Catalyst- and solvent-free aminolysis of the asymmetric derivatives of Evans’ chiral N-acyloxazolidinones: enantioselective synthesis of chiral amides and its applications
Lu, Hui-Rong; Geng, Hui; Ding, Guan-Tian; Huang, Pei-Qiang; Green Chemistry 24 (2022) 4405–4413; doi:10.1039/D2GC00662F

data_7244855
_publ_section_title
;
 Catalyst- and solvent-free aminolysis of the asymmetric derivatives of
 Evans&#x2019; chiral N-acyloxazolidinones: enantioselective synthesis of
 chiral amides and its applications
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              4405
_journal_page_last               4413
_journal_paper_doi               10.1039/D2GC00662F
_journal_volume                  24
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.03.08 svn.r54f81f84 for OlexSys, GUI svn.r6485)
;
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2022-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.74880(10)
_cell_length_b                   9.78030(10)
_cell_length_c                   14.75820(10)
_cell_measurement_reflns_used    10337
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.0860
_cell_measurement_theta_min      5.4060
_cell_volume                     1407.14(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     77.00 115.00   0.50    0.05    --  107.76  77.00-120.00   76
  2  \w    124.00 157.00   0.50    0.05    --  107.76  77.00-120.00   66
  3  \w    102.00 178.00   0.50    0.05    --  107.76  45.00-150.00  152
  4  \w    130.00 162.00   0.50    0.05    --  107.76  30.00 -30.00   64
  5  \w     90.00 126.00   0.50    0.05    --  107.76  30.00 -30.00   72
  6  \w     83.00 148.00   0.50    0.05    --  107.76  61.00 120.00  130
  7  \w    -65.00  32.00   0.50    0.05    --  -43.10  57.00-180.00  194
  8  \w    -26.00   8.00   0.50    0.05    --  -43.10  19.00 -60.00   68
  9  \w    -25.00  28.00   0.50    0.05    --  -43.10  19.00 -30.00  106
 10  \w    -28.00  34.00   0.50    0.05    --  -43.10  38.00  60.00  124
 11  \w     33.00  85.00   0.50    0.05    --   43.10-125.00 120.00  104
 12  \w     84.00 117.00   0.50    0.05    --  107.76-125.00 120.00   66
 13  \w     42.00  79.00   0.50    0.05    --  107.76-125.00 120.00   74
 14  \w     34.00 113.00   0.50    0.05    --  107.76-125.00  90.00  158
 15  \w     87.00 117.00   0.50    0.05    --  107.76-125.00 -60.00   60
 16  \w     77.00 109.00   0.50    0.05    --  107.76 -94.00-150.00   64
 17  \w     34.00  65.00   0.50    0.05    --  107.76 -94.00-150.00   62
 18  \w     37.00 115.00   0.50    0.05    --  107.76-125.00-180.00  156
 19  \w     78.00 104.00   0.50    0.05    --  107.76 -94.00 -60.00   52
 20  \w     40.00  65.00   0.50    0.05    --  107.76 -77.00 -30.00   50
 21  \w     33.00  59.00   0.50    0.05    --  107.76 -61.00   0.00   52
 22  \w     46.00  71.00   0.50    0.05    --  107.76 -61.00  60.00   50
 23  \w     71.00  99.00   0.50    0.05    --  107.76 -77.00 -30.00   56
 24  \w     39.00  68.00   0.50    0.05    --  107.76 -61.00-120.00   58
 25  \w     33.00  58.00   0.50    0.05    --  107.76 -61.00-150.00   50
 26  \w    122.00 162.00   0.50    0.05    --  107.76 125.00 -90.00   80
 27  \w    149.00 174.00   0.50    0.05    --  107.76 125.00 -30.00   50
 28  \w     92.00 170.00   0.50    0.05    --  107.76 125.00 -60.00  156
 29  \w    100.00 126.00   0.50    0.05    --  107.76 125.00 -30.00   52
 30  \w     92.00 126.00   0.50    0.05    --  107.76 125.00  60.00   68
 31  \w    134.00 177.00   0.50    0.05    --  107.76 125.00  60.00   86
 32  \w    -42.00 -14.00   0.50    0.05    --  -90.25  45.00 120.00   56
 33  \w    -88.00 -63.00   0.50    0.05    --  -90.25  77.00  30.00   50
 34  \w    -55.00 -23.00   0.50    0.05    --  -90.25  77.00  30.00   64
 35  \w    -42.00 -15.00   0.50    0.05    --  -90.25  61.00  30.00   54
 36  \w    -48.00 -15.00   0.50    0.05    --  -90.25  45.00  30.00   66
 37  \w    -49.00 -13.00   0.50    0.05    --  -90.25  45.00   0.00   72
 38  \w    -48.00 -14.00   0.50    0.05    --  -90.25  45.00 -90.00   68
 39  \w    -44.00 -15.00   0.50    0.05    --  -90.25  45.00-120.00   58
 40  \w   -151.00 -72.00   0.50    0.05    --  -90.25 -61.00 -90.00  158
 41  \w   -116.00 -80.00   0.50    0.05    --  -43.10-125.00-120.00   72
 42  \w   -118.00 -93.00   0.50    0.05    --  -43.10-125.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0028132000
_diffrn_orient_matrix_UB_12      0.0108335000
_diffrn_orient_matrix_UB_13      -0.1041446000
_diffrn_orient_matrix_UB_21      -0.1526762000
_diffrn_orient_matrix_UB_22      0.0402133000
_diffrn_orient_matrix_UB_23      0.0036229000
_diffrn_orient_matrix_UB_31      0.0406249000
_diffrn_orient_matrix_UB_32      0.1518900000
_diffrn_orient_matrix_UB_33      0.0064684000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14481
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.279
_diffrn_reflns_theta_min         5.426
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       cube
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       0.0104(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0316P)^2^+0.2156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2789
_reflns_number_total             2818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00662f2.cif
_cod_data_source_block           exp_2769
_cod_depositor_comments          'Adding full bibliography for 7244855.cif.'
_cod_database_code               7244855
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.894
_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:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00C(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C005(H005), C006(H006), C009(H009), C00A(H00A), C00D(H00F),
 C00E(H00G), C00F(H00H), C00G(H00I), C00H(H00J), C00I(H00K)
2.d Idealised Me refined as rotating group:
 C00J(H00L,H00M,H00N)
;
_shelx_res_checksum              14694
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.457