Synthesis of 2-Substituted Benzofurans and Indoles Using Functionalized Titanium Benzylidene Reagents on Solid Phase
Calum Macleod; Gordon J. McKiernan; Emma J. Guthrie; Louis J. Farrugia; Dieter W. Hamprecht; Jackie Macritchie; Richard C. Hartley; Journal of Organic Chemistry 68 (2003) 387–401; doi:10.1021/jo026384o

data_4022295
_publ_section_title
;
 Synthesis of 2-Substituted Benzofurans and Indoles Using
 Functionalized Titanium Benzylidene Reagents on Solid Phase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              387
_journal_page_last               401
_journal_paper_doi               10.1021/jo026384o
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H22 N2 O S4'
_chemical_formula_sum            'C20 H22 N2 O S4'
_chemical_formula_weight         434.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2002-08-12T10:20:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.1150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2666(2)
_cell_length_b                   19.2594(5)
_cell_length_c                   10.7649(2)
_cell_measurement_reflns_used    10059
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     2081.12(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.881576E-1
_diffrn_orient_matrix_UB_12      0.463338E-1
_diffrn_orient_matrix_UB_13      -0.24344E-2
_diffrn_orient_matrix_UB_21      -0.194118E-1
_diffrn_orient_matrix_UB_22      -0.107918E-1
_diffrn_orient_matrix_UB_23      -0.92378E-1
_diffrn_orient_matrix_UB_31      -0.241577E-1
_diffrn_orient_matrix_UB_32      0.459597E-1
_diffrn_orient_matrix_UB_33      -0.2869E-3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11736
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.47
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
   P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
   (1965), 18, 1035-1038
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.4331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3268
_reflns_number_total             4752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026384o_s1_1.cif
_cod_data_source_block           cpd48
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022295