#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/43/4074378.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_4074378
loop_
_publ_author_name
'Mitu, Simona'
'Baird, Michael C.'
_publ_section_title
;
 Carboxylic Acids as Lewis Bases:  Structures and Properties of
 Strongly Acidic Carboxylic Acid Adducts of B(C6F5)3
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              4888
_journal_paper_doi               10.1021/om060601k
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C22 H8 B F15 O2'
_chemical_formula_weight         600.09
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.076(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1619(11)
_cell_length_b                   14.3044(14)
_cell_length_c                   15.1871(15)
_cell_measurement_temperature    180(2)
_cell_volume                     2207.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12715
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8584
_exptl_absorpt_correction_type   'Empirical (Bruker SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0329
_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)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0596
_reflns_number_gt                2594
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060601ksi20060807_114331.cif
_cod_data_source_block           mb12
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4074378
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
B1 B 0.7371(2) 0.26719(15) 0.41040(14) 0.0318(5) Uani 1 1 d .
O1 O 0.60985(12) 0.29438(8) 0.46272(8) 0.0319(3) Uani 1 1 d .
O2 O 0.40795(13) 0.31257(10) 0.50507(9) 0.0503(4) Uani 1 1 d .
C1 C 0.85314(18) 0.29072(13) 0.48233(11) 0.0317(5) Uani 1 1 d .
C2 C 0.85836(19) 0.37774(14) 0.52290(12) 0.0368(5) Uani 1 1 d .
C3 C 0.9569(2) 0.40574(15) 0.57944(13) 0.0451(6) Uani 1 1 d .
C4 C 1.0595(2) 0.34677(18) 0.59698(13) 0.0483(6) Uani 1 1 d .
C5 C 1.0629(2) 0.26162(16) 0.55758(14) 0.0431(5) Uani 1 1 d .
C6 C 0.9605(2) 0.23462(14) 0.50283(13) 0.0379(5) Uani 1 1 d .
C7 C 0.75769(18) 0.33993(12) 0.32907(11) 0.0288(4) Uani 1 1 d .
C8 C 0.87583(19) 0.33757(13) 0.28548(12) 0.0349(5) Uani 1 1 d .
C9 C 0.9125(2) 0.40102(14) 0.22255(13) 0.0404(5) Uani 1 1 d .
C10 C 0.8272(2) 0.47109(14) 0.19843(12) 0.0434(6) Uani 1 1 d .
C11 C 0.7092(2) 0.47608(14) 0.23856(13) 0.0407(5) Uani 1 1 d .
C12 C 0.67767(19) 0.41268(13) 0.30268(12) 0.0341(5) Uani 1 1 d .
C13 C 0.71869(18) 0.15757(13) 0.38445(11) 0.0306(5) Uani 1 1 d .
C14 C 0.71777(18) 0.11993(13) 0.30053(12) 0.0324(5) Uani 1 1 d .
C15 C 0.69155(18) 0.02782(13) 0.28154(12) 0.0350(5) Uani 1 1 d .
C16 C 0.66081(19) -0.03226(13) 0.34769(13) 0.0375(5) Uani 1 1 d .
C17 C 0.66071(19) 0.00009(14) 0.43267(13) 0.0382(5) Uani 1 1 d .
C18 C 0.68996(19) 0.09213(13) 0.44907(12) 0.0346(5) Uani 1 1 d .
C19 C 0.4898(2) 0.28466(12) 0.44652(12) 0.0326(5) Uani 1 1 d .
C20 C 0.4299(2) 0.24184(16) 0.36689(14) 0.0356(5) Uani 1 1 d .
H20A H 0.4787(18) 0.2591(11) 0.3180(12) 0.035(5) Uiso 1 1 d .
H20B H 0.4482(17) 0.1803(13) 0.3725(11) 0.040(6) Uiso 1 1 d .
C21 C 0.2843(2) 0.25875(19) 0.35346(18) 0.0471(6) Uani 1 1 d .
H21A H 0.260(2) 0.3258(16) 0.3517(13) 0.067(7) Uiso 1 1 d .
H21B H 0.255(2) 0.2350(13) 0.2984(14) 0.055(7) Uiso 1 1 d .
H21C H 0.233(2) 0.2297(15) 0.4018(15) 0.073(8) Uiso 1 1 d .
C22 C 0.4639(2) 0.3519(2) 0.58715(14) 0.0813(9) Uani 1 1 d .
H22A H 0.3924 0.3705 0.6259 0.122 Uiso 1 1 calc R
H22B H 0.5177 0.4067 0.5734 0.122 Uiso 1 1 calc R
H22C H 0.5188 0.3048 0.6168 0.122 Uiso 1 1 calc R
F2 F 0.76220(11) 0.44123(7) 0.50485(7) 0.0463(3) Uani 1 1 d .
F3 F 0.95490(12) 0.49166(9) 0.61650(8) 0.0678(4) Uani 1 1 d .
F4 F 1.15780(12) 0.37339(10) 0.65245(8) 0.0714(4) Uani 1 1 d .
F5 F 1.16699(11) 0.20490(9) 0.57156(8) 0.0606(4) Uani 1 1 d .
F6 F 0.97076(11) 0.14889(8) 0.46630(7) 0.0518(3) Uani 1 1 d .
F8 F 0.96383(11) 0.26900(8) 0.30559(7) 0.0467(3) Uani 1 1 d .
F9 F 1.03166(12) 0.39598(8) 0.18644(8) 0.0607(4) Uani 1 1 d .
F10 F 0.86098(13) 0.53344(9) 0.13755(8) 0.0680(4) Uani 1 1 d .
F11 F 0.62402(12) 0.54547(8) 0.21757(8) 0.0618(4) Uani 1 1 d .
F12 F 0.55968(11) 0.42733(7) 0.34119(7) 0.0475(3) Uani 1 1 d .
F14 F 0.74023(11) 0.17495(7) 0.22946(6) 0.0438(3) Uani 1 1 d .
F15 F 0.69145(11) -0.00208(7) 0.19749(7) 0.0475(3) Uani 1 1 d .
F16 F 0.62767(11) -0.12116(7) 0.33003(7) 0.0529(3) Uani 1 1 d .
F17 F 0.62949(12) -0.05783(7) 0.49897(7) 0.0534(3) Uani 1 1 d .
F18 F 0.68645(11) 0.12042(7) 0.53414(7) 0.0474(3) 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'
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'
F F 0.0171 0.0103 '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
O1 B1 C13 105.54(15)
O1 B1 C1 101.61(14)
C13 B1 C1 116.13(16)
O1 B1 C7 109.99(15)
C13 B1 C7 116.56(15)
C1 B1 C7 105.93(15)
C19 O1 B1 132.86(15)
C19 O2 C22 117.24(16)
C6 C1 C2 113.33(18)
C6 C1 B1 126.07(17)
C2 C1 B1 120.26(17)
F2 C2 C3 116.53(18)
F2 C2 C1 119.22(17)
C3 C2 C1 124.2(2)
F3 C3 C4 119.88(19)
F3 C3 C2 120.8(2)
C4 C3 C2 119.3(2)
F4 C4 C5 120.2(2)
F4 C4 C3 120.1(2)
C5 C4 C3 119.6(2)
F5 C5 C4 119.8(2)
F5 C5 C6 120.6(2)
C4 C5 C6 119.6(2)
F6 C6 C5 116.11(18)
F6 C6 C1 120.01(18)
C5 C6 C1 123.85(19)
C12 C7 C8 113.13(17)
C12 C7 B1 128.28(17)
C8 C7 B1 118.17(17)
F8 C8 C9 116.57(18)
F8 C8 C7 118.94(17)
C9 C8 C7 124.48(19)
F9 C9 C10 120.11(19)
F9 C9 C8 120.50(19)
C10 C9 C8 119.37(19)
F10 C10 C11 121.1(2)
F10 C10 C9 120.3(2)
C11 C10 C9 118.56(19)
F11 C11 C10 120.02(18)
F11 C11 C12 119.7(2)
C10 C11 C12 120.26(19)
F12 C12 C11 115.01(18)
F12 C12 C7 120.81(17)
C11 C12 C7 124.17(19)
C14 C13 C18 112.96(17)
C14 C13 B1 126.66(16)
C18 C13 B1 120.16(16)
F14 C14 C15 115.07(16)
F14 C14 C13 120.54(17)
C15 C14 C13 124.37(17)
F15 C15 C16 120.17(17)
F15 C15 C14 120.03(17)
C16 C15 C14 119.76(17)
F16 C16 C15 120.70(18)
F16 C16 C17 120.24(18)
C15 C16 C17 119.04(18)
F17 C17 C16 120.04(18)
F17 C17 C18 120.55(17)
C16 C17 C18 119.40(18)
F18 C18 C17 116.76(17)
F18 C18 C13 118.77(17)
C17 C18 C13 124.44(17)
O1 C19 O2 118.00(17)
O1 C19 C20 126.45(18)
O2 C19 C20 115.54(18)
C19 C20 C21 115.61(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 O1 1.579(2)
B1 C13 1.627(3)
B1 C1 1.628(3)
B1 C7 1.631(3)
O1 C19 1.248(2)
O2 C19 1.292(2)
O2 C22 1.472(2)
C1 C6 1.385(3)
C1 C2 1.390(2)
C2 F2 1.358(2)
C2 C3 1.367(3)
C3 F3 1.352(2)
C3 C4 1.364(3)
C4 F4 1.349(2)
C4 C5 1.358(3)
C5 F5 1.347(2)
C5 C6 1.375(3)
C6 F6 1.351(2)
C7 C12 1.376(2)
C7 C8 1.382(2)
C8 F8 1.358(2)
C8 C9 1.374(3)
C9 F9 1.341(2)
C9 C10 1.371(3)
C10 F10 1.334(2)
C10 C11 1.357(3)
C11 F11 1.351(2)
C11 C12 1.373(3)
C12 F12 1.360(2)
C13 C14 1.383(2)
C13 C18 1.391(2)
C14 F14 1.3587(19)
C14 C15 1.374(2)
C15 F15 1.3462(19)
C15 C16 1.363(3)
C16 F16 1.341(2)
C16 C17 1.371(3)
C17 F17 1.346(2)
C17 C18 1.372(2)
C18 F18 1.3550(19)
C19 C20 1.477(3)
C20 C21 1.509(3)
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
C13 B1 O1 C19 -51.0(2)
C1 B1 O1 C19 -172.55(17)
C7 B1 O1 C19 75.6(2)
O1 B1 C1 C6 135.03(18)
C13 B1 C1 C6 21.1(3)
C7 B1 C1 C6 -110.0(2)
O1 B1 C1 C2 -52.0(2)
C13 B1 C1 C2 -165.95(16)
C7 B1 C1 C2 62.9(2)
C6 C1 C2 F2 176.78(16)
B1 C1 C2 F2 3.0(3)
C6 C1 C2 C3 -1.6(3)
B1 C1 C2 C3 -175.42(18)
F2 C2 C3 F3 1.7(3)
C1 C2 C3 F3 -179.88(17)
F2 C2 C3 C4 -176.95(17)
C1 C2 C3 C4 1.5(3)
F3 C3 C4 F4 1.2(3)
C2 C3 C4 F4 179.81(17)
F3 C3 C4 C5 -178.09(18)
C2 C3 C4 C5 0.5(3)
F4 C4 C5 F5 -2.3(3)
C3 C4 C5 F5 176.96(18)
F4 C4 C5 C6 178.48(17)
C3 C4 C5 C6 -2.2(3)
F5 C5 C6 F6 1.0(3)
C4 C5 C6 F6 -179.82(17)
F5 C5 C6 C1 -177.08(17)
C4 C5 C6 C1 2.1(3)
C2 C1 C6 F6 -178.19(16)
B1 C1 C6 F6 -4.8(3)
C2 C1 C6 C5 -0.2(3)
B1 C1 C6 C5 173.17(18)
O1 B1 C7 C12 -3.2(3)
C13 B1 C7 C12 116.8(2)
C1 B1 C7 C12 -112.3(2)
O1 B1 C7 C8 168.73(15)
C13 B1 C7 C8 -71.2(2)
C1 B1 C7 C8 59.7(2)
C12 C7 C8 F8 179.96(16)
B1 C7 C8 F8 6.8(2)
C12 C7 C8 C9 0.6(3)
B1 C7 C8 C9 -172.56(18)
F8 C8 C9 F9 -2.5(3)
C7 C8 C9 F9 176.92(17)
F8 C8 C9 C10 179.05(16)
C7 C8 C9 C10 -1.5(3)
F9 C9 C10 F10 1.5(3)
C8 C9 C10 F10 179.92(17)
F9 C9 C10 C11 -177.68(18)
C8 C9 C10 C11 0.8(3)
F10 C10 C11 F11 -0.5(3)
C9 C10 C11 F11 178.64(17)
F10 C10 C11 C12 -178.31(17)
C9 C10 C11 C12 0.8(3)
F11 C11 C12 F12 -0.9(3)
C10 C11 C12 F12 176.92(17)
F11 C11 C12 C7 -179.71(16)
C10 C11 C12 C7 -1.9(3)
C8 C7 C12 F12 -177.59(16)
B1 C7 C12 F12 -5.3(3)
C8 C7 C12 C11 1.2(3)
B1 C7 C12 C11 173.42(18)
O1 B1 C13 C14 121.88(19)
C1 B1 C13 C14 -126.5(2)
C7 B1 C13 C14 -0.5(3)
O1 B1 C13 C18 -52.4(2)
C1 B1 C13 C18 59.3(2)
C7 B1 C13 C18 -174.77(17)
C18 C13 C14 F14 178.14(16)
B1 C13 C14 F14 3.5(3)
C18 C13 C14 C15 0.0(3)
B1 C13 C14 C15 -174.63(18)
F14 C14 C15 F15 1.0(3)
C13 C14 C15 F15 179.22(17)
F14 C14 C15 C16 -176.56(16)
C13 C14 C15 C16 1.7(3)
F15 C15 C16 F16 -1.3(3)
C14 C15 C16 F16 176.23(17)
F15 C15 C16 C17 -179.54(17)
C14 C15 C16 C17 -2.0(3)
F16 C16 C17 F17 1.2(3)
C15 C16 C17 F17 179.41(17)
F16 C16 C17 C18 -177.51(17)
C15 C16 C17 C18 0.7(3)
F17 C17 C18 F18 0.4(3)
C16 C17 C18 F18 179.06(16)
F17 C17 C18 C13 -177.64(17)
C16 C17 C18 C13 1.0(3)
C14 C13 C18 F18 -179.35(16)
B1 C13 C18 F18 -4.4(3)
C14 C13 C18 C17 -1.3(3)
B1 C13 C18 C17 173.66(18)
B1 O1 C19 O2 178.07(16)
B1 O1 C19 C20 -0.4(3)
C22 O2 C19 O1 -1.2(3)
C22 O2 C19 C20 177.4(2)
O1 C19 C20 C21 -166.19(19)
O2 C19 C20 C21 15.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21158303
2 PubChem 139104857
