Rh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with Vinylsilanes via C–H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives
Khake, Shrikant M.; Chatani, Naoto; ACS Catalysis 11 (2021) 12375–12383; doi:10.1021/acscatal.1c03603

data_4519062
_publ_section_title
;
 Rh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with
 Vinylsilanes via C--H Activation/Alkene Cyclization: Access to Highly
 Regioselective Indoline Derivatives
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              12375
_journal_page_last               12383
_journal_paper_doi               10.1021/acscatal.1c03603
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C31 H27 N3 Si'
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                109.919(6)
_cell_angle_beta                 90.438(4)
_cell_angle_gamma                106.701(6)
_cell_formula_units_Z            2
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_cell_length_b                   10.5860(7)
_cell_length_c                   13.7057(7)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.99
_cell_measurement_theta_min      4.60
_cell_volume                     1226.40(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
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_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10259
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.044
_diffrn_reflns_theta_min         3.454
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.639
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_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0971
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2811
_refine_ls_wR_factor_ref         0.3174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3121
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03603_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1226.39(13)
_cod_database_code               4519062
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.494
_shelx_estimated_absorpt_t_max   0.821
_shelx_res_checksum              46882
_shelx_hkl_checksum              84416