Electrophilic aromatic substitution using fluorinated isoxazolines at the C5 position via C–F bond cleavage
Sato, Kazuyuki; Kuroki, Tomohiro; Minami, Haruka; Sato, Azusa; Karuo, Yukiko; Tarui, Atsushi; Kawai, Kentaro; Omote, Masaaki; RSC Advances 14 (2024) 39543–39549; doi:10.1039/D4RA07102F

data_7249697
_publ_section_title
;
 Electrophilic aromatic substitution using fluorinated isoxazolines at the
 C5 position via C--F bond cleavage
;
_journal_issue                   53
_journal_name_full               'RSC Advances'
_journal_page_first              39543
_journal_page_last               39549
_journal_paper_doi               10.1039/D4RA07102F
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C23 H19 F2 N O'
_chemical_formula_sum            'C23 H19 F2 N O'
_chemical_formula_weight         363.39
_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             2024-04-18
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-04-19 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3894(2)
_cell_length_b                   6.21370(10)
_cell_length_c                   16.7372(2)
_cell_measurement_reflns_used    19760
_cell_measurement_temperature    120.0(4)
_cell_measurement_theta_max      76.6980
_cell_measurement_theta_min      2.5370
_cell_volume                     1797.88(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(4)
_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 0.996
_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      6.00  34.00   0.50    0.10    --   43.16  94.00-119.85   56
  2  \w     21.00 117.00   0.50    0.10    --   43.16  57.00-150.00  192
  3  \w     21.00 117.00   0.50    0.10    --   43.16  57.00 -60.00  192
  4  \w      6.00  34.00   0.50    0.10    --   43.16  94.00  11.65   56
  5  \w      9.00  42.00   0.50    0.10    --   43.16  89.00 130.21   66
  6  \w    -31.00 123.00   0.50    0.10    --   43.16   8.00-124.00  308
  7  \w     38.00 106.00   0.50    0.39    --  113.00 -95.00   0.00  136
  8  \w     19.00  95.00   0.50    0.10    --   43.16-125.00 -60.00  152
  9  \w     19.00  95.00   0.50    0.10    --   43.16-125.00-150.00  152
 10  \w     41.00 112.00   0.50    0.39    --  113.00-125.00 -30.00  142
 11  \w     41.00 112.00   0.50    0.39    --  113.00-125.00   0.00  142
 12  \w     41.00 112.00   0.50    0.39    --  113.00-125.00  60.00  142
 13  \w     41.00 112.00   0.50    0.39    --  113.00-125.00 150.00  142
 14  \w     41.00 112.00   0.50    0.39    --  113.00-125.00  90.00  142
 15  \w     41.00 112.00   0.50    0.39    --  113.00-125.00-150.00  142
 16  \w     39.00 109.00   0.50    0.39    --  113.00 -78.00-125.72  140
 17  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00-150.00   74
 18  \w     39.00 106.00   0.50    0.39    --  113.00 -77.00 -60.00  134
 19  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00   0.00   74
 20  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00 -30.00   74
 21  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00-120.00   74
 22  \w     39.00 106.00   0.50    0.39    --  113.00 -77.00  30.00  134
 23  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00  60.00   74
 24  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00 120.00   74
 25  \w     39.00  76.00   0.50    0.39    --  113.00 -61.00 150.00   74
 26  \w    -36.00  35.00   0.50    0.10    --   43.16 -19.00  60.00  142
 27  \w     37.00 178.00   0.50    0.39    --  113.00   8.00-124.00  282
 28  \w     90.00 178.00   0.50    0.39    --  113.00  61.00-150.00  176
 29  \w     91.00 178.00   0.50    0.39    --  113.00  45.00-120.00  174
 30  \w     91.00 178.00   0.50    0.39    --  113.00  45.00 -90.00  174
 31  \w     63.00 178.00   0.50    0.39    --  113.00  15.00   0.00  230
 32  \w     63.00 178.00   0.50    0.39    --  113.00  15.00 120.00  230
 33  \w     63.00 178.00   0.50    0.39    --  113.00  15.00 150.00  230
 34  \w     91.00 178.00   0.50    0.39    --  113.00  45.00 120.00  174
 35  \w     86.00 178.00   0.50    0.39    --  113.00  83.00 157.40  184
 36  \w     86.00 178.00   0.50    0.39    --  113.00  90.00  57.81  184
 37  \w     80.00 178.00   0.50    0.39    --  113.00 125.00 -30.00  196
 38  \w     90.00 178.00   0.50    0.39    --  113.00  95.00 -52.27  176
 39  \w     80.00 178.00   0.50    0.39    --  113.00 125.00-180.00  196
 40  \w   -123.00  33.00   0.50    0.10    --  -43.16  -8.00  60.00  312
 41  \w   -120.00 -20.00   0.50    0.10    --  -43.16 -38.00 -30.00  200
 42  \w   -174.00 -81.00   0.50    0.39    -- -104.50 -77.00   0.00  186
 43  \w   -174.00 -75.00   0.50    0.39    -- -104.50 -77.00  30.00  198
 44  \w   -117.00 -14.00   0.50    0.10    --  -43.16 -77.00  90.00  206
 45  \w   -174.00 -75.00   0.50    0.39    -- -104.50 -77.00  67.24  198
 46  \w   -174.00 -28.00   0.50    0.39    -- -104.50  -8.00  60.00  292
 47  \w    -66.00 -30.00   0.50    0.39    -- -104.50  61.00 120.00   72
 48  \w    -96.00 -30.00   0.50    0.39    -- -104.50  77.00  60.00  132
 49  \w    -66.00 -30.00   0.50    0.39    -- -104.50  61.00   0.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0130187000
_diffrn_orient_matrix_UB_12      0.0228639000
_diffrn_orient_matrix_UB_13      -0.0892020000
_diffrn_orient_matrix_UB_21      -0.0879479000
_diffrn_orient_matrix_UB_22      -0.0137651000
_diffrn_orient_matrix_UB_23      -0.0238312000
_diffrn_orient_matrix_UB_31      -0.0061316000
_diffrn_orient_matrix_UB_32      0.2464903000
_diffrn_orient_matrix_UB_33      0.0068573000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40254
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.006
_diffrn_reflns_theta_min         2.556
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethylacetate'
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0345P)^2^+0.7896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             3825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07102f2.cif
_cod_data_source_block           x-1339_auto
_cod_database_code               7249697
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H19 F2 N O'
_chemical_oxdiff_usercomment     5aH
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C26(H26C,H26A,H26B), C27(H27A,H27C,H27B)
;
_shelx_res_checksum              41792
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in  perfluoropolyether oil'
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.755