Silver(i)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols.
Zhu, Yu; Shen, Xin-Rui; Tang, Hai-Tao; Lin, Min; Zhan, Zhuang-Ping; Organic & biomolecular chemistry 12 (2014) 9514–9518; doi:10.1039/c4ob02020k

data_7154145
_publ_section_title
;
 Silver(i)-catalyzed annulation for the regioselective synthesis of
 N-imino-\g-carbolinium ylides from hydrazones of indole-3-carbonyl
 derivatives and propargylic alcohols.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9514
_journal_page_last               9518
_journal_paper_doi               10.1039/c4ob02020k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C33 H30 N3 O3 S2'
_chemical_formula_weight         580.72
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.36(3)
_cell_angle_beta                 95.09(3)
_cell_angle_gamma                102.82(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8264(16)
_cell_length_b                   11.561(2)
_cell_length_c                   16.718(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1455.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0405
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12592
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1727
_refine_ls_wR_factor_ref         0.2362
_reflns_number_gt                4342
_reflns_number_total             5699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02020k2.cif
_cod_data_source_block           tri
_cod_depositor_comments
'Adding full bibliography for 7154145--7154146.cif.'
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7154145