Directed metalation cascade to access highly functionalized thieno[2,3-f]benzofuran and exploration as building blocks for organic electronics.
Aeschi, Yves; Li, Hui; Cao, Zhencai; Chen, Songjie; Amacher, Anneliese; Bieri, Nathalie; Özen, Bilal; Hauser, Juerg; Decurtins, Silvio; Tan, Songting; Liu, Shi-Xia; Organic letters 15 (2013) 5586–5589; doi:10.1021/ol402787d

data_1556251
_publ_section_title
;
 Directed metalation cascade to access highly functionalized
 thieno[2,3-f]benzofuran and exploration as building blocks for organic
 electronics.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5586
_journal_page_last               5589
_journal_paper_doi               10.1021/ol402787d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C32 H46 O S Si2'
_chemical_formula_sum            'C32 H46 O S Si2'
_chemical_formula_weight         534.93
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 122.537(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.91950(10)
_cell_length_b                   15.25430(10)
_cell_length_c                   13.8533(2)
_cell_measurement_reflns_used    15494
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.7583
_cell_measurement_theta_min      1.7402
_cell_volume                     1589.05(5)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
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_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
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_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0965
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0372697
_diffrn_orient_matrix_UB_12      0.0309112
_diffrn_orient_matrix_UB_13      -0.0453663
_diffrn_orient_matrix_UB_21      0.0322499
_diffrn_orient_matrix_UB_22      0.0347244
_diffrn_orient_matrix_UB_23      0.0403722
_diffrn_orient_matrix_UB_31      0.0804526
_diffrn_orient_matrix_UB_32      0.0004026
_diffrn_orient_matrix_UB_33      0.0011281
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30735
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        31.5
_diffrn_reflns_theta_max         31.83
_diffrn_reflns_theta_min         2.196
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.80534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       prism
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.4147
_exptl_crystal_size_mid          0.1751
_exptl_crystal_size_min          0.0949
_refine_diff_density_max         2.174
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5198
_refine_ls_number_restraints     231
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.081
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1335P)^2^+1.4122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2325
_refine_ls_wR_factor_ref         0.2443
_reflns_number_gt                4299
_reflns_number_total             5198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol402787d_si_001.cif
_cod_data_source_block           12sd051
_cod_original_cell_volume        1589.04(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556251