Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related Isoquinoline Alkaloids from the Genus <i>Corydalis</i>.
Trost, Barry M.; Hung, Chao-I Joey; Jiao, Zhiwei; Journal of the American Chemical Society 141 (2019) 16085–16092; doi:10.1021/jacs.9b08441

data_4128308
_publ_section_title
;
 Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related
 Isoquinoline Alkaloids from the Genus <i>Corydalis</i>.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16085
_journal_page_last               16092
_journal_paper_doi               10.1021/jacs.9b08441
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H25 N O7'
_chemical_formula_sum            'C24 H25 N O7'
_chemical_formula_weight         439.45
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.08410(10)
_cell_length_b                   7.08410(10)
_cell_length_c                   41.0624(10)
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.45
_cell_measurement_theta_min      4.30
_cell_volume                     2060.69(6)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            44271
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.537
_diffrn_reflns_theta_min         4.307
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8297
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0427P)^2^+0.2642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3914
_reflns_number_total             3937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08441_si_002.cif
_cod_data_source_block           sucjn1
_cod_original_cell_volume        2060.70(8)
_cod_database_code               4128308
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.820
_shelx_estimated_absorpt_t_max   0.917
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              10542
_shelx_hkl_checksum              50825