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_7249669
_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 O3'
_chemical_formula_sum            'C9 H6 N4 O3'
_chemical_formula_weight         218.18
_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
_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                77.3481(15)
_cell_angle_beta                 87.0582(15)
_cell_angle_gamma                80.0249(18)
_cell_formula_units_Z            2
_cell_length_a                   5.89689(13)
_cell_length_b                   8.54466(18)
_cell_length_c                   9.10721(12)
_cell_measurement_reflns_used    7668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      80.4840
_cell_measurement_theta_min      4.9550
_cell_volume                     440.931(15)
_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 0.990
_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     17.00  80.00   0.50    0.05    --   44.13  77.00 150.00  126
  2  \w     17.00 117.00   0.50    0.05    --   44.13  77.00  60.00  200
  3  \w     17.00 117.00   0.50    0.05    --   44.13  77.00 -30.00  200
  4  \w     25.00 121.00   0.50    0.05    --   44.13  33.00 -47.00  192
  5  \w     25.00 121.00   0.50    0.05    --   44.13  33.00 -47.00  192
  6  \w     91.00 178.00   0.50    0.10    --  117.50  77.00-120.00  174
  7  \w     97.00 178.00   0.50    0.10    --  117.50  61.00-180.00  162
  8  \w     97.00 178.00   0.50    0.10    --  117.50  61.00-180.00  162
  9  \w     98.00 178.00   0.50    0.10    --  117.50  45.00 -90.00  160
 10  \w     91.00 178.00   0.50    0.10    --  117.50  77.00 120.00  174
 11  \w     91.00 178.00   0.50    0.10    --  117.50  77.00 150.00  174
 12  \w     91.00 178.00   0.50    0.10    --  117.50  77.00 150.00  174
 13  \w     98.00 178.00   0.50    0.10    --  117.50  45.00 120.00  160
 14  \w     98.00 178.00   0.50    0.10    --  117.50  45.00  90.00  160
 15  \w     98.00 178.00   0.50    0.10    --  117.50  30.00   0.00  160
 16  \w     98.00 178.00   0.50    0.10    --  117.50  45.00 -30.00  160
 17  \w     98.00 178.00   0.50    0.10    --  117.50  33.00 -47.00  160
 18  \w     98.00 178.00   0.50    0.10    --  117.50  45.00 -90.00  160
 19  \w     98.00 178.00   0.50    0.10    --  117.50  45.00-150.00  160
 20  \w     86.00 178.00   0.50    0.10    --  117.50  15.00-120.00  184
 21  \w     86.00 178.00   0.50    0.10    --  117.50  15.00  60.00  184
 22  \w     86.00 178.00   0.50    0.10    --  117.50  15.00  60.00  184
 23  \w     98.00 178.00   0.50    0.10    --  117.50  30.00  90.00  160
 24  \w     86.00 178.00   0.50    0.10    --  117.50  15.00 150.00  184
 25  \w     45.00 147.00   0.50    0.10    --  117.50 -83.00 -24.56  204
 26  \w     47.00 111.00   0.50    0.10    --  117.50-125.00 120.00  128
 27  \w     34.00  94.00   0.50    0.05    --   44.13-125.00  60.00  120
 28  \w     47.00 111.00   0.50    0.10    --  117.50-125.00  30.00  128
 29  \w     47.00 111.00   0.50    0.10    --  117.50-125.00   0.00  128
 30  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00  30.00  120
 31  \w     47.00 111.00   0.50    0.10    --  117.50-125.00-150.00  128
 32  \w     47.00 111.00   0.50    0.10    --  117.50-125.00-180.00  128
 33  \w     47.00 111.00   0.50    0.10    --  117.50-125.00-180.00  128
 34  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00-180.00  120
 35  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00-120.00  120
 36  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00 -90.00  120
 37  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00 -60.00  120
 38  \w     34.00  94.00   0.50    0.05    --   44.13-125.00-180.00  120
 39  \w     45.00 105.00   0.50    0.10    --  117.50 -95.00   0.00  120
 40  \w     45.00 150.00   0.50    0.10    --  117.50 -88.00  60.98  210
 41  \w     45.00 150.00   0.50    0.10    --  117.50 -88.00  60.98  210
 42  \w     45.00 147.00   0.50    0.10    --  117.50 -83.00 -24.56  204
 43  \w     45.00 145.00   0.50    0.10    --  117.50 -79.00-163.36  200
 44  \w     45.00 145.00   0.50    0.10    --  117.50 -79.00-163.36  200
 45  \w     45.00 105.00   0.50    0.10    --  117.50 -77.00-180.00  120
 46  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00-150.00   52
 47  \w     45.00 105.00   0.50    0.10    --  117.50 -77.00-150.00  120
 48  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00-120.00   52
 49  \w     45.00 105.00   0.50    0.10    --  117.50 -77.00  60.00  120
 50  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00  30.00   52
 51  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00  60.00   52
 52  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00  90.00   52
 53  \w     45.00  71.00   0.50    0.10    --  117.50 -61.00 120.00   52
 54  \w    -34.00  27.00   0.50    0.05    --   44.13 -19.00  90.00  122
 55  \w    -34.00  27.00   0.50    0.05    --   44.13 -19.00   0.00  122
 56  \w    -32.00  38.00   0.50    0.05    --   44.13 -33.00 153.00  140
 57  \w     95.00 178.00   0.50    0.10    --  117.50 125.00 120.00  166
 58  \w    -38.00  33.00   0.50    0.05    --  -44.13  33.00 -47.00  142
 59  \w    -51.00 -21.00   0.50    0.10    --  -96.00  45.00  90.00   60
 60  \w    -51.00 -21.00   0.50    0.10    --  -96.00  45.00 120.00   60
 61  \w    -51.00 -21.00   0.50    0.10    --  -96.00  45.00 150.00   60
 62  \w    -86.00 -25.00   0.50    0.10    --  -96.00 125.00 150.00  122
 63  \w    -86.00 -25.00   0.50    0.10    --  -96.00 125.00   0.00  122
 64  \w   -121.00 -24.00   0.50    0.05    --  -44.13 -33.00 153.00  194
 65  \w   -173.00 -75.00   0.50    0.10    --  -96.00 -33.00 153.00  196
;
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.742
_diffrn_reflns_theta_min         4.977
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_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    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0073(13)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0529P)^2^+0.1804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1832
_reflns_number_total             1923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1n_z481102
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_database_code               7249669
_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   0.779
_shelx_estimated_absorpt_t_max   0.880
_shelx_res_checksum              29901
_shelx_hkl_checksum              28238