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_4037144
_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 Br N O4'
_chemical_formula_weight         440.27
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.2700(10)
_cell_angle_beta                 81.7680(10)
_cell_angle_gamma                71.2150(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3639(2)
_cell_length_b                   8.9633(2)
_cell_length_c                   17.8417(5)
_cell_measurement_temperature    170(2)
_cell_volume                     940.07(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15829
_diffrn_reflns_theta_full        27.71
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    2.216
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0480P)^2^+0.3074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                3805
_reflns_number_total             4352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01596_si_002.cif
_cod_data_source_block           mo_2015124_0ma
_cod_original_cell_volume        940.07(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4037144