Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters.
Wu, Hua; Wang, Qian; Zhu, Jieping; Journal of the American Chemical Society 141 (2019) 11372–11377; doi:10.1021/jacs.9b04551

data_4127390
_publ_section_title
;
 Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the
 Construction of Quaternary Stereocenters.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11372
_journal_page_last               11377
_journal_paper_doi               10.1021/jacs.9b04551
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_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
_audit_creation_date             2018-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.32811(6)
_cell_length_b                   10.96364(7)
_cell_length_c                   16.54433(9)
_cell_measurement_reflns_used    20130
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      75.8960
_cell_measurement_theta_min      4.8230
_cell_volume                     1510.603(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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     17.00  43.00   1.00    1.00    --   50.00  79.00 -38.90   26
  2  \w     35.00  61.00   1.00    1.00    --   66.00  76.00 -13.24   26
  3  \w     35.00  62.00   1.00    1.00    --   66.00  75.00  17.21   27
  4  \w     33.00  70.00   1.00    1.00    --   66.00  77.00  61.76   37
  5  \w     91.00 135.00   1.00    1.00    --   66.00  77.00  61.76   44
  6  \w    109.00 140.00   1.00    1.00    --   66.00  75.00  17.21   31
  7  \w     99.00 135.00   1.00    1.00    --   62.00  77.00 103.45   36
  8  \w     92.00 118.00   1.00    1.00    --   62.00  77.00 148.93   26
  9  \w     83.00 150.00   1.00    2.00    --  111.85  61.00 120.00   67
 10  \w     84.00 109.00   1.00    2.00    --  111.85  61.00  60.00   25
 11  \w     87.00 114.00   1.00    2.00    --  111.85  61.00  90.00   27
 12  \w     79.00 148.00   1.00    2.00    --  111.85  77.00  30.00   69
 13  \w    117.00 178.00   1.00    2.00    --  111.85  77.00 -30.00   61
 14  \w    134.00 166.00   1.00    2.00    --  111.85  61.00-120.00   32
 15  \w    131.00 158.00   1.00    2.00    --  111.85  77.00-180.00   27
 16  \w    103.00 137.00   1.00    1.00    --   74.00  77.00 -89.24   34
 17  \w     86.00 175.00   1.00    2.00    --  111.85  61.00-150.00   89
 18  \w     79.00 105.00   1.00    2.00    --  111.85  77.00-120.00   26
 19  \w     84.00 163.00   1.00    2.00    --  111.85  61.00 -90.00   79
 20  \w     83.00 110.00   1.00    2.00    --  111.85  61.00 -60.00   27
 21  \w     83.00 109.00   1.00    2.00    --  111.85  61.00 -30.00   26
 22  \w     83.00 109.00   1.00    2.00    --  111.85  61.00   0.00   26
 23  \w     84.00 144.00   1.00    2.00    --  111.85  61.00  30.00   60
 24  \w     79.00 104.00   1.00    2.00    --  111.85  77.00 120.00   25
 25  \w     81.00 169.00   1.00    2.00    --  111.85  77.00 150.00   88
 26  \w     84.00 110.00   1.00    2.00    --  111.85  61.00 150.00   26
 27  \w     80.00 105.00   1.00    2.00    --  111.85  77.00  90.00   25
 28  \w     80.00 158.00   1.00    2.00    --  111.85  77.00  60.00   78
 29  \w     80.00 106.00   1.00    2.00    --  111.85  77.00 -90.00   26
 30  \w     79.00 175.00   1.00    2.00    --  111.85  77.00 -60.00   96
 31  \w     79.00 104.00   1.00    2.00    --  111.85  77.00-180.00   25
 32  \w     79.00 104.00   1.00    2.00    --  111.85  77.00-150.00   25
 33  \w     83.00 123.00   1.00    2.00    --  111.85  61.00-120.00   40
 34  \w     79.00 106.00   1.00    2.00    --  111.85  77.00 -30.00   27
 35  \w     79.00 124.00   1.00    2.00    --  111.85  77.00   0.00   45
 36  \w     42.00  70.00   1.00    1.00    --   70.00  77.00 -61.41   28
 37  \w     41.00  73.00   1.00    1.00    --   74.00  77.00 -89.24   32
 38  \w     41.00 149.00   1.00    1.00    --   74.00  77.00-156.28  108
 39  \w     39.00 138.00   1.00    2.00    --  111.85 -45.00-150.00   99
 40  \w     53.00 122.00   1.00    2.00    --  111.85-125.00  30.00   69
 41  \w     77.00 102.00   1.00    2.00    --  111.85 -94.00  90.00   25
 42  \w     43.00 121.00   1.00    2.00    --  111.85 -61.00   0.00   78
 43  \w     35.00  70.00   1.00    1.00    --   40.91-125.00-180.00   35
 44  \w      2.00  80.00   1.00    1.00    --   40.91 -99.00-150.00   78
 45  \w     37.00  67.00   1.00    1.00    --   40.91-125.00 -30.00   30
 46  \w      3.00  78.00   1.00    1.00    --   40.91 -99.00  30.00   75
 47  \w     34.00 102.00   1.00    2.00    --  111.85 -94.00 150.00   68
 48  \w     29.00  65.00   1.00    1.00    --   62.00  77.00 103.45   36
 49  \w     37.00  62.00   1.00    1.00    --   70.00  77.00 177.94   25
 50  \w     29.00  55.00   1.00    1.00    --   62.00  77.00 148.93   26
 51  \w     11.00  36.00   1.00    1.00    --   46.00  84.00  74.52   25
 52  \w      5.00  30.00   1.00    1.00    --   42.00  90.00  25.04   25
 53  \w     20.00  45.00   1.00    1.00    --   54.00  81.00 -96.20   25
 54  \w     21.00  46.00   1.00    1.00    --   54.00  79.00-160.94   25
 55  \w      6.00  31.00   1.00    1.00    --   42.00  87.00-106.93   25
 56  \w    -75.00 -16.00   1.00    1.00    --  -40.91 -38.00-120.00   59
 57  \w   -110.00 -80.00   1.00    1.00    --  -40.91 -38.00-120.00   30
 58  \w   -118.00 -10.00   1.00    1.00    --  -40.91 -19.00 -30.00  108
 59  \w    -55.00 -13.00   1.00    1.00    --  -40.91 -57.00 150.00   42
 60  \w   -113.00 -62.00   1.00    1.00    --  -40.91 -57.00 150.00   51
 61  \w     31.00 108.00   1.00    2.00    --  111.85 -94.00-120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0217614000
_diffrn_orient_matrix_UB_12      -0.0868243000
_diffrn_orient_matrix_UB_13      0.0723955000
_diffrn_orient_matrix_UB_21      -0.0172053000
_diffrn_orient_matrix_UB_22      0.1104858000
_diffrn_orient_matrix_UB_23      0.0568734000
_diffrn_orient_matrix_UB_31      -0.1828891000
_diffrn_orient_matrix_UB_32      -0.0000605000
_diffrn_orient_matrix_UB_33      -0.0139610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25302
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.075
_diffrn_reflns_theta_min         4.839
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.591
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0376P)^2^+0.2223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3091
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04551_si_002.cif
_cod_data_source_block           hwu-six-1
_cod_original_cell_volume        1510.604(17)
_cod_database_code               4127390
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H18 O2'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C3(H3), C20(H20), C2(H2), C19(H19), C18(H18), C16(H16),
 C17(H17)
2.c Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1)
;
_shelx_res_checksum              5655
_shelx_hkl_checksum              78286
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.058
_oxdiff_exptl_absorpt_empirical_full_min 0.623