Organocatalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to chiral α-aryl-α-hydroxy carboxylic acids
Jiao, Lihui; Zhao, Xiaowei; Liu, Huixin; Ye, Xinyi; Li, Yun; Jiang, Zhiyong; Organic Chemistry Frontiers 3 (2016) 470–; doi:10.1039/C5QO00428D

data_1553231
_publ_section_title
;
 Organocatalytic asymmetric conjugate addition of
 diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to
 chiral \a-aryl-\a-hydroxy carboxylic acids
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              470
_journal_paper_doi               10.1039/C5QO00428D
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H18 N2 O5'
_chemical_formula_sum            'C23 H18 N2 O5'
_chemical_formula_weight         402.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4957)
;
_audit_update_record
;
2015-08-07 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.486(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6839(2)
_cell_length_b                   11.0556(3)
_cell_length_c                   12.4153(4)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.0350
_cell_measurement_theta_min      3.7020
_cell_volume                     1011.32(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -74.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  150.0000 25

  2 omega    2.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 27

  3 omega   30.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 38

  4 omega   -2.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 44

  5 omega   44.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 81

  6 omega   20.00   49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000 -180.0000 29

  7 omega   14.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 84

  8 omega  -13.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   60.0000 86

  9 omega    0.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 61

 10 omega   59.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 66

 11 omega   90.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -158.0000 -120.0000 36

 12 omega   66.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 59

 13 omega   40.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 72

 14 omega   45.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 30

 15 omega   54.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 49

 16 omega   82.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 93

 17 omega   42.00   72.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 30

 18 omega   41.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 65

 19 omega   45.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 30

 20 omega   42.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 43

 21 omega   53.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  150.0000 50

 22 omega   47.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 42

 23 omega   41.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 44

 24 omega   74.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 35

 25 omega   97.00  123.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 26

 26 omega  139.00  166.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 27

 27 omega   85.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -60.0000 80

 28 omega   43.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 46

 29 omega   41.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 48

 30 omega   71.00   96.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 25

 31 omega   41.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 48

 32 omega  -77.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 45

 33 omega  -70.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  -30.0000 100

 34 omega   35.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 90

 35 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   90.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0024426000
_diffrn_orient_matrix_UB_12      0.0339856000
_diffrn_orient_matrix_UB_13      -0.1199088000
_diffrn_orient_matrix_UB_21      0.0287044000
_diffrn_orient_matrix_UB_22      0.1338334000
_diffrn_orient_matrix_UB_23      0.0352605000
_diffrn_orient_matrix_UB_31      0.2070028000
_diffrn_orient_matrix_UB_32      -0.0189959000
_diffrn_orient_matrix_UB_33      0.0334947000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7363
_diffrn_reflns_theta_full        67.02
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0563P)^2^+0.0959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                3205
_reflns_number_total             3596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00428d2.cif
_cod_data_source_block           lee11067
_cod_original_cell_volume        1011.33(5)
_cod_database_code               1553231
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'