Densely Substituted l-Proline Esters as Catalysts for Asymmetric Michael Additions of Ketones to Nitroalkenes.
Ruiz-Olalla, Andrea; Retamosa, María de Gracia; Cossío, Fernando P; The Journal of organic chemistry 80 (2015) 5588–5599; doi:10.1021/acs.joc.5b00495

data_4031035
_publ_section_title
;
 Densely Substituted l-Proline Esters as Catalysts for Asymmetric Michael
 Additions of Ketones to Nitroalkenes.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5588
_journal_page_last               5599
_journal_paper_doi               10.1021/acs.joc.5b00495
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H27 N1 O5'
_chemical_formula_sum            'C21 H27 N O5'
_chemical_formula_weight         373.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
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_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-26T12:45:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.762(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.497(3)
_cell_length_b                   5.4370(7)
_cell_length_c                   16.731(3)
_cell_measurement_reflns_used    1338
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.94
_cell_measurement_theta_min      2.778
_cell_measurement_wavelength     1.54184
_cell_volume                     1913.6(5)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
  1 omega  -19.00   31.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2006   57.0000  -30.0000 50

  2 omega  -57.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2006   57.0000 -120.0000 89

  3 omega   15.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2006   57.0000    0.0000 93

  4 omega   24.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2006   57.0000   90.0000 90

  5 omega -114.00  -38.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   68.0000  -41.0874 76

  6 omega -114.00  -50.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   69.0000   38.6188 64

  7 omega  -52.00  -26.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   70.0000  -97.7670 26

  8 omega -115.00  -66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   69.0000 -149.3120 49

  9 omega -108.00  -46.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   65.0000  144.7986 62

 10 omega  -99.00  -55.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   69.0000   76.4216 44

 11 omega -115.00  -83.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   69.0000  -64.8411 32

 12 omega -114.00  -60.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   70.0000  -97.7670 54

 13 omega   81.00  120.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000  142.1595 39

 14 omega  120.00  150.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 30

 15 omega   83.00  113.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   59.0000  148.0616 30

 16 omega   94.00  144.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   56.0000   98.1039 50

 17 omega   83.00  132.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 49

 18 omega   83.00  116.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   66.0000   82.5202 33

 19 omega   83.00  141.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 58

 20 omega   84.00  154.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   60.0000  -36.2705 70

 21 omega   85.00  128.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 43

 22 omega   91.00  138.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 47

 23 omega   81.00  151.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   68.0000 -170.4103 70

 24 omega   85.00  128.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 43

 25 omega   84.00  121.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 37

 26 omega   86.00  118.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 32

 27 omega   84.00  140.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   53.0000   61.9496 56

 28 omega   97.00  128.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 31

 29 omega   93.00  125.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 32

 30 omega   84.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   54.0000   22.0610 31

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.036858
_diffrn_orient_matrix_UB_12      0.0812874
_diffrn_orient_matrix_UB_13      -0.0926239
_diffrn_orient_matrix_UB_21      0.0013941
_diffrn_orient_matrix_UB_22      -0.2663756
_diffrn_orient_matrix_UB_23      -0.0309176
_diffrn_orient_matrix_UB_31      -0.0632402
_diffrn_orient_matrix_UB_32      -0.0527256
_diffrn_orient_matrix_UB_33      0.012841
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7354
_diffrn_reflns_theta_full        64.91
_diffrn_reflns_theta_max         64.91
_diffrn_reflns_theta_min         2.82
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.4045
_exptl_crystal_size_mid          0.0451
_exptl_crystal_size_min          0.0331
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1674
_reflns_number_gt                2171
_reflns_number_total             2992
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo5b00495_si_001.cif
_cod_data_source_block           a2014485_graci1
_cod_depositor_comments          'Adding full bibliography for 4031035.cif.'
_cod_database_code               4031035