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_4518407
_publ_section_title
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 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_absolute_configuration unk
_chemical_formula_sum            'C25 H25 B0 F0 N O2'
_chemical_formula_weight         371.46
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.12120(6)
_cell_length_b                   13.75566(14)
_cell_length_c                   18.96034(18)
_cell_measurement_reflns_used    43263
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      60.4440
_cell_measurement_theta_min      3.4260
_cell_volume                     1857.29(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      99.9(4)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42680
_diffrn_reflns_theta_full        52.04
_diffrn_reflns_theta_max         52.04
_diffrn_reflns_theta_min         3.45
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0447P)^2^+0.3388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                3120
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs0c05156_si_002.cif
_cod_data_source_block           xlt-3
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value ' unk ' was
changed to 'unk' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4518407