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_7249668
_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         'C9 H6 N4 O2'
_chemical_formula_sum            'C9 H6 N4 O2'
_chemical_formula_weight         202.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_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                 108.588(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2076(3)
_cell_length_b                   6.3054(2)
_cell_length_c                   8.5808(3)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3350
_cell_measurement_theta_min      5.6650
_cell_volume                     420.91(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.976
_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   -123.00 -32.00   0.50    0.20    --  -46.47 -24.00 140.00  182
  2  \w    -30.00  30.00   0.50    0.20    --  -46.47  24.00 -54.00  120
  3  \w     32.00 123.00   0.50    0.20    --   46.47  24.00 -54.00  182
  4  \w    -29.00  30.00   0.50    0.20    --   46.47 -24.00 140.00  118
  5  \w   -167.00 -77.00   0.50    0.80    --  -91.75 -24.00 140.00  180
  6  \w     99.00 178.00   0.50    0.80    --  113.25  24.00 -54.00  158
  7  \w     30.00 119.00   0.50    0.20    --   46.47  57.00  90.00  178
  8  \w     23.00 119.00   0.50    0.20    --   46.47  76.00  -3.62  192
  9  \w     30.00 119.00   0.50    0.20    --   46.47  57.00  90.00  178
 10  \w     32.00 120.00   0.50    0.20    --   46.47  38.00  30.00  176
 11  \w    -29.00  27.00   0.50    0.20    --   46.47 -19.00  30.00  112
 12  \w     32.00 120.00   0.50    0.20    --   46.47  38.00  90.00  176
 13  \w    -51.00 -19.00   0.50    0.80    --  -91.75  45.00  60.00   64
 14  \w   -164.00 -74.00   0.50    0.80    --  -91.75 -61.00  60.00  180
 15  \w    -51.00 -19.00   0.50    0.80    --  -91.75  45.00 120.00   64
 16  \w   -164.00 -69.00   0.50    0.80    --  -91.75 -73.00  52.40  190
 17  \w   -164.00 -68.00   0.50    0.80    --  -91.75 -77.00 120.00  192
 18  \w   -164.00 -68.00   0.50    0.80    --  -91.75 -77.00  90.00  192
 19  \w   -164.00 -69.00   0.50    0.80    --  -91.75 -74.00  10.53  190
 20  \w   -146.00 -74.00   0.50    0.80    --  -91.75 -65.00  29.82  144
 21  \w    -94.00 -68.00   0.50    0.80    --  -91.75 -77.00  60.00   52
 22  \w   -151.00-124.00   0.50    0.80    --  -91.75 -76.00  75.40   54
 23  \w    -96.00 -71.00   0.50    0.80    --  -91.75 -77.00   0.00   50
 24  \w    -94.00 -68.00   0.50    0.80    --  -91.75 -77.00  30.00   52
 25  \w    -99.00 -68.00   0.50    0.80    --  -91.75 -76.00  75.40   62
 26  \w   -157.00-131.00   0.50    0.80    --  -91.75 -74.00  10.53   52
 27  \w   -124.00 -72.00   0.50    0.80    --  -91.75 -66.00  53.50  104
 28  \w    -51.00 -26.00   0.50    0.80    --  -91.75  45.00  90.00   50
 29  \w    -95.00 -69.00   0.50    0.80    --  -91.75 -74.00  99.43   52
 30  \w    117.00 143.00   0.50    0.80    --  113.25  61.00  60.00   52
 31  \w    142.00 168.00   0.50    0.80    --  113.25  15.00   0.00   52
 32  \w    153.00 178.00   0.50    0.80    --  113.25 125.00 150.00   50
 33  \w     42.00  71.00   0.50    0.80    --  113.25 -61.00 150.00   58
 34  \w    102.00 135.00   0.50    0.80    --  113.25 125.00  30.00   66
 35  \w     92.00 137.00   0.50    0.80    --  113.25  77.00 -30.00   90
 36  \w    107.00 177.00   0.50    0.80    --  113.25  61.00   0.00  140
 37  \w    105.00 131.00   0.50    0.80    --  113.25 125.00 150.00   52
 38  \w    131.00 176.00   0.50    0.80    --  113.25  30.00-180.00   90
 39  \w     43.00  68.00   0.50    0.80    --  113.25 -61.00 120.00   50
 40  \w     78.00 106.00   0.50    0.80    --  113.25-106.00  27.50   56
 41  \w     41.00  70.00   0.50    0.80    --  113.25 -77.00   0.00   58
 42  \w    107.00 178.00   0.50    0.80    --  113.25  45.00 150.00  142
 43  \w     41.00  68.00   0.50    0.80    --  113.25 -61.00 -60.00   54
 44  \w    136.00 162.00   0.50    0.80    --  113.25  77.00  90.00   52
 45  \w     90.00 128.00   0.50    0.80    --  113.25  77.00  90.00   76
 46  \w     41.00  69.00   0.50    0.80    --  113.25 -95.00  60.00   56
 47  \w    136.00 162.00   0.50    0.80    --  113.25  77.00-120.00   52
 48  \w    105.00 131.00   0.50    0.80    --  113.25  77.00-120.00   52
 49  \w     44.00  70.00   0.50    0.80    --  113.25 -61.00-120.00   52
 50  \w    111.00 137.00   0.50    0.80    --  113.25  61.00  90.00   52
 51  \w     90.00 134.00   0.50    0.80    --  113.25  77.00  30.00   88
 52  \w     90.00 119.00   0.50    0.80    --  113.25  77.00  60.00   58
 53  \w     98.00 145.00   0.50    0.80    --  113.25  61.00-150.00   94
 54  \w    100.00 145.00   0.50    0.80    --  113.25  45.00  30.00   90
 55  \w    141.00 167.00   0.50    0.80    --  113.25  61.00  30.00   52
 56  \w     83.00 109.00   0.50    0.80    --  113.25-125.00 -60.00   52
 57  \w     43.00  69.00   0.50    0.80    --  113.25 -61.00   0.00   52
 58  \w    104.00 144.00   0.50    0.80    --  113.25  61.00 120.00   80
 59  \w    149.00 175.00   0.50    0.80    --  113.25  61.00 120.00   52
 60  \w    100.00 125.00   0.50    0.80    --  113.25  15.00   0.00   50
 61  \w     55.00  81.00   0.50    0.80    --  113.25 -77.00-150.00   52
 62  \w    100.00 126.00   0.50    0.80    --  113.25  15.00 120.00   52
 63  \w     51.00  77.00   0.50    0.80    --  113.25-125.00   0.00   52
 64  \w    153.00 178.00   0.50    0.80    --  113.25 125.00  30.00   50
 65  \w     99.00 151.00   0.50    0.80    --  113.25  61.00-120.00  104
 66  \w     99.00 130.00   0.50    0.80    --  113.25  61.00  30.00   62
 67  \w     43.00  91.00   0.50    0.80    --  113.25 -95.00 120.00   96
 68  \w     62.00  93.00   0.50    0.80    --  113.25 -77.00  60.00   62
 69  \w    112.00 138.00   0.50    0.80    --  113.25 -88.00 -35.15   52
 70  \w    153.00 178.00   0.50    0.80    --  113.25  61.00  60.00   50
 71  \w    113.00 143.00   0.50    0.80    --  113.25  45.00   0.00   60
 72  \w     81.00 106.00   0.50    0.80    --  113.25 -95.00 -90.00   50
 73  \w     44.00  70.00   0.50    0.80    --  113.25 -95.00 -90.00   52
;
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8017
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.668
_diffrn_reflns_theta_min         5.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_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            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0549P)^2^+0.1653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                918
_reflns_number_total             979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1q_z480101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7249668
_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   0.753
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              80072
_shelx_hkl_checksum              93250