Organocatalytic Enantioselective Michael Addition between 3-(3-hydroxy-1H-pyrazol-1-yl)Oxindole and β-Nitrostyrene for the Preparation of Chiral Di-substituted Oxindoles.
Song, Xiang-Jia; Ren, Hong-Xia; Xiang, Min; Li, Chen-Yi; Zou, Ying; Li, Xia; Huang, Zhi-Cheng; Tian, Fang; Wang, Li-Xin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03337

data_4038550
_publ_section_title
;
 Organocatalytic Enantioselective Michael Addition between
 3-(3-hydroxy-1H-pyrazol-1-yl)Oxindole and \b-Nitrostyrene for the
 Preparation of Chiral Di-substituted Oxindoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03337
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 N4 O4'
_chemical_formula_sum            'C26 H22 N4 O4'
_chemical_formula_weight         454.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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  1 omega -108.00  -55.80   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   50.90   76.70   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   46.00   98.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   72.00   97.80   0.3000    1.0000
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  5 omega   17.00  105.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 294

  6 omega   81.00  109.50   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   54.00   94.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   11.00   43.10   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   65.00  105.20   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega    1.00   27.10   0.3000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 87

 11 omega   54.00   79.80   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 86

 12 omega   43.00   93.10   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega   39.00  108.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 187

 15 omega   53.00   84.50   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 105

 16 omega   50.00   95.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 150

 17 omega   48.00   78.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega  104.00  175.10   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   48.00  108.00   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   73.00  161.50   0.3000    5.0000
omega____ theta____ kappa____ phi______ frames
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0484547000
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_diffrn_orient_matrix_UB_21      -0.1617032000
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_diffrn_orient_matrix_UB_31      -0.0100967000
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_diffrn_reflns_number            18675
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        67.070
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
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 Flack x determined using 2748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
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_refine_ls_abs_structure_Flack   -0.05(11)
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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_refine_ls_goodness_of_fit_ref   1.026
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_refine_ls_restrained_S_all      1.026
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.2416P] where P=(Fo^2^+2Fc^2^)/3'
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_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
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_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C10'(H10C,H10D), C20'(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C12'(H12'), C13'(H13'), C14'(H14'),
 C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C22'(H22'), C23'(H23'),
 C24'(H24'), C25'(H25'), C26'(H26')
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O4'(H4'A)
;
_olex2_submission_special_instructions 'No special instructions were received'