Palladium catalyzed asymmetric allylic alkylation of isoquinolinedione derivatives in the preparation of quaternary carbon stereocenters.
Li, Ying-Xian; Cheng, Cheng; Tang, Lei; Yang, Yuan-Yong; Organic & biomolecular chemistry 18 (2020) 4551–4555; doi:10.1039/d0ob00765j

data_7157519
_publ_section_title
;
 Palladium catalyzed asymmetric allylic alkylation of isoquinolinedione
 derivatives in the preparation of quaternary carbon stereocenters.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4551
_journal_page_last               4555
_journal_paper_doi               10.1039/d0ob00765j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H29 N O S'
_chemical_formula_sum            'C32 H29 N O S'
_chemical_formula_weight         475.62
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-01-14 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.25182(19)
_cell_length_b                   14.2225(3)
_cell_length_c                   10.38203(19)
_cell_measurement_reflns_used    3749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.3640
_cell_measurement_theta_min      5.4150
_cell_volume                     1310.10(5)
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -57.00  -2.00   1.00    1.00    --  -40.98 125.00-120.00   55
  2  \w     18.00 113.00   1.00    1.00    --   40.98  38.00-180.00   95
  3  \w    131.00 175.00   1.00    1.00    --  106.95 125.00-120.00   44
  4  \w    102.00 140.00   1.00    1.00    --  106.95 125.00 -30.00   38
  5  \w     74.00 135.00   1.00    1.00    --  106.95 -30.00   0.00   61
  6  \w    106.00 132.00   1.00    1.00    --  106.95 -61.00  90.00   26
  7  \w     34.00 127.00   1.00    1.00    --  106.95 -30.00-120.00   93
  8  \w     48.00 119.00   1.00    1.00    --  106.95-125.00-150.00   71
  9  \w     27.00  85.00   1.00    1.00    --  106.95 -15.00-180.00   58
 10  \w    -95.00  -4.00   1.00    1.00    --  -40.98 125.00 150.00   91
;
_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      -0.0588680000
_diffrn_orient_matrix_UB_12      0.0002194000
_diffrn_orient_matrix_UB_13      0.1248547000
_diffrn_orient_matrix_UB_21      -0.1427104000
_diffrn_orient_matrix_UB_22      -0.0530276000
_diffrn_orient_matrix_UB_23      -0.0797227000
_diffrn_orient_matrix_UB_31      0.0798877000
_diffrn_orient_matrix_UB_32      -0.0942947000
_diffrn_orient_matrix_UB_33      0.0446051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4890
_diffrn_reflns_point_group_measured_fraction_full 0.709
_diffrn_reflns_point_group_measured_fraction_max 0.678
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.527
_diffrn_reflns_theta_min         4.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80494
_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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(17)
_refine_ls_extinction_coef       0.0149(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.340
_reflns_Friedel_fraction_full    0.393
_reflns_Friedel_fraction_max     0.359
_reflns_number_gt                3452
_reflns_number_total             3578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00765j2.cif
_cod_data_source_block           lyx620
_cod_depositor_comments          'Adding full bibliography for 7157519.cif.'
_cod_original_cell_volume        1310.09(4)
_cod_database_code               7157519
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.862
_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. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C3 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C15(H15)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C21(H21), C30(H30), C18(H18), C24(H24), C20(H20), C13(H13), C9(H9),
 C2(H2), C19(H19), C29(H29), C6(H6), C27(H27), C12(H12), C28(H28), C3(H3),
 C10(H10), C5(H5), C4(H4)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              70281
_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.817