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_1502232
_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         'C21 H13 Br1 O3'
_chemical_formula_sum            'C21 H13 Br O3'
_chemical_formula_weight         393.22
_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                 103.456(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.8336(13)
_cell_length_b                   3.9719(2)
_cell_length_c                   25.7332(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3263.8(2)
_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_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10037
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    2.536
_exptl_absorpt_correction_T_max  0.6581
_exptl_absorpt_correction_T_min  0.2455
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.717
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.717
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1025P)^2^+21.3710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2403
_reflns_number_total             2837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201062r_si_002.cif
_cod_data_source_block           a11179
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1502232