Synergistic Cu/Pd-catalyzed asymmetric allylation: a facile access to α-quaternary cysteine derivatives.
Wu, Hui-Min; Zhang, Zongpeng; Wei, Liang; Dong, Xiu-Qin; Wang, Chun-Jiang; Chemical communications (Cambridge, England) 57 (2021) 6538–6541; doi:10.1039/d1cc01754c

data_7128378
_publ_section_title
;
 Synergistic Cu/Pd-catalyzed asymmetric allylation: a facile access to
 \a-quaternary cysteine derivatives.
;
_journal_issue                   53
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6538
_journal_page_last               6541
_journal_paper_doi               10.1039/d1cc01754c
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 Br N O2 S'
_chemical_formula_sum            'C20 H18 Br N O2 S'
_chemical_formula_weight         416.32
_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     direct
_audit_creation_date             2020-07-28
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-03-31 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.68190(10)
_cell_length_b                   5.89500(10)
_cell_length_c                   20.17430(10)
_cell_measurement_reflns_used    15912
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5700
_cell_measurement_theta_min      2.1960
_cell_volume                     913.31(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -14.00  14.00   0.50    0.50    --    0.00 -82.00-180.00   56
  2  \w      8.00  47.00   0.50    0.50    --   32.00  71.00  -9.25   78
  3  \w     15.00  52.00   0.50    0.50    --   40.00  67.00 -96.21   74
  4  \w     15.00  86.00   0.50    0.50    --   40.00  71.00 159.26  142
  5  \w      6.00  68.00   0.50    0.50    --   44.00 -68.00 158.21  124
  6  \w     31.00  59.00   0.50    0.50    --   52.00  63.00  85.67   56
  7  \w    116.00 145.00   0.50    0.50    --   56.00  72.00  22.07   58
  8  \w     29.00  60.00   0.50    0.50    --   56.00  72.00  22.07   62
  9  \w     32.00  73.00   0.50    0.50    --   60.00  75.00 -69.13   82
 10  \w     33.00  78.00   0.50    0.50    --   60.00  72.00-143.00   90
 11  \w    121.00 149.00   0.50    0.50    --   60.00  72.00-143.00   56
 12  \w     38.00 104.00   0.50    0.50    --   64.00  72.00   5.36  132
 13  \w     36.00  70.00   0.50    0.50    --   64.00  75.00  60.64   68
 14  \w     37.00  66.00   0.50    0.50    --   64.00  75.00 128.80   58
 15  \w     36.00  72.00   0.50    0.50    --   64.00  75.00-110.49   72
 16  \w     44.00  94.00   0.50    0.50    --   72.00  74.00 -44.00  100
 17  \w    117.00 161.00   0.50    0.50    --   72.00  75.00 136.90   88
 18  \w     46.00 107.00   0.50    0.50    --   72.00  75.00 136.90  122
 19  \w     48.00  74.00   0.50    0.50    --   76.00  75.00  66.40   52
 20  \w    114.00 167.00   0.50    0.50    --   80.00  63.00 101.00  106
 21  \w     56.00  84.00   0.50    0.50    --   80.00  63.00 101.00   56
 22  \w     56.00  86.00   0.50    0.50    --   84.00  75.00 -65.33   60
 23  \w    122.00 173.00   0.50    0.50    --   84.00  57.00-143.99  102
 24  \w     63.00 108.00   0.50    0.50    --   84.00  57.00-143.99   90
 25  \w    106.00 132.00   0.50    0.50    --   88.00  68.00 160.81   52
 26  \w     63.00  94.00   0.50    0.50    --   88.00  68.00 160.81   62
 27  \w    119.00 183.00   0.50    0.50    --   94.60  68.00  47.72  128
 28  \w     69.00 113.00   0.50    0.50    --   94.60  68.00  47.72   88
 29  \w      8.00 115.00   0.50    0.50    --   94.60 -61.00  30.00  214
 30  \w     36.00  62.00   0.50    0.50    --   94.60 -82.00-180.00   52
 31  \w     67.00 100.00   0.50    0.50    --   94.60  72.00-129.15   66
 32  \w     77.00 135.00   0.50    0.50    --   94.60  45.00 -60.00  116
 33  \w     32.00 103.00   0.50    0.50    --   94.60 -61.00 120.00  142
 34  \w    150.00 175.00   0.50    0.50    --   94.60  77.00  90.00   50
 35  \w     81.00 119.00   0.50    0.50    --   94.60  77.00  90.00   76
 36  \w    159.00 184.00   0.50    0.50    --   94.60  45.00-120.00   50
 37  \w     79.00 184.00   0.50    0.50    --   94.60  61.00 120.00  210
 38  \w     83.00 110.00   0.50    0.50    --   94.60  77.00  60.00   54
 39  \w    152.00 179.00   0.50    0.50    --   94.60  61.00  30.00   54
 40  \w    115.00 184.00   0.50    0.50    --   94.60  61.00 -90.00  138
 41  \w     71.00 146.00   0.50    0.50    --   94.60  61.00  30.00  150
 42  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 -90.00   52
 43  \w    136.00 162.00   0.50    0.50    --   94.60  61.00-180.00   52
 44  \w      5.00 125.00   0.50    0.50    --   94.60 -82.00  30.00  240
 45  \w    144.00 169.00   0.50    0.50    --   94.60  77.00  60.00   50
 46  \w     83.00 141.00   0.50    0.50    --   94.60  45.00-120.00  116
 47  \w     80.00 108.00   0.50    0.50    --   94.60  61.00-180.00   56
 48  \w     58.00 120.00   0.50    0.50    --   94.60 -82.00-120.00  124
 49  \w     86.00 174.00   0.50    0.50    --   94.60  61.00 -42.22  176
 50  \w     10.00  49.00   0.50    0.50    --   94.60 -82.00-120.00   78
 51  \w     73.00 120.00   0.50    0.50    --   94.60 -82.00-180.00   94
 52  \w     79.00 182.00   0.50    0.50    --   94.60  77.00 -30.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1388343000
_diffrn_orient_matrix_UB_12      -0.1012099000
_diffrn_orient_matrix_UB_13      0.0478317000
_diffrn_orient_matrix_UB_21      -0.1220848000
_diffrn_orient_matrix_UB_22      0.0369282000
_diffrn_orient_matrix_UB_23      0.0584668000
_diffrn_orient_matrix_UB_31      -0.0778671000
_diffrn_orient_matrix_UB_32      -0.2381290000
_diffrn_orient_matrix_UB_33      -0.0112738000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18153
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.736
_diffrn_reflns_theta_min         2.191
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0213
_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^)+(0.0324P)^2^+0.4277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3567
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01754c2.cif
_cod_data_source_block           20200728_whm3pbr
_cod_depositor_comments          'Adding full bibliography for 7128378.cif.'
_cod_database_code               7128378
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.363
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C9(H9), C11(H11), C15(H15), C16(H16), C21(H21),
 C22(H22), C14(H14), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 1.703
_oxdiff_exptl_absorpt_empirical_full_min 0.513