Enantioselective amination of 4-alkylisoquinoline-1,3(2H,4H)-dione derivatives
Cheng, Cheng; Li, Ying-Xian; Jia, Xue-Min; Zhang, Ji-Quan; Zhao, Yong-Long; Feng, Wei; Tang, Lei; Yang, Yuan-Yong; RSC Advances 10 (2020) 42912–42915; doi:10.1039/D0RA07806A

data_7241624
_publ_section_title
;
 Enantioselective amination of 4-alkylisoquinoline-1,3(2H,4H)-dione
 derivatives
;
_journal_issue                   70
_journal_name_full               'RSC Advances'
_journal_page_first              42912
_journal_page_last               42915
_journal_paper_doi               10.1039/D0RA07806A
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C16.5 H18 Cl0.5 N1.5 O3)'
_chemical_formula_sum            'C33 H36 Cl N3 O6'
_chemical_formula_weight         606.10
_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
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_audit_update_record
;
2020-06-14 deposited with the CCDC.	2020-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.588(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7532(4)
_cell_length_b                   22.6105(9)
_cell_length_c                   13.3665(6)
_cell_measurement_reflns_used    8380
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      73.3960
_cell_measurement_theta_min      3.2520
_cell_volume                     3243.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2018/3 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -30.00  -4.00   1.00    1.00    --   40.98 -57.00 -90.00   26
  2  \w     32.00 125.00   1.00    2.00    --  106.95 -30.00  30.00   93
  3  \w     82.00 109.00   1.00    2.00    --  106.95 -45.00 150.00   27
  4  \w     54.00 133.00   1.00    2.00    --  106.95 -45.00 -60.00   79
  5  \w     80.00 152.00   1.00    2.00    --  106.95  30.00-150.00   72
  6  \w    126.00 175.00   1.00    2.00    --  106.95  30.00-180.00   49
  7  \w    125.00 170.00   1.00    2.00    --  106.95 125.00  90.00   45
  8  \w     33.00 135.00   1.00    2.00    --  106.95 -30.00-150.00  102
  9  \w    -49.00  -3.00   1.00    1.00    --  -40.98 125.00 150.00   46
 10  \w   -104.00 -21.00   1.00    1.00    --  -40.98 -38.00 -60.00   83
 11  \w    -68.00  19.00   1.00    1.00    --  -40.98  57.00 120.00   87
 12  \w    -75.00 -24.00   1.00    2.00    --  -41.23 -38.00 150.00   51
 13  \w    -90.00 -20.00   1.00    2.00    --  -41.23 -38.00-150.00   70
 14  \w    -33.00  34.00   1.00    2.00    --   41.23 -38.00 -30.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0722538000
_diffrn_orient_matrix_UB_12      0.0540775000
_diffrn_orient_matrix_UB_13      -0.0359984000
_diffrn_orient_matrix_UB_21      0.0973644000
_diffrn_orient_matrix_UB_22      -0.0079212000
_diffrn_orient_matrix_UB_23      0.0886107000
_diffrn_orient_matrix_UB_31      0.0767054000
_diffrn_orient_matrix_UB_32      -0.0406817000
_diffrn_orient_matrix_UB_33      -0.0648530000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            10317
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.645
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.087
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
;
 Flack x determined using 3230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     788
_refine_ls_number_reflns         10317
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0684P)^2^+11.5516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2168
_refine_ls_wR_factor_ref         0.2191
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_full    0.656
_reflns_Friedel_fraction_max     0.595
_reflns_number_gt                9680
_reflns_number_total             10317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra07806a2.cif
_cod_data_source_block           395-2_tw
_cod_database_code               7241624
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.836
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6402(13)
 0.3598(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C11, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C11 \\sim C16: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C10B(H10C,H10D), C17B(H17C,H17D), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N3B(H3B), N3(H3), C19B(H19B), C7B(H7B), C19(H19), C5(H5), C14(H14),
 C16B(H16B), C16(H16), C22B(H22B), C2(H2), C15B(H15B), C20B(H20B), C4(H4),
 C4B(H4B), C5B(H5B), C15(H15), C23B(H23B), C22(H22), C20(H20), C12(H12),
 C3(H3A), C12B(H12B), C23(H23), C14B(H14B), C6B(H6B), C13(H13), C13B(H13B)
5.c Idealised Me refined as rotating group:
 C27B(H27D,H27E,H27F), C28(H28A,H28B,H28C), C33B(H33D,H33E,H33F), C26B(H26D,
 H26E,H26F), C26(H26A,H26B,H26C), C32B(H32D,H32E,H32F), C28B(H28D,H28E,H28F),
 C32(H32A,H32B,H32C), C31B(H31D,H31E,H31F), C31(H31A,H31B,H31C), C27(H27A,H27B,
 H27C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              15646
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.593