Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines.
Wang, Yue; Li, Er-Qing; Duan, Zheng; Chemical science 13 (2022) 8131–8136; doi:10.1039/d2sc02771b

data_1567190
_publ_section_title
;
 Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral
 tetrahydroquinolines.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              8131
_journal_page_last               8136
_journal_paper_doi               10.1039/d2sc02771b
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C28 H26 N3 O3'
_chemical_formula_sum            'C28 H26 N3 O3'
_chemical_formula_weight         452.52
_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             2022-01-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-01-05 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.501(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.647(3)
_cell_length_b                   20.509(7)
_cell_length_c                   8.8540(18)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.41
_cell_volume                     1538.7(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         1.986
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7061
_exptl_absorpt_correction_type   refdelf
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    0.977
_exptl_crystal_description       block
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 2493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.075(13)
_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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         7032
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0653
_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^)+(0.1455P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1925
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5950
_reflns_number_total             7032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02771b2.cif
_cod_data_source_block           mo_20211228m_0m
_cod_depositor_comments
'Adding full bibliography for 1567188--1567191.cif.'
_cod_database_code               1567190
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C00N(H00N), C00O(H00O)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G), C00J(H00J),
 C00L(H00L), C00M(H00M), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C00I(H00A,H00C,H00F), C00U(H00H,H00I,H00K)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              973
_shelx_hkl_checksum              89619
_shelx_fab_checksum              47980
_olex2_submission_special_instructions 'No special instructions were received'