Catalytic enantioselective radical coupling of activated ketones with <i>N</i>-aryl glycines.
Liu, Yang; Liu, Xiangyuan; Li, Jiangtao; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong; Chemical science 9 (2018) 8094–8098; doi:10.1039/c8sc02948b

data_1549848
_publ_section_title
;
 Catalytic enantioselective radical coupling of activated ketones with
 <i>N</i>-aryl glycines.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              8094
_journal_page_last               8098
_journal_paper_doi               10.1039/c8sc02948b
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 Br N O4'
_chemical_formula_sum            'C23 H22 Br N O4'
_chemical_formula_weight         456.32
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-13 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3737(3)
_cell_length_b                   10.0127(4)
_cell_length_c                   24.6580(8)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5840
_cell_measurement_theta_min      4.7510
_cell_volume                     2067.41(13)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -104.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000    0.0000 86

  2 omega  -37.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -60.0000 72

  3 omega  -84.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -156.0000  -27.0000 26

  4 omega  -63.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 30

  5 omega -106.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 25

  6 omega   73.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 36

  7 omega   63.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 37

  8 omega   64.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 43

  9 omega  -17.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -60.0000 28

 10 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -60.0000 26

 11 omega   46.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 52

 12 omega  142.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 29

 13 omega   46.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 47

 14 omega   52.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 55

 15 omega   38.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 25

 16 omega   38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 26

 17 omega  103.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 70

 18 omega   49.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 37

 19 omega   61.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 30

 20 omega   38.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 21 omega   38.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0316523000
_diffrn_orient_matrix_UB_12      -0.0178492000
_diffrn_orient_matrix_UB_13      -0.0610897000
_diffrn_orient_matrix_UB_21      0.0547842000
_diffrn_orient_matrix_UB_22      -0.1446706000
_diffrn_orient_matrix_UB_23      0.0102599000
_diffrn_orient_matrix_UB_31      -0.1728620000
_diffrn_orient_matrix_UB_32      -0.0491544000
_diffrn_orient_matrix_UB_33      -0.0079547000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7569
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.585
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.955
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87948
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.029(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0569P)^2^+0.0499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3281
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02948b2.cif
_cod_data_source_block           ly170031
_cod_depositor_comments
'Adding full bibliography for 1549848--1549849.cif.'
_cod_original_cell_volume        2067.40(14)
_cod_database_code               1549848
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C26H23N2O4Br1
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.590
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1B)
;
_olex2_submission_special_instructions 'No special instructions were received'