Preparation of functional benzofurans, benzothiophenes, and indoles using ester, thioester, and amide via intramolecular Wittig reactions.
Syu, Siang-en; Lee, Yu-Ting; Jang, Yeong-Jiunn; Lin, Wenwei; Organic letters 13 (2011) 2970–2973; doi:10.1021/ol201062r

data_1502234
_publ_section_title
;
 Preparation of functional benzofurans, benzothiophenes, and indoles using
 ester, thioester, and amide via intramolecular Wittig reactions.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2970
_journal_page_last               2973
_journal_paper_doi               10.1021/ol201062r
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C28 H20 Cl N O2'
_chemical_formula_sum            'C28 H20 Cl N O2'
_chemical_formula_weight         437.90
_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                86.8120(10)
_cell_angle_beta                 86.1960(10)
_cell_angle_gamma                82.0110(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8960(2)
_cell_length_b                   8.4620(2)
_cell_length_c                   18.5120(6)
_cell_measurement_reflns_used    5452
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     1066.23(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9677
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.458
_exptl_absorpt_correction_T_min  0.8216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0536
_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^)+(0.1002P)^2^+0.1124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1675
_reflns_number_gt                2824
_reflns_number_total             3705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201062r_si_004.cif
_cod_data_source_block           11879
_cod_database_code               1502234