5-<i>exo</i>-Selective asymmetric bromolactonization of stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea.
Sugano, Masayuki; Inokuma, Tsubasa; Yamaoka, Yousuke; Yamada, Ken-Ichi; Organic & biomolecular chemistry 22 (2024) 1765–1769; doi:10.1039/d3ob01895d

data_7159709
_publ_section_title
;
 5-<i>exo</i>-Selective asymmetric bromolactonization of
 stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1765
_journal_page_last               1769
_journal_paper_doi               10.1039/d3ob01895d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_chemical_melting_point          434
_chemical_name_systematic
(S)-3-[(R)-Bromo(4-methylphenyl)methyl]isobenzofuran-1(3H)-one
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      78
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-08
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.67730(10)
_cell_length_b                   8.67730(10)
_cell_length_c                   17.8920(5)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.8160
_cell_measurement_theta_min      5.0670
_cell_volume                     1347.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -84.00 -38.00   0.50    0.50    --    5.00  60.00  30.00   92
  2  \w    -84.00 -38.00   0.50    0.50    --    5.00  60.00   0.00   92
  3  \w   -136.00  43.00   0.50    0.50    --  -46.70  40.00 120.00  358
  4  \w   -136.00  43.00   0.50    0.50    --  -46.70  41.00 169.92  358
  5  \w   -146.00  -9.00   0.50    0.50    --  -97.40  45.00 174.81  274
  6  \w    -42.00  -8.00   0.50    0.50    --  -97.40  26.00 178.02   68
  7  \w    -35.00 -10.00   0.50    0.50    --  -97.40  32.00 179.74   50
  8  \w    -33.00  -8.00   0.50    0.50    --  -97.40  43.00 178.72   50
  9  \w   -141.00 -37.00   0.50    0.50    --  -97.40  59.00 118.47  208
 10  \w    -84.00 -58.00   0.50    0.50    --  -97.40  32.00 179.74   52
 11  \w    -35.00  -9.00   0.50    0.50    --  -97.40  44.00 165.51   52
 12  \w   -147.00 -39.00   0.50    0.50    --  -97.40  60.00  91.30  216
 13  \w   -122.00 -18.00   0.50    0.50    --  -97.40  40.00 150.00  208
 14  \w   -143.00 -26.00   0.50    0.50    --  -97.40  49.00 164.50  234
 15  \w    -38.00 -10.00   0.50    0.50    --  -97.40  44.00 170.60   56
 16  \w    -34.00  -9.00   0.50    0.50    --  -97.40  45.00 161.26   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1510848000
_diffrn_orient_matrix_UB_12      -0.0556810000
_diffrn_orient_matrix_UB_13      -0.0363554000
_diffrn_orient_matrix_UB_21      -0.0471921000
_diffrn_orient_matrix_UB_22      0.1683645000
_diffrn_orient_matrix_UB_23      -0.0141293000
_diffrn_orient_matrix_UB_31      0.0806815000
_diffrn_orient_matrix_UB_32      -0.0046845000
_diffrn_orient_matrix_UB_33      -0.0767750000
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9588
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.221
_diffrn_reflns_theta_min         5.097
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0635
_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^)+(0.1340P)^2^+1.7227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                2554
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01895d3.cif
_cod_data_source_block           220708ky_auto
_cod_depositor_comments          'Adding full bibliography for 7159709.cif.'
_cod_original_cell_volume        1347.19(5)
_cod_database_code               7159709
_shelx_estimated_absorpt_t_max   0.684
_shelx_estimated_absorpt_t_min   0.493
_shelx_res_checksum              53582