Borylation on benzo[1,2-b:4,5-b']- and naphtho[1,2-b:5,6-b']dichalcogenophenes: different chalcogene atom effects on borylation reaction depending on fused ring structure.
Nakano, Masahiro; Shinamura, Shoji; Sugimoto, Ryusuke; Osaka, Itaru; Miyazaki, Eigo; Takimiya, Kazuo; Organic letters 14 (2012) 5448–5451; doi:10.1021/ol302521d

data_1508705
_publ_section_title
;
 Borylation on benzo[1,2-b:4,5-b']- and
 naphtho[1,2-b:5,6-b']dichalcogenophenes: different chalcogene atom
 effects on borylation reaction depending on fused ring structure.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5448
_journal_page_last               5451
_journal_paper_doi               10.1021/ol302521d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C40 H68 B2 O4 S2 Si2'
_chemical_formula_sum            'C40 H68 B2 O4 S2 Si2'
_chemical_formula_weight         754.86
_chemical_name_common            TIPS-Bpin-BDT
_chemical_name_systematic
; 
TIPS-Bpin-BDT 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 113.6966(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.3238(9)
_cell_length_b                   13.3375(7)
_cell_length_c                   14.9419(11)
_cell_measurement_reflns_used    5888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2248.9(3)
_computing_cell_refinement       'CrystalClear 1.3.5'
_computing_data_collection       'CrystalClear 1.3.5'
_computing_data_reduction        'CrystalClear 1.3.5'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.71
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17021
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         17150
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.58(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1197P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                6307
_reflns_number_total             7605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302521d_si_001.cif
_cod_data_source_block           TIPS-Bpin-BDT
_cod_database_code               1508705