Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline derivatives with 2-tributylstannylfuran: an efficient synthesis of (3-indolyl)stannanes
Jun Liu; Xin Xie; Yuanhong Liu; Chem.Commun. 50 (2013) 11794–; doi:10.1039/c3cc46524a

data_7110124
_publ_section_title
;
 Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline
 derivatives with 2-tributylstannylfuran: an efficient synthesis of
 (3-indolyl)stannanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11794
_journal_paper_doi               10.1039/c3cc46524a
_journal_volume                  50
_journal_year                    2013
_chemical_formula_sum            'C33 H45 I N2 O2 S Sn'
_chemical_formula_weight         779.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 114.579(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   37.522(3)
_cell_length_b                   11.2412(10)
_cell_length_c                   18.3416(15)
_cell_measurement_reflns_used    4612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.499
_cell_measurement_theta_min      4.781
_cell_volume                     7035.3(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20793
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0939
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6916
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                4791
_reflns_number_total             6916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46524a.txt
_cod_data_source_block           cd212594
_cod_original_cell_volume        7035.4(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7110124