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_7123724
_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         'C28 H25 N3 O4'
_chemical_formula_sum            'C28 H25 N3 O4'
_chemical_formula_weight         467.51
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-05-22 deposited with the CCDC.    2019-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.576(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0685(2)
_cell_length_b                   18.8284(6)
_cell_length_c                   8.1393(2)
_cell_measurement_reflns_used    5378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6080
_cell_measurement_theta_min      4.6770
_cell_volume                     1230.65(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 1.000
_diffrn_measurement_details
;
  1 omega  -62.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   30.0000 98

  2 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -90.0000 87

  3 omega  -52.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 28

  4 omega  -91.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -180.0000 35

  5 omega   16.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 61

  6 omega   33.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 31

  7 omega  -14.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 26

  8 omega  -29.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 32

  9 omega  -32.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -180.0000 35

 10 omega   28.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 30

 11 omega    8.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 25

 12 omega   63.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 37

 13 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 26

 14 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -180.0000 26

 15 omega    7.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 53

 16 omega  -32.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 48

 17 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 26

 18 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 51

 19 omega   76.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 28

 20 omega   93.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 53

 21 omega   83.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 31

 22 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 55

 23 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 26

 24 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 26

 25 omega   39.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 51

 26 omega   39.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 35

 27 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 85

 28 omega   56.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 71

 29 omega   38.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 30 omega   40.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 60

 31 omega   38.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 52

 32 omega   93.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 82

 33 omega   60.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 46

 34 omega   40.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 30

 35 omega   49.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 76

 36 omega   79.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 71

 37 omega   67.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

 38 omega  113.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 32

 39 omega   44.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 30

 40 omega  112.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 26

 41 omega  152.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 26

 42 omega  141.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 32

 43 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 26

 44 omega   57.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

 45 omega  100.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0858620000
_diffrn_orient_matrix_UB_12      0.0693271000
_diffrn_orient_matrix_UB_13      -0.0458920000
_diffrn_orient_matrix_UB_21      0.1623502000
_diffrn_orient_matrix_UB_22      -0.0412871000
_diffrn_orient_matrix_UB_23      -0.0166846000
_diffrn_orient_matrix_UB_31      -0.0554473000
_diffrn_orient_matrix_UB_32      -0.0136153000
_diffrn_orient_matrix_UB_33      -0.1837719000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.697
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87065
_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    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       0.0069(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0509P)^2^+0.1102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4196
_reflns_number_total             4407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04057a2.cif
_cod_data_source_block           201803167
_cod_original_cell_volume        1230.64(6)
_cod_database_code               7123724
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H20N2O8
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C27
 1.55 with sigma of 0.02
 C25-C26A
 1.55 with sigma of 0.02
 C27A-C25
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C28) = Uanis(C28A)
Uanis(C27) = Uanis(C27A)
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27A)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
5.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C26A(H26D,H26E,H26F), C27(H27A,H27B,H27C), C27A(H27D,
 H27E,H27F), C28(H28A,H28B,H28C), C28A(H28D,H28E,H28F)
;
_olex2_submission_special_instructions 'No special instructions were received'