Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp(3))-H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine.
Mori, Keiji; Kawasaki, Taro; Akiyama, Takahiko; Organic letters 14 (2012) 1436–1439; doi:10.1021/ol300180w

data_1507159
_publ_section_title
;
 Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed
 C(sp(3))-H Bond Functionalization and Its Application to Formal Synthesis
 of (+-)-Tetrahydropalmatine.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1436
_journal_page_last               1439
_journal_paper_doi               10.1021/ol300180w
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C26 H29 N O6 S'
_chemical_formula_weight         483.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 107.0020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6511(8)
_cell_length_b                   21.4131(18)
_cell_length_c                   11.8730(10)
_cell_measurement_reflns_used    6351
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.40
_cell_volume                     2346.4(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13095
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0546P)^2^+1.1024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                4675
_reflns_number_total             5324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300180w_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1507159