Zn(OTf)2-mediated annulations of N-propargylated tetrahydrocarbolines: divergent synthesis of four distinct alkaloidal scaffolds
Yorimoto, Sadaiwa; Tsubouchi, Akira; Mizoguchi, Haruki; Oikawa, Hideaki; Tsunekawa, Yoshiaki; Ichino, Tomoya; Maeda, Satoshi; Oguri, Hiroki; Chemical Science  (2019) –; doi:10.1039/C9SC01507H

data_1550964
_publ_section_title
;
 Zn(OTf)2-mediated annulations of N-propargylated tetrahydrocarbolines:
 divergent synthesis of four distinct alkaloidal scaffolds
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01507H
_journal_year                    2019
_chemical_formula_moiety         'C16 H18 N2'
_chemical_formula_sum            'C16 H18 N2'
_chemical_formula_weight         238.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_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_update_record
;
2019-03-27 deposited with the CCDC.    2019-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.1973(16)
_cell_length_b                   11.006(3)
_cell_length_c                   16.413(4)
_cell_measurement_reflns_used    8490
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      3.09
_cell_volume                     1300.1(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider, et al., 2002)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1697
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12176
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             512.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1249 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00000
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                1611
_reflns_number_total             2978
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9sc01507h2.cif
_cod_data_source_block           User-defined
_cod_original_cell_volume        1300.1(5)
_cod_database_code               1550964