A PASE synthesis of tetrazoloquinolines and its applications in the syntheses of bioactive compounds
Zhang, Xiaofeng; Nallapati, Sashirekha; Johnson, Shea; Chen, Xian; Lim, Jongwon; Green Chemistry 27 (2025) 10980–10987; doi:10.1039/D5GC00908A

data_7250813
_publ_section_title
;
 A PASE synthesis of tetrazoloquinolines and its applications in the
 syntheses of bioactive compounds
;
_journal_issue                   36
_journal_name_full               'Green Chemistry'
_journal_page_first              10980
_journal_page_last               10987
_journal_paper_doi               10.1039/D5GC00908A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C12 H9 F N4 O2'
_chemical_formula_sum            'C12 H9 F N4 O2'
_chemical_formula_weight         260.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-25
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-02-19 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.095(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.18790(10)
_cell_length_b                   19.4145(3)
_cell_length_c                   13.7194(3)
_cell_measurement_reflns_used    7575
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.9030
_cell_measurement_theta_min      3.9410
_cell_volume                     1106.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_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 0.999
_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   -120.00 -32.00   0.50    0.22    --  -46.48 -38.00  60.00  176
  2  \w   -120.00 -32.00   0.50    0.22    --  -46.48 -38.00 150.00  176
  3  \w    -63.00  27.00   0.50    0.22    --  -46.48  57.00 -60.00  180
  4  \w    -29.00  26.00   0.50    0.22    --   46.48 -19.00-120.00  110
  5  \w    -25.00  70.00   0.50    0.22    --   46.48 -77.00-180.00  190
  6  \w   -176.00 -33.00   0.50    1.00    -- -105.96   0.00-150.00  286
  7  \w    -71.00 -33.00   0.50    1.00    -- -105.96  61.00 120.00   76
  8  \w    -71.00 -33.00   0.50    1.00    -- -105.96  61.00   0.00   76
  9  \w    -71.00 -33.00   0.50    1.00    -- -105.96  61.00 -30.00   76
 10  \w    -71.00 -33.00   0.50    1.00    -- -105.96  61.00-120.00   76
 11  \w   -105.00 -33.00   0.50    1.00    -- -105.96  77.00  60.00  144
 12  \w   -105.00 -33.00   0.50    1.00    -- -105.96  77.00 -60.00  144
 13  \w   -125.00 -33.00   0.50    1.00    -- -105.96 142.00 146.09  184
 14  \w   -112.00 -36.00   0.50    1.00    -- -105.96 125.00-150.00  152
 15  \w   -176.00 -89.00   0.50    1.00    -- -105.96 -54.00-140.87  174
 16  \w   -176.00 -91.00   0.50    1.00    -- -105.96 -45.00 120.00  170
 17  \w   -121.00 -33.00   0.50    1.00    -- -105.96 138.00 108.26  176
 18  \w   -176.00 -91.00   0.50    1.00    -- -105.96 -49.00-176.28  170
 19  \w   -176.00 -33.00   0.50    1.00    -- -105.96   0.00-150.00  286
 20  \w     33.00 106.00   0.50    1.00    --  105.96 -94.00 -90.00  146
 21  \w     33.00 105.00   0.50    1.00    --  105.96 -77.00 -30.00  144
 22  \w     92.00 177.00   0.50    1.00    --  105.96  45.00  30.00  170
 23  \w     36.00 112.00   0.50    1.00    --  105.96-125.00 120.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1307103000
_diffrn_orient_matrix_UB_12      -0.0071502000
_diffrn_orient_matrix_UB_13      -0.0997305000
_diffrn_orient_matrix_UB_21      0.1153054000
_diffrn_orient_matrix_UB_22      0.0754074000
_diffrn_orient_matrix_UB_23      0.0072339000
_diffrn_orient_matrix_UB_31      0.3270610000
_diffrn_orient_matrix_UB_32      -0.0237449000
_diffrn_orient_matrix_UB_33      0.0528854000
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12028
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.576
_diffrn_reflns_theta_max         66.576
_diffrn_reflns_theta_min         3.966
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0961P)^2^+0.1778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1721
_reflns_number_total             1940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc00908a2.cif
_cod_data_source_block           es20080-1762-p1_a_auto
_cod_depositor_comments
'Adding full bibliography for 7250813--7250814.cif.'
_cod_database_code               7250813
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O N F'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.574
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.898
_oxdiff_exptl_absorpt_empirical_full_min 0.474