Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based Polycyclic Privileged Scaffolds as α1-Adrenergic Receptor Antagonists
Zeng Li; Jing Li; Nan Yang; Ying Chen; Yu Zhou; Xun Ji; Lei Zhang; Jinfang Wang; Xin Xie; Hong Liu; Journal of Organic Chemistry 78 (2013) 10802–10811; doi:10.1021/jo4017887

data_4028719
_publ_section_title
;
 Gold(I)-Catalyzed Cascade Approach for the Synthesis of Tryptamine-Based
 Polycyclic Privileged Scaffolds as \a1-Adrenergic Receptor Antagonists
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10802
_journal_page_last               10811
_journal_paper_doi               10.1021/jo4017887
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39
_chemical_name_common            3be
_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
_audit_update_record
;
2012-12-20 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3759(3)
_cell_length_b                   13.0992(4)
_cell_length_c                   11.4895(3)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.87
_cell_measurement_theta_min      4.50
_cell_volume                     1710.87(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27556
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0354P)^2^+0.5628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                3276
_reflns_number_total             3936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4017887_si_003.cif
_cod_data_source_block           C21H20N2O2
_cod_database_code               4028719