CPA-catalyzed asymmetric domino thia-Michael/aldol reactions for simultaneous chiral center and axial chirality formation.
Wang, Xilong; Luo, Yu; Zhao, Jiaji; Luo, Shuang; Organic & biomolecular chemistry 21 (2023) 6697–6701; doi:10.1039/d3ob01087b

data_7159517
_publ_section_title
;
 CPA-catalyzed asymmetric domino thia-Michael/aldol reactions for
 simultaneous chiral center and axial chirality formation.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6697
_journal_page_last               6701
_journal_paper_doi               10.1039/d3ob01087b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H18 O2 S'
_chemical_formula_sum            'C23 H18 O2 S'
_chemical_formula_weight         358.43
_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_block_doi                 10.5517/ccdc.csd.cc27l1b7
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-25 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36850(10)
_cell_length_b                   10.75200(10)
_cell_length_c                   15.87320(10)
_cell_measurement_reflns_used    26328
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8590
_cell_measurement_theta_min      2.8040
_cell_volume                     1745.60(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -83.00   9.00   0.50    0.05    --  -46.62 103.00 124.00  184
  2  \w     -5.00  83.00   0.50    0.05    --   46.62-103.00  22.00  176
  3  \w   -110.00 -27.00   0.50    0.05    -- -100.00 103.00 124.00  166
  4  \w     34.00 110.00   0.50    0.05    --  107.00-103.00  22.00  152
  5  \w     86.00 178.00   0.50    0.05    --  107.00 103.00 124.00  184
  6  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 150.00   96
  7  \w    -63.00  26.00   0.50    0.05    --  -46.62  57.00  90.00  178
  8  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-180.00   96
  9  \w   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00 -30.00  192
 10  \w    -62.00  29.00   0.50    0.05    --  -46.62  19.00-120.00  182
 11  \w     15.00  95.00   0.50    0.05    --   46.62-125.00-150.00  160
 12  \w   -115.00 -25.00   0.50    0.05    -- -100.00  30.00   0.00  180
 13  \w   -117.00 -27.00   0.50    0.05    -- -100.00 125.00 -90.00  180
 14  \w   -115.00 -25.00   0.50    0.05    -- -100.00  30.00 150.00  180
 15  \w   -124.00 -27.00   0.50    0.05    -- -100.00  77.00 120.00  194
 16  \w   -173.00 -82.00   0.50    0.05    -- -100.00 -61.00 -60.00  182
 17  \w   -173.00 -82.00   0.50    0.05    -- -100.00-103.00  22.00  182
 18  \w     34.00 125.00   0.50    0.05    --  107.00 -61.00  30.00  182
 19  \w     93.00 178.00   0.50    0.05    --  107.00  45.00-120.00  170
 20  \w     34.00 117.00   0.50    0.05    --  107.00-125.00  90.00  166
 21  \w     76.00 178.00   0.50    0.05    --  107.00 125.00 -30.00  204
 22  \w     34.00 117.00   0.50    0.05    --  107.00-125.00-120.00  166
 23  \w     34.00 125.00   0.50    0.05    --  107.00 -61.00-180.00  182
 24  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 25  \w     90.00 178.00   0.50    0.05    --  107.00  61.00 150.00  176
 26  \w     34.00 117.00   0.50    0.05    --  107.00-125.00 -30.00  166
 27  \w     92.00 178.00   0.50    0.05    --  107.00  30.00-150.00  172
 28  \w     89.00 178.00   0.50    0.05    --  107.00  15.00 -60.00  178
 29  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 -90.00  150
 30  \w     93.00 178.00   0.50    0.05    --  107.00  45.00 120.00  170
 31  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 150.00  150
 32  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 -60.00  150
 33  \w     34.00 117.00   0.50    0.05    --  107.00-125.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1417286000
_diffrn_orient_matrix_UB_12      0.0396470000
_diffrn_orient_matrix_UB_13      0.0341516000
_diffrn_orient_matrix_UB_21      -0.0480479000
_diffrn_orient_matrix_UB_22      0.1316157000
_diffrn_orient_matrix_UB_23      0.0175730000
_diffrn_orient_matrix_UB_31      -0.0172944000
_diffrn_orient_matrix_UB_32      -0.0404715000
_diffrn_orient_matrix_UB_33      0.0905542000
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.042
_diffrn_reflns_theta_min         2.822
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(15)
_refine_ls_extinction_coef       0.0028(4)
_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   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         7207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0588P)^2^+0.6378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                7061
_reflns_number_total             7207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01087b2.cif
_cod_data_source_block           fanwx_98_200922
_cod_depositor_comments          'Adding full bibliography for 7159517.cif.'
_cod_database_code               7159517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOS
_shelx_estimated_absorpt_t_max   0.668
_shelx_estimated_absorpt_t_min   0.621
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C35(H35), C49(H49), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C47(H47), C15(H15), C41(H41), C21(H21), C32(H32), C31(H31), C29(H29),
 C39(H39), C5(H5), C20(H20), C40(H40), C38(H38), C44(H44), C30(H30), C45(H45),
 C46(H46), C12(H12), C19(H19), C18(H18), C14(H14), C4(H4), C6(H6), C13(H13)
2.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O24(H24), O50(H50)
;
_shelx_res_checksum              65679
_shelx_hkl_checksum              6719
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.781