Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
Yao-Zong Liu; Jie Zhang; Peng-Fei Xu; Yong-Chun Luo; Journal of Organic Chemistry 76 (2011) 7551–7555; doi:10.1021/jo201123p

data_4026572
_publ_section_title
;
 Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to
 \a,\b-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7551
_journal_page_last               7555
_journal_paper_doi               10.1021/jo201123p
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration none
_chemical_formula_sum            'C19 H18 Cl N O3'
_chemical_formula_weight         343.79
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.112(11)
_cell_length_b                   12.822(19)
_cell_length_c                   16.77(2)
_cell_measurement_reflns_used    734
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.83
_cell_measurement_theta_min      2.79
_cell_volume                     1744(4)
_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-97 (Sheldrick, 2008)'
_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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.1129
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6878
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0049P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                1436
_reflns_number_total             3251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201123p_si_001.cif
_cod_data_source_block           p212121
_cod_database_code               4026572