Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer
He, Yingying; Li, Hongtao; Song, Longlong; Chen, Lili; Liu, Shunying; New Journal of Chemistry 48 (2024) 7754–7760; doi:10.1039/D4NJ00347K

data_7063108
_publ_section_title
;
 Efficient synthesis of bioactive isoindolinone derivatives containing
 continuous quaternary carbons by intermolecular OH transfer
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7754
_journal_page_last               7760
_journal_paper_doi               10.1039/D4NJ00347K
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H20 F3 N O5'
_chemical_formula_sum            'C25 H20 F3 N O5'
_chemical_formula_weight         471.42
_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
_audit_creation_date             2023-11-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-17 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.561(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2517(2)
_cell_length_b                   20.7292(7)
_cell_length_c                   13.3563(5)
_cell_measurement_reflns_used    7354
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.1830
_cell_measurement_theta_min      3.3810
_cell_volume                     2229.93(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_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    -36.00 -10.00   1.00    2.00    --    0.00 -77.00 150.00   26
  2  \w     -9.00  24.00   1.00    2.00    --    0.00 -37.00   0.00   33
  3  \w    -89.00 -38.00   1.00    2.00    --    0.00 -37.00   0.00   51
  4  \w    -89.00 -27.00   1.00    2.00    --    0.00 -77.00  90.00   62
  5  \w    -14.00  33.00   1.00    2.00    --    0.00 -77.00  90.00   47
  6  \w    -56.00  20.00   1.00    2.00    --    0.00 -37.00-150.00   76
  7  \w     86.00 158.00   1.00    4.00    --   92.10  45.00  30.00   72
  8  \w     58.00 128.00   1.00    4.00    --   92.10 -82.00 120.00   70
  9  \w     59.00 116.00   1.00    4.00    --   92.10 -61.00 120.00   57
 10  \w      3.00 120.00   1.00    4.00    --   92.10 -61.00   0.00  117
 11  \w     78.00 104.00   1.00    4.00    --   92.10 -61.00-180.00   26
 12  \w     77.00 103.00   1.00    4.00    --   92.10 -82.00 -90.00   26
 13  \w     50.00  76.00   1.00    4.00    --   92.10 -82.00 -60.00   26
 14  \w     79.00 104.00   1.00    4.00    --   92.10 -82.00 -60.00   25
 15  \w     10.00  35.00   1.00    4.00    --   92.10 -82.00 120.00   25
 16  \w     61.00 128.00   1.00    4.00    --   92.10 -82.00-150.00   67
 17  \w      5.00  30.00   1.00    4.00    --   92.10 -82.00-150.00   25
 18  \w     21.00  47.00   1.00    4.00    --   92.10 -61.00-180.00   26
 19  \w     94.00 120.00   1.00    4.00    --   92.10 -82.00  60.00   26
 20  \w      3.00 118.00   1.00    4.00    --   92.10 -45.00 120.00  115
 21  \w      6.00  68.00   1.00    4.00    --   92.10 -45.00-120.00   62
 22  \w     77.00 107.00   1.00    4.00    --   92.10 -45.00-120.00   30
 23  \w      3.00 127.00   1.00    4.00    --   92.10 -82.00   0.00  124
 24  \w     97.00 175.00   1.00    4.00    --   92.10  45.00 -60.00   78
 25  \w      5.00  44.00   1.00    4.00    --   92.10 -61.00 120.00   39
 26  \w     91.00 182.00   1.00    4.00    --   92.10  45.00  60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0758011000
_diffrn_orient_matrix_UB_12      0.0589812000
_diffrn_orient_matrix_UB_13      -0.0431445000
_diffrn_orient_matrix_UB_21      0.0453929000
_diffrn_orient_matrix_UB_22      0.0295396000
_diffrn_orient_matrix_UB_23      0.1083810000
_diffrn_orient_matrix_UB_31      0.1694504000
_diffrn_orient_matrix_UB_32      -0.0342951000
_diffrn_orient_matrix_UB_33      0.0192672000
_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  0.1630
_diffrn_reflns_av_unetI/netI     0.1141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23442
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         3.390
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (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    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_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     619
_refine_ls_number_reflns         6757
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1169P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2167
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.690
_reflns_Friedel_fraction_max     0.690
_reflns_number_gt                5476
_reflns_number_total             6757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00347k2.cif
_cod_data_source_block           exp_3737_auto
_cod_depositor_comments          'Adding full bibliography for 7063108.cif.'
_cod_database_code               7063108
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.765
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O6-C32
 1.42 with sigma of 0.01
 O6-C28
 1.42 with sigma of 0.01
 H29-H32B
 1.9 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3A), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C20(H20), C22(H22), C23(H23), C24(H24), N2(H2A), C26(H26), C27(H27),
 C29(H29), C30(H30), C36(H36), C37(H37), C38(H38), C39(H39), C45(H45), C47(H47),
  C48(H48), C49(H49)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C32(H32A,H32B,H32C), C43(H43A,H43B,H43C)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O9(H9)
;
_shelx_res_checksum              24841
_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 2.890
_oxdiff_exptl_absorpt_empirical_full_min 0.113