Chiral Spirooxindole-Butenolide Synthesis through Asymmetric N-Heterocyclic Carbene-Catalyzed Formal (3 + 2) Annulation of 3-Bromoenals and Isatins.
Zheng, Chenguang; Yao, Weijun; Zhang, Yucheng; Ma, Cheng; Organic letters 16 (2014) 5028–5031; doi:10.1021/ol502365r

data_1517910
_publ_section_title
;
 Chiral Spirooxindole-Butenolide Synthesis through Asymmetric
 N-Heterocyclic Carbene-Catalyzed Formal (3 + 2) Annulation of
 3-Bromoenals and Isatins.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5028
_journal_page_last               5031
_journal_paper_doi               10.1021/ol502365r
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N O3'
_chemical_formula_sum            'C20 H19 N O3'
_chemical_formula_weight         321.36
_space_group_IT_number           94
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4n 2n'
_symmetry_space_group_name_H-M   'P 42 21 2'
_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                   15.41590(12)
_cell_length_b                   15.41590(12)
_cell_length_c                   15.6014(2)
_cell_measurement_reflns_used    15173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3183
_cell_measurement_theta_min      4.0280
_cell_volume                     3707.67(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37061
_diffrn_reflns_theta_full        67.43
_diffrn_reflns_theta_max         67.43
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.8251
_exptl_absorpt_correction_T_min  0.7927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_platon_squeeze_details
;
;
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack (1983), 1382 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1002P)^2^+0.2999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                3140
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502365r_si_002.cif
_cod_data_source_block           120703_zcg120703(4a)
_cod_original_cell_volume        3707.68(7)
_cod_original_sg_symbol_Hall     'P 4n 2n '
_cod_database_code               1517910