Palladium(II)-catalyzed asymmetric C-H carbonylation to diverse isoquinoline derivatives bearing all-carbon quaternary stereocenters.
Li, Yan; Cheng, Xiu-Fen; Fei, Fan; Wu, Tian-Rui; Bian, Kang-Jie; Zhou, Xin; Wang, Xi-Sheng; Chemical communications (Cambridge, England) 56 (2020) 11605–11608; doi:10.1039/d0cc05219a

data_7127120
_publ_section_title
;
 Palladium(II)-catalyzed asymmetric C-H carbonylation to diverse
 isoquinoline derivatives bearing all-carbon quaternary stereocenters.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11605
_journal_page_last               11608
_journal_paper_doi               10.1039/d0cc05219a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 N O3'
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-01 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.37420(10)
_cell_length_b                   8.59040(10)
_cell_length_c                   12.08780(10)
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8710
_cell_measurement_theta_min      5.1160
_cell_volume                     751.656(15)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9272
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.836
_diffrn_reflns_theta_min         3.725
_exptl_absorpt_coefficient_mu    0.698
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.193
_refine_ls_abs_structure_details
;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0606
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                2783
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05219a2.cif
_cod_data_source_block           exp_47
_cod_depositor_comments
'Adding full bibliography for 7127117--7127120.cif.'
_cod_database_code               7127120
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.768
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H006)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H007), C12(H00D), C14(H00E), C13(H00F), C15(H00G), C2(H00H), C5(H00I),
 C3(H00J), C4(H00K)
2.c Idealised Me refined as rotating group:
 C17(H00A,H00B,H00C), C20(H00L,H00M,H00N)
2.d Idealised tetrahedral OH refined as rotating group:
 O18(H001)
;
_shelx_res_checksum              8520
_shelx_hkl_checksum              77618
_olex2_submission_special_instructions 'No special instructions were received'