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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/36/7103618.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_7103618
loop_
_publ_author_name
'Denis, Jean-Marc'
'Forintos, Henrietta'
'Szelke, Helga'
'Toupet, Loic'
'Pham, Thi-Nhàn'
'Madec, Pierre-Jean'
'Gaumont, Annie-Claude'
_publ_section_title
;
 B(C6F5)3-catalyzed formation of B--P bonds by dehydrocoupling of
 phosphine--boranes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   1
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              54
_journal_page_last               55
_journal_paper_doi               10.1039/b206559b
_journal_year                    2003
_chemical_formula_sum            'C20 H6 B F15 S'
_chemical_formula_weight         574.12
_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                90.00
_cell_angle_beta                 110.101(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.7574(7)
_cell_length_b                   11.8948(5)
_cell_length_c                   20.2990(9)
_cell_measurement_temperature    293(2)
_cell_volume                     4026.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4604
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.307
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0724
_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)+(0.0978P)²+16.0484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.2138
_reflns_number_gt                3119
_reflns_number_total             4604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b206559b.txt
_cod_data_source_block           jmd
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2018-03-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C40 H12 B2 F30 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1148.24
_cod_database_code               7103618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80954(6) 0.01319(10) 0.10737(6) 0.0439(3) Uani 1 1 d . . .
F1 F 0.73391(16) -0.0845(2) 0.20132(13) 0.0525(7) Uani 1 1 d . . .
F2 F 0.68226(19) -0.2726(3) 0.24406(15) 0.0670(9) Uani 1 1 d . . .
F3 F 0.57801(19) -0.4133(2) 0.14860(18) 0.0670(9) Uani 1 1 d . . .
F4 F 0.53090(18) -0.3626(2) 0.00955(16) 0.0569(7) Uani 1 1 d . . .
F5 F 0.57904(15) -0.1767(2) -0.03387(12) 0.0461(6) Uani 1 1 d . . .
F6 F 0.54851(15) -0.00494(19) 0.11527(13) 0.0434(6) Uani 1 1 d . . .
F7 F 0.50388(16) 0.1593(2) 0.18145(14) 0.0492(7) Uani 1 1 d . . .
F8 F 0.57480(17) 0.3645(2) 0.19756(14) 0.0525(7) Uani 1 1 d . . .
F9 F 0.69588(16) 0.4003(2) 0.14484(14) 0.0510(7) Uani 1 1 d . . .
F10 F 0.74612(14) 0.2332(2) 0.08259(14) 0.0466(6) Uani 1 1 d . . .
F11 F 0.58097(14) 0.1861(2) -0.02983(12) 0.0413(6) Uani 1 1 d . . .
F12 F 0.54374(15) 0.2101(2) -0.16561(12) 0.0460(6) Uani 1 1 d . . .
F13 F 0.59616(17) 0.0594(2) -0.24155(12) 0.0507(7) Uani 1 1 d . . .
F14 F 0.69287(17) -0.1125(2) -0.17485(14) 0.0539(7) Uani 1 1 d . . .
F15 F 0.73584(15) -0.1355(2) -0.03585(13) 0.0464(6) Uani 1 1 d . . .
C1 C 0.8523(3) -0.1252(4) 0.1205(3) 0.0521(11) Uani 1 1 d . . .
H1A H 0.8357 -0.1644 0.1545 0.063 Uiso 1 1 calc R . .
H1B H 0.9098 -0.1196 0.1372 0.063 Uiso 1 1 calc R . .
H1C H 0.8345 -0.1656 0.0769 0.063 Uiso 1 1 calc R . .
C2 C 0.8511(3) 0.0634(4) 0.0429(3) 0.0510(11) Uani 1 1 d . . .
H2A H 0.8334 0.1390 0.0298 0.061 Uiso 1 1 calc R . .
H2B H 0.8334 0.0159 0.0022 0.061 Uiso 1 1 calc R . .
H2C H 0.9086 0.0619 0.0626 0.061 Uiso 1 1 calc R . .
C3 C 0.6611(2) -0.1214(3) 0.0808(2) 0.0373(9) Uani 1 1 d . . .
C4 C 0.6843(3) -0.1527(4) 0.1519(2) 0.0436(10) Uani 1 1 d . . .
C5 C 0.6580(3) -0.2490(4) 0.1747(3) 0.0506(11) Uani 1 1 d . . .
C6 C 0.6067(3) -0.3203(4) 0.1279(3) 0.0501(11) Uani 1 1 d . . .
C7 C 0.5826(3) -0.2947(4) 0.0577(3) 0.0444(10) Uani 1 1 d . . .
C8 C 0.6095(3) -0.1963(4) 0.0362(2) 0.0395(9) Uani 1 1 d . . .
C9 C 0.6547(2) 0.1022(3) 0.0999(2) 0.0365(9) Uani 1 1 d . . .
C10 C 0.5911(2) 0.0917(3) 0.1247(2) 0.0358(9) Uani 1 1 d . . .
C11 C 0.5652(3) 0.1767(4) 0.1584(2) 0.0399(9) Uani 1 1 d . . .
C12 C 0.6010(3) 0.2802(4) 0.1663(2) 0.0420(10) Uani 1 1 d . . .
C13 C 0.6620(3) 0.2976(3) 0.1400(2) 0.0406(9) Uani 1 1 d . . .
C14 C 0.6870(2) 0.2100(4) 0.1090(2) 0.0396(9) Uani 1 1 d . . .
C15 C 0.6630(2) 0.0239(3) -0.0237(2) 0.0350(8) Uani 1 1 d . . .
C16 C 0.6134(2) 0.1104(3) -0.0617(2) 0.0336(8) Uani 1 1 d . . .
C17 C 0.5917(2) 0.1245(3) -0.1337(2) 0.0362(9) Uani 1 1 d . . .
C18 C 0.6178(3) 0.0496(4) -0.1721(2) 0.0404(9) Uani 1 1 d . . .
C19 C 0.6668(3) -0.0376(4) -0.1379(2) 0.0399(9) Uani 1 1 d . . .
C20 C 0.6884(2) -0.0468(3) -0.0659(2) 0.0383(9) Uani 1 1 d . . .
B1 B 0.6850(3) 0.0023(4) 0.0596(2) 0.0357(9) Uani 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'
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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
C1 S1 C2 98.8(2) . . ?
C1 S1 B1 109.8(2) . . ?
C2 S1 B1 108.3(2) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C4 113.4(4) . . ?
C8 C3 B1 126.0(4) . . ?
C4 C3 B1 119.9(4) . . ?
F1 C4 C5 117.3(4) . . ?
F1 C4 C3 119.2(4) . . ?
C5 C4 C3 123.5(4) . . ?
F2 C5 C6 119.6(4) . . ?
F2 C5 C4 120.0(4) . . ?
C6 C5 C4 120.4(4) . . ?
F3 C6 C5 121.9(4) . . ?
F3 C6 C7 119.4(5) . . ?
C5 C6 C7 118.7(4) . . ?
F4 C7 C6 120.6(4) . . ?
F4 C7 C8 119.8(4) . . ?
C6 C7 C8 119.6(4) . . ?
F5 C8 C3 121.0(4) . . ?
F5 C8 C7 114.7(4) . . ?
C3 C8 C7 124.3(4) . . ?
C14 C9 C10 112.6(4) . . ?
C14 C9 B1 122.9(4) . . ?
C10 C9 B1 124.3(3) . . ?
F6 C10 C11 115.3(3) . . ?
F6 C10 C9 120.6(4) . . ?
C11 C10 C9 124.1(4) . . ?
F7 C11 C12 119.8(4) . . ?
F7 C11 C10 120.4(4) . . ?
C12 C11 C10 119.8(4) . . ?
F8 C12 C11 120.1(4) . . ?
F8 C12 C13 120.9(4) . . ?
C11 C12 C13 118.9(4) . . ?
F9 C13 C14 121.1(4) . . ?
F9 C13 C12 119.8(4) . . ?
C14 C13 C12 119.1(4) . . ?
F10 C14 C13 116.2(4) . . ?
F10 C14 C9 118.3(4) . . ?
C13 C14 C9 125.4(4) . . ?
C20 C15 C16 112.5(4) . . ?
C20 C15 B1 122.5(4) . . ?
C16 C15 B1 124.9(4) . . ?
F11 C16 C17 114.5(3) . . ?
F11 C16 C15 121.2(3) . . ?
C17 C16 C15 124.3(4) . . ?
F12 C17 C18 120.2(4) . . ?
F12 C17 C16 120.0(4) . . ?
C18 C17 C16 119.8(4) . . ?
F13 C18 C17 121.0(4) . . ?
F13 C18 C19 120.1(4) . . ?
C17 C18 C19 118.9(4) . . ?
F14 C19 C18 119.8(4) . . ?
F14 C19 C20 120.9(4) . . ?
C18 C19 C20 119.3(4) . . ?
F15 C20 C19 116.1(4) . . ?
F15 C20 C15 118.6(4) . . ?
C19 C20 C15 125.2(4) . . ?
C15 B1 C3 115.3(3) . . ?
C15 B1 C9 113.9(3) . . ?
C3 B1 C9 111.3(3) . . ?
C15 B1 S1 108.2(3) . . ?
C3 B1 S1 105.3(3) . . ?
C9 B1 S1 101.6(3) . . ?
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
S1 C1 1.794(5) . ?
S1 C2 1.810(5) . ?
S1 B1 2.091(5) . ?
F1 C4 1.355(5) . ?
F2 C5 1.353(5) . ?
F3 C6 1.345(5) . ?
F4 C7 1.355(5) . ?
F5 C8 1.358(5) . ?
F6 C10 1.353(4) . ?
F7 C11 1.342(5) . ?
F8 C12 1.352(5) . ?
F9 C13 1.350(5) . ?
F10 C14 1.361(5) . ?
F11 C16 1.348(4) . ?
F12 C17 1.342(4) . ?
F13 C18 1.333(5) . ?
F14 C19 1.345(5) . ?
F15 C20 1.357(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C8 1.372(6) . ?
C3 C4 1.408(6) . ?
C3 B1 1.630(6) . ?
C4 C5 1.375(6) . ?
C5 C6 1.363(7) . ?
C6 C7 1.373(7) . ?
C7 C8 1.389(6) . ?
C9 C14 1.391(6) . ?
C9 C10 1.391(6) . ?
C9 B1 1.636(6) . ?
C10 C11 1.384(6) . ?
C11 C12 1.369(6) . ?
C12 C13 1.379(6) . ?
C13 C14 1.368(6) . ?
C15 C20 1.382(6) . ?
C15 C16 1.401(5) . ?
C15 B1 1.619(6) . ?
C16 C17 1.388(6) . ?
C17 C18 1.366(6) . ?
C18 C19 1.378(6) . ?
C19 C20 1.382(6) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 F1 -178.7(4) . . . . ?
B1 C3 C4 F1 -7.4(6) . . . . ?
C8 C3 C4 C5 0.2(6) . . . . ?
B1 C3 C4 C5 171.4(4) . . . . ?
F1 C4 C5 F2 -0.3(7) . . . . ?
C3 C4 C5 F2 -179.2(4) . . . . ?
F1 C4 C5 C6 178.7(4) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
F2 C5 C6 F3 1.1(7) . . . . ?
C4 C5 C6 F3 -177.9(4) . . . . ?
F2 C5 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
F3 C6 C7 F4 -0.5(7) . . . . ?
C5 C6 C7 F4 -179.2(4) . . . . ?
F3 C6 C7 C8 177.4(4) . . . . ?
C5 C6 C7 C8 -1.4(7) . . . . ?
C4 C3 C8 F5 177.6(4) . . . . ?
B1 C3 C8 F5 7.0(6) . . . . ?
C4 C3 C8 C7 -0.8(6) . . . . ?
B1 C3 C8 C7 -171.4(4) . . . . ?
F4 C7 C8 F5 0.8(6) . . . . ?
C6 C7 C8 F5 -177.1(4) . . . . ?
F4 C7 C8 C3 179.3(4) . . . . ?
C6 C7 C8 C3 1.5(7) . . . . ?
C14 C9 C10 F6 174.9(3) . . . . ?
B1 C9 C10 F6 -1.2(6) . . . . ?
C14 C9 C10 C11 -3.4(6) . . . . ?
B1 C9 C10 C11 -179.5(4) . . . . ?
F6 C10 C11 F7 2.4(6) . . . . ?
C9 C10 C11 F7 -179.2(4) . . . . ?
F6 C10 C11 C12 -175.7(4) . . . . ?
C9 C10 C11 C12 2.7(6) . . . . ?
F7 C11 C12 F8 0.3(6) . . . . ?
C10 C11 C12 F8 178.4(4) . . . . ?
F7 C11 C12 C13 -177.7(4) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
F8 C12 C13 F9 -0.6(6) . . . . ?
C11 C12 C13 F9 177.4(4) . . . . ?
F8 C12 C13 C14 179.7(4) . . . . ?
C11 C12 C13 C14 -2.3(6) . . . . ?
F9 C13 C14 F10 -1.3(6) . . . . ?
C12 C13 C14 F10 178.4(4) . . . . ?
F9 C13 C14 C9 -178.3(4) . . . . ?
C12 C13 C14 C9 1.4(7) . . . . ?
C10 C9 C14 F10 -175.6(3) . . . . ?
B1 C9 C14 F10 0.5(6) . . . . ?
C10 C9 C14 C13 1.4(6) . . . . ?
B1 C9 C14 C13 177.5(4) . . . . ?
C20 C15 C16 F11 178.2(3) . . . . ?
B1 C15 C16 F11 1.6(6) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
B1 C15 C16 C17 -176.5(4) . . . . ?
F11 C16 C17 F12 1.6(5) . . . . ?
C15 C16 C17 F12 179.9(3) . . . . ?
F11 C16 C17 C18 -176.9(3) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
F12 C17 C18 F13 -0.3(6) . . . . ?
C16 C17 C18 F13 178.3(4) . . . . ?
F12 C17 C18 C19 -179.9(4) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
F13 C18 C19 F14 0.1(6) . . . . ?
C17 C18 C19 F14 179.7(4) . . . . ?
F13 C18 C19 C20 -179.7(4) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
F14 C19 C20 F15 -0.6(6) . . . . ?
C18 C19 C20 F15 179.1(4) . . . . ?
F14 C19 C20 C15 -178.1(4) . . . . ?
C18 C19 C20 C15 1.7(7) . . . . ?
C16 C15 C20 F15 -179.0(3) . . . . ?
B1 C15 C20 F15 -2.3(6) . . . . ?
C16 C15 C20 C19 -1.6(6) . . . . ?
B1 C15 C20 C19 175.1(4) . . . . ?
C20 C15 B1 C3 -54.3(5) . . . . ?
C16 C15 B1 C3 122.0(4) . . . . ?
C20 C15 B1 C9 175.3(4) . . . . ?
C16 C15 B1 C9 -8.4(5) . . . . ?
C20 C15 B1 S1 63.2(4) . . . . ?
C16 C15 B1 S1 -120.5(4) . . . . ?
C8 C3 B1 C15 -15.9(6) . . . . ?
C4 C3 B1 C15 174.1(4) . . . . ?
C8 C3 B1 C9 115.8(4) . . . . ?
C4 C3 B1 C9 -54.3(5) . . . . ?
C8 C3 B1 S1 -135.0(4) . . . . ?
C4 C3 B1 S1 54.9(4) . . . . ?
C14 C9 B1 C15 -68.1(5) . . . . ?
C10 C9 B1 C15 107.6(4) . . . . ?
C14 C9 B1 C3 159.6(4) . . . . ?
C10 C9 B1 C3 -24.7(5) . . . . ?
C14 C9 B1 S1 48.0(4) . . . . ?
C10 C9 B1 S1 -136.3(4) . . . . ?
C1 S1 B1 C15 -98.6(3) . . . . ?
C2 S1 B1 C15 8.3(4) . . . . ?
C1 S1 B1 C3 25.2(3) . . . . ?
C2 S1 B1 C3 132.1(3) . . . . ?
C1 S1 B1 C9 141.3(3) . . . . ?
C2 S1 B1 C9 -111.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180711
