.997
_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      8.00 117.00   0.50    0.10    --   41.39  75.00 163.00  218
  2  \w    -34.00  76.00   0.50    0.05    --    0.00  75.00 163.00  220
  3  \w    -34.00  76.00   0.50    0.05    --    0.00  75.00 163.00  220
  4  \w    -33.00  75.00   0.50    0.10    --   41.39 -75.00  36.00  216
  5  \w    -33.00  75.00   0.50    0.10    --   41.39 -75.00  36.00  216
  6  \w    -75.00  34.00   0.50    0.05    --    0.00 -75.00  36.00  218
  7  \w     34.00  99.00   0.50    0.10    --   41.39-125.00  60.00  130
  8  \w     34.00  99.00   0.50    0.10    --   41.39-125.00 -60.00  130
  9  \w     41.00 106.00   0.50    0.15    --  121.50 -95.00 -60.00  130
 10  \w     41.00 106.00   0.50    0.15    --  121.50 -95.00 -60.00  130
 11  \w     41.00 106.00   0.50    0.15    --  121.50 -95.00   0.00  130
 12  \w     56.00  82.00   0.50    0.15    --  121.50 -95.00  30.00   52
 13  \w     45.00 158.00   0.50    0.15    --  121.50 -82.00 -14.91  226
 14  \w     45.00 158.00   0.50    0.15    --  121.50 -82.00 -14.91  226
 15  \w     47.00  98.00   0.50    0.15    --  121.50 -75.00  36.00  102
 16  \w     47.00 105.00   0.50    0.15    --  121.50 -77.00 120.00  116
 17  \w     69.00 110.00   0.50    0.15    --  121.50 -78.00 163.36   82
 18  \w     47.00 105.00   0.50    0.15    --  121.50 -77.00  90.00  116
 19  \w     47.00 105.00   0.50    0.15    --  121.50 -77.00  60.00  116
 20  \w     62.00  87.00   0.50    0.15    --  121.50 -77.00 -90.00   50
 21  \w     53.00  79.00   0.50    0.15    --  121.50  11.00-173.02   52
 22  \w     87.00 178.00   0.50    0.15    --  121.50  77.00-180.00  182
 23  \w     87.00 178.00   0.50    0.15    --  121.50  77.00-180.00  182
 24  \w     92.00 178.00   0.50    0.15    --  121.50  61.00-120.00  172
 25  \w    147.00 177.00   0.50    0.15    --  121.50  61.00-120.00   60
 26  \w     91.00 170.00   0.50    0.15    --  121.50  77.00 -60.00  158
 27  \w     93.00 119.00   0.50    0.15    --  121.50  61.00  30.00   52
 28  \w     92.00 178.00   0.50    0.15    --  121.50  45.00  60.00  172
 29  \w     92.00 178.00   0.50    0.15    --  121.50  45.00  90.00  172
 30  \w     92.00 178.00   0.50    0.15    --  121.50  45.00 120.00  172
 31  \w     88.00 178.00   0.50    0.15    --  121.50  75.00 163.00  180
 32  \w     96.00 134.00   0.50    0.15    --  121.50  61.00 120.00   76
 33  \w     92.00 120.00   0.50    0.15    --  121.50  45.00 120.00   56
 34  \w     63.00 146.00   0.50    0.15    --  121.50 178.00 -60.00  166
 35  \w     63.00 146.00   0.50    0.15    --  121.50 178.00  30.00  166
 36  \w     63.00 146.00   0.50    0.15    --  121.50 178.00  30.00  166
 37  \w     -1.00  29.00   0.50    0.10    --   41.39  96.00 -82.03   60
 38  \w    -86.00 -13.00   0.50    0.10    --  -41.39 125.00 -90.00  146
 39  \w    -51.00 -21.00   0.50    0.15    -- -100.00  45.00-120.00   60
 40  \w    -51.00 -21.00   0.50    0.15    -- -100.00  45.00 -60.00   60
 41  \w    -51.00 -21.00   0.50    0.15    -- -100.00  45.00  30.00   60
 42  \w    -98.00 -24.00   0.50    0.15    -- -100.00  75.00 163.00  148
 43  \w   -175.00 -66.00   0.50    0.15    -- -100.00 -75.00  36.00  218
 44  \w   -175.00 -66.00   0.50    0.15    -- -100.00 -75.00  36.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.299
_diffrn_reflns_theta_min         5.322
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.169
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.472
_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    2.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.00130(18)
_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   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0353P)^2^+1.0468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1947
_reflns_number_total             1994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1m_z476101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249666
_publ_contact_name               'Aida I. Samigullina'
_publ_contact_email              s_aida_88@mail.ru
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.357
_shelx_estimated_absorpt_t_max   0.672
_shelx_res_checksum              8511
_shelx_hkl_checksum              26257