Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes.
Jin, Qiaowen; Zheng, Changwu; Zhao, Gang; Zou, Gang; The Journal of organic chemistry 82 (2017) 4840–4850; doi:10.1021/acs.joc.7b00571

data_4032537
_publ_section_title
;
 Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective
 Conjugate Addition of Oxindoles to Electron-Deficient \b-Haloalkenes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4840
_journal_page_last               4850
_journal_paper_doi               10.1021/acs.joc.7b00571
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H33 F6 N2 O3, C H Cl3, Br'
_chemical_formula_sum            'C27 H34 Br Cl3 F6 N2 O3'
_chemical_formula_weight         734.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9751(4)
_cell_length_b                   17.1860(7)
_cell_length_c                   21.3036(8)
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_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.30
_cell_volume                     3286.0(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.399
_diffrn_reflns_theta_min         3.304
_exptl_absorpt_coefficient_mu    4.530
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 2117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0514
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5421
_reflns_number_total             6036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00571_si_001.cif
_cod_data_source_block           t_0ma
_cod_database_code               4032537
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.409
_shelx_estimated_absorpt_t_max   0.550
_shelx_res_checksum              19194
_shelx_hkl_checksum              51518