Organocatalytic asymmetric tandem α-functionalization/1,3-proton shift reaction of benzylidene succinimides with β-trifluoromethyl enones.
Zhang, Xia-Yan; You, Yong; Wang, Zhen-Hua; Zhao, Jian-Qiang; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 56 (2020) 13449–13452; doi:10.1039/d0cc05474g

data_7127362
_publ_section_title
;
 Organocatalytic asymmetric tandem \a-functionalization/1,3-proton shift
 reaction of benzylidene succinimides with \b-trifluoromethyl enones.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13449
_journal_page_last               13452
_journal_paper_doi               10.1039/d0cc05474g
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 Br F3 N O5'
_chemical_formula_sum            'C26 H23 Br F3 N O5'
_chemical_formula_weight         566.36
_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             2018-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4781(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.78349(14)
_cell_length_b                   25.2447(4)
_cell_length_c                   11.5445(2)
_cell_measurement_reflns_used    8668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7120
_cell_measurement_theta_min      4.2030
_cell_volume                     2557.44(7)
_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 0.991
_diffrn_measurement_details
;
  1 omega  -74.00  -46.80   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 34

  2 omega  -68.00  -20.80   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000   30.0000 59

  3 omega  -15.00   34.60   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000   30.0000 62

  4 omega  -98.00  -38.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   60.0000 75

  5 omega   57.00  105.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -180.0000 60

  6 omega   40.00  112.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -160.0000    8.0000 90

  7 omega   71.00  109.40   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 48

  8 omega   60.00  100.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 50

  9 omega    1.00   34.60   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 42

 10 omega   18.00  103.60   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 107

 11 omega   40.00   68.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 35

 12 omega   15.00   87.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 90

 13 omega   45.00  103.40   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 73

 14 omega   -4.00   28.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000    0.0000 40

 15 omega   40.00   80.00   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -117.0000  160.0000 50

 16 omega   63.00   90.20   0.8000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 34

 17 omega   83.00  107.80   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 31

 18 omega   83.00  107.80   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 31

 19 omega   38.00   65.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 34

 20 omega   49.00   87.40   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 48

 21 omega   44.00   75.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 39

 22 omega   38.00   93.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 69

 23 omega   37.00   68.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 39

 24 omega   89.00  159.40   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 88

 25 omega   44.00   71.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 34

 26 omega   91.00  155.00   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 80

 27 omega   88.00  160.00   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 90

 28 omega   40.00   98.40   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 73

 29 omega   39.00   92.60   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 67

 30 omega   37.00   68.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 39

 31 omega   59.00   86.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 34

 32 omega   46.00   97.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 64

 33 omega   53.00  104.20   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 64

 34 omega   46.00  114.00   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 85

 35 omega   60.00  114.40   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 68

 36 omega   52.00   89.60   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 47

 37 omega   80.00  140.80   0.8000   25.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0388173000
_diffrn_orient_matrix_UB_12      -0.0552272000
_diffrn_orient_matrix_UB_13      -0.0471814000
_diffrn_orient_matrix_UB_21      -0.0248897000
_diffrn_orient_matrix_UB_22      -0.0242830000
_diffrn_orient_matrix_UB_23      0.1200959000
_diffrn_orient_matrix_UB_31      -0.1694731000
_diffrn_orient_matrix_UB_32      -0.0090697000
_diffrn_orient_matrix_UB_33      -0.0344484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19354
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.936
_diffrn_reflns_theta_min         3.502
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82517
_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    1.471
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 3691 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0733P)^2^+0.7141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                8737
_reflns_number_total             9594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05474g3.cif
_cod_data_source_block           201812497
_cod_depositor_comments          'Adding full bibliography for 7127362.cif.'
_cod_original_cell_volume        2557.43(7)
_cod_database_code               7127362
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C16H22O7N1F3Br1
_shelx_estimated_absorpt_t_max   0.773
_shelx_estimated_absorpt_t_min   0.719
_reflns_odcompleteness_completeness 99.98
_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:
 C6(H6), C6'(H6')
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C5'(H5'A,H5'B), C7'(H7'A,H7'B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C20(H20), C21(H21), C11'(H11'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'),
  C17'(H17'), C18'(H18'), C20'(H20'), C21'(H21')
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C24'(H24D,H24E,
 H24F), C25'(H25D,H25E,H25F), C26'(H26D,H26E,H26F)
;
_olex2_submission_special_instructions 'No special instructions were received'