#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/72/4067218.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_4067218
loop_
_publ_author_name
'Dureen, Meghan A.'
'Brown, Christopher C.'
'Stephan, Douglas W.'
_publ_section_title
;
 Deprotonation and Addition Reactions of Frustrated Lewis Pairs with
 Alkynes
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6594
_journal_paper_doi               10.1021/om1009044
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C43 H27 B F15 S'
_chemical_formula_weight         871.52
_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                82.846(2)
_cell_angle_beta                 74.407(2)
_cell_angle_gamma                85.779(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9881(3)
_cell_length_b                   11.0871(4)
_cell_length_c                   17.1835(6)
_cell_measurement_temperature    150(2)
_cell_volume                     1816.98(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26701
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             882
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7604
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0532
_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)+(0.0649P)²+0.9838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                4817
_reflns_number_total             7604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1009044_si_002.cif
_cod_data_source_block           (PhCH2)2S(Ph)CC(H)B(C6F5)3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4067218
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 1.08821(8) 0.31263(6) 0.22715(4) 0.02406(18) Uani 1 1 d .
F1 F 0.92996(18) 0.93460(14) 0.12958(10) 0.0308(4) Uani 1 1 d .
F2 F 0.82341(19) 1.00994(15) 0.00366(11) 0.0351(4) Uani 1 1 d .
F3 F 0.74541(18) 0.84489(15) -0.07892(10) 0.0332(4) Uani 1 1 d .
F4 F 0.77513(19) 0.60281(15) -0.03163(10) 0.0335(4) Uani 1 1 d .
F5 F 0.88646(18) 0.52557(14) 0.08986(10) 0.0310(4) Uani 1 1 d .
F6 F 1.05137(17) 0.66435(15) 0.34835(10) 0.0315(4) Uani 1 1 d .
F7 F 0.8799(2) 0.69433(19) 0.49358(11) 0.0459(5) Uani 1 1 d .
F8 F 0.6108(2) 0.7694(2) 0.50771(11) 0.0543(6) Uani 1 1 d .
F9 F 0.51591(18) 0.81472(19) 0.37140(12) 0.0475(5) Uani 1 1 d .
F10 F 0.68099(17) 0.78644(16) 0.22754(10) 0.0331(4) Uani 1 1 d .
F11 F 1.07420(17) 0.89806(15) 0.27018(10) 0.0313(4) Uani 1 1 d .
F12 F 1.31406(18) 1.00300(16) 0.22225(11) 0.0378(5) Uani 1 1 d .
F13 F 1.51424(18) 0.93738(17) 0.08990(12) 0.0423(5) Uani 1 1 d .
F14 F 1.46253(18) 0.75908(17) 0.00681(11) 0.0390(5) Uani 1 1 d .
F15 F 1.22324(17) 0.65084(15) 0.05318(10) 0.0314(4) Uani 1 1 d .
C1 C 1.0302(3) 0.5445(2) 0.19908(17) 0.0205(6) Uani 1 1 d .
H1A H 1.0990 0.5221 0.1525 0.025 Uiso 1 1 calc R
C2 C 0.9905(3) 0.4506(2) 0.25550(17) 0.0212(6) Uani 1 1 d .
C3 C 0.8784(3) 0.4382(2) 0.33253(17) 0.0228(6) Uani 1 1 d .
C4 C 0.7403(3) 0.4433(3) 0.3293(2) 0.0298(7) Uani 1 1 d .
H4A H 0.7183 0.4587 0.2785 0.036 Uiso 1 1 calc R
C5 C 0.6355(3) 0.4258(3) 0.4004(2) 0.0389(8) Uani 1 1 d .
H5A H 0.5413 0.4299 0.3980 0.047 Uiso 1 1 calc R
C6 C 0.6654(4) 0.4026(3) 0.4746(2) 0.0429(9) Uani 1 1 d .
H6A H 0.5923 0.3903 0.5230 0.051 Uiso 1 1 calc R
C7 C 0.8017(4) 0.3973(3) 0.4786(2) 0.0384(8) Uani 1 1 d .
H7A H 0.8227 0.3808 0.5297 0.046 Uiso 1 1 calc R
C8 C 0.9079(3) 0.4161(3) 0.40800(18) 0.0288(7) Uani 1 1 d .
H8A H 1.0016 0.4139 0.4110 0.035 Uiso 1 1 calc R
C9 C 1.2271(3) 0.2950(3) 0.2795(2) 0.0305(7) Uani 1 1 d .
H9A H 1.1868 0.2988 0.3385 0.037 Uiso 1 1 calc R
H9B H 1.2767 0.2150 0.2717 0.037 Uiso 1 1 calc R
C10 C 1.3270(3) 0.3951(3) 0.24553(19) 0.0274(7) Uani 1 1 d .
C11 C 1.3320(3) 0.4886(3) 0.2904(2) 0.0346(8) Uani 1 1 d .
H11A H 1.2720 0.4898 0.3436 0.042 Uiso 1 1 calc R
C12 C 1.4243(3) 0.5813(3) 0.2583(2) 0.0422(9) Uani 1 1 d .
H12A H 1.4268 0.6458 0.2894 0.051 Uiso 1 1 calc R
C13 C 1.5124(3) 0.5793(3) 0.1811(2) 0.0426(9) Uani 1 1 d .
H13A H 1.5765 0.6419 0.1593 0.051 Uiso 1 1 calc R
C14 C 1.5073(4) 0.4862(4) 0.1355(2) 0.0440(9) Uani 1 1 d .
H14A H 1.5673 0.4851 0.0823 0.053 Uiso 1 1 calc R
C15 C 1.4149(3) 0.3948(3) 0.1675(2) 0.0355(8) Uani 1 1 d .
H15A H 1.4112 0.3312 0.1359 0.043 Uiso 1 1 calc R
C16 C 0.9837(3) 0.1866(3) 0.2802(2) 0.0337(8) Uani 1 1 d .
H16A H 1.0417 0.1103 0.2742 0.040 Uiso 1 1 calc R
H16B H 0.9526 0.1971 0.3388 0.040 Uiso 1 1 calc R
C17 C 0.8577(3) 0.1755(3) 0.2492(2) 0.0366(8) Uani 1 1 d .
C18 C 0.7454(5) 0.1181(4) 0.3005(3) 0.0787(16) Uani 1 1 d .
H18A H 0.7451 0.0913 0.3553 0.094 Uiso 1 1 calc R
C19 C 0.6297(5) 0.0991(4) 0.2713(4) 0.096(2) Uani 1 1 d .
H19A H 0.5528 0.0571 0.3063 0.115 Uiso 1 1 calc R
C20 C 0.6274(5) 0.1395(4) 0.1949(4) 0.0746(15) Uani 1 1 d .
H20A H 0.5493 0.1259 0.1761 0.089 Uiso 1 1 calc R
C21 C 0.7363(4) 0.2000(4) 0.1443(3) 0.0621(12) Uani 1 1 d .
H21A H 0.7332 0.2310 0.0907 0.075 Uiso 1 1 calc R
C22 C 0.8517(4) 0.2163(4) 0.1709(2) 0.0489(10) Uani 1 1 d .
H22A H 0.9287 0.2565 0.1346 0.059 Uiso 1 1 calc R
C23 C 0.9190(3) 0.7263(2) 0.11469(16) 0.0205(6) Uani 1 1 d .
C24 C 0.8983(3) 0.8488(2) 0.08869(17) 0.0226(6) Uani 1 1 d .
C25 C 0.8418(3) 0.8899(3) 0.02489(18) 0.0245(7) Uani 1 1 d .
C26 C 0.8016(3) 0.8071(3) -0.01654(17) 0.0241(7) Uani 1 1 d .
C27 C 0.8180(3) 0.6846(3) 0.00690(16) 0.0229(6) Uani 1 1 d .
C28 C 0.8764(3) 0.6477(2) 0.07080(17) 0.0222(6) Uani 1 1 d .
C29 C 0.8785(3) 0.7236(2) 0.27850(17) 0.0230(6) Uani 1 1 d .
C30 C 0.9189(3) 0.7040(3) 0.35038(18) 0.0255(7) Uani 1 1 d .
C31 C 0.8333(3) 0.7186(3) 0.42635(18) 0.0311(7) Uani 1 1 d .
C32 C 0.6967(3) 0.7567(3) 0.43412(19) 0.0356(8) Uani 1 1 d .
C33 C 0.6501(3) 0.7788(3) 0.3652(2) 0.0319(7) Uani 1 1 d .
C34 C 0.7397(3) 0.7629(3) 0.29036(18) 0.0255(7) Uani 1 1 d .
C35 C 1.1360(3) 0.7611(2) 0.16789(17) 0.0204(6) Uani 1 1 d .
C36 C 1.1683(3) 0.8539(2) 0.20598(17) 0.0225(6) Uani 1 1 d .
C37 C 1.2926(3) 0.9122(3) 0.18151(18) 0.0262(7) Uani 1 1 d .
C38 C 1.3937(3) 0.8808(3) 0.11454(19) 0.0280(7) Uani 1 1 d .
C39 C 1.3666(3) 0.7913(3) 0.07322(18) 0.0267(7) Uani 1 1 d .
C40 C 1.2409(3) 0.7353(3) 0.09993(17) 0.0231(6) Uani 1 1 d .
B1 B 0.9863(3) 0.6891(3) 0.1929(2) 0.0219(7) Uani 1 1 d .
C51 C 0.9449(7) 1.0175(9) 0.5146(6) 0.164(4) Uiso 1 1 d D
H51A H 0.9350 1.0787 0.4691 0.197 Uiso 1 1 calc R
H51C H 0.9685 1.0663 0.5531 0.197 Uiso 1 1 calc R
C52 C 0.7922(7) 1.0073(7) 0.5565(4) 0.126(2) Uiso 1 1 d D
H52A H 0.7740 0.9221 0.5802 0.151 Uiso 1 1 calc R
H52C H 0.7666 1.0594 0.6015 0.151 Uiso 1 1 calc R
C53 C 0.7071(19) 1.0436(19) 0.5009(12) 0.508(16) Uiso 1 1 d D
H53A H 0.6088 1.0346 0.5299 0.762 Uiso 1 1 calc R
H53B H 0.7321 0.9921 0.4564 0.762 Uiso 1 1 calc R
H53C H 0.7226 1.1288 0.4789 0.762 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 0.0033 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
C2 S1 C16 107.52(14) .
C2 S1 C9 106.54(14) .
C16 S1 C9 100.01(15) .
C2 C1 B1 133.8(3) .
C1 C2 C3 132.5(3) .
C1 C2 S1 111.7(2) .
C3 C2 S1 115.75(19) .
C4 C3 C8 118.9(3) .
C4 C3 C2 119.2(3) .
C8 C3 C2 121.8(3) .
C5 C4 C3 119.8(3) .
C6 C5 C4 121.0(3) .
C5 C6 C7 119.9(3) .
C6 C7 C8 119.8(3) .
C7 C8 C3 120.6(3) .
C10 C9 S1 109.2(2) .
C11 C10 C15 119.2(3) .
C11 C10 C9 120.8(3) .
C15 C10 C9 119.9(3) .
C10 C11 C12 120.4(3) .
C13 C12 C11 119.9(3) .
C14 C13 C12 120.0(3) .
C15 C14 C13 119.9(3) .
C14 C15 C10 120.6(3) .
C17 C16 S1 112.9(2) .
C18 C17 C22 118.2(4) .
C18 C17 C16 118.3(4) .
C22 C17 C16 123.4(3) .
C17 C18 C19 119.5(5) .
C20 C19 C18 120.8(4) .
C19 C20 C21 120.3(4) .
C20 C21 C22 119.8(5) .
C21 C22 C17 121.4(4) .
C28 C23 C24 113.7(3) .
C28 C23 B1 126.9(2) .
C24 C23 B1 119.4(2) .
F1 C24 C25 116.6(2) .
F1 C24 C23 119.2(2) .
C25 C24 C23 124.2(3) .
F2 C25 C26 119.7(3) .
F2 C25 C24 121.0(3) .
C26 C25 C24 119.3(3) .
F3 C26 C25 120.5(3) .
F3 C26 C27 120.3(3) .
C25 C26 C27 119.2(3) .
F4 C27 C26 119.7(2) .
F4 C27 C28 120.9(2) .
C26 C27 C28 119.4(3) .
F5 C28 C23 120.9(2) .
F5 C28 C27 114.9(2) .
C23 C28 C27 124.1(3) .
C30 C29 C34 112.7(3) .
C30 C29 B1 120.2(3) .
C34 C29 B1 126.8(3) .
F6 C30 C31 115.5(3) .
F6 C30 C29 119.3(3) .
C31 C30 C29 125.1(3) .
F7 C31 C32 119.2(3) .
F7 C31 C30 121.4(3) .
C32 C31 C30 119.4(3) .
F8 C32 C33 121.1(3) .
F8 C32 C31 120.4(3) .
C33 C32 C31 118.5(3) .
F9 C33 C32 119.5(3) .
F9 C33 C34 120.4(3) .
C32 C33 C34 120.1(3) .
F10 C34 C33 114.3(3) .
F10 C34 C29 121.4(3) .
C33 C34 C29 124.3(3) .
C36 C35 C40 112.5(3) .
C36 C35 B1 126.8(2) .
C40 C35 B1 120.6(2) .
F11 C36 C37 114.4(2) .
F11 C36 C35 121.1(2) .
C37 C36 C35 124.4(3) .
F12 C37 C38 119.6(3) .
F12 C37 C36 120.1(3) .
C38 C37 C36 120.3(3) .
F13 C38 C39 121.2(3) .
F13 C38 C37 120.8(3) .
C39 C38 C37 118.1(3) .
F14 C39 C38 119.8(3) .
F14 C39 C40 120.5(3) .
C38 C39 C40 119.7(3) .
F15 C40 C39 114.8(2) .
F15 C40 C35 120.2(2) .
C39 C40 C35 125.0(3) .
C1 B1 C29 110.5(2) .
C1 B1 C23 109.7(2) .
C29 B1 C23 111.9(2) .
C1 B1 C35 105.6(2) .
C29 B1 C35 114.0(2) .
C23 B1 C35 104.9(2) .
C51 C51 C52 155.9(14) 2_776
C53 C52 C51 111.5(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.800(3) .
S1 C16 1.805(3) .
S1 C9 1.833(3) .
F1 C24 1.353(3) .
F2 C25 1.348(3) .
F3 C26 1.348(3) .
F4 C27 1.343(3) .
F5 C28 1.356(3) .
F6 C30 1.356(3) .
F7 C31 1.348(3) .
F8 C32 1.341(4) .
F9 C33 1.350(3) .
F10 C34 1.351(3) .
F11 C36 1.360(3) .
F12 C37 1.356(3) .
F13 C38 1.339(3) .
F14 C39 1.346(3) .
F15 C40 1.357(3) .
C1 C2 1.336(4) .
C1 B1 1.629(4) .
C2 C3 1.485(4) .
C3 C4 1.392(4) .
C3 C8 1.394(4) .
C4 C5 1.382(4) .
C5 C6 1.376(5) .
C6 C7 1.377(5) .
C7 C8 1.385(4) .
C9 C10 1.502(4) .
C10 C11 1.378(4) .
C10 C15 1.392(4) .
C11 C12 1.390(5) .
C12 C13 1.383(5) .
C13 C14 1.383(5) .
C14 C15 1.381(5) .
C16 C17 1.510(5) .
C17 C18 1.369(5) .
C17 C22 1.381(5) .
C18 C19 1.416(7) .
C19 C20 1.339(7) .
C20 C21 1.358(7) .
C21 C22 1.380(5) .
C23 C28 1.378(4) .
C23 C24 1.394(4) .
C23 B1 1.654(4) .
C24 C25 1.378(4) .
C25 C26 1.371(4) .
C26 C27 1.378(4) .
C27 C28 1.383(4) .
C29 C30 1.387(4) .
C29 C34 1.390(4) .
C29 B1 1.642(4) .
C30 C31 1.376(4) .
C31 C32 1.374(4) .
C32 C33 1.374(5) .
C33 C34 1.378(4) .
C35 C36 1.386(4) .
C35 C40 1.387(4) .
C35 B1 1.674(4) .
C36 C37 1.380(4) .
C37 C38 1.374(4) .
C38 C39 1.371(4) .
C39 C40 1.381(4) .
C51 C51 1.141(13) 2_776
C51 C52 1.508(7) .
C52 C53 1.445(9) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139099898
