#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/27/4112729.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_4112729
loop_
_publ_author_name
'Huadong Wang'
'Charles Edwin Webster'
'Lisa M. Pérez'
'Michael B. Hall'
'François P. Gabbaï'
_publ_section_title
;
 Reaction of the 1,8-Bis(diphenylmethylium)naphthalenediyl Dication with
 Fluoride: Formation of a Cation Containing a C-F\\rightarrowC Bridge
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8189
_journal_page_last               8196
_journal_paper_doi               10.1021/ja048501y
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C36 H26 B F5'
_chemical_formula_weight         564.38
_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                110.71(3)
_cell_angle_beta                 104.54(3)
_cell_angle_gamma                95.19(3)
_cell_formula_units_Z            2
_cell_length_a                   10.190(2)
_cell_length_b                   10.273(2)
_cell_length_c                   14.506(3)
_cell_measurement_temperature    110(2)
_cell_volume                     1347.7(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      110(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5824
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.609492
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             584
_exptl_crystal_size_max          1.10
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0325
_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)+(0.0432P)²+0.4525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                3373
_reflns_number_total             3860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja048501ysi20040315_035736.cif
_cod_data_source_block           1F
_cod_original_cell_volume        1347.7(5)
_cod_database_code               4112729
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
F F 0.45916(8) 0.08618(9) 0.68982(6) 0.0204(2) Uani 1 1 d .
C01 C 0.31771(15) 0.08288(16) 0.64242(12) 0.0189(3) Uani 1 1 d .
C02 C 0.49073(16) 0.05720(16) 0.85367(11) 0.0180(3) Uani 1 1 d .
C1 C 0.26006(15) 0.17492(16) 0.72618(12) 0.0179(3) Uani 1 1 d .
C2 C 0.13986(16) 0.21693(16) 0.68836(13) 0.0211(4) Uani 1 1 d .
H2A H 0.0968 0.1788 0.6173 0.025 Uiso 1 1 calc R
C3 C 0.07989(16) 0.31403(17) 0.75179(13) 0.0235(4) Uani 1 1 d .
H3A H -0.0041 0.3350 0.7238 0.028 Uiso 1 1 calc R
C4 C 0.14678(16) 0.37738(16) 0.85530(13) 0.0222(4) Uani 1 1 d .
H4A H 0.1115 0.4473 0.8974 0.027 Uiso 1 1 calc R
C5 C 0.33615(17) 0.40929(16) 1.00729(12) 0.0224(4) Uani 1 1 d .
H5A H 0.2965 0.4771 1.0471 0.027 Uiso 1 1 calc R
C6 C 0.45684(17) 0.38122(16) 1.05416(13) 0.0233(4) Uani 1 1 d .
H6A H 0.5022 0.4329 1.1241 0.028 Uiso 1 1 calc R
C7 C 0.51181(16) 0.27312(16) 0.99525(12) 0.0207(4) Uani 1 1 d .
H7A H 0.5956 0.2551 1.0268 0.025 Uiso 1 1 calc R
C8 C 0.44485(15) 0.19161(16) 0.89077(12) 0.0177(3) Uani 1 1 d .
C9 C 0.32392(15) 0.22921(16) 0.83621(12) 0.0177(3) Uani 1 1 d .
C10 C 0.26845(16) 0.33837(16) 0.89938(12) 0.0196(4) Uani 1 1 d .
C11 C 0.32305(15) 0.15349(16) 0.56588(12) 0.0200(4) Uani 1 1 d .
C12 C 0.24573(17) 0.09059(18) 0.46223(13) 0.0250(4) Uani 1 1 d .
H12A H 0.1896 0.0012 0.4365 0.030 Uiso 1 1 calc R
C13 C 0.25180(18) 0.1608(2) 0.39659(14) 0.0313(4) Uani 1 1 d .
H13A H 0.1997 0.1179 0.3272 0.038 Uiso 1 1 calc R
C14 C 0.33422(18) 0.29320(19) 0.43350(14) 0.0302(4) Uani 1 1 d .
H14A H 0.3373 0.3401 0.3895 0.036 Uiso 1 1 calc R
C15 C 0.41270(18) 0.35617(18) 0.53690(14) 0.0285(4) Uani 1 1 d .
H15A H 0.4690 0.4454 0.5622 0.034 Uiso 1 1 calc R
C16 C 0.40751(17) 0.28674(17) 0.60263(13) 0.0240(4) Uani 1 1 d .
H16A H 0.4608 0.3294 0.6717 0.029 Uiso 1 1 calc R
C21 C 0.24635(16) -0.07274(16) 0.58903(12) 0.0198(4) Uani 1 1 d .
C22 C 0.30840(17) -0.16727(17) 0.52560(12) 0.0237(4) Uani 1 1 d .
H22A H 0.3932 -0.1349 0.5201 0.028 Uiso 1 1 calc R
C23 C 0.24454(18) -0.30818(17) 0.47113(13) 0.0266(4) Uani 1 1 d .
H23A H 0.2862 -0.3700 0.4287 0.032 Uiso 1 1 calc R
C24 C 0.11879(18) -0.35806(18) 0.47923(13) 0.0272(4) Uani 1 1 d .
H24A H 0.0757 -0.4529 0.4421 0.033 Uiso 1 1 calc R
C25 C 0.05785(17) -0.26644(17) 0.54262(13) 0.0253(4) Uani 1 1 d .
H25A H -0.0260 -0.2999 0.5489 0.030 Uiso 1 1 calc R
C26 C 0.12114(16) -0.12402(17) 0.59730(12) 0.0214(4) Uani 1 1 d .
H26A H 0.0791 -0.0628 0.6397 0.026 Uiso 1 1 calc R
C31 C 0.63587(15) 0.06190(16) 0.86652(12) 0.0189(3) Uani 1 1 d .
C32 C 0.70299(16) -0.04674(16) 0.88155(12) 0.0208(4) Uani 1 1 d .
H32A H 0.6527 -0.1263 0.8824 0.025 Uiso 1 1 calc R
C33 C 0.84298(16) -0.03499(18) 0.89503(12) 0.0250(4) Uani 1 1 d .
H33A H 0.8870 -0.1067 0.9047 0.030 Uiso 1 1 calc R
C34 C 0.91819(17) 0.08375(18) 0.89410(13) 0.0278(4) Uani 1 1 d .
H34A H 1.0127 0.0913 0.9037 0.033 Uiso 1 1 calc R
C35 C 0.85435(17) 0.19152(18) 0.87906(13) 0.0265(4) Uani 1 1 d .
H35A H 0.9057 0.2706 0.8785 0.032 Uiso 1 1 calc R
C36 C 0.71485(16) 0.18050(17) 0.86502(12) 0.0216(4) Uani 1 1 d .
H36A H 0.6719 0.2523 0.8544 0.026 Uiso 1 1 calc R
C41 C 0.39201(15) -0.07361(16) 0.81835(12) 0.0183(3) Uani 1 1 d .
C42 C 0.27655(16) -0.07295(17) 0.85544(12) 0.0199(3) Uani 1 1 d .
H42A H 0.2622 0.0123 0.8989 0.024 Uiso 1 1 calc R
C43 C 0.18493(16) -0.19707(17) 0.82810(13) 0.0237(4) Uani 1 1 d .
H43A H 0.1104 -0.1959 0.8543 0.028 Uiso 1 1 calc R
C44 C 0.20434(17) -0.32402(17) 0.76120(13) 0.0252(4) Uani 1 1 d .
H44A H 0.1420 -0.4077 0.7422 0.030 Uiso 1 1 calc R
C45 C 0.31563(17) -0.32695(17) 0.72257(12) 0.0237(4) Uani 1 1 d .
H45A H 0.3272 -0.4124 0.6774 0.028 Uiso 1 1 calc R
C46 C 0.40958(16) -0.20367(16) 0.75073(12) 0.0204(4) Uani 1 1 d .
H46A H 0.4846 -0.2065 0.7250 0.024 Uiso 1 1 calc R
B1 B 0.18639(19) 0.42694(19) 0.19836(15) 0.0236(4) Uani 1 1 d .
F1 F 0.20604(11) 0.56545(10) 0.20463(8) 0.0397(3) Uani 1 1 d .
F2 F 0.11119(10) 0.41279(11) 0.26307(8) 0.0359(3) Uani 1 1 d .
F3 F 0.11377(12) 0.33685(11) 0.09690(8) 0.0440(3) Uani 1 1 d .
F4 F 0.31425(10) 0.39180(11) 0.22786(8) 0.0377(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'
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
C01 F C02 111.11(9)
F C01 C21 106.63(12)
F C01 C11 103.91(11)
C21 C01 C11 112.80(13)
F C01 C1 108.20(12)
C21 C01 C1 115.17(13)
C11 C01 C1 109.37(12)
F C01 C02 44.70(7)
C21 C01 C02 95.04(10)
C11 C01 C02 144.53(10)
C1 C01 C02 75.16(9)
C31 C02 C41 122.92(14)
C31 C02 C8 117.99(14)
C41 C02 C8 118.59(13)
C31 C02 F 90.40(10)
C41 C02 F 99.58(10)
C8 C02 F 86.73(9)
C31 C02 C01 114.58(10)
C41 C02 C01 85.23(9)
C8 C02 C01 76.62(9)
F C02 C01 24.19(4)
C2 C1 C9 118.58(14)
C2 C1 C01 114.43(14)
C9 C1 C01 126.76(13)
C1 C2 C3 123.21(15)
C4 C3 C2 118.85(15)
C3 C4 C10 120.91(15)
C6 C5 C10 122.06(15)
C5 C6 C7 118.78(15)
C8 C7 C6 122.04(15)
C7 C8 C9 120.13(14)
C7 C8 C02 112.81(14)
C9 C8 C02 125.81(14)
C10 C9 C1 117.26(14)
C10 C9 C8 115.84(14)
C1 C9 C8 126.79(14)
C4 C10 C5 118.93(14)
C4 C10 C9 120.58(15)
C5 C10 C9 120.48(14)
C12 C11 C16 118.99(15)
C12 C11 C01 122.55(14)
C16 C11 C01 118.45(14)
C11 C12 C13 120.24(16)
C14 C13 C12 120.58(16)
C13 C14 C15 119.45(16)
C16 C15 C14 120.29(16)
C15 C16 C11 120.44(16)
C26 C21 C22 118.70(15)
C26 C21 C01 123.22(14)
C22 C21 C01 118.04(14)
C23 C22 C21 120.44(16)
C22 C23 C24 120.38(16)
C25 C24 C23 119.64(16)
C24 C25 C26 120.33(16)
C21 C26 C25 120.49(16)
C36 C31 C32 118.56(14)
C36 C31 C02 118.60(14)
C32 C31 C02 122.84(14)
C33 C32 C31 120.08(15)
C32 C33 C34 120.00(15)
C33 C34 C35 120.92(15)
C36 C35 C34 119.54(16)
C35 C36 C31 120.89(15)
C46 C41 C42 118.46(14)
C46 C41 C02 122.20(14)
C42 C41 C02 119.29(14)
C43 C42 C41 120.77(15)
C42 C43 C44 119.69(15)
C45 C44 C43 120.56(15)
C46 C45 C44 120.35(15)
C45 C46 C41 120.15(15)
F1 B1 F4 109.12(14)
F1 B1 F2 110.42(14)
F4 B1 F2 109.25(14)
F1 B1 F3 108.94(15)
F4 B1 F3 110.05(15)
F2 B1 F3 109.06(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F C01 1.4243(17)
F C02 2.4444(17)
C01 C21 1.522(2)
C01 C11 1.535(2)
C01 C1 1.537(2)
C01 C02 3.242(2)
C02 C31 1.438(2)
C02 C41 1.446(2)
C02 C8 1.460(2)
C1 C2 1.383(2)
C1 C9 1.437(2)
C2 C3 1.399(2)
C3 C4 1.363(2)
C4 C10 1.407(2)
C5 C6 1.357(2)
C5 C10 1.420(2)
C6 C7 1.400(2)
C7 C8 1.394(2)
C8 C9 1.451(2)
C9 C10 1.437(2)
C11 C12 1.387(2)
C11 C16 1.393(2)
C12 C13 1.392(2)
C13 C14 1.376(3)
C14 C15 1.388(3)
C15 C16 1.386(2)
C21 C26 1.386(2)
C21 C22 1.400(2)
C22 C23 1.380(2)
C23 C24 1.385(2)
C24 C25 1.377(2)
C25 C26 1.392(2)
C31 C36 1.408(2)
C31 C32 1.413(2)
C32 C33 1.378(2)
C33 C34 1.387(2)
C34 C35 1.388(2)
C35 C36 1.373(2)
C41 C46 1.409(2)
C41 C42 1.411(2)
C42 C43 1.377(2)
C43 C44 1.389(2)
C44 C45 1.384(2)
C45 C46 1.380(2)
B1 F1 1.386(2)
B1 F4 1.388(2)
B1 F2 1.388(2)
B1 F3 1.391(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139119167
