Highly diastereo- and enantioselective C2 addition of 5<i>H</i>-oxazol-4-ones to γ-keto-α,β-unsaturated esters.
Lin, Li; Wang, Mei; Zhou, Jiawei; Li, Fei; Liu, Huiyun; Chemical communications (Cambridge, England) 59 (2023) 3606–3609; doi:10.1039/d3cc00554b

data_7131352
_publ_section_title
;
 Highly diastereo- and enantioselective C2 addition of
 5<i>H</i>-oxazol-4-ones to &#x3b3;-keto-&#x3b1;,&#x3b2;-unsaturated
 esters.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3606
_journal_page_last               3609
_journal_paper_doi               10.1039/d3cc00554b
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 N O5'
_chemical_formula_sum            'C24 H25 N O5'
_chemical_formula_weight         407.45
_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             2014-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.23 svn.r3114 for OlexSys, GUI svn.r4973)
;
_audit_update_record
;
2015-03-30 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1825(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.14183(12)
_cell_length_b                   7.64267(12)
_cell_length_c                   20.2119(3)
_cell_measurement_reflns_used    3865
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      69.6340
_cell_measurement_theta_min      7.8010
_cell_volume                     1101.52(3)
_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
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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      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega    7.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 27

  2 omega  -73.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   90.0000 50

  3 omega  -12.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   90.0000 59

  4 omega  -17.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 74

  5 omega   53.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 69

  6 omega    1.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 64

  7 omega   34.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 89

  8 omega   29.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 84

  9 omega  -11.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 56

 10 omega   47.00  118.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 71

 11 omega   35.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 32

 12 omega   52.00  129.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 77

 13 omega   39.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 64

 14 omega   40.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 42

 15 omega  125.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 48

 16 omega   51.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 37

 17 omega   36.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 49

 18 omega   35.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 71

 19 omega   81.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 97

 20 omega   37.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 77

 21 omega  111.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 62

 22 omega   77.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 31

 23 omega   42.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -150.0000 136
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1603034000
_diffrn_orient_matrix_UB_12      -0.0379823000
_diffrn_orient_matrix_UB_13      0.0522311000
_diffrn_orient_matrix_UB_21      -0.0138068000
_diffrn_orient_matrix_UB_22      0.1885394000
_diffrn_orient_matrix_UB_23      0.0262729000
_diffrn_orient_matrix_UB_31      -0.1441766000
_diffrn_orient_matrix_UB_32      -0.0603444000
_diffrn_orient_matrix_UB_33      0.0490914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7064
_diffrn_reflns_theta_full        69.66
_diffrn_reflns_theta_max         69.66
_diffrn_reflns_theta_min         6.19
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57327
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.089
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0510P)^2^+0.0375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                3891
_reflns_number_total             4053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3cc00554b2.cif
_cod_data_source_block           wangmei1223
_cod_depositor_comments          'Adding full bibliography for 7131352.cif.'
_cod_database_code               7131352
_reflns_odcompleteness_completeness 99.63
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O4(0.47) O5(0.47) C10(0.47) C11(0.47) H11A(0.47) H11B(0.47)
 H11C(0.47) O4'(0.53) O5'(0.53) C10'(0.53) C11'(0.53) H11D(0.53) H11E(0.53)
 H11F(0.53)
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C11(H11A,H11B,
 H11C), C11'(H11D,H11E,H11F)
;
_olex2_submission_special_instructions 'No special instructions were received'