A palladium-catalyzed sequential Heck coupling/C-C bond activation approach to oxindoles with all-carbon-quaternary centers.
Mao, Guoliang; Meng, Chenxiang; Cheng, Fangyuan; Wu, Wenbo; Gao, Yuan-Yuan; Li, Gao-Wei; Liu, Lantao; Organic & biomolecular chemistry 20 (2022) 1642–1646; doi:10.1039/d1ob02440j

data_7158503
_publ_section_title
;
 A palladium-catalyzed sequential Heck coupling/C-C bond activation
 approach to oxindoles with all-carbon-quaternary centers.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1642
_journal_page_last               1646
_journal_paper_doi               10.1039/d1ob02440j
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-11-06 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.0190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2614(3)
_cell_length_b                   13.2824(5)
_cell_length_c                   8.9573(3)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      53.709
_cell_measurement_theta_min      5.248
_cell_volume                     923.51(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      294(2)
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_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8924
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.624
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       prismatic
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_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
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_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
; 
 Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_coef       0.12(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.0713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3110
_reflns_number_total             3570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02440j2.cif
_cod_data_source_block           mo_d8v21393_0m
_cod_depositor_comments          'Adding full bibliography for 7158503.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158503
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              96641