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_7127119
_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         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-27 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.87176(11)
_cell_length_b                   12.32287(17)
_cell_length_c                   16.6389(3)
_cell_measurement_reflns_used    6914
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4480
_cell_measurement_theta_min      4.4470
_cell_volume                     1614.02(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.867
_diffrn_reflns_theta_min         4.465
_exptl_absorpt_coefficient_mu    0.673
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0436
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2995
_reflns_number_total             3210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05219a2.cif
_cod_data_source_block           liyan-cxf-co-meoh
_cod_depositor_comments
'Adding full bibliography for 7127117--7127120.cif.'
_cod_database_code               7127119
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.775
_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. Rigid bond restraints
 C3, C4, C5, C6, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of
0.001
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C6(H6), C12(H12), C4(H4), C13(H13), C3(H3), C14(H14),
 C5(H5)
4.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_shelx_res_checksum              63727
_shelx_hkl_checksum              26847
_olex2_submission_special_instructions 'No special instructions were received'