A novel one-pot four-component access to tetrahydro-beta-carbolines by a coupling-amination-aza-annulation-Pictet-Spengler sequence (CAAPS).
Karpov, Alexei S; Oeser, Thomas; Müller, Thomas J J; Chemical communications (Cambridge, England)  (2004) 1502–1503; doi:10.1039/b404559a

data_7102719
_publ_section_title
;
 A novel one-pot four-component access to tetrahydro-beta-carbolines by
 a coupling-amination-aza-annulation-Pictet-Spengler sequence (CAAPS).
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1502
_journal_page_last               1503
_journal_paper_doi               10.1039/b404559a
_journal_year                    2004
_chemical_formula_sum            'C27 H30 Cl2 N2 O4 S'
_chemical_formula_weight         549.49
_chemical_name_systematic
;
Tetrahydro-beta-carboline
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 94.869(2)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   12.022(1)
_cell_length_b                   14.950(1)
_cell_length_c                   14.663(1)
_cell_measurement_reflns_used    6730
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.29
_cell_volume                     2625.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23151
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_correction_T_min  0.9276
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     877
_refine_ls_number_reflns         10561
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                9120
_reflns_number_total             10561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b404559a.txt
_cod_data_source_block           aka13
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7102719