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_1550963
_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 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_update_record
;
2019-03-27 deposited with the CCDC.    2019-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.6644(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   17.1343(2)
_cell_length_b                   10.09453(12)
_cell_length_c                   15.4280(2)
_cell_measurement_reflns_used    16415
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      2.60
_cell_volume                     2665.58(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 5.0rc6'
_computing_publication_material  'CrystalStructure 5.0rc6 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25304
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         2.582
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088.00
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0416P)^2^+1.2236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4374
_reflns_number_total             4873
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9sc01507h2.cif
_cod_data_source_block           SX17021R
_cod_database_code               1550963
_shelx_res_checksum              8431