A four-component reaction to access 3,3-disubstituted indolines <i>via</i> the palladium-norbornene-catalyzed <i>ortho</i> amination/<i>ipso</i> conjunctive coupling.
Rago, Alexander J.; Ye, Rong; Liu, Xin; Dong, Guangbin; Chemical science 15 (2024) 1318–1323; doi:10.1039/d3sc06409c

data_1570559
_publ_section_title
;
 A four-component reaction to access 3,3-disubstituted indolines
 <i>via</i> the palladium-norbornene-catalyzed <i>ortho</i>
 amination/<i>ipso</i> conjunctive coupling.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1318
_journal_page_last               1323
_journal_paper_doi               10.1039/d3sc06409c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C17 H18 N'
_chemical_formula_sum            'C17 H18 N'
_chemical_formula_weight         236.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-25 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5075(2)
_cell_length_b                   9.6128(2)
_cell_length_c                   16.4841(4)
_cell_measurement_reflns_used    9036
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      78.5180
_cell_measurement_theta_min      4.5800
_cell_volume                     1348.08(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (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_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -107.00 -78.00   0.50    0.20    --  -47.50   0.00-120.00   58
  2  \w   -105.00 -79.00   0.50    0.20    --  -47.50   0.00 -30.00   52
  3  \w   -119.00 -94.00   0.50    0.20    --  -47.50   0.00 150.00   50
  4  \w    -11.00  28.00   0.50    0.20    --  -47.50  19.00 150.00   78
  5  \w    -59.00  17.00   0.50    0.20    --  -47.50  57.00  90.00  152
  6  \w     51.00 110.00   0.50    1.00    --  113.25-125.00-120.00  118
  7  \w     81.00 106.00   0.50    1.00    --  113.25 -94.00-180.00   50
  8  \w     42.00  68.00   0.50    1.00    --  113.25 -94.00-180.00   52
  9  \w     78.00 106.00   0.50    1.00    --  113.25 -94.00-120.00   56
 10  \w     57.00  83.00   0.50    1.00    --  113.25 -94.00 -60.00   52
 11  \w     60.00 105.00   0.50    1.00    --  113.25-110.00  48.00   90
 12  \w     46.00  71.00   0.50    1.00    --  113.25 -61.00 -90.00   50
 13  \w     44.00  71.00   0.50    1.00    --  113.25 -61.00-120.00   54
 14  \w     64.00  92.00   0.50    0.20    --   47.50-125.00-120.00   56
 15  \w     15.00  65.00   0.50    0.20    --   47.50-110.00  48.00  100
 16  \w    103.00 174.00   0.50    1.00    --  113.25  30.00-120.00  142
 17  \w    104.00 178.00   0.50    1.00    --  113.25  45.00 -60.00  148
 18  \w    102.00 128.00   0.50    1.00    --  113.25  45.00 -30.00   52
 19  \w     25.00 118.00   0.50    0.20    --   47.50  77.00 150.00  186
 20  \w     82.00 143.00   0.50    1.00    --  113.25 110.00 143.00  122
 21  \w     94.00 119.00   0.50    1.00    --  113.25 125.00   0.00   50
 22  \w    131.00 174.00   0.50    1.00    --  113.25 125.00   0.00   86
 23  \w    -73.00  -8.00   0.50    0.20    --  -47.50 110.00 143.00  130
 24  \w   -108.00 -56.00   0.50    1.00    -- -106.00 110.00 143.00  104
 25  \w    -95.00 -46.00   0.50    1.00    -- -106.00 125.00  60.00   98
 26  \w   -107.00 -40.00   0.50    1.00    -- -106.00 105.00  52.62  134
 27  \w   -111.00 -38.00   0.50    1.00    -- -106.00 125.00 -60.00  146
 28  \w    -75.00 -35.00   0.50    1.00    -- -106.00  61.00  60.00   80
 29  \w    -62.00 -34.00   0.50    1.00    -- -106.00  61.00 120.00   56
 30  \w    -67.00 -36.00   0.50    1.00    -- -106.00  61.00   0.00   62
 31  \w    -75.00 -33.00   0.50    1.00    -- -106.00  61.00 -90.00   84
 32  \w    -69.00 -36.00   0.50    1.00    -- -106.00  61.00-180.00   66
 33  \w   -142.00 -92.00   0.50    1.00    -- -106.00-110.00  48.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13761
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.313
_diffrn_reflns_theta_min         5.327
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0697P)^2^+0.2881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2657
_reflns_number_total             2832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06409c2.cif
_cod_data_source_block           ry_1_183b_1
_cod_depositor_comments          'Adding full bibliography for 1570559.cif.'
_cod_database_code               1570559
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Others
 Fixed Sof: C15B(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C16B(0.5) H16A(0.5)
 H16B(0.5) H16C(0.5) C15A(0.5) H15D(0.5) H15E(0.5) H15F(0.5) C16A(0.5)
 H16D(0.5) H16E(0.5) H16F(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15B(H15A,H15B,H15C), C16B(H16A,H16B,H16C), C15A(H15D,H15E,
 H15F), C16A(H16D,H16E,H16F)
;
_shelx_res_checksum              89684
_shelx_hkl_checksum              86827
_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
;