N-Heterocyclic Carbene Catalytic [4 + 2] Cyclization of 3-Alkylenyloxindoles with Enals: γ-Carbon Activation for Enantioselective Assembly of Spirocarbocyclic Oxindoles.
Yao, Hong; Zhou, Yu; Chen, Xia; Zhang, Pengfei; Xu, Jinyi; Liu, Hong; The Journal of organic chemistry 81 (2016) 8888–8899; doi:10.1021/acs.joc.6b01596

data_4037145
_publ_section_title
;
 N-Heterocyclic Carbene Catalytic [4 + 2] Cyclization of
 3-Alkylenyloxindoles with Enals: \g-Carbon Activation for
 Enantioselective Assembly of Spirocarbocyclic Oxindoles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8888
_journal_page_last               8899
_journal_paper_doi               10.1021/acs.joc.6b01596
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C22 H18 Cl N O3'
_chemical_formula_weight         379.82
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 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            8
_cell_length_a                   24.739(2)
_cell_length_b                   6.5307(6)
_cell_length_c                   22.413(2)
_cell_measurement_temperature    296(2)
_cell_volume                     3621.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0971
_diffrn_reflns_av_sigmaI/netI    0.1303
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14322
_diffrn_reflns_theta_full        24.40
_diffrn_reflns_theta_max         24.40
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.234
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                2723
_reflns_number_total             5505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01596_si_003.cif
_cod_data_source_block           mo_2015008_0ma
_cod_original_cell_volume        3621.0(5)
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               4037145