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_1569581
_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 H19 Br N2 O2'
_chemical_formula_sum            'C23 H19 Br N2 O2'
_chemical_formula_weight         435.31
_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     iterative
_audit_creation_date             2023-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.764(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5962(6)
_cell_length_b                   5.2216(2)
_cell_length_c                   15.4025(6)
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      74.1640
_cell_measurement_theta_min      3.0460
_cell_volume                     953.38(8)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.953
_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  26.00   0.50   30.00    --  -47.20  92.00  58.00  206
  2  \w    -19.00  77.00   0.50   30.00    --   47.20 -92.00 -54.00  192
  3  \w    102.00 178.00   0.50  120.00    --  107.11  92.00  58.00  152
  4  \w    -60.00  26.00   0.50   30.00    --  -47.20  37.00  60.00  172
  5  \w   -120.00 -94.00   0.50   30.00    --  -47.20-125.00  30.00   52
  6  \w   -120.00 -94.00   0.50   30.00    --  -47.20-125.00   0.00   52
  7  \w   -120.00 -94.00   0.50   30.00    --  -47.20-125.00 -30.00   52
  8  \w     34.00 120.00   0.50  120.00    --  107.11 -37.00  30.00  172
  9  \w    110.00 178.00   0.50  120.00    --  107.11  77.00 120.00  136
 10  \w     32.00 120.00   0.50  120.00    --  107.11 -19.00  60.00  176
 11  \w    110.00 178.00   0.50  120.00    --  107.11  77.00   0.00  136
 12  \w    103.00 178.00   0.50  120.00    --  107.11  57.00-150.00  150
 13  \w    103.00 178.00   0.50  120.00    --  107.11  57.00  90.00  150
 14  \w     35.00  80.00   0.50  120.00    --  107.11 -92.00 -54.00   90
 15  \w     35.00 120.00   0.50   30.00    --   47.20  37.00  90.00  170
 16  \w     35.00 120.00   0.50   30.00    --   47.20  37.00 150.00  170
 17  \w     35.00 120.00   0.50   30.00    --   47.20  37.00 -30.00  170
 18  \w     35.00 120.00   0.50   30.00    --   47.20  37.00  30.00  170
 19  \w     34.00  95.00   0.50   30.00    --   47.20-125.00 -90.00  122
 20  \w     35.00 120.00   0.50   30.00    --   47.20  37.00-120.00  170
 21  \w     35.00 130.00   0.50  120.00    --  107.11 -77.00  60.00  190
 22  \w     95.00 141.00   0.50  120.00    --  107.11  37.00-180.00   92
;
_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      0.0682879000
_diffrn_orient_matrix_UB_12      0.0934966000
_diffrn_orient_matrix_UB_13      0.0978532000
_diffrn_orient_matrix_UB_21      0.0954828000
_diffrn_orient_matrix_UB_22      -0.1878409000
_diffrn_orient_matrix_UB_23      0.0029651000
_diffrn_orient_matrix_UB_31      0.0557881000
_diffrn_orient_matrix_UB_32      0.2075250000
_diffrn_orient_matrix_UB_33      -0.0412423000
_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  0.0828
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8482
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.307
_diffrn_reflns_theta_min         3.049
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666
_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    1.516
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1237P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.562
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.671
_reflns_number_gt                2823
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01656k2.cif
_cod_data_source_block           sar-07ra
_cod_original_cell_volume        953.38(7)
_cod_database_code               1569581
_shelx_shelxl_version_number     2019/2
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         C23H19N2O2Br
_chemical_oxdiff_usercomment     as-496
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.656
_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*), C2'*(H2'*), C4"(H4"), C8(H8), C7*(H7*), C2"*(H2"*), C3'*(H3'*), C3"*
 (H3"*), C3"(H3"), C7(H7), C2"(H2"), C2'(H2'), C3'(H3'), C4'(H4')
;
_shelx_res_checksum              5569
_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 2.698
_oxdiff_exptl_absorpt_empirical_full_min 0.404