Enantioselective Synthesis of Isoquinoline-1,3(2H,4H)-dione Derivatives via Chiral Phosphoric Acid Catalyzed aza-Friedel−Crafts Reaction
you, yong; Lu, Wen-Ya; Xie, Ke-Xin; Zhao, Jian-Qiang; Wang, Zhen-Hua; Yuan, Weicheng; Chemical Communications  (2019) –; doi:10.1039/C9CC04057A

data_7123725
_publ_section_title
;
 Enantioselective Synthesis of Isoquinoline-1,3(2H,4H)-dione Derivatives
 via Chiral Phosphoric Acid Catalyzed aza-Friedel&#x2212;Crafts Reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04057A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_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             2019-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-22 deposited with the CCDC.    2019-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.05116(14)
_cell_length_b                   10.41903(19)
_cell_length_c                   21.8099(4)
_cell_measurement_reflns_used    5985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9810
_cell_measurement_theta_min      4.0420
_cell_volume                     1829.53(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    '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 0.996
_diffrn_measurement_details
;
  1 omega  -49.00   37.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 86

  2 omega -106.00    4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000   60.0000 110

  3 omega  -34.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000    0.0000 93

  4 omega   -1.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   60.0000 108

  5 omega   17.00   49.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -122.0000  101.0000 32

  6 omega   50.00  111.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -157.0000   35.0000 61

  7 omega   11.00   38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 27

  8 omega   12.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -60.0000 34

  9 omega   11.00   65.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 54

 10 omega   45.00   72.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 27

 11 omega    1.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -120.0000 58

 12 omega  -27.00    4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -19.0000 -150.0000 31

 13 omega   81.00  110.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 29

 14 omega   46.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 27

 15 omega   36.00  118.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -119.0000 -169.0000 82

 16 omega   41.00   82.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 41

 17 omega   40.00   89.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 49

 18 omega   63.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 27

 19 omega   93.00  154.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 61

 20 omega   37.00   68.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 31

 21 omega   42.00   67.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 25

 22 omega   47.00   97.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 50

 23 omega   95.00  177.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 82

 24 omega   47.00   92.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 45

 25 omega   87.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 45

 26 omega   48.00  108.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 60

 27 omega   44.00  107.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 63

 28 omega   42.00   88.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 46

 29 omega   79.00  107.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 28

 30 omega   55.00   83.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 28

 31 omega   50.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 40

 32 omega   42.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 48

 33 omega   41.00  132.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -60.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1507779000
_diffrn_orient_matrix_UB_12      0.0237304000
_diffrn_orient_matrix_UB_13      0.0419610000
_diffrn_orient_matrix_UB_21      -0.1160997000
_diffrn_orient_matrix_UB_22      0.0070002000
_diffrn_orient_matrix_UB_23      0.0560268000
_diffrn_orient_matrix_UB_31      0.0189010000
_diffrn_orient_matrix_UB_32      -0.1458525000
_diffrn_orient_matrix_UB_33      0.0095145000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.919
_diffrn_reflns_theta_min         4.054
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69935
_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    1.334
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0642P)^2^+0.1997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3303
_reflns_number_total             3496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04057a2.cif
_cod_data_source_block           20190237
_cod_database_code               7123725
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31ON5
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.902
_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
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_date_sample_data_collection 1551180331.22
_olex2_submission_special_instructions 'No special instructions were received'