Asymmetric Aerobic Decarboxylative Povarov Reactions of N-Aryl α-Amino Acids with Methylenephthalimidines via Cooperative Photoredox and Chiral Brønsted Acid Catalysis
Li, Jiangtao; Gu, Ziwei; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong; Chemical Communications  (2019) –; doi:10.1039/C9CC07380A

data_7124286
_publ_section_title
;
 Asymmetric Aerobic Decarboxylative Povarov Reactions of N-Aryl \a-Amino
 Acids with Methylenephthalimidines via Cooperative Photoredox and Chiral
 Br\/onsted Acid Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07380A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C17 H15 Br N2 O), C4 H8 O2'
_chemical_formula_sum            'C38 H38 Br2 N4 O4'
_chemical_formula_weight         774.54
_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             2019-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-06 deposited with the CCDC.    2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.51375(16)
_cell_length_b                   16.8250(3)
_cell_length_c                   22.3825(6)
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1420
_cell_measurement_theta_min      4.7360
_cell_volume                     3582.74(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    8.00   37.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   90.0000 58

  2 omega -101.00  -74.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 54

  3 omega  -61.00  -34.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 54

  4 omega -100.00  -52.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000    0.0000 96

  5 omega  -35.00    0.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   90.0000 70

  6 omega    2.00   57.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 110

  7 omega    0.00   36.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 72

  8 omega  -15.00   15.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 60

  9 omega    3.00   30.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 54

 10 omega   -4.00   22.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 52

 11 omega   13.00   54.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 82

 12 omega  -26.00   -1.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  150.0000 50

 13 omega  -32.00   30.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -30.0000 124

 14 omega   13.00   68.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 110

 15 omega   81.00  107.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 52

 16 omega   59.00   96.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 74

 17 omega   -7.00   61.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   30.0000 136

 18 omega   13.00   40.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 54

 19 omega    3.00   76.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 146

 20 omega   15.00   92.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  120.0000 154

 21 omega   59.00  106.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 94

 22 omega  -34.00   42.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -90.0000 152

 23 omega   35.00   76.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 82

 24 omega  -23.00    5.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 56

 25 omega   55.00   87.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 64

 26 omega   56.00   84.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 56

 27 omega  112.00  137.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 50

 28 omega   43.00   91.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 96

 29 omega   39.00   93.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 108

 30 omega   74.00  123.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 98

 31 omega  125.00  159.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 68

 32 omega   39.00  103.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 128

 33 omega   38.00   65.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000   10.0000 54

 34 omega   46.00  109.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 126

 35 omega   71.00  111.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 80

 36 omega   38.00   69.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 62

 37 omega   37.00   90.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 106

 38 omega   38.00   91.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 106

 39 omega   60.00   90.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 60

 40 omega   44.00  109.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 130

 41 omega  111.00  138.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 54

 42 omega   83.00  108.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 50

 43 omega   45.00   71.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 52

 44 omega  120.00  178.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 116

 45 omega   84.00  110.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 52

 46 omega   37.00   72.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 70

 47 omega   90.00  117.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000   10.0000 54

 48 omega   39.00  152.00   0.5000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  120.0000 226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0326915000
_diffrn_orient_matrix_UB_12      0.0746473000
_diffrn_orient_matrix_UB_13      -0.0373169000
_diffrn_orient_matrix_UB_21      -0.0128269000
_diffrn_orient_matrix_UB_22      -0.0517914000
_diffrn_orient_matrix_UB_23      -0.0564638000
_diffrn_orient_matrix_UB_31      -0.1580572000
_diffrn_orient_matrix_UB_32      -0.0112445000
_diffrn_orient_matrix_UB_33      0.0123134000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30235
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60829
_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    1.436
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 2286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0857P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5765
_reflns_number_total             6408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07380a2.cif
_cod_data_source_block           201903ljt1
_cod_original_cell_volume        3582.73(13)
_cod_database_code               7124286
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Br1
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.698
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C16'(H16')
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15'(H15C,H15D), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C1'(H1'),
 C3'(H3'), C4'(H4'), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14')
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17'(H17D,H17E,H17F), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'