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_7249667
_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_absolute_configuration ad
_chemical_formula_moiety         'C8 H3 F N4 O3'
_chemical_formula_sum            'C8 H3 F N4 O3'
_chemical_formula_weight         222.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 105.4990(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.14289(10)
_cell_length_b                   5.60083(7)
_cell_length_c                   9.26194(11)
_cell_measurement_reflns_used    7007
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.0170
_cell_measurement_theta_min      4.9330
_cell_volume                     407.048(9)
_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 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     42.00  99.00   0.50    0.08    --  111.50-125.00 150.00  114
  2  \w     69.00 104.00   0.50    0.08    --  111.50 -95.00 120.00   70
  3  \w     42.00  70.00   0.50    0.08    --  111.50 -95.00   0.00   56
  4  \w     57.00 101.00   0.50    0.08    --  111.50 -95.00 -30.00   88
  5  \w     95.00 137.00   0.50    0.08    --  111.50 -86.00-142.81   84
  6  \w     50.00  99.00   0.50    0.08    --  111.50-125.00 -90.00   98
  7  \w     46.00  72.00   0.50    0.08    --  111.50 -77.00 -90.00   52
  8  \w     41.00  67.00   0.50    0.08    --  111.50 -61.00-120.00   52
  9  \w     42.00  86.00   0.50    0.08    --  111.50 -77.00-120.00   88
 10  \w     40.00  65.00   0.50    0.08    --  111.50 -61.00 -60.00   50
 11  \w     41.00  69.00   0.50    0.08    --  111.50 -61.00   0.00   56
 12  \w     40.00  65.00   0.50    0.08    --  111.50 -61.00  60.00   50
 13  \w     41.00  66.00   0.50    0.08    --  111.50 -61.00 120.00   50
 14  \w     44.00  70.00   0.50    0.08    --  111.50 -61.00 150.00   52
 15  \w     42.00  69.00   0.50    0.08    --  111.50 -61.00 -90.00   54
 16  \w    106.00 145.00   0.50    0.08    --  111.50  15.00 -60.00   78
 17  \w     90.00 117.00   0.50    0.08    --  111.50  77.00   0.00   54
 18  \w     92.00 161.00   0.50    0.08    --  111.50  77.00  30.00  138
 19  \w    144.00 170.00   0.50    0.08    --  111.50  77.00   0.00   52
 20  \w     95.00 143.00   0.50    0.08    --  111.50  77.00 -30.00   96
 21  \w     90.00 116.00   0.50    0.08    --  111.50  77.00 -60.00   52
 22  \w     90.00 129.00   0.50    0.08    --  111.50  77.00 -90.00   78
 23  \w    153.00 178.00   0.50    0.08    --  111.50  61.00  60.00   50
 24  \w    141.00 167.00   0.50    0.08    --  111.50  77.00 120.00   52
 25  \w    143.00 173.00   0.50    0.08    --  111.50  61.00 150.00   60
 26  \w    100.00 125.00   0.50    0.08    --  111.50  61.00 150.00   50
 27  \w     92.00 119.00   0.50    0.08    --  111.50  77.00 120.00   54
 28  \w     97.00 150.00   0.50    0.08    --  111.50  61.00   0.00  106
 29  \w    145.00 171.00   0.50    0.08    --  111.50  61.00 -60.00   52
 30  \w    110.00 177.00   0.50    0.08    --  111.50  61.00 -37.49  134
 31  \w     97.00 133.00   0.50    0.08    --  111.50  61.00 -60.00   72
 32  \w     97.00 135.00   0.50    0.08    --  111.50  61.00 -90.00   76
 33  \w    139.00 173.00   0.50    0.08    --  111.50  61.00 -90.00   68
 34  \w    102.00 178.00   0.50    0.08    --  111.50  34.00-134.00  152
 35  \w    102.00 178.00   0.50    0.08    --  111.50  34.00-134.00  152
 36  \w    152.00 178.00   0.50    0.08    --  111.50  15.00 -60.00   52
 37  \w    101.00 140.00   0.50    0.08    --  111.50  61.00  30.00   78
 38  \w    107.00 133.00   0.50    0.08    --  111.50  45.00  30.00   52
 39  \w    -24.00  39.00   0.50    0.05    --   48.14 -34.00  67.00  126
 40  \w     34.00 120.00   0.50    0.05    --   48.14  57.00   0.00  172
 41  \w    100.00 130.00   0.50    0.08    --  111.50 125.00-150.00   60
 42  \w    141.00 170.00   0.50    0.08    --  111.50 125.00-150.00   58
 43  \w     27.00 120.00   0.50    0.05    --   48.14  77.00 -60.00  186
 44  \w     38.00 122.00   0.50    0.05    --   48.14  34.00-134.00  168
 45  \w     38.00 122.00   0.50    0.05    --   48.14  34.00-134.00  168
 46  \w    -27.00  26.00   0.50    0.05    --  -48.14  19.00  30.00  106
 47  \w    -39.00  26.00   0.50    0.05    --  -48.14  34.00-134.00  130
 48  \w    -51.00 -18.00   0.50    0.08    --  -90.00  45.00  30.00   66
 49  \w    -71.00 -18.00   0.50    0.08    --  -90.00  61.00  60.00  106
 50  \w   -122.00 -37.00   0.50    0.05    --  -48.14 -34.00  67.00  170
 51  \w   -122.00 -37.00   0.50    0.05    --  -48.14 -34.00  67.00  170
 52  \w   -120.00 -37.00   0.50    0.05    --  -48.14 -38.00   0.00  166
 53  \w   -108.00 -74.00   0.50    0.08    --  -90.00 -68.00 -86.31   68
 54  \w   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00 -60.00  186
 55  \w   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00 -30.00  186
 56  \w   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00   0.00  186
 57  \w   -161.00 -68.00   0.50    0.08    --  -90.00 -77.00  30.00  186
 58  \w   -163.00 -79.00   0.50    0.08    --  -90.00 -34.00  67.00  168
 59  \w   -161.00 -73.00   0.50    0.08    --  -90.00 -65.00 -26.23  176
 60  \w   -161.00 -73.00   0.50    0.08    --  -90.00 -65.00 -37.68  176
 61  \w   -161.00 -74.00   0.50    0.08    --  -90.00 -62.00 -66.56  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.527
_diffrn_reflns_theta_min         4.955
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.387
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.662
_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    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1752
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0398P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                1741
_reflns_number_total             1752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01068j2.cif
_cod_data_source_block           1k_z475101
_cod_depositor_comments
'Adding full bibliography for 7249665--7249669.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7249667
_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   0.689
_shelx_estimated_absorpt_t_max   0.909
_shelx_res_checksum              46166
_shelx_hkl_checksum              95663