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_1508704
_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 O6 Si2'
_chemical_formula_sum            'C40 H68 B2 O6 Si2'
_chemical_formula_weight         722.74
_chemical_name_common            TIPS-Bpin-BDF
_chemical_name_systematic
; 
 TIPS-Bpin-BDF 
;
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.699(7)
_cell_angle_beta                 86.956(7)
_cell_angle_gamma                83.755(7)
_cell_formula_units_Z            1
_cell_length_a                   7.7423(18)
_cell_length_b                   11.828(3)
_cell_length_c                   12.677(3)
_cell_measurement_reflns_used    8053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.24
_cell_measurement_theta_min      6.10
_cell_volume                     1107.3(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10180
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9100
_exptl_absorpt_correction_T_min  0.8692
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             394
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.4266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1902
_reflns_number_gt                4079
_reflns_number_total             4858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302521d_si_001.cif
_cod_data_source_block           TIPS-Bpin-BDF
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1508704