Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of 3-Allylidene-2(3<i>H</i>)-oxindoles and 3-Allylidene-2(3<i>H</i>)-benzofuranones.
Parveen, Naziya; Sekar, Govindasamy; The Journal of organic chemistry 85 (2020) 4682–4694; doi:10.1021/acs.joc.9b03397

data_4038112
_publ_section_title
;
 Palladium Nanoparticle-Catalyzed Stereoselective Domino Synthesis of
 3-Allylidene-2(3<i>H</i>)-oxindoles and
 3-Allylidene-2(3<i>H</i>)-benzofuranones.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4682
_journal_page_last               4694
_journal_paper_doi               10.1021/acs.joc.9b03397
_journal_volume                  85
_journal_year                    2020
_chemical_formula_sum            'C23 H15 Cl O2'
_chemical_formula_weight         358.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.874(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7179(9)
_cell_length_b                   12.4696(12)
_cell_length_c                   7.5883(8)
_cell_measurement_reflns_used    1424
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.73
_cell_volume                     879.95(15)
_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'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0306
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5733
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.633
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                2049
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03397_si_002.cif
_cod_data_source_block           4cl
_cod_depositor_comments
'Adding full bibliography for 4038109--4038113.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4038112
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              86908
_shelx_hkl_checksum              94701