Rawal's catalyst as an effective stimulant for the highly asymmetric Michael addition of β-keto esters to functionally rich nitro-olefins.
Suresh Kumar, A.; Prabhakar Reddy, T.; Madhavachary, R.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 14 (2016) 5494–5499; doi:10.1039/c5ob02178b

data_7154803
_publ_section_title
;
 Rawal's catalyst as an effective stimulant for the highly asymmetric
 Michael addition of \b-keto esters to functionally rich nitro-olefins.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5494
_journal_page_last               5499
_journal_paper_doi               10.1039/c5ob02178b
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H24 N2 O8'
_chemical_formula_sum            'C19 H24 N2 O8'
_chemical_formula_weight         408.40
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-16
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Olex2 1.2
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2015-10-20 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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  1 omega  -43.00  -17.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -24.00   44.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   26.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6182   57.0000  150.0000 77

  4 omega   42.00   70.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   37.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -25.00   39.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   16.00   42.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   52.00  109.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   81.00  175.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   56.00   86.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega  121.00  147.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  179.0000   60.0000 26

 12 omega   38.00   87.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 49

 13 omega   39.00   66.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 27

 14 omega   52.00   78.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

 15 omega   84.00  140.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   42.00  134.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 92

 17 omega  103.00  169.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 66
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_number            8310
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_diffrn_reflns_theta_max         71.864
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_density_diffrn    1.263
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_refine_ls_abs_structure_details
;
 Flack x determined using 704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       0.0018(3)
_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   0.996
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3936
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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^)+(0.0380P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
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_cod_depositor_comments          'Adding full bibliography for 7154803.cif.'
_cod_original_cell_volume        2147.43(19)
_cod_database_code               7154803
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C19 H24 N2 O8'
_chemical_oxdiff_usercomment     SURESH
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
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_olex2_submission_special_instructions 'No special instructions were received'