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_7249665
_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
_atom_sites_solution_secondary   difmap
_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                 93.2790(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.14290(3)
_cell_length_b                   8.10668(5)
_cell_length_c                   17.96048(8)
_cell_measurement_reflns_used    16938
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3890
_cell_measurement_theta_min      4.8920
_cell_volume                     892.941(8)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      8.00 122.00   0.50    0.05    --   40.59  29.00-166.00  228
  2  \w     15.00 115.00   0.50    0.05    --   40.59  57.00 -90.00  200
  3  \w     15.00 115.00   0.50    0.05    --   40.59  57.00 -30.00  200
  4  \w    110.00 140.00   0.50    0.05    --  119.50 111.00 150.00   60
  5  \w     63.00 122.00   0.50    0.05    --   40.59 178.00  90.00  118
  6  \w     63.00 122.00   0.50    0.05    --   40.59 178.00   0.00  118
  7  \w     72.00  98.00   0.50    0.05    --  119.50 178.00-150.00   52
  8  \w     67.00 133.00   0.50    0.05    --  119.50 178.00-180.00  132
  9  \w    103.00 178.00   0.50    0.05    --  119.50 111.00-120.00  150
 10  \w    117.00 143.00   0.50    0.05    --  119.50 111.00   0.00   52
 11  \w    140.00 171.00   0.50    0.05    --  119.50 111.00  30.00   62
 12  \w    147.00 173.00   0.50    0.05    --  119.50 111.00  60.00   52
 13  \w    135.00 161.00   0.50    0.05    --  119.50  77.00 -90.00   52
 14  \w     92.00 137.00   0.50    0.05    --  119.50  77.00 -30.00   90
 15  \w     87.00 114.00   0.50    0.05    --  119.50  77.00 -90.00   54
 16  \w     95.00 128.00   0.50    0.05    --  119.50  77.00-150.00   66
 17  \w     87.00 157.00   0.50    0.05    --  119.50  77.00-120.00  140
 18  \w    153.00 178.00   0.50    0.05    --  119.50  77.00-150.00   50
 19  \w     92.00 140.00   0.50    0.05    --  119.50  77.00 -60.00   96
 20  \w     95.00 121.00   0.50    0.05    --  119.50  61.00-120.00   52
 21  \w     97.00 139.00   0.50    0.05    --  119.50  61.00 -60.00   84
 22  \w    101.00 127.00   0.50    0.05    --  119.50  61.00 -90.00   52
 23  \w     97.00 129.00   0.50    0.05    --  119.50  61.00   0.00   64
 24  \w    134.00 173.00   0.50    0.05    --  119.50  45.00 -30.00   78
 25  \w    149.00 174.00   0.50    0.05    --  119.50  61.00   0.00   50
 26  \w    102.00 127.00   0.50    0.05    --  119.50  45.00 -30.00   50
 27  \w     96.00 150.00   0.50    0.05    --  119.50  45.00  60.00  108
 28  \w     92.00 117.00   0.50    0.05    --  119.50  77.00 150.00   50
 29  \w    125.00 167.00   0.50    0.05    --  119.50  77.00 150.00   84
 30  \w     87.00 178.00   0.50    0.05    --  119.50  30.00  30.00  182
 31  \w     73.00  99.00   0.50    0.05    --  119.50  17.00   8.75   52
 32  \w     53.00  79.00   0.50    0.05    --  119.50   8.00  17.88   52
 33  \w     42.00 178.00   0.50    0.05    --  119.50  15.00-120.00  272
 34  \w     87.00 178.00   0.50    0.05    --  119.50  29.00-166.00  182
 35  \w     42.00  67.00   0.50    0.05    --  119.50  15.00-120.00   50
 36  \w     91.00 150.00   0.50    0.05    --  119.50 -79.00 -90.17  118
 37  \w     67.00 104.00   0.50    0.05    --  119.50 -77.00 -90.00   74
 38  \w     46.00  76.00   0.50    0.05    --  119.50 -77.00   0.00   60
 39  \w     47.00  95.00   0.50    0.05    --  119.50 -77.00-180.00   96
 40  \w    -41.00  34.00   0.50    0.05    --   40.59 -29.00  32.00  150
 41  \w     56.00  82.00   0.50    0.05    --  119.50 -77.00  90.00   52
 42  \w     49.00  79.00   0.50    0.05    --  119.50 -77.00 150.00   60
 43  \w     49.00  99.00   0.50    0.05    --  119.50 -77.00 120.00  100
 44  \w    121.00 156.00   0.50    0.05    --  119.50 -84.00 166.67   70
 45  \w     46.00  72.00   0.50    0.05    --  119.50-111.00 150.00   52
 46  \w     52.00 108.00   0.50    0.05    --  119.50-111.00  90.00  112
 47  \w     61.00  87.00   0.50    0.05    --  119.50 -95.00  90.00   52
 48  \w     74.00 108.00   0.50    0.05    --  119.50-111.00 150.00   68
 49  \w     41.00 105.00   0.50    0.05    --  119.50 -95.00 -30.00  128
 50  \w     79.00 104.00   0.50    0.05    --  119.50-111.00 -60.00   50
 51  \w     49.00  76.00   0.50    0.05    --  119.50-111.00 -60.00   54
 52  \w     41.00  67.00   0.50    0.05    --  119.50 -95.00-150.00   52
 53  \w     44.00  84.00   0.50    0.05    --  119.50 -95.00-120.00   80
 54  \w    124.00 155.00   0.50    0.05    --  119.50 -86.00   1.97   62
 55  \w   -122.00  -8.00   0.50    0.05    --  -40.59 -29.00  32.00  228
 56  \w    -71.00 -23.00   0.50    0.05    --  -98.00  61.00   0.00   96
 57  \w    -34.00  42.00   0.50    0.05    --  -40.59  29.00-166.00  152
 58  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -90.00  214
 59  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -97.42  214
 60  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -90.00  214
 61  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -60.00  214
 62  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -30.00  214
 63  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -30.00  214
 64  \w   -172.00 -68.00   0.50    0.05    --  -98.00 -69.00 -21.33  208
 65  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00   0.00  214
 66  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -77.00 -60.00  214
 67  \w   -172.00 -68.00   0.50    0.05    --  -98.00 -70.00 -84.81  208
 68  \w   -172.00 -65.00   0.50    0.05    --  -98.00 -76.00-125.94  214
 69  \w   -172.00 -70.00   0.50    0.05    --  -98.00 -63.00 -63.34  204
 70  \w   -172.00 -71.00   0.50    0.05    --  -98.00 -61.00 -90.00  202
 71  \w   -172.00 -70.00   0.50    0.05    --  -98.00 -65.00 -55.88  204
 72  \w   -172.00 -71.00   0.50    0.05    --  -98.00 -61.00   0.00  202
 73  \w   -175.00 -71.00   0.50    0.05    --  -98.00 -47.00-132.29  208
 74  \w   -177.00 -71.00   0.50    0.05    --  -98.00 -43.00 -64.67  212
 75  \w   -177.00 -65.00   0.50    0.05    --  -98.00 -29.00  32.00  224
;
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.728
_diffrn_reflns_theta_min         4.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.327
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.268
_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    2.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0059(2)
_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   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0195P)^2^+1.0428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             1935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1i_z483101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249665
_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   0.280
_shelx_estimated_absorpt_t_max   0.413
_shelx_res_checksum              35371
_shelx_hkl_checksum              18239