Base-catalyzed regio- and stereoselective addition of isatins to trifluoromethylated alkynes for preparation of <i>N</i>-alkenylisatins.
Ma, Minglan; Liu, Guangyuan; Meng, Fangyu; Li, Qiang; Zhou, Yirong; Organic & biomolecular chemistry 23 (2025) 10496–10501; doi:10.1039/d5ob01514f

data_7160822
_publ_section_title
;
 Base-catalyzed regio- and stereoselective addition of isatins to
 trifluoromethylated alkynes for preparation of <i>N</i>-alkenylisatins.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10496
_journal_page_last               10501
_journal_paper_doi               10.1039/d5ob01514f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C17 H10 F3 N O2'
_chemical_formula_sum            'C17 H10 F3 N O2'
_chemical_formula_weight         317.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-28 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.57550(10)
_cell_length_b                   10.62760(10)
_cell_length_c                   14.31220(10)
_cell_measurement_reflns_used    25608
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.1980
_cell_measurement_theta_min      3.1380
_cell_volume                     1433.65(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9914
_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    -70.00 -30.00   0.50    0.50    --    0.00 -42.00 -97.00   80
  2  \w    -25.00  15.00   0.50    0.50    --    0.00 -42.00 -97.00   80
  3  \w     71.00  97.00   0.50    0.50    --   95.80 -42.00 -97.00   52
  4  \w    131.00 170.00   0.50    0.50    --   95.80  42.00  55.00   78
  5  \w     10.00  47.00   0.50    0.50    --    0.00  42.00  55.00   74
  6  \w     12.00  47.00   0.50    0.50    --   36.00  71.00 -45.02   70
  7  \w     14.00  70.00   0.50    0.50    --   40.00  71.00  69.42  112
  8  \w     60.00 131.00   0.50    0.50    --   44.00  72.00 160.39  142
  9  \w     17.00  43.00   0.50    0.50    --   44.00  72.00 160.39   52
 10  \w    -42.00  62.00   0.50    0.50    --   44.00 -42.00 146.06  208
 11  \w     33.00  70.00   0.50    0.50    --   56.00  75.00 -31.84   74
 12  \w     32.00  65.00   0.50    0.50    --   60.00  75.00 170.98   66
 13  \w     33.00  58.00   0.50    0.50    --   60.00  75.00 -58.54   50
 14  \w     32.00  68.00   0.50    0.50    --   60.00  75.00  47.78   72
 15  \w     37.00  81.00   0.50    0.50    --   64.00  73.00 109.53   88
 16  \w     37.00  87.00   0.50    0.50    --   64.00  74.00-153.36  100
 17  \w     42.00  72.00   0.50    0.50    --   68.00  75.00-120.95   60
 18  \w     44.00  86.00   0.50    0.50    --   72.00  74.00 -26.89   84
 19  \w     44.00  77.00   0.50    0.50    --   72.00  74.00  56.41   66
 20  \w     44.00  75.00   0.50    0.50    --   72.00  75.00-108.54   62
 21  \w     46.00 109.00   0.50    0.50    --   72.00  75.00  -6.59  126
 22  \w     44.00  76.00   0.50    0.50    --   72.00  75.00 -62.34   64
 23  \w    128.00 161.00   0.50    0.50    --   76.00  73.00 112.01   66
 24  \w     48.00  90.00   0.50    0.50    --   76.00  75.00 135.53   84
 25  \w    111.00 165.00   0.50    0.50    --   76.00  72.00-172.43  108
 26  \w     50.00 107.00   0.50    0.50    --   76.00  72.00-172.43  114
 27  \w     50.00  85.00   0.50    0.50    --   76.00  73.00 112.01   70
 28  \w     71.00 101.00   0.50    0.50    --   95.80  71.00 -62.71   60
 29  \w     79.00 182.00   0.50    0.50    --   95.80  61.00  90.00  206
 30  \w     87.00 127.00   0.50    0.50    --   95.80 -82.00  60.00   80
 31  \w     41.00 123.00   0.50    0.50    --   95.80 -82.00  30.00  164
 32  \w     72.00 180.00   0.50    0.50    --   95.80  61.00-150.00  216
 33  \w     75.00 112.00   0.50    0.50    --   95.80  61.00 120.00   74
 34  \w     72.00 184.00   0.50    0.50    --   95.80  61.00 -90.00  224
 35  \w     73.00 112.00   0.50    0.50    --   95.80  76.00  -8.98   78
 36  \w     43.00  81.00   0.50    0.50    --   95.80 -82.00  60.00   76
 37  \w     57.00 127.00   0.50    0.50    --   95.80 -82.00-150.00  140
 38  \w      6.00 118.00   0.50    0.50    --   95.80 -61.00-180.00  224
 39  \w     47.00 126.00   0.50    0.50    --   95.80 -82.00 120.00  158
 40  \w     76.00 185.00   0.50    0.50    --   95.80  58.00 147.70  218
 41  \w     86.00 111.00   0.50    0.50    --   95.80 -82.00   0.00   50
 42  \w      9.00  74.00   0.50    0.50    --   95.80 -82.00   0.00  130
 43  \w    159.00 184.00   0.50    0.50    --   95.80  61.00-120.00   50
 44  \w      7.00  32.00   0.50    0.50    --   95.80 -82.00 120.00   50
 45  \w     76.00 185.00   0.50    0.50    --   95.80  48.00  68.87  218
 46  \w     73.00 162.00   0.50    0.50    --   95.80  61.00  30.00  178
 47  \w     76.00 119.00   0.50    0.50    --   95.80 -82.00 -90.00   86
 48  \w     68.00 182.00   0.50    0.50    --   95.80  72.00 -21.85  228
 49  \w     74.00 120.00   0.50    0.50    --   95.80  61.00-120.00   92
 50  \w     68.00  94.00   0.50    0.50    --   95.80  71.00  60.30   52
 51  \w    134.00 165.00   0.50    0.50    --   95.80  59.00 169.72   62
 52  \w     72.00 119.00   0.50    0.50    --   95.80  59.00 169.72   94
 53  \w     79.00 181.00   0.50    0.50    --   95.80  54.00 -63.52  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1255306000
_diffrn_orient_matrix_UB_12      0.0109707000
_diffrn_orient_matrix_UB_13      0.0535946000
_diffrn_orient_matrix_UB_21      -0.0088511000
_diffrn_orient_matrix_UB_22      0.1423028000
_diffrn_orient_matrix_UB_23      -0.0206853000
_diffrn_orient_matrix_UB_31      -0.1042587000
_diffrn_orient_matrix_UB_32      -0.0254157000
_diffrn_orient_matrix_UB_33      -0.0930670000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32088
_diffrn_reflns_theta_full        74.4479
_diffrn_reflns_theta_max         74.45
_diffrn_reflns_theta_min         5.17
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4698
_exptl_crystal_description       needle
_exptl_crystal_F_000             650.6707
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.1707
_refine_diff_density_min         -0.3038
_refine_diff_density_rms         0.0586
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             8.5627
_refine_ls_goodness_of_fit_ref   1.0655
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0655
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.6746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                2839
_reflns_number_total             2898
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5ob01514f2.cif
_cod_data_source_block           20250321_1
_cod_depositor_comments          'Adding full bibliography for 7160822.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7160822
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C12(H12), C11(H11), C7(H7), C6(H6), C5(H5),
 C4(H4), C16(H16)
;
_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 2.550
_oxdiff_exptl_absorpt_empirical_full_min 0.566