Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas
Aryal, Sushant; Hone, Christopher A.; Polson, Matthew I. J.; Foley, Daniel J.; Chemical Science 14 (2023) 7905–7912; doi:10.1039/D3SC01656K

data_1569582
_publ_section_title
;
 Enantioselective synthesis of hydantoins by chiral acid-catalysed
 condensation of glyoxals and ureas
;
_journal_issue                   29
_journal_name_full               'Chemical Science'
_journal_page_first              7905
_journal_page_last               7912
_journal_paper_doi               10.1039/D3SC01656K
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_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     dual
_audit_creation_date             2023-01-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-12 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.641(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0926(2)
_cell_length_b                   5.4361(2)
_cell_length_c                   13.6728(3)
_cell_measurement_reflns_used    11644
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      77.0850
_cell_measurement_theta_min      3.6100
_cell_volume                     894.45(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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   -120.00 -35.00   0.50    2.50    --  -47.45 -41.00   1.00  170
  2  \w    -60.00  25.00   0.50    2.50    --  -47.45  41.00 154.00  170
  3  \w    -25.00  60.00   0.50    2.50    --   47.45 -41.00   1.00  170
  4  \w     35.00 120.00   0.50    2.50    --   47.45  41.00 154.00  170
  5  \w     35.00 120.00   0.50   10.00    --  107.75 -41.00   1.00  170
  6  \w     96.00 178.00   0.50   10.00    --  107.75  41.00 154.00  164
  7  \w   -120.00 -73.00   0.50    2.50    --  -47.45-125.00 150.00   94
  8  \w   -121.00 -35.00   0.50    2.50    --  -47.45 -37.00 -30.00  172
  9  \w     34.00  95.00   0.50    2.50    --   47.45-125.00 -90.00  122
 10  \w     33.00 120.00   0.50    2.50    --   47.45  57.00-120.00  174
 11  \w     33.00 120.00   0.50    2.50    --   47.45  57.00 -90.00  174
 12  \w     33.00 120.00   0.50    2.50    --   47.45  57.00 -60.00  174
 13  \w     91.00 178.00   0.50   10.00    --  107.75  61.00 -60.00  174
 14  \w     35.00 106.00   0.50   10.00    --  107.75 -94.00  30.00  142
 15  \w     94.00 178.00   0.50   10.00    --  107.75  15.00-120.00  168
 16  \w     85.00 178.00   0.50   10.00    --  107.75  77.00-150.00  186
 17  \w     95.00 170.50   0.50   10.00    --  107.75 125.00  60.00  151
 18  \w     85.00 178.00   0.50   10.00    --  107.75  77.00-180.00  186
 19  \w     91.00 178.00   0.50   10.00    --  107.75  61.00-180.00  174
 20  \w    102.00 178.00   0.50   10.00    --  107.75  77.00-120.00  152
 21  \w     94.00 178.00   0.50   10.00    --  107.75  51.00-131.23  168
 22  \w     35.00 106.00   0.50   10.00    --  107.75 -94.00   0.00  142
 23  \w     91.00 178.00   0.50   10.00    --  107.75  61.00-120.00  174
 24  \w     96.50 178.00   0.50   10.00    --  107.75  77.00 -60.00  163
 25  \w     94.00 178.00   0.50   10.00    --  107.75  15.00  90.00  168
 26  \w    100.50 178.00   0.50   10.00    --  107.75  77.00 -90.00  155
 27  \w     36.00 121.00   0.50   10.00    --  107.75 -45.00-120.00  170
 28  \w     91.00 178.00   0.50   10.00    --  107.75  61.00 -90.00  174
 29  \w     91.00 178.00   0.50   10.00    --  107.75  61.00-150.00  174
 30  \w     95.00 178.00   0.50   10.00    --  107.75  45.00 -60.00  166
 31  \w     36.00 178.00   0.50   10.00    --  107.75   0.00 120.00  284
 32  \w     95.00 178.00   0.50   10.00    --  107.75  45.00 -90.00  166
 33  \w     95.00 178.00   0.50   10.00    --  107.75  30.00 -60.00  166
 34  \w     95.00 178.00   0.50   10.00    --  107.75  36.00-105.71  166
 35  \w     33.00 121.00   0.50   10.00    --  107.75 -30.00-180.00  176
 36  \w     35.00  99.00   0.50   10.00    --  107.75-125.00   0.00  128
 37  \w   -120.00 -25.00   0.50    2.50    --  -47.45 -77.00 120.00  190
 38  \w     25.00 120.00   0.50    2.50    --   47.45  77.00   0.00  190
 39  \w     33.00 120.00   0.50    2.50    --   47.45  57.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0203578000
_diffrn_orient_matrix_UB_12      0.0342088000
_diffrn_orient_matrix_UB_13      0.1122041000
_diffrn_orient_matrix_UB_21      -0.1110864000
_diffrn_orient_matrix_UB_22      0.1388417000
_diffrn_orient_matrix_UB_23      -0.0006207000
_diffrn_orient_matrix_UB_31      -0.0602124000
_diffrn_orient_matrix_UB_32      -0.2447077000
_diffrn_orient_matrix_UB_33      0.0153018000
_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  0.0890
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15907
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.465
_diffrn_reflns_theta_min         3.673
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0550
_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^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                3289
_reflns_number_total             3500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01656k2.cif
_cod_data_source_block           sar-04a
_cod_database_code               1569582
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C23H20N2O2
_chemical_oxdiff_usercomment     AS-330
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C'(H'A,H'B), C"(H"A,H"B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7*(H7*), C3"(H3"), C2'*(H2'*), C2"(H2"), C2"*(H2"*), C3'(H3'), C8*
 (H8*), C9(H9), C2'(H2'), C7(H7), C4"(H4"), C3"*(H3"*), C4'(H4'), C3'*(H3'*)
;
_shelx_res_checksum              21492
_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 6.600
_oxdiff_exptl_absorpt_empirical_full_min 0.384