Enantioselective Synthesis of Vicinal Amino Alcohols Promoted by Fluorine-Containing Counteranions
Yang, Yu-Chen; Wu, Jia-Long; Zhang, Sheng-Ye; Sun, Teng; Liu, Xu; Zhao, Yanan; Wang, Lijia; Chemical Science  (2025) –; doi:10.1039/D5SC06853C

data_1576345
_publ_section_title
;
 Enantioselective Synthesis of Vicinal Amino Alcohols Promoted by
 Fluorine-Containing Counteranions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06853C
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H25 N O3 S'
_chemical_formula_sum            'C29 H25 N O3 S'
_chemical_formula_weight         467.56
_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             2024-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-08-06 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.55950(10)
_cell_length_b                   15.9767(2)
_cell_length_c                   19.4896(3)
_cell_measurement_reflns_used    13646
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.4160
_cell_measurement_theta_min      3.5810
_cell_volume                     2353.87(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -88.00   5.00   1.00    1.00    --    0.00 -37.00 150.00   93
  2  \w    -17.00  27.00   1.00    1.00    --    0.00 -37.00-180.00   44
  3  \w    -11.00  25.00   1.00    1.00    --    0.00 -57.00 -90.00   36
  4  \w    -27.00  21.00   1.00    1.00    --    0.00  37.00 150.00   48
  5  \w     58.00  88.00   1.00    1.00    --    0.00  37.00 150.00   30
  6  \w    -75.00 -29.00   1.00    1.00    --    0.00 -57.00 -90.00   46
  7  \w      4.00 113.00   1.00    2.00    --   92.10 -61.00-180.00  109
  8  \w     40.00  71.00   1.00    2.00    --   92.10 -45.00 -90.00   31
  9  \w    106.00 181.00   1.00    2.00    --   92.10 -15.00 -60.00   75
 10  \w     51.00 120.00   1.00    2.00    --   92.10 -61.00  60.00   69
 11  \w     28.00  54.00   1.00    2.00    --   92.10 -82.00-120.00   26
 12  \w     90.00 115.00   1.00    2.00    --   92.10 -82.00-120.00   25
 13  \w     73.00 103.00   1.00    2.00    --   92.10  45.00  60.00   30
 14  \w    123.00 170.00   1.00    2.00    --   92.10  45.00  60.00   47
 15  \w      3.00  47.00   1.00    2.00    --   92.10 -61.00  60.00   44
 16  \w      4.00 116.00   1.00    2.00    --   92.10 -82.00  60.00  112
 17  \w     30.00  81.00   1.00    2.00    --   92.10 -45.00-180.00   51
 18  \w     63.00 107.00   1.00    2.00    --   92.10 -82.00 -30.00   44
 19  \w      6.00  41.00   1.00    2.00    --   92.10 -82.00 150.00   35
 20  \w     91.00 117.00   1.00    2.00    --   92.10 -82.00 150.00   26
 21  \w     24.00  50.00   1.00    2.00    --   92.10 -82.00 -30.00   26
 22  \w     94.00 182.00   1.00    2.00    --   92.10  61.00 120.00   88
 23  \w     22.00 128.00   1.00    2.00    --   92.10 -82.00-180.00  106
 24  \w     10.00 119.00   1.00    2.00    --   92.10 -61.00 -60.00  109
 25  \w      8.00  86.00   1.00    2.00    --   92.10 -15.00 -60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206270000
_diffrn_orient_matrix_UB_12      0.0248082000
_diffrn_orient_matrix_UB_13      -0.0759591000
_diffrn_orient_matrix_UB_21      0.0186229000
_diffrn_orient_matrix_UB_22      -0.0929909000
_diffrn_orient_matrix_UB_23      -0.0195801000
_diffrn_orient_matrix_UB_31      -0.2019724000
_diffrn_orient_matrix_UB_32      -0.0059304000
_diffrn_orient_matrix_UB_33      -0.0094805000
_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  0.0558
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0450P)^2^+0.3648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3921
_reflns_number_total             4181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06853c2.cif
_cod_data_source_block           exp_3888_auto
_cod_database_code               1576345
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(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:
 C11(H11), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C9(H9), C14(H14), C24(H24), C7(H7), C8(H8), C28(H28), C2(H2),
 C25(H25), C5(H5), C21(H21), C3(H3), C15(H15), C4(H4), C27(H27), C19(H19),
 C20(H20), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              60903
_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 2.211
_oxdiff_exptl_absorpt_empirical_full_min 0.585