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_4029435
_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_moiety         'C23 H18 N2 O4 S'
_chemical_formula_sum            'C23 H18 N2 O4 S'
_chemical_formula_weight         418.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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_date             2013-01-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.475(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2604(4)
_cell_length_b                   15.8897(5)
_cell_length_c                   13.0090(6)
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      29.0396
_cell_measurement_theta_min      3.0434
_cell_volume                     2011.61(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11337
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.05
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9387
_exptl_absorpt_correction_T_min  0.9281
_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_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0598P)^2^+0.9135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                2984
_reflns_number_total             4113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500432c_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4029434--4029435.cif.'
_cod_database_code               4029435
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.057) H2(0.082) H3(0.087) H1'(0.057) H3'(0.087) H2'(0.082)
 H5(0.045) H14(0.078) H8(0.047) H24(0.057) H23(0.072) H12(0.066) H20(0.067)
 H13(0.075) H15(0.067) H22(0.08) H21(0.081) H17A(0.114) H17B(0.114) H17C(0.114)
 Fixed X: H1(0.9563) H2(1.0156) H3(0.8379) H1'(0.6455) H3'(1.0057) H2'(0.8359)
 H5(0.7309) H14(1.1318) H8(0.5302) H24(0.406) H23(0.2933) H12(1.1421)
 H20(0.3619) H13(1.2475) H15(0.9058) H22(0.2091) H21(0.2433) H17A(0.8436)
 H17B(0.9996) H17C(0.9205)
 Fixed Y: H1(0.0256) H2(-0.1208) H3(-0.1939) H1'(-0.0869) H3'(-0.1273) H2'(-
 0.1908) H5(0.1258) H14(0.2978) H8(0.0546) H24(-0.0461) H23(-0.101) H12(0.1707)
 H20(0.1855) H13(0.2546) H15(0.2562) H22(-0.0127) H21(0.1303) H17A(0.045)
 H17B(0.0543) H17C(0.1297)
 Fixed Z: H1(0.3406) H2(0.3398) H3(0.2135) H1'(0.1509) H3'(0.3424) H2'(0.1955)
 H5(0.2559) H14(0.3075) H8(0.0762) H24(0.3214) H23(0.4337) H12(0.0444)
 H20(0.4265) H13(0.193) H15(0.2791) H22(0.538) H21(0.5346) H17A(-0.1425) H17B(-
 0.0755) H17C(-0.1455)
;