Conjugate Addition-Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis.
Yin, Yanli; Dai, Yating; Jia, Hongshao; Li, Jiangtao; Bu, Liwei; Qiao, Baokun; Zhao, Xiaowei; Jiang, Zhiyong; Journal of the American Chemical Society 140 (2018) 6083–6087; doi:10.1021/jacs.8b01575

data_4132100
_publ_section_title
;
 Conjugate Addition-Enantioselective Protonation of N-Aryl Glycines to
 \a-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric
 Catalysis.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6083
_journal_page_last               6087
_journal_paper_doi               10.1021/jacs.8b01575
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 Br N2'
_chemical_formula_sum            'C26 H23 Br N2'
_chemical_formula_weight         443.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.064(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.7031(11)
_cell_length_b                   5.8682(4)
_cell_length_c                   16.6098(8)
_cell_measurement_reflns_used    3325
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6560
_cell_measurement_theta_min      4.0510
_cell_volume                     2115.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -34.00    5.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   23.0000  175.0000 39

  2 omega  -46.00  -19.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   60.0000 27

  3 omega    0.00   26.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   60.0000 26

  4 omega   24.00   52.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000    0.0000 28

  5 omega   74.00  103.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   30.0000 29

  6 omega    9.00   35.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 26

  7 omega   69.00   95.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 26

  8 omega   82.00  107.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 25

  9 omega   -4.00   53.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 57

 10 omega   23.00   49.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 26

 11 omega   -2.00   45.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 47

 12 omega   -7.00   19.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  106.0000 -103.1625 26

 13 omega   58.00  106.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 48

 14 omega    9.00   35.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 26

 15 omega   59.00  105.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 46

 16 omega   65.00  109.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 44

 17 omega    3.00   32.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   92.0000   16.9221 29

 18 omega   18.00   66.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 48

 19 omega   63.00  105.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 42

 20 omega   16.00   41.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 25

 21 omega   63.00   89.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 26

 22 omega   38.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 27

 23 omega   83.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 30

 24 omega   39.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 57

 25 omega   88.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 27

 26 omega  124.00  166.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 42

 27 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 28 omega   89.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 26

 29 omega   95.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 26

 30 omega   88.00  157.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 69

 31 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 32 omega   38.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 59

 33 omega   39.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 59

 34 omega   83.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 36

 35 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 36 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 37 omega   88.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

 38 omega   88.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 31

 39 omega  142.00  168.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 26

 40 omega   82.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 41 omega   86.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 26

 42 omega  118.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 58

 43 omega   88.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 26

 44 omega   82.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 93

 45 omega   91.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 25

 46 omega   92.00  123.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 31

 47 omega   80.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 48 omega   71.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 36

 49 omega  138.00  166.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 28

 50 omega  128.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 42

 51 omega   88.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0542303000
_diffrn_orient_matrix_UB_12      0.0036110000
_diffrn_orient_matrix_UB_13      0.0380385000
_diffrn_orient_matrix_UB_21      0.0432789000
_diffrn_orient_matrix_UB_22      -0.0810031000
_diffrn_orient_matrix_UB_23      0.0850799000
_diffrn_orient_matrix_UB_31      0.0148121000
_diffrn_orient_matrix_UB_32      0.2496672000
_diffrn_orient_matrix_UB_33      0.0271010000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8232
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.108
_diffrn_reflns_theta_max         67.108
_diffrn_reflns_theta_min         4.074
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0448P)^2^+0.8809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                3130
_reflns_number_total             3456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01575_si_001.cif
_cod_data_source_block           yz8058a
_cod_database_code               4132100
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C26H23N2Br1
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.684
_reflns_odcompleteness_completeness 99.95
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'