3-Benzyl-2,4,6-triphenyl­pyrylium tetra­fluoro­borate

Jara, F.; Domínguez, M.; Rezende, M.C.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536806028285

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 8| August 2006| Pages o3495-o3497

https://doi.org/10.1107/S1600536806028285

3-Benzyl-2,4,6-triphenylpyrylium tetrafluoroborate

Francisco Jara,^a Moisés Domínguez,^a Marcos C. Rezende,^a Edward R. T. Tiekink,^b ^* James L. Wardell ^c and Solange M. S. V. Wardell ^d ‡

^aFacultad de Quimica y Biologia, Universidad de Santiago, Casilla 40, Correo 33, Santiago, Chile, ^bDepartment of Chemistry, The University of Texas at San Antonio, 6900 North Loop 1604 West, San Antonio, Texas 78249-0698, USA, ^cDepartment of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, and, Instituto de Química, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, and ^dComplexo Tecnológico de Medicamentos Farmanguinhos, Av. Comandante Guaranys 447, Jacarepaguá – Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: edward.tiekink@utsa.edu

(Received 12 July 2006; accepted 20 July 2006; online 26 July 2006)

The central OC₅ ring in the cation of the title compound, C₃₀H₂₃O⁺·BF₄⁻, has considerable aromatic character but the pendant aromatic rings are not coplanar. The crystal structure comprises undulating layers of cations separated by BF₄⁻ anions with significant intermolecular interactions between them.

Comment

The structure of the title compound, (I) (Fig. 1 and Table 1), shows significant twisting of the pendant aromatic rings out of the central plane. The dihedral angles between the O1/C1–C5 ring and the C6–C11, C12–C17 and C25–C30 rings are 28.14 (10), 56.70 (11) and 83.44 (10)°, respectively. Within the central ring, which formally carries a positive charge, the two O—C distances are equal within experimental error and the C—C distances lie in the relatively narrow range 1.361 (3)–1.414 (3) Å. These observations strongly suggest substantial delocalization of π-electron density over this ring.

In the crystal structure there are a number of intermolecular interactions linking the ions. The primary interactions operating in the crystal structure are illustrated in Fig. 2. Here, B—F⋯H contacts are highlighted as golden dashed lines. The first contact occurs between the two components of the asymmetric unit so that C20—H20⋯F4 is 2.49 Å, C20⋯F4 is 3.355 (3) Å and the angle at H20 is 152°. The second F⋯H contact involves the C8ⁱ and F3 atoms so that C8ⁱ—H8ⁱ⋯F3 is 2.55 Å, C8ⁱ⋯F3 is 3.321 (3) Å and the angle at H8 is 139 Å [symmetry code: (i) 1 − x, 1 − y, −z]. The remaining two F atoms serve to link two central O1/C1–C5 rings. The parameters associated with these interactions are B1—F1⋯ring centroid(O1/C1–C5) = 3.091 (2) Å and angle at F1 = 114.52 (15)°, and B1—F2⋯ring centroid(O1/C1–C5)ⁱⁱ = 3.080 (2) Å and angle at F2 = 118.59 (17)° [symmetry code: (ii) 1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z]. Formally, these might be considered as F⋯ring centroid(O1/C1–C5) interactions, but as seen in the B—F⋯ring centroid(O1/C1–C5) angles there is significant bending in the angles so that F1 approaches atoms O1 and C1 at 2.9508 (24) and 2.9766 (28) Å, respectively, with the other F1⋯C distances being greater than 3.3 Å. A similar situation pertains for the interactions involving atom F2. Thus, the F2⋯O1ⁱⁱ, F2⋯C1ⁱⁱ and F2⋯C5ⁱⁱ distances are 2.9270 (22), 3.1280 (28) and 3.1845 (26) Å, respectively, the remaining F2⋯Cⁱⁱ distances being greater than 3.5 Å. The only other significant intermolecular contact in the structure of (I) is also illustrated in Fig. 2, i.e. a C18ⁱⁱⁱ—H18Aⁱⁱⁱ⋯ring centroid(C6–C11) contact with an H18Aⁱⁱⁱ⋯ring centroid distance of 2.98 Å and an angle of 152° at the H18Aⁱⁱⁱ atom. The global crystal structure may be described as comprising undulating layers of cations interspersed with anions (see Fig. 3).

Figure 1
The asymmetric unit of (I)

showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Figure 2
Environment about the BF₄⁻ anion in (I)

(Crystal Impact, 2006

). Color code: O (red), C (grey), B (brown) and H (green).

Figure 3
Packing diagram for (I)

, viewed approximately down the a axis (Crystal Impact, 2006

). Color code as for Fig. 2

Experimental

The title compound was isolated as a by-product in the preparation of 2-(4-hyroxyphenyl)-4,6-diphenylpyrylium tetrafluoroborate from 1,3-diphenylpropenone and 4-hydroxyphenylethanone in the presence of boron trifluoride etherate (Aliaga et al., 1997 ). The two products were separated by fractional crystallization from acetic acid. The title compound, recrystallized from AcOH, had melting point and spectroscopic properties in agreement with literature values (Marton et al., 1999 ).

Crystal data

C₃₀H₂₃O⁺·BF⁴⁻
M_r = 486.29
Monoclinic, P 2₁ /c
a = 10.6170 (3) Å
b = 13.2065 (3) Å
c = 17.1985 (5) Å
β = 102.784 (1)°
V = 2351.68 (11) Å³
Z = 4
D_x = 1.374 Mg m⁻³
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 (2) K
Block, pale yellow
0.24 × 0.10 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.834, T_max = 1
25644 measured reflections
4136 independent reflections
3347 reflections with I > 2σ(I)
R_int = 0.042
θ_max = 25.0°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.142
S = 1.05
4136 reflections
325 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0667P)² + 2.1496P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—C1	1.341 (3)
O1—C5	1.350 (3)
C1—C2	1.361 (3)
C2—C3	1.397 (3)
C3—C4	1.414 (3)
C4—C5	1.381 (3)

C1—O1—C5	122.38 (17)

All H atoms were allowed to ride on their parent atoms in the riding-model approximation at C—H distances of 0.95–0.99 Å, and with U_iso(H) = 1.2U_eq(C). Evidence of some disorder in the position of the BF₄⁻ anion can be noted from Fig. 1. However, multiple positions could not be resolved.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Crystal Impact, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806028285/hg2068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806028285/hg2068Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006); software used to prepare material for publication: SHELXL97.

3-Benzyl-2,4,6-triphenylpyrylium tetrafluoroborate top

Crystal data top

C₃₀H₂₃O⁺·BF₄⁻	F(000) = 1008
M_r = 486.29	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 5538 reflections
a = 10.6170 (3) Å	θ = 2.9–27.5°
b = 13.2065 (3) Å	µ = 0.10 mm⁻¹
c = 17.1985 (5) Å	T = 120 K
β = 102.784 (1)°	Block, pale yellow
V = 2351.68 (11) Å³	0.24 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	4136 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3347 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
φ and ω scans	h = −12→12
Absorption correction: multi scan (SADABS; Sheldrick, 2003)	k = −15→15
T_min = 0.834, T_max = 1	l = −20→20
25644 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0667P)² + 2.1496P] where P = (F_o² + 2F_c²)/3
4136 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.57576 (17)	0.50732 (15)	0.27361 (13)	0.0707 (7)
F2	0.71621 (18)	0.63183 (12)	0.25861 (12)	0.0559 (5)
F3	0.70332 (18)	0.48944 (15)	0.18351 (10)	0.0588 (5)
F4	0.78734 (18)	0.48523 (15)	0.31391 (11)	0.0636 (5)
O1	0.40466 (14)	0.33118 (11)	0.27331 (9)	0.0202 (3)
C1	0.4465 (2)	0.31678 (16)	0.20605 (13)	0.0190 (5)
C2	0.5580 (2)	0.26442 (16)	0.20922 (13)	0.0201 (5)
H2	0.5889	0.2550	0.1620	0.024*
C3	0.6273 (2)	0.22436 (16)	0.28119 (13)	0.0200 (5)
C4	0.5820 (2)	0.24083 (16)	0.35153 (13)	0.0193 (5)
C5	0.4691 (2)	0.29537 (16)	0.34461 (13)	0.0195 (5)
C6	0.3624 (2)	0.36022 (16)	0.13507 (13)	0.0187 (5)
C7	0.4156 (2)	0.38924 (16)	0.07108 (13)	0.0216 (5)
H7	0.5057	0.3818	0.0744	0.026*
C8	0.3370 (2)	0.42882 (17)	0.00296 (13)	0.0245 (5)
H8	0.3727	0.4482	−0.0408	0.029*
C9	0.2061 (2)	0.44013 (17)	−0.00133 (14)	0.0260 (5)
H9	0.1523	0.4681	−0.0479	0.031*
C10	0.1527 (2)	0.41098 (18)	0.06188 (15)	0.0281 (6)
H10	0.0627	0.4188	0.0584	0.034*
C11	0.2304 (2)	0.37063 (17)	0.12982 (14)	0.0242 (5)
H11	0.1938	0.3500	0.1729	0.029*
C12	0.7417 (2)	0.16057 (17)	0.27859 (13)	0.0207 (5)
C13	0.7277 (2)	0.07825 (18)	0.22708 (15)	0.0268 (5)
H13	0.6450	0.0621	0.1954	0.032*
C14	0.8336 (2)	0.01974 (19)	0.22177 (16)	0.0324 (6)
H14	0.8229	−0.0366	0.1866	0.039*
C15	0.9547 (2)	0.04247 (18)	0.26704 (15)	0.0305 (6)
H15	1.0270	0.0019	0.2633	0.037*
C16	0.9694 (2)	0.12461 (19)	0.31768 (15)	0.0298 (6)
H16	1.0528	0.1412	0.3483	0.036*
C17	0.8643 (2)	0.18334 (19)	0.32446 (14)	0.0271 (5)
H17	0.8755	0.2391	0.3603	0.033*
C18	0.6405 (2)	0.18787 (17)	0.42883 (13)	0.0213 (5)
H18A	0.6771	0.1228	0.4156	0.026*
H18B	0.5698	0.1715	0.4558	0.026*
C19	0.7452 (2)	0.24305 (17)	0.48847 (13)	0.0213 (5)
C20	0.7977 (2)	0.33477 (18)	0.47235 (15)	0.0278 (5)
H20	0.7641	0.3688	0.4235	0.033*
C21	0.8997 (2)	0.3768 (2)	0.52801 (17)	0.0366 (6)
H21	0.9354	0.4395	0.5166	0.044*
C22	0.9499 (2)	0.3289 (2)	0.59937 (16)	0.0376 (7)
H22	1.0217	0.3571	0.6359	0.045*
C23	0.8946 (2)	0.2396 (2)	0.61708 (15)	0.0344 (6)
H23	0.9263	0.2073	0.6669	0.041*
C24	0.7929 (2)	0.19681 (18)	0.56234 (13)	0.0249 (5)
H24	0.7552	0.1355	0.5751	0.030*
C25	0.3994 (2)	0.31854 (16)	0.40788 (13)	0.0207 (5)
C26	0.4613 (2)	0.36439 (17)	0.47898 (14)	0.0247 (5)
H26	0.5509	0.3796	0.4884	0.030*
C27	0.3916 (2)	0.38770 (18)	0.53592 (14)	0.0284 (5)
H27	0.4333	0.4201	0.5841	0.034*
C28	0.2617 (2)	0.36415 (18)	0.52307 (14)	0.0277 (6)
H28	0.2147	0.3797	0.5626	0.033*
C29	0.2000 (2)	0.31797 (18)	0.45261 (15)	0.0278 (5)
H29	0.1109	0.3017	0.4440	0.033*
C30	0.2680 (2)	0.29533 (17)	0.39466 (14)	0.0239 (5)
H30	0.2253	0.2642	0.3462	0.029*
B1	0.6920 (3)	0.5292 (2)	0.25495 (17)	0.0271 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0457 (10)	0.0742 (13)	0.1045 (17)	−0.0265 (9)	0.0432 (11)	−0.0448 (12)
F2	0.0666 (12)	0.0319 (9)	0.0727 (13)	−0.0064 (8)	0.0231 (10)	−0.0016 (8)
F3	0.0723 (12)	0.0718 (13)	0.0360 (10)	−0.0067 (10)	0.0199 (9)	−0.0175 (9)
F4	0.0644 (12)	0.0754 (13)	0.0489 (11)	0.0126 (10)	0.0083 (9)	0.0235 (10)
O1	0.0210 (8)	0.0222 (8)	0.0177 (8)	0.0011 (6)	0.0051 (6)	0.0023 (6)
C1	0.0221 (11)	0.0188 (11)	0.0171 (11)	−0.0036 (9)	0.0061 (9)	−0.0006 (9)
C2	0.0204 (11)	0.0231 (11)	0.0180 (11)	0.0003 (9)	0.0065 (9)	0.0015 (9)
C3	0.0183 (11)	0.0196 (11)	0.0224 (12)	−0.0035 (9)	0.0048 (9)	0.0017 (9)
C4	0.0196 (11)	0.0191 (11)	0.0186 (11)	−0.0028 (9)	0.0030 (9)	0.0028 (9)
C5	0.0229 (11)	0.0174 (11)	0.0178 (11)	−0.0026 (9)	0.0035 (9)	0.0038 (9)
C6	0.0210 (11)	0.0173 (11)	0.0168 (11)	0.0012 (9)	0.0021 (9)	−0.0022 (9)
C7	0.0223 (11)	0.0205 (11)	0.0217 (12)	0.0008 (9)	0.0042 (10)	−0.0008 (9)
C8	0.0332 (13)	0.0218 (12)	0.0180 (12)	−0.0020 (10)	0.0046 (10)	−0.0011 (9)
C9	0.0310 (13)	0.0194 (11)	0.0217 (12)	0.0014 (10)	−0.0071 (10)	−0.0012 (9)
C10	0.0199 (11)	0.0271 (13)	0.0349 (14)	0.0039 (10)	0.0012 (11)	−0.0013 (11)
C11	0.0217 (11)	0.0269 (12)	0.0242 (13)	0.0025 (10)	0.0055 (10)	−0.0008 (10)
C12	0.0207 (11)	0.0239 (12)	0.0186 (11)	−0.0003 (9)	0.0066 (9)	0.0058 (9)
C13	0.0216 (11)	0.0277 (13)	0.0314 (13)	−0.0040 (10)	0.0064 (10)	−0.0005 (10)
C14	0.0325 (14)	0.0236 (12)	0.0440 (16)	0.0005 (10)	0.0150 (12)	−0.0025 (11)
C15	0.0262 (13)	0.0280 (13)	0.0415 (15)	0.0067 (10)	0.0167 (11)	0.0132 (11)
C16	0.0207 (12)	0.0403 (15)	0.0281 (13)	0.0013 (11)	0.0046 (10)	0.0096 (11)
C17	0.0250 (12)	0.0340 (13)	0.0220 (12)	0.0013 (10)	0.0044 (10)	0.0009 (10)
C18	0.0211 (11)	0.0238 (11)	0.0195 (12)	−0.0002 (9)	0.0055 (9)	0.0038 (9)
C19	0.0197 (11)	0.0253 (12)	0.0200 (12)	0.0033 (9)	0.0066 (9)	−0.0013 (9)
C20	0.0268 (12)	0.0302 (13)	0.0285 (13)	−0.0028 (10)	0.0104 (11)	−0.0017 (11)
C21	0.0319 (14)	0.0358 (15)	0.0476 (17)	−0.0100 (11)	0.0205 (13)	−0.0147 (13)
C22	0.0247 (13)	0.0554 (18)	0.0333 (15)	−0.0026 (12)	0.0080 (11)	−0.0216 (13)
C23	0.0291 (13)	0.0493 (16)	0.0233 (13)	0.0099 (12)	0.0024 (11)	−0.0080 (12)
C24	0.0264 (12)	0.0281 (12)	0.0207 (12)	0.0063 (10)	0.0065 (10)	−0.0008 (10)
C25	0.0241 (11)	0.0189 (11)	0.0204 (12)	0.0032 (9)	0.0077 (9)	0.0043 (9)
C26	0.0250 (12)	0.0252 (12)	0.0239 (13)	0.0013 (10)	0.0052 (10)	0.0016 (10)
C27	0.0354 (14)	0.0281 (13)	0.0214 (12)	0.0036 (11)	0.0055 (11)	−0.0022 (10)
C28	0.0337 (13)	0.0281 (13)	0.0257 (13)	0.0072 (10)	0.0158 (11)	0.0035 (10)
C29	0.0248 (12)	0.0268 (13)	0.0342 (14)	0.0019 (10)	0.0115 (11)	0.0035 (11)
C30	0.0253 (12)	0.0234 (12)	0.0234 (12)	0.0012 (9)	0.0061 (10)	0.0009 (10)
B1	0.0270 (14)	0.0263 (14)	0.0298 (15)	0.0001 (11)	0.0099 (12)	−0.0016 (12)

Geometric parameters (Å, º) top

F1—B1	1.373 (3)	C14—H14	0.9500
F2—B1	1.378 (3)	C15—C16	1.378 (4)
F3—B1	1.366 (3)	C15—H15	0.9500
F4—B1	1.392 (3)	C16—C17	1.385 (3)
O1—C1	1.341 (3)	C16—H16	0.9500
O1—C5	1.350 (3)	C17—H17	0.9500
C1—C2	1.361 (3)	C18—C19	1.521 (3)
C1—C6	1.461 (3)	C18—H18A	0.9900
C2—C3	1.397 (3)	C18—H18B	0.9900
C2—H2	0.9500	C19—C24	1.400 (3)
C3—C4	1.414 (3)	C19—C20	1.386 (3)
C3—C12	1.488 (3)	C20—C21	1.392 (4)
C4—C5	1.381 (3)	C20—H20	0.9500
C4—C18	1.509 (3)	C21—C22	1.378 (4)
C5—C25	1.476 (3)	C21—H21	0.9500
C6—C11	1.391 (3)	C22—C23	1.382 (4)
C6—C7	1.397 (3)	C22—H22	0.9500
C7—C8	1.382 (3)	C23—C24	1.386 (3)
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.384 (3)	C24—H24	0.9500
C8—H8	0.9500	C25—C30	1.398 (3)
C9—C10	1.387 (3)	C25—C26	1.392 (3)
C9—H9	0.9500	C26—C27	1.387 (3)
C10—C11	1.380 (3)	C26—H26	0.9500
C10—H10	0.9500	C27—C28	1.383 (3)
C11—H11	0.9500	C27—H27	0.9500
C12—C13	1.389 (3)	C28—C29	1.385 (3)
C12—C17	1.397 (3)	C28—H28	0.9500
C13—C14	1.384 (3)	C29—C30	1.386 (3)
C13—H13	0.9500	C29—H29	0.9500
C14—C15	1.381 (4)	C30—H30	0.9500

C1—O1—C5	122.38 (17)	C16—C17—H17	120.0
O1—C1—C2	119.2 (2)	C12—C17—H17	120.0
O1—C1—C6	114.02 (18)	C4—C18—C19	117.97 (18)
C2—C1—C6	126.7 (2)	C4—C18—H18A	107.8
C1—C2—C3	120.7 (2)	C19—C18—H18A	107.8
C1—C2—H2	119.6	C4—C18—H18B	107.8
C3—C2—H2	119.6	C19—C18—H18B	107.8
C2—C3—C4	119.20 (19)	H18A—C18—H18B	107.2
C2—C3—C12	117.49 (19)	C24—C19—C20	118.8 (2)
C4—C3—C12	123.20 (19)	C24—C19—C18	117.8 (2)
C5—C4—C3	117.36 (19)	C20—C19—C18	123.3 (2)
C5—C4—C18	119.88 (19)	C19—C20—C21	119.8 (2)
C3—C4—C18	122.05 (19)	C19—C20—H20	120.1
O1—C5—C4	121.08 (19)	C21—C20—H20	120.1
O1—C5—C25	111.18 (18)	C22—C21—C20	121.2 (2)
C4—C5—C25	127.68 (19)	C22—C21—H21	119.4
C11—C6—C7	119.9 (2)	C20—C21—H21	119.4
C11—C6—C1	120.9 (2)	C21—C22—C23	119.2 (2)
C7—C6—C1	119.14 (19)	C21—C22—H22	120.4
C8—C7—C6	119.8 (2)	C23—C22—H22	120.4
C8—C7—H7	120.1	C22—C23—C24	120.2 (2)
C6—C7—H7	120.1	C22—C23—H23	119.9
C9—C8—C7	119.8 (2)	C24—C23—H23	119.9
C9—C8—H8	120.1	C19—C24—C23	120.6 (2)
C7—C8—H8	120.1	C19—C24—H24	119.7
C8—C9—C10	120.6 (2)	C23—C24—H24	119.7
C8—C9—H9	119.7	C30—C25—C26	119.9 (2)
C10—C9—H9	119.7	C30—C25—C5	118.7 (2)
C11—C10—C9	120.0 (2)	C26—C25—C5	121.4 (2)
C11—C10—H10	120.0	C27—C26—C25	119.7 (2)
C9—C10—H10	120.0	C27—C26—H26	120.2
C6—C11—C10	119.9 (2)	C25—C26—H26	120.2
C6—C11—H11	120.1	C26—C27—C28	120.4 (2)
C10—C11—H11	120.1	C26—C27—H27	119.8
C13—C12—C17	118.9 (2)	C28—C27—H27	119.8
C13—C12—C3	119.3 (2)	C29—C28—C27	120.0 (2)
C17—C12—C3	121.7 (2)	C29—C28—H28	120.0
C12—C13—C14	120.3 (2)	C27—C28—H28	120.0
C12—C13—H13	119.8	C28—C29—C30	120.3 (2)
C14—C13—H13	119.8	C28—C29—H29	119.9
C15—C14—C13	120.7 (2)	C30—C29—H29	119.9
C15—C14—H14	119.7	C25—C30—C29	119.7 (2)
C13—C14—H14	119.7	C25—C30—H30	120.1
C14—C15—C16	119.3 (2)	C29—C30—H30	120.1
C14—C15—H15	120.4	F1—B1—F3	113.1 (2)
C16—C15—H15	120.4	F1—B1—F2	111.4 (2)
C17—C16—C15	120.9 (2)	F3—B1—F2	111.5 (2)
C17—C16—H16	119.6	F1—B1—F4	106.8 (2)
C15—C16—H16	119.6	F3—B1—F4	107.5 (2)
C16—C17—C12	119.9 (2)	F2—B1—F4	106.2 (2)

Footnotes

‡Additional correspondence e-mail: solangewardell@yahoo.co.uk

Acknowledgements

The authors thank the EPSRC X-ray Crystallographic Service, University of Southampton, for the data collection.

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