#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508706.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1508706
loop_
_publ_author_name
'Nakano, Masahiro'
'Shinamura, Shoji'
'Sugimoto, Ryusuke'
'Osaka, Itaru'
'Miyazaki, Eigo'
'Takimiya, Kazuo'
_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 Se2 Si2'
_chemical_formula_sum            'C40 H68 B2 O4 Se2 Si2'
_chemical_formula_weight         848.66
_chemical_name_common            TIPS-Bpin-BDS
_chemical_name_systematic
; 
 TIPS-Bpin-BDS  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.371(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.433(8)
_cell_length_b                   13.331(8)
_cell_length_c                   14.725(10)
_cell_measurement_reflns_used    6234
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2240(2)
_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 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0660
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16035
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_number         16353
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         1.605
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0644
_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/[σ²(Fo²)+(0.1315P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                3822
_reflns_number_total             4951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302521d_si_001.cif
_cod_data_source_block           TIPS-Bpin-BDS
_cod_original_cell_volume        2240(3)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1508706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Se1 Se 0.25628(3) 0.12094(2) 0.45163(3) 0.05127(19) Uani 1 1 d
Si1 Si 0.23473(8) 0.32354(7) 0.31291(7) 0.0540(3) Uani 1 1 d
O1 O 0.2299(2) -0.0566(2) 0.5637(2) 0.0737(9) Uani 1 1 d
O2 O 0.3669(3) -0.1688(2) 0.6480(3) 0.0835(10) Uani 1 1 d
C1 C 0.4238(2) -0.0439(2) 0.5421(2) 0.0414(6) Uani 1 1 d
C2 C 0.3937(2) 0.0439(2) 0.4844(2) 0.0409(6) Uani 1 1 d
C3 C 0.3158(3) 0.2098(2) 0.3825(2) 0.0490(7) Uani 1 1 d
C4 C 0.4197(3) 0.1781(2) 0.3876(2) 0.0468(7) Uani 1 1 d
C5 C 0.4679(3) 0.0868(2) 0.4431(2) 0.0413(6) Uani 1 1 d
C6 C 0.1811(4) -0.1105(3) 0.6241(4) 0.0746(13) Uani 1 1 d
C7 C 0.2977(8) -0.2283(8) 0.7694(6) 0.161(4) Uani 1 1 d
C8 C 0.2214(7) -0.2942(5) 0.6063(8) 0.136(3) Uani 1 1 d
C9 C 0.2636(4) -0.1980(3) 0.6653(4) 0.0710(11) Uani 1 1 d
C10 C 0.1851(10) -0.0388(6) 0.7031(7) 0.155(4) Uani 1 1 d
C11 C 0.0572(6) -0.1352(7) 0.5635(8) 0.165(5) Uani 1 1 d
C12 C 0.3394(5) 0.4100(4) 0.2873(4) 0.0820(14) Uani 1 1 d
C13 C 0.3799(7) 0.3846(5) 0.2078(7) 0.119(3) Uani 1 1 d
C14 C 0.4470(6) 0.4366(5) 0.3777(6) 0.124(3) Uani 1 1 d
C15 C 0.1565(6) 0.3833(4) 0.3812(5) 0.101(2) Uani 1 1 d
C16 C 0.2182(9) 0.4082(7) 0.4854(5) 0.153(4) Uani 1 1 d
C17 C 0.0792(9) 0.4739(7) 0.3244(7) 0.187(5) Uani 1 1 d
C18 C 0.1222(5) 0.2822(4) 0.1874(3) 0.0871(15) Uani 1 1 d
C20 C 0.0148(5) 0.2354(6) 0.1907(6) 0.145(3) Uani 1 1 d
C21 C 0.1696(9) 0.2082(6) 0.1340(5) 0.137(3) Uani 1 1 d
B8 B 0.3398(3) -0.0914(3) 0.5846(3) 0.0478(8) Uani 1 1 d
H1 H 0.4612 0.2140 0.3549 0.057 Uiso 1 1 d
H2 H 0.2330 -0.2470 0.7823 0.197 Uiso 1 1 d
H3 H 0.3534 -0.2822 0.7856 0.197 Uiso 1 1 d
H4 H 0.3370 -0.1722 0.8122 0.197 Uiso 1 1 d
H5 H 0.1523 -0.3175 0.6118 0.161 Uiso 1 1 d
H6 H 0.2022 -0.2799 0.5366 0.161 Uiso 1 1 d
H7 H 0.2798 -0.3437 0.6269 0.161 Uiso 1 1 d
H8 H 0.2689 -0.0201 0.7423 0.173 Uiso 1 1 d
H9 H 0.1453 0.0210 0.6779 0.173 Uiso 1 1 d
H10 H 0.1588 -0.0687 0.7487 0.173 Uiso 1 1 d
H11 H 0.0120 -0.0760 0.5363 0.198 Uiso 1 1 d
H12 H 0.0517 -0.1763 0.5061 0.198 Uiso 1 1 d
H13 H 0.0222 -0.1719 0.5989 0.198 Uiso 1 1 d
H14 H 0.4296 0.3281 0.2259 0.134 Uiso 1 1 d
H15 H 0.3119 0.3680 0.1481 0.134 Uiso 1 1 d
H16 H 0.4183 0.4397 0.1934 0.134 Uiso 1 1 d
H17 H 0.5003 0.3804 0.3974 0.145 Uiso 1 1 d
H18 H 0.4889 0.4917 0.3644 0.145 Uiso 1 1 d
H19 H 0.4282 0.4545 0.4321 0.145 Uiso 1 1 d
H20 H 0.2603 0.3502 0.5191 0.184 Uiso 1 1 d
H21 H 0.2674 0.4616 0.4914 0.184 Uiso 1 1 d
H22 H 0.1614 0.4244 0.5126 0.184 Uiso 1 1 d
H23 H 0.1312 0.5304 0.3311 0.193 Uiso 1 1 d
H24 H 0.0406 0.4586 0.2568 0.193 Uiso 1 1 d
H25 H 0.0250 0.4925 0.3516 0.193 Uiso 1 1 d
H26 H -0.0190 0.2800 0.2244 0.174 Uiso 1 1 d
H27 H -0.0421 0.2208 0.1277 0.174 Uiso 1 1 d
H28 H 0.0355 0.1744 0.2293 0.174 Uiso 1 1 d
H29 H 0.1891 0.1457 0.1709 0.158 Uiso 1 1 d
H30 H 0.1115 0.1925 0.0695 0.158 Uiso 1 1 d
H31 H 0.2371 0.2330 0.1281 0.158 Uiso 1 1 d
H32 H 0.0979 0.3340 0.3809 0.131 Uiso 1 1 d
H33 H 0.0965 0.3397 0.1452 0.102 Uiso 1 1 d
H34 H 0.2981 0.4726 0.2676 0.098 Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_publ_flag
C2 Se1 C3 88.32(14) . yes
C15 Si1 C3 109.7(2) . yes
C15 Si1 C12 113.7(3) . yes
C3 Si1 C12 109.76(19) . yes
C15 Si1 C18 108.2(3) . yes
C3 Si1 C18 108.87(19) . yes
C12 Si1 C18 106.4(2) . yes
B8 O1 C6 108.6(3) . yes
B8 O2 C9 109.4(3) . yes
C5 C1 C2 116.3(3) 3_656 yes
C5 C1 B8 122.1(3) 3_656 yes
C2 C1 B8 121.6(3) . yes
C1 C2 C5 122.3(3) . yes
C1 C2 Se1 127.2(2) . yes
C5 C2 Se1 110.5(2) . yes
C4 C3 Si1 125.8(3) . yes
C4 C3 Se1 110.3(2) . yes
Si1 C3 Se1 123.9(2) . yes
C3 C4 C5 118.1(3) . yes
C1 C5 C2 121.4(3) 3_656 yes
C1 C5 C4 125.9(3) 3_656 yes
C2 C5 C4 112.7(3) . yes
O1 C6 C11 109.2(5) . yes
O1 C6 C10 105.6(5) . yes
C11 C6 C10 108.6(7) . yes
O1 C6 C9 104.3(3) . yes
C11 C6 C9 116.6(5) . yes
C10 C6 C9 112.0(6) . yes
O2 C9 C7 110.2(5) . yes
O2 C9 C6 103.1(3) . yes
C7 C9 C6 119.8(5) . yes
O2 C9 C8 104.7(5) . yes
C7 C9 C8 104.8(6) . yes
C6 C9 C8 113.3(5) . yes
C13 C12 C14 106.9(6) . yes
C13 C12 Si1 119.7(5) . yes
C14 C12 Si1 114.1(4) . yes
C16 C15 C17 110.0(6) . yes
C16 C15 Si1 120.3(5) . yes
C17 C15 Si1 112.9(4) . yes
C20 C18 C21 106.4(6) . yes
C20 C18 Si1 114.3(4) . yes
C21 C18 Si1 113.8(4) . yes
O2 B8 O1 111.9(3) . yes
O2 B8 C1 124.8(3) . yes
O1 B8 C1 123.2(3) . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C2 1.885(3) . yes
Se1 C3 1.894(3) . yes
Si1 C15 1.835(6) . yes
Si1 C3 1.882(3) . yes
Si1 C12 1.885(5) . yes
Si1 C18 1.904(5) . yes
O1 B8 1.358(5) . yes
O1 C6 1.451(5) . yes
O2 B8 1.342(5) . yes
O2 C9 1.458(5) . yes
C1 C5 1.399(4) 3_656 yes
C1 C2 1.408(4) . yes
C1 B8 1.550(5) . yes
C2 C5 1.412(4) . yes
C3 C4 1.332(5) . yes
C4 C5 1.456(4) . yes
C5 C1 1.399(4) 3_656 yes
C6 C11 1.479(9) . yes
C6 C10 1.490(10) . yes
C6 C9 1.513(6) . yes
C7 C9 1.475(8) . yes
C8 C9 1.520(9) . yes
C12 C13 1.485(10) . yes
C12 C14 1.509(8) . yes
C15 C16 1.456(10) . yes
C15 C17 1.563(8) . yes
C18 C20 1.491(8) . yes
C18 C21 1.519(10) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C5 0.1(5) 3_656 . yes
B8 C1 C2 C5 -178.5(3) . . yes
C5 C1 C2 Se1 -179.2(2) 3_656 . yes
B8 C1 C2 Se1 2.2(4) . . yes
C3 Se1 C2 C1 178.8(3) . . yes
C3 Se1 C2 C5 -0.6(2) . . yes
C15 Si1 C3 C4 -144.5(4) . . yes
C12 Si1 C3 C4 -18.9(4) . . yes
C18 Si1 C3 C4 97.2(4) . . yes
C15 Si1 C3 Se1 38.0(3) . . yes
C12 Si1 C3 Se1 163.6(3) . . yes
C18 Si1 C3 Se1 -80.3(3) . . yes
C2 Se1 C3 C4 0.8(3) . . yes
C2 Se1 C3 Si1 178.6(2) . . yes
Si1 C3 C4 C5 -178.5(2) . . yes
Se1 C3 C4 C5 -0.8(4) . . yes
C1 C2 C5 C1 -0.1(5) . 3_656 yes
Se1 C2 C5 C1 179.3(2) . 3_656 yes
C1 C2 C5 C4 -179.1(3) . . yes
Se1 C2 C5 C4 0.3(3) . . yes
C3 C4 C5 C1 -178.7(3) . 3_656 yes
C3 C4 C5 C2 0.3(4) . . yes
B8 O1 C6 C11 -138.4(6) . . yes
B8 O1 C6 C10 105.0(6) . . yes
B8 O1 C6 C9 -13.1(5) . . yes
B8 O2 C9 C7 -143.1(6) . . yes
B8 O2 C9 C6 -14.1(5) . . yes
B8 O2 C9 C8 104.7(5) . . yes
O1 C6 C9 O2 16.0(5) . . yes
C11 C6 C9 O2 136.4(6) . . yes
C10 C6 C9 O2 -97.7(6) . . yes
O1 C6 C9 C7 138.8(6) . . yes
C11 C6 C9 C7 -100.7(8) . . yes
C10 C6 C9 C7 25.1(9) . . yes
O1 C6 C9 C8 -96.6(5) . . yes
C11 C6 C9 C8 23.8(8) . . yes
C10 C6 C9 C8 149.7(6) . . yes
C15 Si1 C12 C13 -160.7(4) . . yes
C3 Si1 C12 C13 76.0(5) . . yes
C18 Si1 C12 C13 -41.7(5) . . yes
C15 Si1 C12 C14 71.0(5) . . yes
C3 Si1 C12 C14 -52.3(5) . . yes
C18 Si1 C12 C14 -170.0(5) . . yes
C3 Si1 C15 C16 51.7(7) . . yes
C12 Si1 C15 C16 -71.7(7) . . yes
C18 Si1 C15 C16 170.3(6) . . yes
C3 Si1 C15 C17 -175.7(6) . . yes
C12 Si1 C15 C17 61.0(7) . . yes
C18 Si1 C15 C17 -57.0(7) . . yes
C15 Si1 C18 C20 -42.2(5) . . yes
C3 Si1 C18 C20 76.9(5) . . yes
C12 Si1 C18 C20 -164.8(5) . . yes
C15 Si1 C18 C21 -164.8(4) . . yes
C3 Si1 C18 C21 -45.6(5) . . yes
C12 Si1 C18 C21 72.6(5) . . yes
C9 O2 B8 O1 6.4(6) . . yes
C9 O2 B8 C1 -175.4(4) . . yes
C6 O1 B8 O2 4.7(5) . . yes
C6 O1 B8 C1 -173.5(4) . . yes
C5 C1 B8 O2 8.5(6) 3_656 . yes
C2 C1 B8 O2 -173.0(4) . . yes
C5 C1 B8 O1 -173.6(3) 3_656 . yes
C2 C1 B8 O1 4.9(5) . . yes
