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_4022298
_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_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H23 N1 O2 S2'
_chemical_formula_sum            'C16 H23 N O2 S2'
_chemical_formula_weight         325.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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             2002-08-09T17:15:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.43970(10)
_cell_length_b                   11.8345(2)
_cell_length_c                   15.6919(3)
_cell_measurement_reflns_used    2784
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     1753.01(5)
_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)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      0.865701E-1
_diffrn_orient_matrix_UB_12      -0.43327E-1
_diffrn_orient_matrix_UB_13      -0.167732E-1
_diffrn_orient_matrix_UB_21      0.404114E-1
_diffrn_orient_matrix_UB_22      0.695853E-1
_diffrn_orient_matrix_UB_23      -0.26759E-1
_diffrn_orient_matrix_UB_31      0.457699E-1
_diffrn_orient_matrix_UB_32      0.205109E-1
_diffrn_orient_matrix_UB_33      0.553513E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5110
_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        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
   P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst.
   (1965), 18, 1035-1038
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       0.0060(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0225P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0677
_reflns_number_gt                4571
_reflns_number_total             5110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026384o_s1_4.cif
_cod_data_source_block           cpd51a
_cod_database_code               4022298