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_1549849
_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         'C26 H32 N2 O8 S'
_chemical_formula_sum            'C26 H32 N2 O8 S'
_chemical_formula_weight         532.59
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                64.561(5)
_cell_angle_beta                 87.812(3)
_cell_angle_gamma                84.160(3)
_cell_formula_units_Z            1
_cell_length_a                   6.25857(15)
_cell_length_b                   10.3600(6)
_cell_length_c                   11.9013(6)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4080
_cell_measurement_theta_min      4.0480
_cell_volume                     693.22(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -102.00  -15.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 174

  2 omega  -49.00   37.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 172

  3 omega  -49.00   37.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 172

  4 omega   57.00  111.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  178.0000  120.0000 108

  5 omega  -32.00   65.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -77.0000   60.0000 194

  6 omega   -4.00   77.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015  -99.0000   60.0000 162

  7 omega    3.00   81.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015 -106.0000  -66.0000 156

  8 omega   14.00  107.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015   37.0000   60.0000 186

  9 omega   -1.00  109.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015   19.0000    0.0000 220

 10 omega   18.00  105.00   0.5000    0.7500
omega____ theta____ kappa____ phi______ frames
    -       36.7015   57.0000 -180.0000 174

 11 omega   37.00   91.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 108

 12 omega   71.00   98.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 54

 13 omega   39.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 116

 14 omega   41.00  106.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 130

 15 omega   54.00   91.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 74

 16 omega   39.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 114

 17 omega   78.00  176.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 196

 18 omega   37.00   89.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 104

 19 omega   87.00  129.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 84

 20 omega   61.00   88.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 54

 21 omega   37.00   65.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 56

 22 omega   38.00   85.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 94

 23 omega   62.00   99.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 74

 24 omega   62.00  115.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 106

 25 omega   90.00  156.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 132

 26 omega   41.00   81.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 80

 27 omega   41.00   90.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  150.0000 98

 28 omega   48.00  111.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 126

 29 omega  -81.00  -55.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 52

 30 omega  -45.00  -17.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 56

 31 omega   -3.00   22.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.0000   96.0000   22.9385 50

 32 omega    4.00   33.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 58

 33 omega   52.00   77.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 50

 34 omega   74.00   99.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 50

 35 omega    1.00   26.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   96.0000 -128.5753 50

 36 omega    8.00   13.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000  169.1242 10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0636941000
_diffrn_orient_matrix_UB_12      0.0295853000
_diffrn_orient_matrix_UB_13      -0.1332340000
_diffrn_orient_matrix_UB_21      0.0100387000
_diffrn_orient_matrix_UB_22      -0.1627493000
_diffrn_orient_matrix_UB_23      0.0385284000
_diffrn_orient_matrix_UB_31      -0.2388513000
_diffrn_orient_matrix_UB_32      0.0014828000
_diffrn_orient_matrix_UB_33      0.0361554000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5942
_diffrn_reflns_point_group_measured_fraction_full 0.668
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_theta_full        67.151
_diffrn_reflns_theta_max         67.151
_diffrn_reflns_theta_min         4.113
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82605
_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    1.276
_exptl_crystal_description       prism
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.007(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0982P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.343
_reflns_Friedel_fraction_full    0.342
_reflns_Friedel_fraction_max     0.342
_reflns_number_gt                5297
_reflns_number_total             5942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02948b2.cif
_cod_data_source_block           ly20070a_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1549848--1549849.cif.'
_cod_database_code               1549849
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.769
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5856(17)
 0.4144(17)
2. 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
3. Restrained distances
 C23-C25
 1.55 with sigma of 0.02
 C23-C25A
 1.55 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C25A) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C24) \\sim Ueq, Uanis(C24A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C25) = Uanis(C25A)
Uanis(C24) = Uanis(C24A)
Uanis(C26) = Uanis(C26A)
5. Others
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
6.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F), C25(H25A,H25B,H25C),
 C25A(H25D,H25E,H25F), C26(H26A,H26B,H26C), C26A(H26D,H26E,H26F)
;
_olex2_submission_special_instructions 'No special instructions were received'