Tandem Michael addition-ring transformation reactions of 3-hydroxyoxindoles/3-aminooxindoles with olefinic azlactones: direct access to structurally diverse spirocyclic oxindoles.
Cui, Bao-Dong; Zuo, Jian; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Wu, Zhi-Jun; Zhang, Xiao-Mei; Yuan, Wei-Cheng; The Journal of organic chemistry 79 (2014) 5305–5314; doi:10.1021/jo500432c

data_4029434
_publ_section_title
;
 Tandem Michael addition-ring transformation reactions of
 3-hydroxyoxindoles/3-aminooxindoles with olefinic azlactones: direct
 access to structurally diverse spirocyclic oxindoles.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5305
_journal_page_last               5314
_journal_paper_doi               10.1021/jo500432c
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C27 H23 N3 O4'
_chemical_formula_weight         453.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 94.9420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.48520(10)
_cell_length_b                   16.6744(2)
_cell_length_c                   15.2017(2)
_cell_measurement_reflns_used    9748
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.5485
_cell_measurement_theta_min      4.6755
_cell_volume                     2395.36(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20369
_diffrn_reflns_theta_full        69.68
_diffrn_reflns_theta_max         69.68
_diffrn_reflns_theta_min         5.30
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.8128
_exptl_absorpt_correction_T_min  0.7630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0032(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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0734P)^2^+0.3199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3807
_reflns_number_total             4480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500432c_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4029434--4029435.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4029434