Regiodivergent annulation of alkynyl indoles to construct spiro-pseudoindoxyl and tetrahydro-β-carbolines.
Zhang, Yong-Qiang; Zhu, Dao-Yong; Jiao, Zhi-Wei; Li, Bao-Sheng; Zhang, Fu-Min; Tu, Yong-Qiang; Bi, Zhigang; Organic letters 13 (2011) 3458–3461; doi:10.1021/ol201194n

data_1502254
_publ_section_title
;
 Regiodivergent annulation of alkynyl indoles to construct
 spiro-pseudoindoxyl and tetrahydro-\b-carbolines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3458
_journal_page_last               3461
_journal_paper_doi               10.1021/ol201194n
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C32 H28 N2 O3 S'
_chemical_formula_weight         520.62
_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                78.378(8)
_cell_angle_beta                 85.363(8)
_cell_angle_gamma                84.178(8)
_cell_formula_units_Z            2
_cell_length_a                   9.135(6)
_cell_length_b                   10.753(7)
_cell_length_c                   13.533(8)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.09
_cell_measurement_theta_min      2.25
_cell_volume                     1292.9(14)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.1089
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8933
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0822
_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^)+(0.0806P)^2^+0.0383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1992
_reflns_number_gt                2402
_reflns_number_total             4586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201194n_si_002.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502254