Construction of Protoberberine Alkaloid Core through Palladium Carbene Bridging C‒H Bond Functionalization and Pyridine Dearomatization
Xin, Luoting; Wan, Wan; Yu, Yinghua; Wan, Qiuling; Ma, Liyao; Huang, Xueliang; ACS Catalysis  (2021) 1570–1577; doi:10.1021/acscatal.0c05156

data_4518406
_publ_section_title
;
 Construction of Protoberberine Alkaloid Core through Palladium Carbene
 Bridging C--H Bond Functionalization and Pyridine Dearomatization
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1570
_journal_page_last               1577
_journal_paper_doi               10.1021/acscatal.0c05156
_journal_year                    2021
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.248(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7743(8)
_cell_length_b                   23.418(6)
_cell_length_c                   8.802(2)
_cell_measurement_reflns_used    10348
_cell_measurement_temperature    110.82(11)
_cell_measurement_theta_max      60.5250
_cell_measurement_theta_min      4.7120
_cell_volume                     1369.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110.82(11)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus metaljet'
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34150
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14919
_diffrn_reflns_theta_full        60.59
_diffrn_reflns_theta_max         60.59
_diffrn_reflns_theta_min         4.75
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.4494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                2704
_reflns_number_total             3096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs0c05156_si_003.cif
_cod_data_source_block           exp_5599
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4518406