Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides.
Le, Christine M.; Sperger, Theresa; Fu, Rui; Hou, Xiao; Lim, Yong Hwan; Schoenebeck, Franziska; Lautens, Mark; Journal of the American Chemical Society 138 (2016) 14441–14448; doi:10.1021/jacs.6b08925

data_4131052
_publ_section_title
;
 Stereoselective Synthesis of Methylene Oxindoles via
 Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl
 Chlorides.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14441
_journal_page_last               14448
_journal_paper_doi               10.1021/jacs.6b08925
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H15 Cl F N O'
_chemical_formula_sum            'C22 H15 Cl F N O'
_chemical_formula_weight         363.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.188(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4120(7)
_cell_length_b                   10.3695(8)
_cell_length_c                   17.6799(11)
_cell_measurement_reflns_used    6484
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.71
_cell_measurement_theta_min      4.75
_cell_volume                     1707.9(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29249
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.276
_diffrn_reflns_theta_max         67.276
_diffrn_reflns_theta_min         4.747
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0538P)^2^+0.8361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08925_si_002.cif
_cod_data_source_block           d1613_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4131052
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.752
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              40711
_shelx_hkl_checksum              98650