Gold-Catalyzed Domino Cycloisomerization/Pictet-Spengler Reaction of 2-(4-Aminobut-1-yn-1-yl)anilines with Aldehydes: Synthesis of Tetrahydropyrido[4,3-b]indole Scaffolds
B. V. Subba Reddy; Manisha Swain; S.Madhusudana Reddy; J. S. Yadav; B. Sridhar; Journal of Organic Chemistry 77 (2012) 11355–11361; doi:10.1021/jo302068e

data_4027782
_publ_section_title
;
 Gold-Catalyzed Domino Cycloisomerization/Pictet-Spengler Reaction of
 2-(4-Aminobut-1-yn-1-yl)anilines with Aldehydes: Synthesis of
 Tetrahydropyrido[4,3-b]indole Scaffolds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11355
_journal_page_last               11361
_journal_paper_doi               10.1021/jo302068e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H21 F N2 O2 S'
_chemical_formula_sum            'C24 H21 F N2 O2 S'
_chemical_formula_weight         420.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.792(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.906(4)
_cell_length_b                   14.318(3)
_cell_length_c                   18.234(4)
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.44
_cell_volume                     4114.3(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38686
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         7245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+1.2291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                5440
_reflns_number_total             7245
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo302068e_si_001.cif
_cod_data_source_block           an72
_cod_original_cell_volume        4114.1(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027782