Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis.
Duan, Shaobo; Li, Sanliang; Ye, Xinyi; Du, Nuan-Nuan; Tan, Choon-Hong; Jiang, Zhiyong; The Journal of organic chemistry 80 (2015) 7770–7778; doi:10.1021/acs.joc.5b01081

data_4031281
_publ_section_title
;
 Enantioselective Synthesis of Dialkylated \a-Hydroxy Carboxylic Acids
 through Asymmetric Phase-Transfer Catalysis.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7770
_journal_page_last               7778
_journal_paper_doi               10.1021/acs.joc.5b01081
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration S
_chemical_formula_moiety         'C23 H17 Br F N O2'
_chemical_formula_sum            'C23 H17 Br F N O2'
_chemical_formula_weight         438.29
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-27
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.27393(18)
_cell_length_b                   16.0274(5)
_cell_length_c                   20.1850(5)
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.4320
_cell_measurement_theta_min      4.3700
_cell_volume                     2029.70(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    5.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 35

  2 omega   -4.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 27

  3 omega  -69.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 33

  4 omega   51.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 72

  5 omega   57.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 58

  6 omega   71.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  165.0000 -133.0000 41

  7 omega   39.00   72.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 33

  8 omega   42.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 26

  9 omega   45.00  120.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 75

 10 omega   40.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 29

 11 omega   73.00  133.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  165.0000 -133.0000 60

 12 omega   50.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 48

 13 omega   41.00   82.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 41

 14 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 26

 15 omega    5.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       55.7033  -57.0000  -30.0000 30

 16 omega   -4.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       55.7033  -37.0000   90.0000 86

 17 omega   54.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -50.0000   60.0000 32

 18 omega   59.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -43.0000 -143.0000 32

 19 omega   60.00  101.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066 -111.0000  -60.0000 41

 20 omega   52.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066  -25.0000    0.0000 39

 21 omega  101.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      111.4066   12.0000   60.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0499577000
_diffrn_orient_matrix_UB_12      -0.0525195000
_diffrn_orient_matrix_UB_13      0.0620202000
_diffrn_orient_matrix_UB_21      -0.1228402000
_diffrn_orient_matrix_UB_22      0.0630047000
_diffrn_orient_matrix_UB_23      0.0431850000
_diffrn_orient_matrix_UB_31      -0.2066219000
_diffrn_orient_matrix_UB_32      -0.0501537000
_diffrn_orient_matrix_UB_33      -0.0106110000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7791
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.521
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description
;
;
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0501
_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^)+(0.1056P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3075
_reflns_number_total             3632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01081_si_003.cif
_cod_data_source_block           20150349
_cod_depositor_comments
'Adding full bibliography for 4031281--4031282.cif.'
_cod_database_code               4031281
_chemical_oxdiff_formula         C20H20N4O4F1Br1
_shelx_estimated_absorpt_t_max   0.586
_shelx_estimated_absorpt_t_min   0.511
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              98305
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'