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_7123726
_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         'C21 H25 N3 O4'
_chemical_formula_sum            'C21 H25 N3 O4'
_chemical_formula_weight         383.44
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-28
_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            8
_cell_length_a                   10.81497(10)
_cell_length_b                   10.81497(10)
_cell_length_c                   37.0777(4)
_cell_measurement_reflns_used    7175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5840
_cell_measurement_theta_min      4.2390
_cell_volume                     4336.74(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 0.994
_diffrn_measurement_details
;
  1 omega  -13.00   36.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 98

  2 omega -100.00  -74.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 52

  3 omega  -55.00  -25.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000  -30.0000 60

  4 omega  -32.00    3.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 70

  5 omega   22.00   69.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 94

  6 omega   -3.00   23.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 52

  7 omega   16.00   44.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  120.0000 56

  8 omega   27.00   73.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 92

  9 omega   23.00  105.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 164

 10 omega   60.00   96.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 72

 11 omega   58.00   88.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 60

 12 omega   77.00  107.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 60

 13 omega   49.00  105.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 112

 14 omega   89.00  144.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 110

 15 omega   37.00   88.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 102

 16 omega   54.00  109.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 110

 17 omega   55.00  126.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 142

 18 omega   39.00   89.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 100

 19 omega   38.00   70.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 64

 20 omega   38.00   91.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 106

 21 omega   59.00  127.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0046067000
_diffrn_orient_matrix_UB_12      0.1353626000
_diffrn_orient_matrix_UB_13      -0.0128498000
_diffrn_orient_matrix_UB_21      0.1415092000
_diffrn_orient_matrix_UB_22      -0.0006373000
_diffrn_orient_matrix_UB_23      -0.0049174000
_diffrn_orient_matrix_UB_31      -0.0162123000
_diffrn_orient_matrix_UB_32      -0.0442663000
_diffrn_orient_matrix_UB_33      -0.0391952000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            18060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.892
_diffrn_reflns_theta_min         4.258
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79333
_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    1.175
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0704P)^2^+0.2009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3750
_reflns_number_total             4153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04057a2.cif
_cod_data_source_block           20190238
_cod_original_cell_volume        4336.74(9)
_cod_database_code               7123726
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31ON5
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 99.92
_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. Restrained distances
 N1-C14
 1.45 with sigma of 0.02
 N1-C14A
 1.45 with sigma of 0.02
 C14A-C15A
 1.55 with sigma of 0.02
 C15A-C16A
 1.55 with sigma of 0.02
 C15-C16
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
4. Others
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=
 Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D), C15(H15A,H15B), C15A(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'