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_4519061
_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            'C21 H26 Cl2 N3 Rh'
_chemical_formula_weight         494.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                83.552(2)
_cell_angle_beta                 89.982(2)
_cell_angle_gamma                67.377(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1752(2)
_cell_length_b                   8.6053(2)
_cell_length_c                   18.3209(5)
_cell_measurement_reflns_used    8022
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.29
_cell_volume                     1036.44(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.738
_diffrn_reflns_theta_min         2.240
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0313P)^2^+0.3439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4690
_reflns_number_total             5118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03603_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4519061
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.560
_shelx_estimated_absorpt_t_max   0.669
_shelx_res_checksum              46850
_shelx_hkl_checksum              87315