#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:04:00 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178883 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/12/4111246.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_4111246
loop_
_publ_author_name
'Anand Sundararaman'
'Krishnan Venkatasubbaiah'
'Maria Victor'
'Lev N. Zakharov'
'Arnold L. Rheingold'
'Frieder Jäkle'
_publ_section_title
;
 Electronic Communication and Negative Binding Cooperativity in
 Diborylated Bithiophenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16554
_journal_page_last               16565
_journal_paper_doi               10.1021/ja064396b
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C53 H28 B2 F20 S2'
_chemical_formula_weight         1130.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.157(2)
_cell_angle_beta                 105.488(2)
_cell_angle_gamma                93.159(2)
_cell_formula_units_Z            1
_cell_length_a                   7.6711(8)
_cell_length_b                   11.9741(12)
_cell_length_c                   13.8819(13)
_cell_measurement_temperature    218(2)
_cell_volume                     1223.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      218(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7447
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0901P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1427
_reflns_number_gt                3377
_reflns_number_total             4294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja064396bsi20060621_110315.cif
_cod_data_source_block           fjak6
_cod_database_code               4111246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04574(8) 0.84107(4) 0.43223(4) 0.0441(2) Uani 1 1 d . . .
B1 B 0.0245(3) 0.7460(2) 0.24044(17) 0.0423(6) Uani 1 1 d . . .
F1 F 0.3407(2) 0.62173(14) 0.26945(13) 0.0794(5) Uani 1 1 d . . .
F2 F 0.3877(3) 0.42835(18) 0.35836(18) 0.1193(8) Uani 1 1 d . . .
F3 F 0.1187(3) 0.33014(16) 0.42301(16) 0.1151(8) Uani 1 1 d . . .
F4 F -0.1936(3) 0.42920(15) 0.40283(13) 0.0957(6) Uani 1 1 d . . .
F5 F -0.2410(2) 0.62285(15) 0.31551(13) 0.0785(5) Uani 1 1 d . . .
F6 F -0.14276(19) 0.57069(10) 0.08836(9) 0.0572(4) Uani 1 1 d . . .
F7 F -0.1743(2) 0.57537(13) -0.10636(10) 0.0732(5) Uani 1 1 d . . .
F8 F -0.0357(2) 0.75585(15) -0.17900(9) 0.0799(5) Uani 1 1 d . . .
F9 F 0.1393(2) 0.93062(12) -0.05124(10) 0.0644(4) Uani 1 1 d . . .
F10 F 0.18111(19) 0.92599(11) 0.14371(9) 0.0564(4) Uani 1 1 d . . .
C1 C -0.0056(3) 0.97581(17) 0.45033(15) 0.0414(5) Uani 1 1 d . . .
C2 C -0.0541(3) 1.02524(19) 0.36104(15) 0.0498(6) Uani 1 1 d . . .
H2A H -0.0884 1.0993 0.3555 0.060 Uiso 1 1 calc R . .
C3 C -0.0471(3) 0.95433(18) 0.27968(15) 0.0481(5) Uani 1 1 d . . .
H3A H -0.0754 0.9765 0.2137 0.058 Uiso 1 1 calc R . .
C4 C 0.0051(3) 0.84839(18) 0.30391(14) 0.0430(5) Uani 1 1 d . . .
C5 C 0.0511(3) 0.63067(17) 0.29029(14) 0.0450(5) Uani 1 1 d . . .
C6 C 0.2059(4) 0.5764(2) 0.30291(17) 0.0560(6) Uani 1 1 d . . .
C7 C 0.2321(4) 0.4764(2) 0.3477(2) 0.0732(8) Uani 1 1 d . . .
C8 C 0.0971(5) 0.4277(2) 0.3801(2) 0.0728(8) Uani 1 1 d . . .
C9 C -0.0611(4) 0.4774(2) 0.36926(18) 0.0666(7) Uani 1 1 d . . .
C10 C -0.0814(3) 0.5771(2) 0.32563(17) 0.0545(6) Uani 1 1 d . . .
C11 C 0.0163(3) 0.74961(17) 0.12603(14) 0.0412(5) Uani 1 1 d . . .
C12 C -0.0695(3) 0.66144(18) 0.05696(15) 0.0446(5) Uani 1 1 d . . .
C13 C -0.0880(3) 0.6623(2) -0.04389(16) 0.0520(6) Uani 1 1 d . . .
C14 C -0.0189(3) 0.7532(2) -0.08046(15) 0.0539(6) Uani 1 1 d . . .
C15 C 0.0698(3) 0.8420(2) -0.01577(16) 0.0493(5) Uani 1 1 d . . .
C16 C 0.0866(3) 0.83845(18) 0.08455(15) 0.0426(5) Uani 1 1 d . . .
C17 C 0.5469(4) 0.8478(2) -0.0363(3) 0.0729(8) Uani 0.795(6) 1 d PD A 1
H17A H 0.5868 0.9145 -0.0591 0.087 Uiso 0.795(6) 1 calc PR A 1
C18 C 0.5640(5) 0.8417(3) 0.0637(3) 0.0734(12) Uani 0.795(6) 1 d PD A 1
H18A H 0.6126 0.9048 0.1081 0.088 Uiso 0.795(6) 1 calc PR A 1
C19 C 0.5122(5) 0.7466(4) 0.1001(3) 0.0992(12) Uani 0.795(6) 1 d PD A 1
H19A H 0.5249 0.7423 0.1690 0.119 Uiso 0.795(6) 1 calc PR A 1
C20 C 0.4381(6) 0.6538(4) 0.0308(5) 0.0897(16) Uani 0.795(6) 1 d PD A 1
H20A H 0.4008 0.5864 0.0534 0.108 Uiso 0.795(6) 1 calc PR A 1
C21 C 0.4213(4) 0.6622(3) -0.0671(4) 0.0911(11) Uani 0.795(6) 1 d PD A 1
H21A H 0.3726 0.6000 -0.1125 0.109 Uiso 0.795(6) 1 calc PR A 1
C22 C 0.4745(5) 0.7609(4) -0.1029(3) 0.0741(13) Uani 0.795(6) 1 d PD A 1
C23 C 0.4549(8) 0.7671(5) -0.2113(4) 0.147(2) Uani 0.795(6) 1 d PD A 1
H23A H 0.4982 0.8412 -0.2235 0.221 Uiso 0.795(6) 1 calc PR A 1
H23B H 0.3282 0.7528 -0.2479 0.221 Uiso 0.795(6) 1 calc PR A 1
H23C H 0.5255 0.7113 -0.2336 0.221 Uiso 0.795(6) 1 calc PR A 1
C17A C 0.5469(4) 0.8478(2) -0.0363(3) 0.0729(8) Uani 0.205(6) 1 d PD A 2
H17B H 0.5898 0.9130 0.0063 0.087 Uiso 0.205(6) 1 calc PR A 2
C18A C 0.533(3) 0.8476(16) -0.1386(11) 0.109(7) Uani 0.205(6) 1 d PD A 2
H18B H 0.5854 0.9116 -0.1594 0.131 Uiso 0.205(6) 1 calc PR A 2
C19A C 0.4549(8) 0.7671(5) -0.2113(4) 0.147(2) Uani 0.205(6) 1 d PD A 2
H19B H 0.4294 0.7749 -0.2806 0.177 Uiso 0.205(6) 1 calc PR A 2
C20A C 0.417(3) 0.6683(17) -0.1659(12) 0.153(13) Uani 0.205(6) 1 d PD A 2
H20B H 0.3868 0.6014 -0.2073 0.183 Uiso 0.205(6) 1 calc PR A 2
C21A C 0.4213(4) 0.6622(3) -0.0671(4) 0.0911(11) Uani 0.205(6) 1 d PD A 2
H21B H 0.3736 0.5976 -0.0449 0.109 Uiso 0.205(6) 1 calc PR A 2
C22A C 0.4979(19) 0.7540(12) -0.0003(10) 0.101(8) Uani 0.205(6) 1 d PD A 2
C23A C 0.5122(5) 0.7466(4) 0.1001(3) 0.0992(12) Uani 0.205(6) 1 d PD A 2
H23D H 0.5681 0.8165 0.1369 0.149 Uiso 0.205(6) 1 calc PR A 2
H23E H 0.5862 0.6857 0.1246 0.149 Uiso 0.205(6) 1 calc PR A 2
H23F H 0.3923 0.7325 0.1095 0.149 Uiso 0.205(6) 1 calc PR A 2
C24 C 0.5160(9) -0.0507(7) 0.4775(11) 0.125(4) Uani 0.50 1 d PD . .
C25 C 0.4581(6) 0.0284(6) 0.4160(4) 0.1152(14) Uani 1 1 d D . .
C26 C 0.4242(10) 0.1343(7) 0.4460(7) 0.101(2) Uani 0.50 1 d PD . .
C27 C 0.4501(7) 0.1615(5) 0.5496(7) 0.157(2) Uani 1 1 d D . .
C28 C 0.5056(12) 0.0878(14) 0.6198(7) 0.146(6) Uani 0.50 1 d PD . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_3
C1 S1 C4 93.17(10) . .
C4 B1 C11 122.5(2) . .
C4 B1 C5 118.63(18) . .
C11 B1 C5 118.88(18) . .
C2 C1 C1 128.3(3) . 2_576
C2 C1 S1 110.87(15) . .
C1 C1 S1 120.8(2) 2_576 .
C1 C2 C3 112.9(2) . .
C4 C3 C2 114.39(19) . .
C3 C4 B1 132.09(19) . .
C3 C4 S1 108.65(15) . .
B1 C4 S1 119.23(16) . .
C6 C5 C10 114.6(2) . .
C6 C5 B1 123.0(2) . .
C10 C5 B1 122.4(2) . .
F1 C6 C5 118.6(2) . .
F1 C6 C7 117.8(2) . .
C5 C6 C7 123.6(2) . .
F2 C7 C8 120.5(3) . .
F2 C7 C6 120.4(3) . .
C8 C7 C6 119.1(3) . .
F3 C8 C7 120.2(3) . .
F3 C8 C9 119.7(3) . .
C7 C8 C9 120.2(3) . .
F4 C9 C8 119.8(3) . .
F4 C9 C10 121.1(3) . .
C8 C9 C10 119.2(3) . .
F5 C10 C9 117.2(2) . .
F5 C10 C5 119.4(2) . .
C9 C10 C5 123.4(3) . .
C16 C11 C12 114.34(18) . .
C16 C11 B1 124.64(18) . .
C12 C11 B1 121.00(19) . .
F6 C12 C13 116.75(19) . .
F6 C12 C11 119.74(18) . .
C13 C12 C11 123.5(2) . .
F7 C13 C14 120.1(2) . .
F7 C13 C12 120.5(2) . .
C14 C13 C12 119.4(2) . .
F8 C14 C13 120.4(2) . .
F8 C14 C15 119.9(2) . .
C13 C14 C15 119.8(2) . .
F9 C15 C16 120.7(2) . .
F9 C15 C14 119.90(19) . .
C16 C15 C14 119.4(2) . .
F10 C16 C15 116.18(19) . .
F10 C16 C11 120.24(18) . .
C15 C16 C11 123.5(2) . .
C22 C17 C18 121.6(3) . .
C19 C18 C17 121.2(4) . .
C18 C19 C20 117.7(4) . .
C21 C20 C19 120.0(4) . .
C20 C21 C22 121.4(4) . .
C17 C22 C21 118.1(4) . .
C17 C22 C23 121.9(4) . .
C21 C22 C23 120.0(4) . .
C25 C24 C28 68.6(11) . 2_656
C25 C24 C24 64.1(8) . 2_656
C28 C24 C24 132.7(17) 2_656 2_656
C25 C24 C27 126.8(12) . 2_656
C28 C24 C27 58.1(8) 2_656 2_656
C24 C24 C27 168.9(18) 2_656 2_656
C25 C24 C25 119.5(7) . 2_656
C28 C24 C25 171.6(12) 2_656 2_656
C24 C24 C25 55.5(9) 2_656 2_656
C27 C24 C25 113.6(10) 2_656 2_656
C25 C24 C26 174.9(11) . 2_656
C28 C24 C26 116.2(10) 2_656 2_656
C24 C24 C26 111.1(16) 2_656 2_656
C27 C24 C26 58.0(6) 2_656 2_656
C25 C24 C26 55.6(7) 2_656 2_656
C24 C25 C26 124.6(9) . .
C24 C25 C24 60.5(7) . 2_656
C26 C25 C24 64.2(6) . 2_656
C24 C25 C28 56.8(7) . 2_656
C26 C25 C28 178.6(6) . 2_656
C24 C25 C28 117.3(7) 2_656 2_656
C25 C26 C27 118.3(7) . .
C25 C26 C24 60.3(6) . 2_656
C27 C26 C24 58.0(6) . 2_656
C28 C27 C24 58.9(8) . 2_656
C28 C27 C26 122.9(8) . .
C24 C27 C26 63.9(7) 2_656 .
C27 C28 C24 62.9(6) . 2_656
C27 C28 C25 117.4(8) . 2_656
C24 C28 C25 54.5(7) 2_656 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.703(2) .
S1 C4 1.732(2) .
B1 C4 1.507(3) .
B1 C11 1.576(3) .
B1 C5 1.578(3) .
F1 C6 1.342(3) .
F2 C7 1.330(3) .
F3 C8 1.339(3) .
F4 C9 1.343(3) .
F5 C10 1.345(3) .
F6 C12 1.342(3) .
F7 C13 1.338(3) .
F8 C14 1.342(2) .
F9 C15 1.337(3) .
F10 C16 1.343(2) .
C1 C2 1.372(3) .
C1 C1 1.445(4) 2_576
C2 C3 1.390(3) .
C3 C4 1.383(3) .
C5 C6 1.360(3) .
C5 C10 1.384(3) .
C6 C7 1.380(4) .
C7 C8 1.351(4) .
C8 C9 1.358(4) .
C9 C10 1.365(4) .
C11 C16 1.387(3) .
C11 C12 1.394(3) .
C12 C13 1.370(3) .
C13 C14 1.366(4) .
C14 C15 1.375(3) .
C15 C16 1.367(3) .
C17 C22 1.343(5) .
C17 C18 1.365(5) .
C18 C19 1.353(5) .
C19 C20 1.416(6) .
C20 C21 1.339(6) .
C21 C22 1.388(5) .
C22 C23 1.478(6) .
C24 C25 1.326(11) .
C24 C28 1.362(17) 2_656
C24 C27 1.415(9) 2_656
C24 C25 1.446(14) 2_656
C25 C26 1.374(9) .
C26 C27 1.416(10) .
C27 C28 1.351(12) .
C28 C25 1.516(15) 2_656
