Orthogonally functionalized naphthodithiophenes: selective protection and borylation.
Shinamura, Shoji; Sugimoto, Ryusuke; Yanai, Naoyuki; Takemura, Noriko; Kashiki, Tomoya; Osaka, Itaru; Miyazaki, Eigo; Takimiya, Kazuo; Organic letters 14 (2012) 4718–4721; doi:10.1021/ol301797g

data_1508595
_publ_section_title
;
 Orthogonally functionalized naphthodithiophenes: selective protection and
 borylation.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4718
_journal_page_last               4721
_journal_paper_doi               10.1021/ol301797g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C44 H70 B2 O4 S2 Si2'
_chemical_formula_sum            'C44 H70 B2 O4 S2 Si2'
_chemical_formula_weight         804.92
_chemical_name_common            NDT3-TIPS-Bpin
_chemical_name_systematic
; 
NDT3-TIPS-Bpin 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000(13)
_cell_angle_beta                 115.3550(16)
_cell_angle_gamma                90.0000(13)
_cell_formula_units_Z            4
_cell_length_a                   25.371(17)
_cell_length_b                   15.486(10)
_cell_length_c                   15.010(10)
_cell_measurement_reflns_used    6474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0043
_cell_volume                     5329(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19747
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         6037
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0922
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1424P)^2^+2.4873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.2706
_reflns_number_gt                4257
_reflns_number_total             6037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301797g_si_002.cif
_cod_data_source_block           NDT3-TIPS-Bpin
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        5330(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1508595