#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:04:00 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178883 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/12/4111247.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_4111247
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            'C60 H38 B2 F20 N2 S2'
_chemical_formula_weight         1252.66
_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                105.5130(10)
_cell_angle_beta                 100.7860(10)
_cell_angle_gamma                105.9230(10)
_cell_formula_units_Z            1
_cell_length_a                   9.07300(10)
_cell_length_b                   12.8466(2)
_cell_length_c                   13.1240(2)
_cell_measurement_reflns_used    4251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.86
_cell_measurement_theta_min      3.64
_cell_volume                     1360.24(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.868
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0244
_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       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10305
_diffrn_reflns_theta_full        69.05
_diffrn_reflns_theta_max         69.05
_diffrn_reflns_theta_min         3.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.893
_exptl_absorpt_correction_T_max  0.8481
_exptl_absorpt_correction_T_min  0.7391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.102
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.9880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                3764
_reflns_number_total             4384
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja064396bsi20060621_110355.cif
_cod_data_source_block           111905_0m
_cod_original_cell_volume        1360.24(3)
_cod_database_code               4111247
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
S1 S 0.39509(8) 0.59384(5) 0.61388(5) 0.0264(2) Uani 1 1 d .
B1 B 0.2900(3) 0.7937(2) 0.6429(3) 0.0237(6) Uani 1 1 d .
N1 N 0.1246(2) 0.73453(17) 0.66835(18) 0.0242(5) Uani 1 1 d .
F6 F 0.37265(18) 1.05527(12) 0.71305(13) 0.0331(4) Uani 1 1 d .
F10 F 0.07118(18) 0.70355(12) 0.42423(13) 0.0340(4) Uani 1 1 d .
F1 F 0.30289(18) 0.77413(13) 0.87313(13) 0.0347(4) Uani 1 1 d .
F9 F -0.0132(2) 0.82070(15) 0.29796(14) 0.0418(4) Uani 1 1 d .
F5 F 0.59332(18) 0.95696(13) 0.66612(13) 0.0333(4) Uani 1 1 d .
F4 F 0.84702(19) 1.05673(14) 0.84185(15) 0.0443(4) Uani 1 1 d .
F7 F 0.28361(19) 1.16873(13) 0.58562(15) 0.0389(4) Uani 1 1 d .
F8 F 0.0936(2) 1.05474(15) 0.37617(15) 0.0417(4) Uani 1 1 d .
F2 F 0.5567(2) 0.87580(15) 1.04615(13) 0.0419(4) Uani 1 1 d .
F3 F 0.8334(2) 1.01825(15) 1.03486(14) 0.0455(5) Uani 1 1 d .
C13 C 0.2377(3) 1.0534(2) 0.5444(3) 0.0315(6) Uani 1 1 d .
C8 C 0.7050(3) 0.9683(2) 0.9464(2) 0.0348(7) Uani 1 1 d .
C6 C 0.4336(3) 0.8459(2) 0.8602(2) 0.0293(6) Uani 1 1 d .
C9 C 0.7113(3) 0.9881(2) 0.8494(3) 0.0330(6) Uani 1 1 d .
C5 C 0.4316(3) 0.8633(2) 0.7608(2) 0.0247(6) Uani 1 1 d .
C10 C 0.5777(3) 0.9355(2) 0.7594(2) 0.0281(6) Uani 1 1 d .
C3 C 0.4086(3) 0.7047(2) 0.4814(2) 0.0265(6) Uani 1 1 d .
H3 H 0.4014 0.7594 0.4460 0.032 Uiso 1 1 calc R
C16 C 0.1352(3) 0.8199(2) 0.4668(2) 0.0297(6) Uani 1 1 d .
C14 C 0.1406(3) 0.9960(2) 0.4389(3) 0.0335(7) Uani 1 1 d .
C2 C 0.4769(3) 0.6197(2) 0.4450(2) 0.0271(6) Uani 1 1 d .
H2 H 0.5194 0.6120 0.3836 0.033 Uiso 1 1 calc R
C18 C -0.0831(3) 0.7640(2) 0.7472(2) 0.0318(6) Uani 1 1 d .
H18 H -0.1275 0.8158 0.7855 0.038 Uiso 1 1 calc R
C21 C 0.0475(3) 0.6203(2) 0.6348(2) 0.0297(6) Uani 1 1 d .
H21 H 0.0919 0.5699 0.5944 0.036 Uiso 1 1 calc R
C1 C 0.4751(3) 0.55002(19) 0.5077(2) 0.0228(5) Uani 1 1 d .
C20 C -0.0936(3) 0.5743(2) 0.6572(2) 0.0329(6) Uani 1 1 d .
H20 H -0.1442 0.4933 0.6340 0.039 Uiso 1 1 calc R
C7 C 0.5651(3) 0.8966(2) 0.9523(2) 0.0330(6) Uani 1 1 d .
C17 C 0.0587(3) 0.8051(2) 0.7247(2) 0.0284(6) Uani 1 1 d .
H17 H 0.1126 0.8858 0.7495 0.034 Uiso 1 1 calc R
C4 C 0.3542(3) 0.7020(2) 0.5704(2) 0.0236(6) Uani 1 1 d .
C11 C 0.2395(3) 0.8730(2) 0.5720(2) 0.0264(6) Uani 1 1 d .
C12 C 0.2838(3) 0.9919(2) 0.6086(2) 0.0279(6) Uani 1 1 d .
C15 C 0.0871(3) 0.8780(2) 0.3991(2) 0.0322(6) Uani 1 1 d .
C19 C -0.1612(3) 0.6467(2) 0.7137(2) 0.0328(6) Uani 1 1 d .
H19 H -0.2592 0.6166 0.7292 0.039 Uiso 1 1 calc R
C25 C 0.4876(5) 0.6165(3) 0.1711(3) 0.0551(10) Uani 1 1 d .
H25 H 0.5620 0.6924 0.2074 0.066 Uiso 1 1 calc R
C23 C 0.2201(5) 0.4892(3) 0.0861(3) 0.0642(12) Uani 1 1 d .
H23 H 0.1087 0.4760 0.0657 0.077 Uiso 1 1 calc R
C24 C 0.3267(5) 0.6009(3) 0.1402(3) 0.0572(10) Uani 1 1 d .
C22 C 0.2747(6) 0.3954(3) 0.0610(3) 0.0641(12) Uani 1 1 d .
C26 C 0.5444(5) 0.5249(3) 0.1507(3) 0.0542(10) Uani 1 1 d .
C27 C 0.4356(5) 0.4151(3) 0.0950(3) 0.0567(10) Uani 1 1 d .
H27 H 0.4730 0.3520 0.0800 0.068 Uiso 1 1 calc R
C30 C 0.2688(6) 0.7020(3) 0.1634(4) 0.0740(12) Uani 1 1 d .
H30A H 0.3476 0.7660 0.2262 0.111 Uiso 1 1 calc R
H30B H 0.1666 0.6797 0.1807 0.111 Uiso 1 1 calc R
H30C H 0.2546 0.7260 0.0984 0.111 Uiso 1 1 calc R
C29 C 0.7212(5) 0.5440(4) 0.1882(4) 0.0718(12) Uani 1 1 d .
H29A H 0.7376 0.4697 0.1695 0.108 Uiso 1 1 calc R
H29B H 0.7614 0.5832 0.2682 0.108 Uiso 1 1 calc R
H29C H 0.7789 0.5916 0.1512 0.108 Uiso 1 1 calc R
C28 C 0.1576(6) 0.2752(3) -0.0033(4) 0.0837(16) Uani 1 1 d .
H28A H 0.1536 0.2570 -0.0814 0.126 Uiso 1 1 calc R
H28B H 0.0512 0.2710 0.0051 0.126 Uiso 1 1 calc R
H28C H 0.1920 0.2198 0.0249 0.126 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 93.38(12) . .
C4 B1 N1 113.59(19) . .
C4 B1 C11 109.9(2) . .
N1 B1 C11 102.66(19) . .
C4 B1 C5 105.81(19) . .
N1 B1 C5 108.8(2) . .
C11 B1 C5 116.3(2) . .
C21 N1 C17 118.2(2) . .
C21 N1 B1 124.2(2) . .
C17 N1 B1 117.6(2) . .
F7 C13 C14 119.7(2) . .
F7 C13 C12 120.6(3) . .
C14 C13 C12 119.7(2) . .
F3 C8 C9 120.5(3) . .
F3 C8 C7 120.3(3) . .
C9 C8 C7 119.2(2) . .
F1 C6 C5 120.8(2) . .
F1 C6 C7 115.1(2) . .
C5 C6 C7 124.1(3) . .
F4 C9 C8 120.1(2) . .
F4 C9 C10 120.4(3) . .
C8 C9 C10 119.5(3) . .
C6 C5 C10 113.8(2) . .
C6 C5 B1 127.2(2) . .
C10 C5 B1 118.2(2) . .
F5 C10 C9 116.3(2) . .
F5 C10 C5 119.8(2) . .
C9 C10 C5 123.9(3) . .
C4 C3 C2 115.0(2) . .
F10 C16 C11 120.0(2) . .
F10 C16 C15 115.5(2) . .
C11 C16 C15 124.4(2) . .
F8 C14 C13 120.2(2) . .
F8 C14 C15 120.2(3) . .
C13 C14 C15 119.5(2) . .
C1 C2 C3 112.8(2) . .
C17 C18 C19 119.6(3) . .
N1 C21 C20 122.1(3) . .
C2 C1 C1 128.8(3) . 2_666
C2 C1 S1 109.98(19) . .
C1 C1 S1 121.1(3) 2_666 .
C21 C20 C19 119.5(3) . .
F2 C7 C8 120.2(2) . .
F2 C7 C6 120.4(3) . .
C8 C7 C6 119.5(3) . .
N1 C17 C18 122.2(2) . .
C3 C4 B1 128.6(2) . .
C3 C4 S1 108.78(18) . .
B1 C4 S1 121.80(19) . .
C16 C11 C12 113.7(2) . .
C16 C11 B1 119.6(2) . .
C12 C11 B1 126.6(2) . .
F6 C12 C13 115.5(2) . .
F6 C12 C11 120.8(2) . .
C13 C12 C11 123.7(3) . .
F9 C15 C14 120.2(2) . .
F9 C15 C16 121.0(2) . .
C14 C15 C16 118.8(3) . .
C20 C19 C18 118.5(3) . .
C24 C25 C26 122.2(3) . .
C24 C23 C22 121.0(4) . .
C25 C24 C23 117.9(4) . .
C25 C24 C30 121.0(3) . .
C23 C24 C30 121.1(4) . .
C27 C22 C23 118.9(3) . .
C27 C22 C28 120.8(4) . .
C23 C22 C28 120.3(4) . .
C27 C26 C25 118.5(4) . .
C27 C26 C29 120.3(4) . .
C25 C26 C29 121.2(3) . .
C22 C27 C26 121.4(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.723(3) .
S1 C4 1.738(2) .
B1 C4 1.619(4) .
B1 N1 1.625(4) .
B1 C11 1.648(3) .
B1 C5 1.652(4) .
N1 C21 1.346(3) .
N1 C17 1.353(3) .
F6 C12 1.349(3) .
F10 C16 1.356(3) .
F1 C6 1.358(3) .
F9 C15 1.338(3) .
F5 C10 1.349(3) .
F4 C9 1.342(3) .
F7 C13 1.345(3) .
F8 C14 1.344(3) .
F2 C7 1.340(3) .
F3 C8 1.342(3) .
C13 C14 1.370(4) .
C13 C12 1.383(4) .
C8 C9 1.372(4) .
C8 C7 1.378(4) .
C6 C5 1.379(4) .
C6 C7 1.386(4) .
C9 C10 1.382(4) .
C5 C10 1.400(4) .
C3 C4 1.355(4) .
C3 C2 1.417(4) .
C16 C11 1.385(4) .
C16 C15 1.387(4) .
C14 C15 1.374(4) .
C2 C1 1.367(4) .
C18 C17 1.368(4) .
C18 C19 1.382(4) .
C21 C20 1.377(4) .
C1 C1 1.453(5) 2_666
C20 C19 1.380(4) .
C11 C12 1.388(4) .
C25 C24 1.382(6) .
C25 C26 1.392(5) .
C23 C24 1.391(5) .
C23 C22 1.408(6) .
C24 C30 1.510(5) .
C22 C27 1.374(6) .
C22 C28 1.514(5) .
C26 C27 1.383(5) .
C26 C29 1.517(6) .
