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_1502233
_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 H21 N O2'
_chemical_formula_sum            'C28 H21 N O2'
_chemical_formula_weight         403.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.874(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7694(9)
_cell_length_b                   9.5633(7)
_cell_length_c                   17.9026(16)
_cell_measurement_reflns_used    26597
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     2443.9(3)
_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 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.1194
_diffrn_reflns_av_sigmaI/netI    0.1942
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14165
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.0595
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.2267
_refine_ls_R_factor_gt           0.1015
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004
_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          0.2623
_refine_ls_wR_factor_ref         0.3320
_reflns_number_gt                1593
_reflns_number_total             4098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201062r_si_003.cif
_cod_data_source_block           11727
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1502233